NO743637L - - Google Patents
Info
- Publication number
- NO743637L NO743637L NO743637A NO743637A NO743637L NO 743637 L NO743637 L NO 743637L NO 743637 A NO743637 A NO 743637A NO 743637 A NO743637 A NO 743637A NO 743637 L NO743637 L NO 743637L
- Authority
- NO
- Norway
- Prior art keywords
- polymer
- stated
- alkyl
- vinylbenzyltrialkylammonium
- monomers
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 claims description 32
- -1 vinylbenzylammonium halide Chemical group 0.000 claims description 29
- 239000004816 latex Substances 0.000 claims description 24
- 229920000126 latex Polymers 0.000 claims description 24
- 239000000178 monomer Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 15
- WZFYQPIIFRIINF-UHFFFAOYSA-N (4-ethenylphenyl)methyl-(18-methylnonadecyl)azanium;chloride Chemical compound [Cl-].CC(C)CCCCCCCCCCCCCCCCC[NH2+]CC1=CC=C(C=C)C=C1 WZFYQPIIFRIINF-UHFFFAOYSA-N 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000001450 anions Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229910052736 halogen Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- RWYPHSUSLQLHSV-UHFFFAOYSA-N (4-ethenylphenyl)methyl-(14-methylpentadecyl)azanium;chloride Chemical compound [Cl-].CC(C)CCCCCCCCCCCCC[NH2+]CC1=CC=C(C=C)C=C1 RWYPHSUSLQLHSV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 150000003841 chloride salts Chemical group 0.000 claims 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- 239000004094 surface-active agent Substances 0.000 description 11
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 10
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 7
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 7
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 7
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 125000002091 cationic group Chemical group 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000002940 repellent Effects 0.000 description 3
- 239000005871 repellent Substances 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- LLBHHBLFOCEPJC-UHFFFAOYSA-M (4-ethenylphenyl)methyl-dimethyl-octadecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=C(C=C)C=C1 LLBHHBLFOCEPJC-UHFFFAOYSA-M 0.000 description 2
- VJJZJBUCDWKPLC-UHFFFAOYSA-N 3-methoxyapigenin Chemical compound O1C2=CC(O)=CC(O)=C2C(=O)C(OC)=C1C1=CC=C(O)C=C1 VJJZJBUCDWKPLC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 description 2
- 229950010007 dimantine Drugs 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- IMBKASBLAKCLEM-UHFFFAOYSA-L ferrous ammonium sulfate (anhydrous) Chemical compound [NH4+].[NH4+].[Fe+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O IMBKASBLAKCLEM-UHFFFAOYSA-L 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 238000003911 water pollution Methods 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- DEGZUQBZHACZKW-UHFFFAOYSA-N 2-(methylamino)ethyl 2-methylprop-2-enoate Chemical compound CNCCOC(=O)C(C)=C DEGZUQBZHACZKW-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
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- CHNGPLVDGWOPMD-UHFFFAOYSA-N 2-ethylbutyl 2-methylprop-2-enoate Chemical compound CCC(CC)COC(=O)C(C)=C CHNGPLVDGWOPMD-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- FSVQAZDYQRQQKH-UHFFFAOYSA-N 2-methylbutan-2-yl prop-2-enoate Chemical compound CCC(C)(C)OC(=O)C=C FSVQAZDYQRQQKH-UHFFFAOYSA-N 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- ULYIFEQRRINMJQ-UHFFFAOYSA-N 3-methylbutyl 2-methylprop-2-enoate Chemical compound CC(C)CCOC(=O)C(C)=C ULYIFEQRRINMJQ-UHFFFAOYSA-N 0.000 description 1
- ZVYGIPWYVVJFRW-UHFFFAOYSA-N 3-methylbutyl prop-2-enoate Chemical compound CC(C)CCOC(=O)C=C ZVYGIPWYVVJFRW-UHFFFAOYSA-N 0.000 description 1
- NUIMPSFZBALNHW-UHFFFAOYSA-N 6-but-3-enyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(CCC=C)=N1 NUIMPSFZBALNHW-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KGQLBLGDIQNGSB-UHFFFAOYSA-N benzene-1,4-diol;methoxymethane Chemical compound COC.OC1=CC=C(O)C=C1 KGQLBLGDIQNGSB-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- GTBGXKPAKVYEKJ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(C)=C GTBGXKPAKVYEKJ-UHFFFAOYSA-N 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 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
- FKIRSCKRJJUCNI-UHFFFAOYSA-N ethyl 7-bromo-1h-indole-2-carboxylate Chemical compound C1=CC(Br)=C2NC(C(=O)OCC)=CC2=C1 FKIRSCKRJJUCNI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZNAOFAIBVOMLPV-UHFFFAOYSA-N hexadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C(C)=C ZNAOFAIBVOMLPV-UHFFFAOYSA-N 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- YOZHLACIXDCHPV-UHFFFAOYSA-N n-(methoxymethyl)-2-methylprop-2-enamide Chemical compound COCNC(=O)C(C)=C YOZHLACIXDCHPV-UHFFFAOYSA-N 0.000 description 1
- UMBBGOALZMAJSF-UHFFFAOYSA-N n-benzylethenamine;hydrochloride Chemical compound [Cl-].C=C[NH2+]CC1=CC=CC=C1 UMBBGOALZMAJSF-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YOTGRUGZMVCBLS-UHFFFAOYSA-N pentadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCOC(=O)C(C)=C YOTGRUGZMVCBLS-UHFFFAOYSA-N 0.000 description 1
- GOZDOXXUTWHSKU-UHFFFAOYSA-N pentadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCOC(=O)C=C GOZDOXXUTWHSKU-UHFFFAOYSA-N 0.000 description 1
- GYDSPAVLTMAXHT-UHFFFAOYSA-N pentyl 2-methylprop-2-enoate Chemical compound CCCCCOC(=O)C(C)=C GYDSPAVLTMAXHT-UHFFFAOYSA-N 0.000 description 1
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 1
- 229940043349 potassium metabisulfite Drugs 0.000 description 1
- 235000010263 potassium metabisulphite Nutrition 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- VYGBQXDNOUHIBZ-UHFFFAOYSA-L sodium formaldehyde sulphoxylate Chemical compound [Na+].[Na+].O=C.[O-]S[O-] VYGBQXDNOUHIBZ-UHFFFAOYSA-L 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-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
- ATZHWSYYKQKSSY-UHFFFAOYSA-N tetradecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)=C ATZHWSYYKQKSSY-UHFFFAOYSA-N 0.000 description 1
- XZHNPVKXBNDGJD-UHFFFAOYSA-N tetradecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C=C XZHNPVKXBNDGJD-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/41—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups
- D21H17/44—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups cationic
- D21H17/45—Nitrogen-containing groups
- D21H17/455—Nitrogen-containing groups comprising tertiary amine or being at least partially quaternised
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
- D06M15/3562—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms containing nitrogen
-
- 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
- C08F26/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2402—Coating or impregnation specified as a size
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Textile Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paper (AREA)
- Polymerisation Methods In General (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Description
Tittel: Latekspolymer, samt fremgangsmåte for fremstilling av en slik.
. Oppfinnelsen vedrører stabiliserte polymerer, deres fremstilling og anvendelse, idet polymerene i henhold til oppfinnelsen har lateksstabiliserende enheter inkorporert i sine makromolekyler. De lateksstabiliserende enheter er enheter av ett eller flere
vinylbenzyltrialkylammoniumsalter, spesielt vinylbenzyltrialkyl-ammoniumhalogenider. Oppfinnelsen tilveiebringer latekspolymerer som inneholder enheter av ett eller flere vinylbenzyltrialkylammoniumsalter som lateksstabilisator.
Latekspolymerene i henhold til oppfinnelsen unngår de problemer som er forbundet med den konvensjonelle anvendelse av anjoniske, ikke-joniske og katjoniske emulgatorer som lateks-stabilisatorer. Disse problemer innbefatter for sterk skumming,
vannfølsorahet, mykning og migrering.
Latekspolymerene i henhold til oppfinnelsen er generelt anvendelige, men har tre spesifikke områder for spesiell anvendelse:
(1) Som impregnoringsmidler for økning av stivhet, vann-resistens, styrke, glatthet eller vekt hos forskjellige materialer, for eksempel papir, tøy og liknende. Laboratorieresultater indikerer at det kan fremstilles polymerer i henhold til oppfinnelsen som er gunstige sammenliknet med kolofonium for denne anvendelse; (2) Som bindemidler, og for denne anvendelse kan de eliminere anvendelsen av hollender-deponeringshjelpemidler. Hoved-problemene ved hollenderdeponeringen med hensyn til latekser fremstilt under anvendelse av konvensjonelle overflateaktive midler, er skum og vannforurensning. Dessuten kreves det deponeringshjelpemidler under deponeringen* Skummet kan faktisk interferere med deponeringsprosessen og kan kreve bruk av hjelpe-avskummende midler og andre additiver. Det overflateaktive middel og det skumhindrende middel kan så komme inn i avvannet med resulterende forurensnings-problemer. Polymerene i henhold til oppfinnelsen kan deponeres på tremassen uten å kreve ytterligere deponeringshjelpemidler eller skumhindrende midler, hvilket forenkler hele operasjonen og over-vinner økologiske problemer med hensyn til vannforurensning. (3) Som ekstender-bindemidler for fluorkarbon-vannav-støtende midler. Den normale prosess for å gjøre et ikke-vevet underlag resistent for vann og alkohol, for eksempel for anvendelse i engangsplagg for kirurgisk hospitalbruk, er først å behandle underlaget med et lateksbindemiddel som inneholder et konvensjonelt overflateaktivt middel. Underlaget behandles så med den nødvendige mengde av kationisk vannavstøtende middel. En totrinnsprosess kreves, da lateksen, hvis det fremstilles med et anjonisk overflateaktivt middel, er uforlikelig med det vannavstøtende middel. Når det syntetiseres under anvendelse av et ikke-jonisk overflateaktivt middel, er det nødvendige høye nivå eller avstøtningsevnen vanskelig å oppnå. Dette fenomen er beslektet med det overflateaktive middels evne til å migrere. Når det overflateaktive middel er gjort fast i polymerryggraden, og når det er kationisk i sin ladning, kan ikke-migrering og forlikelighet oppnås.
Vinylbenzyltrialkylammoniumsalter som er nyttige i polymerene i henhold til oppfinnelsen, innbefatter dem som har følgende strukturformel:
hvor R1 er et alkylradikal, for eksempel et rettkjedet eller forgrenet alkylrådikal som inneholder 3-22 karbonatomer og som fortrinnsvis inneholder 12-18 karbonatomer, for eksempel oktyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl,pentadecyl, heksa-decyl, heptadecyl, nonodecyl, eikosyl, henekosyl og dokosyl;
X Q er et anion, for eksempel et halogenidi, for eksempel bromid
og klorid, hydroksyd, fulfat, nitrat, acetat eller oksalat. Det foretrukne anion er klorid.
Substituentene på benzenringen står fortrinnsvis i para-stilling.
For at latekspolymerene i henhold til oppfinnelsen skal
være effektivt stabilisert, har det vist seg at de fortrinnsvis bør være polymerisasjonsprodukter av en blanding av monomerer som inneholder minst 0,2Svekt% vinylberizyltrialkylammoniumsalt. Foretrukne polymerer inneholder fra 0,25 til ca. 5 vektfl, regnet på hele polymeren, av vinylbenzyltrialkylammoniumsaltenhetene,, og det foretrukne område er fra 0,5 til 2,54 ay de angitte enheter i hele polymeren. De Ønskede latekser kan fremstilles ved kopolymerisering , . av vinylbenzyltrialkylammoniumhalogenid-monomeren med for. eksempel en eller flere av de følgende monomerer:
(a) monomerer av formelen
hvor R 2er hydrogen eller alkyl, for eksempel lavere alkyl med 1-4 karbonatomer, og R 3 er et rettkjedet, forgrenet eller.cyklisk
alkyl-, alicoksyalkyi- eller alkyltioalkylradikal hvor alkylgruppen inneholder fra ca. 1 til ca. 20 karbonatomer, og cykloalkylradikalet inneholder 5-6 nukleære karbonatomer. Eksempler på disse radikaler omfatter metyl, etyl, propyl, n-butyl, 2-etylheksylj, heptyl, heksyl, oktyl, 2-metylbutyl, l-metjtlbutyl, butoksybutyl, 2-metylpentyl, metoksymetyl, etoksyetyl, cyklopentyl, cykloheksyl, isobutyl, etyltioetyl, metyltioetyl, etyltiopropyl, 6^metylnonyl, decyl,
dodecyl, tetradecyl og pentadecyl. R 3 kan også være ureido, hydroksy-lavere alkyl med 1-5 karbonatomer, for eksempel hydroksymetyl, hydroksyetyl, hydroksypropyl, hydroksybutyl og hydToksypentyl;
2„3-©poksypropyl, amino- lavere alkyl, for eksempel.aminometyl og åminoetyl, mono- eller di- lavere alkyl-amino- lavere alkyl, for eksempel tert-butylaminoetyl og dimetylaminoetyl.
(b) Monomerer av formelen
hvor R 4 er hydrogen, metyl eller halogen, for eksempel klor o.l., c og R er hydrogen, halogen, for eksempel klor o.l.; lavere-alkanoyloksy, for eksempel acetoksy o.l., cyano, formyl, fenyl, karbamoyl, N-hydroksymetyl, tolyl, metoksyetyl, 2,4-diaméno-s-triazinyl- lavere alkyl eller epoksy.
Spesifikke foretrukne eksempler på monomerene (a) og (b) innbefatter: etylen, metylmetakrylat, etylmetakrylat, propylmeta-krylat, isopropylmetaakrylat, n-butylmetacrylat, isobutylmetakrylat, sek.-butylmetakrylat, tert.-butylmetakrylat, pentylmetakrylat, iso-pentylmetakrylat, tert.-pentylmetakrylat, heksylmetakrylat, cyklo-héksylmetakrylat, 2-etylbutylmetakrylat, 2-etylheksylmetakrylat, oktylmetakrylat, decylmetakrylat, laurylmetakrylat, myristylmeta-krylat, cetylmetakrylat, stearylmetakrylat, metylakrylat, etylakrylat, propylakrylat, isopropylakrylat, butylakrylat, isobutyl-akrylat, sek.-butylakrylat, tert.-butylakrylat, pentylakrylat, isopentylakrylat, tert.-pentylakrylat, heksylakrylat, oktylakrylat, 2-etylheksylakrylat, vinylacetat, tetradecylakrylat, akrylamid, pentadecylakrylat, styren, pentadecylmetakrylat, yinyltoluen, metakrylamid, N-metylolakrylamid, glycidylmetakrylat, metyl-aminoetylmetakrylat, tert.-butylaminoetylmetakrylat, dimetylamino-etylmetakrylat, 6-(3-butenyl)-2,4-diamino-s-triazin, hydroksypropyl-metakrylat,' hydroksyetylmetakrylat, akrylnitril, metakrylnitril, metoksymetylmetakrylamid, N-metylolmetakrylamid, akrolein, meta-krolein og 3,4-epoksy-l-buten.
Vannfølsorame materialer, for eksempel isocyanater, bør ikke brukes i vandige systemer med mindre de er blokkert, for eksempel ved omsetning med en fenol som beskytter isocyanatet inntil påfølgende oppvarmning eller inntil anvendelsen av andre reak-sjonsmekanismer, for eksempel anvendelse av kalsium-, sink- eller tinnforbindelsekatalysator som er konvensjonelt på området.
Halogenid-anjonene er slike som generelt anvendes som
X selv om andre anjoner kan anvendes og gi liknende resultater.
, Disse andre anjoner innbefatter hydroksyd, sulfat, nitrat, acetat, formiat og oksalat. Disse anjoner kan innføres i monomeren eller polymeren under anvendelse av kjente jonebytteteknikker.
De foretrukne emulsjonskopolymerer har én-rablekylvekt på mellom ca. 70.000 og 2.000.000 og fortrinnsvis mellom 250.000 og 1.000.000 og fremstilles ved emulsjonskopoiymerisering av de valgte monomerer i,de riktige forhold. Konvensjonelle emulsjonspolymerisa-sjonsteknikker er beskrevet i U.S.-PS 2.754.280 og 2.795.654.
En polymerisasjonsinitiator av friradikaltypen, for eksempel ammonium-eller kaliumpersulfat, kan anvendes alene eller i tilknytning til en akselerator, for eksempel kalium-metabisulfitt, eller natrium-tidsulfat. Organiske peroksyder, for eksempel benzoylperoksyd og tert.-butylhydroperoksyd, er også nyttige initiatorer. Initiatoren og akseleratoren, vanligvis referert til som katalysator, kan anvendes i mengder på 0,1 - 10% hver, basert på vekten av monomerer som skal kopolymeriserés. Mengden kan, som angitt ovenfor, justeres for regulering av polymerens grenseviskositetstall. Temperaturen kan være fra romtemperatur til ca. 95°C.
Vinylbenzyltrialkylammoniumhalogenidene er kjente for-bindelser og kan fremstilles ved kjente metoder, for eksempel ved omsetning av et alkyldimetylamin med et vinyibenzylhalogenid.
Følgende eksempte* illustrerer noen utførelsesformer av produktene i henhold til oppfinnelsen og fremgangsmåter for fremstilling av dem. I eksemplene angir alle prosenter vekt med mindre annet er angitt.
Eksempel 1
Lateks av butylakrylat (60%), styren (37,5%) dimétylstearyl-4-vinylbenzylammoniumklorid
Trinn A - Dimetylstearyl- 4- vinylbenzylammoniumklorid
Et kvaternært nitrogen-overflateaktivt middel, dimetylstearyl-4-vinylbenzylammoniumklorid, fremstilles ved langsom tilsetning av 4-vinyibenzyiklorid (488 g; 3,2 mol.) til en reaksjonskolbe
som inneholder vann (2400 g) , metyleteren av hydrokinon (4,4 g), kaliumjodid (0,8 g) og dimetylstearylamin J960 g; 3,2 mol)» Temperaturen holdes ved 45-50°C i de 30 minutter som tilsetningen varer. Løsningen, som først er tåket, blir klar og viskøs. Etter ca.
1,5 timer indikerer titrering av reaksjonsblandingen at 98% av aminet har reagert. Løsningen med 37% faststoffer, anvendes som en komono-mer og det eneste overflateaktive middel i følgende forsøk.
Trinn B Polymerisasjon av dimetylstearylr4~vinylbenzylammoniumklorid med butylakrylat og styren
Til en egnet reaksjonskolbe som er utstyrt med et termo-meter, nitrogenspyling, rører, kjøler og tilsetningstrakter, føres vann (1800 g) og 100 g av en blanding av butylakrylat (840 g), styren (562 g) og 48 g av den overflateaktive løsning fra trinn A. Polymerisasjonen startes ved 58°C ved tilsetning til kolben av et initieringssystem som består av tert.-butylhydroperoksyd (0,6 g), ferro-ammoniumsulfat (10 ml av 0,1% løsning) og natriumformaldehydsulfoksylat ("Formopon" 0,6 g). Når polymerisasjonen er begynt, hvilket tilkjennegir ved en eksoterm på ca. 5°C, tilsettes den gjenværende monomerblanding, som nå inneholder tert.-butylhydroperoksyd (4 ml) og ytterligere 48 g overflatéaktiv løsning, gradvis i løpet av 3 timer. Samtidig tilsettes en løsning av "Formopon" (3,0 g) i vann (100 ml). Det dannes en stabil lateks, 39,5% faststoffer med en partikkelstørrelse på ca. 0,12 um. Sammensetningen er 60% butylakrylat, 37,5% styren og 2,5% dimetylstearyl-4-vinylbenzylammoniumklorid.
Eksempel 2
Lateks av etylakrylat (60%), styren (37%) og dimetylstearyl-4-vinylbenzylammoniumklorid ( 3%)
På liknende måte som beskrevet i eksempel 1, fremstilles en stabil latekspolymer, 39,5% faststoffer, ved å erstatte butyl-akrylatet fra eksempel 1 med etylakrylat og ved å følge den fremgangsmåte som er beskrevet der. Det gummifrie produkt, med sammen-setning 60% etylakrylat, 37% styren og 3% dimetylstearyl-4-vinylbenzylammoniumklorid, har en partikkelstørrelse på 0,10 ym.
Eksempel 3
Lateks av vinylacetat (97,5%) og dimetylstearyl-4-vinylbenzylammoniumklorid
Det fremstilles en stabil kationisk lateks ved å tilsette, i et tidsrom av 3,5 timer, en løsning&y vinylacetat (681 g) og tert.-butylhydroperoksyd (2,0 ml) til en passende reaksjonskolbe som inneholder vann (649 g), stearyldimetyl-4-vinylbenzylammoniumklorid-løsning (153,0 g) og initioringssystemet som består av tert.- butylhydroperoksyd (10,6 g), ferro-ammoniurasulfat (10 ml, 0,1$) og natriumformaldehydsulfoksylat (0,6 g) . Under tilsetningen tilsettes også en løsning som inneholder en ytterligere mengde av natriujfi-formaldehyd-sulfoksylat (1,5 g) og stearyldimetyl-4-vinylbenzylammoniumklorid (46,5 g) langsomt. Ved slutten av reaksjonsperioden er faststoffinnholdet 39,9%. Sammensetningen av sluttproduktet er 97,5% vinylacetat og 2,5% dimetylstearyl-4-vinylbenzylammoniumklorid.
Eksempel. 4
Lateks av vinylacetat (60%), etylakrylat (37,5%) og diraetylstearyl-4- vinylbenzylammoniumklorid ( 2, 5%)
Til en kolbe som inneholder 649 g vann og 50 g av en blanding av etylakrylat (261 g), vinylacetat (420 g) og dimetylstearyl-4-vinylbenzylammoniumklorid-løsning (153 g), tilsettes et initieringssystem som er identisk med det som ble anvendt i eksempel 1. Etter at eksotermen h«r gitt seg, tilsettes den gjenværende blanding av monomerer gradvis i et tidsrom av 3 timer mens reaksjonstemperaturen holdes på 60-65°C. Faststoffinnholdet i den blåhvite lateks er 37,8%. Sammensetningen er 60% vinylacetat, 37,5% etylakrylat og 2,5% dimetylstearyl-4-vinylbenzylammoniumklorid.
Eksempel 5
Lateks av butylakryait (40%), metylmetaakrylat (57,5%) og dimetylstearyl- 4- vinylbenzylammoniumklorid.
Til én kolbe som inneholder 900 g vann og 50 g av en blanding av butylakrylat (280 g), metylmetakrylat (406 g) og dimetylstearyl-4-vinylbenzylammoniumklorid-løsning (24 g) tilsettes et initieringssystem som er identisk med det som ble anvendt i eksempel 1. Etter at eksotermen har gitt seg, tilsettes den gjenværende blanding av monomerer gradvis i et tidsrom av 3 timer mens reaksjonstemperaturen holdes på 60-65°C, Faststoffinnholdet i den blåhvite lateks er 40%. Sammensetningen er 40% butylakrylat, 57,5% metylmetakrylat og 2,5% dimetylstearyl-4-vinylbenzylammoniumklorid.
Eksempel 6
Dimetyllauryl-4-vinylbenzylammoniumklorid og dimetylmyristyl-4-vinylbenzylammoniumklorid
Et kvaternært overflateaktivt middel fremstilles som beskrevet i trinn Å, eksempel 1, med unntagelse av at reagensene er av en blanding av n-C12~ og n-C14-dimetylaminer (388 g; 1,61 mol), 4-vinylbenzylklorid (1,61 mol), metyleterhydroquinon (2,4 g), kaliumjodid (0,4 g) og vann (1200 g) . Omdannelse til blaiidingen av dimetyllauryl-4-vinylbenzylammoniuniklorid og dimetylmyristyl-4-vinylbenzylammoniumklorid er større enn 95,5%, bestemt ved ti* - trering. Faststoffinnholdet er 34,6%.
Eksempler 7 til 16
På liknende måte som beskrevet i eksempel 1, ble det fremstilt ytterligere polymerer. Det ble således, ved å erstatte dimetylstearylaminet i trinn A, eksempel 1, med et annet egnet alkyldimetylamin og ved i alt vesentlig å følge den fremgangsmåte som er beskrevet der, oppnådd ytterligere vinylbenzylalkyldiraetyl-ammoniumhalogenider som ble omsatt med hvisse monomerer slik at man fikk de ønskede lateksprodukter som har de stabiliserende overflateaktivt middel-enheter i sin ryggrad. Følgende ligning, sett sammen med tabell I, illustrerer utgangs-monomermaterialene.
Bksempel 17 Impregnering
Polymeremulsjoner inkorporeres i papir ved deponering på 500 CSF "Chésapeake" ubleket kraftmasse ved pH 4,5* Basisvekten holdes på ca. 220 g/m 2. Etter fremstillingen tørkes papiret ved 93,3°C på trommeltørken i en 1\ minutters cyklus. Emulsjonene inkorporeres i en mengde av 0,5%, regnet på massen, ved først å tilsette 0,1%, regnet på massen, av et katjonisk impregneringshjelpe-middel (tørr vekt i begge tilfeller). v Eksempel 18
Hollenderdeponering
Polymerene i henhold til oppfinnelsen deponeres i en "Valley"-hbllender i en mengde av 30% på en ikke oppslått a-hårdved-sulfitt-masse. Det foretas deponeringer ved 1% konsistens, som deretter fortynnes til 0,25% konsistens.
Eksempel 19
Vannavstøtning
Det lages et bad ved å fortynne 5 deler av emulsjonen fra eksempel 1 med vann og tilsette 0,5 del av et fluorkarbon (*'FC 824"- en 3M fluorkarbon). Det: endelige badfaststoff er 3,5%.
Claims (12)
1. Latekspolymer, karakterisert ved at den omfatter vinylbenzyltrialkylammoniumsalt som er kopolymeri-sert med én eller flere andre monomerer.
2. Polymer som angitt i krav i, karakterisert ved at den består av en monomerblanding som inneholder mirst 0,25'vektt vinylbenzyltrialkylammoniumsalt.
3. Polymer som angitt i krav 1 eller 2, karakterisert ved at den inneholder 0,25-5,0 vekt% vinylbenzyltri-alkylammoh iumsaltenheter.
4. Polymer som angitt i krav 3, karakterisert v e d at den inneholder 0,5-2,5 vektfc vinylbenzylalkylammonium-saltenheter.
5. Polymer som angitt i hvilket som helst av de foregående krav, karakterisert ved at vinylbenzyltrialkylammoniumsaltet har den generelle formel
1 6
hvor R er alkyl, og X er et anion.
6. Polymer som angitt i krav 5, karakterisert ved at vinylbenzyltrialkylammoniumsaltet har den generelle formel
hvor R 1 er alkyl, og X 9 er et anion.
7. Polymer som angitt i hvilket som helst av de foregående krav, karakterisert ved at vinylbenzyltrialkyl-ammoniumenhetene omfatter enheter av vinylbenzylåmmoniumhalogenid.
8. Polymer som angitt i hvilket som helst av de foregående krav, karakterisert ved at den også inneholder enheter av én eller flere av de følgende monomerer:(a) monomerer av formelen
hvor R 2 er, hydrogen eller alkyl, og R 3er et rettkjedet, forgrenet eller cyklisk alkyl-, alkoksyalkyl- eller alkyltioalkylradikal, ureido, hydroksy-lavere alkyl, 2, 3-epoksypropyl, amino-lavere alkyl eller mono- eller di- lavere alkylamino- lavere alkyl eller hydroksy-lavere alkylamino-lavere alkyl eller.(b) monomerer av formelen
hvor R4 er hydrogen, metyl eller halogen, og R5 er hydrogen, halogen, lavere alkanoyloksy, cyan, formyl, fenyl, karbamoyl, N-hydroksyetyl, tolyl, metoksyetyl, 2, 4-diamino-s-triazihyl-lavere alkyl eller epoksy.
9. Polymer som angitt i hvilket som helst av kravene 6 til 8, karakterisert ved at R1 er alkyl med fra 8 til 22 karbonatomer, og X <9> er et halogen-anion.
10. Polymer som angitt i krav 9, karakterisert ved at R er alkyl med 12-18 karbonatomer, og X Qer klorid.
11. Polymer som anggtt i krav 10, karakterisert ved at vinylbenzyltrialkylamraoniumsaltet omfatter dimetylstearyl-4-vinylbenzylammoniumklorid og/eller dimetyllauryl-4-vinylbenzylammoniumklorid,og/eller dimetylmyristyl-4-vinylbenzylammoniumklorid.
12. Fremgangsmåte for fremstilling av en latekspolymer, karakterisert ved polymerisering av en monomerblanding som omfatter ett eller flere vinylbenzyltrialkylammoniumsalter og en eller flere andre monomerer.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/405,221 US4017440A (en) | 1973-10-10 | 1973-10-10 | Polymers stabilized with polymerizable vinylbenzyltrialkyl ammonium salt surfactant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO743637L true NO743637L (no) | 1975-05-05 |
Family
ID=23602789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO743637A NO743637L (no) | 1973-10-10 | 1974-10-09 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US4017440A (no) |
| JP (1) | JPS5066546A (no) |
| BE (1) | BE820933A (no) |
| CA (1) | CA1037181A (no) |
| DE (1) | DE2447611A1 (no) |
| ES (1) | ES430641A1 (no) |
| FI (1) | FI57960C (no) |
| FR (1) | FR2247505B1 (no) |
| GB (1) | GB1480426A (no) |
| IN (1) | IN142982B (no) |
| IT (1) | IT1022677B (no) |
| NL (1) | NL7413367A (no) |
| NO (1) | NO743637L (no) |
| SE (1) | SE7412710L (no) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4017440A (en) * | 1973-10-10 | 1977-04-12 | Rohm And Haas Company | Polymers stabilized with polymerizable vinylbenzyltrialkyl ammonium salt surfactant |
| US4403063A (en) * | 1977-06-03 | 1983-09-06 | Hercules Incorporated | Organic pigments |
| US4343729A (en) * | 1977-06-03 | 1982-08-10 | Hercules Incorporated | Organic pigments |
| US4414353A (en) * | 1977-06-03 | 1983-11-08 | Hercules Incorporated | Organic pigments |
| US4403062A (en) * | 1977-06-03 | 1983-09-06 | Hercules Incorporated | Organic pigments |
| US4282060A (en) * | 1977-06-03 | 1981-08-04 | Hercules Incorporated | Organic pigments |
| US4404310A (en) * | 1977-06-03 | 1983-09-13 | Hercules Incorporated | Organic pigments |
| US4348257A (en) * | 1977-06-03 | 1982-09-07 | Hercules Incorporated | Organic pigments |
| US4178205A (en) * | 1977-08-17 | 1979-12-11 | The Dow Chemical Company | High strength non-woven fibrous material |
| US4187142A (en) * | 1977-08-17 | 1980-02-05 | The Dow Chemical Company | Method for forming high strength composites |
| US4189345A (en) * | 1977-08-17 | 1980-02-19 | The Dow Chemical Company | Fibrous compositions |
| US4456724A (en) * | 1978-05-25 | 1984-06-26 | Hercules Incorporated | Organic pigments |
| AU529801B2 (en) * | 1978-06-19 | 1983-06-23 | Monsanto Company | Paper additives |
| JPS5620009A (en) * | 1979-07-27 | 1981-02-25 | Asahi Chem Ind Co Ltd | New acryl copolymer, production thereof, coating obtained therefrom and use of the coating |
| JPS5626096A (en) * | 1979-08-02 | 1981-03-13 | Dainippon Ink & Chemicals | Sizing agent for cationic paper making |
| US4426489A (en) | 1980-02-21 | 1984-01-17 | The Dow Chemical Company | Surface active polymeric surfactants containing side chain hydrophobes |
| US4434267A (en) | 1980-06-16 | 1984-02-28 | Hercules Incorporated | Organic pigments |
| US4483959A (en) * | 1981-10-13 | 1984-11-20 | Hercules Incorporated | Organic pigments |
| FR2540127B1 (no) * | 1983-01-28 | 1985-03-29 | Rhone Poulenc Spec Chim | |
| FR2540123A1 (fr) * | 1983-01-28 | 1984-08-03 | Rhone Poulenc Spec Chim | Dispersions aqueuses stables et amphoteres de polymeres synthetiques |
| FR2540126A1 (fr) * | 1983-01-28 | 1984-08-03 | Rhone Poulenc Spec Chim | Latex stables et amphoteres de copolymeres a base de dienes conjugues |
| JPS59209636A (ja) * | 1983-05-13 | 1984-11-28 | Sumitomo Naugatuck Co Ltd | 低重合度ポリマ−分散剤 |
| JPS6025537A (ja) * | 1983-07-22 | 1985-02-08 | Sumitomo Naugatuck Co Ltd | 低重合度ポリマ−乳化剤 |
| DE3401573A1 (de) * | 1984-01-18 | 1985-07-25 | Bayer Ag, 5090 Leverkusen | Kationisches leimungsmittel fuer papier und verfahren zu seiner herstellung |
| US4684708A (en) * | 1985-03-11 | 1987-08-04 | Akzo N.V. | Cationic grafted starch copolymers |
| US5176748A (en) * | 1988-07-05 | 1993-01-05 | Bercen, Inc. | Alkenyl succinic anhydride emulsion |
| US5006413A (en) * | 1989-09-05 | 1991-04-09 | E. I. Du Pont De Nemours And Company | Waterbased methylol (meth)acrylamide acrylic polymer and polyurethane containing coating composition |
| JPH0680732A (ja) * | 1991-06-10 | 1994-03-22 | Otsuka Chem Co Ltd | ビニル系共重合体 |
| US5314945A (en) * | 1990-12-03 | 1994-05-24 | E. I. Du Pont De Nemours And Company | Waterbased coating compositions of methylol(meth)acrylamide acrylic polymer, polyurethane and melamine crosslinking agent |
| US5344902A (en) * | 1991-06-18 | 1994-09-06 | Occidental Research Corporation | Polymerization with initiator and quaternary ammonium salt |
| DE69927832T3 (de) * | 1998-08-07 | 2011-05-05 | Mallard Creek Polymers, Inc. | Neue latexzusammensetzung für beschichtung von verschiedenen substraten |
| US20050065284A1 (en) * | 1999-08-06 | 2005-03-24 | Venkataram Krishnan | Novel latex compositions for deposition on various substrates |
| US7368296B2 (en) | 2002-01-17 | 2008-05-06 | Applied Biosystems | Solid phases optimized for chemiluminescent detection |
| US7781498B2 (en) * | 2003-07-03 | 2010-08-24 | Mallard Creek Polymers, Inc. | Cationic latex as a carrier for bioactive ingredients and methods for making and using the same |
| US7981946B2 (en) * | 2003-07-03 | 2011-07-19 | Mallard Creek Polymers, Inc. | Antimicrobial and antistatic polymers and methods of using such polymers on various substrates |
| US7491753B2 (en) * | 2003-07-03 | 2009-02-17 | Mallard Creek Polymers, Inc. | Antimicrobial and antistatic polymers and methods of using such polymers on various substrates |
| JP2007023075A (ja) * | 2005-07-12 | 2007-02-01 | Fujifilm Holdings Corp | 有機変性層状珪酸塩を含有するポリエステル樹脂組成物 |
| US20070048249A1 (en) | 2005-08-24 | 2007-03-01 | Purdue Research Foundation | Hydrophilized bactericidal polymers |
| US20080233062A1 (en) * | 2006-08-24 | 2008-09-25 | Venkataram Krishnan | Cationic latex as a carrier for active ingredients and methods for making and using the same |
| US20080207774A1 (en) * | 2006-08-24 | 2008-08-28 | Venkataram Krishnan | Anionic latex as a carrier for active ingredients and methods for making and using the same |
| CA2661486C (en) | 2006-08-24 | 2013-04-23 | Mallard Creek Polymers, Inc. | Cationic latex as a carrier for bioactive ingredients and methods for making and using the same |
| JP6397784B2 (ja) * | 2015-03-10 | 2018-09-26 | デクセリアルズ株式会社 | 熱硬化性樹脂組成物、及び熱硬化性シート |
| EP3629731A1 (en) | 2017-05-27 | 2020-04-08 | Poly Group LLC | Dispersible antimicrobial complex and coatings therefrom |
| WO2018232417A1 (en) | 2017-06-16 | 2018-12-20 | Poly Group LLC | Polymeric antimicrobial surfactant |
| EP3680289B1 (en) * | 2017-09-15 | 2022-06-15 | LG Chem, Ltd. | Polymeric composition, polymer capsule, and fabric softener composition including same |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2009015A (en) * | 1933-06-19 | 1935-07-23 | Rohm & Haas | Cellulose solutions |
| US2595225A (en) * | 1950-02-09 | 1952-05-06 | Du Pont | Polymeric poly-quaternary ammonium salts |
| GB705887A (no) * | 1951-07-17 | |||
| US2744130A (en) * | 1952-04-11 | 1956-05-01 | Du Pont | Quaternary ammonium monomers and polymers thereof |
| US2884057A (en) * | 1954-02-25 | 1959-04-28 | American Cyanamid Co | Paper of improved dry strength and method of making same |
| US2941969A (en) * | 1954-08-26 | 1960-06-21 | American Cyanamid Co | Copolymer of a quaternary ammonium compound and acrylonitrile, solution thereof, and fiber formed therefrom |
| US3015605A (en) * | 1958-06-17 | 1962-01-02 | American Cyanamid Co | Paper sized with linear cationic polymer |
| US3068213A (en) * | 1959-12-01 | 1962-12-11 | American Cyanamid Co | Cationic copolymeric quaternary salts of chloromethyl styrene and acrylamide |
| DE1233604B (de) * | 1961-09-08 | 1967-02-02 | Du Pont | Verfahren zur Herstellung Aminoxydgruppen enthaltender Mischpolymerisate |
| US3702799A (en) * | 1969-04-04 | 1972-11-14 | Rohm & Haas | Polymers of quaternary ammonium compounds used as wet strength agents in paper |
| US3780092A (en) * | 1969-10-20 | 1973-12-18 | Kendall & Co | Monomeric emulsion stabilizers |
| US3925442A (en) * | 1971-01-28 | 1975-12-09 | Kendall & Co | Monomeric emulsion stabilizers |
| US4017440A (en) * | 1973-10-10 | 1977-04-12 | Rohm And Haas Company | Polymers stabilized with polymerizable vinylbenzyltrialkyl ammonium salt surfactant |
-
1973
- 1973-10-10 US US05/405,221 patent/US4017440A/en not_active Expired - Lifetime
-
1974
- 1974-08-26 CA CA207,749A patent/CA1037181A/en not_active Expired
- 1974-09-17 GB GB4038574A patent/GB1480426A/en not_active Expired
- 1974-09-21 IN IN2102/CAL/74A patent/IN142982B/en unknown
- 1974-10-02 FR FR7433217A patent/FR2247505B1/fr not_active Expired
- 1974-10-03 ES ES430641A patent/ES430641A1/es not_active Expired
- 1974-10-05 DE DE19742447611 patent/DE2447611A1/de not_active Withdrawn
- 1974-10-08 IT IT2817874A patent/IT1022677B/it active
- 1974-10-08 FI FI2935/74A patent/FI57960C/fi active
- 1974-10-09 JP JP11570974A patent/JPS5066546A/ja active Pending
- 1974-10-09 NO NO743637A patent/NO743637L/no unknown
- 1974-10-09 SE SE7412710A patent/SE7412710L/xx not_active Application Discontinuation
- 1974-10-10 BE BE149415A patent/BE820933A/xx unknown
- 1974-10-10 NL NL7413367A patent/NL7413367A/xx not_active Application Discontinuation
-
1976
- 1976-11-15 US US05/741,599 patent/US4152201A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IN142982B (no) | 1977-09-17 |
| DE2447611A1 (de) | 1975-04-17 |
| FR2247505B1 (no) | 1979-02-16 |
| ES430641A1 (es) | 1977-06-16 |
| FI293574A (no) | 1975-04-11 |
| US4152201A (en) | 1979-05-01 |
| GB1480426A (en) | 1977-07-20 |
| NL7413367A (nl) | 1975-04-14 |
| IT1022677B (it) | 1978-04-20 |
| FI57960B (fi) | 1980-07-31 |
| SE7412710L (no) | 1975-04-11 |
| FR2247505A1 (no) | 1975-05-09 |
| FI57960C (fi) | 1980-11-10 |
| CA1037181A (en) | 1978-08-22 |
| US4017440A (en) | 1977-04-12 |
| JPS5066546A (no) | 1975-06-04 |
| BE820933A (fr) | 1975-04-10 |
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