CN106753173B - Preparation method of modified water-based polyurethane pressure-sensitive adhesive - Google Patents
Preparation method of modified water-based polyurethane pressure-sensitive adhesive Download PDFInfo
- Publication number
- CN106753173B CN106753173B CN201611160998.7A CN201611160998A CN106753173B CN 106753173 B CN106753173 B CN 106753173B CN 201611160998 A CN201611160998 A CN 201611160998A CN 106753173 B CN106753173 B CN 106753173B
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- Prior art keywords
- parts
- sensitive adhesive
- reaction
- pressure
- modified
- Prior art date
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- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims abstract description 59
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 32
- 239000004814 polyurethane Substances 0.000 title claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 27
- -1 polysiloxane Polymers 0.000 claims abstract description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 229920002545 silicone oil Polymers 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 45
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 28
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 230000035484 reaction time Effects 0.000 claims description 16
- 238000002156 mixing Methods 0.000 claims description 15
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 14
- 229920000570 polyether Polymers 0.000 claims description 14
- CCJAYIGMMRQRAO-UHFFFAOYSA-N 2-[4-[(2-hydroxyphenyl)methylideneamino]butyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCCCN=CC1=CC=CC=C1O CCJAYIGMMRQRAO-UHFFFAOYSA-N 0.000 claims description 13
- 239000003963 antioxidant agent Substances 0.000 claims description 13
- 230000003078 antioxidant effect Effects 0.000 claims description 13
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 8
- 230000003712 anti-aging effect Effects 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 8
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical group CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 7
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 7
- 239000012188 paraffin wax Substances 0.000 claims description 7
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 7
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- MTLWTRLYHAQCAM-UHFFFAOYSA-N 2-[(1-cyano-2-methylpropyl)diazenyl]-3-methylbutanenitrile Chemical compound CC(C)C(C#N)N=NC(C#N)C(C)C MTLWTRLYHAQCAM-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 238000004945 emulsification Methods 0.000 claims description 6
- 230000001804 emulsifying effect Effects 0.000 claims description 6
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 5
- 239000004970 Chain extender Substances 0.000 claims description 4
- 239000003995 emulsifying agent Substances 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 4
- 150000007529 inorganic bases Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 3
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 claims description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 2
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical group CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 claims description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 claims description 2
- ZBTGXRBMYGTQHK-UHFFFAOYSA-N azanium;2-nonylphenolate Chemical group N.CCCCCCCCCC1=CC=CC=C1O ZBTGXRBMYGTQHK-UHFFFAOYSA-N 0.000 claims description 2
- XOZUGNYVDXMRKW-AATRIKPKSA-N azodicarbonamide Chemical compound NC(=O)\N=N\C(N)=O XOZUGNYVDXMRKW-AATRIKPKSA-N 0.000 claims description 2
- 235000019399 azodicarbonamide Nutrition 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000007865 diluting Methods 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
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- 238000010517 secondary reaction Methods 0.000 claims description 2
- 239000012974 tin catalyst Substances 0.000 claims description 2
- 229960001124 trientine Drugs 0.000 claims description 2
- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 claims description 2
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 claims description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 13
- 238000004132 cross linking Methods 0.000 abstract description 2
- 239000003607 modifier Substances 0.000 abstract description 2
- 108090000623 proteins and genes Proteins 0.000 abstract description 2
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 description 15
- 239000000853 adhesive Substances 0.000 description 14
- 239000003292 glue Substances 0.000 description 14
- 238000002834 transmittance Methods 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 10
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 5
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 5
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 5
- 235000011130 ammonium sulphate Nutrition 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical group CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 5
- 239000005060 rubber Substances 0.000 description 5
- 239000012943 hotmelt Substances 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000003878 thermal aging Methods 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- UFQDKRWQSFLPQY-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-3-ium;chloride Chemical compound Cl.C1CN=CN1 UFQDKRWQSFLPQY-UHFFFAOYSA-N 0.000 description 1
- 239000004156 Azodicarbonamide Substances 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- YDVJBLJCSLVMSY-UHFFFAOYSA-N carbamoyl cyanide Chemical compound NC(=O)C#N YDVJBLJCSLVMSY-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 239000000080 wetting agent 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
- 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
- C09J175/08—Polyurethanes from polyethers
-
- 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
- C08G18/28—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
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy groups
-
- 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
- C08G18/48—Polyethers
- C08G18/4829—Polyethers containing at least three hydroxy groups
-
- 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
- C08G18/61—Polysiloxanes
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
-
- 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
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
-
- 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
-
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention relates to a preparation method of a modified water-based polyurethane pressure-sensitive adhesive, belonging to the technical field of pressure-sensitive adhesives. The method comprises the following steps: preparing a modified polysiloxane prepolymer, adding the polysiloxane prepolymer into the preparation of the water-based polyurethane pressure-sensitive adhesive for modification, and further preparing the water-based pressure-sensitive adhesive. The polysiloxane prepolymer is a modifier, can improve the gene crosslinking property of the surface of the waterborne polyurethane, improves the adhesion of the polyurethane, and simultaneously, because the surface hydrophilicity of the polysiloxane prepolymer is poor, the problem of poor fog surface effect of the pressure-sensitive adhesive caused by poor dispersibility after the polysiloxane prepolymer is modified by adding the hydroxyl silicone oil is solved. The pressure-sensitive adhesive has the advantages of high bonding strength and good matte effect.
Description
Technical Field
The invention relates to a preparation method of a modified water-based polyurethane pressure-sensitive adhesive, belonging to the technical field of pressure-sensitive adhesives.
Background
Pressure sensitive adhesives are a class of adhesives that are sensitive to pressure. The preparation method is mainly used for preparing the pressure-sensitive adhesive tape. In general, the peeling force of a pressure-sensitive adhesive (peeling force exhibited after pressure-bonding an adhesive tape to an adherend surface) < cohesive force of the adhesive (force between pressure-sensitive adhesive molecules) < cohesive force of the adhesive (adhesion force between the adhesive and a base material). The pressure-sensitive adhesive can not be degummed and the like in the using process. The pressure-sensitive adhesive is mainly a solvent-type or latex-type adhesive of acrylic and rubber series. Because of the requirements of high-speed operation, reasonable coating and elimination of solvent public hazard problems, the warm-melt pressure-sensitive adhesive, heat-collecting melt adhesive and pressure-sensitive adhesive are developed, and the hot-melt pressure-sensitive adhesive has the characteristics of no solvent, no pollution and more convenient use. It is applied in molten state, cooled and solidified, and then lightly pressed by fingers to obtain the adhesive effect.
The resin composition can be classified into rubber type and resin type according to the main resin component. The rubber type can be divided into natural rubber and synthetic rubber; the resin type also includes mainly acrylic type, silicone type and polyurethane type. The rubber pressure-sensitive adhesive is prepared by adding other auxiliary components such as tackifying resin, plasticizer, filler, viscosity regulator, vulcanizing agent, anti-aging agent, solvent and the like in addition to the main component of rubber. Besides the main resin, the resin pressure-sensitive adhesive also needs to be added with auxiliary agents such as a defoaming agent, a leveling agent, a wetting agent and the like. According to the characters and dispersion media, the pressure-sensitive adhesive can be divided into water-soluble pressure-sensitive adhesive, solvent-type pressure-sensitive adhesive, emulsion-type pressure-sensitive adhesive, hot-melt pressure-sensitive adhesive and calendering pressure-sensitive adhesive, wherein the water-soluble pressure-sensitive adhesive, the hot-melt pressure-sensitive adhesive and the solvent-type pressure-sensitive adhesive are mainstream pressure-sensitive adhesive products in the market, and the hot-melt pressure-sensitive adhesive is a newly developed pressure-sensitive adhesive variety.
The Waterborne Polyurethane (WPU) adhesive has a structure containing urethane groups (-NHCOO-) which have strong polarity and can form hydrogen bonds with each other, so that the cohesive force of the Waterborne Polyurethane (WPU) adhesive is large, and the adhesive force of the Waterborne Polyurethane (WPU) adhesive with polar substances is strong; in addition, the adhesive has the characteristics of no toxicity, no environmental pollution and the like, so the adhesive gradually becomes an important component in the field of adhesives. CN104448219A discloses an aqueous polyurethane resin for pressure sensitive adhesive, which is prepared by the following steps: firstly, carrying out reduced pressure dehydration on hydroxyl-terminated polyester polyol, adding diisocyanate into a reaction kettle after cooling, reacting at 70-90 ℃ for 110-120 min, finally adding a dimethylolpropionic acid solution, and continuing to react for 110-120 min; after the reaction is finished, cooling the materials to 50-55 ℃, adding triethylamine for neutralization, fully stirring for 8-10 min, stopping stirring, simultaneously rapidly injecting deionized water into the reaction kettle, starting a stirring and emulsifying machine, emulsifying for 8-10 min, then adding an ethylenediamine solution, continuing to emulsify for 8-10 min, stopping emulsifying, continuing to stir for 90-120 min, and filtering and discharging. However, the pressure-sensitive adhesive described above has a problem that the adhesiveness is lowered after long-term use.
Disclosure of Invention
The purpose of the invention is: the problem that the viscosity of the polyurethane pressure-sensitive adhesive is reduced after long-term use is solved. According to the invention, the polysiloxane is adopted to modify the aqueous polyurethane pressure-sensitive adhesive, so that the viscosity of the aqueous polyurethane pressure-sensitive adhesive after long-term use is effectively improved.
The technical scheme is as follows:
a preparation method of modified water-based polyurethane pressure-sensitive adhesive comprises the following steps:
step 1, uniformly mixing 30-45 parts by weight of hydroxyl silicone oil, 6-12 parts by weight of silane coupling agent, 2-4 parts by weight of inorganic base and 12-15 parts by weight of ethyl acetate, and heating to react in a nitrogen atmosphere to obtain a modified polysiloxane prepolymer;
step 2, uniformly mixing 15-25 parts of toluene-2, 4-diisocyanate (TDI), 12-15 parts of polyether, 10-20 parts of N-hydroxymethyl acrylamide (N-MA), 10-12 parts of modified polysiloxane prepolymer and 1-1.5 parts of azo initiator, heating, adding 0.5-1 part of organic tin catalyst for primary reaction, adding 3-5 parts of chain extender for secondary reaction, adding 15-25 parts of acetone for diluting the reactant, cooling, adding 1-4 parts of neutralizer for neutralizing to form salt, adding 15-20 parts of water, 4-6 parts of paraffin, 0.5-1 part of antioxidant, 0.5-1 part of anti-aging agent and 4-6 parts of emulsifier, mixing, emulsifying at high speed, and evaporating to remove acetone under reduced pressure to finally obtain the aqueous polyurethane pressure-sensitive adhesive.
In the step 1, the silane coupling agent is one or more of bis- (gamma-triethoxysilylpropyl) tetrasulfide (Si69), bis (triethoxysilylpropyl) disulfide (Si75), gamma-mercaptopropyltriethoxysilane (KH-580), gamma-aminopropyltriethoxysilane (KH-550) and gamma- (2, 3-epoxypropoxy) propyltrimethoxysilane (KH-560).
In the step 1, the inorganic base is selected from one or a mixture of two of NaOH and KOH.
In the step 1, the reaction temperature is 90-100 ℃, and the reaction time is 2-6 h.
In the step 2, the temperature rise refers to the temperature rise to 75-85 ℃.
In the step 2, the reaction time of the first reaction is 2-4 h, and the temperature of the first reaction is 80-85 ℃; the reaction time of the second reaction is 1-3 h, and the temperature of the first reaction is 70-75 ℃.
In the step 2, the azo initiator is selected from one or more of dimethyl azodiisobutyrate, azodiisobutyamidine hydrochloride, azodicarbonamide, azodiisopropyl imidazoline hydrochloride, azoisobutyryl cyano formamide, azodicyclohexyl formonitrile, azodicyan valeric acid, azodiisopropyl imidazoline, azodiisobutyronitrile, azodiisovaleronitrile and azodiisoheptanonitrile.
In the step 2, the organotin catalyst is dibutyl tin dilaurate.
In the step 2, the polyether refers to polyether E-210, polyether N330 or polyether 2000.
In the step 2, the chain extender is one or a mixture of more of l, 4-butanediol, neopentyl glycol, ethylene glycol, diethylene glycol, glycerol, maleic anhydride, trimethylolpropane, ethylenediamine, diethylenetriamine, triethylene tetramine or dimethylolpropionic acid.
In the step 2, the emulsifier is nonylphenol polyoxyethylene ether ammonium sulfate or sodium dodecyl sulfate; the antioxidant is antioxidant 168 or antioxidant 1010; the anti-aging agent is anti-aging agent AW 66.
In the step 2, the high-speed emulsification refers to stirring at a speed of 3000-3500 rpm.
Advantageous effects
The polysiloxane prepolymer is a modifier, can improve the gene crosslinking property of the surface of the waterborne polyurethane, improves the adhesion of the polyurethane, and simultaneously, because the surface hydrophilicity of the polysiloxane prepolymer is poor, the problem of poor fog surface effect of the pressure-sensitive adhesive caused by poor dispersibility after the polysiloxane prepolymer is modified by adding the hydroxyl silicone oil is solved. The pressure-sensitive adhesive has the advantages of high bonding strength and good matte effect.
Detailed Description
Example 1
Step 1, uniformly mixing 30 parts of hydroxyl silicone oil, 6 parts of Si69 silane coupling agent, 2 parts of NaOH and 12 parts of ethyl acetate in parts by weight, and heating to react at 90 ℃ for 2 hours in a nitrogen atmosphere to obtain a modified polysiloxane prepolymer;
step 2, uniformly mixing 15 parts of toluene-2, 4-diisocyanate (TDI), 10 parts of polyether N33012, 10 parts of N-hydroxymethyl acrylamide (N-MA), 10 parts of modified polysiloxane prepolymer and 1 part of azobisisovaleronitrile, heating to 75 ℃, adding 0.5 part of dibutyl tin dilaurate to carry out a first reaction, wherein the reaction time of the first reaction is 2 hours, the temperature of the first reaction is 80 ℃, adding 3 parts of ethylene glycol to carry out a second reaction, the reaction time of the second reaction is 1 hour, the temperature of the first reaction is 70 ℃, adding 15 parts of acetone to dilute the reactant, cooling, adding 1 part of neutralizer to neutralize into salt, adding 15 parts of water, 4 parts of paraffin, 10100.5 parts of antioxidant, AW 660.5 parts of antioxidant and 4 parts of ammonium nonylphenol polyoxyethylene ether sulfate are mixed, high-speed emulsification is carried out at 3000rpm, and acetone is removed by reduced pressure evaporation, so that the water-based polyurethane pressure-sensitive adhesive can be obtained finally.
Example 2
Step 1, uniformly mixing 45 parts of hydroxyl silicone oil, 12 parts of Si69 silane coupling agent, 4 parts of NaOH and 15 parts of ethyl acetate in parts by weight, and heating to react at 100 ℃ for 6 hours in a nitrogen atmosphere to obtain a modified polysiloxane prepolymer;
step 2, uniformly mixing 25 parts of toluene-2, 4-diisocyanate (TDI), 15 parts of polyether N3301, 20 parts of N-hydroxymethyl acrylamide (N-MA), 12 parts of modified polysiloxane prepolymer and 1.5 parts of azobisisovaleronitrile, heating to 85 ℃, adding 1 part of dibutyl tin dilaurate to carry out a first reaction, wherein the reaction time of the first reaction is 4 hours, the temperature of the first reaction is 85 ℃, adding 5 parts of ethylene glycol to carry out a second reaction, the reaction time of the second reaction is 3 hours, the temperature of the first reaction is 75 ℃, adding 25 parts of acetone to dilute the reactant, cooling, adding 4 parts of neutralizing agent to neutralize into salt, adding 20 parts of water, mixing 6 parts of paraffin, 10101 parts of antioxidant, AW 661 parts of antioxidant and 6 parts of nonylphenol polyoxyethylene ether ammonium sulfate, emulsifying at high speed of 3500rpm, and evaporating under reduced pressure to remove acetone to finally obtain the aqueous polyurethane pressure-sensitive adhesive.
Example 3
Step 1, uniformly mixing 42 parts of hydroxyl silicone oil, 8 parts of Si69 silane coupling agent, 3 parts of NaOH and 13 parts of ethyl acetate in parts by weight, and heating to react at 95 ℃ for 4 hours in a nitrogen atmosphere to obtain a modified polysiloxane prepolymer;
step 2, uniformly mixing 20 parts of toluene-2, 4-diisocyanate (TDI), 13 parts of polyether N33013, 15 parts of N-hydroxymethyl acrylamide (N-MA), 11 parts of modified polysiloxane prepolymer and 1.2 parts of azobisisovaleronitrile, heating to 80 ℃, adding 0.8 part of dibutyl tin dilaurate to perform a first reaction, wherein the reaction time of the first reaction is 3 hours, the temperature of the first reaction is 82 ℃, adding 4 parts of ethylene glycol to perform a second reaction, the reaction time of the second reaction is 2 hours, the temperature of the first reaction is 72 ℃, adding 20 parts of acetone to dilute the reactant, cooling, adding 2 parts of neutralizer to neutralize into salt, adding 17 parts of water, 5 parts of paraffin, 10100.7 parts of antioxidant, 660.8 parts of antioxidant AW and 5 parts of nonylphenol polyoxyethylene ether ammonium sulfate are mixed, high-speed emulsification is carried out at 3200rpm, and acetone is removed by reduced pressure distillation, so that the water-based polyurethane pressure-sensitive adhesive can be finally obtained.
Comparative example 1
The difference from example 3 is that: the waterborne polyurethane is not modified by polysiloxane prepolymer.
20 parts of toluene-2, 4-diisocyanate (TDI), 13 parts of polyether N, 15 parts of N-hydroxymethyl acrylamide (N-MA) and 1.2 parts of azobisisovaleronitrile are uniformly mixed, the temperature is increased to 80 ℃, 0.8 part of dibutyl tin dilaurate is added for a first reaction, the reaction time of the first reaction is 3 hours, the temperature of the first reaction is 82 ℃,4 parts of ethylene glycol is added for a second reaction, the reaction time of the second reaction is 2 hours, the temperature of the first reaction is 72 ℃, 20 parts of acetone is added to dilute the reaction product, 2 parts of neutralizer is added after the temperature is reduced to neutralize the reaction product into salt, 17 parts of water, 5 parts of paraffin, 10100.7 parts of antioxidant, 660.8 parts of anti-aging agent AW and 5 parts of ammonium sulfate of nonylphenol polyoxyethylene ether are added to mix, high-speed emulsification is carried out at 3200rpm, acetone is evaporated under reduced pressure, and finally the water-based polyurethane pressure-sensitive adhesive can be obtained.
Comparative example 2
The difference from example 3 is that: the polysiloxane prepolymer is not modified by hydroxyl silicone oil.
Step 1, uniformly mixing 8 parts by weight of Si69 silane coupling agent, 3 parts by weight of NaOH and 13 parts by weight of ethyl acetate, and heating to react at 95 ℃ for 4 hours in a nitrogen atmosphere to obtain polysiloxane prepolymer;
step 2, uniformly mixing 20 parts of toluene-2, 4-diisocyanate (TDI), 13 parts of polyether N33013, 15 parts of N-hydroxymethyl acrylamide (N-MA), 11 parts of polysiloxane prepolymer and 1.2 parts of azobisisovaleronitrile, heating to 80 ℃, adding 0.8 part of dibutyl tin dilaurate to carry out a first reaction, wherein the reaction time of the first reaction is 3 hours, the temperature of the first reaction is 82 ℃, adding 4 parts of ethylene glycol to carry out a second reaction, the reaction time of the second reaction is 2 hours, the temperature of the first reaction is 72 ℃, adding 20 parts of acetone to dilute the reactant, cooling, adding 2 parts of neutralizer to neutralize into salt, adding 17 parts of water, 5 parts of paraffin, 10100.7 parts of antioxidant, 660.8 parts of antioxidant AW and 5 parts of nonylphenol polyoxyethylene ether ammonium sulfate are mixed, high-speed emulsification is carried out at 3200rpm, and acetone is removed by reduced pressure distillation, so that the water-based polyurethane pressure-sensitive adhesive can be finally obtained.
Performance testing
Comparative example 3 was prepared by using a commercially available silicone pressure-sensitive adhesive, and the permanent adhesion was measured according to the American Standard PSTC-7; peel force was tested according to U.S. Standard PSTC-1; the matte effect was tested by visual inspection, the lower the transmittance, the better the matte effect.
Table 1 performance test data for examples 1 to 3 and the control
| Example 1 | Example 2 | Example 3 | Comparative example 1 | Comparative example 2 | Comparative example 3 | |
| Hold and glue Force of | ﹥5 h | ﹥5 h | ﹥6 h | ﹥4 h | ﹥4 h | ﹥4h |
| Peeling off Force of | Not less than 9N, after stripping No residual glue | Not less than 9N, after stripping No residual glue | Not less than 10N, after stripping No residual glue | Not less than 6N, after stripping No residual glue | Not less than 7N, after stripping No residual glue | Not less than 5N, after stripping No residual glue |
| Fog face Effect | Low transmittance of light | Low transmittance of light | Low transmittance of light | Low transmittance of light | High transmittance of light | High transmittance of light |
As can be seen from the table above, the pressure-sensitive adhesive provided by the invention has better adhesive strength and stripping effect compared with the commercial products; compared with the comparative example 1, the example 3 has the advantages that the lasting adhesion effect can be improved after the polysiloxane prepolymer is adopted to modify the waterborne polyurethane; in addition, after the polysiloxane prepolymer is modified by adopting the hydroxyl silicone oil, the problem of poor dispersibility can be solved, and the fog surface effect of the pressure-sensitive adhesive is improved.
The pressure-sensitive adhesive tape was placed in an oven at 80 ℃ for 24 hours, taken out, and the above test items were repeated, with the results shown in Table 2.
TABLE 2 Performance test data for examples 1-3 and the control after thermal aging
| Example 1 | Example 2 | Example 3 | Comparative example 1 | Comparative example 2 | Comparative example 3 | |
| Hold and glue Force of | ﹥5 h | ﹥5 h | ﹥5 h | ﹥4 h | ﹥4 h | ﹥4h |
| Peeling off Force of | Not less than 8N, after stripping No residual glue | Not less than 8N, after stripping No residual glue | Not less than 8N, after stripping No residual glue | Not less than 4N, after stripping Residual glue | Not less than 4N, after stripping Residual glue | Not less than 2N, after stripping Residual glue |
| Fog face Effect | Low transmittance of light | Low transmittance of light | Low transmittance of light | Low transmittance of light | High transmittance of light | High transmittance of light |
As can be seen from the table, the modified pressure-sensitive adhesive still has good bonding effect after thermal aging.
Claims (7)
1. A preparation method of modified water-based polyurethane pressure-sensitive adhesive is characterized by comprising the following steps:
step 1, uniformly mixing 30-45 parts by weight of hydroxyl silicone oil, 6-12 parts by weight of silane coupling agent, 2-4 parts by weight of inorganic base and 12-15 parts by weight of ethyl acetate, and heating to react in a nitrogen atmosphere to obtain a modified polysiloxane prepolymer;
step 2, uniformly mixing 15-25 parts of toluene-2, 4-diisocyanate, 12-15 parts of polyether, 10-20 parts of N-hydroxymethyl acrylamide, 10-12 parts of modified polysiloxane prepolymer and 1-1.5 parts of azo initiator, heating, adding 0.5-1 part of organic tin catalyst for primary reaction, adding 3-5 parts of chain extender for secondary reaction, adding 15-25 parts of acetone for diluting the reactant, cooling, adding 1-4 parts of neutralizer for neutralizing to form salt, adding 15-20 parts of water, 4-6 parts of paraffin, 0.5-1 part of antioxidant, 0.5-1 part of anti-aging agent and 4-6 parts of emulsifier for mixing, emulsifying at high speed, and evaporating acetone under reduced pressure to obtain the aqueous polyurethane pressure-sensitive adhesive; the antioxidant is antioxidant 168 or antioxidant 1010; the anti-aging agent is anti-aging agent AW 66.
2. The method for preparing the modified waterborne polyurethane pressure-sensitive adhesive according to claim 1, wherein in the step 1, the silane coupling agent is one or more of bis- (gamma-triethoxysilylpropyl) tetrasulfide, bis (triethoxysilylpropyl) disulfide, gamma-mercaptopropyltriethoxysilane, gamma-aminopropyltriethoxysilane, and gamma- (2, 3-epoxypropoxy) propyltrimethoxysilane.
3. The method for preparing the modified aqueous polyurethane pressure-sensitive adhesive according to claim 1, wherein in the step 1, the inorganic base is selected from one or a mixture of two of NaOH and KOH; the reaction temperature is 90-100 ℃, and the reaction time is 2-6 h.
4. The preparation method of the modified waterborne polyurethane pressure-sensitive adhesive according to claim 1, wherein in the step 2, the temperature rise refers to a temperature rise to 75-85 ℃; the reaction time of the first reaction is 2-4 h, and the temperature of the first reaction is 80-85 ℃; the reaction time of the second reaction is 1-3 h, and the temperature of the second reaction is 70-75 ℃.
5. The method according to claim 1, wherein in step 2, the azo initiator is selected from one or more of dimethyl azobisisobutyrate, azobisisobutyramidine hydrochloride, azobisformamide, azobisisopropylimidazoline hydrochloride, azobisisobutyronitrile, azobisdicyclohexyl carbonitrile, azobiscyanovaleric acid, azobisisopropylimidazoline, azobisisobutyronitrile, azobisisovaleronitrile, and azobisisoheptonitrile.
6. The method for preparing the modified aqueous polyurethane pressure-sensitive adhesive according to claim 1, wherein in the step 2, the organotin catalyst is dibutyl tin dilaurate; the polyether refers to polyether N330 or polyether 2000; the chain extender is one or a mixture of more of l, 4-butanediol, neopentyl glycol, ethylene glycol, diethylene glycol, glycerol, maleic anhydride, trimethylolpropane, ethylenediamine, diethylenetriamine, triethylene tetramine or dimethylolpropionic acid.
7. The method for preparing the modified aqueous polyurethane pressure-sensitive adhesive according to claim 1, wherein the emulsifier is ammonium nonylphenol polyoxyethylene ether sulfate or sodium dodecyl sulfate; the high-speed emulsification means stirring at a speed of 3000-3500 rpm.
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| CN103923321A (en) * | 2014-04-22 | 2014-07-16 | 北京海斯迪克新材料有限公司 | Polysiloxane with UV (Ultraviolet) and moisture double curing groups and preparation method thereof |
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