JPH0441161B2 - - Google Patents
Info
- Publication number
- JPH0441161B2 JPH0441161B2 JP59032274A JP3227484A JPH0441161B2 JP H0441161 B2 JPH0441161 B2 JP H0441161B2 JP 59032274 A JP59032274 A JP 59032274A JP 3227484 A JP3227484 A JP 3227484A JP H0441161 B2 JPH0441161 B2 JP H0441161B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- weight
- latex
- temperature
- hydrazine
- 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
- 238000006243 chemical reaction Methods 0.000 claims description 55
- 229920000642 polymer Polymers 0.000 claims description 41
- 229920000126 latex Polymers 0.000 claims description 38
- 239000004816 latex Substances 0.000 claims description 37
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 28
- 229910052751 metal Inorganic materials 0.000 claims description 23
- 239000002184 metal Substances 0.000 claims description 23
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 22
- 238000005984 hydrogenation reaction Methods 0.000 claims description 18
- 239000011541 reaction mixture Substances 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 12
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 11
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 11
- 239000007800 oxidant agent Substances 0.000 claims description 11
- 150000001993 dienes Chemical class 0.000 claims description 10
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 150000002432 hydroperoxides Chemical class 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 6
- 229910021645 metal ion Inorganic materials 0.000 claims description 6
- 244000043261 Hevea brasiliensis Species 0.000 claims description 5
- 229920003052 natural elastomer Polymers 0.000 claims description 5
- 229920001194 natural rubber Polymers 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 239000005062 Polybutadiene Substances 0.000 claims description 4
- 239000012190 activator Substances 0.000 claims description 4
- 229920002857 polybutadiene Polymers 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229920001195 polyisoprene Polymers 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 claims 1
- 229910017052 cobalt Inorganic materials 0.000 claims 1
- 239000010941 cobalt Substances 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 239000011133 lead Substances 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 229910052709 silver Inorganic materials 0.000 claims 1
- 239000004332 silver Substances 0.000 claims 1
- 239000011135 tin Substances 0.000 claims 1
- 229910052718 tin Inorganic materials 0.000 claims 1
- 230000009467 reduction Effects 0.000 description 33
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 29
- 150000001336 alkenes Chemical class 0.000 description 26
- 238000004458 analytical method Methods 0.000 description 25
- 239000003999 initiator Substances 0.000 description 20
- 229920001971 elastomer Polymers 0.000 description 19
- 239000005060 rubber Substances 0.000 description 19
- 229920000459 Nitrile rubber Polymers 0.000 description 14
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 13
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 230000035484 reaction time Effects 0.000 description 10
- -1 (o- Chemical class 0.000 description 8
- 239000002518 antifoaming agent Substances 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000003760 magnetic stirring Methods 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
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 description 1
- XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 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
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- ZIUWGZFVIRSZAN-UHFFFAOYSA-N [Ag].[Se].[Po] Chemical compound [Ag].[Se].[Po] ZIUWGZFVIRSZAN-UHFFFAOYSA-N 0.000 description 1
- UKUJCSBWRBWNAV-UHFFFAOYSA-N [Sn].[V] Chemical compound [Sn].[V] UKUJCSBWRBWNAV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Inorganic materials Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- JRTYPQGPARWINR-UHFFFAOYSA-N palladium platinum Chemical compound [Pd].[Pt] JRTYPQGPARWINR-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/02—Hydrogenation
-
- 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
- C08F8/04—Reduction, e.g. hydrogenation
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US468816 | 1983-02-22 | ||
| US06/468,816 US4452950A (en) | 1983-02-22 | 1983-02-22 | Process for hydrogenation of carbon-carbon double bonds in an unsaturated polymer in latex form |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59161415A JPS59161415A (ja) | 1984-09-12 |
| JPH0441161B2 true JPH0441161B2 (OSRAM) | 1992-07-07 |
Family
ID=23861354
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59032274A Granted JPS59161415A (ja) | 1983-02-22 | 1984-02-22 | 不飽和ポリマ−中の炭素−炭素二重結合の水素化方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4452950A (OSRAM) |
| EP (1) | EP0117221B1 (OSRAM) |
| JP (1) | JPS59161415A (OSRAM) |
| AU (1) | AU559579B2 (OSRAM) |
| BR (1) | BR8400562A (OSRAM) |
| CA (1) | CA1216598A (OSRAM) |
| DE (1) | DE3480401D1 (OSRAM) |
| ES (1) | ES8506329A1 (OSRAM) |
| MY (1) | MY100004A (OSRAM) |
Families Citing this family (75)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5244943A (en) * | 1986-02-28 | 1993-09-14 | Nippon Zeon Co., Ltd. | Nitrile group-containing highly saturated polymer rubber latex and process for production thereof |
| JPH0832802B2 (ja) * | 1986-02-28 | 1996-03-29 | 日本ゼオン株式会社 | 破断強度に優れた加硫フィルム形成用水性分散体 |
| DE3618907A1 (de) * | 1986-06-05 | 1987-12-10 | Bayer Ag | Verbundwerkstoffe aus vorbehandeltem fasermaterial und vulkanisaten aus hnbr |
| US4914160A (en) * | 1988-06-23 | 1990-04-03 | Hormoz Azizian | Deuteration of unsaturated polymers and copolymers |
| US4945135A (en) * | 1988-07-25 | 1990-07-31 | California Institute Of Technology | Ring opening metathesis polymerization of strained cyclic ethers |
| US5362810A (en) * | 1988-09-15 | 1994-11-08 | Bayer Aktiengesellschaft | Thermoplastic molding compositions of aromatic polyether sulfone and hydrogenated nitrile rubber |
| US4925900A (en) * | 1988-09-16 | 1990-05-15 | Polysar Limited | Halogenated-hydrogenated acrylonitrile-butadiene rubber |
| JP2732273B2 (ja) * | 1988-12-29 | 1998-03-25 | 日本ゼオン株式会社 | ニトリル基含有水素化重合体の製造方法 |
| ES2067028T3 (es) * | 1989-05-11 | 1995-03-16 | Olin Corp | Un proceso para minimizar los residuos de hidrazina libre en polimeros de latex. |
| US4954614A (en) * | 1989-05-11 | 1990-09-04 | Olin Corporation | Process for minimizing residual hydrazine in polymer latices |
| US5068313A (en) * | 1989-05-16 | 1991-11-26 | Olin Corporation | Process for minimizing residual free hydrazine in polymer latices |
| US5171833A (en) * | 1989-05-16 | 1992-12-15 | Olin Corporation | Process for minimizing residual free hydrazine in polymer latices |
| US5302696A (en) * | 1989-05-16 | 1994-04-12 | Olin Corporation | Process for minimizing residual free hydrazine in polymer latices |
| US5319016A (en) * | 1989-07-04 | 1994-06-07 | Chisso Corporation | Emulsion adhesive composition and process for production thereof |
| US5057601A (en) * | 1989-11-06 | 1991-10-15 | Olin Corporation | Process for producing a gel-free coagulated rubber with low ethylenic unsaturation |
| US5039737A (en) * | 1990-02-22 | 1991-08-13 | The Goodyear Tire & Rubber Company/Olin Corp. | Ozonolysis of hydrogenated latices |
| JP2876813B2 (ja) * | 1990-05-29 | 1999-03-31 | ダイキン工業株式会社 | 含フッ素塗料用重合体および組成物 |
| US5221714A (en) * | 1991-04-04 | 1993-06-22 | The Goodyear Tire & Rubber Company | Blend of rubber latices containing a hydrogenated rubber latex |
| US5254761A (en) * | 1992-05-18 | 1993-10-19 | The Goodyear Tire & Rubber Company | Process for selective reduction of unsaturated organic compounds |
| US5242961A (en) * | 1992-05-28 | 1993-09-07 | Shell Oil Company | Color prevention in titanium catalyzed hydrogenated diene polymers |
| US5314741A (en) * | 1992-10-07 | 1994-05-24 | The Goodyear Tire & Rubber Company | Rubber article having protective coating |
| US5397839A (en) * | 1993-12-13 | 1995-03-14 | Advanced Elastomer Systems, L.P. | Polyester-hydrogenated diene rubber compositions |
| US5902889A (en) * | 1997-09-18 | 1999-05-11 | The Goodyear Tire & Rubber Company | Process for hydrogenation of carbon-carbon double bonds of a water-soluble olefinically unsaturated carboxylic acid salt |
| DE19753302A1 (de) * | 1997-12-01 | 1999-06-02 | Basf Ag | Verfahren zur selektiven Hydrierung von ethylenisch ungesättigten Doppelbindungen in Polymerisaten |
| NL1009841C2 (nl) * | 1998-08-11 | 2000-02-15 | Dsm Nv | Werkwijze voor de hydrogenering van koolstof-koolstof dubbele bindingen van een onverzadigd polymeer. |
| US6521694B2 (en) | 1998-08-11 | 2003-02-18 | Dsm N.V. | Process for hydrogenation of carbon-carbon double bonds of an unsaturated polymer |
| US6576336B1 (en) * | 1998-09-11 | 2003-06-10 | Unitech Corporation, Llc | Electrically conductive and electromagnetic radiation absorptive coating compositions and the like |
| US7282260B2 (en) * | 1998-09-11 | 2007-10-16 | Unitech, Llc | Electrically conductive and electromagnetic radiation absorptive coating compositions and the like |
| NL1014201C2 (nl) * | 1999-07-09 | 2001-01-10 | Dsm Nv | Werkwijze voor de hydrogenering van een polymeer dat is opgebouwd uit dieenmonomeereenheden en monomeereenheden die een nitrilgroep bevatten. |
| ATE293130T1 (de) | 1999-12-08 | 2005-04-15 | Dow Global Technologies Inc | Verfahren zur hydrierung von ungesättigten polymeren |
| NL1014197C2 (nl) * | 2000-01-27 | 2001-07-30 | Dsm Nv | Werkwijze voor de hydrogenering van een polymeer dat is opgebouwd uit dieenmonomeereenheden en monomeereenheden die een nitrilgroep bevatten. |
| DE10019215A1 (de) | 2000-04-18 | 2001-10-25 | Basf Ag | Neue Schlagzähmodifier auf Basis von (teil)hydrierten butadienhaltigen Dispersionen |
| EP1182215B1 (en) * | 2000-08-25 | 2011-04-06 | Kaneka Corporation | Method for purification of vinyl polymers |
| US6709758B2 (en) * | 2001-11-09 | 2004-03-23 | Lord Corporation | Room temperature curable X-HNBR coating |
| US6777026B2 (en) * | 2002-10-07 | 2004-08-17 | Lord Corporation | Flexible emissive coatings for elastomer substrates |
| CA2482355A1 (fr) * | 2002-04-11 | 2003-11-13 | Atofina | Procede d'hydrogenation de polymeres en milieu disperse |
| BR0312937A (pt) * | 2002-07-19 | 2005-06-21 | Dsm Ip Assets Bv | Processo para a preparação de um polìmero hidrogenado |
| US6516884B1 (en) | 2002-07-23 | 2003-02-11 | Halliburton Energy Services, Inc. | Stable well cementing methods and compositions |
| US6844412B2 (en) * | 2002-07-25 | 2005-01-18 | Lord Corporation | Ambient cured coatings and coated rubber products therefrom |
| JP4748933B2 (ja) * | 2003-12-08 | 2011-08-17 | ニッタ株式会社 | ゴム状弾性体とその製造法 |
| WO2005056612A1 (ja) * | 2003-12-08 | 2005-06-23 | Nitta Corporation | ゴム状製品又はゴム状物質含有製品 |
| JP4610261B2 (ja) * | 2004-08-26 | 2011-01-12 | ニッタ株式会社 | 樹脂改質剤及び該樹脂改質剤を含む樹脂組成物 |
| JP5030377B2 (ja) * | 2004-11-08 | 2012-09-19 | ニッタ株式会社 | 変性ラテックス、及び天然ポリイソプレノイド水素添加物又はその変性体含有製品 |
| US7722144B2 (en) * | 2004-04-19 | 2010-05-25 | Hewlett-Packard Development Company, L.P. | Fluid ejection device |
| US7528204B2 (en) * | 2004-05-17 | 2009-05-05 | The Goodyear Tire & Rubber Company | Hydrogenation and epoxidation of polymers made by controlled polymerization |
| US7411015B2 (en) * | 2005-07-08 | 2008-08-12 | Zeon Chemicals, L.P. | Process for preventing gel formation in lattices of hydrogenated, low molecular weight, functionalized elastomers |
| JP4895600B2 (ja) * | 2005-12-20 | 2012-03-14 | 住友ゴム工業株式会社 | タイヤ用ゴム組成物およびそれを用いたサイドウォールを有するタイヤ |
| JP5001571B2 (ja) * | 2006-04-04 | 2012-08-15 | 株式会社ブリヂストン | ゴム組成物及びそれを用いた空気入りタイヤ。 |
| JP2008184572A (ja) * | 2007-01-31 | 2008-08-14 | Bridgestone Corp | 変性水添天然ゴムの製造方法、変性水添天然ゴム、ゴム組成物及びそれを用いた空気入りタイヤ |
| WO2009054926A2 (en) | 2007-10-19 | 2009-04-30 | Lord Corporation | Suspension system for aircraft auxiliary power unit with elastomeric member |
| EP2075263A1 (en) | 2007-12-17 | 2009-07-01 | Lanxess Inc. | Hydrogenation of a diene-based polymer latex |
| EP2072535A1 (en) | 2007-12-17 | 2009-06-24 | Lanxess Inc. | Hydrogenation of diene-based polymer latex |
| EP2289947A1 (en) | 2009-08-26 | 2011-03-02 | University Of Waterloo | Nano-sized hydrogenated diene-based latex particles |
| EP2289948A1 (en) | 2009-08-26 | 2011-03-02 | University Of Waterloo | Nano-sized hydrogenated diene-based latex particles |
| EP2289991A1 (en) | 2009-08-26 | 2011-03-02 | University Of Waterloo | Nano-sized diene-based polymer latex particles |
| EP2325237A1 (de) | 2009-11-19 | 2011-05-25 | LANXESS Deutschland GmbH | Feinteilige stabile Suspensionen funktionalisierter, ganz oder teilweise hydrierter Nitrilkautschuke |
| EP2824116B1 (en) | 2012-03-06 | 2017-01-04 | Sumitomo Rubber Industries, Ltd. | Hydrogenated branched conjugated diene copolymer, rubber composition, and pneumatic tire |
| EP2676970B1 (en) | 2012-06-22 | 2015-04-08 | University Of Waterloo | Hydrogenation of diene-based polymers |
| EP2676971B1 (en) | 2012-06-22 | 2015-04-08 | University Of Waterloo | Hydrogenation of a diene-based polymer latex |
| CN102911293B (zh) * | 2012-11-13 | 2014-06-25 | 北京化工大学 | 磁性纳米四氧化三铁催化剂常压氢化不饱和聚合物的方法 |
| JP6355581B2 (ja) | 2015-03-20 | 2018-07-11 | 住友ゴム工業株式会社 | 高分子複合体及びその製造方法、並びに、タイヤ用ゴム組成物及び空気入りタイヤ |
| CN106866844B (zh) * | 2017-03-06 | 2018-06-29 | 北京化工大学 | 乳液法制备氢化天然胶的方法 |
| JP6946722B2 (ja) | 2017-05-08 | 2021-10-06 | 住友ゴム工業株式会社 | ゴム組成物、加硫ブラダー及び空気入りタイヤ |
| JP7119342B2 (ja) | 2017-11-02 | 2022-08-17 | 住友ゴム工業株式会社 | ジエン系共重合体及びゴム組成物 |
| JP6992477B2 (ja) | 2017-12-14 | 2022-01-13 | 住友ゴム工業株式会社 | タイヤ用ゴム組成物及び空気入りタイヤ |
| CN109879987A (zh) * | 2019-03-29 | 2019-06-14 | 青岛科技大学 | 一种氢化异戊胶及其制备方法 |
| JP7338391B2 (ja) | 2019-10-15 | 2023-09-05 | 住友ゴム工業株式会社 | ベーストレッド用組成物及びタイヤ |
| JP7731189B2 (ja) | 2019-10-15 | 2025-08-29 | 住友ゴム工業株式会社 | タイヤ用組成物及びタイヤ |
| EP3808569B1 (en) | 2019-10-15 | 2023-11-15 | Sumitomo Rubber Industries, Ltd. | Tire composition and tire |
| JP7512610B2 (ja) | 2020-02-25 | 2024-07-09 | 住友ゴム工業株式会社 | タイヤ用組成物及びタイヤ |
| JP7501180B2 (ja) | 2020-07-10 | 2024-06-18 | 住友ゴム工業株式会社 | タイヤ |
| JP7521284B2 (ja) | 2020-07-10 | 2024-07-24 | 住友ゴム工業株式会社 | タイヤ用ゴム組成物及びタイヤ |
| US11827723B1 (en) * | 2020-07-27 | 2023-11-28 | Dane K. Parker | Method for the diimide hydrogenation of emulsified unsaturated polymers |
| CN112745460B (zh) * | 2020-12-30 | 2022-06-17 | 青岛科技大学 | 一种饱和极性聚合物及其制备方法 |
| CN119119520B (zh) * | 2024-10-28 | 2025-08-26 | 日照市晨晖橡塑制品有限公司 | 一种耐腐蚀性能优良的防喷器胶芯制备工艺 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2414578A (en) * | 1943-09-14 | 1947-01-21 | Shell Dev | Hydrogenation of polyallyl alcohol |
| US3898208A (en) * | 1971-06-21 | 1975-08-05 | Dow Chemical Co | Hydrogenation of oil-insoluble diene polymers |
| JPS5740811B2 (OSRAM) * | 1973-05-08 | 1982-08-30 | ||
| US3959239A (en) * | 1975-05-05 | 1976-05-25 | Mobil Oil Corporation | Use of nickel cyclooctadiene as a hydrogenation catalyst |
| DE2748884C2 (de) * | 1977-11-02 | 1982-05-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur katalytischen Hydrierung von Polymerisaten konjugierter Diene |
| US4221872A (en) * | 1977-11-28 | 1980-09-09 | Ici Australia Limited | Process for removing unsaturation from ion exchange resins containing unquaternized amino groups by hydrogenation with imine |
-
1983
- 1983-02-22 US US06/468,816 patent/US4452950A/en not_active Expired - Lifetime
-
1984
- 1984-02-08 CA CA000447003A patent/CA1216598A/en not_active Expired
- 1984-02-09 BR BR8400562A patent/BR8400562A/pt not_active IP Right Cessation
- 1984-02-17 EP EP84630023A patent/EP0117221B1/en not_active Expired
- 1984-02-17 DE DE8484630023T patent/DE3480401D1/de not_active Expired
- 1984-02-21 ES ES529890A patent/ES8506329A1/es not_active Expired
- 1984-02-21 AU AU24775/84A patent/AU559579B2/en not_active Ceased
- 1984-02-22 JP JP59032274A patent/JPS59161415A/ja active Granted
-
1987
- 1987-07-17 MY MYPI8701035A patent/MY100004A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU559579B2 (en) | 1987-03-12 |
| BR8400562A (pt) | 1984-09-25 |
| EP0117221A1 (en) | 1984-08-29 |
| EP0117221B1 (en) | 1989-11-08 |
| DE3480401D1 (en) | 1989-12-14 |
| AU2477584A (en) | 1984-08-30 |
| ES529890A0 (es) | 1985-07-01 |
| US4452950A (en) | 1984-06-05 |
| JPS59161415A (ja) | 1984-09-12 |
| CA1216598A (en) | 1987-01-13 |
| MY100004A (en) | 1988-10-26 |
| ES8506329A1 (es) | 1985-07-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0441161B2 (OSRAM) | ||
| KR100344137B1 (ko) | 수소화고무의제조방법 | |
| US4503196A (en) | Polymer hydrogenation process | |
| JPS59133203A (ja) | 重合体の水添方法 | |
| JP5714585B2 (ja) | ナノサイズの水素化ジエン系ラテックス粒子 | |
| WO2002002650A1 (fr) | Procede d'hydrognation d'un polymere | |
| CN107108764B (zh) | 高饱和腈橡胶的制造方法 | |
| US7385010B2 (en) | Hydrogenation of diene-based polymer latex | |
| JP5289680B2 (ja) | ジエン系重合体ラテックスの水素化 | |
| KR100219260B1 (ko) | 리빙 중합체 수첨용 신규 촉매 및 촉매를 이용한 수첨방법 | |
| JP4456478B2 (ja) | 分散媒体中のポリマーの水素化方法 | |
| US5561197A (en) | Hydrogenation of diene copolymers | |
| JP5474274B2 (ja) | 不飽和（共）重合体の選択的水素化方法 | |
| JP4110267B2 (ja) | 触媒回収方法 | |
| WO1990002765A3 (en) | Selective catalytic process for preparing n-halothiosulfonamide modified terpolymers and catalysts therefor | |
| JPS6335642B2 (OSRAM) | ||
| KR20040063007A (ko) | 고속분사 노즐 장착 반응기로부터 제조된리튬하이드라이드를 사용한 고분자의 수첨공정 | |
| KR100287961B1 (ko) | 공역디엔을 포함하는 고분자의 수소첨가 방법 | |
| KR100332464B1 (ko) | 공액디엔 중합체의 선택적 수소화를 위한 촉매 및 이를이용한 수소화 방법 | |
| JPH0578562B2 (OSRAM) | ||
| KR19990015840A (ko) | 올레핀성 리빙중합체의 이중결합의 선택적 수소화를 위한 신촉매제조 및 이를 이용한 수첨 방법 | |
| JPH04505176A (ja) | ポリマーラテックス中における残留遊離ヒドラジンを最小にする方法 | |
| IL31274A (en) | Uranium,arsenic,antimony and molybdenum oxidation catalysts and promoters therefor | |
| JPH0311058A (ja) | ｓｅｃ―ブチルトルエンヒドロペルオキシドの製造方法 | |
| KR19990074608A (ko) | 공역디엔 중합체의 수소화 방법 |