CN114478929A - Polyurethane prepolymer modified matte hydroxypropyl dispersion and preparation method thereof - Google Patents
Polyurethane prepolymer modified matte hydroxypropyl dispersion and preparation method thereof Download PDFInfo
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- CN114478929A CN114478929A CN202111680264.2A CN202111680264A CN114478929A CN 114478929 A CN114478929 A CN 114478929A CN 202111680264 A CN202111680264 A CN 202111680264A CN 114478929 A CN114478929 A CN 114478929A
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- polyurethane prepolymer
- hydroxypropyl
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- 229920001730 Moisture cure polyurethane Polymers 0.000 title claims abstract description 62
- -1 hydroxypropyl Chemical group 0.000 title claims abstract description 54
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 239000006185 dispersion Substances 0.000 title claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000000178 monomer Substances 0.000 claims abstract description 24
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 239000012948 isocyanate Substances 0.000 claims abstract description 13
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 13
- 229920005862 polyol Polymers 0.000 claims abstract description 12
- 150000003077 polyols Chemical class 0.000 claims abstract description 12
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims abstract description 10
- 239000003999 initiator Substances 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
- 239000012975 dibutyltin dilaurate Substances 0.000 claims abstract description 8
- 239000008367 deionised water Substances 0.000 claims abstract description 7
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 27
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 12
- 230000003472 neutralizing effect Effects 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 7
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 claims description 6
- JJRDRFZYKKFYMO-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-ylperoxy)butane Chemical group CCC(C)(C)OOC(C)(C)CC JJRDRFZYKKFYMO-UHFFFAOYSA-N 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 5
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 3
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 claims description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical group CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 239000013538 functional additive Substances 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000005303 weighing Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 abstract description 3
- 239000007787 solid Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000003973 paint Substances 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 230000004913 activation Effects 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- FEWFXBUNENSNBQ-UHFFFAOYSA-N 2-hydroxyacrylic acid Chemical compound OC(=C)C(O)=O FEWFXBUNENSNBQ-UHFFFAOYSA-N 0.000 description 3
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 3
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 3
- 239000012752 auxiliary agent Substances 0.000 description 3
- 229960002887 deanol Drugs 0.000 description 3
- 239000012972 dimethylethanolamine Substances 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 238000009775 high-speed stirring Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229940119545 isobornyl methacrylate Drugs 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000012855 volatile organic compound Substances 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 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
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- IFXDUNDBQDXPQZ-UHFFFAOYSA-N 2-methylbutan-2-yl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)CC IFXDUNDBQDXPQZ-UHFFFAOYSA-N 0.000 description 1
- RFSCGDQQLKVJEJ-UHFFFAOYSA-N 2-methylbutan-2-yl benzenecarboperoxoate Chemical compound CCC(C)(C)OOC(=O)C1=CC=CC=C1 RFSCGDQQLKVJEJ-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical group CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000000809 air pollutant Substances 0.000 description 1
- 231100001243 air pollutant Toxicity 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
-
- 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
- C08F285/00—Macromolecular compounds obtained by polymerising monomers on to preformed graft polymers
-
- 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
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/003—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
Abstract
The invention discloses a polyurethane prepolymer modified matte hydroxypropyl dispersoid and a preparation method thereof, and the polyurethane prepolymer modified matte hydroxypropyl dispersoid comprises a component A and a component B, wherein the component A comprises the following components in parts by weight: 3-5 parts of PMA, 3-6 parts of polyol, 3-5 parts of isocyanate and three-ten-thousandth of dibutyltin dilaurate, wherein the component B comprises the following components in parts by weight: 3-20 parts of solvent, 23-71 parts of mixed monomer, 2-9 parts of initiator, 2-6 parts of carboxyl-containing monomer, 2-10 parts of neutralizer and 200-700 parts of deionized water, wherein PMA is used as the solvent, and dibutyltin dilaurate is used as the catalyst; the polyurethane prepolymer modified matte hydroxypropyl dispersoid prepared by the invention has the advantages of good water resistance, high hardness, good matte performance, lower overall cost and wide market prospect, and avoids instability caused by adding matting powder.
Description
Technical Field
The invention belongs to the technical field of chemical water-based coatings, and particularly relates to a polyurethane prepolymer modified matte hydroxypropyl dispersoid and a preparation method thereof.
Background
With the enhancement of environmental awareness and the soundness of environmental regulations, the use of Volatile Organic Compounds (VOCs) and Harmful Air Pollutants (HAPs) in traditional solvent-based coatings is increasingly restricted, and the requirements of people on environmental protection and healthy life are higher and higher, so that more and more enterprises begin to try to develop water-based coatings and water-based emulsions. Aqueous hydroxypropyl dispersions have gained much better development in the market due to their excellent gloss, excellent weatherability and relatively low price.
The aqueous hydroxypropyl dispersions are divided into two categories: primary dispersions and secondary dispersions. The first-level dispersoid in the current market adopts an emulsion polymerization mode, and an emulsifier is added to ensure that the emulsifier is remained in the emulsion, so that the water resistance and the fullness of a paint film of the coating are reduced, and the improvement is difficult. While the secondary dispersions have high fullness, high degree of crosslinking and high water resistance, but are lower in hardness, too high in cost and free of matte properties.
In order to solve the above technical problems, research for improving water resistance, fullness and hardness of the aqueous hydroxypropyl dispersion has been carried out. For example, Chinese patent application publication No. CN 111944402A discloses a high-water-resistance water-based two-component matte finish paint, which comprises a component A and a component B, wherein the component A comprises 15-40 parts by weight of water-based hydroxy acrylic acid secondary dispersion, 40-65 parts by weight of water-based hydroxy acrylic acid emulsion, 0.1-1.0 part by weight of wetting agent, 0.3-0.6 part by weight of dispersing agent, 4-8 parts by weight of film forming auxiliary agent, 0.3-1.0 part by weight of defoaming agent, 0.3-1 part by weight of rheological auxiliary agent, 3-5 parts by weight of hand feeling auxiliary agent, 0.1-0.3 part by weight of flatting agent, 3-8 parts by weight of flatting agent, 1-10 parts by weight of deionized water, and the component B comprises 76-83 parts by weight of water-based isocyanate (HDI) curing agent and 16-22 parts by weight of environment-friendly solvent. By selecting a compound system of the aqueous hydroxyl acrylic acid secondary dispersion and the first-level aqueous hydroxyl acrylic emulsion with better resistance as a film forming main substance, the high fullness, high crosslinking degree and high water resistance of the aqueous secondary dispersion are combined with the low cost of the aqueous first-level dispersion, so that the technical problems of poor fullness, low hardness and poor water resistance of the existing aqueous paint are effectively solved, and the large-scale popularization is facilitated. Although the invention effectively solves the technical problems of poor fullness, low hardness, poor water resistance, no matte performance and the like of the existing water-based hydroxypropyl dispersion, the matte performance of the invention is the technical characteristic brought by adding the matting agent, and the matting effect is not ideal and has no stability.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a polyurethane prepolymer modified matte hydroxypropyl dispersoid and a preparation method thereof.
In order to achieve the purpose, the invention designs a polyurethane prepolymer modified matte hydroxypropyl dispersoid which comprises a component A and a component B, wherein the component A is a polyurethane prepolymer, and the main raw materials comprise the following components in parts by weight:
the preparation of the polyurethane prepolymer needs to react NCO in the raw materials completely;
the component B is other functional additives and comprises the following raw materials in parts by weight:
preferably, the polyurethane prepolymer modified matte hydroxypropyl dispersoid further comprises a solvent used by the PMA in the process of preparing the polyurethane prepolymer, and a catalyst used by the dibutyltin dilaurate in the process of preparing the polyurethane prepolymer.
Preferably, the polyurethane prepolymer modified matte hydroxypropyl dispersoid further comprises a neutralizing agent in the component B, wherein the neutralization degree of the neutralizing agent is 70-150%.
Preferably, the polyurethane prepolymer modified matte hydroxypropyl dispersoid further comprises a neutralizing agent in the component B, and the neutralizing degree of the neutralizing agent is preferably 90-130%.
Preferably, the polyurethane prepolymer modified matte hydroxypropyl dispersoid further comprises one or more of polyether diol, polyester diol, polycarbonate diol, polytetrahydrofuran diol, glycerol, trimethylolpropane and pentaerythritol as the polyhydric alcohol in the component A.
Preferably, the polyurethane prepolymer modified matte hydroxypropyl dispersion further comprises a polyol in the component A, preferably polyether polyol 1000,800,500 and glycerol.
Preferably, the polyurethane prepolymer modified matte hydroxypropyl dispersion further comprises isocyanate in the component A, wherein the isocyanate is one or more of hexamethylene diisocyanate, diphenylmethane diisocyanate, toluene diisocyanate and isophorone diisocyanate.
Preferably, the polyurethane prepolymer modified matte hydroxypropyl dispersion further comprises isocyanate in the component A, preferably isophorone diisocyanate.
Preferably, the polyurethane prepolymer modified matte hydroxypropyl dispersoid further comprises a solvent in the component B, wherein the solvent is one or a mixture of butyl acetate, No. 100 solvent oil, No. 150 solvent oil, No. 200 solvent oil, isopropanol, n-butanol, ethylene glycol ethyl ether, ethylene glycol butyl ether, propylene glycol methyl ether, propylene glycol ethyl ether, propylene glycol butyl ether, propylene glycol methyl ether acetate, diethylene glycol methyl ether and diethylene glycol butyl ether.
Preferably, the polyurethane prepolymer modified matte hydroxypropyl dispersoid further comprises a solvent in the component B, preferably No. 100 solvent naphtha, ethylene glycol butyl ether, propylene glycol butyl ether and diethylene glycol butyl ether.
Preferably, the polyurethane prepolymer modified matte hydroxypropyl dispersoid further comprises an initiator in the component B, wherein the initiator is one or a mixture of a plurality of azodiisobutyronitrile, azodiisoheptanonitrile, benzoyl peroxide, di-tert-butyl peroxide, di-tert-amyl peroxide, tert-butyl peroxybenzoate, tert-amyl peroxybenzoate, tert-butyl peroxy-2-ethyl hexanoate and tert-amyl peroxy-2-ethyl hexanoate.
Preferably, the polyurethane prepolymer modified matte hydroxypropyl dispersion further comprises an initiator in the component B, preferably tert-butyl peroxide and tert-amyl peroxide.
Preferably, the polyurethane prepolymer modified matte hydroxypropyl dispersion further comprises a mixed monomer in the component B, wherein the mixed monomer is vinyl acetate, methyl (meth) acrylate, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, N-butyl (meth) acrylate, isooctyl (meth) acrylate, octadecyl (meth) acrylate, lauryl (meth) acrylate, isobornyl (meth) acrylate, cyclohexyl (meth) acrylate, styrene, acrylonitrile, acrylamide, N-hydroxymethyl (meth) acrylamide, glycidyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, ethylene glycol di (meth) acrylate, 1, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, One or more mixtures of trimethylolpropane tri (meth) acrylate.
Preferably, the polyurethane prepolymer modified matte hydroxypropyl dispersion further comprises a mixed monomer in the component B, wherein the mixed monomer is preferably methyl (meth) acrylate, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, n-butyl (meth) acrylate, isooctyl (meth) acrylate, isobornyl (meth) acrylate or styrene.
Preferably, the polyurethane prepolymer modified matte hydroxypropyl dispersoid further comprises a carboxyl-containing monomer in the component B, wherein the carboxyl-containing monomer is one or more of fumaric acid, crotonic acid, itaconic acid, acrylic acid and methacrylic acid.
Preferably, the polyurethane prepolymer modified matte hydroxypropyl dispersoid further comprises a carboxyl-containing monomer in the component B, and the carboxyl-containing monomer is preferably acrylic acid and methacrylic acid.
The preparation method of the polyurethane prepolymer modified matte hydroxypropyl dispersoid comprises the following specific steps:
preparation of a component A:
(1) weighing 3-5 parts of PMA, 3-6 parts of polyol, 3-5 parts of isocyanate and three-ten-thousandth of dibutyltin dilaurate according to parts by weight;
(2) adding 3-5 parts of PMA into a reaction kettle, adding 3-6 parts of polyol and 3-5 parts of isocyanate into the reaction kettle, finally adding three-ten-thousandth of dibutyltin dilaurate for catalysis, and reacting for 5 hours at 70 ℃ until NCO is completely reacted to obtain a polyurethane prepolymer;
the preparation method of the polyurethane prepolymer modified matte hydroxypropyl dispersoid comprises the following steps:
(1) taking 2-6 parts by weight of prepared polyurethane prepolymer, adding 2-6 parts by weight of polyurethane prepolymer and 3-20 parts by weight of solvent into a reaction kettle, and heating to 140-155 ℃;
(2) preparing a mixture A from 15-45 parts by weight of mixed monomers and 1-5 parts by weight of initiator, dropwise adding the mixture A into a reaction kettle for 3-5 hours, and keeping the temperature for 40min after dropwise adding;
(3) preparing 8-26 parts by weight of mixed monomer, 2-6 parts by weight of monomer containing carboxyl and 1-4 parts by weight of initiator into a mixture B, dropwise adding the mixture B into a reaction kettle for 1-2 hours, and keeping the temperature for 3 hours after dropwise adding;
(4) cooling to 70-100 ℃, adding 2-10 parts by weight of neutralizing agent, and then adding 200 parts by weight of deionized water to carry out dispersion, thus obtaining the polyurethane prepolymer modified matte hydroxypropyl dispersoid.
Compared with the prior art, the invention has the following advantages:
1. the water resistance is good, and the hardness is high;
2. instability caused by adding the matting powder is avoided, and the matte performance is good;
3. and the cost is saved.
Detailed Description
The present invention will be further described with reference to the following examples. The following examples will assist those skilled in the art in further understanding the invention, but are not intended to limit the invention in any way. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention.
Example 1
This example is intended to demonstrate a method for preparing a polyurethane prepolymer, as follows:
adding 60g of PMA into a reaction kettle, adding 30g of glycerol, continuously adding 1000 g of polyether polyol, adding 72g of isophorone diisocyanate, finally adding 0.1g of T-12, heating to 70 ℃, reacting for 5 hours, testing the NCO content, filtering after the test is qualified, and discharging for later use.
Example 2
This example is intended to show a method for preparing a hydroxy acrylate emulsion comprising a polyurethane prepolymer, comprising:
(1) adding 30g of propylene glycol butyl ether into a reaction kettle, adding 15g of No. 100 solvent oil, continuously adding 30g of polyurethane prepolymer (example 1), heating to 140 ℃ and 150 ℃, and introducing nitrogen for 30 min; mixing 40g of hydroxypropyl methacrylate, 40g of methyl methacrylate, 40g of styrene, 20g of isobornyl methacrylate, 25g of isooctyl acrylate and 3g of tert-amyl peroxide, uniformly stirring to obtain a mixed monomer, after the temperature is raised to the reaction temperature, dripping the mixed monomer into the reaction kettle at a constant speed, controlling the dripping time to be 4h, and after the dripping is finished, keeping the temperature at 150 ℃ for 40 min;
(2) keeping the product of the first step at the temperature of 140-;
(3) cooling the reaction to 100 ℃, adding 12.3g of dimethylethanolamine into the reaction kettle, stirring for 40min, adding 280g of deionized water at 70-80 ℃ under a high-speed stirring state, controlling the water to be added within 40min, and stirring for 1h after the water is added to obtain the milky white blue-colored polyurethane prepolymer modified acrylate dispersoid.
The dispersion has a solid content of 45 percent, a viscosity of 300-1500mpa.s, is stable when stored at 40 ℃ for 40 days, and has an acid value calculated by the solid part as follows: 28.48mgKOH/g, the hydroxyl content is 2.63 percent according to the solid content, the modified water-based hydroxypropyl dispersoid is matched with Bayhydur2655 water-based isocyanate curing agent of Bayer company, the baking is carried out at 70 ℃ for 30m in, the pencil hardness can reach H-2H, the paint film adhesion is 0 grade, the impact resistance can reach more than 50kg, the 60-degree angle gloss is below 10 degrees, the water resistance at 40 ℃ is 20 days, the acid resistance is 120 hours, and the neutral salt fog resistance is 240 hours. The plate surface is flat, and the activation period is as long as more than 6 hours. Suitable for the resin of the matte polyurethane finish and the application of the primer-topcoat resin.
Example 3
This example is intended to show the preparation of a hydroxy acrylate emulsion as follows:
(1) adding 36g of propylene glycol butyl ether into a reaction kettle, adding 15g of No. 100 solvent oil, heating to 140 ℃ and 150 ℃, and introducing nitrogen for 30 min; mixing 40g of hydroxypropyl methacrylate, 54g of methyl methacrylate, 40g of styrene, 20g of isobornyl methacrylate, 25g of isooctyl acrylate and 3g of tert-amyl peroxide, uniformly stirring to obtain a mixed monomer, after the temperature is raised to the reaction temperature, dripping the mixed monomer into the reaction kettle at a constant speed, controlling the dripping time to be 4 hours, and keeping the temperature at 150 ℃ for 40min after the dripping is finished;
(2) keeping the product of the first step at the temperature of 140-;
(3) cooling the reaction to 100 ℃, adding 12.3g of dimethylethanolamine into the reaction kettle, stirring for 40min, adding 280g of deionized water at 70-80 ℃ under a high-speed stirring state, controlling the water to be added within 40min, and stirring for 1h after the water is added to obtain the milky-white blue-light acrylate dispersoid.
The dispersion has a solid content of 45 percent, a viscosity of 300-800mpa.s, is stable when stored at 40 ℃ for 30 days, and has an acid value calculated by the solid part as follows: 28.48mgKOH/g, the hydroxyl content is 2.63 percent calculated by solid parts, the modified water-based hydroxypropyl dispersoid is matched with Bayhydur2655 water-based isocyanate curing agent of Bayer company, the mixture is baked for 30min at 70 ℃, the pencil hardness can reach H, the paint film adhesion can reach 0 level, the impact resistance can reach 40kg, the 60-degree angle gloss is 83-92 degrees, the water resistance at 40 ℃ is 5 days, and the chemical resistance is good. The plate surface is flat, and the activation period is as long as 4 hours. Is suitable for the application of resin of high-gloss polyurethane finish paint and primer-topcoat resin.
Example 4
This example aims to show a method for preparing a polyurethane prepolymer, comprising:
adding 120g of PMA into a reaction kettle, adding 60g of glycerol, adding 80g of polyether polyol 500 and 80g of polyether polyol 800, then adding 144g of isophorone diisocyanate, adding 0.3g of T-12, heating to 70 ℃, reacting for 5 hours, testing the NCO content, filtering after the test is qualified, and discharging for later use.
Example 5
This example is intended to show a method for preparing a hydroxy acrylate emulsion comprising a polyurethane prepolymer, comprising:
(1) adding 300g of propylene glycol butyl ether into a reaction kettle, adding 150g of No. 100 solvent oil, adding 200g of polyurethane prepolymer (example 4), heating to 140 ℃ and 150 ℃, and introducing nitrogen for 30 min; mixing 400g of hydroxypropyl methacrylate, 400g of methyl methacrylate, 400g of styrene, 200g of isobornyl methacrylate, 250g of isooctyl acrylate and 30g of tert-amyl peroxide, uniformly stirring to obtain a mixed monomer, after the temperature is raised to the reaction temperature, dripping the mixed monomer into the reaction kettle at a constant speed, controlling the dripping time to be 4h, and keeping the temperature at 150 ℃ for 40min after the dripping is finished;
(2) keeping the product of the first step at the temperature of 140-;
(3) and cooling the reaction to 100 ℃, adding 123g of dimethylethanolamine into the reaction kettle, stirring for 40min, adding 2800g of deionized water at 70-80 ℃ under a high-speed stirring state, controlling the water to be added within 40min, and stirring for 1h after the water is added to obtain the milky white blue-light polyurethane prepolymer modified acrylate dispersoid.
The dispersion has a solid content of 45 percent, a viscosity of 300-800mpa.s, is stable when stored at 40 ℃ for 40 days, and has an acid value calculated by the solid part as follows: 31.64mgKOH/g, the hydroxyl content is 2.92 percent according to the solid content, the modified water-based hydroxypropyl dispersoid is matched with Bayhydur2655 water-based isocyanate curing agent of Bayer company, the mixture is baked for 30min at 70 ℃, the pencil hardness can reach 2H, the paint film adhesion is 0 grade, the impact resistance can reach more than 50kg, the 60-degree angle gloss is below 10 degrees, the water resistance at 40 ℃ is 15 days, the acid resistance is 120H, and the neutral salt fog resistance is 240H. The plate surface is flat, and the activation period is as long as more than 6 hours. Suitable for the resin of the matte polyurethane finish and the application of the primer-topcoat resin.
Paint film performance tests were conducted below for examples 2, 3 and 5, and the results are shown in table 1 below:
TABLE 1
| Example 2 | Example 3 | Example 5 | |
| Hardness of | H-2H | H | 2H |
| Adhesion force | Level 0 | Level 0 | Level 0 |
| Impact of | Front and back 50kg | Front and back 40kg | Front and back 50kg |
| Gloss (60 degree) | 7.5 | 88.9 | 6.8 |
| Water-resistant (40 ℃ C.) | 20d | 5d | 15d |
| Acid resistance | 120h | 72h | 120h |
| Neutral salt spray | 240h | 120h | 240h |
| Activation period (30 ℃ C.) | 6h | 4h | 6h |
As can be seen from the above Table 1, the addition of the polyurethane prepolymer has a great influence on the gloss, the resistance is significantly improved, the hardness and the water resistance are also improved, and the defects of instability, poor extinction effect and the like caused by the addition of the extinction powder are completely avoided.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (11)
1. A polyurethane prepolymer modified matte hydroxypropyl dispersoid comprises a component A and a component B, wherein the component A is a polyurethane prepolymer, and the main raw materials comprise the following components in parts by weight:
the preparation of the polyurethane prepolymer needs to react NCO in the raw materials completely;
the component B is other functional additives and comprises the following raw materials in parts by weight:
2. the polyurethane prepolymer modified matte hydroxypropyl dispersion of claim 1, wherein the PMA is used as a solvent in the preparation of a polyurethane prepolymer, and the dibutyltin dilaurate is used as a catalyst in the preparation of a polyurethane prepolymer.
3. The polyurethane prepolymer modified matte hydroxypropyl dispersion of claim 1, wherein the neutralization degree of the neutralizing agent in the component B is 70-150%.
4. The polyurethane prepolymer modified matte hydroxypropyl dispersion as claimed in claim 3, wherein the neutralization degree of the neutralizing agent in the component B is preferably 90-130%.
5. The polyurethane prepolymer modified matte hydroxypropyl dispersion as claimed in claim 1, wherein the polyol in the component A is preferably polyether polyol 1000,800,500 and glycerol.
6. The polyurethane prepolymer modified matte hydroxypropyl dispersion according to claim 1, wherein the isocyanate in the component A is preferably isophorone diisocyanate.
7. The polyurethane prepolymer modified matte hydroxypropyl dispersion as claimed in claim 1, wherein the solvent in the component B is preferably No. 100 solvent oil, ethylene glycol butyl ether, propylene glycol butyl ether and diethylene glycol butyl ether.
8. The polyurethane prepolymer modified matte hydroxypropyl dispersion as claimed in claim 1, wherein the initiator in the component B is preferably tert-butyl peroxide or tert-amyl peroxide.
9. The polyurethane prepolymer modified matte hydroxypropyl dispersion as claimed in claim 1, wherein the mixed monomer in component B is preferably methyl (meth) acrylate, hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, n-butyl (meth) acrylate, isooctyl (meth) acrylate, isobornyl (meth) acrylate, or styrene.
10. The polyurethane prepolymer modified matte hydroxypropyl dispersion as claimed in claim 1, wherein the carboxyl-containing monomer in the component B is preferably acrylic acid and methacrylic acid.
11. The polyurethane prepolymer modified matte hydroxypropyl dispersion as claimed in any one of claims 1 to 4, wherein the preparation of the component A comprises the following steps:
(1) weighing 3-5 parts of PMA, 3-6 parts of polyol, 3-5 parts of isocyanate and three-ten-thousandth of dibutyltin dilaurate according to parts by weight;
(2) adding 3-5 parts of PMA into a reaction kettle, adding 3-6 parts of polyol and 3-5 parts of isocyanate into the reaction kettle, finally adding three-ten-thousandth of dibutyltin dilaurate for catalysis, and reacting for 5 hours at 70 ℃ until NCO is completely reacted to obtain a polyurethane prepolymer;
the preparation method of the polyurethane prepolymer modified matte hydroxypropyl dispersoid comprises the following steps:
(1) taking 2-6 parts by weight of prepared polyurethane prepolymer, adding 2-6 parts by weight of polyurethane prepolymer and 3-20 parts by weight of solvent into a reaction kettle, and heating to 140-155 ℃;
(2) preparing 15-45 parts by weight of mixed monomer and 1-5 parts by weight of initiator into a mixture A, dropwise adding the mixture A into a reaction kettle for 3-5 hours, and keeping the temperature for 40min after dropwise adding;
(3) preparing 8-26 parts by weight of mixed monomer, 2-6 parts by weight of monomer containing carboxyl and 1-4 parts by weight of initiator into a mixture B, dropwise adding the mixture B into a reaction kettle for 1-2 hours, and keeping the temperature for 3 hours after dropwise adding;
(4) cooling to 70-100 ℃, adding 2-10 parts by weight of neutralizing agent, and then adding 200 parts by weight of deionized water to carry out dispersion, thus obtaining the polyurethane prepolymer modified matte hydroxypropyl dispersoid.
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| CN115569089A (en) * | 2022-11-09 | 2023-01-06 | 郑州圣莱特空心微珠新材料有限公司 | Matte nail polish gel and preparation method thereof |
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