JP2021084958A - 接着剤 - Google Patents
接着剤 Download PDFInfo
- Publication number
- JP2021084958A JP2021084958A JP2019214606A JP2019214606A JP2021084958A JP 2021084958 A JP2021084958 A JP 2021084958A JP 2019214606 A JP2019214606 A JP 2019214606A JP 2019214606 A JP2019214606 A JP 2019214606A JP 2021084958 A JP2021084958 A JP 2021084958A
- Authority
- JP
- Japan
- Prior art keywords
- meth
- acid
- compound
- acrylate
- adhesive
- 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.)
- Granted
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 106
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 106
- 150000001875 compounds Chemical class 0.000 claims abstract description 152
- 239000000463 material Substances 0.000 claims abstract description 38
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims abstract description 24
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 22
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims description 19
- 239000012790 adhesive layer Substances 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000031700 light absorption Effects 0.000 claims description 3
- -1 methacryloyl group Chemical group 0.000 abstract description 131
- 238000001723 curing Methods 0.000 abstract description 58
- 230000001678 irradiating effect Effects 0.000 abstract description 11
- 230000033116 oxidation-reduction process Effects 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 99
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 54
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 50
- 239000010408 film Substances 0.000 description 42
- 239000002253 acid Substances 0.000 description 31
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 19
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 18
- 239000000178 monomer Substances 0.000 description 17
- 229920005862 polyol Polymers 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 150000003077 polyols Chemical class 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 14
- 125000004122 cyclic group Chemical group 0.000 description 14
- 239000005056 polyisocyanate Substances 0.000 description 14
- 229920001228 polyisocyanate Polymers 0.000 description 14
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 230000006872 improvement Effects 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 description 12
- 125000002723 alicyclic group Chemical group 0.000 description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 11
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 11
- 229920000728 polyester Polymers 0.000 description 11
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 229920002635 polyurethane Polymers 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 9
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 9
- 239000004814 polyurethane Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 150000003926 acrylamides Chemical class 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 230000001476 alcoholic effect Effects 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 150000004985 diamines Chemical class 0.000 description 7
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 7
- 239000011976 maleic acid Substances 0.000 description 7
- 239000011572 manganese Substances 0.000 description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
- 229910052753 mercury Inorganic materials 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 125000004430 oxygen atom Chemical group O* 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 6
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 125000005396 acrylic acid ester group Chemical group 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 6
- 150000007519 polyprotic acids Polymers 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 6
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 5
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000010941 cobalt Substances 0.000 description 5
- 229910017052 cobalt Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical group O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 5
- 229960002143 fluorescein Drugs 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000004926 polymethyl methacrylate Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- SVTBMSDMJJWYQN-UHFFFAOYSA-N hexylene glycol Natural products CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 229910001507 metal halide Inorganic materials 0.000 description 4
- 150000005309 metal halides Chemical class 0.000 description 4
- 230000005012 migration Effects 0.000 description 4
- 238000013508 migration Methods 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 125000006353 oxyethylene group Chemical group 0.000 description 4
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
- 239000002985 plastic film Substances 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 3
- CDSULTPOCMWJCM-UHFFFAOYSA-N 4h-chromene-2,3-dione Chemical class C1=CC=C2OC(=O)C(=O)CC2=C1 CDSULTPOCMWJCM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 235000015278 beef Nutrition 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- DBZJJPROPLPMSN-UHFFFAOYSA-N bromoeosin Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C(O)C(Br)=C1OC1=C(Br)C(O)=C(Br)C=C21 DBZJJPROPLPMSN-UHFFFAOYSA-N 0.000 description 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 3
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000009501 film coating Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- XMMDVXFQGOEOKH-UHFFFAOYSA-N n'-dodecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCNCCCN XMMDVXFQGOEOKH-UHFFFAOYSA-N 0.000 description 3
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920005906 polyester polyol Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001302 tertiary amino group Chemical group 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 3
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical class C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 3
- 229920001567 vinyl ester resin Polymers 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 3
- 229910052724 xenon Inorganic materials 0.000 description 3
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 3
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 2
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 2
- KHOUKKVJOPQVJM-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCC(CO)(CO)CO KHOUKKVJOPQVJM-UHFFFAOYSA-N 0.000 description 2
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 2
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Abstract
Description
二段階の硬化を行う方法として、例えば、特許文献1では、照射する紫外線の照射時間を変更する方法が開示されており、特許文献2では、光照射を行って仮硬化した後に、熱を加えて本硬化を行う方法が開示されている。
しかし、特許文献1に開示されている方法では、光開始剤の開裂反応を同種の波長域で行っていることから、硬化反応の制御が容易でないという問題があった。また、特許文献2に開示されている方法では、耐熱性が低い基材には使用できないという問題があった。
なお、本明細書では、「(メタ)アクリロイル」、「(メタ)アクリル酸」、「(メタ)アクリレート」、及び「(メタ)アクリロイルオキシ」とは、特に説明がない限り、それぞれ、「アクリロイル及び/又はメタクリロイル」、「アクリル酸及び/又はメタクリル酸」、「アクリレート及び/又はメタクリレート」、並びに「アクリロイルオキシ及び/又はメタクリロイルオキシ」を表すものとする。また、「仮硬化」とは、接着剤から形成された接着剤層が、接着力を有しながらも一旦基材等に張り合わせた後に容易に剥離することができる状態を指す。「本硬化」とは、仮硬化よりも硬化反応が進み、接着剤層が、基材等から容易に剥離できない状態を指す。
本明細書における光増感剤(A)とは、活性エネルギー線を吸収して励起し、励起エネルギーを酸素に与え得るものを指す。詳細には、活性エネルギー線を吸収することにより励起し、その励起三重項エネルギーが酸素分子へエネルギー移動することにより、一重項酸素を発生させ得るものを指す。光増感剤(A)は、紫外(200nm)〜近赤外(900nm)領域に光吸収性を有するものが好ましく、三重項エネルギーレベルが100kJ/mol以上あるものが好ましく、励起一重項から励起三重項への項間交差効率が0.01以上であるものが好ましい。
2’,4’,5’,7’−テトラブロモ‐フルオロセイン(Solvent Red43)、2’,4’,5’,7’−テトラブロモ−フルオロセイン−ナトリウム塩(エオシンY、Acid Red87)、4’,5’−ジブロモ−2’,7’−ジニトロ−フルオロセイン−ナトリウム塩(エオシンB、Acid Red91)、2’,7’−ジクロロ−フルオロセイン、2’,7’−ジクロロ−フルオロセイン−ナトリウム塩、4’,5’−ジブロモ−フルオロセイン(Solvent Red72)、4’,5’−ジブロモ−フルオロセイン−ナトリウム塩、2’,7’−ジブロモ−フルオロセイン、2’,7’−ジブロモ−フルオロセイン−ナトリウム塩、4’,5’−ジクロロ−フルオロセイン、4’,5’−ジクロロ−フルオロセイン−ナトリウム塩、4’,5’−ジヨード−フルオロセイン(Solvent Red73)、4’,5’−ジヨード−フルオロセイン−ナトリウム塩、2’,7’−ジヨード−フルオロセイン、2’,7’−ジヨード−フルオロセイン−ナトリウム塩、トリブロモ−フルオロセイン、トリブロモ−フルオロセイン−ナトリウム塩、2’,4’,5’,7’−テトラクロロ−フルオロセイン、2’,4’,5’,7’−テトラクロロ−フルオロセイン−ナトリウム塩、2’,4’,5’,7’−テトラヨード−フルオロセイン、2’,4’,5’,7’−テトラヨード−フルオロセイン‐ナトリウム塩(エリスロシンB、Acid Red51)、フルオロセイン(Solvent Yellow94)、フルオロセイン−ナトリウム塩、4−アミノフルオロセイン、5−アミノフルオロセイン、3,4,5,6−テトラクロロ−フルオロセイン、3,4,5,6−テトラクロロ−フルオロセイン−ナトリウム塩、エオシン−1−ヘキサデシルピリジニウム塩、2’,4’,5’,7’−テトラブロモ−3,4,5,6−テトラクロロ−フルオロセイン−ナトリウム塩(フロキシンB、Acid Red92)、2’,4’,5’,7’−テトラヨード−3,4,5,6−テトラクロロ−フルオロセイン−ナトリウム塩(ローズベンガル、Acid Red94)、2’,4’,5’,7’−テトラヨード−3,4,5,6−テトラクロロ−フルオロセイン−ビス(トリエチルアンモニウム)塩。
二重結合を有する化合物(B)(以下「化合物(B)」と略記することがある)は、分子内に少なくとも1個の炭素−炭素二重結合を有する化合物である。化合物(B)は、そのものが本発明の接着剤に活性エネルギー線を照射した際に発生した活性種によって重合・架橋する。
例えば、(メタ)アクリル酸メトキシジエチレングリコール、(メタ)アクリル酸エトキシジエチレングリコール、(メタ)アクリル酸エトキシポリエチレングリコール、ジ(メタ)アクリル酸ジエチレングリコール、ジ(メタ)アクリル酸トリエチレングリコール、ジ(メタ)アクリル酸テトラエチレングリコール、ジ(メタ)アクリル酸ポリエチレングリコール等の脂肪族(メタ)アクリル酸エステル類;
ブレンマーADE−200、ブレンマーADE−300、ブレンマーADE−400A、ブレンマーADE−600、ブレンマーPME−100、ブレンマーPME−200、ブレンマーPME−400、ブレンマーPME−1000、ブレンマーPE−200、ブレンマーPE−350、ブレンマー50POEP−800B、ブレンマーPLE−200、ブレンマーPSE−1300、ブレンマーPDE−100、ブレンマーPDE−150、ブレンマーPDE−200、ブレンマーPDE−400、ブレンマーPDE−600、ブレンマーPDBE−200A、ブレンマーPDBE−450A、ブレンマーALE−200、ブレンマーAME−400、ブレンマーAAE−300 (以上、日油化学社製)、ニューフロンティアPE−200、ニューフロンティアPE−300、ニューフロンティアPE−400、ニューフロンティアPE−600、ニューフロンティアBPE−4、ニューフロンティアBPE−10、ニューフロンティアBPE−20、ニューフロンティアTMP−3、ニューフロンティアTMP−15、ニューフロンティアGE3A、ニューフロンティアNP−4、ニューフロンティアN−177E、ニューフロンティアME−3、ニューフロンティアME−4S、ニューフロンティアMPE−600、ニューフロンティアHBPE−4、ニューフロンティアTMP−3、ニューフロンティアPETA−4、ニューフロンティアMPEM−400、ニューフロンティアMPEM−1000、ニューフロンティアPEM−1000、ニューフロンティアBPEM−4、ニューフロンティアBPEM−10、ニューフロンティアHBPEM−10(第一工業製薬社製)、SR−101、SR−150、SR−210、SR−230、SR−252、SR−256、SR−259、SR−272、SR−415、SR−480、SR−494、SR−504、SR−540、SR−550、SR−602、SR−610、SR−9035、SR−344、SR−349、SR−454、SR−499、SR−502、SR−601、SR−9038(サートマー社製)、アロニックスM−260、アロニックスM−102、アロニックスM−113、アロニックスM−114、アロニックスM−210、アロニックスM−240、アロニックスM−350、アロニックスM−360、アロニックスM−370、(東亞合成社製)、NKエステルAM−30G、NKエステルAM−90G、NKエステルAM−130G、NKエステルAM−230G、NKエステルAMP−20GY、NKエステルA−200、NKエステルA−400、NKエステルA−600、NKエステルA−1000、NKエステルA−1206PE、NKエステルA−0612PE、NKエステルA−0412PE、NKエステルA−1000PER、NKエステルA−3000PER、NKエステル A−BPE−4、NKエステルA−BPE−10、NKエステルA−BPE−20、NKエステルA−BPE−30、NKエステル ABE−300、NKエステルA−B1206PE、NKエステルA−TMPT−3EO、NKエステルA−TMPT−9EO、NKエステルAT−20E、NKエステルAT−30E、NKエステルA−GLY−3E、NKエステルA−GLY−6E、NKエステルA−GLY−9E、NKエステルA−GLY−20E、NKエステルATM−4EL、NKエステルATM−8EL、NKエステルATM−4E、NKエステルATM−35E、NKエステルAD−TMP−4E、NKエステルA−DPH−12E、NKエコノマーA−PG5027E、NKエコノマーA−PG5054E、NKエステルM−40G、NKエステルM−90G、NKエステルM−130G、NKエステルM−230G、NKエステルS−20E、NKエステルS−12E、NKエステルEH−4E、NKエステルB−20G、NKエステル9G、NKエステル14G、NKエステル23G、NKエコノマー1000PER、NKエステルBPE−200、NKエステルBPE−300、NKエステルBPE−500、NKエステルBPE−900、NKエステルBPE−1300N、NKエステルGLY−3E、NKエステルGLY−6E、NKエステルGLY−9E、NKエステルGLY−20E、NKエステルTMPT−3EO、NKエステルTMPT−9EO、NKエステルTM−4EL、NKエステルTM−4E、NKエステルTM−35E、NKエステルD−TMP−4E、NKエステルM−DPH−6E、NKエステルM−DPH−12E、NKエコノマーM−PG5027E、NKエコノマーM−PG5054E、NKエステルATM−120E、NKエステルA−DPH−48E、NKエステルA−DPH−96E (以上、新中村化学社製)、Miramer M142、Miramer M144、Miramer M164、Miramer M166、Miramer M170、Miramer M232、Miramer M2100、Miramer M2200、Miramer M2300、Miramer M280、Miramer M282、Miramer M284、Miramer M286、Miramer M290、Miramer M2040、Miramer M3160、Miramer M3190、Miramer M3150、Miramer M4004、Miramer M193、Miramer M241、Miramer M2101、Miramer M2301(MIWON社製)、ライトアクリレートEC−A、ライトアクリレートMTG−A、ライトアクリレートEHDG−AT、ライトアクリレート130A、ライトアクリレートP2H−A、ライトアクリレートP−200A、ライトアクリレートBP−4EAL、ライトアクリレート3EG−A、ライトアクリレート4EG−A、ライトアクリレート9EG−A、ライトアクリレート14EG−A、ライトアクリレートTMP−6EO−3A (以上共栄社化学社製)、ビスコート190、ビスコート360、ビスコート700HV、ビスマーMPE400A、ビスマーMPE550A(以上大阪有機化学社製)、ネオマーPM201(三洋化成工業社製)、EBECRYL110、PEG400DA−D、EBECRYL11(以上ダイセルオルネクス社製)。
例えば、(メタ)アリルアルコール、イソプロペニルアルコール等の水酸基含有の脂肪族(メタ)アリルアルコール類ないしは(メタ)アリルエーテル類;
例えば、プロペンジオール等の複数の水酸基を有する二重結合基含有化合物類;
例えば、(メタ)アクリル酸1,2−シクロヘキサンジメタノール、(メタ)アクリル酸1,3−シクロヘキサンジメタノール、(メタ)アクリル酸1,4−シクロヘキサンジメタノール、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシメチル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシエチル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシプロピル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシブチル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシデシル、(メタ)アクリル酸2−ヒドロキシ−3−フェノキシオクタデシル、(メタ)アクリル酸モノヒドロキシエチルフタレート、(メタ)アクリル酸2−(4−ベンゾイル−3−ヒドロキシフェノキシ)エチル等の水酸基とヘテロ環以外の環状構造を有する(メタ)アクリル酸エステル類;
例えば、2−(2’−ヒドロキシ−5’−(メタ)アクリロイルオキシエチルフェニル
)−2H−ベンゾトリアゾール、等の水酸基含有ベンゾトリアゾール系(メタ)アクリル酸エステル類;
例えば、(メタ)アクリル酸スルホフェノキシエチル等のスルホニル基含有の(メタ)アクリル酸環状エステル類;
例えば、(メタ)アクリロイルオキシエチルジメチルベンジルアンモニウム−p−トルエンスルホネート等のスルホニル基含有の(メタ)アクリル酸環状エステル類の金属塩やアンモニウム塩類;
例えば、5−ビニルビシクロ[2.2.1]ヘプタ−2−エン、2,5−ビス(アリルオキシ)ノルボルナン等のアルケニル基含有の環状化合物類;
例えば、スチレン、2−メチルスチレン等の芳香族ビニル系単量体類;
例えば、シクロヘキシルビニルエーテル、シクロキシルメチルビニルエーテル等の環状ビニルエーテル類;
例えば、ビニルフェニルペンチルエーテル、ビニルフェニルヘキシルエーテル等の長鎖アルキル基を有する芳香族ビニルエーテル系単量体類;
例えば、イソプロペニルフェニルメチルブチルエーテル、イソプロペニルフェニルメチルペンチルエーテル等の長鎖アルキル基を有するイソプロペニルフェニル系単量体類;
例えば、コハク酸ビニルフェニルノニル、ヘキサヒドロフタル酸ビニルフェニルメチルデシル等のジカルボン酸のモノ長鎖アルキルエステル系環状単量体類;
例えば、スチレンスルホン酸、2−プロペニルオキシベンゼンスルホン酸等のアルケニル基含有環状スルホン酸類;
例えば、スチレンスルホン酸アンモニウム、スチレンスルホン酸モノメチルアンモニウム等のスチレンスルホン酸のアンモニウム塩類;
スチレンスルホン酸ナトリウム等のスチレンスルホン酸の金属塩類等が挙げられる。
例えば、1−(メタ)アリル−1H−イミダゾール、1−(メタ)アリル−2−メチル−1H−イミダゾール等の窒素原子含有の六員環を有するビニル基含有化合物類;
例えば、1−ビニル−1H−ベンゾイミダゾール、1−ビニル−5,6−ジメチル−1H−ベンゾイミダゾール等の窒素原子含有のヘテロ多環系エテニル基含有化合物類;
例えば、1−メチル−4,5−ジビニル−1H−イミダゾール等の窒素原子含有のヘテロ環構造と二個以上のビニル基を有する化合物類;
例えば、1−(メタ)アリル−3,5−ジメチル−1H−ピラゾール、1−(1−メチルプロピル)−5−(メタ)アリルピリミジン等の窒素原子含有のヘテロ環状構造を有する(メタ)アリル基含有化合物類;
例えば、2−(メタ)アリル−1H−インドール、3−(メタ)アリル−1H−インドール等の窒素原子含有のヘテロ多環構造を有する(メタ)アリル基含有化合物類;
例えば、メチルマレイミド、エチルマレイミド等の窒素原子と酸素原子の双方を有するマレイミド誘導体類;
例えば、2−ビニルオキサゾール、2−フェニル−4−ビニルオキサゾール等の窒素原子以外に酸素原子を含むヘテロ環状構造を有するビニル基含有化合物類;
例えば、(メタ)アクリル酸グリシジル、(メタ)アクリル酸(3,4−エポキシシクロヘキシル)メチル等の酸素原子を有するヘテロ環含有(メタ)アクリル酸エステル類;
例えば、グリシジルシンナマート、アリルグリシジルエーテル等のグリシジル基含有ビニルエステル類;
例えば、2−ビニルチアゾ−ル、4−メチル−5−ビニルチアゾール等の窒素原子以外に硫黄原子を含むヘテロ環状構造を有するビニル基含有化合物類等が挙げられ、これらは、1種だけを用いてもよいし、あるいは、複数種を併用してもよい。
例えば、(メタ)アクリル酸(メタ)アリル、(メタ)アクリル酸ビニル等のさらに二重結合基を含有する(メタ)アクリル酸エステル類;
例えば、(メタ)アクリル酸パーフルオロメチル、(メタ)アクリル酸パーフルオロエチル等の(メタ)アクリル酸パーフルオロアルキルエステル類;
例えば、(メタ)アクリル酸2−メトキシエチル、(メタ)アクリル酸2−エトキシエチル等のアルコキシ基含有(メタ)アクリル酸エステル類;
例えば、(メタ)アクリル酸のアルキレンオキサイド付加物などのアルキレンオキサイド含有(メタ)アクリル酸誘導体類;
例えば、(メタ)アクリル酸(メトキシカルボニル)メチル、(メタ)アクリル酸(メトキシカルボニル)エチル等のカルボニル基を1つ有する脂肪族系の(メタ)アクリル酸エステル類;
例えば、(メタ)アクリル酸2−オキソブタノイルエチル、(メタ)アクリル酸2−オキソブタノイルプロピル等のカルボニル基を2つ有する脂肪族系の(メタ)アクリル酸エステル類;
例えば、アセト酢酸ビニル等のアシル基を有する脂肪族系のビニル化合物類;
例えば、ベンゾイル酢酸ビニル、ベンゾイルプロピオン酸ビニル等のアシル基を有する芳香族系のビニル化合物類;
例えば、アセト酢酸(メタ)アリル、アセトプロピオン酸(メタ)アリル等のアシル基を有する脂肪族系の(メタ)アリル化合物類;
例えば、3−(メタ)アクリロイルオキシプロピルメチルジメトキシシラン、3−(メタ)アクリロイルオキシプロピルトリメトキシシラン等のアルコキシシリル基含有(メタ)アクリル酸エステル類;
例えば、メチルビニルエーテル、エチルビニルエーテル等の脂肪族ビニルエーテル類;
例えば、プロピレングリコールジビニルエーテル1,4−シクロヘキサンジオールジビニルエーテル(CHODVE)、トリメチロールプロパントリビニルエーテル、ジペンタエリスリトールテトラビニルエーテル、ジトリメチロールプロパンテトラビニルエーテル、ジペンタエリスリトールヘキサビニルエーテル等の多官能のビニルエーテル類;
例えば、(メタ)アクリルアミド、N−メチル(メタ)アクリルアミド等の脂肪族系の(メタ)アクリルアミド類;
例えば、N−メトキシメチル(メタ)アクリルアミド、N−メトキシエチル(メタ)アクリルアミド等のN−アルコキシ基含有の(メタ)アクリルアミド類;
例えば、(メタ)アクリロニトリル、マレインニトリル、フマロニトリル等のニトリル基含有二重結合基含有化合物類;
例えば、酢酸(メタ)アリル、ヤシ油脂肪酸、ピバリン酸ビニル等の飽和カルボン酸の(メタ)アリルエステル類;
例えば、(メタ)アクリル酸N−メチルアミノエチル、(メタ)アクリル酸N−エチルアミノエチル等の1級、および/または2級のアミノ基を有する(メタ)アクリル酸エステル類;
例えば、(メタ)アクリル酸ヒドラジド、2−(2−フリル)−3−(5−ニトロ−2−フリル)(メタ)アクリル酸ヒドラジド等のヒドラジノ基を有する(メタ)アクリル酸エステル類;
例えば、(メタ)アクリル酸ジメチルアミノエチル、(メタ)アクリル酸ジエチルアミノエチル等の3級アミノ基を有する(メタ)アクリル酸エステル類;
例えば、モノメチルアミノエチル(メタ)アクリルアミド、モノエチルアミノエチル(メタ)アクリルアミド等の1級、および/または2級のアミノ基を有する(メタ)アクリルアミド類;
例えば、ジメチルアミノエチル(メタ)アクリルアミド、ジエチルアミノエチル(メタ)アクリルアミド等の3級のアミノ基を有する(メタ)アクリルアミド類;
例えば、ビニルアミン、メチルビニルアミン等の1級、および/または2級のアミノ基を有するビニル化合物類;
例えば、N−エチル−N−ニトロソビニルアミン等の3級アミノ基含有のビニル系化合物類;
例えば、マレイミド、メチルマレイミド等の窒素原子と酸素原子の双方を有するマレイミド誘導体類のヘテロ環状の二重結合基含有化合物類等が挙げられるが、特にこれらに限定されるものではない。これらは、1種だけを用いてもよいし、あるいは、複数種を併用してもよい。
酸化還元触媒(C)は、原子価状態が2以上の状態で存在する事の出来る金属塩又は錯体である。酸化還元触媒(C)は、後述する有機還元剤(D)によって変換された過酸化水素を酸化還元反応により分解し、活性ラジカルを発生させる役割を果たしている。
本発明において、有機還元剤(D)は、ヒドリド移動による還元、つまりは水素供与体となり得るものである。有機還元剤(D)は、光増感剤(A)に活性エネルギー線を照射する事で発生した一重項酸素に水素を供与して過酸化水素を発生させる役割を果たす。また同時にそれとは異なる波長を照射した際にラジカルを放出する。
本発明において、上記成分に加えて、二重結合を有する化合物(B)に該当しないオリゴマー(E)を含んでも良い。オリゴマー(E)を使用することによって、耐熱性又は耐湿熱性を向上させることが容易となる。
ポリエステル系オリゴマー(e1)としては、主鎖骨格に多塩基酸と多価アルコールを重縮合して得られるポリエステルの末端あるいはポリエステル鎖中の水酸基と(メタ)アクリル酸、マレイン酸などの分子内に1個以上のカルボキシル基を有するα,β−エチレン性不飽和二重結合基含有化合物とのエステル化によって得られる化合物、あるいはポリエステルの末端あるいはポリエステル鎖中のカルボキシル基と(メタ)アクリル酸2−ヒドロキシエチル、(メタ)アクリル酸2−ヒドロキシプロピルなどの前述の化合物(b2−1−1)とのエステル化によって得られる化合物である。その他、酸無水物と(メタ)アクリル酸グリシジルと少なくとも1個の水酸基を有する化合物とから得られるポリエステルオリゴマー等もポリエステルオリゴマー(e1)として使用可能である。
比較的高分子量のポリオール類としては、より具体的には、例えば、高分子量ポリエステルポリオール、高分子量ポリアミドポリオール、高分子量ポリカーボネートポリオール及び高分子量ポリウレタンポリオールが挙げられる。高分子量ポリカーボネートポリオールは、上記の比較的低分子量のジオールと炭酸エステル又はホスゲンとの反応によって得られる。
上記高分子量ポリアミドポリオールの市販品としては、富士化成工業社製のTPAE617等を使用できる。
上記高分子量ポリカーボネートポリオールの市販品としては、例えば、パーストープ社製のオキシマーN112、旭化成ケミカルズ社製のPCDLシリーズ、クラレ社製のクラレポリオールPMHCシリーズ、クラレポリオールCシリーズ等が挙げられる。
その他に、ポリカプロラクトンジオール、ポリ(β−メチル−γ−バレロラクトン)ジオール、ポリバレロラクトンジオール等のラクトン類を開環重合して得られるポリエステルポリオール等も、上記高分子量ポリオールとして使用できる高分子量ポリオールに含まれる。
ポリウレタン系オリゴマー(e2)は、少なくとも1個以上のイソシアネート基を有する化合物と(メタ)アクリル酸、(メタ)アクリル酸2−カルボキシエチルに代表される脂肪族系α,β−不飽和二重結合基含有カルボン酸類やその酸無水物類または、脂環や芳香環を有するα,β−不飽和二重結合基含有カルボン酸類やその酸無水物類とを反応させて得られる化合物、あるいは少なくとも1個のイソシアネート基を有する化合物と上述の多価アルコールとを反応させて得られる末端イソシアネート基のウレタンプレポリマーと前記化合物(b2−1−1)を反応させて得られる化合物、あるいは少なくとも1個のイソシアネート基を有する化合物と多価アルコールとを反応させて得られる末端イソシアネート基のウレタンプレポリマーと、更に少なくとも1個以上のアミノ基を有する化合物とを反応させて得られる末端イソシアネート基のウレタンプレポリマーと前記化合物(b2−1−1)とを反応させて得られる化合物である。また、イソシアネート基とアミノ基とを反応させて得られるウレア結合基を含有したものもポリウレタン系オリゴマー(e2)に含む。
ポリエポキシ系オリゴマー(e3)は、グリシジル基を有する化合物とヒドロキシエチル(メタ)アクリレート、(メタ)アクリル酸、マレイン酸などの分子内に1個以上の水酸基やカルボキシル基を有する(メタ)アクリロイル基含有化合物との反応により得られる化合物であり、実質的にグリシジル基を有さず、かつ(メタ)アクリロイル基含有化合物を有する化合物である。代表例としてビスフェノール型、エポキシ化油型、フェノールノボラック型、脂環型が挙げられる。ビスフェノール型ポリエポキシ系オリゴマーとしては、ビスフェノール類とエピクロルヒドリンとを反応させて得られるビスフェノール型ジグリシジルエーテルと(メタ)アクリル酸などの分子内に1個以上のカルボキシル基を有する(メタ)アクリロイル基含有化合物とを反応して得られるものである。
本発明では、オリゴマー(E)として、アクリル系オリゴマー(e4)を使用することもできる。使用可能な化合物の具体例として、(メタ)アクリロイル基を有する変性ポリエーテル、アミン変性された(メタ)アクリロイル基含有化合物、並びに、アルキッド樹脂、スピロアセタール樹脂、ポリブタジエン樹脂、ポリチオールポリエン樹脂及び多価アルコール等の各種化合物に(メタ)アクリロイル基を付加させた変性(メタ)アクリロイル基含有化合物、からなる群より選択される1以上の化合物の、オリゴマーまたはプレポリマーを使用することができる。
しかし、本発明は、上記成分(e2)以外のオリゴマー成分を使用した場合についても、その他の構成成分を適切に配合することによって、所望とする特性を容易に得ることができる。
<その他成分(F)>
本発明の接着剤は、本発明による効果を損なわない範囲であれば、各種添加剤等、その他の成分(F)を適宜配合することも可能である。例えば、ラジカル重合性(転換率)向上、重合硬化収縮率低減、熱膨張率低減、寸法安定性向上、弾性率向上、粘度調整、熱伝導率向上、強度向上、靭性向上、及び着色向上等の観点から、有機又は無機の充填剤を配合することができる。このような充填剤は、ポリマー、セラミックス、金属、金属酸化物、金属塩の材料から構成されるものであってよい。また、その形状については、特に限定されず、例えば、粒子状及び繊維状等であってよい。なお、上記ポリマー系の材料を配合する場合には、フェノール系、ヒンダードアミン系等の酸化防止剤、シランカップリング剤、光増感剤、柔軟性付与剤、可塑剤、難燃化剤、保存安定剤、紫外線吸収剤、チクソトロピー付与剤、分散安定剤、流動性付与剤、発砲剤、防カビ剤、帯電防止剤、磁性体、表面張力調整剤、スリッピング剤、アンチブロッキング剤、レベリング剤、赤外吸収剤、及び消泡剤等の独立した充填剤としてだけではなく、ポリマーブレンド又はポリマーアロイとして、接着剤中に、溶解、半溶解又はミクロ分散させることも可能である。
接着剤の低粘度化、及び基材への濡れ広がり性を向上させるために、接着剤中に水または有機溶剤等の溶剤を含有させても良い。
本発明の接着剤は、液状、ペースト状のいずれの形態でも使用することができるが、液状であることが使用しやすさの観点から好ましい。接着剤が液状である場合、接着剤の粘度は1〜1500mPa・sであることが好ましく、10〜1300mPa・sであることがより好ましく、20〜1000mPa・sであることが更に好ましい。粘度が1500mPa・sより低ければ基材に塗工した場合、0.1〜6μmの薄膜塗工が容易になり、透過率等の光学的特性を出すことが可能になる。また、粘度が1mPa・sより高いと接着剤の膜厚制御が容易になる。
接着剤層とは、本発明の接着剤から形成された層を指す。接着剤層は、接着剤を基材等に塗工して形成しても良いし、接着剤をそのままフィルム状に加工して形成しても良い。
接着剤の硬化方法としては、所定の波長の光を照射して仮硬化を行った後、所定の波長とは異なる波長の光を照射して本硬化を行う方法が好ましい。ここで、「仮硬化」とは、硬化反応がある程度進行して接着性を有しながらも基材等から剥離できる状態を意味し、「本硬化」とは、基材等から剥離困難な状態または硬化反応が完全に進行して終了した状態を意味する。仮硬化を行う際の光照射に用いる波長は、可視域が好ましく、400〜800nmが好ましい。また、本硬化を行う際の光照射に用いる波長は、紫外域が好ましく、250〜399nmが好ましい。仮硬化を行う際に400〜800nmの光を照射することで、光増感剤(A)が酸素を一重項酸素に変換した後、還元剤(D)が過酸化水素に変換し、最終的には酸化還元触媒(C)の作用によって効率よくラジカルが発生されると考えられる。このプロセスを経ることで、通常懸念される酸素阻害による重合反応への悪影響を回避することができる。更に、本硬化を行う際に250〜399nmの波長を用いることで、還元剤自身がラジカル種に変化して、多量のラジカルが発生されると考えられる。すなわち、照射する光の波長を使い分けることによって、仮硬化、本硬化といった段階で接着剤の硬化の制御が可能であることが、本発明の特徴の一つとして挙げられる。
基材(G)は、接着シ−トに用いられる。基材(G)は、透明フィルム、又は透明ガラス板を使用することが好ましい。但し、一方の基材として、透明フィルム又は透明ガラス板を使用すれば、他方の基材として活性エネルギー線が透過し難い基材、例えば、木材、金属板、プラスチック板、紙加工品等の材料からなる基材を使用することもできる。この場合、透明フィルム又は透明ガラス板側から活性エネルギー線を照射することによって、樹脂組成物の重合硬化を行うことが可能である。
<接着シート>
基材と、本発明の接着剤から形成される接着剤層とを備えた接着シートについて説明する。 本発明において、接着シートは、以下のようにして得ることができる。
ここでの仮硬化とは、接着力を有しながらも、一旦基材を張り合わせた後も容易に引きはがすことができる状態を指す。接着剤を仮硬化することにより、仮止めを行うことが可能になる。また本硬化とは、仮硬化よりも重合反応が進み、張り合わせた基材同士が固定された状態を指す。
《分子量》
数平均分子量(Mn)と重量平均分子量(Mw)の測定は、東ソー株式会社製GPC(ゲルパーミエーションクロマトグラフィー)「HLC−8320GPC」を用いた。カラムは、「TSKgel SuperHZ 1000」、「TSKgel SuperHZ 2000」、「TSKgel SuperHZM−N」、「TSKgel MultiporeHXL−M」から選択して用い、溶媒としてはテトロヒドロフラン、測定温度40℃で行った。分子量の決定は、標準物質としてポリスチレンの換算で行った。
共栓三角フラスコ中に試料を、約1gを精密に量り採り、トルエン/エタノール(容量比:トルエン/エタノール=2/1)混合液100mlを加えて溶解した。更にアセチル化剤(無水酢酸25gをピリジンで溶解し、容量100mlとした溶液)を正確に5ml加え、約1時間攪拌した。これに、フェノールフタレイン試液を指示薬として加え、30秒間持続した。その後、溶液が淡紅色を呈するまで0.1Nアルコール性水酸化カリウム溶液で滴定した。
水酸基価は次式により求めた。水酸基価は樹脂の乾燥状態の数値とした(単位:mgKOH/g)。
水酸基価(mgKOH/g)=[{(b−a)×F×28.25}/S]/(不揮発分濃度/100)+D
ただし、S:試料の採取量(g)
a:0.1Nアルコール性水酸化カリウム溶液の消費量(ml)
b:空実験の0.1Nアルコール性水酸化カリウム溶液の消費量(ml)
F:0.1Nアルコール性水酸化カリウム溶液の力価
D:酸価(mgKOH/g)
共栓三角フラスコ中に試料を、約1gを精密に量り採り、トルエン/エタノール(容積比:トルエン/エタノール=2/1)混合液100mlを加えて溶解した。これに、フェノールフタレイン試液を指示薬として加え、30秒間保持した後、溶液が淡紅色を呈するまで0.1Nアルコール性水酸化カリウム溶液で滴定した。
乾燥状態の樹脂の値として、酸価(mgKOH/g)を次式により求めた。
酸価(mgKOH/g)={(5.611×a×F)/S}/(不揮発分濃度/100)
ただし、S:試料の採取量(g)
a:0.1Nアルコール性水酸化カリウム溶液の消費量(ml)
F:0.1Nアルコール性水酸化カリウム溶液の力価
[配合例1〜44]
酸素濃度が10%以下に置換された遮光されたガラス瓶に、表2、3に示す配合量で材料を仕込み、攪拌機にて十分に攪拌を行い、十分に脱泡を行った後、配合例に示す接着剤をそれぞれ得た。尚、表2、3において、数値は部を表し、空欄は配合していないことを表す。表2中、配合例1〜17は本発明の接着剤であり、配合例18〜20は本発明の接着剤ではない。表1に実施例および比較例で使用した材料の略号を示す。
調製した接着剤を、基材として片面にコロナ処理が施された厚み100μmのポリ(メチルメタクリレート)(PMMA)フィルムのコロナ処理された面に、塗工直後の厚みが1μmとなるように接着剤を塗工し、接着剤層が形成された接着シートAを作成した。
◎ :20.0以上181.0秒未満。特に良好。
○ :181.0秒以上401.0秒未満。良好。
△ :401.0秒以上。使用可。
× :粘着力増加せず。不良。
仮硬化性評価試験において初期粘着力が3(N/cm)以上の値を示すシートAに対して、片面にコロナ処理が施された厚み100μmのポリ(メチルメタクリレート)フィルムのコロナ処理がされた面を接着剤層に張り合わせた後、活性エネルギー線照射装置(東芝社製 高圧水銀灯)で最大照度300mW/cm2、積算光量300mJ/cm2の紫外線(照射波長254〜405nm)を照射して、接着シートCを作成した。
ローラー法に準拠して測定した。得られた接着シートCを、25mm×150mmのサイズにカッターを用いて裁断して測定用サンプルとした。サンプルを両面粘着テープ(トーヨーケム社製DF8712S)を使用して、ラミネータを用いて接着シートCのフィルムの表面を金属板上に貼り付けて、固定化した積層体Cと金属板との測定用の積層体を得た。接着シートCの2枚のPMMAフィルムの間に予め切り込みを設けておき、23℃、相対湿度50%の条件下で、300mm/分の速度で金属板に張り付いていない方のPMMAフィルムを引き剥がし、接着剤の剥離強度とした。この剥離強度を下記4段階で評価した。
(評価基準)
◎:剥離力が5.0(N/25mm)以上、剥離不可またはシート破壊。(極めて良好)
○:剥離力が1.0(N/25mm)以上5.0(N/25mm)未満。(良好)
△:剥離力が0.5(N/25mm)以上1.0(N/25mm)未満。(使用可)
×:剥離力が0.5(N/25mm)未満。(不良)
Claims (6)
- 光増感剤(A)と、二重結合を有する化合物(B)と、酸化還元触媒(C)と、有機還元剤(D)とを含んでなる接着剤。
- 光増感剤(A)が、200〜900nm領域の光吸収性を有することを特徴とする、請求項1記載の接着剤。
- 二重結合を有する化合物(B)が、アクリロイル基および/またはメタアクリロイル基を有する化合物を含むことを特徴とする請求項1または2記載の接着剤。
- 基材と、請求項1〜3いずれか記載の接着剤から形成される接着剤層とを備えた接着シ−ト。
- 請求項1〜3いずれか記載の接着剤に、所定の波長の光を照射した後、所定の波長とは異なる波長の光を照射する接着剤の硬化方法。
- 基材上に請求項1〜3いずれか記載の接着剤を塗工し、所定の波長の光を照射した後に、所定の波長とは異なる波長の光を照射する接着シ−トの製造方法。
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JPH03182240A (ja) * | 1989-12-11 | 1991-08-08 | Sogo Shika Iryo Kenkyusho:Kk | 有機溶剤を含むライナー、並びに該ライナー及び光重合型接着剤から成る歯科矯正用ブラケット接着剤系 |
JP2014527099A (ja) * | 2011-07-25 | 2014-10-09 | ヘンケル・チャイナ・カンパニー・リミテッド | Uv照射硬化型−レドックス硬化型接着剤系を用いる基材の接着方法 |
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