CN107987716A - A kind of phenyl compound and UV type cathode electrophoresis dope and its preparation and application - Google Patents
A kind of phenyl compound and UV type cathode electrophoresis dope and its preparation and application Download PDFInfo
- Publication number
- CN107987716A CN107987716A CN201711147163.2A CN201711147163A CN107987716A CN 107987716 A CN107987716 A CN 107987716A CN 201711147163 A CN201711147163 A CN 201711147163A CN 107987716 A CN107987716 A CN 107987716A
- Authority
- CN
- China
- Prior art keywords
- parts
- product
- catalyst
- electrophoresis
- cathode electrophoresis
- 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.)
- Granted
Links
- 238000001962 electrophoresis Methods 0.000 title claims abstract description 81
- -1 phenyl compound Chemical class 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 239000003960 organic solvent Substances 0.000 claims abstract description 29
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 21
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003112 inhibitor Substances 0.000 claims abstract description 20
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000000576 coating method Methods 0.000 claims abstract description 17
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000011248 coating agent Substances 0.000 claims abstract description 14
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 7
- 239000002270 dispersing agent Substances 0.000 claims abstract description 7
- 239000003999 initiator Substances 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 44
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 35
- 238000003756 stirring Methods 0.000 claims description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 24
- 239000012224 working solution Substances 0.000 claims description 22
- 239000000178 monomer Substances 0.000 claims description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 18
- 229920005989 resin Polymers 0.000 claims description 18
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 14
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 13
- 239000011259 mixed solution Substances 0.000 claims description 12
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 10
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 10
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000006185 dispersion Substances 0.000 claims description 9
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000839 emulsion Substances 0.000 claims description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 8
- 238000004587 chromatography analysis Methods 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229910000838 Al alloy Inorganic materials 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 238000012544 monitoring process Methods 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical group COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 5
- 229940005561 1,4-benzoquinone Drugs 0.000 claims description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 4
- BBCLXYJRPRRZQW-UHFFFAOYSA-N 2-phenylnaphthalen-1-amine Chemical class C1=CC2=CC=CC=C2C(N)=C1C1=CC=CC=C1 BBCLXYJRPRRZQW-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 4
- 229960000583 acetic acid Drugs 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000004310 lactic acid Substances 0.000 claims description 4
- 235000014655 lactic acid Nutrition 0.000 claims description 4
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical group C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 claims description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 3
- LDMRLRNXHLPZJN-UHFFFAOYSA-N 3-propoxypropan-1-ol Chemical compound CCCOCCCO LDMRLRNXHLPZJN-UHFFFAOYSA-N 0.000 claims description 3
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
- 239000012362 glacial acetic acid Substances 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- 235000013772 propylene glycol Nutrition 0.000 claims description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000009471 action Effects 0.000 claims description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 2
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 claims 1
- HJOVHMDZYOCNQW-UHFFFAOYSA-N Isophorone Natural products CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 claims 1
- WQPDQJCBHQPNCZ-UHFFFAOYSA-N cyclohexa-2,4-dien-1-one Chemical compound O=C1CC=CC=C1 WQPDQJCBHQPNCZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- XVKKIGYVKWTOKG-UHFFFAOYSA-N diphenylphosphoryl(phenyl)methanone Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 XVKKIGYVKWTOKG-UHFFFAOYSA-N 0.000 claims 1
- 125000006838 isophorone group Chemical group 0.000 claims 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- 230000002459 sustained effect Effects 0.000 claims 1
- 239000000047 product Substances 0.000 description 53
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- 238000001723 curing Methods 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 10
- 229910021641 deionized water Inorganic materials 0.000 description 10
- 230000002572 peristaltic effect Effects 0.000 description 10
- 238000001816 cooling Methods 0.000 description 8
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
- 239000004925 Acrylic resin Substances 0.000 description 7
- 229920000178 Acrylic resin Polymers 0.000 description 7
- 235000019270 ammonium chloride Nutrition 0.000 description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical group CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 238000000016 photochemical curing Methods 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 238000004448 titration Methods 0.000 description 5
- 238000005292 vacuum distillation Methods 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000001652 electrophoretic deposition Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000010422 painting Methods 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 238000004070 electrodeposition Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- OSNIIMCBVLBNGS-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-2-(dimethylamino)propan-1-one Chemical compound CN(C)C(C)C(=O)C1=CC=C2OCOC2=C1 OSNIIMCBVLBNGS-UHFFFAOYSA-N 0.000 description 1
- RSJWKIDVVZWYTD-UHFFFAOYSA-N 1-(2-isocyanatopropan-2-yl)-2-prop-1-en-2-ylbenzene Chemical class CC(=C)C1=CC=CC=C1C(C)(C)N=C=O RSJWKIDVVZWYTD-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 241000208340 Araliaceae Species 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000019082 Osmanthus Nutrition 0.000 description 1
- 241000333181 Osmanthus Species 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- JHQMEZRRZJJNAI-UHFFFAOYSA-N [(2-methylphenyl)-phenylphosphoryl]-phenylmethanone Chemical compound CC1=CC=CC=C1P(=O)(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 JHQMEZRRZJJNAI-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000009466 transformation Effects 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
- C09D5/4419—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 otherwise than by polymerisation reactions only involving carbon-to-carbon unsaturated bonds
- C09D5/4465—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- 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
- C09D5/18—Fireproof paints including high temperature resistant paints
-
- 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
- C09D5/4488—Cathodic paints
- C09D5/4492—Cathodic paints containing special additives, e.g. grinding agents
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
- C25D13/00—Electrophoretic coating characterised by the process
- C25D13/04—Electrophoretic coating characterised by the process with organic material
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Molecular Biology (AREA)
- Electrochemistry (AREA)
- Metallurgy (AREA)
- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The invention belongs to the technical field of electrophoretic coating, discloses a kind of phenyl compound and UV type cathode electrophoresis dope and its preparation and application.The structural formula of the phenyl compound is Formulas I.The UV types cathode electrophoresis dope is made of following component by weight:10~25 parts of dimethylaminoethyl methacrylate, 15~30 parts of methyl methacrylate, 4~20 parts of hydroxy-ethyl acrylate, 15~30 parts of butyl acrylate, 5~20 parts of styrene, 5~20 parts of diisocyanate, 0.2~1 part of catalyst, 1~2 part of polymerization inhibitor, 1~10 part of radical initiator, 2~8 parts of dispersant, 2~8 parts of photoinitiator, 5~30 parts of phenyl compound, 3~10 parts of neutralizer, 102~210 parts of organic solvent, 100~1500 parts of water.The UV types cathode electrophoresis dope has preferable heat resistance, hardness and glossiness;It is used to prepare electrophoresis product.
Description
Technical field
The invention belongs to the technical field of electrophoretic coating, and in particular to a kind of phenyl compound and UV type cathode electrophoresis dope
And preparation method and application.
Background technology
Electrophoretic coating is main because having the advantages that paint film is homogeneous, hardness is high, the transparency is good, efficient and energy saving and low stain
To apply and be applied in automobile production.Compared with anode electrophoresis dope, there is more excellent anti-corrosion after cathode electrophoresis dope application
Ability, throwing power are high and because its utilization efficiency of coatings is high, film is uniformly from the influence of coated article shape, good decorating effect, environment
Polluting the advantages that small is not only widely used in painting dressing automobiles field, and in metal surfaces such as building materials, furniture, hardware and craftworks
Anti-corrosion and furnishing fields are also widely used.
What the curing mode of conventional electrophoretic paint was generally taken is to be heating and curing, and required solidification temperature is very high, cures temperature
Degree limits the application in heatsensitive substrates such as plastics, timber generally at 140~180 DEG C, and hardening time is longer.It is purple
Outer photocuring technology be using apply film resin occurs under ultraviolet light polymerization bridging reaction, the short time under conditions of low temperature
The interior curing process that can just complete.And ultraviolet light cures electrophoretic coating except because its solidification temperature is relatively low, curing rate is fast, no
Common electrophoretic painting is only applicable to, is additionally suitable for other products.Therefore comprehensive UV cures and electrophoretic painting advantage
Ultraviolet light (UV) Curable Cationic Electrodeposition Coatings have great application development prospect.
But it is few suitable for the species of the photoinitiator of UV Curable Cationic Electrodeposition Coatings at present, new photoinitiator but still
In the laboratory research stage, there is a distance from actual industrial production application, need further to be studied;Coated solidified mistake
Influence and flash process application problem of the journey to paint film property also need to further study.There is also hardness of paint film, heat-resisting at the same time
Property and low in glossiness problem.
Ultraviolet light curing cathodic electrophoretic coating common at present is there are poor heat resistance, and hardness is low, and glossiness is low, and pliability is poor
The problems such as.Therefore it is highly desirable to provide and a kind of has hardness and the high cathode electrophoresis dope of glossiness concurrently with UV type heat resistances.
The content of the invention
The shortcomings that in order to solve the prior art and shortcoming, primary and foremost purpose of the invention are synthesizing a kind of rigid structure
Heat-resistant monomer (i.e. phenyl compound) and preparation method thereof.
Another object of the present invention is to provide a kind of UV type cathode electrophoresis dopes prepared using above-mentioned phenyl compound
And its method.By using phenyl compound, the present invention solves UV type cathode electrophoresis dope poor heat resistances, and hardness is low, gloss
Spend low, the technical problem such as pliability difference.
It is still another object of the present invention to provide the application using above-mentioned UV types cathode electrophoresis dope.The UV types cathode electricity
It is electrophoretic paint used in preparing electrophoresis product.
The purpose of the present invention is achieved through the following technical solutions:
A kind of phenyl compound, its structural formula are
The preparation method of the phenyl compound be using organic solvent as reaction medium, using benzaldehyde and methyl acrylate as
Reaction raw materials, reaction raw materials are reacted under the action of catalyst, and purifying, obtains phenyl compound.The benzaldehyde and third
The molar ratio of e pioic acid methyl ester is (2~10) mol:(3~15) mol.
The amount ratio of the benzaldehyde and catalyst is (2~10) mol:(2~12) mol;The benzaldehyde with it is organic molten
The amount ratio of agent is (2~10) mol:(50~200) ml.
The catalyst is triethylamine, triethylene diamine, tetrabutyl Ammonium hydrogen sulfate, four butyl bromation amine, triethylbenzyl
One or more of ammonium chloride, 4-dimethylaminopyridine;The organic solvent is tetrahydrofuran, ethyl acetate, methanol, dimethyl
One or more of sulfoxide, dimethylformamide.
The temperature of the reaction is room temperature, and whether the reaction is completed by thin-layered chromatography TLC monitoring reactions.
The purifying refers to wash the product after reaction with saturated aqueous ammonium chloride, is then extracted, had with extract
Machine mutually uses desiccant dryness, filters, and revolving, silica gel column chromatography, revolving, obtains phenyl compound.
The extract is one or more of carbon tetrachloride, alcohol, ethyl acetate;The drier is anhydrous slufuric acid
One or more of magnesium, anhydrous sodium sulfate, natrium carbonicum calcinatum.
The temperature of the revolving is 30~60 DEG C;The time of desiccant dryness is 6~10h.
50~the 300ml of saturated aqueous ammonium chloride, extract dosage are 10~50ml, drier dosage be 5~
10g。
The phenyl compound is used to prepare UV type cathode electrophoresis dopes.
A kind of UV type cathode electrophoresis dopes prepared using above-mentioned phenyl compound, by following component group by weight
Into:10~25 parts of dimethylaminoethyl methacrylate (DMAEMA), 15~30 parts of methyl methacrylate (MMA), acrylic acid
4~20 parts of hydroxyl ethyl ester (HEA), 15~30 parts of butyl acrylate (BA), 5~20 parts of styrene (St), diisocyanate 5~20
Part, 0.2~1 part of catalyst, 1~2 part of polymerization inhibitor, 1~10 part of radical initiator, 2~8 parts of dispersant, photoinitiator 2~8
Part, 5~30 parts of phenyl compound, 3~10 parts of neutralizer, 102~210 parts of organic solvent, 100~1500 parts of water.
The diisocyanate is isophorone diisocyanate (IPDI).
The catalyst is triethylamine, dibutyl tin laurate, triethylene diamine, tetrabutyl Ammonium hydrogen sulfate, the tetrabutyl
One or more of amine bromide, triethylbenzyl ammonium chloride, 4-dimethylaminopyridine.
The polymerization inhibitor for hydroquinone, 1,4-benzoquinone, 2,6- toluene di-tert-butyl phenols, beta-phenyl naphthylamines, to the tert-butyl group
One or more of catechol.
The radical initiator is one in azodiisobutyronitrile, azo-bis-iso-dimethyl, benzoyl peroxide
More than kind.
The dispersant is ethylene glycol monobutyl ether, in propyleneglycoles monobutyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether
More than one.
The photoinitiator is 1- hydroxycyclohexyl phenyl ketones, 2- hydroxy-2-methyl -1- phenylacetones, 2,4,6- tri-
One in methyl benzoyl-diphenyl phosphine oxide, 2- hydroxy-2-methyls -1- [4- (2- hydroxyl-oxethyls) phenyl] -1- acetone
More than kind.
The neutralizer is one or more of lactic acid, glacial acetic acid, nitric acid, bishydroxymethyl propionic acid.
The organic solvent is propylene glycol methyl ether acetate, ethyl acetate, methanol, dimethyl sulfoxide (DMSO), methyl iso-butyl ketone (MIBK)
One or more of.
The preparation method of the UV types cathode electrophoresis dope, comprises the following steps:
(1) by 10~25 parts of dimethylaminoethyl methacrylate (DMAEMA), methyl methacrylate (MMA) 15~30
Part, 2~10 parts of hydroxy-ethyl acrylate (HEA), 15~30 parts of butyl acrylate (BA), 5~20 parts of styrene (St), free radical draw
Send out 1~10 part of agent and 50~100 parts of organic solvent is uniformly mixed, obtain mixed monomer solution;(stirring turns under conditions of stirring
Speed is 120~200r/min), in 70 DEG C~90 DEG C, into 50~100 parts of organic solvents, mixed monomer solution is added dropwise, drips
4~6h is kept the temperature after finishing, it is 50wt%~70wt% to be evaporated under reduced pressure to solid content, obtains product A;
(2) 0.5~1 part of 5~20 parts of diisocyanate and polymerization inhibitor are uniformly mixed, then at 40~70 DEG C, are added dropwise
By 2~10 parts of hydroxy-ethyl acrylate (HEA) and 0.1~0.5 part of mixture mixed of catalyst, after dripping, continue anti-
Should, when the content of the theoretical value after the content of-NCO in reaction system reaches semiclosed, reaction is terminated, obtains product B;
(3) 0.1~0.5 part of catalyst, 0.5~1 part of polymerization inhibitor are dissolved in 2~10 parts of organic solvents, obtain catalyst
With the mixed solution of polymerization inhibitor;The mixed solution of catalyst and polymerization inhibitor is uniformly mixed with the product B of step (2), is mixed
Compound;Under conditions of stirring (speed of agitator is 100~150r/min), in 40 DEG C~70 DEG C, into the product A of step (1)
Mixture is added dropwise, is added dropwise, keeps the temperature 3~4h, obtains resin product;
(4) in 40 DEG C~70 DEG C, 3~10 parts of neutralizer is added to the resin product of step (3), stirs evenly, is down to room
Temperature, adds 2~8 parts of dispersant, 5~30 parts of 2~8 parts of photoinitiator and phenyl compound, is uniformly dispersed, it is gradually added 100~
1500 parts of water make it that solid content is 10~20%, and high speed emulsion dispersion, curing, obtaining UV types cathode electrophoresis dope, (i.e. UV light is consolidated
Change the acids cathode electrophoresis dope of modified propylene).
The condition of high speed emulsion dispersion described in step (4) is to disperse 20~60min under 3000~6000r/min rotating speeds,
The condition of curing is to cure 24~48h with 150~250r/min.
Stirred evenly described in step (4) and refer to stir 20~60min with the speed of 120~200r/min;It is described scattered
Uniformly refer to stir 5~10min with 180~250r/min rotating speeds.
The temperature being evaporated under reduced pressure described in step (1) is 40 DEG C~70 DEG C;Need to cool down before vacuum distillation;The dropwise addition need to be
It is added dropwise in 2-3h;
The content of-NCO di-n-butylamine method titration determination in the reaction system of step (2);
Being added dropwise described in step (2) need to be added dropwise in 1~2h;
Being added dropwise described in step (3) needs to be added dropwise in 1~2h.
The UV types cathode electrophoresis dope is used to prepare electrophoresis product.
The electrophoresis product includes substrate pole plate and is deposited on the UV types cathode electrophoresis dope deposition of substrate polar board surface
Layer.The substrate pole plate is the iron plate that phosphorating treatment is crossed.
The specific preparation method of the electrophoresis product is:Using UV types cathode electrophoresis dope as working solution, made with aluminium alloy plate
For anode, using substrate pole plate as cathode, electrophoretic process is carried out, is cleaned, dry, UV lamp irradiation, obtains electrophoresis product.The cathode
Spacing with anode is 8~15cm;100~150V of supply voltage of the electrophoresis, the time of electrophoresis is 60~180s;It is described clear
Wash and refer to clean cathode plate surface supernatant liquid with deionized water, the drying is in 60~100 DEG C of dry 2~3min, the UV lamp
The condition of irradiation is that 10~60s is irradiated under the UV lamp of 1000W~2000W.
The deposit thickness is 10~15 μm.
The beneficial effects of the invention are as follows:The phenyl compound of the present invention has the phenyl ring for stablizing rigid structure, while has again
There is reactive group;Phenyl compound is prepared UV type cathode electrophoresis dopes by the present invention together with other monomers so that UV cathodes electricity
Heat resistance, hardness and the glossiness of swimming coating all obtained lifting.Therefore modified UV cathode electrophoresis dopes have wide answer
Use prospect.
Brief description of the drawings
Fig. 1 is (right for acrylic ester prepolymer in embodiment 1 (corresponding is product A prepared by step (2)), photosensitive resin
What is answered is resin product prepared by step (4)) and semiclosed IPDI prepolymers (product B prepared by step (3)) infrared absorption light
Spectrogram.
Embodiment
The present invention is described in further detail with specific embodiment below in conjunction with the accompanying drawings, however, the present invention is not limited thereto.
Thin-layered chromatography TLC is that suitable stationary phase is coated on glass plate, into a thin uniform layer;After point sample, expansion after, according to than
Shifting value (Rf) with raw material by the same method gained chromatogram Rf value (Rf) compare, to monitor whether reaction is completed;When occur with
When raw material point compares polarity larger point, reaction terminates.
The TLC eluents refer to respectively ethyl acetate and n-hexane.
Embodiment 1
(1) by benzaldehyde (2mol), methyl acrylate (4mol), 4-dimethylaminopyridine (3mol) and organic solvent four
Whether hydrogen furans (50ml) is uniformly mixed, and is stirred at normal temperatures, completed by thin-layered chromatography TLC monitoring reactions, reaction terminates
Afterwards, washed and dissolved with saturated aqueous ammonium chloride (50ml), extracted with ethyl acetate (10ml), anhydrous slufuric acid is added to by organic
Magnesium (5g) dries 6h, filters, and vacuum rotary steam goes out solvent at 30 DEG C, and silica gel column chromatography, 30 DEG C of revolvings, obtain phenyl compound;
(2) by 10 parts of dimethylaminoethyl methacrylate (DMAEMA), 15 parts of methyl methacrylate (MMA), propylene
Sour 4 parts of hydroxyl ethyl ester (HEA), 15 parts of butyl acrylate (BA), 5 parts of styrene (St), 2 parts of azo-bis-iso-dimethyl and organic
50 parts of solvent propylene glycol methyl ether acetate is uniformly mixed, and obtains mixed monomer solution;(the speed of agitator under conditions of stirring
For 120r/min), in 75 DEG C, into 50 parts of organic solvent propylene glycol methyl ether acetates, mixed monomer solution is added dropwise, control is wriggled
Pump drop speed 10rpm, is added dropwise in 2h, keeps the temperature 4h, cooling discharging, and 40 DEG C of vacuum distillations to solid content are 50wt% or so,
Obtain product A;
(3) 0.5 part of 5 parts of isophorone diisocyanate (IPDI) and hydroquinone are uniformly mixed, then in stirring and
Under the conditions of 40 DEG C, it is added dropwise by 2 parts of hydroxy-ethyl acrylate (HEA) and 0.1 part of mixture mixed of triethylamine, passes through wriggling
Pump, control drop speed 4rpm, is added dropwise in 2h;It is added dropwise after rear 5min that (method refers to state with di-n-butylamine method titration
Mark GBT 18446-2009) in measure reaction system-NCO content, until the content of-NCO reach semiclosed after theoretical value (-
NCO, 9.18%) content, terminates reaction, obtains product B;
(4) 0.1 part of triethylamine, 0.5 part of hydroquinone are dissolved in 2 parts of organic solvent propylene glycol methyl ether acetates, obtained
The mixed solution of catalyst and polymerization inhibitor;The mixed solution of catalyst and polymerization inhibitor is uniformly mixed with the product B of step (3),
Obtain mixture;Under conditions of stirring (speed of agitator 100r/min), in 40 DEG C, it is added dropwise into the product A of step (2) mixed
Compound, is added dropwise using peristaltic pump, is added dropwise in control drop speed 5rpm, 2h, insulation 3h (is characterized using Fourier infrared spectrograph
Analysis, it is ensured that isocyano and hydroxyl reaction are complete), obtain resin product;
(5) in 40 DEG C, 3 parts of lactic acid is added to the resin product of step (4), is stirred with the mixing speed of 120r/min
20min;Then room temperature is down to, adds 3 parts of ethylene glycol monobutyl ether, 3 parts of 1- hydroxycyclohexyl phenyl ketones and phenyl compound 5
Part, 10min is stirred with 180r/min rotating speeds, so as to be uniformly dispersed;Deionized water to solid content is gradually added into three times to be reduced to
20% (mass percent), carries out emulsion dispersion (disperseing 60min under 3000r/min rotating speeds), with 150r/ with high speed dispersor
Min cures 48h, obtains the acids cathode electrophoresis dope working solution of UV types cathode electrophoresis dope i.e. UV photocurings modified propylene;
(6) using above-mentioned UV types cathode electrophoresis dope as working solution (ability cathode electrophoresis working solution), ability cathode electrophoresis working solution is added
Enter in electrophoresis tank, be stirred with 150r/min rotating speeds;By the use of clean aluminium alloy plate as anode, after being cleaned with ethanol and acetone
5 × 7.5cm phosphatizations plate (parkerized iron plate) be used as cathode, both are equally immersed in working solution, between adjustment plate
Away from for 8cm;After regulating power source voltage 100V, deenergization after electrophoresis 180s;Cathode plate surface supernatant liquid is cleaned using deionized water,
Drain and be placed on air dry oven in 70 DEG C of dry 3min, removal surface moisture;After pole plate cooling, 1000W is placed on
UV lamp under irradiate 20s, obtain the smooth electrophoresis product in surface.
Acrylic ester prepolymer (corresponding is product A prepared by step (2)), photosensitive resin are (corresponding in the present embodiment
It is resin product prepared by step (4)) and semiclosed IPDI prepolymers (product B prepared by step (3)) infrared absorpting light spectra
As shown in Figure 1.
Electrophoretic deposition layer thickness is 10 μm, pencil hardness 3H in the electrophoresis product, and heat resistance is 100 DEG C of retention properties
Constant, glossiness 70, it is 100 that resistance to butanone, which wipes number, and adhesive force is 0 grade.
Embodiment 2
(1) by benzaldehyde (5mol), methyl acrylate (7mol), triethylene diamine (6mol) and organic solvent acetic acid second
Whether ester (100ml) is uniformly mixed, and is stirred at normal temperatures, completed by thin-layered chromatography TLC monitoring reactions, after reaction,
Washed and dissolved with saturated aqueous ammonium chloride (100ml), extracted with ethyl acetate (30ml), anhydrous sodium sulfate is added to by organic
(6g) dries 8h, filters, and vacuum rotary steam goes out solvent at 40 DEG C, and silica gel column chromatography, 40 DEG C of revolvings, obtain phenyl compound;
(2) by 15 parts of dimethylaminoethyl methacrylate (DMAEMA), 20 parts of methyl methacrylate (MMA), propylene
Sour 6 parts of hydroxyl ethyl ester (HEA), 20 parts of butyl acrylate (BA), 8 parts of styrene (St), 4 parts of azodiisobutyronitrile and there is ethyl acetate
80 parts are uniformly mixed, and obtain mixed monomer solution;Under conditions of stirring (speed of agitator 175r/min), in 80 DEG C,
Into 80 parts of organic solvent ethyl acetate, mixed monomer solution is added dropwise, control peristaltic pump drop speed 12rpm, drips in 2.5h
Finish, keep the temperature 5h, cooling discharging, 50 DEG C of vacuum distillations to solid content are 60wt% or so, obtain product A;
(3) 10 parts of isophorone diisocyanate (IPDI) and 0.7 part of 2,6- toluene di-tert-butyl phenol are uniformly mixed,
Then under the conditions of stirring with 50 DEG C, it is added dropwise by the 0.3 part of mixing of 5 parts of hydroxy-ethyl acrylate (HEA) and dibutyl tin laurate
The mixture formed, by peristaltic pump, control drop speed 6rpm, is added dropwise in 1.5h;It is added dropwise after rear 10min with two just
In butylamine method titration (method refers to national standard GBT18446-2009) measure reaction system-NCO content, until the content of-NCO
The content of theoretical value (- NCO, 9.18%) after reaching semiclosed, terminates reaction, obtains product B;
(4) 0.3 part of dibutyl tin laurate, 0.6 part of 2,6- toluene di-tert-butyl phenols are dissolved in 5 parts of organic solvent second
In acetoacetic ester, the mixed solution of catalyst and polymerization inhibitor is obtained;By the production of the mixed solution of catalyst and polymerization inhibitor and step (3)
Thing B is uniformly mixed, and obtains mixture;Under conditions of stirring (speed of agitator 120r/min), in 60 DEG C, to step (2)
Mixture is added dropwise in product A, is added dropwise using peristaltic pump, is added dropwise in control drop speed 6rpm, 1.5h, insulation 4h (uses Fourier
Leaf infrared spectrometer phenetic analysis, it is ensured that isocyano and hydroxyl reaction are complete), obtain resin product;
(5) in 50 DEG C, 5 parts of glacial acetic acid is added to the resin product of step (4), is stirred with the mixing speed of 150r/min
30min;Then room temperature is down to, adds 4 parts of ethylene glycol monobutyl ether, 4 parts of 2- hydroxy-2-methyl -1- phenylacetones and phenyl chemical combination
10 parts of thing, stirs 8min with 200r/min rotating speeds, is uniformly dispersed;Deionized water to solid content is gradually added into three times to be reduced to
15%, emulsion dispersion (disperseing 50min under 4000r/min rotating speeds) is carried out with high speed dispersor, 40h is cured with 200r/min, is obtained
To the acids cathode electrophoresis dope working solution of UV types cathode electrophoresis dope, that is, UV photocuring modified propylenes;
(6) using above-mentioned UV types cathode electrophoresis dope as working solution (ability cathode electrophoresis working solution), ability cathode electrophoresis working solution is added
Enter in electrophoresis tank, be stirred with 180r/min rotating speeds;By the use of clean aluminium alloy plate as anode, after being cleaned with ethanol and acetone
5 × 7.5cm phosphatizations plate (parkerized iron plate) be used as cathode, both are equally immersed in working solution, between adjustment plate
Away from for 10cm;After regulating power source voltage 120V, deenergization after electrophoresis 100s;Floated using deionized water cleaning cathode plate surface
Liquid, drains and is placed on air dry oven in 80 DEG C of dry 3min, removal surface moisture;After pole plate cooling, it is placed on
30s is irradiated under the UV lamp of 1000W, obtains the smooth electrophoresis product in surface.
Electrophoretic deposition layer thickness is 12 μm, pencil hardness 6H in the electrophoresis product, and heat resistance is 120 DEG C of retention properties
Constant, glossiness 80, it is 300 that resistance to butanone, which wipes number, and adhesive force is 0 grade.
Embodiment 3
(1) by benzaldehyde (7mol), methyl acrylate (10mol), tetrabutyl Ammonium hydrogen sulfate (8mol) and organic solvent
Whether methanol (150ml) is uniformly mixed, and is stirred at normal temperatures, completed by thin-layered chromatography TLC monitoring reactions, reaction terminates
Afterwards, washed and dissolved with saturated aqueous ammonium chloride (200ml), extracted with ethyl acetate (40ml), anhydrous sulphur is added to by organic
Filtered after the dry 9h of sour sodium (8g), vacuum rotary steam goes out solvent at 50 DEG C, and silica gel column chromatography, 50 DEG C of revolvings, obtain phenyl compound;
(2) by 20 parts of dimethylaminoethyl methacrylate (DMAEMA), 25 parts of methyl methacrylate (MMA), propylene
Sour 8 parts of hydroxyl ethyl ester (HEA), 25 parts of butyl acrylate (BA), 10 parts of styrene (St), 5 parts of azodiisobutyronitrile and organic solvent
90 parts of methanol is uniformly mixed, and obtains mixed monomer solution;Under conditions of stirring (speed of agitator 180r/min), in 85
DEG C, into 90 parts of organic solvent methanol, mixed monomer solution is added dropwise, control peristaltic pump drop speed 14rpm, drips in 2.5h
Finish, keep the temperature 5h, discharge after cooling, 65 DEG C of vacuum distillations to solid content are 65%, obtain product A;
(3) 0.8 part of 15 parts of isophorone diisocyanate (IPDI) and 1,4-benzoquinone are uniformly mixed, then in stirring and 60
Under the conditions of DEG C, it is added dropwise by 8 parts of hydroxy-ethyl acrylate (HEA) and 0.4 part of mixture mixed of tetrabutyl Ammonium hydrogen sulfate, passes through
Peristaltic pump, control drop speed 8rpm, is added dropwise in 1h;Di-n-butylamine method titration (method ginseng is used after rear 10min is added dropwise
Examine national standard GBT 18446-2009)-NCO content is measured in reaction system, the theory after the content of-NCO reaches semiclosed
It is worth the content of (- NCO, 9.18%), terminates reaction, obtain product B;
(4) 0.4 part of tetrabutyl Ammonium hydrogen sulfate, 0.8 part of 1,4-benzoquinone are dissolved in 8 parts of organic solvent methanol, obtain catalyst
With the mixed solution of polymerization inhibitor;The mixed solution of catalyst and polymerization inhibitor is uniformly mixed with the product B of step (3), is mixed
Compound;Under conditions of stirring (speed of agitator 140r/min), in 50 DEG C, mixture is added dropwise into the product A of step (2),
It is added dropwise, is added dropwise in control drop speed 7rpm, 1.2h, insulation 3h (uses Fourier infrared spectrograph characterization point using peristaltic pump
Analysis, it is ensured that isocyano and hydroxyl reaction are complete), obtain resin product;
(5) in 60 DEG C, 8 parts of nitric acid is added to the resin product of step (4), is stirred with the mixing speed of 180r/min
50min;Then room temperature is down to, adds 6 parts of propyleneglycoles monobutyl ether, 2,4,6- trimethylbenzoy-dipheny phosphine oxides 6
20 parts of part and phenyl compound, stir 6min with 220r/min, it is uniformly dispersed;Deionized water is gradually added into three times to admittedly
Content is reduced to 10%, emulsion dispersion (disperseing 30min under 5000r/min rotating speeds) is carried out with high speed dispersor, with 180r/min
30h is cured, obtains the acids cathode electrophoresis dope working solution of UV types cathode electrophoresis dope i.e. UV photocurings modified propylene;
(6) using above-mentioned UV types cathode electrophoresis dope as working solution (ability cathode electrophoresis working solution), ability cathode electrophoresis working solution is added
Enter in electrophoresis tank, be stirred with 200r/min rotating speeds;By the use of clean aluminium alloy plate as anode, after being cleaned with ethanol and acetone
5 × 7.5cm phosphatizations plate (parkerized iron plate) be used as cathode, both are equally immersed in working solution, between adjustment plate
Away from for 12cm;After regulating power source voltage 100V, deenergization after electrophoresis 180s;Floated using deionized water cleaning cathode plate surface
Liquid, drains and is placed on air dry oven in 90 DEG C of dry 3min, removal surface moisture;After pole plate cooling, it is placed on
50s is irradiated under the UV lamp of 2000W, obtains the smooth electrophoresis product in surface.
Electrophoretic deposition layer thickness is 14 μm, pencil hardness 5H in the electrophoresis product, and heat resistance is 110 DEG C of retention properties
Constant, glossiness 60, it is 120 that resistance to butanone, which wipes number, and adhesive force is 0 grade.
Embodiment 4
(1) by benzaldehyde (10mol), methyl acrylate (15mol), 4-dimethylaminopyridine (12mol) and organic molten
Whether agent dimethylformamide (200ml) is uniformly mixed, and is stirred at normal temperatures, completed by thin-layered chromatography TLC monitoring reactions,
After reaction, washed and dissolved with saturated aqueous ammonium chloride (300ml), extracted with ethyl acetate (50ml), by organic addition
Filtered after entering the dry 9h of natrium carbonicum calcinatum (10g), 60 DEG C of vacuum rotary steams go out solvent, and silica gel column chromatography, 60 DEG C of revolvings, obtain phenyl
Compound;
(2) by 25 parts of dimethylaminoethyl methacrylate (DMAEMA), 30 parts of methyl methacrylate (MMA), propylene
Sour 10 parts of hydroxyl ethyl ester (HEA), 30 parts of butyl acrylate (BA), 15 parts of styrene (St), 7 parts of benzoyl peroxide and organic solvent
100 parts of methyl iso-butyl ketone (MIBK) is uniformly mixed, and obtains mixed monomer solution;(the speed of agitator 200r/ under conditions of stirring
Min), in 85 DEG C, into 100 parts of organic solvent methyl iso-butyl ketone (MIBK)s, mixed monomer solution, control peristaltic pump drop speed is added dropwise
15rpm, is added dropwise in 3h, keeps the temperature 6h, discharges after cooling, and 40 DEG C of vacuum distillations to solid content are 70%, obtain product A;
(3) 1 part of 20 parts of isophorone diisocyanate (IPDI) and beta-phenyl naphthylamines are uniformly mixed, then in stirring and
Under the conditions of 70 DEG C, it is added dropwise by 10 parts of hydroxy-ethyl acrylate (HEA) and 0.5 part of mixture mixed of 4-dimethylaminopyridine,
By peristaltic pump, control drop speed 8rpm, is added dropwise in 1h;Di-n-butylamine method titration (side is used after rear 20min is added dropwise
Method refers to national standard GBT 18446-2009)-NCO content is measured in reaction system, until after the content of-NCO reaches semiclosed
The content of theoretical value (- NCO, 9.18%), terminates reaction, obtains product B;
(4) 0.5 part of 4-dimethylaminopyridine, 1 part of beta-phenyl naphthylamines are dissolved in 10 parts of organic solvent methyl iso-butyl ketone (MIBK)s,
Obtain the mixed solution of catalyst and polymerization inhibitor;The mixed solution of catalyst and polymerization inhibitor is mixed with the product B of step (3)
It is even, obtain mixture;Under conditions of stirring (speed of agitator 150r/min), in 50 DEG C, dripped into the product A of step (2)
Add mixture, be added dropwise using peristaltic pump, is added dropwise in control drop speed 8rpm, 1h, insulation 4h (uses Fourier infrared spectrograph
Phenetic analysis, it is ensured that isocyano and hydroxyl reaction are complete), obtain resin product;
(5) in 70 DEG C, 10 parts of bishydroxymethyl propionic acid is added to the resin product of step (4), with the stirring of 200r/min
Speed stirs 60min;Then room temperature is down to, adds 8 parts of propylene glycol monopropyl ether, 2- hydroxy-2-methyls -1- [4- (2- '-hydroxyethoxies
Base) phenyl] 30 parts of 8 parts of -1- acetone and phenyl compound, stir 5min with 250r/min, it is uniformly dispersed;It is gradual in three times
Add deionized water to solid content and be reduced to 10%, carry out emulsion dispersion with high speed dispersor (disperses under 6000r/min rotating speeds
20min), 24h is cured with 150r/min, obtains the UV types cathode electrophoresis dope i.e. acids ability cathode electrophoresis of UV photocurings modified propylene
Coating working solution;
(6) using above-mentioned UV types cathode electrophoresis dope as working solution (ability cathode electrophoresis working solution), ability cathode electrophoresis working solution is added
Enter in electrophoresis tank, be stirred with 250r/min rotating speeds;By the use of clean aluminium alloy plate as anode, after being cleaned with ethanol and acetone
5 × 7.5cm phosphatizations plate (parkerized iron plate) be used as cathode, both are equally immersed in working solution, between adjustment plate
Away from for 15cm;After regulating power source voltage 100V, deenergization after electrophoresis 180s;Floated using deionized water cleaning cathode plate surface
Liquid, drains and is placed on air dry oven in 100 DEG C of dry 3min, removal surface moisture;After pole plate cooling, it is placed on
10s is irradiated under the UV lamp of 2000W, obtains the smooth electrophoresis product in surface.
Electrophoretic deposition layer thickness is 15 μm in the electrophoresis product;Pencil hardness is 4H;Heat resistance is 100 DEG C of retention properties
It is constant;Glossiness is 65;It is 90 that resistance to butanone, which wipes number,;Adhesive force is 0 grade.
Comparative example 5
1. the preparation of acrylic resin
The azodiisobutyronitrile for accounting for monomer gross mass 3% is mixed with monomer, wherein monomers methyl methacrylate, benzene second
Alkene, butyl methacrylate and methacrylic acid -2-2 hydroxyl ethyl esters, dosage are respectively 79,21,22 and 44.4g, methacrylic acid
The dosage of diethylamine ethyl ester is 16.8g;Monomer is slowly dropped into the container equipped with solvent butanone at 75 DEG C, its dosage is monomer
1.5 times of gross mass, when reaction 4 is small, makes monomer conversion reach more than 98%, obtain acrylic resin product;
2. acrylic resin modified preparation
0.5wt% (the 0.5% of acrylic resin product quality) catalyst dibutyltin osmanthus is added into acrylic resin product
Sour dibutyl tin, is slowly added dropwise isopropenyl-alpha, alpha-dimethylbenzyl isocyanates between 42.4g at 60 DEG C, when reaction 3 is small,
Appropriate absolute ethyl alcohol is added, removes the isocyanates for failing reaction, vacuum extracts solvent, obtains acrylic resin modified;
3. ultraviolet light cures the preparation of cathod coating
It is 1 in acrylic resin modified middle addition mass ratio:1 2- hydroxy-2-methyls propiophenone and 1- hexahydrotoluenes
Benzophenone photoinitiator, its dosage are the 1.5wt% of resin, and it is 6.0 to be neutralized with lactic acid to pH value, and is diluted with deionized water
It is 15% to solid content, ultraviolet light curing cathodic electrophoretic coating is configured to through high speed dispersion;
4. ultraviolet light curing cathodic electrophoretic coating performance detection
Using the ultraviolet light curing cathodic electrophoretic coating of preparation as electrophoresis groove liquid, under 25 DEG C of temperature, voltage 20V, to not
Steel surface of becoming rusty carries out electrophoretic painting.Stainless steel plate after application flashes 10 minutes at 60 DEG C, in room temperature, 1kW high pressure Hg lamp spokes
Cure crosslinking 55 seconds according to lower.Coating thickness is measured as 25 μm, pencil hardness 3H, is not decomposed at 90 DEG C, glossiness 60.
The above 1~4 is only the embodiment of the present invention, and 5 be comparative example, from embodiment 1~4 and comparative example
In 5 performance comparison, the heat resistance and glossiness of the compound modified UV cathode electrophoresis dopes of synthesis of phenyl are obviously improved, right
In not thereby limiting the scope of the invention for pressure electrophoretic coating, every equivalent structure using present specification
Or equivalent process transformation, other related technical areas are directly or indirectly used in, are similarly included in the guarantor of the present invention
In the range of shield.
Claims (10)
- A kind of 1. phenyl compound, it is characterised in that:Its structural formula is Formulas I
- 2. the preparation method of phenyl compound according to claim 1, it is characterised in that:To be situated between by reaction of organic solvent Matter, using benzaldehyde and methyl acrylate as reaction raw materials, reaction raw materials are reacted under the action of catalyst, and purifying, obtains Phenyl compound.
- 3. the preparation method of phenyl compound according to claim 2, it is characterised in that:The catalyst is triethylamine, triethylene diamine, tetrabutyl Ammonium hydrogen sulfate, four butyl bromation amine, triethylbenzyl chlorination One or more of amine, 4-dimethylaminopyridine;The organic solvent is tetrahydrofuran, ethyl acetate, methanol, dimethyl are sub- One or more of sulfone, dimethylformamide;The molar ratio of the benzaldehyde and methyl acrylate is (2~10) mol:(3~15) mol;The amount ratio of the benzaldehyde and catalyst is (2~10) mol:(2~12) mol;The benzaldehyde and organic solvent Amount ratio is (2~10) mol:(50~200) ml;The temperature of the reaction is room temperature, and whether the reaction is completed by thin-layered chromatography TLC monitoring reactions.
- 4. a kind of UV types cathode electrophoresis dope is prepared using phenyl compound described in claim 1.
- 5. UV types cathode electrophoresis dope according to claim 4, it is characterised in that:It is made of following component by weight: 10~25 parts of dimethylaminoethyl methacrylate, 15~30 parts of methyl methacrylate, 4~20 parts of hydroxy-ethyl acrylate, third 15~30 parts of olefin(e) acid butyl ester, 5~20 parts of styrene, 5~20 parts of diisocyanate, 0.2~1 part of catalyst, 1~2 part of polymerization inhibitor, 1~10 part of radical initiator, 2~8 parts of dispersant, 2~8 parts of photoinitiator, 5~30 parts of phenyl compound, neutralizer 3~10 Part, 102~210 parts of organic solvent, 100~1500 parts of water.
- 6. UV types cathode electrophoresis dope according to claim 5, it is characterised in that:The diisocyanate is isophorone two Isocyanates;The catalyst is triethylamine, dibutyl tin laurate, triethylene diamine, tetrabutyl Ammonium hydrogen sulfate, the tetrabutyl One or more of amine bromide, triethylbenzyl ammonium chloride, 4-dimethylaminopyridine;The polymerization inhibitor for hydroquinone, 1,4-benzoquinone, 2,6- toluene di-tert-butyl phenols, beta-phenyl naphthylamines, to tert-butyl o benzene One or more of diphenol;The radical initiator is azodiisobutyronitrile, azo-bis-iso-dimethyl, in benzoyl peroxide it is a kind of with On;The dispersant is one in ethylene glycol monobutyl ether, propyleneglycoles monobutyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether More than kind;The photoinitiator is 1- hydroxycyclohexyl phenyl ketones, 2- hydroxy-2-methyl -1- phenylacetones, 2,4,6- trimethyls In benzoyl-diphenyl phosphine oxide, 2- hydroxy-2-methyls -1- [4- (2- hydroxyl-oxethyls) phenyl] -1- acetone it is a kind of with On;The neutralizer is one or more of lactic acid, glacial acetic acid, nitric acid, bishydroxymethyl propionic acid;The organic solvent is propylene glycol methyl ether acetate, ethyl acetate, methanol, dimethyl sulfoxide (DMSO), methyl iso-butyl ketone (MIBK) it is mixed One or more of compound.
- 7. according to the preparation method of the UV types cathode electrophoresis dope of claim 5 or 6, it is characterised in that:Comprise the following steps:(1) by 10~25 parts of dimethylaminoethyl methacrylate, 15~30 parts of methyl methacrylate, hydroxy-ethyl acrylate 2 ~10 parts, 15~30 parts of butyl acrylate, 5~20 parts of styrene, 1~10 part of radical initiator and organic solvent 50~100 Part is uniformly mixed, and obtains mixed monomer solution;Under conditions of stirring, in 70 DEG C~90 DEG C, to 50~100 parts of organic solvents In, mixed monomer solution is added dropwise, 4~6h is kept the temperature after being added dropwise, it is 50wt%~70wt% to be evaporated under reduced pressure to solid content, is obtained Product A;(2) 0.5~1 part of 5~20 parts of diisocyanate and polymerization inhibitor are uniformly mixed, then at 40~70 DEG C, are added dropwise by third 2~10 parts of olefin(e) acid hydroxyl ethyl ester and 0.1~0.5 part of mixture mixed of catalyst, after dripping, sustained response, works as reaction During the content of the theoretical value after the content of-NCO reaches semiclosed in system, reaction is terminated, obtains product B;(3) 0.1~0.5 part of catalyst, 0.5~1 part of polymerization inhibitor are dissolved in 2~10 parts of organic solvents, obtain catalyst and resistance The mixed solution of poly- agent;The mixed solution of catalyst and polymerization inhibitor is uniformly mixed with the product B of step (2), obtains mixture; Under conditions of stirring, in 40 DEG C~70 DEG C, mixture is added dropwise into the product A of step (1), is added dropwise, keep the temperature 3~4h, Obtain resin product;(4) in 40 DEG C~70 DEG C, 3~10 parts of neutralizer is added to the resin product of step (3), stirs evenly, is down to room temperature, add Enter 5~30 parts of 2~8 parts of dispersant, 2~8 parts of photoinitiator and phenyl compound, be uniformly dispersed, be gradually added 100~1500 parts Water make it that solid content is 10~20%, and high speed emulsion dispersion, curing, obtains UV type cathode electrophoresis dopes.
- 8. the preparation method of UV types cathode electrophoresis dope according to claim 7, it is characterised in that:It is high described in step (4) The condition of fast emulsion dispersion is to disperse 20~60min under 3000~6000r/min rotating speeds, and the condition of curing is with 150~250r/ Min cures 24~48h.
- 9. according to the application of any one of the claim 4~6 UV types cathode electrophoresis dope, it is characterised in that:The UV types are cloudy Pole electrophoretic coating is used to prepare electrophoresis product.
- 10. application according to claim 9, it is characterised in that:The specific preparation method of the electrophoresis product is:With UV types Cathode electrophoresis dope is working solution, using aluminium alloy plate as anode, using substrate pole plate as cathode, carries out electrophoretic process, cleans, do Dry, UV lamp irradiation, obtains electrophoresis product;The spacing of the cathode and anode is 8~15cm;100~150V of supply voltage of the electrophoresis, the time of electrophoresis is 60 ~180s;The condition of the UV lamp irradiation is that 10~60s is irradiated under the UV lamp of 1000W~2000W.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201711147163.2A CN107987716B (en) | 2017-11-17 | 2017-11-17 | Phenyl compound and UV type cathode electrophoretic coating as well as preparation and application thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201711147163.2A CN107987716B (en) | 2017-11-17 | 2017-11-17 | Phenyl compound and UV type cathode electrophoretic coating as well as preparation and application thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN107987716A true CN107987716A (en) | 2018-05-04 |
CN107987716B CN107987716B (en) | 2020-06-19 |
Family
ID=62031566
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201711147163.2A Expired - Fee Related CN107987716B (en) | 2017-11-17 | 2017-11-17 | Phenyl compound and UV type cathode electrophoretic coating as well as preparation and application thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN107987716B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114316660A (en) * | 2021-12-17 | 2022-04-12 | 广东工业大学 | Water-based ultraviolet-curing cathode electrophoretic coating and preparation method thereof |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107163664A (en) * | 2017-06-14 | 2017-09-15 | 深圳市天泽科技实业有限公司 | Ultraviolet light solidifies the preparation method of cathode electrodip painting |
-
2017
- 2017-11-17 CN CN201711147163.2A patent/CN107987716B/en not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107163664A (en) * | 2017-06-14 | 2017-09-15 | 深圳市天泽科技实业有限公司 | Ultraviolet light solidifies the preparation method of cathode electrodip painting |
Non-Patent Citations (1)
Title |
---|
ANTONIO LATORRE ET AL: "study of the stereoselectivity of the nucleophilic epoxidation of 3-hydroxy-2-methylene esters", 《TETRAHEDRON》 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114316660A (en) * | 2021-12-17 | 2022-04-12 | 广东工业大学 | Water-based ultraviolet-curing cathode electrophoretic coating and preparation method thereof |
WO2023109123A1 (en) * | 2021-12-17 | 2023-06-22 | 广东深展实业有限公司 | Water-based ultraviolet curing cathode electrophoretic coating and preparation method therefor |
Also Published As
Publication number | Publication date |
---|---|
CN107987716B (en) | 2020-06-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN105585879B (en) | One kind can quick-setting acrylic resin paint | |
CN103289553B (en) | Transparent high wear-resistant acrylic acid cathode electrophoretic paint and preparation method thereof | |
CN100503757C (en) | Ultraviolet light solidifying paint containing POSS and its preparation method | |
CN104448282A (en) | Alkyd acrylic ester and photocureable coating thereof | |
CN113416477B (en) | Photosensitive phytic acid doped polyaniline-based ultraviolet-curing anticorrosive paint and preparation method thereof | |
CN111138290B (en) | Aromatic ring-containing benzophenone derivative and preparation method and application thereof | |
CN112358592B (en) | Polyurethane structure photoinitiator and preparation method thereof | |
CN113861808B (en) | Roller-coated UV white primer with excellent UV ink wettability and preparation method thereof | |
WO2023109123A1 (en) | Water-based ultraviolet curing cathode electrophoretic coating and preparation method therefor | |
CN106479338B (en) | A kind of preparation method with hydrophobic cationic acrylate resin cathode electrophoresis dope | |
CN107987716A (en) | A kind of phenyl compound and UV type cathode electrophoresis dope and its preparation and application | |
CN112321812A (en) | Polyester type composite photoinitiator and preparation method thereof | |
CN105176155A (en) | UV cured cathode electrophoresis paint with side chain containing ammonium salt positive ions and preparation method therefor | |
CN104672366A (en) | High-solid low-viscosity acrylic resin and preparation method thereof | |
CN107974191A (en) | A kind of naphthyl modified compound and UV types cathode electrophoresis dope and its preparation and application | |
CN113801565A (en) | UV-cured water-based cathode electrophoretic coating and preparation method and application thereof | |
CN106867433B (en) | A kind of naphthalene curing agent, UV solidification heat resistant type pressure sensitive adhesive and pressure sensitive adhesive tape and preparation method | |
CN103819654B (en) | Special resin for water-based ultraviolet curing coating and preparation method and application thereof | |
WO2015127794A1 (en) | Photocuring coating and preparation method therefor | |
CN113651904B (en) | Photopolymerizable single-component thioxanthone photoinitiator | |
CN111303372A (en) | Graphene oxide modified water-based closed isocyanate curing agent and preparation method thereof | |
CN112391095B (en) | Photo-curing epoxy acrylate cathode electrophoretic coating and preparation and application thereof | |
CN106433435A (en) | LED-UV cured cationic acrylic acid cathode electrophoretic paint and application thereof | |
CN101768402A (en) | Method for producing acrylic anodic electrophoretic coating | |
CN108456275A (en) | The preparation method of the ultrafast dry car refinishing paint Hydroxylated acrylic resin of low temperature |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20200619 |