JPS6353181B2 - - Google Patents
Info
- Publication number
- JPS6353181B2 JPS6353181B2 JP4765180A JP4765180A JPS6353181B2 JP S6353181 B2 JPS6353181 B2 JP S6353181B2 JP 4765180 A JP4765180 A JP 4765180A JP 4765180 A JP4765180 A JP 4765180A JP S6353181 B2 JPS6353181 B2 JP S6353181B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- alkyl group
- carbon atoms
- amino acid
- vinylbenzyl
- 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
- 150000001875 compounds Chemical class 0.000 claims description 51
- -1 amino acid compound Chemical class 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 7
- WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 5
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000000126 substance Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 6
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229960003237 betaine Drugs 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 150000003839 salts Chemical group 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 4
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- CJJIVIUZNZALQE-UHFFFAOYSA-N 2-[2-hydroxyethyl(1-phenylprop-2-enyl)amino]acetic acid Chemical compound OCCN(CC(O)=O)C(C=C)C1=CC=CC=C1 CJJIVIUZNZALQE-UHFFFAOYSA-N 0.000 description 2
- KMHPOGIZUITZEP-UHFFFAOYSA-N 2-[2-hydroxyethyl(1-phenylprop-2-enyl)amino]ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(CCO)C(C=C)C1=CC=CC=C1 KMHPOGIZUITZEP-UHFFFAOYSA-N 0.000 description 2
- AJTVSSFTXWNIRG-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanesulfonic acid Chemical compound OCC[NH+](CCO)CCS([O-])(=O)=O AJTVSSFTXWNIRG-UHFFFAOYSA-N 0.000 description 2
- AMUPVRGELSJGKT-UHFFFAOYSA-N 3-[2-hydroxyethyl(1-phenylprop-2-enyl)amino]propanoic acid Chemical compound OC(=O)CCN(CCO)C(C=C)C1=CC=CC=C1 AMUPVRGELSJGKT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- FOUZISDNESEYLX-UHFFFAOYSA-N N-hydroxyethyl glycine Natural products OCCNCC(O)=O FOUZISDNESEYLX-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 229940000635 beta-alanine Drugs 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229960003080 taurine Drugs 0.000 description 2
- PGYBQLSNQQMAFE-UHFFFAOYSA-N (1-phenylprop-2-enylamino)methanol Chemical compound OCNC(C=C)C1=CC=CC=C1 PGYBQLSNQQMAFE-UHFFFAOYSA-N 0.000 description 1
- FXLJHFCTYDFUER-UHFFFAOYSA-N 1-bromoprop-2-enylbenzene Chemical compound C=CC(Br)C1=CC=CC=C1 FXLJHFCTYDFUER-UHFFFAOYSA-N 0.000 description 1
- XOSWHKPBBJLUBE-UHFFFAOYSA-N 2-(1-phenylprop-2-enylamino)acetic acid Chemical compound OC(=O)CNC(C=C)C1=CC=CC=C1 XOSWHKPBBJLUBE-UHFFFAOYSA-N 0.000 description 1
- YPXRPPMJYNVONP-UHFFFAOYSA-N 2-(1-phenylprop-2-enylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)CCNC(C=C)C1=CC=CC=C1 YPXRPPMJYNVONP-UHFFFAOYSA-N 0.000 description 1
- CVONSVCROOVQEL-UHFFFAOYSA-N 2-(1-phenylprop-2-enylamino)ethanol Chemical compound OCCNC(C=C)C1=CC=CC=C1 CVONSVCROOVQEL-UHFFFAOYSA-N 0.000 description 1
- FANMLHZQQYHZFU-UHFFFAOYSA-N 2-(13-phenylpentadec-14-enylamino)ethanol Chemical compound OCCNCCCCCCCCCCCCC(C=C)C1=CC=CC=C1 FANMLHZQQYHZFU-UHFFFAOYSA-N 0.000 description 1
- BVIXTPMSXQAQBG-UHFFFAOYSA-N 2-(2-hydroxyethylamino)ethanesulfonic acid Chemical compound OCCNCCS(O)(=O)=O BVIXTPMSXQAQBG-UHFFFAOYSA-N 0.000 description 1
- WUHXNMJSNJXJEZ-UHFFFAOYSA-N 2-(hydroxymethylamino)ethanesulfonic acid Chemical compound OCNCCS(O)(=O)=O WUHXNMJSNJXJEZ-UHFFFAOYSA-N 0.000 description 1
- WBTIFBJEYFLFFW-UHFFFAOYSA-N 2-(hydroxymethylazaniumyl)acetate Chemical compound OCNCC(O)=O WBTIFBJEYFLFFW-UHFFFAOYSA-N 0.000 description 1
- HPXJGCZHVSOCOV-UHFFFAOYSA-N 2-[2-hydroxydodecyl(1-phenylprop-2-enyl)amino]ethanesulfonic acid Chemical compound CCCCCCCCCCC(O)CN(CCS(O)(=O)=O)C(C=C)C1=CC=CC=C1 HPXJGCZHVSOCOV-UHFFFAOYSA-N 0.000 description 1
- RIZNUXPFUYLDBS-UHFFFAOYSA-N 2-[2-hydroxyethyl(1-phenylprop-2-enyl)amino]ethanol Chemical compound OCCN(CCO)C(C=C)C1=CC=CC=C1 RIZNUXPFUYLDBS-UHFFFAOYSA-N 0.000 description 1
- DCULPMMMNWBFCE-UHFFFAOYSA-N 2-[dodecyl(2-hydroxyethyl)amino]ethanesulfonic acid Chemical compound CCCCCCCCCCCCN(CCO)CCS(O)(=O)=O DCULPMMMNWBFCE-UHFFFAOYSA-N 0.000 description 1
- PVADOOQKMYVERE-UHFFFAOYSA-N 2-[dodecyl(2-hydroxyethyl)azaniumyl]acetate Chemical compound CCCCCCCCCCCC[NH+](CCO)CC([O-])=O PVADOOQKMYVERE-UHFFFAOYSA-N 0.000 description 1
- JCWKXYWFVPKZOE-UHFFFAOYSA-N 2-[hydroxymethyl(1-phenylprop-2-enyl)amino]acetic acid Chemical compound OC(=O)CN(CO)C(C=C)C1=CC=CC=C1 JCWKXYWFVPKZOE-UHFFFAOYSA-N 0.000 description 1
- YLXUSCWRBKQKAR-UHFFFAOYSA-N 2-[hydroxymethyl(1-phenylprop-2-enyl)amino]ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(CO)C(C=C)C1=CC=CC=C1 YLXUSCWRBKQKAR-UHFFFAOYSA-N 0.000 description 1
- REHNPQSZCUTTKZ-UHFFFAOYSA-N 2-ethylhexyl ethenesulfonate Chemical compound CCCCC(CC)COS(=O)(=O)C=C REHNPQSZCUTTKZ-UHFFFAOYSA-N 0.000 description 1
- JCXVGKHPBDUOHN-UHFFFAOYSA-N 3-(1-phenylprop-2-enylamino)propanoic acid Chemical compound OC(=O)CCNC(C=C)C1=CC=CC=C1 JCXVGKHPBDUOHN-UHFFFAOYSA-N 0.000 description 1
- DWHWDRLMROVVSD-UHFFFAOYSA-N 3-(hydroxymethylamino)propanoic acid Chemical compound OCNCCC(O)=O DWHWDRLMROVVSD-UHFFFAOYSA-N 0.000 description 1
- HHHQGSPGSZWCEQ-UHFFFAOYSA-N 3-[bis(2-hydroxyethyl)amino]propanoic acid Chemical compound OCCN(CCO)CCC(O)=O HHHQGSPGSZWCEQ-UHFFFAOYSA-N 0.000 description 1
- IJGGDEKIITVLSS-UHFFFAOYSA-N 3-[dodecyl(2-hydroxyethyl)amino]propanoic acid Chemical compound CCCCCCCCCCCCN(CCO)CCC(O)=O IJGGDEKIITVLSS-UHFFFAOYSA-N 0.000 description 1
- ZDYRZFIFSRNXKY-UHFFFAOYSA-N 3-[hydroxymethyl(1-phenylprop-2-enyl)amino]propanoic acid Chemical compound OC(=O)CCN(CO)C(C=C)C1=CC=CC=C1 ZDYRZFIFSRNXKY-UHFFFAOYSA-N 0.000 description 1
- KUQZJTBEIIRXJP-UHFFFAOYSA-N 6-(2-hydroxyethylamino)hexanoic acid Chemical compound OCCNCCCCCC(O)=O KUQZJTBEIIRXJP-UHFFFAOYSA-N 0.000 description 1
- WPVYGGHBGPAEAB-UHFFFAOYSA-N 6-(hydroxymethylamino)hexanoic acid Chemical compound OCNCCCCCC(O)=O WPVYGGHBGPAEAB-UHFFFAOYSA-N 0.000 description 1
- VSIDOCNQOBCCKX-UHFFFAOYSA-N 6-[2-hydroxyethyl(1-phenylprop-2-enyl)amino]hexanoic acid Chemical compound OC(=O)CCCCCN(CCO)C(C=C)C1=CC=CC=C1 VSIDOCNQOBCCKX-UHFFFAOYSA-N 0.000 description 1
- OAVOLDKPUFUHAT-UHFFFAOYSA-N 6-[bis(2-hydroxyethyl)amino]hexanoic acid Chemical compound OCCN(CCO)CCCCCC(O)=O OAVOLDKPUFUHAT-UHFFFAOYSA-N 0.000 description 1
- ICGFGEUMVZFJKG-UHFFFAOYSA-N 6-[dodecyl(2-hydroxyethyl)amino]hexanoic acid Chemical compound CCCCCCCCCCCCN(CCO)CCCCCC(O)=O ICGFGEUMVZFJKG-UHFFFAOYSA-N 0.000 description 1
- FMMNZOAIQGOEAD-UHFFFAOYSA-N 6-[hydroxymethyl(1-phenylprop-2-enyl)amino]hexanoic acid Chemical compound OC(=O)CCCCCN(CO)C(C=C)C1=CC=CC=C1 FMMNZOAIQGOEAD-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical class NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- DQGSVNTZGRLFGR-UHFFFAOYSA-N C=CC(C1=CC=CC=C1)[N+](CCO)(CCO)CC([O-])=O Chemical compound C=CC(C1=CC=CC=C1)[N+](CCO)(CCO)CC([O-])=O DQGSVNTZGRLFGR-UHFFFAOYSA-N 0.000 description 1
- MQVYNDUABXIYLD-UHFFFAOYSA-N CCCCCCCCCCCC[N+](CCO)(CC([O-])=O)C(C=C)C1=CC=CC=C1 Chemical compound CCCCCCCCCCCC[N+](CCO)(CC([O-])=O)C(C=C)C1=CC=CC=C1 MQVYNDUABXIYLD-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 1
- FSVCELGFZIQNCK-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)glycine Chemical compound OCCN(CCO)CC(O)=O FSVCELGFZIQNCK-UHFFFAOYSA-N 0.000 description 1
- PPDDDJFBMYJHBK-UHFFFAOYSA-N N-(2-hydroxyethyl)-beta-alanine Chemical compound OCCNCCC(O)=O PPDDDJFBMYJHBK-UHFFFAOYSA-N 0.000 description 1
- YPIGGYHFMKJNKV-UHFFFAOYSA-N N-ethylglycine Chemical compound CC[NH2+]CC([O-])=O YPIGGYHFMKJNKV-UHFFFAOYSA-N 0.000 description 1
- 101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- QGVVOGDAIQQAQE-UHFFFAOYSA-N butyl ethenesulfonate Chemical compound CCCCOS(=O)(=O)C=C QGVVOGDAIQQAQE-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- UWSRZFFEFYLWIA-UHFFFAOYSA-N dodecyl ethenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C=C UWSRZFFEFYLWIA-UHFFFAOYSA-N 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- MWFJXRUUPWIALU-UHFFFAOYSA-N ethyl ethenesulfonate Chemical compound CCOS(=O)(=O)C=C MWFJXRUUPWIALU-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- OIGSXRLVIQGTAV-UHFFFAOYSA-N methyl ethenesulfonate Chemical compound COS(=O)(=O)C=C OIGSXRLVIQGTAV-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4765180A JPS56145249A (en) | 1980-04-10 | 1980-04-10 | Polymerizable amino acid compound |
| GB8111045A GB2075970B (en) | 1980-04-10 | 1981-04-08 | Polymerisable amino acid compounds and their production |
| DE19813114360 DE3114360A1 (de) | 1980-04-10 | 1981-04-09 | Polymerisierbare aminosaeureverbindungen und ihre herstellung |
| CA000375135A CA1161436A (en) | 1980-04-10 | 1981-04-09 | Polymerizable amino acid compounds and their production |
| US06/372,729 US4452746A (en) | 1980-04-10 | 1982-04-28 | Polymerizable amino acid compounds and their production |
| US06/594,826 US4543216A (en) | 1980-04-10 | 1984-03-29 | Polymerizable amino acid compounds and their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4765180A JPS56145249A (en) | 1980-04-10 | 1980-04-10 | Polymerizable amino acid compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56145249A JPS56145249A (en) | 1981-11-11 |
| JPS6353181B2 true JPS6353181B2 (enrdf_load_stackoverflow) | 1988-10-21 |
Family
ID=12781151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4765180A Granted JPS56145249A (en) | 1980-04-10 | 1980-04-10 | Polymerizable amino acid compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56145249A (enrdf_load_stackoverflow) |
-
1980
- 1980-04-10 JP JP4765180A patent/JPS56145249A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56145249A (en) | 1981-11-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS62270603A (ja) | アルコキシ化した／カチオンで改質したアミドを含むポリマ−およびその製造法 | |
| US1977253A (en) | Epichlorhydrin-amine condensation product | |
| JPH08231478A (ja) | 新規な第４級アンモニウム塩及びその製造法 | |
| JP2003171401A (ja) | ヒドロキシアルキルセルロースの製造方法 | |
| JPS6353181B2 (enrdf_load_stackoverflow) | ||
| JPS5973560A (ja) | 重合性スルホベタイン化合物ならびにその製法 | |
| CN112225843A (zh) | 一种三元阻垢剂及其制备方法 | |
| JPH0518849B2 (enrdf_load_stackoverflow) | ||
| KR19980018802A (ko) | 산과 아민 작용기 모두를 함유하는 중합체 조성물 제조방법(process for preparing polymer compositions containing both acid and amine functionality | |
| JPS5838475B2 (ja) | 含フッ素界面活性剤 | |
| US4543216A (en) | Polymerizable amino acid compounds and their production | |
| JPS6353182B2 (enrdf_load_stackoverflow) | ||
| JPH03223239A (ja) | 新規ベタイン及びそれを含有する分散剤 | |
| JP4737788B2 (ja) | ポリビニルアミン塩とその用途 | |
| JPS5826906B2 (ja) | 重合性アミノ酸化合物 | |
| JP2750875B2 (ja) | 新規アゾアミジン塩及びその製法 | |
| JP2000136250A (ja) | 加硫促進剤としてのキサントゲン酸アリ―ルグアニジニウムの使用およびそれの製造方法 | |
| JPH0469141B2 (enrdf_load_stackoverflow) | ||
| US4180629A (en) | Polymers containing a reactive aromatic system based on p-phenylenediamine derivatives | |
| JPS598275B2 (ja) | ポリオキサポリフルオロアルカンルイノ コウゾウオモツスルホンサンユウドウタイオヨビ ソノセイゾウホウホウ | |
| US4111858A (en) | Process for the preparation of polyhydroxy methylene ethers and ion exchangers composed thereof | |
| US4127732A (en) | Monomers and polymers containing the reactive aromatic system and method for their preparation | |
| CA1071230A (en) | Monomers containing a reactive aromatic system and method for their preparation | |
| JP2008528781A (ja) | ビニルアルコール−ｎ−ビニルアミン共重合体及びその製造方法 | |
| JP3713841B2 (ja) | カチオン性微粒子ゲルおよびその製造方法 |