CN118146478A - Dimer acid modified polyurethane acrylate resin and preparation method and application thereof - Google Patents
Dimer acid modified polyurethane acrylate resin and preparation method and application thereof Download PDFInfo
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- CN118146478A CN118146478A CN202410027241.9A CN202410027241A CN118146478A CN 118146478 A CN118146478 A CN 118146478A CN 202410027241 A CN202410027241 A CN 202410027241A CN 118146478 A CN118146478 A CN 118146478A
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- dimer acid
- acid modified
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- weight
- polyester polyol
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- 239000000539 dimer Substances 0.000 title claims abstract description 80
- 239000002253 acid Substances 0.000 title claims abstract description 77
- 239000004925 Acrylic resin Substances 0.000 title claims abstract description 41
- 239000004814 polyurethane Substances 0.000 title claims abstract description 38
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims description 37
- 230000003287 optical effect Effects 0.000 claims abstract description 48
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 40
- 230000001070 adhesive effect Effects 0.000 claims abstract description 38
- 239000000853 adhesive Substances 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 23
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 19
- -1 isocyano pentaerythritol triacrylate Chemical compound 0.000 claims abstract description 19
- 230000008569 process Effects 0.000 claims abstract description 12
- 239000003085 diluting agent Substances 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000000178 monomer Substances 0.000 claims description 20
- 238000010438 heat treatment Methods 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 11
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 10
- 125000005442 diisocyanate group Chemical group 0.000 claims description 9
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 7
- 239000012760 heat stabilizer Substances 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- 239000012298 atmosphere Substances 0.000 claims description 6
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 claims description 4
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 4
- 239000001361 adipic acid Substances 0.000 claims description 4
- 235000011037 adipic acid Nutrition 0.000 claims description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 4
- 150000002009 diols Chemical class 0.000 claims description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 claims description 4
- 229920000178 Acrylic resin Polymers 0.000 claims description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- 229940043375 1,5-pentanediol Drugs 0.000 claims description 2
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 2
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 claims description 2
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 claims description 2
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 2
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 claims description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 2
- UQOQXWZPXFPRBR-UHFFFAOYSA-K bismuth dodecanoate Chemical compound [Bi+3].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O UQOQXWZPXFPRBR-UHFFFAOYSA-K 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 claims description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-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
- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 claims description 2
- RLJWTAURUFQFJP-UHFFFAOYSA-N propan-2-ol;titanium Chemical compound [Ti].CC(C)O.CC(C)O.CC(C)O.CC(C)O RLJWTAURUFQFJP-UHFFFAOYSA-N 0.000 claims description 2
- 229960004063 propylene glycol Drugs 0.000 claims description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N tetraisopropyl titanate Substances CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 2
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 2
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 claims description 2
- 238000002834 transmittance Methods 0.000 abstract description 13
- 230000032683 aging Effects 0.000 abstract 1
- 239000002994 raw material Substances 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000002313 adhesive film Substances 0.000 description 7
- 239000004568 cement Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000001723 curing Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 239000002390 adhesive tape Substances 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- PENBDSUEMPXNAM-UHFFFAOYSA-N 2-isocyanoprop-2-enoic acid Chemical compound [N+](#[C-])C(C(=O)O)=C PENBDSUEMPXNAM-UHFFFAOYSA-N 0.000 description 1
- 239000004821 Contact adhesive Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 239000002801 charged material Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002699 waste material 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
- 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
- C08G18/4244—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups
- C08G18/4247—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids
- C08G18/425—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids the polyols containing one or two ether 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
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid 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
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The application discloses a dimer acid modified polyurethane acrylate resin which is prepared from the following components in parts by weight: 50-60 parts by weight of dimer acid modified polyester polyol; 25-35 parts by weight of isocyano pentaerythritol triacrylate end-capping agent; 15-20 parts of reactive diluent. The dimer acid modified polyurethane acrylate resin has the advantages of simple process, low odor, less pollution, stable storage, high light transmittance and excellent ageing resistance, and has high peel strength and holding power under the conditions of high temperature and high humidity, thereby effectively solving the problems of easy debonding and low peel strength of the traditional OCA optical adhesive under the conditions of high temperature.
Description
Technical Field
The application relates to dimer acid modified polyurethane acrylate resin, and a preparation method and application thereof, and belongs to the technical field of optical adhesives.
Background
In recent years, with the increasing volume of flexible electronic devices delivered, optically clear adhesive films (OCA optical adhesives) have been widely used in the production of folding screens. The OCA optical adhesive is a special double-sided adhesive without base material and optical transparency, and the double sides are adhered with release films, so that the OCA optical adhesive has the characteristics of colorless transparency, visible light transmittance of more than 90%, high adhesive strength, mild curing, small curing shrinkage and the like.
With the popularization of flexible screens and large-size screens, the flexible screens are used as important components of various electronic touch display screens, and the performance requirements on the flexible screens and the large-size screens are also becoming severe. Particularly, when the flexible screen is used in a high-temperature and high-humidity environment, the problems of reduced adhesive property, reduced elasticity, foaming and the like are very easy to occur, so that the OCA optical adhesive is required to have certain high-temperature and high-humidity resistance, and the bonding of the screen is ensured to be kept complete and free from defects.
The modification of OCA optical cement is one of the effective methods for improving the high temperature and high humidity resistance. The invention discloses an OCA optical adhesive, a preparation method thereof and an OCA optical adhesive film, wherein the OCA optical adhesive is hydrophobic through grafting fluorine-containing groups and monomers of silicon-oxygen bonds on the molecular chain of the OCA optical adhesive, so that the optical adhesive has moisture resistance. However, the OCA optical adhesive provided by the invention still has the problems of insufficient light transmittance and poor high temperature resistance.
In addition, the method of blending modification is also possible. Patent publication No. CN116675823A reports an organosilicon modified polyester polyurethane acrylate prepolymer, a preparation method and an OCA optical cement prepared by the same, wherein the organosilicon modified polyester polyurethane acrylate prepolymer is added into the system, and the high-temperature and high-humidity resistance performance is improved through an interpenetrating network of organosilicon in the OCA adhesive film. However, the invention also has the problems of insufficient system compatibility, low light transmittance and high fog.
Therefore, in order to solve the above-mentioned problems, there is a need to develop an OCA optical adhesive which has high transmittance, excellent adhesion performance and high temperature and high humidity resistance.
Disclosure of Invention
In order to cope with the application scene of the flexible screen in an extreme environment and solve the problems that the OCA optical adhesive in the prior art cannot achieve high light transmittance resistance, excellent adhesive property and high temperature and high humidity resistance, the application provides dimer acid modified polyurethane acrylate resin, a preparation method and the prepared OCA optical adhesive.
The application adopts the following technical scheme:
The dimer acid modified polyurethane acrylate resin is characterized by being prepared from the following components in parts by weight:
50-60 parts by weight of dimer acid modified polyester polyol;
25-35 parts by weight of isocyano pentaerythritol triacrylate end-capping agent;
15-20 parts of reactive diluent.
The dimer acid has extremely long free carbon chain and excellent barrier property to water vapor, and the dimer acid modified polyester polyol is adopted as one of the formula components, so that the dimer acid modified polyurethane acrylate resin can be applied to OCA optical cement, and the OCA optical cement has good bonding property and high-temperature and high-humidity resistance.
In the dimer acid modified polyurethane acrylate resin, the isocyano pentaerythritol triacrylate end capping agent can react with dimer acid modified polyester polyol to generate double bond end capped dimer acid modified polyurethane acrylate resin, which can be used for participating in the subsequent photo-curing of the OCA adhesive film.
Optionally, the dimer acid modified polyester polyol is prepared by reacting the following components in parts by weight:
50-65 parts by weight of a polyester polyol synthetic monomer;
35-50 parts of dimer acid.
Optionally, the polyester polyol synthetic monomer is selected from at least one of a diol monomer and a diacid monomer.
Optionally, the diol monomer is at least one selected from ethylene glycol, 1, 2-propylene glycol, dipropylene glycol, 2-methyl-1, 3-propylene glycol, 1, 4-butanediol, 1, 5-pentanediol, neopentyl glycol and 1, 6-hexanediol.
Optionally, the diacid monomer is selected from at least one of succinic acid, adipic acid, azelaic acid, sebacic acid, cyclohexanedicarboxylic acid, and phthalic acid.
The polyester polyol contains polar ester bonds, has strong intermolecular forces, and thus has high cohesive force and high temperature resistance. However, the ester bond is not waterproof and is easy to hydrolyze, so that the use requirement of the OCA optical adhesive cannot be met. In contrast, the dimer acid modified polyester polyol with good hydrophobicity and high temperature and high humidity resistance is obtained by adopting the technical scheme.
Alternatively, the molar ratio of hydroxyl groups to carboxylic acid groups in the preparation of the dimer acid modified polyester polyol is greater than 1.
Alternatively, the molar ratio of hydroxyl groups to carboxylic acid groups in the preparation of the dimer acid-modified polyester polyol is in the range of 1.01 to 1.50:1.
Alternatively, the molar ratio of hydroxyl groups to carboxylic acid groups in the preparation of the dimer acid-modified polyester polyol is in the range of 1.05 to 1.1:1.
The diol monomer, the dimer acid and the diacid monomer all have two functional groups, and the linear hydroxyl end-capped polyester resin is obtained through esterification polycondensation reaction, and the hydroxyl end-capped polyester resin can react with an isocyano pentaerythritol triacrylate end-capping agent to obtain double-bond end-capped dimer acid modified polyurethane acrylate resin.
The dimer acid modified polyester polyol prepared by the technical scheme has an acid value of less than 2mg KOH/g, a molecular weight of 1000-4000 and a hydroxyl value of 28-112mg KOH/g.
Optionally, the isocyano pentaerythritol triacrylate end-capping agent is prepared from the following components in parts by weight:
50-65 parts by weight of pentaerythritol triacrylate;
35-50 parts of diisocyanate.
Optionally, the reactive diluent is at least one selected from butyl acrylate, N-amyl acrylate, cyclotrimethylolpropane formal acrylate, trimethylolpropane triacrylate, ethoxyethoxyethyl acrylate, acryloylmorpholine, pentaerythritol triacrylate, N-vinyl pyrrolidone, tripropylene glycol diacrylate, N-vinyl caprolactam, triethylene glycol diacrylate.
By adding the reactive diluent in the reaction process, the viscosity of the dimer acid modified polyurethane acrylate resin can be effectively reduced, and the uniform dispersion and reaction of the dimer acid modified polyester polyol and the isocyano pentaerythritol triacrylate end-capping agent are facilitated.
Optionally, the catalyst is at least one selected from tetraisopropyl titanate, tetra-n-butyl titanate, tetra-tert-butyl titanate, stannous octoate, dibutyl tin dilaurate and bismuth laurate.
Optionally, the heat stabilizer comprises at least one of triphenyl phosphate, triethyl methylphosphonate, and triethyl phosphonoacetate.
According to another aspect of the present application, there is provided a method for preparing the above dimer acid modified urethane acrylate resin, characterized by comprising the steps of:
and (3) heating the mixture containing the dimer acid modified polyester polyol, the isocyano pentaerythritol triacrylate end-capping agent and the reactive diluent in an inactive atmosphere to react I, so as to obtain the dimer acid modified polyurethane acrylate resin.
Optionally, the conditions for heating reaction I include: the reaction temperature is 50-70 ℃ and the reaction time is 5-7 h.
By adopting the technical scheme, the preparation process is simple and convenient, no solvent is needed, the environment is protected, no pollution is caused or the pollution is less, and the prepared dimer acid modified polyurethane acrylate resin can be used for preparing OCA optical cement.
Optionally, the amounts of the components in the combination are as follows:
50-65 parts by weight of a polyester polyol synthetic monomer;
35-50 parts by weight of dimer acid;
0.09 to 0.15 weight portion of catalyst;
0.08 to 0.15 weight portion of heat stabilizer
Optionally, the dimer acid modified polyester polyol is prepared by the following method:
and (3) carrying out step heating reaction on the mixture containing dimer acid, polyester polyol synthetic monomer, catalyst and heat stabilizer in an inactive atmosphere to obtain the dimer acid modified polyester polyol.
Preferably, the conditions of the step-wise temperature-increasing reaction include: heating to 120-130 ℃, reacting for 1-2 h, continuously heating to 170-180 ℃, reacting for 1-2 h, and finally heating to 210-220 ℃ and reacting for 2-3 h.
The dimer acid modified polyester polyol prepared by the bulk polymerization method does not need a solvent, is environment-friendly and pollution-free or pollution-free, and has good hydrolysis resistance and high temperature resistance. The molecular weight distribution and monomer composition distribution of the resin can be regulated by gradual heating and gradual polymerization, so that the dimer acid modified polyester polyol with uniform structure and performance can be obtained.
Optionally, the isocyano pentaerythritol triacrylate capping agent is prepared by the following method:
and (3) heating the mixture containing diisocyanate and pentaerythritol triacrylate in an inactive atmosphere to react II to obtain the isocyano pentaerythritol triacrylate end-capping agent.
Optionally, the molar ratio of the diisocyanate to the pentaerythritol triacrylate is 1:1, a step of;
Optionally, the conditions for heating reaction II include: the reaction temperature is 50-60 ℃ and the reaction time is 4-6 h.
Optionally, the diisocyanate is at least one selected from isophorone diisocyanate, dicyclohexylmethane diisocyanate and hexamethylene diisocyanate.
The high-reactivity isocyanoacrylate end-capping agent synthesized by the method has good reactivity and is favorable for reacting with dimer acid modified polyester polyol.
According to another aspect of the present application, there is also provided an OCA optical adhesive prepared from the following components in parts by weight:
99.8 to 99.9 weight portions of dimer acid modified polyurethane acrylic resin;
0.1 to 0.2 weight portion of photoinitiator;
The dimer acid modified polyurethane acrylate resin is selected from one of the dimer acid modified polyurethane acrylate resin and the dimer acid modified polyurethane acrylate resin prepared by the preparation method according to any one of the above.
By adopting the technical scheme, the prepared OCA optical adhesive has good performances of light transmittance, bonding strength, high-temperature resistance, high-humidity resistance and the like, and can be used in the fields of flexible screens and the like.
Optionally, the photoinitiator is selected from at least one of 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenyl acetone, 2,4, 6-trimethylbenzoyl diphenyl phosphine oxide, 2-phenylbenzyl-2-dimethyl amine-1- (4-morpholinophenyl) butanone, benzil dimethyl ether, 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-acetone.
By adopting the photoinitiator, the curing rate of the dimer acid modified polyurethane acrylate resin can be effectively improved, and the curing time is shortened.
Optionally, the OCA optical cement is prepared by the following method: mixing dimer acid modified polyurethane acrylic resin and a photoinitiator according to a certain mass percentage, and then coating and curing to obtain the OCA optical adhesive.
By adopting the preparation method, the operation is simple, the material dispersion is uniform, the reaction is controllable, and the prepared OCA optical adhesive has good performances of light transmittance, bonding strength, high temperature resistance, high humidity resistance and the like.
The application has the beneficial effects that:
The dimer acid modified polyurethane acrylate resin prepared by the application is prepared by using dimer acid, dihydric alcohol, dibasic acid, heat stabilizer and catalyst, then the dimer acid modified polyurethane acrylate resin is further prepared by using the polyester polyol, no solvent is used in the preparation process, no waste liquid is generated, the environment is protected, no pollution or less pollution is caused, and the OCA optical adhesive prepared by using the dimer acid modified polyurethane acrylate resin has the advantages of good optical performance, bonding performance, high temperature and high humidity resistance and the like. In addition, the technical scheme of the application includes that the isocyano pentaerythritol triacrylate blocking agent is synthesized through pentaerythritol triacrylate and diisocyanate in one step, the blocking agent has high reaction activity, and can react with dimer acid modified polyester polyol, so that the prepared polyurethane acrylate resin has terminal carbon-carbon double bonds, and good photocuring performance is provided for the polyurethane acrylate resin.
Detailed Description
The present application is described in detail below with reference to examples, but the present application is not limited to these examples.
Unless otherwise indicated, all starting materials in the examples of the present application were purchased commercially.
Unless otherwise indicated, the test methods all employ conventional methods and instrumentation.
Preparation example 1 dimer acid-modified polyester polyol
Under the protection of nitrogen, 175.37g of adipic acid, 60.67g of sebacic acid, 191.6g of dipropylene glycol, 55.15g of 2-methyl-1, 3-propanediol, 289.17g of dimer acid, 0.77g of tetra-n-butyl titanate and 0.81g of triphenyl phosphate are added into a reaction kettle, the mixture is stirred and heated to 120 ℃ for 1h, the mixture is continuously heated to 170 ℃ for 2h, the mixture is finally heated to 210 ℃ for 2h, and the mixture is cooled and discharged to obtain the dimer acid modified polyester polyol.
Preparation examples 2 to 3
The same preparation method as in preparation example 1 was used, except that: some of the raw material types, amounts of addition and synthesis process parameters were different from those of preparation example 1 (as shown in Table 1), and the rest of the experimental procedures were identical to those of preparation example 1.
Comparative preparation example 1 polyester polyol
Under the protection of nitrogen, 219.21g of adipic acid, 101.12g of sebacic acid, 191.6g of dipropylene glycol, 55.15g of 2-methyl-1, 3-propanediol, 0.77g of tetra-n-butyl titanate and 0.81g of triphenyl phosphate are added into a reaction kettle, stirred and heated to 120 ℃ for 1h, continuously heated to 170 ℃ for 2h, finally heated to 210 ℃ for 2h, cooled and discharged to obtain the polyester polyol.
Comparative preparation example 2
The same preparation method as comparative preparation example 1 was employed, except that: some of the raw material types, amounts of addition and synthesis process parameters were different from those of preparation example 1 (as shown in Table 1), and the rest of the experimental procedures were identical to those of preparation example 1.
Preparation examples 1-3 and comparative preparation examples 1-2 were prepared by the kinds of raw materials, amounts of fed materials and synthesis process parameters as shown in Table 1:
TABLE 1 raw materials, feed amounts and synthesis process parameters
Example 1
(1) Preparation of isocyano pentaerythritol triacrylate end-capping agent
Under the protection of nitrogen, 16.86g of hexamethylene diisocyanate and 29.89g of pentaerythritol triacrylate are added into a reaction kettle, stirred and heated to 60 ℃, and reacted for 4 hours under the heat preservation, thus obtaining 46.75g of isocyano pentaerythritol triacrylate end-capping agent, and the next synthesis is directly carried out without discharging after the reaction is finished.
(2) Preparation of dimer acid modified polyurethane acrylate resin
Under the protection of nitrogen, 100.24g of dimer acid modified polyester polyol obtained in preparation example 1 and 30g of butyl acrylate serving as a reactive diluent are directly added into the reaction kettle containing 46.75g of isocyano pentaerythritol triacrylate end-capping agent, stirred and heated to 60 ℃, reacted for 5 hours, cooled and discharged to obtain the dimer acid modified polyurethane acrylate resin.
Examples 2 to 7
Examples 2 to 7 were identical to the preparation process of example 1 except that the synthesis process of the isocyano pentaerythritol triacrylate capping agent in step (1) was identical to example 1 except that some of the raw material types, amounts of the raw materials and synthesis process parameters (as shown in table 2) were different; preparation of dimer acid-modified polyurethane acrylate resin in step (2) the experimental procedure was the same as in example 1 except that part of the raw material types, the amounts of the charged materials and the synthesis process parameters were different from those of example 1 (as shown in table 2).
The types of raw materials, amounts of raw materials charged and synthesis process parameters used in examples 1 to 7 are shown in Table 2:
TABLE 2 raw material types, amounts of fed materials and Synthesis Process parameters in examples 1 to 7
Comparative example 1
The preparation was the same as in example 1, except that: dimer acid-modified polyester polyol was obtained from commercial sources (CH 6256 of Shanghai Chu Han New Material technology Co., ltd.) and the types of the remaining raw materials, the amounts of the raw materials and the synthetic process parameters were the same as in example 1.
Application example 1 preparation of OCA optical adhesive
100G of dimer acid modified polyurethane acrylate resin (from example 1) and 0.1g of photoinitiator 1-hydroxycyclohexyl phenyl ketone are mixed, and after being fully and uniformly stirred, OCA optical cement is obtained through defoaming, gluing and UV curing.
Application examples 2 to 7
The application examples 2 to 7 differ from the application example 1 in that: the types and amounts of the raw materials used were different from those of application example 1, and the rest of the experimental procedures were the same as application example 1. The types and amounts of the raw materials used in application examples 1 to 7 are shown in Table 3:
TABLE 3 kinds and amounts of raw materials in application examples 1 to 7
OCA optical adhesive prepared in application examples 1-7 is coated on a PET release film with the thickness of 0.1mm, and is cured under an ultraviolet lamp with the ultraviolet energy of 1600mJ/cm < 2 >, so as to obtain the optical adhesive tape.
Test example 1
The optical adhesives prepared in the above application examples 1 to 7 were subjected to light transmittance, haze, adhesive strength and heat resistance (humidity) using the following detection method/test method:
(1) Transmittance and haze: using a WGT-S light transmittance/haze tester to test the light transmittance and haze of transparent glass with the thickness of 1mm, and taking test data as a blank; and (3) sticking the OCA optical adhesive tapes prepared in application examples 1-7 on a glass sheet, tearing off a release film, testing the light transmittance and the haze of a sample to be tested, and subtracting the value of a blank sample to obtain the value of the sample.
(2) Adhesive strength: OCA optical tapes were tested for 180℃peel strength according to GB/T2792-1998.
(3) High temperature and high humidity resistance test: OCA optical adhesives of application examples 1 to 7 were subjected to sample preparation according to GB/T2792-1998, placed in a constant temperature test chamber at 85℃and 85% rh for 500 hours, and the 180℃peel strength of the samples was again measured after 500 hours.
(4) Water contact angle test: and (3) carrying out a water contact angle test on an OCA optical adhesive layer sample on the PET release film by adopting a contact angle measuring instrument, wherein the size of a water drop is 5 mu l, testing after 30s is stable, and taking an average value after measuring at different positions for 5 times.
The test results experimental data are shown in table 4:
TABLE 4 Performance data of OCA optical gums before and after high temperature and high humidity experiments
As is clear from application examples 1 to 7 in combination with tables 1 to 4, the OCA optical adhesive prepared by using the present application has good optical, adhesive and high temperature and high humidity resistance properties.
Application example 1 and application example 5 are compared, which shows that the prepared OCA optical adhesive has high-temperature and high-humidity resistance under the irradiation of ultraviolet light by the dimer acid modified polyurethane acrylate resin and the photoinitiator. The main reason is that after the long carbon chain dimer acid structure is introduced on the molecular structure of the OCA optical adhesive, the water contact angle of the OCA adhesive film is obviously improved, and the OCA optical adhesive has barrier property to water vapor, so that the high-temperature and high-humidity resistance of the OCA optical adhesive can be obviously improved. As can be seen from comparative application examples 2 and 6, as the content of dimer acid in the dimer acid-modified polyester polyol increases, the water contact adhesive and the high temperature and high humidity resistance of the OCA optical adhesive also increase. In addition, a large number of carbon-carbon double bonds are introduced at the molecular end of the dimer acid modified polyurethane acrylate resin, so that the UV-curable performance of the resin is endowed, the crosslinked OCA optical adhesive film can be prepared, and the peel strength of the adhesive film is further improved.
While the application has been described in terms of preferred embodiments, it will be understood by those skilled in the art that various changes and modifications can be made without departing from the scope of the application, and it is intended that the application is not limited to the specific embodiments disclosed.
Claims (10)
1. The dimer acid modified polyurethane acrylate resin is characterized by being prepared from the following components in parts by weight:
50-60 parts by weight of dimer acid modified polyester polyol;
25-35 parts by weight of isocyano pentaerythritol triacrylate end-capping agent;
15-20 parts of reactive diluent.
2. The dimer acid modified polyurethane acrylate resin according to claim 1, wherein the dimer acid modified polyester polyol is prepared by reacting the following components in parts by weight:
50-65 parts by weight of a polyester polyol synthetic monomer;
35-50 parts of dimer acid.
3. The dimer acid modified polyurethane acrylate resin according to claim 1, wherein the isocyano pentaerythritol triacrylate capping agent is prepared from the following components in parts by weight:
50-65 parts by weight of pentaerythritol triacrylate;
35-50 parts by weight of diisocyanate;
Preferably, the reactive diluent is at least one selected from butyl acrylate, N-pentyl acrylate, cyclotrimethylolpropane formal acrylate, trimethylolpropane triacrylate, ethoxyethoxyethyl acrylate, acryloylmorpholine, pentaerythritol triacrylate, N-vinyl pyrrolidone, tripropylene glycol diacrylate, N-vinyl caprolactam, triethylene glycol diacrylate.
4. The dimer acid modified urethane acrylate resin according to claim 2, wherein said polyester polyol synthetic monomer is selected from at least one of a diol monomer and a diacid monomer;
Preferably, the dihydric alcohol monomer is at least one selected from ethylene glycol, 1, 2-propylene glycol, dipropylene glycol, 2-methyl-1, 3-propylene glycol, 1, 4-butanediol, 1, 5-pentanediol, neopentyl glycol and 1, 6-hexanediol;
preferably, the diacid monomer is selected from at least one of succinic acid, adipic acid, azelaic acid, sebacic acid, cyclohexanedicarboxylic acid, phthalic acid.
5. The dimer acid modified urethane acrylate resin according to claim 2, characterized in that said catalyst is selected from at least one of tetraisopropyl titanate, tetra-n-butyl titanate, tetra-t-butyl titanate, stannous octoate, dibutyltin dilaurate, bismuth laurate;
Preferably, the heat stabilizer comprises at least one of triphenyl phosphate, triethyl methylphosphonate, and triethyl phosphonoacetate.
6. The method for producing a dimer acid modified urethane acrylate resin according to any one of claims 1 to 5, characterized by comprising the steps of:
and (3) heating the mixture containing the dimer acid modified polyester polyol, the isocyano pentaerythritol triacrylate end-capping agent and the reactive diluent in an inactive atmosphere to react I, so as to obtain the dimer acid modified polyurethane acrylate resin.
7. The process of claim 6, wherein the heating of reaction I comprises: the reaction temperature is 50-70 ℃ and the reaction time is 5-7 h;
Preferably, the amounts of the components in the combination are as follows:
50-65 parts by weight of a polyester polyol synthetic monomer;
35-50 parts by weight of dimer acid;
0.09 to 0.15 weight portion of catalyst;
0.08 to 0.15 weight portion of heat stabilizer.
8. The method of claim 6, wherein the dimer acid modified polyester polyol is prepared by the method of:
the mixture containing dimer acid and polyester polyol synthetic monomer, catalyst and heat stabilizer is subjected to step heating reaction in an inactive atmosphere to obtain dimer acid modified polyester polyol;
Preferably, the conditions of the step-wise temperature-increasing reaction include: heating to 120-130 ℃, reacting for 1-2 h, continuously heating to 170-180 ℃, reacting for 1-2 h, and finally heating to 210-220 ℃ and reacting for 2-3 h.
9. The preparation method of claim 6, wherein the isocyano pentaerythritol triacrylate capping agent is prepared by the following method:
heating a mixture containing diisocyanate and pentaerythritol triacrylate in an inactive atmosphere to react II to obtain the isocyano pentaerythritol triacrylate end-capping agent;
Preferably, the molar ratio of the diisocyanate to the pentaerythritol triacrylate is 1:1, a step of;
preferably, the conditions for heating reaction II include: the reaction temperature is 50-60 ℃ and the reaction time is 4-6 h;
Preferably, the diisocyanate is at least one selected from isophorone diisocyanate, dicyclohexylmethane diisocyanate, and hexamethylene diisocyanate.
10. The OCA optical adhesive is characterized by being prepared from the following components in parts by weight:
99.8 to 99.9 weight portions of dimer acid modified polyurethane acrylic resin;
0.1 to 0.2 weight portion of photoinitiator;
The dimer acid modified urethane acrylate resin is selected from one of the dimer acid modified urethane acrylate resins according to any one of claims 1 to 5 and the dimer acid modified urethane acrylate resins prepared by the preparation method according to any one of claims 6 to 9.
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