CA1106536A - High nitrile resins containing maleic anhydride - Google Patents
High nitrile resins containing maleic anhydrideInfo
- Publication number
- CA1106536A CA1106536A CA303,189A CA303189A CA1106536A CA 1106536 A CA1106536 A CA 1106536A CA 303189 A CA303189 A CA 303189A CA 1106536 A CA1106536 A CA 1106536A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- styrene
- group
- carbon atoms
- parts
- 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
- 150000002825 nitriles Chemical class 0.000 title claims abstract description 14
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 229920005989 resin Polymers 0.000 title description 6
- 239000011347 resin Substances 0.000 title description 6
- 239000000178 monomer Substances 0.000 claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 150000001993 dienes Chemical class 0.000 claims abstract description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 32
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 10
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 10
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 8
- 229920001971 elastomer Polymers 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical class CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 claims description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 5
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000004711 α-olefin Substances 0.000 claims description 5
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical class CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 4
- -1 methyl vinyl ethers Chemical class 0.000 claims description 4
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 229910001882 dioxygen Inorganic materials 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 229920000459 Nitrile rubber Polymers 0.000 claims 2
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 claims 2
- 239000012736 aqueous medium Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000003999 initiator Substances 0.000 claims 1
- 230000004888 barrier function Effects 0.000 abstract description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 24
- 229920000642 polymer Polymers 0.000 description 12
- 230000005540 biological transmission Effects 0.000 description 9
- 229940044600 maleic anhydride Drugs 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229940102838 methylmethacrylate Drugs 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
- FKTLISWEAOSVBS-UHFFFAOYSA-N 2-prop-1-en-2-yloxyprop-1-ene Chemical compound CC(=C)OC(C)=C FKTLISWEAOSVBS-UHFFFAOYSA-N 0.000 description 1
- WVLIQUPRRVSTGK-UHFFFAOYSA-N 6-(1,3-dioxopropan-2-yl)pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC(C(C=O)C=O)=N1 WVLIQUPRRVSTGK-UHFFFAOYSA-N 0.000 description 1
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical class CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 1
- DDZUQFPWZCKEBL-UHFFFAOYSA-N C(=CC1=CC=CC=C1)/C/1=C/C(=O)OC1=O.C(C=C)#N Chemical compound C(=CC1=CC=CC=C1)/C/1=C/C(=O)OC1=O.C(C=C)#N DDZUQFPWZCKEBL-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical class CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical class CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical class CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- AWJZTPWDQYFQPQ-UHFFFAOYSA-N methyl 2-chloroprop-2-enoate Chemical compound COC(=O)C(Cl)=C AWJZTPWDQYFQPQ-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical class CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical class C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical class CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical class CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 239000008096 xylene 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
- C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
- C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
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)
- Compositions Of Macromolecular Compounds (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80657777A | 1977-06-15 | 1977-06-15 | |
| US806,577 | 1977-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1106536A true CA1106536A (en) | 1981-08-04 |
Family
ID=25194353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA303,189A Expired CA1106536A (en) | 1977-06-15 | 1978-05-12 | High nitrile resins containing maleic anhydride |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS546091A (en, 2012) |
| AT (1) | AT366708B (en, 2012) |
| AU (1) | AU518735B2 (en, 2012) |
| BE (1) | BE868108A (en, 2012) |
| CA (1) | CA1106536A (en, 2012) |
| CH (1) | CH637661A5 (en, 2012) |
| DE (1) | DE2824713A1 (en, 2012) |
| DK (1) | DK155608C (en, 2012) |
| FR (1) | FR2394577B1 (en, 2012) |
| GB (1) | GB1599360A (en, 2012) |
| IT (1) | IT1096376B (en, 2012) |
| NL (1) | NL7806484A (en, 2012) |
| SE (1) | SE443364B (en, 2012) |
| ZA (1) | ZA782898B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2747822C2 (de) * | 1977-10-26 | 1985-05-30 | Bayer Ag, 5090 Leverkusen | Thermoplastische Formmassen |
| JP4746684B2 (ja) * | 2009-03-24 | 2011-08-10 | 有限会社長州電気 | 伸縮装置 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2734888A (en) * | 1951-08-31 | 1956-02-14 | Projducts | |
| DE919140C (de) * | 1951-12-05 | 1954-10-14 | Roehm & Haas G M B H | Verfahren zur Verbesserung der Eigenschaften von Acrylnitrilmischpolymerisaten |
| JPS4920294A (en, 2012) * | 1972-06-16 | 1974-02-22 | ||
| US3998907A (en) * | 1972-08-29 | 1976-12-21 | Arco Polymers, Inc. | Rubber-modified dicarboxylic acid imide copolymers |
| IT1043117B (it) * | 1975-10-03 | 1980-02-20 | Snam Progetti | Resine antiurto e metodo per la loro areparazione |
| DD252541A5 (de) * | 1985-12-04 | 1987-12-23 | Max-Planck-Gesellschaft Zur Foerderung Der Wissenschaften E. V.,De | Verfahren zur herstellung von phosphoverbindungen enthaltenden arzneimitteln fuer die tumorbehandlung |
-
1978
- 1978-05-12 CA CA303,189A patent/CA1106536A/en not_active Expired
- 1978-05-19 ZA ZA00782898A patent/ZA782898B/xx unknown
- 1978-05-22 AU AU36323/78A patent/AU518735B2/en not_active Expired
- 1978-05-30 AT AT0393378A patent/AT366708B/de not_active IP Right Cessation
- 1978-05-31 GB GB25677/78A patent/GB1599360A/en not_active Expired
- 1978-06-06 DE DE19782824713 patent/DE2824713A1/de not_active Ceased
- 1978-06-06 IT IT24274/78A patent/IT1096376B/it active
- 1978-06-12 FR FR7817464A patent/FR2394577B1/fr not_active Expired
- 1978-06-14 CH CH649078A patent/CH637661A5/de not_active IP Right Cessation
- 1978-06-14 SE SE7806875A patent/SE443364B/sv not_active IP Right Cessation
- 1978-06-14 BE BE188558A patent/BE868108A/xx not_active IP Right Cessation
- 1978-06-14 JP JP7312778A patent/JPS546091A/ja active Granted
- 1978-06-15 NL NL7806484A patent/NL7806484A/xx not_active Application Discontinuation
- 1978-06-15 DK DK269978A patent/DK155608C/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE7806875L (sv) | 1978-12-16 |
| ZA782898B (en) | 1979-05-30 |
| DK155608C (da) | 1989-10-16 |
| FR2394577A1 (fr) | 1979-01-12 |
| GB1599360A (en) | 1981-09-30 |
| DK155608B (da) | 1989-04-24 |
| FR2394577B1 (fr) | 1985-11-15 |
| SE443364B (sv) | 1986-02-24 |
| CH637661A5 (en) | 1983-08-15 |
| AT366708B (de) | 1982-05-10 |
| AU3632378A (en) | 1979-11-29 |
| BE868108A (fr) | 1978-10-02 |
| JPS6315286B2 (en, 2012) | 1988-04-04 |
| ATA393378A (de) | 1981-09-15 |
| IT7824274A0 (it) | 1978-06-06 |
| JPS546091A (en) | 1979-01-17 |
| IT1096376B (it) | 1985-08-26 |
| AU518735B2 (en) | 1981-10-15 |
| NL7806484A (nl) | 1978-12-19 |
| DK269978A (da) | 1978-12-16 |
| DE2824713A1 (de) | 1979-01-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |