JPH0325445B2 - - Google Patents
Info
- Publication number
- JPH0325445B2 JPH0325445B2 JP18598289A JP18598289A JPH0325445B2 JP H0325445 B2 JPH0325445 B2 JP H0325445B2 JP 18598289 A JP18598289 A JP 18598289A JP 18598289 A JP18598289 A JP 18598289A JP H0325445 B2 JPH0325445 B2 JP H0325445B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- hydroxyethyl
- bis
- alkyl substituted
- substituted product
- 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
- 229920000728 polyester Polymers 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 20
- -1 oxirane compound Chemical class 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000007519 polyprotic acids Polymers 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 42
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 42
- 229960003237 betaine Drugs 0.000 description 42
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 15
- 239000002253 acid Substances 0.000 description 10
- 150000008040 ionic compounds Chemical class 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 125000003010 ionic group Chemical group 0.000 description 6
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000011342 resin composition Substances 0.000 description 5
- 239000002966 varnish Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 229920000180 alkyd Polymers 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 229960003080 taurine Drugs 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- 239000004640 Melamine resin Substances 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
- 239000004743 Polypropylene Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- OBESRABRARNZJB-UHFFFAOYSA-N aminomethanesulfonic acid Chemical compound NCS(O)(=O)=O OBESRABRARNZJB-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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- WJZMWKFYCKUIFG-UHFFFAOYSA-N (1,3-dihydroxybutan-2-ylamino)methanesulfonic acid Chemical compound CC(O)C(CO)NCS(O)(=O)=O WJZMWKFYCKUIFG-UHFFFAOYSA-N 0.000 description 1
- PKZDOMDVIGMNRK-UHFFFAOYSA-N (1,3-dihydroxypropan-2-ylamino)methanesulfonic acid Chemical compound OCC(CO)NCS(O)(=O)=O PKZDOMDVIGMNRK-UHFFFAOYSA-N 0.000 description 1
- ZRYQPUHICKOCHT-UHFFFAOYSA-N (1,4-dihydroxybutan-2-ylamino)methanesulfonic acid Chemical compound OCCC(CO)NCS(O)(=O)=O ZRYQPUHICKOCHT-UHFFFAOYSA-N 0.000 description 1
- ATCHKIMLWBNVAG-UHFFFAOYSA-N (1,5-dihydroxypentan-2-ylamino)methanesulfonic acid Chemical compound OCCCC(CO)NCS(O)(=O)=O ATCHKIMLWBNVAG-UHFFFAOYSA-N 0.000 description 1
- HJBQUHBIKSCKCX-UHFFFAOYSA-N (1-hydroxypropan-2-ylamino)methanesulfonic acid Chemical compound OCC(C)NCS(O)(=O)=O HJBQUHBIKSCKCX-UHFFFAOYSA-N 0.000 description 1
- CKFNBZXQTFWLFR-UHFFFAOYSA-N (2,3-dihydroxypropylamino)methanesulfonic acid Chemical compound OCC(O)CNCS(O)(=O)=O CKFNBZXQTFWLFR-UHFFFAOYSA-N 0.000 description 1
- JBOWGOOXLSDXHE-UHFFFAOYSA-N (2-hydroxyethylamino)methanesulfonic acid Chemical compound OCCNCS(O)(=O)=O JBOWGOOXLSDXHE-UHFFFAOYSA-N 0.000 description 1
- RIDJPQGDTBCLEB-UHFFFAOYSA-N (2-hydroxypentylamino)methanesulfonic acid Chemical compound CCCC(O)CNCS(O)(=O)=O RIDJPQGDTBCLEB-UHFFFAOYSA-N 0.000 description 1
- PQAQSDMCVNNRPF-UHFFFAOYSA-N (2-hydroxypropylamino)methanesulfonic acid Chemical compound CC(O)CNCS(O)(=O)=O PQAQSDMCVNNRPF-UHFFFAOYSA-N 0.000 description 1
- ZYKSOHSRGWRHSL-UHFFFAOYSA-N (3-hydroxybutan-2-ylamino)methanesulfonic acid Chemical compound CC(O)C(C)NCS(O)(=O)=O ZYKSOHSRGWRHSL-UHFFFAOYSA-N 0.000 description 1
- ZZGGNGUMBKOMNR-UHFFFAOYSA-N (3-hydroxypropylamino)methanesulfonic acid Chemical compound OCCCNCS(O)(=O)=O ZZGGNGUMBKOMNR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- GAGVEJJWDAKMKT-UHFFFAOYSA-N 1-(1,3-dihydroxybutan-2-ylamino)ethanesulfonic acid Chemical compound CC(O)C(CO)NC(C)S(O)(=O)=O GAGVEJJWDAKMKT-UHFFFAOYSA-N 0.000 description 1
- WCIOHEPFXBTXKX-UHFFFAOYSA-N 1-(1,3-dihydroxypropan-2-ylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)C(C)NC(CO)CO WCIOHEPFXBTXKX-UHFFFAOYSA-N 0.000 description 1
- KSAGECAVVVWXMB-UHFFFAOYSA-N 1-(1,4-dihydroxybutan-2-ylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)C(C)NC(CO)CCO KSAGECAVVVWXMB-UHFFFAOYSA-N 0.000 description 1
- KWNPNQVRRGKPPV-UHFFFAOYSA-N 1-(1,5-dihydroxypentan-2-ylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)C(C)NC(CO)CCCO KWNPNQVRRGKPPV-UHFFFAOYSA-N 0.000 description 1
- ZDQKCIWYITVPCE-UHFFFAOYSA-N 1-(1-hydroxypropan-2-ylamino)ethanesulfonic acid Chemical compound OCC(C)NC(C)S(O)(=O)=O ZDQKCIWYITVPCE-UHFFFAOYSA-N 0.000 description 1
- JPTCDCPGMMYCMQ-UHFFFAOYSA-N 1-(2,3-dihydroxypropylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)C(C)NCC(O)CO JPTCDCPGMMYCMQ-UHFFFAOYSA-N 0.000 description 1
- PIYPSTPVGGEDHM-UHFFFAOYSA-N 1-(2,3-dihydroxypropylimino)ethanesulfonic acid;propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O.OS(=O)(=O)C(C)=NCC(O)CO PIYPSTPVGGEDHM-UHFFFAOYSA-N 0.000 description 1
- MSITZPOLAKHHPS-UHFFFAOYSA-N 1-(2-hydroxyethylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)C(C)NCCO MSITZPOLAKHHPS-UHFFFAOYSA-N 0.000 description 1
- CBLSSEJRGZZCOD-UHFFFAOYSA-N 1-(2-hydroxyethylimino)ethanesulfonic acid;propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O.OS(=O)(=O)C(C)=NCCO CBLSSEJRGZZCOD-UHFFFAOYSA-N 0.000 description 1
- CHZQDPAIWIAAHB-UHFFFAOYSA-N 1-(2-hydroxypentylamino)ethanesulfonic acid Chemical compound CCCC(O)CNC(C)S(O)(=O)=O CHZQDPAIWIAAHB-UHFFFAOYSA-N 0.000 description 1
- DVHSSBNUFRJZKH-UHFFFAOYSA-N 1-(2-hydroxypropylamino)ethanesulfonic acid Chemical compound CC(O)CNC(C)S(O)(=O)=O DVHSSBNUFRJZKH-UHFFFAOYSA-N 0.000 description 1
- LLNUVVPGAMKQPP-UHFFFAOYSA-N 1-(2-hydroxypropylimino)ethanesulfonic acid;propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O.CC(O)CN=C(C)S(O)(=O)=O LLNUVVPGAMKQPP-UHFFFAOYSA-N 0.000 description 1
- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical group CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
- DEWNBQJQGQWRTD-UHFFFAOYSA-N 1-(3-hydroxybutan-2-ylamino)ethanesulfonic acid Chemical compound CC(O)C(C)NC(C)S(O)(=O)=O DEWNBQJQGQWRTD-UHFFFAOYSA-N 0.000 description 1
- BZQLSTFTJDXEGQ-UHFFFAOYSA-N 1-(3-hydroxypropylamino)ethanesulfonic acid Chemical compound OS(=O)(=O)C(C)NCCCO BZQLSTFTJDXEGQ-UHFFFAOYSA-N 0.000 description 1
- RGVGYONXICSLJS-UHFFFAOYSA-N 1-(octylamino)ethanesulfonic acid Chemical compound CCCCCCCCNC(C)S(O)(=O)=O RGVGYONXICSLJS-UHFFFAOYSA-N 0.000 description 1
- LPZGYBWDXRMVSM-UHFFFAOYSA-N 1-[(2-hydroxy-2-methylbutyl)amino]ethanesulfonic acid Chemical compound CCC(C)(O)CNC(C)S(O)(=O)=O LPZGYBWDXRMVSM-UHFFFAOYSA-N 0.000 description 1
- AJSQNBBXWBOUKU-UHFFFAOYSA-N 1-[(3-hydroxy-2,3-dimethylbutan-2-yl)amino]ethanesulfonic acid Chemical compound OS(=O)(=O)C(C)NC(C)(C)C(C)(C)O AJSQNBBXWBOUKU-UHFFFAOYSA-N 0.000 description 1
- HOFGQVZDMWVXAG-UHFFFAOYSA-N 1-[(4-hydroxy-2,5-dimethylhexan-3-yl)amino]ethanesulfonic acid Chemical compound CC(C)C(O)C(C(C)C)NC(C)S(O)(=O)=O HOFGQVZDMWVXAG-UHFFFAOYSA-N 0.000 description 1
- XFMJGEXUSVPGHF-UHFFFAOYSA-N 1-[(6-hydroxy-6-methylheptan-2-yl)amino]ethanesulfonic acid Chemical compound OS(=O)(=O)C(C)NC(C)CCCC(C)(C)O XFMJGEXUSVPGHF-UHFFFAOYSA-N 0.000 description 1
- QUJWSPDEAXJFOK-UHFFFAOYSA-N 1-[2-ethylhexyl(2-hydroxyethyl)amino]ethanesulfonic acid Chemical compound CCCCC(CC)CN(CCO)C(C)S(O)(=O)=O QUJWSPDEAXJFOK-UHFFFAOYSA-N 0.000 description 1
- BUCFARXZLZCGOE-UHFFFAOYSA-N 1-[2-hydroxyethyl(2-hydroxypropyl)amino]ethanesulfonic acid Chemical compound CC(O)CN(CCO)C(C)S(O)(=O)=O BUCFARXZLZCGOE-UHFFFAOYSA-N 0.000 description 1
- SEKMULURMKFJGV-UHFFFAOYSA-N 1-[2-hydroxyethyl(methyl)amino]ethanesulfonic acid Chemical compound OS(=O)(=O)C(C)N(C)CCO SEKMULURMKFJGV-UHFFFAOYSA-N 0.000 description 1
- XILUTCXOBRZLPP-UHFFFAOYSA-N 1-[2-hydroxyethyl(octadecyl)amino]ethanesulfonic acid Chemical compound CCCCCCCCCCCCCCCCCCN(CCO)C(C)S(O)(=O)=O XILUTCXOBRZLPP-UHFFFAOYSA-N 0.000 description 1
- XSINBDAPJDOHEQ-UHFFFAOYSA-N 1-[2-hydroxyethyl(propan-2-yl)amino]ethanesulfonic acid Chemical compound OCCN(C(C)C)C(C)S(O)(=O)=O XSINBDAPJDOHEQ-UHFFFAOYSA-N 0.000 description 1
- BPNMADJECVITOE-UHFFFAOYSA-N 1-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-(2-hydroxyethyl)amino]ethanesulfonic acid Chemical compound OS(=O)(=O)C(C)N(CCO)C(CO)(CO)CO BPNMADJECVITOE-UHFFFAOYSA-N 0.000 description 1
- QATWXMJWRQHACE-UHFFFAOYSA-N 1-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-(3-hydroxypropyl)amino]ethanesulfonic acid Chemical compound OS(=O)(=O)C(C)N(C(CO)(CO)CO)CCCO QATWXMJWRQHACE-UHFFFAOYSA-N 0.000 description 1
- NCDVKGXYZVVEKW-UHFFFAOYSA-N 1-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]ethanesulfonic acid Chemical compound OS(=O)(=O)C(C)NC(CO)(CO)CO NCDVKGXYZVVEKW-UHFFFAOYSA-N 0.000 description 1
- XGSWGUYQUXSWPH-UHFFFAOYSA-N 1-[[3-hydroxy-2,2-bis(hydroxymethyl)propyl]amino]ethanesulfonic acid Chemical compound OS(=O)(=O)C(C)NCC(CO)(CO)CO XGSWGUYQUXSWPH-UHFFFAOYSA-N 0.000 description 1
- AWNZTLUTNFWQBA-UHFFFAOYSA-N 1-[bis(1,3-dihydroxypropan-2-yl)amino]ethanesulfonic acid Chemical compound OS(=O)(=O)C(C)N(C(CO)CO)C(CO)CO AWNZTLUTNFWQBA-UHFFFAOYSA-N 0.000 description 1
- LBLLTPWNHONJSS-UHFFFAOYSA-N 1-[bis(2,3-dihydroxypropyl)amino]ethanesulfonic acid Chemical compound OCC(O)CN(C(C)S(O)(=O)=O)CC(O)CO LBLLTPWNHONJSS-UHFFFAOYSA-N 0.000 description 1
- LDIXMPCPQLSOGZ-UHFFFAOYSA-N 1-[bis(2-hydroxypropyl)amino]ethanesulfonic acid Chemical compound CC(O)CN(CC(C)O)C(C)S(O)(=O)=O LDIXMPCPQLSOGZ-UHFFFAOYSA-N 0.000 description 1
- PZSVWOVHWJVYBZ-UHFFFAOYSA-N 1-[bis(4-hydroxybutyl)amino]ethanesulfonic acid Chemical compound OCCCCN(C(C)S(O)(=O)=O)CCCCO PZSVWOVHWJVYBZ-UHFFFAOYSA-N 0.000 description 1
- XZXFRBZDKMCDLX-UHFFFAOYSA-N 1-[decyl(2-hydroxyethyl)amino]ethanesulfonic acid Chemical compound CCCCCCCCCCN(CCO)C(C)S(O)(=O)=O XZXFRBZDKMCDLX-UHFFFAOYSA-N 0.000 description 1
- WSGLREZRFOOMBK-UHFFFAOYSA-N 1-[ethyl(2-hydroxyethyl)amino]ethanesulfonic acid Chemical compound OCCN(CC)C(C)S(O)(=O)=O WSGLREZRFOOMBK-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- LKMJVFRMDSNFRT-UHFFFAOYSA-N 2-(methoxymethyl)oxirane Chemical compound COCC1CO1 LKMJVFRMDSNFRT-UHFFFAOYSA-N 0.000 description 1
- MWWWDFKXDNOIOM-UHFFFAOYSA-N 2-[2,3-dihydroxypropyl(2-sulfoethyl)amino]ethanesulfonic acid Chemical compound OCC(O)CN(CCS(O)(=O)=O)CCS(O)(=O)=O MWWWDFKXDNOIOM-UHFFFAOYSA-N 0.000 description 1
- LFNQFOQYYCWETF-UHFFFAOYSA-N 2-[2-hydroxyethyl(2-sulfoethyl)amino]ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(CCO)CCS(O)(=O)=O LFNQFOQYYCWETF-UHFFFAOYSA-N 0.000 description 1
- YSXIUIYMUUGPDV-UHFFFAOYSA-N 2-[2-hydroxypropyl(2-sulfoethyl)amino]ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(CC(O)C)CCS(O)(=O)=O YSXIUIYMUUGPDV-UHFFFAOYSA-N 0.000 description 1
- ZYVWJXKLTZGSND-UHFFFAOYSA-N 2-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-(2-sulfoethyl)amino]ethanesulfonic acid Chemical compound OS(=O)(=O)CCN(C(CO)(CO)CO)CCS(O)(=O)=O ZYVWJXKLTZGSND-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- HDFANJWLIHRCOD-UHFFFAOYSA-N CC([N+](C)(C)CCO)S([O-])(=O)=O Chemical compound CC([N+](C)(C)CCO)S([O-])(=O)=O HDFANJWLIHRCOD-UHFFFAOYSA-N 0.000 description 1
- URWRDOGAEBRVFP-UHFFFAOYSA-N CC([N+](C)(CCO)CCO)S([O-])(=O)=O Chemical compound CC([N+](C)(CCO)CCO)S([O-])(=O)=O URWRDOGAEBRVFP-UHFFFAOYSA-N 0.000 description 1
- HTUNTHPOXXKGTA-UHFFFAOYSA-N CC([N+](CCCO)(CCCO)CCCO)S([O-])(=O)=O Chemical compound CC([N+](CCCO)(CCCO)CCCO)S([O-])(=O)=O HTUNTHPOXXKGTA-UHFFFAOYSA-N 0.000 description 1
- DIYSPTACUYCYJK-UHFFFAOYSA-N CC([N+](CCCO)(CCO)CCO)S([O-])(=O)=O Chemical compound CC([N+](CCCO)(CCO)CCO)S([O-])(=O)=O DIYSPTACUYCYJK-UHFFFAOYSA-N 0.000 description 1
- RSYOCNAQGDEQCB-UHFFFAOYSA-N CC([N+](CCO)(CCO)CCO)S([O-])(=O)=O Chemical compound CC([N+](CCO)(CCO)CCO)S([O-])(=O)=O RSYOCNAQGDEQCB-UHFFFAOYSA-N 0.000 description 1
- XXCLEQNBNCXICZ-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCC[N+](CCO)(CCO)C(C)S([O-])(=O)=O Chemical compound CCCCCCCCCCCCCCCCCC[N+](CCO)(CCO)C(C)S([O-])(=O)=O XXCLEQNBNCXICZ-UHFFFAOYSA-N 0.000 description 1
- MXOKUEMJNUPANI-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCC[N+](CCO)(CCO)CS([O-])(=O)=O Chemical compound CCCCCCCCCCCCCCCCCC[N+](CCO)(CCO)CS([O-])(=O)=O MXOKUEMJNUPANI-UHFFFAOYSA-N 0.000 description 1
- HAUJDNZXCCIBFK-UHFFFAOYSA-N CCCCCCCCCCCC[N+](C)(CCO)C(C)S([O-])(=O)=O Chemical compound CCCCCCCCCCCC[N+](C)(CCO)C(C)S([O-])(=O)=O HAUJDNZXCCIBFK-UHFFFAOYSA-N 0.000 description 1
- NZEYTKZGXPSBQK-UHFFFAOYSA-N CCCCCCCCCCCC[N+](C)(CCO)CS([O-])(=O)=O Chemical compound CCCCCCCCCCCC[N+](C)(CCO)CS([O-])(=O)=O NZEYTKZGXPSBQK-UHFFFAOYSA-N 0.000 description 1
- GGZKXUAEMNYIPW-UHFFFAOYSA-N CCCCCCCCCCCC[N+](CCO)(CCO)C(C)S([O-])(=O)=O Chemical compound CCCCCCCCCCCC[N+](CCO)(CCO)C(C)S([O-])(=O)=O GGZKXUAEMNYIPW-UHFFFAOYSA-N 0.000 description 1
- SOWKJPUKAAQQCF-UHFFFAOYSA-N CCCCCCCCCCCC[N+](CCO)(CCO)CS([O-])(=O)=O Chemical compound CCCCCCCCCCCC[N+](CCO)(CCO)CS([O-])(=O)=O SOWKJPUKAAQQCF-UHFFFAOYSA-N 0.000 description 1
- JAQRVUAJOYDNDP-UHFFFAOYSA-N CCCC[N+](CCO)(CCO)C(C)S([O-])(=O)=O Chemical compound CCCC[N+](CCO)(CCO)C(C)S([O-])(=O)=O JAQRVUAJOYDNDP-UHFFFAOYSA-N 0.000 description 1
- VGSQXMLUGGIFOV-UHFFFAOYSA-N CCCC[N+](CCO)(CCO)CS([O-])(=O)=O Chemical compound CCCC[N+](CCO)(CCO)CS([O-])(=O)=O VGSQXMLUGGIFOV-UHFFFAOYSA-N 0.000 description 1
- NFSXWGPEWLPDQC-UHFFFAOYSA-N CC[N+](CC)(CCO)C(C)S([O-])(=O)=O Chemical compound CC[N+](CC)(CCO)C(C)S([O-])(=O)=O NFSXWGPEWLPDQC-UHFFFAOYSA-N 0.000 description 1
- HOIJGGRZHOHYDV-UHFFFAOYSA-N CC[N+](CC)(CCO)CS([O-])(=O)=O Chemical compound CC[N+](CC)(CCO)CS([O-])(=O)=O HOIJGGRZHOHYDV-UHFFFAOYSA-N 0.000 description 1
- QMTSYAANTYKJQZ-UHFFFAOYSA-N CC[N+](CCO)(CCO)C(C)S([O-])(=O)=O Chemical compound CC[N+](CCO)(CCO)C(C)S([O-])(=O)=O QMTSYAANTYKJQZ-UHFFFAOYSA-N 0.000 description 1
- ZBMCNOUYTFQUKR-UHFFFAOYSA-N CC[N+](CCO)(CCO)CS([O-])(=O)=O Chemical compound CC[N+](CCO)(CCO)CS([O-])(=O)=O ZBMCNOUYTFQUKR-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- YLZHNTBCLNQMLB-UHFFFAOYSA-N OCC[N+](CCO)(CCO)CS([O-])(=O)=O Chemical compound OCC[N+](CCO)(CCO)CS([O-])(=O)=O YLZHNTBCLNQMLB-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 description 1
- XFDDEDPXWWDFNI-UHFFFAOYSA-N [(2-hydroxy-2-methylbutyl)amino]methanesulfonic acid Chemical compound CCC(C)(O)CNCS(O)(=O)=O XFDDEDPXWWDFNI-UHFFFAOYSA-N 0.000 description 1
- ZVJCQJFLTURTGT-UHFFFAOYSA-N [(3-hydroxy-2,3-dimethylbutan-2-yl)amino]methanesulfonic acid Chemical compound CC(C)(O)C(C)(C)NCS(O)(=O)=O ZVJCQJFLTURTGT-UHFFFAOYSA-N 0.000 description 1
- LNVNUIXOGJXBRW-UHFFFAOYSA-N [(4-hydroxy-2,5-dimethylhexan-3-yl)amino]methanesulfonic acid Chemical compound CC(C)C(O)C(C(C)C)NCS(O)(=O)=O LNVNUIXOGJXBRW-UHFFFAOYSA-N 0.000 description 1
- NPQJWLJSDQMSGX-UHFFFAOYSA-N [(6-hydroxy-6-methylheptan-2-yl)amino]methanesulfonic acid Chemical compound OS(=O)(=O)CNC(C)CCCC(C)(C)O NPQJWLJSDQMSGX-UHFFFAOYSA-N 0.000 description 1
- JZULKPPOIHIZEK-UHFFFAOYSA-N [2-ethylhexyl(2-hydroxyethyl)amino]methanesulfonic acid Chemical compound CCCCC(CC)CN(CCO)CS(O)(=O)=O JZULKPPOIHIZEK-UHFFFAOYSA-N 0.000 description 1
- KYFAHAKVXGRRDG-UHFFFAOYSA-N [2-hydroxyethyl(2-hydroxypropyl)amino]methanesulfonic acid Chemical compound CC(O)CN(CCO)CS(O)(=O)=O KYFAHAKVXGRRDG-UHFFFAOYSA-N 0.000 description 1
- SYMHEMHRBWYNOY-UHFFFAOYSA-N [2-hydroxyethyl(dimethyl)azaniumyl]methanesulfonate Chemical compound C[N+](C)(CCO)CS([O-])(=O)=O SYMHEMHRBWYNOY-UHFFFAOYSA-N 0.000 description 1
- LUHGKZSCXVBPTE-UHFFFAOYSA-N [2-hydroxyethyl(methyl)amino]methanesulfonic acid Chemical compound OCCN(C)CS(O)(=O)=O LUHGKZSCXVBPTE-UHFFFAOYSA-N 0.000 description 1
- SKICMVSMOLKFLK-UHFFFAOYSA-N [2-hydroxyethyl(octadecyl)amino]methanesulfonic acid Chemical compound CCCCCCCCCCCCCCCCCCN(CCO)CS(O)(=O)=O SKICMVSMOLKFLK-UHFFFAOYSA-N 0.000 description 1
- NQDGGAAGHZVHHY-UHFFFAOYSA-N [2-hydroxyethyl(propan-2-yl)amino]methanesulfonic acid Chemical compound OCCN(C(C)C)CS(O)(=O)=O NQDGGAAGHZVHHY-UHFFFAOYSA-N 0.000 description 1
- BGWFCLNFARSEHI-UHFFFAOYSA-N [O-]S(C[N+](CCCO)(CCCO)CCCO)(=O)=O Chemical compound [O-]S(C[N+](CCCO)(CCCO)CCCO)(=O)=O BGWFCLNFARSEHI-UHFFFAOYSA-N 0.000 description 1
- DANNREMKINEOLN-UHFFFAOYSA-N [O-]S(C[N+](CCCO)(CCO)CCO)(=O)=O Chemical compound [O-]S(C[N+](CCCO)(CCO)CCO)(=O)=O DANNREMKINEOLN-UHFFFAOYSA-N 0.000 description 1
- WSKRAXWXFIHUAQ-UHFFFAOYSA-N [[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-(2-hydroxyethyl)amino]methanesulfonic acid Chemical compound OCCN(CS(O)(=O)=O)C(CO)(CO)CO WSKRAXWXFIHUAQ-UHFFFAOYSA-N 0.000 description 1
- HSGICLVATMHDOJ-UHFFFAOYSA-N [[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-(3-hydroxypropyl)amino]methanesulfonic acid Chemical compound OCCCN(CS(O)(=O)=O)C(CO)(CO)CO HSGICLVATMHDOJ-UHFFFAOYSA-N 0.000 description 1
- RCXGZLKESHOKOB-UHFFFAOYSA-N [[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]methanesulfonic acid Chemical compound OCC(CO)(CO)NCS(O)(=O)=O RCXGZLKESHOKOB-UHFFFAOYSA-N 0.000 description 1
- JCMLTOPJOYVULD-UHFFFAOYSA-N [[3-hydroxy-2,2-bis(hydroxymethyl)propyl]amino]methanesulfonic acid Chemical compound OCC(CO)(CO)CNCS(O)(=O)=O JCMLTOPJOYVULD-UHFFFAOYSA-N 0.000 description 1
- OCUJDFSHRDUACV-UHFFFAOYSA-N [bis(1,3-dihydroxypropan-2-yl)amino]methanesulfonic acid Chemical compound OCC(CO)N(CS(O)(=O)=O)C(CO)CO OCUJDFSHRDUACV-UHFFFAOYSA-N 0.000 description 1
- TVMNSBSWKAAJGU-UHFFFAOYSA-N [bis(2,3-dihydroxypropyl)amino]methanesulfonic acid Chemical compound OCC(O)CN(CS(O)(=O)=O)CC(O)CO TVMNSBSWKAAJGU-UHFFFAOYSA-N 0.000 description 1
- JDRSLPWHTUIYIT-UHFFFAOYSA-N [bis(2-hydroxyethyl)amino]methanesulfonic acid Chemical compound OCCN(CCO)CS(O)(=O)=O JDRSLPWHTUIYIT-UHFFFAOYSA-N 0.000 description 1
- GGYXBYPAEDPOSL-UHFFFAOYSA-N [bis(2-hydroxypropyl)amino]methanesulfonic acid Chemical compound CC(O)CN(CC(C)O)CS(O)(=O)=O GGYXBYPAEDPOSL-UHFFFAOYSA-N 0.000 description 1
- UBMYDGNIMPWMNZ-UHFFFAOYSA-N [bis(4-hydroxybutyl)amino]methanesulfonic acid Chemical compound OCCCCN(CS(O)(=O)=O)CCCCO UBMYDGNIMPWMNZ-UHFFFAOYSA-N 0.000 description 1
- GNHAZNFNXZTFLA-UHFFFAOYSA-N [decyl(2-hydroxyethyl)amino]methanesulfonic acid Chemical compound CCCCCCCCCCN(CCO)CS(O)(=O)=O GNHAZNFNXZTFLA-UHFFFAOYSA-N 0.000 description 1
- IHGBHNVXXQBPLQ-UHFFFAOYSA-N [ethyl(2-hydroxyethyl)amino]methanesulfonic acid Chemical compound OCCN(CC)CS(O)(=O)=O IHGBHNVXXQBPLQ-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
- Paints Or Removers (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18598289A JPH02138335A (ja) | 1989-07-20 | 1989-07-20 | オイルフリーポリエステルの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18598289A JPH02138335A (ja) | 1989-07-20 | 1989-07-20 | オイルフリーポリエステルの製造法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5604880A Division JPS56151727A (en) | 1980-04-26 | 1980-04-26 | Novel oil free-polyester and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02138335A JPH02138335A (ja) | 1990-05-28 |
| JPH0325445B2 true JPH0325445B2 (enrdf_load_stackoverflow) | 1991-04-08 |
Family
ID=16180290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18598289A Granted JPH02138335A (ja) | 1989-07-20 | 1989-07-20 | オイルフリーポリエステルの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02138335A (enrdf_load_stackoverflow) |
-
1989
- 1989-07-20 JP JP18598289A patent/JPH02138335A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02138335A (ja) | 1990-05-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4482698A (en) | Thermosetting coating composition containing a blocked acid as catalyst | |
| RU2265035C2 (ru) | Фотоактивируемая композиция покрытия | |
| US4069178A (en) | Process for preparation of water-soluble, silicone modified alkyd resins | |
| US4104240A (en) | High solids pigment coating composition | |
| JPH0156105B2 (enrdf_load_stackoverflow) | ||
| SK308792A3 (en) | Single-component paint agent and its using for production of acid-resistant coating | |
| JP5348515B1 (ja) | 酸化重合型不飽和樹脂用硬化促進剤、印刷インキ及び塗料 | |
| JP2019510093A (ja) | 優れた耐熱性および溶媒への溶解性を有するポリエステル樹脂、ならびにこれを含有するコーティング組成物 | |
| US5102961A (en) | Isocyanate modified blocked sulfonic acid ester as a crosslinking catalyst | |
| PT798325E (pt) | Compostos poli-hidroxilicos adequados para a sintese de poliuretanos | |
| JPS6270456A (ja) | 水に運ばれるハイソリツドコ−テイング組成物 | |
| JPH06507932A (ja) | 熱硬化性塗料組成物 | |
| US5691400A (en) | Compositions | |
| TW568943B (en) | Carboxyl-functional polyester resin, and power paint formulation containing the resin and its preparation | |
| JPH0325445B2 (enrdf_load_stackoverflow) | ||
| JPH0757855B2 (ja) | ヒドロキシル基を含有する付加重合体と、アミノプラスト樹脂架橋剤とをベースとし、ヒドロキシル基を有する酸触媒を含有する被覆組成物およびその製造方法 | |
| JP5418729B2 (ja) | 印刷インキ及び塗料 | |
| US5674965A (en) | Epoxy compounds for use as components of aqueous coating compositions | |
| MX2007008505A (es) | Agentes de control de reologia para composiciones de recubrimiento. | |
| JPS6219219B2 (enrdf_load_stackoverflow) | ||
| US3766118A (en) | Water soluble alkyd resins | |
| JPH0127107B2 (enrdf_load_stackoverflow) | ||
| JPS61203177A (ja) | 水性樹脂組成物 | |
| JPS5975946A (ja) | 水分散性ポリエステルの製造方法 | |
| JPS5938994B2 (ja) | 塗料用樹脂組成物 |