DE1300700B - Verfahren zur Herstellung eines licht- und waermestabilisierten Vinylchloridmischpolymeren - Google Patents
Verfahren zur Herstellung eines licht- und waermestabilisierten VinylchloridmischpolymerenInfo
- Publication number
- DE1300700B DE1300700B DEM46821A DEM0046821A DE1300700B DE 1300700 B DE1300700 B DE 1300700B DE M46821 A DEM46821 A DE M46821A DE M0046821 A DEM0046821 A DE M0046821A DE 1300700 B DE1300700 B DE 1300700B
- Authority
- DE
- Germany
- Prior art keywords
- tin
- vinyl chloride
- vinyl
- heat
- percent
- 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.)
- Pending
Links
- 229920001577 copolymer Polymers 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 22
- -1 hydrocarbon tin salt Chemical class 0.000 claims description 21
- 229910052718 tin Inorganic materials 0.000 claims description 18
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 17
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 16
- 229930195733 hydrocarbon Natural products 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- LPUCKLOWOWADAC-UHFFFAOYSA-M tributylstannyl 2-methylprop-2-enoate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(=O)C(C)=C LPUCKLOWOWADAC-UHFFFAOYSA-M 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 3
- 239000002685 polymerization catalyst Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- YSUXTNDMKYYZPR-UHFFFAOYSA-M tributylstannyl prop-2-enoate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(=O)C=C YSUXTNDMKYYZPR-UHFFFAOYSA-M 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 16
- 239000002253 acid Substances 0.000 description 7
- UCZLBERYFYDXOM-UHFFFAOYSA-N ethenyltin Chemical class [Sn]C=C UCZLBERYFYDXOM-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- JCJXEBAQTMCZGK-UHFFFAOYSA-N ethenyl(triphenyl)stannane Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(C=C)C1=CC=CC=C1 JCJXEBAQTMCZGK-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 3
- RZBBHEJLECUBJT-UHFFFAOYSA-N 6-methylheptyl 2-sulfanylacetate Chemical compound CC(C)CCCCCOC(=O)CS RZBBHEJLECUBJT-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- CDNRJNMBEAKKLM-UHFFFAOYSA-N bis(ethenyl)tin Chemical compound C=C[Sn]C=C CDNRJNMBEAKKLM-UHFFFAOYSA-N 0.000 description 2
- CUALHXSYIVGILB-UHFFFAOYSA-N butyl(ethenyl)tin Chemical compound CCCC[Sn]C=C CUALHXSYIVGILB-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- GEAOJWKXHMGANA-UHFFFAOYSA-N $l^{1}-stannane Chemical class [SnH] GEAOJWKXHMGANA-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- UZQYLGRYMHXVSW-UHFFFAOYSA-L C(CCC)C=C[Sn](Cl)Cl Chemical compound C(CCC)C=C[Sn](Cl)Cl UZQYLGRYMHXVSW-UHFFFAOYSA-L 0.000 description 1
- YPJPBEZEFUNXNG-UHFFFAOYSA-N CCCC[O-].CCCC[O-].C=C[Sn++]C=C Chemical compound CCCC[O-].CCCC[O-].C=C[Sn++]C=C YPJPBEZEFUNXNG-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000723347 Cinnamomum Species 0.000 description 1
- 206010068188 Heat illness Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OHPGJOIDOCNNMF-UHFFFAOYSA-N [(e)-hex-1-enyl]tin Chemical compound CCCC\C=C\[Sn] OHPGJOIDOCNNMF-UHFFFAOYSA-N 0.000 description 1
- UCJOBZKBTWHHRK-UHFFFAOYSA-L [dibutyl(2-methylprop-2-enoyloxy)stannyl] 2-methylprop-2-enoate Chemical compound CC(=C)C([O-])=O.CC(=C)C([O-])=O.CCCC[Sn+2]CCCC UCJOBZKBTWHHRK-UHFFFAOYSA-L 0.000 description 1
- HWPOXWPJPZMRPT-UHFFFAOYSA-L [dodecanoyloxy-bis(ethenyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](C=C)(C=C)OC(=O)CCCCCCCCCCC HWPOXWPJPZMRPT-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- DCEMWIQWJGGEFS-UHFFFAOYSA-M benzyl-chloro-bis(ethenyl)stannane Chemical compound C(=C)[Sn](CC1=CC=CC=C1)(C=C)Cl DCEMWIQWJGGEFS-UHFFFAOYSA-M 0.000 description 1
- FQFLLLUVRQHMHB-UHFFFAOYSA-L bis(ethenyl)-diiodostannane Chemical compound C=C[Sn](I)(I)C=C FQFLLLUVRQHMHB-UHFFFAOYSA-L 0.000 description 1
- HOSLAVQYAKGJTN-UHFFFAOYSA-N bis(ethenyl)-dimethoxystannane Chemical compound C(=C)[Sn](OC)(OC)C=C HOSLAVQYAKGJTN-UHFFFAOYSA-N 0.000 description 1
- GDUPVDKWJIGZIO-UHFFFAOYSA-N bis(ethenyl)-diphenylstannane Chemical compound C=1C=CC=CC=1[Sn](C=C)(C=C)C1=CC=CC=C1 GDUPVDKWJIGZIO-UHFFFAOYSA-N 0.000 description 1
- KISOQBMUZOGSDL-UHFFFAOYSA-M bromo-dibutyl-ethenylstannane Chemical compound CCCC[Sn](Br)(C=C)CCCC KISOQBMUZOGSDL-UHFFFAOYSA-M 0.000 description 1
- NCCUONVVYJEMRV-UHFFFAOYSA-M butyl-bis(ethenyl)stannanylium;chloride Chemical compound [Cl-].CCCC[Sn+](C=C)C=C NCCUONVVYJEMRV-UHFFFAOYSA-M 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- DWWAAPZMRWAYDL-UHFFFAOYSA-M chloro-bis(ethenyl)-(2-methylphenyl)stannane Chemical compound C1(=C(C=CC=C1)[Sn](C=C)(C=C)Cl)C DWWAAPZMRWAYDL-UHFFFAOYSA-M 0.000 description 1
- OEEKDHUOTUHEEY-UHFFFAOYSA-M chloro-tris(ethenyl)stannane Chemical compound C=C[Sn](Cl)(C=C)C=C OEEKDHUOTUHEEY-UHFFFAOYSA-M 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- FFKSUTHTFIDTNU-UHFFFAOYSA-N dibutyl-bis(ethenyl)stannane Chemical compound CCCC[Sn](C=C)(C=C)CCCC FFKSUTHTFIDTNU-UHFFFAOYSA-N 0.000 description 1
- DUULYVQITMWRAC-UHFFFAOYSA-M dibutyl-chloro-ethenylstannane Chemical compound CCCC[Sn](Cl)(C=C)CCCC DUULYVQITMWRAC-UHFFFAOYSA-M 0.000 description 1
- LWHKXKZPLXYXRO-UHFFFAOYSA-L dichloro-bis(ethenyl)stannane Chemical compound C=C[Sn](Cl)(Cl)C=C LWHKXKZPLXYXRO-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229920005570 flexible polymer Polymers 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229920006280 packaging film Polymers 0.000 description 1
- 239000012785 packaging film Substances 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- MZIYQMVHASXABC-UHFFFAOYSA-N tetrakis(ethenyl)stannane Chemical compound C=C[Sn](C=C)(C=C)C=C MZIYQMVHASXABC-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- URNVMBADOXXKOA-UHFFFAOYSA-K trichloro(ethenyl)stannane Chemical compound Cl[Sn](Cl)(Cl)C=C URNVMBADOXXKOA-UHFFFAOYSA-K 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F214/02—Monomers containing chlorine
- C08F214/04—Monomers containing two carbon atoms
- C08F214/06—Vinyl chloride
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F30/00—Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F30/04—Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US846796A US3069394A (en) | 1959-10-16 | 1959-10-16 | Stable polymers of vinyl chloride and unsaturated organotin compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1300700B true DE1300700B (de) | 1969-08-07 |
Family
ID=25298967
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEM46821A Pending DE1300700B (de) | 1959-10-16 | 1960-10-14 | Verfahren zur Herstellung eines licht- und waermestabilisierten Vinylchloridmischpolymeren |
Country Status (6)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3201376A (en) * | 1961-06-27 | 1965-08-17 | Thiokol Chemical Corp | Curable copolymers containing carboxyl and organo-metallic carboxylate and process for their preparation |
| US7244827B2 (en) * | 2000-04-12 | 2007-07-17 | Agensys, Inc. | Nucleic acid and corresponding protein entitled 24P4C12 useful in treatment and detection of cancer |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE564652A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1957-02-12 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2253128A (en) * | 1939-04-26 | 1941-08-19 | Du Pont | Compounds of group iv-beta elements with alpha-beta unsaturated acids |
| US2318959A (en) * | 1940-04-04 | 1943-05-11 | Pittsburgh Plate Glass Co | Artificial glass |
| US2832750A (en) * | 1951-06-21 | 1958-04-29 | Metal & Thermit Corp | Organo tin compounds, method of making same, and mixtures thereof with halogen-containing resins |
| US2873288A (en) * | 1956-09-18 | 1959-02-10 | Metal & Thermit Corp | Process for the preparation of vinyl tin compounds |
-
0
- NL NL256859D patent/NL256859A/xx unknown
- BE BE596011D patent/BE596011A/xx unknown
- NL NL108115D patent/NL108115C/xx active
-
1959
- 1959-10-16 US US846796A patent/US3069394A/en not_active Expired - Lifetime
-
1960
- 1960-10-06 GB GB34341/60A patent/GB919735A/en not_active Expired
- 1960-10-14 CH CH1157660A patent/CH412334A/fr unknown
- 1960-10-14 DE DEM46821A patent/DE1300700B/de active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE564652A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1957-02-12 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL256859A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1900-01-01 |
| CH412334A (fr) | 1966-04-30 |
| BE596011A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1900-01-01 |
| US3069394A (en) | 1962-12-18 |
| GB919735A (en) | 1963-02-27 |
| NL108115C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1900-01-01 |
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