JPS6154343B2 - - Google Patents
Info
- Publication number
- JPS6154343B2 JPS6154343B2 JP9719280A JP9719280A JPS6154343B2 JP S6154343 B2 JPS6154343 B2 JP S6154343B2 JP 9719280 A JP9719280 A JP 9719280A JP 9719280 A JP9719280 A JP 9719280A JP S6154343 B2 JPS6154343 B2 JP S6154343B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- hydroxyethyl
- alkyl substituted
- bis
- parts
- 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
- 229920001225 polyester resin Polymers 0.000 claims description 28
- 239000004645 polyester resin Substances 0.000 claims description 28
- 239000000839 emulsion Substances 0.000 claims description 24
- 239000003995 emulsifying agent Substances 0.000 claims description 17
- 239000004925 Acrylic resin Substances 0.000 claims description 12
- 229920000178 Acrylic resin Polymers 0.000 claims description 12
- 239000008199 coating composition Substances 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 12
- 239000012736 aqueous medium Substances 0.000 claims description 7
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 5
- 229920000877 Melamine resin Polymers 0.000 claims description 2
- 239000004640 Melamine resin Substances 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000005650 substituted phenylene 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
- 239000002253 acid Substances 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 19
- -1 oxirane compound Chemical class 0.000 description 18
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 11
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 5
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 241000894007 species Species 0.000 description 5
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 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
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction 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
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229920003180 amino resin Polymers 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 125000003010 ionic group Chemical group 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 150000007519 polyprotic acids Polymers 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- AJTVSSFTXWNIRG-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanesulfonic acid Chemical compound OCC[NH+](CCO)CCS([O-])(=O)=O AJTVSSFTXWNIRG-UHFFFAOYSA-N 0.000 description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 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
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-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
- 150000007513 acids Chemical class 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 238000010556 emulsion polymerization method Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 150000008040 ionic compounds Chemical class 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
- 239000000944 linseed oil Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000003813 safflower oil Substances 0.000 description 2
- 235000005713 safflower oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 229960003080 taurine Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 239000002383 tung oil Substances 0.000 description 2
- WJZMWKFYCKUIFG-UHFFFAOYSA-N (1,3-dihydroxybutan-2-ylamino)methanesulfonic acid Chemical compound CC(O)C(CO)NCS(O)(=O)=O WJZMWKFYCKUIFG-UHFFFAOYSA-N 0.000 description 1
- PKZDOMDVIGMNRK-UHFFFAOYSA-N (1,3-dihydroxypropan-2-ylamino)methanesulfonic acid Chemical compound OCC(CO)NCS(O)(=O)=O PKZDOMDVIGMNRK-UHFFFAOYSA-N 0.000 description 1
- ZRYQPUHICKOCHT-UHFFFAOYSA-N (1,4-dihydroxybutan-2-ylamino)methanesulfonic acid Chemical compound OCCC(CO)NCS(O)(=O)=O ZRYQPUHICKOCHT-UHFFFAOYSA-N 0.000 description 1
- ATCHKIMLWBNVAG-UHFFFAOYSA-N (1,5-dihydroxypentan-2-ylamino)methanesulfonic acid Chemical compound OCCCC(CO)NCS(O)(=O)=O ATCHKIMLWBNVAG-UHFFFAOYSA-N 0.000 description 1
- HJBQUHBIKSCKCX-UHFFFAOYSA-N (1-hydroxypropan-2-ylamino)methanesulfonic acid Chemical compound OCC(C)NCS(O)(=O)=O HJBQUHBIKSCKCX-UHFFFAOYSA-N 0.000 description 1
- CKFNBZXQTFWLFR-UHFFFAOYSA-N (2,3-dihydroxypropylamino)methanesulfonic acid Chemical compound OCC(O)CNCS(O)(=O)=O CKFNBZXQTFWLFR-UHFFFAOYSA-N 0.000 description 1
- JBOWGOOXLSDXHE-UHFFFAOYSA-N (2-hydroxyethylamino)methanesulfonic acid Chemical compound OCCNCS(O)(=O)=O JBOWGOOXLSDXHE-UHFFFAOYSA-N 0.000 description 1
- RIDJPQGDTBCLEB-UHFFFAOYSA-N (2-hydroxypentylamino)methanesulfonic acid Chemical compound CCCC(O)CNCS(O)(=O)=O RIDJPQGDTBCLEB-UHFFFAOYSA-N 0.000 description 1
- PQAQSDMCVNNRPF-UHFFFAOYSA-N (2-hydroxypropylamino)methanesulfonic acid Chemical compound CC(O)CNCS(O)(=O)=O PQAQSDMCVNNRPF-UHFFFAOYSA-N 0.000 description 1
- ZYKSOHSRGWRHSL-UHFFFAOYSA-N (3-hydroxybutan-2-ylamino)methanesulfonic acid Chemical compound CC(O)C(C)NCS(O)(=O)=O ZYKSOHSRGWRHSL-UHFFFAOYSA-N 0.000 description 1
- ZZGGNGUMBKOMNR-UHFFFAOYSA-N (3-hydroxypropylamino)methanesulfonic acid Chemical compound OCCCNCS(O)(=O)=O ZZGGNGUMBKOMNR-UHFFFAOYSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- 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
- 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
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
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- 239000003784 tall oil Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 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
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9719280A JPS5721464A (en) | 1980-07-15 | 1980-07-15 | Paint composition |
| CA000381657A CA1194638A (en) | 1980-07-15 | 1981-07-14 | Aqueous emulsification of solids by use of a polyester emulsifier |
| DE3153333A DE3153333C2 (zh) | 1980-07-15 | 1981-07-15 | |
| US06/283,743 US4368287A (en) | 1980-07-15 | 1981-07-15 | Emulsifier and compositions comprising same |
| GB8121990A GB2080816B (en) | 1980-07-15 | 1981-07-15 | Polyesters and their use as emulsifiers |
| DE19813127919 DE3127919A1 (de) | 1980-07-15 | 1981-07-15 | Emulgator und diesen enthaltende mischungen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9719280A JPS5721464A (en) | 1980-07-15 | 1980-07-15 | Paint composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5721464A JPS5721464A (en) | 1982-02-04 |
| JPS6154343B2 true JPS6154343B2 (zh) | 1986-11-21 |
Family
ID=14185714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9719280A Granted JPS5721464A (en) | 1980-07-15 | 1980-07-15 | Paint composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5721464A (zh) |
-
1980
- 1980-07-15 JP JP9719280A patent/JPS5721464A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5721464A (en) | 1982-02-04 |
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