JPH0312092B2 - - Google Patents
Info
- Publication number
- JPH0312092B2 JPH0312092B2 JP2673689A JP2673689A JPH0312092B2 JP H0312092 B2 JPH0312092 B2 JP H0312092B2 JP 2673689 A JP2673689 A JP 2673689A JP 2673689 A JP2673689 A JP 2673689A JP H0312092 B2 JPH0312092 B2 JP H0312092B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- hydroxyethyl
- bis
- alkyl substituted
- alkyd resin
- 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 59
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 229920005989 resin Polymers 0.000 claims description 20
- 239000011347 resin Substances 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 15
- 239000000194 fatty acid Substances 0.000 claims description 15
- 229930195729 fatty acid Natural products 0.000 claims description 15
- 150000004665 fatty acids Chemical class 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000010685 fatty oil Substances 0.000 claims description 3
- 125000002947 alkylene group Chemical group 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
- 239000002966 varnish Substances 0.000 description 23
- 238000000576 coating method Methods 0.000 description 18
- 239000011248 coating agent Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- 239000000049 pigment Substances 0.000 description 14
- -1 methylcyclohexentricarboxylic anhydride Chemical class 0.000 description 13
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 12
- 239000008199 coating composition Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 239000003973 paint Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- 239000011342 resin composition Substances 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 229920003180 amino resin Polymers 0.000 description 7
- 239000001054 red pigment Substances 0.000 description 7
- 229920001187 thermosetting polymer Polymers 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000003010 ionic group Chemical group 0.000 description 6
- 235000019198 oils Nutrition 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
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920000642 polymer Polymers 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
- 239000004606 Fillers/Extenders Substances 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
- 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
- 238000002156 mixing Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000003960 organic solvent Substances 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
- 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
- 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
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-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
- 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
- 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
- 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
- 239000000945 filler Substances 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
- 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
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 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
- 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
- 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
- ZZGGNGUMBKOMNR-UHFFFAOYSA-N (3-hydroxypropylamino)methanesulfonic acid Chemical compound OCCCNCS(O)(=O)=O ZZGGNGUMBKOMNR-UHFFFAOYSA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 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
- 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
- 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
- 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
- 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
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- 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
- 239000004640 Melamine resin Substances 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
- 229910006069 SO3H Inorganic materials 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
- 239000007983 Tris buffer Substances 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
- 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
- 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
- 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
- 238000005260 corrosion Methods 0.000 description 1
- 238000001723 curing Methods 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
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001747 exhibiting effect Effects 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
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 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
- 239000004033 plastic Substances 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 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
- 125000001424 substituent group Chemical group 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
- 239000003784 tall oil Substances 0.000 description 1
- 229960003080 taurine Drugs 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
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 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
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2673689A JPH02630A (ja) | 1989-02-07 | 1989-02-07 | アルキド樹脂の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2673689A JPH02630A (ja) | 1989-02-07 | 1989-02-07 | アルキド樹脂の製造法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11086579A Division JPS5634725A (en) | 1979-08-30 | 1979-08-30 | Alkyd resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02630A JPH02630A (ja) | 1990-01-05 |
| JPH0312092B2 true JPH0312092B2 (fr) | 1991-02-19 |
Family
ID=12201592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2673689A Granted JPH02630A (ja) | 1989-02-07 | 1989-02-07 | アルキド樹脂の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02630A (fr) |
-
1989
- 1989-02-07 JP JP2673689A patent/JPH02630A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02630A (ja) | 1990-01-05 |
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