US3502425A - Process for the production of water-insoluble azo-dyestuffs on textile materials consisting of cellulose fibers or natural silk - Google Patents

Process for the production of water-insoluble azo-dyestuffs on textile materials consisting of cellulose fibers or natural silk Download PDF

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US3502425A
US3502425A US473481A US3502425DA US3502425A US 3502425 A US3502425 A US 3502425A US 473481 A US473481 A US 473481A US 3502425D A US3502425D A US 3502425DA US 3502425 A US3502425 A US 3502425A
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acid
water
dyestuffs
hydroxy
production
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Hasso Hertel
Werner Kirst
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Hoechst AG
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    • 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
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
    • D06P1/12—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes prepared in situ
    • D06P1/127—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes prepared in situ using a stabilised diazo component, e.g. diazoamino, anti-diazotate or nitrosamine R-N=N-OK, diazosulfonate, hydrazinesulfonate, R-N=N-N-CN
    • 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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/039—Disazo dyes characterised by the tetrazo component
    • C09B35/04—Disazo dyes characterised by the tetrazo component the tetrazo component being a benzene derivative
    • 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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/039—Disazo dyes characterised by the tetrazo component
    • C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
    • 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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/039—Disazo dyes characterised by the tetrazo component
    • C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
    • C09B35/10—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type
    • C09B35/14—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type from hydroxy compounds
    • 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
    • C09B41/00—Special methods of performing the coupling reaction

Definitions

  • X represents hydrogen, lower alkyl or lower alkoxy
  • R represents lower alkyl
  • Alk represents alkylene having 1 or 2 carbon atoms
  • Y represents the grouping --COOMe or SO Me wherein Me stands for the monovalent radical of an alkali metal or alkaline earth metal, (3) a wetting or dispersing agent and, optionally, (4) inorganic or organic salts, and subsequently forming the dyestufi in the same bath, without intermediate drying by treatment with acid agents at a temperature below 40 C.
  • water-insoluble azo-dyestuifs can be produced on textile material consisting of vegetable fibers by printing the textile material with printing pastes which contain a tetrazo-amino compound of an aromatic diamine and an o-hydroxy-carboxylic acid aryl amide, drying the textile material and developing the dyestufi by a treatment with an acid at an elevated temperature. It has also been proposed to add mixtures of such tetrazoamino compounds and o-hydroxy-carboxylic acid amides onto cellulose fabrics, to dry the fabrics and to subsequently provoke coupling by a treatment with an acid. Thus, these processes require 3 stages for the production of a dyemg.
  • water-insoluble azo-dyestuifs can be produced on textile material consisting of cellulose fibers or natural silk in a considerably simpler manner by treating the textile material in an alkaline bath which contains an aryl amide of the 5-hydroxy-1,2,l,2-benzocarbazole-4carboxylic acid and a tetrazo-amino compound of the general formula in which X represents hydrogen, lower alkyl or lower alkoxy, R represents lower alkyl, Alk represents alkylene having 1 or 2 carbon atoms and Y represents the grouping --OOOMe or SO Me in which Me stands for the monovalent radical of an alkali metal or alkaline earth metal, furthermore a wetting or dispersing agent and, if required or desired, inorganic or organic salts, and subsequently provoking the formation of the dyestufi by a treatment with acid agents at a temperature below 40 C.
  • the process of the present invention is carried out in the following manner: the textile material in the form of hanks, wound bodies, combed or loose material is treated in an alkaline bath which contains the coupling component and a tetrazoamino compound of the indicated composition, a wetting or dispersing agent, and, if desired or required, inorganic or organic salts, for example, sodium chloride, a sodium phosphate, sodium sulfate or sodium acetate.
  • the treatment is carried out for a period of at least 10 minutes in order to allow the coupling component to fix sufliciently and uniformly onto the textile material.
  • the process is carried out at room temperature or at a slightly elevated temperature, advantageously below 35 C.
  • an organic acid for example, formic acid, acetic acid, tartaric acid, citric acid, lactic acid or glycolic acid or a mixture of these acids or a mixture of a mineral acid, for example, hydrochloric acid or sulfuric acid
  • an organic acid is added to the bath in a quantity such that the total quantity of alkali in the bath and on the textile material is neutralised and a pH-value in the range of about 5.5 and 7 is reached.
  • the addition of acid must be carried out very carefully, because if the indicated pH-range is exceeded or if the pH is below the indicated range, the strength of the dyestuif is reduced.
  • the process is preferably carried out in the presence of suitable buffers, for example, trisodium phosphate, which permit the adjustment to the optimum pH-value.
  • suitable buffers for example, trisodium phosphate, which permit the adjustment to the optimum pH-value.
  • care must be taken that no local pH-variations occur.
  • the temperatures should be below 40 C. At this temperature, thedyestuff is formed on the textile material.
  • the material is washed in a neutral or acid bath, if desired or required in the presence of dispersing agents, washed again, and the dyeing thus produced is processed as usual. In this manner, level dyeings which are fast to rubbing are obtained.
  • arylamides of 5-hydroxy-1,2, 1,2'-benzocarbazole-4-carboxylic acid which are distinguished by a high substantivity towards the textile material used.
  • Suitable compounds for use in the process are, for example,
  • tetrazo-amino compounds there may be used the compounds obtained by coupling tetrazotized benzidine or the 3,3'-dialkylor 3,3'-dialkoxy derivatives thereof with alkali metal salts or alkaline earth metal salts of N- alkylamino-acetic acids, N-alkylamino-propionic acids or N-alkylamino-ethane sulfonic acids.
  • the compounds usually applied in the ice colour technique for example, the condensation products of higher molecular fatty acids and protein degradation products, the condensation products of higher molecular fatty acids and aminoalkyl-sulfonic acids, the condensation products of formaldehyde and naphthalene-sulfonic acids, or purified sulfite cellulose waste layer.
  • the process of the invention can be applied to textile material consisting of natural or regenerated cellulose or natural silk.
  • the process of the present invention is much simpler.
  • the dyebath is usually drained after the impregnation with the coupling component, the goods are centrifuged, squeezed with suction or rinsed intermediately and the dyestuif is developed in a second bath with a diazonium compound.
  • the process of the present invention combines impregnation and development in one bath and after the period of time necessary'for fixing the coupling component, coupling is effected without any other intercalated operation, which considerably reduces the time required for the whole dyeing operation.
  • the process of the present invention using substantive coupling components and the above-indicated tetrazo-amino compounds is distinguished by the fact that the development of the dyestuffs can be carried out at low temperatures and that after the addition of the acid it is not necessary to increase the temperature.
  • a further advantage of the process of the invention resides in the fact that the tetrazo-amino compounds are present in the alkaline bath in the form of dissolved alkali metal salts and, therefore, completely penetrate into the material to be dyed, which ensures complete coupling, whereas when water-insoluble diazo-amino compounds are used, these are deposited on the surface of the material to be dyed, resulting in a poor penetration of the dye and insuificient fastness to rubbing.
  • a tetrazo-amino compound having a strength of 33% and obtained from tetrazotized 4,4 -diamino-3,3'-dimethoxy-diphenyl and the sodium salt of N-methyltaurine, 47 cc. of a sodium hydroxide solution having 38 B., 55.2 g. of trisodium phosphate and 13. g. of a condensation product of oleic acid and methyltaurine in about 13,000 cc. of water having 30 C.
  • a process for the production of water-insoluble azodyestuffs on textile material of cellulose or silk which comprises treating said textile material in an alkaline bath which contains (1) an arylamide of the S-hydroxy- 1,2,l',2'-benzocarbazole-4-carboxylic acid, (2) a tetrazoamino compound of the formula R wherein X is hydrogen, lower alkyl or lower alkoxy, R is lower alkyl, Alk is lower alkylene having 1 or 2 carbon atoms and Y is the grouping COOMe or SO Me wherein Me stands for the monovalent radical of an alkali metal or alkaline earth metal, and (3) a dispersing agent, and then treating the goods in the same bath, without an intermediate drying step at a temperature References Cited UNITED STATES PATENTS 2,205,663 6/1940 Lecher et a1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)

Description

United States Patent M PROCESS FOR THE PRODUCTION OF WATER-IN- SOLUBLE AZO-DYESTUFFS ON TEXTILE MA- TERIALS CONSISTING OF CELLULOSE FIBERS OR NATURAL SILK Hasso Hertel and Werner Kirst, Oifenbach am Main, Germany, assignors to Farbwerke Hoechst Aktiengesellschaft vormals Meister Lucius & Bruning, Frankfurt am Main, Germany, a corporation of Germany No Drawing. Filed July 20, 1965, Ser. No. 473,481 Claims priority, appliclzrrtigrggrmany, July 31, 1964,
US. Cl. 8-45 2 Claims ABSTRACT OF THE DISCLOSURE The production of water-insoluble axe-dyestuffs on textile materials of cellulose fibers or natural silk by treating the textile material in an alkaline bath containing (1) an aryl amide of the -hydroxy-1,2,1',2'-benzocarbazo1e- 4-carboxy1ic acid, (2) a tetrazo-amino compound of the formula:
wherein X represents hydrogen, lower alkyl or lower alkoxy, R represents lower alkyl, Alk represents alkylene having 1 or 2 carbon atoms and Y represents the grouping --COOMe or SO Me wherein Me stands for the monovalent radical of an alkali metal or alkaline earth metal, (3) a wetting or dispersing agent and, optionally, (4) inorganic or organic salts, and subsequently forming the dyestufi in the same bath, without intermediate drying by treatment with acid agents at a temperature below 40 C.
It is known that water-insoluble azo-dyestuifs can be produced on textile material consisting of vegetable fibers by printing the textile material with printing pastes which contain a tetrazo-amino compound of an aromatic diamine and an o-hydroxy-carboxylic acid aryl amide, drying the textile material and developing the dyestufi by a treatment with an acid at an elevated temperature. It has also been proposed to add mixtures of such tetrazoamino compounds and o-hydroxy-carboxylic acid amides onto cellulose fabrics, to dry the fabrics and to subsequently provoke coupling by a treatment with an acid. Thus, these processes require 3 stages for the production of a dyemg.
Now, we have found that water-insoluble azo-dyestuifs can be produced on textile material consisting of cellulose fibers or natural silk in a considerably simpler manner by treating the textile material in an alkaline bath which contains an aryl amide of the 5-hydroxy-1,2,l,2-benzocarbazole-4carboxylic acid and a tetrazo-amino compound of the general formula in which X represents hydrogen, lower alkyl or lower alkoxy, R represents lower alkyl, Alk represents alkylene having 1 or 2 carbon atoms and Y represents the grouping --OOOMe or SO Me in which Me stands for the monovalent radical of an alkali metal or alkaline earth metal, furthermore a wetting or dispersing agent and, if required or desired, inorganic or organic salts, and subsequently provoking the formation of the dyestufi by a treatment with acid agents at a temperature below 40 C.
The process of the present invention is carried out in the following manner: the textile material in the form of hanks, wound bodies, combed or loose material is treated in an alkaline bath which contains the coupling component and a tetrazoamino compound of the indicated composition, a wetting or dispersing agent, and, if desired or required, inorganic or organic salts, for example, sodium chloride, a sodium phosphate, sodium sulfate or sodium acetate. The treatment is carried out for a period of at least 10 minutes in order to allow the coupling component to fix sufliciently and uniformly onto the textile material. In general, the process is carried out at room temperature or at a slightly elevated temperature, advantageously below 35 C. When the coupling component has fixed to a large extent and has levelled, an organic acid, for example, formic acid, acetic acid, tartaric acid, citric acid, lactic acid or glycolic acid or a mixture of these acids or a mixture of a mineral acid, for example, hydrochloric acid or sulfuric acid, with an organic acid is added to the bath in a quantity such that the total quantity of alkali in the bath and on the textile material is neutralised and a pH-value in the range of about 5.5 and 7 is reached. The addition of acid must be carried out very carefully, because if the indicated pH-range is exceeded or if the pH is below the indicated range, the strength of the dyestuif is reduced. Therefore, the process is preferably carried out in the presence of suitable buffers, for example, trisodium phosphate, which permit the adjustment to the optimum pH-value. When mixtures of mineral or organic acids are used, care must be taken that no local pH-variations occur.
The temperatures should be below 40 C. At this temperature, thedyestuff is formed on the textile material. The material is washed in a neutral or acid bath, if desired or required in the presence of dispersing agents, washed again, and the dyeing thus produced is processed as usual. In this manner, level dyeings which are fast to rubbing are obtained.
As coupling components, there may be used in the process of the present invention arylamides of 5-hydroxy-1,2, 1,2'-benzocarbazole-4-carboxylic acid which are distinguished by a high substantivity towards the textile material used. Suitable compounds for use in the process are, for example,
1-(5'-hydroxy-1',2',1",2"-benzocarbazole-4'-carboyl amino -4-methoxybenzene, 1- (5-hydroxy-1,2', 1",2-benzocarbazole-4'-carboylamino 2-methyl-4-methoxybenzene, 1-(5'-hydroxy-1',2',1",2"benzocarbazo1e-4-carboylamino) -4-chlorobenzene, 1-(5-hydroxy-1',2',1,2"-benzocarbazole-4-carboylamino) -4-methylb enzene, 1-(5'-hydroxy-1,2',1",2"-benzocarbazole-4'-carboylamino) -2-methoxybenzene, 1-(5'-hydroxy-1',2',1",2"-benzocarbazole-4-carboylamino) 3 ,4-dimethoxybenzene, 1 (5'-hydroxy-1',2',1",2"-benzocarbazole-4-carboylamino) -2-methoxy-5chlorobenzene, 1-(5'-hydroxy-1',2, 1",2"-benzocarbazole-4'-carboy1- amino) -3-methyl-4-methoxyb enzene, 1- (5'-hydroxy-1,2',1",2"-benzocarbazole-4'-carboylamino -2,5 -dimethoxybenzene or 1-(5-hydroxy-1,2',1",2"-benzocarbazole-4-carboylamino) -2,4-dimethoxybenzene.
As tetrazo-amino compounds, there may be used the compounds obtained by coupling tetrazotized benzidine or the 3,3'-dialkylor 3,3'-dialkoxy derivatives thereof with alkali metal salts or alkaline earth metal salts of N- alkylamino-acetic acids, N-alkylamino-propionic acids or N-alkylamino-ethane sulfonic acids.
As wetting or dispersing agents, there may be used the compounds usually applied in the ice colour technique, for example, the condensation products of higher molecular fatty acids and protein degradation products, the condensation products of higher molecular fatty acids and aminoalkyl-sulfonic acids, the condensation products of formaldehyde and naphthalene-sulfonic acids, or purified sulfite cellulose waste layer.
The process of the invention can be applied to textile material consisting of natural or regenerated cellulose or natural silk.
Compared with the. dyeing processes using ice colours, the process of the present invention is much simpler. In the known dyeing processes, the dyebath is usually drained after the impregnation with the coupling component, the goods are centrifuged, squeezed with suction or rinsed intermediately and the dyestuif is developed in a second bath with a diazonium compound. In contradistinction thereto, the process of the present invention combines impregnation and development in one bath and after the period of time necessary'for fixing the coupling component, coupling is effected without any other intercalated operation, which considerably reduces the time required for the whole dyeing operation.
From German Patent 1,057,061 it is known that waterinsoluble azo-dyestutfs can be produced on vegetable fibers by treating these fibers at long goods-to-liquor ratios in a bath containing a coupling component and a diazoamino or tetraZo-amino compound without solubilising groups and by subsequently developing the dyestuif by a treatment in an acid bath.
Compared with this process, the process of the present invention using substantive coupling components and the above-indicated tetrazo-amino compounds is distinguished by the fact that the development of the dyestuffs can be carried out at low temperatures and that after the addition of the acid it is not necessary to increase the temperature. A further advantage of the process of the invention resides in the fact that the tetrazo-amino compounds are present in the alkaline bath in the form of dissolved alkali metal salts and, therefore, completely penetrate into the material to be dyed, which ensures complete coupling, whereas when water-insoluble diazo-amino compounds are used, these are deposited on the surface of the material to be dyed, resulting in a poor penetration of the dye and insuificient fastness to rubbing.
The following examples illustrate the invention but they are not intended to limit it thereto:
EXAMPLE Cross-wound bobbins of cotton were pre-wetted with a highly effective wetting agent and then treated for 30 minutes at 30 C., at a goods-to-liquor ratio of 1:13, in a bath that had been prepared as follows:
36 g. of 1-(5hydroxy 1',2',1",2" benzocarbazole-4'- carboylamino)4-methoxybenzene were dissolved in 80 cc. of denatured ethanol, 18 cc. of sodium hydroxide solution having 38 B., 72 cc. of water having 70 C. and 36 cc. of a formaldehyde solution having a strength of 30%, and the whole was introduced into a bath containing 140 g. of a tetrazo-amino compound having a strength of 33% and obtained from tetrazotized 4,4 -diamino-3,3'-dimethoxy-diphenyl and the sodium salt of N-methyltaurine, 47 cc. of a sodium hydroxide solution having 38 B., 55.2 g. of trisodium phosphate and 13. g. of a condensation product of oleic acid and methyltaurine in about 13,000 cc. of water having 30 C.
After about 15 minutes, 260 g. of sodium chloride were added and the treatment was continued for 15 minutes. Then, 138 cc. of a 50% acetic acid were added portionwise and the treatment of the goods was continued for 30 minutes at a pH-value in the range of 6 to 6.5. The goods were then rinsed with a solution containing, per liter of water, 0.5 g. of a condensation product of oleic acid and methyltaurine, treated for 15 minutes at 60 C. with a solution containing, per liter of water, 3. g., of a mixture consisting of 63% of percholorethylene, 17% of a reaction product of about 10 mols of ethylene oxide with 1 mol of nonylphenol, and 20% of isopropyl alcohol, and 0.5 g. of the sodium salt of nitrilotriacetic acid, rinsed, treated at the boiling temperatures for 15 minutes with a solution containing, per liter of water, 1 g. of a condensation product of oleic acid and methyltaurine, 0.5 g. of the sodium. salt of nitrilotriacetic acid and 0.5 g. of soda ash, rinsed and dried.
A bluish black dyeing having good properties of fastness was obtained.
The following table lists a number of further components which may be used according to the present invention and the tints of the azo-dyestuffs produced on cellulose fibers.
Tetrazoamino-compound from tetrazotized Coupling component Tint 4,4-diaminodiphenyl and 1-(5-hydroxy-1,2,1",2- Black.
the sodium salt of N- benzocarbazole-4'-carboylmethyltaurine. amino)-4-methoxybenzene.
4,4-diamir1odiphenyl and ..do Do.
the sodium salt of sarcosme.
4,4-diamino-3,3'-dimethyl- ..do Do.
diphenyl and the sodium salt of N methyltaurine.
4,4 -diamino-3,3-dimethoxy- 1-(5-hydroxy-1 ,2 ,1 ,2- Bluediphenyl and the sodium benzocarbaZole-4-carb0ylblack. salt of N methyltaurine. amino) -2-methy1-4- methoxybenzene. 4,4-diam1no-3,3-dimethyl- 1- (5-hydroxy-1,2 ,1" ,2 Black.
diphenyl and the sodium benzocarbazole4-carboylsalt of sareosine. amino)-2,4-dimethoxybenzene.
(,4-diamino-3,3-dimethyldo D0.
diphenyl and the sodium salt of N-methyltaun'ne.
4,4-diamino-3,3-dimethoxydo Do.
diphenyl and the sodium salt of sarcosine.
4,4-diamino-3,3-dimethoxy- ..do D0.
diphenyl and the potassium salt of N methyltaurine.
We claim:
1. A process for the production of water-insoluble azodyestuffs on textile material of cellulose or silk, which comprises treating said textile material in an alkaline bath which contains (1) an arylamide of the S-hydroxy- 1,2,l',2'-benzocarbazole-4-carboxylic acid, (2) a tetrazoamino compound of the formula R wherein X is hydrogen, lower alkyl or lower alkoxy, R is lower alkyl, Alk is lower alkylene having 1 or 2 carbon atoms and Y is the grouping COOMe or SO Me wherein Me stands for the monovalent radical of an alkali metal or alkaline earth metal, and (3) a dispersing agent, and then treating the goods in the same bath, without an intermediate drying step at a temperature References Cited UNITED STATES PATENTS 2,205,663 6/1940 Lecher et a1. 845 2,214,559 9/1940 Lecher et a1 844 3,003,844 10/1961 Jelinek et a1 845 3,183,052 5/1965 Sommer et a1 846 GEORGE E. LESMES, Primary Examiner J. R. MILLER, Assistant Examiner
US473481A 1964-07-31 1965-07-20 Process for the production of water-insoluble azo-dyestuffs on textile materials consisting of cellulose fibers or natural silk Expired - Lifetime US3502425A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040083560A1 (en) * 2001-03-08 2004-05-06 Jean-Marie Adam Method of clouring porous material

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2205663A (en) * 1940-06-25 Ice color producing composition
US2214559A (en) * 1939-07-15 1940-09-10 American Cyanamid Co Stable solution for producing ice colors
US3003844A (en) * 1957-06-10 1961-10-10 Gen Aniline & Film Corp Stable solution for producing ice colors
US3183052A (en) * 1961-10-18 1965-05-11 Hoechst Ag Process for the continuous production of brown water-insoluble azo-dyestuffs on fabrics of vegetable fibers

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2205663A (en) * 1940-06-25 Ice color producing composition
US2214559A (en) * 1939-07-15 1940-09-10 American Cyanamid Co Stable solution for producing ice colors
US3003844A (en) * 1957-06-10 1961-10-10 Gen Aniline & Film Corp Stable solution for producing ice colors
US3183052A (en) * 1961-10-18 1965-05-11 Hoechst Ag Process for the continuous production of brown water-insoluble azo-dyestuffs on fabrics of vegetable fibers

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040083560A1 (en) * 2001-03-08 2004-05-06 Jean-Marie Adam Method of clouring porous material
US7041143B2 (en) * 2001-03-08 2006-05-09 Ciba Specialty Chemicals Corporation Method of coloring porous material

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DE1544487A1 (en) 1970-04-30

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