GB966813A - Manufacture of organo tin compounds - Google Patents
Manufacture of organo tin compoundsInfo
- Publication number
- GB966813A GB966813A GB29519/62A GB2951962A GB966813A GB 966813 A GB966813 A GB 966813A GB 29519/62 A GB29519/62 A GB 29519/62A GB 2951962 A GB2951962 A GB 2951962A GB 966813 A GB966813 A GB 966813A
- Authority
- GB
- United Kingdom
- Prior art keywords
- catalyst
- tin
- triethyl
- hydride
- tin hydride
- 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 organo tin compounds Chemical class 0.000 title abstract 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000003054 catalyst Substances 0.000 abstract 26
- CPRPKIMXLHBUGA-UHFFFAOYSA-N triethyltin Chemical compound CC[Sn](CC)CC CPRPKIMXLHBUGA-UHFFFAOYSA-N 0.000 abstract 16
- 150000001875 compounds Chemical class 0.000 abstract 8
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- IPOBVSHPVYWJQC-UHFFFAOYSA-N 1,1,2,2,2-pentakis-phenylethylbenzene Chemical compound C1=CC=CC=C1C(C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 IPOBVSHPVYWJQC-UHFFFAOYSA-N 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 abstract 3
- WCRDXYSYPCEIAK-UHFFFAOYSA-N dibutylstannane Chemical compound CCCC[SnH2]CCCC WCRDXYSYPCEIAK-UHFFFAOYSA-N 0.000 abstract 3
- 229930195733 hydrocarbon Natural products 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 3
- WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 abstract 2
- WTUNIDHBATXPCT-UHFFFAOYSA-N 2-methylpropylstannane Chemical compound C(C(C)C)[SnH3] WTUNIDHBATXPCT-UHFFFAOYSA-N 0.000 abstract 2
- GCYHRYNSUGLLMA-UHFFFAOYSA-N 2-prop-2-enoxyethanol Chemical compound OCCOCC=C GCYHRYNSUGLLMA-UHFFFAOYSA-N 0.000 abstract 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 abstract 2
- 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
- 239000004641 Diallyl-phthalate Substances 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract 2
- 150000005840 aryl radicals Chemical group 0.000 abstract 2
- 229960003328 benzoyl peroxide Drugs 0.000 abstract 2
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 2
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 abstract 2
- WCOXDAZXJKCQGG-UHFFFAOYSA-N diethylstannane Chemical compound CC[SnH2]CC WCOXDAZXJKCQGG-UHFFFAOYSA-N 0.000 abstract 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 abstract 2
- 230000007717 exclusion Effects 0.000 abstract 2
- 150000002429 hydrazines Chemical group 0.000 abstract 2
- 150000002430 hydrocarbons Chemical group 0.000 abstract 2
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 abstract 2
- 229940038597 peroxide anti-acne preparations for topical use Drugs 0.000 abstract 2
- 150000002978 peroxides Chemical group 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- XITUCBPWFUBODR-UHFFFAOYSA-N (2-ethyl-1,1,2-triphenylbutyl)benzene Chemical compound C1(=CC=CC=C1)C(C(CC)(CC)C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 XITUCBPWFUBODR-UHFFFAOYSA-N 0.000 abstract 1
- KRMMZNOTUOIFQX-UHFFFAOYSA-N 1,1,2,2-tetraphenylhydrazine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)N(C=1C=CC=CC=1)C1=CC=CC=C1 KRMMZNOTUOIFQX-UHFFFAOYSA-N 0.000 abstract 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 abstract 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 abstract 1
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 abstract 1
- BQMDKTJDFSUWPK-UHFFFAOYSA-N 2-methyl-2-phenyldiazenylpropanenitrile Chemical compound N#CC(C)(C)N=NC1=CC=CC=C1 BQMDKTJDFSUWPK-UHFFFAOYSA-N 0.000 abstract 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- JGRRPAAAASIEPU-UHFFFAOYSA-N C(=C)C1=CC=C(C=C1)C=C.C(C)[SnH2]CC Chemical compound C(=C)C1=CC=C(C=C1)C=C.C(C)[SnH2]CC JGRRPAAAASIEPU-UHFFFAOYSA-N 0.000 abstract 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- FAOSYNUKPVJLNZ-UHFFFAOYSA-N butylstannane Chemical compound CCCC[SnH3] FAOSYNUKPVJLNZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- TZPZCTBZJKZFGY-UHFFFAOYSA-N chloro-tris(2-methylpropyl)silane Chemical compound CC(C)C[Si](Cl)(CC(C)C)CC(C)C TZPZCTBZJKZFGY-UHFFFAOYSA-N 0.000 abstract 1
- 229920006037 cross link polymer Polymers 0.000 abstract 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 abstract 1
- 150000001993 dienes Chemical class 0.000 abstract 1
- ZKCZXVODRKOWIY-UHFFFAOYSA-N diphenylstannane Chemical compound C=1C=CC=CC=1[SnH2]C1=CC=CC=C1 ZKCZXVODRKOWIY-UHFFFAOYSA-N 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 abstract 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 abstract 1
- UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical compound C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 abstract 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 abstract 1
- YFMFSCRSAWIWOP-UHFFFAOYSA-N phenyl(trityl)diazene Chemical compound C1=CC=CC=C1N=NC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 YFMFSCRSAWIWOP-UHFFFAOYSA-N 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- AAQVTXYBPJPWQR-UHFFFAOYSA-N tributyl(octyl)stannane Chemical compound CCCCCCCC[Sn](CCCC)(CCCC)CCCC AAQVTXYBPJPWQR-UHFFFAOYSA-N 0.000 abstract 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 abstract 1
- NFHRNKANAAGQOH-UHFFFAOYSA-N triphenylstannane Chemical compound C1=CC=CC=C1[SnH](C=1C=CC=CC=1)C1=CC=CC=C1 NFHRNKANAAGQOH-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
- C07F7/22—Tin compounds
- C07F7/2284—Compounds with one or more Sn-N linkages
-
- 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
- C07F7/22—Tin compounds
- C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen
-
- 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
- C07F7/22—Tin compounds
- C07F7/2224—Compounds having one or more tin-oxygen linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Organotin compounds are prepared by adding alkyl or aryl tin hydrides of formula RnSnH4-n wherein R is an alkyl or aryl radical and n is a number up to 3, to olefines, olefinic compounds or compounds of general formulae O=CR1R11 or R1N=CR11R111 wherein R1, R11-R111 are any aliphatic, aromatic or heterocyclic hydrocarbon radical, said addition being effected with exclusion of air and at a temperature below 120 DEG C. in the presence as catalyst of a compound which decomposes to form free-radicals at the temperature employed. Catalysts specified include azo-compounds, peroxides, hydrazine compounds and hydrocarbon substituted ethanes such as hexaphenyl ethane, and analogous compounds capable of forming free radicals at temperatures up to 120 DEG C. Free-radical forming compounds containing free carboxyl groups or other protondonating functional groups such as sulphinic acid groups are not suitable as catalysts. The reaction is carried out at temperatures as low as possible, with a maximum of 90 DEG -120 DEG C. The products may be monomeric or polymeric depending on the components. The examples are summarised as follows: Example 1. Triethyl tin hydride is reacted with methyl methacrylate in presence of azoisobutyronitrile (I); Example 2, as 1 using di-tert. butyl peroxide; Example 3, triethyl tin hydride, ethyl ester of undecylenoic acid and catalyst I; Example 4, triethyl tin hydride, alpha octene and catalyst I; Example 5, as 4 using phenyl azoisobutyronitrile; Example 6, as 5 using tri-n-butyl hydride giving tributyl octyl tin; Example 7, (C2H5)3Sn-(CH2)3-O-COCH3, from triethyl tin hydride, allyl acetate and phenyl azotriphenyl methane. Example 8, as 7 using hexaphenyl ethane, tetraphenyl -dibiphenyl ethane, diethyl-bis-fluorenyl or tetraphenyl-diethyl ethane; Example 9, as 8 using tetraphenyl hydrazine as catalyst; Example 10, (C2H5)3Sn(CH2)3-OH from triethyl tin hydride, allyl alcohol and catalyst I; Example 12, (C4H9)2Sn(CH2-CH2-CH2 -OCOCH3)2 from dibutyl tin dihydride, allyl-acetate and catalyst I; Example 13, (C8H17)3 Sn-(CH2)3-O-(CH2)2-OH from tri-n-octyl tin hydride, ethylene glycol mono-allyl ether and catalyst I; Example 14, (C2H5)3Sn-CH2-CH2-C12H8N from triethyl tin hydride, N-vinyl-carbazole and catalyst I; Example 15, (C2H5)3 Sn-(CH2)2-O-(CH2)3-CH3 from triethyl tin hydride, vinyl butyl ether and catalyst I; Example 16, (C2H5)3Sn-(CH2)2-CONH2 from triethyl tin hydride, acrylic amide and catalyst I; Example 17, as 16 using tri-n-butyl tin hydride giving (C4H9)3Sn-(CH2)2-CONH2; Example 18, (C2H5)3Sn-(CH2)2-CN from triethyl tin hydride, acrylonitrile and catalyst I; Example 19, (C6H5)3\t Sn-CH2-CHCH3-COOCH3 from triphenyl tin hydride, methyl methacrylate and catalyst I; Example 20, as 19 using triethyl tin hydride giving (C2H5)3Sn-CH2-CHCH3 -COOCH3; Example 21, triethyl tin hydride, styrene and catalyst I; Example 22, triethyl tin hydride, vinyl acetate and catalyst I; Example 23, (C2H5)3Sn \N(C6H5)-CH2-C6H5 from triethyl tin hydride, benzalaniline and catalyst I; Example 24, as Example 1, using methyl or ethyl azoisobutyrate as catalyst; Example 25, C4H9Sn(CH2-CH (CH3)COOCH3) from n-butyl tin trihydride, methyl methacrylate and catalyst I; Example 26, a glass-like polymer from diethyl tin dihydride p-divinyl benzene and catalyst I; Example 27, (C2H5)3Sn-(CH2)4-CH=CH2 from triethyl tin hydride, diallyl and catalyst I, and (C2H5)3Sn -CH2-CH2-C6H4-CH=CH2 from triethyl tin hydride and p-divinyl benzene-this product may be polymerised by benzoyl peroxide; Example 28, (C2H5)2Sn(CH2-CH2-CH2 -O-CH2-CH2-OH)2 from diethyl tin dihydride, ethylene glycol mono-allyl ether and catalyst I; Example 29, di-n-butyl tin dihydride, diallyl phthalate and catalyst I; Example 30, a solid cross-linked polymer from isobutyl tin trihydride, ethylene glycol dimethacrylate and azoisobutyrodinitrile; and Example 31, (C6H5)2Sn(CH2-CHCH3 -COOCH3)2 from diphenyl tin dihydride, methyl methacrylate and catalyst I.ALSO:Polymeric products containing tin are prepared by adding alkyl or aryl tin hydrides of formula RnSnH4-n wherein R is an alkyl or aryl radical and n is a number up to 3 to compounds containing more than one unsaturated group, e.g. diolefins with exclusion of air and at a temperature below 120 DEG C. in the presence as catalyst of a compound which decomposes to form free radicals at the temperature employed. Catalysts specified include azo-compounds, peroxides, hydrazine compounds and hydrocarbon substituted ethanes such as hexaphenyl ethane. The products are produced according to the reaction: nR2SnH2+nH2C=CH.R1.CH=CH2---> (-R2Sn-CH2.CH2.R1.CH2.CH2-) In the examples the following are reacted: Example 26, p-divinylbenzene, diethyl tin dihydride and azo-iso-butyronitrile; Example 27, p-divinyl benzene, triethyl tin hydride and azo-isobutyronitrile give (C2H5)3Sn-CH2-CH2-C6H4\t -CH=CH2 which may be polymerized by benzoylperoxide; Example 29, diallylphthalate, di-n-butyl tin dihydride and azo-isobutyronitrile; Example 30, ethylene glycol dimethacrylate, isobutyl tin trihydride and azo-isobutyronitrile.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEZ8888A DE1212531B (en) | 1961-08-02 | 1961-08-02 | Process for the production of organic tin compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB966813A true GB966813A (en) | 1964-08-19 |
Family
ID=7620669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB29519/62A Expired GB966813A (en) | 1961-08-02 | 1962-08-01 | Manufacture of organo tin compounds |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1212531B (en) |
| GB (1) | GB966813A (en) |
| NL (2) | NL133332C (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3976672A (en) | 1974-12-26 | 1976-08-24 | Uniroyal Inc. | (Hydrocarbylphenylsulfonyl)alkyltrimethylstannanes |
| US4260552A (en) * | 1974-12-26 | 1981-04-07 | Uniroyal, Inc. | Tetrasubstituted organotin compounds |
| US5051521A (en) * | 1988-04-21 | 1991-09-24 | Rhone-Poulenc Chimie | Novel tin (IV) compounds |
| WO2007075562A2 (en) * | 2005-12-16 | 2007-07-05 | E. I. Du Pont De Nemours And Company | Protected air-activated organotin catalysts for polyurethane synthesis |
| WO2007075561A1 (en) * | 2005-12-16 | 2007-07-05 | E. I. Du Pont De Nemours And Company | Protected air-activated organotin catalysts for polyurethane synthesis and processes therefore |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3519666A (en) * | 1968-02-09 | 1970-07-07 | Gulf Research Development Co | Triorganotin derivatives of cyclic compounds |
-
0
- NL NL281589D patent/NL281589A/xx unknown
- NL NL133332D patent/NL133332C/xx active
-
1961
- 1961-08-02 DE DEZ8888A patent/DE1212531B/en active Pending
-
1962
- 1962-08-01 GB GB29519/62A patent/GB966813A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3976672A (en) | 1974-12-26 | 1976-08-24 | Uniroyal Inc. | (Hydrocarbylphenylsulfonyl)alkyltrimethylstannanes |
| US4260552A (en) * | 1974-12-26 | 1981-04-07 | Uniroyal, Inc. | Tetrasubstituted organotin compounds |
| US5051521A (en) * | 1988-04-21 | 1991-09-24 | Rhone-Poulenc Chimie | Novel tin (IV) compounds |
| US5084543A (en) * | 1988-04-21 | 1992-01-28 | Rhone-Poulenc Chimie | Tin (iv) compounds |
| WO2007075562A2 (en) * | 2005-12-16 | 2007-07-05 | E. I. Du Pont De Nemours And Company | Protected air-activated organotin catalysts for polyurethane synthesis |
| WO2007075561A1 (en) * | 2005-12-16 | 2007-07-05 | E. I. Du Pont De Nemours And Company | Protected air-activated organotin catalysts for polyurethane synthesis and processes therefore |
| WO2007075562A3 (en) * | 2005-12-16 | 2007-08-30 | Du Pont | Protected air-activated organotin catalysts for polyurethane synthesis |
| US8026333B2 (en) | 2005-12-16 | 2011-09-27 | E. I. Du Pont De Nemours And Company | Protected air-activated organotin catalysts for polyurethane synthesis and processes therefore |
Also Published As
| Publication number | Publication date |
|---|---|
| NL133332C (en) | 1900-01-01 |
| NL281589A (en) | 1900-01-01 |
| DE1212531B (en) | 1966-03-17 |
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