Vinyl Sulfone Fiber Reactive Dyes

pburch.net/dyeing/remazol.shtml

Web www.pburch.net

You are here: Home > All About Hand

Dyeing > About Dyes > Fiber Reactive Dyes
> Vinyl Sulfone Fiber Reactive Dyes

Vinyl Sulfone dyes, also known as Remazol® dyes after the trademarked name under
which they were first introduced, are a type of fiber reactive dye that is often used in silk
painting. Although silk paintings made with vinyl sulfone dyes are usually steamed to set
the dye, the dyes can also be "batch cured" at warm room temperatures.
Unlike some fiber reactive dyes, vinyl sulfones can be used as true reactive dyes on
cotton, silk, AND wool. Of course, wool must never be subjected to the high pHs used in
dyeing cotton, and it requires high heat, unlike cotton. Like all dyes that work on cotton,
vinyl sulfones can also be used on linen, hemp, and other cellulose (plant) fibers.

Vinyl sulfone dyes are a type of fiber reactive dye that is less reactive than, for example,
Procion MX dyes, and thus they both last longer in solution in water, and require more
heat for the reaction with the fiber. This means that they can actually be purchased
already dissolved in water, unlike Procion MX or Cibacron F dyes, eliminating the one
slightly hazardous step of working with powdered dyes.

The lower reactivity of Vinyl sulfones is not the whole story, however. Unlike Drimarene K
and Cibacron F dye, Vinyl sulfones contain a 'masking' group, on the reactive part of the
molecule, which prevents them from reacting with the dye water until it is removed. This
makes the dyes much longer lasting in water! The masking group of at least some of the
Remazols can be removed at high pH (i.e, with soda ash or pot ash or sodium silicate),
which is suitable for cotton, or, if the dye solution is heated to a high enough
temperature, at mildly acid pH, which is suitable for wool. The latter is a slower process.
[Thanks to Doug Wilson for describing this on the Dyerslist mailing list; he referenced the
book Wool Dyeing, edited by David M. Lewis and published by the Society of Dyers and
Colorists.]

Table of Contents:

How to use Vinyl sulfone fiber reactive dyes

1/12
Keep it warm!
If you are omitting the heat-setting step altogether, using soda ash as when dyeing with
Procion MX dye, it is best to place the freshly dyed items in a warm place overnight,
ideally between between 40 and 60 degrees Celsius (104 and 140 degrees Fahrenheit),
though somewhat cooler temperaures can be used. You can achieve this by placing
buckets or sealed bags containing your dyed items in a sinkful of hot water, or by placing
your items on waterproof sheeting on top of a heating pad or under an electric blanket,
or on top of the refrigerator in a warm kitchen. You can wrap your items to keep them
damp (and/or use urea when mixing your dyes), and place them in a slightly warm oven.
Or you can seal them in plastic and microwave them briefly, until the fabric is hot to the
touch. (Sealing in plastic keeps the microwave clean, and it keeps your fabric from drying
out, so it does not burn. Watch closely so that the steam inside does not burst the
plastic.

Look at the pros' instructions

Request instructions from your supplier, or see the helpful web pages below.
Instructions may not be completely interchangeable, as it is possible that the dye
solutions sold by the different companies may be different in concentration!

The old (now discontinued) Createx Colors Liquid Fiber Dyes included instructions
for tie-dyeing and immersion dyeing with soda ash without heat fixing, and for
hand painting and silk screening with heat setting (microwaving, baking, or
steaming)
PRO Chemical & Dye's
Batik Oetoro says to use the same instructions as for their fiber reactive Drimarene
K dyes, but with temperatures of 40°C to 60°C (104°F to 140°F); their methods for
Drimarene K include immersion dyeing with dyebath between 35 and 50 degrees C,
or 95-122 F; after-fixing with Drimafix; tie-dyeing; and drying with hair dryer.
Jacquard Red Label Silk Colors Instructions (steam-set instructions only)
Tobasign
multi-language tie-dye instructions slideshow (mixing Tobafix with dye and
water, no heat)
Instructions for fabric painting and immersion dyeing (fixing at room
temperature with Tobafix)

Where to buy specific single-hue unmixed Remazol dyes

Different brand names are applied to the vinyl sulfone dyes for sale. In the US, they are
available as PRO Chemical & Dye's Liquid Reactive Dyes, as Createx Colors Liquid Fiber
Dyes (now discontinued), and as Jacquard Red Label Silk Colors. In Australia, they are
sold under the name of Remazol dyes by Batik Oetoro and by KraftKolour. In Europe,

2/12
they are sold as Granat Remazolfarver by Granat Farvekompagniet, in Denmark, as
Tobasign Dyes by Tobasign, in Spain, and as Ostazin V dyes by Synthesia in the Czech
Republic.

The Remazol brand name is owned by Dystar, which still manufacturers many vinyl
sulfone dyes. Vinyl sulfone dyes are also manufactured by other companies now. Dystar
has obtained Oeko-Tex Standard 100 certification (PDF) for many of its Remazol and
Procion HE dyes.

Notice, in the table below, that each company carries different Remazol dyes. You may
find that only one company carries your very favorite dye color. A similar color can often
be mixed from other primaries, but it may have slightly different properties, or be less
glowingly bright, or perhaps less subtle. In most cases, they also sell a number of other
useful colors, which they have blended from two or more other colors. These can be
good to use, but to truly know the properties of your dyes, you must consider them
individually. You can also mix any color you wish, if you start with a good set of
primaries, ideally including colors that closely approximate the cyan, magenta, and
yellow widely used as printer's primaries, plus some dull, dark colors to be used in mixing
dark, deep shades. Unlike most types of fiber reactive dyes that can be used at room
remperature, the vinyl sulfones include a couple of single-color unmixed blacks.

Each of these dye companies sells the dye directly to the public through their web site,
except for Createx Colors and Jacquard, both of which sell through multiple retailers.
One supplier for Createx Colors is Dick Blick; one supplier for Jacquard Red Label Silk
Colors is Jalt.com, and they can be special-ordered from Dharma Trading Company.
[Createx Remazols have been discontinued from all sources, although there was a report from
a user that one can still buy them by calling the Createx company directly.]

Note that not every dye in each line of dyes is of this dye class. Jacquard includes one
Procion H-E bifunctional dye as their Red Label Magenta. PRO Chemical & Dye's Fuchsia
LR308 uses instead a magenta from the Levafix line, Levafix Brilliant Red E-6BA, which I
find very beautiful. ProChem's Sun Yellow and Golden Yellow are of undisclosed dye
types (their 'Golden Yellow' is more tan than golden in color). Although Dylon Permanent,
Dylon Washing Machine, and Dylon Hand dyes all contain mostly Drimarene K type dyes,
their Black contains mostly Reactive Black 5, a highly satisfactory Remazol type dye.

Recommended mixing primaries in the Jacquard Red Label line are yellow, magenta,
cyan, and black; their web site includes a table for mixing different colors from these
four. Don't use ProChem's 'Golden Yellow' as a mixing primary, because it is a tan color,
not yellow, to my eye; it should be very useful as a toning mixer, however, for dulling
down overly bright color mixtures. ProChem's 'Sun Yellow' is a good bright color for
mixing, as are their Intense Blue and Turquoise; I personally prefer their Fuchsia to their
Mixing Red as a primary.

3/12
In the table below, "JR" stands for Jacquard Red Label Dyes; "BO" stands for Batik Oetoro;
"KK" for Kraftkolour; "GF" stands for Granat Farvekompagniet; and SYN stands for
Synthesia. "PRO" stands for PRO Chemical & Dye. Note that Jacquard Red Label Silk
Colors also include many other colors, which are, according to the manufacturers,
mixtures of two or more colors of dye.

Jacquard Green Label Silk Colors contain the same dyes as Jacquard Red Label Silk
Colors, but in the Green Label dyes, the concentration is half that of the Red Label dyes,
and the Green Label dye mixtures have been acidified and appear to contain some
(unidentified) chemicals not found in the Red Label dye mixtures. Jacquard Red Label Silk
Colors are more dilute than ProChem's Liquid Fiber Reactive Dyes; Jacquard Red Label
Black 759 is approximately one-fourth the strength of ProChem's Black 50% LR604.

The notes in the right hand column, below, are merely points of interest. I do not believe
that the metals contained in a few of the dyes amount to enough to cause problems with
disposal in home septic systems. It's interesting, to me, to note that blues often contain
copper, since copper compounds themselves are often beautiful blues.

CI other
code name names retailers notes

Yellow GR Reactive Gelb GR BO, GF, no metals

Yellow SYN
15

Yellow Reactive Gelb RTN GF

RTN Yellow
24

Yellow GL Reactive Brill. Gelb GF, KK, incl. in PRO Leaf Green;
Yellow GL JVS JVS fair/good disch.;
37 JVS 600 excellent lightfastness
Bright
Yellow

Yellow FG Reactive SYN

Yellow
42

Yellow R Reactive BO, GF dischargeable (?)

Yellow
77

Yellow 3R ? JVS 601 JVS dischargeable (?); JVS fair/good

Golden disch;
Yellow fair lightfastness
4/12
Yellow Reactive Brill. Gelb GF dischargeable (?)
R4GL Yellow 4GL
160

Yellow 4G Reactive SYN dischargeable (?)

Yellow
186

Orange Reactive
2R Orange
7

Orange Reactive Brill. JR, BO, dischargeable (?)

3R Orange Orange 3R; GF, KK,
16 Red Label PRO,
706 SYN
Apricot;
Strong
Orange
LR202

Orange Reactive
2G Orange
72

Orange Reactive
2RL Orange
82

Golden Reactive KK
Yellow Orange
RNL 107

Bordeaux Reactive Bordox B; JR, JV, GF JVS 20% strength

B Red 49 Red Label
717 Digital
JV 604
Bordeaux

Rubine Reactive
CB Red 60

Red C2G Reactive

Red 106

5/12
Red R2G see JV 602 Red 25% strength; fair/good disch.;
above? fair lightfastness

Red BS Reactive
Red 111

Red 3BSA ? JVS 603 JVS

Magenta

Red 5B Reactive SYN

Red 35

Procion Reactive Red Label JR reactive red #152 is actually a

H-E 8B Red 152 715 binfunctional dye, Procion H-E
Magenta 8B, not a vinyl sulfone

Levafix Reactive BO not a vinyl sulfone: found in PRO

Brilliant Red 159 LR 308 Fuchsia and mixtures
Red E-
6BA

Red 6B Reactive BO
Red 174

Red RF3B Reactive Brill. Rot GF, KK no metals; dischargeable (?)

Red 180 F3B

Red RB Reactive Red VS- PRO,

Red 198 MRBL SYN
Mixing Red
LR305

Red Violet Reactive

R Violet 4

Violet 5R Reactive Brill. Violet JR, BO, non-dischargeable (?)

Violet 5 5R; GF, KK
Red Label ,SYN
718 Purple

6/12
Blue R Reactive Red Label JV?, JR, no metals; non-dischargeable (?)
(Special) Blue 19 722 Royal BO, GF,
Blue; KK, PRO,
Intense SYN
blue
LR406
JV 606
Blue?

Blue R? see JVS 606 JVS good disch;

above? Blue? fair lightfastness

Turquoise Reactive Türkisblau BO, GF, contains copper

Blue G Blue 21 G133 KK, PRO, PRO describes as "copper
SYN, JV? phthalo- cyanine dye solution";
non-dischargeable (?)

Turquoise see JV 605 JVS contains copper

Blue GA above? Turquoise? fair/good non-dischargeability;
poor lightfastness

Blue 3R Reactive Blau 3R GF

Blue 28

Green 6B Reactive BO, KK

Blue 38

Dark Blue Reactive

HR Blue 89

Blue 3G Reactive
Blue 98

Navy Blue Reactive Brill. Blau GF, KK

GG Blue BB133
203

Navy Blue Reactive BO

6G Blue
218

Blue BB Reactive contains copper

Blue
220

7/12
 Navy Blue Reactive JV 607 50% strength;
RGB Blue Navy good disch.;
250 fair lightfastness

Brown GR Reactive Braun GR BO, GF, non-dischargeable (?)

Brown KK
18

Black B Reactive Schwarz B; JR, BO, no metals; some versions might

Black 5 Red Label GF, KK, also contain a tiny quantity of an
759 Black PRO, unidentified dye; also found in
SYN Dylon Permanent dye "12 Black";
dischargeable (?);

Black RL Reactive Schwarz GF

Black 31 RL

Black N ? JV Black GF JVS: 40% strength

608 good disch.
very poor lightfastness

- Back to top -

About the Chemistry of the Vinyl Sulfone dyes

Here is a quote from Cellulosics Dyeing (ed. John Shore, 1995, Society of Dyers and
Colourists), p 200:

8/12
 The Remazol (Hoesht) vinylsulfone dyes, containing the characteristic 2-
suphatoethylsulphonyl precursor grouping, are intermediate in reactivity between the
high-reactivity heterocyclic systems, such as dichlorotriazone [Procion MX type] or
difluropyrimidine, and the low-reactivity ranges, such as aminochlorotriazine [Procion H]
or trichloropyrimidine. Exhaust dyeing temperatures between 40 and 60 degrees C may
be chosen, depending on pH, since caustic soda [NaOH] is often selected to bring about
alkaline hydrolysis of the precursor sulphate ester. [Use "ph" in "sulphate" if you're
British, "f" if American.] These dyes are applicable by a wide variety of batchwise and
continuous processes. The substantivity [tendency to cling to the fiber even when
unreacted] of many of these dyes is markedly lower than that of typical haloheterocycloic
dyes [eg Procion MX or Cibacron F]. Not only has the vinylsulphone group, unlike the
heterocyclic ring systems, little if any inherent affinity for cellulose, but the terminal
sulphato group enhances the aqueous solubility of the precursor form before 1,2-
elimination to the vinylsulphone. In contrast to the haloheterocyclic systems, the dye-fibre
bonds formed by the vinylsulphone dyes are at their weakest under alkaline conditions.

I.e., use temperatures between 40 and 60 C (104 and 140 F), and use alkaline conditions
(high pH, as usual with fiber reactive dyes). High pH *might* work for discharging. It
should resist acid perspiration better than Procion MX or Cibacron F dyes, if that's a
problem for you. It should be vastly easier to wash out of the fabric than Procion MX or
Cibacron F dyes. Note: vinyl sulfone dyes should be rinsed in cool water to remove
auxiliary chemicals and normalize pH before it is rinsed in hot water; an initial rinse in
hot water may break some of the bonds between dye and fiber.

structure,
if
available
(click on
image
for
enlarged
view) CI name chemical name

C.I. Cuprate(4-), [4,5-dihydro-4-[[8-hydroxy-7-[[2-hydroxy-

Reactive 5-methoxy-4-[[2- (sulfooxy)ethyl]sulfonyl]phenyl]azo]-
Blue 220, 6-sulfo-2-naphthalenyl]azo]-5-oxo-1-(4-sulfophenyl)-
aka 1H- pyrazole-3-carboxylato(6-)]-, sodium
Remazol
Br. Blue BB

9/12
 Reactive [benzensulfonic acid, 4-(4,5-dihydro-4-((2- methoxy-5-
Yellow 15 methyl-4-((2-(sulfooxy)ethyl) sulfonyl)phenyl)azo)-3-
methyl-5- oxo-1H-pyrazol-1-yl)-] (CAS Reg. No. 60958-
41-0)

Reactive 2-Naphthalenesulfonic acid, 6-(acetylamino)- 4-

Orange 16 hydroxy- 3-((4-((2-(sulfooxy)ethyl) sulfonyl)phenyl)azo)-
, disodium salt

Reactive [2-naphthalenesulfonic acid, 7-(acetylamino)- 4-

Orange 78 hydroxy-3-((4-((2-(sulfooxy)ethyl) sulfonyl)phenyl)azo)-]
CAS Reg. No. 68189-39-9)

Reactive [5-(benzoylamino)-4-hydroxy-3-((1-sulfo- 6-((2-

Red 180 (sulfooxy)ethyl)sulfonyl)-2-naphthalenyl)azo)-2,7-
naphthalenedisulfonic acid, tetrasodium salt] (CAS
Reg. No. 98114-32-0)

Reactive 5-(Acetylamino)-4-hydroxy-3-[[2-hydroxy-4-[[2-
Violet 5 (sulfooxy)ethyl]sulfonyl]phenyl]azo]-2,7-
naphthalenedisulfonic acid trisodium salt [CAS 12226-
38-9]

Reactive [2-anthracene-sulfonic acid, 1-amino-9,10- dihydro-

Blue No. 19 9,10-dioxo-4-((3-((2-
(sulfooxy)ethyl)sulfonyl)phenyl)amino)-, disodium salt]
(CAS Reg. No. 2580-78-1)

Reactive [copper, (29H,31H-phthalocyaninato(2-)-

Blue 21 N29,N30,N31,N32)-, sulfo((4-((2-
sulfooxy)ethyl)sulfonyl)phenyl)amino) sulfonyl derivs]
(CAS Reg. No. 73049-92-0)

Reactive [2,7-naphthalenedisulfonic acid, 4-amino-5- hydroxy-

Black 5 3,6-bis((4-((2-(sulfooxy)ethyl)sulfonyl)phenyl)azo)-
tetrasodium salt] (CAS Reg. No. 17095-24-8)

Using Remazol Dyes for Chemical Resist Dyeing

Vinyl sulfone dyes are particularly useful for chemical resist dyeing, in which two
different types of fiber reactive dyes are used to print foreground and background in
different colors. This technique allows you to print one color right on top of another
color, such as bright yellow figures on a dark blue background, without having to do a
separate discharge step.
10/12
One method is to mix either Cibacron F or Procion MX dye with soda ash and a chemical
called BASF Chemical Resist, apply it to cotton fabric, let it dry, then mix up remazol dye
with soda ash or 'Basilen Fixing Agent', apply it to the same piece of fabric, and then
steam the piece. The result is a design of Procion MX or Cibacron F dye surrounded by a
background of Remazol dye. The Remazol dye does not react with the fabric where the
chemical resist has been placed.

Sources for instructions

DyersLIST list-owner Pat William provided instructions for chemical resist dyeing with
remazol dyes on two pages whcih were located on the DyersLIST website at Eastern
Michigan University. They are no longer there, but the Internet Archive still makes them
available. Here are links for the two PDF pages with the instructions:

Chemical Resist Process: Two Methods of Working with Two

Different Families of Reactive Dyes [PDF] and
Chemical Resist measurement charts [PDF]

Kate Wells gives recipes for chemical resist printing, including specific
recommendations for which Remazol dyes are the best choices to use,
in her book Fabric Dyeing and Printing .

Sources for resist chemicals

It appears that there are no longer any known sources for buying BASF Chemical Resist.
(For speculation as to what chemical(s) may have been contained in BASF Chemical
Resist, see the Dye Forum discussions, "chemical resist dyeing with fiber reactive dyes"
and "Looking for the Liquid Reactive Resist Agent for Chemical Resist.")

The resist chemical used to prevent the vinyl sulfone dyes from attaching to the fabric is
sold by Jacquard Products under the name Chemical Reactive Resist. Their web site lists
four mail-order sources in the US: Binders Art Supplies and Frames, Fabrics to Dye For,
Bates Art & Designs Supply, and Hull's Art Supply and Framing. The chemical, previously
known as BASF Chemical Reactive Resist, is also available in industrial quantities from
BTC Specialty Chemical Distribution.

Another chemical, Basilen Fixing Agent, is often substituted in this method for the soda
ash otherwise used to fix the fiber reactive dyes to the fabric, with the advantage of
permitting a longer wait time before steaming.
A good alternative for contrasting colors in figure and ground is to first dye the fabric
with a reactive dye that discharges well with a reducing discharge agent, then overprint
with a vat dye; the reducing agents required for solubilizing the vat dyes will also
discharge suitable reactive dyes.

11/12
 - Back to top -

Last updated: September 30, 2011

Page created: May 1, 2005
Downloaded: Wednesday, January 15, 2020

12/12