Professional Documents
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UVEB Technology 319 Web
UVEB Technology 319 Web
UVEB Technology 319 Web
Vol. 5, No. 3
UV Curing Enhances
Print & Packaging
Waterbased Resins in Inkjet Inks
Curable Pressure
Sensitive Adhesives
ANNUAL
BUYERS
GUIDE
EDITION
COLUMNS
8 UV Curing Technology
“Do you have time to answer a few questions...”
By Jim Raymont, EIT LLC
For over two decades Honle UV America has been raising the
bar in the development of new UV/LED curing technology that
has made the printing, coating, and adhesive assembly industries
worldSE@AIKNALNKòP=>HA,QNATLANPEOAHEAOEJQJHKcking the
potential of UV/LED light and transforming its power into a variety
KB?QOPKIAJCEJAANA@?QNEJCOKHQPEKJOPD=PSEHHI=TEIEVAyour
productiREPU=J@LNKòP=>EHEPy
,QNATLANPAJCEJAANO=NAKJD=J@BKNKJOEPAAvaluations,
they’ll make recommendations on UV/LED equipment, and
support you and yKQNOP=BBPDNKQCDKQPPDAHEBAKBKQNLNK@Q?PO
JETCURE LED
2020 RadTech Conference Abstract will present a Surface Summit Event at the Dearborn Inn.
Deadlines Near RadTech is a co-sponsor of the event.
Abstract deadlines
are approaching for Registration for the Fall Member Meeting is open. Register, check
the 2020 RadTech for more information and see updates at www.radtech.org.
UV+EB Technology
Conference and Abstracts Due November 30
the 2020 IUVA for ICULTA 2020 in Berlin
Americas Conference, scheduled for March 8 through 11, 2020. Two years after the first successful International Conference
For the first time, the conferences will be co-located at the Disney on UV LED Technologies & Applications (ICULTA) the next
Coronado Springs Resort in Orlando, Florida, offering attendees conference is set for April 26 through 29, 2020, at the MELIÃ
a complete picture of the UV/EB industry, including applications Hotel in Berlin, Germany. The submission deadline for oral and
in curing, disinfection, sterilization, sensing and more. The poster presentation abstracts is November 30.
co-located events are expected to attract more than 1,400 total
attendees. ICULTA will bring together pioneers, leaders and experts from
science and industry to discuss progress and innovations in the
Abstracts for RadTech conference presentations are due development of UV LEDs and the broad spectrum of applications.
September 20, 2019. Presentations should be no longer than 25 The conference is jointly organized by the German consortium
minutes with five minutes for questions. Potential presenters may Advanced UV for Life and the International Ultraviolet
fill out the online Abstract Submission Form. The description Association (IUVA). The event offers an international platform
should be sufficiently comprehensive to allow assessment of the for experts in UV LED technology and applications, who are
paper’s scope and content. For more information, visit https:// invited to participate as a speaker, attendee, exhibitor and/or
radtech2020.com/index.php/call-for-papers/ or contact Mickey sponsor. For more information, visit http://www.ICULTA.com.
Fortune at mickey@radtech.org or 240.643.0517.
Design Students Encouraged
Conference exhibitor and sponsor information is available at to Enter Poster Competition
https://radtech2020.com or www.iuva.org. The Technical Association for the Graphic Arts (TAGA) and
RadTech are partnering again on the UV+EB Technology Student
NIST, RadTech Developing Workshop Poster Design Competition, which offers students cash prizes for
for Use of Photopolymer Materials creative poster designs. Experience in UV/EB technology – while
in Additive Manufacturing widely used in graphic arts and food packaging, as well as in 3D
In a partnership with the National Institute of Standards and printing/additive manufacturing, electronics and a number of
Technology (NIST), RadTech is organizing a two-day road- metal, wood and plastics applications – is not required.
mapping workshop for the use of photopolymer materials in RadTech will display and celebrate winning entries at the 2020
additive manufacturing. The workshop is set for October 29 and RadTech Conference at Disney’s Coronado Springs Resort in
30 in Boulder, Colorado. Orlando, Florida, March 9 through 12, 2020.
Member feedback is sought on setting workshop goals and Entries must be submitted to RadTech by December 31, 2019.
program details. Members and others who are actively involved in Interested graphic arts and design students are encouraged to learn
the 3D printing and additive manufacturing supply chain can help more and register at https://www.taga.org/radtech/.
by providing comments and ideas to Mickey Fortune at mickey@
radtech.org. RadTech Joins Academy of Inventors
to Create Trade Association Chapter
RadTech Fall Member Meeting Set RadTech has joined the National Academy of Inventors as a
for November 4 in Michigan Member Institution. The academy is a US nonprofit organization
The RadTech Fall Member Meeting is scheduled for November 4 dedicated to encouraging inventors and recognizing achievements
at the Dearborn Inn, Dearborn, Michigan. that have made a “tangible impact on the quality of life, economic
development and the welfare of society.” While traditionally
Meetings and new initiatives will focus on UV LED, 3D printing, focused on academia, NAI has accepted RadTech as the first
application support, transportation, and printing and packaging. nonprofit trade association chapter.
RadTech also will host tours at Ford Motor Company in the
morning before the meeting. “In recognition of the many inventors in our technology space,
and to build on RadTech’s fast developing ‘RadLaunch’ effort to
On November 5, Plastics Decorating magazine (published by support start-ups, we look forward to the opportunity to engage
Peterson Publications, which also publishes UV+EB Technology) with the NAI community and are excited to start our own, unique
Part one: The ability to accurately and repeatedly measure a UV Figure 1. The above graph is a good example of sample rate
source depends, in part, on the radiometer’s ability to gather and and resolution.
store an adequate number of observations (samples) under the UV
source.
Today’s technology allows radiometers to sample at extremely high Part One discussed the sample rate of the radiometer. Part Two
rates (e.g., >30,000 Hz). Through the use of electronic/data (not deals with how to properly interpret the data collected.
optical) filters, effective (equivalent) sample rates ranging from 128 Figures 2 and 3 show data for a single non-focused UV lamp,
to 2048 Hz can be set by the user. collected under identical conditions except for the effective sample
rate of the radiometer. Only the UVA (EIT 320 to 390 nm) is
Faster sampling rates provide greater resolution, especially as the shown; the X axis is time and Y axis is UV irradiance.
speeds of some applications (digital printers) approach 500 to 600
feet (150 to 180 meters) per minute. The ability to collect data The data in Figure 2 were collected at an effective sample rate of
128 Hz. The peak irradiance is 318.3 mW/cm2, and the energy
8 | UV+EB Technology • Issue 3, 2019 uvebtechnology.com + radtech.org
Figure 3. The peak irradiance in this example is 618.0 mW/cm2
and the total energy density is 139.9 mJ/cm2.
Figure 5. Two irradiance profiles of another lamp at effective
sample rates of 128 Hz and 2048 Hz.
Reit sees mass production as the next step for Pylux. “While
we are pretty early in the process,” he said “our core is always
going to be new product development and innovating on specific
technical metrics. Of course, we’re always looking for that first
commercial validation in incorporation of your materials into
some mass-produced device. We already have some validation IST AMERICA U.S. OPERATIONS
HANDCURE
from major Japanese chemical film manufacturers, which are 121-123 Capista Drive
Shorewood, IL 60404-8851
doing some commercial licensing and development contracts Tel. +1 815 733 5345
info@usa.ist-uv.com
LED Mobile Curing
with us. It’s in the pilot stage. Ultimately, once we go into mass www.ist-uv.com
The rubber band – A valuable learning aid Entropy Change. What about the change in entropy, DS? Clearly,
The properties of any material depend on its composition and as the rubber band is stretched, the macromolecules become
molecular structure. Most rubber bands are made from natural much more ordered. Therefore, there is a substantial decrease in
sources of rubber because of the elasticity of such materials2. entropy (DS = negative). This does not favor spontaneous change
But, it is the molecular structure of a rubber band – a lightly and, of course, stretching is not a spontaneous process. Rather,
crosslinked polymer – and the resultant fascinating physical contraction of the rubber band takes place spontaneously when
properties it produces that are the subject of this discussion. DS = positive.
Thermodynamics of stretching. When you stretch a rubber Free Energy Change. While positive changes in entropy favor
band, what do you see? Feel? Observe? Stretch it and immediately spontaneity, it is the free energy change of a process, ∆G, that
touch it to your forehead or chin. What do you feel? Now, with it actually determines whether or not a process is spontaneous.
stretched, release it and allow it to retract back, and then quickly To evaluate ∆G, the change in enthalpy, the change in entropy
touch it again. What do you feel this time? What would happen if and the Kelvin temperature must all be taken into consideration.
you stretched the rubber band and, while stretched, you warmed it Equation 1 shows the relationship among these four parameters.
with a hair dryer? Would it expand farther, or would it contract?
∆G = ∆H - TDS Equation 1
Enthalpy Change. When you stretched the rubber band, you
should have noted that it was warmer than before stretching. When the sign of ∆G is negative, the process will be
This indicates that the enthalpy change, ∆H, is exothermic (more thermodynamically spontaneous. When the rubber band is
negative) during stretching. When you then allowed a stretched stretched, ∆H is quite negative. But, so is DS! The entropy change
rubber band to contract, you should have felt that it was cooler is sufficiently negative when stretched to produce a “TDS” value
to the touch. The process of contraction or relaxation from a more negative than ∆H, and this produces a positive value for
stretched position is endothermic; the rubber band is absorbing ∆G. Thus, stretching is non-spontaneous, while relaxation is
energy from its surroundings. Note that this is a purely physical spontaneous – even though the former is exothermic and the latter
process. No change in composition has occurred, yet there is is endothermic. The relaxation process is entropy driven!
a detectable and reproducible thermodynamic result. Since the
composition remained the same before and after stretching, it is So, what happens when you warm a stretched rubber band? If
clear a structural change at the molecular level has taken place. it expands, as many might expect, the temperature (T) would
increase and its entropy
would decrease. Thus,
Relaxed Rubber Band Stretched Rubber Band “TDS” would become
S-T-R-E-T-C-H more negative. ∆G
would then become
more positive. But, if it
RELAX
AX contracts on heating, T
would increase but DS
Figure 1. Figure 2.
M any commercial sheetfed litho printing presses that are used to print on flat steel sheets for the can
industry, or on paper or plastic sheets, utilize traditional UV arc lamps that are cooled by a combination
of water and air to help prevent overheating critical press parts. These UV lamps are placed after each printing
station or deck and will cure each ink color after it is printed. These presses have very little space for the
lamp; as a result, the lamps can become cumbersome to maintain, generate a lot of heat – which can damage
the press – and typically have short lamp and reflector life since they are not adequately cooled due to poor
air flow. Since these presses have a tight space constraint in which to mount a lamp, it can limit which type of
lamp can be used. Therefore, microwave lamps are almost never used since they are too large. However, after
the sheet is printed, there almost always is a set of lamps to complete the curing on a conveyor. In this case,
any lamp type could be used to complete
the ink cure. This paper will explore a Table 1. Arc lamp
comparison of lamp types to use for inter-
deck ink curing and final ink curing. It is High-Powered ARC Lamp Technology
part of a larger study on various lamp, ink High Peak Irradiance 7 watts/cm2
and varnish combinations. The three lamp Long Lamp Life – 2,000 to 4,000 Hours
systems chosen are the high-powered arc
lamp, microwave lamp and UV LED multi- UV Output Uniformity
wavelength lamp system. Ability to Use Various Spectrum Bulbs
Very Few Replacement Parts
UV source/Chemistry background
Three major categories of UV sources are
commonly used in industry: arc, microwave Table 2. Microwave lamp
and UV LED lamps. In addition, UV LED
Microwave Lamp Technology
lamps can be further divided into single
wavelength and multi-wavelength lamps. No Electrode = Long Life Bulbs 6,000 to 8,000 hours
Each UV source has its advantages, as Small Diameter Bulbs = Higher Intensity 6.8 watts/cm2
shown in Tables 1-3. Ability to Use Various Broad Spectrum Bulbs
To a company seeking to either convert to Fast ON/OFF – No Shutters Required
a UV-curable system on a can coating line
or simply to upgrade an older system, these Table 3. UV LED
advantages all look attractive, and there is no
obvious winner amongst the three UV source UV-LED lamp Technology
contenders. Lower Heat Generation
Instant ON/OFF – No Shutters
There also is the question of the proper
formulated ink and varnish to be coated. No Ozone Created; Therefore No Exhaust System
A wide variety of ink and varnishes are Needed
formulated specifically for broadband energy Modular Compact Design
sources, such as arc or microwave and UV No Mercury
LED formulated varnishes. This could get
complicated for the converter in the case that Higher Energy Efficiency
Experimental conditions
The coating line was set up as shown in Figure
1. The UV lamps used in the evaluation are the Figure 1. Coating line configuration
Miltec UV HPI™ 23" Arc Lamp UV System,
Miltec UV Xtrema Plus™ Microwave Powered
UV System, Miltec UV 385nm UV LED and a
Miltec UV LED Multi-spectrum UV. The black
UV-curable ink was obtained from Sun Chemical.
The UV broadband-curable varnishes were
obtained from Watson Standard, while the UV
LED-formulated clear varnishes were obtained
from UVitec. Ink application was done per the
supplier recommendation for each ink type, using a
Little Joe Proofing Press. All clear varnishes were
applied via drawdown. The Watson Standard 971-
0452-L varnish was applied at the standard film
weight of 22 to 26 mg per sq.in. The UVitec UV
LED varnish was applied at a film weight of 22 to
Figure 2. Experimental plan
26 mg per sq.in.
Results
The experimental plan is illustrated in Figure 2.
page 18
16 | UV+EB Technology • Issue 3, 2019 uvebtechnology.com + radtech.org
ARC UV
MICROWAVE UV
Your ONLY
source for all UV
technologies
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TECHNOLOGY
Printing &
of which type of formulations can be used, it was noted in
Packaging
Innovations
Wood Fin
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Technolog ng
EB Application
Advancementsy
many other experimental runs that it is important to align the
photoinitiator absorbance with the emitted UV spectrum. This is a
Ultraso nicFood
UV-Inkjet on Acous
Assisted Drying tically
TECHNOLOGY
Packaging
America
International North America
Official Publica
tion of RadTec
h Internat
UV LED formulation or an Hg lamp formulation.
ional North
America
P erforming print finishing services, Feiereisen, Inc., is a family-owned business with headquarters in Cedar
Rapids, Iowa. In business since 1933, the nationwide provider recently created a custom-designed, diecut
pocket folder with a series of single, two-sided inserts, titled Finish With Style, to promote itself as a graphic
arts finisher. Touching on some of the more traditional finishing techniques, like diecutting and laminating,
this piece also “stresses one of Feiereisen’s newest available services, which is an extremely high-end digital
enhancement press that prints inline digital spot UV and digital foils,” Feiereisen’s President Greg Ortmann
commented.
Jack Noonan, marketing manager at MGI, said that the Konica Minolta MGI JETvarnish 3DS with iFoil was
used to create the a unique product, and that “this digital decorative solution is the only print enrichment
process to utilize three inline methods of curing.” He continued, “IR is for low-level, flat 2D spot coats and
rounded, domed smooth effects. The LED is for freezing and pinning high-build 3D textures and sculpted
image effects. And then, the full-powered UV is for final curing
of all clear ink (varnish polymer) treatments.” Additionally, the
UV lamp system provides the final curing method for embossed
foil applications where a hyper-sensitive foil roller is calibrated
with pixel-to-micron inkjet management. Knowing what the
JETvarnish can do, Ortmann said Feiereisen decided to use
this equipment to showcase the company’s capabilities.
The project earned a Gold Leaf award for Best Use of Digital
Inkjet-Coating from the Foil and Specialty Effects Association
(FSEA).
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LII CTGA Promo Piece
Submitted by: Label Impressions, Inc.
BRONZE
Univacco Ribbon
Submitted by: Univacco Technology Inc.
SILVER BRONZE
Beverage Series Tap Cleveland Cake
Submitted by: Univacco Technology Inc. Submitted by: Tap Packaging Solutions
SILVER BRONZE
Print Panther Belladonna Premium Cannabis
Presentation Folder Submitted by: Ross Printing
Submitted by: Print
Panther
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Pause
Submitted by:
Jostens
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Ariel & The Big Baby/Rapunzel Finds a Friend
Submitted by: Bertelsmann Printing Group USA
Waterbased UV LED-
By Jo Ann
Arceneaux, Tong
Wang and
Curable Compositions
Hwei-Ling Yau,
allnex USA Inc.;
and Michel
Tielemans,
Kevin Poelmans
and Laurence
Boutreau, allnex
for Graphics Applications
Belgium SA/NV
Abstract
W ith the increasing regulatory pressure on acrylate monomers, the energy-curable graphics market
has started to investigate the use of energy-curable waterborne resins and polyurethane dispersions
(PUDs). Some products are particularly suitable for food contact applications, as illustrated by comprehensive
migration tests and compliance with existing regulations. These energy-curable waterborne resins and PUDs
also find utility in the development of next-generation low-viscosity inkjet inks and overprint varnishes where
re-dispersibility in water is required. Data on the performance of these waterborne systems cured with both
mercury lamps and LED lamps will be presented.
EC PUD 1
EC PUD 2
EC PUD 3
EC PUD 912
EC PUD 929
EC PUD 953
The 100% solids energy-curable (EC) inkjet inks are very fast
curing, with improved resolution and color strength. They have
better resistance properties and are low in VOCs. However,
some of the more opaque inks are difficult to cure because of
film thickness. These EC inkjet inks are based on acrylated
oligomers and monomers, pigments, additives and photoinitiators.
They must contain high levels of acrylated monomers to reduce
viscosity, and more of the monomer is mono-functional, due to
the very low viscosity requirements. This monomer use results
in odor and safety concerns, and in many cases, the Globally
Harmonized System (GHS) labeling is not user friendly. The Figure 2. Composition of EC PUD 929
photoinitiator (PI) and its fragments also may create concerns for
food packaging applications. [If electron beam (EB) cure is used,
no PI is necessary, and this concern is eliminated.] Energy-curable
inkjet inks do not dry in the print heads, so nozzle blockage is not
a concern.2,3
Save money,
space and Solvent-free UV LED
energy and mercury solutions
from LESCO
CUSTOM SHUTTERED
Since 1960 American Ultraviolet has provided tens Call 800-288-9288, or visit americanultraviolet.com
of thousands of customers with effective standard to discuss your UV curing requirements. If we
and custom UV solutions and LED UV curing don’t already have the perfect system, we’ll
systems that: design and manufacture an insightful solution
• Quickly, safely, responsibly cure inks, that will provide remarkable results for you
adhesives and coatings and your customers, as we’ve been doing
• Work in a broad range of research and since 1960.
manufacturing settings
• Are backed by expert advise, proven www.americanultraviolet.com
value, superior support, and 1-800-288-9288 • 1-800-615-3726
product warranties mstines@auvco.com
INKJET INKS
page 26
5HWURÀWSKRVHRQFRP
INKJET INKS
page 28
Ink reactivity
Ink reactivity, or cure speed, can be
affected by several variables. These
include double-bond concentration of the
ink, photoinitiator concentration, lamp type
and output (wavelength and intensity),
pigment color and concentration, and ink
thickness, to name a few. With UV LED
lamps, oxygen inhibition of the free radical
polymerization also impacts surface cure
speed.9 Figure 7. Cure speed (m/min) of EC PUD-based CMYK inkjet inks with mercury lamps
microns depth using the peak area at 810 cm-1 (C=C) and the 610 tapes) and reported as percent coating that remained on the
reference peak area at 764 cm-1.10 substrate.
Higher double-bond conversions were obtained with TPO-L With rigid PVC and HIPs, 100% adhesion was obtained for all
versus BAPO, consistent with the cure speed results. (The EC PUD coatings. The coating based on EC PUD 929 had 100%
exception was the 6% PI level cured at 90°C.) For room adhesion to all of the substrates. EC PUD 912 and EC PUD 953
temperature cure, 1% TPO-L was as good as 3 or 6%. At 90°C, page 32
3.0% TPO-L gave the best double-bond conversion. For BAPO,
6% levels gave the best double-bond conversion for both cure
temperatures.
References
These adhesion data show
1. Handbook of Industrial Inkjet Printing, Volume I, pp 27-28. W.
Zapka, Ed. Wiley-VCH 2018.
that through cure was achieved
2. Ibid., pp 129-138.
3. Ibid., pp 59-111.
for all EC PUDs, even though
4. Ibid., pp 48-56.
5. Ibid., pp 108-111.
surface cure was not.
32 | UV+EB Technology • Issue 3, 2019 uvebtechnology.com + radtech.org
Bringing it
all Together.
With nearly 6,000 employees in 20 countries, NAGASE supplies innovative, quality materials
to the chemicals market globally.
We offer a wide portfolio of UV/EB raw materials, including cationic and free radical solutions,
hybrid grades, acrylamides, thiols, long wavelength and UV-LED active photoinitiators,
photosensitizers and more to enhance formulations from coatings to additive manufacturing.
NagaseAmerica.com
0LZRQ«WKHGHULYDWLRQÁRZV
from “Original Beauty”
As the leading-edge supplier of the
highest market quality materials, Miwon
now offers unique Monomers and
Oligomers as compliant alternatives
(HAP/Toluene - Free materials) to meet
increasingly stringent downstream end-
use ink, coating & adhesive market
formulation requirements.
3D PRINTING RESINS/ PL Industries, division of Esstech, Inc., Precision Ink Corp., 1, 2, 3, 6 GEW (EC) Limited, 2, 3
1, 2 Sappi North America, 1, 2, 4, 5, 6 Hamamatsu Photonics Deutschland
PHOTOPOLYMERS Siltech Corporation, 2 Sartomer Americas GmbH, 1, 2, 3
ZEXI USA LLC, 1, 2 Siegwerk EIC LLC, 3, 4, 6 Hanovia Specialty Lighting LLC, 3
Allied PhotoChemical, Inc. Sun Chemical, 1, 2, 3, 4, 5, 6 Honle UV America , Inc., 2, 3
Allnex USA Inc. UV III Systems, Inc. IST America Corporation, 2, 3
BASF Dispersions & Resins Van Technologies, Inc. (Mfgr of KJCJ Consulting, 1, 2, 3
DDU Enterprises Inc. GreenLight Coatings), 1, 2, 3, 6 Kyocera International, Inc., 2
Nagase America Corporation Wikoff Color Corporation, 1, 4, 6 Miltec UV, 2, 3
Penn Color, Inc. Nedap UV, 2, 3
PL Industries, division of Esstech, Inc. OWLE Technologies, 2
RAHN USA Corporation CONSULTING SERVICES PCT Ebeam and Integration, 1
Sartomer Americas Phoseon Technology, 2
Siltech Corporation BCH North America Inc. Allied PhotoChemical, Inc.
Prime UV – IR, 2, 3
Wikoff Color Corporation 15720 Brixam Hill Avenue Carestream
Sappi North America, 1
ChemQuest Technology Institute
Charlotte, NC 28277 Sartomer Americas
DDU Enterprises Inc.
Ushio America, Inc., 2
Phone: 704-470-2340 Dvorchak Enterprises LLC
UV III Systems, Inc., 3
Website: bch-bruehl.com Energy Sciences, Inc.
IST America Corporation
KJCJ Consulting
Kromachem Inc.
National Polymer
Sartomer Americas COATING EQUIPMENT/ PL Industries, division of Esstech, Inc.
502 Thomas Jones Way MACHINERY Prime UV – IR
Exton, PA 19341
Allied PhotoChemical, Inc. CURE/DOSE Honle UV America, Inc.
Phone: 610-363-4100
American Ultraviolet MEASUREMENT 261 Cedar Hill St. Bldg. C
Website: sartomer.com Ashland Marlboro, MA 01752
DDU Enterprises Inc. EQUIPMENT
Phone: 508-229-7774
Energy Sciences, Inc.
Excelitas Technologies 1. Sensors Fax: 508-229-8530
Prime UV – IR Website: HonleUV.com
ADDITIVES Vergason Technology Inc. Boston Electronics, 1
DDU Enterprises Inc.
1. Acrylamides EIT Instrument Markets, 1
COATINGS Energy Sciences, Inc., 1
2. Cationic Solutions
3. Free Radical Solutions GEW (EC) Limited, 1
1. 100% Solids Hamamatsu Photonics Deutschland
4. Thiois 2. Clear Coat GmbH, 1
3. Pigmented Honle UV America , Inc., 1
Allnex USA Inc. 4. Solventborne
BASF Dispersions & Resins Prime UV – IR, 1
5. Silicone-based
Dymax Corporation, 1 6. Water-based
Hybrid Plastics Inc., 2, 3, 4 IST America Corporation
Kromachem Inc., 3 ACTEGA North America, Inc., 1, 2, 3, 6 121 - 123 Capista Drive
Nagase America Corporation, 1, 2, 3, 4 Alberdingk Boley, 2, 3, 6 Shorewood, IL 60404-8851
PL Industries, division of Esstech, Inc. Allied PhotoChemical, Inc., 1, 2, 3, 4, 6 Phone: 815-733-5345
Ashland, 1, 2, 4, 5, 6
Website: ist-uv.com
ADHESIVES/SEALANTS Carestream, 1, 2, 3, 4, 5, 6
Dvorchak Enterprises LLC, 1, 2, 3, 4, 6
ACTEGA North America, Inc. Energy Sciences, Inc., 1 EIT Instrument Markets
Alberdingk Boley Hauthaway Corporation, 6 .HOO\V)RUG3OD]D6(
Ashland INX International Ink Co. /HHVEXUJ, VA 201
BASF Dispersions & Resins KJCJ Consulting, 1, 2, 3, 4, 6
Kromachem Inc., 3, 6 Phone: 703-478-0700
Carestream Email: uv@eit.com
Dymax Corporation Michelman, 6
Miltec UV Website: eit.com
Excelitas Technologies
Miltec UV National Polymer
National Polymer Nazdar Ink Technologies, 2, 3, 4, 5, 6
PL Industries, division of Esstech, Inc. Penn Color, Inc., 1, 2, 3, 4, 5, 6 Nedap N.V.
Precision Ink Corp. CURING SOURCES Parallelweg 2
Sartomer Americas 7141 DC Groenlo
Wikoff Color Corporation 1. Electron Beam
2. UV LED The Netherlands
3. Ultraviolet Phone: +31 544 471860
CATIONIC Website: nedap-uv.com
Allied PhotoChemical, Inc.
1. Photoinitiators Allied Photochemical, Inc. American Ultraviolet, 2, 3
2. Monomers/Oligomers 16024 Angelo Drive Ashland, 1, 2
Macomb, MI 48042 Boston Electronics, 2 CUSTOM FORMULATED
Aal Chem, 1, 2 Carestream, 2, 3 PRODUCTS
BCH, 1 Phone: 586-232-3637 ChemQuest Technology Institute, 2, 3
Hampford Research, 1 Fax: 586-232-3889 DDU Enterprises Inc., 3 Allied PhotoChemical, Inc.
Hybrid Plastics Inc., 2 Website: alliedphotochemical.com Dymax Corporation, 2, 3 Ashland
KJCJ Consulting, 1, 2 Email: mkelly@alliedphotochemical.com Energy Sciences, Inc., 1 Carestream
Nagase America Corporation, 1, 2 Excelitas Technologies ChemQuest Technology Institute
DDU Enterprises Inc. Kromachem Inc. Energy Sciences, Inc., 2 IGM Resins Inc., 1, 2
Hauthaway Corporation Miwon North America INX International Ink Co., 1, 2, 4 KJCJ Consulting, 1, 2
Hybrid Plastics Inc. National Polymer Kao Collins Inc., 1 Miwon North America, 1, 2
Kopp Glass PL Industries, division of Esstech, Inc. KJCJ Consulting, 1, 2 Nagase America Corporation, 1, 2
Kromachem Inc Sappi North America Kromachem Inc., 1, 2 National Polymer
Miltec UV Sartomer Americas Miltec UV PL Industries, division of Esstech, Inc.,
National Polymer Siltech Corporation Nazdar Ink Technologies, 1, 2, 3, 4 1, 2
Penn Color, Inc. ZEXI USA LLC Penn Color, Inc., 1, 2 RAHN USA Corporation, 1, 2
Precision Ink Corp. Precision Ink Corp., 2, 4 Sartomer Americas
Sartomer Americas Siegwerk EIC LLC, 1, 2, 3, 4 Siltech Corporation, 1
Van Technologies, Inc. (Mfgr of Sun Chemical, 1, 2, 3, 4
GreenLight Coatings) Wikoff Color Corporation, 1, 2, 3, 4
Wikoff Color Corporation ZEXI USA LLC, 1, 2, 3, 4
ZEXI USA LLC
LED CURING
PL Industries, division of EQUIPMENT/MACHINERY
Esstech, Inc.
48 Powhattan Avenue 1. Conveyer Miwon North America
Essington, PA 19029
2. Spot 100 Arrandale Blvd., Suite 104
3. In-line
Exton, PA 19341
Phone: 610-299-4118 4. Hand-held
Allied Photochemical, Inc. Fax: 610-521-4600 Phone: 484-872-8177
16024 Angelo Drive Website: plindustries.esstechinc.com Allied PhotoChemical, Inc., 1, 2, 3, 4 Fax: 484-872-8717
Macomb, MI 48042 American Ultraviolet, 1, 2, 3, 4 Website: miramer.com
Ashland, 1
Phone: 586-232-3637
ChemQuest Technology Institute, 1, 3
Fax: 586-232-3889 ELECTRON BEAM DDU Enterprises Inc., 1, 2, 3, 4
Website: alliedphotochemical.com CURING EQUIPMENT/ Dymax Corporation, 1, 2, 4
Email: mkelly@alliedphotochemical.com Excelitas Technologies, 1, 2, 3, 4
MACHINERY
GEW (EC) Limited, 3
1. Wide Web Hamamatsu Photonics Deutschland
2. Narrow Web GmbH, 1, 2, 3, 4
Heraeus Noblelight America LLC
Energy Sciences, Inc., 1, 2 Honle UV America, Inc., 1, 2, 3, 4
IST America Corporation, 1, 2, 3, 4 Nagase America
Hamamatsu Photonics Deutschland
GmbH, 1, 2 Miltec UV, 1, 3 Corporation
KJCJ Consulting, 1, 2 Nedap UV, 1, 2, 3, 4 546 Fifth Avenue, 16th Floor
PCT Ebeam and Integration, 1, 2 OWLE Technologies New York, NY 10036
Sartomer Americas Prime UV – IR, 1, 2, 3, 4
502 Thomas Jones Way Ushio America, Inc., 2 Phone: 212-703-1340
Exton, PA 19341 EMULSIONS/ Fax: 212-398-0687
Website: nagaseamerica.com
Phone: 610-363-4100 DISPERSIONS
Website: sartomer.com
Alberdingk Boley
BASF Dispersions & Resins OLIGOMERS
Hauthaway Corporation
Kromachem Inc. 1. Acrylate
National Polymer 2. Methacrylate
CUSTOM RAW Penn Color, Inc. 3. Other
ZEXI USA LLC IST America Corporation
MATERIALS 121 - 123 Capista Drive Aal Chem, 1, 2, 3
Shorewood, IL 60404-8851 Allnex USA Inc.
Alberdingk Boley GLASS OPTICS BASF Dispersions & Resins
BCH Phone: 815-733-5345 BCH, 3
ChemQuest Technology Institute DDU Enterprises Inc. Website: ist-uv.com Dymax Corporation, 1, 2
Dymax Corporation Kopp Glass Hybrid Plastics Inc., 1, 2, 3
Hauthaway Corporation Miltec UV IGM Resins Inc., 1, 2, 3
IGM Resins Inc. Prime UV – IR KJCJ Consulting, 1, 2, 3
Kopp Glass Miwon North America, 1, 2, 3
LIGHT STABILIZERS
HYBRID POLYMERS
Aal Chem
Hybrid Plastics Inc. BASF Dispersions & Resins
KJCJ Consulting IGM Resins Inc.
Nagase America Corporation PL Industries, division of Esstech, Inc.
National Polymer
MONOMERS
INKS
BCH North America Inc. 1. Acrylate
BCH North America Inc.
15720 Brixam Hill Avenue 1. Inkjet 15720 Brixam Hill Avenue
2. Other
Charlotte, NC 28277 2. Flexo Charlotte, NC 28277
Phone: 704-470-2340 3. Screen Aal Chem, 1, 2 Phone: 704-470-2340
Website: bch-bruehl.com
4. Offset Allnex USA Inc. Website: bch-bruehl.com
BASF Dispersions & Resins
ACTEGA North America, Inc., 2, 3 Hybrid Plastics Inc., 1, 2
Allied PhotoChemical, Inc.
uvebtechnology.com + radtech.org UV+EB Technology • Issue 3, 2019 | 37
PRODUCTS/SERVICES
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513-794-4285 Printing & Packaging, Wood and Building Industries Served: Biomedical/Medical,
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Chagrin Falls, OH 44023 and Building Products
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410-604-2900 215-345-6550
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Medical, Ceramics, Glass, Industrial, Inkjet/
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Insights | www.insights.basf.com
By Chris Orilall,
Zack Weinert, Jon
Scholte, Chuck
Recent Progress in UV-/EB-
Curable Pressure Sensitive
Dong, and Jeff
Klang, Arkema
Inc., Sartomer
Adhesives
Business Unit
Abstract
E nergy-curable pressure sensitive adhesives (EC-PSAs) eliminate the need for drying, solvent extraction
or preheating steps (compared to traditional waterborne, solventborne and hot melt methods). These
processing benefits make such adhesives particularly suitable for temperature-sensitive substrates and in-line
application. Here, we demonstrate structure-property relationships between PSA formulation and properties
such as tack, peel strength, shear resistance and temperature performance. Highlights include screening the
viscoelastic properties and investigating routes to higher shear adhesion failure temperature (SAFT) PSAs.
Introduction
Adhesives are nonmetallic materials used to bond other materials by adhesion to their surfaces and cohesion
within the adhesive layer. Two different processes describe most adhesive bonding: 1) the adhesion
phenomenon or 2) by PSA action. In the former, adhesive fluid is transformed into a solid upon bonding.
A PSA, however, conserves its fluid state after its bond building. Therefore, some notable benefits of PSAs
are that the resistance to de-bonding is moderate and the joint may be delaminated without destroying the
laminate components.1
Today, the three main PSA technologies are waterborne (WB-PSA), solventborne (SBPSA) and hot melts
(HM-PSA). The global demand for these types of PSAs totals ~ 93%, with the rest being UV-curable hot
melts (UVHM-PSA) and silicone-based PSAs.2 Broadly speaking, SBPSAs and UVHM-PSAs tend to offer
“high” performance, HM-PSAs offer medium performance and WB-PSAs offer lower performance at the
lowest cost. Each of these technologies has its advantages, but also distinct disadvantages: low solvent/
plasticizer resistance for HM-PSAs, high concentration of volatile organic compounds (VOC) for SB-PSAs
and large equipment footprints required for WB-PSAs.
Herein, we present a UV-curable or electron beam (EB)-curable PSA made from 100% solids, i.e., no
solvents. These energy-curable systems are sometimes referred to as EC-PSA “syrup” formulations. The
product can be applied as a viscous liquid system without the need for heat (depending on the viscosity
requirements of the coating unit). Without solvents or water, this product eliminates the need for highly
regulated solvent extraction systems or for time-consuming oven-drying steps. As a result, EC-PSAs can lead
to higher productivity and lower manufacturing costs vs. conventional PSA products. Additionally, rapid cure,
improved dimension accuracy, heat resistance, chemical resistance and heavy coating weights are possible. To
use EC-PSAs, existing lines can be retrofitted with a UV lamp, a UV-LED lamp or an EB unit. Additionally,
EC-PSA syrups provide ideal formulation platforms for cure-in-place (CIP) automated applications. As will
be discussed, the viscosity of the EC-PSA formulation can be adjusted by varying the ratio of components,
thus tailoring the formulation for use in any deposition system. More so, this approach allows for control over
the performance of the PSA through choice and composition of starting ingredients.
Certain trends were observed for the EC-PSA in its cured state. We also investigated the choice of photoinitiator on PSA
When the adhesive Tg was greater than the service temperature, performance. Here, we investigated PSA performance of a
50 | UV+EB Technology • Issue 3, 2019 uvebtechnology.com + radtech.org
base UV PSA formulation
(CN 9073) with 5% loading of
either 2,4,6-trimethylbenzoyl-
diphenyl phosphine oxide (TPO),
Omnirad® 184, Omnirad®
2022 or Omnirad® 4265 and
with 3% loading of phenylbis
2,4,6-trimethylbenzoyl-
phosphine oxide (BAPO) (to
standardize amount of radicals
generated). PSA performance for
formulations with these different
photoinitiators is captured in
Table 2. (PSA adhesives were
all 68 μm thick and cured using
H bulb at 400 mJ/cm2). The
results indicate that the choice of
photoinitiator is crucial to PSA Figure 2. Range of UV PSA performance (tack and peel) achievable to-date.
performance and is dependent on
the other components in the formulation and on curing conditions. employed, while no photoinitiator was required for EB curing.
Just as different adhesive properties can be accessed within UV
UV PSA vs. EB PSA. We investigated the PSA performance of curing alone, different PSA performances were observed between
a base energy-curable formulation (CN 9073) cured via UV and the two curing methods. The main advantage of EB curing was
EB (Table 3). For the UV-curable formulation, 5% TPO was higher shear and unprecedented high SAFT. We also have seen
page 52
Versatility of EC-PSAs
Figure 2 captures the range of PSA performance
(tack and peel) achievable to-date via UV
curing. While this figure does not capture the
viscosity of each data point, it does demonstrate
how EC-PSAs can be tailored to meet very
specific PSA application targets. One interesting
advantage that EC-PSAs may be able to offer is
low tack with high peel strength, which could
potentially be useful for applications where
minimal pressure is required for bonding.
Furthermore, Figure 3 shows the range of SAFT
values that can be achieved by either UV PSA
or EB PSA. In the case of EB-cured PSAs,
SAFT values of > 400°F are unprecedented, and
current research and development efforts are
focused on extending the achievable property
spaces of both UV- and EB-PSAs, e.g., UV-
PSAs with high SAFT and high peel strength. Figure 3. Overview of the achievable SAFT values as a function of peel strength
We have attributed higher SAFT values for EB for UV-PSAs and EB-PSAs.
PSAS to the higher acrylate conversion for EB
cure vs. UV cure, which directly results in higher crosslinking ability to tailor each formulation to specific performance targets
density for EB PSAs vs UV PSAs. makes this approach very versatile.
Conclusion References
In summary, we found that a number of variables affect EC-PSA 1. Benedek. Pressure-Sensitive Adhesives and Applications, 2nd ed.
properties, including rheology and chemical characteristics. The (2004) New York, NY. Marcel Dekker, Inc.
2. AWA Global Specialty Pressure-Sensitive Tape Market Study 2016.
relationships between different measures of adhesive performance
3. Petrie, Edward M., “Formulating UV-Curing Liquid Pressure-
were analyzed, as were different methods of curing PSAs.
Sensitive Adhesives,” Adhesives and Sealants Industry Magazine.
Specifically, the choice and amount of oligomer, monomer, November 2008.
photoinitiator and additives are all crucial to the starting point 4. J. Lu and C. Dong. Radiation Curable Pressure Sensitive Adhesives.
liquid formulation. With this wealth of available chemistry, the Radtech 2016.
range of achievable EC-PSA performance is quite broad, and the 5. “Viscoelastic Properties of Pressure Sensitive Adhesives,” The
Journal of Adhesion, 60:1-4, 233-248.
6. C. A. Dahlquist. Proc. Nottingham Conference on Adhesion. Part
III, Chapter 5, p. 134.
One interesting advantage
Acknowledgments
that EC-PSAs may be able to The authors want to thank Zachary Hoffman, Kejun Chen and
offer is low tack with high peel the rest of the research and development team at Sartomer. We
also thank Sara Reynaud of the Arkema Analytical department
strength, which could potentially for training, support and advice concerning the rheology of PSAs.
We thank our PSA counterparts at Bostik and Arkema Coating
be useful for applications where Resins. We would also like to thank Im Rangwalla at Energy
Science Inc. (ESI) for the coating and curing of EB-PSA samples.
minimal pressure is required for
bonding.
UV LED Low-Migration
By Jake Staples,
Technical Team
Leader, Ashland
Laminating Adhesives
for Flexible Packaging
T he global flexible packaging market continues to evolve as shifts in consumer preference lean more
toward convenience in single-serve or grab-n-go options, extended shelf life and sustainability. In addition
to consumers driving innovation in flexible packaging, wide web and narrow web converters are beginning to
converge into the packaging space as they see increased opportunity in equipment and coating technologies,
thereby lowering the barrier to entry. With the advancements in ultraviolet light emitting diodes (UV LED)
curing technology, opportunities in the flexible packaging space become more available to the converter base.
Many drivers are attributed to the growth in the flexographic packaging market, including consumer
preferences (particularly from millennials, who desire convenience and single-serve packaging), the need
for increased shelf life, pet food manufacturers moving away from multiwall bags to flexible packaging and
growing interest in moving away from rigid to flexible structures.
Due to the significant growth in flexographic flexible packaging, the limitations of traditional UV curing
technologies that currently prohibit label and flexible packaging converters from participating in this segment
have been exposed. This is particularly true in the food and beverage segment, which is more than 50% of
mercury lamps, as well as additional environmental, operational such as PET, PE, PP, paper and foil, among others. The two
and performance benefits (see Table 2). constructions are unwound on press from their respective rolls.
The laminating adhesive is applied to the substrate with lower
UV LED laminating process absorption properties before being nipped or pressed to the second
In flexible packaging applications, the process of laminating substrate. Formulation application methods include flexo, gravure
is used to securely bond two or more flexible constructions, and coaters. The two substrates, combined with the wet adhesive
sandwiched between both layers,
Table 3. Most common flexible packaging structures then are passed underneath the UV
LED source for immediate cure (see
Figure 1). Pressure-sensitive adhesives
(PSAs), on the other hand, are dry
cured, since the first construction and
PSA are passed under the UV source
before being pressed to the second
construction.
and protective over-varnishes A. High temperature, heat sterilized or retorted [ca. 121ºC
(250ºF)]
now are enabling nonyellowing B. Boiling water sterilized (100ºC)
C. Hot filled or pasteurized above 66ºC (150ºF)
in the final cure at increasing D. Hot filled or pasteurized below 66ºC (150ºF)
E. Room temperature filled and stored (no thermal treatment in
press speeds that are the container)
approaching those of UV LED F. Refrigerated storage (no thermal treatment in the container)
G. Frozen storage (no thermal treatment in the container)
cured inks. H. Frozen or refrigerated storage: ready prepared foods intended
to be reheated in container at time of use
page 62
LOW MIGRATION
EXCELLENT ADHESION
OPTIMIZED REACTIVITY
INNOVATING
Follow us on:
WITH YOU IN MIND
sartomer.com
LAMINATING ADHESIVES
page 60
A-10: control < DL < DL ND B-10: control < DL < DL ND C-10: control < DL < DL ND
A-11: control < DL < DL ND B-11: control < DL < DL ND C-11: control < DL < DL ND
A-12: control < DL < DL ND B-12: control < DL < DL ND C-12: control < DL < DL ND
*Consumption Factor
I. Irradiation (ionizing radiation) Furthermore, UV LED technology has the advantage of providing
J. Cooking at temperatures exceeding 121ºC (250ºF) a curing process that is reliable, repeatable and extremely
controllable. With low migration and regulatory compliance, it is
Another key aspect to consider when evaluating the structure critical that process variables are monitored and kept within the
is the type of functional barrier being used. The functional defined operating window.
barrier prevents a varying degree of migration of the nonfood
contact material in what is being pouched – particularly if the UV LED technology, coupled with UV LED-formulated
contents are food. However, there is little guidance from the laminating adhesives for low-migration applications, represent
FDA or European Union that defines performance of an adequate an innovative and sustainable technological trend that will have
functional barrier and its corresponding acceptable migration growing importance in flexible packaging for those early adopters
levels.2 Ultimately, it is the converter and contract packager’s searching for market differentiation in the narrow, mid and wide
responsibility to determine the needed functional barrier. When web space.
testing the structural compliance of the package, ensure the hazard
information of the migrants and safe dietary levels are reviewed. Experimental
The FDA default exposure values can be used to determine the Laminations were made on the Mark Andy P5 press with a Mark
exposure level of the package, such as percent of diet exposed Andy Gen 2 ProLED (Phoseon FP601), 20 W/cm², 395 nm, flat
to the packaging type. This can be calculated by dividing the glass emitting window, UV LED curing station. The flexographic
safe dietary level by the exposure where a detection limit can be anilox for applying the adhesive was 360 lpi/5.42 bcm. Multi-
derived. Plastics (MP) 2 mil PE was the base, and MP 75 gauge PP was
the overlaminate. The laminating adhesives tested were Ashland
The same FDA regulatory requirements that apply to today’s Adhesive 1 and Adhesive 2. The press was run up to 500 fpm
packaging standards also are applicable when transitioning from a and at LED power settings ranging from 25% to 100%. Neither
traditional laminating adhesive, such as solvent-free, to UV LED. adhesive displayed any yellowing. The best adhesive bonds
As long as the appropriate steps are taken in the risk assessment for this construction were achieved by Adhesive 1, so these
of the packaging – including component migration, toxicological laminations were chosen for migration testing. Initial hand peels
data established limits and performing tests in all applicable food resulted in destructive bonds up to 500 fpm at 25% power.
types, temperatures and conditions – UV LED technology is a
viable, efficient and green method of cure.
The data are presented in Table 5. These results indicated that Acknowledgements
the samples made at up to 300 fpm are safe for use in food The author acknowledges Dr. Joseph Spinnato of Ashland for
packaging. The laminations made at 500 fpm had migration of his work on the migration risk assessment, Jennifer Heathcote of
both monomers above the limit. Eminence UV for her advice during the press trial and Catherine
Heckman of Ashland for her assistance. The trial was supported
A second round of laminations were made in the lab. A Harper by FlintGroup through the use of its pilot press.
flexographic hand proofer with a 260l pi/5.48 bcm anilox was
References
used for applying the adhesive to the samples, and they were
1. Smithers Pira, 1/2014, Global printing market to top $980 billion by
cured with an American UV fitted with a Heraeus 16W/cm², 395 2018, <www.smitherspira.com/news/2014/january/global-printing-
nm, UV LED at 100% power. MP 3 mil PE was the base, and market-to-top-980-billion-by-2018>
MP 75 gauge PP was the overlaminate. The laminating adhesive 2. FDA, 12/14/2017, Packaging & Food Contact Substances
tested was Adhesive 1. The conveyor belt was run up to 500 (FCS), <www.fda.gov/Food/IngredientsPackagingLabeling/
fpm. Migration testing was conducted by placing the laminations PackagingFCS>
in aluminum and glass cells with the food contact side of the
construction exposed to the food simulant. The food simulants Jake Staples, technical team leader for Ashland, specializes in
were 95% ethanol to cover fatty food types and 10% ethanol radiation curable coatings, primers and adhesives, with more
to cover aqueous food types and 10ml/sq.in. was applied as the than 17 years of energy-curable expertise – particularly within
default amount. the development of UV LED and EB technologies. His roles
include product development, application support and technical
Three conditions were tested. Condition of Use C (hot fill above sales. He has presented at industry conferences, including
150°F) was tested by holding the food simulant in the cells at RadTech events. He earned a BA in physics from Carthage
66°C for two hours, followed by 10 days at 40°C. Condition College and an MS in mechanical engineering from the University
of Use E (room temperature fill and storage with no thermal of Wisconsin-Milwaukee.
treatment) was tested by holding the food simulant in the cells at
40°C for 10 days. HPLC-MS analysis was performed to detect
any components of the adhesive in the food simulant, and the data
were reviewed by a food packaging toxicologist who performed a
risk assessment. A safe threshold of 50 ppb was set by taking into
account toxicological data and daily consumption factor of 1%
used in FCN 642. The data are presented in Table 6. These results
indicated that all the samples are safe for use in food packaging.
Plastics Decorating Magazine to Host The Coating Tech Institute at Carestream’s Windsor, Colorado,
Surface Summit in Michigan facility October 22 through 24, 2019. A user conference for the
Plastics Decorating magazine, Topeka, Kansas, will host its first slot die coating industry, Coating Tech Institute is presented with
sponsored event, The Surface Summit, on November 5, 2019, in classroom teaching followed by hands-on learning opportunities
Dearborn, Michigan. The one-day educational opportunity will in Carestream’s laboratory and on its pilot coating line. Session
offer technical papers and workshops targeting surface treatment topics include rheology, defect resolution, troubleshooting and
and curing technologies for molded plastics in a variety of end- beyond. For more information, visit www.coatingtechinstitute.com.
use markets. In addition to programming, a Supplier Trade
Fair will provide access to leading industry members and their Carbon® and Arkema Partner
latest technologies. Increasing the value to attendees, RadTech to Advance Digital Manufacturing
North America International will host that association’s Fall Redwood City, California-based Carbon, a digital manufacturing
Meeting on the day prior to The Surface Summit. Attendees of company, and Arkema, an international provider of advanced liquid
both events will receive valuable industry insights and technical resins solutions through its Sartomer business line, announced a
knowledge to improve the use of surface pretreatment, cleaning strategic partnership to deliver a new era of materials performance
and curing methods in their own facilities. For registration and and supply chain model for Carbon’s manufacturing partners.
more information, visit www.plasticsdecorating.com/surface- Arkema has made an investment of $20 million to Carbon® Growth
summit-2019. Funding Round to support the next generation of fully integrated
digital manufacturing platforms with a deeper collaboration,
Hydromer Launches Next Generation Website cutting-edge materials and innovative solutions. For more
Branchburg, New Jersey-based Hydromer Inc., offering specialty information, visit www.Carbon3d.com and www.arkema.com.
polymers and surface coating technologies, contract coating
services and custom-designed equipment, announced the launch PCT Ebeam and Integration Enters HP
of its next generation website. The site features new capabilities to Graphics Solutions Partner Program
accelerate current and future clients’ ability to access information PCT Ebeam and Integration, LLC (PCT), Davenport, Iowa, an
about products and services. This includes the capability to electron beam systems provider, has announced its participation
interact globally on a 24/7 basis with customer service experts in the HP Graphics Solutions Partner Program. This program
and to browse the website in several different ways, according facilitates HP Graphic Arts customers’ growth and profitability
to individualized search preferences. Download access for “on- through partner solutions and technologies for numerous printing
the-spot” content such as white papers, brochures and product applications. PCT’s Core 100 ebeam system provides curing of
information also is available. For more information, visit overprint varnishes (OPVs) for flexible packaging production
www.hydromer.com. without lamination and is ideal for demanding applications
including hot-fill, pasteurization, form fill and seal, and lidding.
Technical Industry Resource Eminence UV Gloss, matte and soft-touch OPV finishes are available to design
Now Available effects for packaging possibilities. The process provides fast,
A new Chicago-based enterprise – Eminence UV – has launched solvent-free, instantly cured, digitally printed packaging. For
to provide consulting and resources on arc, microwave and UV more information, visit www.pctebi.com.
LED curing equipment, and related applications. The company
offers UV curing guidance to converters, manufacturers Jim DeFife Receives
and OEMs seeking unbiased technical assistance. Eminence Global Achievement Award
UV assists clients in the decision-making process, shortcuts Jim DeFife, vice president Pressure-Sensitive
development timelines and helps navigate new UV curing Materials at Multi-Color Corporation, Batavia,
purchases and retrofits. Founder Jennifer Heathcote has held Ohio, has received the prestigious R. Stanton
roles in UV since 1998, including applications engineering, Avery Global Achievement Award 2019.
sales, business development and general management. Heathcote DeFife has been a driving force in the global
is an authority on conventional UV systems and UV LED label industry for almost 40 years, with a
technology, as well as their use across a range of industrial curing career focus on the development of technical
applications. For more information, visit eminenceuv.com. solutions that have revolutionized and grown
the pressure-sensitive market – first with
Coating Tech Slot Dies to Host Coating Tech Avery Dennison and then, for the past 17 years, with Spear and
Institute at Carestream Multi-Color. Sponsored by Avery Dennison, the R. Stanton Avery
Coating Tech Slot Dies – an Eau Claire, Wisconsin-based Global Achievement Award recognizes an innovation or idea that
custom manufacturer of slot dies – and Rochester, New York- has helped transform and advance the label industry across the
headquartered Carestream – a partner in simultaneous, precision world. For more information, visit www.labelawards.com.
multilayer coating technology and manufacturing – will host
2017 Quarter 2
Print + Digital
Vol. 3, No. 2
Don’t miss this chance to stay uptodate on
new technologies and learn about the latest
developments in the industry.
le
Exploring UV-Curab
ions
Composite Formulat
UV LED for
Floor Coatings
The Challenges
of Measuring UV
Photoinitiators for
s
LED-Cured Coating
of Photocurable Urethane
and Development
Director,
Performance
Coatings
International
Laboratories Acrylates
Introduction
U rethane acrylates (methacrylates) are valuable oligomers widely used in industry. They are used in
adhesives, protective and decorative coatings, dental fillings, labels, inks and as coatings for optical fiber.
As review, synthesis of the most common and simple urethane acrylates consists of two steps and includes
three reagents: polyol-diol (P) polyether or polyester, diisocyanate (D) and a capping agent – hydroxyl-
substituted acrylate (A). The most common diisocynates are isophorone diisocyanate (IPDI), tolylene
diisocyanate (TDI), methylene diphenyl diisocyanate (MDI) and p-phenylene diisocyanate (PPDI). The
acrylate often is 2-hydroxyethyl acrylate (HEA) or 2–hydroxyethyl methacrylate (HEMA).
In the first step, the polyol-diol reacts with an excess of the diisocyanate. After that the oligomer D–P is
capped with the acrylate (the second step). Elevated temperatures and catalysts are required in each of the
two steps. The final oligomer should result in all reagents having reacted with each other. The number of used
equivalents (n) of NCO of the diisocyanate will be equal to the sum of OH equivalents of the polyol-diol and
the acrylate:
Completion of a reaction is usually controlled by infrared (IR). Fortunately, the NCO group has strong
absorption in the mid-IR spectrum (2270 cm-1)1,2, and it allows monitoring of the disappearance of NCO
with high accuracy. Selection of one or another diisocynate, polyol-dio, acrylate and a molecular weight of
polyol-diols allows the creation of urethane acrylates with a wide range of physical/mechanical properties in
the cured and the liquid state. Further, a ratio of ingredients n(D): n(P): n(A) can be varied. Such variation
obviously leads to the changes in properties of the final product. Certainly, variation of n(D): n(P): n(A)
should not violate Equation 1.
The method described above often is called direct synthesis.1 It is possible to run a reverse synthesis.1 In
reverse synthesis, the first step is a reaction between the diisocyanate and the acrylate, with subsequent
reaction of D–A with the polyol-diol. Interestingly, the same amounts of the same diisocyanate, polyol-
diol and acrylate lead to products with quite different properties prepared by the direct or reverse synthesis.
Reverse addition leads to lower molecular weight (MW) and lower viscosity (ƞ) of the final urethane acrylate.
Direct vs. reverse synthesis is another purposeful way to change properties of the synthesized urethane
acrylates with the same amount of the same reagents.1
Low Free monomer (LF) oligomers. In the first stage of (direct) synthesis, chemists often take n(D) = 2
n(P). A naïve expectation is that the product D–P will have a structure as presented in Figure 1a. However,
formation of the product presented in Figure 1b occurs. Macromolecules presented in Figure 1b are formed
by chain extension of the primary D-P products by the second polyol-diol molecule. In a general case, both
products schematically presented in Figure 1 are formed. Moreover, NCO-terminated macromolecules may
include more than two polyol-diol molecules in their structures.
Products of a reaction between diisocynates with polyol-diols change under condition n(D) ≥ 10 n(P). Under
such a condition, a chain extension (Figure 1b) is negligible because the polyol-diols are surrounded by a
68 | UV+EB Technology • Issue 3, 2019 uvebtechnology.com + radtech.org
Thus, the product formed under the condition
n(D) ≥ 10 n(P) is presented on the Figure
1a. The mixture has an excess of non-reacted
diisocynate. Diisocynate can be stripped under
vacuum, and an individual product (Figure
1a) is an LF oligomer or LF prepolymer. LF
stands for the extremely low concentration
of non-reactive hazardous free diisocynate.
LF oligomers are commercially available
at a modest cost. They are not hazardous:
reactive–NCO is present, but it is bound to
a macromolecule polyol-diol. LF oligomers
are thermally cured with different curative
agents [1,4- butanediol, 2-aminoethanol, 4,4’-
methylenebis(2-chloroaniline) (MOCA), others]
in the preforms. Wheels, belts, balls and other
high–performance objects are made from the
cured LF oligomers.
Capping of LF oligomers
MWD Different commercial LF oligomers can be
MWD
capped with hydroxyl acrylates in order to get
a b urethane acrylate. It is the one-step reaction
mentioned in the title. The capping agent will
Figure 2. Pictorial presentation of molecular weight distribution of the capped LF be HEA. The molecular weight distribution of
oligomers (a) and of relative common urethane acrylates (b). Common urethane urethane acrylate made with LF oligomers will
acrylates consist of all the strips presented in this figure. The horizontal scale for be smaller than those of analogous common
two molecular weight distributions is the same. urethane acrylates. (See Figure 2.) The h of
common urethane acrylate is higher than that of
large excess of diisocynates. Rate (or probability) of a reaction relative urethane acrylates made with LF oligomers (cf., above).
of polyol-diols with diisocynates is much higher than with P–D Oligomers with relatively low h are valuable because they require
because [D]>>[P–D]. Moreover, a rate constant of a reaction of a none (or a small amount) of reactive diluent, which changes
hydroxyl group with free diisocynates usually is higher than that properties of the final curable coating.
of a reaction of –OH with a second –NCO of D–P.3 page 71
uvebtechnology.com + radtech.org UV+EB Technology • Issue 3, 2019 | 69
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Figure 3. GPC traces of common urethane acrylate (a) and of the relevant urethane acrylate made with LF oligomer.
One will notice that common urethane acrylates include low A summary of properties of materials prepared by direct vs.
molecular weight compound HEA-D-HEA (Figure 2b). Low reverse synthesis,1 prepared at different D/P ratios2 and acrylated
MW additives usually have a detrimental effect on the elastic LF vs. common urethane acrylates4 is presented in the cited
properties of the cured coatings. HEA–D–HEA are usually literature.
solid compounds under ambient conditions. Cure of specially
prepared melted A–D–A compounds leads to their shatter under The possible application of LF oligomers in the
light or to very hard coatings. Urethane acrylates prepared from coatings for optical fiber
LF oligomers do not have A-D-A. The latter compound often Acrylated LF oligomers may find an application in photocurable
is called diadduct. Experimental data (Figure 3) confirm the coatings for optical fiber. The primary coating of optical fiber
statements made above. should be elastomeric, soft, have high elongation-to-break, low
Tg, low storage (elastic) modulus and low molecular weight
page 72
uvebtechnology.com + radtech.org UV+EB Technology • Issue 3, 2019 | 71
LOW FREE OLIGOMERS
page 71
distribution.5 (Many of these requirements listed above are 3. Szycher, M. Szycher’s Handbook of Polyurethanes; CRC Press:
interdependent.) Low molecular weight distribution of coatings Boca Raton, FL, 1999, ch 2.
for optical fiber is required for a speedy application of coating.5 4. Zhu, Z.; Khudyakov, I.V.; Rosenberg, R.O. Radiation-Curable
LF oligomers capped by HEA or another acrylate are promising Polyurethane. US6943202B2.
5. Khudyakov; I.V.; Purvis; M. B.; Overton, B. J. Formulation of UV-
candidates of coatings for optical fiber.
curable coatings for optical fiber for a fast cure. US 6887918.
Conclusions.
Acknowledgment. The author is grateful to Vince Gajewski (ret.)
Photocurable urethane acrylates can be made in one stage by the
and Jerry Bryce of COIM USA for useful discussions.
catalyzed addition of hydroxyl-substituted acrylate to commercial
LF oligomers. A variety of commercially available LF oligomers,
Igor V. Khudyakov, PhD, DSc, is research and development
as well as capping agents, allows simple synthesis urethane
director at Performance Coatings International Laboratories,
acrylate oligomers with different properties in the liquid and
Bangor, Pennsylvania. PCI is a manufacturer and supplier of
cured state. That makes LF oligomers especially valuable for
high-performance oligomers and coatings, including thermal and
small or startup companies that intend to produce cost-effective
UV-curable coatings with high abrasion resistance. Khudyakov
products with a wide range of applications. Additional benefits of
holds 21 US patents, has written or contributed to more than
such urethane acrylates are their relatively low viscosity and low
200 scientific and technical publications, and has presented at a
molecular weight distribution.
number of conferences, including RadTech International North
America and RadTech Europe. For more information, email ivk@
References
1. Swiderski, K.W.; Khudyakov, I.V. Industrial & Engineering pcoatingsintl.com or startatj@aol.com.
Chemistry Research, 2004, 43, 6281.
2. Khudyakov, I.V.; Swiderski, K.W.; Greer, R.W. Journal of Applied
Polymer Science, 2006, 99, 489.
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