CA1111172A - Rubber-modified acrylonitrile-vinyl ether-indene polymers - Google Patents
Rubber-modified acrylonitrile-vinyl ether-indene polymersInfo
- Publication number
- CA1111172A CA1111172A CA294,622A CA294622A CA1111172A CA 1111172 A CA1111172 A CA 1111172A CA 294622 A CA294622 A CA 294622A CA 1111172 A CA1111172 A CA 1111172A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- vinyl ether
- indene
- acrylonitrile
- 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
- 229920000642 polymer Polymers 0.000 title abstract description 9
- 229920002554 vinyl polymer Polymers 0.000 title abstract description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims abstract description 38
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 28
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims abstract description 18
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000002825 nitriles Chemical class 0.000 claims abstract description 8
- 229920001577 copolymer Polymers 0.000 claims abstract description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 239000000178 monomer Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000001993 dienes Chemical class 0.000 claims description 11
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229920001971 elastomer Polymers 0.000 claims description 7
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 229910001882 dioxygen Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 239000003999 initiator Substances 0.000 claims 1
- 239000012262 resinous product Substances 0.000 claims 1
- -1 acrylonitrile Chemical class 0.000 abstract description 6
- 230000004888 barrier function Effects 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 3
- 229920003244 diene elastomer Polymers 0.000 abstract description 2
- 239000002952 polymeric resin Substances 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000004615 ingredient Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- 229920000126 latex Polymers 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical class CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 2
- 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- FSVCELGFZIQNCK-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)glycine Chemical compound OCCN(CCO)CC(O)=O FSVCELGFZIQNCK-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 description 1
- YAOJJEJGPZRYJF-UHFFFAOYSA-N 1-ethenoxyhexane Chemical class CCCCCCOC=C YAOJJEJGPZRYJF-UHFFFAOYSA-N 0.000 description 1
- IOSXLUZXMXORMX-UHFFFAOYSA-N 1-ethenoxypentane Chemical class CCCCCOC=C IOSXLUZXMXORMX-UHFFFAOYSA-N 0.000 description 1
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 1
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
- DDXZFLFMKZXQOT-UHFFFAOYSA-N 2-fluoroprop-2-enenitrile Chemical compound FC(=C)C#N DDXZFLFMKZXQOT-UHFFFAOYSA-N 0.000 description 1
- YOWQWFMSQCOSBA-UHFFFAOYSA-N 2-methoxypropene Chemical compound COC(C)=C YOWQWFMSQCOSBA-UHFFFAOYSA-N 0.000 description 1
- SUNXFMPZAFGPFW-UHFFFAOYSA-N 2-methyl-5-(1-sulfanylpropan-2-yl)cyclohexane-1-thiol Chemical compound SCC(C)C1CCC(C)C(S)C1 SUNXFMPZAFGPFW-UHFFFAOYSA-N 0.000 description 1
- TVONJMOVBKMLOM-UHFFFAOYSA-N 2-methylidenebutanenitrile Chemical compound CCC(=C)C#N TVONJMOVBKMLOM-UHFFFAOYSA-N 0.000 description 1
- NKELPOAIHNHDDV-UHFFFAOYSA-N CCCCC(CCCCCCC)S.C1C=CC2=CC=CC=C12 Chemical compound CCCCC(CCCCCCC)S.C1C=CC2=CC=CC=C12 NKELPOAIHNHDDV-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910002567 K2S2O8 Inorganic materials 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052783 alkali metal Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 235000019394 potassium persulphate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000003039 volatile agent 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)
- Graft Or Block Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US773,531 | 1977-03-02 | ||
| US05/773,531 US4082819A (en) | 1977-03-02 | 1977-03-02 | Rubber-modified acrylonitrile-vinyl ether-indene polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1111172A true CA1111172A (en) | 1981-10-20 |
Family
ID=25098578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA294,622A Expired CA1111172A (en) | 1977-03-02 | 1978-01-09 | Rubber-modified acrylonitrile-vinyl ether-indene polymers |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4082819A (en, 2012) |
| JP (1) | JPS53109592A (en, 2012) |
| AT (1) | AT351765B (en, 2012) |
| AU (1) | AU513652B2 (en, 2012) |
| BE (1) | BE863462A (en, 2012) |
| CA (1) | CA1111172A (en, 2012) |
| DE (1) | DE2802355A1 (en, 2012) |
| DK (1) | DK26178A (en, 2012) |
| FR (1) | FR2382466A1 (en, 2012) |
| GB (1) | GB1571374A (en, 2012) |
| IT (1) | IT1091966B (en, 2012) |
| NL (1) | NL7800611A (en, 2012) |
| SE (1) | SE7800330L (en, 2012) |
| ZA (1) | ZA78201B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2565840B2 (ja) * | 1993-08-03 | 1996-12-18 | ショーボンド建設株式会社 | 橋梁構造物の縦目地用伸縮継手構造 |
| FR2832060B1 (fr) * | 2001-11-09 | 2004-07-09 | Oreal | Composition contenant un ester n-acyle d'acide amine et un filtre uv structuree par un polyamide |
| LT3181567T (lt) | 2012-09-10 | 2019-07-25 | Principia Biopharma Inc. | Pirazolpirimidino junginiai kaip kinazės slopikliai |
| AU2015218713B2 (en) | 2014-02-21 | 2019-10-10 | Principia Biopharma Inc. | Salts and solid form of a BTK inhibitor |
| CA2970723C (en) | 2014-12-18 | 2023-09-05 | Principia Biopharma Inc. | Treatment of pemphigus |
| TW201718572A (zh) | 2015-06-24 | 2017-06-01 | 普林斯匹亞生物製藥公司 | 酪胺酸激酶抑制劑 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3950454A (en) * | 1974-12-09 | 1976-04-13 | Standard Oil Company | Polymerizates of olefinic nitriles and diene rubbers |
| US3947527A (en) * | 1975-02-21 | 1976-03-30 | The Standard Oil Company | Polymerizates of olefinic nitriles and diene rubbers |
| US4020128A (en) * | 1976-02-13 | 1977-04-26 | Standard Oil Company | Polymerizates of olefinic nitriles and diene rubbers |
-
1977
- 1977-03-02 US US05/773,531 patent/US4082819A/en not_active Expired - Lifetime
-
1978
- 1978-01-09 CA CA294,622A patent/CA1111172A/en not_active Expired
- 1978-01-11 SE SE7800330A patent/SE7800330L/xx unknown
- 1978-01-12 IT IT19221/78A patent/IT1091966B/it active
- 1978-01-12 ZA ZA00780201A patent/ZA78201B/xx unknown
- 1978-01-13 GB GB1433/78A patent/GB1571374A/en not_active Expired
- 1978-01-17 AU AU32491/78A patent/AU513652B2/en not_active Expired
- 1978-01-18 DK DK26178A patent/DK26178A/da unknown
- 1978-01-18 NL NL7800611A patent/NL7800611A/xx not_active Application Discontinuation
- 1978-01-20 DE DE19782802355 patent/DE2802355A1/de not_active Withdrawn
- 1978-01-24 AT AT50678A patent/AT351765B/de not_active IP Right Cessation
- 1978-01-27 FR FR7802308A patent/FR2382466A1/fr not_active Withdrawn
- 1978-01-30 BE BE184747A patent/BE863462A/xx unknown
- 1978-02-28 JP JP2343078A patent/JPS53109592A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT1091966B (it) | 1985-07-06 |
| AU513652B2 (en) | 1980-12-11 |
| IT7819221A0 (it) | 1978-01-12 |
| GB1571374A (en) | 1980-07-16 |
| JPS53109592A (en) | 1978-09-25 |
| AU3249178A (en) | 1979-07-26 |
| JPS623848B2 (en, 2012) | 1987-01-27 |
| DK26178A (da) | 1978-09-03 |
| DE2802355A1 (de) | 1978-09-07 |
| NL7800611A (nl) | 1978-09-05 |
| FR2382466A1 (fr) | 1978-09-29 |
| US4082819A (en) | 1978-04-04 |
| ZA78201B (en) | 1978-12-27 |
| AT351765B (de) | 1979-08-10 |
| ATA50678A (de) | 1979-01-15 |
| BE863462A (fr) | 1978-05-16 |
| SE7800330L (sv) | 1978-09-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |