DE1302758B - Verfahren zur Herstellung von hartba ren, flussigen bis viskosen Losungen von Mischpolymerisaten - Google Patents
Verfahren zur Herstellung von hartba ren, flussigen bis viskosen Losungen von MischpolymerisatenInfo
- Publication number
 - DE1302758B DE1302758B DE19601302758D DE1302758DA DE1302758B DE 1302758 B DE1302758 B DE 1302758B DE 19601302758 D DE19601302758 D DE 19601302758D DE 1302758D A DE1302758D A DE 1302758DA DE 1302758 B DE1302758 B DE 1302758B
 - Authority
 - DE
 - Germany
 - Prior art keywords
 - copolymer
 - anhydride
 - epoxy
 - mixture
 - solution
 - 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.)
 - Pending
 
Links
- 229920001577 copolymer Polymers 0.000 title claims description 76
 - 238000000034 method Methods 0.000 title claims description 25
 - 238000004519 manufacturing process Methods 0.000 title claims description 14
 - 239000007788 liquid Substances 0.000 title claims description 6
 - 239000002904 solvent Substances 0.000 claims description 47
 - 150000008064 anhydrides Chemical class 0.000 claims description 43
 - 239000003054 catalyst Substances 0.000 claims description 31
 - 239000002253 acid Substances 0.000 claims description 27
 - 239000000178 monomer Substances 0.000 claims description 25
 - 229920000647 polyepoxide Polymers 0.000 claims description 22
 - 229920006395 saturated elastomer Polymers 0.000 claims description 22
 - 238000006116 polymerization reaction Methods 0.000 claims description 17
 - 150000007513 acids Chemical class 0.000 claims description 16
 - 150000001298 alcohols Chemical class 0.000 claims description 16
 - 239000003431 cross linking reagent Substances 0.000 claims description 9
 - 238000007334 copolymerization reaction Methods 0.000 claims description 8
 - 150000002763 monocarboxylic acids Chemical class 0.000 claims description 5
 - 150000007524 organic acids Chemical class 0.000 claims description 3
 - 239000003960 organic solvent Substances 0.000 claims description 3
 - 235000005985 organic acids Nutrition 0.000 claims description 2
 - 239000000203 mixture Substances 0.000 description 66
 - 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 52
 - 229920000642 polymer Polymers 0.000 description 47
 - 239000004593 Epoxy Chemical class 0.000 description 45
 - BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 26
 - 150000002118 epoxides Chemical class 0.000 description 26
 - CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 21
 - 239000004342 Benzoyl peroxide Substances 0.000 description 20
 - OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 20
 - 235000019400 benzoyl peroxide Nutrition 0.000 description 20
 - LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 18
 - 125000002887 hydroxy group Chemical group [H]O* 0.000 description 18
 - 230000009969 flowable effect Effects 0.000 description 17
 - 229920001451 polypropylene glycol Polymers 0.000 description 17
 - 238000010992 reflux Methods 0.000 description 17
 - LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 17
 - XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 15
 - 239000003085 diluting agent Substances 0.000 description 15
 - 229920001223 polyethylene glycol Polymers 0.000 description 15
 - 239000000047 product Substances 0.000 description 15
 - HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 15
 - PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
 - 238000009835 boiling Methods 0.000 description 14
 - MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 13
 - 239000000463 material Substances 0.000 description 13
 - -1 ether alcohols Chemical class 0.000 description 12
 - 238000010438 heat treatment Methods 0.000 description 12
 - 238000003756 stirring Methods 0.000 description 12
 - LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
 - 239000002202 Polyethylene glycol Substances 0.000 description 11
 - 150000002148 esters Chemical class 0.000 description 11
 - 238000002360 preparation method Methods 0.000 description 11
 - FUIQBJHUESBZNU-UHFFFAOYSA-N 2-[(dimethylazaniumyl)methyl]phenolate Chemical compound CN(C)CC1=CC=CC=C1O FUIQBJHUESBZNU-UHFFFAOYSA-N 0.000 description 10
 - 239000011541 reaction mixture Substances 0.000 description 9
 - SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
 - 229920002556 Polyethylene Glycol 300 Polymers 0.000 description 7
 - YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
 - 238000000465 moulding Methods 0.000 description 7
 - BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 6
 - 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 6
 - 125000004432 carbon atom Chemical group C* 0.000 description 6
 - 238000006243 chemical reaction Methods 0.000 description 6
 - 150000001875 compounds Chemical class 0.000 description 6
 - 150000005846 sugar alcohols Polymers 0.000 description 6
 - 238000005266 casting Methods 0.000 description 5
 - MUTGBJKUEZFXGO-UHFFFAOYSA-N hexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21 MUTGBJKUEZFXGO-UHFFFAOYSA-N 0.000 description 5
 - 238000002156 mixing Methods 0.000 description 5
 - 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
 - ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
 - NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
 - PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
 - OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
 - 229910052799 carbon Inorganic materials 0.000 description 4
 - 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
 - 150000002334 glycols Chemical class 0.000 description 4
 - WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
 - 239000011976 maleic acid Substances 0.000 description 4
 - VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
 - 229920002554 vinyl polymer Polymers 0.000 description 4
 - XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
 - KGPFHDDLZCYWAO-UHFFFAOYSA-N 2-(4-tert-butylphenoxy)ethanol Chemical compound CC(C)(C)C1=CC=C(OCCO)C=C1 KGPFHDDLZCYWAO-UHFFFAOYSA-N 0.000 description 3
 - UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 3
 - LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
 - KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
 - DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
 - HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
 - 238000010521 absorption reaction Methods 0.000 description 3
 - 150000008065 acid anhydrides Chemical class 0.000 description 3
 - MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
 - 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
 - FLBJFXNAEMSXGL-UHFFFAOYSA-N het anhydride Chemical compound O=C1OC(=O)C2C1C1(Cl)C(Cl)=C(Cl)C2(Cl)C1(Cl)Cl FLBJFXNAEMSXGL-UHFFFAOYSA-N 0.000 description 3
 - VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
 - 230000000704 physical effect Effects 0.000 description 3
 - 229920000570 polyether Polymers 0.000 description 3
 - 239000012429 reaction media Substances 0.000 description 3
 - 229920005989 resin Polymers 0.000 description 3
 - 239000011347 resin Substances 0.000 description 3
 - KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 2
 - VSKCCZIUZNTICH-ZPYUXNTASA-N (e)-but-2-enoic acid;ethenyl acetate Chemical compound C\C=C\C(O)=O.CC(=O)OC=C VSKCCZIUZNTICH-ZPYUXNTASA-N 0.000 description 2
 - IQBLWPLYPNOTJC-FPLPWBNLSA-N (z)-4-(2-ethylhexoxy)-4-oxobut-2-enoic acid Chemical group CCCCC(CC)COC(=O)\C=C/C(O)=O IQBLWPLYPNOTJC-FPLPWBNLSA-N 0.000 description 2
 - JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
 - NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
 - 229930185605 Bisphenol Natural products 0.000 description 2
 - VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
 - KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
 - LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
 - 239000004721 Polyphenylene oxide Substances 0.000 description 2
 - ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
 - 150000001412 amines Chemical class 0.000 description 2
 - 238000005452 bending Methods 0.000 description 2
 - 230000015572 biosynthetic process Effects 0.000 description 2
 - IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
 - JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
 - UTOVMEACOLCUCK-PLNGDYQASA-N butyl maleate Chemical group CCCCOC(=O)\C=C/C(O)=O UTOVMEACOLCUCK-PLNGDYQASA-N 0.000 description 2
 - 238000004132 cross linking Methods 0.000 description 2
 - RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
 - ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
 - FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
 - 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 2
 - 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 2
 - 230000002349 favourable effect Effects 0.000 description 2
 - NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 2
 - 239000011521 glass Substances 0.000 description 2
 - 235000011187 glycerol Nutrition 0.000 description 2
 - ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
 - NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical group COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 description 2
 - LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
 - 150000002989 phenols Chemical class 0.000 description 2
 - 239000000376 reactant Substances 0.000 description 2
 - CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
 - 239000007787 solid Substances 0.000 description 2
 - 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
 - 239000000126 substance Substances 0.000 description 2
 - 238000005292 vacuum distillation Methods 0.000 description 2
 - DJKGDNKYTKCJKD-BPOCMEKLSA-N (1s,4r,5s,6r)-1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic acid Chemical compound ClC1=C(Cl)[C@]2(Cl)[C@H](C(=O)O)[C@H](C(O)=O)[C@@]1(Cl)C2(Cl)Cl DJKGDNKYTKCJKD-BPOCMEKLSA-N 0.000 description 1
 - BOVQCIDBZXNFEJ-UHFFFAOYSA-N 1-chloro-3-ethenylbenzene Chemical compound ClC1=CC=CC(C=C)=C1 BOVQCIDBZXNFEJ-UHFFFAOYSA-N 0.000 description 1
 - KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
 - UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
 - OGMSGZZPTQNTIK-UHFFFAOYSA-N 1-methyl-2-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1C OGMSGZZPTQNTIK-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
 - JTINZFQXZLCHNS-UHFFFAOYSA-N 2,2-bis(oxiran-2-ylmethoxymethyl)butan-1-ol Chemical compound C1OC1COCC(CO)(CC)COCC1CO1 JTINZFQXZLCHNS-UHFFFAOYSA-N 0.000 description 1
 - FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
 - AUABZJZJXPSZCN-UHFFFAOYSA-N 2-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC=C1O AUABZJZJXPSZCN-UHFFFAOYSA-N 0.000 description 1
 - LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
 - YMOONIIMQBGTDU-UHFFFAOYSA-N 2-bromoethenylbenzene Chemical class BrC=CC1=CC=CC=C1 YMOONIIMQBGTDU-UHFFFAOYSA-N 0.000 description 1
 - ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 1
 - MEQQGPZLHWVQBZ-UHFFFAOYSA-N 2-methylidene-4-phenylhex-5-enoic acid Chemical compound C(=C)C(C1=CC=CC=C1)CC(C(=O)O)=C MEQQGPZLHWVQBZ-UHFFFAOYSA-N 0.000 description 1
 - JQXYBDVZAUEPDL-UHFFFAOYSA-N 2-methylidene-5-phenylpent-4-enoic acid Chemical compound OC(=O)C(=C)CC=CC1=CC=CC=C1 JQXYBDVZAUEPDL-UHFFFAOYSA-N 0.000 description 1
 - 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
 - GRWFFFOEIHGUBG-UHFFFAOYSA-N 3,4-Epoxy-6-methylcyclohexylmethyl-3,4-epoxy-6-methylcyclo-hexanecarboxylate Chemical compound C1C2OC2CC(C)C1C(=O)OCC1CC2OC2CC1C GRWFFFOEIHGUBG-UHFFFAOYSA-N 0.000 description 1
 - LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
 - ZWKNLRXFUTWSOY-UHFFFAOYSA-N 3-phenylprop-2-enenitrile Chemical class N#CC=CC1=CC=CC=C1 ZWKNLRXFUTWSOY-UHFFFAOYSA-N 0.000 description 1
 - 241000554155 Andes Species 0.000 description 1
 - WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
 - OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
 - FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
 - FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
 - SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
 - 239000005977 Ethylene Substances 0.000 description 1
 - YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
 - GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
 - ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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 - 239000012190 activator Substances 0.000 description 1
 - 239000003513 alkali Substances 0.000 description 1
 - 235000011114 ammonium hydroxide Nutrition 0.000 description 1
 - 125000003118 aryl group Chemical group 0.000 description 1
 - FWYSSOIRLVHQNC-UHFFFAOYSA-M benzyl(trimethyl)azanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)CC1=CC=CC=C1 FWYSSOIRLVHQNC-UHFFFAOYSA-M 0.000 description 1
 - KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
 - GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
 - 229910052794 bromium Inorganic materials 0.000 description 1
 - AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
 - 239000000920 calcium hydroxide Substances 0.000 description 1
 - 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
 - 150000001721 carbon Chemical group 0.000 description 1
 - 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
 - 230000003197 catalytic effect Effects 0.000 description 1
 - 239000007795 chemical reaction product Substances 0.000 description 1
 - 239000003795 chemical substances by application Substances 0.000 description 1
 - 239000000460 chlorine Substances 0.000 description 1
 - 229910052801 chlorine Inorganic materials 0.000 description 1
 - HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
 - 229940018557 citraconic acid Drugs 0.000 description 1
 - 238000001816 cooling Methods 0.000 description 1
 - IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
 - 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 1
 - LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
 - 239000012969 di-tertiary-butyl peroxide Substances 0.000 description 1
 - 150000001991 dicarboxylic acids Chemical class 0.000 description 1
 - GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
 - XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
 - SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
 - 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 1
 - 239000000839 emulsion Substances 0.000 description 1
 - 125000003700 epoxy group Chemical group 0.000 description 1
 - AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 1
 - RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
 - 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
 - 230000005496 eutectics Effects 0.000 description 1
 - 239000012467 final product Substances 0.000 description 1
 - VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical class O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
 - 150000003944 halohydrins Chemical class 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
 - 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
 - 239000008240 homogeneous mixture Substances 0.000 description 1
 - 239000012456 homogeneous solution Substances 0.000 description 1
 - 150000004679 hydroxides Chemical class 0.000 description 1
 - 150000002440 hydroxy compounds Chemical class 0.000 description 1
 - 150000007529 inorganic bases Chemical class 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
 - 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
 - 238000005259 measurement Methods 0.000 description 1
 - 238000002844 melting Methods 0.000 description 1
 - 229920003145 methacrylic acid copolymer Polymers 0.000 description 1
 - 229940117841 methacrylic acid copolymer Drugs 0.000 description 1
 - 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
 - 125000005394 methallyl group Chemical group 0.000 description 1
 - 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
 - XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
 - ZIYVHBGGAOATLY-UHFFFAOYSA-N methylmalonic acid Chemical class OC(=O)C(C)C(O)=O ZIYVHBGGAOATLY-UHFFFAOYSA-N 0.000 description 1
 - 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
 - 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 1
 - 150000007530 organic bases Chemical class 0.000 description 1
 - 150000002894 organic compounds Chemical class 0.000 description 1
 - 150000002978 peroxides Chemical class 0.000 description 1
 - 150000004965 peroxy acids Chemical class 0.000 description 1
 - 150000007519 polyprotic acids Polymers 0.000 description 1
 - 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
 - 125000001453 quaternary ammonium group Chemical group 0.000 description 1
 - 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
 - 239000011369 resultant mixture Substances 0.000 description 1
 - 150000003839 salts Chemical class 0.000 description 1
 - 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
 - 239000011877 solvent mixture Substances 0.000 description 1
 - 239000000600 sorbitol Substances 0.000 description 1
 - 150000003440 styrenes Chemical class 0.000 description 1
 - 125000001424 substituent group Chemical group 0.000 description 1
 - 229940014800 succinic anhydride Drugs 0.000 description 1
 - CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
 - UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
 - 229920001187 thermosetting polymer Polymers 0.000 description 1
 - ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
 - JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
 - 239000000080 wetting agent Substances 0.000 description 1
 
Classifications
- 
        
- C—CHEMISTRY; METALLURGY
 - C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
 - C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
 - C08F22/00—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 carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
 
 - 
        
- 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
 
 - 
        
- 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
 - C08F220/00—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
 - C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
 - C08F220/04—Acids; Metal salts or ammonium salts thereof
 
 - 
        
- 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
 - C08F220/00—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
 - C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
 - C08F220/04—Acids; Metal salts or ammonium salts thereof
 - C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
 
 - 
        
- 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
 - C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
 - C08F283/10—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule
 
 - 
        
- C—CHEMISTRY; METALLURGY
 - C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
 - C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
 - C08K5/00—Use of organic ingredients
 - C08K5/04—Oxygen-containing compounds
 - C08K5/15—Heterocyclic compounds having oxygen in the ring
 - C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
 - C08K5/1515—Three-membered rings
 
 - 
        
- C—CHEMISTRY; METALLURGY
 - C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
 - C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
 - C08L57/00—Compositions of unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
 
 - 
        
- C—CHEMISTRY; METALLURGY
 - C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
 - C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
 - C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
 
 
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)
 - Paints Or Removers (AREA)
 
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title | 
|---|---|---|---|
| US78804659A | 1959-01-21 | 1959-01-21 | |
| US78805859A | 1959-01-21 | 1959-01-21 | 
Publications (1)
| Publication Number | Publication Date | 
|---|---|
| DE1302758B true DE1302758B (de) | 1972-01-13 | 
Family
ID=27120733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date | 
|---|---|---|---|
| DE19601302758D Pending DE1302758B (de) | 1959-01-21 | 1960-01-20 | Verfahren zur Herstellung von hartba ren, flussigen bis viskosen Losungen von Mischpolymerisaten | 
Country Status (4)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title | 
|---|---|---|---|---|
| CA1321851C (en) * | 1988-01-11 | 1993-08-31 | Kathleen Anne Hughes | Process for preparing functionalized polymeric compositions | 
| DE4242039A1 (de) * | 1992-12-12 | 1994-06-16 | Stockhausen Chem Fab Gmbh | Copolymerisate und ihre Verwendung zur Behandlung von Leder | 
| US7342075B2 (en) * | 2002-10-31 | 2008-03-11 | Basf Corporation | Carbamate functional addition polymers and method for their preparation | 
| WO2009130915A1 (ja) * | 2008-04-25 | 2009-10-29 | 株式会社日本触媒 | ポリアクリル酸(塩)系吸水性樹脂およびその製造方法 | 
| CN113278114B (zh) * | 2021-05-21 | 2023-01-31 | 安徽科邦树脂科技有限公司 | 一种功能性环氧改性丙烯酸酯乳液及其制备方法 | 
- 
        0
        
- NL NL127629D patent/NL127629C/xx active
 - NL NL247578D patent/NL247578A/xx unknown
 
 - 
        1960
        
- 1960-01-12 GB GB114960A patent/GB896821A/en not_active Expired
 - 1960-01-20 DE DE19601302758D patent/DE1302758B/de active Pending
 - 1960-01-21 FR FR816328A patent/FR1248212A/fr not_active Expired
 
 
Also Published As
| Publication number | Publication date | 
|---|---|
| GB896821A (en) | 1962-05-16 | 
| NL247578A (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) | |
| NL127629C (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) | |
| FR1248212A (fr) | 1960-12-09 | 
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