16-04-2017

Chemistry of Dyes

Lecture 13
April 10, 2017

Disclaimer: This was prepared for learning/teaching purpose using the content from various 
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Color Perception

•Specialized cone cells in our eyes respond to

visible light
g and signal
g color to the brain.

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Color Perception

•There are three

different kinds of
human cone cells
varying in their
sensitivities to
different colors of
light: blue, green, and
red.
•Leads to trichromatic
color vision. •Sometimes called long,
medium and short cones.

Color Perception

•Birds
Bi d hhave f
four
different kinds of
cones (one in the UV).

•Dogs have only two

(no green).

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Color Perception

The Bird’s View

•Birds
Bi d hhave f
four
different kinds of
cones (one in the UV).

•Dogs have only two

(no green).

Color Perception

•Objects appear colored when they reflect light of

that color.

•Red cones
respond,
signalling to the
brain that the
apple is “red”.

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Absorbance of Light

•A pigment generally
absorbs light that is
complementary to that
observed.

•Absorbance data can be

correlated to the identity
of pigment.

Absorbance of Light

Food Coloring Data:

Yellow: 425 nm
(absorbs violet)
Red: 522 nm
(absorbs cyan)
Blue: 610 nm
(absorbs orange)

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Primary Colors of Pigments

•Equally adding adjacent pigments leads to the
development of color wheels.

primary colors secondary colors tertiary colors

Complementary colors
•Colors opposite each other on color wheels are
complementary colors.
green yellow

cyan red

blue magenta
•Pigments of complementary colors add in equal
amounts to give black.

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Plant & Animal-Based (Organic) Pigments

Indigo

Tyrian
purple

Madder lake
(alizarin)

Common Sources of Pigments

Marigolds Grape
Juice

Beets Cochineal
Beetles

Walnut hulls Kool-Aid

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Colorants

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Colorants

Colorants

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Coloured organic compounds

• Often contain unsaturated groups, -C=O, -C=C,

-N=N-
• Usually part of extended delocalised electron
system called the chromophore.
• Electrons in double bonds more spread out -
require less energy to excite than those in single
bonds particularly in conjugated system.
• Absorption of radiation in visible region.

Groups, energy and colour

• -OH, -NH2 , or NR2 attached to chromophores to enhance
or modify the colours.
• Lone pair electrons become involved in the delocalised
system.
• Small changes change the energy of light absorbed and
therefore the colour.
• Dyes often different colours in acids and alkalis - useful
indicators.
• Methyl orange bond to H+ at pH 3.5
3 5 and below - red,
red
+
above pH3.5 there is no H bonded and the dye is yellow.

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The relationship between color and

wavelength of absorbed light

Recapping
• Coloured substances absorb radiation in the
visible region of the EM spectrum.
spectrum
• Absorb energy - outermost electrons
promoted to excited state.
• Same electrons involved in bonding or lone
p
pairs.
• Innermost electrons more tightly held by
attraction to the nucleus - more energy
needed for excitation.

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Pulling theory together

• Some transitions
needing less energy
are brought about by
visible light
• Excitation energy is
greater when UV light
is absorbed.
• Compounds absorbing
UV radiation appear
colourless.

Dyes make the world more colorful

With the first

Pick of the first
berry,
y, dyes
y were
discovered.

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Natural dyes will dye…

cotton silk

flax

ramie
wool and other
natural
fibers

Fastness

Refers to the tendency

y of a dye
y

to resist fading as a result of

washing or exposure to
light

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Plant dyes

Rule of thumb:
One pound of plant
material to one pound
of fiber.

Plants are simmered or

f
fermented
t d tto release
l
the dye into the
dyebath.

Mordants

Mordants are chemicals

which help the dye
molecules bind to the
fibers. Iron, copper,
chrome, alum, and
urea are often used
with
ith plant-base
l tb d
dyes.

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The dyeing process

Prepare dyebath
Wash and thoroughly wet fiber
Mordant
Simmer, ferment, or solar dye
Mordant or additive
Rinse
Dry

Keep good records!

Results will vary from dyelot to dyelot.
That’ss half the fun!
That

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Indigo Blue
Indigofera tinctoria, a member
of the Fabaceae.

Dyed articles are green until the

dye is exposed to oxygen.

The process is messy and smelly.

You can buy indigo powder or
cakes of dye that have already
been fermented and are ready
to dye.

BLUE and PURPLE

Berries. Often not washfast.

Alkanet—blue-purple

Woad, the blue dye of ancient Britons

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PURPLE

Orchil lichens. Beautiful colors, but rare,

and require fermentation with urea.

Logwood—bluish purples, or
gray-lavender with additives

Pink and Red

Brazilwood—South American
t
tree whose
h wood
d yields
i ld red
dddye.

Madder, Rubia tinctorum

Roots yield a red, pink, or
reddish-brown dye.

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Yellow and Orange

Weld, Reseda, or Mignonette—
Shades of yellow and gold

Eggs dyed with onion

skins, gold to brown

Yellow and Orange

Turmeric, saffron, and safflower are
used as food flavoringg and dye,
y , but theyy
will dye fabric as well.

Goldenrod, common locally,

Gives a good yellow dye.

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Greens
Many plants will yield a green dye
--mostly chlorophyll—but these are often
not colorfast. More successful greens can
be obtained by dyeing yellow over blue or
vice versa. Indigo
g and weld make a ggood
green.

Tan, Brown, and Black

Many plants will

i yield
i tan
or brown. The addition
of iron makes colors
“sadder” or blacker, though
it can be damaging to
fibers Oak galls,
fibers. galls rich in
tannic acid, can be used to
darken colors.

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Natural dyes Synthetic dyes

Natural fibers: cellulose

(polysaccharides)

Cellulose Fibers
Cotton
Linen

Cellulose Derivatives
(viscose) Rayon
(viscose) Acetate

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Natural fibers: proteins

Protein Fibers: silk and wool

Synthetic fibers:
Cellulose
Derivatives
(viscose)
Rayon
(viscose) Acetate

The chemical process

Making Viscose Rayon 

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Synthetic fibers:
Viscose Acetate

The chemical process

Making Viscose Acetate

How Dyes Attach to Fibers

Mordants bind to dyes and to fibers

Acid dyes use electrostatic interactions

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How Dyes Attach to Fibers

How a reactive dye binds to fibers

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