CA1249899A - Polydimethylsiloxanes having improved thermal stability - Google Patents
Polydimethylsiloxanes having improved thermal stabilityInfo
- Publication number
- CA1249899A CA1249899A CA000478985A CA478985A CA1249899A CA 1249899 A CA1249899 A CA 1249899A CA 000478985 A CA000478985 A CA 000478985A CA 478985 A CA478985 A CA 478985A CA 1249899 A CA1249899 A CA 1249899A
- Authority
- CA
- Canada
- Prior art keywords
- percent
- weight
- acetylacetonate
- omega
- bis
- 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
- 235000013870 dimethyl polysiloxane Nutrition 0.000 title claims abstract description 32
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 title claims abstract description 29
- -1 Polydimethylsiloxanes Polymers 0.000 title description 15
- 239000000203 mixture Substances 0.000 claims abstract description 60
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 17
- PYPNFSVOZBISQN-LNTINUHCSA-K cerium acetylacetonate Chemical compound [Ce+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O PYPNFSVOZBISQN-LNTINUHCSA-K 0.000 claims abstract description 11
- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims description 30
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 21
- 150000001735 carboxylic acids Chemical class 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 14
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 10
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 claims description 10
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 8
- 239000012530 fluid Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 230000001590 oxidative effect Effects 0.000 abstract description 9
- 239000000314 lubricant Substances 0.000 abstract description 4
- 239000000835 fiber Substances 0.000 abstract description 2
- SHWZFQPXYGHRKT-FDGPNNRMSA-N (z)-4-hydroxypent-3-en-2-one;nickel Chemical compound [Ni].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O SHWZFQPXYGHRKT-FDGPNNRMSA-N 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000000654 additive Substances 0.000 description 15
- 230000000996 additive effect Effects 0.000 description 9
- 239000002253 acid Substances 0.000 description 7
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 6
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000011833 salt mixture Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical class C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
- 150000000703 Cerium Chemical class 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical class [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229920005610 lignin Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003232 pyrogallols Chemical class 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0091—Complexes with metal-heteroatom-bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/620,972 US4528313A (en) | 1984-06-15 | 1984-06-15 | Polydimethylsiloxanes having improved thermal stability |
| US620,972 | 1984-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1249899A true CA1249899A (en) | 1989-02-07 |
Family
ID=24488176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000478985A Expired CA1249899A (en) | 1984-06-15 | 1985-04-12 | Polydimethylsiloxanes having improved thermal stability |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4528313A (OSRAM) |
| EP (1) | EP0166279B1 (OSRAM) |
| JP (1) | JPS6112749A (OSRAM) |
| CA (1) | CA1249899A (OSRAM) |
| DE (1) | DE3570686D1 (OSRAM) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4528313A (en) * | 1984-06-15 | 1985-07-09 | Dow Corning Corporation | Polydimethylsiloxanes having improved thermal stability |
| JPS6211768A (ja) * | 1985-07-10 | 1987-01-20 | Shin Etsu Chem Co Ltd | 室温硬化性シリコ−ンゴム組成物 |
| JPS62149751A (ja) * | 1985-12-25 | 1987-07-03 | Dow Corning Kk | 耐熱性ポリオルガノシロキサン組成物 |
| US4677147A (en) * | 1986-03-24 | 1987-06-30 | Dow Corning Corporation | Bakeware release coating |
| US4801642A (en) * | 1987-12-28 | 1989-01-31 | Dow Corning Corporation | Thermally stable organosiloxane compositions and method for preparing same |
| US4898903A (en) * | 1989-03-14 | 1990-02-06 | Dow Corning Corporation | Thermally stable fluorinated organosiloxane gel composition |
| US5059649A (en) * | 1989-11-08 | 1991-10-22 | Dow Corning Corporation | Storage stable one-part fluorosilicone gel compositions exhibiting improved thermal stability |
| JP3088011B2 (ja) * | 1990-01-30 | 2000-09-18 | 東レ・ダウコーニング・シリコーン株式会社 | 加熱硬化性オルガノポリシロキサン組成物 |
| EP0440168A3 (en) * | 1990-01-30 | 1993-01-07 | Dow Corning Toray Silicone Company, Limited | One-part curable organosiloxane composition |
| US5204384A (en) * | 1991-01-23 | 1993-04-20 | Dow Corning Toray Silicone Co., Ltd. | One-part curable organosiloxane composition |
| DE4401606A1 (de) * | 1994-01-20 | 1995-07-27 | Wacker Chemie Gmbh | Hitzestabilisierte, zu Elastomeren vernetzbare Organopolysiloxanmassen |
| RU2291877C1 (ru) * | 2005-11-09 | 2007-01-20 | Федеральное государственное унитарное предприятие "Государственный научно-исследовательский институт химии и технологии элементоорганических соединений" (ФГУП ГНИИХТЭОС) | Кремнийорганические карбоксилаты редкоземельных элементов в качестве термостабилизаторов полидиорганосилоксановых жидкостей и способ их получения |
| FR2907458A1 (fr) * | 2006-10-24 | 2008-04-25 | Rhodia Recherches & Tech | Composition silicone elastomere reticulant a chaud, thermiquement stable |
| JP2008291069A (ja) * | 2007-05-22 | 2008-12-04 | Momentive Performance Materials Japan Kk | 熱伝導性シリコーングリース組成物 |
| RU2357979C1 (ru) * | 2007-11-07 | 2009-06-10 | Открытое акционерное общество "Всероссийский научно-исследовательский институт по переработке нефти" | Способ получения присадки к олиго-(поли-)органосилоксанам |
| FR2954332B1 (fr) * | 2009-12-22 | 2012-01-13 | Michelin Soc Tech | Article notamment pneumatique avec melange de caoutchouc externe comportant un sel de lanthanide |
| EP2764055B1 (en) * | 2011-10-06 | 2018-03-21 | Dow Corning Corporation | Method of forming a gel having improved thermal stability |
| RU2649392C2 (ru) | 2014-04-11 | 2018-04-03 | Федеральное государственное бюджетное учреждение науки Институт синтетических полимерных материалов им. Н.С. Ениколопова Российской академии наук (ИСПМ РАН) | Функциональные металлосилоксаны, продукты их частичного гидролиза и их применение |
| JP6409704B2 (ja) | 2015-07-24 | 2018-10-24 | 信越化学工業株式会社 | シリコーンゲル組成物及びシリコーンゲル硬化物 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2445567A (en) * | 1948-07-20 | Stabilizing organo-substituted | ||
| US2465296A (en) * | 1944-09-20 | 1949-03-22 | Westinghouse Electric Corp | Metal chelate stabilized organic silicon compositions and products thereof |
| US4070343A (en) * | 1975-09-26 | 1978-01-24 | Toray Silicone Company, Ltd. | Heat stable organopolysiloxane composition |
| US4528313A (en) * | 1984-06-15 | 1985-07-09 | Dow Corning Corporation | Polydimethylsiloxanes having improved thermal stability |
-
1984
- 1984-06-15 US US06/620,972 patent/US4528313A/en not_active Expired - Lifetime
-
1985
- 1985-04-12 CA CA000478985A patent/CA1249899A/en not_active Expired
- 1985-06-07 EP EP85107031A patent/EP0166279B1/en not_active Expired
- 1985-06-07 DE DE8585107031T patent/DE3570686D1/de not_active Expired
- 1985-06-13 JP JP60129115A patent/JPS6112749A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0166279A2 (en) | 1986-01-02 |
| EP0166279A3 (en) | 1987-01-14 |
| EP0166279B1 (en) | 1989-05-31 |
| JPS6112749A (ja) | 1986-01-21 |
| DE3570686D1 (en) | 1989-07-06 |
| JPS6354309B2 (OSRAM) | 1988-10-27 |
| US4528313A (en) | 1985-07-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |