GB786020A - Organopolysiloxane nitriles - Google Patents
Organopolysiloxane nitrilesInfo
- Publication number
- GB786020A GB786020A GB15829/56A GB1582956A GB786020A GB 786020 A GB786020 A GB 786020A GB 15829/56 A GB15829/56 A GB 15829/56A GB 1582956 A GB1582956 A GB 1582956A GB 786020 A GB786020 A GB 786020A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- siloxane
- hydrolysed
- polysiloxane
- formula
- 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
- 229920001296 polysiloxane Polymers 0.000 title abstract 6
- 150000002825 nitriles Chemical class 0.000 title abstract 3
- -1 polysiloxanes Polymers 0.000 abstract 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 8
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 235000019441 ethanol Nutrition 0.000 abstract 3
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- 239000005046 Chlorosilane Substances 0.000 abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 abstract 2
- 150000001734 carboxylic acid salts Chemical class 0.000 abstract 2
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 abstract 2
- 229920001577 copolymer Polymers 0.000 abstract 2
- NWKBSEBOBPHMKL-UHFFFAOYSA-N dichloro(methyl)silane Chemical compound C[SiH](Cl)Cl NWKBSEBOBPHMKL-UHFFFAOYSA-N 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 229910052739 hydrogen Chemical group 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000005909 Kieselgur Substances 0.000 abstract 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004965 Silica aerogel Substances 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 239000003610 charcoal Substances 0.000 abstract 1
- XGLLBUISUZEUMW-UHFFFAOYSA-N chloromethyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(CCl)OCC XGLLBUISUZEUMW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 229910052570 clay Inorganic materials 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 abstract 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 239000003517 fume Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 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 abstract 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 239000010453 quartz Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000005060 rubber Substances 0.000 abstract 1
- 229910000077 silane Inorganic materials 0.000 abstract 1
- 239000004408 titanium dioxide Substances 0.000 abstract 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 239000011787 zinc oxide Substances 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
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-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
- 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
-
- 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
- C07F7/12—Organo silicon halides
- C07F7/14—Preparation thereof from optionally substituted halogenated silanes and hydrocarbons hydrosilylation reactions
-
- 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention comprises polysiloxanes of the formula: <FORM:0786020/IV (a)/1> wherein R1 is CH3 or H, n has an average value of 1 to 3, and R is a monovalent hydrocarbon radical free from aliphatic unsaturation. They may be prepared by (1) reacting the corresponding unsaturated nitrile with a silane of the formula RSiHCl2 in the presence of platinum dispersed on charcoal, and then hydrolysing; or (2) condensing a chloromethylalkoxysilane with an ethyl cyanoacetate in the presence of sodium, hydrolysing and decarboxylating the product to give a cyanoethyl siloxane. Copolymers containing 0.1 to 99.9 mol. per cent of the above units, the remainder being units of the formula R11mSiO 4-m/2 , where R11 is a monovalent hydrocarbon radical, may be prepared by cohydrolysing the corresponding chlorosilanes or by catalytic interaction of the siloxanes. In the above formul , R may be alkyl, cycloalkyl, aryl or aralkyl. R11 may be similar and also includes alkenyl radicals. The polysiloxane nitriles form rubbers when vulcanized with, for example, peroxides; combinations of alkyl polysilicates with carboxylic acid salts; combinations of hydrogen-containing siloxanes and carboxylic acid salts; or, when the siloxane contains alkenyl groups, sulphur with or without accelerators. Fillers may also be incorporated, e.g. silica aerogel, fume silicas, diatomaceous earth, titanium dioxide, clay, zinc oxide, ferric oxide and crushed quartz. In the examples: (1) the compound MeSi(Cl)2(CH2)4CN is prepared from CH2 = CHCH2CH2CN and MeSiHCl2, and is hydrolysed to a syrupy polysiloxane of unit formula NC(CH2)4Si(Me)O. This is copolymerized with an equimolecular amount of octamethylcyclotetrasiloxane; (2) the compound (EtO)2 SiMeCH2C.(CN).HCOOEt is prepared by refluxing chloromethylmethyldiethoxysilane with ethyl cyanoacetate in ethyl alcohol containing sodium. This is hydrolysed with KOH in ethanol, the ethanol is removed and the siloxane neutralized with HCl. This is decarboxylated by heating at 185 DEG C. to give a rubbery siloxane of unit formula NC(CH2)2Si(Me)O; (3) the compound NC(CH2)3SiMeCl2 is prepared from MeSiHCl2 and allyl cyanide, and is hydrolysed to a viscous siloxane NC(CH2)3Si(Me)O; (4) NC.CHMeCOOEt is used instead of the ethyl cyanoacetate in Example (2) and a polysiloxane NC.CHMeCH2Si(Me)O is obtained; (5) PhSi (Cl2)(CH2)4CN is prepared from PhSiHCl2 an CH2 = CHCH2CH2CN, and is hydrolysed to a viscous siloxane NC(CH2)4Si(Ph)O. This is reacted with 0.01 mol. per cent of hexamethyldisiloxane in the presence of Me3SiOK to give a liquid trimethylsilyl end-blocked polysiloxane; (6) a resinous copolymer of NC(CH2)3 Si(Me)O, monovinylsiloxane, octadecylmethylsiloxane, phenylmethylsiloxane and monomethylsiloxane is obtained by hydrolysis of the corresponding chlorosilanes.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US786020XA | 1955-07-18 | 1955-07-18 | |
| US1115026XA | 1955-07-18 | 1955-07-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB786020A true GB786020A (en) | 1957-11-06 |
Family
ID=26760733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB15829/56A Expired GB786020A (en) | 1955-07-18 | 1956-05-22 | Organopolysiloxane nitriles |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1115026B (en) |
| GB (1) | GB786020A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2907784A (en) * | 1957-06-28 | 1959-10-06 | Union Carbide Corp | Preparation of cyanoalkylsilanes employing trihydrocarbyl phosphine catalysts |
| US2970150A (en) * | 1957-12-17 | 1961-01-31 | Union Carbide Corp | Processes for the reaction of silanic hydrogen-bonded siloxanes with unsaturated organic compounds with a platinum catalyst |
| US2971972A (en) * | 1959-03-30 | 1961-02-14 | Gen Electric | Addition reaction |
| DE1115463B (en) * | 1958-11-17 | 1961-10-19 | Union Carbide Corp | Process for the preparation of organopolysiloxanes |
| US3026278A (en) * | 1957-11-29 | 1962-03-20 | Union Carbide Corp | Cyanoalkylsiloxane copolymers |
| US3112332A (en) * | 1958-06-25 | 1963-11-26 | Union Carbide Corp | Cyanoalkylsilanediols |
| US3167573A (en) * | 1960-11-14 | 1965-01-26 | Wacker Chemie Gmbh | Cyanoethylation of organosilanes |
| US3328347A (en) * | 1961-12-18 | 1967-06-27 | Gen Electric | Nitrile-containing organosilicon polymers |
-
1956
- 1956-05-22 GB GB15829/56A patent/GB786020A/en not_active Expired
- 1956-07-17 DE DED23372A patent/DE1115026B/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2907784A (en) * | 1957-06-28 | 1959-10-06 | Union Carbide Corp | Preparation of cyanoalkylsilanes employing trihydrocarbyl phosphine catalysts |
| US3026278A (en) * | 1957-11-29 | 1962-03-20 | Union Carbide Corp | Cyanoalkylsiloxane copolymers |
| US2970150A (en) * | 1957-12-17 | 1961-01-31 | Union Carbide Corp | Processes for the reaction of silanic hydrogen-bonded siloxanes with unsaturated organic compounds with a platinum catalyst |
| US3112332A (en) * | 1958-06-25 | 1963-11-26 | Union Carbide Corp | Cyanoalkylsilanediols |
| DE1115463B (en) * | 1958-11-17 | 1961-10-19 | Union Carbide Corp | Process for the preparation of organopolysiloxanes |
| US2971972A (en) * | 1959-03-30 | 1961-02-14 | Gen Electric | Addition reaction |
| US3167573A (en) * | 1960-11-14 | 1965-01-26 | Wacker Chemie Gmbh | Cyanoethylation of organosilanes |
| US3328347A (en) * | 1961-12-18 | 1967-06-27 | Gen Electric | Nitrile-containing organosilicon polymers |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1115026B (en) | 1961-10-12 |
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