CN113336923A - Preparation method of waterborne alkyd resin containing carbonyl groups and coating thereof - Google Patents
Preparation method of waterborne alkyd resin containing carbonyl groups and coating thereof Download PDFInfo
- Publication number
- CN113336923A CN113336923A CN202010880628.0A CN202010880628A CN113336923A CN 113336923 A CN113336923 A CN 113336923A CN 202010880628 A CN202010880628 A CN 202010880628A CN 113336923 A CN113336923 A CN 113336923A
- Authority
- CN
- China
- Prior art keywords
- acid
- alkyd resin
- oil fatty
- carbonyl
- fatty acid
- 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.)
- Pending
Links
- 229920000180 alkyd Polymers 0.000 title claims abstract description 71
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 title claims abstract description 41
- 238000000576 coating method Methods 0.000 title claims abstract description 28
- 239000011248 coating agent Substances 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims description 7
- 238000000034 method Methods 0.000 claims abstract description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 230000032050 esterification Effects 0.000 claims abstract description 8
- 238000005886 esterification reaction Methods 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 6
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 23
- 239000000194 fatty acid Substances 0.000 claims description 23
- 229930195729 fatty acid Natural products 0.000 claims description 23
- 150000004665 fatty acids Chemical class 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 8
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 229920002125 Sokalan® Polymers 0.000 claims description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 6
- 239000002518 antifoaming agent Substances 0.000 claims description 6
- 239000002270 dispersing agent Substances 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
- 239000000178 monomer Substances 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 239000002562 thickening agent Substances 0.000 claims description 6
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 6
- 239000008158 vegetable oil Substances 0.000 claims description 6
- 239000000080 wetting agent Substances 0.000 claims description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 5
- 235000010233 benzoic acid Nutrition 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 238000004806 packaging method and process Methods 0.000 claims description 5
- 150000007519 polyprotic acids Polymers 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 claims description 4
- 239000002131 composite material Substances 0.000 claims description 4
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
- 239000003784 tall oil Substances 0.000 claims description 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 2
- PNNFEYPWPCDLOC-UPHRSURJSA-N (z)-2,3-dichlorobut-2-enedioic acid Chemical compound OC(=O)C(\Cl)=C(\Cl)C(O)=O PNNFEYPWPCDLOC-UPHRSURJSA-N 0.000 claims description 2
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 2
- LXOFYPKXCSULTL-UHFFFAOYSA-N 2,4,7,9-tetramethyldec-5-yne-4,7-diol Chemical compound CC(C)CC(C)(O)C#CC(C)(O)CC(C)C LXOFYPKXCSULTL-UHFFFAOYSA-N 0.000 claims description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 2
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 claims description 2
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 claims description 2
- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 claims description 2
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 claims description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 2
- 239000004135 Bone phosphate Chemical class 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- 235000019486 Sunflower oil Nutrition 0.000 claims description 2
- 229920013802 TRITON CF-10 Polymers 0.000 claims description 2
- UOJLTGJDEASXFF-UHFFFAOYSA-N [Mn].[Co].[Fe] Chemical compound [Mn].[Co].[Fe] UOJLTGJDEASXFF-UHFFFAOYSA-N 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 claims description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 2
- HCOMFAYPHBFMKU-UHFFFAOYSA-N butanedihydrazide Chemical compound NNC(=O)CCC(=O)NN HCOMFAYPHBFMKU-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 239000004359 castor oil Substances 0.000 claims description 2
- 235000019438 castor oil Nutrition 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 235000012343 cottonseed oil Nutrition 0.000 claims description 2
- 239000002385 cottonseed oil Substances 0.000 claims description 2
- VESYLILPTXPEDK-UHFFFAOYSA-N cyclohexane-1,1-dicarbohydrazide Chemical compound NNC(=O)C1(C(=O)NN)CCCCC1 VESYLILPTXPEDK-UHFFFAOYSA-N 0.000 claims description 2
- ZWLIYXJBOIDXLL-UHFFFAOYSA-N decanedihydrazide Chemical compound NNC(=O)CCCCCCCCC(=O)NN ZWLIYXJBOIDXLL-UHFFFAOYSA-N 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- SWRGUMCEJHQWEE-UHFFFAOYSA-N ethanedihydrazide Chemical compound NNC(=O)C(=O)NN SWRGUMCEJHQWEE-UHFFFAOYSA-N 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 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 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 239000000944 linseed oil Substances 0.000 claims description 2
- 235000021388 linseed oil Nutrition 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- LGYJSPMYALQHBL-UHFFFAOYSA-N pentanedihydrazide Chemical compound NNC(=O)CCCC(=O)NN LGYJSPMYALQHBL-UHFFFAOYSA-N 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 239000002600 sunflower oil Substances 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002383 tung oil Substances 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims 2
- 150000003077 polyols Chemical class 0.000 claims 2
- YBDQLHBVNXARAU-UHFFFAOYSA-N 2-methyloxane Chemical compound CC1CCCCO1 YBDQLHBVNXARAU-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 238000007792 addition Methods 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 239000000049 pigment Substances 0.000 claims 1
- PSIKPHJLTVSQFO-UHFFFAOYSA-N propanedihydrazide Chemical compound NNC(=O)CC(=O)NN PSIKPHJLTVSQFO-UHFFFAOYSA-N 0.000 claims 1
- 238000001035 drying Methods 0.000 abstract description 14
- 239000003973 paint Substances 0.000 abstract description 10
- 238000004132 cross linking Methods 0.000 abstract description 8
- 229920005989 resin Polymers 0.000 abstract description 7
- 239000011347 resin Substances 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract description 2
- 239000007787 solid Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 6
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 229940040102 levulinic acid Drugs 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000012855 volatile organic compound Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- ZNGSVRYVWHOWLX-KHFUBBAMSA-N (1r,2s)-2-(methylamino)-1-phenylpropan-1-ol;hydrate Chemical compound O.CN[C@@H](C)[C@H](O)C1=CC=CC=C1.CN[C@@H](C)[C@H](O)C1=CC=CC=C1 ZNGSVRYVWHOWLX-KHFUBBAMSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- ZWLFGLCGZUVIEA-UHFFFAOYSA-N nonanedihydrazide Chemical compound NNC(=O)CCCCCCCC(=O)NN ZWLFGLCGZUVIEA-UHFFFAOYSA-N 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/46—Polyesters chemically modified by esterification
- C08G63/48—Polyesters chemically modified by esterification by unsaturated higher fatty oils or their acids; by resin 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
-
- 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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/08—Anti-corrosive paints
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Paints Or Removers (AREA)
Abstract
The invention relates to a waterborne alkyd resin containing carbonyl groups and a coating thereof. The resin has the main structure of an alkyd resin and has carbonyl groups capable of post-crosslinking. Wherein the mass of the acetyl C1-C8 carboxylic acid containing carbonyl groups accounts for 0.3-2 wt% of the solid resin. During the esterification process for the synthesis of alkyd resins, carbonyl groups which can be post-crosslinked are introduced into the alkyd resin by carbonyl-containing carboxylic acids. The carbonyl group-containing alkyd resin is used for preparing a coating, and a hydrazide compound is added to perform a crosslinking reaction, so that the prepared paint film further improves the resistance and the drying performance of the paint film on the basis of keeping the advantages of fullness, high gloss and the like of the alkyd resin paint film.
Description
Technical Field
The invention relates to a waterborne alkyd resin containing carbonyl groups and a coating thereof, belonging to the technical field of coatings.
Background
The traditional solvent-type alkyd resin has excellent comprehensive performance, but the content of the traditional solvent-type alkyd resin is too high, and the volatile organic compounds are finally and completely discharged into the atmosphere in the construction and drying processes, so that the environment is polluted, and the consumption of non-renewable petrochemical resources is increased. Because the water has the advantages of no toxicity, no combustion, low price, renewability and the like, the water is used for replacing the organic solvent, so that the emission of the organic solvent can be reduced, the cost is reduced, and the safety of production and constructors is improved. With the increasing awareness of the environmental protection of humans, a great number of researchers have moved their focus to environmentally friendly waterborne alkyds.
The water-based alkyd resin takes water as a solvent, can obviously reduce the discharge of VOC, reduces the pollution to the environment and the harm to human bodies, and has the advantages of compatibility, gloss retention, easy cleaning and the like. However, most waterborne alkyd coatings inherently suffer from a number of performance deficiencies. Due to the introduction of hydrophilic groups, the water resistance of the alkyd resin is slightly poorer than that of the traditional solvent-based alkyd resin. The water-based alkyd resin coating takes water as a solvent, so that the water volatilization speed is low, the surface tension is high, the drying process is more easily influenced by humidity and the like, and adverse factors such as possible hydrolysis of a drier and possible complex inactivation of an amine neutralizer and the drier exist, so that the general water-based alkyd resin has poor drying performance. Waterborne alkyds generally have difficulty meeting or exceeding the specifications of solvent-borne resins.
At present, the waterborne modified alkyd resin at home and abroad mainly comprises the following methods of polyurethane modification, acrylic acid modification, epoxy resin modification, organic silicon modification and the like. For example, Issman chemical company, in patent CN1365368, describes an emulsion of an acrylic-modified waterborne alkyd or urethane-modified alkyd dispersion in water. Patent CN101838389A describes an epoxy modified waterborne alkyd resin and a preparation method thereof. Patent CN108059908A describes an acrylic acid modified water-based alkyd resin paint and a preparation method thereof. Patent CN107778489A introduces an organosilicon modified waterborne alkyd resin and a preparation method thereof. These patents improve the drying and corrosion resistance of waterborne alkyds primarily by modification by copolymerization or grafting with other resins. However, there are few reports on improvement of drying property and corrosion resistance of waterborne alkyd resin by introduction of post-crosslinking group, and only documents such as "synthetic research on double-crosslinking acrylic resin modified waterborne alkyd resin" are scattered.
Disclosure of Invention
The invention aims to provide carbonyl group-containing waterborne alkyd resin with excellent comprehensive performance and high drying rate and a coating thereof. The resin can be widely used for water-based metal coatings, light anticorrosive coatings, water-based wood coatings and building coatings, and has great application potential.
In order to solve the technical problems, the invention provides the following technical scheme:
a method for preparing a waterborne alkyd resin containing carbonyl groups, comprising the steps of:
s1, introducing inert gas into vegetable oil fatty acid, polyalcohol, monobasic acid, carboxylic acid containing carbonyl and polybasic acid to remove esterification moisture, carrying out low-temperature esterification for 1h at 180 ℃, then heating to 240 ℃, and carrying out high-temperature esterification until the acid value is less than 10mg KOH/g, thereby obtaining a basic alkyd resin polymer;
s2, cooling the basic alkyd resin polymer prepared in the step S1 to 170 ℃, preserving heat, adding a water-based monomer, and reacting until the acid value is 35-50mg KOH/g;
s3, adding ethylene glycol monobutyl ether into the alkyd resin prepared in the step S2, diluting, cooling to below 70 ℃, adding a neutralizer with the acid value of 100% of that of the alkyd resin while stirring, and stirring for 30min-1h to mix uniformly. Cooling to room temperature after adding, filtering, and packaging.
Preferably, the weight ratio of the materials in the step S1 is 30-60 percent of vegetable oil fatty acid, 10-30 percent of polyalcohol, 10-40 percent of polybasic acid, 5-15 percent of monobasic acid and 0.3-2 percent of carboxylic acid containing carbonyl; step S2, the weight ratio of the materials is 80-95% of basic alkyd resin polymer and 5-20% of water-based monomer; the weight ratio of the materials in the step S3 is 65-70% of carbonyl-containing alkyd resin, 5-10% of neutralizer and 20-30% of ethylene glycol monobutyl ether.
Preferably, the vegetable oil fatty acid is a drying oil fatty acid or a semi-drying oil fatty acid, such as one or a mixture of more than two of flax oil fatty acid, soybean oil fatty acid, cottonseed oil fatty acid, sunflower oil fatty acid, tall oil fatty acid, dehydrated castor oil fatty acid and tung oil fatty acid.
Preferably, the carboxylic acid containing carbonyl group is one or a mixture of more than two of acetyl C1-C8 carboxylic acid.
Preferably, the polyhydric alcohol is one or a mixture of more than two of glycerol, trimethylolpropane, trimethylolethane, pentaerythritol and dipentaerythritol.
Preferably, the monoacid is one or a mixture of more than two of benzoic acid, abietic acid, hexahydrobenzoic acid, 2-ethylhexanoic acid and p-tert-butylbenzoic acid.
Preferably, the polybasic acid is one or a mixture of more than two of phthalic anhydride, isophthalic acid, terephthalic acid, maleic anhydride, fumaric acid, dichloromaleic acid, succinic acid, adipic acid, suberic acid, azelaic acid, sebacic acid, trimellitic anhydride and trimesic acid.
Preferably, the neutralizing agent is one or a mixture of more than two of KOH, NaOH, LiOH, triethylamine, diethanolamine and ammonia water.
Preferably, the water-based monomer is one or a mixture of more than two of tribasic acid such as trimellitic anhydride and the like, dimethylolpropionic acid, and polycarboxylic acrylic acid and ester prepolymer.
A preparation method of a carbonyl group-containing water-based alkyd resin coating comprises the following steps of:
step 1, dissolving a hydrazide compound in water, adding the synthesized waterborne alkyd resin with carbonyl groups, and dispersing at high speed and mixing uniformly;
and 2, adding a dispersing agent, a drier, a wetting agent and color paste, dispersing at a high speed, uniformly mixing, adding a thickening agent to adjust viscosity, and defoaming by using a defoaming agent.
Preferably, the weight ratio of the materials of the water-based alkyd resin coating is that the water-based alkyd resin containing carbonyl, the hydrazide compound, water, the dispersant, the wetting agent, the color paste, the drier, the thickening agent and the defoaming agent is 10-50 percent, 0.05-0.5 percent, 20-50 percent, 0.5-1.5 percent, 0.2-0.5 percent, 10-50 percent, 0.1-4 percent, 0.5-2 percent and 0.1-0.5 percent.
Preferably, the hydrazide compound is one or a mixture of more than two of oxalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, glutaric acid dihydrazide, adipic acid dihydrazide, cyclohexane dicarboxylic acid dihydrazide, azelaic acid dihydrazide and sebacic acid dihydrazide.
Preferably, the dispersant is at least one of BYK-191, BYK-190 and Orotan 681; the wetting agent is at least one of Surfynol TG, Surfynol AD01, Triton CF-10 and Tego 270.
Preferably, the defoaming agent is at least one of BYK-022, BYK-011, BYK-093, Tego 822 and Tego902 w. The thickener is at least one of Rheolate 299, Acrysol RM-8W, Acrysol RM-12W and Acrysol RM-5000.
Preferably, the aqueous drier is one or more of an environment-friendly aqueous iron drier, an aqueous cobalt drier, an aqueous iron-cobalt-manganese composite drier and a composite thereof.
Compared with the prior art, the invention has the following beneficial effects: the water-based alkyd resin coating promotes double bonds to generate crosslinking mainly through oxygen absorption in the drying film-forming process, and has the defects of over-slow drying speed, slow hardness rise and the like. The carbonyl group-containing water-based alkyd resin coating overcomes the defect of slow oxygen absorption and air drying of the common water-based alkyd resin coating through post-crosslinking of carbonyl and hydrazide groups in the coating film forming process, and has the advantages of high drying speed, high hardness rise, high gloss, good initial water resistance and the like. Can be widely used for water-based metal coatings, light anticorrosive coatings, water-based wood coatings and building coatings, and has great application potential.
Detailed Description
Example 1:
241.8g of soyaoleic acid, 179.6g of trimethylolpropane, 25.9g of benzoic acid, 150.7g of isophthalic acid and 2g of levulinic acid were charged into a 1L four-necked flask equipped with a stirrer, a thermometer, a condenser and an oil-water separator, reacted at 180 ℃ for 1 hour, heated to 240 ℃ and then reacted at an acid value of 10mgKOH/g with heat preservation. Reducing the temperature to 170 ℃, adding 47g of trimellitic anhydride, and reacting until the acid value is less than 40 mgKOH/g. Cooling the alkyd resin to 70 ℃, adding 195.65g of ethylene glycol monobutyl ether, adding 49.69g of triethylamine, stirring for 30min, uniformly mixing, cooling to room temperature, filtering and packaging.
The raw materials of the paint prepared by the waterborne alkyd resin containing carbonyl groups are shown in the following table:
example 2:
170g of linoleic acid, 160g of pentaerythritol, 40g of benzoic acid, 150g of terephthalic acid and 3g of levulinic acid are added into a 1L four-neck flask provided with a stirrer, a thermometer, a condenser and an oil-water separation device, the mixture is reacted for 1 hour at 180 ℃, and then the temperature is raised to 240 ℃, and the reaction is carried out until the acid value is 10 mgKOH/g. Reducing the temperature to 170 ℃, adding 52.3g of trimellitic anhydride, and reacting until the acid value is less than 40 mgKOH/g.
Cooling the alkyd resin to 70 ℃, adding 174g of ethylene glycol monobutyl ether, adding ammonia water to neutralize to be neutral, stirring for 30min, uniformly mixing, cooling to room temperature, filtering and packaging.
The raw materials of the paint prepared by the waterborne alkyd resin containing carbonyl groups are shown in the following table:
example 3:
240g of tall oil fatty acid, 179.6g of trimethylolpropane, 15g of benzoic acid, 150.7g of phthalic anhydride and 12g of levulinic acid are added into a 1L four-neck flask provided with a stirrer, a thermometer, a condenser and an oil-water separation device, reacted for 1 hour at 180 ℃, heated to 240 ℃, and reacted with heat preservation until the acid value reaches 10 mgKOH/g. Reducing the temperature to 170 ℃, adding 46.5g of trimellitic anhydride, and reacting until the acid value is less than 40 mgKOH/g.
Cooling the alkyd resin to 70 ℃, adding 193.93g of ethylene glycol monobutyl ether, adding 39.81g of triethylamine, stirring for 30min, uniformly mixing, cooling to room temperature, filtering and packaging.
The raw materials of the paint prepared by the waterborne alkyd resin containing carbonyl groups are shown in the following table:
the properties of the unmodified waterborne alkyd coating and the carbonyl group-containing modified waterborne alkyd coating are compared in the following table.
From the above results, it is clear that the modified waterborne alkyd containing carbonyl groups has better drying and water resistance properties than the unmodified waterborne alkyd.
The resin of the present invention has the main structure of alkyd resin and has carbonyl groups capable of post-crosslinking. Wherein the mass of the acetyl C1-C8 carboxylic acid containing carbonyl groups accounts for 0.3-2 wt% of the solid resin. During the esterification process for the synthesis of alkyd resins, carbonyl groups which can be post-crosslinked are introduced into the alkyd resin by carbonyl-containing carboxylic acids. The carbonyl group-containing alkyd resin is used for preparing a coating, and a hydrazide compound is added to perform a crosslinking reaction, so that the prepared paint film further improves the resistance and the drying performance of the paint film on the basis of keeping the advantages of fullness, high gloss and the like of the alkyd resin paint film.
The foregoing description of the invention has been presented for purposes of illustration and description, and is intended to be exemplary only and is not intended to limit the scope of the invention, which is to be construed as broadly as the invention may be embodied in the form of a key-word or a key-word.
Claims (10)
1. A preparation method of waterborne alkyd resin containing carbonyl groups is characterized by comprising the following steps:
s1, introducing inert gas into vegetable oil fatty acid, polyalcohol, monobasic acid, carboxylic acid containing carbonyl and polybasic acid to remove esterification moisture, carrying out low-temperature esterification for 1h at 180 ℃, then heating to 240 ℃, and carrying out high-temperature esterification until the acid value is less than 10mg KOH/g, thereby obtaining a basic alkyd resin polymer;
s2, cooling the basic alkyd resin polymer prepared in the step S1 to 170 ℃, preserving heat, adding a water-based monomer, and reacting until the acid value is 35-50mg KOH/g;
s3, adding ethylene glycol monobutyl ether into the alkyd resin prepared in the step S2, diluting, cooling to below 70 ℃, adding a neutralizer with the acid value of 100% of the alkyd resin while stirring, stirring for 30min-1h, uniformly mixing, cooling to room temperature after the addition, filtering, and packaging.
2. The method of claim 1, wherein the ratio of the vegetable oil fatty acid, the polyol, the polyacid, the monoacid, the carboxylic acid containing carbonyl group in the weight ratio of 30-60 to 10-30 to 10-40 to 5-15 to 0.3-2% is used in step S1; step S2, the weight ratio of the materials is 80-95% of basic alkyd resin polymer and 5-20% of water-based monomer; the weight ratio of the materials in the step S3 is 65-70% of carbonyl-containing alkyd resin, 5-10% of neutralizer and 20-30% of ethylene glycol monobutyl ether.
3. The method for producing a carbonyl group-containing aqueous alkyd resin according to claim 2, wherein the vegetable oil fatty acid is one or a mixture of two or more of linseed oil fatty acid, soybean oil fatty acid, cottonseed oil fatty acid, sunflower oil fatty acid, tall oil fatty acid, dehydrated castor oil fatty acid, tung oil fatty acid; the carboxylic acid containing carbonyl is one or a mixture of more than two of acetyl C1-C8 carboxylic acid.
4. A process according to claim 3, wherein the polyol is one or a mixture of two or more of glycerol, trimethylolpropane, trimethylolethane, pentaerythritol, dipentaerythritol; the monoacid is one or a mixture of more than two of benzoic acid, abietic acid, hexahydrobenzoic acid, 2-ethylhexanoic acid and p-tert-butylbenzoic acid; the polybasic acid is one or a mixture of more than two of phthalic anhydride, isophthalic acid, terephthalic acid, maleic anhydride, fumaric acid, dichloromaleic acid, succinic acid, adipic acid, suberic acid, azelaic acid, sebacic acid, trimellitic anhydride and trimesic acid.
5. The method for preparing a carbonyl group-containing waterborne alkyd resin according to claim 4, wherein the waterborne monomer is one or a mixture of more than two of trimellitic acid anhydride and other tribasic acids, dimethylolpropionic acid, and polycarboxylic acrylic acid and ester prepolymers; the neutralizing agent is one or a mixture of more than two of KOH, NaOH, LiOH, triethylamine, diethanolamine and ammonia water.
6. A method for preparing a carbonyl group-containing waterborne alkyd resin coating, wherein the coating consists of the carbonyl group-containing waterborne alkyd resin, pigment and filler, auxiliary agent, solvent and hydrazide compound, which is defined by any one of claims 1 to 5, and comprises the following steps:
step 1, dissolving a hydrazide compound in water, adding the synthesized waterborne alkyd resin with carbonyl groups, and dispersing at high speed and mixing uniformly;
and 2, adding a dispersing agent, a drier, a wetting agent and color paste, dispersing at a high speed, uniformly mixing, adding a thickening agent to adjust viscosity, and defoaming by using a defoaming agent.
7. The process according to claim 6, wherein the weight ratio of the materials fed is carbonyl-containing aqueous alkyd resin: hydrazide compounds: water, dispersant, wetting agent, color paste, drier, thickener and defoaming agent in the weight ratio of 10-50 to 0.05-0.5 to 20-50 to 0.5-1.5 to 0.2-0.5 to 10-50 to 0.1-4 to 0.5-2 to 0.1-0.5.
8. The method of claim 7, wherein the hydrazide compound is one or more selected from the group consisting of oxalic dihydrazide, malonic dihydrazide, succinic dihydrazide, glutaric dihydrazide, adipic dihydrazide, cyclohexane dicarboxylic dihydrazide, azelaic dihydrazide and sebacic dihydrazide.
9. The method of claim 8, wherein the dispersant is at least one of BYK-191, BYK-190, Orotan 681; the wetting agent is at least one of Surfynol TG, Surfynol AD01, Triton CF-10 and Tego 270; the defoaming agent is at least one of BYK-022, BYK-011, BYK-093, Tego 822 and Tego902 w; the thickener is at least one of Rheolate 299, Acrysol RM-8W, Acrysol RM-12W and Acrysol RM-5000.
10. The method of claim 9, wherein the aqueous drier is one or more of an environmentally friendly aqueous iron drier, an aqueous cobalt drier, an aqueous iron-cobalt-manganese composite drier, and a composite thereof.
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| CN116376409A (en) * | 2023-03-01 | 2023-07-04 | 长沙学院 | Anticorrosive paint and preparation method and application thereof |
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