GB861817A - Improvements in or relating to the polymerization of diallyl phthalate - Google Patents
Improvements in or relating to the polymerization of diallyl phthalateInfo
- Publication number
- GB861817A GB861817A GB1114658A GB1114658A GB861817A GB 861817 A GB861817 A GB 861817A GB 1114658 A GB1114658 A GB 1114658A GB 1114658 A GB1114658 A GB 1114658A GB 861817 A GB861817 A GB 861817A
- Authority
- GB
- United Kingdom
- Prior art keywords
- monomer
- prepolymer
- modifier
- diallyl phthalate
- weight
- 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
- 239000004641 Diallyl-phthalate Substances 0.000 title abstract 4
- 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 title abstract 4
- 238000006116 polymerization reaction Methods 0.000 title abstract 4
- 239000000178 monomer Substances 0.000 abstract 6
- -1 methyl- Chemical group 0.000 abstract 5
- 239000003607 modifier Substances 0.000 abstract 5
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- BVQVLAIMHVDZEL-UHFFFAOYSA-N 1-phenyl-1,2-propanedione Chemical group CC(=O)C(=O)C1=CC=CC=C1 BVQVLAIMHVDZEL-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000001879 gelation Methods 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- JESIHYIJKKUWIS-UHFFFAOYSA-N 1-(4-Methylphenyl)ethanol Chemical compound CC(O)C1=CC=C(C)C=C1 JESIHYIJKKUWIS-UHFFFAOYSA-N 0.000 abstract 1
- KPJKMUJJFXZGAX-UHFFFAOYSA-N 2-chloropropan-2-ylbenzene Chemical compound CC(C)(Cl)C1=CC=CC=C1 KPJKMUJJFXZGAX-UHFFFAOYSA-N 0.000 abstract 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical group [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 238000004132 cross linking Methods 0.000 abstract 1
- QYFBSUCRERIFQO-UHFFFAOYSA-N dioxane-3,6-dione Chemical class O=C1CCC(=O)OO1 QYFBSUCRERIFQO-UHFFFAOYSA-N 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 235000013312 flour Nutrition 0.000 abstract 1
- 239000003292 glue Substances 0.000 abstract 1
- 150000002432 hydroperoxides Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical group [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 abstract 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000395 magnesium oxide Substances 0.000 abstract 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000001451 organic peroxides Chemical class 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 235000019832 sodium triphosphate Nutrition 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 abstract 1
- 229920001169 thermoplastic Polymers 0.000 abstract 1
- 229920001187 thermosetting polymer Polymers 0.000 abstract 1
- 239000004416 thermosoftening plastic Substances 0.000 abstract 1
- 239000002023 wood Substances 0.000 abstract 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
- C08F18/00—Homopolymers and 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 an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F18/02—Esters of monocarboxylic acids
- C08F18/04—Vinyl esters
- C08F18/08—Vinyl acetate
Landscapes
- Chemical & Material Sciences (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)
Abstract
A solid diallyl phthalate prepolymer is prepared from diallyl phthalate by polymerizing at an elevated temperature, e.g. above 70 DEG C., a mixture containing diallyl phthalate monomer, water, an organic peroxide or organic hydroperoxide catalyst, and a polymerization modifier of the formula <FORM:0861817/IV (a)/1> where X is chlorine or a hydroxyl radical or any group which can be converted to a hydroxyl group under reaction conditions, R is a methyl and/or ethyl and/or propyl radical, m is 0 to 4, the total number of carbon atoms in the R substituents is less than 5, and n is 0 to (4 - m), the modifier comprising 1 to 50% by weight based on the monomer, the reaction being discontinued before substantial gelation occurs by lowering the temperature below the polymerization temperature, unreacted monomer being separated from the prepolymer formed, and solid prepolymer recovered. Optional dispersing-agents, e.g. animal glue, clay and sodium tripolyphosphate, may be employed for the reaction. When dimethyl benzyl chloride or dimethyl benzyl alcohol is used as polymerization modifier, optimum ratios by weight thereof to monomer are 1 : 3.5 and 1.4. Other modifiers specified are benzyl alcohol and methyl-, isopropyl-, o-chlor-, and p-chlor-benzyl alcohols. It is stated that the modifier apparently functions to control the chain length of the polymer; excess cross-linking does not occur and a prepolymer is obtained without gelation. The proportion of water may be from 2 to 600% by weight of monomer. Catalysts in a proportion of 0.1 to 10% by weight of monomer are exemplified by benzoyl, acetyl benzoyl and succinyl peroxides and t-butyl perbenzoate. Of the isomeric diallyl phthalates that may be employed, orthophthalates are preferred. The prepolymers can be moulded to acetone-soluble thermoplastic or thermoset products at moderate temperatures and pressures. Chopped fibres, magnesium oxide and wood flour may be incorporated in the cured prepolymer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1114658A GB861817A (en) | 1958-04-09 | 1958-04-09 | Improvements in or relating to the polymerization of diallyl phthalate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1114658A GB861817A (en) | 1958-04-09 | 1958-04-09 | Improvements in or relating to the polymerization of diallyl phthalate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB861817A true GB861817A (en) | 1961-03-01 |
Family
ID=9980879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1114658A Expired GB861817A (en) | 1958-04-09 | 1958-04-09 | Improvements in or relating to the polymerization of diallyl phthalate |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB861817A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3339291A1 (en) * | 1982-10-30 | 1984-05-03 | Osaka Soda Co. Ltd., Osaka | DIALLYLTEREPHTHALATE COPOLYMERES |
-
1958
- 1958-04-09 GB GB1114658A patent/GB861817A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3339291A1 (en) * | 1982-10-30 | 1984-05-03 | Osaka Soda Co. Ltd., Osaka | DIALLYLTEREPHTHALATE COPOLYMERES |
| FR2535327A1 (en) * | 1982-10-30 | 1984-05-04 | Osaka Soda Co Ltd | COPOLYMER OF DIALLYL TEREPHTHALATE AND COMPOSITION COMPRISING SUCH A COPOLYMER |
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