CA1078989A - Polymerizates of olefinic nitriles and diene rubbers - Google Patents
Polymerizates of olefinic nitriles and diene rubbersInfo
- Publication number
- CA1078989A CA1078989A CA239,064A CA239064A CA1078989A CA 1078989 A CA1078989 A CA 1078989A CA 239064 A CA239064 A CA 239064A CA 1078989 A CA1078989 A CA 1078989A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- acrylonitrile
- indene
- butadiene
- 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
- 229920003244 diene elastomer 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 70
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims abstract description 54
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 46
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000000178 monomer Substances 0.000 claims abstract description 29
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 150000001993 dienes Chemical class 0.000 claims abstract description 13
- 150000002148 esters Chemical class 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 18
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 229920001971 elastomer Polymers 0.000 claims description 13
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- 239000000839 emulsion Substances 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 229910001882 dioxygen Inorganic materials 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 239000003999 initiator Substances 0.000 claims 1
- 239000002952 polymeric resin Substances 0.000 claims 1
- 229920003002 synthetic resin Polymers 0.000 claims 1
- 239000007789 gas Substances 0.000 abstract description 9
- -1 acrylonitrile Chemical class 0.000 abstract description 6
- 239000007787 solid Substances 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 230000035699 permeability Effects 0.000 abstract description 3
- 239000007788 liquid Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract 1
- 230000000704 physical effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 229920000642 polymer Polymers 0.000 description 17
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 15
- 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 12
- 239000004615 ingredient Substances 0.000 description 12
- 229920000126 latex Polymers 0.000 description 11
- 230000005540 biological transmission Effects 0.000 description 10
- 238000007720 emulsion polymerization reaction Methods 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000000977 initiatory effect Effects 0.000 description 8
- 239000005060 rubber Substances 0.000 description 8
- 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 5
- 229940010048 aluminum sulfate Drugs 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 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
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 238000013031 physical testing Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 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
- TVONJMOVBKMLOM-UHFFFAOYSA-N 2-methylidenebutanenitrile Chemical compound CCC(=C)C#N TVONJMOVBKMLOM-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
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical class CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 1
- MPFMFFPEMCAIKK-UHFFFAOYSA-N C=CC#N.COC(=O)C=C.C1=CC=C2CC=CC2=C1 Chemical compound C=CC#N.COC(=O)C=C.C1=CC=C2CC=CC2=C1 MPFMFFPEMCAIKK-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
- 239000004908 Emulsion polymer Substances 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
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- FSVCELGFZIQNCK-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)glycine Chemical compound OCCN(CCO)CC(O)=O FSVCELGFZIQNCK-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical class CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction 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
- 229940087305 limonene Drugs 0.000 description 1
- 235000001510 limonene Nutrition 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- GYDSPAVLTMAXHT-UHFFFAOYSA-N pentyl 2-methylprop-2-enoate Chemical class CCCCCOC(=O)C(C)=C GYDSPAVLTMAXHT-UHFFFAOYSA-N 0.000 description 1
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical class CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 1
- 229920003217 poly(methylsilsesquioxane) Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 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
- 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
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/915—Polymer from monoethylenic cyclic hydrocarbon
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/933—Blend of limited gas permeability
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)
- Polymerisation Methods In General (AREA)
- Polyamides (AREA)
- Lubricants (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/531,185 US3950454A (en) | 1974-12-09 | 1974-12-09 | Polymerizates of olefinic nitriles and diene rubbers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1078989A true CA1078989A (en) | 1980-06-03 |
Family
ID=24116604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA239,064A Expired CA1078989A (en) | 1974-12-09 | 1975-11-05 | Polymerizates of olefinic nitriles and diene rubbers |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US3950454A (en, 2012) |
| JP (1) | JPS5921329B2 (en, 2012) |
| AR (1) | AR210478A1 (en, 2012) |
| AT (1) | AT342297B (en, 2012) |
| BE (1) | BE836397A (en, 2012) |
| BG (1) | BG31077A3 (en, 2012) |
| CA (1) | CA1078989A (en, 2012) |
| CH (1) | CH618196A5 (en, 2012) |
| CS (1) | CS189733B2 (en, 2012) |
| DD (1) | DD124120A5 (en, 2012) |
| DE (1) | DE2552234C2 (en, 2012) |
| DK (1) | DK546475A (en, 2012) |
| EG (1) | EG12591A (en, 2012) |
| ES (1) | ES443152A1 (en, 2012) |
| FI (1) | FI59606C (en, 2012) |
| FR (1) | FR2294207A1 (en, 2012) |
| GB (1) | GB1491120A (en, 2012) |
| IE (1) | IE42202B1 (en, 2012) |
| IL (1) | IL48442A (en, 2012) |
| IN (1) | IN144757B (en, 2012) |
| IT (1) | IT1050743B (en, 2012) |
| LU (1) | LU73945A1 (en, 2012) |
| NL (1) | NL7513695A (en, 2012) |
| NO (1) | NO754132L (en, 2012) |
| PH (1) | PH11192A (en, 2012) |
| RO (1) | RO67246A (en, 2012) |
| SE (1) | SE7513811L (en, 2012) |
| SU (1) | SU625617A3 (en, 2012) |
| TR (1) | TR18986A (en, 2012) |
| ZA (1) | ZA756978B (en, 2012) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4154778A (en) * | 1975-11-27 | 1979-05-15 | Kureha Kagaku Kogyo Kabushiki Kaisha | Process for producing a graft polymer |
| US4020128A (en) * | 1976-02-13 | 1977-04-26 | Standard Oil Company | Polymerizates of olefinic nitriles and diene rubbers |
| US4107237A (en) * | 1977-02-17 | 1978-08-15 | The Standard Oil Company | Rubber-modified acrylonitrile-styrene-indene interpolymers |
| US4082819A (en) * | 1977-03-02 | 1978-04-04 | The Standard Oil Company | Rubber-modified acrylonitrile-vinyl ether-indene polymers |
| US4102947A (en) * | 1977-04-11 | 1978-07-25 | The Standard Oil Company | Rubber-modified acrylonitrile copolymers prepared in aqueous suspension |
| US4082820A (en) * | 1977-06-15 | 1978-04-04 | The Standard Oil Company | High softening maleic anhydride copolymers |
| US4224097A (en) * | 1978-11-24 | 1980-09-23 | Standard Oil Company | Solvent bonding of high acrylonitrile copolymers |
| JPS6086135A (ja) * | 1983-10-19 | 1985-05-15 | Nippon Zeon Co Ltd | 耐スチ−ム性の改善されたゴム組成物 |
| JPH072895B2 (ja) * | 1984-03-01 | 1995-01-18 | 日本ゼオン株式会社 | 耐衝撃性フェノール系樹脂組成物 |
| US4761455A (en) * | 1987-06-12 | 1988-08-02 | The Standard Oil Company | Poly(vinyl chloride) compositions and polymeric blending agents useful therefor |
| US5106925A (en) * | 1990-12-21 | 1992-04-21 | The Standard Oil Company | Preparation of melt-processable acrylonitrile/methacrylonitrile copolymers |
| US5618901A (en) * | 1993-11-10 | 1997-04-08 | The Standard Oil Company | Process for making a high nitrile multipolymer prepared from acrylonitrile and olefinically unsaturated monomers |
| US20060205881A1 (en) * | 2005-03-08 | 2006-09-14 | Michael Gozdiff | Blends of diene rubber with thermoplastic copolymer modifield with nitrile rubber |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3426102A (en) * | 1965-08-18 | 1969-02-04 | Standard Oil Co | Polymerizates of olefinic nitriles and diene-nitrile rubbers |
| GB1213700A (en) * | 1967-09-14 | 1970-11-25 | Borg Warner | Transparent high impact graft polymers |
| US3586737A (en) * | 1969-02-13 | 1971-06-22 | Standard Oil Co | Impact-resistant rubber-modified olefinic nitrile-acrylic ester polymers |
| JPS5037700B1 (en, 2012) * | 1971-04-23 | 1975-12-04 | ||
| US3846509A (en) * | 1971-10-27 | 1974-11-05 | American Cyanamid Co | Acrylonitrile-acrylate copolymers reinforced with grafted butadiene rubber |
-
1974
- 1974-12-09 US US05/531,185 patent/US3950454A/en not_active Expired - Lifetime
-
1975
- 1975-11-04 IN IN2111/CAL/75A patent/IN144757B/en unknown
- 1975-11-05 CA CA239,064A patent/CA1078989A/en not_active Expired
- 1975-11-06 ZA ZA00756978A patent/ZA756978B/xx unknown
- 1975-11-07 IL IL48442A patent/IL48442A/xx unknown
- 1975-11-14 GB GB47032/75A patent/GB1491120A/en not_active Expired
- 1975-11-20 TR TR18986A patent/TR18986A/xx unknown
- 1975-11-21 DE DE2552234A patent/DE2552234C2/de not_active Expired
- 1975-11-24 NL NL7513695A patent/NL7513695A/xx not_active Application Discontinuation
- 1975-11-27 BG BG031619A patent/BG31077A3/xx unknown
- 1975-11-28 AT AT907475A patent/AT342297B/de not_active IP Right Cessation
- 1975-12-01 CH CH1558475A patent/CH618196A5/de not_active IP Right Cessation
- 1975-12-02 ES ES443152A patent/ES443152A1/es not_active Expired
- 1975-12-03 IT IT29979/75A patent/IT1050743B/it active
- 1975-12-03 FI FI753405A patent/FI59606C/fi not_active IP Right Cessation
- 1975-12-03 EG EG713/75A patent/EG12591A/xx active
- 1975-12-03 DK DK546475A patent/DK546475A/da not_active Application Discontinuation
- 1975-12-06 DD DD189946A patent/DD124120A5/xx unknown
- 1975-12-08 JP JP50146796A patent/JPS5921329B2/ja not_active Expired
- 1975-12-08 LU LU73945A patent/LU73945A1/xx unknown
- 1975-12-08 RO RO7584138A patent/RO67246A/ro unknown
- 1975-12-08 SU SU752196559A patent/SU625617A3/ru active
- 1975-12-08 FR FR7537435A patent/FR2294207A1/fr active Granted
- 1975-12-08 BE BE162546A patent/BE836397A/xx unknown
- 1975-12-08 PH PH17845A patent/PH11192A/en unknown
- 1975-12-08 SE SE7513811A patent/SE7513811L/xx unknown
- 1975-12-08 NO NO754132A patent/NO754132L/no unknown
- 1975-12-08 IE IE2665/75A patent/IE42202B1/en unknown
- 1975-12-09 CS CS758364A patent/CS189733B2/cs unknown
- 1975-12-10 AR AR261424A patent/AR210478A1/es active
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