GB836241A - Improvements in organophosphorus-silicon compounds - Google Patents
Improvements in organophosphorus-silicon compoundsInfo
- Publication number
- GB836241A GB836241A GB15123/57A GB1512357A GB836241A GB 836241 A GB836241 A GB 836241A GB 15123/57 A GB15123/57 A GB 15123/57A GB 1512357 A GB1512357 A GB 1512357A GB 836241 A GB836241 A GB 836241A
- Authority
- GB
- United Kingdom
- Prior art keywords
- silane
- phosphonoethyl
- dibutyl
- diethyl
- radical
- 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
- -1 alkenyl silane Chemical compound 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229920001296 polysiloxane Polymers 0.000 abstract 4
- 229920001577 copolymer Polymers 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 abstract 2
- GTFCGGRNRKNFAC-UHFFFAOYSA-N 2-[bis(2-chloroethoxy)phosphoryl]ethyl-diethoxy-phenylsilane Chemical compound ClCCOP(=O)(OCCCl)CC[Si](C1=CC=CC=C1)(OCC)OCC GTFCGGRNRKNFAC-UHFFFAOYSA-N 0.000 abstract 1
- SQYIVIJLGCGFQX-UHFFFAOYSA-N 2-[dibutyl(2,2-diethoxyethenyl)silyl]ethylphosphonic acid Chemical compound C(CCC)[Si](C=C(OCC)OCC)(CCP(=O)(O)O)CCCC SQYIVIJLGCGFQX-UHFFFAOYSA-N 0.000 abstract 1
- LJHPWEYOQVNDEC-UHFFFAOYSA-N 2-[diethoxy(5-methylnonan-5-yloxy)silyl]ethylphosphonic acid Chemical compound C(CCC)C(C)(O[Si](OCC)(OCC)CCP(=O)(O)O)CCCC LJHPWEYOQVNDEC-UHFFFAOYSA-N 0.000 abstract 1
- WQFSKNIIXSZPJV-UHFFFAOYSA-N 2-[diethoxymethyl(dimethyl)silyl]ethylphosphonic acid Chemical compound C[Si](C(OCC)OCC)(CCP(=O)(O)O)C WQFSKNIIXSZPJV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- JVZDKVMDAXTVQH-UHFFFAOYSA-N 3-[diethoxy(3-methylpentan-3-yloxy)silyl]propylphosphonic acid Chemical compound CCC(C)(CC)O[Si](OCC)(OCC)CCCP(O)(O)=O JVZDKVMDAXTVQH-UHFFFAOYSA-N 0.000 abstract 1
- DMVJYXPKKMXPRJ-UHFFFAOYSA-N C(CCC)C=1C(=C(C=CC1)[Si](C1=CC=CC=C1)(OCC)CCP(=O)(O)O)CCCC Chemical compound C(CCC)C=1C(=C(C=CC1)[Si](C1=CC=CC=C1)(OCC)CCP(=O)(O)O)CCCC DMVJYXPKKMXPRJ-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 239000003849 aromatic solvent Substances 0.000 abstract 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 abstract 1
- JSODCNQNZVRUFT-UHFFFAOYSA-N bis(2-dibutoxyphosphorylethyl)-diethoxysilane Chemical compound C(CCC)OP(=O)(OCCCC)CC[Si](OCC)(OCC)CCP(=O)(OCCCC)OCCCC JSODCNQNZVRUFT-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000004132 cross linking Methods 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- UBIJTWDKTYCPMQ-UHFFFAOYSA-N hexachlorophosphazene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 UBIJTWDKTYCPMQ-UHFFFAOYSA-N 0.000 abstract 1
- 229920001519 homopolymer Polymers 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000010687 lubricating oil Substances 0.000 abstract 1
- 125000005394 methallyl group Chemical group 0.000 abstract 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 239000005060 rubber Substances 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
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 229910052718 tin Inorganic materials 0.000 abstract 1
- IZRJPHXTEXTLHY-UHFFFAOYSA-N triethoxy(2-triethoxysilylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CC[Si](OCC)(OCC)OCC IZRJPHXTEXTLHY-UHFFFAOYSA-N 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052726 zirconium Inorganic materials 0.000 abstract 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
- C08G77/30—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen phosphorus-containing groups
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
- C07F9/4012—Esters of acyclic acids which can have further substituents on alkyl substituted by B, Si, P or a metal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
Abstract
The invention comprises organophosphorus derivatives of silicon having the general formula <FORM:0836241/IV (a)/1> where R and R11 are monovalent hydrocarbon or halogenated hydrocarbon radicals, R1 is a monovalent hydrocarbon radical, all of them being free from aliphatic unsaturation, Z is an alkylene radical of at least 2 carbon atoms or such a radical in which a hydrogen atom is replaced by a silanyl radical, m is 1, 2 or 3, n is 0, 1 or 2, and m+n is not more than 3. They may be prepared by reacting a di-organohydrogen phosphite of the formula HP(O)(OR)2 with an alkenyl silane of the formula AmSi(R11)n(OR1)4-m-n, where A is an alkenyl group, e.g. vinyl, allyl or methallyl. A catalyst is preferably employed, particularly azo and peroxy compounds, potassium metal and potassium organo derivatives. Temperatures are generally from about 75 DEG C. upwards. The compounds can be hydrolysed, alone or with other hydrolysable silanes, silanols or siloxanols, to give polysiloxanes. Copolymers may also be formed by co-condensing the homopolymer with other polysiloxanes. The examples describe the preparation of: diethyl and dibutyl phosphonoethyltriethoxysilane; diethyl and dimethyl phosphonoethyldiethoxymethyl silane; diethyl phosphonopropyl triethoxy silane; di-(chloroethyl)phosphonoethyl diethoxyphenyl silane; dibutyl phosphonoethyl ethoxydiphenyl silane; bis-(dibutyl phosphonoethyl)-diethoxy silane; dibutyl phosphonoethyl diethoxyvinyl silane; and the compound 2-(diethyl phosphono), 2-(triethoxysilyl)-ethyl triethoxy silane is also mentioned. The preparation of polysiloxanes, including copolymers, from the above compounds is described, using as catalysts phosphorus oxychloride, phosphonitrilic chloride trimer or tetramer or fuming sulphuric acid. Some cross-linking may develop through hydrolysis of the OR group on the phosphorus to give <FORM:0836241/IV (a)/2> groupings. As further condensing agents, there are also specified zinc, tin and zirconium octoates and tetramethyl ammonium hydroxide. Copolymers of units derived from the above compounds with dimethyl siloxane units which are end-blocked by trimethylsiloxy units are useful as lubricating oils. The polysiloxane gums are convertible to rubbers by the use of the usual fillers and curing agents, and are unaffected by high-energy electrons and are resistant to aromatic solvents.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US836241XA | 1956-05-31 | 1956-05-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB836241A true GB836241A (en) | 1960-06-01 |
Family
ID=22179588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB15123/57A Expired GB836241A (en) | 1956-05-31 | 1957-05-13 | Improvements in organophosphorus-silicon compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB836241A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0525573A1 (en) * | 1991-07-29 | 1993-02-03 | Sanwa Kagaku Kenkyusho Co., Ltd. | Organogermanium and organosilicon compounds, process for the preparation of the same and use thereof |
| EP0720985A1 (en) * | 1995-01-05 | 1996-07-10 | Wacker-Chemie GmbH | Organo silicon compounds containing phosphorus |
| WO2002055587A1 (en) * | 2001-01-09 | 2002-07-18 | Queen Mary & Westfield College | Organopolysiloxanes containing phosphonic groups, methods for the production and use thereof |
-
1957
- 1957-05-13 GB GB15123/57A patent/GB836241A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0525573A1 (en) * | 1991-07-29 | 1993-02-03 | Sanwa Kagaku Kenkyusho Co., Ltd. | Organogermanium and organosilicon compounds, process for the preparation of the same and use thereof |
| EP0720985A1 (en) * | 1995-01-05 | 1996-07-10 | Wacker-Chemie GmbH | Organo silicon compounds containing phosphorus |
| US5627296A (en) * | 1995-01-05 | 1997-05-06 | Wacker-Chemie Gmbh | Phosphorus-containing organosilicon compounds |
| WO2002055587A1 (en) * | 2001-01-09 | 2002-07-18 | Queen Mary & Westfield College | Organopolysiloxanes containing phosphonic groups, methods for the production and use thereof |
| US7064226B2 (en) | 2001-01-09 | 2006-06-20 | Phosphonics Limited | Organopolysiloxanes containing phosphonic groups, method for the production and use thereof |
| US7728159B2 (en) * | 2001-01-09 | 2010-06-01 | Phosphonics Limited | Organopolysiloxanes containing phosphonic groups, method for the production and use thereof |
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