GB2168364A - Sulphates of oxyalkylated amines and their use as dyeing assistants - Google Patents
Sulphates of oxyalkylated amines and their use as dyeing assistants Download PDFInfo
- Publication number
- GB2168364A GB2168364A GB08530471A GB8530471A GB2168364A GB 2168364 A GB2168364 A GB 2168364A GB 08530471 A GB08530471 A GB 08530471A GB 8530471 A GB8530471 A GB 8530471A GB 2168364 A GB2168364 A GB 2168364A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compounds
- dyed
- printed
- acid
- 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.)
- Withdrawn
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- 238000004043 dyeing Methods 0.000 title claims abstract description 44
- 150000001412 amines Chemical class 0.000 title claims description 11
- 150000003467 sulfuric acid derivatives Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 29
- 239000000758 substrate Substances 0.000 claims abstract description 25
- 150000003839 salts Chemical group 0.000 claims abstract description 20
- 239000004753 textile Substances 0.000 claims abstract description 14
- 238000007639 printing Methods 0.000 claims abstract description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000004952 Polyamide Substances 0.000 claims abstract description 8
- 239000012458 free base Substances 0.000 claims abstract description 8
- 229920002647 polyamide Polymers 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 7
- 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 claims abstract description 6
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 5
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 5
- 239000011734 sodium Substances 0.000 claims abstract description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 4
- 239000011591 potassium Substances 0.000 claims abstract description 4
- 239000000975 dye Substances 0.000 claims description 19
- 210000002268 wool Anatomy 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 15
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 11
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 5
- 239000001117 sulphuric acid Substances 0.000 claims description 5
- 235000011149 sulphuric acid Nutrition 0.000 claims description 5
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 claims description 2
- 241001662103 Cryptocarya corrugata Species 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000004744 fabric Substances 0.000 description 8
- -1 sulphate anion Chemical class 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 239000004202 carbamide Substances 0.000 description 7
- 238000005886 esterification reaction Methods 0.000 description 6
- 150000004696 coordination complex Chemical class 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CQPFMGBJSMSXLP-UHFFFAOYSA-M acid orange 7 Chemical compound [Na+].OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 CQPFMGBJSMSXLP-UHFFFAOYSA-M 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 235000015424 sodium Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- FPVGTPBMTFTMRT-UHFFFAOYSA-L disodium;2-amino-5-[(4-sulfonatophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-UHFFFAOYSA-L 0.000 description 2
- 235000019233 fast yellow AB Nutrition 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- AWFYPPSBLUWMFQ-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=C2 AWFYPPSBLUWMFQ-UHFFFAOYSA-N 0.000 description 1
- XDVOLDOITVSJGL-UHFFFAOYSA-N 3,7-dihydroxy-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical class O1B(O)OB2OB(O)OB1O2 XDVOLDOITVSJGL-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 241001584775 Tunga penetrans Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- XPRMZBUQQMPKCR-UHFFFAOYSA-L disodium;8-anilino-5-[[4-[(3-sulfonatophenyl)diazenyl]naphthalen-1-yl]diazenyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C3=CC=CC=C3C(N=NC=3C4=CC=CC(=C4C(NC=4C=CC=CC=4)=CC=3)S([O-])(=O)=O)=CC=2)=C1 XPRMZBUQQMPKCR-UHFFFAOYSA-L 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical group C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- VPNOHCYAOXWMAR-UHFFFAOYSA-N docosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCN VPNOHCYAOXWMAR-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000009975 hank dyeing Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- BUHXFUSLEBPCEB-UHFFFAOYSA-N icosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCN BUHXFUSLEBPCEB-UHFFFAOYSA-N 0.000 description 1
- 238000009981 jet dyeing Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical class COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000009969 top dyeing Methods 0.000 description 1
- 125000005209 triethanolammonium group Chemical group 0.000 description 1
- 238000009976 warp beam dyeing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/326—Polymers modified by chemical after-treatment with inorganic compounds containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing 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
- 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
- D06P1/6076—Nitrogen-containing polyethers or their quaternary derivatives addition products of amines and alkylene oxides or oxiranes
-
- 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
- D06P3/06—Material containing basic nitrogen containing amide groups using acid dyes
-
- 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
- D06P3/10—Material containing basic nitrogen containing amide groups using reactive dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
In a process for dyeing or printing a polyamide-containing textile substrate, the substrate is contacted either before or during dyeing or printing, with one or more compounds of formula I <IMAGE> in which R1 is C18-22alkyl or C18-22 alkenyl each R2, independently, is hydrogen, sodium, potassium, ammonium or substituted ammonium R3 is hydrogen or -SO3R2 in each (CmH2mO &rparstr& unit, independently, m is 2, 3 or 4 and n + p is a number from 17 to 23 in free base or in protonated or quaternary salt form.
Description
SPECIFICATION
Improvements in or relating to organic compounds
The invention relates to fatty amine polyoxyalkyl sulphates useful as dyeing assistants for the dyeing or printing of a textile substrate comprising natural or synthetic polyamide fibers.
The present invention provides a process for dyeing or printing a textile substrate comprising natural or synthetic polyamide fibres, which process comprises contacting the textile substrate to be dyed or printed either before or during dyeing or printing, with an effective amount of one or more compounds of formula I
in which
R1 is C18.22alkyl or C182 alkenyl, each
R2, independently, is hydrogen, sodium, potassium, ammonium or substituted ammonium P3 is hydrogen or -SO3R2 in each (CmH2mOf unit, independently, m is 2,3 or 4 and n + p is a number from 17 to 23 in free base form or in protonated or quaternary salt form.
The compounds of formula I in free base or salt form are new and form also part of the invention.
When R1 is C18.22alkyl, it is preferably stearly, arachidyl or behenyl. When R1 is C18.22alkenyl, it is preferably oleyl.
Substituted ammonium as R2 is preferably an ammonium substituted by up to three ss-, y- or -hydroxy-C2 4alkyl groups, e.g. mono-, di- ortriethanolammonium.
When P3 is -SO3R2, the two R2,s are peferably identical.
Preferably R2 is ammonium.
Preferably P3 is -S03R2.
In each (CmH2mQJ unit, independently, m is preferably 2 or 3, more preferably 2. Preferably all the (CmH2mOt units present in the molecule are identical.
n + p is preferably from 18 to 22, more preferably 20.
The expression "free base form" refers to the central nitrogen atom in the compound of formula I, in a non protonated or non quaternary form.
Preferred compounds of formula I are those in which P3 is -SO3R2, particularly these in which R1 is stearyl, arachidyl or benhenyl, P2 is ammonium, R3 is -SO3NH4, m = 2 and n + p = 20, more preferably a mixture of such in which R1 is stearyl, arachidyl and behenyl.
Preferred salts of compounds of formula I are the quaternary salts, e.g. those containing as an anion a chloride, bromide, methylsulphate or sulphate anion.
The compounds of formula I are prepared by esterifying the addition product of 17-23 mols C2.4alkylene oxide (per mol amine) to an amine of formula II R,NH2 II in which P1 is as defined above, or a mixture thereof, with sulphuric acid or a functional derivative thereof, and, where desired, converting the resulting compounds of formula I in free acid or base form into an appropriate salt form or vice versa.
The addition of C2.4alkylene oxide to the amine of formula II may be carried out according to known methods, conveniently in the presence of a catalyst, e.g. sodium or potassium hydroxide.
The mo no- or di-esterification of the polyalkoxylated amine with sulphuric acid or a functional derivative thereof may be effected in accordance with known methods. Suitable functional derivatives of sulphuric acid include the anhydride, halides and amides. Preferably the polyalkoxylated amine is mono- or di-esterified by reaction with sulphamic acid, thus giving directly the compounds of formula I in which R2 is ammonium. The esterification is conveniently carried out at a temperature from 90 to 1200C. Depending on the amount of sulphuric acid or functional derivative thereof used, one final hydroxy group present in the polyalkylated amine or both final hydroxy groups may be esterified.Preferably the esterification is carried out in the presence of a solubilising agent, more preferably urea; such is preferably added in an amount of from 20 to 25% by weight of the final esterified compound. Once the esterification is complete, it is not necessary to remove the urea from the reaction product. Preferably the resulting sulphates of formula I are used in admixture with urea.
Compounds of formula I in which P2 has one of the indicated significances, e.g. hydrogen, may be converted in known manner into a corresponding compound of formula I in which R2 has another indicated significance, e.g. distinct from hydrogen.
The conversion of compounds of formula I in free base form into a corresponding protonated or quaternary form or vice versa may be carried out according to known methods. Suitable protonating and quaternizing agents include hydrochloric acid, hydrobromic acid, dimethylsulphate, methyl or ethyl bromide and benzylchoride.
The compounds of formula I and their salts are useful dyeing assistants for dyeing or printing textiles comprising natural or synthetic polamides or a mixture thereof, such as wool, silk or nylon, of which wool is particularly preferred. The substrate may also be a blend or natural or synthetic polyamides with further synthetic fibres such as polyester. The material can be in any conventional form, for example as fibres, filaments, yarns, woven or knitted goods or carpets.
The compounds of formula I and their salts are conveniently used in an amount of from 0.2 to 4% by weight, preferably 0.5 to 3% by weight based on the weight of the substrate to be dyed or printed.
The process of the invention may be used for dyeing the textile substrate with a dyestuff or a mixture of dyestuffs suitable for dyeing natural or synthetic polyamides, preferably acid wool dyestuffs. Suitable acid wool dyestuffs include various dyestuff classes which may contain at least one sulphonic acid group and optionally at least one group capable or reacting with the polyamide fibre.Preferred acid wool dyestuffs are for example triphenylmethane dyestuffs containing at least two sulphonic acid groups, metal-free mono- or disazo dyestuffs containing at least one sulphonic acid group and and optionally at least one fibre-reacting group, metallized monoazo, disazo, azomethine and formazane dyestuffs, particularly copper, chromium, nickel or cobalt dyestuff complexes, especially those in which a metal atom is bound with two azo dyestuff molecules or with one azo dyestuff molecule and one azomethine dyestuff molecule, containing optionally at least one sulphonic acid group and optionally at least one fibre-reacting group, and anthraquinone dyestuffs containing at least one sulphonic acid group, particularly those belonging to the 1 -amino-4arylaminoanthraquinone-2-sulphonic acid and 1,4-diarylamino-or 1-cycloalkylamino-4arylaminoanthraquinonesulphonic acid classes. More preferred metal complex dyestuffs are disazo metal complex dyestuffs containing two sulphonic acid groups and 1:2 chromium or cobalt complexes whose ligands are selected from monoazo, disazo and azomethine dyestuffs, especially 1:2 chromium or cobalt mixed complexes of azo dyestuffs.
Fibre-reacting groups are for example halogenated heterocyclic groups such as mono- chlorotriazinyl, dichlorotriazinyl, monofluoro triazinyl, monofluoropyrimidinyl, difluoropyrimidinyl, fluorochloropyrimidinyl, dichloroquinoxalinyl or methylsulphone-chloromethylprimidinyl, or vinylsulphone groups. When a dyestuff containing at least one fibre-reacting group is used, preferably such a dyestuff is used in combination with a fibre-reacting group free dyestuff.
The amount of dyestuffs may vary within a broad range, depending on the desired tinctorial depth. In general suitable amounts are in the range of from 0.001 to 10% by weight based on the weight of the substrate.
According to the invention, the substrate to be dyed or printed is contact with the compounds of formula I, in free base or salt form, either before or during dyeing or printing. The treatment with the compounds of the invention is conveniently carried out from an acidic aqueous medium, preferably such having a pH within the isoelectric range of the natural polyamides, i.e. pH 4-5.5, particularly 4.5-5. Such conditions are particularly preferred when the substrate to be dyed is wool. The desired pH values may be adjusted by addition to the treatment or dyeing medium containing the compounds of formula I, of an inorganic or organic acid such as sulphuric acid, phosphoric acid or a lower aliphatic carboxylic acid, for example formic, acetic or oxalic acid, and/or a salt such as ammonium acetate, ammonium sulphate or sodium acetate.
When the compounds of formula I ortheir salts are applied on the substrate before dyeing or printing, this application may be carried out according to known methods such as by exhaust, padding or printing.
Preferably they are applied on the substrate by exhaust, conveniently at a temperature of from 60 to 1 20"C, particularly 80 to 102"C. The liquor to goods ratio may vary; advantageously it is from 4:1 to 100:1, preferably 1:1 to 50:1. After an effective treatment time, for example from 20 to 120 minutes, the treatment bath may be either discharged and replaced or cooled and, after addition of the dyestuffs, used for dyeing.
When dyeing or printing in the presence of the compounds of formula I or their salts, such may be carried out in accordance with known methods, preferably by exhaust. The liquor two goods ratio, dyeing temperature and pH are peferably as indicated above. The acid or salt, dyeing assistant of formula I and the dyestuff(s) are added to the bath preferably at a temperature from 30 to 70"C, the dyebath is then heated to the desired dyeing temperature and dyeing is conveniently effected for a period of from 20 to 120, preferably 30 to 60 minutes. When dyeing is complete, the substrate is rinsed and dried in a conventional manner.
The treatment with a compound of the invention or dyeing in the presence of a compound of the invention may be carried out in a known dyeing machine, for example winch beck machine, top dyeing machine, packing machine, beam dyeing machine, paddle dyeing machine, jigger, jet dyeing machine or hank dyeing machine.
In the process of the invention, the compounds of formula I and their salts produce on the textile substrate a good levelling action. Intensive dyeings with improved rubbing fastnesses are obtained in a high yield, the dyeing assistants of formula I exerting no negative influence on the other fastnesses such as light and wet fastnesses of the dyeings or printings.
The compounds of the invention hinder the dichroism of 1:2 metal complex dyestuffs thus resulting in an improved fibre levelness. Furthermore, they exhibit a substantially low retarding effect, which allows the use of combination of 1:2 metal complex, acid and/or fibre-reacting dyestuffs. They also improve significantly the take-up of the dyestuffs.When used as dyeing assistants for dyeing wool particularly with 1:2 metal complex dyestuffs, they have such an assistant action such that good dyeing results can be produced in the absence of an anionic product having an affinity for wool fibres as used in the hitherto known wool dyeing processes, for example compounds containing at least one sulphonic acid group preferably bound on an aromatic ring such as a naphthalene or benzene ring, e.g. the reaction products of naphthalene sulphonic acid with formaldehyde, as well as in the absence of a hydrosoluble tetraboric acid salt, e.g. borax.
In the presence of hydrophobic sulphonic acid group free 1:2 metal complex dyestuffs, the compounds of formula I and their salts have an anti-precipitating action; particularly they impede the formation of insoluble products such as produced by dehydration of dyestuff-dyeing assistant addition products.
The following Examples, in which all parts and percentages are by weight, illustrate the invention. The temperatures are in degrees Centigrade.
Example 1
300 g (1 mol) of a commercial fatty amine (mean MW = 300) containing about 48% by weight of stearylamine, 40% by weight behenylamine and 12% by weight arachidylamine are reacted with 880 g (20 mols) ethylene oxide at 160-170 in the presence of 3 g sodium hydroxide for 6 to 8 hours while stirring. The resulting reaction mixture is cooled to 70-75". While stirring, there are added 388 g urea within 15 minutes and then 194 g (2 mols) amidosulphonic acid within 30 minutes, the reaction mixture being simuitaneously heated to 1000. After 6 hours stirring at 110 the esterification is complete. The resulting product may be used as such or as an aqueous solution.
Example 2
The procedure of Example 1 is repeated except that after the esterification has been completed, the reaction mixture is cooled to 85" and 126 g dimethyl sulphate are added dropwise thereto while stirring slowly. When the addition is complete, the reaction mixture is further heated for 6 hours at 1000. The resulting methylsulphate salt may be used as such or as an aqueous solution.
Example 3
10 Parts of a wool fabric are wetted at 400 in 400 parts water. To this bath there are added 0.2 parts of the dyeing assistant of formula I prepared in Example 1 and containing about 25% by weight urea, 0.1 part of the dyestuff C.l. Acid Red 399, and acetic acid in an amount sufficient to adjust the pH of the dyebath to about 4.8.
The whole is heated within 40 minutes to the boil and dyeing is performed for 60 minutes at the same temperature. After cooling of the dyebath, the fabric is withdrawn, rinsed and dried.
The wool fabric is dyed in a level red shade having good fastness properties.
By following the same procedure as disclosed above in Example 3 but using a mixture of compounds of formula I in which R1 is as defined above, R2 is sodium or ethanolammonium, R3 is hydrogen and n + p is either 17 or 23, dyeings with good levelness are obtained on wool. Instead of C.l. Acid Red 399, the following dyestuffs may be used, giving dyeings with good levelness: C.l. Acid Yellow 21, C.l. Acid Yellow 235, C.I. Acid
Orange 95, C.l. Acid Orange 168, C.l. Acid Red 263, C.l. Acid Blue 113, C.l. Acid Blue 269 or C.l. Acid Blue 334 or mixtures thereof.
The dyeing assistant of formula I used in Example 3 may also be replaced by a mixture of compounds of formula la
in which R1 is a mixture of alkyl groups containing about 48% stearyl, 12% arachidyl and 40% behenyl, n + p = 20, R4 is methyl and X0 is CH30SO3C' together with compounds of such formula la in which R4 is benzyl and XO is Ciao. When dyeing in the presence of this mixture is carried out according to the procedure of
Example 3, the wool substrate is dyed in a level and fast shade.
Example 4
The procedure of Example 3 is repeated but using 0.1875 parts of a compound of formula I in which R1 is oleyl, R2 is triethanolammonium, R3 is hydrogen, m = 3 and n + p = 18 in admixture with 0.0625 parts urea.
A level red dyeing on wool with good fastness properties is thus obtained.
Example 5
The procedure of Example 3 is repeated except that 10 parts 6.6 nylon are dyed with 0.3 parts C.l. Acid Blue 269.
A navy blue dyeing with high levelness and fastness properties is obtained.
Example 6
10 Parts of a wool fabric are introduced in 200 parts water at 40 containing 0.3 parts of a compound of formula I in which R1 is a mixture of alkyl groups containing about 48% stearyl, 12% arachidyl and 40% behenyl, R2 is ammonium, R3 is -S03NH4, m = 4 and n + p = 22 together with 0.07 parts urea. The pH of the bath is adjusted to about 4.8 by the addition of acetic acid. The whole is then heated within 30 minutes to the boil and the fabric is treated at the boil for 60 minutes. The bath is discharged and replaced by 400 parts water at 40 containing 0.15 parts C.l. Acid Orange 168. After adjustment of the bath to pH 4.8 by addition of acetic acid, the whole is heated within 40 minutes to the boil and the fabric is dyed for 60 minutes at the boil.
After cooling, the fabric is withdrawn from the bath, rinsed and dried.
An evenly dyed orange red fabric having good fastnesses is obtained.
In Examples 3 to 6, the dyeing assistant of formula I used may be replaced either by the dyeing assistant of formula I of Example 2 in the corresponding amount, or by a mixture of compounds of formula i in which R1 is a mixture of stearyl, behenyl and arachidyl as defined above, R2 is ammonium, R3 is -SO3NH4, m is 2 and n + piseitherl7or23.
Claims (18)
1. A compounds of formula I
in which
R1 is C,822alkyl orC15.22 alkenyl, each
R2, independently, is hydrogen, sodium, potassium, ammonium or substituted ammonium
R3 is hydrogen or -S03R2
in each (CmH2mOt unit, independently, m is 2,3 or4 and n + p is a number from 17 to 23 in free base form or in protonated or quaternary salt form.
2. A compound according to Claim 1, in which R1 is stearyl, arachidyl or behenyl.
3. A compound according to Claim 1 or 2, in which R3 is -SO3R2.
4. A compound according to any one of the preceding claims in which in each (CmH2mOi unit m is 2 or 3.
5. A compound according to any one of the preceding claims in which n + p is from 18 to 22.
6. A compound according to any one of the preceding claims in which R1 is stearyl, arachidyl or behenyl,
R3 is -SO3R2, R2 is ammonium, m is 2 and n + p is 20.
7. A process for the production of a compound of formula I as defined in Claim 1 or a mixture thereof, comprising esterifying the addition product of 17-23 mols C2.4alkylene oxide (per mole amine) to an amine of formula II
R1NH2 II in which R1 is as defined in Claim 1, or a mixture thereof, with sulphuric acid or a functionai derivative thereof and, where desired, converting the resulting compounds of formula I in free acid or base form into an appropriate salt form or vice versa.
8. A process for dyeing or printing a textile substrate comprising natural or synthetic polyamide fibres, which process comprises contacting the textile substrate to be dyed or printed either before or during dyeing or printing, with an effective amount of one or more compounds of formula I
in which
R1 is C1822alkyl or C18-22 alkenyl, each
R2, independently, is hydrogen, sodium, potassium, ammonium or substituted ammonium
R3 is hydrogen or -SO3R2 in each (CmH2mOt unit, independently, m is 2,3 or4 and n + p is a number from 17 to 23 in free base form or in protonated or quaternary salt form.
9. A process according to Claim 8, in which the textile substrate to be dyed or printed is contacted with one or more compounds of formula I as defined in any one of Claims 2 to 5.
10. A process according to Claim 8 or 9, in which the textile substrate to be dyed or printed is contacted with one or more of compounds of formula I in which R1 is stearyl, arachidyl and/or behenyl, R2 is ammonium, R3 is -SO3NH4, m is 2 and n + p is 20.
11. A process according to any one of Claims 8 to 10, in which the compounds of formula I and their salts are used in an amount of from 0.2 to 4% by weight based on the weight of the substrate to be dyed or printed.
12. A process according to Claim 11, in which the compounds of formula I and their salts are used in an amount of from 0.5 to 3% by weight based on the weight of the substrate to be dyed or printed.
13. A process according to any one of Claims 8 to 12, in which the textile substrate is dyed or printed with an acid wool dyestuff.
14. A process according to Claim 13, in which the acid wool dyestuff is a dyestuff containing at least one sulphuric acid group and optionally at least one fibre-reacting group.
15. A process according to Claim 14, in which the acid wood dyestuff is a triphenylmethane dyestuff containing at least two sulphonic acid groups, a metal-free mono- or disazo dyestuff containing at least one sulphonic acid group and optionally at least one fibre-reacting group, a metallized monoazo, disazo, azomethine or formazane dyestuff containing optionally at least one sulphonic acid group and optionally at least one fibre-reacting group, and/or an anthraquinone dyestuff containing at least one sulphuric acid group.
16. A process according to any one of Claims 8 to 15, in which the textile substrate to be dyed or printed comprises wool.
17. A process substantially as hereinbefore described with reference to Examples 1 to 6.
18. A textile substrate whenever dyed or printed according to the process as defined in any one of Claims 8 to 17.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3445645 | 1984-12-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8530471D0 GB8530471D0 (en) | 1986-01-22 |
| GB2168364A true GB2168364A (en) | 1986-06-18 |
Family
ID=6252786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08530471A Withdrawn GB2168364A (en) | 1984-12-14 | 1985-12-11 | Sulphates of oxyalkylated amines and their use as dyeing assistants |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS61145157A (en) |
| FR (1) | FR2574791A1 (en) |
| GB (1) | GB2168364A (en) |
| IT (1) | IT1200158B (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4802887A (en) * | 1985-06-27 | 1989-02-07 | Sandoz Ltd. | Compositions comprising a water-soluble metal complex dye, an oxyalklated amine sulphate ester and a dispersing agent |
| EP0442844A1 (en) * | 1990-02-14 | 1991-08-21 | Ciba-Geigy Ag | Process for dyeing of wool with reactive dyes |
| WO2001005872A1 (en) * | 1999-07-16 | 2001-01-25 | Basf Aktiengesellschaft | Zwitterionic polyetherpolyamines and a process for their production |
| WO2001009430A1 (en) * | 1999-08-03 | 2001-02-08 | Clariant Finance (Bvi) Limited | Process for dyeing or printing polyamide fibres |
| US6703523B1 (en) | 1999-07-16 | 2004-03-09 | Basf Aktiengesellschaft | Zwitterionic polyetherpolyamines and process for their production |
| WO2009009653A2 (en) * | 2007-07-12 | 2009-01-15 | Johnson & Johnson Consumer Companies, Inc. | A fade-resistant coloring composition containing an acid dye and a cationic conditioning agent for a keratin- containing substrate |
| EP2246099A3 (en) * | 2008-11-25 | 2014-04-16 | Henkel AG & Co. KGaA | New colouring agent |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1777337A1 (en) * | 2005-10-07 | 2007-04-25 | Clariant International Ltd. | Method of dyeing polyamide fibres |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB465200A (en) * | 1935-08-26 | 1937-04-26 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of valuable condensation products containing nitrogen, phosphorus or sulphur |
| GB888661A (en) * | 1958-01-24 | 1962-01-31 | Ciba Ltd | Acid esters of amino polyethylene glycols |
| GB1087415A (en) * | 1963-06-25 | 1967-10-18 | Marchon Products Ltd | Novel surface-active betaines and preparation and use thereof |
| GB1143090A (en) * | 1965-03-18 | 1969-02-19 | Ciba Ltd | New derivatives of polyglycol compounds and process for their manufacture |
| GB1470712A (en) * | 1973-04-09 | 1977-04-21 | Gaf Corp | Oxyalkylated amine derivatives and their use as amphoteric surface active agnets |
-
1985
- 1985-12-09 FR FR8518383A patent/FR2574791A1/en not_active Withdrawn
- 1985-12-11 GB GB08530471A patent/GB2168364A/en not_active Withdrawn
- 1985-12-12 IT IT48916/85A patent/IT1200158B/en active
- 1985-12-13 JP JP60279355A patent/JPS61145157A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB465200A (en) * | 1935-08-26 | 1937-04-26 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of valuable condensation products containing nitrogen, phosphorus or sulphur |
| GB888661A (en) * | 1958-01-24 | 1962-01-31 | Ciba Ltd | Acid esters of amino polyethylene glycols |
| GB1087415A (en) * | 1963-06-25 | 1967-10-18 | Marchon Products Ltd | Novel surface-active betaines and preparation and use thereof |
| GB1143090A (en) * | 1965-03-18 | 1969-02-19 | Ciba Ltd | New derivatives of polyglycol compounds and process for their manufacture |
| GB1470712A (en) * | 1973-04-09 | 1977-04-21 | Gaf Corp | Oxyalkylated amine derivatives and their use as amphoteric surface active agnets |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4802887A (en) * | 1985-06-27 | 1989-02-07 | Sandoz Ltd. | Compositions comprising a water-soluble metal complex dye, an oxyalklated amine sulphate ester and a dispersing agent |
| EP0442844A1 (en) * | 1990-02-14 | 1991-08-21 | Ciba-Geigy Ag | Process for dyeing of wool with reactive dyes |
| US5145486A (en) * | 1990-02-14 | 1992-09-08 | Ciba-Geigy Corporation | Process for dyeing wool with reactive dyes |
| WO2001005872A1 (en) * | 1999-07-16 | 2001-01-25 | Basf Aktiengesellschaft | Zwitterionic polyetherpolyamines and a process for their production |
| US6703523B1 (en) | 1999-07-16 | 2004-03-09 | Basf Aktiengesellschaft | Zwitterionic polyetherpolyamines and process for their production |
| WO2001009430A1 (en) * | 1999-08-03 | 2001-02-08 | Clariant Finance (Bvi) Limited | Process for dyeing or printing polyamide fibres |
| WO2009009653A2 (en) * | 2007-07-12 | 2009-01-15 | Johnson & Johnson Consumer Companies, Inc. | A fade-resistant coloring composition containing an acid dye and a cationic conditioning agent for a keratin- containing substrate |
| WO2009009653A3 (en) * | 2007-07-12 | 2009-04-16 | Johnson & Johnson Consumer | A fade-resistant coloring composition containing an acid dye and a cationic conditioning agent for a keratin- containing substrate |
| EP2246099A3 (en) * | 2008-11-25 | 2014-04-16 | Henkel AG & Co. KGaA | New colouring agent |
Also Published As
| Publication number | Publication date |
|---|---|
| IT8548916A0 (en) | 1985-12-12 |
| IT1200158B (en) | 1989-01-05 |
| GB8530471D0 (en) | 1986-01-22 |
| FR2574791A1 (en) | 1986-06-20 |
| JPS61145157A (en) | 1986-07-02 |
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| Date | Code | Title | Description |
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| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |