US3893801A - Transfer dyeing - Google Patents

Transfer dyeing Download PDF

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Publication number
US3893801A
US3893801A US369970A US36997073A US3893801A US 3893801 A US3893801 A US 3893801A US 369970 A US369970 A US 369970A US 36997073 A US36997073 A US 36997073A US 3893801 A US3893801 A US 3893801A
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Prior art keywords
ink
amino
printed
backing material
transfer
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Expired - Lifetime
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US369970A
Inventor
Cyril Eric Vellins
Leonard Fox Dixon
Bryan Ronald Hinchliffe
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Holliday Co Ltd L B
L B Holliday & Co Ltd
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Holliday Co Ltd L B
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Priority to GB2821972A priority Critical patent/GB1390864A/en
Application filed by Holliday Co Ltd L B filed Critical Holliday Co Ltd L B
Priority to US369970A priority patent/US3893801A/en
Priority to BE132297A priority patent/BE800954A/en
Priority to FR7321988A priority patent/FR2190066A5/fr
Application granted granted Critical
Publication of US3893801A publication Critical patent/US3893801A/en
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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • B41M5/3852—Anthraquinone or naphthoquinone dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/003—Transfer printing
    • D06P5/004—Transfer printing using subliming dyes
    • D06P5/006—Transfer printing using subliming dyes using specified dyes

Definitions

  • ABSTRACT A method for transfer printing onto a synthetic fabric is provided utilizing an ink comprising a base medium and at least one dyestuff having the formula:
  • X is an unsubstituted alkyl group having from 1 to 6 carbon atoms
  • Y and Z are cyanoor hy-- drogen, at least one of Y and Z being cyano.
  • X is an alkyl group having from 1 to 6 carbon atoms which may be substituted, or a cycloalkyl group containing 6 carbon atoms, Y or Z is cyano the other being hydrogen or both Y and Z are cyano;
  • X is an alkyl group having from 1 to 6 carbon atoms which may be substituted or a cycloalkyl group containing six carbon atoms
  • Y is cyano or hydrogen and Z is cyano.
  • the transfer backing material containing the printed design is contacted with the synthetic material which is to be dyed and heated at a temperature in the range of from 180 to 230C. for a period of from 10 seconds to 2 minutes, preferably from seconds to 30 seconds, but the precise conditions will depend on the materials employed and the desired results.
  • the transfer printing process involves the conversion to the vapour phase by heat of the dyestuff which has been previously printed onto an inert support, followed by penetration and adsorption into the synthetic material to be dyed.
  • Suitable alkyl or cycloalkyl groups represented by X in formula (1) above are saturated alkyl groups such as methyl, ethyl, normal or isopropyl, butyl or cyclohexyl.
  • compounds of formula (I) are l-amino-2-cyano4-methylaminoanthraquinone, lamino-3-cyano-4-cyclohexylaminoanthraquinone, lamino-Z,3-dicyano-4 methylaminoanthraquinone, lamino-2,3-dicyano-4-ethylaminoanthraquinone and l-amino-2,3-dicyano-4-n-butylaminoanthraquinone.
  • the design may be printed on the backing material, normally paper, by any of the usual paper printing processes such as a flexographic, lithographic, gravure, letter press or screen printing process.
  • the printing ink is formulated to be. suitable for the desired process, but in general is made up of one or more solvents, a resinous or oily bindingand thickening material, and the desired dyestuff, either in finely divided form or wholly or in part in solution.
  • the binding material should not decompose or transfer at the required transfer temperature.
  • EXAMPLE 1 20 g of 1-amino-4-butylamino anthraquinone-Z- sodium sulphonate, 25 g of potassium cyanide, 5 g sodium carbonate and 1000 g of water are heated to 90C. until the product has completely precipitated from the original blue solution. The reaction mixture is then filtered, washed with water and dried to give a mixture of l-amino-2,3-dicyano-4- butylaminoanthraquinone mixed with small amounts of the corresponding 2 and 3 mononitriles.
  • the ink may be printed by flexographic roller onto a paper base, dried, and the paper contacted with a polyester fabric at 215C. for 20 seconds.
  • the resulting clear blue dyeing has good fastness to washing and light.
  • Good prints may be obtained on other synthetic fibres and films, such as nylon and acrylic diand triacetate. On the latter fibres, gas fume fastness is also excellent.
  • EXAMPLE 2 A mixture of 22 parts of modified phenolic resin, e.g. Alsynol RL 23, and 48 parts of bleached linseed oil is heated to 260C. and thereafter cooled to C. 30 Parts of linseed oil modified alkyd resin, e.g. Alsynol PN 53 are added, the mixture being cooled to 40C. when 15 parts of the dye of example 1 are added and 3 the mixture is milled. After the addition of 6 parts of 6% cobalt naphthenate (6% cobalt), an ink suitable for offset or litho printing on paper is produced. Heat transfer to fabric gives similar results of example 1.
  • EXAMPLE 3 A mixture of lO g l-amino-4-bromoanthraquinone- 2-sodium sulphonate, 96 g 60% aqueous ethylamine solution, g sodium carbonate, 0.75 g copper acetate and 1000 ml water is heated in a stainless steel autoclave at 95-l00C. for 3 hours. Excess ethylamine is removed by venting and the solution of l-amino-4- ethylaminoanthraquinone-2-sulpnonic acid is further diluted to 3 litres with water. l44 g sodium cyanide and g sodium carbonate are then added and the mixture is heated to reflux until the product has precipitated.
  • the dye is then filtered, washed with hot water and dried, to give a mixture of mainly l-amino-4- ethylamino-2,3-dicyano anthraquinone, together with small amounts of the corresponding 2 and 3 monocyano derivatives.
  • This dye may be converted to an ink equally well by the processes used in Examples 1 and 2.
  • EXAMPLE 4 A mixture of 20 g of 1-amino-4-cyclohexylamino anthraquinone-Z-sodium sulphonate, 40 g of potassium cyanide and 1000 ml of water are refluxed for 2 hours, filtered, washed and dried. The product is mainly 1- amino-3-cyano-4-cyclohexylaminoanthraquinone.
  • Transfer prints on to synthetic fibres were a bright reddish blue of good wash and light fastness.
  • the results were qually good when applied from ink coated paper prepared with inks as in the previous examples.
  • EXAMPLE 5 20 g of l-amino-4-methylaminoanthraquinone-2- sodium sulphone, 25 g of potassium cyanide, 5 g of sodium carbonate and 1000 ml water are heated at 8595C. for 3 hours. The mixture is filtered, washed with hot water and dried, to give a mixture of cyano derivatives which is mainly l-amino-2-cyano-4- methylaminoanthraquinone.
  • a mixture of 20 parts of the above dye, parts of calcium carbonate extender, 12.5 parts of long oil linseed isophthalic acid alkyd resin, 25 parts of medium viscosity linseed oil and 12.5 parts of heavy viscosity linseed oil is passed through a triple roll mill to give an offset litho ink. Papers so printed gave good heat transfer prints on synthetic fibres.
  • EXAMPLE 6 A mixture of equal parts of the dyestuffs of Examples 1 and 5 was made into an ink and printed as in Example l. Deeper blue shades on transfer printing were obtained than by the use of either dye singly. We claim:
  • a method of transfer printing comprising printing with an ink a desired design onto a transfer backing-material, and thereafter transferring the printed design by the application'of heat from the backing material to a synthetic fabric which is to be dyed or printed, the ink comprising a base medium and at least one dyestuff having the formula I NH X in which: X is unsubstituted alkyl group having from l to 6 carbon atoms; Y is cyano or hydrogen and Z is cyano.
  • saturated alkyl group is selected from the group consisting of methyl, ethyl, normal propyl, isopropyl or butyl.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Coloring (AREA)
  • Color Printing (AREA)

Abstract

A method for transfer printing onto a synthetic fabric is provided utilizing an ink comprising a base medium and at least one dyestuff having the formula:

IN WHICH: X is an unsubstituted alkyl group having from 1 to 6 carbon atoms, Y and Z are cyano or hydrogen, at least one of Y and Z being cyano.

Description

United States Patent 91 Vellins et al.
[451 July 8,1975
[ TRANSFER DYEING [75] Inventors: Cyril Eric Vellins, Cheadle; Leonard Fox Dixon, Elland; Bryan Ronald l-Iinchliffe, Huddersfield, all of England [73] Assignee: L. B. Holliday & Co. Limited,
Huddersfield, England [22] Filed: June 14, 1973 [21] Appl. No.: 369,970
OTHER PUBLICATIONS Fox et al., Dec. 1969, J. Soc. Dyers & Col., pp. 614-616.
Primary ExaminerDona1d Levy Attorney, Agent, or Firm-William R. Liberman, Esq.
[57] ABSTRACT A method for transfer printing onto a synthetic fabric is provided utilizing an ink comprising a base medium and at least one dyestuff having the formula:
in which: X is an unsubstituted alkyl group having from 1 to 6 carbon atoms, Y and Z are cyanoor hy-- drogen, at least one of Y and Z being cyano.
12 Claims, N0 Drawings TRANSFER DYEING This invention relates to transfer dyeing or printing.
According to our invention we provide a method of transfer printing in which an ink comprising a base medium, and at least one dyestuff of formula (I) in which:
X is an alkyl group having from 1 to 6 carbon atoms which may be substituted, or a cycloalkyl group containing 6 carbon atoms, Y or Z is cyano the other being hydrogen or both Y and Z are cyano;
is printed in a desired design, alone or together with one or more other dyestuffs, on to a transfer backing material, and in which the printed design is thereafter transferred from the backing material to a synthetic material which is to be dyed or printed by the application of heat.
According to one aspect of our invention, we provide a method of transfer printing in which an ink comprising a base medium and at least one dyestuff of formula (I):
in which:
X is an alkyl group having from 1 to 6 carbon atoms which may be substituted or a cycloalkyl group containing six carbon atoms, Y is cyano or hydrogen and Z is cyano.
is printed in a desired design, alone or together with one or more other dyestuffs, on to a transfer backing material, and in which the printed design is thereafter transferred from the backing material to a synthetic material which is to be dyed or printed by the application of heat.
In general, the transfer backing material containing the printed design is contacted with the synthetic material which is to be dyed and heated at a temperature in the range of from 180 to 230C. for a period of from 10 seconds to 2 minutes, preferably from seconds to 30 seconds, but the precise conditions will depend on the materials employed and the desired results.
The transfer printing process involves the conversion to the vapour phase by heat of the dyestuff which has been previously printed onto an inert support, followed by penetration and adsorption into the synthetic material to be dyed.
Suitable alkyl or cycloalkyl groups represented by X in formula (1) above are saturated alkyl groups such as methyl, ethyl, normal or isopropyl, butyl or cyclohexyl.
Specific examples of compounds of formula (I) are l-amino-2-cyano4-methylaminoanthraquinone, lamino-3-cyano-4-cyclohexylaminoanthraquinone, lamino-Z,3-dicyano-4 methylaminoanthraquinone, lamino-2,3-dicyano-4-ethylaminoanthraquinone and l-amino-2,3-dicyano-4-n-butylaminoanthraquinone.
The design may be printed on the backing material, normally paper, by any of the usual paper printing processes such as a flexographic, lithographic, gravure, letter press or screen printing process. The printing ink is formulated to be. suitable for the desired process, but in general is made up of one or more solvents, a resinous or oily bindingand thickening material, and the desired dyestuff, either in finely divided form or wholly or in part in solution. The binding material should not decompose or transfer at the required transfer temperature.
Mixtures of dyes of formula (1) may be used to give, in some cases, greater depths of shade. If the cyano compounds are prepared by the processes described in US. Pat. No. 1,938,029, natural mixtures result which are commercially attractive.
One possibility is to have substantially equal amounts of 2-cyano and 3-cyano derivatives. Another is to have a preponderance of 2,3-dicyano compound and only small amounts of the 2-cyano and 3-cyano compounds. The following examples illustrate the application of the process.
EXAMPLE 1 20 g of 1-amino-4-butylamino anthraquinone-Z- sodium sulphonate, 25 g of potassium cyanide, 5 g sodium carbonate and 1000 g of water are heated to 90C. until the product has completely precipitated from the original blue solution. The reaction mixture is then filtered, washed with water and dried to give a mixture of l-amino-2,3-dicyano-4- butylaminoanthraquinone mixed with small amounts of the corresponding 2 and 3 mononitriles.
5 parts of the above dye mixture are ground to a fine dispersion in a ball mill with parts of the following solution:
50 parts of shellac 50 parts of methylated spirits (64 o.p.)
8.5 parts of monoethanolamine 3.5 parts of morpholine 0.3 parts of silicone antifoam agent 15 parts water The ink may be printed by flexographic roller onto a paper base, dried, and the paper contacted with a polyester fabric at 215C. for 20 seconds. The resulting clear blue dyeing has good fastness to washing and light. Good prints may be obtained on other synthetic fibres and films, such as nylon and acrylic diand triacetate. On the latter fibres, gas fume fastness is also excellent.
EXAMPLE 2 A mixture of 22 parts of modified phenolic resin, e.g. Alsynol RL 23, and 48 parts of bleached linseed oil is heated to 260C. and thereafter cooled to C. 30 Parts of linseed oil modified alkyd resin, e.g. Alsynol PN 53 are added, the mixture being cooled to 40C. when 15 parts of the dye of example 1 are added and 3 the mixture is milled. After the addition of 6 parts of 6% cobalt naphthenate (6% cobalt), an ink suitable for offset or litho printing on paper is produced. Heat transfer to fabric gives similar results of example 1.
EXAMPLE 3 A mixture of lO g l-amino-4-bromoanthraquinone- 2-sodium sulphonate, 96 g 60% aqueous ethylamine solution, g sodium carbonate, 0.75 g copper acetate and 1000 ml water is heated in a stainless steel autoclave at 95-l00C. for 3 hours. Excess ethylamine is removed by venting and the solution of l-amino-4- ethylaminoanthraquinone-2-sulpnonic acid is further diluted to 3 litres with water. l44 g sodium cyanide and g sodium carbonate are then added and the mixture is heated to reflux until the product has precipitated. The dye is then filtered, washed with hot water and dried, to give a mixture of mainly l-amino-4- ethylamino-2,3-dicyano anthraquinone, together with small amounts of the corresponding 2 and 3 monocyano derivatives.
50 parts of the above dye and 50 parts of hydroxypropyl cellulose are sand ground with water to a fine dispersion, and then spray dried. 12 parts of the above mixture with 5 parts of ethyl cellulose are mixed with 78 parts of isopropanol. The resulting ink when coated on paper gives good bright blue heat transfer prints when transferred as in Example 1.
This dye may be converted to an ink equally well by the processes used in Examples 1 and 2.
EXAMPLE 4 A mixture of 20 g of 1-amino-4-cyclohexylamino anthraquinone-Z-sodium sulphonate, 40 g of potassium cyanide and 1000 ml of water are refluxed for 2 hours, filtered, washed and dried. The product is mainly 1- amino-3-cyano-4-cyclohexylaminoanthraquinone. 5 parts of a 50% mixture of this dye with 50% ethyl cellulose (prepared similarly to example 3) were diluted with 45 parts of methylethylketone and 45 parts of ethanol, and the viscosity was adjusted by addition as necessary of ethyl cellulose to give an ink suitable for rotogravure or heliogravure.
Transfer prints on to synthetic fibres were a bright reddish blue of good wash and light fastness. The results were qually good when applied from ink coated paper prepared with inks as in the previous examples.
EXAMPLE 5 20 g of l-amino-4-methylaminoanthraquinone-2- sodium sulphone, 25 g of potassium cyanide, 5 g of sodium carbonate and 1000 ml water are heated at 8595C. for 3 hours. The mixture is filtered, washed with hot water and dried, to give a mixture of cyano derivatives which is mainly l-amino-2-cyano-4- methylaminoanthraquinone. A mixture of 20 parts of the above dye, parts of calcium carbonate extender, 12.5 parts of long oil linseed isophthalic acid alkyd resin, 25 parts of medium viscosity linseed oil and 12.5 parts of heavy viscosity linseed oil is passed through a triple roll mill to give an offset litho ink. Papers so printed gave good heat transfer prints on synthetic fibres.
EXAMPLE 6 A mixture of equal parts of the dyestuffs of Examples 1 and 5 was made into an ink and printed as in Example l. Deeper blue shades on transfer printing were obtained than by the use of either dye singly. We claim:
l. A method of transfer printing comprising printing with an ink a desired design onto a transfer backing-material, and thereafter transferring the printed design by the application'of heat from the backing material to a synthetic fabric which is to be dyed or printed, the ink comprising a base medium and at least one dyestuff having the formula I NH X in which: X is unsubstituted alkyl group having from l to 6 carbon atoms; Y is cyano or hydrogen and Z is cyano.
3. A method according to claim 2 in which the transfer backing material containing the printed design is contacted with the synthetic fabric to be dyed and heated at a temperature in the range of from to 230C. for a period of from 5 seconds to 1 minute.
'4. A method according to claim 3 in which the heating period is for from 5 seconds to 30 seconds. I
5 A method according to claim 1 in which the saturated alkyl group is methyl, ethyl, normal propyl or isopropyl or butyl. I
6. A method according to claim 1 in which the compound (I) v is l-amino-2-cyano-4- methylaminoanthraquinone. I
7. A method according to claim 2 in which the saturated alkyl group is selected from the group consisting of methyl, ethyl, normal propyl, isopropyl or butyl.
8. A method according to claim 2 in which mixtures of two or more compounds (I) are employed.
9. A-method according to claim in which the compound (l) is 1-amino-2,3-dicyano-4-methylamino anthraquinone. i
6 10. A method according to claim 1 in which the comthraquinone. poimd (I) l'ammo'z3'dcyano'lethylammo 12. A method according to claim 1 in which mixtures qumone.
11. A method according to claim 1 in which the comof two or more compounds (I) are employedpound (l) is l-amino-2,3-dicyano-4-n-butylamino an- 5

Claims (12)

1. A METHOD OF TRANSFER PRINTING COMPRISING PRINTING WITH AN INK A DESIRED DESIGN ONTO A TRANSFUR BACKING MATERIAL, AND THEREAFTER TRANSFERRING THE PRINTED DESIGN BY APPLICATION OF HEAT FROM THE BACKING MATERIAL TO A SYSTHETIC FABRIC WHICH IS TO BE DYED OR PRINTED, THE INK COMPRISING A BASE MEDIUM AND AT LEAST ONE DYESTUFF HAVING THE FORMULA
2. A method of transfer printing comprising printing with an ink a desired design onto a transfer backing material, and thereafter transferring the printed design by the application of heat from the backing material to a synthetic fabric which is to be dyed or printed, the ink comprising a base medium and at least one dyestuf having the formula
3. A method according to claim 2 in which the transfer backing material containing the printed design is contacted with the synthetic fabric to be dyed and heated at a temperature in the range of from 180* to 230*C. for a period of from 5 seconds to 1 minute.
4. A method according to claim 3 in which the heating period is for from 5 seconds to 30 seconds.
5. A method according to claim 1 in which the saturated alkyl group is methyl, ethyl, normal propyl or isopropyl or butyl.
6. A method according to claim 1 in which the compound (I) is 1-amino-2-cyano-4-methylaminoanthraquinone.
7. A method according to claim 2 in which the saturated alkyl group is selected from the group consisting of methyl, ethyl, normal propyl, isopropyl or butyl.
8. A method according to claim 2 in which mixtures of two or more compOunds (I) are employed.
9. A method according to claim 1 in which the compound (I) is 1-amino-2,3-dicyano-4-methylamino anthraquinone.
10. A method according to claim 1 in which the compound (I) is 1-amino-2,3-dicyano-4-ethylamino anthraquinone.
11. A method according to claim 1 in which the compound (I) is 1-amino-2,3-dicyano-4-n-butylamino anthraquinone.
12. A method according to claim 1 in which mixtures of two or more compounds (I) are employed.
US369970A 1972-06-16 1973-06-14 Transfer dyeing Expired - Lifetime US3893801A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB2821972A GB1390864A (en) 1972-06-16 1972-06-16 Transfer printing
US369970A US3893801A (en) 1972-06-16 1973-06-14 Transfer dyeing
BE132297A BE800954A (en) 1972-06-16 1973-06-15 TRANSFER PRINTING OR DYING
FR7321988A FR2190066A5 (en) 1972-06-16 1973-06-15

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB2821972A GB1390864A (en) 1972-06-16 1972-06-16 Transfer printing
US369970A US3893801A (en) 1972-06-16 1973-06-14 Transfer dyeing

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US369970A Expired - Lifetime US3893801A (en) 1972-06-16 1973-06-14 Transfer dyeing

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BE (1) BE800954A (en)
FR (1) FR2190066A5 (en)
GB (1) GB1390864A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4050891A (en) * 1976-12-17 1977-09-27 Crompton & Knowles Corporation Heat transfer black dyestuff A
US4093416A (en) * 1976-01-02 1978-06-06 Ciba-Geigy Ag Process for printing carpets
CN106748902A (en) * 2016-12-30 2017-05-31 江苏道博化工有限公司 One kind 1 amino 4 of synthesis（Ethylamino）The method of the sulfonic acid of 9,10 anthraquinone 2
JP2019206665A (en) * 2018-05-30 2019-12-05 日本化薬株式会社 Anthraquinone compound and dyeing method

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1938029A (en) * 1930-03-02 1933-12-05 Gen Aniline Works Inc Manufacture of aminoanthraquinone-nitriles
US3707346A (en) * 1970-01-16 1972-12-26 Ciba Geigy Ag Sublimatory transfer dyeing with 2-cyano-1,4-diamino anthraquinones

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1938029A (en) * 1930-03-02 1933-12-05 Gen Aniline Works Inc Manufacture of aminoanthraquinone-nitriles
US3707346A (en) * 1970-01-16 1972-12-26 Ciba Geigy Ag Sublimatory transfer dyeing with 2-cyano-1,4-diamino anthraquinones

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4093416A (en) * 1976-01-02 1978-06-06 Ciba-Geigy Ag Process for printing carpets
US4050891A (en) * 1976-12-17 1977-09-27 Crompton & Knowles Corporation Heat transfer black dyestuff A
CN106748902A (en) * 2016-12-30 2017-05-31 江苏道博化工有限公司 One kind 1 amino 4 of synthesis（Ethylamino）The method of the sulfonic acid of 9,10 anthraquinone 2
JP2019206665A (en) * 2018-05-30 2019-12-05 日本化薬株式会社 Anthraquinone compound and dyeing method

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Publication number Publication date
GB1390864A (en) 1975-04-16
BE800954A (en) 1973-10-01
FR2190066A5 (en) 1974-01-25

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