GB1047037A - Treatment of textile fibres and polymeric sheet materials - Google Patents
Treatment of textile fibres and polymeric sheet materialsInfo
- Publication number
- GB1047037A GB1047037A GB19494/64A GB1949464A GB1047037A GB 1047037 A GB1047037 A GB 1047037A GB 19494/64 A GB19494/64 A GB 19494/64A GB 1949464 A GB1949464 A GB 1949464A GB 1047037 A GB1047037 A GB 1047037A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenol
- aromatic
- ethylene oxide
- methyl
- ortho
- 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
Links
- 239000000463 material Substances 0.000 title abstract 9
- 239000004753 textile Substances 0.000 title abstract 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 13
- -1 octyl phenyl Chemical group 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 6
- 150000001491 aromatic compounds Chemical class 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 4
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 abstract 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- 239000007864 aqueous solution Substances 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 229910015900 BF3 Inorganic materials 0.000 abstract 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N S-phenyl benzenesulfonothioate Natural products C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 235000010292 orthophenyl phenol Nutrition 0.000 abstract 2
- 239000004306 orthophenyl phenol Substances 0.000 abstract 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 abstract 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- 239000004803 Di-2ethylhexylphthalate Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 244000068988 Glycine max Species 0.000 abstract 1
- 235000010469 Glycine max Nutrition 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004677 Nylon Substances 0.000 abstract 1
- 239000004698 Polyethylene Substances 0.000 abstract 1
- 239000004743 Polypropylene Substances 0.000 abstract 1
- 239000004372 Polyvinyl alcohol Substances 0.000 abstract 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 abstract 1
- 229920000297 Rayon Polymers 0.000 abstract 1
- 235000021355 Stearic acid Nutrition 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 229910052788 barium Inorganic materials 0.000 abstract 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000005018 casein Substances 0.000 abstract 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 abstract 1
- 235000021240 caseins Nutrition 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 239000000460 chlorine Chemical group 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000000068 chlorophenyl group Chemical group 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000006289 hydroxybenzyl group Chemical group 0.000 abstract 1
- 229920001778 nylon Polymers 0.000 abstract 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 229920000573 polyethylene Polymers 0.000 abstract 1
- 229920000139 polyethylene terephthalate Polymers 0.000 abstract 1
- 239000005020 polyethylene terephthalate Substances 0.000 abstract 1
- 229920001155 polypropylene Polymers 0.000 abstract 1
- 229920002451 polyvinyl alcohol Polymers 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- 239000005033 polyvinylidene chloride Substances 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- 239000008117 stearic acid Substances 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 229920002994 synthetic fiber Polymers 0.000 abstract 1
- 239000004758 synthetic textile Substances 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/53—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
-
- 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
- Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S524/91—Antistatic compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Compounds suitable for use in the treatment of textile materials and polymeric sheet materials are produced by condensing an aromatic compound containing an aromatic moiety and an aromatic phenolic moiety having at least one phenolic hydroxy group, of which a -methyl benzyl para phenol a -methyl benzyl ortho phenol, ortho phenyl phenol, para phenyl phenol and 4-methyl-41-hydroxy diphenyl sulphone are specified, with 5-20 moles of ethylene oxide per phenolic hydroxy group contained within the compound. In Example I a -methyl benzyl para phenol is prepared by the reaction of phenol with styrene in the presence of a catalyst consisting of boron trifluoride and an aqueous solution of hypophosphorous acid, and is then condensed with 9 moles of ethylene oxide.ALSO:Compounds suitable for use in the treatment of textile materials and polymeric sheet materials are produced by condensing an aromatic compound containing an aromatic moiety and an aromatic phenolic moiety having at least one phenolic hydroxy group, of which a -methyl benzyl para phenol, a -methyl benzyl ortho phenol, ortho phenyl phenol, para phenyl phenol and 4-methyl-41-hydroxy diphenyl sulphone are specified, with 5-20 moles of ethylene oxide per phenolic hydroxy group contained within the compound. In Example XI, a resin mixture is prepared from polyvinyl chloride, di-2-ethyl hexyl phthalate, epoxidized soya bean oil, stearic acid, a barium octoate-zinc octoate stabilizer and a condensate of 1 mole of a -methyl benzyl ortho phenol with 9.1 moles of ethylene oxide and made into sheet material.ALSO:A catalytic composition comprises boron trifluoride and an aqueous solution of hypophosphorous acid.ALSO:Natural and synthetic textile materials in the form of fibre, continuous or spun yarns, filaments, rovings, slivers or tops are lubricated and rendered antistatic by treating them with a water-soluble compound produced by condensing an aromatic compound containing an aromatic moiety and an aromatic phenolic moiety having at least one phenolic hydroxy group with 5-20 moles of ethylene oxide per phenolic hydroxy group contained in the compound. The aromatic compound which is condensed with the ethylene oxide may be <FORM:1047037/D1-D2/1> in which R is an aryl or substituted aryl radical containing 6-24 carbon atoms, e.g. phenyl. chlorophenyl, octyl phenyl, diphenyl, hydroxy benzyl, dioctyl-o-hydroxy benzyl or 2-hydroxy-3-(ortho hydroxy benzyl) phenyl, X is hydrogen, chlorine, bromine or a straight or branched chain alkyl radical containing 1-15 carbon atoms and R1 and R2 which may be the same or different are hydrogen or alkyl radicals containing 1-5 carbon atoms. The compounds may be applied to the textile materials from an aqueous solution or solution in an organic solvent, e.g. ether, methyl alcohol, ethyl alcohol or acetone, in an amount of from 0.01-1.3% by weight. Textile materials made from cellulose acetate, nylon, polyethylene terephthalate, acrylic, viscose rayon, polyvinylidene chloride, copolymers of acrylonitrile and polyvinyl alcohol, polyethylene, polypropylene, cotton, wool, linen, silk, casein or vicara fibres may be treated.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28101763A | 1963-05-16 | 1963-05-16 | |
| US575537A US3333983A (en) | 1963-05-16 | 1966-08-29 | Antistatic polymeric materials containing ethylene oxide condensation products of phenolic derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1047037A true GB1047037A (en) | 1966-11-02 |
Family
ID=26960658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19494/64A Expired GB1047037A (en) | 1963-05-16 | 1964-05-11 | Treatment of textile fibres and polymeric sheet materials |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3333983A (en) |
| DE (1) | DE1469503C3 (en) |
| FR (1) | FR1397579A (en) |
| GB (1) | GB1047037A (en) |
| NL (1) | NL147801B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2227491A (en) * | 1989-01-26 | 1990-08-01 | Armstrong World Ind Inc | Antistatic surface covering materials |
| EP2653512A3 (en) * | 2012-04-18 | 2014-09-10 | Dow Global Technologies LLC | Aqueous coating compositions including phenylphenol ethoxylate surfactants |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3428481A (en) * | 1966-07-06 | 1969-02-18 | Du Pont | Antistatic lubricating composition for textile fibers |
| US3653955A (en) * | 1968-05-20 | 1972-04-04 | Deering Milliken Res Corp | Antistatic fiber treatments |
| US3620823A (en) * | 1969-05-19 | 1971-11-16 | Monsanto Co | Process of improving the resistance of soiling of melt spun fibers |
| US3770494A (en) * | 1969-12-18 | 1973-11-06 | Asahi Chemical Ind | Modified acrylonitrile polymer fibers |
| US3873353A (en) * | 1973-03-05 | 1975-03-25 | Allied Chem | Antistatic fiber |
| US3907689A (en) * | 1973-08-29 | 1975-09-23 | Eastman Kodak Co | Textile treating composition and textile yarn treated therewith |
| US3947613A (en) * | 1974-08-07 | 1976-03-30 | The United States Of America As Represented By The Secretary Of Agriculture | Process for reducing agent migration during treatment of knitted cotton fabric |
| DE3126551C2 (en) * | 1981-07-04 | 1983-12-15 | Rolf Dr. 8700 Würzburg Siegel | Manufacturing process for materials for immobilizing proteins and carbohydrate groups |
| US4457874A (en) * | 1981-08-19 | 1984-07-03 | Diamond Shamrock Chemicals Company | Condensation products of substituted phenol sulfonic acid and formaldehyde |
| US4479826A (en) * | 1982-07-09 | 1984-10-30 | Diamond Shamrock Chemicals Company | Condensation products of substituted phenol sulfonic acid and formaldehyde |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1970578A (en) * | 1930-11-29 | 1934-08-21 | Ig Farbenindustrie Ag | Assistants for the textile and related industries |
| US2213477A (en) * | 1935-12-12 | 1940-09-03 | Gen Aniline & Film Corp | Glycol and polyglycol ethers of isocyclic hydroxyl compounds |
| GB614594A (en) * | 1946-07-16 | 1948-12-17 | Geoffrey Philip Lee | Improved articles prepared wholly or in part from polythene compositions |
| NL98396C (en) * | 1953-03-13 |
-
1964
- 1964-04-30 FR FR973160A patent/FR1397579A/en not_active Expired
- 1964-05-11 GB GB19494/64A patent/GB1047037A/en not_active Expired
- 1964-05-15 DE DE1469503A patent/DE1469503C3/en not_active Expired
- 1964-05-15 NL NL646405428A patent/NL147801B/en not_active IP Right Cessation
-
1966
- 1966-08-29 US US575537A patent/US3333983A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2227491A (en) * | 1989-01-26 | 1990-08-01 | Armstrong World Ind Inc | Antistatic surface covering materials |
| GB2227491B (en) * | 1989-01-26 | 1993-01-06 | Armstrong World Ind Inc | Surface covering materials |
| EP2653512A3 (en) * | 2012-04-18 | 2014-09-10 | Dow Global Technologies LLC | Aqueous coating compositions including phenylphenol ethoxylate surfactants |
| US8901213B2 (en) | 2012-04-18 | 2014-12-02 | Dow Global Technologies Llc | Aqueous coating compositions including phenylphenol ethoxylate surfactants |
Also Published As
| Publication number | Publication date |
|---|---|
| US3333983A (en) | 1967-08-01 |
| NL6405428A (en) | 1964-11-17 |
| DE1469503B2 (en) | 1973-10-11 |
| DE1469503A1 (en) | 1969-01-30 |
| DE1469503C3 (en) | 1974-05-16 |
| FR1397579A (en) | 1965-04-30 |
| NL147801B (en) | 1975-11-17 |
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