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You are here: Home > All About Hand Dyeing > FAQs > Procion Dye FAQs > What is the chemical structure of Procion MX dye?



What is the chemical structure of Procion MX dye?

Procion MX dyes are described as dichlorotriazine dyes, while Procion H dyes are less reactive monochlorotriazines. Here are the full chemical names and/or structures for several Procion MX dyes. Note the cyclical structure with two chlorine atoms on it: these are the reactive sites that react with -OH groups on the cellulose fiber to create the strong covalent bonds that are responsible for the dichlorotriazines' extremely high washfastness. Procion H or monochlorotriazine dyes have one, rather than two, of these chlorines, for a similarly strong bond, but higher heat requirements due to their reduced reactivity - which also makes them store well in water, unlike the Procion MX dyes.

It is often quite difficult to determine the structures of dyes from the literature, because the manufacturers tend to try to keep this information a secret.

Some selected sources are given in the information below, suitable for purchases by hand dyers. (Chemical suppliers are too expensive, and most industrial sources require too large a minimum order size.)

Chemistry beginners should note that the drawings below are somewhat simplified. Most carbon atoms are indicated only as an angle where two lines, indicating covalent bonds, meet. If only three lines meet in one angle, there is also a hydrogen atom attached to that carbon. Carbon atoms may also be denoted with the letter C. Chlorine is Cl, Nitrogen is N, Oxygen is O, Sulfur is S, Copper is Cu, and Chromium is Cr.

I. Dichlorotriazine (MX) dyes with drawings

Yellow MX-8G

Colour Index name: reactive yellow 86

from http://www.chemblink.com/products/57359-00-9.htm
Image from chemblink.com

Full chemical name: [1,3-benzenedisulfonic acid, 4-((5- aminocarbonyl-1-ethyl-1,6-dihydro-2-hydroxy-4-methyl-6-oxo-3- pyridinyl)azo)-6-(4,6-dichloro-1,3,5-triazin-2-yl)amino)-, disodium salt] (CAS Reg. No. 61951-86-8; also 70865-29-1)

Available wherever Procion MX type dyes are sold.

Yellow MX-R

structure of
yellow R

Available from Kraftkolour.

Yellow MX-4R

ofyellow 4R

(no known source)

Orange MX-G

Colour Index Reactive Orange 1

image from chemicalbook.com
Image from Chemical Book

Sometimes available from Standard Dye or Classic Dye.

Orange MX-2R

reactive orange 4 structure

Colour Index name: reactive orange 4

Molecular Formula: C24H16Cl2N6O10S3; Molecular Weight: 715.527.

Full chemical name: 1,5-Naphthalenedisulfonic acid, 2-[[6-[(4,6-dichloro- 1,3,5-triazin-2-yl) methylamino]- 1-hydroxy-3-sulfo -2-naphthalenyl]azo]-, trisodium salt. (CAS 70616-90-9.)

Available wherever Procion MX type dyes are sold.

Brown MX-GRN

Colour Index name: reactive brown 23

from http://www.molport.com/buy-chemicals/moleculelink/about-this-molecule/6136277
Image from MolPort.com

IUPAC name:trisodium 2-{2-[4-(2-{4-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-5-sulfonatonaphthalen-1-yl}diazen-1-yl)-2,5-dimethylphenyl]diazen-1-yl}benzene-1,4-disulfonate

Alternative chemical name: 1,4-Benzenedisulfonic acid, 2-[[4-[[4-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]- 5-sulfo-1-naphthalenyl]azo]- 2,5-dimethylphenyl]azo]-, trisodium salt. (CAS 68892-31-9.)

Rubine MX-B

structure of
rubine B

Full chemical name: Cuprate(3-),[2-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-5-hydroxy-6-[(2-hydroxy-5-sulfophenyl)azo]-1,7-naphthalenedisulfonato(5-)]-,trisodium (CAS 16038-15-6).

[Note correction: chemical name and CAS number formerly listed on this page for reactive red 6 had been accidentally duplicated from CI Reactive Red 1.]

Colour Index name: reactive red 6

Chemical formula: C19H7Cl2CuN6O11S3•3 Na

Molecular weight: 794.91

Copper content by weight (not including buffers, salts, etc., added to the powder during manufacture) would be just under 8%.

Sold by Colorado Wholesale Dyes as "14 Cherry".

Red MX-2B

structure of red

Colour Index name: reactive red 1

Full chemical name: 2,7-Naphthalenedisulfonic acid, 5-[(4,6-dichloro-1,3,5- triazin-2-yl)amino]-4-hydroxy- 3-[(2-sulfophenyl)azo]-, trisodium salt (CAS 17752-85-1).

(Sometimes available from Standard Dye or Classic Dye.)

Red MX-5B

structure of
red 5B

Colour Index name: reactive red 2; variously known as light red, mixing red, or clear red

Full chemical name: 2,7-Naphthalenedisulfonic acid, 5-[(4,6-dichloro- 1,3,5-triazin-2-yl)amino]- 4-hydroxy-3-(phenylazo)-, disodium salt

Empirical Formula (Hill Notation): C19H13Cl2N6NaO7S2, Formula Weight: 595.37, CAS Number: 17804-49-8; Dye content 40% (Sigma-Aldrich)

Available wherever Procion MX type dyes are sold.

Red MX-8B

structure ofred

Colour Index name: reactive red 11; known everywhere as Fuchsia

Full chemical name: [5-((4,6-dichloro-1,3,5-triazin-2- yl)amino)-4-hydroxy-3-((1-sulfo-2-naphthalenyl)azo)-2, 7- naphthalenedisulfonic acid, trisodium salt] (CAS Reg. No. 12226-08-3)

Available wherever Procion MX type dyes are sold.

Blue MX-R

structure of
blue R

Colour Index name: reactive blue 4; known as Sky blue, Basic blue, or Clear blue

Full chemical name: [2-anthracenesulfonic acid, 1-amino-4-(3- ((4,6-dichloro-s-triazin-2-yl)amino)- 4-sulfoanilino)-9,10-dihydro-9,10- dioxo, disodium salt] (CAS Reg. No. 4499-01-8)

also given as "2-Anthracenesulfonic acid, 1-amino-4-[[3-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]- 4-sulfophenyl]amino]-9,10-dihydro-9,10-dioxo-" (CAS 13324-20-4)

Empirical Formula (Hill Notation): C23H14Cl2N6O8S2, Formula Weight: 637.43, CAS Number: 13324-20-4

Available wherever Procion MX type dyes are sold.

Turquoise MX-G

Colour Index name: reactive blue 140

turquoise The structure of reactive blue 140 is not precisely known, because it is a heterogenous mixture of several closely related molecules. As indicated by the subscripts m and n in the picture, there may be one or two sulfonate groups on the phthalocyanine ring, there may be two or three dichlorotriazine sections per copper phthalocyanine, and the positions of these different items on the phthalocyanine ring are unknown and presumably random. In addition, this dye molecule, especially if kept in solution for several days, tends to 'stack up' to form aggregates of two or more molecules, causing the hue to shift to be more blue and less green. See "A Beautiful Blue: Procion Turquoise MX-G".

Available wherever Procion MX type dyes are sold.

II. Dichlorotriazine (MX) dyes with full chemical names but no drawings

Yellow MX-3R and Yellow MX-3RA

Colour Index name: reactive orange 86

Full chemical name: (probably) 1,3,6-Naphthalenetrisulfonic acid, 7-[[2-[(aminocarbonyl)amino]- 4-[(4,6-dichloro-1,3,5- triazin-2-yl)amino]phenyl]azo]-, trisodium salt" (CAS 57359-00-9)

Available almost everywhere that Procion MX type dyes are sold.

Brown MX-5BR

Colour Index Reactive Brown 10

CAS 70788-63-5

Chromate(3-), bis[2-[[6-[(4,6-dichloro-1,3,5-triazin-2-yl) amino]-1-hydroxy-3-sulfo-2-naphthalenyl]azo]benzoato(3-)]-, disodium hydrogen.

Formerly an important componant in mixing black and neutral shades. Currently no known source.

(Thanks to Dan Snyder for this identification.)

Blue MX-G

Colour Index name: reactive blue 163

Full chemical name: triphenodioxazinedisulfonic acid, 6,13- dichloro-3, 10-bis((4-((4.6-dichloro-1,3,5-triazin-2-yl)amino) sulfophenyl)amino)-, tetrasodium salt (CAS Reg. No. 72847-56-4)

Available from ProChem, G&S Dye, Fibrecrafts, and Jacquard Products.

Blue MX-2G

Colour Index Reactive Blue 109

CAS 70865-31-5

2,7-Naphthalenedisulfonic acid, 4-amino-6-[[5-[(4,6-dichloro-1,3,5-triazin-2-yl) amino]-2-sulfophenyl]azo]- 3-[(2,5-disulfophenyl)azo]-5-hydroxy-, pentasodium salt.

Available wherever Procion MX type dyes are sold.

(Thanks to Dan Snyder for this identification.)

III. Dichlorotriazine (MX) dyes with no structures or full chemical names available

Yellow MX-6G

Colour Index Reactive yellow 1

CAS 25489-31-0

Available from Synthesia in the Czech Republic and some other sources.

Yellow MX-4G

reactive yellow 22

CAS 12226-49-2

Available from ProChem.

Yellow MX-GR

reactive yellow 7

CAS 12226-46-9

Available from ProChem and Dharma.

Red MX-G

reactive red 5

Available from Fibrecrafts in the UK.

Magenta MX-B

reactive violet 13

CAS 12270-87-0

Available from Kraftkolour (and also from ProChem if my guess about the identity of their Boysenberry Procion dye is correct).

Violet MX-2R

(often mislabeled violet MX-G, a meaningless dye code)

reactive violet 14

CAS 12270-88-1

Available from Jacquard Products, ProChem, and Dharma.

Blue MX-7RX

reactive blue 161

CAS 71872-77-0

Available from Aljo Mfg in New York and Quilt & Art in Germany.

Navy MX-3R

(sometimes sold as Navy MX-G)

reactive blue 9

CAS 12225-37-5

Sometimes available from Standard Dye.

Blue MX-4GD

reactive blue 168

Available from ProChem and from Quilt and Art in Germany.

Blue MX-3G

reactive blue 1

Sometimes available from Aljo Mfg. or Standard Dye.

IV. full names of unknown dichlorotriazine (MX) dyes (need identification with MX codes or CI names)

CAS 129009-88-7 "2-Naphthalenesulfonic acid, 7-[(4,6-dichloro- 1,3,5-triazin-2-yl)amino]- 4-hydroxy- 3-[[4-[[2-(sulfooxy)ethyl]sulfonyl]phenyl]azo]-, disodium salt"

CAS 57583-69-4 "2,7-Naphthalenedisulfonic acid, 5-[(4,6-dichloro-1,3,5-triazin-2-yl)amino] -4-hydroxy-3-[(1-sulfo-2-naphthalenyl)azo]-, trisodium salt"

CAS 61433-40-7 "2,7-Naphthalenedisulfonic acid, 4-amino- 6-[[5-[(4,6-dichloro-1,3,5 -triazin -2-yl)amino]-2-sulfophenyl]azo]- 3-[(2,5-disulfophenyl)azo]-5-hydroxy-"

CAS 68992-03-0 "1,5-Naphthalenedisulfonic acid, 2-[[1-amino-7- [[5-[(4,6-dichloro- 1,3,5- triazin-2-yl)amino]- 2-sulfophenyl]azo]- 8-hydroxy-3,6-disulfo- 2-naphthalenyl]azo]-, pentasodium salt"

CAS 70776-20-4 "Benzenesulfonic acid, 5-[[4-[(4,6-dichloro-1,3,5-triazin-2-yl) methylamino]phenyl]azo]- 2-[2-(4-nitro-2-sulfophenyl)ethenyl]-, disodium salt"

CAS 83929-55-9 "Phenazinium, 3-[[4-[(4,6-dichloro-1,3,5-triazin-2-yl) amino]-2-sulfophenyl]amino]- 7-[ethyl[(3-sulfophenyl)methyl]amino]- 5-(4-methoxy-3-sulfophenyl)-, inner salt, disodium salt"

CAS 83949-27-3 "Phenazinium, 3-[[4-[(4,6-dichloro- 1,3,5-triazin-2-yl) amino]-2-sulfophenyl]amino]- 7-[ethyl[(3-sulfophenyl)methyl] amino]-5-(4-sulfophenyl)-, inner salt, disodium salt"

CAS 85946-19-6 "1H-Pyrazole-3-carboxylic acid, 4-[[5-[(4,6-dichloro-1,3,5- triazin-2-yl)amino]- 2-sulfophenyl]azo]- 4,5-dihydro-5-oxo-1-(4-sulfophenyl)-"

CAS 94133-47-8 "4,11-Triphenodioxazinedisulfonic acid, 6,13-dichloro- 3,10-bis[[4-[(4,6-dichloro-1,3,5-triazin-2-yl) amino]disulfophenyl]amino]-"

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