US3141728A - Process for the improvement of the fastness to washing of direct dyeings on cellulose-containing materials - Google Patents

Process for the improvement of the fastness to washing of direct dyeings on cellulose-containing materials Download PDF

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US3141728A
US3141728A US77026A US7702660A US3141728A US 3141728 A US3141728 A US 3141728A US 77026 A US77026 A US 77026A US 7702660 A US7702660 A US 7702660A US 3141728 A US3141728 A US 3141728A
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washing
cellulose
fastness
containing materials
dyeings
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US77026A
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Bockmann Klaus
Taube Carl
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Bayer AG
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Bayer 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
    • D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/655—Compounds containing ammonium groups
    • D06P1/66—Compounds containing ammonium groups containing quaternary ammonium 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
    • 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
    • D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/52—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
    • D06P1/56—Condensation products or precondensation products prepared with aldehydes
    • 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
    • D06P5/02—After-treatment
    • D06P5/04—After-treatment with organic compounds
    • D06P5/06—After-treatment with organic compounds containing nitrogen
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/918—Cellulose textile

Definitions

  • the object of the present invention is to provide a process for the improvement of the fastness to washing of direct dyeings on cellulose-containing materials by means of quaternary polyalkylene-polyamines and hardenable resinous intermediate products; this process consists in treating the direct dyeings on cellulose-containing ma terials with the polyalkylene-polyamines and the resinous intermediate products simultaneously and subsequently hardening the resinous intermediate products.
  • the fastness to washing of direct dyeings on cellulose materials such as cotton and, particularly, staple fibre is increased to a substantially greater extent by the simultaneous use of the above mentioned agents than by using them separately.
  • the dyeings which tend to change their shade upon treatment with quaternary polyalkylene-polyamines show a reduced change of shade in most cases where hardenable resinous intermediate products are used at the same time.
  • Quaternary polyalkylene-polyamines suitable for the process according to the invention are chiefly the compounds obtainable by contacting ditertiary ethylene diamines with aliphatic dihalogen compounds which are described in US. Patent No. 3,009,761, furthermore quaternized polypropylene polyamines derived from the mineral acid esters of 1-amino-3-propanol which are described in German Patent No. 1,040,503 and the quaternary ammonium compounds of higher molecular weight to be used in combination with water-soluble sulfates as described in British Patent No. 761,668.
  • hardenable resinous intermediate products there may be considered for example dimethylol-urea, dimethylol ethylene urea, dimethylol-dihydroxyethylene-urea, tetramethylol-acetylene-diurea, hexamethylol-melamine and their alkyl ethers.
  • the proportions of quaternary polyalkylene-polyamines and hardenable resinous intermediate products may vary within wide limits. In general, it is advantageous to use the hardenable resinous intermediate products in an excess of about the double or triple quantity by weight.
  • Example I A staple fibre fabric dyed with 2% of the dyestufi ob-' tainable according to Example 1 of US. Patent No. 2,712,006 is impregnated with the aqueous solution described below, then squeezed until its increase of weight amounts to 100% by weight, dried at 100 C. and heated to 150 C. for 5 minutes. The fabric is finally soaped as usual at C. for 3 0 minutes, then rinsed and dried. The dyeing of the fabric thus treated has an excellent fastness to washing.
  • the solution employed contained per litre 50 g. of dimethylol-dihydroxyethylene-urea, 10 g. of magnesium chloride and 20 g. of the solution containing a quaternary polyalkylene-polyamine and being prepared by heating a mixture of 11.6 grams of l,2-bis-(dimethyl-amino)- ethane and 12.7 grams of 1,4-dichloro-butane to 90- C. for about 40 hours, dissolving the reaction product in 50 millilitres of water and making up the solution with water to a total weight of grams after the addition of 30 grams or ammonium sulfate.
  • Example 2 A staple fibre fabric is dyed with 1% .of the dyestufi obtainable by coupling 1 mol of tetrazotized 4,4'-diamino- 3,3'-dihydroxyphenyl with 2 mols of 2-amino-5-hydroxynaphthalene-1,7-disulfonic acid and subsequently converting the disazo compound formed into the copper complex.
  • the fabric is finally impregnated with the aqueous solution described below, then squeezed until its increase of weight amounts to 100% by weight, dried at 80100 C. and heated to C. for 5 minutes.
  • the fabric is finally soaped, rinsed and dried in conventional manner.
  • the dyeing thus treated has an excellent fastness to Washing.
  • the aqueous solution employed contained per litre 50 g. of dimethylol-dihydroxyethylene-urea, 10 g. of magnesium chloride, 5 g. of ammonium chloride and 30 g. of the solution containing a quaternary polyalkylene-polyamine and being prepared according to Example 1 of German Patent No. 1,040,503 in the following manner: 26 g. l-amino-3-chloropropane hydrochloride were added to 40 g. of 40% aqueous sodium hydroxide solution and stirred at room temperature for 24 hours. Then the solution from which sodium chloride had separated was heated for two hours to 35-40 C., for 2 hours to 60-65 C. and for 2 hours on the boiling water bath. Thereupon in the course of about 4 hours 55 g. of dimethyl sulfate were dropped into the solution which was always kept weakly alkaline by the addition of sodium hydroxide solution. Finally the neutral solution was made up with water to g. and filtered.
  • the dyeing is also very fast to washing if aftertreated in the manner described above with a solution containing per litre 50 g. of dimethylol-dihydroxyethylene-urea, 10 g. of magnesium chloride and 40 g. of the solution containing a quaternary polyalkylene-polyamine and being prepared according to Example 3 of German patent specification No. 960,178 in the following manner: 90 parts by weight of polyethylene-imine (50%) were dissolved in 200 parts by weight of water and per alkylated at 20 C. with 300 parts by weight of dimethyl sulfate under neutralization with calcium hydroxide. Thereupon mineral acid was added and the reaction mixture was heated for some hours to 90-95 C. After neutralizing the reaction product with ammonia the precipitated calcium sulfate was filtered off and the filtrate filled up to 1500 parts by weight.
  • Example 3 A staple fibre fabric dyed with 2% of the dyestuff of Eaxmple 1 of US. Patent No. 2,917,504 is impregnated with the aqueous solution described below, then squeezed until its increase of weight amounts to 100% by weight, dried at 80100% C. and heated to 140 C. for 10 minutes. The fabric is finally soaped, rinsed and dried in conventional manner. The dyeing of the fabric thus treated is very fast to washing.
  • the aqueous solution employed contained per litre 100 g. of .hexamethylol-melamine, 10 g. of zinc chloride and 20 g. of the solution containing a quaternary polyalkylene-polyamine and. being prepared according to Example 1 above.
  • Example 4 Mercerized cotton dyed with 1.5% of the dyestufi of Example 3 of US. Patent No. 2,777,839 is impregnated with the aqueous solution described below, then squeezed until its increase of weight amounts to 100% by weight, dried at 80100 C. and heated to 160 C. for 3-4 minutes. The cotton is finally soaped, rinsed and dried in conventional manner. The dyeing of the cotton has an excellent fastness to washing.
  • the aqueous solution employed contains per litre 75 g. of dimethylol-dihydroxyethylene-urea, 10 g. of magnesium chloride and 15 g. of the solution containing a quaternary polyalkylene-polyamine and being prepared according I to Example 1 above.
  • Process for improving the fastness to Washing of direct dyeings an cellulose-containing materials which comprises treating the direct dyeings on cellulose-containing materials with a quaternary polyalkylene-polyamine and a resinous intermediate product simultaneously and subsequently hardening the resinous intermediate product.
  • polyalkylenepolyamine is a member of the group consisting of compounds obtainable by contacting ditertiary ethylene diamines with aliphatic dihalogen compounds, quaternized polypropylene polyamines derived from the sulfuric acid ester of 1-amino-3-propanol and quaternary ammonium compounds of higher molecular weight in combination with Water soluble sulfates.
  • the resinous intermediate product is a member of the group consisting of dimethylol-urea, dimethylol-ethylene-urea, dimethylol dihydroxyethylene urea, tetramethylol acetylene diurea, hexamethylol-melamine and their alkyl ethers.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)

Description

3,141,728 Patented July 21, 1964 PROCESS FOR THE IMPROVEMENT OF THE FAST- NESS T WASHING 0F DIRECT DYEINGS ON CELLULOSE-CONTAINING MATERIALS Klaus Biiekmann, Cologne-Starnmheim, and Carl Taube, Leverkusen, Germany, assignors to Farbenfabriken Bayer Aktiengesellschaft, Leverkusen, Germany, a corporation of Germany No Drawing. Filed Dec. 20, 1960, Ser. No. 77,026 Claims priority, application Germany Dec. 23, 1959 3 Claims. (Cl. 8-74) It is known that the fastness to washing of direct dyeings on cellulose-containing materials can be improved by means of quaternary polyalkylene-polyamines and it is further known that the fastness to washing of such dyeings can also be increased by applying to the cellulose-containing materials hardenable resinous intermediate products and by then hardening these intermediate products, for example by heating to temperatures above 100 C. Finally, it is also known that hardenable resinous intermediate products have been applied to cellulose materials which had previously been dyed with direct dyestuffs and after-treated with quaternary polyalkylene-polyamines, and that the intermediate products have been subsequently hardened.
The object of the present invention is to provide a process for the improvement of the fastness to washing of direct dyeings on cellulose-containing materials by means of quaternary polyalkylene-polyamines and hardenable resinous intermediate products; this process consists in treating the direct dyeings on cellulose-containing ma terials with the polyalkylene-polyamines and the resinous intermediate products simultaneously and subsequently hardening the resinous intermediate products.
Surprisingly, the fastness to washing of direct dyeings on cellulose materials such as cotton and, particularly, staple fibre, is increased to a substantially greater extent by the simultaneous use of the above mentioned agents than by using them separately. Moreover, the dyeings which tend to change their shade upon treatment with quaternary polyalkylene-polyamines, show a reduced change of shade in most cases where hardenable resinous intermediate products are used at the same time.
Quaternary polyalkylene-polyamines suitable for the process according to the invention are chiefly the compounds obtainable by contacting ditertiary ethylene diamines with aliphatic dihalogen compounds which are described in US. Patent No. 3,009,761, furthermore quaternized polypropylene polyamines derived from the mineral acid esters of 1-amino-3-propanol which are described in German Patent No. 1,040,503 and the quaternary ammonium compounds of higher molecular weight to be used in combination with water-soluble sulfates as described in British Patent No. 761,668.
As hardenable resinous intermediate products there may be considered for example dimethylol-urea, dimethylol ethylene urea, dimethylol-dihydroxyethylene-urea, tetramethylol-acetylene-diurea, hexamethylol-melamine and their alkyl ethers.
The proportions of quaternary polyalkylene-polyamines and hardenable resinous intermediate products may vary within wide limits. In general, it is advantageous to use the hardenable resinous intermediate products in an excess of about the double or triple quantity by weight.
The following examples serve to illustrate the invention without, however, limiting the scope thereof.
Example I A staple fibre fabric dyed with 2% of the dyestufi ob-' tainable according to Example 1 of US. Patent No. 2,712,006 is impregnated with the aqueous solution described below, then squeezed until its increase of weight amounts to 100% by weight, dried at 100 C. and heated to 150 C. for 5 minutes. The fabric is finally soaped as usual at C. for 3 0 minutes, then rinsed and dried. The dyeing of the fabric thus treated has an excellent fastness to washing.
The solution employed contained per litre 50 g. of dimethylol-dihydroxyethylene-urea, 10 g. of magnesium chloride and 20 g. of the solution containing a quaternary polyalkylene-polyamine and being prepared by heating a mixture of 11.6 grams of l,2-bis-(dimethyl-amino)- ethane and 12.7 grams of 1,4-dichloro-butane to 90- C. for about 40 hours, dissolving the reaction product in 50 millilitres of water and making up the solution with water to a total weight of grams after the addition of 30 grams or ammonium sulfate.
If a cotton fabric dyed with the indicated dyestuff is after-treated in the manner described above, the dyeing is fast to repeated washing at 95 C.
Example 2 A staple fibre fabric is dyed with 1% .of the dyestufi obtainable by coupling 1 mol of tetrazotized 4,4'-diamino- 3,3'-dihydroxyphenyl with 2 mols of 2-amino-5-hydroxynaphthalene-1,7-disulfonic acid and subsequently converting the disazo compound formed into the copper complex. The fabric is finally impregnated with the aqueous solution described below, then squeezed until its increase of weight amounts to 100% by weight, dried at 80100 C. and heated to C. for 5 minutes. The fabric is finally soaped, rinsed and dried in conventional manner. The dyeing thus treated has an excellent fastness to Washing.
The aqueous solution employed contained per litre 50 g. of dimethylol-dihydroxyethylene-urea, 10 g. of magnesium chloride, 5 g. of ammonium chloride and 30 g. of the solution containing a quaternary polyalkylene-polyamine and being prepared according to Example 1 of German Patent No. 1,040,503 in the following manner: 26 g. l-amino-3-chloropropane hydrochloride were added to 40 g. of 40% aqueous sodium hydroxide solution and stirred at room temperature for 24 hours. Then the solution from which sodium chloride had separated was heated for two hours to 35-40 C., for 2 hours to 60-65 C. and for 2 hours on the boiling water bath. Thereupon in the course of about 4 hours 55 g. of dimethyl sulfate were dropped into the solution which was always kept weakly alkaline by the addition of sodium hydroxide solution. Finally the neutral solution was made up with water to g. and filtered.
The dyeing is also very fast to washing if aftertreated in the manner described above with a solution containing per litre 50 g. of dimethylol-dihydroxyethylene-urea, 10 g. of magnesium chloride and 40 g. of the solution containing a quaternary polyalkylene-polyamine and being prepared according to Example 3 of German patent specification No. 960,178 in the following manner: 90 parts by weight of polyethylene-imine (50%) were dissolved in 200 parts by weight of water and per alkylated at 20 C. with 300 parts by weight of dimethyl sulfate under neutralization with calcium hydroxide. Thereupon mineral acid was added and the reaction mixture was heated for some hours to 90-95 C. After neutralizing the reaction product with ammonia the precipitated calcium sulfate was filtered off and the filtrate filled up to 1500 parts by weight.
Example 3 A staple fibre fabric dyed with 2% of the dyestuff of Eaxmple 1 of US. Patent No. 2,917,504 is impregnated with the aqueous solution described below, then squeezed until its increase of weight amounts to 100% by weight, dried at 80100% C. and heated to 140 C. for 10 minutes. The fabric is finally soaped, rinsed and dried in conventional manner. The dyeing of the fabric thus treated is very fast to washing.
The aqueous solution employed contained per litre 100 g. of .hexamethylol-melamine, 10 g. of zinc chloride and 20 g. of the solution containing a quaternary polyalkylene-polyamine and. being prepared according to Example 1 above.
Example 4 Mercerized cotton dyed with 1.5% of the dyestufi of Example 3 of US. Patent No. 2,777,839 is impregnated with the aqueous solution described below, then squeezed until its increase of weight amounts to 100% by weight, dried at 80100 C. and heated to 160 C. for 3-4 minutes. The cotton is finally soaped, rinsed and dried in conventional manner. The dyeing of the cotton has an excellent fastness to washing.
The aqueous solution employed contains per litre 75 g. of dimethylol-dihydroxyethylene-urea, 10 g. of magnesium chloride and 15 g. of the solution containing a quaternary polyalkylene-polyamine and being prepared according I to Example 1 above.
We claim:
1. Process for improving the fastness to Washing of direct dyeings an cellulose-containing materials which comprises treating the direct dyeings on cellulose-containing materials with a quaternary polyalkylene-polyamine and a resinous intermediate product simultaneously and subsequently hardening the resinous intermediate product.
2. Process according to claim 1 where the polyalkylenepolyamine is a member of the group consisting of compounds obtainable by contacting ditertiary ethylene diamines with aliphatic dihalogen compounds, quaternized polypropylene polyamines derived from the sulfuric acid ester of 1-amino-3-propanol and quaternary ammonium compounds of higher molecular weight in combination with Water soluble sulfates.
3. Process according to claim 1 wherein the resinous intermediate product is a member of the group consisting of dimethylol-urea, dimethylol-ethylene-urea, dimethylol dihydroxyethylene urea, tetramethylol acetylene diurea, hexamethylol-melamine and their alkyl ethers.
References Cited in the tile of this patent UNITED STATES PATENTS 2,093,651 Widmer et al Sept. 21, 1937 2,312,199 Tallis et a1. Feb. 23, 1943 2,777,839 Bockmann et al Ian. 15, 1957 2,917,504 Bockmann et a1 Dec. 15, 1959 2,955,014 Segal et a1. Oct. 4, 1960 2,973,239 Gortvai Feb. 28, 1961 3,009,761 Taube et a1. Nov. 21, 1961

Claims (1)

1. PROCESS FOR IMPROVING THE FASTNESS TO WASHING OF DIRECT DYEINGS AN CELLULOSE-CONTAINING MATERIALS WHICH COMPRISES TREATING THE DIRECT DYEINGS ON CELLULOSE-CONTAINING MATERIALS WITH A QUATERNARY POLYALKYLENE-POLYOMINE AND A RESINOUS INTERMEDIATE PRODUCT SIMULTANEOUSLY AND SUBSEQUENTLY HARDENING THE RESINOUS INTERMEDIATE PRODUCT.
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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4167393A (en) * 1978-08-21 1979-09-11 The Dow Chemical Company Method for binding a water-soluble direct dye to paper
US4263009A (en) * 1978-01-31 1981-04-21 Milliken Research Corporation Method for improving the dyeing characteristics of textile materials containing polyolefin fibers and products produced thereby
WO1981002423A1 (en) * 1980-02-22 1981-09-03 Sandoz Ag Colouring means and method for colouring cellulose fibers
DE3217835A1 (en) * 1981-05-16 1982-12-02 Sandoz-Patent-GmbH, 7850 Lörrach Dyeing products and method for aftertreating dyeings
US4417898A (en) * 1981-09-11 1983-11-29 Rolf Hasler Continuous dyeing process which provides improved wetfastness: alkandlamine-containing dye liquor and after-treatment with fixing agent
FR2532341A1 (en) * 1982-08-30 1984-03-02 Sandoz Sa PROCESS FOR IMPROVING THE SOLIDITIES OF OPTICAL DYES OR BRIGHTENERS ON A SUBSTRATE CONTAINING POLYAMIDE FIBERS OR FIBERS CONTAINING HYDROXY GROUPS
US4436524A (en) 1981-05-16 1984-03-13 Sandoz Ltd. After treating composition for direct or reactive dyeings on cellulose
US4439203A (en) * 1981-05-14 1984-03-27 Sandoz Ltd. Process for improving the wetfastness of dyeings, printings and optical brightenings on cellulosic substrates and compositions useful therefor
US4439208A (en) * 1981-06-22 1984-03-27 Sandoz Ltd. Method for improving the fastness of dyeings with basic dyes on cellulosic substrates
US4443223A (en) * 1980-09-24 1984-04-17 Sandoz Ltd. Composition and method for improving the fastness of direct and reactive dyeings on cellulose-containing substrates
US4452606A (en) * 1981-05-14 1984-06-05 Sandoz Ltd. Compositions useful for improving the fastness of dyeings on cellulosic substrates: precondensates of N-methylol compound with polyalkylene polyamine-epihalohydrin product
US4764176A (en) * 1985-07-22 1988-08-16 Sandoz Ltd. Method for preventing the brightening effect of optical brightening agents on textiles
US20080163437A1 (en) * 2007-01-10 2008-07-10 Xinggao Fang Cellulosic textiles treated with hyperbranched polyethyleneimine derivatives
US20080164439A1 (en) * 2007-01-10 2008-07-10 Xinggao Fang Textiles treated with hyperbranched polyethyleneimine derivatives for odor control properties
US20090246258A1 (en) * 2008-03-28 2009-10-01 Piyush Shukla Antimicrobial and odor adsorbing textile

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2093651A (en) * 1933-02-09 1937-09-21 Gustave A Widmer Dyeing fibrous materials
US2312199A (en) * 1939-11-22 1943-02-23 Courtaulds Ltd Treatment of cellulosic textile materials
US2777839A (en) * 1953-04-18 1957-01-15 Bayer Ag Grey trisazo dyestuffs
US2917504A (en) * 1954-08-25 1959-12-15 Bayer Ag Tetrakisazo dyestuffs
US2955014A (en) * 1955-03-04 1960-10-04 Segal Leon Process of treating native cellulose with a liquid alkylenepolyamine and a textile resin
US2973239A (en) * 1956-11-19 1961-02-28 United Merchants & Mfg Color fixing agents
US3009761A (en) * 1957-01-19 1961-11-21 Bayer Ag Polyquaternary ammonium compounds

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2093651A (en) * 1933-02-09 1937-09-21 Gustave A Widmer Dyeing fibrous materials
US2312199A (en) * 1939-11-22 1943-02-23 Courtaulds Ltd Treatment of cellulosic textile materials
US2777839A (en) * 1953-04-18 1957-01-15 Bayer Ag Grey trisazo dyestuffs
US2917504A (en) * 1954-08-25 1959-12-15 Bayer Ag Tetrakisazo dyestuffs
US2955014A (en) * 1955-03-04 1960-10-04 Segal Leon Process of treating native cellulose with a liquid alkylenepolyamine and a textile resin
US2973239A (en) * 1956-11-19 1961-02-28 United Merchants & Mfg Color fixing agents
US3009761A (en) * 1957-01-19 1961-11-21 Bayer Ag Polyquaternary ammonium compounds

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4263009A (en) * 1978-01-31 1981-04-21 Milliken Research Corporation Method for improving the dyeing characteristics of textile materials containing polyolefin fibers and products produced thereby
US4167393A (en) * 1978-08-21 1979-09-11 The Dow Chemical Company Method for binding a water-soluble direct dye to paper
WO1981002423A1 (en) * 1980-02-22 1981-09-03 Sandoz Ag Colouring means and method for colouring cellulose fibers
US4410652A (en) * 1980-02-22 1983-10-18 Sandoz Ltd. Reaction products useful for improving the wetfastness of direct and reactive dyes on cellulosic substrates
US4443223A (en) * 1980-09-24 1984-04-17 Sandoz Ltd. Composition and method for improving the fastness of direct and reactive dyeings on cellulose-containing substrates
US4439203A (en) * 1981-05-14 1984-03-27 Sandoz Ltd. Process for improving the wetfastness of dyeings, printings and optical brightenings on cellulosic substrates and compositions useful therefor
US4452606A (en) * 1981-05-14 1984-06-05 Sandoz Ltd. Compositions useful for improving the fastness of dyeings on cellulosic substrates: precondensates of N-methylol compound with polyalkylene polyamine-epihalohydrin product
US4436524A (en) 1981-05-16 1984-03-13 Sandoz Ltd. After treating composition for direct or reactive dyeings on cellulose
DE3217835A1 (en) * 1981-05-16 1982-12-02 Sandoz-Patent-GmbH, 7850 Lörrach Dyeing products and method for aftertreating dyeings
US4439208A (en) * 1981-06-22 1984-03-27 Sandoz Ltd. Method for improving the fastness of dyeings with basic dyes on cellulosic substrates
US4417898A (en) * 1981-09-11 1983-11-29 Rolf Hasler Continuous dyeing process which provides improved wetfastness: alkandlamine-containing dye liquor and after-treatment with fixing agent
FR2532341A1 (en) * 1982-08-30 1984-03-02 Sandoz Sa PROCESS FOR IMPROVING THE SOLIDITIES OF OPTICAL DYES OR BRIGHTENERS ON A SUBSTRATE CONTAINING POLYAMIDE FIBERS OR FIBERS CONTAINING HYDROXY GROUPS
US4475918A (en) * 1982-08-30 1984-10-09 Sandoz Ltd. Composition and method for improving the fastness of anionic dyes and brighteners on cellulosic and polyamide fibers
CH669705GA3 (en) * 1982-08-30 1989-04-14
US4764176A (en) * 1985-07-22 1988-08-16 Sandoz Ltd. Method for preventing the brightening effect of optical brightening agents on textiles
US20080163437A1 (en) * 2007-01-10 2008-07-10 Xinggao Fang Cellulosic textiles treated with hyperbranched polyethyleneimine derivatives
US20080164439A1 (en) * 2007-01-10 2008-07-10 Xinggao Fang Textiles treated with hyperbranched polyethyleneimine derivatives for odor control properties
US20090246258A1 (en) * 2008-03-28 2009-10-01 Piyush Shukla Antimicrobial and odor adsorbing textile

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