CA1079893A - Shock-resistant resin and method for their preparation - Google Patents
Shock-resistant resin and method for their preparationInfo
- Publication number
- CA1079893A CA1079893A CA262,091A CA262091A CA1079893A CA 1079893 A CA1079893 A CA 1079893A CA 262091 A CA262091 A CA 262091A CA 1079893 A CA1079893 A CA 1079893A
- Authority
- CA
- Canada
- Prior art keywords
- maleic imide
- ethylene
- shock
- mixture
- terpolymer
- 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
- 239000011347 resin Substances 0.000 title claims abstract description 29
- 229920005989 resin Polymers 0.000 title claims abstract description 29
- 230000035939 shock Effects 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title abstract description 5
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 229920001897 terpolymer Polymers 0.000 claims abstract description 25
- 150000004291 polyenes Chemical class 0.000 claims abstract description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 22
- -1 ethylene, propylene Chemical group 0.000 claims description 17
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical class O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 13
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 11
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 claims description 7
- WXACXMWYHXOSIX-UHFFFAOYSA-N 5-propan-2-ylidenecyclopenta-1,3-diene Chemical compound CC(C)=C1C=CC=C1 WXACXMWYHXOSIX-UHFFFAOYSA-N 0.000 claims description 4
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims 1
- 239000000178 monomer Substances 0.000 abstract description 15
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract description 12
- 239000005977 Ethylene Substances 0.000 abstract description 12
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract description 7
- 150000003949 imides Chemical class 0.000 abstract description 3
- 229920006397 acrylic thermoplastic Polymers 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 abstract 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002348 vinylic group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 229920013728 elastomeric terpolymer Polymers 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical group C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- BTOVVHWKPVSLBI-UHFFFAOYSA-N 2-methylprop-1-enylbenzene Chemical compound CC(C)=CC1=CC=CC=C1 BTOVVHWKPVSLBI-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000703 anti-shock Effects 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000004968 peroxymonosulfuric acids Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
- C08F255/06—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms on to ethene-propene-diene terpolymers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT27951/75A IT1043117B (it) | 1975-10-03 | 1975-10-03 | Resine antiurto e metodo per la loro areparazione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1079893A true CA1079893A (en) | 1980-06-17 |
Family
ID=11222655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA262,091A Expired CA1079893A (en) | 1975-10-03 | 1976-09-27 | Shock-resistant resin and method for their preparation |
Country Status (20)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4485215A (en) * | 1983-05-11 | 1984-11-27 | Atlantic Richfield Company | Molding composition |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1106536A (en) * | 1977-06-15 | 1981-08-04 | George S. Li | High nitrile resins containing maleic anhydride |
| US4197263A (en) * | 1977-06-15 | 1980-04-08 | The Standard Oil Company | High nitrile resins containing maleic anhydride |
| US4223096A (en) * | 1977-12-27 | 1980-09-16 | Monsanto Company | Rubber-modified terpolymer with improved molding characteristics |
| JPS5518479A (en) * | 1978-07-24 | 1980-02-08 | Monsanto Co | Rubber denatured terpolymer |
| US4381373A (en) * | 1980-12-11 | 1983-04-26 | Mitsubishi Monsanto Chemical Company | Heat resistant resin composition |
| US4374951A (en) * | 1981-09-11 | 1983-02-22 | Monsanto Company | Polyblends comprising N-phenylmaleimide copolymers and SAN copolymers |
| US4504627A (en) * | 1983-09-12 | 1985-03-12 | Atlantic Richfield Company | Methylmethacrylate/N-phenylmaleimide copolymer-containing polymer alloys |
| JPS6176512A (ja) * | 1984-09-21 | 1986-04-19 | Toa Nenryo Kogyo Kk | メチルスチレン共重合体 |
| NL8501660A (nl) * | 1985-06-08 | 1987-01-02 | Dsm Resins Bv | Bismaleimide samenstellingen. |
| JPS63241014A (ja) * | 1986-11-21 | 1988-10-06 | Sumitomo Chem Co Ltd | 変性共重合体ゴムおよびその製造方法 |
| EP0628578A3 (de) * | 1993-06-11 | 1995-09-27 | Chemie Linz Gmbh | 2,6-Dimethylphenylphenymaleinimid als Comonomeres für Styrolcopolymerisate und Vinylchloridcopolymerisate. |
| DE4321344A1 (de) * | 1993-06-26 | 1995-01-05 | Chemie Linz Deutschland | 2,6-Dimethylphenylmaleinimid als Comonomeres für Styrolcopolymerisate und Vinylchloridkomopolymerisate |
| US6239221B1 (en) | 1995-09-13 | 2001-05-29 | Bayer Antwerpen S.A./N.V. | Low gloss weatherable polymer composition |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL107983C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1957-01-09 | 1900-01-01 | ||
| US3708555A (en) * | 1970-02-24 | 1973-01-02 | Gaylord Ass | Grafting of a mixture of styrene and maleic anhydride onto backbone polymers containing active or labile hydrogen atoms |
| US3687905A (en) * | 1970-03-16 | 1972-08-29 | Lubrizol Corp | Reaction product of carboxylic acid with degraded ethylene-propylene interpolymer |
| US3882194A (en) * | 1973-01-26 | 1975-05-06 | Chemplex Co | Cografted copolymers of a polyolefin, an acid or acid anhydride and an ester monomer |
| US3981958A (en) * | 1973-04-19 | 1976-09-21 | Toyoda Gosei Kabushiki-Kaisha (Toyoda Synthetics Co., Ltd.) | Graft copolymers and process for producing same |
-
1975
- 1975-10-03 IT IT27951/75A patent/IT1043117B/it active
-
1976
- 1976-09-13 ZA ZA765466A patent/ZA765466B/xx unknown
- 1976-09-15 AU AU17756/76A patent/AU1775676A/en not_active Expired
- 1976-09-16 IL IL50500A patent/IL50500A0/xx unknown
- 1976-09-20 CS CS766081A patent/CS196322B2/cs unknown
- 1976-09-20 US US05/724,602 patent/US4127617A/en not_active Expired - Lifetime
- 1976-09-27 CA CA262,091A patent/CA1079893A/en not_active Expired
- 1976-09-29 FR FR7629197A patent/FR2326436A1/fr active Granted
- 1976-09-30 NO NO763349A patent/NO763349L/no unknown
- 1976-09-30 YU YU02397/76A patent/YU239776A/xx unknown
- 1976-09-30 SE SE7610880A patent/SE7610880L/xx unknown
- 1976-10-01 BE BE171192A patent/BE846881A/xx unknown
- 1976-10-01 SU SU762406156A patent/SU764611A3/ru active
- 1976-10-01 DE DE2644492A patent/DE2644492B2/de not_active Ceased
- 1976-10-01 LU LU75918A patent/LU75918A1/xx unknown
- 1976-10-01 DD DD195105A patent/DD126282A5/xx unknown
- 1976-10-01 DK DK443676A patent/DK443676A/da unknown
- 1976-10-01 JP JP51117320A patent/JPS5243896A/ja active Pending
- 1976-10-01 GB GB40946/76A patent/GB1543358A/en not_active Expired
- 1976-10-04 NL NL7610972A patent/NL7610972A/xx not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4485215A (en) * | 1983-05-11 | 1984-11-27 | Atlantic Richfield Company | Molding composition |
| AU569922B2 (en) * | 1983-05-11 | 1988-02-25 | Atlantic Richfield Company | Graft copolymer composition |
Also Published As
| Publication number | Publication date |
|---|---|
| NO763349L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-04-05 |
| US4127617A (en) | 1978-11-28 |
| FR2326436A1 (fr) | 1977-04-29 |
| DE2644492B2 (de) | 1978-07-20 |
| DE2644492A1 (de) | 1977-04-07 |
| IT1043117B (it) | 1980-02-20 |
| FR2326436B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-04-18 |
| GB1543358A (en) | 1979-04-04 |
| SU764611A3 (ru) | 1980-09-15 |
| BE846881A (fr) | 1977-04-01 |
| JPS5243896A (en) | 1977-04-06 |
| NL7610972A (nl) | 1977-04-05 |
| ZA765466B (en) | 1977-08-31 |
| LU75918A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-05-06 |
| AU1775676A (en) | 1978-03-23 |
| SE7610880L (sv) | 1977-04-04 |
| CS196322B2 (en) | 1980-03-31 |
| YU239776A (en) | 1983-04-27 |
| DD126282A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-07-06 |
| DK443676A (da) | 1977-04-04 |
| IL50500A0 (en) | 1976-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |