GB877862A - Polymerisation catalysts for certain unsaturated organic compounds - Google Patents
Polymerisation catalysts for certain unsaturated organic compoundsInfo
- Publication number
- GB877862A GB877862A GB21293/59A GB2129359A GB877862A GB 877862 A GB877862 A GB 877862A GB 21293/59 A GB21293/59 A GB 21293/59A GB 2129359 A GB2129359 A GB 2129359A GB 877862 A GB877862 A GB 877862A
- Authority
- GB
- United Kingdom
- Prior art keywords
- peroxide
- compound
- diallyl
- organic compounds
- catalyst
- 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
- 239000003054 catalyst Substances 0.000 title abstract 3
- 150000002894 organic compounds Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- -1 peroxy compound Chemical class 0.000 abstract 3
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- WJLUBOLDZCQZEV-UHFFFAOYSA-M hexadecyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCCCCCC[N+](C)(C)C WJLUBOLDZCQZEV-UHFFFAOYSA-M 0.000 abstract 2
- 150000002736 metal compounds Chemical class 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 2
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 abstract 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 abstract 1
- MGYMHQJELJYRQS-UHFFFAOYSA-N Ascaridole Chemical compound C1CC2(C)OOC1(C(C)C)C=C2 MGYMHQJELJYRQS-UHFFFAOYSA-N 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004641 Diallyl-phthalate Substances 0.000 abstract 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- MGYMHQJELJYRQS-ZJUUUORDSA-N ascaridole Natural products C1C[C@]2(C)OO[C@@]1(C(C)C)C=C2 MGYMHQJELJYRQS-ZJUUUORDSA-N 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- 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 1
- 238000009835 boiling Methods 0.000 abstract 1
- 150000001649 bromium compounds Chemical class 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 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
- 239000012933 diacyl peroxide Substances 0.000 abstract 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000005609 naphthenate group Chemical group 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- OUJKULZFRNPRHO-UHFFFAOYSA-N prop-2-enyl 2-(2-oxo-2-prop-2-enoxyethoxy)acetate Chemical compound C=CCOC(=O)COCC(=O)OCC=C OUJKULZFRNPRHO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 235000007586 terpenes Nutrition 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 229920001169 thermoplastic Polymers 0.000 abstract 1
- 239000012815 thermoplastic material Substances 0.000 abstract 1
- 239000004416 thermosoftening plastic Substances 0.000 abstract 1
- 239000011135 tin Substances 0.000 abstract 1
- 229910052718 tin Inorganic materials 0.000 abstract 1
- 239000010936 titanium Substances 0.000 abstract 1
- 229910052719 titanium Inorganic materials 0.000 abstract 1
- PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01R—ELECTRICALLY-CONDUCTIVE CONNECTIONS; STRUCTURAL ASSOCIATIONS OF A PLURALITY OF MUTUALLY-INSULATED ELECTRICAL CONNECTING ELEMENTS; COUPLING DEVICES; CURRENT COLLECTORS
- H01R33/00—Coupling devices specially adapted for supporting apparatus and having one part acting as a holder providing support and electrical connection via a counterpart which is structurally associated with the apparatus, e.g. lamp holders; Separate parts thereof
- H01R33/05—Two-pole devices
- H01R33/46—Two-pole devices for bayonet type base
-
- 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
- C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
-
- 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
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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
A process for polymerizing unsaturated organic compounds with a boiling point above 100 DEG C., having at least one carbon to carbon double bond and excluding vinyl acetate comprises using as catalyst a system comprising (1) an organic peroxy compound; (2) a tertiary amine or quaternary base and (3) a soluble metal compound. The polymerizable compound preferably contains at least two ethylenically unsaturated groups per molecule such as diglycol dimethacrylate, diallyl phthalate, triallyl cyanurate, diallyl diglycolate or 2 : 4-diallyl-6-amino-5-triazine and this compound may be copolymerized with a compound containing only one ethylenically unsaturated group such as styrene or methyl methacrylate. Polymerization may be effected in stages up to 100 DEG C. to form a thermoplastic sheet which is converted at 140 DEG -160 DEG C. to a substantially non-thermoplastic material. The peroxy compound may be a symmetrical diacyl peroxide such as lauroyl or benzoyl peroxide, a terpene peroxide such as ascaridol or an alkyl or dialkyl peroxide such as cumene hydroperoxide or di-(tertiary butyl)-peroxide. The base may be octa or hexadecyl trimethyl ammonium hydroxide, trimethylamine, N-diethyl-ethanolamine or ethyl morpholine. The soluble metal compounds may be chlorides, bromides or naphthenates of aluminium, titanium, manganese, copper, zinc and tin. In specific examples cumene hydroperoxide, aluminium chloride in carbon tetrachloride, and mixed octadecyl and hexadecyl trimethyl ammonium hydroxide in isopropanol is used as the catalyst.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA877862X | 1958-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB877862A true GB877862A (en) | 1961-09-20 |
Family
ID=4172766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21293/59A Expired GB877862A (en) | 1958-06-28 | 1959-06-22 | Polymerisation catalysts for certain unsaturated organic compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB877862A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1185817B (en) * | 1962-05-11 | 1965-01-21 | Goldschmidt Ag Th | Process for the preparation of polymers which contain the triazine ring |
| EP0296141A3 (en) * | 1987-05-13 | 1990-02-07 | Monsanto Company | Allyloxy activated surface coatings |
| EP0296140A3 (en) * | 1987-05-13 | 1990-02-14 | Monsanto Company | Allyloxy-activated surface coatings |
-
1959
- 1959-06-22 GB GB21293/59A patent/GB877862A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1185817B (en) * | 1962-05-11 | 1965-01-21 | Goldschmidt Ag Th | Process for the preparation of polymers which contain the triazine ring |
| EP0296141A3 (en) * | 1987-05-13 | 1990-02-07 | Monsanto Company | Allyloxy activated surface coatings |
| EP0296140A3 (en) * | 1987-05-13 | 1990-02-14 | Monsanto Company | Allyloxy-activated surface coatings |
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