Ecological Compliance

in
Synthetic Organic Dyes - New Challenges
Dr. Pankaj Desai

COLOURTEX INDUSTRIES PRIVATE LIMITED 1

12/04/2022
 AGENDA

 Current Ecological and Toxicological requirements

 Examples of affected currently available commercial dyestuff

 Possible way forward……………

12/04/2022 COLOURTEX INDUSTRIES PRIVATE LIMITED 2

 AGENDA

 Current Ecological and Toxicological requirements

 Examples of affected currently available commercial dyestuff

 Possible way forward……………

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 WHAT IS EXPECTED OF A DYE?
Before 1990s

 APPLICATION
 Quality Consistency

 ECONOMY
 Competitive Price

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 WHAT IS EXPECTED OF A DYE?
In 21 century
st

 APPLICATION
 Quality Consistency
 State of the art Fastness properties
 Maximum flexibility

 ECONOMY
 Competitive Price
 Economical in Use

 ECOLOGY & TOXICOLOGY

 Legislation
 Eco Labels
 Retailers / Brands RSL & MRSL…………..

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 CORPORATE ACCOUNTABILITY
IN THE 21ST CENTURY
The Triple Bottom Line

Building Long Term Stakeholder Value

Environmental
Social
Economic
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 ORIGIN OF ECO-LABELS:

• Consumer Awareness
Cleaner Technologies

• Responsible Care®

• Right to Know

• Greens Movement

Eco Friendly Products

• Judicial Activism

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 THE BASICS OF ECO-LABELS:

An Eco-Label provides brief information on environment related product qualities. It

enables consumers to identify,

1. 2.
Raw material that do not Products manufactured
contains chemicals harmful using environment friendly
to the user Processes.

3.
Products that are eventually
safe for use and disposal.

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 CRITERIA FOR ECO-LABELS

• Group I – Baby Wear

• Group II – Textiles in Direct Contact with Skin.

• Group III – Textiles with No Direct Contact With Skin.

• Group IV – Decoration Materials.

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TYPICAL ECO-PARAMETERS FOR THE FINISHED TEXTILES
Eco-Parameter Permissible Limits
Presence Of Banned amines <20 ppm
1
Aniline <50 ppm (Gr.-I <20)
2 Presence Of PCP 0.5 ppm (Gr.-I 0.05)
3 Presence of Heavy Metals Customer Specific
Gr-I 16 ppm
Gr-II 75 ppm
4 Presence of Formaldehyde
Gr-III 150 ppm
Gr-IV 300 ppm
5 Residual Pesticides 1 ppm (Gr-I o.5 ppm)
6 Allergic Dyes 50 ppm
7 Chlorinated Benzenes & Toluenes 1 ppm
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TYPICAL ECO-PARAMETERS FOR THE FINISHED TEXTILES
Eco-Parameter Permissible Limits
PCP- 0.05 - 0.5 ppm
TeCP- 0.05 - 0.5 ppm
8 Chlorinated Phenols TrCP- 0.2 - 2.0 ppm
DCP- 0.5 - 3.0 ppm
MCP- 0.5 – 3.0 ppm
9 Phthalates Sum of all 0.1ppm
10 PAH <10 ppm (Gr.-I <5)
AP <10 ppm
11
APEO <100 ppm
12 Quinoline <50 ppm

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 MANUFACTURING RESTRICTED SUBSTANCE LIST (MRSL)
Substances/
ETAD Limit in mg/kg [ppm] ZDHC Limit in mg/kg [ppm]
Substance groups
PAAs (Banned Amines) 200 150
ETAD heavy metal limits 4 plus 10 for ETAD heavy metal limits4 plus
Heavy metals
Cr(VI) 10 for Cr(VI)
Chlorobenzenes/ 1,2-dichlorobenzene 1000
200
Chlorotoluenes Sum of all others 200
20 (sum of tetra/ PCPs)
Chlorophenols 20 (sum of tetra/ pentachlorophenols)
50 (sum of mono-, di-, and tri-)
Organotin compounds 5 5 ; 20 for DBT
PCBs 50 -
Short-chained
chlorinated paraffins 50 50
(SCCPs)
APEO / AP 500 500
sum of substances in group I: 0.001
Dioxins and Furans sum of substances in group I and II: 0.005 -
sum of substances in group I, II and III: 0.1
Formaldehyde
200 -
(CAS 50-00-0)
PAH, polycyclic
20 Benzo[α]pyrene ; 100 sum 20 Benzo[α]pyrene; 200 sum
hydrocarbons
Quinoline (CAS 91-22-5) 1000 -

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 AGENDA

 Introduction of Colourtex Industries Private Limited

 Current Ecological and Toxicological requirements

 Examples of affected currently available commercial dyestuff

 Possible way forward……………

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 Impact of such new requirements on Commercially available products

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 DISPERSE YELLOW 241:

CH3
Cl N N CN

Cl HO O
N
C2H5

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 DISPERSE YELLOW 241:

CH3
Diazotization & Coupling with Cl N N
Cl NH2 CN
CH3

CN
Cl HO O
Cl N
C2H5
HO O
N
C2H5
DISPERSE YELLOW 241:

General Specification for Disperse Yellow 241

Strength and Shade should be identical to Reference Standard

Purity by HPLC: Min. 98%

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 DISPERSE YELLOW 241:

Typical analytical report of commercially available Disperse Yellow 241.

Shade and Strength identical to Reference standard

Purity by HPLC: Min. 98%
Chlorinated Benzenes (CBs) 2000 - 5000 ppm
(Mainly ODCB)

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 DISPERSE YELLOW 241:

Requirement as per MRSL in Disperse Yellow 241.

Shade and Strength identical to Reference standard

Purity by HPLC: Min. 98%
Chlorinated Benzenes (CBs) 2000 - 5000 ppm
(Mainly ODCB)
(Limits for ODCB Max. 1000 ppm
&
for other CBs Max. 200 ppm)

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 DISPERSE RED 152 /153:

Cl
N N
N
N
Cl S CN
R R = -H / -CH3

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 DISPERSE RED 152 /153:
Synthesis of 2-Amino-5:6 / 6:7- Dichloro benzothiazole:

Cl
N

NH2
Cl S

General Specification for 2-Amino-5:6 / 6:7- Dichloro benzothiazole:

Purity by HPLC: Min. 98%

3:4 DCA Content: Max. 0.1%
3:4 DCPh thiourea Content: Max. 0.5%

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 DISPERSE RED 152 /153:

Synthesis of 2-Amino-5:6 / 6:7- Dichloro benzothiazole:

Typical analytical report of commercially available 2-Amino-5:6 / 6:7- DCBT:

Purity by HPLC: Min. 98%

3:4 DCA Content: Max. 0.1%
3:4 DCPh thiourea Content: Max. 0.5%
Chlorinated Phenols (CPs) 50 - 100 ppm
Chlorinated Benzenes (CBs) 2000 - 5000 ppm
PolyChlorinated Biphenyls (PCBs) 100 - 200 ppm
Dioxines Generally present but not analyzed
Furans because of high cost of analysis

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 DISPERSE RED 152 /153:

Cl Cl
N N N
1. Diazotization N
NH2 2. Coupling with N
Cl S Cl S CN
N R R = -H / -CH3

CN
R R = -H / -CH3

General Specification for Disperse Red 152/153:

Strength and Shade should be identical to Reference Standard

Purity by HPLC: Min. 98%

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 DISPERSE RED 152 /153:

Typical analytical report of commercially available Disperse Red 152/153:

Shade and Strength identical to Reference standard

Purity by HPLC: Min. 98%
Chlorinated Phenols (CPs) 20 - 100 ppm
Chlorinated Benzenes (CBs) 2000 - 5000 ppm
PolyChlorinated Biphenyls (PCBs) 50 - 100 ppm
Dioxines Generally present but not analyzed
Furans because of high cost of analysis

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 DISPERSE RED 152 /153:

Requirement as per MRSL in Disperse Red 152/153:

Shade and Strength identical to Reference standard

Purity by HPLC: Min. 98%
Chlorinated Phenols (CPs) 20 - 100 ppm (<20 ppm)
Chlorinated Benzenes (CBs) 2000 - 5000 ppm (<200 ppm)
PolyChlorinated Biphenyls (PCBs) 50 - 100 ppm(<50 ppm)
Dioxines Generally present but not analyzed
Furans because of high cost of analysis

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 DISPERSE ORANGE 30:

Cl

CH2CH2CN

O2N N N N

CH2CH2OCOCH3

Cl

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 DISPERSE ORANGE 30:

Synthesis of 2:6-Dichloro-4-Nitro Aniline:

Cl

Chlorination in acid condition

O2N NH2 H2N NO2
With Cl2

Cl

4-Nitro Aniline 2:6-Dichloro-4-Nitro Aniline

General Specification for 2:6-Dichloro-4-Nitro Aniline:

Purity by HPLC: Min. 98%

PNA Content: Max. 0.1%
OCPNA Content: Max. 0.5%

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 DISPERSE ORANGE 30:

Synthesis of 2:6-Dichloro-4-Nitro Aniline:

Typical analytical report of commercially available DCPNA:

Purity by HPLC: Min. 98%

PNA Content: Max. 0.1%
OCPNA Content: Max. 0.5%
Chlorinated Phenols (CPs) 250 - 500 ppm
Chlorinated Benzenes (CBs) 250 - 500 ppm
PolyChlorinated Biphenyls (PCBs) 200 - 400 ppm

Dioxines Generally present but not analyzed

Furans because of high cost of analysis

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 DISPERSE ORANGE 30:

Cl Cl

CH2CH2CN

O2N NH2
Diazotization & Coupling with O2N N N N
CH2CH2CN
CH2CH2OCOCH3
N
Cl Cl
CH2CH2OCOCH3
DISPERSE ORANGE 30

General Specification for Disperse Orange 30

Strength and Shade should be identical to Reference Standard

Purity by HPLC: Min. 98%

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 DISPERSE ORANGE 30:

Typical analytical report of commercially available Disperse Orange 30.

Shade and Strength identical to Reference standard

Purity by HPLC: Min. 98%
Chlorinated Phenols (CPs) 500 - 1000 ppm
Chlorinated Benzenes (CBs) 250 - 500 ppm
PolyChlorinated Biphenyls (PCBs) 100 - 200 ppm
Dioxines Generally present but not analyzed
Furans because of high cost of analysis

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 DISPERSE ORANGE 30:

Requirement as per MRSL in Disperse Orange 30.

Shade and Strength identical to Reference standard

Purity by HPLC: Min. 98%
Chlorinated Phenols (CPs) 500 - 1000 ppm (<20 ppm)
Chlorinated Benzenes (CBs) 250 - 500 ppm (<200 ppm)
PolyChlorinated Biphenyls (PCBs) 100 - 200 ppm (<50 ppm)
Generally present Dioxines
but not analyzed
Furans because of high
cost of analysis

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 DISPERSE ORANGE 30:

Other Disperse Dyes based on DCPNA:

• Disperse Orange 62
• Disperse Brown 22
• Disperse Orange 41
• Disperse Yellow 163 …………………………..

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 Other Products and Parameters

Product Name Restricted Substance

Disperse Violet 28; Disperse Violet 26/31, Chloro Benzenes

Disperse Blue 60

Disperse Orange 288 Chloro Toluenes

Disperse Blue 79.1/291/291.1 and all products based Chloro Phenoles /PCBs
on 2-Chloro DNA

Disperse Red 118 Disperse Orange 37/76

All Disperse and Acids dyes based on PNA PCA

All Disperse Blacks and Navy Mixtures CBs/CTs/ CPs / PCBs

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 Other Products and Parameters

Product Name Restricted Substance

Reactive Black 5 and mixtures based on it. p-Chloro Aniline

Acid Dyes Based on Alpha Naphthyl Amine (ANA) BNA & Aniline
AB-113, AR-299, AR-119, ABl-26…etc

Acid Brown 298, Acid Orange 33 Aniline

2NADPSA and 4NADPSA based Acid Dyes Aniline

Any Tobia’s acid based Acid, Reactive and Direct Dyes BNA

Beta Naphthol Naphthalene

Dispersing Agents Quinoline, Naphthalene &

Formaldehyde

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 Revealed: hidden source of hazardous textile pollutants
Study conducted by NimkarTek and published in EcoTextile News; 22 October 2018

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 AGENDA

 Introduction of Colourtex Industries Private Limited

 Current Ecological and Toxicological requirements

 Examples of affected currently available commercial dyestuff

 Possible way forward……………

12/04/2022 COLOURTEX INDUSTRIES PRIVATE LIMITED 35

 Possible way forward……….

• Bring Awareness across the supply chain

• Optimize current processes to control Restricted Substances.

• Develop New Process to Eliminate Restricted Substances.

• Develop Alternative New Products With Similar Dyeing and

Fastness Properties

Need to take these as new opportunities and develop effective solutions for
industries..........

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 THANKS

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