US3278253A - Process for dyeing textile materials in an aqueous bath containing a dyestuff in the presence of a trifunctional triazine - Google Patents
Process for dyeing textile materials in an aqueous bath containing a dyestuff in the presence of a trifunctional triazine Download PDFInfo
- Publication number
- US3278253A US3278253A US303425A US30342563A US3278253A US 3278253 A US3278253 A US 3278253A US 303425 A US303425 A US 303425A US 30342563 A US30342563 A US 30342563A US 3278253 A US3278253 A US 3278253A
- Authority
- US
- United States
- Prior art keywords
- dyeing
- dyestuff
- parts
- acid
- active
- 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 58
- 239000000975 dye Substances 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 18
- 239000000463 material Substances 0.000 title claims description 16
- 239000004753 textile Substances 0.000 title claims description 13
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 34
- 239000004952 Polyamide Substances 0.000 claims description 20
- 229920002647 polyamide Polymers 0.000 claims description 20
- 239000002253 acid Substances 0.000 description 23
- 239000000047 product Substances 0.000 description 20
- 239000004744 fabric Substances 0.000 description 15
- 239000000835 fiber Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 12
- -1 alkali metal cation Chemical class 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 7
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 7
- 239000007859 condensation product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 210000002268 wool Anatomy 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 150000003973 alkyl amines Chemical class 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229920001567 vinyl ester resin Polymers 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 2
- 240000008886 Ceratonia siliqua Species 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 229920001281 polyalkylene Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000000979 retarding effect Effects 0.000 description 2
- 238000009999 singeing Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- QQNXPCCFPQRLMK-UHFFFAOYSA-N S(O)(O)(=O)=O.OCCS(=O)(=O)CCO Chemical class S(O)(O)(=O)=O.OCCS(=O)(=O)CCO QQNXPCCFPQRLMK-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 238000006359 acetalization reaction Methods 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000003416 augmentation Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical group C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 1
- 235000019233 fast yellow AB Nutrition 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 229940116317 potato starch Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 239000008096 xylene 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
- D06P1/64—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
- D06P1/647—Nitrogen-containing carboxylic acids or their salts
-
- 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
- D06P1/628—Compounds containing nitrogen
-
- 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
- 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
- D06P3/246—Polyamides; Polyurethanes using polymeric dyes
-
- 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 improvements in the dyeing of textile materials such as yarns, filaments, fibers and fabrics having a basis of synthetic linear polyamides, as, for example, nylon. More particularly, the present invention relates to an improved process for dyeing yarns, filaments, fibers and fabrics made of, or essentially consisting of, synthetic linear polyamides with acid dyestuffs, complex metal dyestuffs or reactive dyestuffs or mixtures thereof.
- textile materials made from polyamides can be dyed with various dyestuffs, for example, with acid wool dyestuffs, metal complex dyestuffs or chrome dyestuffs, at temperatures below and above 100 C.
- various dyestuffs for example, with acid wool dyestuffs, metal complex dyestuffs or chrome dyestuffs, at temperatures below and above 100 C.
- the dyeings thus produced are not satisfactory, because in most cases it is not possible to level irregularities of the yarn which are mainly caused by variations of the titer and differences in stretching and fixing. These yarn irregularities are distinctly visible after dyeing as streaks, bands or in the form of an unsettled appearance, depending on the type of goods, and they considerably reduce the sales value of the goods.
- these products are capable of levelling out the streakiness occurring with polyamide fibers when dyeing with acid dyestuffs; in the case of difficult dyeings with acid dyestuff combinations, they exhibit retarding effects which are different for each component of the dyestuff combination, so that dyestuff losses and alterations of shade are caused.
- the full effect of the mixtures is attained at temperatures above C., so that anti-oxidizers must be used to prevent possible oxidations taking place at these high temperatures.
- fabric irregularities cannot be levelled out satisfactorily and a strong retardative effect is observed with some dyestuffs.
- a drawback is also the necessity of exactly adjusting the pH-value of the dyebath for obtaining optimum effects.
- Another object of this invention is the provision of an aqueous dyebath comprising an acid dyestuff, a complex metal dyestuff, a reactive dyestuff or a mixture thereof and a particularly effective dyeing assistant.
- Formula I R represents hydrogen or a low molecular alkyl radical
- A represents an aliphatic, aromatic, araliphatic, or cycloaliphatic radicals
- n an integer from 1 to 3
- X represents halogen, preferably chlorine or the group wherein R, A, Z and n have the meanings given above.
- R, A, Z and n have the meanings given above.
- compounds of the Formula I there are preferably used compounds in which R represents a hydrogen atom,
- A represents an alkylene radical having 1-4 carbon atoms
- the compounds of the present invention permit dyeing at temperatures of up to 130 C. without the addition of protective agents and without incurring the risk of damaging the fibres. By application of this high temperature, in many cases the yield and the levelness are rather improved.
- Another advantage in the use of the assistants of the present invention is that dull shades on polyamide textiles are obtained, since in practice the luster of the dyed goods has always been objected to.
- the assistants having the Formula I can be prepared, for example, by reacting amines of the formula NH'A' '(Z)n with cyanuric chloride preferably in an aqueous medium, at a reaction temperature ranging from to 100 C., while neutralizing the hydrogen chloride liberated.
- neutralizing agents there may be preferably used mineral acid-binding agents, for example, alkali metal hydroxides, carbonates or hydrogen carbonates, and alkaline earth metal hydroxides, carbonates or hydrogen carbonates.
- the 2,4,6 s triazine tri aminobenzene fi hydroxyethylsulfone sulfuric acid esters can also be prepared by reacting cyanuric chloride with aminobenzenefl-hydroxyethylsulfone in the melt or in a higher-boiling organic solvent, for example, xylene and subsequent esterification of the trihydroxy compound formed with concentrated sulfuric acid.
- the addition products of alkylene oxide to alkylamines or polyalkylene polyamines prefearably the compounds obtained by the addition of 2-30 mols of ethylene oxide to 1 mol of an alkylamine having at least one alkyl radical with 8-18 carbon atoms or of a substituted alkylamine, for example, a compound of the formula in which R stands for alkyl radical having 8-18 carbon atoms, or 1 mol of a polyalkylene polyamine such as ethylene diamine, diethylene triamine or hexamethylene diamine; condensation products of melamine, formaldehyde and one compound obtained by the addition of prefer-ably 8-80 mols of ethylene oxide to 1 mol of triethanolamine, or the products obtained by acid condensation of formaldehyde and addition products of alkylene oxide, preferably of 8-50 mols of ethylene oxide
- the ratio of the anion-active to the cation-active compound used if desired or required can vary within wide limits.
- the anionactive compounds encompassed by the Formula I may be used with good results alone.
- the ratio of the individual components may be adjusted to the prevailing circumstances of each individual case.
- the components can be used in equal amounts, but it generally proved advantageous to use an excess of anionactive compound. It is preferred to use a ratio of 3 parts by weight of anion-active compound to 1 part by weight of cation-active compound.
- a non-ionic surface-active compound for example, the product obtained by the addition of 20-40 mols of ethylene oxide to 1 mol of an alkyl phenol having an alkyl radical with about 8-12 carbon atoms.
- the dyeing conditions such as the dyebath temperature, the pH of the dyebath, the proportion of dyestuff in the dyebath and the liquor ratio, may be varied as desired.
- the dyebath is preferably heated to a temperature of at least to C.; mostly, the dyeing is carried out at the normal boiling point of the dyebath. Augmentation of the dyeing temperature to about l20130 C. is possible, but is in most cases not necessary to obtain streakless dyeings with good depth of shade.
- the dyebath should have an acid pH.
- the pH value may range between about 3 and 6, preferably between 3 and 4.
- the small quantity of 0.5-3 percent by weight of the anion-active dyeing assistant or of the mixture of anion-active and cation-active substances according to the invention which gives good results even with deep shades, is a considerable advantage.
- a quantity of only 0.5-2 percent by weight, referred to the weight of the goods will already be sufiicient.
- anionactive compounds of the Formula I such as contain the group SO CH CH -OSO Y (Y having the meaning given in Formula I and rinsing the goods after dyeing for 1 to 20 minutes at temperatures in the range of 60 and 90 C. with an aqueous alkaline bath in the presence of a high molecular compound containing at least 3 hydroxyl groups.
- aqueous alkaline bath in the presence of a high molecular compound containing at least 3 hydroxyl groups.
- reactive vinylsulfone groups in the anion-active dyeing assistant which cause cross-linking with the added compounds containing hydroxy groups.
- This fastnessimproving treatment can also be carried out by padding with alkalies and compounds containing hydroxyl groups the dyeings produced on polyamide fabrics in the presence of compounds of the Formula I containing the group -SO CH CH -OSO Y and then further treating the fabric as usual on the stenter at temperatures in the range of 90 and 180 C. for a period from 30 seconds to 10 minutes.
- alkalies for the aftertreatment there may be used in particular alkali metal hydroxides, alkali metal carbonates and alkali metal bicarbonates, as well as alkali metal salts of organic acids which pass over into hydroxides or carbonates at elevated temperatures.
- alkali metal hydroxides sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, and the corresponding bicarbonates, sodium acetate, potassium acetate as well as the sodium or potassium salt of trichloroacetic acid.
- the alkalies are generally used in amounts from about 0.3 to 10 percent by weight, preferably 0.3 to 5 percent by weight, referred to the weight of the goods.
- the quantity should be so chosen as to give a pH of at least 8. If compounds are used, which pass into alkalies at elevated temperatures, for example, the sodium salt of trichloroacetic acid, one can work under neutral or weakly acid conditions.
- polyvinyl alcohols having K-values from about to 100 (according to Fickentscher, Cellulosechemie, tome 13, page 58 (1932)), polyvinyl alcohols which can be either fully hydrolyzed or partly hydrolyzed and have a residual acetyl content of 090% as well as polyvinyl acetals containing hydroxyl groups, i.e.
- partly acetalized polyvinyl alcohols for example, acetalized with formaldehyde, acetaldehyde, benzaldehyde or other aliphatic or aromatic aldehydes, with an acetalization degree of 099% and K-values from 10 to 100.
- copolymers of monomeric vinyl compounds such as vinyl chloride, acrylic acid esters, methacrylic acid esters, acrylonitrile, styrene, etc. with vinyl esters such as vinyl formiate, vinyl acetate, vinyl propionate, etc., into which hydroxyl groups have been introduced by partial hydrolysis.
- the proportion of vinyl ester groups in the mentioned copolymers can vary between 0.5 and 99%, the degree of hydrolyzation of the vinyl ester component can vary from about 10 to 100%.
- suitable resins or partially hydrolyzed graft polymers of vinyl esters with polyethylene glycols for example, those obtained according to the German specifications 1,081,229 and 1,094,457.
- hydroxyl-containing compounds of natural origin there may be used inter alia carbohydrates such as starches (wheat starch, rice starch, potato starch, etc.) tragacanth, tannine, locust bean flour as well as locust bean flours that are partially etherified with lower, monoor dihydric aliphatic alcohols having 14 carbon atoms, modified star-ch preparations for example, British rubber, sugar, and sugar alcohols, furthermore cellulose esterified with lower carboxylic acids or lower alcohols having 14 carbon atoms or etherified cellulose, for example, methyl cellulose, carboxymethyl cellulose, etc.
- carbohydrates such as starches (wheat starch, rice starch, potato starch, etc.) tragacanth, tannine, locust bean flour as well as locust bean flours that are partially etherified with lower, monoor dihydric aliphatic alcohols having 14 carbon atoms, modified star-ch preparations for example, British rubber, sugar, and sugar alcohols, furthermore cellulose ester
- Example 1 100 parts of a polyamide fabric consisting in warp and beam of endless filaments, normally dyeing 'with streaks only, are dyed in a closed dyeing apparatus for 1 hour at 100 C. with 2 parts of an acid wool dyestuff strongly responding to yarn irregularities and having the general formula 1000 parts of water, after having brought the dyebath to the above temperature in the course of 40-50 minutes. After rinsing and drying, there is obtained a streakless, fast, grey dyeing.
- An improved fastness can be obtained, when treating the goods in the first rinsing bath with 2 parts of sodium trichloroacetate, or 2 parts of sodium bicarbonate alone or together with 2 parts of tannine, for 20 minutes at 60-80 C.
- the described aftertreatment can be carried out by padding on a foulard and drying the dyed fabric on a stenter for 5 minutes at 140 C.
- Example 2 parts of the fabric described in Example 1 are dyed as described in Example 1 with a dyebath having the following composition:
- Example 3 100 parts of the polyamide fabric which can be dyed with streaks only and which is described in Example 1,
- Example 4 100 parts of the polyamide fabric described in Example 1 which can be dyed with streaks only are dyed under the conditions described in Example 1 with a dyebath having the following composition:
- Example 5 parts of the fabric of polyamide described in Example 1, which can be dyed with streaks only, are dyed with a combination of acid dyestuffs of 4 parts of the red dyestuff A, 3.6 parts of the yellow dyestuff B, 0.05 part of the blue dyestulf C.
- Example 6 100 parts of the fabric described in Example 1 are dyed, after singeing, for 10 minutes at 30 0., with a bath having the following composition:
- the dyed goods are then rinsed and dried. There is obtained a level grey dyeing.
- the nodules formed by the singeing would be dyed deeper owing to their greater afiinity for the dyestuif than the fabric.
- Example 7 100 parts of the fabric described in Example 1 are dyed for 15 minutes at 30 C. with a bath having the following composition: 1000 parts of water, 3 parts of 2,4,6-.tri-(1-aminobenzene-2,4-disulfonic aoid)-s-triazine, 1 part of the condensation product of 6 mols of ethylene oxide and 1 mol of laurylamine, and 3 parts of acetic acid (30% strength).
- R is a member selected from the group consisting of hydrogen and a low molecular alkyl radical
- A is a member selected from the group consisting of an alkylene radical having 1-4 carbon atoms, a phenylene and naphthylene radical, a substituted phenylene and a substituted naphthylene radical
- Z is a member selected from the group consisting of SO Y, -OSO Y, COOY, and SO CH CH OSO Y (Y being a member selected from the group consisting of hydrogen and a salt-forming cation) and n is an integer from 1 to 3, as an assistant for levelling the dyeing.
- Process for dyeing textile materials having a basis of a synthetic linear polyamide which comprises bringing said textile materials into contact with an aqueous dye- 10 bath containing an acid wool dyestuff in the presence of a colorless compound of the formula i Z n-AN(;J ⁇ (IJNAZ n N ⁇ /N C in which R is a member selected from the group consisting of hydrogen and a low molecular alkyl radical, A is a member selected from the group consisting of an alkylene radical having 1-4 carbon atoms, a phenylene and a naphthylene radical, a substituted phenylene and a substituted naphthylene radical, Z represents the group SO CH CH OSO Y (Y being a member selected from the group consisting of hydrogen and a salt-forming cation) and n is an integer from 1 to 3, as an assistant for levelling the dyeing, and rinsing the dyed materials in an aqueous alkaline bath containing a high molecular
- Process for dyeing textile materials having a basis of a synthetic linear polyamine which comprises bringing said textile materials into contact with an aqueous dyebath containing a dyestuff for said materials in the presence of a colorless compound of the formula RI IAZu in which R is a member selected from the group consisting of hydrogen and a low molecular alkyl radical, A is a member selected from the group consisting of an alkylene radical having 1-4 carbon atoms, a phenylene and a naphthylene radical, a substituted phenylene and a substituted naphthylene radical, Z is a member selected from the group consisting of --SO Y, COOY, and SO CH CH OSO Y (Y being a member selected from the group consisting of hydrogen and a salt-forming cation) and n is an integer from 1 to 3, and a complexforming weakly cation-active product as assistants for levelling the dyeing.
- R is a member selected from the group consisting of hydrogen and
- a process as defined in claim 5, wherein the complex-forming Weakly cationic active product is an addition product of 2 to 30 mols of ethylene oxide per mol of an alkylamine having an alkyl radical with 8 to 18 carbon atoms.
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- Engineering & Computer Science (AREA)
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Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF37646A DE1290519B (de) | 1962-08-22 | 1962-08-22 | Verfahren zum streifenfreien Faerben von Textilmaterialien aus Polyamiden |
Publications (1)
Publication Number | Publication Date |
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US3278253A true US3278253A (en) | 1966-10-11 |
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Application Number | Title | Priority Date | Filing Date |
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US303425A Expired - Lifetime US3278253A (en) | 1962-08-22 | 1963-08-20 | Process for dyeing textile materials in an aqueous bath containing a dyestuff in the presence of a trifunctional triazine |
Country Status (10)
Country | Link |
---|---|
US (1) | US3278253A (no) |
AT (1) | AT252170B (no) |
BE (1) | BE636485A (no) |
CH (1) | CH403707A (no) |
DE (1) | DE1290519B (no) |
DK (1) | DK108362C (no) |
FR (1) | FR1367257A (no) |
GB (1) | GB1060718A (no) |
NL (2) | NL125292C (no) |
NO (1) | NO120472B (no) |
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3481903A (en) * | 1967-05-15 | 1969-12-02 | Gaetano F D Alelio | Chelating compositions comprising products of aldehydes and triazine derivatives |
US3519627A (en) * | 1968-04-09 | 1970-07-07 | Ashland Oil Inc | Carboxyl-containing ethers of amino-triazine/aldehyde condensates |
US3615739A (en) * | 1963-12-31 | 1971-10-26 | Geigy Chem Corp | Floor polishing composition containing substituted {11 -triazines |
US3743477A (en) * | 1967-07-03 | 1973-07-03 | Sandoz Ltd | Process for reserving textiles of natural polyamide fibres and of synthetic fibres dyeable with acid dyes |
US3890091A (en) * | 1972-09-08 | 1975-06-17 | Hoechst Ag | Level dyeing of wool polyimine or polyamine and sulfonated phenylene amino-chlorotriazine treated |
US3930795A (en) * | 1972-09-08 | 1976-01-06 | Hoechst Aktiengesellschaft | Process for the level dyeing of wool |
US4132850A (en) * | 1977-06-29 | 1979-01-02 | American Cyanamid Company | Tri-substituted triazines |
US4183929A (en) * | 1977-06-29 | 1980-01-15 | American Cyanamid Company | Tri-substituted triazines |
US4444563A (en) * | 1981-09-07 | 1984-04-24 | Ciba-Geigy Corporation | Dyeing assistant and use thereof in dyeing or printing synthetic polyamide fibre materials |
EP0118983A2 (en) * | 1983-02-11 | 1984-09-19 | Wool Development International Limited | Textile treatment |
EP0174794A2 (en) * | 1984-09-14 | 1986-03-19 | Wool Development International Limited | Textile treatment |
EP0175225A2 (de) * | 1984-09-15 | 1986-03-26 | Hoechst Aktiengesellschaft | Faserreaktive Triazinverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung |
US4587338A (en) * | 1983-09-16 | 1986-05-06 | Hoechst Aktiengesellschaft | Perfluoroalkyl esters of anthranilic acids |
US4617390A (en) * | 1982-02-23 | 1986-10-14 | Basf Aktiengesellschaft | S-triazine derivatives |
US4695632A (en) * | 1976-06-12 | 1987-09-22 | Bayer Aktiengesellschaft | Quaternary reactive compounds |
US4886882A (en) * | 1985-09-07 | 1989-12-12 | Basf Aktiengesellschaft | Hydroxyoxaalkylmelamines |
US5571444A (en) * | 1989-09-11 | 1996-11-05 | Invicta Group Industries Pty Ltd. | Textile treatment |
WO1997035848A1 (de) * | 1996-03-25 | 1997-10-02 | Basf Aktiengesellschaft | Triazinderivate als fixiermittel beim färben und als vernetzer |
US5792222A (en) * | 1996-03-04 | 1998-08-11 | Ciba Specialty Chemicals Corporation | Process for dyeing natural or synthetic polyamide fibre materials |
US6022378A (en) * | 1996-06-21 | 2000-02-08 | Lenzing Aktiengesellschaft | Process for the treatment of cellulose fibres and of assemblies made from these fibres |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0102926B1 (de) * | 1982-09-03 | 1987-01-07 | Ciba-Geigy Ag | Färbereihilfsmittel und seine Verwendung beim Färben oder Bedrucken von synthetischen Polyamidfasermaterialien |
US4859207A (en) * | 1987-07-27 | 1989-08-22 | Ciba-Geigy Corporation | Process for dyeing textile planar fabrics made from polyamides: with melamine compound as resist agent |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3054699A (en) * | 1957-06-12 | 1962-09-18 | Ici Ltd | Water-soluble latent curing catalysts for textile treatment resins |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE580952A (no) * | 1958-07-24 |
-
0
- NL NL296874D patent/NL296874A/xx unknown
- NL NL125292D patent/NL125292C/xx active
- BE BE636485D patent/BE636485A/xx unknown
-
1962
- 1962-08-22 DE DEF37646A patent/DE1290519B/de active Pending
-
1963
- 1963-08-19 CH CH1021563A patent/CH403707A/de unknown
- 1963-08-20 US US303425A patent/US3278253A/en not_active Expired - Lifetime
- 1963-08-20 AT AT666563A patent/AT252170B/de active
- 1963-08-21 NO NO149809A patent/NO120472B/no unknown
- 1963-08-21 DK DK400163AA patent/DK108362C/da active
- 1963-08-22 FR FR945342A patent/FR1367257A/fr not_active Expired
- 1963-08-22 GB GB33373/63A patent/GB1060718A/en not_active Expired
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3054699A (en) * | 1957-06-12 | 1962-09-18 | Ici Ltd | Water-soluble latent curing catalysts for textile treatment resins |
Cited By (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3615739A (en) * | 1963-12-31 | 1971-10-26 | Geigy Chem Corp | Floor polishing composition containing substituted {11 -triazines |
US3481903A (en) * | 1967-05-15 | 1969-12-02 | Gaetano F D Alelio | Chelating compositions comprising products of aldehydes and triazine derivatives |
US3743477A (en) * | 1967-07-03 | 1973-07-03 | Sandoz Ltd | Process for reserving textiles of natural polyamide fibres and of synthetic fibres dyeable with acid dyes |
US3519627A (en) * | 1968-04-09 | 1970-07-07 | Ashland Oil Inc | Carboxyl-containing ethers of amino-triazine/aldehyde condensates |
US3890091A (en) * | 1972-09-08 | 1975-06-17 | Hoechst Ag | Level dyeing of wool polyimine or polyamine and sulfonated phenylene amino-chlorotriazine treated |
US3930795A (en) * | 1972-09-08 | 1976-01-06 | Hoechst Aktiengesellschaft | Process for the level dyeing of wool |
US4695632A (en) * | 1976-06-12 | 1987-09-22 | Bayer Aktiengesellschaft | Quaternary reactive compounds |
US4132850A (en) * | 1977-06-29 | 1979-01-02 | American Cyanamid Company | Tri-substituted triazines |
US4183929A (en) * | 1977-06-29 | 1980-01-15 | American Cyanamid Company | Tri-substituted triazines |
US4444563A (en) * | 1981-09-07 | 1984-04-24 | Ciba-Geigy Corporation | Dyeing assistant and use thereof in dyeing or printing synthetic polyamide fibre materials |
US4617390A (en) * | 1982-02-23 | 1986-10-14 | Basf Aktiengesellschaft | S-triazine derivatives |
EP0118983A2 (en) * | 1983-02-11 | 1984-09-19 | Wool Development International Limited | Textile treatment |
US4563189A (en) * | 1983-02-11 | 1986-01-07 | Wool Development International Ltd. | Treatment of fibers with arylating agents to enhance disperse dyeability |
EP0118983A3 (en) * | 1983-02-11 | 1986-07-16 | Wool Development International Limited | Textile treatment |
US4587338A (en) * | 1983-09-16 | 1986-05-06 | Hoechst Aktiengesellschaft | Perfluoroalkyl esters of anthranilic acids |
EP0174794A2 (en) * | 1984-09-14 | 1986-03-19 | Wool Development International Limited | Textile treatment |
US4950301A (en) * | 1984-09-14 | 1990-08-21 | Wool Development International Limited | Keratinous textile treatment with arylating compounds containing fibre reactive groups |
EP0174794A3 (en) * | 1984-09-14 | 1987-09-16 | Wool Development International Limited | Textile treatment |
EP0175225A2 (de) * | 1984-09-15 | 1986-03-26 | Hoechst Aktiengesellschaft | Faserreaktive Triazinverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung |
EP0175225A3 (de) * | 1984-09-15 | 1987-04-29 | Hoechst Aktiengesellschaft | Faserreaktive Triazinverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung |
US4886882A (en) * | 1985-09-07 | 1989-12-12 | Basf Aktiengesellschaft | Hydroxyoxaalkylmelamines |
US5571444A (en) * | 1989-09-11 | 1996-11-05 | Invicta Group Industries Pty Ltd. | Textile treatment |
US5792222A (en) * | 1996-03-04 | 1998-08-11 | Ciba Specialty Chemicals Corporation | Process for dyeing natural or synthetic polyamide fibre materials |
US5922865A (en) * | 1996-03-04 | 1999-07-13 | Ciba Specialty Chemicals Corporation | Process for dyeing natural or synthetic polyamide fiber materials |
WO1997035848A1 (de) * | 1996-03-25 | 1997-10-02 | Basf Aktiengesellschaft | Triazinderivate als fixiermittel beim färben und als vernetzer |
US6120562A (en) * | 1996-03-25 | 2000-09-19 | Basf Aktiengesellschaft | Triazine derivatives as fixers in coloring and as cross-linking agents |
US6022378A (en) * | 1996-06-21 | 2000-02-08 | Lenzing Aktiengesellschaft | Process for the treatment of cellulose fibres and of assemblies made from these fibres |
Also Published As
Publication number | Publication date |
---|---|
FR1367257A (fr) | 1964-07-17 |
CH1021563A4 (no) | 1965-08-31 |
DK108362C (da) | 1967-11-27 |
CH403707A (de) | 1966-06-15 |
NO120472B (no) | 1970-10-26 |
NL125292C (no) | |
AT252170B (de) | 1967-02-10 |
BE636485A (no) | |
NL296874A (no) | |
DE1290519B (de) | 1969-03-13 |
GB1060718A (en) | 1967-03-08 |
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