JPH051283B2 - - Google Patents
Info
- Publication number
- JPH051283B2 JPH051283B2 JP59195633A JP19563384A JPH051283B2 JP H051283 B2 JPH051283 B2 JP H051283B2 JP 59195633 A JP59195633 A JP 59195633A JP 19563384 A JP19563384 A JP 19563384A JP H051283 B2 JPH051283 B2 JP H051283B2
- Authority
- JP
- Japan
- Prior art keywords
- alkali
- group
- polymer
- solution
- halobenzyl
- 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 - Lifetime
Links
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 50
- 239000000243 solution Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 229920000642 polymer Polymers 0.000 claims description 24
- 239000003513 alkali Substances 0.000 claims description 18
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 125000006277 halobenzyl group Chemical group 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 9
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical group [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 8
- -1 3-mercaptopropionamide diphenylamine Chemical group 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000004714 phosphonium salts Chemical group 0.000 claims description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical group [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 150000004703 alkoxides Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001805 chlorine compounds Chemical group 0.000 claims description 2
- 238000006731 degradation reaction Methods 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Chemical group 0.000 claims description 2
- 239000011574 phosphorus Chemical group 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- NFVMNXZFSKGLDR-UHFFFAOYSA-N 2,6-ditert-butyl-4-sulfanylphenol Chemical compound CC(C)(C)C1=CC(S)=CC(C(C)(C)C)=C1O NFVMNXZFSKGLDR-UHFFFAOYSA-N 0.000 claims 1
- BXAVKNRWVKUTLY-UHFFFAOYSA-N 4-sulfanylphenol Chemical group OC1=CC=C(S)C=C1 BXAVKNRWVKUTLY-UHFFFAOYSA-N 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 229910000103 lithium hydride Inorganic materials 0.000 claims 1
- 235000015320 potassium carbonate Nutrition 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 235000017550 sodium carbonate Nutrition 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 230000006866 deterioration Effects 0.000 description 17
- 229920001971 elastomer Polymers 0.000 description 15
- 239000003112 inhibitor Substances 0.000 description 15
- 239000005060 rubber Substances 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 229920003048 styrene butadiene rubber Polymers 0.000 description 11
- 239000002174 Styrene-butadiene Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 230000003712 anti-aging effect Effects 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 5
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 150000003839 salts Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical class C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- FMMQDMHSGNXJSQ-UHFFFAOYSA-N n,n-diphenylhydroxylamine Chemical compound C=1C=CC=CC=1N(O)C1=CC=CC=C1 FMMQDMHSGNXJSQ-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000003408 phase transfer catalysis Methods 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 230000002000 scavenging effect Effects 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- YHHHHJCAVQSFMJ-FNORWQNLSA-N (3e)-deca-1,3-diene Chemical compound CCCCCC\C=C\C=C YHHHHJCAVQSFMJ-FNORWQNLSA-N 0.000 description 1
- AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- IUGGPPCFRKABQM-UHFFFAOYSA-N 1-aminononan-2-one Chemical group CCCCCCCC(=O)CN IUGGPPCFRKABQM-UHFFFAOYSA-N 0.000 description 1
- YBVUOVWOBHAPDH-UHFFFAOYSA-N 2-(2-sulfanylethoxy)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCS YBVUOVWOBHAPDH-UHFFFAOYSA-N 0.000 description 1
- IGLWCQMNTGCUBB-UHFFFAOYSA-N 3-methylidenepent-1-ene Chemical compound CCC(=C)C=C IGLWCQMNTGCUBB-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-O butylazanium Chemical compound CCCC[NH3+] HQABUPZFAYXKJW-UHFFFAOYSA-O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010058 rubber compounding Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KCSOHLKZTZMKQA-UHFFFAOYSA-M tetraheptylazanium;iodide Chemical compound [I-].CCCCCCC[N+](CCCCCCC)(CCCCCCC)CCCCCCC KCSOHLKZTZMKQA-UHFFFAOYSA-M 0.000 description 1
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/40—Introducing phosphorus atoms or phosphorus-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- General 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)
Description
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é ã«èšèŒã®æ¹æ³ã ïŒïŒ åèšã®ã¢ã«ã«ãªæ°Žæº¶æ¶²ãæ°Žé žåãããªãŠã
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æ³ã ïŒïŒ åèšã®ã¢ã«ã«ãªæ°Žæº¶æ¶²ãæ°Žé žåã«ãªãŠã æ°Ž
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æ³ã ïŒïŒ åèšã®åå¿æž©åºŠã60°ä¹è³80âã§ããç¹èš±
è«æ±ã®ç¯å²ç¬¬ïŒé ã«èšèŒã®æ¹æ³ã ïŒïŒ åèšã®ã¢ã«ã«ãªååç©ãNaHïŒKHïŒ
LiHïŒNaïŒLiïŒïŒ«ïŒNaOHïŒNaHCO3ïŒKOHïŒ
K2CO3ïŒNa2CO3åã³K2HCO3ãããªã矀ããéž
æãããååç©ã®é氎溶液ã§ããç¹èš±è«æ±ã®ç¯å²
第ïŒé ã«èšèŒã®æ¹æ³ã
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US533717 | 1983-09-19 | ||
| US06/533,717 US4481337A (en) | 1983-09-19 | 1983-09-19 | Process for the preparation of modified polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6088009A JPS6088009A (ja) | 1985-05-17 |
| JPH051283B2 true JPH051283B2 (ja) | 1993-01-07 |
Family
ID=24127166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59195633A Granted JPS6088009A (ja) | 1983-09-19 | 1984-09-18 | å€æ§éåç©ã®è£œé æ¹æ³ |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4481337A (ja) |
| EP (1) | EP0136250B1 (ja) |
| JP (1) | JPS6088009A (ja) |
| BR (1) | BR8404461A (ja) |
| CA (1) | CA1225795A (ja) |
| DE (1) | DE3476209D1 (ja) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4804028A (en) * | 1986-03-05 | 1989-02-14 | The Goodyear Tire & Rubber Company | Non-staining vulcanized elastomeric composition and tires having sidewalls comprising said composition |
| US4946717A (en) * | 1986-03-10 | 1990-08-07 | The Goodyear Tire & Rubber Company | Water based precure paint for rubber articles |
| US4988773A (en) * | 1986-05-27 | 1991-01-29 | Basf Aktiengesellschaft | Homopolymers or block copolymers of vinylaromatics and/or dienes with ammonium groups, and preparation of same |
| US4981917A (en) * | 1987-08-12 | 1991-01-01 | Atochem North America, Inc. | Process for preparing polymer bound antioxidant stabilizers |
| US4857596A (en) * | 1987-08-12 | 1989-08-15 | Pennwalt Corporation | Polymer bound antioxidant stabilizers |
| JPH01180803A (ja) * | 1988-01-12 | 1989-07-18 | Shionogi & Co Ltd | å®å®ãªæ®ºè«çµæç© |
| US4940741A (en) * | 1988-06-17 | 1990-07-10 | National Starch And Chemical Investment Holding Corporation | Process for the production of hardboard |
| US8025010B1 (en) | 1990-09-18 | 2011-09-27 | Alliant Techsystems Inc. | Method for reducing charge retention properties of solid propellants |
| US5171789A (en) * | 1990-10-09 | 1992-12-15 | The Goodyear Tire & Rubber Company | Poly(oxydiphenylamines) |
| GB9502225D0 (en) * | 1995-02-04 | 1995-03-22 | Zeneca Ltd | Method |
| RS62835B1 (sr) * | 2014-09-12 | 2022-02-28 | Cooper Tire & Rubber Co | Prirodna guma otporna na oksidaciju i postupak njene proizvodnje |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2694702A (en) * | 1951-04-13 | 1954-11-16 | Dow Chemical Co | Soluble chloromethylated polymers of styrene and alpha-methyl styrene, their quaternary ammonium salts and method of making the same |
| US3022253A (en) * | 1958-03-24 | 1962-02-20 | Dow Chemical Co | Resinous insoluble nitrogen-containing polymers derived from vinylbenzyl chloride and vinylpyridines |
| US3168502A (en) * | 1961-03-09 | 1965-02-02 | American Cyanamid Co | Polymer composed of phosphonium salts |
| CA1053832A (en) * | 1973-11-08 | 1979-05-01 | Polysar Limited | Polymeric antioxidants |
| AU497808B2 (en) * | 1975-04-21 | 1979-01-11 | Dow Chemical Company, The | Latexes |
| US4074035A (en) * | 1975-04-22 | 1978-02-14 | Exxon Research & Engineering Co. | Halomethylated aromatic interpolymers |
| US4452939A (en) * | 1983-02-28 | 1984-06-05 | The Goodyear Tire & Rubber Company | Process for the preparation of high molecular weight polymeric antidegradants |
-
1983
- 1983-09-19 US US06/533,717 patent/US4481337A/en not_active Expired - Lifetime
-
1984
- 1984-09-05 CA CA000462404A patent/CA1225795A/en not_active Expired
- 1984-09-05 BR BR8404461A patent/BR8404461A/pt not_active IP Right Cessation
- 1984-09-07 DE DE8484630133T patent/DE3476209D1/de not_active Expired
- 1984-09-07 EP EP84630133A patent/EP0136250B1/en not_active Expired
- 1984-09-18 JP JP59195633A patent/JPS6088009A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| BR8404461A (pt) | 1985-07-30 |
| CA1225795A (en) | 1987-08-18 |
| EP0136250A3 (en) | 1985-05-08 |
| EP0136250A2 (en) | 1985-04-03 |
| EP0136250B1 (en) | 1989-01-18 |
| DE3476209D1 (en) | 1989-02-23 |
| US4481337A (en) | 1984-11-06 |
| JPS6088009A (ja) | 1985-05-17 |
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