CA1201848A - Water dilutable cathodic depositable resinous binder production and use - Google Patents
Water dilutable cathodic depositable resinous binder production and useInfo
- Publication number
- CA1201848A CA1201848A CA000375383A CA375383A CA1201848A CA 1201848 A CA1201848 A CA 1201848A CA 000375383 A CA000375383 A CA 000375383A CA 375383 A CA375383 A CA 375383A CA 1201848 A CA1201848 A CA 1201848A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- group
- alkyl
- double bond
- epoxy
- 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
- 239000011230 binding agent Substances 0.000 title claims abstract description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 235000020354 squash Nutrition 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 150000001412 amines Chemical class 0.000 claims abstract description 27
- 238000004070 electrodeposition Methods 0.000 claims abstract description 23
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 239000000178 monomer Substances 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 11
- 125000001302 tertiary amino group Chemical group 0.000 claims abstract description 10
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 7
- 238000004132 cross linking Methods 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 43
- 238000000576 coating method Methods 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 239000000243 solution Substances 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- -1 hydroxyalkyl ester Chemical class 0.000 claims description 18
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 239000011248 coating agent Substances 0.000 claims description 11
- 239000000049 pigment Substances 0.000 claims description 10
- 238000000151 deposition Methods 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 150000002989 phenols Chemical class 0.000 claims description 7
- 150000003141 primary amines Chemical class 0.000 claims description 7
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 238000010790 dilution Methods 0.000 claims description 4
- 239000012895 dilution Substances 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- JJRUAPNVLBABCN-UHFFFAOYSA-N 2-(ethenoxymethyl)oxirane Chemical compound C=COCC1CO1 JJRUAPNVLBABCN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- AYBUVZZNQPZMCD-UHFFFAOYSA-N ethyl n-(oxiran-2-ylmethyl)carbamate Chemical compound CCOC(=O)NCC1CO1 AYBUVZZNQPZMCD-UHFFFAOYSA-N 0.000 claims 2
- 150000002825 nitriles Chemical class 0.000 claims 2
- 229920001187 thermosetting polymer Polymers 0.000 claims 2
- OZCWUNHGNVXCCO-UHFFFAOYSA-N oxiran-2-ylmethyl hydrogen carbonate Chemical compound OC(=O)OCC1CO1 OZCWUNHGNVXCCO-UHFFFAOYSA-N 0.000 claims 1
- WEVYNWIJRMVEMS-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enyl carbonate Chemical compound C=CCOC(=O)OCC1CO1 WEVYNWIJRMVEMS-UHFFFAOYSA-N 0.000 claims 1
- 229920005989 resin Polymers 0.000 abstract description 60
- 239000011347 resin Substances 0.000 abstract description 60
- 239000003973 paint Substances 0.000 abstract description 26
- 229920001568 phenolic resin Polymers 0.000 abstract description 13
- 239000005011 phenolic resin Substances 0.000 abstract description 13
- 229920003180 amino resin Polymers 0.000 abstract description 11
- 238000007334 copolymerization reaction Methods 0.000 abstract description 7
- 239000007795 chemical reaction product Substances 0.000 abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
- 239000007787 solid Substances 0.000 description 21
- 239000004593 Epoxy Substances 0.000 description 20
- 229960000583 acetic acid Drugs 0.000 description 14
- 235000011054 acetic acid Nutrition 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000002585 base Substances 0.000 description 11
- 229910000831 Steel Inorganic materials 0.000 description 10
- 239000010959 steel Substances 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
- 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 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 7
- 239000003822 epoxy resin Substances 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 6
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 230000008021 deposition Effects 0.000 description 5
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
- 125000005395 methacrylic acid group Chemical class 0.000 description 5
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 239000004310 lactic acid Substances 0.000 description 4
- 235000014655 lactic acid Nutrition 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- BVOSSZSHBZQJOI-UHFFFAOYSA-N 1-Hexen-3-ol Chemical compound CCCC(O)C=C BVOSSZSHBZQJOI-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004807 desolvation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 230000004224 protection Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- VHVMXWZXFBOANQ-UHFFFAOYSA-N 1-Penten-3-ol Chemical compound CCC(O)C=C VHVMXWZXFBOANQ-UHFFFAOYSA-N 0.000 description 1
- LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- HFYAEUXHCMTPOL-UHFFFAOYSA-N 3-Methyl-1-penten-3-ol Chemical compound CCC(C)(O)C=C HFYAEUXHCMTPOL-UHFFFAOYSA-N 0.000 description 1
- HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- RMROKSJZWXILAT-UHFFFAOYSA-N 5-amino-1-(methylamino)pentan-2-ol Chemical compound CNCC(O)CCCN RMROKSJZWXILAT-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- 229920003264 Maprenal® Polymers 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- AAVHHYWBSVSPPN-SCSAIBSYSA-N [(2r)-2-methyloxiran-2-yl]methanol Chemical compound OC[C@]1(C)CO1 AAVHHYWBSVSPPN-SCSAIBSYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- MKUWVMRNQOOSAT-UHFFFAOYSA-N but-3-en-2-ol Chemical compound CC(O)C=C MKUWVMRNQOOSAT-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001652 electrophoretic deposition Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 229940063559 methacrylic acid Drugs 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- JILXUIANNUALRZ-UHFFFAOYSA-N n',n'-diethylbutane-1,4-diamine Chemical compound CCN(CC)CCCCN JILXUIANNUALRZ-UHFFFAOYSA-N 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
- C09D5/4407—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications with polymers obtained by polymerisation reactions involving only carbon-to-carbon unsaturated bonds
- C09D5/4415—Copolymers wherein one of the monomers is based on an epoxy resin
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S524/901—Electrodepositable compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
- Binders And Loading Units For Sheaves (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
- Nonmetallic Welding Materials (AREA)
- Prevention Of Electric Corrosion (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3014290A DE3014290C2 (de) | 1980-04-15 | 1980-04-15 | Verfahren zur Herstellung von wasserverdünnbaren, kathodisch abscheidbaren und wärmehärtenden, stickstoffbasischen Bindemitteln |
| DEP3014290.6-44 | 1980-04-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1201848A true CA1201848A (en) | 1986-03-11 |
Family
ID=6099973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000375383A Expired CA1201848A (en) | 1980-04-15 | 1981-04-13 | Water dilutable cathodic depositable resinous binder production and use |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4376848A (en, 2012) |
| EP (1) | EP0039425B1 (en, 2012) |
| JP (1) | JPS56163167A (en, 2012) |
| AT (1) | ATE6265T1 (en, 2012) |
| BR (1) | BR8102288A (en, 2012) |
| CA (1) | CA1201848A (en, 2012) |
| DE (2) | DE3014290C2 (en, 2012) |
| ES (1) | ES501330A0 (en, 2012) |
| MX (1) | MX158007A (en, 2012) |
| PT (1) | PT72842B (en, 2012) |
| ZA (1) | ZA812509B (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5884871A (ja) * | 1981-11-16 | 1983-05-21 | Nippon Paint Co Ltd | 陰極析出型電着塗料組成物およびその製造法 |
| US4459393A (en) * | 1981-12-09 | 1984-07-10 | Shell Oil Company | Process for the preparation of self-linking resinous binders and their use in surface coating compositions |
| EP0082214B1 (de) * | 1981-12-22 | 1985-05-22 | Lackwerke Wülfing GmbH + Co. | Verfahren zur Herstellung von wärmehärtenden, kathodisch abscheidbaren, wässrigen Elektrotauchlacken und deren Verwendung |
| AT375953B (de) * | 1983-03-21 | 1984-09-25 | Vianova Kunstharz Ag | Verfahren zur herstellung von selbstvernetzenden, kathodisch abscheidbaren etl-bindemitteln auf basis modifizierter alkylphenol-formaldehyd -kondensationsprodukte |
| DE3422474A1 (de) * | 1984-06-16 | 1985-12-19 | Basf Ag, 6700 Ludwigshafen | Hitzehaertbares ueberzugsmittel und seine verwendung |
| US5034279A (en) * | 1986-09-12 | 1991-07-23 | Minnesota Mining & Manufacturing Company | Water-compatible coating composition |
| US4822464A (en) * | 1986-09-12 | 1989-04-18 | Minnesota Mining And Manufacturing Company | Water-compatible coating resin |
| US4904360A (en) * | 1986-09-12 | 1990-02-27 | Minnesota Mining And Manufacturing Company | Water-compatible coating composition |
| US4913968A (en) * | 1986-09-12 | 1990-04-03 | Minnesota Mining And Manufacturing Company | Water-compatible coating resin |
| GB2266721A (en) * | 1992-03-26 | 1993-11-10 | Sericol Ltd | Radiation curable compounds and compositions |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2795572A (en) * | 1957-06-11 | Their polymers | ||
| DE862888C (de) | 1941-05-21 | 1953-01-15 | Basf Ag | Verfahren zur Herstellung von Urethanen, die Oxidogruppen enthalten |
| DE1546840C3 (de) | 1965-02-27 | 1975-05-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zum Herstellen von Überzügen |
| US3414634A (en) * | 1965-10-22 | 1968-12-03 | Air Reduction | Copolymers of vinyl glycidyl ether |
| US3619398A (en) | 1968-10-31 | 1971-11-09 | Ppg Industries Inc | Electrodeposition process |
| DE2002756A1 (de) | 1970-01-22 | 1971-07-29 | Basf Ag | Kathodisch abscheidbare UEberzugsmittel |
| CA986639A (en) | 1971-10-28 | 1976-03-30 | Robert R. Zwack | Cationic electrodepositable compositions |
| US4033917A (en) * | 1975-05-12 | 1977-07-05 | Desoto, Inc. | Electrodeposition of aqueous dispersions of copolymers of polyethylenically unsaturated epoxy-amine adducts |
| US4036800A (en) * | 1975-06-04 | 1977-07-19 | Desoto, Inc. | Electrodeposition of aqueous dispersions of amine functional urethane copolymers |
| DE2541801C3 (de) | 1975-09-19 | 1981-07-02 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von im wesentlichen epoxidgruppenfreien Lackbindemitteln und deren Verwendung |
| DE2707482C2 (de) | 1976-07-19 | 1982-07-29 | Vianova Kunstharz AG, 8402 Werndorf | Verfahren zur Herstellung von Bindemitteln für Elektrotauchlacke |
| AU507206B2 (en) * | 1976-08-18 | 1980-02-07 | Celanese Polymer Specialities Company | Modified epoxy resins |
| US4093594A (en) * | 1976-08-18 | 1978-06-06 | Celanese Polymer Specialties Company | Process for preparing cathodically depositable coating compositions |
| BE857754A (fr) * | 1976-08-18 | 1978-02-13 | Celanese Polymer Special Co | Composition de resine pour revetements, notamment par electrodeposition cathodique |
| DE2801523B2 (de) * | 1978-01-14 | 1980-06-04 | Metallgesellschaft Ag, 6000 Frankfurt | Kathodisch abscheidbares Überzugsmittel |
| US4248753A (en) * | 1978-08-28 | 1981-02-03 | Ppg Industries, Inc. | Michael adducts of polymeric materials useful in coating applications |
| US4297261A (en) * | 1980-06-23 | 1981-10-27 | Ppg Industries, Inc. | Cationic polymers and their use in electrodeposition |
-
1980
- 1980-04-15 DE DE3014290A patent/DE3014290C2/de not_active Expired
-
1981
- 1981-04-03 US US06/250,639 patent/US4376848A/en not_active Expired - Fee Related
- 1981-04-10 DE DE8181102758T patent/DE3162229D1/de not_active Expired
- 1981-04-10 AT AT81102758T patent/ATE6265T1/de not_active IP Right Cessation
- 1981-04-10 EP EP81102758A patent/EP0039425B1/de not_active Expired
- 1981-04-13 PT PT72842A patent/PT72842B/pt unknown
- 1981-04-13 CA CA000375383A patent/CA1201848A/en not_active Expired
- 1981-04-14 BR BR8102288A patent/BR8102288A/pt unknown
- 1981-04-14 ES ES501330A patent/ES501330A0/es active Granted
- 1981-04-15 MX MX186894A patent/MX158007A/es unknown
- 1981-04-15 ZA ZA00812509A patent/ZA812509B/xx unknown
- 1981-04-15 JP JP5780181A patent/JPS56163167A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4376848A (en) | 1983-03-15 |
| ZA812509B (en) | 1982-04-28 |
| BR8102288A (pt) | 1981-12-01 |
| DE3162229D1 (en) | 1984-03-22 |
| PT72842B (en) | 1982-03-30 |
| DE3014290C2 (de) | 1983-04-21 |
| EP0039425B1 (de) | 1984-02-15 |
| DE3014290A1 (de) | 1981-10-29 |
| EP0039425A2 (de) | 1981-11-11 |
| JPS56163167A (en) | 1981-12-15 |
| EP0039425A3 (en) | 1982-05-19 |
| PT72842A (en) | 1981-05-01 |
| JPS6223992B2 (en, 2012) | 1987-05-26 |
| MX158007A (es) | 1988-12-29 |
| ATE6265T1 (de) | 1984-03-15 |
| ES8203926A1 (es) | 1982-04-01 |
| ES501330A0 (es) | 1982-04-01 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |