CA1245668A - Organosiloxane polymers and treatment of fibres therewith - Google Patents
Organosiloxane polymers and treatment of fibres therewithInfo
- Publication number
- CA1245668A CA1245668A CA000440369A CA440369A CA1245668A CA 1245668 A CA1245668 A CA 1245668A CA 000440369 A CA000440369 A CA 000440369A CA 440369 A CA440369 A CA 440369A CA 1245668 A CA1245668 A CA 1245668A
- Authority
- CA
- Canada
- Prior art keywords
- groups
- group
- organosiloxanes
- fibres
- organosiloxane
- 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
- 125000005375 organosiloxane group Chemical group 0.000 title claims abstract description 48
- 238000011282 treatment Methods 0.000 title claims abstract description 9
- 229920000642 polymer Polymers 0.000 title abstract description 5
- 239000004753 textile Substances 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 11
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000005864 Sulphur Substances 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 239000000839 emulsion Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 abstract description 8
- -1 aminosiloxanes Chemical class 0.000 description 19
- 239000004744 fabric Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 10
- 229920001296 polysiloxane Polymers 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- 238000011067 equilibration Methods 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 235000014121 butter Nutrition 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000008268 mayonnaise Substances 0.000 description 5
- 235000010746 mayonnaise Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004900 laundering Methods 0.000 description 4
- 239000004006 olive oil Substances 0.000 description 4
- 235000008390 olive oil Nutrition 0.000 description 4
- 239000012188 paraffin wax Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 3
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 2
- FFGHLLOLFQHABK-UHFFFAOYSA-L dibutyltin(2+);dodecane-1-thiolate Chemical compound CCCCCCCCCCCCS[Sn](CCCC)(CCCC)SCCCCCCCCCCCC FFGHLLOLFQHABK-UHFFFAOYSA-L 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229910020175 SiOH Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- NBJODVYWAQLZOC-UHFFFAOYSA-L [dibutyl(octanoyloxy)stannyl] octanoate Chemical compound CCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCC NBJODVYWAQLZOC-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004855 creaseproofing Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011953 free-radical catalyst Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000003039 volatile agent Substances 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/28—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen sulfur-containing groups
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/647—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing polyether sequences
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Silicon Polymers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8232646 | 1982-11-16 | ||
| GB8232646 | 1982-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1245668A true CA1245668A (en) | 1988-11-29 |
Family
ID=10534282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000440369A Expired CA1245668A (en) | 1982-11-16 | 1983-11-03 | Organosiloxane polymers and treatment of fibres therewith |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US4599438A (en, 2012) |
| EP (1) | EP0109214B1 (en, 2012) |
| JP (1) | JPS59100136A (en, 2012) |
| CA (1) | CA1245668A (en, 2012) |
| DE (1) | DE3364275D1 (en, 2012) |
| ES (1) | ES8602169A1 (en, 2012) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4501619A (en) * | 1983-11-14 | 1985-02-26 | Dow Corning Corporation | Aqueous emulsions of carboxyl-containing silicone fluids and a method for their preparation |
| JPS60191039A (ja) * | 1984-03-07 | 1985-09-28 | Shin Etsu Chem Co Ltd | 光フアイバ−用被覆材 |
| JP2538246B2 (ja) * | 1987-04-24 | 1996-09-25 | 東レ・ダウコーニング・シリコーン株式会社 | 繊維処理剤 |
| MY106342A (en) * | 1989-05-02 | 1995-05-30 | Colgate Palmolive Co | Antistatic compositions, antistatic detergent compositions and articles |
| JP2561903B2 (ja) * | 1990-07-27 | 1996-12-11 | 竹本油脂株式会社 | 綿ベールの製造方法及び該製造方法によって得られる綿ベール |
| US5300239A (en) * | 1990-08-24 | 1994-04-05 | Dow Corning Toray Silicone Co., Ltd. | Water-repellent and oil-repellent treatment |
| US5383903A (en) * | 1992-08-20 | 1995-01-24 | United States Surgical Corporation | Dimethylsiloxane-alkylene oxide copolymer coatings for filaments |
| US5879749A (en) * | 1997-09-16 | 1999-03-09 | National Starch And Chemical Investment Holding Corporation | Crosslinkable fabric care compositions |
| US6136215A (en) * | 1999-09-02 | 2000-10-24 | Dow Corning Corporation | Fiber treatment composition containing amine-, polyol-, amide-functional siloxanes |
| US6171515B1 (en) * | 1999-09-02 | 2001-01-09 | Dow Corning Corporation | Fiber treatment composition containing amine-, polyol-, functional siloxanes |
| CA2415762A1 (en) * | 2000-07-07 | 2002-01-17 | Milliken & Company | Textile substrates having durable water repellency and soil release and method for producing same |
| US7294357B2 (en) | 2001-09-28 | 2007-11-13 | Tyco Healthcare Group Lp | Plasma coated sutures |
| US6558409B1 (en) | 2001-09-28 | 2003-05-06 | Tyco Healthcare Group Lp | Plasma treated surgical needles and methods for their manufacture |
| US20040147188A1 (en) * | 2003-01-28 | 2004-07-29 | 3M Innovative Properties Company | Fluorochemical urethane composition for treatment of fibrous substrates |
| WO2006106362A1 (en) * | 2005-04-06 | 2006-10-12 | Dow Corning Corporation | Organosiloxane compositions |
| GB0506939D0 (en) * | 2005-04-06 | 2005-05-11 | Dow Corning | Organosiloxane compositions |
| GB0905204D0 (en) | 2009-03-26 | 2009-05-13 | Dow Corning | Preparation of organosiloxane polymers |
| GB0905205D0 (en) | 2009-03-26 | 2009-05-13 | Dow Corning | Preparation of organosiloxane polymer |
| DE102010021465A1 (de) | 2010-05-25 | 2011-12-01 | Clariant International Ltd. | Wässrige Polyurethan-Polyharnstoff-Dispersionen |
| DE102011107873B4 (de) | 2011-07-19 | 2015-12-03 | Stahl International Bv | Verfahren zur Herstellung von Seitenketten enthaltenden Polyurethan-Polyharnstoffen und deren wässrigen Dispersionen |
| CN104387962A (zh) * | 2014-12-08 | 2015-03-04 | 江苏诺飞新材料科技有限公司 | 抗沾污有机硅表面处理剂 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3318843A (en) * | 1967-05-09 | Process for making equilibration of organopolysiloxanes using phos- phorous-containing catalysts | ||
| JPS35795B1 (en, 2012) * | 1955-08-22 | 1960-02-09 | ||
| US3629309A (en) * | 1956-10-12 | 1971-12-21 | Union Carbide Corp | Organosilicon compounds and processes for producing the same |
| US2875177A (en) * | 1957-03-20 | 1959-02-24 | Gen Electric | Preparation of organopolysiloxanes containing silicon-bonded carboxyalkyl groups |
| US3227579A (en) * | 1960-08-15 | 1966-01-04 | Gen Electric | Water repellent compositions |
| US3177178A (en) * | 1962-12-24 | 1965-04-06 | Gen Electric | Process for making organopolysiloxanes |
| US3271359A (en) * | 1962-12-24 | 1966-09-06 | Gen Electric | Equilibration of organopolysiloxanes using phosphorus-containing catalysts |
| NL133796C (en, 2012) * | 1965-01-21 | 1900-01-01 | ||
| BE754332A (fr) * | 1969-08-05 | 1971-02-03 | Dow Corning | Copolymeres de siloxanes a fonctionnalite carboxyle utiles comme agent d'encollage et papier encolle a l'aide de ces copolymeres |
| US3639156A (en) * | 1970-05-19 | 1972-02-01 | Us Agriculture | Siloxane polymers for soil-repellent and soil-release textile finishes |
| US3715377A (en) * | 1971-12-16 | 1973-02-06 | Gen Electric | Preparation of organosilicone esters |
| US3812201A (en) * | 1972-02-25 | 1974-05-21 | Corning Corp | Textile finishing composition and process |
| US3884860A (en) * | 1974-04-15 | 1975-05-20 | Dow Corning | Carboxy-functional silicones |
| US4311626A (en) * | 1980-09-25 | 1982-01-19 | Toray Silicone Company, Ltd. | Silicone compositions for the treatment of fibers |
-
1983
- 1983-10-24 EP EP83306429A patent/EP0109214B1/en not_active Expired
- 1983-10-24 DE DE8383306429T patent/DE3364275D1/de not_active Expired
- 1983-10-31 US US06/546,793 patent/US4599438A/en not_active Expired - Lifetime
- 1983-11-03 CA CA000440369A patent/CA1245668A/en not_active Expired
- 1983-11-15 ES ES527273A patent/ES8602169A1/es not_active Expired
- 1983-11-16 JP JP58214231A patent/JPS59100136A/ja active Granted
-
1985
- 1985-12-27 US US06/813,807 patent/US4624676A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4599438A (en) | 1986-07-08 |
| JPS6233250B2 (en, 2012) | 1987-07-20 |
| ES527273A0 (es) | 1985-11-01 |
| ES8602169A1 (es) | 1985-11-01 |
| EP0109214A1 (en) | 1984-05-23 |
| JPS59100136A (ja) | 1984-06-09 |
| DE3364275D1 (en) | 1986-07-31 |
| EP0109214B1 (en) | 1986-06-25 |
| US4624676A (en) | 1986-11-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |