CN114409883B - Aluminate glue modified polyester, preparation method thereof, paint and resin membrane - Google Patents
Aluminate glue modified polyester, preparation method thereof, paint and resin membrane Download PDFInfo
- Publication number
- CN114409883B CN114409883B CN202111580556.9A CN202111580556A CN114409883B CN 114409883 B CN114409883 B CN 114409883B CN 202111580556 A CN202111580556 A CN 202111580556A CN 114409883 B CN114409883 B CN 114409883B
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- China
- Prior art keywords
- aluminate
- acid
- modified polyester
- polyester
- glue
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- 229920000728 polyester Polymers 0.000 title claims abstract description 96
- 150000004645 aluminates Chemical class 0.000 title claims abstract description 76
- 239000003292 glue Substances 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 32
- 229920005989 resin Polymers 0.000 title claims abstract description 19
- 239000011347 resin Substances 0.000 title claims abstract description 19
- 239000012528 membrane Substances 0.000 title abstract description 7
- 239000003973 paint Substances 0.000 title description 7
- 239000002253 acid Substances 0.000 claims abstract description 46
- 239000000178 monomer Substances 0.000 claims description 45
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 30
- 102000008186 Collagen Human genes 0.000 claims description 20
- 108010035532 Collagen Proteins 0.000 claims description 20
- 229920001436 collagen Polymers 0.000 claims description 20
- 239000007788 liquid Substances 0.000 claims description 20
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 17
- 229910052710 silicon Inorganic materials 0.000 claims description 17
- 239000010703 silicon Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 229910000077 silane Inorganic materials 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000006011 modification reaction Methods 0.000 claims description 7
- 238000005886 esterification reaction Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- -1 silane compound Chemical class 0.000 claims description 5
- 239000008199 coating composition Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000006482 condensation reaction Methods 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical group 0.000 claims description 2
- 238000000576 coating method Methods 0.000 abstract description 15
- 239000011248 coating agent Substances 0.000 abstract description 14
- 239000004568 cement Substances 0.000 abstract description 3
- 229910010272 inorganic material Inorganic materials 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 230000004048 modification Effects 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 238000012986 modification Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 9
- 229910000831 Steel Inorganic materials 0.000 description 8
- 230000018044 dehydration Effects 0.000 description 8
- 238000006297 dehydration reaction Methods 0.000 description 8
- 239000010959 steel Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 238000009863 impact test Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000005070 sampling Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229910001593 boehmite Inorganic materials 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000007385 chemical modification Methods 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000002086 nanomaterial Substances 0.000 description 3
- 238000011056 performance test Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- RXGUIWHIADMCFC-UHFFFAOYSA-N 2-Methylpropyl 2-methylpropionate Chemical compound CC(C)COC(=O)C(C)C RXGUIWHIADMCFC-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229920003180 amino resin Polymers 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000011362 coarse particle Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 150000007519 polyprotic acids Chemical class 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- HDYRYUINDGQKMC-UHFFFAOYSA-M acetyloxyaluminum;dihydrate Chemical compound O.O.CC(=O)O[Al] HDYRYUINDGQKMC-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- CSDREXVUYHZDNP-UHFFFAOYSA-N alumanylidynesilicon Chemical compound [Al].[Si] CSDREXVUYHZDNP-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 229940009827 aluminum acetate Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- BVFSYZFXJYAPQJ-UHFFFAOYSA-N butyl(oxo)tin Chemical compound CCCC[Sn]=O BVFSYZFXJYAPQJ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical group 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000020985 whole grains Nutrition 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
- 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
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K7/00—Use of ingredients characterised by shape
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
- C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
-
- 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
- C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
- C09D161/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
-
- 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
-
- 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
- C09D7/61—Additives non-macromolecular inorganic
- C09D7/62—Additives non-macromolecular inorganic modified by treatment with other compounds
-
- 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
- C09D7/70—Additives characterised by shape, e.g. fibres, flakes or microspheres
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2227—Oxides; Hydroxides of metals of aluminium
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/011—Nanostructured additives
Abstract
The application discloses an aluminate glue modified polyester, a preparation method thereof, a coating and a resin membrane, and relates to the technical field of organic-inorganic compound preparation. An aluminate cement modified polyester comprising: a sheet-like aluminate gum unit and an acid-based polyester unit; wherein the flaky aluminate gum unit and the acid-based polyester unit are connected through an ester bond. The modified polyester of the present application improves the heat resistance and film-forming hardness and impact resistance of the polyester.
Description
Technical Field
The application relates to the technical field of organic-inorganic compound preparation, in particular to an aluminate glue modified polyester, a preparation method thereof, a coating and a resin membrane.
Background
Polyester is a generic term for high molecular weight compounds obtained by polycondensation of a dihydric alcohol or a dibasic acid or a polyhydric alcohol with a polyprotic acid. The polyester has good processability, large hardness of the cured adhesive layer, good transparency and high brightness, can be quickly solidified under normal temperature pressurization, and has good heat resistance, wear resistance, chemical resistance and mechanical property.
The polyester is mainly used for bonding glass fiber reinforced plastic, hard plastic, concrete, electric filling and sealing and the like. Polyesters are also widely used in the coatings industry. However, the existing polyesters have the following defects: the polyester has large molecular weight, poor solubility and high viscosity, and is difficult to chemically modify with other resins/components.
The physical modification of the polyester is carried out during the formation of the polymer, and generally blending is adopted. The chemical modification of polyester is carried out in the synthesis process, and a third monomer and a fourth monomer are added outside the basic monomers to change the macromolecular structure so as to achieve the aim of improving certain physical and chemical properties. There are many common mechanisms between chemical modification and physical modification, not only depending on each other in implementation.
The modified polyesters commonly used at present include: silicone modified polyesters, acrylic modified polyesters, epoxy modified polyesters (polyester polyols), and the like. The modified polyester can be used for heat-resistant paint, packing paint, coil steel paint/lamination. In order to enhance the functions of corrosion resistance, graffiti resistance, stain resistance, fingerprint resistance, reflection resistance, self-repairing and the like of the polyester coating, nano materials can be added into the polyester coating. However, the problems of high cost of the nano material, dispersion process threshold and the like limit the wide application of the material.
Disclosure of Invention
In order to solve the defects in the art, the application provides an aluminate glue modified polyester, a preparation method thereof, a coating and a resin membrane.
According to one aspect of the application, an aluminate cement modified polyester comprises: a sheet-like aluminate gum unit and an acid-based polyester unit;
wherein the flaky aluminate gum unit and the acid-based polyester unit are connected through an ester bond.
According to some embodiments of the application, the acid-based polyester is prepared by esterification of an acid-based monomer and a hydroxyl monomer.
According to some embodiments of the application, the sheet-like glue units are made from a collagen aluminate solution and silane by a surface modification reaction.
According to some embodiments of the application, the collagen aluminate liquor is selected from sheet-like aluminate gums.
According to another aspect of the present application, there is provided a method for preparing an aluminate-modified polyester, comprising:
preparation of an aluminate glue prepolymerization liquid: carrying out surface modification reaction on the aluminate collagen liquid and a silicon-based monomer;
preparation of acid-based polyester prepolymer: reacting an acid-based monomer with a hydroxyl monomer;
preparation of modified polyester: and (3) carrying out esterification reaction and condensation reaction on the aluminate glue prepolymerization solution and the acid-based polyester prepolymerization solution under the condition of a catalyst.
According to some embodiments of the application, the collagen aluminate liquor is selected from sheet-like aluminate gums.
According to some embodiments of the application, the collagen aluminate solution comprises 0.5-1.5% of the total weight of the modified polyester.
According to some embodiments of the application, the mass of the silicon-based monomer is less than or equal to 5% of the total weight of the collagen aluminate solution.
According to some embodiments of the application, the mass ratio of the collagen aluminate solution to the acid-based monomer is (0.5-3): 100. The preferred mass ratio is (1-2): 100.
According to some embodiments of the application, the modified polyester has an acid value of 53 to 70mgKOH/g.
According to some embodiments of the application, the silicon-based monomer is a silane compound.
According to some embodiments of the application, the silane is selected from one or more of epoxy, amine, and hydroxyl containing groups.
According to some embodiments of the application, the acid-based monomer is selected from one or more of a group consisting of a polybasic organic acid having 4 to 36 carbon atoms, an ester, and an anhydride.
According to some embodiments of the application, the hydroxyl monomer is selected from polyols having a carbon number of 2-14.
According to some embodiments of the application, the catalyst comprises: an organotin.
According to some embodiments of the application, the organotin structural formula is: r is R n SnX m ;
Wherein n=1 to 4, m=0 to 3, x is halogen, and R is alkyl or aryl.
According to still another aspect of the present application, there is provided a coating composition comprising the modified polyester described above, or a modified polyester prepared by the above method.
According to still another aspect of the present application, there is provided a resin film comprising the above modified polyester, or the modified polyester produced by the above method.
The application has the beneficial effects that:
the application provides an aluminate glue modified polyester. The aluminate glue modified polyester can improve the heat resistance, film forming hardness and impact resistance of the polyester. The aluminate glue can generate strong force in the polyester structure, and the polyester maintains the acid value of 53-70mgKOH/g, can balance the increase of internal force, and can adjust the viscosity of the product and improve the hardness. So that it can remain dissolved in the solvent (without being applied as a coating resin due to a large increase in viscosity).
The application provides a preparation method of aluminate glue modified polyester, which is characterized in that acid-based polyester and silane modified flaky aluminate glue react by a melt copolymerization method to prepare flaky aluminate glue modified polyester. Wherein the polybasic acid and the polyhydric alcohol are esterified to form polyester with acid groups, and the flaky aluminate gum unit, namely the silane modified flaky aluminate gum is derived from aluminum-based monomer (flaky aluminate gum) and silicon-based unit monomer which are mixed and formed through surface modification reaction. The reaction method is efficient, has no byproduct generation, has high reaction yield, and has industrial mass production prospect.
The modified polyester of the application combines nano aluminate glue with polyester through chemical modification technology. The hardness of the polyester can be improved by adding a small amount of aluminate glue, the wear resistance is improved, and the polyester can also be applied to improving the physical properties of traditional coil steel and mechanical baking varnish.
Detailed Description
As mentioned above, in the background art, the modification of the polyester at present has the problems of high cost, dispersion technology threshold and the like. Aiming at the problems, the application provides an aluminate glue modified polyester, a preparation method thereof, a coating and a resin membrane.
The technical solutions of the present application will be clearly and completely described in conjunction with the embodiments of the present application, and it is apparent that the described embodiments are some embodiments of the present application, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the application without making any inventive effort, are intended to be within the scope of the application.
It is particularly pointed out that similar substitutions and modifications to the application will be apparent to those skilled in the art, which are all deemed to be included in the application. It will be apparent to those skilled in the relevant art that variations and modifications can be made in the methods and applications described herein, or in the appropriate variations and combinations, without departing from the spirit and scope of the application. It will be apparent that the described embodiments are only some, but not all, embodiments of the application.
The application is carried out according to the conventional conditions or the conditions suggested by manufacturers if the specific conditions are not noted, and the raw materials or auxiliary materials and the reagents or instruments are conventional products which can be obtained commercially if the manufacturers are not noted.
According to the technical conception of the application, an aluminate glue modified polyester, a preparation method thereof, a coating and a resin membrane are provided.
The present application will be described in detail below.
[ modified aluminate glue ]
The aluminate collagen liquid (acidic aqueous alumina sol) is flaky alumina;
the modified aluminate glue is an alumina composite silane group and comprises an aluminum-based monomer and a silane monomer.
The aluminum oxide monomer is nano aluminum oxide with a sheet structure. The length of the flake is 1-800nm, the ratio of length to width is 1-1000, the average thickness is 1-500nm, and the whole grain diameter is 1-900nm.
If the particle size is too large, a uniform transparent resin cannot be formed.
The modified aluminate glue has the effect of improving the physical property of the product by adding a small amount, and the nano alumina with other shapes does not have the effect.
The silane has the function of surface modification, and the nano material and the polyester have good dispersing function by virtue of the surface modification.
The collagen aluminate solution accounts for 0.5 to 1.5 percent of the total weight of the modified polyester.
According to an embodiment of the present application, the alumina source is selected from alumina hydrate, aluminum nitrate, aluminum sulfate, aluminum acetate, aluminum chloride, aluminum hydroxide, aluminum oxide, and the like;
optionally alumina monohydrate, boehmite particles, alumina sol.
The boehmite particles are not particularly limited, and examples thereof include "DISPARL" and "DISPAL" manufactured by Sasol corporation, "Seawamori" (registered trademark) manufactured by He-Kagaku Kogyo Co., ltd., and "boehmite powder" manufactured by Damine chemical industry Co., ltd.
According to an embodiment of the present application, the alumina sol particles (sheet-like aluminate glue) are not particularly limited, examples of the "AS-200", "AS-550", "AS-520" and "Sichuan-Messaging" are alumina sols produced by Nissan chemical industries, inc., and examples of the "10A", "10C", "10D", "A2", "CSA-110A", "F-1000", "F-3000" and "Al-L7", "Al-ML15", "Al-C20" and "AS-L10" are alumina sols produced by Sichuan chemical industries, inc.
Wherein AS-200 is a flaky aluminate glue, AS-550, AS-520 is spherical nano alumina Sichuan grinding and chemical, and alumina sol of '10A', '10C', '10D', 'A2', 'CSA-110A', 'F-1000', 'F-3000' rod/flaky structure, and multi-wood chemical 'Al-L7', 'Al-ML 15', 'Al-C20', 'AS-L10' and the like are nano flaky structures.
[ silicon-based monomer ]
The silicon-based monomer is selected from the group consisting of a siloxane compound having a reactive end group. For the reactive end groups, in particular, the silicon-based monomers are selected from organic groups having epoxy groups, amine groups and hydroxyl groups.
The mass of the silicon-based monomer is less than or equal to 5 percent of the total weight of the aluminate collagen liquid.
[ acid-based polyesters ]
The acid-based polyester is prepared by esterification reaction of acid-based monomers and hydroxyl monomers.
The acid-based monomer is selected from monocarboxylic acid, dicarboxylic acid anhydride or acid, and polycarboxylic acid anhydride or acid;
the hydroxyl monomer is selected from monohydric alcohol, dihydric alcohol and polyhydric alcohol.
The mass ratio of the aluminate collagen liquid to the acid-based monomer is (0.5-3) 200.
The preferred mass ratio is (1-2): 100.
[ catalyst ]
The crosslinking catalyst for the reaction is selected from organotin;
the organic tin has a general formula: r is R n SnX m (n=1-4, m=0-3, x is halogen, R is alkyl or aryl), a group of metal organic compounds, and combinations thereof.
The organotin can be selected from the following: (CH) 3 ) n SnCl m 、C 4 H 10 O 2 Sn、C 4 H 11 ClO 2 Sn、C 28 H 54 O 6 Sn, etc. (n=1-4, m=0-3).
[ method for producing modified polyester ]
A preparation method of an aluminate glue modified polyester comprises the following steps:
a) Preparing a flaky alumina prepolymer (aluminate glue prepolymer):
mixing the aluminate collagen liquid (flaky alumina unit monomer) with a silicon-based unit monomer, and performing a surface modification reaction to form flaky alumina prepolymer.
b) Preparing an acid-based polyester prepolymer:
the acid-based polyester prepolymer is prepared by reacting an acid-based monomer with a hydroxyl monomer.
c) Preparation of aluminate glue modified polyester:
forming modified polyester through esterification and condensation reaction of the products of the step a) and the step b) under the condition of a crosslinking catalyst; wherein the weight of the self-flaked alumina units is 0.5 to 1.5 percent based on the total weight of the modified polyester; the acid value of the modified polyester is 53-70mgKOH/g.
[ resin film ]
A resin film comprising said aluminate-modified polyester.
[ coating composition ]
A coating composition comprising said aluminate-modified polyester.
The paint comprises the following raw materials: 20 to 45 weight percent of aluminate cement modified polyester, 10 to 45 weight percent of amino resin, 15 to 45 weight percent of filler and 25 to 45 weight percent of high boiling point solvent.
The filler is selected from one or more of titanium dioxide, silicon dioxide and silicon carbide.
The high boiling point solvent is selected from one or more of propylene glycol methyl ether acetate, glycol ether acetate, butyl acetate, isobutyl isobutyrate, 3-ether ethyl propionate and methyl isoamyl ketone.
The coating further comprises a pigment selected from inorganic pigments such as carbon black, iron oxide red pigments; and may also be selected from organic pigments such as phthalocyanine blue and the like.
The preparation method of the coating is a preparation method commonly used in the field, and is obtained by mixing amino resin, flaky alumina composite organic modified polyester, pigment, filler, organosilicon auxiliary agent and high-boiling point solvent.
The flaky alumina and silane are organically modified to prepare the alumina modified polyester, and the prepared modified coating has higher heat resistance and good hardness.
The present application will be described in detail with reference to specific examples.
EXAMPLE 1 nanometer aluminate gum 1% and 10% modification amount
a) Preparation of aluminate glue prepolymerization liquid
90.26g of nano sheet-shaped aluminate gum soluble AS200 with solid content of 10% and 0.09g of AD-124 are added into a four-port reaction bottle, a nitrogen and oil-water separator is arranged on the reaction bottle, stirring is started and heating is carried out to 100 ℃, the reaction is carried out until oil-free dripping-shaped objects are generated, the temperature is reduced, and the reaction bottle is taken out for standby.
b) Preparation of polyester prepolymer with acid group
Another four-mouth reaction bottle is taken, 195.93g of isophthalic acid, 195.93g of phthalic anhydride, 126.18g of adipic acid, 90.13g of neopentyl glycol and 391.85g of trimethylolpropane are added, the temperature is raised to 90 ℃, a small amount of pure water is added to help to dissolve, and the preparation of the polyester prepolymer with acid groups is completed after the reactants are in liquid state.
c) Preparation of flaky aluminate glue modified polyester
Adding the aluminate glue prepolymerization liquid obtained in the step 1) into the polyester prepolymerization liquid with acid groups obtained in the step 2), stirring under nitrogen, heating to 100 ℃, and removing the water of flaky alumina for about 3 hours;
continuously heating to 140 ℃ for about 3 hours, and carrying out ring opening modification and esterification reaction on the epoxy functional group and the acid group; after the moisture is removed, 0.4g of monobutyl tin oxide is added, the reaction is continuously heated to 220 ℃, a small amount of dimethylbenzene is added for reflux, the water is assisted to be collected into an oil-water separation pipe, and the heat preservation reflux is carried out for 9 hours, so that the nano aluminate glue modified polyester is obtained. Sample sampling is carried out, the measured acid value is 50mgKOH/g, the hydroxyl value is 234mgKOH/g, the product viscosity is measured, the dehydration amount is recorded, the dehydration amount is 106.44g, the viscosity is more than Z8, and the addition proportion of the organically modified flaky alumina is calculated to be 1%.
Examples 2 to 7
The preparation method is the same as in example 1, and the content difference of each component is shown in Table 1:
table 1 example component contents
Note that: AD124 is 3-glycidoxypropyl trimethoxysilane
Comparative example 1: omitting the step of heating to 140 ℃ for about 3 hours
The preparation is the same as in example 1, except that there is no step of heating to 140℃for about 3 hours. Without this 140 ℃ heating step, the nanoaluminate gum cannot be fused with the polyester, resulting in resin cloudiness and coarse particles. The reaction product was not available for subsequent performance measurements.
Comparative example 2: nano alumina AS520 added 1%
The preparation method is the same AS in example 1, except that the aluminate gum sol AS200 is replaced by 90.26g of nano aluminate gum sol AS520.
The reaction is continuously heated to 220 ℃, a small amount of dimethylbenzene is added for reflux, water is assisted to be collected into an oil-water separation pipe, the temperature is kept for reflux for 9 hours, sample sampling is carried out, the measured acid value is 9.8mgKOH/g, the hydroxyl value is 234mgKOH/g, the viscosity of the product is measured, the dehydration amount is recorded, the dehydration amount is 106.44g, and the viscosity is Z5-Z6.
Comparative example 3: nano alumina ASFP-20 addition 1%
The preparation method is the same AS in example 1, except that the nano-aluminate colloidal sol AS200 is replaced by 90.26g of nano-aluminate colloidal sol ASFP-20.
The reaction is continuously heated to 220 ℃, a small amount of dimethylbenzene is added for reflux, water is assisted to be collected into an oil-water separation tube, the temperature is kept for reflux for 9 hours for sample sampling, the measured acid value is 7.5mgKOH/g, the hydroxyl value is 234mgKOH/g, the viscosity of the product is measured, the dehydration amount is recorded, the dehydration amount is 106.44g, and the viscosity is Z4-Z5.
Comparative example 4: 10% of modified amount, 0.9g of AD-124
The preparation was the same as in example 1 except that the amount of AD-124 was changed to 0.90g.
The reaction is continuously heated to 220 ℃, a small amount of dimethylbenzene is added for reflux, water is assisted to be collected into an oil-water separation pipe, the temperature is kept for reflux for 9 hours for sample sampling, the measured acid value is 7.5mgKOH/g, the hydroxyl value is 234mgKOH/g, the viscosity of the product is measured, the dehydration amount is 106.44g, and the product is diluted to 70% viscosity of Z4-Z5 by using propylene glycol methyl ether acetate solvent.
Comparative example 5: nano alumina AS200 added 3%
The preparation method is the same AS in example 1, except that the dosage of the nano-aluminate colloidal sol AS200 is changed to 270.78g.
The reaction is continuously heated to 220 ℃, a small amount of dimethylbenzene is added for reflux, water is assisted to be collected into an oil-water separation tube, the temperature is kept for reflux for 9 hours for sample sampling, the product is colloidal Gel when the measured dehydration amount is 77.23g, the solvent cannot be diluted, and the viscosity and the subsequent performance test cannot be measured.
Test examples
[ method for producing coating/test piece production ]
The formulation ratio of the modified polyester coating is formulated according to the following table 2 ratio.
Table 2 modified polyester paint formulation
[ Pencil hardness ]
The pencil hardness is a test piece hardness value of 4H or more under operation according to JIS K5400-5-4, defined as PASS.
IMPACT strength IMPACT
Impact strength was measured in accordance with the ball drop test, operating according to the method of GB/T1732-1993, in sequence:
ball impact test height of 300g steel ball: 30cm drop phenomenon: no broken piece is generated;
ball impact test height of 300g steel ball: 50cm height drop phenomenon: no broken piece is generated;
500g steel ball at ball drop impact test height: 30cm height drop phenomenon: no broken piece is generated;
500g steel ball at ball drop impact test height: 50cm height drop phenomenon: no broken piece is generated;
any of the above 4 phases results in no fragmentation, defined as PASS (PASS).
If the test is passed, the previous stage value is recorded (for example, 0.5 Kg.30 cm in Table 3 represents a test of passing 500g steel ball at a ball drop impact test height of 30cm, but failing 500g steel ball at a ball drop impact test height of 50 cm).
TABLE 3 results of Performance test of examples 1-7
Table 4 results of Performance test of comparative examples 2 to 3
Comparative example | Dewatering amount of polyester | OHV | Appearance of resin | Hardness of pencil | IMPACT |
2 | 106.44 | 234.29 | Transparent and transparent | 2H | 0.5kg*50cm |
3 | 106.44 | 234.29 | Semitransparent light | 2H | 0.5kg*50cm |
The application synthesizes the organic-inorganic composite aluminum-silicon modified polyester coating by a one-pot method. The nano aluminate glue can be stably dispersed in a system of dibasic acid and polyhydric alcohol due to modification of epoxy functional group silane in the synthesis step.
According to the OHV (mgKOH/g) values of examples 1 to 7, as compared with example 1, it was found that the rise in viscosity was not related to the molecular weight, and the acid value was a key factor affecting the viscosity of the product.
As is clear from comparative example 1, the absence of the heating at 140℃in step c) in the synthesis step does not allow the nano-aluminate gum to fuse with the polyester, resulting in an external turbidity of the resin and coarse particles.
The films obtained in comparative examples 2 to 3 were not sufficiently hard although they were excellent in impact resistance. It is shown that testing other different types of nano-alumina (e.g., DENKA, ASFP20 or AS 520) does not have the effect of the present application at the same addition ratio. Examples 1 to 7 of the present application can provide functional films having a hardness of 4H and having both flexibility and impact resistance.
Comparative example 4 shows that: when the addition amount of the modifier AD124 is too large, the crosslinking becomes excessive, which causes an increase in the viscosity of the resin.
Comparative example 5 shows that: when the addition amount of the modified aluminate glue is too large, the crosslinking is excessive, so that the viscosity of the resin is increased to gel, and the subsequent measurement cannot be performed.
The above description of the embodiments is only for aiding in the understanding of the method of the present application and its core ideas. It should be noted that it will be apparent to those skilled in the art that various modifications and adaptations of the application can be made without departing from the principles of the application and these modifications and adaptations are intended to be within the scope of the application as defined in the following claims.
Claims (9)
1. An aluminate-modified polyester, comprising: a sheet-like aluminate gum unit and an acid-based polyester unit;
wherein the flaky aluminate gum unit and the acid-based polyester unit are connected through an ester bond;
the flaky aluminate glue unit is prepared from aluminate collagen liquid and silicon-based monomers through a surface modification reaction; the aluminate collagen liquid is selected from flaky aluminate glue, the silicon-based monomer is silane compound with reactive end groups, and the aluminate collagen liquid is flaky alumina;
the mass ratio of the silicon-based monomer to the acid-based monomer is (0.5-3) 100, wherein the mass ratio of the silicon-based monomer is less than or equal to 5% of the total weight of the collagen aluminate solution.
2. The preparation method of the aluminate glue modified polyester is characterized by comprising the following steps:
preparation of an aluminate glue prepolymerization liquid: carrying out surface modification reaction on the aluminate collagen liquid and a silicon-based monomer;
preparation of acid-based polyester prepolymer: reacting an acid-based monomer with a hydroxyl monomer;
preparation of modified polyester: the aluminate glue prepolymerization liquid and the acid-based polyester prepolymerization liquid are subjected to esterification reaction and condensation reaction under the condition of a catalyst;
the aluminate glue prepolymerization liquid aluminate glue is flaky alumina prepolymerization liquid, the aluminate collagen liquid is flaky alumina, and the silicon-based monomer is silane compound with a reactive end group;
the mass ratio of the silicon-based monomer to the acid-based monomer is (0.5-3) 100, wherein the mass ratio of the silicon-based monomer is less than or equal to 5% of the total weight of the collagen aluminate solution.
3. The method of claim 2, wherein the collagen aluminate solution comprises 0.5 to 1.5% by weight of the total modified polyester.
4. The production method according to claim 2, wherein the modified polyester has an acid value of 53 to 70mgKOH/g.
5. The method according to claim 2, wherein,
the silane compound having a reactive end group is selected from one or more of epoxy group, amine group and hydroxyl group.
6. The preparation method according to claim 2, wherein the acid-based monomer is one or more selected from the group consisting of a polybasic organic acid having 4 to 36 carbon atoms, an ester, and an acid anhydride;
the hydroxyl monomer is selected from polyols with 2-14 carbon atoms.
7. The method of preparing according to claim 2, wherein the catalyst comprises: an organotin;
the organic tin has the structural general formula: r is R n SnX m ;
Wherein n=1 to 4, m=0 to 3, x is halogen, and R is alkyl or aryl.
8. A coating composition comprising the modified polyester of claim 1, or the modified polyester prepared by the method of any one of claims 2-7.
9. A resin film comprising the modified polyester of claim 1, or the modified polyester prepared by the method of any one of claims 2 to 7.
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CN110407238A (en) * | 2019-08-23 | 2019-11-05 | 济南大学 | A kind of method that crystal seed method prepares flaky alpha-alumina crystals |
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