Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
  • C08G73/02—Polyamines
  • C08G73/0206—Polyalkylene(poly)amines
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
  • C08G73/02—Polyamines
  • C08G73/0206—Polyalkylene(poly)amines
  • C08G73/0213—Preparatory process
  • C08G73/022—Preparatory process from polyamines and epihalohydrins
• • 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
  • D06P1/60—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 polyethers
  • D06P1/607—Nitrogen-containing polyethers or their quaternary derivatives
• • 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
  • D06P1/62—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 low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic 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
  • D06P1/64—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 low-molecular-weight organic compounds without sulfate or sulfonate groups
  • D06P1/642—Compounds containing nitrogen
  • D06P1/6422—Compounds containing nitro or nitroso 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
  • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
  • D06P3/02—Material containing basic nitrogen
  • D06P3/04—Material containing basic nitrogen containing amide groups
  • D06P3/14—Wool
• • 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
  • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
  • D06P3/02—Material containing basic nitrogen
  • D06P3/04—Material containing basic nitrogen containing amide groups
  • D06P3/24—Polyamides; Polyurethanes
• • 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

Definitions

• the present invention relates to a method of increasing the depth of shade of dyed natural or synthetic polyamide fibre materials by treatment with specific polyamines before, during or after dyeing.
• the present invention relates to a method of increasing the depth of shade of dyed natural or synthetic polyamide fibre materials, which comprises treating the fibre material - before, during or after dyeing - with an aqueous liquor comprising a polyamine, the polyamine being the product of reaction of a compound containing at least two primary amino groups with ethylene oxide, propylene oxide, 1 ,2-epoxybutane, a chloroalkylamine or an aromatic compound having at least one -COCI, -S0 3 CI or -SO 2 -Z substituent wherein Z is vinyl, 2-chloroethyl or 2-sulfatoethyl, or the product of reaction of a compound containing at least two primary amino groups with an unsaturated aliphatic cyano compound and subsequent hydrogenation.
• Aliphatic, aromatic, araliphatic or cydoaliphatic di- or poly-amines can be used to prepare the polyamines that can be used in the method according to the invention.
• aromatic di- and poly-amines are understood to indude both carbocydic and heterocydic compounds.
• cydoaliphatic compounds includes both carbocydic and heterocydic ring systems.
• suitable diamines are aliphatic diamines such as, for example, 1 ,2-diamino- ethane, 1,2-diaminopropane, 1 ,3-diaminopropane, 1,4-diaminobutane and 1,6-diamino- hexane.
• suitable aliphatic di- or poly-amines are dimeric, oligomeric or polymeric ethyleneimines.
• Aromatic diamines are, for example, 1,2-diaminobenzene, 1,3-diaminobenzene, 1,4-diamino- benzene, 1 ,4-diaminonaphthalene, 1,5-diaminonaphthalene, 1,8-diaminonaphthalene, 2,5- diaminotoluene and 2,4-diaminopyridine.
• Araliphatic diamines are, for example, 4-aminobenzylamine, 4-(2-aminoethyl)-aniline and 1 ,4-bis(aminomethyl)benzene.
• Suitable cydoaliphatic diamines are, inter alia, 1 ,2-diaminocydohexane, 1 ,3-diaminocyclo- hexane, 1 ,4-diaminocydohexane and isophoronediamine.
• the primary amino groups of the diamines are reacted, in accordance with methods known per S ⁇ , with epoxides such as ethylene oxide, propylene oxide or 1 ,2-epoxybutane, with chloroalkylamines such as, for example, 1-dimethylamino-2-chloropropane or 1-dimethyl- amino-2-chloroethane, with aromatic carboxylic acid chlorides such as benzoyl chloride or 4-aminobenzoyl chloride, with aromatic sulfonic acid chlorides such as benzene sulfochloride or 4-aminobenzene sulfochloride, or with reactive aromatic sulfonyl compounds such as, for example, 4-(2-sulfatoethylsulfonyl)-aniline.
• epoxides such as ethylene oxide, propylene oxide or 1 ,2-epoxybutane
• chloroalkylamines such as, for example, 1-dimethyla
• A is a divalent aliphatic, aromatic, araliphatic or cydoaliphatic radical
• X ⁇ . X 2 , X 3 and X 4 are, each independently of the others, a linear or branched, divalent, aliphatic radical containing from 2 to 6 carbon atoms, and the radicals R 1 to Re are, each independently of the others, hydrogen, C ⁇ -C ⁇ alkyl or amino-(C 2 -Ce)alkyl, or the product of reaction of a compound of formula (1 ) or (2), wherein at least one of the radicals R 1 to Re is hydrogen, with ethylene oxide, propylene oxide, 1 ,2-epoxybutane, a chloroalkylamine or an aromatic compound having at least one -COCI, ⁇ SOaCI or -SO2-Z substituent wherein Z is vinyl, 2-chloroethyl or 2-sultatoethyl.
• Aliphatic radicals A in formulae (1) and (2) are, for example, ethylene, propylene, trimethylene, tetramethylene, hexamethylene, decamethylene or linear or branched alkylene interrupted by one or more -NH-, -N-alkyl- or -N-alkylene-Nh groups.
• Suitable aromatic radicals A in formulae (1) and (2) are, for example, 1 ,2-phenylene, 1,3- phenylene, 1,4-phenytene, naphthalene-1 ,4-diyl, naphthalene-1, 5-diyl, naphthalene-1 ,6-diyl and pyridine-2,4-diyl.
• Suitable aliphatic radicals X 1t X 2 , X 3 and X 4 in formulae (1) and (2) are, for example, ethylene, propylene, trimethylene, propane-1,1-diyl or tetramethylene.
• Ci-C ⁇ Alkyl as one of the radicals R to Re can be, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, neopentyl or n-hexyl.
• a in formula (1) or (2) is preferably an aliphatic radical.
• Preferred polyamines are compounds of formula (1) or (2) wherein A is linear or branched C 2 -C ⁇ U alkylene or linear or branched C 4 -C ⁇ oalkylene interrupted by one or more -NH-, -N-C ⁇ -C 6 alkyl- or -N-C ⁇ -C ⁇ alkylene-NH 2 - groups.
• x is a number from 1 to 20 and y is a number from 0 to 20
• Y is a linear or branched C 2 -C 6 alkylene radical and R 7 and Re are, each independently of the other, hydrogen, C 1 -C6- alkyl or amino-(C 2 -C 6 )alkyl.
• R 7 and Re in formula (3) are preferably hydrogen, methyl or ethyl.
• Z is vinyl, 2-chloroethyl or 2-sulfatoethyl, w is 0 or 1
• Rn and R 12 are, each independently of the other, hydrogen or C ⁇ -C 6 alkyl, z is 0 or 1
• Y is C 2 -C 6 alkylene, preferably ethylene, propylene, trimethylene or tetramethylene
• R 13 and R are, each independently of the other, halogen, -OR ⁇ 5 , -NH 2l -NHR15 or -NR 15 R ⁇ ⁇
• R ⁇ S and R ⁇ 6 are, each independently of the other, a linear or branched C ⁇ -Ci 2 alkyl radical which is unsubstituted or which may be substituted by one or more hydroxyl, amino, sulfo or C 6 -C 24 aryl groups.
• Espedally preferred polyamines are the compounds of formulae (100)- (109)
• the compounds of formulae (1) and (2) are known or can be prepared according to known methods, for example by reacting the diamine of formula H 2 N-A-NH 2 with the appropriate aminoalkyl chlorides of formulae CI-X ⁇ -NR 1 R 2 , CI-X ⁇ -NRaR ⁇ CI-X ⁇ -NR 5 R 6 and CI-Xt-NRyRu wherein A, X to X» and R to Re are as defined hereinbefore.
• the polyamines employed in the method according to the invention are advantageously used, irrespective of the liquor ratio, in an amount of from 0.01 to 15 % by weight, preferably from 0.1 to 10 % by weight and especially from 0.5 to 7 % by weight, based on the weight of the polyamide fibre material.
• the treatment of the polyamide fibre material with the polyamine may be carried out after, during or, preferably, before the dyeing.
• the method according to the invention is advantageously carried out by adding the polyamine to the dye liquor in the above-mentioned amount and dyeing the fibre material in the usual manner.
• the treatment of the polyamide fibre material with the polyamines is carried out before the dyeing.
• the textile material is advantageously rinsed with water at RT (room temperature) or slightly elevated temperature.
• Suitable polyamide fibre material indudes natural polyamide fibre material, e.g. wool or silk, and synthetic polyamide fibre material, e.g. polyamide-6 or polyamide-6.6, and fibre blends, e.g. wool/cellulose or polyamide/cellulose fibre blends, polyamide/wool fibre blends or polyamide/elastane fibre blends.
• the fibre material is preferably synthetic polyamide fibre material, especially microfibres.
• the textile material can be used in any form, e.g. in the form of fibres, yarn, woven fabric or knitted fabric.
• the treatment of the polyamide fibre material with the polyamines is preferably carried out in accordance with the exhaust process, in which case the liquor ratio can be seleded from within a wide range and is, for example, from 1 :4 to 1 :100, preferably from 1 :5 to 1 :40 and especially from 1 : 10 to 1 :40.
• Special apparatus is not required.
• customary dyeing apparatus e.g. open baths, winch becks, jigs, or paddle, jet or circulation apparatus, may be used.
• the procedure is advantageously carried out at a temperature of, for example, from 20 to
• the treatment time may be, for example, from 10 to 60 minutes and preferably from 15 to 40 minutes.
• the pH of the liquor is generally from 7 to 13, preferably from 8 to 12.5 and especially from 10 to 12.
• the liquor can comprise, in addition to the adjuvant according to the invention, further customary additives, such as electrolytes, e.g. sodium chloride or sodium sulfate, dispersants and wetting agents, pH-regulators and antifoams.
• electrolytes e.g. sodium chloride or sodium sulfate
• dispersants and wetting agents e.g. sodium chloride or sodium sulfate
• pH-regulators and antifoams e.g. sodium chloride or sodium sulfate
• Dyeing is carried out using, for example, anionic dyes or reactive dyes; any customary anionic dye or reactive dye, as described, for example, in Colour Index, 3rd edition (1971), is. suitable.
• anionic dyes indude sulfo-group-containing monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine and formazan dyes.
• the anionic dyes used in dyeing the polyamide fibre material are either in the form of their free sulfonic adds or, preferably, in the form of their salts.
• the dyes used in the dyeing of the polyamide fibre material may comprise further additives, e.g. sodium chloride or dextrin.
• Dyeing of the polyamide fibre material can be carried out in accordance with customary dyeing or printing methods, for example in accordance with the padding or exhaust process.
• the dye liquors or printing pastes may comprise, in addition to water and the dyes, further additives, for example wetting agents, antifoams, levelling agents or agents that influence the characteristics of the textile material, for example softeners, flame-retardants, or dirt-, water- and oil-repellents, and also water-softeners and natural or synthetic thickeners, for example alginates and cellulose ethers.
• the amounts in which dyes are used in the dye baths can vary within wide limits depending on the required depth of shade; in general, amounts of from 0.01 to 15 % by weight, especially from 0.01 to 10 % by weight, based on the material to be dyed, have proved to be advantageous.
• Dyeing with anionic dyes or reactive dyes is preferably earned out at a pH of from 1 to 8 and especially from 2 to 7.
• the liquor ratio can be selected from within a wide range, for example from 1 :3 to 1 :50, preferably from 1 :5 to 1 :30.
• Dyeing is preferably carried out at from 50 to 130 ⁇ C and especially from 80 to 120 ⁇ C.
• dyeings of dyes e.g. anionic dyes or reactive dyes
• polyamide fibre material which dyeings exhibit a substantial improvement in terms of the depth of shade, without the fastness-to-washing or fastness-to-light properties being adversely affected.
• the invention relates also to a textile adjuvant comprising an aqueous solution of a polyamine as defined hereinbefore.
• the textile adjuvants according to the invention may comprise, as further additives, for example wetting agents, dispersants or pH-regulators.
• the product is then hydrogenated at 150°C and 80 bar in ethanol, using Raney nickel and ammonia as catalyst. After filtering off the catalyst, the ethanol is drawn off using a rotary evaporator. 275 g of a brown, clear, slightly viscous liquid are obtained.
• Triton B 3 drops are introduced into a 350 ml sulfonating flask and heated to 70°C. After adding 58.5 g of 4-(2-sulfatoethylsulfonyl)-aniline, the mixture is stirred at 70°C for 2 hours. A turbid, brown solution of medium viscosity having an assay value of 50 % is obtained.
• the intermediate is then hydrogenated at 150°C and 80 bar in ethanol, using Raney nickel and ammonia as catalyst. After filtering off the catalyst, the ethanol is drawn off using a rotary evaporator.
• Example I.8. is repeated using 43 g of pentaethylenehexamine instead of polyethylene- imine.
• a solution of 43.1 g of polyethyleneimine having a molecular weight of 800 and 20 g of water is then added. After reacting at pH 9.5 for 3 hours, the solution is filtered.
• the product is then hydrogenated in ethanol at 70°C and 60 bar using Raney cobalt. After filtering off the Raney cobalt, the ethanol is drawn off using a rotary evaporator. 148 g of a dear, yellow liquid are obtained. 1 .9 g of the resulting product, 47.5 g of water, 1 drop of Triton B and ' 17.4 g of 4-(2- sulfatoethylsulfonyl)-aniline are introduced into a 350 ml sulfonating flask and heated at 70 C C. The reaction mixture is stirred at that temperature for 2 hours. 86.2 g of water are added; the product solution is cooled, filtered and collected. 167 g of a clear, red-brown liquid are obtained.
• the product is then hydrogenated in ethanol at 70°C and 60 bar using Raney cobalt. After filtering off the Raney cobalt, the ethanol is drawn off using a rotary evaporator. 323 g of a dear, yellow liquid are obtained.
• 20.6 g of the resulting product, 47.5 g of water, 1 drop of Triton B and 17.4 g of 4-(2- sulfatoethylsulfonyl)-aniline are introduced into a 350 ml sulfonating flask and heated at 70°C. The reaction mixture is stirred for 2 hours at that temperature. 100.2 g of water are added; the product solution is cooled, filtered and collected. 180 g of a dear, brown liquid are obtained.
• the fabric is rinsed with water, first at 25°C and then at 50 - 60°C, and subsequently with dilute acetic acid (pH 6.0) at 25°C.
• the pretreated fabric is immersed, at RT, in 50 g of a liquor adjusted to pH 3 using 80 % acetic acid and containing 8 % Eriofast Red 2B (Ciba Specialty Chemicals) and 1 g/litre of Tinovetin JUN (wetting agent, Ciba Specialty Chemicals).
• the liquor is then heated to 98°C at a heating rate of 2°C/minute. After 60 minutes at 98°C, the liquor is cooled to 60°C at 3°C/minute.
• the fabric is rinsed first at 50°C with water, then for 20 minutes at 70 ⁇ C with aqueous Na 2 C0 3 solution (1 g/litre), at 30-40°C with water and finally at RT with dilute acetic acid (0.5 ml of 80 % acetic acid per litre) and again with water.
• Example 11.1. is repeated using 1.50 g of the product of Preparation Example I.2.
• Example 11.1. is repeated using 1.20 g of the product of Preparation Example I.3.
• Example 11.1. is repeated using 0.62 g of the product of Preparation Example I.4.
• Example 11.1. is repeated using 0.50 g of the product of Preparation Example I.5.
• Example 11.1. is repeated using 0.30 g of the produd of Preparation Example I.6.
• Example 11.1. is repeated using 0.30 g of the product of Preparation Example 1.7.
• Example 11.1. is repeated using 0.95 g of the produd of Preparation Example I.8.
• Example 11.1. is repeated using 1.70 g of the product of Preparation Example I.9.
• Example 11.1. is repeated using 0.25 g of the product of Preparation Example 1.10.
• Example 11.1. is repeated using 0.25 g of the product of Preparation Example 1.11.

Landscapes

• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• Coloring (AREA)

Priority Applications (1)

Applications Claiming Priority (3)

Publications (1)

Family

ID=34878288

Family Applications (1)

Country Status (4)

Families Citing this family (3)

Family Cites Families (4)

• 2005
  • 2005-02-09 EP EP05707974A patent/EP1716285A1/de not_active Withdrawn
  • 2005-02-09 WO PCT/EP2005/050552 patent/WO2005080669A1/en not_active Application Discontinuation
  • 2005-02-09 CN CNA2005800050141A patent/CN1918337A/zh active Pending
  • 2005-02-09 BR BRPI0507904-7A patent/BRPI0507904A/pt not_active IP Right Cessation

Non-Patent Citations (1)

Also Published As

Similar Documents

Legal Events