CN110194945A - Solvent-free Laminating adhesive of a kind of UV/EB solidification and preparation method thereof - Google Patents
Solvent-free Laminating adhesive of a kind of UV/EB solidification and preparation method thereof Download PDFInfo
- Publication number
- CN110194945A CN110194945A CN201811468739.XA CN201811468739A CN110194945A CN 110194945 A CN110194945 A CN 110194945A CN 201811468739 A CN201811468739 A CN 201811468739A CN 110194945 A CN110194945 A CN 110194945A
- Authority
- CN
- China
- Prior art keywords
- acrylate
- laminating adhesive
- solvent
- free laminating
- photoinitiator
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000012939 laminating adhesive Substances 0.000 title claims abstract description 48
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 238000007711 solidification Methods 0.000 title abstract description 17
- 230000008023 solidification Effects 0.000 title abstract description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 42
- 239000000178 monomer Substances 0.000 claims abstract description 37
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 19
- 239000002518 antifoaming agent Substances 0.000 claims abstract description 13
- 239000002270 dispersing agent Substances 0.000 claims abstract description 13
- 238000009736 wetting Methods 0.000 claims abstract description 13
- 239000002318 adhesion promoter Substances 0.000 claims abstract description 10
- 229920000728 polyester Polymers 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 6
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical group OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000853 adhesive Substances 0.000 claims abstract description 4
- 230000001070 adhesive effect Effects 0.000 claims abstract description 4
- 229920001083 polybutene Polymers 0.000 claims abstract description 4
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 3
- 229920000570 polyether Polymers 0.000 claims abstract description 3
- 150000003254 radicals Chemical class 0.000 claims abstract description 3
- -1 tetrahydrofurfuryl acrylate ester Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 7
- 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 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 5
- FPUXVOPOMLHSJA-UHFFFAOYSA-N OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCON1C(=O)NC(=O)NC1=O Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCON1C(=O)NC(=O)NC1=O FPUXVOPOMLHSJA-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-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
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 claims description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical class [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical group C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical class CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 claims description 2
- 230000008859 change Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 2
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical group CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical group C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical group CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims 1
- APZPSKFMSWZPKL-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(CO)CO APZPSKFMSWZPKL-UHFFFAOYSA-N 0.000 claims 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 1
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 claims 1
- YMCOIFVFCYKISC-UHFFFAOYSA-N ethoxy-[2-(2,4,6-trimethylbenzoyl)phenyl]phosphinic acid Chemical compound CCOP(O)(=O)c1ccccc1C(=O)c1c(C)cc(C)cc1C YMCOIFVFCYKISC-UHFFFAOYSA-N 0.000 claims 1
- YSVJDJBOLBXSIT-UHFFFAOYSA-N methanol prop-2-enoic acid Chemical compound OC.OC(=O)C=C.OC(=O)C=C YSVJDJBOLBXSIT-UHFFFAOYSA-N 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 150000003376 silicon Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 239000004033 plastic Substances 0.000 abstract description 5
- 229920003023 plastic Polymers 0.000 abstract description 5
- 238000009459 flexible packaging Methods 0.000 abstract description 4
- 239000003292 glue Substances 0.000 abstract description 4
- 231100000252 nontoxic Toxicity 0.000 abstract description 3
- 230000003000 nontoxic effect Effects 0.000 abstract description 3
- 238000004806 packaging method and process Methods 0.000 abstract description 2
- 238000010894 electron beam technology Methods 0.000 description 33
- 238000000034 method Methods 0.000 description 6
- ZOJPTQRKWVDKTP-UHFFFAOYSA-N decane methanol prop-2-enoic acid Chemical compound C(C=C)(=O)O.C(C=C)(=O)O.CO.CO.CCCCCCCCCC ZOJPTQRKWVDKTP-UHFFFAOYSA-N 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- GNEPLYVYORHREW-UHFFFAOYSA-N 1,1,3,3,6-pentamethyl-7-nitro-2h-inden-5-amine Chemical compound CC1=C(N)C=C2C(C)(C)CC(C)(C)C2=C1[N+]([O-])=O GNEPLYVYORHREW-UHFFFAOYSA-N 0.000 description 3
- 238000007599 discharging Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000002985 plastic film Substances 0.000 description 3
- 229920006255 plastic film Polymers 0.000 description 3
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 3
- 239000012855 volatile organic compound Substances 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- ZLXYJUZXHDRQMJ-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol prop-1-ene Chemical group C=CC.C=CC.C=CC.C(O)C(CC)(CO)CO ZLXYJUZXHDRQMJ-UHFFFAOYSA-N 0.000 description 1
- XVZXOLOFWKSDSR-UHFFFAOYSA-N Cc1cc(C)c([C]=O)c(C)c1 Chemical group Cc1cc(C)c([C]=O)c(C)c1 XVZXOLOFWKSDSR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- QLFCQAOYVVVLHY-UHFFFAOYSA-N NC(=O)N.CCO[N+]#[C-] Chemical compound NC(=O)N.CCO[N+]#[C-] QLFCQAOYVVVLHY-UHFFFAOYSA-N 0.000 description 1
- QCXXDZUWBAHYPA-UHFFFAOYSA-N OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.O=C1NC(=O)NC(=O)N1 Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.O=C1NC(=O)NC(=O)N1 QCXXDZUWBAHYPA-UHFFFAOYSA-N 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 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 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000003915 air pollution Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- GGPVNYCGLUEERR-UHFFFAOYSA-N cyclopenten-1-yl prop-2-enoate Chemical compound C=CC(=O)OC1=CCCC1 GGPVNYCGLUEERR-UHFFFAOYSA-N 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- MWQBWSPPTQGZII-UHFFFAOYSA-N ethoxy(phenyl)phosphinic acid Chemical compound CCOP(O)(=O)C1=CC=CC=C1 MWQBWSPPTQGZII-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical compound O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
- C09J163/10—Epoxy resins modified by unsaturated compounds
-
- 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
- C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The present invention provides a kind of UV/EB solidification solvent-free Laminating adhesive, is made of the raw material of following mass percent: oligomer: 35-55%, activated monomer: 40-60%, photoinitiator: 0-8%, auxiliary agent: 2-5%；Wherein, oligomer is urethane acrylate, epoxy acrylate, polyester acrylate, polyether acrylate, acrylate, any one or more in polybutene acrylate；Activated monomer is any one or more in simple function group, difunctional or multi-functional acrylate；Photoinitiator is any one or more in free radical photo-initiation；Auxiliary agent is adhesion promoter, defoaming agent, any one or more in wetting dispersing agent.The invention also discloses preparation methods.Product of the invention is efficient, safe and environment-friendly, the nontoxic adhesive of one kind for making glue instantaneous solidification.It is mainly used in packaging industry, plastics are compound between plastics, and combined strength bination is high, and speed is fast, the laminating adhesive requirement being able to satisfy in Flexible-Packaging Industry.
Description
Technical field
The present invention relates to chemical material fields, and in particular to solvent-free Laminating adhesive of a kind of UV/EB solidification and preparation method thereof.
Background technique
" prevention and control of air pollution action plan " abbreviation of publication on September 10th, 2013: ten, atmosphere, it is provided that packages printing
Industry volatile organic matter comprehensive improvement requirement.Packages printing industry VOCs improvement rises to State-level packages printing industry
VOCs discharge amount is about 1,000,000 -- and 2,000,000 tons, plastic flexible package industry VOCs discharge amount about 80%.It is required that it is total to expand pollutant
Control range is measured, promotes Volatile organic emissions overall control in key area, key industry.National total emission volumn decline
10% or more, 15% or more key area decline.
In order to meet existing packages printing industry volatile organic matter comprehensive improvement requirement, upgrading improvement is carried out on material
Become very urgent.
Summary of the invention
In order to overcome drawbacks described above of the existing technology, it is an object of the present invention to a kind of UV/EB solidifications without molten
Agent Laminating adhesive, it has environmentally friendly (Laminating adhesive is nontoxic, harmless, and 100% contains admittedly, and noresidue after solidification does not migrate), energy conservation, fast
The features such as speed solidification, solvent-type film-covered adhesive can be substituted, fully meet laminating adhesive requirement in Flexible-Packaging Industry.
The second object of the present invention is to provide the preparation method of the Laminating adhesive.
One of in order to achieve the object of the present invention, used technical solution is:
A kind of solvent-free Laminating adhesive of UV/EB solidification, is made of the raw material of following mass percent:
Oligomer: 35-55%, activated monomer: 40-60%, photoinitiator: 0-8%, auxiliary agent: 2-5 %；
Wherein, the oligomer is urethane acrylate, epoxy acrylate, polyester acrylate, polyoxyalkylene acrylate
Ester, acrylate, any one or more in polybutene acrylate；
The activated monomer be in simple function group, difunctional or multi-functional acrylate any one or it is more
Kind；
The photoinitiator is any one or more in free radical photo-initiation；
The auxiliary agent is adhesion promoter, defoaming agent, any one or more in wetting dispersing agent.
Monofunctional acrylates' ester is isobornyl methacrylate, acrylic acid in one of the embodiments,
Isobornyl thiocyanoacetate, ethoxyethoxyethyl acrylate, hydroxyethyl methacrylate, tetrahydrofurfuryl acrylate ester, three hydroxyl of ring
Methylpropane formal acrylate, acryloyl morpholine, any one or more in double cyclopentenyl acrylate；
In a preferred embodiment of the invention, the bifunctional acrylate is 1,6- hexanediyl
Ester, dipropylene glycol diacrylate, neopentylglycol diacrylate, any one in tricyclic decane dimethanol diacrylate
Or it is a variety of；
In a preferred embodiment of the invention, the multi-functional acrylate is trimethylolpropane tris propylene
It is acid esters, three (2- ethoxy) isocyanuric acid triacrylates, pentaerythritol triacrylate, pentaerythritol tetraacrylate, double
Any one or more in six acrylate of pentaerythrite；
In a preferred embodiment of the invention, the photoinitiator be 2- hydroxy-2-methyl -1- phenylacetone,
1- hydroxy-cyclohexyl-phenyl ketone, 2,4,6- trimethylbenzoy-dipheny phosphine oxide, (2,4,6- trimethylbenzoyl
Base) phenyl-phosphonic acid ethyl ester, any one or more in bis- (2,4,6- trimethylbenzoyl) phenyl phosphine oxides；
In a preferred embodiment of the invention, the adhesion promoter is γ-aminopropyl-triethoxy silicon
Alkane, γ-aminopropyl trimethoxysilane, γ-(the third oxygen of 2,3- epoxy) propyl trimethoxy silicane, γ-methacryloxypropyl
In base propyl trimethoxy silicane, two oleic acid acyloxy of isopropyl (dioctyl phosphoric acid acyloxy) titanate esters any one or it is more
Kind；
In a preferred embodiment of the invention, the defoaming agent is organic silicon defoaming agent；
In a preferred embodiment of the invention, the wetting dispersing agent is organic silicon wetting dispersing agent.
The second object of the present invention is to provide a kind of UV/EB preparation method for solidifying solvent-free Laminating adhesive, in order to realize
The second object of the present invention, used technical solution is:
A kind of UV/EB solidifies the preparation method of solvent-free Laminating adhesive, comprising the following steps:
(1) activated monomer, photoinitiator, auxiliary agent are added into Scattered Kettle, is completely dissolved photoinitiator and auxiliary agent, and
It is even to be dispersed in activated monomer, mixing speed is controlled, makes the temperature of mixture in Scattered Kettle not higher than 45 DEG C；
(2) after the mixture in step (1) is completely dissolved and is uniformly dispersed, be added oligomer, control mixing speed and
Temperature (500 ± 10 revs/min of mixing speed, temperature≤45 DEG C), makes oligomer be completely dissolved and be uniformly dispersed, obtains UV/EB
Solidify solvent-free Laminating adhesive.
The beneficial effects of the present invention are: a kind of solvent-free Laminating adhesive of related UV/EB solidification refers to (ultraviolet by UV
Light) or EB (electron beam) irradiation, to make efficient, safe and environment-friendly, the nontoxic adhesive of one kind of glue instantaneous solidification.It is main
To be applied to packaging industry, plastics are compound between plastics, and combined strength bination is high, and speed is fast, is able to satisfy in Flexible-Packaging Industry
Laminating adhesive requirement.
Specific embodiment
The present invention is further illustrated by the following examples, but these embodiments must not be used to explain to the present invention
Limitation.
Embodiment 1
A kind of solvent-free Laminating adhesive of UV/EB solidification, is made of following raw material:
Oligomer: urethane acrylate 28g, polyester acrylate 10g；
Activated monomer: simple function group acrylate reactive monomer methacrylic acid isobornyl thiocyanoacetate 25g, bifunctional group third
Olefin(e) acid ester activated monomer 1,6- hexanediyl ester 25g, multifunctional group's acrylate reactive monomer pentaerythrite 3 third
Olefin(e) acid ester 5g；
Photoinitiator: 2- hydroxy-2-methyl -1- phenylacetone 3g, 1- hydroxy-cyclohexyl-phenyl ketone 2g；
Auxiliary agent: adhesion promoter (KH-550) 2g, defoaming agent (model BYK-067A) 0.3g, ground wetting dispersing agent
(BYK-UV3500)o.3g。
One of the implementation case UV/EB solidifies the preparation method of solvent-free Laminating adhesive, is prepared by the following method:
Activated monomer (simple function group acrylate reactive monomer methacrylic acid isobornyl thiocyanoacetate 25g, difunctionality are added into Scattered Kettle
Group's acrylate reactive monomer 1,6- hexanediyl ester 25g, multifunctional group's acrylate reactive monomer Ji Wusi
Alcohol triacrylate 5g), and photoinitiator (2- hydroxy-2-methyl -1- phenylacetone 3g, 1- hydroxy-cyclohexyl-phenyl ketone
2g), auxiliary agent (adhesion promoter (KH-560) 2g, defoaming agent (model BYK-067A) 0.3g, ground wetting dispersing agent
(BYK-UV3500) o.3g it), is completely dissolved photoinitiator and auxiliary agent, and is dispersed in activated monomer, control stirring speed
Degree makes the temperature of mixture in Scattered Kettle not higher than 45 DEG C；Oligomer (urethane acrylate 28g, polyester acrylate is added
10g), mixing speed and temperature are controlled, oligomer is made to be completely dissolved and be uniformly dispersed, discharging packed, obtain a kind of UV/
EB solidifies solvent-free Laminating adhesive.
The UV/EB mixed solidifies solvent-free laminating adhesive adhesiveness 1700mpa.s (25 DEG C), and UV/EB solidification is solvent-free
Laminating adhesive is suitable for various flexible package compound membrane materials, measures its laminating adhesive intensity.Specific data are shown in Table one.
Embodiment 2
A kind of solvent-free Laminating adhesive of UV/EB solidification, is made of following raw material:
Oligomer: polybutene acrylate 18g, epoxy acrylate 20g；
Activated monomer: simple function group acrylate reactive monomer tetrahydrofurfuryl acrylate 25g, bifunctional group's propylene
Acid esters activated monomer tricyclic decane dimethanol diacrylate 25g, multifunctional three (2- hydroxyl second of group's acrylate reactive monomer
Base) isocyanuric acid triacrylate 5g；
Photoinitiator: 2,4,6- trimethylbenzoy-dipheny phosphine oxide 2g, 1- hydroxy-cyclohexyl-phenyl ketone
3g；
Auxiliary agent: adhesion promoter (KH-560) 2g, defoaming agent (model BYK-067A) 0.3g, ground wetting dispersing agent
(BYK-UV3500)o.3g。
One of the implementation case UV/EB solidifies the preparation method of solvent-free Laminating adhesive, is prepared by the following method:
Activated monomer (simple function group acrylate reactive monomer tetrahydrofurfuryl acrylate 25g, difunctional are added into Scattered Kettle
Body acrylate reactive monomer tricyclic decane dimethanol diacrylate 25g, multifunctional group's acrylate reactive monomer three
(2- ethoxy) isocyanuric acid triacrylate 5g), photoinitiator (2,4,6- trimethylbenzoy-dipheny phosphine oxides
2g, 1- hydroxy-cyclohexyl-phenyl ketone 3g), auxiliary agent (adhesion promoter (KH-560) 2g, defoaming agent (model BYK-
067A) 0.3g, ground wetting dispersing agent (BYK-UV3500) is o.3g), it is completely dissolved photoinitiator and auxiliary agent, and uniformly divide
It is dispersed in activated monomer, controls mixing speed, make the temperature of mixture in Scattered Kettle not higher than 45 DEG C；Oligomer (poly- ammonia is added
Ester acrylate 28g, polyester acrylate 10g), mixing speed and temperature are controlled, oligomer is made to be completely dissolved and be uniformly dispersed,
Discharging packed, obtain a kind of UV/EB and solidify solvent-free Laminating adhesive.
The UV/EB mixed solidifies solvent-free laminating adhesive adhesiveness 2000mpa.s (25 DEG C), and UV/EB solidification is solvent-free
Laminating adhesive is suitable for various flexible package compound membrane materials, measures its laminating adhesive intensity.Specific data are shown in Table one.
Embodiment 3
A kind of solvent-free Laminating adhesive of UV/EB solidification, is made of following raw material:
Oligomer: polyether acrylate 23g, acrylate 15g；
Activated monomer: simple function group acrylate reactive monomer propylene morpholide 25g, bifunctional group's acrylate are living
Property monomer tricyclic decane dimethanol diacrylate 25g, multifunctional group's acrylate reactive monomer three (2- ethoxy) isocyanide
Urea acid triacrylate 5g；
Photoinitiator: 2,4,6- trimethylbenzoy-dipheny phosphine oxide 4g, bis- (2,4,6- trimethylbenzoyls
Base) phenyl phosphine oxide 1g；
Auxiliary agent: adhesion promoter (KH-570) 2g, defoaming agent (model BYK-067A) 0.3g, ground wetting dispersing agent
(BYK-UV3500)o.3g。
One of the implementation case UV/EB solidifies the preparation method of solvent-free Laminating adhesive, is prepared by the following method:
Activated monomer (simple function group acrylate reactive monomer tetrahydrofurfuryl acrylate 25g, difunctional are added into Scattered Kettle
Body acrylate reactive monomer tricyclic decane dimethanol diacrylate 25g, multifunctional group's acrylate reactive monomer three
(2- ethoxy) isocyanuric acid triacrylate 5g), photoinitiator (2,4,6- trimethylbenzoy-dipheny phosphine oxides
2g, 1- hydroxy-cyclohexyl-phenyl ketone 3g), auxiliary agent (adhesion promoter (KH-560) 2g, defoaming agent (model BYK-
067A) 0.3g, ground wetting dispersing agent (BYK-UV3500) is o.3g), it is completely dissolved photoinitiator and auxiliary agent, and uniformly divide
It is dispersed in activated monomer, controls mixing speed, make the temperature of mixture in Scattered Kettle not higher than 45 DEG C；Oligomer (poly- ammonia is added
Ester acrylate 28g, polyester acrylate 10g), mixing speed and temperature are controlled, oligomer is made to be completely dissolved and be uniformly dispersed,
Discharging packed, obtain a kind of UV/EB and solidify solvent-free Laminating adhesive.
The UV/EB mixed solidifies solvent-free laminating adhesive adhesiveness 2300mpa.s (25 DEG C), and UV/EB solidification is solvent-free
Laminating adhesive is suitable for various flexible package compound membrane materials, measures its laminating adhesive intensity.Specific data are shown in Table one.
UV/EB of the invention solidify film that solvent-free Laminating adhesive is applicable in be PET, CPP, PVDC, PE, NY etc. and its
Its some plastic film in Flexible-Packaging Industry.
UV/EB of the invention solidifies solvent-free Laminating adhesive, be irradiated by UV (ultraviolet lamp) or EB (electron beam) glue from
Liquid moment becomes solid-state, to reach compound to plastic film progress.
It is as follows that UV/EB of the invention solidifies solvent-free Laminating adhesive implementing process: being consolidated UV/EB using solvent-free complex method
Change solvent-free Laminating adhesive and spread is measured by metering roll, glue is then transferred to by one of film by transferring roller
On, finally another film substrate is shone by composite roll and film laminating before in UV (ultraviolet lamp) or EB (electron beam)
Solidified under penetrating, tests its laminating adhesive intensity.Table one
In above table plastic film pass through sided corona treatment, treated 38 dynes of surface tension >.
The above is only a preferred embodiment of the present invention, is not intended to restrict the invention, although referring to embodiment to the present invention
It is described in detail, it for those skilled in the art, still can be to skill documented by foregoing embodiments
Art scheme is modified or equivalent replacement of some of the technical features, but all in the spirit and principles in the present invention
Within, any modification, equivalent replacement, improvement and so on should all be included in the protection scope of the present invention.
Claims (8)
1. a kind of UV/EB solidifies solvent-free Laminating adhesive, which is characterized in that be made of the raw material of following mass percent:
Oligomer: 35-55%, activated monomer: 40-60%, photoinitiator: 0-8%, auxiliary agent: 2-5%；
Wherein, the oligomer is urethane acrylate, epoxy acrylate, polyester acrylate, polyether acrylate, third
Any one or more in alkene acid ester resin, polybutene acrylate；
The activated monomer is any one or more in simple function group, difunctional or multi-functional acrylate；
The photoinitiator is any one or more in free radical photo-initiation；
The auxiliary agent is adhesion promoter, defoaming agent, any one or more in wetting dispersing agent.
2. a kind of UV/EB as described in claim 1 solidifies solvent-free Laminating adhesive, which is characterized in that the simple function group third
Olefin(e) acid ester is isobornyl methacrylate, isobornyl acrylate, ethoxyethoxyethyl acrylate, methacrylic acid
Hydroxyl ethyl ester, tetrahydrofurfuryl acrylate ester, ring trimethylolpropane formal acrylate, acryloyl morpholine, double cyclopentenyl
Any one or more in acrylate.
3. a kind of UV/EB as described in claim 1 solidifies solvent-free Laminating adhesive, which is characterized in that the difunctional third
Olefin(e) acid ester is 1,6 hexanediol diacrylate, dipropylene glycol diacrylate, neopentylglycol diacrylate, tricyclic decane two
Any one or more in methanol diacrylate.
4. a kind of UV/EB as described in claim 1 solidifies solvent-free Laminating adhesive, which is characterized in that the polyfunctional group third
Olefin(e) acid ester is trimethylolpropane trimethacrylate, three (2- ethoxy) isocyanuric acid triacrylates, three propylene of pentaerythrite
Acid esters, pentaerythritol tetraacrylate, any one or more in double pentaerythritol methacrylate.
5. a kind of UV/EB as described in claim 1 solidifies solvent-free Laminating adhesive, which is characterized in that the photoinitiator is
2- hydroxy-2-methyl -1- phenylacetone, 1- hydroxy-cyclohexyl-phenyl ketone, 2,4,6- trimethylbenzoy-dipheny oxygen
Change phosphine, (2,4,6- trimethylbenzoyl) phenyl-phosphonic acid ethyl ester, in bis- (2,4,6- trimethylbenzoyl) phenyl phosphine oxides
Any one or more.
6. a kind of UV/EB as described in claim 1 solidifies solvent-free Laminating adhesive, which is characterized in that the adhesive force promotes
Agent is γ-aminopropyl triethoxysilane, γ-aminopropyl trimethoxysilane, γ-(the third oxygen of 2,3- epoxy) propyl front three
Oxysilane, γ-methacryloxypropyl trimethoxy silane, isopropyl two oleic acid acyloxy (dioctyl phosphoric acid acyl-oxygen
Base) any one or more in titanate esters.
7. a kind of UV/EB as described in claim 1 solidifies solvent-free Laminating adhesive, which is characterized in that the defoaming agent is to have
Machine silicon class defoaming agent；The wetting dispersing agent is organic silicon wetting dispersing agent.
8. a kind of UV/EB as described in claim 1-7 any one claim solidifies the preparation method of solvent-free Laminating adhesive,
It is characterized by:
A kind of UV/EB solidifies the preparation method of solvent-free Laminating adhesive, comprising the following steps:
(1) activated monomer, photoinitiator, auxiliary agent are added into Scattered Kettle, is completely dissolved photoinitiator and auxiliary agent, and uniformly divide
It is dispersed in activated monomer, controls 500 ± 10 revs/min of mixing speed, make the temperature of mixture in Scattered Kettle not higher than 45 DEG C；
(2) after the mixture in step (1) is completely dissolved and is uniformly dispersed, oligomer is added, controls mixing speed 500 ± 10
Rev/min, temperature≤45 DEG C make oligomer be completely dissolved and be uniformly dispersed, and obtain UV/EB and solidify solvent-free Laminating adhesive.
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| CN112159642A (en) * | 2020-09-25 | 2021-01-01 | 中广核达胜加速器技术有限公司 | Adhesive, preparation method and curing method of flame-retardant glass fiber tape |
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| CN112662318A (en) * | 2020-12-22 | 2021-04-16 | 上海康达化工新材料集团股份有限公司 | Anti-falling UV adhesive for bonding small household appliances |
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| CN113698907A (en) * | 2021-08-24 | 2021-11-26 | 浙江安雅新材料有限公司 | Ultraviolet-curing laminated adhesive for labels and preparation method thereof |
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| CN114561184A (en) * | 2022-02-23 | 2022-05-31 | 东莞市山盟科技有限公司 | Full-solid-content photocuring insulating adhesive and preparation process thereof |
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