JPH0127107B2 - - Google Patents
Info
- Publication number
- JPH0127107B2 JPH0127107B2 JP11086579A JP11086579A JPH0127107B2 JP H0127107 B2 JPH0127107 B2 JP H0127107B2 JP 11086579 A JP11086579 A JP 11086579A JP 11086579 A JP11086579 A JP 11086579A JP H0127107 B2 JPH0127107 B2 JP H0127107B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- hydroxyethyl
- alkyl substituted
- bis
- 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
- 229920000180 alkyd Polymers 0.000 claims description 54
- 229920005989 resin Polymers 0.000 claims description 24
- 239000011347 resin Substances 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 19
- 239000008199 coating composition Substances 0.000 claims description 17
- 239000003973 paint Substances 0.000 claims description 11
- 229920003180 amino resin Polymers 0.000 claims description 9
- 125000003010 ionic group Chemical group 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000005650 substituted phenylene group Chemical group 0.000 claims description 3
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 41
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 41
- 229960003237 betaine Drugs 0.000 description 41
- 239000002966 varnish Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- 238000000576 coating method Methods 0.000 description 18
- 239000011248 coating agent Substances 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 14
- 239000000049 pigment Substances 0.000 description 14
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 13
- 235000014113 dietary fatty acids Nutrition 0.000 description 13
- 239000000194 fatty acid Substances 0.000 description 13
- 229930195729 fatty acid Natural products 0.000 description 13
- 150000004665 fatty acids Chemical class 0.000 description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- -1 methylcyclohexenetricarboxylic anhydride Chemical class 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 239000001054 red pigment Substances 0.000 description 7
- 239000011342 resin composition Substances 0.000 description 7
- 229920001187 thermosetting polymer Polymers 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OBESRABRARNZJB-UHFFFAOYSA-N aminomethanesulfonic acid Chemical compound NCS(O)(=O)=O OBESRABRARNZJB-UHFFFAOYSA-N 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 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 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000944 linseed oil Substances 0.000 description 3
- 235000021388 linseed oil Nutrition 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- ZZGGNGUMBKOMNR-UHFFFAOYSA-N (3-hydroxypropylamino)methanesulfonic acid Chemical compound OCCCNCS(O)(=O)=O ZZGGNGUMBKOMNR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 235000019485 Safflower oil Nutrition 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
- LUHGKZSCXVBPTE-UHFFFAOYSA-N [2-hydroxyethyl(methyl)amino]methanesulfonic acid Chemical compound OCCN(C)CS(O)(=O)=O LUHGKZSCXVBPTE-UHFFFAOYSA-N 0.000 description 2
- JDRSLPWHTUIYIT-UHFFFAOYSA-N [bis(2-hydroxyethyl)amino]methanesulfonic acid Chemical compound OCCN(CCO)CS(O)(=O)=O JDRSLPWHTUIYIT-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000011362 coarse particle Substances 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000013007 heat curing Methods 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
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 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
- 150000007519 polyprotic acids Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000003813 safflower oil Substances 0.000 description 2
- 235000005713 safflower oil Nutrition 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 239000005028 tinplate Substances 0.000 description 2
- 239000002383 tung oil Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- SZCWBURCISJFEZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)COC(=O)C(C)(C)CO SZCWBURCISJFEZ-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
- 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
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-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
- 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
- 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
- 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
- PHPOQUFMMUKPTA-UHFFFAOYSA-N 1-[bis(2-hydroxyethyl)amino]ethanesulfonic acid Chemical compound OS(=O)(=O)C(C)N(CCO)CCO PHPOQUFMMUKPTA-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
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-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
- 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
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-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
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- BEJQXBXPRXFJDP-UHFFFAOYSA-N 3-(3,3-dihydroxypropoxy)propane-1,1-diol Chemical compound OC(O)CCOCCC(O)O BEJQXBXPRXFJDP-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- REYODCKFARPTPY-UHFFFAOYSA-N 4-(2-hydroxyethylamino)benzenesulfonic acid Chemical compound OCCNC1=CC=C(S(O)(=O)=O)C=C1 REYODCKFARPTPY-UHFFFAOYSA-N 0.000 description 1
- XTIVJKBCSHQGOX-UHFFFAOYSA-N 4-[bis(2-hydroxyethyl)amino]benzenesulfonic acid Chemical compound OCCN(CCO)C1=CC=C(S(O)(=O)=O)C=C1 XTIVJKBCSHQGOX-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 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
- 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
- ZZDQYULSWKMXGZ-UHFFFAOYSA-N C[N+](CCO)(CCO)CS([O-])(=O)=O Chemical compound C[N+](CCO)(CCO)CS([O-])(=O)=O ZZDQYULSWKMXGZ-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
- 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
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 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
- 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
- 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
- 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
- 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
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 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
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000001530 fumaric acid Substances 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- ZZSIDSMUTXFKNS-UHFFFAOYSA-N perylene red Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N(C(=O)C=1C2=C3C4=C(OC=5C=CC=CC=5)C=1)C(=O)C2=CC(OC=1C=CC=CC=1)=C3C(C(OC=1C=CC=CC=1)=CC1=C2C(C(N(C=3C(=CC=CC=3C(C)C)C(C)C)C1=O)=O)=C1)=C2C4=C1OC1=CC=CC=C1 ZZSIDSMUTXFKNS-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
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- 230000001737 promoting effect Effects 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 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
- 239000003784 tall oil Substances 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Description
本発明は新規なアルキド樹脂を用いた塗料組成
物に関する。
イオン性官能基を高分子化合物に導入すると、
その高分子化合物の物理的・化学的性質に大きな
影響を与える。また、このようなイオン性官能基
は、低分子の化合物として用いられるよりも高分
子化合物にくみ込まれた場合に、その性質がより
強調されたり複合されたりして現われる。このた
め、イオン性官能基含有高分子化合物に関する研
究が近来盛んに行なわれ、特に対イオンをなすカ
チオンとアニオンが共有結合を経て結合された、
即ち内部塩構造の、反応性、界面活性、電気化学
的性質、生物化学的性質を呈する両性イオン基を
有する高分子化合物への関心が高まりつつある。
本発明の目的は、上記両性イオン基を有する新
規なアルキド樹脂を用いた塗料組成物を提供する
ことにある。
即ち、本発明の要旨は、第１に、樹脂分子中に
式、
〔式中、ＡはC1〜C5の直鎖もしくは分枝状ア
ルキレン基、フエニレン基または置換フエニレン
基を表わす。〕
で示される両性イオン基を有するアルキド樹脂を
主成分とすることを特徴とする塗料組成物、第２
に、上記アルギド樹脂100重量部およびアミノプ
ラスト樹脂５〜100重量部を主成分とすることを
特徴とする塗料組成物に存する。
本発明の新規アルキド樹脂は、樹脂分子中に上
記式〔〕で示される両性イオン基を有するアル
キド樹脂である。上記式〔〕で示される両性イ
オン基のうちで特にＮ原子の置換基として少なく
とも１つの水素原子を有するものは次の互変異性
体の混合物として存在する。
また、上記両性イオン基は環境により、そのイ
オン形態を異にする。例えば、PHの変化により
なる変化をする。従つて、環境条件を制御するこ
とにより異なつた反応性、界面活性、電気化学的
性質などを発現させることができる。
本発明アルキド樹脂の製造法としては、反応成
分中のアルコール成分の一つとして、式、
〔式中、R1は少なくとも１個のヒドロキシル
基を持つC1〜C20のアルキル基、R2およびR3は相
互に同一もしくは異なつて水素原子、C1〜C20の
アルキル基、少なくとも１個のヒドロキシル基お
よび／またはスルホン酸基を持つアルキル基また
は環状基を表わし、Ａは前記と同意義。〕
で示されるヒドロキシル基含有両イオン性化合物
を全反応成分中0.05〜30％（重量％、以下同様）、
好ましくは0.1〜20％にて使用することを特徴と
し、その他の点については通常のアルキド樹脂の
原料成分および反応条件・方式が採用されてよ
い。かかる通常の反応条件・方式としては、例え
ば北岡協三著「塗料用合成樹脂入門」（1974年５
月25日高分子刊行会発行、92〜127頁）、あるいは
D.H.ソロモン，ジヨーン・ウイリー・アンド・
サン著「ザ・ケミストリー・オブ・オルガニツ
ク・フイルム・フオーマーズ」（75〜87頁、1967
年）の記載内容に準じて実施する。即ち、反応成
分として、
ａ 多価アルコール、
ｂ 多塩基酸化合物、
ｃ 脂肪酸および／または油、および
ｄ 上記ヒドロキシル基含有両イオン性化合物
を使用し、これらを適当な溶媒中で後記実施例の
如き要領に準じ、エステル化反応および要すれば
エステル交換反応を行つて本発明アルキド樹脂を
製造する。なお、本発明アルキド樹脂にあつて
は、当該反応成分ｄを使用する限り、各種の樹脂
で変性されたアルキド樹脂、例えばロジン変性ア
ルキド樹脂、フエノール変性アルキド樹脂、エポ
キシ変性アルキド樹脂、ビニル変性アルキド樹
脂、イソシアナート変性アルキド樹脂、シリコン
変性アルギド樹脂なども包含される。
上記多価アルコールとしては、通常アルキド樹
脂原料として用いられるものでよく、例えばエチ
レングリコール、プロピレングリコール、１，３
―ブチレングリコール、１，６―ヘキサングリコ
ール、ジエチレングリコール、ジプロピレングリ
コール、ネオペンチルグリコール、トリエチレン
グリコール、２，２―ジメチル―３―ヒドロキシ
プロピル―２，２―ジメチル―３―ヒドロキシプ
ロピオネート、水素化ビスフエノールＡ、ビスフ
エノールジヒドロキシプロピルエーテル、グリセ
リン、トリメチロールエタン、トリメチロールプ
ロパン、トリスヒドロキシメチルアミノメタン、
ペンタエリトリツト、ジペンタエリトリツトなど
が挙げられ、これらの１種または２種以上を使用
に供する。使用量は特に制限はないが、通常全反
応成分中２〜90％の範囲で選定すればよい。
上記多塩基酸化合物としては、通常アルキド樹
脂原料として用いられるものでよく、例えば無水
フタル酸、イソフタル酸、テレフタル酸、無水コ
ハク酸、アジピン酸、アゼライン酸、セバシン
酸、テトラヒドロ無水フタル酸、ヘキサヒドロ無
水フタル酸、テトラブロム無水フタル酸、テトラ
クロル無水フタル酸、無水ヘツト酸、無水ハイミ
ツク酸、無水マレイン酸、フマル酸、イタコン
酸、無水トリメリツト酸、メチルシクロヘキセン
トリカルボン酸無水物、無水ピロメリツト酸など
が挙げられ、これらの１種または２種以上を使用
に供する。使用量は特に制限はないが、通常全反
応成分中２〜90％の範囲で選定すればよい。
上記反応成分Ｃの脂肪酸としては、通常のもの
でよく、例えば大豆油脂肪酸、アマニ油脂肪酸、
サフラワー油脂肪酸、トール油脂肪酸、ヤシ油脂
肪酸、脱水ヒマシ油脂肪酸、キリ油脂肪酸、合脂
肪酸などが挙げられ、またかかる脂肪酸に代えま
たは併用される油としては、通常の例えばヒマシ
油、ヤシ油、アマニ油、パーム核油、サフラワー
油、大豆油、キリ油、脱水ヒマシ油などが挙げら
れ、それぞれ１種または２種以上を使用に供す
る。かかる反応成分Ｃの使用量は特に制限はない
が、通常全反応成分中１〜80％の範囲で選定すれ
ばよい。
上記ヒドロキシル基含有両イオン性化合物とし
ては、例えばＮ―（２―ヒドロキシエチル）アミ
ノメタンスルホン酸とそのＮ―アルキル置換体
（Ｎ―メチル―Ｎ―（２―ヒドロキシエチル）ア
ミノメタンスルホン酸、Ｎ―エチル―Ｎ―（２―
ヒドロキシエチル）アミノメタンスルホン酸、Ｎ
―イソプロピル―Ｎ―（２―ヒドロキシエチル）
アミノメタンスルホン酸、Ｎ―（２―エチルヘキ
シル）―Ｎ―（２―ヒドロキシエチル）アミノメ
タンスルホン酸、Ｎ―デシル―Ｎ―（２―ヒドロ
キシエチル）アミノメタンスルホン酸、Ｎ―ステ
アリル―Ｎ―（２―ヒドロキシエチル）アミノメ
タンスルホン酸など）およびＮ，Ｎ―ジアルキル
置換体（Ｎ，Ｎ―ジメチル―Ｎ―（２―ヒドロキ
シエチル）アンモニオメタンスルホン酸ベタイ
ン、Ｎ，Ｎ―ジエチル―Ｎ―（２―ヒドロキシエ
チル）アンモニオメタンスルホン酸ベタイン、Ｎ
―メチル―Ｎ―ドデシル―Ｎ―（２―ヒドロキシ
エチル）アンモニオメタンスルホン酸ベタインな
ど）、Ｎ―（２―ヒドロキシ―１―メチルエチル）
アミノメタンスルホン酸とそのＮ―アルキル置換
体およびＮ，Ｎ―ジアルキル置換体、Ｎ―（２―
ヒドロキシプロピル）アミノメタンスルホン酸と
そのＮ―アルキル置換体およびＮ，Ｎ―ジアルキ
ル置換体、Ｎ―（３―ヒドロキシプロピル）アミ
ノメタンスルホン酸とそのＮ―アルキル置換体お
よびＮ，Ｎ―ジアルキル置換体、Ｎ―（２―プロ
ピル―２―ヒドロキシエチル）アミノメタンスル
ホン酸とそのＮ―アルキル置換体およびＮ，Ｎ―
ジアルキル置換体、Ｎ―（２―メチル―２―エチ
ル―２―ヒドロキシエチル）アミノメタンスルホ
ン酸とそのＮ―アルキル置換体およびＮ，Ｎ―ジ
アルキル置換体、Ｎ―（１，２―ジメチル―２―
ヒドロキシエチル）アミノメタンスルホン酸とそ
のＮ―アルキル置換体およびＮ，Ｎ―ジアルキル
置換体、Ｎ―（１，１，２，２―テトラメチル―
２―ヒドロキシエチル）アミノメタンスルホン酸
とそのＮ―アルキル置換体およびＮ，Ｎ―ジアル
キル置換体、Ｎ―（１―メチル―５，５―ジメチ
ル―５―ヒドロキシペンチル）アミノメタンスル
ホン酸とそのＮ―アルキル置換体およびＮ，Ｎ―
ジアルキル置換体、Ｎ―（１，２―ジイソプロピ
ル―２―ヒドロキシエチル）アミノメタンスルホ
ン酸とそのＮ―アルキル置換体およびＮ，Ｎ―ジ
アルキル置換体、Ｎ―（２，３―ジヒドロキシプ
ロピル）アミノメタンスルホン酸とそのＮ―アル
キル置換体およびＮ，Ｎ―ジアルキル置換体、Ｎ
―（１―ヒドロキシメチル―２―ヒドロキシエチ
ル）アミノメタンスルホン酸とそのＮ―アルキル
置換体およびＮ，Ｎ―ジアルキル置換体、Ｎ―
（１―ヒドロキシメチル―２―メチル―２―ヒド
ロキシエチル）アミノメタンスルホン酸とそのＮ
―アルキル置換体およびＮ，Ｎ―ジアルキル置換
体、Ｎ―（１―ヒドロキシメチル―３―ヒドロキ
シプロピル）アミノメタンスルホン酸とそのＮ―
アルキル置換体およびＮ，Ｎ―ジアルキル置換
体、Ｎ―（―（γ―ヒドロキシプロピル）―２
―ヒドロキシエチル）アミノメタンスルホン酸と
そのＮ―アルキル置換体およびＮ，Ｎ―ジアルキ
ル置換体、Ｎ―（１，１―ビス（ヒドロキシメチ
ル）―２―ヒドロキシエチル）アミノメタンスル
ホン酸とそのＮ―アルキル置換体およびＮ，Ｎ―
ジアルキル置換体、Ｎ―（２，２―ビス（ヒドロ
キシメチル）―３―ヒドロキシプロピル）アミノ
メタンスルホン酸とそのＮ―アルキル置換体およ
びＮ，Ｎ―ジアルキル置換体、Ｎ，Ｎ―ビス（２
―ヒドロキシエチル）アミノメタンスルホン酸と
そのＮ―アルキル置換体（Ｎ―メチル―Ｎ，Ｎ―
ビス（２―ヒドロキシエチル）アンモニオメタン
スルホン酸ベタイン、Ｎ―エチル―Ｎ，Ｎ―ビス
（２―ヒドロキシエチル）アンモニオメタンスル
ホン酸ベタイン、Ｎ―ブチル―Ｎ，Ｎ―ビス（２
―ヒドロキシエチル）アンモニオメタンスルホン
酸ベタイン、Ｎ―ドデシル―Ｎ，Ｎ―ビス（２―
ヒドロキシエチル）アンモニオメタンスルホン酸
ベタイン、Ｎ―ステアリル―Ｎ，Ｎ―ビス（２―
ヒドロキシエチル）アンモニオメタンスルホン酸
ベタインなど）、Ｎ―（２―ヒドロキシエチル）
―Ｎ―（２―ヒドロキシプロピル）アミノメタン
スルホン酸とそのＮ―アルキル置換体、Ｎ，Ｎ―
ビス（２―ヒドロキシプロピル）アミノメタンス
ルホン酸とそのＮ―アルキル置換体、Ｎ，Ｎ―ビ
ス（４―ヒドロキシブチル）アミノメタンスルホ
ン酸とそのＮ―アルキル置換体、Ｎ―（２―ヒド
ロキシエチル）―Ｎ―（１，１―ビス（ヒドロキ
シメチル）―２―ヒドロキシエチル）アミノメタ
ンスルホン酸とそのＮ―アルキル置換体、Ｎ―
（３―ヒドロキシプロピル）―Ｎ―（１，１―ビ
ス（ヒドロキシメチル）―２―ヒドロキシエチ
ル）アミノメタンスルホン酸とそのＮ―アルキル
置換体、Ｎ，Ｎ―ビス（２，３―ジヒドロキシプ
ロピル）アミノメタンスルホン酸とそのＮ―アル
キル置換体、Ｎ，Ｎ―ビス―（１―ヒドロキシメ
チル）―２―ヒドロキシエチル）アミノメタンス
ルホン酸とそのＮ―アルキル置換体、Ｎ，Ｎ―ビ
ス（１，１―（ビスヒドロキシメチル）―２―ヒ
ドロキシエチル）アミノメタンスルホン酸とその
Ｎ―アルキル置換体、Ｎ，Ｎ，Ｎ―トリス―（２
―ヒドロキシエチル）アンモニオメタンスルホン
酸ベタイン、Ｎ，Ｎ―ビス―（２―ヒドロキシエ
チル）―Ｎ―（３―ヒドロキシプロピル）アンモ
ニオメタンスルホン酸ベタイン、Ｎ，Ｎ，Ｎ―ト
リス（３―ヒドロキシプロピル）アンモニオメタ
ンスルホン酸ベタイン、
Ｎ―（２―ヒドロキシエチル）アミノエタンス
ルホン酸とそのＮ―アルキル置換体（Ｎ―メチル
―Ｎ―（２―ヒドロキシエチル）アミノエタンス
ルホン酸、Ｎ―エチル―Ｎ―（２―ヒドロキシエ
チル）アミノエタンスルホン酸、Ｎ―イソプロピ
ル―Ｎ―（２―ヒドロキシエチル）アミノエタン
スルホン酸、Ｎ―（２―エチルヘキシル）―Ｎ―
（２―ヒドロキシエチル）アミノエタンスルホン
酸、Ｎ―デシル―Ｎ―（２―ヒドロキシエチル）
アミノエタンスルホン酸、Ｎ―ステアリル―Ｎ―
（２―ヒドロキシエチル）アミノエタンスルホン
酸など）およびＮ，Ｎ―ジアルキル置換体（Ｎ，
Ｎ―ジメチル―Ｎ―（２―ヒドロキシエチル）ア
ンモニオエタンスルホン酸ベタイン、Ｎ，Ｎ―ジ
エチル―Ｎ―（２―ヒドロキシエチル）アンモニ
オエタンスルホン酸ベタイン、Ｎ―メチル―Ｎ―
ドデシル―Ｎ―（２―ヒドロキシエチル）アンモ
ニオエタンスルホン酸ベタインなど）、Ｎ―（２
―ヒドロキシ―１―メチルエチル）アミノエタン
スルホン酸とそのＮ―アルキル置換体およびＮ，
Ｎ―ジアルキル置換体、Ｎ―（２―ヒドロキシプ
ロピル）アミノエタンスルホン酸とそのＮ―アル
キル置換体およびＮ，Ｎ―ジアルキル置換体、Ｎ
―（３―ヒドロキシプロピル）アミノエタンスル
ホン酸とそのＮ―アルキル置換体およびＮ，Ｎ―
ジアルキル置換体、Ｎ―（２―プロピル―２―ヒ
ドロキシエチル）アミノエタンスルホン酸とその
Ｎ―アルキル置換体およびＮ，Ｎ―ジアルキル置
換体、Ｎ―（２―メチル―２―エチル―２―ヒド
ロキシエチル）アミノエタンスルホン酸とそのＮ
―アルキル置換体およびＮ，Ｎ―ジアルキル置換
体、Ｎ―（１，２―ジメチル―２―ヒドロキシエ
チル）アミノエタンスルホン酸とそのＮ―アルキ
ル置換体およびＮ，Ｎ―ジアルキル置換体、Ｎ―
（１，１，２，２―テトラメチル―２―ヒドロキ
シエチル）アミノエタンスルホン酸とそのＮ―ア
ルキル置換体およびＮ，Ｎ―ジアルキル置換体、
Ｎ―（１―メチル―５，５―ジメチル―５―ヒド
ロキシペンチル）アミノエタンスルホン酸とその
Ｎ―アルキル置換体およびＮ，Ｎ―ジアルキル置
換体、Ｎ―（１，２ジイソプロピル―２―ヒドロ
キシエチル）アミノエタンスルホン酸とそのＮ―
アルキル置換体およびＮ，Ｎ―ジアルキル置換
体、Ｎ―（２，３―ジヒドロキシプロピル）アミ
ノエタンスルホン酸とそのＮ―アルキル置換体お
よびＮ，Ｎ―ジアルキル置換体、Ｎ―（１―ヒド
ロキシメチル―２―ヒドロキシエチル）アミノエ
タンスルホン酸とそのＮ―アルキル置換体および
Ｎ，Ｎ―ジアルキル置換体、Ｎ―（１―ヒドロキ
シメチル―２―メチル―２―ヒドロキシエチル）
アミノエタンスルホン酸とそのＮ―アルキル置換
体およびＮ，Ｎ―ジアルキル置換体、Ｎ―（１―
ヒドロキシメチル―３―ヒドロキシプロピル）ア
ミノエタンスルホン酸とそのＮ―アルキル置換体
およびＮ，Ｎ―ジアルキル置換体、Ｎ―（１―
（γ―ヒドロキシプロピル）―２―ヒドロキシエ
チル）アミノエタンスルホン酸とそのＮ―アルキ
ル置換体およびＮ，Ｎ―ジアルキル置換体、Ｎ―
（１，１―ビス（ヒドロキシメチル）―２―ヒド
ロキシエチル）アミノエタンスルホン酸とそのＮ
―アルキル置換体およびＮ，Ｎ―ジアルキル置換
体、Ｎ―（２，２―ビス（ヒドロキシメチル）―
３―ヒドロキシプロピル）アミノエタンスルホン
酸とそのＮ―アルキル置換体およびＮ，Ｎ―ジア
ルキル置換体、Ｎ，Ｎ―ビス（２―ヒドロキシエ
チル）アミノエタンスルホン酸とそのＮ―アルキ
ル置換体（Ｎ―メチル―Ｎ，Ｎ―ビス（２―ヒド
ロキシエチル）アンモニオエタンスルホン酸ベタ
イン、Ｎ―エチル―Ｎ，Ｎ―ビス（２―ヒドロキ
シエチル）アンモニオエタンスルホン酸ベタイ
ン、Ｎ―ブチル―Ｎ，Ｎ―ビス（２―ヒドロキシ
エチル）アンモニオエタンスルホン酸ベタイン、
Ｎ―ドデシル―Ｎ，Ｎ―ビス（２―ヒドロキシエ
チル）アンモニオエタンスルホン酸ベタイン、Ｎ
―ステアリル、Ｎ，Ｎ―ビス（２―ヒドロキシエ
チル）アンモニオエタンスルホン酸ベタインな
ど）、Ｎ―（２―ヒドロキシエチル）―Ｎ―（２
―ヒドロキシプロピル）アミノエタンスルホン酸
とそのＮ―アルキル置換体、Ｎ，Ｎ―ビス（２―
ヒドロキシプロピル）アミノエタンスルホン酸と
そのＮ―アルキル置換体、Ｎ，Ｎ―ビス（４―ヒ
ドロキシブチル）アミノエタンスルホン酸とその
Ｎ―アルキル置換体、Ｎ―（２―ヒドロキシエチ
ル）―Ｎ―（１，１―ビス（ヒドロキシメチル）
―２―ヒドロキシエチル）アミノエタンスルホン
酸とそのＮ―アルキル置換体、Ｎ―（３―ヒドロ
キシプロピル）―Ｎ―（１，１―ビス（ヒドロキ
シメチル）―２―ヒドロキシエチル）アミノエタ
ンスルホン酸とそのＮ―アルキル置換体、Ｎ，Ｎ
―ビス（２，３―ジヒドロキシプロピル）アミノ
エタンスルホン酸とそのＮ―アルキル置換体、
Ｎ，Ｎ―ビス（１―（ヒドロキシメチル）―２―
ヒドロキシエチル）アミノエタンスルホン酸とそ
のＮ―アルキル置換体、Ｎ，Ｎ―ビス―（１，１
―（ビスヒドロキシメチル）―２―ヒドロキシエ
チル）アミノエタンスルホン酸とそのＮ―アルキ
ル置換体、Ｎ，Ｎ，Ｎ―トリス―（２―ヒドロキ
シエチル）アンモニオエタンスルホン酸ベタイ
ン、Ｎ，Ｎ―ビス―（２―ヒドロキシエチル）―
Ｎ―（３―ヒドロキシプロピル）アンモニオエタ
ンスルホン酸ベタイン、Ｎ，Ｎ，Ｎ―トリス（３
―ヒドロキシプロピル）アンモニオエタンスルホ
ン酸ベタイン、
３―｛Ｎ―（２―ヒドロキシエチル）｝アミノ
プロパンスルホン酸―(1)とそのＮ―アルキル置換
体（３―｛Ｎ―メチル―Ｎ―（２―ヒドロキシエ
チル）｝アミノプロパンスルホン酸―(1)，３―
｛Ｎ―エチル―Ｎ―（２―ヒドロキシエチル）｝ア
ミノプロパンスルホン酸―(1)，３―｛Ｎ―イソプ
ロピル―Ｎ―（２―ヒドロキシエチル）｝アミノ
プロパンスルホン酸―(1)，３―｛Ｎ―（２―エチ
ルヘキシル）―Ｎ―（２―ヒドロキシエチル）｝
アミノプロパンスルホン酸―(1)，３―｛Ｎ―デシ
ル―Ｎ―（２―ヒドロキシエチル）｝アミノプロ
パンスルホン酸―(1)，３―｛Ｎ―ステアリル―Ｎ
―（２―ヒドロキシエチル）｝アミノプロパンス
ルホン酸―(1)など）およびＮ，Ｎ―ジアルキル置
換体（３―｛Ｎ，Ｎ―ジメチル―Ｎ―（２―ヒド
ロキシエチル）｝アンモニオプロパンスルホン酸
―(1)ベタイン、３―｛Ｎ，Ｎ―ジエチル―Ｎ―
（２―ヒドロキシエチル）｝アンモニオプロパンス
ルホン酸―(1)ベタイン、３―｛Ｎ―メチル―Ｎ―
ドデシル―Ｎ―（２―ヒドロキシエチル）｝アン
モニオプロパンスルホン酸―(1)ベタインなど）、
３―｛Ｎ―（２―ヒドロキシ―１―メチルエチ
ル）｝アミノプロパンスルホン酸―(1)とそのＮ―
アルキル置換体およびＮ，Ｎ―ジアルキル置換
体、３―｛Ｎ―（２―ヒドロキシプロピル）｝ア
ミノプロパンスルホン酸―(1)とそのＮ―アルキル
置換体およびＮ，Ｎ―ジアルキル置換体、３―
｛Ｎ―（３―ヒドロキシプロピル）｝アミノプロパ
ンスルホン酸―(1)とそのＮ―アルキル置換体およ
びＮ，Ｎ―ジアルキル置換体、３―｛Ｎ―（２―
プロピル―２―ヒドロキシエチル）｝アミノプロ
パンスルホン酸―(1)とそのＮ―アルキル置換体お
よびＮ，Ｎ―ジアルキル置換体、３―｛Ｎ―（２
―メチル―２―エチル―２―ヒドロキシエチル）｝
アミノプロパンスルホン酸―(1)とそのＮ―アルキ
ル置換体およびＮ，Ｎ―ジアルキル置換体、３―
｛Ｎ―（１，２―ジメチル―２―ヒドロキシエチ
ル）｝アミノプロパンスルホン酸―(1)とそのＮ―
アルキル置換体およびＮ，Ｎ―ジアルキル置換
体、３―｛Ｎ―（１，１，２，２―テトラメチル
―２―ヒドロキシエチル）｝アミノプロパンスル
ホン酸―(1)とそのＮ―アルキル置換体およびＮ，
Ｎ―ジアルキル置換体、３―｛Ｎ―（１―メチル
―５，５―ジメチル―５―ヒドロキシペンチル）｝
アミノプロパンスルホン酸―(1)とそのＮ―アルキ
ル置換体およびＮ，Ｎ―ジアルキル置換体、３―
｛Ｎ―（１，２―ジイソプロピル―２―ヒドロキ
シエチル）｝アミノプロパンスルホン酸―(1)とそ
のＮ―アルキル置換体およびＮ，Ｎ―ジアルキル
置換体、３―｛Ｎ―（２，３―ジヒドロキシプロ
ピル）｝アミノプロパンスルホン酸―(1)とそのＮ
―アルキル置換体およびＮ，Ｎ―ジアルキル置換
体、３―｛Ｎ―（１―ヒドロキシメチル―２―ヒ
ドロキシエチル）｝アミノプロパンスルホン酸―
(1)とそのＮ―アルキル置換体およびＮ，Ｎ―ジア
ルキル置換体、３―｛Ｎ―（１―ヒドロキシメチ
ル―２―メチル―２―ヒドロキシエチル）｝アミ
ノプロパンスルホン酸―(1)とそのＮ―アルキル置
換体およびＮ，Ｎ―ジアルキル置換体、３―｛Ｎ
―（１―ヒドロキシメチル―３―ヒドロキシプロ
ピル）｝アミノプロパンスルホン酸―(1)とそのＮ
―アルキル置換体およびＮ，Ｎ―ジアルキル置換
体、３―｛Ｎ―（１―（γ―ヒドロキシプロピ
ル）―２―ヒドロキシエチル）｝アミノプロパン
スルホン酸―(1)とそのＮ―アルキル置換体および
Ｎ，Ｎ―ジアルキル置換体、３―｛Ｎ―（１，１
―ビス（ヒドロキシメチル）―２―ヒドロキシエ
チル）｝アミノプロパンスルホン酸―(1)とそのＮ
―アルキル置換体およびＮ，Ｎ―ジアルキル置換
体、３―｛Ｎ―（２，２―ビス（ヒドロキシメチ
ル）―３―ヒドロキシプロピル）｝アミノプロパ
ンスルホン酸―(1)とそのＮ―アルキル置換体およ
びＮ，Ｎ―ジアルキル置換体、３―｛Ｎ，Ｎ―ビ
ス（２―ヒドロキシエチル）｝アミノプロパンス
ルホン酸―(1)とそのＮ―アルキル置換体（３―
｛Ｎ―メチル―Ｎ，Ｎ―ビス（２―ヒドロキシエ
チル）｝アンモニオプロパンスルホン酸―(1)ベタ
イン、３―｛Ｎ―エチル―Ｎ，Ｎ―ビス（２―ヒ
ドロキシエチル）｝アンモニオプロパンスルホン
酸―(1)ベタイン、３―｛Ｎ―ブチル―Ｎ，Ｎ―ビ
ス（２―ヒドロキシエチル）｝アンモニオプロパ
ンスルホン酸―(1)ベタイン、３―｛Ｎ―ドデシル
―Ｎ，Ｎ―ビス（２―ヒドロキシエチル）｝アン
モニオプロパンスルホン酸―(1)ベタイン、３―
｛Ｎ―ステアリル―Ｎ，Ｎ―ビス（２―ヒドロキ
シエチル）｝アンモニオプロパンスルホン酸―(1)
ベタインなど）、３―｛Ｎ―（２―ヒドロキシエ
チル）―Ｎ―（２―ヒドロキシプロピル）｝アミ
ノプロパンスルホン酸―(1)とそのＮ―アルキル置
換体、３―｛Ｎ，Ｎ―ビス（２―ヒドロキシプロ
ピル）｝アミノプロパンスルホン酸―(1)とそのＮ
―アルキル置換体、３―｛Ｎ，Ｎ―ビス（４―ヒ
ドロキシブチル）｝アミノプロパンスルホン酸―
(1)とそのＮ―アルキル置換体、３―｛Ｎ―（２―
ヒドロキシエチル）―Ｎ―（１，１―ビス（ヒド
ロキシメチル）―２―ヒドロキシエチル）｝アミ
ノプロパンスルホン酸―(1)とそのＮ―アルキル置
換体、３―｛Ｎ―（３―ヒドロキシプロピル）―
Ｎ―（１，１―ビス（ヒドロキシメチル）―２―
ヒドロキシエチル）｝アミノプロパンスルホン酸
―(1)とそのＮ―アルキル置換体、３―｛Ｎ，Ｎ―
ビス（２，３―ジヒドロキシプロピル）｝アミノ
プロパンスルホン酸―(1)とそのＮ―アルキル置換
体、３―｛Ｎ，Ｎ―ビス（１―（ヒドロキシメチ
ル）―２―ヒドロキシエチル）｝アミノプロパン
スルホン酸―(1)とそのＮ―アルキル置換体、３―
｛Ｎ，Ｎ―ビス（１，１―（ビスヒドロキシメチ
ル）―２―ヒドロキシエチル）｝アミノプロパン
スルホン酸―(1)とそのＮ―アルキル置換体、３―
｛Ｎ，Ｎ，Ｎ―トリス―（２―ヒドロキシエチ
ル）｝アンモニオプロパンスルホン酸―(1)ベタイ
ン、３―｛Ｎ，Ｎ―ビス―（２―ヒドロキシエチ
ル）―Ｎ―（３―ヒドロキシプロピル）｝アンモ
ニオプロパンスルホン酸―(1)ベタイン、３―
｛Ｎ，Ｎ，Ｎ―トリス（３―ヒドロキシプロピ
ル）｝アンモニオプロパンスルホン酸―(1)ベタイ
ン、
５―｛Ｎ―（２―ヒドロキシエチル）｝アミノ
ペンタンスルホン酸―(1)とそのＮ―アルキル置換
体（５―｛Ｎ―メチル―Ｎ―（２―ヒドロキシエ
チル）｝アミノペンタンスルホン酸―(1)，５―
｛Ｎ―エチル―Ｎ―（２―ヒドロキシエチル）｝ア
ミノペンタンスルホン酸―(1)，５―｛Ｎ―イソプ
ロピル―Ｎ―（２―ヒドロキシエチル）｝アミノ
ペンタンスルホン酸―(1)，５―｛Ｎ―（２―エチ
ルヘキシル）―Ｎ―（２―ヒドロキシエチル）｝
アミノペンタンスルホン酸―(1)，５―｛Ｎ―デシ
ル―Ｎ―（２―ヒドロキシエチル）｝アミノペン
タンスルホン酸―(1)，５―｛Ｎ―ステアリル―Ｎ
―（２―ヒドロキシエチル）｝アミノペンタンス
ルホン酸―(1)など）およびＮ，Ｎ―ジアルキル置
換体（５―｛Ｎ，Ｎ―ジメチル―Ｎ―（２―ヒド
ロキシエチル）｝アンモニオペンタンスルホン酸
―(1)ベタイン、５―｛Ｎ，Ｎ―ジエチル―Ｎ―
（２―ヒドロキシエチル）アンモニオペンタンス
ルホン酸―(1)ベタイン、５―｛Ｎ―メチル―Ｎ―
ドデシル―Ｎ―（２―ヒドロキシエチル）｝アン
モニオペンタンスルホン酸―(1)ベタインなど）、
５―｛Ｎ，Ｎ―ビス―（２―ヒドロキシエチル）｝
アミノペンタンスルホン酸―(1)とそのＮ―アルキ
ル置換体（５―｛Ｎ―メチル―Ｎ，Ｎ―ビス（２
―ヒドロキシエチル）｝アンモニオペンタンスル
ホン酸―(1)ベタイン、５―｛Ｎ―エチル―Ｎ，Ｎ
―ビス（２―ヒドロキシエチル）｝アンモニオペ
ンタンスルホン酸―(1)ベタイン、５―｛Ｎ―ブチ
ル―Ｎ，Ｎ―ビス（２―ヒドロキシエチル）｝ア
ンモニオペンタンスルホン酸―(1)ベタイン、５―
｛Ｎ―ドデシル―Ｎ，Ｎ―ビス（２―ヒドロキシ
エチル）｝アンモニオペンタンスルホン酸―(1)ベ
タイン、５―｛Ｎ―ステアリル―Ｎ，Ｎ―ビス
（２―ヒドロキシエチル）｝アンモニオペンタンス
ルホン酸―(1)ベタインなど）、５―｛Ｎ，Ｎ，Ｎ
―トリス―（２―ヒドロキシエチル）｝アンモニ
オペンタンスルホン酸―(1)ベタイン、
Ｎ―（２―ヒドロキシエチル）イミノジエタン
スルホン酸、Ｎ―（２―ヒドロキシプロピル）イ
ミノジエタンスルホン酸、Ｎ―（２，３―ジヒド
ロキシプロピル）イミノジエタンスルホン酸、Ｎ
―（１，１―ビス（ヒドロキシメチル）―２―ヒ
ドロキシエチル）イミノジエタンスルホン酸、Ｎ
―（２―ヒドロキシエチル）イミノエタンスルホ
ン酸プロパンスルホン酸、Ｎ―（２―ヒドロキシ
プロピル）イミノエタンスルホン酸プロパンスル
ホン酸、Ｎ―（２，３―ジヒドロキシプロピル）
イミノエタンスルホン酸プロパンスルホン酸、Ｎ
―（１，１―ビス（ヒドロキシメチル）―２―ヒ
ドロキシエチル）イミノエタンスルホン酸プロパ
ンスルホン酸、
Ｎ―（２―ヒドロキシエチル）オルタニル酸、
Ｎ―（２―ヒドロキシエチル）メタニル酸、Ｎ―
（２―ヒドロキシエチル）スルフアニル酸、Ｎ，
Ｎ―ビス―（２―ヒドロキシエチル）オルタニル
酸、Ｎ，Ｎ―ビス―（２―ヒドロキシエチル）メ
タニル酸、Ｎ，Ｎ―ビス―（２―ヒドロキシエチ
ル）スルフアニル酸
などが挙げられ、これらの１種または２種以上を
使用に供する。使用量は、全反応成分中0.05〜30
％、好ましくは0.1〜20％の範囲で選定する。
0.05％未満であると、本発明アルキド樹脂の反応
性、界面活性、電気化学的性質が十分に発現され
ず、また30％を越えると、本発明アルキド樹脂の
粘度が高くなる傾向にあり、貯蔵安定性が悪くな
る。かかるヒドロキシル基含有両イオン性化合物
は、使用に際してそのままであるいは塩基性物質
（例えばアンモニア、有機アミン、アルカリ金属）
との塩として用いればよい。また、この両イオン
性化合物の本発明アルキド樹脂への配合計算にあ
つては、当該化合物をアルコール成分として計算
すればよい。即ち、１分子内の含有ヒドロキシル
基の総和が１個の場合は１価アルコール、２個の
場合は２価アルコール、３個の場合は３価アルコ
ール、そしてｎ個の場合はｎ価アルコールとして
計算する。
なお、かかる１〜３価アルコールとして計算し
た場合の、本発明アルキド樹脂の代表的構造例を
上記式〔〕の両性イオン基を中心に模式する
と、以下の通りとなる。（但し、はエステル結
合鎖を持つ樹脂分子を表わす。）
１価の場合
The present invention relates to a coating composition using a novel alkyd resin. When ionic functional groups are introduced into polymer compounds,
It has a great influence on the physical and chemical properties of the polymer compound. Moreover, when such an ionic functional group is incorporated into a high molecular compound rather than when used as a low molecular compound, its properties appear more emphasized or complex. For this reason, research on polymeric compounds containing ionic functional groups has been actively conducted in recent years, and in particular, cations and anions forming counterions are bonded through covalent bonds.
That is, there is increasing interest in polymer compounds having an internal salt structure and having amphoteric ionic groups exhibiting reactivity, surface activity, electrochemical properties, and biochemical properties. An object of the present invention is to provide a coating composition using the novel alkyd resin having the above-mentioned amphoteric ionic group. That is, the gist of the present invention is, firstly, that the resin molecule contains the formula, [In the formula, A represents a C 1 to C 5 linear or branched alkylene group, phenylene group, or substituted phenylene group. ] A coating composition characterized in that the main component is an alkyd resin having an amphoteric ionic group represented by
The present invention provides a coating composition comprising 100 parts by weight of the algide resin and 5 to 100 parts by weight of the aminoplast resin as main components. The novel alkyd resin of the present invention is an alkyd resin having an amphoteric ionic group represented by the above formula [] in the resin molecule. Among the amphoteric ionic groups represented by the above formula [], those having at least one hydrogen atom as a substituent for the N atom exist as a mixture of the following tautomers. Moreover, the above-mentioned amphoteric ionic group changes its ionic form depending on the environment. For example, due to changes in PH make a change. Therefore, by controlling the environmental conditions, different reactivity, surface activity, electrochemical properties, etc. can be expressed. In the method for producing the alkyd resin of the present invention, as one of the alcohol components in the reaction components, the formula: [In the formula, R 1 is a C 1 to C 20 alkyl group having at least one hydroxyl group, R 2 and R 3 are each the same or different and are a hydrogen atom, a C 1 to C 20 alkyl group, and at least one represents an alkyl group or cyclic group having hydroxyl groups and/or sulfonic acid groups, and A has the same meaning as above. ] The hydroxyl group-containing amphoteric compound represented by 0.05 to 30% (wt%, the same applies hereinafter) of the total reaction components,
It is characterized in that it is preferably used in an amount of 0.1 to 20%, and in other respects, ordinary alkyd resin raw material components and reaction conditions and methods may be employed. Such normal reaction conditions and methods include, for example, Kyozo Kitaoka, "Introduction to Synthetic Resins for Paints" (May 1974).
Published by Kobunshi Kansaikai, March 25th, pp. 92-127), or
DH Solomon, John Willey &
Sun, The Chemistry of Organic Film Formers (pp. 75-87, 1967)
Implemented in accordance with the contents described in 2007). That is, as reaction components, a polyhydric alcohol, b polybasic acid compound, c fatty acid and/or oil, and d the above hydroxyl group-containing amphoteric compound are used, and these are mixed in an appropriate solvent as in the example below. The alkyd resin of the present invention is produced by carrying out an esterification reaction and, if necessary, a transesterification reaction according to the procedure. In addition, in the case of the alkyd resin of the present invention, as long as the reaction component d is used, alkyd resins modified with various resins, such as rosin-modified alkyd resins, phenol-modified alkyd resins, epoxy-modified alkyd resins, and vinyl-modified alkyd resins can be used. , isocyanate-modified alkyd resin, silicone-modified algide resin, and the like are also included. The above-mentioned polyhydric alcohol may be those normally used as raw materials for alkyd resins, such as ethylene glycol, propylene glycol, 1,3
-Butylene glycol, 1,6-hexane glycol, diethylene glycol, dipropylene glycol, neopentyl glycol, triethylene glycol, 2,2-dimethyl-3-hydroxypropyl-2,2-dimethyl-3-hydroxypropionate, hydrogen bisphenol A, bisphenol dihydroxypropyl ether, glycerin, trimethylolethane, trimethylolpropane, trishydroxymethylaminomethane,
Examples include pentaerythritol and dipentaerythritol, and one or more of these may be used. The amount used is not particularly limited, but it may be selected in the range of 2 to 90% of the total reaction components. The above-mentioned polybasic acid compounds may be those normally used as alkyd resin raw materials, such as phthalic anhydride, isophthalic acid, terephthalic acid, succinic anhydride, adipic acid, azelaic acid, sebacic acid, tetrahydrophthalic anhydride, hexahydroanhydride. Examples include phthalic acid, tetrabromophthalic anhydride, tetrachlorophthalic anhydride, hectic anhydride, hemicic anhydride, maleic anhydride, fumaric acid, itaconic acid, trimellitic anhydride, methylcyclohexenetricarboxylic anhydride, pyromellitic anhydride, etc. One or more of these may be used. The amount used is not particularly limited, but it may be selected in the range of 2 to 90% of the total reaction components. The fatty acid of the reaction component C may be any ordinary fatty acid, such as soybean oil fatty acid, linseed oil fatty acid,
Examples include safflower oil fatty acids, tall oil fatty acids, coconut oil fatty acids, dehydrated castor oil fatty acids, tung oil fatty acids, synthetic fatty acids, etc. Oils that can be used in place of or in combination with such fatty acids include conventional oils such as castor oil and coconut oil. , linseed oil, palm kernel oil, safflower oil, soybean oil, tung oil, dehydrated castor oil, etc., and one or more of each can be used. The amount of reaction component C to be used is not particularly limited, but it is usually selected within the range of 1 to 80% of the total reaction components. Examples of the hydroxyl group-containing amphoteric compounds include N-(2-hydroxyethyl)aminomethanesulfonic acid and its N-alkyl substituted product (N-methyl-N-(2-hydroxyethyl)aminomethanesulfonic acid, N-methyl-N-(2-hydroxyethyl)aminomethanesulfonic acid, -Ethyl-N-(2-
hydroxyethyl)aminomethanesulfonic acid, N
-isopropyl-N-(2-hydroxyethyl)
Aminomethanesulfonic acid, N-(2-ethylhexyl)-N-(2-hydroxyethyl)aminomethanesulfonic acid, N-decyl-N-(2-hydroxyethyl)aminomethanesulfonic acid, N-stearyl-N-( (2-hydroxyethyl)aminomethanesulfonic acid, etc.) and N,N-dialkyl substituted products (N,N-dimethyl-N-(2-hydroxyethyl)ammoniomethanesulfonic acid betaine, N,N-diethyl-N-( 2-Hydroxyethyl)ammoniomethanesulfonic acid betaine, N
-Methyl-N-dodecyl-N-(2-hydroxyethyl)ammoniomethanesulfonic acid betaine, etc.), N-(2-hydroxy-1-methylethyl)
Aminomethanesulfonic acid and its N-alkyl substituted products, N,N-dialkyl substituted products, N-(2-
hydroxypropyl)aminomethanesulfonic acid and its N-alkyl substituted products and N,N-dialkyl substituted products, N-(3-hydroxypropyl)aminomethanesulfonic acid and its N-alkyl substituted products and N,N-dialkyl substituted products , N-(2-propyl-2-hydroxyethyl)aminomethanesulfonic acid and its N-alkyl substituted products and N,N-
Dialkyl substituted product, N-(2-methyl-2-ethyl-2-hydroxyethyl)aminomethanesulfonic acid and its N-alkyl substituted product and N,N-dialkyl substituted product, N-(1,2-dimethyl-2 ―
hydroxyethyl)aminomethanesulfonic acid and its N-alkyl substituted products and N,N-dialkyl substituted products, N-(1,1,2,2-tetramethyl-
2-hydroxyethyl)aminomethanesulfonic acid and its N-alkyl substituted products and N,N-dialkyl substituted products, N-(1-methyl-5,5-dimethyl-5-hydroxypentyl)aminomethanesulfonic acid and its N -Alkyl substituted product and N,N-
Dialkyl substituted product, N-(1,2-diisopropyl-2-hydroxyethyl)aminomethanesulfonic acid and its N-alkyl substituted product and N,N-dialkyl substituted product, N-(2,3-dihydroxypropyl)aminomethane Sulfonic acid and its N-alkyl substituted product and N,N-dialkyl substituted product, N
-(1-hydroxymethyl-2-hydroxyethyl)aminomethanesulfonic acid and its N-alkyl substituted products and N,N-dialkyl substituted products, N-
(1-hydroxymethyl-2-methyl-2-hydroxyethyl)aminomethanesulfonic acid and its N
-Alkyl substituted product and N,N-dialkyl substituted product, N-(1-hydroxymethyl-3-hydroxypropyl)aminomethanesulfonic acid and its N-
Alkyl substituted product and N,N-dialkyl substituted product, N-(-(γ-hydroxypropyl)-2
-Hydroxyethyl)aminomethanesulfonic acid and its N-alkyl substituted products and N,N-dialkyl substituted products, N-(1,1-bis(hydroxymethyl)-2-hydroxyethyl)aminomethanesulfonic acid and its N- Alkyl substituent and N,N-
Dialkyl substituted product, N-(2,2-bis(hydroxymethyl)-3-hydroxypropyl)aminomethanesulfonic acid and its N-alkyl substituted product and N,N-dialkyl substituted product, N,N-bis(2
-Hydroxyethyl)aminomethanesulfonic acid and its N-alkyl substituted product (N-methyl-N,N-
Bis(2-hydroxyethyl)ammoniomethanesulfonic acid betaine, N-ethyl-N,N-bis(2-hydroxyethyl)ammoniomethanesulfonic acid betaine, N-butyl-N,N-bis(2
-Hydroxyethyl)ammoniomethanesulfonic acid betaine, N-dodecyl-N,N-bis(2-
hydroxyethyl)ammoniomethanesulfonic acid betaine, N-stearyl-N,N-bis(2-
hydroxyethyl)ammoniomethanesulfonic acid betaine, etc.), N-(2-hydroxyethyl)
-N-(2-hydroxypropyl)aminomethanesulfonic acid and its N-alkyl substituted product, N,N-
Bis(2-hydroxypropyl)aminomethanesulfonic acid and its N-alkyl substituted product, N,N-bis(4-hydroxybutyl)aminomethanesulfonic acid and its N-alkyl substituted product, N-(2-hydroxyethyl) -N-(1,1-bis(hydroxymethyl)-2-hydroxyethyl)aminomethanesulfonic acid and its N-alkyl substituted product, N-
(3-Hydroxypropyl)-N-(1,1-bis(hydroxymethyl)-2-hydroxyethyl)aminomethanesulfonic acid and its N-alkyl substituted product, N,N-bis(2,3-dihydroxypropyl) Aminomethanesulfonic acid and its N-alkyl substituted product, N,N-bis-(1-hydroxymethyl)-2-hydroxyethyl)aminomethanesulfonic acid and its N-alkyl substituted product, N,N-bis(1, 1-(bishydroxymethyl)-2-hydroxyethyl)aminomethanesulfonic acid and its N-alkyl substituted product, N,N,N-tris-(2
-Hydroxyethyl)ammoniomethanesulfonic acid betaine, N,N-bis-(2-hydroxyethyl)-N-(3-hydroxypropyl)ammoniomethanesulfonic acid betaine, N,N,N-tris(3-hydroxy (propyl)ammoniomethanesulfonic acid betaine, N-(2-hydroxyethyl)aminoethanesulfonic acid and its N-alkyl substituted products (N-methyl-N-(2-hydroxyethyl)aminoethanesulfonic acid, N-ethyl- N-(2-hydroxyethyl)aminoethanesulfonic acid, N-isopropyl-N-(2-hydroxyethyl)aminoethanesulfonic acid, N-(2-ethylhexyl)-N-
(2-hydroxyethyl)aminoethanesulfonic acid, N-decyl-N-(2-hydroxyethyl)
Aminoethanesulfonic acid, N-stearyl-N-
(2-hydroxyethyl)aminoethanesulfonic acid, etc.) and N,N-dialkyl substituted products (N,
N-dimethyl-N-(2-hydroxyethyl)ammonioethanesulfonic acid betaine, N,N-diethyl-N-(2-hydroxyethyl)ammonioethanesulfonic acid betaine, N-methyl-N-
dodecyl-N-(2-hydroxyethyl)ammonioethanesulfonic acid betaine, etc.), N-(2-hydroxyethyl),
-Hydroxy-1-methylethyl)aminoethanesulfonic acid and its N-alkyl substituted products and N,
N-dialkyl substituted product, N-(2-hydroxypropyl)aminoethanesulfonic acid and its N-alkyl substituted product and N,N-dialkyl substituted product, N
-(3-hydroxypropyl)aminoethanesulfonic acid and its N-alkyl substituted products and N,N-
Dialkyl substituted product, N-(2-propyl-2-hydroxyethyl)aminoethanesulfonic acid and its N-alkyl substituted product and N,N-dialkyl substituted product, N-(2-methyl-2-ethyl-2-hydroxy ethyl)aminoethanesulfonic acid and its N
-Alkyl substituted product and N,N-dialkyl substituted product, N-(1,2-dimethyl-2-hydroxyethyl)aminoethanesulfonic acid and its N-alkyl substituted product and N,N-dialkyl substituted product, N-
(1,1,2,2-tetramethyl-2-hydroxyethyl)aminoethanesulfonic acid and its N-alkyl substituted products and N,N-dialkyl substituted products,
N-(1-methyl-5,5-dimethyl-5-hydroxypentyl)aminoethanesulfonic acid and its N-alkyl substituted products and N,N-dialkyl substituted products, N-(1,2 diisopropyl-2-hydroxyethyl ) Aminoethanesulfonic acid and its N-
Alkyl substituted product and N,N-dialkyl substituted product, N-(2,3-dihydroxypropyl)aminoethanesulfonic acid and its N-alkyl substituted product and N,N-dialkyl substituted product, N-(1-hydroxymethyl- 2-hydroxyethyl)aminoethanesulfonic acid and its N-alkyl substituted products and N,N-dialkyl substituted products, N-(1-hydroxymethyl-2-methyl-2-hydroxyethyl)
Aminoethanesulfonic acid and its N-alkyl and N,N-dialkyl substituted products, N-(1-
Hydroxymethyl-3-hydroxypropyl)aminoethanesulfonic acid and its N-alkyl- and N,N-dialkyl-substituted products, N-(1-
(γ-Hydroxypropyl)-2-hydroxyethyl)aminoethanesulfonic acid and its N-alkyl substituted products and N,N-dialkyl substituted products, N-
(1,1-bis(hydroxymethyl)-2-hydroxyethyl)aminoethanesulfonic acid and its N
-Alkyl substituted product and N,N-dialkyl substituted product, N-(2,2-bis(hydroxymethyl)-
3-hydroxypropyl)aminoethanesulfonic acid and its N-alkyl substituted products and N,N-dialkyl substituted products, N,N-bis(2-hydroxyethyl)aminoethanesulfonic acid and its N-alkyl substituted products (N- Methyl-N,N-bis(2-hydroxyethyl)ammonioethanesulfonic acid betaine, N-ethyl-N,N-bis(2-hydroxyethyl)ammonioethanesulfonic acid betaine, N-butyl-N,N- Bis(2-hydroxyethyl)ammonioethanesulfonic acid betaine,
N-dodecyl-N,N-bis(2-hydroxyethyl)ammonioethanesulfonic acid betaine, N
-stearyl, N,N-bis(2-hydroxyethyl)ammonioethanesulfonic acid betaine, etc.), N-(2-hydroxyethyl)-N-(2
-Hydroxypropyl)aminoethanesulfonic acid and its N-alkyl substituted product, N,N-bis(2-
hydroxypropyl)aminoethanesulfonic acid and its N-alkyl substituted product, N,N-bis(4-hydroxybutyl)aminoethanesulfonic acid and its N-alkyl substituted product, N-(2-hydroxyethyl)-N-( 1,1-bis(hydroxymethyl)
-2-hydroxyethyl)aminoethanesulfonic acid and its N-alkyl substituted product, N-(3-hydroxypropyl)-N-(1,1-bis(hydroxymethyl)-2-hydroxyethyl)aminoethanesulfonic acid and Its N-alkyl substituent, N,N
-bis(2,3-dihydroxypropyl)aminoethanesulfonic acid and its N-alkyl substituted product,
N,N-bis(1-(hydroxymethyl)-2-
hydroxyethyl) aminoethanesulfonic acid and its N-alkyl substituted product, N,N-bis-(1,1
-(bishydroxymethyl)-2-hydroxyethyl)aminoethanesulfonic acid and its N-alkyl substituted product, N,N,N-tris-(2-hydroxyethyl)ammonioethanesulfonic acid betaine, N,N-bis -(2-hydroxyethyl)-
N-(3-hydroxypropyl)ammonioethanesulfonic acid betaine, N,N,N-tris(3
-Hydroxypropyl)ammonioethanesulfonic acid betaine, 3-{N-(2-hydroxyethyl)}aminopropanesulfonic acid-(1) and its N-alkyl substituted product (3-{N-methyl-N-(2) -Hydroxyethyl)}Aminopropanesulfonic acid-(1),3-
{N-ethyl-N-(2-hydroxyethyl)}aminopropanesulfonic acid-(1),3-{N-isopropyl-N-(2-hydroxyethyl)}aminopropanesulfonic acid-(1),3- {N-(2-ethylhexyl)-N-(2-hydroxyethyl)}
Aminopropanesulfonic acid-(1),3-{N-decyl-N-(2-hydroxyethyl)}Aminopropanesulfonic acid-(1),3-{N-stearyl-N
-(2-hydroxyethyl)}aminopropanesulfonic acid-(1), etc.) and N,N-dialkyl substituted products (3-{N,N-dimethyl-N-(2-hydroxyethyl)}ammoniopropanesulfonic acid -(1)Betaine, 3-{N,N-diethyl-N-
(2-hydroxyethyl)}ammoniopropanesulfonic acid-(1) betaine, 3-{N-methyl-N-
dodecyl-N-(2-hydroxyethyl)}ammoniopropanesulfonic acid-(1) betaine, etc.),
3-{N-(2-hydroxy-1-methylethyl)}aminopropanesulfonic acid-(1) and its N-
Alkyl substituted product and N,N-dialkyl substituted product, 3-{N-(2-hydroxypropyl)}aminopropanesulfonic acid-(1) and its N-alkyl substituted product and N,N-dialkyl substituted product, 3-
{N-(3-hydroxypropyl)}aminopropanesulfonic acid-(1) and its N-alkyl substituted products and N,N-dialkyl substituted products, 3-{N-(2-
propyl-2-hydroxyethyl)}aminopropanesulfonic acid-(1) and its N-alkyl substituted products and N,N-dialkyl substituted products, 3-{N-(2
-methyl-2-ethyl-2-hydroxyethyl)}
Aminopropanesulfonic acid-(1) and its N-alkyl substituted products and N,N-dialkyl substituted products, 3-
{N-(1,2-dimethyl-2-hydroxyethyl)}aminopropanesulfonic acid-(1) and its N-
Alkyl substituted product and N,N-dialkyl substituted product, 3-{N-(1,1,2,2-tetramethyl-2-hydroxyethyl)}aminopropanesulfonic acid-(1) and its N-alkyl substituted product and N,
N-dialkyl substituted product, 3-{N-(1-methyl-5,5-dimethyl-5-hydroxypentyl)}
Aminopropanesulfonic acid-(1) and its N-alkyl substituted products and N,N-dialkyl substituted products, 3-
{N-(1,2-diisopropyl-2-hydroxyethyl)}aminopropanesulfonic acid-(1) and its N-alkyl substituted products and N,N-dialkyl substituted products, 3-{N-(2,3- dihydroxypropyl)}aminopropanesulfonic acid-(1) and its N
-Alkyl substituted product and N,N-dialkyl substituted product, 3-{N-(1-hydroxymethyl-2-hydroxyethyl)}aminopropanesulfonic acid-
(1) and its N-alkyl substituted products and N,N-dialkyl substituted products, 3-{N-(1-hydroxymethyl-2-methyl-2-hydroxyethyl)}aminopropanesulfonic acid-(1) and its N-alkyl substituents and N,N-dialkyl substituents, 3-{N
-(1-hydroxymethyl-3-hydroxypropyl)}aminopropanesulfonic acid-(1) and its N
-Alkyl substituted product and N,N-dialkyl substituted product, 3-{N-(1-(γ-hydroxypropyl)-2-hydroxyethyl)}aminopropanesulfonic acid-(1) and its N-alkyl substituted product and N,N-dialkyl substituted product, 3-{N-(1,1
-bis(hydroxymethyl)-2-hydroxyethyl)}aminopropanesulfonic acid-(1) and its N
-Alkyl substituted product and N,N-dialkyl substituted product, 3-{N-(2,2-bis(hydroxymethyl)-3-hydroxypropyl)}aminopropanesulfonic acid-(1) and its N-alkyl substituted product and N,N-dialkyl substituted product, 3-{N,N-bis(2-hydroxyethyl)}aminopropanesulfonic acid-(1) and its N-alkyl substituted product (3-
{N-methyl-N,N-bis(2-hydroxyethyl)}ammoniopropanesulfonic acid-(1) betaine, 3-{N-ethyl-N,N-bis(2-hydroxyethyl)}ammoniopropane Sulfonic acid - (1) betaine, 3-{N-butyl-N,N-bis(2-hydroxyethyl)} ammoniopropanesulfonic acid - (1) betaine, 3-{N-dodecyl-N,N-bis (2-hydroxyethyl)}ammoniopropanesulfonic acid-(1) betaine, 3-
{N-stearyl-N,N-bis(2-hydroxyethyl)}ammoniopropanesulfonic acid-(1)
3-{N-(2-hydroxyethyl)-N-(2-hydroxypropyl)}aminopropanesulfonic acid-(1) and its N-alkyl substituted products, 3-{N,N-bis( 2-hydroxypropyl)}aminopropanesulfonic acid-(1) and its N
-Alkyl substituted product, 3-{N,N-bis(4-hydroxybutyl)}aminopropanesulfonic acid-
(1) and its N-alkyl substituted product, 3-{N-(2-
hydroxyethyl)-N-(1,1-bis(hydroxymethyl)-2-hydroxyethyl)}aminopropanesulfonic acid-(1) and its N-alkyl substituted product, 3-{N-(3-hydroxypropyl) ―
N-(1,1-bis(hydroxymethyl)-2-
hydroxyethyl)}aminopropanesulfonic acid-(1) and its N-alkyl substituted product, 3-{N,N-
Bis(2,3-dihydroxypropyl)}aminopropanesulfonic acid-(1) and its N-alkyl substituted product, 3-{N,N-bis(1-(hydroxymethyl)-2-hydroxyethyl)}aminopropane Sulfonic acid-(1) and its N-alkyl substituted product, 3-
{N,N-bis(1,1-(bishydroxymethyl)-2-hydroxyethyl)}aminopropanesulfonic acid-(1) and its N-alkyl substituted product, 3-
{N,N,N-tris-(2-hydroxyethyl)}ammoniopropanesulfonic acid-(1) betaine, 3-{N,N-bis-(2-hydroxyethyl)-N-(3-hydroxypropyl) )}Ammoniopropanesulfonic acid-(1) betaine, 3-
{N,N,N-tris(3-hydroxypropyl)}ammoniopropanesulfonic acid-(1) betaine, 5-{N-(2-hydroxyethyl)}aminopentanesulfonic acid-(1) and its N- Alkyl substituted product (5-{N-methyl-N-(2-hydroxyethyl)}aminopentanesulfonic acid-(1),5-
{N-ethyl-N-(2-hydroxyethyl)}aminopentanesulfonic acid-(1),5-{N-isopropyl-N-(2-hydroxyethyl)}aminopentanesulfonic acid-(1),5- {N-(2-ethylhexyl)-N-(2-hydroxyethyl)}
Aminopentanesulfonic acid-(1),5-{N-decyl-N-(2-hydroxyethyl)}Aminopentanesulfonic acid-(1),5-{N-stearyl-N
-(2-hydroxyethyl)}aminopentanesulfonic acid-(1), etc.) and N,N-dialkyl substituted products (5-{N,N-dimethyl-N-(2-hydroxyethyl)}ammoniopentanesulfonic acid -(1)Betaine, 5-{N,N-diethyl-N-
(2-Hydroxyethyl)ammoniopentanesulfonic acid-(1) betaine, 5-{N-methyl-N-
dodecyl-N-(2-hydroxyethyl)}ammoniopentanesulfonic acid-(1) betaine, etc.),
5-{N,N-bis-(2-hydroxyethyl)}
Aminopentanesulfonic acid-(1) and its N-alkyl substituted product (5-{N-methyl-N,N-bis(2
-hydroxyethyl)}ammoniopentanesulfonic acid-(1) betaine, 5-{N-ethyl-N,N
-Bis(2-hydroxyethyl)}ammoniopentanesulfonic acid-(1) betaine, 5-{N-butyl-N,N-bis(2-hydroxyethyl)}ammoniopentanesulfonic acid-(1)betaine, 5-
{N-dodecyl-N,N-bis(2-hydroxyethyl)}ammoniopentanesulfonic acid-(1)betaine, 5-{N-stearyl-N,N-bis(2-hydroxyethyl)}ammoniopentane Sulfonic acid-(1) betaine, etc.), 5-{N, N, N
-Tris-(2-hydroxyethyl)}ammoniopentanesulfonic acid-(1) betaine, N-(2-hydroxyethyl)iminodiethanesulfonic acid, N-(2-hydroxypropyl)iminodiethanesulfonic acid, N -(2,3-dihydroxypropyl)iminodiethanesulfonic acid, N
-(1,1-bis(hydroxymethyl)-2-hydroxyethyl)iminodiethanesulfonic acid, N
-(2-hydroxyethyl)iminoethanesulfonic acid propanesulfonic acid, N-(2-hydroxypropyl)iminoethanesulfonic acid propanesulfonic acid, N-(2,3-dihydroxypropyl)
Iminoethanesulfonic acid propanesulfonic acid, N
-(1,1-bis(hydroxymethyl)-2-hydroxyethyl)iminoethanesulfonic acid, propanesulfonic acid, N-(2-hydroxyethyl)orthanylic acid,
N-(2-hydroxyethyl)metanilic acid, N-
(2-hydroxyethyl)sulfanilic acid, N,
Examples include N-bis-(2-hydroxyethyl)orthanilic acid, N,N-bis-(2-hydroxyethyl)methanilic acid, N,N-bis-(2-hydroxyethyl)sulfanilic acid, and these 1 The species or species are provided for use. The amount used is 0.05 to 30 of the total reaction components.
%, preferably in the range of 0.1 to 20%.
If it is less than 0.05%, the reactivity, surface activity, and electrochemical properties of the alkyd resin of the present invention will not be sufficiently expressed, and if it exceeds 30%, the viscosity of the alkyd resin of the present invention will tend to increase, making storage difficult. Stability deteriorates. Such hydroxyl group-containing zwitterionic compounds may be used as such or with basic substances (e.g. ammonia, organic amines, alkali metals).
It can be used as a salt. Furthermore, when calculating the addition of this amphoteric compound to the alkyd resin of the present invention, the compound may be calculated as an alcohol component. In other words, if the total number of hydroxyl groups contained in one molecule is 1, it is calculated as a monohydric alcohol, if it is 2, it is a dihydric alcohol, if it is 3, it is a trihydric alcohol, and if there are n hydroxyl groups, it is calculated as an n-hydric alcohol. do. A typical structural example of the alkyd resin of the present invention when calculated as such a mono- to trihydric alcohol is as follows when modeled around the amphoteric ionic group of the above formula []. (However, represents a resin molecule with an ester bond chain.) In the case of monovalent
【式】または[expression] or
【式】 ２価の場合【formula】 In the case of bivalent
【式】または[expression] or
【式】 ３価の場合【formula】 In the case of trivalent
【式】または[expression] or
【式】
上記ヒドロキシル基含有両イオン性化合物の合
成法としては、常法が採用されてよく、例えば以
下の反応方式が挙げられる。
本発明アルキド樹脂は、良好な顔料分散性を示
し、両性イオン基をもたない通常のアルキド樹脂
と比べ、分散時間が短縮され、また調整された顔
料ペーストの粘度も低くなり、良好な色調の着色
塗膜の形成に寄与する。
本発明の塗料組成物は、当該アルキド樹脂を主
成分とするものであり、これに要すれば通常の有
機系または無機系の着色顔料、体質顔料、防錆顔
料、その他添加剤（充填材、増量材、増粘剤な
ど）、更に表面調整剤、ドライヤー、有機溶剤等
を適量混入し、常温で分散混合することにより調
製される。かかる組成物を被塗物に通常の方法で
膜厚５〜500μにて塗装し、次いで常温乾燥する
ことにより塗膜が形成される。勿論、この組成物
は常温乾燥に代えまたは加えて焼付乾燥も採用で
きる。
本発明の熱硬化性樹脂組成物は、当該アルキド
樹脂とアミノプラスト樹脂を主成分とするもので
ある。
前記アミノプラスト樹脂としては、通常のもの
であつてよく、例えばメラミン樹脂、グアナミン
樹脂、尿素樹脂等の１種または２種以上をそのま
まで、または必要ならば有機溶媒に溶解して使用
に供すればよい。かかるアミノプラスト樹脂の使
用量は、特に制限されるものではないが、通常上
記アルキド樹脂100部に対し５〜1000部、好まし
くは７〜90部の範囲で選定する。５部未満である
と、十分な架橋被膜が形成されない為その耐溶剤
性、耐化学薬品性が満足されず、また100部を越
えると、形成被膜は脆くなりすぎる傾向にある。
上記アルキド樹脂とアミノプラスト樹脂もしく
はその溶液を所定割合で配合せしめ、室温で撹拌
混合して目的とする樹脂組成物を調製する。かか
る樹脂組成物において、当該アルキド樹脂中の両
性イオン基がアミノプラスト樹脂と有効に架橋反
応をおこし、加えてアルキド樹脂中のカルボキシ
ル基やヒドロキシル基とアミノプラスト樹脂との
架橋反応をも促進させる作用を有する。このため
被膜形成の焼付乾燥に、通常のアルキド樹脂を用
いた組成物の如き高温・長時間といつた条件は必
要なく、例えば70〜220℃の温度で30秒〜120分と
いう緩和な条件が採用されてよい。また、同じ温
度と時間の焼付条件下では上記の通常組成物と比
べ、架橋反応がより進行した三次元化被膜を得る
ことができる。このように、本発明樹脂組成物は
エネルギー資源の節約に寄与しながら、熱硬化に
よつて耐久性良好な被膜を形成する。即ち、広く
熱硬化性の成型加工用原料として使用でき、また
特に焼付乾燥型塗料組成物への使用に有用であつ
て、この場合被塗物の種類も金属木材、紙系、プ
ラスチツク系に広く適用することが可能となる。
上記焼付乾燥型塗料組成物は、当該樹脂組成物
に必要に応じ通常の有機系または無機系の着色顔
料、体質顔料、防錆顔料、そ他添加剤（充填材、
増量材、増粘剤など）、更に表面調整剤、有機溶
剤等の少なくとも１種を適量混入し、常温で分散
混合することにより調製される。かかる組成物を
被塗物に通常の方法で膜厚５〜500μにて塗装し、
次いで焼付乾燥することにより外観、耐久性とも
に良好な三次元塗膜が形成される。特に、各種顔
料を使用する場合は、適量の本発明アルキド樹脂
と顔料と必要に応じ有機溶媒等を混入し、室温で
分散混合した後、残りの本発明アルキド樹脂とア
ミノプラスト樹脂とその他添加剤等を混合撹拌し
て該塗料組成物を調製することもできる。
この塗料組成物にあつては、前述の本発明樹脂
組成物にみられる反応促進効果は何ら損なわれる
ことなく、同様の焼付低温効果を有する。
次に、実施例、参考例および比較例を挙げて本
発明を具体的に説明する。
参考例 １
（第１段反応）撹拌器、窒素導入管、温度制御
装置、コンデンサー、デカンターを備えた２コ
ルベンに、アマニ油994部とペンタエリトリツト
183部とナフテン酸鉛15部を仕込み、窒素雰囲気
下で温度を240℃に上げて30分間撹拌したところ、
メタノールトレランスが無限大となつた。（第２
段反応）内容物の温度を150℃に下げ、撹拌をと
めて無水フタル酸321部とＮ，Ｎ―ビス―（２―
ヒドロキシエチル）アミノメタンスルホン酸5.5
部とキシレン45部を仕込んだ。再び撹拌を関始
し、温度を徐々に上げながら生成する水をキシレ
ンと共沸還流させて除去した。約２時間かけて温
度を240℃にし、さらに同一温度でカルボン酸相
当の酸価が８になるまで撹拌と脱水をを継続し
て、反応を終了した。得られた樹脂は油長65、酸
価8.5、水酸価50、数平均分子量（ｎ）1800で
あつた。この樹脂をキシレンで希釈して不揮発分
70％のアルキドワニスを得た。このワニスの粘度
は、ガードナー粘度計でＺであつた。
参考例２〜９および比較例１〜２
表１の原料を表１に示す量で用いる以外は、参
考例１と同様にして表１のアルキド樹脂ワニスを
得た。[Formula] As a method for synthesizing the above-mentioned hydroxyl group-containing amphoteric compound, conventional methods may be employed, and examples include the following reaction method. The alkyd resin of the present invention exhibits good pigment dispersibility, shortens the dispersion time, and lowers the viscosity of the prepared pigment paste compared to ordinary alkyd resins that do not have zwitterionic groups, resulting in good color tone. Contributes to the formation of colored coatings. The coating composition of the present invention has the alkyd resin as a main component, and if necessary, conventional organic or inorganic coloring pigments, extender pigments, antirust pigments, and other additives (fillers, It is prepared by mixing appropriate amounts of fillers, thickeners, etc.), surface conditioners, dryers, organic solvents, etc., and dispersing and mixing at room temperature. A coating film is formed by applying such a composition to an object to be coated in a conventional manner to a film thickness of 5 to 500 μm, and then drying at room temperature. Of course, this composition can be dried by baking instead of or in addition to drying at room temperature. The thermosetting resin composition of the present invention contains the alkyd resin and the aminoplast resin as main components. The aminoplast resin may be any of the usual ones, such as one or more of melamine resin, guanamine resin, urea resin, etc., which may be used as is or, if necessary, dissolved in an organic solvent. Bye. The amount of the aminoplast resin to be used is not particularly limited, but is usually selected in the range of 5 to 1000 parts, preferably 7 to 90 parts, based on 100 parts of the above alkyd resin. If the amount is less than 5 parts, a sufficient crosslinked film will not be formed, resulting in unsatisfied solvent resistance and chemical resistance, and if it exceeds 100 parts, the formed film will tend to become too brittle. The above-mentioned alkyd resin and aminoplast resin or a solution thereof are blended in a predetermined ratio and mixed with stirring at room temperature to prepare a desired resin composition. In such a resin composition, the amphoteric ionic group in the alkyd resin effectively causes a crosslinking reaction with the aminoplast resin, and in addition, the action of promoting the crosslinking reaction between the carboxyl group or hydroxyl group in the alkyd resin and the aminoplast resin. has. For this reason, baking drying for film formation does not require conditions such as high temperatures and long periods of time as with compositions using ordinary alkyd resins, but mild conditions such as 30 seconds to 120 minutes at a temperature of 70 to 220°C are required. May be adopted. Further, under the baking conditions of the same temperature and time, a three-dimensional film in which the crosslinking reaction has progressed more can be obtained compared to the above-mentioned ordinary composition. In this manner, the resin composition of the present invention forms a highly durable coating through thermosetting while contributing to the saving of energy resources. That is, it can be widely used as a raw material for thermosetting molding processing, and is particularly useful for use in bake-drying paint compositions, and in this case, the types of objects to be coated can range from metal wood, paper, and plastic. It becomes possible to apply. The above-mentioned bake-drying paint composition may contain conventional organic or inorganic coloring pigments, extender pigments, anti-rust pigments, and other additives (fillers,
It is prepared by mixing an appropriate amount of at least one of a filler, a thickener, etc.), a surface conditioner, an organic solvent, etc., and dispersing and mixing the mixture at room temperature. The composition is coated on the object to be coated in a conventional manner to a film thickness of 5 to 500μ,
Then, by baking and drying, a three-dimensional coating film with good appearance and durability is formed. In particular, when using various pigments, mix an appropriate amount of the alkyd resin of the present invention, the pigment, and an organic solvent as necessary, disperse and mix at room temperature, and then add the remaining alkyd resin of the present invention, aminoplast resin, and other additives. The coating composition can also be prepared by mixing and stirring the following. This coating composition has the same low-temperature baking effect without impairing the reaction accelerating effect seen in the resin composition of the present invention described above. Next, the present invention will be specifically explained with reference to Examples, Reference Examples, and Comparative Examples. Reference example 1 (1st stage reaction) 994 parts of linseed oil and pentaerythritol were placed in a two-kolben equipped with a stirrer, nitrogen inlet tube, temperature control device, condenser, and decanter.
When 183 parts and 15 parts of lead naphthenate were charged, the temperature was raised to 240°C under a nitrogen atmosphere, and the mixture was stirred for 30 minutes.
Methanol tolerance has become infinite. (Second
Stage reaction) The temperature of the contents was lowered to 150°C, stirring was stopped, and 321 parts of phthalic anhydride and N,N-bis(2-
Hydroxyethyl)aminomethanesulfonic acid 5.5
and 45 parts of xylene. Stirring was started again, and the water produced was removed by azeotropic reflux with xylene while gradually increasing the temperature. The temperature was raised to 240° C. over about 2 hours, and stirring and dehydration were continued at the same temperature until the acid value equivalent to carboxylic acid reached 8 to complete the reaction. The resulting resin had an oil length of 65, an acid value of 8.5, a hydroxyl value of 50, and a number average molecular weight (n) of 1,800. This resin is diluted with xylene to remove the non-volatile content.
A 70% alkyd varnish was obtained. The viscosity of this varnish was Z on a Gardner viscometer. Reference Examples 2 to 9 and Comparative Examples 1 to 2 Alkyd resin varnishes shown in Table 1 were obtained in the same manner as in Reference Example 1, except that the raw materials shown in Table 1 were used in the amounts shown in Table 1.
【表】【table】
【表】
参考例 10
撹拌器、窒素導入管、温度制御装置、コンデン
サー、デカンターを備えた２コルベンに、脱水
ヒマシ油脂肪酸81部、ヤシ油脂肪酸59部、トリメ
チロールプロパン121部、無水フタル酸715部、ジ
エチレングリコール481部、Ｎ―メチル―Ｎ―
（１―ヒドロキシメチル―２―ヒドロキシエチル）
アミノメタンスルホン酸80部とキシレン45部を仕
込み、撹拌しながら温度を240℃に上げた。生成
する水をキシレンと共沸還流させて除去しながら
反応を継続し、カルボン酸相当の酸価が８になつ
た時に反応を終了した。得られた樹脂は油長10、
酸価22.5、水酸価100、n800であつた。この樹
脂をキシレンで稀釈して不揮発分60％のアルキド
ワニスを得た。このワニスの粘度はＺであつた。
参考例11〜14および比較例３
表２の原料を表２に示す量で用いる以外は、参
考例10と同様にして表２のアルキド樹脂ワニスを
得た。[Table] Reference example 10 In a two-colben equipped with a stirrer, nitrogen inlet tube, temperature control device, condenser, and decanter, 81 parts of dehydrated castor oil fatty acid, 59 parts of coconut oil fatty acid, 121 parts of trimethylolpropane, and 715 parts of phthalic anhydride. parts, diethylene glycol 481 parts, N-methyl-N-
(1-hydroxymethyl-2-hydroxyethyl)
80 parts of aminomethane sulfonic acid and 45 parts of xylene were charged, and the temperature was raised to 240°C while stirring. The reaction was continued while the produced water was removed by azeotropic reflux with xylene, and the reaction was terminated when the acid value equivalent to the carboxylic acid reached 8. The obtained resin has an oil length of 10,
The acid value was 22.5, the hydroxyl value was 100, and the n800. This resin was diluted with xylene to obtain an alkyd varnish with a nonvolatile content of 60%. The viscosity of this varnish was Z. Reference Examples 11 to 14 and Comparative Example 3 Alkyd resin varnishes shown in Table 2 were obtained in the same manner as Reference Example 10, except that the raw materials shown in Table 2 were used in the amounts shown in Table 2.
【表】
実施例 １
参考例２で得られたアルキド樹脂ワニス158部
とブチル化メラミン樹脂ワニス（大日本インキ社
製「スーパーベツカミンＧ―821―60」）8.5部と
石油系溶剤（東燃石油社製「ソルベツソ―100」）
100部をラボミキサーで室温にて撹拌混合して、
熱硬化性樹脂組成物を調製した。この組成物をブ
リキ板上に乾燥膜厚が30μになるように塗装し、
100℃、120℃、140℃、160℃の温度でそれぞれ20
分間熱硬化させて透明な塗膜を得た。この塗膜を
ソツクスレー抽出器で４時間アセトン抽出した結
果、100℃硬化塗膜で68％、120℃硬化塗膜で88
％、140℃硬化塗膜で92％、そして160℃硬化塗膜
で96％が残留した。
実施例 ２
参考例２で得られたアルキド樹脂ワニスを用い
るかわりに参考例３で得られたアルキド樹脂ワニ
スを117部用い、「スーパーベツカミンＧ―821―
60」を50部用いる以外は実施例１と同様にして熱
硬化性樹脂組成物を調製した。この組成物をブリ
キ板上に乾燥膜厚が40μになるように塗装し、
140℃で20分間硬化させて透明な塗膜を得た。こ
のものの鉛筆硬度はＨで架橋密度は2.08×10-3モ
ル／cm3であつた。
比較例 ４
参考例３で得られたアルキド樹脂ワニスのかわ
りに比較例２で得られたアルキド樹脂ワニスを用
いる以外は実施例２と同様にして透明な塗膜を得
た。このものの鉛筆硬度はHBで架橋密度は1.22
×10-3モル／cm3であつた。
実施例 ３
参考例２で得られたアルキド樹脂ワニスを用い
るかわりに参考例４，５，６，８，９，10，11，
12，13，14で得られた樹脂を133部（参考例８の
樹脂は114部）用い、「スーパーベツカミンＧ―
821―60」を33部用い、熱硬化温度を120℃とする
以外は実施例１と同様にして各種透明塗膜を得
た。ソツクスレ―抽出器によるアセトン抽出残留
分はいずれも87％以上であつた。
実施例４，５および比較例５
参考例１，７、比較例１で得られたアルキド樹
脂ワニス50部にそれぞれ、酸化チタン顔料（石原
産業社製「タイペークＲ―820」）27部、炭酸カル
シウム顔料（丸尾カルシウム社製「重炭」）10部、
ナフテン酸鉛0.3部、脂肪族系炭化水素混合溶媒
（日本石油社製「特ソル」）８部を配合し、ペイン
トコンデイシヨナーで30分間分散混合して白色塗
料組成物を得た。このものを鋼板上に乾燥膜厚が
40μになるように塗装し、室温で乾燥させた時の
諸特性を表３に示す。[Table] Example 1 158 parts of the alkyd resin varnish obtained in Reference Example 2, 8.5 parts of butylated melamine resin varnish (“Super Betsucomin G-821-60” manufactured by Dainippon Ink Co., Ltd.), and petroleum-based solvent (Tonen Sekiyu Co., Ltd.) ``Solbetsu So-100'')
Stir and mix 100 parts with a lab mixer at room temperature.
A thermosetting resin composition was prepared. This composition was painted on a tin plate so that the dry film thickness was 30μ,
20 respectively at temperatures of 100℃, 120℃, 140℃ and 160℃
A transparent coating film was obtained by heat curing for a minute. This coating film was extracted with acetone for 4 hours using a Soxhlet extractor. As a result, the coating film cured at 100°C was 68%, and the coating film cured at 120°C was 88%.
%, 92% remained in the film cured at 140°C, and 96% remained in the film cured at 160°C. Example 2 Instead of using the alkyd resin varnish obtained in Reference Example 2, 117 parts of the alkyd resin varnish obtained in Reference Example 3 was used, and "Super Betsucomin G-821-
A thermosetting resin composition was prepared in the same manner as in Example 1 except that 50 parts of "60" were used. This composition was coated on a tin plate to a dry film thickness of 40μ,
A transparent coating film was obtained by curing at 140°C for 20 minutes. This product had a pencil hardness of H and a crosslinking density of 2.08×10 -3 mol/cm 3 . Comparative Example 4 A transparent coating film was obtained in the same manner as in Example 2, except that the alkyd resin varnish obtained in Comparative Example 2 was used instead of the alkyd resin varnish obtained in Reference Example 3. The pencil hardness of this product is HB and the crosslink density is 1.22.
×10 -3 mol/cm 3 . Example 3 Instead of using the alkyd resin varnish obtained in Reference Example 2, Reference Examples 4, 5, 6, 8, 9, 10, 11,
Using 133 parts of the resin obtained in Steps 12, 13, and 14 (114 parts of the resin in Reference Example 8),
Various transparent coating films were obtained in the same manner as in Example 1 except that 33 parts of "821-60" were used and the heat curing temperature was 120°C. The residual content of acetone extracted using a Soxhlet extractor was 87% or more in all cases. Examples 4 and 5 and Comparative Example 5 50 parts of the alkyd resin varnish obtained in Reference Examples 1 and 7 and Comparative Example 1 were added with 27 parts of titanium oxide pigment ("Tipeque R-820" manufactured by Ishihara Sangyo Co., Ltd.) and calcium carbonate. 10 parts of pigment (“heavy charcoal” manufactured by Maruo Calcium Co., Ltd.),
0.3 parts of lead naphthenate and 8 parts of an aliphatic hydrocarbon mixed solvent ("Tokusol" manufactured by Nippon Oil Co., Ltd.) were blended and mixed for 30 minutes using a paint conditioner to obtain a white paint composition. This material is coated on a steel plate with a dry film thickness.
Table 3 shows the properties when coated to a thickness of 40μ and dried at room temperature.
【表】
実施例 ６
参考例３で得たアルキド樹脂ワニス225部にア
ンスラキノン系赤色顔料（チバ社製「クロモフタ
ールレツドA3B」）90部、キシレン132部、エチ
レングリコールモノブチルエーテル53部を加え、
ペイントコンデイシヨナーで２時間混合分散して
粗粒5μの赤色顔料分散ペーストを得た。
上記顔料分散ペースト28部に参考例３で得たア
ルキド樹脂ワニス40部と「スーパーベツカミンＧ
―821―60」28部をラボミキサーで撹拌しながら
加え、20分間混合して赤色熱硬化性塗料組成物を
得た。
上記塗料組成物を、予めアルキド―メラミン型
中塗塗料（日本ペイント社製「OTO―778」）で
塗装した鋼板上に、乾燥膜厚が40μになるように
塗装し、140℃に温度設定した焼付炉に20分間入
れて焼付乾燥し、赤色の塗膜を得た。
比較対称のため、参考例３で得たアルキド樹脂
ワニスのかわりに比較例２で得たアルキド樹脂ワ
ニスを用い、ペイントコンデイシヨナーでの混合
分散を３時間行なう以外は同様にして赤色顔料分
散ペーストと塗料組成物および焼付塗膜を得た。
上記ペースト、塗料組成物および塗膜の諸特性
を表４に示す。[Table] Example 6 To 225 parts of the alkyd resin varnish obtained in Reference Example 3, 90 parts of an anthraquinone red pigment ("Chromophthal Red A3B" manufactured by Ciba), 132 parts of xylene, and 53 parts of ethylene glycol monobutyl ether were added. In addition,
The mixture was mixed and dispersed using a paint conditioner for 2 hours to obtain a red pigment dispersion paste with coarse particles of 5 μm. 28 parts of the above pigment dispersion paste, 40 parts of the alkyd resin varnish obtained in Reference Example 3 and "Super Betsucomin G"
-821-60'' was added while stirring using a lab mixer, and mixed for 20 minutes to obtain a red thermosetting coating composition. The above coating composition was applied to a steel plate that had been previously coated with an alkyd-melamine type intermediate coating paint ("OTO-778" manufactured by Nippon Paint Co., Ltd.) to a dry film thickness of 40μ, and baked at a temperature of 140℃. It was baked and dried in an oven for 20 minutes to obtain a red coating. For comparison purposes, a red pigment dispersion paste was prepared in the same manner except that the alkyd resin varnish obtained in Comparative Example 2 was used instead of the alkyd resin varnish obtained in Reference Example 3, and mixing and dispersion with a paint conditioner was carried out for 3 hours. A coating composition and a baked coating were obtained. Table 4 shows the properties of the paste, coating composition, and coating film.
【表】
実施例 ７
参考例12で得たアルキド樹脂ワニス70部にペリ
レン系赤色顔料（BASF社製「パリオーゲンマル
ーン4020」）47部、「ソルベツソ―100」69部、ｎ
―ブタノール14部を加え、ペイントコンデイシヨ
ナーで２時間混合分散して粗粒5μの赤色顔料ペ
ーストを得た。
上記顔料ペースト28部に参考例12で得たアルキ
ド樹脂ワニス40部と「スーパーベツカミンＧ―
821―60」28部をラボミキサーで撹拌しながなら
加え、20分間混合して赤色熱硬化性塗料組成物を
得た。
上記塗料組成物を、予め「OTO―778」で塗装
した鋼板上に、乾燥膜厚が40μになるように塗装
し、140℃に温度設定した焼付炉に20分間入れて
焼付乾燥し、赤色の塗膜を得た。
比較対称のため、参考例12で得たアルキド樹脂
ワニスのかわりに比較例３で得たアルキド樹脂ワ
ニスを用い、ペイントコンデイシヨナーでの混合
分散を３時間行なう以外は同様にして赤色顔料ペ
ーストと塗料組成物および焼付塗膜を得た。
上記塗料組成物および塗膜の諸特性を表５に示
す。[Table] Example 7 70 parts of the alkyd resin varnish obtained in Reference Example 12, 47 parts of perylene red pigment (BASF's "Pariogen Maroon 4020"), 69 parts of "Solbetsuso 100", n
-14 parts of butanol was added and mixed and dispersed for 2 hours using a paint conditioner to obtain a red pigment paste with coarse particles of 5μ. Add 40 parts of the alkyd resin varnish obtained in Reference Example 12 to 28 parts of the above pigment paste and
821-60'' were added while stirring using a lab mixer and mixed for 20 minutes to obtain a red thermosetting coating composition. The above coating composition was applied to a steel plate previously coated with "OTO-778" so that the dry film thickness was 40μ, and baked in a baking oven set at 140℃ for 20 minutes to dry. A coating film was obtained. For comparison purposes, the alkyd resin varnish obtained in Comparative Example 3 was used instead of the alkyd resin varnish obtained in Reference Example 12, and the red pigment paste and the red pigment paste were prepared in the same manner except that the alkyd resin varnish obtained in Comparative Example 3 was mixed and dispersed in a paint conditioner for 3 hours. A coating composition and a baked coating were obtained. Table 5 shows the properties of the above coating composition and coating film.
Claims (1)
ルキレン基、フエニレン基または置換フエニレン
基を表わす。〕 で示される両性イオン基を有するアルキド樹脂を
主成分とすることを特徴とする塗料組成物。 ２ 樹脂分子中に式、 〔式中、ＡはC1〜C6の直鎖もしくは分枝状ア
ルキレン基、フエニレン基または置換フエニレン
基を表わす。〕 で示される両性イオン基を有するアルキド樹脂
100重量部およびアミノプラスト樹脂５〜100重量
部を主成分とすることを特徴とする塗料組成物。 ３ 焼付乾燥型の塗料組成物として適用する上記
第２項記載の組成物。[Claims] 1. In the resin molecule, the formula, [In the formula, A represents a C 1 to C 6 linear or branched alkylene group, phenylene group, or substituted phenylene group. ] A coating composition characterized by containing as a main component an alkyd resin having an amphoteric ionic group represented by the following. 2 Formula in the resin molecule, [In the formula, A represents a C 1 to C 6 linear or branched alkylene group, phenylene group, or substituted phenylene group. ] An alkyd resin having a zwitterionic group represented by
A coating composition characterized in that the main components are 100 parts by weight and 5 to 100 parts by weight of an aminoplast resin. 3. The composition according to item 2 above, which is applied as a bake-drying paint composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11086579A JPS5634725A (en) | 1979-08-30 | 1979-08-30 | Alkyd resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11086579A JPS5634725A (en) | 1979-08-30 | 1979-08-30 | Alkyd resin |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2673689A Division JPH02630A (en) | 1989-02-07 | 1989-02-07 | Alkyd resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5634725A JPS5634725A (en) | 1981-04-07 |
| JPH0127107B2 true JPH0127107B2 (en) | 1989-05-26 |
Family
ID=14546633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11086579A Granted JPS5634725A (en) | 1979-08-30 | 1979-08-30 | Alkyd resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5634725A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56151727A (en) * | 1980-04-26 | 1981-11-24 | Nippon Paint Co Ltd | Novel oil free-polyester and its preparation |
| JPH0441105U (en) * | 1990-08-06 | 1992-04-08 |
-
1979
- 1979-08-30 JP JP11086579A patent/JPS5634725A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5634725A (en) | 1981-04-07 |
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