JPS646222B2 - - Google Patents
Info
- Publication number
- JPS646222B2 JPS646222B2 JP3166181A JP3166181A JPS646222B2 JP S646222 B2 JPS646222 B2 JP S646222B2 JP 3166181 A JP3166181 A JP 3166181A JP 3166181 A JP3166181 A JP 3166181A JP S646222 B2 JPS646222 B2 JP S646222B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- alkyd resin
- water
- resin
- oil
- 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 24
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims description 21
- 239000004334 sorbic acid Substances 0.000 claims description 21
- 229940075582 sorbic acid Drugs 0.000 claims description 21
- 235000010199 sorbic acid Nutrition 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 12
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
- 239000000194 fatty acid Substances 0.000 claims description 7
- 229930195729 fatty acid Natural products 0.000 claims description 7
- 150000004665 fatty acids Chemical class 0.000 claims description 7
- 229920005862 polyol Polymers 0.000 claims description 7
- 150000003077 polyols Chemical class 0.000 claims description 7
- 239000002243 precursor Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000003973 paint Substances 0.000 description 14
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229920001225 polyester resin Polymers 0.000 description 4
- 239000004645 polyester resin Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 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
- 150000007514 bases Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000003549 soybean oil Substances 0.000 description 3
- 235000012424 soybean oil Nutrition 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- 229920000298 Cellophane Polymers 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 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
- 229920000877 Melamine resin Polymers 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000010304 firing Methods 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 229940044600 maleic anhydride Drugs 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-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
- 239000000049 pigment Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- -1 that is Chemical compound 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 239000004246 zinc acetate Substances 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- CUXYLFPMQMFGPL-UHFFFAOYSA-N (9Z,11E,13E)-9,11,13-Octadecatrienoic acid Natural products CCCCC=CC=CC=CCCCCCCCC(O)=O CUXYLFPMQMFGPL-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-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
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-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
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000004135 Bone phosphate Substances 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- CUXYLFPMQMFGPL-SUTYWZMXSA-N all-trans-octadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-SUTYWZMXSA-N 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- JCHMFMSWRWHRFI-HMMYKYKNSA-N ethyl (2e)-2-[(2,5-dichlorophenyl)hydrazinylidene]-2-(2,6-dimethylmorpholin-4-yl)acetate Chemical group C1C(C)OC(C)CN1/C(C(=O)OCC)=N/NC1=CC(Cl)=CC=C1Cl JCHMFMSWRWHRFI-HMMYKYKNSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 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 1
- 150000002334 glycols Chemical class 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- HTUMBQDCCIXGCV-UHFFFAOYSA-N lead oxide Chemical compound [O-2].[Pb+2] HTUMBQDCCIXGCV-UHFFFAOYSA-N 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N lead(II) oxide Inorganic materials [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 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
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
- Paints Or Removers (AREA)
Description
本発明はソルビン酸と無水マレイン酸とを必須
成分とする塗料用樹脂として好適な水希釈型アル
キツド樹脂の製造法に関する。
ソルビン酸と無水マレイン酸又はソルビン酸と
無水マレイン酸との付加反応物を用いたポリエス
テル樹脂の製造法は、特公昭46−25866号公報、
特公昭49−2998号公報にて知られている。
しかしながらソルビン酸と無水マレイン酸との
付加反応物、即ちメチルシクロヘキサン三塩基性
カルボン酸(以下MHTAと略称する)を用いる
場合には、無水MHTAと多価アルコールを混合
加熱してポリエステル樹脂を製造する工程、また
該ポリエステル樹脂を塩基性物質で水溶化する工
程において、場合によつてはミクロゲルと称する
ゲル状の粒子や白濁を生じるという問題があり、
またこれらの欠点を解決するためのソルビン酸と
無水マレイン酸またはマレイン酸に多価アルコー
ルを同時に反応させてポリエステル樹脂を製造す
る方法においては、イソフタル酸、テレフタル酸
等の粉末状ジカルボン酸は未反応粉末の状態で残
り易く、反応を進めるとゲル化するなどして水希
釈性を損なうという欠点がある。
しかして本発明者らは、これらの問題を解決す
べく鋭意検討を重ねたところ、まず(A)油あるいは
脂肪酸と(B)ポリオールと(C)ジカルボン酸とから酸
価80以下(KOHmg/g)のアルキツド樹脂前駆
体を製造したのち、次いで水酸基とカルボキシル
基に不活性で且つソルビン酸を溶解する溶剤の存
在下、(D)ソルビン酸と無水マレイン酸を添加反応
せしめることによつてのみ、得られた樹脂を塗料
用樹脂として用いた場合に、塗膜の硬度、可撓
性、防錆性、耐水性等が一段と向上するという優
れた効果を得るにいたり、本発明を完成した。
本発明におけるアルキツド樹脂前駆体は、(A)
油、脂肪酸、(B)ポリオール、(C)ジカルボン酸をエ
ステル化反応することによつて得られる。まず(A)
として油を用いる場合には、重量比で油を0.6以
下、ポリオールを0.2〜0.5、ジカルボン酸を0.2〜
0.5の割合で、触媒としてリサージなどを用い、
温度240〜260℃で約2時間位エステル交換反応す
る必要がある。次いで必要に応じて酢酸亜鉛等の
エステル化触媒を用いて190〜260℃で約2〜6時
間加熱して酸価80以下(KOHmg/g)、好ましく
は5〜40の範囲になるまで反応する。酸価が80を
越える場合にはジカルボン酸が固体状で残存し、
これが塗膜物性に悪影響を及ぼす。(A)として脂肪
酸を用いる場合には、重量比で脂肪酸を0.6以下、
ポリオールを0.2〜0.5、ジカルボン酸を0.2〜0.5
の割合で、必要に応じて酢酸亜鉛等のエステル化
触媒を用い、温度190〜260℃で約2〜6時間位反
応する。以後の反応は前記同様に行なう。前記ジ
カルボン酸として、イソフタル酸を用いる場合に
は、酸価を35以下、テレフタル酸を用いる場合に
は、酸価が15以下とすることが未反応物をなくす
るために肝要である。
次にアルキツド樹脂前駆体からアルキツド樹脂
を得る際は、前記にてアルキツド樹脂前駆体を製
造した工程にて、それに引続き温度60〜140℃に
て、水酸基とカルボキシル基に不活性で且つソル
ビン酸を溶解する溶剤、具体的にはジオキサン、
ジメチルスルホオキシド、アセトンなどをアルキ
ツド樹脂前駆体に対して0.1〜10重量%、好まし
くは0.5〜5重量%の割合にて添加する。そして
これにソルビン酸と無水マレイン酸とを等モルの
割合で仕込成分全量の5〜50重量%、好ましくは
10〜30重量%添加し、徐々に約150〜180℃にて添
加した溶剤を留去しながら昇温し、酸価30〜70
(KOHmg/g)のアルキツド樹脂が得られるまで
反応する。前記のソルビン酸は、添加された溶剤
の還流によつて反応缶の上部に未反応のまゝで附
着することは全く認められない。
本発明における(A)油、脂肪酸としては、あまに
油、大豆油、ひまし油、やし油、トール油、綿実
油、桐油、糠油及び上記油の脂肪酸、ステアリン
酸、エレオステアリン酸、オレイン酸、リノール
酸、リシノレイン酸、リノレイン酸、ラウリル
酸、ミリスチン酸、カプリン酸、カプリル酸など
があげられ、これら1種又は2種以上併用され
る。
(B)ポリオールとしては、2価あるいはそれ以上
の水酸基を有する公知のポリオールである。具体
的には、エチレングリコール、プロピレングリコ
ール、ジエチレングリコール、トリエチレングリ
コール、ブチレングリコール、ヘキサメチレング
リコール、ネオペンチルグリコール、シクロヘキ
サンジメタノール、水添ビスフエノールA、グリ
セリン、ジグリセリン、トリメチロールエタン、
トリメチロールプロパン、1,2,6―ヘキサン
トリオール、ペンタエリスリトール、ソルビトー
ル、ジペンタエリスリトールなどがあげられ、こ
れら1種又は2種以上併用される。
(C)ジカルボン酸としては、フタル酸、イソフタ
ル酸、テレフタル酸、コハク酸、グルタル酸、ア
ジピン酸、スベリン酸、セバシン酸、イタコン
酸、マレイン酸、フマール酸、ジメチロールプロ
ピオン酸などがあげられ、これら1種又は2種以
上併用される。
本発明におけるアルキツド樹脂は、粘稠な液体
ないし固体であり、アルコール類、ケトン類及び
これらと脂肪族または芳香族炭化水素との混合物
に対し可溶であるから、これらのうちの水可溶性
有機溶剤および/または水などに溶解または分散
してから、塩基性化合物にて中和し水希釈アルキ
ツド樹脂とする。具体的にはアルコール類、ケト
ン類、グリコール類、セルソルブアセテートなど
のエステルおよび/または水にアルキツド樹脂を
溶解あるいは分散し、揮発性の塩基性化合物に
て、PH6〜10好ましくは6〜8に調整する。前記
塩基性化合物としては、アンモニヤ、メチルアミ
ン、エチルアミン、ジエチルアミン、トリエチル
アミン、ブチルアミンなどのアルキルアミン、モ
ノエタノールアミン、ジエタノールアミン、トリ
エタノールアミン、プロパノールアミン、アミノ
メチルプロパノールなどのアルカノールアミン類
やモルホリン、ピリジン、ピペリジンなどがあげ
られ、反応性及び揮発温度に応じて適宜選択され
る。
前記水希釈アルキツド樹脂は、メラミン―フオ
ルムアルデヒド樹脂、グアナミン―フオルムアル
デヒド樹脂、尿素―フオルムアルデヒド樹脂など
のアミノ樹脂さらにフエノール樹脂などを混合し
変性することによつて、アルキツド樹脂単独より
も塗膜硬度、低温硬化性等が向上するのでその使
用が好ましい。その他用途に応じてレベリング
剤、消泡剤、分散剤、タレ防止剤、増粘剤等の添
加剤や炭酸カルシウム、カーボンブラツク、酸化
チタン等の顔料を適宜添加することができる。
本発明における水希釈型アルキツド樹脂は、塗
料用樹脂として用いられると、硬度、可撓性、防
錆性、耐水性等に優れたものであるから、金属容
器、車輛、事務機器、家庭電気製品、金属板、な
どの金属品の塗料ビヒクルとして好適なものであ
る。
次に実施例によつて本発明を具体的に説明す
る。尚例中「部」とあるのは特にことわりのない
限り「重量部」を表わす。
実施例 1
撹拌機、温度計、窒素吹込管、水冷コンデンサ
ーを付した1容フラスコに、大豆油132部、ト
リメチロールプロパン114部、リサーヂ1部を仕
込み240℃で2時間エステル交換反応を行なつた。
内温を150℃まで低げてからイソフタル酸133部を
添加し徐々に加熱した。200℃で4時間反応し酸
価20(KOHmg/g)の清澄な樹脂が得られた。次
いで80℃まで冷却してからジオキン酸8部、ソル
ビン酸22部、無水マレイン酸20部を加えジオキサ
ンを溜去しながら170℃まで2時間を要して昇温
したのち、この温度で2時間反応して、酸価60
(KOHmg/g)のアルキツド樹脂を得た。ソルビ
ン酸添加後のフラスコ上部にはソルビン酸の昇華
物は全く認められなかつた。このアルキツド樹脂
にブチルセロソルブを加えて70重量%溶液とし
た。該樹脂溶液100部にトリエチルアミン7部、
スミマールM50W(住友化学製のメラミン―フオ
ルムアルデヒド樹脂)22部、カーボンブラツク
MA100(三菱化成製)4.6部を加え、充分混練し
顔料を分散させた後に水150部を加えてNo.4フオ
ードカツプ粘度30秒の水性黒色塗料を得た。
該塗料をエアースプレーにて磨き軟鋼板に乾燥
膜厚が20〜30μになるように塗布したのち、140
℃で20分間焼付した。得られた塗膜物性を測定し
第1表に記載した。
対照例 1
実施例1においてジオキサンを添加しないほか
は実施例1と同様にしてアルキツド樹脂の製造を
行なつた。ソルビン酸、無水マレイン酸を添加し
た後の昇温過程中110℃付近からソルビン酸が多
量に昇華し、フラスコ上部壁に付着した。この
まゝ昇温を続け170℃で2時間反応して酸価60
(KOHmg/g)のアルキツド樹脂を得た。このア
ルキツド樹脂にはフラスコ上部壁に付着していた
ソルビン酸の混入が認められた。以後実施例1と
同様にして塗料化、その塗膜物性を第1表に記載
した。
対照例 2
実施例1においてジオキサンに替えてベンゼン
を用いたほかは実施例1と同様にしてアルキツド
樹脂を得た。該アルキツド樹脂にもソルビン酸の
混入が認められた。実施例1と同様にして塗料化
し、その塗膜物性を第1表に記載した。
対照例 3
実施例1において大豆油とトリメチロールプロ
パンとを反応させエステル交換した後に、イソフ
タル酸、無水マレイン酸、ソルビン酸を実施例1
と同じ割合にて一括に仕込み反応を行なつた。昇
温過程中110℃付近からソルビン酸が昇華し、フ
ラスコ上部壁に付着したが、200℃付近からのエ
ステル化反応による生成水によつて反応物中に混
入した。またこの反応物は酸価60(KOHmg/g)
の段階ではイソフタル酸が残存しているスラリー
状のものであつたので、さらに反応を行なつたと
ころ、スラリー状態のまゝ酸価35の段階でゲル化
した。
(注) 塗膜物性測定方法
1 密着性:塗膜にゴバン目状の切目を1mm間隔
につけ、その上にセロテープを一たん貼りつけ
てからはがし、はがれ残つたゴバンの目数を
100目当りで表わす。
2 エリクセン:エリクセン試験機により直径1
インチのポンチを塗膜の表面から押出し、塗膜
表面に傷がつく最長の押出距離(mm)
3 デユポン衝撃:デユポン式衝撃試験機により
500gのおもりをR1/2インチの撃芯上に落下さ
せ、撃芯により塗面が傷つかない最高の落下高
さ(cm)
4 40℃耐水性:40℃の温水に48時間浸漬後の塗
膜の状態観察。
5 耐ソルトスプレー性:塗面にクロスカツトを
付し塗膜上に5%の食塩水を噴霧し、24時間毎
にクロスカツト部にセロハンテープを一たん貼
りつけてからはがした時の塗膜の剥離巾(mm)
The present invention relates to a method for producing a water-dilutable alkyd resin suitable as a paint resin containing sorbic acid and maleic anhydride as essential components. A method for producing polyester resin using an addition reaction product of sorbic acid and maleic anhydride or sorbic acid and maleic anhydride is described in Japanese Patent Publication No. 46-25866,
It is known from Japanese Patent Publication No. 49-2998. However, when using an addition reaction product of sorbic acid and maleic anhydride, that is, methylcyclohexane tribasic carboxylic acid (hereinafter abbreviated as MHTA), polyester resin is produced by mixing and heating anhydrous MHTA and a polyhydric alcohol. In the process, and in the process of water-solubilizing the polyester resin with a basic substance, there is a problem that in some cases, gel-like particles called microgels or cloudiness are generated.
In addition, in the method of producing polyester resin by simultaneously reacting sorbic acid and maleic anhydride or maleic acid with a polyhydric alcohol to solve these drawbacks, powdered dicarboxylic acids such as isophthalic acid and terephthalic acid are unreacted. It has the disadvantage that it tends to remain in a powder state, and as the reaction progresses, it becomes gelled, impairing water dilutability. However, the present inventors conducted extensive studies to solve these problems and found that (A) oil or fatty acid, (B) polyol, and (C) dicarboxylic acid were combined with an acid value of 80 or less (KOHmg/g). ) After producing the alkyd resin precursor of (D), in the presence of a solvent that is inert to the hydroxyl and carboxyl groups and dissolves sorbic acid, only by adding and reacting (D) sorbic acid and maleic anhydride, When the obtained resin is used as a coating resin, the present invention has been completed by obtaining an excellent effect of further improving the hardness, flexibility, rust prevention, water resistance, etc. of the coating film. The alkyd resin precursor in the present invention is (A)
It is obtained by esterifying oil, fatty acid, (B) polyol, and (C) dicarboxylic acid. First (A)
When using oil as an oil, the weight ratio of oil is 0.6 or less, polyol is 0.2 to 0.5, and dicarboxylic acid is 0.2 to 0.5.
Using Resurge etc. as a catalyst at a ratio of 0.5,
It is necessary to carry out the transesterification reaction at a temperature of 240 to 260°C for about 2 hours. Then, if necessary, use an esterification catalyst such as zinc acetate and heat at 190 to 260°C for about 2 to 6 hours to react until the acid value reaches 80 or less (KOHmg/g), preferably in the range of 5 to 40. . If the acid value exceeds 80, the dicarboxylic acid remains in solid form,
This adversely affects the physical properties of the coating film. When using fatty acids as (A), the weight ratio of fatty acids is 0.6 or less,
0.2-0.5 for polyol, 0.2-0.5 for dicarboxylic acid
The reaction is carried out at a temperature of 190 to 260°C for about 2 to 6 hours, using an esterification catalyst such as zinc acetate if necessary. The subsequent reactions are carried out in the same manner as described above. When using isophthalic acid as the dicarboxylic acid, it is important to keep the acid value at 35 or less, and when using terephthalic acid, it is important to keep the acid value at 15 or less in order to eliminate unreacted substances. Next, when obtaining an alkyd resin from an alkyd resin precursor, in the step of manufacturing the alkyd resin precursor described above, sorbic acid that is inert to hydroxyl groups and carboxyl groups is added at a temperature of 60 to 140°C. Solvents that dissolve, specifically dioxane,
Dimethyl sulfoxide, acetone, etc. are added in a proportion of 0.1 to 10% by weight, preferably 0.5 to 5% by weight, based on the alkyd resin precursor. Then, add sorbic acid and maleic anhydride in an equimolar ratio of 5 to 50% by weight of the total amount of ingredients, preferably
Add 10 to 30% by weight and gradually raise the temperature while distilling off the added solvent at approximately 150 to 180 °C to reach an acid value of 30 to 70.
(KOHmg/g) of alkyd resin is obtained. The sorbic acid was not observed to adhere unreacted to the upper part of the reaction vessel due to the reflux of the added solvent. In the present invention, (A) oils and fatty acids include linseed oil, soybean oil, castor oil, coconut oil, tall oil, cottonseed oil, tung oil, bran oil, fatty acids of the above oils, stearic acid, eleostearic acid, oleic acid, Examples include linoleic acid, ricinoleic acid, linoleic acid, lauric acid, myristic acid, capric acid, and caprylic acid, and one or more of these may be used in combination. The polyol (B) is a known polyol having a divalent or higher hydroxyl group. Specifically, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, butylene glycol, hexamethylene glycol, neopentyl glycol, cyclohexanedimethanol, hydrogenated bisphenol A, glycerin, diglycerin, trimethylol ethane,
Examples include trimethylolpropane, 1,2,6-hexanetriol, pentaerythritol, sorbitol, dipentaerythritol, and one or more of these may be used in combination. (C) Dicarboxylic acids include phthalic acid, isophthalic acid, terephthalic acid, succinic acid, glutaric acid, adipic acid, suberic acid, sebacic acid, itaconic acid, maleic acid, fumaric acid, dimethylolpropionic acid, etc. One or more of these may be used in combination. The alkyd resin in the present invention is a viscous liquid or solid, and is soluble in alcohols, ketones, and mixtures of these with aliphatic or aromatic hydrocarbons. And/or after dissolving or dispersing in water etc., it is neutralized with a basic compound to obtain a water diluted alkyd resin. Specifically, alkyd resin is dissolved or dispersed in esters such as alcohols, ketones, glycols, and cellosolve acetate, and/or water, and the pH is adjusted to 6 to 10, preferably 6 to 8, using a volatile basic compound. adjust. Examples of the basic compounds include alkylamines such as ammonia, methylamine, ethylamine, diethylamine, triethylamine, butylamine, alkanolamines such as monoethanolamine, diethanolamine, triethanolamine, propanolamine, and aminomethylpropanol, morpholine, pyridine, Examples include piperidine and the like, and are appropriately selected depending on reactivity and volatilization temperature. The water-diluted alkyd resin can be modified by mixing an amino resin such as a melamine-formaldehyde resin, a guanamine-formaldehyde resin, or a urea-formaldehyde resin, as well as a phenol resin, etc., to make it more effective than the alkyd resin alone. Its use is preferred because it improves coating film hardness, low-temperature curability, etc. Other additives such as leveling agents, antifoaming agents, dispersants, anti-sagging agents, thickeners, etc., and pigments such as calcium carbonate, carbon black, titanium oxide, etc. may be added as appropriate depending on the intended use. When the water-dilutable alkyd resin of the present invention is used as a paint resin, it has excellent hardness, flexibility, rust prevention, water resistance, etc., so it can be used in metal containers, vehicles, office equipment, and home appliances. It is suitable as a paint vehicle for metal products such as metal plates and metal plates. Next, the present invention will be specifically explained with reference to Examples. In addition, "parts" in the examples represent "parts by weight" unless otherwise specified. Example 1 132 parts of soybean oil, 114 parts of trimethylolpropane, and 1 part of litharge were charged into a 1-volume flask equipped with a stirrer, a thermometer, a nitrogen blowing tube, and a water-cooled condenser, and a transesterification reaction was carried out at 240°C for 2 hours. Ta.
After lowering the internal temperature to 150°C, 133 parts of isophthalic acid was added and gradually heated. After reacting at 200°C for 4 hours, a clear resin with an acid value of 20 (KOHmg/g) was obtained. Next, after cooling to 80°C, 8 parts of dioquinic acid, 22 parts of sorbic acid, and 20 parts of maleic anhydride were added, and the temperature was raised to 170°C over 2 hours while distilling off dioxane, and then at this temperature for 2 hours. React, acid value 60
(KOHmg/g) of alkyd resin was obtained. No sublimate of sorbic acid was observed in the upper part of the flask after addition of sorbic acid. Butyl cellosolve was added to this alkyd resin to form a 70% by weight solution. 7 parts of triethylamine to 100 parts of the resin solution,
Sumimaru M50W (melamine-formaldehyde resin manufactured by Sumitomo Chemical) 22 parts, carbon black
After adding 4.6 parts of MA100 (manufactured by Mitsubishi Kasei) and thoroughly kneading to disperse the pigment, 150 parts of water was added to obtain a No. 4 water-based black paint with a Ford Cup viscosity of 30 seconds. The paint was applied to a polished mild steel plate using air spray so that the dry film thickness was 20 to 30μ, and then
Baked for 20 minutes at ℃. The physical properties of the resulting coating film were measured and are listed in Table 1. Control Example 1 An alkyd resin was produced in the same manner as in Example 1 except that dioxane was not added. During the heating process after adding sorbic acid and maleic anhydride, a large amount of sorbic acid sublimated from around 110°C and adhered to the upper wall of the flask. Continue to raise the temperature and react at 170℃ for 2 hours until the acid value reaches 60.
(KOHmg/g) of alkyd resin was obtained. This alkyd resin was found to be contaminated with sorbic acid that had adhered to the upper wall of the flask. Thereafter, a coating was prepared in the same manner as in Example 1, and the physical properties of the coating film are listed in Table 1. Control Example 2 An alkyd resin was obtained in the same manner as in Example 1 except that benzene was used instead of dioxane. The alkyd resin was also found to be contaminated with sorbic acid. A paint was prepared in the same manner as in Example 1, and the physical properties of the paint film are listed in Table 1. Control Example 3 After reacting and transesterifying soybean oil and trimethylolpropane in Example 1, isophthalic acid, maleic anhydride, and sorbic acid were added to Example 1.
The reaction was carried out in batches at the same rate. During the heating process, sorbic acid sublimed from around 110°C and adhered to the upper wall of the flask, but from around 200°C it was mixed into the reaction product by the water produced by the esterification reaction. In addition, this reactant has an acid value of 60 (KOHmg/g)
At the stage , the mixture was in the form of a slurry with residual isophthalic acid, so when the reaction was further carried out, it turned into a gel at an acid value of 35 while remaining in the slurry state. (Note) Paint film physical property measurement method 1 Adhesion: Make gong-like cuts in the paint film at 1 mm intervals, apply cellophane tape on top of it, then peel it off, and measure the number of goblin marks that remain after peeling off.
Expressed in 100 hits. 2 Erichsen: Diameter 1 by Erichsen tester
The longest extrusion distance (mm) when an inch punch is extruded from the surface of the paint film to cause scratches on the paint film surface. 3 Dupont impact: By Dupont impact tester
Drop a 500g weight onto the R1/2 inch firing core, and the maximum drop height (cm) without damaging the paint surface due to the firing core 4 40℃ water resistance: Paint film after 48 hours immersion in 40℃ warm water Observation of the condition. 5. Salt spray resistance: Attach a cross cut to the painted surface, spray 5% salt water onto the paint film, apply cellophane tape to the cross cut part once every 24 hours, and then remove it. Peeling width (mm)
【表】【table】
Claims (1)
して、(A)と(B)と(C)から酸価80以下(KOHmg/g)
のアルキツド樹脂前駆体を製造したのち、次いで
水酸基とカルボキシル基に不活性で且つソルビン
酸を溶解する溶剤の存在下に(D)を添加反応せしめ
ることを特徴とする水希釈型アルキツド樹脂の製
造法。[Claims] 1. (A) Oil or fatty acid (B) Polyol (C) Dicarboxylic acid (D) When producing a water-dilutable alkyd resin consisting of sorbic acid and maleic anhydride, (A) and (B) and (C) with an acid value of 80 or less (KOHmg/g)
A method for producing a water-dilutable alkyd resin, which comprises producing an alkyd resin precursor, and then reacting the hydroxyl group and carboxyl group with (D) in the presence of an inert solvent that dissolves sorbic acid. .
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3166181A JPS57145122A (en) | 1981-03-04 | 1981-03-04 | Production water-thinnable alkyd resin |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3166181A JPS57145122A (en) | 1981-03-04 | 1981-03-04 | Production water-thinnable alkyd resin |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS57145122A JPS57145122A (en) | 1982-09-08 |
JPS646222B2 true JPS646222B2 (en) | 1989-02-02 |
Family
ID=12337323
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP3166181A Granted JPS57145122A (en) | 1981-03-04 | 1981-03-04 | Production water-thinnable alkyd resin |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS57145122A (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3246616A1 (en) * | 1982-12-16 | 1984-06-20 | Henkel KGaA, 4000 Düsseldorf | POLYOL MODIFIED ALKYD RESIN FOR USE IN WATER PAINT |
DE3414244C2 (en) * | 1984-04-14 | 1994-02-10 | Desowag Materialschutz Gmbh | Wood preservative paint, preferably wood preservative paint |
JPH0699649B2 (en) * | 1985-06-17 | 1994-12-07 | 早川ゴム株式会社 | Anticorrosion paint composition |
JPS63122765A (en) * | 1986-11-11 | 1988-05-26 | Dainippon Toryo Co Ltd | Alkyd resin composition for coating |
JPH07102558A (en) * | 1993-09-30 | 1995-04-18 | Soken:Kk | Pile for civil engineering work |
CN108359361A (en) * | 2018-01-30 | 2018-08-03 | 华南理工大学 | Sorbic acid/nanometer particle-modified aqueous alkide resin and preparation method and application |
EP3766914A1 (en) * | 2019-07-16 | 2021-01-20 | PPG Europe B.V. | A coating composition |
-
1981
- 1981-03-04 JP JP3166181A patent/JPS57145122A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS57145122A (en) | 1982-09-08 |
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