DE818693C - Verfahren zum Kopolymerisieren von Monomeren vom Vinyltyp mit einer endstaendigen Methylengruppe - Google Patents
Verfahren zum Kopolymerisieren von Monomeren vom Vinyltyp mit einer endstaendigen MethylengruppeInfo
- Publication number
- DE818693C DE818693C DEN848A DEN0000848A DE818693C DE 818693 C DE818693 C DE 818693C DE N848 A DEN848 A DE N848A DE N0000848 A DEN0000848 A DE N0000848A DE 818693 C DE818693 C DE 818693C
- Authority
- DE
- Germany
- Prior art keywords
- monomers
- monomer
- polymerization
- parts
- vinyl type
- 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
- 239000000178 monomer Substances 0.000 title claims description 130
- 229920002554 vinyl polymer Polymers 0.000 title claims description 39
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims description 36
- 238000000034 method Methods 0.000 title claims description 23
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 title claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 42
- 229920000642 polymer Polymers 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 239000005977 Ethylene Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 description 45
- 239000000203 mixture Substances 0.000 description 34
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 31
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 29
- 150000003254 radicals Chemical class 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- -1 dimethallyl phthalate Chemical compound 0.000 description 14
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 13
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 13
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- ZGHFDIIVVIFNPS-UHFFFAOYSA-N 3-Methyl-3-buten-2-one Chemical compound CC(=C)C(C)=O ZGHFDIIVVIFNPS-UHFFFAOYSA-N 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 229920001519 homopolymer Polymers 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 230000000379 polymerizing effect Effects 0.000 description 9
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000004014 plasticizer Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- 239000002685 polymerization catalyst Substances 0.000 description 4
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 4
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 3
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 3
- DNLWMXNFYAURFM-UHFFFAOYSA-N 4-methylidenenonanamide Chemical compound C(CCCC)C(CCC(=O)N)=C DNLWMXNFYAURFM-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical compound CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 2
- PIGJZPZYWKFDBR-UHFFFAOYSA-N 2,5-dimethyl-1-(4-methylpyridin-2-yl)pyrrole-3-carbaldehyde Chemical compound CC1=CC(C=O)=C(C)N1C1=CC(C)=CC=N1 PIGJZPZYWKFDBR-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- IVKYUXHYUAMPMT-UHFFFAOYSA-N 2-methylprop-2-enyl acetate Chemical compound CC(=C)COC(C)=O IVKYUXHYUAMPMT-UHFFFAOYSA-N 0.000 description 2
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 2
- UKZKMRGYMWHKOD-UHFFFAOYSA-N 4-methylideneoctan-2-one Chemical compound CCCCC(=C)CC(C)=O UKZKMRGYMWHKOD-UHFFFAOYSA-N 0.000 description 2
- OJEUMYNHRBQGPP-UHFFFAOYSA-N 4-methylideneoctanenitrile Chemical compound CCCCC(=C)CCC#N OJEUMYNHRBQGPP-UHFFFAOYSA-N 0.000 description 2
- TVEWFWSJSXPPDM-UHFFFAOYSA-N 6-methyl-4-methylideneheptanamide Chemical compound C(C(C)C)C(CCC(=O)N)=C TVEWFWSJSXPPDM-UHFFFAOYSA-N 0.000 description 2
- KIYGUWOGKAKFBF-UHFFFAOYSA-N 6-methyl-5-methylideneheptanenitrile Chemical compound C(C)(C)C(CCCC#N)=C KIYGUWOGKAKFBF-UHFFFAOYSA-N 0.000 description 2
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 2
- UPIWXMRIPODGLE-UHFFFAOYSA-N butyl benzenecarboperoxoate Chemical compound CCCCOOC(=O)C1=CC=CC=C1 UPIWXMRIPODGLE-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 2
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003214 poly(methacrylonitrile) Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- OYLCUJRJCUXQBQ-UHFFFAOYSA-N 1-hepten-3-one Chemical compound CCCCC(=O)C=C OYLCUJRJCUXQBQ-UHFFFAOYSA-N 0.000 description 1
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 description 1
- SXZSFWHOSHAKMN-UHFFFAOYSA-N 2,3,4,4',5-Pentachlorobiphenyl Chemical compound C1=CC(Cl)=CC=C1C1=CC(Cl)=C(Cl)C(Cl)=C1Cl SXZSFWHOSHAKMN-UHFFFAOYSA-N 0.000 description 1
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- VEGMVELYKJQPQW-UHFFFAOYSA-N 2-bromohept-1-en-3-one Chemical compound BrC(=C)C(CCCC)=O VEGMVELYKJQPQW-UHFFFAOYSA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- TVONJMOVBKMLOM-UHFFFAOYSA-N 2-methylidenebutanenitrile Chemical compound CCC(=C)C#N TVONJMOVBKMLOM-UHFFFAOYSA-N 0.000 description 1
- DJDGWVCBUNYBOO-UHFFFAOYSA-N 2-methylideneoctanoic acid Chemical compound CCCCCCC(=C)C(O)=O DJDGWVCBUNYBOO-UHFFFAOYSA-N 0.000 description 1
- ZLCQPNTYJJEQND-UHFFFAOYSA-N 2-methylprop-2-enenitrile;2-methylprop-2-enoic acid Chemical compound CC(=C)C#N.CC(=C)C(O)=O ZLCQPNTYJJEQND-UHFFFAOYSA-N 0.000 description 1
- ZCPJCSCTKNNSLQ-UHFFFAOYSA-N 2-methylpropyl 4-methylidenehexanoate Chemical compound C(C)C(CCC(=O)OCC(C)C)=C ZCPJCSCTKNNSLQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- OLUOHHXYBBNVPD-UHFFFAOYSA-N 3-chlorobut-3-enenitrile Chemical compound ClC(=C)CC#N OLUOHHXYBBNVPD-UHFFFAOYSA-N 0.000 description 1
- ZXABMDQSAABDMG-UHFFFAOYSA-N 3-ethenoxyprop-1-ene Chemical compound C=CCOC=C ZXABMDQSAABDMG-UHFFFAOYSA-N 0.000 description 1
- QPNJIYXWKHAJEW-UHFFFAOYSA-N 3-fluorobut-3-enenitrile Chemical compound FC(CC#N)=C QPNJIYXWKHAJEW-UHFFFAOYSA-N 0.000 description 1
- UPSCNXYDIMDWOI-UHFFFAOYSA-N 3-methylidenenon-4-enamide Chemical compound C(=CCCCC)C(CC(=O)N)=C UPSCNXYDIMDWOI-UHFFFAOYSA-N 0.000 description 1
- BTLMTXGWGXDULK-UHFFFAOYSA-N 3-methylidenenon-4-enenitrile Chemical compound C(=CCCCC)C(CC#N)=C BTLMTXGWGXDULK-UHFFFAOYSA-N 0.000 description 1
- UOTSYAILGSUTAC-UHFFFAOYSA-N 3-methylidenepentan-2-one Chemical compound CCC(=C)C(C)=O UOTSYAILGSUTAC-UHFFFAOYSA-N 0.000 description 1
- LIBMAGJXZHSEHA-UHFFFAOYSA-N 3-methylidenepentanamide Chemical compound CCC(=C)CC(N)=O LIBMAGJXZHSEHA-UHFFFAOYSA-N 0.000 description 1
- FTEINVAMSSVNGR-UHFFFAOYSA-N 4-chloropent-4-enamide Chemical compound NC(=O)CCC(Cl)=C FTEINVAMSSVNGR-UHFFFAOYSA-N 0.000 description 1
- JOQXGZWETVCGRZ-UHFFFAOYSA-N 4-chloropent-4-enoic acid Chemical compound OC(=O)CCC(Cl)=C JOQXGZWETVCGRZ-UHFFFAOYSA-N 0.000 description 1
- XEBGTWRUQFVRKX-UHFFFAOYSA-N 4-iodopent-4-enamide Chemical compound NC(=O)CCC(I)=C XEBGTWRUQFVRKX-UHFFFAOYSA-N 0.000 description 1
- LYVGZGRXQWDHMJ-UHFFFAOYSA-N 4-methoxypent-4-enamide Chemical compound COC(CCC(=O)N)=C LYVGZGRXQWDHMJ-UHFFFAOYSA-N 0.000 description 1
- ZUVXVCXXZLUIAR-UHFFFAOYSA-N 5-methyl-4-methylidenehexan-3-one Chemical compound CCC(=O)C(=C)C(C)C ZUVXVCXXZLUIAR-UHFFFAOYSA-N 0.000 description 1
- FKWUKKNHLHTXJE-UHFFFAOYSA-N 5-o-ethenyl 1-o-methyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC=C FKWUKKNHLHTXJE-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- PTVSRINJXWDIKP-UHFFFAOYSA-N Ethyl 4-pentenoate Chemical compound CCOC(=O)CCC=C PTVSRINJXWDIKP-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
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000004159 Potassium persulphate Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- JZQAAQZDDMEFGZ-UHFFFAOYSA-N bis(ethenyl) hexanedioate Chemical compound C=COC(=O)CCCCC(=O)OC=C JZQAAQZDDMEFGZ-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- LDAIEITUCJNWGG-UHFFFAOYSA-N butyl 4-chloropent-4-enoate Chemical compound C(CCC)OC(CCC(=C)Cl)=O LDAIEITUCJNWGG-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 210000001520 comb Anatomy 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006392 deoxygenation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- CJSBUWDGPXGFGA-UHFFFAOYSA-N dimethyl-butadiene Natural products CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 description 1
- TWFQJFPTTMIETC-UHFFFAOYSA-N dodecan-1-amine;hydron;chloride Chemical compound [Cl-].CCCCCCCCCCCC[NH3+] TWFQJFPTTMIETC-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- IYNRVIKPUTZSOR-HWKANZROSA-N ethenyl (e)-but-2-enoate Chemical compound C\C=C\C(=O)OC=C IYNRVIKPUTZSOR-HWKANZROSA-N 0.000 description 1
- XJELOQYISYPGDX-UHFFFAOYSA-N ethenyl 2-chloroacetate Chemical compound ClCC(=O)OC=C XJELOQYISYPGDX-UHFFFAOYSA-N 0.000 description 1
- FFYWKOUKJFCBAM-UHFFFAOYSA-N ethenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC=C FFYWKOUKJFCBAM-UHFFFAOYSA-N 0.000 description 1
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
- LZWYWAIOTBEZFN-UHFFFAOYSA-N ethenyl hexanoate Chemical compound CCCCCC(=O)OC=C LZWYWAIOTBEZFN-UHFFFAOYSA-N 0.000 description 1
- BLZSRIYYOIZLJL-UHFFFAOYSA-N ethenyl pentanoate Chemical compound CCCCC(=O)OC=C BLZSRIYYOIZLJL-UHFFFAOYSA-N 0.000 description 1
- BLCTWBJQROOONQ-UHFFFAOYSA-N ethenyl prop-2-enoate Chemical compound C=COC(=O)C=C BLCTWBJQROOONQ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- SQKVCLUVKIDLNQ-UHFFFAOYSA-N ethyl 3-methylbut-3-enoate Chemical compound CCOC(=O)CC(C)=C SQKVCLUVKIDLNQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 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
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 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
- 150000002689 maleic acids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005394 methallyl group Chemical group 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
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- YHIXOVNFGQWPFW-UHFFFAOYSA-N octadecan-1-amine;hydrobromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[NH3+] YHIXOVNFGQWPFW-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- GAZQLDAHHKFOEX-UHFFFAOYSA-N pentyl 4-methylidenenonanoate Chemical compound C(CCCC)C(CCC(=O)OCCCCC)=C GAZQLDAHHKFOEX-UHFFFAOYSA-N 0.000 description 1
- ARKMSERTIJYPIH-UHFFFAOYSA-N pentyl 4-methylideneoct-5-enoate Chemical compound C(=CCC)C(CCC(=O)OCCCCC)=C ARKMSERTIJYPIH-UHFFFAOYSA-N 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 150000004968 peroxymonosulfuric acids Chemical class 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- WLJVNTCWHIRURA-UHFFFAOYSA-L pimelate(2-) Chemical compound [O-]C(=O)CCCCCC([O-])=O WLJVNTCWHIRURA-UHFFFAOYSA-L 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 235000019394 potassium persulphate Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LNIAEVLCVIKUGU-UHFFFAOYSA-M potassium;octadecane-1-sulfonate Chemical compound [K+].CCCCCCCCCCCCCCCCCCS([O-])(=O)=O LNIAEVLCVIKUGU-UHFFFAOYSA-M 0.000 description 1
- PFMVLFSAAABWQD-UHFFFAOYSA-M potassium;octadecyl sulfate Chemical compound [K+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O PFMVLFSAAABWQD-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- PNGBYKXZVCIZRN-UHFFFAOYSA-M sodium;hexadecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCCCCCS([O-])(=O)=O PNGBYKXZVCIZRN-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical class CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 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
- 238000012546 transfer Methods 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1018971XA | 1949-05-07 | 1949-05-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE818693C true DE818693C (de) | 1951-10-25 |
Family
ID=22287050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEN848A Expired DE818693C (de) | 1949-05-07 | 1950-05-07 | Verfahren zum Kopolymerisieren von Monomeren vom Vinyltyp mit einer endstaendigen Methylengruppe |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE818693C (enrdf_load_stackoverflow) |
| FR (1) | FR1018971A (enrdf_load_stackoverflow) |
| GB (1) | GB690937A (enrdf_load_stackoverflow) |
| NL (1) | NL75532C (enrdf_load_stackoverflow) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2794793A (en) * | 1952-10-21 | 1957-06-04 | Eastman Kodak Co | Copolymerization of ethenoid monomers in the presence of polyacrylonitrile |
| DE1019089B (de) * | 1952-10-21 | 1957-11-07 | Eastman Kodak Co | Verfahren zur Herstellung von verspinnbaren Acrylnitril-Polymerisationsprodukten |
| DE1020458B (de) * | 1952-10-21 | 1957-12-05 | Eastman Kodak Co | Verfahren zur Herstellung von verspinnbaren Acrylnitril-Polymerisationsprodukten |
| US2837496A (en) * | 1952-12-31 | 1958-06-03 | Hercules Powder Co Ltd | Graft copolymers and preparation thereof from polymer hydroperoxides |
| DE1062013B (de) * | 1956-06-26 | 1959-07-23 | Hackethal Draht Und Kabel Werk | Verfahren zur Herstellung weicher Mischpolymerisate des Vinylchlorids |
| DE1082734B (de) * | 1957-06-07 | 1960-06-02 | Basf Ag | Verfahren zur Herstellung von schlagfestem Polyvinylchlorid |
| DE1098203B (de) * | 1954-11-26 | 1961-01-26 | Eastman Kodak Co | Verfahren zur Herstellung von Mischpolymerisaten des Vinylchlorids oder Vinylidenchlorids |
| DE1165860B (de) * | 1959-02-26 | 1964-03-19 | Rohm & Haas | Verfahren zur Herstellung waessriger Dispersionen von Pfropfmischpolymerisaten |
| DE1186629B (de) * | 1954-02-03 | 1965-02-04 | Eastman Kodak Co | Verfahren zur Herstellung verspinnbarer Pfropfmischpolymerisate des Acrylnitrils |
| DE1301087B (de) * | 1964-01-02 | 1969-08-14 | Goodyear Tire & Rubber | Verfahren zur Herstellung von Polymerisatperlen |
| DE1302623B (de) * | 1960-03-07 | 1975-03-20 | Rohm and Haas Co., Philadelphia, Pa. (V.StA.) | Verfahren zur herstellung von festen thermoplastischen pfropfmischpolymerisaten |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2840447A (en) * | 1954-04-28 | 1958-06-24 | Du Pont | Process for preparing filaments from dispersions containing graft polymers obtained from ethylenically unsaturated monomers |
| US2842518A (en) * | 1954-09-13 | 1958-07-08 | Borg Warner | Product produced by polymerization of vinylidene chloride-acrylonitrile mixtures onto polychloroprene |
| BE598164A (enrdf_load_stackoverflow) * | 1959-12-18 | |||
| US4163766A (en) | 1973-05-17 | 1979-08-07 | The Standard Oil Company | Impact-resistant olefinic-nitrile olefinic-ester copolymers prepared in the presence of an olefinic-ester copolymer elastomer |
| CA1031893A (en) | 1973-05-17 | 1978-05-23 | The Standard Oil Company | Impact-resistant olefinic-nitrile copolymers |
-
0
- NL NL75532D patent/NL75532C/xx active
-
1950
- 1950-05-05 GB GB1119850A patent/GB690937A/en not_active Expired
- 1950-05-07 DE DEN848A patent/DE818693C/de not_active Expired
- 1950-05-08 FR FR1018971D patent/FR1018971A/fr not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2794793A (en) * | 1952-10-21 | 1957-06-04 | Eastman Kodak Co | Copolymerization of ethenoid monomers in the presence of polyacrylonitrile |
| DE1019089B (de) * | 1952-10-21 | 1957-11-07 | Eastman Kodak Co | Verfahren zur Herstellung von verspinnbaren Acrylnitril-Polymerisationsprodukten |
| DE1020458B (de) * | 1952-10-21 | 1957-12-05 | Eastman Kodak Co | Verfahren zur Herstellung von verspinnbaren Acrylnitril-Polymerisationsprodukten |
| US2837496A (en) * | 1952-12-31 | 1958-06-03 | Hercules Powder Co Ltd | Graft copolymers and preparation thereof from polymer hydroperoxides |
| DE1186629B (de) * | 1954-02-03 | 1965-02-04 | Eastman Kodak Co | Verfahren zur Herstellung verspinnbarer Pfropfmischpolymerisate des Acrylnitrils |
| DE1098203B (de) * | 1954-11-26 | 1961-01-26 | Eastman Kodak Co | Verfahren zur Herstellung von Mischpolymerisaten des Vinylchlorids oder Vinylidenchlorids |
| DE1062013B (de) * | 1956-06-26 | 1959-07-23 | Hackethal Draht Und Kabel Werk | Verfahren zur Herstellung weicher Mischpolymerisate des Vinylchlorids |
| DE1082734B (de) * | 1957-06-07 | 1960-06-02 | Basf Ag | Verfahren zur Herstellung von schlagfestem Polyvinylchlorid |
| DE1165860B (de) * | 1959-02-26 | 1964-03-19 | Rohm & Haas | Verfahren zur Herstellung waessriger Dispersionen von Pfropfmischpolymerisaten |
| DE1302623B (de) * | 1960-03-07 | 1975-03-20 | Rohm and Haas Co., Philadelphia, Pa. (V.StA.) | Verfahren zur herstellung von festen thermoplastischen pfropfmischpolymerisaten |
| DE1301087B (de) * | 1964-01-02 | 1969-08-14 | Goodyear Tire & Rubber | Verfahren zur Herstellung von Polymerisatperlen |
Also Published As
| Publication number | Publication date |
|---|---|
| GB690937A (en) | 1953-04-29 |
| NL75532C (enrdf_load_stackoverflow) | |
| FR1018971A (fr) | 1953-01-15 |
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