US2952506A - Process for even and level dyeing of filament nylon fabrics - Google Patents
Process for even and level dyeing of filament nylon fabrics Download PDFInfo
- Publication number
- US2952506A US2952506A US605941A US60594156A US2952506A US 2952506 A US2952506 A US 2952506A US 605941 A US605941 A US 605941A US 60594156 A US60594156 A US 60594156A US 2952506 A US2952506 A US 2952506A
- Authority
- US
- United States
- Prior art keywords
- dyeing
- acid
- dyes
- nylon
- anionic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000004043 dyeing Methods 0.000 title claims description 63
- 238000000034 method Methods 0.000 title claims description 45
- 239000004744 fabric Substances 0.000 title description 67
- 229920001778 nylon Polymers 0.000 title description 43
- 239000004677 Nylon Substances 0.000 title description 39
- -1 IMIDAZOLINE COMPOUND Chemical class 0.000 claims description 41
- 239000000975 dye Substances 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 25
- 239000000980 acid dye Substances 0.000 claims description 25
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 claims description 21
- 239000000982 direct dye Substances 0.000 claims description 14
- 230000002378 acidificating effect Effects 0.000 claims description 12
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000004753 textile Substances 0.000 claims description 7
- 125000000129 anionic group Chemical group 0.000 description 33
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 125000001931 aliphatic group Chemical group 0.000 description 14
- 239000002270 dispersing agent Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 11
- 239000007859 condensation product Substances 0.000 description 11
- 239000000835 fiber Substances 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
- 239000003513 alkali Substances 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000002462 imidazolines Chemical class 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 150000002191 fatty alcohols Chemical class 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical group 0.000 description 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000009940 knitting Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 238000009987 spinning Methods 0.000 description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
- NDZFCXFEKKJINJ-UHFFFAOYSA-M [Cl-].OCC[N+]1(C(=NCC1)C=CCCCCCCCCCCCCCCC)CCO Chemical compound [Cl-].OCC[N+]1(C(=NCC1)C=CCCCCCCCCCCCCCCC)CCO NDZFCXFEKKJINJ-UHFFFAOYSA-M 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- VAPILSUCBNPFBS-UHFFFAOYSA-L disodium 2-oxido-5-[[4-[(4-sulfophenyl)diazenyl]phenyl]diazenyl]benzoate Chemical compound [Na+].[Na+].Oc1ccc(cc1C([O-])=O)N=Nc1ccc(cc1)N=Nc1ccc(cc1)S([O-])(=O)=O VAPILSUCBNPFBS-UHFFFAOYSA-L 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- CJAYHOLRQJHSIP-NXVVXOECSA-N 2-[(z)-heptadec-2-enyl]-4,5-dihydro-1h-imidazole Chemical compound CCCCCCCCCCCCCC\C=C/CC1=NCCN1 CJAYHOLRQJHSIP-NXVVXOECSA-N 0.000 description 1
- FBMWYZZRSWZLDZ-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-1-ium;hydroxide Chemical compound O.C1CN=CN1 FBMWYZZRSWZLDZ-UHFFFAOYSA-N 0.000 description 1
- AVERNFJXXRIVQN-XSDYUOFFSA-N 5-[(4-ethoxyphenyl)diazenyl]-2-[(e)-2-[4-[(4-ethoxyphenyl)diazenyl]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound C1=CC(OCC)=CC=C1N=NC(C=C1S(O)(=O)=O)=CC=C1\C=C\C1=CC=C(N=NC=2C=CC(OCC)=CC=2)C=C1S(O)(=O)=O AVERNFJXXRIVQN-XSDYUOFFSA-N 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VVAVKBBTPWYADW-UHFFFAOYSA-L Biebrich scarlet Chemical compound [Na+].[Na+].OC1=CC=C2C=CC=CC2=C1N=NC(C(=C1)S([O-])(=O)=O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 VVAVKBBTPWYADW-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UXDDRFCJKNROTO-UHFFFAOYSA-N Glycerol 1,2-diacetate Chemical compound CC(=O)OCC(CO)OC(C)=O UXDDRFCJKNROTO-UHFFFAOYSA-N 0.000 description 1
- 239000004348 Glyceryl diacetate Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
- WLDHEUZGFKACJH-UHFFFAOYSA-K amaranth Chemical compound [Na+].[Na+].[Na+].C12=CC=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=C1N=NC1=CC=C(S([O-])(=O)=O)C2=CC=CC=C12 WLDHEUZGFKACJH-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- LEYJJTBJCFGAQN-UHFFFAOYSA-N chembl1985378 Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 LEYJJTBJCFGAQN-UHFFFAOYSA-N 0.000 description 1
- ZQWICJYATMSSSD-UHFFFAOYSA-M chembl2028584 Chemical compound [Na+].C1=CC=C2C(N=NC3=C4C=CC=CC4=CC=C3O)=C(O)C=C(S([O-])(=O)=O)C2=C1 ZQWICJYATMSSSD-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000009967 direct dyeing Methods 0.000 description 1
- PHOZXQMVPWPNAP-UHFFFAOYSA-L disodium 8-[[4-[4-[(4-ethoxyphenyl)diazenyl]phenyl]phenyl]diazenyl]-7-hydroxynaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].CCOc1ccc(cc1)N=Nc1ccc(cc1)-c1ccc(cc1)N=Nc1c(O)ccc2cc(cc(c12)S([O-])(=O)=O)S([O-])(=O)=O PHOZXQMVPWPNAP-UHFFFAOYSA-L 0.000 description 1
- FBNCDTLHQPLASV-UHFFFAOYSA-L disodium;5-methyl-2-[[5-(4-methyl-2-sulfonatoanilino)-9,10-dioxoanthracen-1-yl]amino]benzenesulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1NC1=CC=CC2=C1C(=O)C1=CC=CC(NC=3C(=CC(C)=CC=3)S([O-])(=O)=O)=C1C2=O FBNCDTLHQPLASV-UHFFFAOYSA-L 0.000 description 1
- 235000019443 glyceryl diacetate Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- KQSBZNJFKWOQQK-UHFFFAOYSA-N hystazarin Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2 KQSBZNJFKWOQQK-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- AMMWFYKTZVIRFN-UHFFFAOYSA-N sodium 3-hydroxy-4-[(1-hydroxynaphthalen-2-yl)diazenyl]-7-nitronaphthalene-1-sulfonic acid Chemical compound [Na+].C1=CC=CC2=C(O)C(N=NC3=C4C=CC(=CC4=C(C=C3O)S(O)(=O)=O)[N+]([O-])=O)=CC=C21 AMMWFYKTZVIRFN-UHFFFAOYSA-N 0.000 description 1
- CQNXJSVLKPHNRI-OXEZCZPGSA-N sodium 5-[(4-hydroxyphenyl)diazenyl]-2-[(E)-2-[4-[(4-hydroxyphenyl)diazenyl]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound C1=CC(=CC=C1N=NC2=CC(=C(C=C2)/C=C/C3=C(C=C(C=C3)N=NC4=CC=C(C=C4)O)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] CQNXJSVLKPHNRI-OXEZCZPGSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- PEAGNRWWSMMRPZ-UHFFFAOYSA-L woodstain scarlet Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 PEAGNRWWSMMRPZ-UHFFFAOYSA-L 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- 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
- D06P1/64—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
- D06P1/6426—Heterocyclic compounds
-
- 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
-
- 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
- Y10S8/90—Basic emulsifiers for dyeing
-
- 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
- Y10S8/907—Nonionic emulsifiers for dyeing
-
- 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
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/924—Polyamide fiber
Definitions
- This invention relates to the even dyeing of textile fabrics, and more particularly to the even and level dyeing of fabrics composed of filaments of a polycarbonamide, more familiarly known as nylon.
- the primary object of the present invention is to provide a new and improved process for dyeing polycarbonamide textile articles.
- a further object is to provide a process for dyeing nylon yarns evenly and levelly by means of anionic dyestufis Without the resulting streaks and shade depth variation that have previously characterized the use of the anionic dyestuffs for the dyeing of nylon fabrics.
- Other objects will appear from the description hereinafter.
- the objects of this invention are accomplished by the process of dyeing polycarbonamide textile articles which comprises dyeing the articles in an aqueous dyeba-th containing an anionic dyestufi selected from the group consisting of direct dyes, acid dyes, acid metallized dyes, and mordant acid dyes and a substituted imidazoline compound selected from the group consisting of (l) a salt of an imidazoline having the general.
- an anionic dyestufi selected from the group consisting of direct dyes, acid dyes, acid metallized dyes, and mordant acid dyes
- a substituted imidazoline compound selected from the group consisting of (l) a salt of an imidazoline having the general.
- R is selected from the group consisting of alkyl, phenyl, hydroxyalkyl, and carboxyalkyl radicals and R is an open aliphatic chain consisting of from ten to 18 carbon atoms, such as I-butyl-2-hexadecyl-irnidazoline, 1- benzyl-Z-hexadecyl imidazoline, 1-(2-hydroxyethy1)-2- heptadecyl-imidazoline, I-(Z-hydroxyethyl) 2 heptadecenyl-imidazoline, and l-(2-hydroxyethyl)-2-undecylimidazoline, (2) a quaternary imidazolinium compound having the general formula wherein R and R are selected from the group consisting of alkyl, phenyl, hydroxyalkyl and carboxyalkyl radicals, R is an open aliphatic chain consisting of from ten to 18 carbon atoms and X
- the amount of the substituted imidazoline compounds which can be used in the process of the present invention can vary between one and ten times the weight of the dyestuffs employed. Many of the anionic dyestuffs suitable for use in the process may be used to dye nylon fabrics evenly and levelly when employing as little as one to two times the weight of the dyestufi of the substituted imidazoline compounds. However, with others of the anionic dyestuffs, although these amounts of the substituted imidazoline compounds give even dyeings from fiber to fiber they may result in unlevel dyeings, i.e. unequal penetration as between the fibers.
- the synthetic linear polycarbonamides are of the general type described in U.S. Patents 2,071,250; 2,071,253 and 2,130,948.
- the contemplated polycarbonamides comprise the reaction products of linear polymer-forming compositions containing amideforming groups, for example reaction materials consisting of bifunctional molecules containing two reactive groups which are complementary to reactive groups in other molecules and which include the. complementary amideforming groups. These polycarbonamides are of two distinct types.
- polycarbonamides contain recurring amide r ps:
- R is a member of the group of hydrogen and monovalent hydrocarbon radicals, as a part of main chain of atoms of the polymer.
- Particularly useful polycarbonamides in the present invention are the simple unsubstituted polycarbonamides, such as those formed by the reaction of tetramethylene diamine with adipic acid, tetramethylene diamine with suberic acid, tetrarnethylene diamine with sebacic acid, hexamethylene diamine with adipic acid, hexamethylene diamine with suberic acid, hexamethylene diamine with sebacic acid, or the polymerization product of epsilon-caprolactam.
- polymers formed from the reaction of two ormore di-. amines with dicarboxylic acids and/or two or more di carboxylic acids with diamines are contemplated in the practice of the-instant invention.
- anionic dyestufis function with the process. of this invention.
- the two most common classes of anionic dyestuffs and two which give excellent light and wash fastness when used on nylons are the acid and direct dyes, but other classes of anionic dyestuffs may be employed in this process as well, such as acid metallized and mordant acid or chrome dyes.
- anionic dyestuffs may be employed in this process as well, such as acid metallized and mordant acid or chrome dyes.
- Examples of certain of the direct dyestuffs which have been successfully employed to dye nylon fabricslevelly and uniformly by the process of this invention include Paper Yellow 3GXA (CI 364), Chrysophenine (CI 365), Chlorantine Fast Yellow SGLL (CI 346), Calcodur Orange GL (CL 653), Calcodur Red SBL (CL 278), Triazol Fast Scarlet B (CI 382). Congo Red (CI 370), Diarnine Fast Red FA- CF (CI 419), and Diphenyl Violet EV Supra (CI 394).
- Examples of acid dyestufis which may be employed include Pontacyl Dark Green (CI 247), Amacid Red 3B (CI 280), Benzyl Red G (CI 275), Brilliant Croceine Scarlet MOO (CI, 252), Anthraquinone Violet 3RAv (CI 1080) and Alizarin Fast Light Blue C (CI 108-8).
- Examples of mordant acid or chrome dyestuifs which may be used include Omega Chrome Orange G (CI 274), Eriochrome Blue Black R (CI 202), Calcochrome Black T (CI 203), Chrome Yellow A (CI 219), and Calcochrome Alizarine Gray 2BLS (Pr. 206).
- Acid metallized dyestufls which may be employed include Neolan Blue 2G (Pr. 144), Neolan Navy Blue RLG (Pr. 561), and Chromacyl Black W (Pr. 143). Not all dyestuffs of each class of anionic dyes enumerated will dye nylon yarns or fabrics equally as well, as is well known. However, the best dyes from among each class can easily be selected, and a large number of the dyestuffs in each named class can be effectively utilized to dye nylon materials evenly and levelly. by the process of this invention,
- the conditions of dyeing employed in theprocess of the present invention are substantially those of the normal dyeing procedure with the particular classes of. anionic dyes employed. That is, with all of the named classes of anionic dyestuffs dyeing is usually carried out at a temperature of from about 200 to about 210 F. and at a pH of from about 2 to about 5.5. The preferred pH with the acid and direct dyestufi's is from about 3 to about 5.
- the length of time of the dyeing to result in even and, level dyeings of nylon is generally from about 1 to about 4 hours.
- the mechanics of carrying out the dyeing are not. critical and may be varied to suit the normal dyeing practice. That is, the fabric may be entered into the bath cold and the bathslowly raised to dyeing temperature after all the ingredients have been added, or the fabric may be added to the bath first and the dyestufi and substituted imidazoline compound added afterwards.
- the order of addition of components to the dyebath, is a matter of choice.
- non-ionic dispersing agents as those containing the condensation products. of polyglycols with higher fatty acids, higher fatty alcohols, amides of higher fatty acids, or long chain alkyl substituted phenols can be added to the dyebath of the present invention to assist in obtaining more level dyeings on certain nylon constructions.
- the non-ionic dispersingagents may be used in concentrations of from about 0.1% to about, 4%.
- non-ionic dispersing agents not only improves the levelness of penetration of the dyes from fiber to fiber but also insures that those fibers on the interior of the skein are evenly dyed with those on the exterior. Consequently, when dyeing certain closely woven fabrics such as taffetas it is preferred to include a non-ionic dispersing agent of the above-described type. in the dyebath.
- imidazoline compounds for example, 1,1 di (2-hydroxyethyl) -2-heptadecenyl imidazolinium chloride, in the same general amounts that are used to evenly dye such fabrics by the process of this invention.
- the bath may be maintained at an acidic pH at or near the boil until the dyeing has become even and level.
- such treating baths contain a non-ionic dispersing agent
- the presence of such an agent for example the condensation product of one mole of stearyl alcohol with 20 moles of ethylene oxide is preferred, since less of the substituted irnidazoline compound is required when a non-ionic dispersant is also present.
- a dyebath was prepared containing 0.25% Pontacyl Dark Green G (CI 247), 1.4% of 1,1-di-(2-hydroxyethyl)-2-heptadecenyl-imidazolinium chloride, and 5% glacial acetic acid in 40 volumes of water, all percentages being based on Weight of the fabric to be dyed.
- a specially knit nylon tricot was employed in the dyeing. This nylon tricot fabric was made up of seven different samples of nylon yarn, spun and drawn under different conditions so as to display different dyeing rates.
- the fabric was knit on a 14 gauge machine with 20 ends of each yarn sample knit side by side in the following order: (1) a sample of normal commercial 70 denier, 34 filament nylon yarn, (2) a sample of the same yarn count spun on a pilot plant spinning machine in the normal manner, (3) a sample of the same yarn drawn at a 3.2% higher than normal draw ratio, (4-) a sample of the same yarn drawn at a 2.6% lower than normal draw ratio, (5) a sample of the yarn spun from the same batch employing a higher than normal air flow in the spinning machine, (6) a sample of yarn spun from the same batch employing C. lower than normal temperature of the melt entering the spinneret, and (7) a sample of the same commercial 70 denier normally spun nylon yarn as in 1) above.
- the specially knit tricot fabric employed was knit from yarns having sufficient differences in the spinning and drawing thereof to demonstrate pronounced dilferences in shade upon dyeing with an acid or direct dyestuff.
- One part of the specially knit tricot fabric was entered into the bath and the temperature of the bath slowly raised to 200 F. The bath was held at this temperature for 3 hours.
- the shade depth variations between the seven different yarns making up the tricot fabric were hardly noticeable to the eye.
- the gray scale ratings of the differences at each knitting junction of the specially knit tricot fabric are based upon the International Geometric Grey Scale of the Society of Dyers and Colorists, wherein a rating of 5 represents negligible shade variation from the next proceedinging sample or section thereof, a rating of 4 represents noticeable variation, a rating of 3 represents appreciable variation, 2. rating of 2 represents considerable variation, a rating of 1 represents much variation and a plus or minus indicates slightly more or less than the given rating.
- the grey scale ratings of the fabric dyed in the above manner are set out in Table I below.
- Pontacyl Dark Green G (CI 247 and 5% of ammonium slowly to 200 acetate in 40 volumes of water, the percentages being based on the weight of the fabric dyed, in the same manner as above.
- the shade depth variations between the seven different yarns composing the specially knit tricot fabric were quite noticeable as between the yarns.
- the grey scale ratings of the difference at each knitting junc- A dyebath was prepared containing the following ingredients: 0.25% Pontacyl Dark Green G (CI 247), 0.5% of l,l-(2-hydroxyethyl)-2-heptadecenyl-imidazolinium chloride, and 16% glyceryl diacetate in 40 volumes of water, all percentages being based on the weight of the fabric to be dyed.
- Example I One part of the same specially knit nylon tricot fabric as employed in Example I was entered into the dyebath. The temperature of the bath was raised to 200 F. and held at this temperature for minutes. The sample of the specially knit tricot fabric was levelly and evenly dyed and the shade depth variations were hardly noticeable to the eye.
- a dyebath was prepared containing the following ingredients: 0.5% of Pontacyl Dark Green G (CI 247 2.5% of l,l-(Z-hydroxyethyl)2-heptadecenylirnidazolinium chloride, 5% glacial acetic acid and 40 volumes of water, all percentages being based on the Weight of the fabric to be dyed.
- 0.5% of Pontacyl Dark Green G CI 247 2.5% of l,l-(Z-hydroxyethyl)2-heptadecenylirnidazolinium chloride
- 5% glacial acetic acid 5%
- EXAMPLE IV A dyebath containing the following ingredients was prepared: 0.5 of Diphenyl Brilliant Violet DB (Pr. 35), 1.0% of l-(2-hydroxyethyl)-2-undecylimidazolinium acetate, and 2% glacial acetic acid based on the weight of the fabric to be dyed.
- 0.5 of Diphenyl Brilliant Violet DB (Pr. 35) 1.0% of l-(2-hydroxyethyl)-2-undecylimidazolinium acetate, and 2% glacial acetic acid based on the weight of the fabric to be dyed.
- One part of nylon taffeta fabric was entered into the dyebath. The temperature of the bath was slowly raised to 200 F. and maintained at this temperature for two hours. The warp streaks present in the fabric were hardly noticeable.
- the levelness of dying was improved by repeating the above dyeing with the exception of substituting formic for acetic acid for pH adjustment and adding 0.25% of the condensation product of 1 mole of stearyl alcohol and 20 moles of ethylene oxide.
- a dyebath was prepared containing the following ingredients: 0.25% of Chromacyl Black W (Pr. 143), 1.0% of condensation product of 1 mole of oleyl alcohol condensed with 15 to 20 moles of ethylene oxide, 2.0% of glacial acetic acid, and 2.0% of 1,l-di-(2-hydroxyethyl)'- Z-heptadecenylimidazolinium chloride in 40 volumes of water based upon the Weight of the fabric to be dyed.
- One part of the specially knit nylon tricot fabric containing seven different yarns spun under different conditions was entered into the dyebath. The dyebath was raised F. and maintained at that temperature for 2 hours. Differences in shade between knit junctions of the specially knit fabric were hardly noticeable.
- a dyebath was prepared containing the following ingredients: 0.25% Pontacyl Dark Green G (CI 247), 2.0% of formic acid, 2.0% of the condensation product of stearyl alcohol condensed with 20 moles of ethylene oxide, and 2.0% of 1,1-di-(2-hydroxyethyl)-2-heptadecylimidazolinium hydroxide in 40 volumes of water, all percentages being based on the weight of the fabric to be dyed.
- One part of the specially knit nylon tricot fabric knit from seven yarns of diiferent dyeing characteristics was entered into the dyebath. The temperature of the dyebath was slowly raised to 200 F. and maintained at that temperature for 2 /2 hours. The shade variations at the knitting junctions were hardly noticeable to the eye after the dyeing procedure outlined above.
- EXAMPLE v11 A dyebath was prepared containing the following ingradients: 1.0% Omega Chrome Orange G (CI 247), 2.0% of formic acid, 1.0 percent of 1,1-di-(2-hydroxyethyl)-2-heptadecenyl-imidazolinium chloride, and 2.0% of the condensation product of 1 mole of stearyl alcohol condensed with 20 moles of ethylene oxide in 40 volumes of water, all percentages being based on the weight of the fabric to be dyed.
- One part of a nylon taffeta fabric Was entered into the dyebath and the dyebath temperature slowly raised to 200 F. This temperature was maintained for 1 hour and the fabric then Washed and dried. The warp streaks normally occurring in nylon taffeta when dyed with chrome dyestuffs were not noticeable to the eye, and the tatfeta was evenly and levelly dyed with good penetration.
- the amount of the various anionic dyestuffs applied to the nylon fabrics by the methods of this invention are substantially those same quantities which may be applied by conventional methods. That is, the employment of the substituted imidazoline compound in the dyebath does not act to increase the susceptibility of the nylon fibers or fabrics to dyeing by these dyes, but on the contrary provides a method for applying the same dyes more uniformly and levelly than can be accomplished by the normal methods.
- R is selected from the group consisting of alkyl
- R and R are selected from the group consisting of alkyl, phenyl, hydroxyalkyl and carboxyalkyl radicals, R is an open aliphatic chain consisting of from 10 to 18 carbon atoms and X is a halogen and (3) a quaternary imidazolinium compound having the general formula wherein R and R are selected from the group consisting of hydroxyalkyl, alkali metal substituted-hydroxyalkyl and alkali metal-substituted carboxyalkyl radicals, and R is an open aliphatic chain consisting of from 10 to 18 carbon atoms.
- a process as defined in claim dyestufi is an acid metallized dye.
- a process for evenly dyeing filament polycarbonamide fabrics which comprises dyeing the fabrics in an aqueous acidic dyebath containing an anionic dyestuff selected from the group consisting of direct dyes, acid dyes, acid metallized dyes, and mordant acid dyes and from one to ten times the weight of the dyestuif of a salt of an imidazoline having the general formula 1 wherein the anionic wherein R is selected from the group consisting of alkyl, phenyl, hydroxyalkyl, and carboxyalkyl radicals, and R is an open aliphatic chain consisting of from 10 to 18 carbon atoms.
- a process for evenly dyeing filament polycarbonamide fabrics which comprises dyeing the fabrics in an aqueous acidic dyebath containing an anionic dyestulf selected from the group consisting of direct dyes, acid dyes, acid metallized dyes, and mordant acid dyes and from one to ten times the weight of the dyestuif of a quaternary imidazolinium compound having the general formula wherein R and R are selected from the group consisting of alkyl, phenyl, hydroxyalkyl, and carboxyalkyl radicals, R is an open aliphatic chain consisting of from ten to 18 carbon atoms, and X is a halogen.
- a process as described in claim 9 wherein the quaternary imidazolinium compound is 1,l-di-(2-hydroxyethyl) -2-heptadecenyl-imidazolinium chloride.
- a process as defined in claim 9 wherein the quaternary imidazolinium compound is 1,1-di-(2-hydroxy ethyl)-2-undecyl-imidazolinium chloride.
- a process for evenly dyeing filament polycarbonamide fabrics which comprises dyeing the fabrics in an aqueous acidic dyebath containing an anionic dyestuif selected from the group consisting of direct dyes, acid dyes, acid metallized dyes, and mordant acid dyes and from one to ten times the weight of the dyestulf of a quaternary imidazolinium compound having the general formula wherein R and R are selected from the group consisting of hydroxyalkyl, alkali metal-substituted hydroxyalkyl and alkali metal-substituted carboxyalkyl radicals and R is an open aliphatic chain consisting of from 10 to 18 carbon atoms.
- a process as described in claim 13 wherein the quaternary imidazolinium compound is 1,1-di-(2-hydroxy ethyl)-2-heptadecyl-imidazolinium hydroxide.
- quaternary imidazolinium compound is the disodium salt of 1-(2-hydroxyethyl)-1-carboxyethyl undecyl-imida zd linium hydroxide.
- a process for evenly dyeing polycarbonamide textile articles which comprises dyeing the article in an aqueous acidic dyebath containing an anionic dyestuif selected from the group consisting of direct dyes, acid dyes, acid metallized dyes, and mordant acid dyes, from 0.1 percent to 4.0 percent of a non-ionic dispersing agent selected from the group consisting of the condensation products of polyglycols with higher fatty acids, the condensation products of polyglycols with higher fatty alcohols, and long chain alkyl-substituted phenols, and from one to ten times the weight of the dyestuff of a substituted imidazoline compound selected from the group consistring of (l) a salt of an imidazoline having the general formula wherein R is selected from the group consisting of alkyl, phenyl, hydroxyalkyl, and carboxyalkyl radicals and R is an open aliphatic chain consisting of from 10 to 18 carbon atoms, (2) a quaternary imid
- R and R are selected from the group consisting of hydroxyalkyl, alkali metal substituted-hydroxyalkyl and alkali metal-substituted carboxyalkyl radicals, and R is an open aliphatic chain consisting of from 10 to 18 carbon atoms.
- a process for evenly dyeing filament polycarbonamide fabrics which comprises dyeing the fabrics in an aqueous acidic dyebath containing an anionic dyestuif selected from the group consisting of direct dyes, acid dyes, acid metallized dyes, and mordant acid dyes, from 0.1 percent to 4.0 percent of a non-ionic dispersing agent which is a condensation product of ethylene oxide with a higher fatty alcohol, and from one to ten times the weight of the dyestutf of a salt of an imidazoline having the general formula wherein R is selected from the group consisting of alkyl, phenyl, hydroxyalkyl, and carboxyalkyl radicals, and R is an open aliphatic chain consisting of from 10 to 18 carbon atoms.
- a process for evenly dyeing filament polycarbonamide fabrics which comprises dyeing the fabrics in an aqueous acidic dyebath containing an anionic dyestuif selected from the group consisting of direct dyes, acid dyes, acid metallized dyes, and mordant acid dyes, from 0.1 percent to 4.0 percent of a non-ionic dispersing agent which is a condensation product of ethylene oxide with a higher fatty alcohol, and'from one to ten times the weight of the dyestuif of a quaternary imidazolinium compound having the general formula wherein R and R are selected from ing of alkyl, phenyl, hydroxyalkyl, and carboxyalkyl radicals, R is an open aliphatic chain consisting of from ten to 18 carbon atoms, and X is a halogen.
- a process for evenly dyeing filament polycarbonamide fabrics which comprises dyeing the fabrics in an aqueous acidic dyebath containing an anionic dyestuif selected from the group consisting of direct dyes, acid dyes, acid metallized dyes, and mordant acid dyes, from 0.1 percent to 4.0 percent of a non-ionic dispersing agent which is a condensation product of ethylene oxide with a higher fatty alcohol, and from one to ten times the weight of the dyestuif of a quaternary imidazolinium compound having the general formula the group consistwherein R and R are selected from the group consisting of hydroxyalkyl, alkali metal-substituted hydroxyalkyl and alkali metal-substituted carboxyalkyl radicals and R is an open aliphatic chain consisting of from 10 to 18 carbon atoms.
- an anionic dyestuif selected from the group consisting of direct dyes, acid dyes, acid metallized dyes, and mordant acid dyes
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
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Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE560259D BE560259A (OSRAM) | 1956-08-24 | ||
| US605941A US2952506A (en) | 1956-08-24 | 1956-08-24 | Process for even and level dyeing of filament nylon fabrics |
| GB31937/56A GB806026A (en) | 1956-08-24 | 1956-10-19 | Process for even and level dyeing of nylon textiles |
| DEC14072A DE1153341B (de) | 1956-08-24 | 1956-12-06 | Verfahren zum gleichmaessigen Faerben von Polyamid-Textilien |
| ES0234195A ES234195A1 (es) | 1956-08-24 | 1957-03-12 | PROCEDIMIENTO PARA TENIR DE MODO UNIFORME ARTiCULOS TEXTILES DE POLICARBONAMIDA |
| FR1181678D FR1181678A (fr) | 1956-08-24 | 1957-08-24 | Procédé pour la teinture égale de fibres textiles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US605941A US2952506A (en) | 1956-08-24 | 1956-08-24 | Process for even and level dyeing of filament nylon fabrics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2952506A true US2952506A (en) | 1960-09-13 |
Family
ID=24425844
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US605941A Expired - Lifetime US2952506A (en) | 1956-08-24 | 1956-08-24 | Process for even and level dyeing of filament nylon fabrics |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2952506A (OSRAM) |
| BE (1) | BE560259A (OSRAM) |
| DE (1) | DE1153341B (OSRAM) |
| ES (1) | ES234195A1 (OSRAM) |
| FR (1) | FR1181678A (OSRAM) |
| GB (1) | GB806026A (OSRAM) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3097043A (en) * | 1963-07-09 | New dyeing process | ||
| US3105732A (en) * | 1961-01-10 | 1963-10-01 | Burlington Industries Inc | Process for dyeing blends of nylon 6 and nylon 66 |
| US3129198A (en) * | 1960-02-08 | 1964-04-14 | Sherwin Williams Co | Quaternary monoimidazoline salts as thermosetting catalysts for resinous blends comprising polyepoxide polymers and acrylic polymers having a plurality of carboxyl groups therein |
| US3179483A (en) * | 1962-02-14 | 1965-04-20 | American Cyanamid Co | Mixtures of cationic and non-ionic surfactants, chlorinated triphenylmethanes and tanning agents and union dyeing therewith |
| US3232695A (en) * | 1966-02-01 | Process for dyetng materials based on polyamedes and composithons therefor | ||
| US3281201A (en) * | 1962-06-22 | 1966-10-25 | Gen Aniline & Film Corp | Process for dyeing of nylon fibers with premetallized and acid dyestuffs |
| US3661504A (en) * | 1966-12-29 | 1972-05-09 | Celanese Corp | Basic dyeable polymer of polyethylene terephthalate shaped article containing 0.5 percent of a sulfonated pyrrole |
| US4322512A (en) * | 1980-07-23 | 1982-03-30 | Armstrong World Industries, Inc. | Process for treating polyamide textile materials with trimellitic anhydride compound |
| US4343923A (en) * | 1980-08-07 | 1982-08-10 | Armstrong World Industries, Inc. | Process for reducing the acid dye uptake of polyamide textile materials with N-acylimidazole compound |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2043164A (en) * | 1936-06-02 | Basic imedazole compounds which are | ||
| US2083182A (en) * | 1934-07-16 | 1937-06-08 | Chem Ind Basel | Composition of matter for dyeing animal fibers |
| US2268273A (en) * | 1939-05-27 | 1941-12-30 | Carbide & Carbon Chem Corp | Textile finishing |
| US2371536A (en) * | 1945-03-13 | Treatment of nylon for modifying | ||
| US2713583A (en) * | 1952-04-10 | 1955-07-19 | Petrolite Corp | Derivatives of imidazolines and pyrimidines |
| US2723178A (en) * | 1951-02-10 | 1955-11-08 | American Cyanamid Co | Method of controlling the migration of metallized dyes between dye bath and fabric |
-
0
- BE BE560259D patent/BE560259A/xx unknown
-
1956
- 1956-08-24 US US605941A patent/US2952506A/en not_active Expired - Lifetime
- 1956-10-19 GB GB31937/56A patent/GB806026A/en not_active Expired
- 1956-12-06 DE DEC14072A patent/DE1153341B/de active Pending
-
1957
- 1957-03-12 ES ES0234195A patent/ES234195A1/es not_active Expired
- 1957-08-24 FR FR1181678D patent/FR1181678A/fr not_active Expired
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2043164A (en) * | 1936-06-02 | Basic imedazole compounds which are | ||
| US2371536A (en) * | 1945-03-13 | Treatment of nylon for modifying | ||
| US2083182A (en) * | 1934-07-16 | 1937-06-08 | Chem Ind Basel | Composition of matter for dyeing animal fibers |
| US2268273A (en) * | 1939-05-27 | 1941-12-30 | Carbide & Carbon Chem Corp | Textile finishing |
| US2723178A (en) * | 1951-02-10 | 1955-11-08 | American Cyanamid Co | Method of controlling the migration of metallized dyes between dye bath and fabric |
| US2713583A (en) * | 1952-04-10 | 1955-07-19 | Petrolite Corp | Derivatives of imidazolines and pyrimidines |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3097043A (en) * | 1963-07-09 | New dyeing process | ||
| US3232695A (en) * | 1966-02-01 | Process for dyetng materials based on polyamedes and composithons therefor | ||
| US3129198A (en) * | 1960-02-08 | 1964-04-14 | Sherwin Williams Co | Quaternary monoimidazoline salts as thermosetting catalysts for resinous blends comprising polyepoxide polymers and acrylic polymers having a plurality of carboxyl groups therein |
| US3105732A (en) * | 1961-01-10 | 1963-10-01 | Burlington Industries Inc | Process for dyeing blends of nylon 6 and nylon 66 |
| US3179483A (en) * | 1962-02-14 | 1965-04-20 | American Cyanamid Co | Mixtures of cationic and non-ionic surfactants, chlorinated triphenylmethanes and tanning agents and union dyeing therewith |
| US3281201A (en) * | 1962-06-22 | 1966-10-25 | Gen Aniline & Film Corp | Process for dyeing of nylon fibers with premetallized and acid dyestuffs |
| US3661504A (en) * | 1966-12-29 | 1972-05-09 | Celanese Corp | Basic dyeable polymer of polyethylene terephthalate shaped article containing 0.5 percent of a sulfonated pyrrole |
| US4322512A (en) * | 1980-07-23 | 1982-03-30 | Armstrong World Industries, Inc. | Process for treating polyamide textile materials with trimellitic anhydride compound |
| US4343923A (en) * | 1980-08-07 | 1982-08-10 | Armstrong World Industries, Inc. | Process for reducing the acid dye uptake of polyamide textile materials with N-acylimidazole compound |
Also Published As
| Publication number | Publication date |
|---|---|
| BE560259A (OSRAM) | |
| GB806026A (en) | 1958-12-17 |
| ES234195A1 (es) | 1957-08-16 |
| DE1153341B (de) | 1963-08-29 |
| FR1181678A (fr) | 1959-06-17 |
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