GB1358350A - Stable silanol compositions and process for making them - Google Patents
Stable silanol compositions and process for making themInfo
- Publication number
- GB1358350A GB1358350A GB2443972A GB2443972A GB1358350A GB 1358350 A GB1358350 A GB 1358350A GB 2443972 A GB2443972 A GB 2443972A GB 2443972 A GB2443972 A GB 2443972A GB 1358350 A GB1358350 A GB 1358350A
- Authority
- GB
- United Kingdom
- Prior art keywords
- silanol
- gamma
- solutions
- stable
- silane
- 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
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 title abstract 6
- 239000000203 mixture Substances 0.000 title abstract 2
- 239000000243 solution Substances 0.000 abstract 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 2
- 238000000605 extraction Methods 0.000 abstract 2
- 239000011342 resin composition Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 abstract 1
- JUVSRZCUMWZBFK-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)-4-methylanilino]ethanol Chemical compound CC1=CC=C(N(CCO)CCO)C=C1 JUVSRZCUMWZBFK-UHFFFAOYSA-N 0.000 abstract 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 abstract 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 abstract 1
- 229930185605 Bisphenol Natural products 0.000 abstract 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 abstract 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 abstract 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000011324 bead Substances 0.000 abstract 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 abstract 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 239000010453 quartz Substances 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 229910000077 silane Inorganic materials 0.000 abstract 1
- 150000004756 silanes Chemical class 0.000 abstract 1
- 150000004819 silanols Chemical class 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- HUAUNKAZQWMVFY-UHFFFAOYSA-M sodium;oxocalcium;hydroxide Chemical compound [OH-].[Na+].[Ca]=O HUAUNKAZQWMVFY-UHFFFAOYSA-M 0.000 abstract 1
- -1 triethylene glycol dimethacrylate ester Chemical class 0.000 abstract 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 abstract 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0836—Compounds with one or more Si-OH or Si-O-metal linkage
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/70—Preparations for dentistry comprising inorganic additives
- A61K6/71—Fillers
- A61K6/76—Fillers comprising silicon-containing compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/70—Preparations for dentistry comprising inorganic additives
- A61K6/71—Fillers
- A61K6/77—Glass
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/20—Purification, separation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dental Preparations (AREA)
Abstract
1358350 Stable silanol solutions; polymerization of bis-methacrylates LEE PHARMACEUTICALS 24 May 1972 [24 May 1971] 24439/72 Headings C3S and C3P Stable solutions of silanols of the formula (HO) 3 Si(CH 2 ) n Y, wherein Y denotes an organofunctional group and n is 0 or an integer of from 1 to 3, are prepared by hydrolysing a silane of the formula X 3 Si(CH 2 ) n Y, wherein X denotes a hydrolysable group, and extracting the resulting silanol from the aqueous solution with a non-polar water-immiscible organic solvent in which the silanol is soluble. Suitable starting silanes are vinyl tris(2-methoxyethoxy)- silane, gamma-methacryloxypropyltrimethoxysilane, beta - (3,4 - epoxy - cyclohexyl)ethyltrimethoxysilane, gamma - glycidoxypropyltrimethoxysilane, gamma - mercaptopropyltrimethoxysilane, gamma - aminopropyltriethoxysilane, and N-beta-(aminoethyl)-gammaaminopropyltrimethoxysilane. Hydrolysis may be carried out with an acid or a base and the solvent solution is preferably neutralized after extraction. Suitable extraction solvents are ethyl ether, chloroform and methylene chloride. Uses.-For improvement of bonding of organic resins to mineral surfaces. Thus quartz, soda lime and glass bead fillers treated with the silanol solutions and subsequently with benzoyl peroxide give improved results when mixed with resin compositions based on a mixture of bisphenol - A - bis - (3 - methacrylate - 2 - hydroxypropyl)ether, triethylene glycol dimethacrylate ester, N - 4 - tolyl - diethanolamine and butylated hydroxytoluene. The above resin composition may also be applied to teeth previously treated successively with the silanol solutions and benzoyl peroxide.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14646571A | 1971-05-24 | 1971-05-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1358350A true GB1358350A (en) | 1974-07-03 |
Family
ID=22517483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2443972A Expired GB1358350A (en) | 1971-05-24 | 1972-05-24 | Stable silanol compositions and process for making them |
Country Status (7)
| Country | Link |
|---|---|
| AU (1) | AU472366B2 (en) |
| CA (1) | CA1006169A (en) |
| CH (1) | CH565853A5 (en) |
| DE (1) | DE2225146B2 (en) |
| FR (1) | FR2139097B1 (en) |
| GB (1) | GB1358350A (en) |
| ZA (1) | ZA722919B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0049365A2 (en) * | 1980-10-02 | 1982-04-14 | Hüls Troisdorf Aktiengesellschaft | Stable aqueous impregnating solutions made from hydrolysed alkyltrialkoxysilanes |
| GB2161489A (en) * | 1984-07-12 | 1986-01-15 | Glaverbel | Articles of filled synthetic polymeric materials and glass bead filler therefor |
| US4617327A (en) * | 1983-11-19 | 1986-10-14 | Bayer Aktiengesellschaft | Inorganic-organic fillers for polymerizable compositions |
| US4624971A (en) * | 1981-01-15 | 1986-11-25 | Battelle Development Corporation | Photo setting composition for coating substrates with an abrasion-resistant transparent or translucent film |
| US5380791A (en) * | 1991-12-20 | 1995-01-10 | Degussa Aktiengesellschaft | Method of producing sulfonated organosilicon compounds and coresponding aqueous solutions |
| CN113652113A (en) * | 2021-09-08 | 2021-11-16 | 科顺防水科技股份有限公司 | Modified silane coupling agent and synthetic method thereof, single-component polyurethane waterproof coating composition and preparation method thereof |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3905110A (en) * | 1972-11-03 | 1975-09-16 | Lee Pharmaceuticals | Composition and method for drying dental surfaces |
| US5332429A (en) † | 1991-05-31 | 1994-07-26 | Minnesota Mining And Manufacturing Company | Method for treating fluoroaluminosilicate glass |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR947460A (en) * | 1946-06-24 | 1949-07-04 | Ici Ltd | Manufacturing process of organic silicon compounds |
| US2827474A (en) * | 1953-05-22 | 1958-03-18 | Allied Chem & Dye Corp | Production of reactive organosilanols |
-
1972
- 1972-05-01 ZA ZA722919A patent/ZA722919B/en unknown
- 1972-05-03 AU AU41830/72A patent/AU472366B2/en not_active Expired
- 1972-05-18 FR FR7218788A patent/FR2139097B1/fr not_active Expired
- 1972-05-23 CA CA142,721A patent/CA1006169A/en not_active Expired
- 1972-05-24 DE DE2225146A patent/DE2225146B2/en active Granted
- 1972-05-24 GB GB2443972A patent/GB1358350A/en not_active Expired
- 1972-05-24 CH CH772172A patent/CH565853A5/xx not_active IP Right Cessation
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0049365A2 (en) * | 1980-10-02 | 1982-04-14 | Hüls Troisdorf Aktiengesellschaft | Stable aqueous impregnating solutions made from hydrolysed alkyltrialkoxysilanes |
| EP0049365A3 (en) * | 1980-10-02 | 1982-06-23 | Dynamit Nobel Aktiengesellschaft | Stable aqueous impregnating solutions made from hydrolysed alkyltrialkoxysilanes |
| US4624971A (en) * | 1981-01-15 | 1986-11-25 | Battelle Development Corporation | Photo setting composition for coating substrates with an abrasion-resistant transparent or translucent film |
| US4617327A (en) * | 1983-11-19 | 1986-10-14 | Bayer Aktiengesellschaft | Inorganic-organic fillers for polymerizable compositions |
| GB2161489A (en) * | 1984-07-12 | 1986-01-15 | Glaverbel | Articles of filled synthetic polymeric materials and glass bead filler therefor |
| US5380791A (en) * | 1991-12-20 | 1995-01-10 | Degussa Aktiengesellschaft | Method of producing sulfonated organosilicon compounds and coresponding aqueous solutions |
| CN113652113A (en) * | 2021-09-08 | 2021-11-16 | 科顺防水科技股份有限公司 | Modified silane coupling agent and synthetic method thereof, single-component polyurethane waterproof coating composition and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1006169A (en) | 1977-03-01 |
| AU472366B2 (en) | 1976-05-20 |
| DE2225146B2 (en) | 1975-08-14 |
| DE2225146A1 (en) | 1972-12-14 |
| FR2139097B1 (en) | 1977-12-23 |
| CH565853A5 (en) | 1975-08-29 |
| FR2139097A1 (en) | 1973-01-05 |
| ZA722919B (en) | 1973-02-28 |
| AU4183072A (en) | 1973-11-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |