DE1206593B - Verfahren zur Herstellung von Vinylesterpolymerisaten - Google Patents
Verfahren zur Herstellung von VinylesterpolymerisatenInfo
- Publication number
- DE1206593B DE1206593B DEST16871A DEST016871A DE1206593B DE 1206593 B DE1206593 B DE 1206593B DE ST16871 A DEST16871 A DE ST16871A DE ST016871 A DEST016871 A DE ST016871A DE 1206593 B DE1206593 B DE 1206593B
- Authority
- DE
- Germany
- Prior art keywords
- vinyl ester
- vinyl
- acid
- anhydride
- trimellitic
- 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
- 229920001567 vinyl ester resin Polymers 0.000 title claims description 24
- 229920000642 polymer Polymers 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 10
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- 239000002685 polymerization catalyst Substances 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 2
- DOBUSJIVSSJEDA-UHFFFAOYSA-L 1,3-dioxa-2$l^{6}-thia-4-mercuracyclobutane 2,2-dioxide Chemical compound [Hg+2].[O-]S([O-])(=O)=O DOBUSJIVSSJEDA-UHFFFAOYSA-L 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000016067 Polianthes tuberosa Nutrition 0.000 description 1
- 244000014047 Polianthes tuberosa Species 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000001427 coherent effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- 229910001987 mercury nitrate Inorganic materials 0.000 description 1
- 229910000370 mercury sulfate Inorganic materials 0.000 description 1
- DNUMSHUWKXQLDT-UHFFFAOYSA-H mercury(2+);diphosphate Chemical compound [Hg+2].[Hg+2].[Hg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O DNUMSHUWKXQLDT-UHFFFAOYSA-H 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- DRXYRSRECMWYAV-UHFFFAOYSA-N nitrooxymercury Chemical compound [Hg+].[O-][N+]([O-])=O DRXYRSRECMWYAV-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- 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)
- 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)
- Furan Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US839566A US3063969A (en) | 1959-09-14 | 1959-09-14 | 4-vinyl trimellitate and/or anhydride and polymers thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1206593B true DE1206593B (de) | 1965-12-09 |
Family
ID=25280084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEST16871A Pending DE1206593B (de) | 1959-09-14 | 1960-09-06 | Verfahren zur Herstellung von Vinylesterpolymerisaten |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3063969A (en, 2012) |
| BE (1) | BE594994A (en, 2012) |
| DE (1) | DE1206593B (en, 2012) |
| GB (1) | GB961960A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1301091B (de) * | 1962-04-11 | 1969-08-14 | Monsanto Chemicals | Verfahren zur Herstellung von Mischpolymerisaten |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3206440A (en) * | 1961-06-29 | 1965-09-14 | Glen W Hedrick | Vinyl esters of maleic anhydride adducts |
| US3183248A (en) * | 1961-08-02 | 1965-05-11 | Standard Oil Co | Esters of trimellitic anhydride |
| US3182073A (en) * | 1962-04-27 | 1965-05-04 | Gen Electric | Trimellitic anhydride derivatives |
| BE631373A (en, 2012) * | 1962-04-27 | |||
| US3207765A (en) * | 1963-03-11 | 1965-09-21 | American Cyanamid Co | Process for production of vinyl trimellitates |
| US4148988A (en) * | 1977-06-28 | 1979-04-10 | Mitsui Petrochemical Industries Ltd. | Curable composition |
| GB2036772B (en) * | 1978-11-06 | 1983-05-05 | Bostik Ltd | Acrylic adhesives |
| DE3204127A1 (de) * | 1982-02-06 | 1983-08-11 | Bayer Ag, 5090 Leverkusen | Acylanhydrozitronensaeurevinylester und ihre herstellung |
| US4480080A (en) * | 1983-01-31 | 1984-10-30 | Eastman Kodak Company | Vinyl-ester polymeric timing layer for color transfer assemblages |
| US4619964A (en) * | 1983-10-03 | 1986-10-28 | Rohm And Haas Company | Stabilized aqueous copolymer dispersions |
| KR101391488B1 (ko) * | 2006-08-09 | 2014-05-07 | 미츠비시 가스 가가쿠 가부시키가이샤 | 산무수물 에스테르와 그 조성물, 열경화성 수지 조성물 및그 경화물 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2245131A (en) * | 1941-06-10 | Process of preparing vinyl esters | ||
| FR733483A (fr) * | 1931-03-30 | 1932-10-06 | Procédé de fabrication de composés vinyliques contenant des groupes hydrophiles | |
| US2332896A (en) * | 1940-05-29 | 1943-10-26 | Gen Electric | Synthetic composition comprising hydrolyzed acetalized copolymers of vinyl esters and unsaturated organic esters |
| US2324426A (en) * | 1940-08-17 | 1943-07-13 | Carborundum Co | Abrasive product |
| US2557639A (en) * | 1947-03-04 | 1951-06-19 | Shell Dev | Esterification with allyl type alcohols |
| US2595852A (en) * | 1949-06-20 | 1952-05-06 | Shell Dev | Process for spray drying soluble fusible polymers of unsaturated esters |
| NL72274C (en, 2012) * | 1949-07-26 | 1952-06-16 | ||
| US2612491A (en) * | 1951-08-25 | 1952-09-30 | Shell Dev | Mixed polycarboxylic acid esters of alkylidene glycols and polymers thereof |
| US2911416A (en) * | 1958-07-30 | 1959-11-03 | Standard Oil Co | Trimellitic double anhydride |
-
0
- BE BE594994D patent/BE594994A/xx unknown
-
1959
- 1959-09-14 US US839566A patent/US3063969A/en not_active Expired - Lifetime
-
1960
- 1960-09-06 DE DEST16871A patent/DE1206593B/de active Pending
- 1960-09-13 GB GB31481/60A patent/GB961960A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1301091B (de) * | 1962-04-11 | 1969-08-14 | Monsanto Chemicals | Verfahren zur Herstellung von Mischpolymerisaten |
Also Published As
| Publication number | Publication date |
|---|---|
| US3063969A (en) | 1962-11-13 |
| GB961960A (en) | 1964-06-24 |
| BE594994A (en, 2012) |
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