CN107254251A - A kind of aqueous UV urethane acrylate dispersoids with self-initiating function and preparation method thereof - Google Patents
A kind of aqueous UV urethane acrylate dispersoids with self-initiating function and preparation method thereof Download PDFInfo
- Publication number
- CN107254251A CN107254251A CN201710565042.3A CN201710565042A CN107254251A CN 107254251 A CN107254251 A CN 107254251A CN 201710565042 A CN201710565042 A CN 201710565042A CN 107254251 A CN107254251 A CN 107254251A
- Authority
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- China
- Prior art keywords
- aqueous
- self
- urethane acrylate
- reaction
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 46
- GTACSIONMHMRPD-UHFFFAOYSA-N 2-[4-[2-(benzenesulfonamido)ethylsulfanyl]-2,6-difluorophenoxy]acetamide Chemical compound C1=C(F)C(OCC(=O)N)=C(F)C=C1SCCNS(=O)(=O)C1=CC=CC=C1 GTACSIONMHMRPD-UHFFFAOYSA-N 0.000 claims abstract description 14
- 101710130081 Aspergillopepsin-1 Proteins 0.000 claims abstract description 14
- 102100031007 Cytosolic non-specific dipeptidase Human genes 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 9
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- 150000001412 amines Chemical class 0.000 claims abstract description 8
- 229960001330 hydroxycarbamide Drugs 0.000 claims abstract description 8
- 239000003112 inhibitor Substances 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims abstract description 6
- 239000000178 monomer Substances 0.000 claims abstract description 6
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 6
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000008367 deionised water Substances 0.000 claims abstract description 4
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 63
- 229920001451 polypropylene glycol Polymers 0.000 claims description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- 238000009413 insulation Methods 0.000 claims description 13
- 239000006185 dispersion Substances 0.000 claims description 12
- 239000011259 mixed solution Substances 0.000 claims description 12
- 150000003077 polyols Chemical class 0.000 claims description 12
- 229920005862 polyol Polymers 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- 238000010792 warming Methods 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 8
- 239000000839 emulsion Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 229920000728 polyester Polymers 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- -1 tert-butyl o Benzenediol Chemical compound 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 5
- 238000013019 agitation Methods 0.000 claims description 5
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 claims description 5
- 229920006150 hyperbranched polyester Polymers 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 230000009467 reduction Effects 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical group CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-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
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 238000006386 neutralization reaction Methods 0.000 claims description 4
- 235000019260 propionic acid Nutrition 0.000 claims description 4
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 claims description 3
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 3
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 claims description 3
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 229920001610 polycaprolactone Polymers 0.000 claims description 3
- 239000004632 polycaprolactone Substances 0.000 claims description 3
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 claims description 2
- HOYRZHJJAHRMLL-UHFFFAOYSA-N 2,6-dinitro-p-cresol Chemical group CC1=CC([N+]([O-])=O)=C(O)C([N+]([O-])=O)=C1 HOYRZHJJAHRMLL-UHFFFAOYSA-N 0.000 claims description 2
- DUMPKRLSSRTFMY-UHFFFAOYSA-N 2-butan-2-yl-3,4-dinitrophenol Chemical group CCC(C)C1=C(O)C=CC([N+]([O-])=O)=C1[N+]([O-])=O DUMPKRLSSRTFMY-UHFFFAOYSA-N 0.000 claims description 2
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical group CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 claims description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 2
- NNTWKXKLHMTGBU-UHFFFAOYSA-N 4,5-dihydroxyimidazolidin-2-one Chemical compound OC1NC(=O)NC1O NNTWKXKLHMTGBU-UHFFFAOYSA-N 0.000 claims description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical group CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
- 235000015511 Liquidambar orientalis Nutrition 0.000 claims description 2
- 239000004870 Styrax Substances 0.000 claims description 2
- 244000028419 Styrax benzoin Species 0.000 claims description 2
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 2
- AFSQFGXTYWXFPP-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OCC1(CO)CCCCC1 AFSQFGXTYWXFPP-UHFFFAOYSA-N 0.000 claims description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229960002887 deanol Drugs 0.000 claims description 2
- 239000012972 dimethylethanolamine Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 2
- 210000000056 organ Anatomy 0.000 claims description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 2
- 229960003742 phenol Drugs 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920005906 polyester polyol Polymers 0.000 claims description 2
- 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 2
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 claims 1
- ZFMFIBDSZCASNS-UHFFFAOYSA-N 2-pentylbenzene-1,4-diol Chemical group CCCCCC1=CC(O)=CC=C1O ZFMFIBDSZCASNS-UHFFFAOYSA-N 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- SOGAXMICEFXMKE-UHFFFAOYSA-N alpha-Methyl-n-butyl acrylate Natural products CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000005456 glyceride group Chemical group 0.000 claims 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- DMFQXOQJSOTYKY-UHFFFAOYSA-N prop-2-ene-1,1-diol;urea Chemical compound NC(N)=O.OC(O)C=C DMFQXOQJSOTYKY-UHFFFAOYSA-N 0.000 claims 1
- 238000007711 solidification Methods 0.000 abstract description 9
- 230000008023 solidification Effects 0.000 abstract description 9
- 239000012528 membrane Substances 0.000 abstract description 7
- 239000003999 initiator Substances 0.000 abstract description 6
- 238000007790 scraping Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 239000011347 resin Substances 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 abstract description 2
- 238000001723 curing Methods 0.000 description 8
- 235000013877 carbamide Nutrition 0.000 description 7
- 239000004202 carbamide Substances 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 238000003848 UV Light-Curing Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003292 glue Substances 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000005474 octanoate group Chemical group 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 150000004672 propanoic acids Chemical class 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- SVLIBCWCEABYRF-UHFFFAOYSA-N 1-ethenyl-1-(2-hydroxyethyl)urea Chemical compound NC(=O)N(C=C)CCO SVLIBCWCEABYRF-UHFFFAOYSA-N 0.000 description 1
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 1
- ZUSRWMNPQGTIBY-UHFFFAOYSA-N N=C=O.N=C=O.C(C1CCCCC1)C1CCCCC1.C(C1CCCCC1)C1CCCCC1 Chemical compound N=C=O.N=C=O.C(C1CCCCC1)C1CCCCC1.C(C1CCCCC1)C1CCCCC1 ZUSRWMNPQGTIBY-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical class COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 125000006838 isophorone group Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- GXZLBUYKJFLNLF-UHFFFAOYSA-N prop-2-ene-1,1-diol Chemical compound OC(O)C=C GXZLBUYKJFLNLF-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001960 triggered effect 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
-
- 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
- C08G18/3271—Hydroxyamines
- C08G18/3293—Hydroxyamines containing heterocyclic 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic 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
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Abstract
The invention discloses a kind of aqueous UV urethane acrylate dispersoids with self-initiating function and preparation method thereof, the aqueous UV urethane acrylate dispersoids include the constitutive material of following parts by weight：10~20 parts of PEPA or PPG；10~30 parts of diisocyanate；2~10 parts of multi-hydroxy carboxy acid；0.04~0.2 part of catalyst；5~15 parts of organic solvent；1~5 part of hydroxycarbamide；0.1~0.6 part of polymerization inhibitor；10~30 parts of monohydroxy acrylate monomer；15~35 parts of oligomer containing light-initiated group and terminal hydroxy group；1~5 part of organic amine；140~180 parts of deionized water.The aqueous UV urethane acrylate dispersoids have self-initiating or trigger function altogether under the effect of micro initiator, and resin solidification efficiency high simultaneously can carry out deep cure, the surface resistance to scraping of glued membrane is good, hardness greatly, weatherability and chemical resistance it is excellent.
Description
Technical field
The present invention relates to aqueous UV curing coating technical field, and in particular to a kind of aqueous UV with self-initiating function gathers
Urethane acrylate dispersion and preparation method thereof.
Background technology
UV-curing technology because its efficiently, energy-conservation, low emission the advantages of quickly grow, light trigger be traditional light consolidate
Important component in change system, the light trigger used at present is largely aromatic compound, itself has certain toxicity,
Undergo after ultraviolet light irradiation, a large amount of undecomposed light trigger small molecules of remaining in cured film all can to environment and contact personnel
Exert an adverse impact, limit application of the photocuring technology in fields such as high request, high standard industries.
Self-initiation ultraviolet-curing system, is not required to light trigger due to it or only needs a small amount of light trigger, it becomes possible to
Free radical is produced under ultraviolet radiation and completes cross-linking and curing reaction, is aroused great concern.And can self-initiating it is aqueous
UV curing system is nontoxic, has more wide application prospect on environmental-protecting performance.Earliest self-initiating solidification is low
Polymers, is the new product of Ya Shilan companies of U.S. research and development, and it is that occur Michael by multi-functional acrylate and 'beta '-ketoester
Made from addition reaction.Related researcher develops many self-initiating curing systems on this basis, still, existing to draw certainly
Hair material or solidification rate are relatively slow or there is certain mixing scattering problem, and the quality to later product is adversely affected.
The content of the invention
The technical problems to be solved by the invention are to overcome the shortcomings of to mention with defect that there is provided one in background above technology
Plant with self-initiating or trigger function altogether under the effect of micro initiator, resin solidification efficiency high simultaneously can carry out deep cure, glue
The surface resistance to scraping of film is good, hardness is big, weatherability and the excellent aqueous UV urethane acrylate dispersoids of chemical resistance, and
Accordingly provide a kind of preparation method of the aqueous UV urethane acrylate dispersoids.
In order to solve the above technical problems, technical scheme proposed by the present invention is：
A kind of aqueous UV urethane acrylate dispersoids with self-initiating function, including the composition of following parts by weight are former
Material：PEPA or 10~20 parts of PPG, 10~30 parts of diisocyanate, 2~10 parts of multi-hydroxy carboxy acid, catalyst
0.04~0.2 part, 5~15 parts of organic solvent, 1~5 part of hydroxycarbamide, 0.1~0.6 part of polymerization inhibitor, monohydroxy acrylate monomer
10~30 parts, 1~5 part of 15~35 parts of oligomer, organic amine containing light-initiated group and terminal hydroxy group, deionized water 140~180
Part.
The above-mentioned aqueous UV urethane acrylate dispersoids with self-initiating function, it is preferred that described containing light-initiated
The oligomer of group and terminal hydroxy group includes the constitutive material of following parts by weight：30~50 parts of hydroxyl light trigger mixed solution,
10~20 parts of diisocyanate, 30~60 parts of polyol polyester acrylate, wherein, the hydroxyl light trigger mixed solution
By the catalyst of the hydroxyl light trigger, the organic solvent of 20~60 parts by weight and 0.1~0.5 parts by weight of 30~70 parts by weight
Composition.
The above-mentioned aqueous UV urethane acrylate dispersoids with self-initiating function, it is preferred that the hydroxyl light
Initiator in Darocur 1173, Irgacure 184, Irgacure 2959, Irgacure 1000, styrax one
Plant or several；The organic solvent is acetone or butanone；The catalyst is organic tin catalyst, selected from the fourth of tin dilaurate two
One or more in Ji Xi, stannous octoate, dibutyl tin dichloride.
The above-mentioned aqueous UV urethane acrylate dispersoids with self-initiating function, it is preferred that two isocyanic acid
Ester is the compound with least one isocyanate-reactive group, selected from IPDI, dicyclohexyl first
Alkane diisocyanate, toluene di-isocyanate(TDI), hexamethylene diisocyanate, methyl diphenylene diisocyanate, hexamethylene two
One or more in isocyanates, tetramethylene diisocyanate.
The above-mentioned aqueous UV urethane acrylate dispersoids with self-initiating function, it is preferred that the polyhydroxy polycarboxylic
Ester acrylate can spend selected from six degrees of functionality, twelve interior organs, one kind or many in the hyperbranched polyester acrylic ester of 18 degrees of functionality
Kind, the mass ratio of polyol polyester acrylate and the hydroxyl light trigger is (1.5~10.0): 1.
The above-mentioned aqueous UV urethane acrylate dispersoids with self-initiating function, it is preferred that the polyester polyols
Alcohol is the one or more in polycaprolactone polyol, polycarbonate polyol, polyadipate dihydric alcohol, point of PEPA
Son amount is 500~2000；The PPG is graft type PPG, polytetrahydrofuran polyol, heterocyclic modified poly-
One or more in ethoxylated polyhydric alcohol, the molecular weight of PPG is 400~1000.
The above-mentioned aqueous UV urethane acrylate dispersoids with self-initiating function, it is preferred that the polyhydroxy carboxylic
Acid is one or both of dihydromethyl propionic acid and dimethylolpropionic acid, multi-hydroxy carboxy acid and the PEPA or polyethers
The mass ratio of polyalcohol is (0.2~0.8): 1；The hydroxycarbamide is selected from hydroxycarbamide, hydroxyethyl vinyl urea, dihydroxymethyl ethene
One or more in urea, hydroxymethyl-2 dihydroxy-ethylene urea, the matter of hydroxycarbamide and the PEPA or PPG
Amount is than being 1: (0.1~0.6).
The above-mentioned aqueous UV urethane acrylate dispersoids with self-initiating function, it is preferred that the polymerization inhibitor is
Phenolic inhibitor, selected from hydroquinones, p methoxy phenol, para hydroxybenzene ether, p-tert-Butylcatechol, two tertiary pentyls pair
In benzenediol, dinitro-p-cresol, dinitro sec-butyl phenol, p-tert-Butylcatechol, di-t-butyl paraethyl phenol
It is one or more of；The monohydroxy acrylate monomer is selected from hydroxyethyl methacrylate, hydroxy-ethyl acrylate, pentaerythrite three
Acrylate, hydroxy propyl methacrylate, 2- hydroxy-n-butyls methacrylate, 3- hydroxy-n-butyls methacrylate,
One in 4- hydroxy-n-butyls methacrylate, cyclohexanedimethanol monomethacrylates, glycerol monomethacrylate
Plant or several.
The above-mentioned aqueous UV urethane acrylate dispersoids with self-initiating function, it is preferred that described containing light-initiated
The mass ratio of the oligomer of group and terminal hydroxy group and the PEPA or PPG is (0.5~3.0): 1；It is described to have
Machine amine is the one or more in triethylamine, dimethylethanolamine, methyl diethanolamine, organic amine and the PEPA or
The mass ratio of PPG is (0.15~0.4): 1.
As a total technical concept, another aspect of the present invention provides a kind of above-mentioned aqueous with self-initiating function
The preparation method of UV urethane acrylate dispersoids, comprises the following steps：
(1) preparation of the oligomer containing light-initiated group and terminal hydroxy group
Hydroxyl light trigger, organic solvent and catalyst are mixed by proportioning, stir molten at 50 DEG C~80 DEG C
Solution obtains hydroxyl light trigger mixed solution, set aside for use to transparency liquid；Diisocyanate is added in reaction vessel, risen
Hydroxyl light trigger mixed solution is added dropwise to 60 DEG C~65 DEG C in temperature while stirring, and it is 0.5 drop/sec~1.5 to control rate of addition
Drop/sec, to all dripping off, 70 DEG C~75 DEG C are warming up to, continues to react 2.0h~4.0h；After NCO% reaches theoretical value, add
Polyol polyester acrylate, insulation reaction 2.0h~4.0h, when NCO% is less than 0.1%, reaction terminates, and obtains drawing containing light
Send out the oligomer of group and terminal hydroxy group；
(2) preparation of aqueous UV urethane acrylate dispersoids
Diisocyanate, PEPA or PPG, multi-hydroxy carboxy acid and catalyst are added by proportioning anti-
Answer in container, be well mixed, be filled with nitrogen, reacted at 60 DEG C~70 DEG C, be incubated in 2.0h~4.0h, course of reaction and add
Enter organic solvent viscosity reduction, detect the NCO% contents of course of reaction, when NCO% contents are close to theoretical value, add dried hydroxyl
Base urea carries out chain extending reaction, insulation reaction 2.0h~4.0h, then detects the NCO% contents of course of reaction, when NCO% contents are close
During theoretical value, polymerization inhibitor and monohydroxy acrylate monomer are added, 0.5h~2.0h is reacted at 60 DEG C~65 DEG C, is then added
Oligomer containing light-initiated group and terminal hydroxy group obtained by step (1) carries out graft reaction, reacted at 60 DEG C~65 DEG C 2.0h~
4.0h, detects the NCO% contents of course of reaction, and reaction temperature is down into 45 DEG C~50 DEG C when NCO% contents are less than 0.1%,
Add organic amine and carry out neutralization reaction, add deionized water, dispersion and emulsion 0.5h~1.5h, is then steamed under high velocity agitation
Solvent, produces the aqueous UV urethane acrylate dispersoids with self-initiating function.
Compared with prior art, the advantage of the invention is that：The aqueous UV polyurethane with self-initiating function of the present invention
Acrylate dispersoid using the structure containing urea bond small molecule carry out chain extending reaction, introduce with help trigger function urea bond with
Tertiary amine structure, while also improving the mechanical property of glued membrane；It is anti-by the grafting with light-initiated group and the oligomer of terminal hydroxy group
Should, light-initiated group has been also introduced into after the end of performed polymer macromolecular, dispersion and emulsion, has obtained the water with self-initiating characteristic
Property UV urethane acrylate dispersoids, the solid content of dispersion is between 25.0%~45.0%, its emulsion storage stability
Well, coating surface resistance to scraping, hardness, chemical resistance are good.The dispersion has dual self-initiating mechanism, in ultraviolet radiation
Under the conditions of, self-initiating can be realized or triggered altogether under being acted under micro initiator, and curing rate is not less than by light-initiated
The aqueous UV urethane acrylates of agent solidification.
Embodiment
For the ease of understanding the present invention, present invention work more comprehensively, is meticulously described below in conjunction with preferred embodiment,
But protection scope of the present invention is not limited to embodiment in detail below.
Unless otherwise defined, the implication that all technical terms used hereinafter are generally understood that with those skilled in the art
It is identical.Technical term used herein is intended merely to describe the purpose of specific embodiment, is not intended to the limitation present invention
Protection domain.
Unless otherwise specified, various raw material, reagent, instrument and equipment used in the present invention etc. can be by city
Field is commercially available or can prepared by existing method.
Embodiment 1：
A kind of aqueous UV urethane acrylate dispersoids with self-initiating function of the invention and preparation method thereof.Should
The preparation method of aqueous UV urethane acrylate dispersoids comprises the following steps：
(1) preparation of the oligomer containing light-initiated group and terminal hydroxy group：
The light triggers of 24.6g Darocurl 173,30g acetone, 0.08g dibutyl tin laurates are added to single port
In flask, stirring and dissolving obtains hydroxyl light trigger mixed solution, set aside for use to transparency liquid at 60 DEG C；By 25.2g
1, hexamethylene-diisocyanate is added in reaction vessel, is warming up to 65 DEG C, the mixing of hydroxyl light trigger is added dropwise while stirring molten
Liquid, controls rate of addition, to all dripping off, to be warming up to 70 DEG C for 1.0 drops/sec, continues to react 4.0h；When NCO% (100g samples
The quality of contained isocyanates (- NCO) group) reach after theoretical value, add 91.2g hyperbranched polyester acrylic esters, insulation
3.0h is reacted, when NCO% is less than 0.1%, reaction terminates, and obtains the oligomer containing light-initiated group and terminal hydroxy group.
(2) preparation of aqueous UV urethane acrylate dispersoids：
By 25.2g IPDIs, 16.7g polycaprolactone diolss, 4.5g dihydromethyl propionic acids and
0.06g dibutyl tin laurates are added in reaction vessel, are well mixed, are filled with nitrogen, are reacted at 60 DEG C, are incubated
12g acetone viscosity reductions are added in 4.0h, course of reaction, the NCO% contents of course of reaction are detected；When NCO% is close to theoretical value,
Dried 2.2g hydroxyethyl vinyls urea is added at 65 DEG C and carries out chain extending reaction, insulation reaction 3.0h detects course of reaction
NCO% contents；When NCO% is close to theoretical value, 0.25g p methoxy phenols, 4.3g hydroxy-ethyl acrylates, 18.1g seasons are added
Penta tetrol triacrylate, 1.5h is reacted at 65 DEG C, add prepared by 28.6g steps (1) containing light-initiated group and terminal hydroxy group
Oligomer and 0.05g dibutyl tin laurates carry out graft reaction, and insulation reaction 2.5h detects the NCO% of course of reaction
Content；When NCO% contents are less than 0.1%, reaction temperature is down to 45 DEG C, 3.4g triethylamines is added and carries out neutralization reaction, then
146g deionized waters are added, under high velocity agitation dispersion and emulsion 1.5h, then steam solvent using Rotary Evaporators, that is, had
There are the aqueous UV urethane acrylate dispersoids of self-initiating function.
By the aqueous UV urethane acrylate dispersoids with self-initiating function, film forming solidifies alone, and test glued membrane is not
Curing rate, hardness, resistance to alcohol performance under the conditions of same curing mode and solidification energy, method of testing are as follows：According to GB/T
6739-2006 determines glued membrane hardness；Glued membrane is immersed in ethanol solution at room temperature and determines resistance to alcohol performance.Test result is such as
Shown in table 1, table 2.
Embodiment 2：
A kind of aqueous UV urethane acrylate dispersoids with self-initiating function of the invention and preparation method thereof.Should
The preparation method of aqueous UV urethane acrylate dispersoids comprises the following steps：
(1) preparation of the oligomer containing light-initiated group and terminal hydroxy group：
36.2g Irgacure2959 light triggers, 35g butanone, 0.15g stannous octoates are added in single-necked flask,
Stirring and dissolving obtains hydroxyl light trigger mixed solution, set aside for use to transparency liquid at 55 DEG C；By 36.5g isophorones two
Isocyanates is added in reaction vessel, is warming up to 65 DEG C, and hydroxyl light trigger mixed solution, control drop are added dropwise while stirring
Acceleration is 1.0 drops/sec and dripped off to whole, is warming up to 75 DEG C, continues to react 3.0h；After NCO% reaches theoretical value, add
97.3g hyperbranched polyester acrylic esters, insulation reaction 3.5h, when NCO% is less than 0.1%, reaction terminates, and obtains containing light-initiated
The oligomer of group and terminal hydroxy group.
(2) preparation of aqueous UV urethane acrylate dispersoids：
By 16.7g PolyTHFs dihydric alcohol, 29.7g dicyclohexyl methyl hydride diisocyanates, 5.0g dimethylolpropionic acids
And 0.08g stannous octoates are added in reaction vessel, it are well mixed, are filled with nitrogen, are reacted at 70 DEG C, is incubated
15g acetone viscosity reductions are added in 2.5h, course of reaction, the NCO% contents of course of reaction are detected；When NCO% is close to theoretical value,
Dried 2.7g hydroxymethyl-2 dihydroxy-ethylene ureas are added at 65 DEG C and carry out chain extending reaction, insulation reaction 3.0h, detection reaction
The NCO% contents of process；When NCO% is close to theoretical value, 0.25g hydroquinones, 4.3g hydroxy-ethyl acrylates, 5.2g first are added
Base hydroxypropyl acrylate, 1.0h is reacted at 65 DEG C, and add prepared by 30.3g steps (1) is low containing light-initiated group and terminal hydroxy group
Polymers and 0.05g stannous octoates carry out graft reaction, and insulation reaction 3.0h detects the NCO% contents of course of reaction；When
When NCO% contents are less than 0.1%, reaction temperature is down to 50 DEG C, 3.4g dimethylethanolamines is added and carries out neutralization reaction, then add
Enter 146g deionized waters, under high velocity agitation dispersion and emulsion 0.5h, then steam solvent using Rotary Evaporators, that is, had
The aqueous UV urethane acrylate dispersoids of self-initiating function.
The properties of the aqueous UV urethane acrylate dispersoids with self-initiating function are tested, tested
Method be the same as Example 1, test result is as shown in table 1, table 2.
Embodiment 3：
A kind of aqueous UV urethane acrylate dispersoids with self-initiating function of the invention and preparation method thereof.Should
The preparation method of aqueous UV urethane acrylate dispersoids comprises the following steps：
(1) preparation of the oligomer containing light-initiated group and terminal hydroxy group：
45.4g Irgacure184 light triggers, 45g acetone, 0.18g dibutyl tin dichlorides are added to single-necked flask
In, stirring and dissolving obtains hydroxyl light trigger mixed solution, set aside for use to transparency liquid at 50 DEG C；By the hexamethylenes of 31.4g bis-
Dicyclohexylmethane diisocyanate is added in reaction vessel, is warming up to 60 DEG C, the mixing of hydroxyl light trigger is added dropwise while stirring molten
Liquid, controls rate of addition, to all dripping off, to be warming up to 70 DEG C for 1.0 drops/sec, continues to react 2.0h；When NCO% reaches theoretical value
Afterwards, addition 72.9g hyperbranched polyester acrylic esters, insulation reaction 4.0h, when NCO% is less than 0.1%, reaction terminates, and obtains
Oligomer containing light-initiated group and terminal hydroxy group.
(2) preparation of aqueous UV urethane acrylate dispersoids：
By 17.5g PCDLs, 26.5g IPDIs, 4.7g dihydromethyl propionic acids and
0.08g dibutyl tin dichlorides are added in reaction vessel, are well mixed, are filled with nitrogen, are reacted at 65 DEG C, are incubated
15g acetone viscosity reductions are added in 2.0h, course of reaction, the NCO% contents of course of reaction are detected；When NCO% is close to theoretical value,
Dried 2.3g hydroxyethyl vinyls urea is added at 70 DEG C and carries out chain extending reaction, insulation reaction 4.0h detects course of reaction
NCO% contents；When NCO% is close to theoretical value, add 0.28g p-tert-Butylcatechols, 5.1g hydroxy propyl methacrylates,
20.6g pentaerythritol triacrylates, 2.0h is reacted at 60 DEG C, and add prepared by 32.9g steps (1) contains light-initiated group and end
The oligomer and 0.06g dibutyl tin dichlorides of hydroxyl carry out graft reaction, and insulation reaction 3.0h detects course of reaction
NCO% contents；When NCO% contents are less than 0.1%, reaction temperature is down to 45 DEG C, 3.6g triethylamines is added and neutralize instead
Should, 146g deionized waters are added, under high velocity agitation dispersion and emulsion 1.5h, then steam solvent using Rotary Evaporators, i.e.,
Obtain the aqueous UV urethane acrylate dispersoids with self-initiating function.
The properties of the aqueous UV urethane acrylate dispersoids with self-initiating function are tested, tested
Method be the same as Example 1, test result is as shown in table 1, table 2.
The standby initiation system the performance test results of aqueous UV urethane acrylate dispersoids in the embodiment 1~3 of table 1
The common initiation system the performance test results of aqueous UV urethane acrylate dispersoids in the embodiment 1~3 of table 2
From table 1, prepared aqueous UV urethane acrylate dispersoids, can on the premise of without additional initiator
Photocuring is realized in initiation by itself photosensitive group, and cured glue film has a preferable performance, solidification energy it is strong and weak right
The self-initiating efficiency of dispersion has certain influence, (the 600mJ/cm under strong energy radiation2), glue film performance is more excellent；Separately
The difference of outer dispersion structure, has an impact to curing efficiency, in such as embodiment 3, using PCDL as body junction
During structure, curing efficiency is better than other polyol structures.From table 2, on the premise of additional trace photoinitiator, low energy
Under (350mJ/cm2) glued membrane can just obtain preferable hardness with it is resistance to alcohol repellency, then improve solidification energy (600mJ/cm2) glued membrane
Performance change less, illustrates prepared dispersion on the basis of micro initiator is added, and can be achieved with efficiently solidification, obtains good
Good film performance.
The preferred embodiments of the present invention are the foregoing is only, are not intended to limit the invention, for the skill of this area
For art personnel, the present invention can have various modifications and variations.Within the spirit and principles of the invention, that is made any repaiies
Change, equivalent substitution, improvement etc., should be included in the scope of the protection.
Claims (10)
1. a kind of aqueous UV urethane acrylate dispersoids with self-initiating function, it is characterised in that including following weight
The constitutive material of part：
2. the aqueous UV urethane acrylate dispersoids according to claim 1 with self-initiating function, its feature exists
In the oligomer containing light-initiated group and terminal hydroxy group includes the constitutive material of following parts by weight：
30~50 parts of hydroxyl light trigger mixed solution；
10~20 parts of diisocyanate；
30~60 parts of polyol polyester acrylate；
Wherein, hydroxyl light trigger of the hydroxyl light trigger mixed solution by 30~70 parts by weight, 20~60 weight
The organic solvent of part and the catalyst composition of 0.1~0.5 parts by weight.
3. the aqueous UV urethane acrylate dispersoids according to claim 2 with self-initiating function, its feature exists
In the hydroxyl light trigger is selected from Darocur 1173, Irgacure 184, Irgacure 2959, Irgacure
1000th, the one or more in styrax；The organic solvent is acetone or butanone；The catalyst is catalyzed for organic tin
Agent, the one or more in dibutyl tin laurate, stannous octoate, dibutyl tin dichloride.
4. the aqueous UV urethane acrylate dispersoids according to claim 2 with self-initiating function, its feature exists
In the diisocyanate is the compound with least one isocyanate-reactive group, selected from the isocyanide of isophorone two
Acid esters, dicyclohexyl methyl hydride diisocyanate, toluene di-isocyanate(TDI), hexamethylene diisocyanate, diphenyl methane two are different
One or more in cyanate, cyclohexane diisocyanate, tetramethylene diisocyanate.
5. the aqueous UV urethane acrylate dispersoids according to claim 2 with self-initiating function, its feature exists
In the polyol polyester acrylate can spend selected from six degrees of functionality, twelve interior organs, the acrylated hyperbranched polyester of 18 degrees of functionality
One or more in ester, the mass ratio of polyol polyester acrylate and the hydroxyl light trigger is (1.5~10.0):
1。
6. the aqueous UV urethane acrylate dispersoids according to claim 1 or 2 with self-initiating function, its feature
It is, the PEPA is polycaprolactone polyol, polycarbonate polyol, one kind in polyadipate dihydric alcohol or several
Kind, the molecular weight of PEPA is 500~2000；The PPG is graft type PPG, PolyTHF
One or more in polyalcohol, heterocyclic modified PPG, the molecular weight of PPG is 400~1000.
7. the aqueous UV urethane acrylate dispersoids according to claim 1 or 2 with self-initiating function, its feature
It is, the multi-hydroxy carboxy acid is one or both of dihydromethyl propionic acid and dimethylolpropionic acid, multi-hydroxy carboxy acid and institute
The mass ratio for stating PEPA or PPG is (0.2~0.8): 1；The hydroxycarbamide is selected from hydroxycarbamide, ethoxy
One or more in ethylene urea, dihydroxymethyl ethylene urea, hydroxymethyl-2 dihydroxy-ethylene urea, hydroxycarbamide and the polyester polyols
The mass ratio of alcohol or PPG is 1: (0.1~0.6).
8. the aqueous UV urethane acrylate dispersoids according to claim 1 or 2 with self-initiating function, its feature
Be, the polymerization inhibitor be phenolic inhibitor, selected from hydroquinones, p methoxy phenol, para hydroxybenzene ether, to tert-butyl o
Benzenediol, two tertiary pentyl hydroquinones, dinitro-p-cresol, dinitro sec-butyl phenol, p-tert-Butylcatechol, two tertiary fourths
One or more in base paraethyl phenol；The monohydroxy acrylate monomer is selected from hydroxyethyl methacrylate, acrylic acid
Hydroxyl ethyl ester, pentaerythritol triacrylate, hydroxy propyl methacrylate, 2- hydroxy-n-butyls methacrylate, 3- hydroxyls are just
Butyl methyl acrylate, 4- hydroxy-n-butyls methacrylate, cyclohexanedimethanol monomethacrylates, monomethyl third
One or more in olefin(e) acid glyceride.
9. the aqueous UV urethane acrylate dispersoids according to claim 1 or 2 with self-initiating function, its feature
It is, the mass ratio of the oligomer and the PEPA or PPG containing light-initiated group and terminal hydroxy group is
(0.5~3.0): 1；The organic amine is the one or more in triethylamine, dimethylethanolamine, methyl diethanolamine, organic
The mass ratio of amine and the PEPA or PPG is (0.15~0.4): 1.
10. it is a kind of such as the aqueous UV urethane acrylates according to any one of claims 1 to 9 with self-initiating function point
The preparation method of granular media, it is characterised in that comprise the following steps：
(1) preparation of the oligomer containing light-initiated group and terminal hydroxy group
Hydroxyl light trigger, organic solvent and catalyst are mixed by proportioning, stirring and dissolving is extremely at 50 DEG C~80 DEG C
Transparency liquid, obtains hydroxyl light trigger mixed solution, set aside for use；Diisocyanate is added in reaction vessel, is warming up to
60 DEG C~65 DEG C, while stirring be added dropwise hydroxyl light trigger mixed solution, control rate of addition for 0.5 drop/sec~1.5 drip/
Second, to all dripping off, 70 DEG C~75 DEG C are warming up to, continues to react 2.0h~4.0h；After NCO% reaches theoretical value, add many
Hydroxyl polyester acrylate, insulation reaction 2.0h~4.0h, when NCO% is less than 0.1%, reaction terminates, and obtains containing light-initiated
The oligomer of group and terminal hydroxy group；
(2) preparation of aqueous UV urethane acrylate dispersoids
Diisocyanate, PEPA or PPG, multi-hydroxy carboxy acid and catalyst are added into reaction by proportioning to hold
In device, it is well mixed, is filled with nitrogen, is reacted at 60 DEG C~70 DEG C, being incubated to add in 2.0h~4.0h, course of reaction has
Machine solvent viscosity reduction, detects the NCO% contents of course of reaction, when NCO% contents are close to theoretical value, adds dried hydroxycarbamide
Chain extending reaction, insulation reaction 2.0h~4.0h are carried out, then detects the NCO% contents of course of reaction, when the close theory of NCO% contents
During value, polymerization inhibitor and monohydroxy acrylate monomer are added, 0.5h~2.0h is reacted at 60 DEG C~65 DEG C, step is then added
(1) oligomer of the gained containing light-initiated group and terminal hydroxy group carries out graft reaction, and 2.0h~4.0h is reacted at 60 DEG C~65 DEG C,
The NCO% contents of course of reaction are detected, reaction temperature 45 DEG C~50 DEG C are down to when NCO% contents are less than 0.1%, addition has
Machine amine carries out neutralization reaction, adds deionized water, dispersion and emulsion 0.5h~1.5h, then steams solvent under high velocity agitation,
Produce the aqueous UV urethane acrylate dispersoids with self-initiating function.
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