US3469930A - Wool dyeing process - Google Patents
Wool dyeing process Download PDFInfo
- Publication number
- US3469930A US3469930A US547157A US3469930DA US3469930A US 3469930 A US3469930 A US 3469930A US 547157 A US547157 A US 547157A US 3469930D A US3469930D A US 3469930DA US 3469930 A US3469930 A US 3469930A
- Authority
- US
- United States
- Prior art keywords
- wool
- parts
- dyeing
- condensate
- phenol
- 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
- 210000002268 wool Anatomy 0.000 title description 31
- 238000004043 dyeing Methods 0.000 title description 21
- 238000000034 method Methods 0.000 title description 13
- -1 alkali metal dodecylbenzene sulphonate Chemical class 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000975 dye Substances 0.000 description 7
- 238000010025 steaming Methods 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 239000000661 sodium alginate Substances 0.000 description 6
- 235000010413 sodium alginate Nutrition 0.000 description 6
- 229940005550 sodium alginate Drugs 0.000 description 6
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 229920000161 Locust bean gum Polymers 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 235000010420 locust bean gum Nutrition 0.000 description 3
- 239000000711 locust bean gum Substances 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 239000001166 ammonium sulphate Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 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 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000019837 monoammonium phosphate Nutrition 0.000 description 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- KUCWUAFNGCMZDB-UHFFFAOYSA-N 2-amino-3-nitrophenol Chemical compound NC1=C(O)C=CC=C1[N+]([O-])=O KUCWUAFNGCMZDB-UHFFFAOYSA-N 0.000 description 1
- CBQDTCDOVVBGMN-UHFFFAOYSA-N 2-methyl-3-octylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1C CBQDTCDOVVBGMN-UHFFFAOYSA-N 0.000 description 1
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 1
- AOSMUQIUXKIWHS-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1.CCCCCCCCC1=CC=C(O)C=C1 AOSMUQIUXKIWHS-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
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- BDKZHNJTLHOSDW-UHFFFAOYSA-N [Na].CC(O)=O Chemical compound [Na].CC(O)=O BDKZHNJTLHOSDW-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 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 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- HQKOBNMULFASAN-UHFFFAOYSA-N chembl1991515 Chemical compound OC1=CC=C(Cl)C=C1N=NC1=C(O)C=CC2=CC=CC=C12 HQKOBNMULFASAN-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910021563 chromium fluoride Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- GDNCXORZAMVMIW-UHFFFAOYSA-N dodecane Chemical compound [CH2]CCCCCCCCCCC GDNCXORZAMVMIW-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- DUUPDCPVCHSTFF-UHFFFAOYSA-N nonane Chemical compound [CH2]CCCCCCCC DUUPDCPVCHSTFF-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- AXMCIYLNKNGNOT-UHFFFAOYSA-N sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/14—Wool
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- 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
- D06P1/613—Polyethers without nitrogen
- D06P1/6131—Addition products of hydroxyl groups-containing compounds with oxiranes
- D06P1/6135—Addition products of hydroxyl groups-containing compounds with oxiranes from aromatic alcohols or from phenols, naphthols
-
- 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
- D06P1/621—Compounds without 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
- 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
- D06P1/621—Compounds without nitrogen
- D06P1/622—Sulfonic acids or their salts
- D06P1/625—Aromatic
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/917—Wool or silk
Definitions
- This invention relates to a new wool dyeing process and more particularly to a new process for dyeing wool in a continuous manner.
- the alkali metal dedecyl benzene sulphonate used in the process is preferably the sodium salt; it is to be understood that by dodecylbenzene sulphonate there are included the commercially available materials of this name which are not pure substances but mixtures of homologues and isomers in which the main constituents are dodecylbenzene sulphonates in which the dodecyl radical can be straight chain or branched.
- the normal range of usage of this assistant lies between 1% and 5% by weight of the padding liquor.
- the preferred condensates of ethylene oxide with an alkyl phenol are those in which from 5 to 15, and more particularly 7.5 to moles of ethylene oxide, condensed with an alkyl phenol in which the alkyl radical or alkyl radicals contain from 5 to 12 carbon atoms, above all those having an octyl or nonyl radical, for example, an octyl or: nonyl phenol or an octyl cresol.
- the normal range of usage of this assistant lies between 1% and 20% by weight of the padding liquor.
- salts well-known as equivalents thereto in dyemg wool for example ammonium sulphate, ammonium acetate and ammonium phosphate.
- a suitable quantity of acid or salt is, for example, from 0.5 to 2% by weight of the padding liquor.
- other well-known adjuvants to dyestufi padding solutions, as used for the dyeing of other fibers for example, thickeners such as sodium alginate and solubilismg agents, such as urea.
- the new dyeing process can be used. to apply all kinds of wool dyestuffs to the fibre; for example, anthraquinone, monoazo, 1:1-meta1 complex monoazo and 1:2-metal complex monoazo dyestuffs having up to 2 sulphonic acid groups, can, in general, be used.
- As fibres which may be dyed there may be mentioned combed slivers, also fabrics, both knitted and woven piece goods.
- the new dyeing process can conveniently be carried out by slop-padding the wool through. the dyestuff solutron, removing excess of solution by passage through rollers and subjecting the wool to a steaming treatment for aperiod of time necessary to fix the dyestutf on the fibre, usually from 15 to 30 minutes being sufficient.
- the process of the invention enables the production of strong, dyeings of an excellent standard of levelness, much superior to those obtained by the use of an alkali metal dodecyl benzene sulphonate alone or an ethylene oxide/alkyl phenol condensate alone.
- Example 1 W001 slubbing is passed through a solution at 20 C. containing 10 parts of the mixed 1:2-chromium complex of 1-(5'-chloro-2-hydroxyphenylazo)-2-naphthol and 6- (4-nitro 2'-hydroxyphenylazo)2-acryloylamino-5-naphthol-7-sulphonic acid, 10 parts of a condensate of 9.5 moles of ethylene oxide with nonyl phenol, 10 parts of sodium dodecyl benzene sulphonate and 7.5 parts of sodium alginate per 1000 parts of liquor, and then wrung out to a liquid content of on the dry weight of wool. It is then passed into a chamber heated to 100 C. with steam and steamed for 20 minutes. A level brown dyeing free from surface frostiness is produced.
- Carbolan Violet Z'RS Cold Index No. 62,165-C.I. Acid Violet 51
- Example 2 Parts Carbolan V1olent ZRS 10 Alkyl/phenol condensate used in Example 1 40 Sodium dodecyl benzene sulphonate 40 Sodium alginate 5 Acetic acid 5 Water 900 Wool slubbing is passed at 50 C. through this solution and then through a pair of rollers to give a pickup of 100% by the material followed by steaming for 15 minutes at 102 C. A level well penetrated dyeing results.
- the 5 parts of sodium alginate can be replaced equally by 5 parts of carboxymethyl cellulose, and the 5 parts of acetic acid can be equally replaced by 20 parts of ammonium dihydrogen phosphate.
- the condensate of 3 4 octyl phenol with 7.5 or 8.5 moles of ethylene oxide there can be used the condensate of 3 4 octyl phenol with 7.5 or 8.5 moles of ethylene oxide, a Example 6 similar result being obtained.
- Example 8 e Parts Pad Wool slubbing at 20 C. to 100% pick-up, steam o Dyestufi of the formula 40 for 15 minutes at 102 C. A level blue dyeing 1s produced. Modified locust bean gum 5 Alkylphenol condensate used in Example 1 40 Example 5 Sodium dodecyl benzene sulphonate 16 7 Parts Chromium fluoride 50 Dyestuff of the formula* 15 Acetic acid Sodium alginate 5 Water 3 9 Acetic acid 8 Alkylphenol condensate used in Example 1 40 1,000 Sodium dodecyl benzene sulphonate (60%) 26 Water 906 5 I Formula 111 t 3-SOH .2 (Coppel PM u ocyrlmne) 23SOZNECH2CIEC1)1.5(3-SO2NLI2)1.3 7O
- the 10 parts of acetic acid may be replaced equally well by 20 parts of oxalic acid.
- a process for dyeing wool by padding the wool in an aqueous acidic solution of a water-soluble wool dyestufi and fixing the dyestufi. on the fibre by steaming, wherein the padding solution contains at least 1% by weight of an alkali metal dodecylbenzene sulphonate and at least 1% by weight of a condensate of ethylene oxide with an alkyl phenol wherein there are from 5 to 15 moles 10 of ethylene oxide per mole of alkyl phenol.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB22137/65A GB1118703A (en) | 1965-05-25 | 1965-05-25 | New wool dyeing process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3469930A true US3469930A (en) | 1969-09-30 |
Family
ID=10174493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US547157A Expired - Lifetime US3469930A (en) | 1965-05-25 | 1966-05-03 | Wool dyeing process |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3469930A (enrdf_load_html_response) |
| BE (1) | BE680952A (enrdf_load_html_response) |
| DE (1) | DE1619580A1 (enrdf_load_html_response) |
| ES (1) | ES327102A1 (enrdf_load_html_response) |
| GB (1) | GB1118703A (enrdf_load_html_response) |
| NL (1) | NL6607243A (enrdf_load_html_response) |
| SE (1) | SE301624B (enrdf_load_html_response) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3860392A (en) * | 1970-02-06 | 1975-01-14 | Pechiney Saint Gobain | Colorant compositions and method |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3377130A (en) * | 1960-08-11 | 1968-04-09 | American Cyanamid Co | Dyed nitrogenous fibers and anionic dye composition therefor |
| US3391985A (en) * | 1963-02-08 | 1968-07-09 | Geigy Ag J R | Process for pad-dyeing and printing wool and synthetic textile fibers in carrier compositions |
-
1965
- 1965-05-25 GB GB22137/65A patent/GB1118703A/en not_active Expired
-
1966
- 1966-05-03 US US547157A patent/US3469930A/en not_active Expired - Lifetime
- 1966-05-12 BE BE680952D patent/BE680952A/xx unknown
- 1966-05-18 DE DE19661619580 patent/DE1619580A1/de active Pending
- 1966-05-24 SE SE7117/66A patent/SE301624B/xx unknown
- 1966-05-24 ES ES0327102A patent/ES327102A1/es not_active Expired
- 1966-05-25 NL NL6607243A patent/NL6607243A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3377130A (en) * | 1960-08-11 | 1968-04-09 | American Cyanamid Co | Dyed nitrogenous fibers and anionic dye composition therefor |
| US3391985A (en) * | 1963-02-08 | 1968-07-09 | Geigy Ag J R | Process for pad-dyeing and printing wool and synthetic textile fibers in carrier compositions |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3860392A (en) * | 1970-02-06 | 1975-01-14 | Pechiney Saint Gobain | Colorant compositions and method |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1619580A1 (de) | 1971-06-09 |
| NL6607243A (enrdf_load_html_response) | 1966-11-28 |
| ES327102A1 (es) | 1967-08-01 |
| GB1118703A (en) | 1968-07-03 |
| BE680952A (enrdf_load_html_response) | 1966-11-14 |
| SE301624B (enrdf_load_html_response) | 1968-06-17 |
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