CN113717325A - Modified waterborne alkyd resin, preparation method thereof and aqueous dispersion containing modified waterborne alkyd resin - Google Patents
Modified waterborne alkyd resin, preparation method thereof and aqueous dispersion containing modified waterborne alkyd resin Download PDFInfo
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- CN113717325A CN113717325A CN202110881209.3A CN202110881209A CN113717325A CN 113717325 A CN113717325 A CN 113717325A CN 202110881209 A CN202110881209 A CN 202110881209A CN 113717325 A CN113717325 A CN 113717325A
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- alkyd resin
- acid
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- ether
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- 229920000180 alkyd Polymers 0.000 title claims abstract description 82
- 239000006185 dispersion Substances 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 40
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 24
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000000178 monomer Substances 0.000 claims abstract description 24
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000008096 xylene Substances 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 17
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 16
- -1 alkyl primary amine Chemical class 0.000 claims abstract description 14
- 239000005711 Benzoic acid Substances 0.000 claims abstract description 12
- 235000010233 benzoic acid Nutrition 0.000 claims abstract description 12
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 11
- 150000001336 alkenes Chemical class 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 10
- 235000015112 vegetable and seed oil Nutrition 0.000 claims abstract description 10
- 239000008158 vegetable oil Substances 0.000 claims abstract description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 9
- 229920005862 polyol Polymers 0.000 claims abstract description 8
- 150000003077 polyols Chemical class 0.000 claims abstract description 8
- 239000003999 initiator Substances 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 238000004321 preservation Methods 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 12
- 239000008367 deionised water Substances 0.000 claims description 11
- 229910021641 deionized water Inorganic materials 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 235000012424 soybean oil Nutrition 0.000 claims description 10
- 239000003549 soybean oil Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical group CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 8
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 6
- 235000021388 linseed oil Nutrition 0.000 claims description 6
- 239000000944 linseed oil Substances 0.000 claims description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 6
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 claims description 5
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 5
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 5
- 239000004359 castor oil Substances 0.000 claims description 5
- 235000019438 castor oil Nutrition 0.000 claims description 5
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 5
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 claims description 4
- BDLXTDLGTWNUFM-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]ethanol Chemical compound CC(C)(C)OCCO BDLXTDLGTWNUFM-UHFFFAOYSA-N 0.000 claims description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 4
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- CUVLMZNMSPJDON-UHFFFAOYSA-N 1-(1-butoxypropan-2-yloxy)propan-2-ol Chemical compound CCCCOCC(C)OCC(C)O CUVLMZNMSPJDON-UHFFFAOYSA-N 0.000 claims description 3
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims description 3
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims 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 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 3
- 239000003921 oil Substances 0.000 claims description 3
- 235000019198 oils Nutrition 0.000 claims description 3
- 239000003760 tallow Substances 0.000 claims description 3
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 2
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 claims description 2
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 claims description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 claims description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 claims description 2
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims 1
- 229940082005 hydrogenated tallow acid Drugs 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- 239000003973 paint Substances 0.000 abstract description 8
- 239000006184 cosolvent Substances 0.000 abstract description 2
- 239000012855 volatile organic compound Substances 0.000 abstract 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical group [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 15
- 238000006136 alcoholysis reaction Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 238000001035 drying Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229960002887 deanol Drugs 0.000 description 4
- 239000012972 dimethylethanolamine Substances 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- QAIHWMZHLIBAFX-QZOPMXJLSA-N (z)-octadec-9-en-1-amine;(z)-octadec-9-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCN.CCCCCCCC\C=C/CCCCCCCC(O)=O QAIHWMZHLIBAFX-QZOPMXJLSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 235000013527 bean curd Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000005338 heat storage Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000006115 industrial coating Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Substances [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000002023 wood 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
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2351/00—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
- C08J2351/08—Characterised by the use of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The invention relates to the technical field of waterborne alkyd resins, and discloses a modified alkyd resin, which comprises, by weight, 10-20 parts of vegetable oil, 0.003-0.012 part of hydroxide, 0.3-1.5 part of benzoic acid, 5-12 parts of dibasic acid, 2-8 parts of polyol, 1-3 parts of xylene and 8-15 parts of an organic solvent; adding 1.2-3.0 parts of acrylic acid, 4-20 parts of styrene, 1-5 parts of alkene monomer containing epoxy group, 4-20 parts of acrylate monomer, 0.3-1.0 part of initiator, 2.5-5 parts of long-chain alkyl primary amine and 1-5 parts of neutralizer into basic alkyd resin; its preparing process is also disclosed. The modified alkyd resin prepared by the method can ensure water dispersibility and stability, so that the initial water resistance of a paint film is further improved, the addition of a cosolvent can be reduced, and VOC (volatile organic compounds) is reduced.
Description
Technical Field
The invention relates to the technical field of waterborne alkyd resins, in particular to a modified waterborne alkyd resin, a preparation method thereof and a water dispersion containing the modified waterborne alkyd resin.
Background
In recent years, with the increasing awareness of the people on environmental protection and the stricter environmental regulations of all countries, the reduction of the VOC content in the paint has become a research hotspot. Alkyd resin refers to a polyester in which fatty acid side chains are introduced, i.e., modified with a fatty acid. The water-based alkyd resin uses renewable vegetable oil or fatty acid as a main raw material and water as a solvent, so that the VOC content is low, the requirement of times on environmental protection is met, and the consumption of petroleum caused by the use of an organic solvent is reduced; and secondly, the water-based alkyd resin has high carbon-hydrogen content in the molecular structure, low molecular polarity and strong adjustability, is widely applied to industrial coating, not only can be used as primer, finish coat and single-layer coating on the surfaces of metal, wood and plastic, but also can be used for corrosion-resistant coating and protection of ships, instruments, office equipment, metal building materials and the like.
Despite the environmental advantages associated with the waterborne nature of alkyds, it should be ensured that the synthetic alkyds retain the advantages of their traditional solvent-based alkyds, such as good storage stability, high gloss, drying properties and water and corrosion resistance. However, the existing water-based alkyd resin generally has the defects of poor water resistance and slow drying speed. In order to improve the problems of poor water resistance and slow drying speed of the waterborne alkyd resin, the waterborne alkyd resin needs to be modified.
At present, the most used modification method is to utilize acrylic acid (ester) monomer to copolymerize and graft alkyd resin, and then use organic amine to neutralize acrylic acid for hydrophilicity, so as to improve the initial drying performance and obtain aqueous dispersion with better stability. In the improved method, in order to ensure the water dispersibility and stability of the resin, more hydrophilic groups exist in the molecular chain of the resin, and the molecular weight is lower, so that the initial water resistance of the resin is poor before double bonds are not oxidized and crosslinked.
Disclosure of Invention
< problems to be solved by the present invention >
The method is used for solving the technical problem of poor initial water resistance of the water-based alkyd resin modified by acrylic acid (ester) monomers in the prior art.
< technical solution adopted in the present invention >
In view of the above-mentioned technical problems, an object of the present invention is to provide a modified waterborne alkyd resin, a method for preparing the same, and an aqueous dispersion comprising the same.
The specific contents are as follows:
the invention provides a modified alkyd resin, which comprises the following components, by weight, 10-20 parts of vegetable oil, 0.003-0.012 part of hydroxide, 0.3-1.5 parts of benzoic acid, 5-12 parts of dibasic acid, 2-8 parts of polyhydric alcohol, 1-3 parts of xylene and 8-15 parts of an organic solvent; 1.2-3.0 parts of acrylic acid, 4-20 parts of styrene, 1-5 parts of alkene monomer containing epoxy group, 4-20 parts of acrylate monomer, 0.3-1.0 part of initiator, 2.5-5 parts of long-chain alkyl primary amine and 1-5 parts of neutralizer are added into the basic alkyd resin.
Secondly, the invention provides a preparation method of the modified alkyd resin, which comprises the following steps:
s1, dissolving oil, polyol and hydroxide in ethanol, sequentially adding benzoic acid, dibasic acid and xylene for reaction, removing the xylene after the reaction is finished, cooling, and adding an organic solvent to obtain a basic alkyd resin;
s2 heating the basic alkyd resin, dripping a blend containing acrylic acid, styrene, an epoxy group-containing alkene monomer and an acrylate monomer, and after dripping is finished, carrying out heat preservation treatment;
s3, after the heat preservation is finished, carrying out primary cooling, adding long-chain alkyl primary amine, and carrying out heat preservation treatment;
and (S4) after the heat preservation is finished, carrying out secondary cooling, adding an amine neutralizer, and carrying out heat preservation treatment to obtain the modified waterborne alkyd resin.
And thirdly, adding deionized water into the modified alkyd resin, and dispersing to obtain a finished product.
< technical mechanism and advantageous effects of the present invention >
(1) According to the method, long-chain primary alkyl amine and an epoxy group-containing alkene monomer are selected as modifiers, and the long-chain primary alkyl amine can react with an epoxy group, carboxyl in alkyd resin and acrylic acid and is grafted to the alkyd resin; the long-chain alkyl has excellent hydrophobicity, so that the initial water resistance of the paint film can be further improved on the premise of ensuring water dispersibility and stability.
(2) The long-chain alkyl primary amine is also a surfactant, has longer molecular weight and lower surface energy, is grafted to the alkyd resin, and can increase the fluidity of the resin and improve the water dilutability by winding the long-chain alkyl, so that the addition of a cosolvent is reduced, and the VOC is reduced.
(3) By adding the alkene monomer containing the epoxy group, long-chain alkyl primary amine can be grafted to a molecular chain better, and further the reaction rate is improved.
(4) Long-chain alkyl primary amines have a relatively high boiling point and a relatively low pungent amine odor, and the resulting aqueous alkyd resin dispersions have a low odor.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The modified alkyd resin comprises, by weight, 10-20 parts of vegetable oil, 0.003-0.012 part of hydroxide, 0.3-1.5 parts of benzoic acid, 5-12 parts of dibasic acid, 2-8 parts of polyol, 1-3 parts of xylene and 8-15 parts of an organic solvent; 1.2-3.0 parts of acrylic acid, 4-20 parts of styrene, 1-5 parts of alkene monomer containing epoxy group, 4-20 parts of acrylate monomer, 0.3-1.0 part of initiator, 2.5-5 parts of long-chain alkyl primary amine and 1-5 parts of neutralizer are added into the basic alkyd resin.
In the present invention, the hydroxide is lithium hydroxide.
In the invention, the epoxy group-containing vinyl monomer is glycidyl methacrylate and/or allyl glycidyl ether.
In the invention, the long-chain alkyl primary amine comprises at least one of dodecylamine, hexadecylamine, oleylamine, octadecylamine, tallow amine and hydrogenated tallow amine. The oleic amine and the tallow amine are unsaturated enamine, have iodine value of 40-100, are grafted on alkyd resin, increase double bond content, improve oxidation crosslinking density, are beneficial to hardness, and improve water resistance and salt spray resistance.
In the present invention, the acrylic monomer includes at least one of methyl methacrylate, butyl acrylate, butyl methacrylate, isobornyl acrylate, isobornyl methacrylate, and hydroxypropyl acrylate.
In the present invention, the vegetable oil includes at least one of soybean oil, linseed oil, or castor oil.
In the present invention, the dibasic acid includes phthalic anhydride and/or isophthalic acid;
the polyhydric alcohol comprises trimethylolpropane and/or pentaerythritol;
the organic solvent comprises at least one of diethylene glycol monobutyl ether, dipropylene glycol monobutyl ether, diethylene glycol monomethyl ether, ethylene glycol tert-butyl ether, propylene glycol ethyl ether, propylene glycol propyl ether, propylene glycol butyl ether, or propylene glycol methyl ether.
In the present invention, the initiator includes benzoyl peroxide and/or t-butyl peroxybenzoate.
In the invention, the neutralizer is amine neutralizer, and the amine neutralizer comprises dimethylethanolamine and/or diethanolamine. The amine neutralizer is selected, the boiling point is high, the pungent amine smell is low, and the prepared alkyd resin aqueous dispersion is low in smell.
Secondly, the invention provides a preparation method of the modified alkyd resin, which comprises the following steps:
s1, dissolving oil, polyol and hydroxide in ethanol, sequentially adding benzoic acid, dibasic acid and xylene for reaction, removing the xylene after the reaction is finished, cooling, and adding an organic solvent to obtain a basic alkyd resin;
s2 heating the basic alkyd resin, dripping a blend containing acrylic acid, styrene, an epoxy group-containing alkene monomer and an acrylate monomer, and after dripping is finished, carrying out heat preservation treatment;
s3, after the heat preservation is finished, carrying out primary cooling, adding long-chain alkyl primary amine, and carrying out heat preservation treatment;
and (S4) after the heat preservation is finished, carrying out secondary cooling, adding an amine neutralizer, and carrying out heat preservation treatment to obtain the modified waterborne alkyd resin.
In particular, the amount of the solvent to be used,
s1, carrying out alcoholysis on the vegetable oil, the polyol and the hydroxide at 230-250 ℃ until the vegetable oil, the polyol and the hydroxide are dissolved in 5 times of volume of 95% ethanol (25 ℃) until the vegetable oil, the polyol and the hydroxide are clear; and adding benzoic acid, dibasic acid and refluxing xylene after alcoholysis is finished, reacting at 170-210 ℃ until the acid value is 16-24 mgKOH/g, cooling to 155-160 ℃, removing xylene in vacuum, cooling to 100 ℃, and adding an organic solvent to obtain the basic alkyd resin.
S2, heating the basic alkyd resin to 125-135 ℃, dropwise adding a mixture of acrylic acid, styrene, an epoxy group-containing alkene monomer, an acrylate monomer and an initiator within 1.5-3.0 h, and preserving heat for 1-3 h after dropwise adding.
S3, cooling to 80-110 ℃ once, adding long-chain alkyl primary amine, and keeping the temperature for 1-2 h.
S4, cooling to 80 ℃ for the second time, adding an amine neutralizer, and keeping the temperature for 0.5-1 h.
And thirdly, adding deionized water into the modified waterborne alkyd resin, and dispersing to obtain a finished product.
Specifically, adding the obtained modified waterborne alkyd resin into deionized water at 80 ℃, and dispersing at high speed for 15-30 min to obtain the modified alkyd dispersion; wherein the adding amount of the deionized water is 35-55 parts.
< example >
Example 1
A preparation method of the modified water-based alkyd resin water dispersion comprises the following steps:
s1 alcoholysis of 14.5 parts of soybean oil, 3.8 parts of pentaerythritol and 0.003 part of lithium hydroxide at 250 ℃ until the soybean oil is dissolved in 5 times of 95% ethanol (25 ℃) and is clear; and after alcoholysis, adding 0.5 part of benzoic acid, 7.2 parts of isophthalic acid and 1.8 parts of reflux xylene, reacting at 170-210 ℃ until the acid value is 16-24 mg KOH/g, cooling to 155-160 ℃, removing xylene in vacuum, cooling to 100 ℃, adding 11.7 parts of butyl cellosolve, and blending to obtain the basic alkyd resin.
S2, heating the basic alkyd resin to 125-135 ℃, dropwise adding a mixture of 1.9 parts of acrylic acid, 11.2 parts of styrene, 1.5 parts of glycidyl methacrylate, 0.1 part of benzoyl peroxide and 0.4 part of tert-butyl peroxybenzoate in 2 hours, and preserving heat for 2 hours after dropwise adding.
S3, cooling to 90 ℃ once, adding 1.5 parts of dodecylamine, and keeping the temperature for 2 hours.
S4, cooling to 80 ℃ for the second time, adding 3.3 parts of dimethylethanolamine, and keeping the temperature for 0.5 h.
And S5, adding 58 parts of deionized water with the temperature of 80 ℃, and dispersing at high speed for 15min to obtain the modified waterborne alkyd resin aqueous dispersion.
Example 2
A preparation method of the modified water-based alkyd resin water dispersion comprises the following steps:
s1 alcoholysis of 10 parts of soybean oil, 5.5 parts of linseed oil, 4.0 parts of pentaerythritol and 0.01 part of lithium hydroxide at 240 ℃ until the materials are dissolved in 5 times of 95% ethanol (25 ℃) and clear; and after alcoholysis, adding 0.5 part of benzoic acid, 6.6 parts of phthalic anhydride and 1.5 parts of reflux xylene, reacting at 170-210 ℃ until the acid value is 16-24 mg KOH/g, cooling to 155-160 ℃, removing xylene in vacuum, cooling to 100 ℃, adding 8.5 parts of propylene glycol propyl ether, 4.2 parts of ethylene glycol tert-butyl ether and 0.3 part of diethylene glycol butyl ether, and blending to obtain the basic alkyd resin.
S2, heating the basic alkyd resin to 125-135 ℃, dropwise adding a mixture of 2.3 parts of acrylic acid, 8.2 parts of styrene, 2.0 parts of glycidyl methacrylate, 4 parts of isobornyl methacrylate, 2 parts of butyl acrylate, 0.3 part of benzoyl peroxide and 0.5 part of tert-butyl peroxybenzoate within 2 hours, and preserving heat for 2 hours after dropwise adding.
S3, cooling to 100 ℃ once, adding 1.5 parts of oleylamine and keeping the temperature for 2 hours.
S4, cooling to 80 ℃ for the second time, adding 3.3 parts of dimethylethanolamine, and keeping the temperature for 0.5 h.
And S5, adding 58 parts of deionized water with the temperature of 80 ℃, and dispersing at high speed for 15min to obtain the modified waterborne alkyd resin aqueous dispersion.
Example 3
A preparation method of the modified water-based alkyd resin water dispersion comprises the following steps:
s1 alcoholysis of 10 parts of soybean oil, 5.5 parts of linseed oil, 4.0 parts of pentaerythritol and 0.01 part of lithium hydroxide at 240 ℃ until the materials are dissolved in 5 times of 95% ethanol (25 ℃) and clear; and after alcoholysis, adding 0.5 part of benzoic acid, 6.6 parts of phthalic anhydride and 1.5 parts of reflux xylene, reacting at 170-210 ℃ until the acid value is 16-24 mg KOH/g, cooling to 155-160 ℃, removing xylene in vacuum, cooling to 100 ℃, adding 13 parts of propylene glycol propyl ether and 2 parts of propylene glycol methyl ether, and blending to obtain the basic alkyd resin.
S2, heating the basic alkyd resin to 125-135 ℃, dropwise adding a mixture of 2.3 parts of acrylic acid, 14 parts of styrene, 0.8 part of glycidyl methacrylate, 0.56 part of allyl glycidyl ether, 5.5 parts of methyl methacrylate, 0.5 part of hydroxypropyl acrylate and 0.7 part of tert-butyl peroxybenzoate within 2 hours, and preserving heat for 2 hours after dropwise adding.
S3, cooling to 100 ℃ once, adding 3.0 parts of oleylamine oleate, and keeping the temperature for 2 hours.
S4, cooling to 80 ℃ for the second time, adding 3.7 parts of diethanolamine, and keeping the temperature for 0.5 h.
And S5, adding 58 parts of deionized water with the temperature of 80 ℃, and dispersing at high speed for 15min to obtain the modified waterborne alkyd resin aqueous dispersion.
Example 4
A preparation method of the modified water-based alkyd resin water dispersion comprises the following steps:
s1 alcoholysis of 10 parts of soybean oil, 5.5 parts of linseed oil, 4.0 parts of pentaerythritol and 0.01 part of lithium hydroxide at 250 ℃ until the mixture is dissolved in 5 times of 95% ethanol (25 ℃) and is clear; and after alcoholysis, adding 0.5 part of benzoic acid, 6.4 parts of phthalic anhydride and 1.5 parts of reflux xylene, reacting at 170-210 ℃ until the acid value is 16-24 mg KOH/g, cooling to 155-160 ℃, removing xylene in vacuum, cooling to 100 ℃, adding 5 parts of propylene glycol propyl ether, 7.9 parts of ethylene glycol tert-butyl ether and 0.1 part of dipropylene glycol butyl ether, and blending to obtain the basic alkyd resin.
S2, heating the basic alkyd resin to 125-135 ℃, dropwise adding a mixture of 1.8 parts of acrylic acid, 7.2 parts of styrene, 1.0 part of glycidyl methacrylate, 1.8 parts of methyl methacrylate and 0.5 part of tert-butyl peroxybenzoate in 1.5h, and preserving heat for 2h after dropwise adding.
S3, cooling to 90 ℃ once, adding 1.0 part of octadecylamine, and keeping the temperature for 1 hour.
S4, cooling to 80 ℃ for the second time, adding 3.7 parts of diethanolamine, and keeping the temperature for 0.5 h.
And S5, adding 58 parts of deionized water with the temperature of 80 ℃, and dispersing at high speed for 15min to obtain the modified waterborne alkyd resin aqueous dispersion.
Example 5
This example differs from example 1 in that soybean oil was replaced with a combination of soybean oil, linseed oil and castor oil, 8 parts soybean oil, 5 parts castor oil and 6 parts castor oil.
< comparative example >
Comparative example 1
This comparative example differs from example 3 in that no glycidyl methacrylate and no oleylamine were added.
Comparative example 2
This comparative example differs from example 1 in that no glycidyl methacrylate was added.
Comparative example 3
This comparative example differs from example 1 in that dodecylamine is not added.
< test example >
Examples 1-4 and comparative examples 1-3 were used as samples, wherein example is indicated as E and comparative example is indicated as C.
(1) The sample was subjected to index measurement, and the results are shown in table 1.
TABLE 1 indices of aqueous modified alkyd resin dispersions
Index (I) | E1 | E2 | E3 | E4 | C1 | C2 | C3 |
Solids content/% | 40 | 40 | 40 | 40 | 40 | 40 | 40 |
viscosity/Pa.s | 1090 | 650 | 720 | 1480 | 8200 | 5000 | 32000 |
pH value | 9 | 8 | 8.5 | 8.5 | 9 | 9 | 9 |
Content of solvent/%) | 10.3 | 10 | 10.2 | 12.2 | 10.3 | 10.3 | 10.3 |
Days/day of 50 ℃ heat storage | >30 | >30 | >30 | >30 | >30 | >30 | >30 |
(2) Adding the sample into the paint, and performing paint film performance measurement
The preparation method comprises the steps of grinding 52 parts of modified waterborne alkyd resin aqueous dispersion, 1.3 parts of waterborne cobalt drier, 50290.3 parts of dispersing agent, 0.25 part of wetting agent 755W, 0.2 part of bentonite, 3 parts of titanium dioxide, 13900.1 parts of defoaming agent, 23 parts of barium sulfate and 3 parts of deionized water for 1 hour at 1500r/min, and dispersing to less than 15 mu m to obtain a first mixture; adding 15 parts of modified aqueous alkyd resin aqueous dispersion, 1.5 parts of deionized water, 0.3 part of pH regulator-dimethylethanolamine, 0.2 part of anti-flash rust agent-sodium nitrite and 0.3 part of carbon black color paste into the first mixture, and stirring for 10min at 600r/min to obtain the coating.
The performance of the paint prepared in the above way is measured according to the method of GB/T25251-2010 alkyd resin paint. Testing environment, temperature is more than 20 ℃, and humidity is less than 65%. The measurement results are shown in Table 2.
TABLE 2 determination of the paint film Properties
Measurement index | E1 | E2 | E3 | E4 | C1 | C2 | C3 |
Time to surface dry | <8h | <8h | <8h | <8h | <8h | <8h | <8h |
Dried bean curd (Jia Fa) | ≤24h | ≤24h | ≤24h | ≤24h | ≤24h | ≤24h | ≤24h |
Hardness (168h) | ≥B | ≥B | ≥B | ≥B | ≥B | ≥B | ≥B |
Initial water resistance (4h) | 72h | 48h | 52h | 60h | 12h | 36h | 16h |
Water-resistant (drying 24h) | 72h | 60h | 70h | 68h | 12h | 40h | 15h |
Water-resistant (Dry 168h) | 120h | 144h | 130h | 98h | 46h | 50h | 48h |
Acid mist resistant (Dry 168h) | 200h | 240h | 210h | 170h | 48h | 100h | 48h |
Adhesion force | ≤1 | ≤1 | ≤1 | ≤1 | ≤2 | ≤1 | ≤1 |
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. The modified alkyd resin is characterized in that the basic alkyd resin comprises, by weight, 10-20 parts of vegetable oil, 0.003-0.012 part of hydroxide, 0.3-1.5 parts of benzoic acid, 5-12 parts of dibasic acid, 2-8 parts of polyhydric alcohol, 1-3 parts of xylene and 8-15 parts of an organic solvent; 1.2-3.0 parts of acrylic acid, 4-20 parts of styrene, 1-5 parts of alkene monomer containing epoxy group, 4-20 parts of acrylate monomer, 0.3-1.0 part of initiator, 2.5-5 parts of long-chain alkyl primary amine and 1-5 parts of neutralizer are added into the basic alkyd resin.
2. The modified alkyd resin of claim 1, wherein the epoxy-containing olefinic monomer is glycidyl methacrylate and/or allyl glycidyl ether.
3. The modified alkyd resin of claim 1 or 2, wherein the long-chain alkyl primary amine comprises at least one of dodecylamine, hexadecylamine, oleylamine, octadecylamine, tallow acid, or hydrogenated tallow acid.
4. The modified alkyd resin of claim 1, wherein the acrylate monomer comprises at least one of methyl methacrylate, butyl acrylate, butyl methacrylate, isobornyl acrylate, isobornyl methacrylate, or hydroxypropyl acrylate.
5. The modified alkyd resin of claim 1, wherein the vegetable oil comprises at least one of soybean oil, linseed oil, or castor oil.
6. The modified alkyd resin of claim 1, 2, 4, 5,
the dibasic acid comprises phthalic anhydride and/or isophthalic acid;
the polyhydric alcohol comprises trimethylolpropane and/or pentaerythritol;
the organic solvent comprises at least one of diethylene glycol monobutyl ether, dipropylene glycol monobutyl ether, diethylene glycol monomethyl ether, ethylene glycol tert-butyl ether, propylene glycol ethyl ether, propylene glycol propyl ether, propylene glycol butyl ether, or propylene glycol methyl ether.
7. A process for the preparation of a modified alkyd resin according to any of claims 1 to 6, comprising the steps of:
s1, dissolving oil, polyol and hydroxide in ethanol, sequentially adding benzoic acid, dibasic acid and xylene for reaction, removing the xylene after the reaction is finished, cooling, and adding an organic solvent to obtain a basic alkyd resin;
s2 heating the basic alkyd resin, dripping a blend containing acrylic acid, styrene, an epoxy group-containing alkene monomer and an acrylate monomer, and after dripping is finished, carrying out heat preservation treatment;
s3, after the heat preservation is finished, carrying out primary cooling, adding long-chain alkyl primary amine, and carrying out heat preservation treatment;
and (S4) after the heat preservation is finished, carrying out secondary cooling, adding an amine neutralizer, and carrying out heat preservation treatment to obtain the modified waterborne alkyd resin.
8. The method according to claim 7, wherein the reaction temperature in S1 is 170-210 ℃, and the determination of the reaction end point is that the acid value is 16-24 mg KOH/g.
9. The process of claim 7, wherein the alkyd resin is prepared by reacting,
in S2, heating to 125-135 ℃, and preserving heat for 1-3 h;
in S3, cooling to 80-110 ℃ for one time, and preserving heat for 1-2 h;
and in S4, cooling to 80 ℃ for the second time, and preserving heat for 0.5-1 h.
10. A modified aqueous alkyd resin dispersion, characterized in that the modified alkyd resin obtained according to claim 1 is dispersed in deionized water to give the finished product.
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