CN108822713B - Preparation method of light-resistant waterborne polyurethane coating and adhesive - Google Patents
Preparation method of light-resistant waterborne polyurethane coating and adhesive Download PDFInfo
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- CN108822713B CN108822713B CN201810774013.2A CN201810774013A CN108822713B CN 108822713 B CN108822713 B CN 108822713B CN 201810774013 A CN201810774013 A CN 201810774013A CN 108822713 B CN108822713 B CN 108822713B
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- China
- Prior art keywords
- light
- reacting
- resistant
- polyurethane coating
- catalyst
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- 239000011527 polyurethane coating Substances 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 239000000853 adhesive Substances 0.000 title abstract description 19
- 230000001070 adhesive effect Effects 0.000 title abstract description 19
- 239000000463 material Substances 0.000 claims abstract description 39
- 239000003054 catalyst Substances 0.000 claims abstract description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000003756 stirring Methods 0.000 claims abstract description 23
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims abstract description 19
- 239000004417 polycarbonate Substances 0.000 claims abstract description 17
- 238000001816 cooling Methods 0.000 claims abstract description 16
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 16
- 150000002009 diols Chemical class 0.000 claims abstract description 15
- 239000012948 isocyanate Substances 0.000 claims abstract description 13
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 13
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims abstract description 12
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims abstract description 12
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims abstract description 12
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims abstract description 12
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 230000001804 emulsifying effect Effects 0.000 claims abstract description 9
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 claims abstract description 8
- DZGWFCGJZKJUFP-UHFFFAOYSA-N Tyramine Natural products NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 229960003732 tyramine Drugs 0.000 claims abstract description 8
- DZGWFCGJZKJUFP-UHFFFAOYSA-O tyraminium Chemical compound [NH3+]CCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-O 0.000 claims abstract description 8
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 23
- JUUBCHWRXWPFFH-UHFFFAOYSA-N Hydroxytyrosol Chemical compound OCCC1=CC=C(O)C(O)=C1 JUUBCHWRXWPFFH-UHFFFAOYSA-N 0.000 claims description 16
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 14
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 13
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 claims description 12
- 229940095066 hydroxytyrosol Drugs 0.000 claims description 8
- 235000003248 hydroxytyrosol Nutrition 0.000 claims description 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 8
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 7
- 229920005610 lignin Polymers 0.000 claims description 7
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 238000001694 spray drying Methods 0.000 claims description 7
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 claims description 7
- GBBSAMQTQCPOBF-UHFFFAOYSA-N 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane Chemical compound CB1OB(C)OB(C)O1 GBBSAMQTQCPOBF-UHFFFAOYSA-N 0.000 claims description 6
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 239000011591 potassium Substances 0.000 claims description 6
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 5
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 claims description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 3
- HJDQVQXEAZRSQI-UHFFFAOYSA-N hexanedioic acid;sodium Chemical compound [Na].[Na].OC(=O)CCCCC(O)=O HJDQVQXEAZRSQI-UHFFFAOYSA-N 0.000 claims description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229920002635 polyurethane Polymers 0.000 description 10
- 239000004814 polyurethane Substances 0.000 description 10
- 238000002310 reflectometry Methods 0.000 description 6
- 239000004970 Chain extender Substances 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 238000011056 performance test Methods 0.000 description 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- KYKFCSHPTAVNJD-UHFFFAOYSA-L sodium adipate Chemical compound [Na+].[Na+].[O-]C(=O)CCCCC([O-])=O KYKFCSHPTAVNJD-UHFFFAOYSA-L 0.000 description 3
- 235000011049 sodium adipate Nutrition 0.000 description 3
- UVMAXIWRKVCCRS-UHFFFAOYSA-N sodium;cyclohexylazanide Chemical compound [Na+].[NH-]C1CCCCC1 UVMAXIWRKVCCRS-UHFFFAOYSA-N 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- SIAVMDKGVRXFAX-UHFFFAOYSA-N 4-carboxyphenylboronic acid Chemical compound OB(O)C1=CC=C(C(O)=O)C=C1 SIAVMDKGVRXFAX-UHFFFAOYSA-N 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229940090960 diethylenetriamine pentamethylene phosphonic acid Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- DUYCTCQXNHFCSJ-UHFFFAOYSA-N dtpmp Chemical compound OP(=O)(O)CN(CP(O)(O)=O)CCN(CP(O)(=O)O)CCN(CP(O)(O)=O)CP(O)(O)=O DUYCTCQXNHFCSJ-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FLFJVPPJGJSHMF-UHFFFAOYSA-L manganese hypophosphite Chemical class [Mn+2].[O-]P=O.[O-]P=O FLFJVPPJGJSHMF-UHFFFAOYSA-L 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920006264 polyurethane film Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/166—Catalysts not provided for in the groups C08G18/18 - C08G18/26
- C08G18/168—Organic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3842—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- C08G18/3844—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing one nitrogen atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6484—Polysaccharides and derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic 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
- C09D5/004—Reflecting paints; Signal paints
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Biochemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention relates to a preparation method of a light-resistant waterborne polyurethane coating and an adhesive, which comprises the steps of adding 0.07-0.13 g of a catalyst, 35-43 g of polycarbonate diol and 12g of isocyanate into a 250ml three-necked bottle with a stirrer, a condenser and a thermometer, reacting at 70-90 ℃ for 1-2 h, adding 1.1-1.3 g of hydroxypropyl methyl cellulose, reacting at 80 ℃ for 1h, adding 1.4-1.6 g of quinolinic acid, cooling to 50-60 ℃ and reacting for 2h to obtain a polyurethane prepolymer A; adding 0.6-0.8 g of light-resistant material, 1.2g of p-chlorobenzoyl chloride and 13.4g of solvent DMF13 into the polyurethane prepolymer A, reacting at 60-90 ℃ for 2-4 h, adding 4g of tyramine, reacting at 80 ℃ for 1h, adding 7.5g of triethylamine for neutralization reaction for 80min, adding 100-120 g of water, stirring and emulsifying for 30-90 min to obtain the light-resistant waterborne polyurethane coating and adhesive, wherein the obtained material has good light resistance.
Description
Technical Field
The invention relates to a preparation method of a waterborne polyurethane coating and an adhesive, in particular to a preparation method of a light-resistant waterborne polyurethane coating and an adhesive.
Background
The coating is traditionally named as paint in China. The coating is a continuous film which is coated on the surface of an object to be protected or decorated and can form firm adhesion with the object to be coated, and is a viscous liquid which is prepared by taking resin, oil or emulsion as a main material, adding or not adding pigments and fillers, adding corresponding auxiliaries and using an organic solvent or water.
The new China is established for 60 years, and along with the development of various industries of national economy, the paint industry matched with the new China is gradually developed from a small industry which is not attractive, into an essential important industry in various fields of national economy. Through the obstinate fighting and development of several generations of people, China becomes the second largest world paint producing country and consuming country and enters the mainstream of the world paint industry development.
201711477655.8 discloses a high-reflection, high-flame-retardant, high-toughness polycarbonate material and a preparation method thereof, which comprises the following raw materials by mass percent: 65-85% of PC resin, 4-12% of flame retardant, 1-5% of toughening agent, 6-20% of titanium dioxide, 0.2-2.0% of anti-ultraviolet agent, 0.1-0.5% of anti-dripping agent and 0.1-0.5% of release agent; the product is obtained by drying, mixing, blending and granulating the raw materials, and finally extruding, cooling with water, granulating and sieving. The product of the invention not only has high reflection and high flame retardant performance, but also has high toughness.
201711369135.5 discloses a flame-retardant, light-resistant and low-VOC polyurethane coating and a preparation method thereof, 0.22g of triethylene tetramine, 70g of polytetrahydrofuran ether glycol and 15g of hexamethylene diisocyanate are added into a 250ml three-necked bottle with a stirrer, a condenser and a thermometer, and the mixture is reacted for 2 hours at 80 ℃ to obtain a polyurethane prepolymer A; adding 0.62g of acetamide and 8.2g of methyl ethyl ketone into the prepolymer A, reacting for 3.5h at 75 ℃, adding 2g of modified manganese hypophosphite prepared in the step (1), 4g of 4-carboxyphenylboronic acid and 2.5g of diethylenetriamine pentamethylenephosphonic acid, reacting for 2h at 80 ℃, adding 7.1g of triethylamine for neutralization reaction for 60min, adding 0.9g of vitamin C and 70g of water, stirring and emulsifying to obtain the polyurethane coating with flame retardance, light fastness and low VOC.
Disclosure of Invention
The invention relates to a preparation method of a light-resistant waterborne polyurethane coating and an adhesive, wherein the route of the design synthesis scheme is that a light-resistant material is self-made, the light-resistant material is used as a chain extender for polyurethane synthesis, the function of the chain extender is utilized to bring the light-resistant function into polyurethane, the light-resistant material has the function of mirror reflection, a light source can be subjected to full emission, the possibility of light absorption of the polyurethane is reduced, and the light resistance of the polyurethane is improved.
The preparation method of the light-resistant waterborne polyurethane coating and the adhesive comprises the following steps:
(1) adding 0.07-0.13 g of catalyst, 35-43 g of polycarbonate diol and 12g of isocyanate into a 250ml three-necked bottle with a stirrer, a condenser and a thermometer, reacting at 70-90 ℃ for 1-2 h, adding 1.1-1.3 g of hydroxypropyl methyl cellulose, reacting at 80 ℃ for 1h, adding 1.4-1.6 g of quinolinic acid, cooling to 50-60 ℃ and reacting for 2h to obtain a polyurethane prepolymer A;
(2) adding 0.6-0.8 g of light-resistant material, 1.2g of p-chlorobenzoyl chloride and 13.4g of solvent DMF13 into the polyurethane prepolymer A, reacting at 60-90 ℃ for 2-4 h, adding 4g of tyramine, reacting at 80 ℃ for 1h, adding 7.5g of triethylamine for neutralization reaction for 80min, adding 100-120 g of water, stirring and emulsifying for 30-90 min to obtain the light-resistant waterborne polyurethane coating and adhesive.
The catalyst is any one of tetramethyl ethylene diamine, hexamethyl phosphoric triamide, trimethyl cyclotriboroxane and diethyl malonate;
the isocyanate is any one of hexamethylene diisocyanate, isophorone diisocyanate and 4,4' -dicyclohexylmethane diisocyanate;
the polycarbonate diol has a molecular weight of 1000 and 2000; the preparation method of the light-resistant material comprises the steps of adding 10g of sodium lignin (Jinanqiyunshan chemical Co., Ltd.), 3g of octamethylcyclotetrasiloxane, a substance A12g and a catalyst A3.3g into a three-neck flask, stirring and reacting for 1-2 h at 70-90 ℃, adding 1.2g of glycolic acid, 2-3g of tetrabutylammonium fluoride and 1-3g of ethylene glycol into the system, stirring and reacting for 1-2 h at 60-90 ℃, adding 3-9g of sodium cyclohexylsulfamate at 60-70 ℃, preserving heat and reacting for 1-3h, cooling and spray drying to obtain the light-resistant material;
the substance A is any one of pentaerythritol, hydroxytyrosol and trimethylolpropane;
the catalyst A is any one of trimethylsilyl acetylene, lithium fluoride, potassium borohydride and adipic acid disodium.
The invention has the advantages that:
(1) the light-resistant material is used as a chain extender for polyurethane synthesis, the function of the chain extender is utilized to bring the light-resistant function into polyurethane, the light-resistant material has the function of mirror reflection, a light source can be subjected to full emission, the possibility of light absorption of the polyurethane is reduced, and the light resistance of the polyurethane is improved;
(2) the tetramethylethylenediamine, hexamethylphosphoric triamide, trimethylcyclotriboroxane and diethyl malonate are used as catalysts of polyurethane prepolymer, so that the polyurethane prepolymer has the advantages of no toxicity and high efficiency, and the hydroxypropyl methyl cellulose and the quinolinic acid have the advantages of improving the toughness of polyurethane;
(3) trimethylsilyl acetylene, lithium fluoride, potassium borohydride and disodium adipate are used as light-resistant material catalysts, and pentaerythritol, hydroxytyrosol and trimethylolpropane have the effect of improving the reflectivity.
Detailed Description
Example 1
The preparation method of the light-resistant waterborne polyurethane coating and the adhesive comprises the following steps:
(1) adding 0.07g of tetramethylethylenediamine, 35g of polycarbonate diol and 12g of hexamethylene diisocyanate into a 250ml three-necked flask with a stirrer, a condenser and a thermometer, reacting at 70 ℃ for 1h, adding 1.1g of hydroxypropyl methyl cellulose, reacting at 80 ℃ for 1h, adding 1.4g of quinolinic acid, cooling to 50 ℃, and carrying out heat preservation reaction for 2h to obtain a polyurethane prepolymer A;
(2) adding 0.6g of light-resistant material, 1.2g of p-chlorobenzoyl chloride and 13.4g of solvent DMF13 into the polyurethane prepolymer A, reacting for 2h at 60 ℃, adding 4g of tyramine, reacting at 80 ℃ for 1h, adding 7.5g of triethylamine, neutralizing for 80min, adding 100g of water, stirring and emulsifying for 30min to obtain the light-resistant waterborne polyurethane coating and adhesive.
The polycarbonate diol has a molecular weight of 1000;
the preparation method of the light-resistant material comprises the steps of adding 10g of sodium lignin (Jinanqiyunshan chemical Co., Ltd.), 3g of octamethylcyclotetrasiloxane, 12g of pentaerythritol and 3.3g of trimethylsilylacetylene into a three-neck flask, stirring and reacting for 1h at 70 ℃, adding 1.2g of glycolic acid, 2g of tetrabutylammonium fluoride and 1g of ethylene glycol into the system, stirring and reacting for 1h at 60 ℃, adding 3g of sodium cyclohexylsulfamate at 60 ℃, keeping the temperature and reacting for 1h, cooling and spray drying to obtain the light-resistant material.
Example 2
The preparation method of the light-resistant waterborne polyurethane coating and the adhesive comprises the following steps:
(1) adding 0.13g of catalyst, 43g of polycarbonate diol and 12g of isocyanate into a 250ml three-necked flask with a stirrer, a condenser and a thermometer, reacting at 90 ℃ for 2h, then adding 1.3g of hydroxypropyl methyl cellulose, reacting at 80 ℃ for 1h, then adding 1.6g of quinolinic acid, cooling to 60 ℃ and reacting for 2h to obtain a polyurethane prepolymer A;
(2) adding 0.8g of light-resistant material, 1.2g of p-chlorobenzoyl chloride and 13.4g of solvent DMF13 into the polyurethane prepolymer A, reacting for 4h at 90 ℃, adding 4g of tyramine, reacting at 80 ℃ for 1h, adding 7.5g of triethylamine for neutralization reaction for 80min, adding 120g of water, stirring and emulsifying for 90min to obtain the light-resistant waterborne polyurethane coating and adhesive.
The catalyst is hexamethylphosphoric triamide;
the isocyanate is isophorone diisocyanate;
the polycarbonate diol has a molecular weight of 2000;
the preparation method of the light-resistant material comprises the steps of adding 10g of sodium lignin (Jinanqiyunshan chemical Co., Ltd.), 3g of octamethylcyclotetrasiloxane, a substance A12g and a catalyst A3.3g into a three-neck flask, stirring and reacting for 2h at 90 ℃, adding 1.2g of glycolic acid, 3g of tetrabutylammonium fluoride and 3g of ethylene glycol into the system, stirring and reacting for 2h at 90 ℃, adding 9g of cyclohexylamino sodium sulfonate at 70 ℃, keeping the temperature and reacting for 3h, cooling and spray-drying to obtain the light-resistant material;
the substance A is hydroxytyrosol;
the catalyst A is lithium fluoride.
Example 3
The preparation method of the light-resistant waterborne polyurethane coating and the adhesive comprises the following steps:
(1) adding 0.10g of catalyst, 39g of polycarbonate diol and 12g of isocyanate into a 250ml three-necked bottle with a stirrer, a condenser and a thermometer, reacting at 80 ℃ for 1.5h, then adding 1.2g of hydroxypropyl methyl cellulose, reacting at 80 ℃ for 1h, then adding 1.5g of quinolinic acid, cooling to 55 ℃ and reacting for 2h to obtain a polyurethane prepolymer A;
(2) adding 0.7g of light-resistant material, 1.2g of p-chlorobenzoyl chloride and 13.4g of solvent DMF13 into the polyurethane prepolymer A, reacting for 3h at 75 ℃, adding 4g of tyramine, reacting at 80 ℃ for 1h, adding 7.5g of triethylamine for neutralization reaction for 80min, adding 110g of water, stirring and emulsifying for 60min to obtain the light-resistant waterborne polyurethane coating and adhesive.
The catalyst is trimethyl cyclotriboroxane;
the isocyanate is 4,4' -dicyclohexylmethane diisocyanate;
the polycarbonate diol has a molecular weight of 2000;
the preparation method of the light-resistant material comprises the steps of adding 10g of sodium lignin (Jinanqiyunshan chemical Co., Ltd.), 3g of octamethylcyclotetrasiloxane, a substance A12g and a catalyst A3.3g into a three-neck flask, stirring and reacting for 1.5h at the temperature of 80 ℃, adding 1.2g of glycolic acid, 2.5g of tetrabutylammonium fluoride and 2g of ethylene glycol into the system, stirring and reacting for 1.5h at the temperature of 75 ℃, adding 6g of cyclohexylamino sodium sulfonate at the temperature of 65 ℃, preserving heat and reacting for 2h, cooling and spray drying to obtain the light-resistant material;
substance A is trimethylolpropane;
the catalyst A is potassium borohydride.
Example 4
The preparation method of the light-resistant waterborne polyurethane coating and the adhesive comprises the following steps:
(1) adding 0.10g of catalyst, 39g of polycarbonate diol and 12g of isocyanate into a 250ml three-necked bottle with a stirrer, a condenser and a thermometer, reacting at 70 ℃ for 1h, then adding 1.1g of hydroxypropyl methyl cellulose, reacting at 80 ℃ for 1h, then adding 1.4g of quinolinic acid, cooling to 50 ℃ and reacting for 2h to obtain a polyurethane prepolymer A;
(2) adding 0.8g of light-resistant material, 1.2g of p-chlorobenzoyl chloride and 13.4g of solvent DMF13 into the polyurethane prepolymer A, reacting for 4h at 90 ℃, adding 4g of tyramine, reacting at 80 ℃ for 1h, adding 7.5g of triethylamine for neutralization reaction for 80min, adding 120g of water, stirring and emulsifying for 90min to obtain the light-resistant waterborne polyurethane coating and adhesive.
The catalyst is diethyl malonate;
the isocyanate is 4,4' -dicyclohexylmethane diisocyanate;
the polycarbonate diol has a molecular weight of 1000;
the preparation method of the light-resistant material comprises the steps of adding 10g of sodium lignin (Jinanqiyunshan chemical Co., Ltd.), 3g of octamethylcyclotetrasiloxane, a substance A12g and a catalyst A3.3g into a three-neck flask, stirring and reacting for 2h at 90 ℃, adding 1.2g of glycolic acid, 2g of tetrabutylammonium fluoride and 1g of ethylene glycol into the system, stirring and reacting for 1h at 60 ℃, adding 3g of sodium cyclohexylsulfamate at 60 ℃, keeping the temperature and reacting for 2h, cooling and spray drying to obtain the light-resistant material;
the substance A is pentaerythritol;
its catalyst A is adipic acid disodium.
Example 5
The preparation method of the light-resistant waterborne polyurethane coating and the adhesive comprises the following steps:
(1) adding 0.07g of catalyst, 35g of polycarbonate diol and 12g of isocyanate into a 250ml three-necked flask with a stirrer, a condenser and a thermometer, reacting at 80 ℃ for 1.5h, then adding 1.2g of hydroxypropyl methylcellulose, reacting at 80 ℃ for 1h, then adding 1.5g of quinolinic acid, cooling to 50 ℃ and reacting for 2h to obtain a polyurethane prepolymer A;
(2) adding 0.6g of light-resistant material, 1.2g of p-chlorobenzoyl chloride and 13.4g of solvent DMF13 into the polyurethane prepolymer A, reacting for 2h at 60 ℃, adding 4g of tyramine, reacting at 80 ℃ for 1h, adding 7.5g of triethylamine, neutralizing for 80min, adding 100g of water, stirring and emulsifying for 60min to obtain the light-resistant waterborne polyurethane coating and adhesive.
The catalyst is diethyl malonate;
the isocyanate is hexamethylene diisocyanate;
the polycarbonate diol has a molecular weight of 1000;
the preparation method of the light-resistant material comprises the steps of adding 10g of sodium lignin (Jinanqiyunshan chemical Co., Ltd.), 3g of octamethylcyclotetrasiloxane, a substance A12g and a catalyst A3.3g into a three-neck flask, stirring and reacting for 1.5h at 80 ℃, adding 1.2g of glycolic acid, 2g of tetrabutylammonium fluoride and 1g of ethylene glycol into the system, stirring and reacting for 1h at 60 ℃, adding 6g of cyclohexylamino sodium sulfonate at 65 ℃, keeping the temperature and reacting for 2h, cooling and spray drying to obtain the light-resistant material;
the substance A is hydroxytyrosol;
the catalyst A is trimethylsilyl acetylene.
Light resistance is measured by measuring its color change under an ultraviolet lamp under simulated sunlight for 48 hours, using a Gretag Macbeth Coloreye spectrophotometer (D65 light source, 10 degree observer, including UV) and measuring the reflectance level of the resin at 10 nanometer (nm) intervals from 360 to 750nm, for example, for 3.2mm thick plaques. The measurements were performed at 10nm wavelength intervals from 360 to 750 nm. The reflectance value at 680nm was used to define the maximum percent reflectance for each material formulation.
TABLE 1 test Properties
| Example 1 | Example 2 | Example 3 | Example 4 | Example 5 | |
| Light resistance/grade | 4.0 | 4.0 | 4.5 | 4.5 | 4.0 |
| Reflectivity/%) | 98.3 | 98.1 | 98.4 | 98.6 | 98.2 |
| Elongation at break/% | 153 | 212 | 187 | 165 | 168 |
Maximum reflectance of sample 201711477655.8 of 97.8, lightfast level 4.0; 201711369135.5, the maximum reflectance was 87.6, and the light fastness rating was 3.0. it can be seen from Table 1 that the light fastness rating and reflectance of the present invention are relatively high.
TABLE 2 Performance test (tetramethylethylenediamine, hexamethylphosphoric triamide, trimethylcyclotriboroxane, diethyl malonate without catalyst)
| Example 1 | Example 2 | Example 3 | Example 4 | Example 5 | |
| Light resistance/grade | 2.0 | 2.0 | 1.5 | 2.5 | 2.0 |
| Reflectivity/%) | 29.3 | 27.2 | 31.3 | 33.7 | 35.2 |
| Elongation at break/% | 21 | 12 | 15 | 17 | 10 |
As can be seen from Table 2, tetramethylethylenediamine, hexamethylphosphoric triamide, trimethylcyclotriboroxane, and diethyl malonate exhibited catalytic effects, and the performance was greatly reduced compared to the performance exhibited when the catalyst was added, but the catalyst was not added.
TABLE 3 Performance test (without hydroxypropyl methylcellulose or quinolinic acid)
| Example 1 | Example 2 | Example 3 | Example 4 | Example 5 | |
| Elongation at break/% (without addition of hydroxypropyl methylcellulose) | 87 | 108 | 164 | 132 | 121 |
| Elongation at break/% (without addition of quinolinic acid) | 103 | 121 | 148 | 128 | 143 |
Table 3 toughness of polyurethane without hydroxypropyl methylcellulose or quinolinic acid added decreases.
TABLE 4 Performance test (without trimethylsilyl acetylene, lithium fluoride, potassium borohydride and disodium adipate)
| Example 1 | Example 2 | Example 3 | Example 4 | Example 5 | |
| Light resistance/grade | 2.0 | 2.5 | 2.0 | 1.0 | 1.5 |
| Reflectivity/%) | 27.3 | 26.1 | 27.4 | 26.7 | 28.3 |
As can be seen from Table 4, the light resistance and reflectance were reduced without adding the light-resistant material.
TABLE 5 Performance test (without trimethylsilyl acetylene, lithium fluoride, potassium borohydride and disodium adipate, with lightfast material)
| Example 1 | Example 2 | Example 3 | Example 4 | Example 5 | |
| Light resistance/grade | 3.0 | 2.5 | 2.5 | 2.5 | 2.0 |
| Reflectivity/%) | 48.2 | 49.4 | 48.5 | 48.7 | 58.3 |
TABLE 6 test of properties (without pentaerythritol, hydroxytyrosol, trimethylolpropane, with lightfast material)
| Example 1 | Example 2 | Example 3 | Example 4 | Example 5 | |
| Light resistance/grade | 3.0 | 3.0 | 3.5 | 3.5 | 3.0 |
| Reflectivity/%) | 46.3 | 51.1 | 56.4 | 57.6 | 59.2 |
Pentaerythritol, hydroxytyrosol, and trimethylolpropane have an effect of improving the reflectance, and as can be seen from tables 5 and 6, the light resistance of the polyurethane film obtained without adding the substance a or pentaerythritol, hydroxytyrosol, and trimethylolpropane and adding the light-resistant material is lowered.
Claims (4)
1. The preparation method of the light-resistant waterborne polyurethane coating comprises the following steps:
(1) adding 0.07-0.13 g of catalyst, 35-43 g of polycarbonate diol and 12g of isocyanate into a 250ml three-necked bottle with a stirrer, a condenser and a thermometer, reacting at 70-90 ℃ for 1-2 h, adding 1.1-1.3 g of hydroxypropyl methyl cellulose, reacting at 80 ℃ for 1h, adding 1.4-1.6 g of quinolinic acid, cooling to 50-60 ℃ and reacting for 2h to obtain a polyurethane prepolymer A;
(2) adding 0.6-0.8 g of light-resistant material, 1.2g of p-chlorobenzoyl chloride and 13.4g of solvent DMF13 into the polyurethane prepolymer A, reacting at 60-90 ℃ for 2-4 h, adding 4g of tyramine, reacting at 80 ℃ for 1h, adding 7.5g of triethylamine for neutralization reaction for 80min, adding 100-120 g of water, stirring and emulsifying for 30-90 min to obtain the light-resistant waterborne polyurethane coating; the preparation method of the light-resistant material comprises the following steps: adding 10g of sodium lignin, 3g of octamethylcyclotetrasiloxane, a substance A12g and a catalyst A3.3g into a three-necked flask, stirring and reacting for 1-2 h at 70-90 ℃, adding 1.2g of glycolic acid, 2-3g of tetrabutylammonium fluoride and 1-3g of ethylene glycol into the system, stirring and reacting for 1-2 h at 60-90 ℃, adding 3-9g of sodium cyclohexylsulfamate at 60-70 ℃, keeping the temperature and reacting for 1-3h, cooling and spray drying to obtain a light-resistant material; the substance A is any one of pentaerythritol, hydroxytyrosol and trimethylolpropane; the catalyst A is any one of trimethylsilyl acetylene, lithium fluoride, potassium borohydride and adipic acid disodium.
2. The process for producing a light-resistant aqueous polyurethane coating material according to claim 1, wherein the catalyst is any one of tetramethylethylenediamine, hexamethylphosphoric triamide, trimethylcyclotriboroxane and diethyl malonate.
3. The process for producing a light-resistant aqueous polyurethane coating material according to claim 1, wherein the isocyanate is any one of hexamethylene diisocyanate, isophorone diisocyanate and 4,4' -dicyclohexylmethane diisocyanate.
4. The method for producing a light-resistant aqueous polyurethane coating material according to claim 1, wherein the polycarbonate diol has a molecular weight of 1000 or 2000.
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