CA1111197A - Process for the preparation of improved styrene acrylic acid copolymers - Google Patents
Process for the preparation of improved styrene acrylic acid copolymersInfo
- Publication number
- CA1111197A CA1111197A CA314,348A CA314348A CA1111197A CA 1111197 A CA1111197 A CA 1111197A CA 314348 A CA314348 A CA 314348A CA 1111197 A CA1111197 A CA 1111197A
- Authority
- CA
- Canada
- Prior art keywords
- acrylic acid
- weight
- bis
- styrene
- initiator
- 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
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229920001577 copolymer Polymers 0.000 title abstract description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000003999 initiator Substances 0.000 claims abstract description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 16
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000002978 peroxides Chemical class 0.000 claims abstract description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 29
- 229920000642 polymer Polymers 0.000 claims description 17
- 229910052742 iron Inorganic materials 0.000 claims description 14
- 238000000465 moulding Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 6
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 claims description 3
- MOWVDDDSMFDTDM-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)hexane Chemical compound CCCCC(C)(OOC(C)(C)C)OOC(C)(C)C MOWVDDDSMFDTDM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000864 peroxy group Chemical group O(O*)* 0.000 claims description 3
- 238000012662 bulk polymerization Methods 0.000 claims description 2
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 claims 1
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical group CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 claims 1
- 230000000704 physical effect Effects 0.000 abstract description 2
- 238000007334 copolymerization reaction Methods 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 description 16
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 10
- 239000000178 monomer Substances 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- -1 for example Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000003134 recirculating effect Effects 0.000 description 3
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 2
- PYOLJOJPIPCRDP-UHFFFAOYSA-N 1,1,3-trimethylcyclohexane Chemical compound CC1CCCC(C)(C)C1 PYOLJOJPIPCRDP-UHFFFAOYSA-N 0.000 description 1
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- 229910001060 Gray iron Inorganic materials 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000010962 carbon steel Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000000243 solution 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- 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
- C08F212/00—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 an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
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)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US852,411 | 1977-11-17 | ||
| US05/852,411 US4275182A (en) | 1977-11-17 | 1977-11-17 | Process for the preparation of improved styrene acrylic acid copolymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1111197A true CA1111197A (en) | 1981-10-20 |
Family
ID=25313243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA314,348A Expired CA1111197A (en) | 1977-11-17 | 1978-10-26 | Process for the preparation of improved styrene acrylic acid copolymers |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4275182A (enExample) |
| EP (1) | EP0002035B1 (enExample) |
| JP (1) | JPS5478788A (enExample) |
| AU (1) | AU521024B2 (enExample) |
| BR (1) | BR7807502A (enExample) |
| CA (1) | CA1111197A (enExample) |
| IT (1) | IT1111068B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4499924A (en) * | 1980-10-14 | 1985-02-19 | Smith International, Inc. | Method of making a drill pipe wear sleeve assembly and product thereof |
| US4397986A (en) * | 1982-03-03 | 1983-08-09 | Ethyl Corporation | Thermoplastic polyester blends |
| JPS5962604A (ja) * | 1982-10-01 | 1984-04-10 | Kanegafuchi Chem Ind Co Ltd | 共重合体の製造方法 |
| JPH0692462B2 (ja) * | 1985-06-03 | 1994-11-16 | 旭化成工業株式会社 | 食品容器用耐熱性熱可塑性樹脂 |
| NZ228160A (en) * | 1988-03-18 | 1990-11-27 | Grace W R & Co | Hot melt gasket comprising an ethylene/olefinic carboxylic acid copolymer |
| US5254650A (en) * | 1988-07-22 | 1993-10-19 | Kayaku Akzo Corporation | Process for the preparation of styrene or styrene derivative-containing copolymers |
| US5340875A (en) * | 1991-08-15 | 1994-08-23 | Arco Chemical Technology | Blends of polybutylene terephthalate resins and methacrylic acid-containing styrenic copolymers |
| CN107325217B (zh) * | 2017-08-01 | 2020-02-14 | 博立尔化工（扬州）有限公司 | 一种制备水性固体苯丙树脂的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2866767A (en) * | 1955-07-20 | 1958-12-30 | Du Pont | Composition containing copolymer of ethylencially unsaturated compounds and a diglycidyl ester of a dicarboxylic acid and process of making same |
| US3035033A (en) * | 1957-12-12 | 1962-05-15 | Dow Chemical Co | Molding grade copolymers and process for preparing the same |
| DE2345814A1 (de) * | 1973-09-11 | 1975-03-20 | Bp Benzin Und Petroleum Ag | Verfahren zur herstellung von styrolacrylsaeure-copolymerisaten und ihre verwendung |
| US3839308A (en) * | 1973-10-01 | 1974-10-01 | Dart Ind Inc | Styrene-methacrylic acid copolymers and their preparation |
-
1977
- 1977-11-17 US US05/852,411 patent/US4275182A/en not_active Expired - Lifetime
-
1978
- 1978-10-26 CA CA314,348A patent/CA1111197A/en not_active Expired
- 1978-10-27 AU AU41111/78A patent/AU521024B2/en not_active Expired
- 1978-11-09 EP EP78101337A patent/EP0002035B1/en not_active Expired
- 1978-11-16 BR BR7807502A patent/BR7807502A/pt unknown
- 1978-11-16 JP JP14056678A patent/JPS5478788A/ja active Granted
- 1978-11-16 IT IT51936/78A patent/IT1111068B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| BR7807502A (pt) | 1979-07-24 |
| EP0002035A1 (en) | 1979-05-30 |
| EP0002035B1 (en) | 1984-06-13 |
| JPS5478788A (en) | 1979-06-23 |
| IT1111068B (it) | 1986-01-13 |
| AU521024B2 (en) | 1982-03-11 |
| AU4111178A (en) | 1980-05-01 |
| JPS6158481B2 (enExample) | 1986-12-11 |
| IT7851936A0 (it) | 1978-11-16 |
| US4275182A (en) | 1981-06-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |