US2960381A - Dyeing of threads, filaments, fibres and the like - Google Patents
Dyeing of threads, filaments, fibres and the like Download PDFInfo
- Publication number
- US2960381A US2960381A US760100A US76010058A US2960381A US 2960381 A US2960381 A US 2960381A US 760100 A US760100 A US 760100A US 76010058 A US76010058 A US 76010058A US 2960381 A US2960381 A US 2960381A
- Authority
- US
- United States
- Prior art keywords
- parts
- phenol
- soap
- weight
- dyeing
- 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 10
- 239000000203 mixture Substances 0.000 claims description 25
- 239000000344 soap Substances 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 claims description 7
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical class CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- CBQDTCDOVVBGMN-UHFFFAOYSA-N 2-methyl-3-octylphenol Chemical class CCCCCCCCC1=CC=CC(O)=C1C CBQDTCDOVVBGMN-UHFFFAOYSA-N 0.000 claims description 4
- -1 CYCLOHEXYL PHENOLS Chemical class 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003240 coconut oil Substances 0.000 description 3
- 235000019864 coconut oil Nutrition 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- NZMDKLUVIWWSBU-UHFFFAOYSA-N 2-cyclohexyl-3,4-dimethylphenol Chemical compound CC1=CC=C(O)C(C2CCCCC2)=C1C NZMDKLUVIWWSBU-UHFFFAOYSA-N 0.000 description 2
- MOPDEMAOEMHGAS-UHFFFAOYSA-N 2-cyclohexyl-3-methylphenol Chemical compound CC1=CC=CC(O)=C1C1CCCCC1 MOPDEMAOEMHGAS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- ZVJYNDILACLBLH-UHFFFAOYSA-N 2-(5-methyl-2-propan-2-ylcyclohexyl)phenol Chemical compound CC(C)C1CCC(C)CC1C1=CC=CC=C1O ZVJYNDILACLBLH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 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
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65118—Compounds containing hydroxyl groups
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
-
- 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
- D06P1/653—Nitrogen-free carboxylic acids or their salts
- D06P1/6533—Aliphatic, araliphatic or cycloaliphatic
-
- 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
- Y10S8/908—Anionic emulsifiers for dyeing
- Y10S8/91—Soap
Definitions
- This invention relates to compositions for use in dyeing threads, filaments, fibres, fabrics and the like.
- An advantageous method of dyeing hydrophobic threads and fabrics of synthetic materials, and in particular of cellulose triacetate, polymers and copolymers of acrylonitrile and polyethylene terephthalate comprises immersing the threads or fabrics in a dyebath containing a dispersed acetate dyestuif in the presence of a cyclohexyl phenol, octyl phenol or octyl cresol as carrier.
- the substituted phenol may be included in the dyebath or the threads or fabric may be impregnated with the substituted phenol before being immersed in the dyebath.
- the effect of the carrier is to facilitate the dyeing operation, giving deeper shades with excellent fastness properties.
- the carrier which is water-insoluble, should be finely and evenly dispersed in the dyebath and remain so at elevated dyeing temperatures.
- the substituted phenol carriers do not readily disperse in water using standard methods and the present invention provides a stable composition containing the carrier which can be quickly stirred into hot water to produce a pretreatment bath or to produce a bath to which the dye may be added or which may be added to a dyebath by the dyer, as required, to produce a stable and even dispersion of the carrier in the water or dyebath.
- a homogeneous composition for use in dyeing threads, filaments, fibres, fabrics and the like consists essentially of a mixture of a soap, a water-miscible alcohol having a boiling point above 75 C., water and a cyclohexyl phenol, octyl phenol, or octyl cresol, the weight of the soap in the mixture being from 40 to 80 percent, and preferably from 60 to 65 percent, of the Weight of the substituted phenol in the mixture.
- each 100 parts by weight of soap in the composition there are preferably from 60 to 200 parts byweight of water and from 150 to 200 parts by weight of the alcohol.
- compositions of the present invention therefore contain the four ingredients specified in the following range of proportions by weight, taking the proportion of soap as the basis:
- Preferred alcohols for use in this invention are npropyl, iso-propyl, and the tertiary-butyl alcohols.
- the soap used may be any of the normal types of soap obtained by neutralising fatty acids containing at least 12 carbon atoms in the molecule, or mixtures of such acids, with an alkali such as caustic soda or caustic potash.
- the soap used preferably has a titer of 20 2,960,381 Patented Nov. 15, 1960 to 40; thus the alkali metal soaps of the fatty acids or mixed fatty acids present in olive oil, coconut oil, palmnut oil and cotton seed oil may be used with advantage in the present invention.
- Preferred compounds are those in which the hydroxyl group is in the para portion relative to the bond joining the benzene and cyclohexyl rings, i.e. para cyclohexyl phenol.
- the cyclohexyl ring may be substituted by alkyl groups as in the methyl cyclohexyl phenol and dimethyl cyclohexyl phenol represented by the formulae OHrCHz CHz-C Ha OHS-CH OHZ-CH Cfis and bornyl phenol (IJHa).
- the compositions according to this invention may be conveniently prepared by mixing together the soap and the water until the soap is fully swollen, and then, while stirring and heating at 60-70 C., adding first the alcohol and then the substituted phenol in the solid or molten state.
- Example 1 16 parts of low (20 to 22) titre soap based mainly on coconut oil were swollen at room temperature with 32v whereupon a clear homogeneous liquid was obtained. On adding this liquid to the requisite volume of hot water at 55 C., to produce a concentration of the substituted phenol of between 1 gram/litre andgramsflitre, a fine stable dispersion was formed which retained its stability on heating to the boil as in dyeing. The liquid obtained can be used for pretreating triacetate fabrics.
- a dispersed dyestufli is preferably added to the dispersion obtained but, the dyestufi may be added to the hot water before the dispersion is added.
- the alcohol may be replaced by n propanol or by tertiary butyl alcohol.
- Example 2 16 parts of low (20 to 22) titre soap based mainly on coconut oil were swollen at room temperature with 32 parts of water. 27 parts by weight of tertiary butyl alcohol were then added and the mixture was heated to 70 C. with continuous stirring. 25 parts of solid octyl phenol were then added and the heating at 70 C. and the stirring were continued until complete homogeneity was obtained. The mixture, on cooling, was a clear homogeneous liquid giving stable finely-divided dispersions for preparing pretreatment baths or dyebaths as described in Example 1.
- cyclohexyl phenols such as para-cyclohexyl phenol, methyl cyclohexyl phenol, bornyl phenol and menthyl phenol may be used.
- a homogeneous composition for use in dyeing filamentary material made by mixing 100 parts by weight of a soap and from to 200 parts by weight of water until the soap is fully swollen, raising the temperature of the mixture to 60 C. to C. and, while maintaining the mixture in said temperature range, stirring into the mixture first from 150 to 200 parts by Weight of a water miscible alcohol having a boiling point above C. and then from 125 to 250 parts of a substituted phenol selected from the group consisting of cyclohexyl phenol, substituted cyclohexyl phenol-s, octyl phenol and octyl cresol.
- composition claimed in claim 1 wherein the soap has a titre of 20 to 40.
- composition claimed in claim 1 wherein the alcohol is isopropanol.
- composition claimed in claim 1 wherein the substituted phenol is dimethyl cyclohexyl phenol.
- composition claimed in claim 1 in which the proportion of substituted phenol is from 154 to 167 parts by weight per parts of soap.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB29493/57A GB839707A (en) | 1957-09-19 | 1957-09-19 | Improved compositions for use in dyeing threads, filaments, fibres, fabrics and the like |
Publications (1)
Publication Number | Publication Date |
---|---|
US2960381A true US2960381A (en) | 1960-11-15 |
Family
ID=10292419
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US760100A Expired - Lifetime US2960381A (en) | 1957-09-19 | 1958-09-10 | Dyeing of threads, filaments, fibres and the like |
Country Status (4)
Country | Link |
---|---|
US (1) | US2960381A (en(2012)) |
BE (1) | BE571349A (en(2012)) |
FR (1) | FR1202580A (en(2012)) |
GB (1) | GB839707A (en(2012)) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3476500A (en) * | 1965-08-09 | 1969-11-04 | Allied Chem | Concentrated colorants |
US3480377A (en) * | 1964-05-06 | 1969-11-25 | Lever Brothers Ltd | Solvent dyeing of living human hair |
US4519805A (en) * | 1980-12-30 | 1985-05-28 | Ciba Geigy Corporation | Vat dye and sulfur dye compositions |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2394689A (en) * | 1944-01-07 | 1946-02-12 | American Viscose Corp | Method of dyeing |
-
0
- BE BE571349D patent/BE571349A/xx unknown
-
1957
- 1957-09-19 GB GB29493/57A patent/GB839707A/en not_active Expired
-
1958
- 1958-09-10 US US760100A patent/US2960381A/en not_active Expired - Lifetime
- 1958-09-15 FR FR1202580D patent/FR1202580A/fr not_active Expired
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2394689A (en) * | 1944-01-07 | 1946-02-12 | American Viscose Corp | Method of dyeing |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3480377A (en) * | 1964-05-06 | 1969-11-25 | Lever Brothers Ltd | Solvent dyeing of living human hair |
US3476500A (en) * | 1965-08-09 | 1969-11-04 | Allied Chem | Concentrated colorants |
US4519805A (en) * | 1980-12-30 | 1985-05-28 | Ciba Geigy Corporation | Vat dye and sulfur dye compositions |
US4886549A (en) * | 1980-12-30 | 1989-12-12 | Ciba-Geiegy Corporation | Vat dye and sulfur dye compositions |
Also Published As
Publication number | Publication date |
---|---|
FR1202580A (fr) | 1960-01-12 |
BE571349A (en(2012)) | |
GB839707A (en) | 1960-06-29 |
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