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You are here: Home > All About Hand Dyeing > About Dyes > Fiber Reactive Dyes > Vinyl Sulfone 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

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!


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, 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.

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.

codeCI nameother namesretailersnotes
Yellow GR Reactive
Yellow 15
Gelb GRBO, GF, SYNno metals
Yellow RTN Reactive
Yellow 24
Gelb RTN GF
Yellow GL Reactive
Yellow 37
Brill. Gelb GL
JVS 600 Bright Yellow
GF, KK, JVS incl. in PRO Leaf Green;
JVS fair/good disch.;
excellent lightfastness
Yellow FG Reactive
Yellow 42
SYN
Yellow R Reactive
Yellow 77
BO, GFdischargeable (?)
Yellow 3R ?JVS 601 Golden Yellow JVSdischargeable (?); JVS fair/good disch;
fair lightfastness
Yellow R4GL Reactive
Yellow 160
Brill. Gelb 4GL GF dischargeable (?)
Yellow 4G Reactive
Yellow 186
SYN dischargeable (?)
Orange 2R Reactive
Orange 7
Orange 3R Reactive
Orange 16
Brill. Orange 3R;
Red Label 706 Apricot;
Strong Orange LR202
JR, BO, GF, KK, PRO, SYNdischargeable (?)
Orange 2G Reactive
Orange 72
Orange 2RL Reactive
Orange 82
Golden
Yellow RNL
Reactive
Orange 107
KK
Bordeaux B Reactive
Red 49
Bordox B;
Red Label 717 Digital
JV 604 Bordeaux
JR, JV, GFJVS 20% strength
Rubine CB Reactive
Red 60
Red C2G Reactive
Red 106
Red R2G see above?JV 602 Red25% strength; fair/good disch.;
fair lightfastness
Red BS Reactive
Red 111
Red 3BSA ?JVS 603 MagentaJVS
Red 5B Reactive
Red 35
SYN
Procion H-E 8B Reactive
Red 152
Red Label 715 MagentaJRreactive red #152 is actually a binfunctional dye, Procion H-E 8B, not a vinyl sulfone
Levafix Brilliant
Red E-6BA
Reactive
Red 159
BOnot a vinyl sulfone: found in PRO LR 308 Fuchsia and mixtures
Red 6B Reactive
Red 174
BO
Red RF3B Reactive
Red 180
Brill. Rot F3BGF, KKno metals; dischargeable (?)
Red RB Reactive
Red 198
Red VS-MRBL
Mixing Red LR305
PRO, SYN
Red Violet R Reactive
Violet 4
Violet 5R Reactive
Violet 5
Brill. Violet 5R;
Red Label 718 Purple
JR, BO, GF, KK ,SYNnon-dischargeable (?)
Blue R (Special) Reactive
Blue 19
Red Label 722 Royal Blue;
Intense blue LR406
JV 606 Blue?
JV?, JR, BO, GF, KK, PRO, SYN no metals; non-dischargeable (?)
Blue R? see above?JVS 606 Blue? JVS good disch;
fair lightfastness
Turquoise Blue G Reactive
Blue 21
Türkisblau G133 BO, GF, KK, PRO, SYN, JV?contains copper
PRO describes as "copper phthalo- cyanine dye solution"; non-dischargeable (?)
Turquoise Blue GA see above? JV 605 Turquoise? JVScontains copper
fair/good non-dischargeability;
poor lightfastness
Blue 3R Reactive
Blue 28
Blau 3R GF
Green 6B Reactive
Blue 38
BO, KK
Dark Blue HR Reactive Blue 89
Blue 3G Reactive
Blue 98
Navy Blue GG Reactive
Blue 203
Brill. Blau BB133 GF, KK
Navy Blue 6G Reactive
Blue 218
BO
Blue BB Reactive
Blue 220
contains copper
Navy Blue RGB Reactive
Blue 250
JV 607 Navy50% strength;
good disch.;
fair lightfastness
Brown GR Reactive
Brown 18
Braun GRBO, GF, KKnon-dischargeable (?)
Black B Reactive
Black 5
Schwarz B;
Red Label 759 Black
JR, BO, GF, KK, PRO, SYNno metals; some versions might also contain a tiny quantity of an unidentified dye; also found in Dylon Permanent dye "12 Black"; dischargeable (?);
Black RL Reactive
Black 31
Schwarz RLGF
Black N ? JV Black 608GFJVS: 40% strength
good disch.
very poor lightfastness


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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:
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 namechemical name
C.I. Reactive Blue 220, aka Remazol Br. Blue BB Cuprate(4-), [4,5-dihydro-4-[[8-hydroxy-7-[[2-hydroxy-5-methoxy-4-[[2- (sulfooxy)ethyl]sulfonyl]phenyl]azo]-6-sulfo-2-naphthalenyl]azo]-5-oxo-1-(4-sulfophenyl)-1H- pyrazole-3-carboxylato(6-)]-, sodium
Reactive Yellow 15 [benzensulfonic acid, 4-(4,5-dihydro-4-((2- methoxy-5-methyl-4-((2-(sulfooxy)ethyl) sulfonyl)phenyl)azo)-3-methyl-5- oxo-1H-pyrazol-1-yl)-] (CAS Reg. No. 60958-41-0)
Reactive Orange 16 2-Naphthalenesulfonic acid, 6-(acetylamino)- 4-hydroxy- 3-((4-((2-(sulfooxy)ethyl) sulfonyl)phenyl)azo)-, disodium salt
Reactive Orange 78 [2-naphthalenesulfonic acid, 7-(acetylamino)- 4-hydroxy-3-((4-((2-(sulfooxy)ethyl) sulfonyl)phenyl)azo)-] CAS Reg. No. 68189-39-9)
Reactive Red 180 [5-(benzoylamino)-4-hydroxy-3-((1-sulfo- 6-((2-(sulfooxy)ethyl)sulfonyl)-2-naphthalenyl)azo)-2,7- naphthalenedisulfonic acid, tetrasodium salt] (CAS Reg. No. 98114-32-0)
Source: http://www.sigmaaldrich.com Reactive Violet 5 5-(Acetylamino)-4-hydroxy-3-[[2-hydroxy-4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]azo]-2,7-naphthalenedisulfonic acid trisodium salt [CAS 12226-38-9]
Reactive Blue No. 19 [2-anthracene-sulfonic acid, 1-amino-9,10- dihydro-9,10-dioxo-4-((3-((2-(sulfooxy)ethyl)sulfonyl)phenyl)amino)-, disodium salt] (CAS Reg. No. 2580-78-1)
Reactive Blue 21 [copper, (29H,31H-phthalocyaninato(2-)- N29,N30,N31,N32)-, sulfo((4-((2- sulfooxy)ethyl)sulfonyl)phenyl)amino) sulfonyl derivs] (CAS Reg. No. 73049-92-0)
Reactive Black 5 [2,7-naphthalenedisulfonic acid, 4-amino-5- hydroxy-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.

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:

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.


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