CA1097607A - Alpha halo substituted asymmetrical diacyl peroxides in co-initiator systems - Google Patents
Alpha halo substituted asymmetrical diacyl peroxides in co-initiator systemsInfo
- Publication number
- CA1097607A CA1097607A CA282,132A CA282132A CA1097607A CA 1097607 A CA1097607 A CA 1097607A CA 282132 A CA282132 A CA 282132A CA 1097607 A CA1097607 A CA 1097607A
- Authority
- CA
- Canada
- Prior art keywords
- accordance
- polymerization
- organic peroxide
- initiator composition
- alkyl
- 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
- 239000003999 initiator Substances 0.000 title claims abstract description 43
- 239000012933 diacyl peroxide Substances 0.000 title claims abstract description 19
- 125000001475 halogen functional group Chemical group 0.000 title claims abstract description 14
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 150000001451 organic peroxides Chemical class 0.000 claims abstract description 20
- 239000000178 monomer Substances 0.000 claims abstract description 12
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000002252 acyl group Chemical group 0.000 claims abstract description 6
- 150000002148 esters Chemical class 0.000 claims abstract description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000005977 Ethylene Substances 0.000 claims abstract description 5
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 230000000977 initiatory effect Effects 0.000 claims abstract description 3
- 125000005634 peroxydicarbonate group Chemical group 0.000 claims abstract description 3
- HYIHPIVFLYWQEM-UHFFFAOYSA-N acetyl 2-chlorooctaneperoxoate Chemical compound CCCCCCC(Cl)C(=O)OOC(C)=O HYIHPIVFLYWQEM-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 238000007334 copolymerization reaction Methods 0.000 claims description 4
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- DIGNJRVMQQDNRE-UHFFFAOYSA-N 2-chlorobutanoyl dodecaneperoxoate Chemical group CCCCCCCCCCCC(=O)OOC(=O)C(Cl)CC DIGNJRVMQQDNRE-UHFFFAOYSA-N 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- NSGQRLUGQNBHLD-UHFFFAOYSA-N butan-2-yl butan-2-yloxycarbonyloxy carbonate Chemical compound CCC(C)OC(=O)OOC(=O)OC(C)CC NSGQRLUGQNBHLD-UHFFFAOYSA-N 0.000 claims 1
- 125000005535 neodecanoate group Chemical group 0.000 claims 1
- QMIAKVBKPMYTJE-UHFFFAOYSA-N propanoyl 2-chlorooctaneperoxoate Chemical group CCCCCCC(Cl)C(=O)OOC(=O)CC QMIAKVBKPMYTJE-UHFFFAOYSA-N 0.000 claims 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract description 2
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 abstract 1
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 150000002976 peresters Chemical class 0.000 description 6
- PQYJRMFWJJONBO-UHFFFAOYSA-N Tris(2,3-dibromopropyl) phosphate Chemical compound BrCC(Br)COP(=O)(OCC(Br)CBr)OCC(Br)CBr PQYJRMFWJJONBO-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920006026 co-polymeric resin Polymers 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 239000003426 co-catalyst Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- 229920003091 Methocel™ Polymers 0.000 description 1
- -1 alkyl peresters Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940057344 bufferin Drugs 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- LQKBKHFGCGFBAF-UHFFFAOYSA-N butyl carboxyoxy carbonate Chemical compound CCCCOC(=O)OOC(O)=O LQKBKHFGCGFBAF-UHFFFAOYSA-N 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- BSVQJWUUZCXSOL-UHFFFAOYSA-N cyclohexylsulfonyl ethaneperoxoate Chemical compound CC(=O)OOS(=O)(=O)C1CCCCC1 BSVQJWUUZCXSOL-UHFFFAOYSA-N 0.000 description 1
- XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NUHSROFQTUXZQQ-UHFFFAOYSA-N isopentenyl diphosphate Chemical compound CC(=C)CCO[P@](O)(=O)OP(O)(O)=O NUHSROFQTUXZQQ-UHFFFAOYSA-N 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SBUYBNIDQXQZSZ-UHFFFAOYSA-N p-aminophenylphosphocholine Chemical compound C[N+](C)(C)CCOP([O-])(=O)OC1=CC=C(N)C=C1 SBUYBNIDQXQZSZ-UHFFFAOYSA-N 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- IWZKICVEHNUQTL-UHFFFAOYSA-M potassium hydrogen phthalate Chemical compound [K+].OC(=O)C1=CC=CC=C1C([O-])=O IWZKICVEHNUQTL-UHFFFAOYSA-M 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 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
- C08F4/00—Polymerisation catalysts
- C08F4/28—Oxygen or compounds releasing free oxygen
- C08F4/32—Organic compounds
- C08F4/38—Mixtures of peroxy-compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US739,416 | 1976-11-08 | ||
| US05/739,416 US4102815A (en) | 1976-11-08 | 1976-11-08 | Alpha halo substituted asymmetrical diacyl peroxides in co-initiator systems |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1097607A true CA1097607A (en) | 1981-03-17 |
Family
ID=24972205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA282,132A Expired CA1097607A (en) | 1976-11-08 | 1977-07-06 | Alpha halo substituted asymmetrical diacyl peroxides in co-initiator systems |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US4102815A (en:Method) |
| JP (1) | JPS5358590A (en:Method) |
| BE (1) | BE860568A (en:Method) |
| CA (1) | CA1097607A (en:Method) |
| DE (1) | DE2748040A1 (en:Method) |
| FR (1) | FR2370060A1 (en:Method) |
| GB (1) | GB1577169A (en:Method) |
| IT (1) | IT1079903B (en:Method) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4279831A (en) * | 1979-08-10 | 1981-07-21 | Argus Chemical Corporation | 2-Chloro-2-alkyl substituted asymmetrical diacyl peroxides |
| US4307217A (en) * | 1979-08-10 | 1981-12-22 | Argus Chemical Corporation | 2-Chloro-2-alkyl substituted asymmetrical diacyl peroxides and polymerization process using same |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3022282A (en) | 1959-08-25 | 1962-02-20 | Us Rubber Co | Polymerization catalyst for vinyl chloride |
| US3420807A (en) * | 1966-12-19 | 1969-01-07 | Wallace & Tiernan Inc | Vinyl chloride polymerization |
| US3652681A (en) * | 1967-10-16 | 1972-03-28 | Argus Chem | Alpha-halo substituted asymmetrical diacyl peroxides |
| US3652524A (en) * | 1967-12-26 | 1972-03-28 | Argus Chem | Process for polymerizing vinyl chloride with low molecular weight acyl peroxycarbonic esters |
| NL6717760A (en:Method) * | 1967-12-28 | 1969-07-01 | ||
| US3558537A (en) * | 1968-01-02 | 1971-01-26 | Argus Chem | Imparting antifogging properties to polyvinyl chloride resins and compositions therefor |
| US3817965A (en) * | 1968-02-27 | 1974-06-18 | Aquitaine Petrole | Polymerization of vinyl compounds in suspension |
| BE754577A (en:Method) * | 1969-08-08 | 1971-02-08 | Wacker Chemie Gmbh | |
| BE756426A (fr) * | 1969-09-23 | 1971-03-22 | Basf Ag | Procede de preparation d'homo- ou de copolymeres de l'ethylene |
| US3687867A (en) * | 1970-04-08 | 1972-08-29 | Argus Chem | Novel co-initiator systems |
| US3763128A (en) * | 1970-04-08 | 1973-10-02 | Argus Chem | Novel co initiator systems |
| US3932372A (en) * | 1970-07-20 | 1976-01-13 | Argus Chemical Corporation | Peroxide co-initiator system for polymerization |
| US3736306A (en) * | 1970-09-14 | 1973-05-29 | Pennwalt Corp | Polymerization of vinyl chloride with blends of peroxide initiators |
| US3778422A (en) * | 1971-05-17 | 1973-12-11 | Tenneco Chem | Process for the production of vinyl halide polymers |
-
1976
- 1976-11-08 US US05/739,416 patent/US4102815A/en not_active Expired - Lifetime
-
1977
- 1977-03-04 US US05/774,289 patent/US4107419A/en not_active Expired - Lifetime
- 1977-07-06 CA CA282,132A patent/CA1097607A/en not_active Expired
- 1977-07-29 IT IT50506/77A patent/IT1079903B/it active
- 1977-08-19 JP JP9943277A patent/JPS5358590A/ja active Pending
- 1977-09-02 FR FR7726766A patent/FR2370060A1/fr active Granted
- 1977-09-23 GB GB39785/77A patent/GB1577169A/en not_active Expired
- 1977-10-26 DE DE19772748040 patent/DE2748040A1/de not_active Withdrawn
- 1977-11-07 BE BE182423A patent/BE860568A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE860568A (fr) | 1978-03-01 |
| FR2370060A1 (fr) | 1978-06-02 |
| IT1079903B (it) | 1985-05-13 |
| GB1577169A (en) | 1980-10-22 |
| DE2748040A1 (de) | 1978-05-18 |
| US4107419A (en) | 1978-08-15 |
| US4102815A (en) | 1978-07-25 |
| JPS5358590A (en) | 1978-05-26 |
| FR2370060B3 (en:Method) | 1980-06-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3420807A (en) | Vinyl chloride polymerization | |
| JPH0364302A (ja) | 可塑剤吸収性の改良された塩化ビニル系重合体の製造方法 | |
| CA1097607A (en) | Alpha halo substituted asymmetrical diacyl peroxides in co-initiator systems | |
| US4749757A (en) | High bulk density PVC resin suspension polymerization with inhibitor | |
| US4464519A (en) | Vinyl chloride-propylene copolymers having increased porosity | |
| US3141870A (en) | Heterogeneous copolymers of ethylene-acrylic esters | |
| US3230203A (en) | Process for the manufacture of copolymers of vinyl chloride | |
| US4746705A (en) | Vinyl chloride polymer composition containing (meth)acrylate-alpha methyl styrene copolymer | |
| CA1057770A (en) | Thermally stable high molecular weight acyl peroxycarbonic esters | |
| US4914169A (en) | Method of polymerizing vinyl chloride | |
| US2971948A (en) | Process for preparing copolymers of vinyl chloride | |
| FI63766B (fi) | Foerfarande foer polymerisation av vinylklorid eller vinylklorid och sampolymeriserbara etyleniskt omaettade monomerer | |
| US3836510A (en) | Vinyl halide terpolymer and bulk process for preparation | |
| CA1059690A (en) | Vinyl halide stripping process | |
| CA1099449A (en) | Internally plasticized vinyl chloride copolymer composition | |
| US3790542A (en) | Method for polymerizing vinyl chloride | |
| US3959241A (en) | Vinyl chloride polymers and copolymers | |
| US3609131A (en) | Copolymers of vinyl chloride and olefins and processes for their preparation | |
| US4391962A (en) | Process for the suspension (CO)polymerization of vinyl chloride | |
| US3838138A (en) | Short cycle,thermally stable vinyl chloride-propylene copolymers | |
| RU2171262C2 (ru) | Способ радикальной (со)полимеризации | |
| US2616881A (en) | Shortstopping vinyl chloride polymerizations with ethylenically-unsaturated ketones | |
| US4070534A (en) | Producing heat stable vinyl chloride polymers at low temperatures in the presence of tetrahydrofuran | |
| US3560463A (en) | Copolymers of ethylene with cetyl vinyl ether or n-octadecyl vinyl ether | |
| EP0324835A1 (en) | Propylene polymerization catalyst and method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |