TWI648321B - Photocurable resin composition - Google Patents
Photocurable resin composition Download PDFInfo
- Publication number
- TWI648321B TWI648321B TW104122988A TW104122988A TWI648321B TW I648321 B TWI648321 B TW I648321B TW 104122988 A TW104122988 A TW 104122988A TW 104122988 A TW104122988 A TW 104122988A TW I648321 B TWI648321 B TW I648321B
- Authority
- TW
- Taiwan
- Prior art keywords
- component
- resin composition
- meth
- photocurable resin
- acrylate
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 66
- -1 tertiary amine compound Chemical class 0.000 claims abstract description 67
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 15
- 150000003512 tertiary amines Chemical group 0.000 claims abstract description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 75
- 239000000463 material Substances 0.000 claims description 22
- 239000003505 polymerization initiator Substances 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 238000005266 casting Methods 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 9
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000853 adhesive Substances 0.000 claims description 6
- 230000001070 adhesive effect Effects 0.000 claims description 6
- VZDDUFFXSBGRMP-UHFFFAOYSA-N 9h-fluoren-1-ylphosphane Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2P VZDDUFFXSBGRMP-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 4
- UMLWXYJZDNNBTD-UHFFFAOYSA-N alpha-dimethylaminoacetophenone Natural products CN(C)CC(=O)C1=CC=CC=C1 UMLWXYJZDNNBTD-UHFFFAOYSA-N 0.000 claims description 4
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 4
- 238000004382 potting Methods 0.000 claims description 4
- 239000000565 sealant Substances 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 claims description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 3
- 125000005410 aryl sulfonium group Chemical group 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- BFIAIMMAHAIVFT-UHFFFAOYSA-N 1-[bis(2-hydroxybutyl)amino]butan-2-ol Chemical compound CCC(O)CN(CC(O)CC)CC(O)CC BFIAIMMAHAIVFT-UHFFFAOYSA-N 0.000 claims description 2
- OZICRFXCUVKDRG-UHFFFAOYSA-N 2-[2-hydroxyethyl(propyl)amino]ethanol Chemical compound CCCN(CCO)CCO OZICRFXCUVKDRG-UHFFFAOYSA-N 0.000 claims description 2
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 claims description 2
- JUVSRZCUMWZBFK-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)-4-methylanilino]ethanol Chemical compound CC1=CC=C(N(CCO)CCO)C=C1 JUVSRZCUMWZBFK-UHFFFAOYSA-N 0.000 claims description 2
- SJIXRGNQPBQWMK-UHFFFAOYSA-N DEAEMA Natural products CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 claims description 2
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 claims description 2
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 claims description 2
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 claims description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims description 2
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 claims description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims 1
- PWBKHZYZYCEMRU-ZVVJOPMHSA-N C(C=C)(=O)NOC=1C=CC=2C[C@@H]3[C@@H]4C=C[C@@H]([C@H]5[C@@]4(C2C1O5)CCN3C)O Chemical compound C(C=C)(=O)NOC=1C=CC=2C[C@@H]3[C@@H]4C=C[C@@H]([C@H]5[C@@]4(C2C1O5)CCN3C)O PWBKHZYZYCEMRU-ZVVJOPMHSA-N 0.000 claims 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 1
- 238000003860 storage Methods 0.000 abstract description 20
- 239000004615 ingredient Substances 0.000 abstract description 7
- 239000007870 radical polymerization initiator Substances 0.000 abstract description 6
- 239000000047 product Substances 0.000 description 24
- 238000002156 mixing Methods 0.000 description 12
- 239000000975 dye Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 8
- 150000001450 anions Chemical class 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 239000005062 Polybutadiene Substances 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 229910021485 fumed silica Inorganic materials 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- DKIDEFUBRARXTE-UHFFFAOYSA-M 3-mercaptopropionate Chemical compound [O-]C(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-M 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 229910052799 carbon Chemical group 0.000 description 3
- 125000004386 diacrylate group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 229920006295 polythiol Polymers 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 2
- XAAILNNJDMIMON-UHFFFAOYSA-N 2'-anilino-6'-(dibutylamino)-3'-methylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C(N(CCCC)CCCC)=CC=C(C2(C3=CC=CC=C3C(=O)O2)C2=C3)C=1OC2=CC(C)=C3NC1=CC=CC=C1 XAAILNNJDMIMON-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- VJKZIQFVKMUTID-UHFFFAOYSA-N 2-diazonio-5-sulfonaphthalen-1-olate Chemical compound N#[N+]C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1[O-] VJKZIQFVKMUTID-UHFFFAOYSA-N 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- OBGBGHKYJAOXRR-UHFFFAOYSA-N 2-methoxy-1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C(OC)=CC(=O)C2=C1 OBGBGHKYJAOXRR-UHFFFAOYSA-N 0.000 description 2
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 206010027146 Melanoderma Diseases 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 238000006845 Michael addition reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000728 polyester Chemical group 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- FJJFSGLWPPEQNH-UHFFFAOYSA-N (1,3,6-trioxo-8-propan-2-ylthiochromeno[2,3-e]isoindol-2-yl) butane-1-sulfonate Chemical compound C(C)(C)C=1C=CC=2SC=3C4=C(C=CC3C(C2C1)=O)C(N(C4=O)OS(=O)(=O)CCCC)=O FJJFSGLWPPEQNH-UHFFFAOYSA-N 0.000 description 1
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- YSWBUABBMRVQAC-UHFFFAOYSA-N (2-nitrophenyl)methanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1[N+]([O-])=O YSWBUABBMRVQAC-UHFFFAOYSA-N 0.000 description 1
- CUHCLROITCDERO-UHFFFAOYSA-N (4-nitrophenyl)methyl 9,10-dimethoxyanthracene-2-sulfonate Chemical compound C=1C=C2C(OC)=C3C=CC=CC3=C(OC)C2=CC=1S(=O)(=O)OCC1=CC=C([N+]([O-])=O)C=C1 CUHCLROITCDERO-UHFFFAOYSA-N 0.000 description 1
- MJYFYGVCLHNRKB-UHFFFAOYSA-N 1,1,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(F)CF MJYFYGVCLHNRKB-UHFFFAOYSA-N 0.000 description 1
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 1
- XYXJKPCGSGVSBO-UHFFFAOYSA-N 1,3,5-tris[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CN1C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C1=O XYXJKPCGSGVSBO-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
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Classifications
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Abstract
本發明之目的係提供一種光硬化性樹脂組成物,其具有優異之膜厚硬化性,且硬化物具有高的遮蔽性,甚至具有優異之貯存安定性。
本發明之光硬化性樹脂組成物,其含有下述(A)至(E)成分。
(A)成分:無色染料(leuco dye)
(B)成分:光酸產生劑(PAG:photo-acid generator)
(C)成分:自由基聚合性化合物(具有3級胺骨架之(甲基)丙烯酸酯除外)
(D)成分:光自由基聚合起始劑
(E)成分:3級胺化合物。
Description
本發明係有關光硬化性樹脂組成物,其具有優異之膜厚硬化性及硬化物具有高的遮蔽性,且具有優異之貯存安定性。
以往,遮蔽性高的一種光硬化性樹脂組成物常用於撓性配線板用的被覆材料(參照日本特開2013-194156號公報)、原始模型之複製品用鑄造材料(參照日本特開平11-060962號公報)、雙凸透鏡之黑條(參照日本特開2013-082924號公報)及電子設備等之組裝用接著劑(參照日本特開2014-025021號公報)等。對光硬化性樹脂組成物賦予遮蔽性的代表方法係可列舉如調配碳黑顏料,惟得到遮蔽性的同時,因紫外線等之活性能量射線的大部分由碳黑吸收,故產生顏料的濃度過高之硬化性不佳的問題。
從上述背景,在日本特開平11-060962號公報中揭示:因含有具有經由光自由基聚合起始劑、酸而著色之特徵的無色染料、光酸產生劑及乙烯性不飽和化合物之澆注用感光性樹脂組成物,使硬化物為黑色,且具有優異之膜厚硬
化性。此係利用「經光的照射而產生之自由基種」比「經光的照射而產生之酸」的產生速度更快。亦即,經由酸而變黑之前,透過光而硬化至底部。
然而,為了在澆注用樹脂中使用雖需有優異之膜厚硬化性,惟在日本特開平11-060962號公報中揭示之澆注用感光性樹脂組成物中的膜厚硬化性並不足。
本發明者等殷鑑於上述課題,專心致志進行檢討。其結果完成有關光硬化性樹脂組成物之本發明。接著,說明本發明之重點。本發明之一實施形態係含有(A)至(E)成分之光硬化性樹脂組成物。
(A)成分:無色染料(leuco dye)
(B)成分:光酸產生劑(PAG:photo-acid generator)
(C)成分:自由基聚合性化合物(具有3級胺骨架之(甲基)丙烯酸酯除外)
(D)成分:光自由基聚合起始劑
(E)成分:3級胺化合物。
本發明之一實施形態係含有(A)至(E)成分之光硬化性樹脂組成物。
(A)成分:無色染料(leuco dye)
(B)成分:光酸產生劑(PAG:photo-acid generator)
(C)成分:自由基聚合性化合物(具有3級胺骨架之(甲基)丙烯酸酯除外)
(D)成分:光自由基聚合起始劑
(E)成分:3級胺化合物
利用該結構,可得到具有優異之膜厚硬化性且硬化物具有高的遮蔽性之光硬化性樹脂組成物。而且,上述光硬化性樹脂可具有優異之貯存安定性。
以下說明本發明之實施形態。而且,本發明並不限於以下之實施形態。
本說明書中,呈示範圍之「X至Y」係「X以上(包含X)至Y以下(包含Y)」之意,「重量」與「質量」、「重量%」與「質量%」及「重量份」與「質量份」視為同義詞。而且,除非另有說明,操作及物性等之測定係在室溫(20至25℃)/相對濕度40至50%之條件下測定。另外,「(甲基)丙烯酸酯」係「丙烯酸酯」或「甲基丙烯酸酯」之意。
本發明之(A)成分的無色染料係經由與酸的接觸而顯色之化合物,可對硬化物賦予遮蔽性。而且,無色染料可依種類而顯色成黑色、藍色、綠色及紅色等,惟從遮蔽性優異之觀點,以得到黑色顯色之無色染料為佳。
(A)成分之中,得到黑色顯色之無色染料並無特別限定,其例可列舉如:3-二丁胺基-6-甲基-7-苯胺基螢光黃
母體、3-二丙基胺基-6-甲基-7-苯胺基螢光黃母體、3-二乙胺基-6-甲基-7-苯胺基螢光黃母體、3-二甲胺基-6-甲基-7-苯胺基螢光黃母體、3-二乙胺基-6-甲基-7-二甲基苯胺基螢光黃母體、3-(4-二乙胺基-2-乙氧基苯基)-3-(1-乙基-2-甲基吲哚-3-基)-4-氮雜苯酞等。該等可使用1種或將2種以上(包含2種)混合使用。該等之中,由硬化物之遮蔽性及光硬化性樹脂組成物之膜厚硬化性的觀點,以3-二丁胺基-6-甲基-7-苯胺基螢光黃母體、3-二乙胺基-6-甲基-7-苯胺基螢光黃母體為佳。
作為本發明之(A)成分的市售品,並無特別限定,可列舉:S-205、BLACK305、ETAC、BLACK100、NIR BLACK78(山田化學工業股份有限公司製造);ODB、ODB-2、ODB-4、ODB-250、Black-XV(山本化成股份有限公司製造)等。
本發明之(A)成分的較佳調配量,相對於下述(C)成分100質量份,係在0.01至20質量份之範圍,以0.05至10質量份為佳,以0.5至5質量份更佳。(A)成分為0.01質量份以上(包含0.01質量份)時,硬化物可具有高的遮蔽性。而且,(A)成分為20質量份以下(包含20質量份)時,光硬化性樹脂組成物可具有優異之膜厚硬化性。
本發明之(B)成分的光酸產生劑係經活性能量射線的照射而產生路易斯酸或布氏酸等酸之化合物。通過由上述(B)成分產生之酸可使上述(A)成分的無色染料顯色。而且,從可兼顧遮蔽性及光硬化性樹脂組成物之膜厚硬化性的觀
點,以在365nm以上之波長區域具有吸收之光酸產生劑為佳。上述(B)成分大致可分為鎓鹽系光酸產生劑與非離子性光酸產生劑。
可在本發明中使用之鎓鹽並無特別限定,其例可列舉如:六氟銻酸鹽陰離子、四氟硼酸鹽陰離子、六氟磷酸鹽陰離子、[PR6]-(惟R各自獨立為氟原子或碳數1至12之氟烷基,至少1個R為碳數1至12之氟烷基。)所示之陰離子、[BR4]-(惟R各自獨立為氟原子或碳數1至12之氟烷基,至少1個R為碳數1至12之氟烷基。)所示之陰離子、[SbR6]-(惟R各自獨立為氟原子或碳數1至12之氟烷基,至少1個R為碳數1至12之氟烷基。)所示之陰離子、六氯銻酸鹽陰離子、三氟甲磺酸離子、或氟磺酸離子等具有抗衡離子之芳基錪鹽、芳基鋶鹽或芳基重氮鹽等。該等可將1種或2種以上(包含2種)混合使用。該等之中,從硬化物的遮蔽性及光硬化性樹脂組成物的膜厚硬化性之觀點,以具有六氟銻酸鹽陰離子、四氟硼酸鹽陰離子、六氟磷酸鹽陰離子、[PR6]-所示之陰離子、[BR4]-所示之陰離子、[SbR6]-所示之陰離子的任一者之抗衡離子的芳基鋶鹽為佳,從對環境的負荷少之觀點,以具有四氟硼酸鹽陰離子、六氟磷酸鹽陰離子、[PR6]-所示之陰離子或[BR4]-所示之陰離子的任一者之抗衡離子的芳基鋶鹽更佳,具體上可列舉如:三芳基鋶-六氟磷酸鹽等。
上述鎓鹽系光酸產生劑之市售品,其例可列舉如:IRGACURE 250、IRGACURE 270(BASF公司製造);WPI-113、WPI-116、WPI-169、WPI-170、WPI-124、WPAG-638、
WPAG-469、WPAG-370、WPAG-367、WPAG-363(和光純藥工業股份有限公司製造);B2380、B2381、C1390、D2238、D2248、D2253、I0591、T1608、T1609、T2041、T2042(東京化成工業股份有限公司製造);AT-6992、AT-6976(ACETO公司製造);CPI-100、CPI-100P、CPI-101A、CPI-200K、CPI-210S(SAN-APRO股份有限公司製造);SP-056、SP-066、SP-130、SP-140、SP-150、SP-170、SP-171、SP-172(ADEKA股份有限公司製造);CD-1010、CD-1011、CD-1012(Sartomer公司製造);San-Aid SI-60、SI-80、SI-100、SI-60L、SI-80L、SI-100L、SI-L145、SI-L150、SI-L160、SI-L110、SI-L147(三新化學工業股份有限公司製造);PI2074(Rhodia Japan製造)等,並無特別限定。
上述非離子性光酸產生劑之例可列舉如:苯甲醯甲基碸型光酸產生劑、鄰硝基苄酯型光酸產生劑、亞胺基磺酸鹽型光酸產生劑、N-羥基亞胺之磺酸酯型光酸產生劑等,惟並不限定於此。該等可使用1種或將2種以上(包含2種)混合使用。非離子性光酸產生劑之具體化合物可列舉如:磺醯基重氮甲烷、肟磺酸鹽、亞胺基磺酸鹽、2-硝基苄基磺酸鹽、二碸、鄰苯三酚磺酸鹽、對-硝基苄基-9,10-二甲氧基蒽-2-磺酸鹽、N-磺醯基-苯碸醯胺、三氟甲磺酸-1,8-萘二甲醯亞胺、九氟丁磺酸-1,8-萘二甲醯亞胺、全氟辛磺酸-1,8-萘二甲醯亞胺、五氟苯磺酸-1,8-萘二甲醯亞胺、九氟丁磺酸-1,3,6-三側氧基-3,6-二氫-1H-11-硫雜-氮雜環五蒽-2-基酯、九氟丁磺酸-8-異丙基-1,3,6-三側氧基-3,6-二氫-1H-11-硫雜-2-氮雜環五蒽
-2-基酯、1,2-萘醌-2-二疊氮基-5-磺酸氯化物、1,2-萘醌-2-二疊氮基-4-磺酸氯化物、1,2-苯醌-2-二疊氮基-4-磺酸氯化物、1,2-萘醌-2-二疊氮基-5-磺酸鈉、1,2-萘醌-2-二疊氮基-4-磺酸鈉、1,2-苯醌-2-二疊氮基-4-磺酸鈉、1,2-萘醌-2-二疊氮基-5-磺酸鉀、1,2-萘醌-2-二疊氮基-4-磺酸鉀、1,2-苯醌-2-二疊氮基-4-磺酸鉀、1,2-萘醌-2-二疊氮基-5-磺酸甲酯、1,2-苯醌-2-二疊氮基-4-磺酸甲酯等。
上述非離子性光酸產生劑之市售品可列舉如:WPAG-145、WPAG-149、WPAG-170、WPAG-199(和光純藥工業股份有限公司製造);D2963、F0362、M1209、M1245(東京化成工業股份有限公司製造);SP-082、SP-103、SP-601、SP-606(ADEKA股份有限公司製造);SIN-11(三寶化學研究所股份有限公司製造);NT-1TF(SAN-APRO股份有限公司製造)等。
本發明之(B)成分之較佳調配量,相對於下述(C)成分100質量份係在0.01至20質量份之範圍,以0.01至10質量份為佳,以0.3至10質量份更佳。上述(B)成分在0.01質量份以上(包含0.01質量份)時,使(A)成分之無色染料顯色效果增大,因此,硬化物可具有高的遮蔽性。而且,(B)成分在20質量份以下(包含20質量份)時,硬化物可具有充分之耐熱性。而且,從顯色性之觀點,相對於(A)成分1質量份,(B)成分以0.1至20質量份為佳。
本發明之(C)成分的自由基聚合性化合物可使用接著劑及塗料等一般使用之具有乙烯性不飽和基之化合物,具體上可列舉含有(甲基)丙烯醯基之化合物等。上述(C)成分係可使用單官能性、二官能性、三官能性及多官能性之單體與寡聚物等。該等可單獨或以2種以上(包含2種)之混合物使用。其中從光硬化性及硬化物之物性優異之觀點,上述(C)成分宜包含寡聚物與單體。亦即,以包含寡聚物、與單官能性、二官能性、三官能性及多官能性之單體的至少1種者為佳。另外,本發明中具有3級胺骨架之(甲基)丙烯酸酯係視為下述的(E)成分。
上述單官能性單體之例可列舉如:丙烯酸、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸三級丁酯、甲基丙烯酸異丁酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸異癸酯、(甲基)丙烯酸丁氧基二乙二醇酯、(甲基)丙烯酸甲氧基聚乙二醇酯、琥珀酸2-甲基丙烯醯氧基乙酯、六氫酞酸2-甲基丙烯醯氧基乙酯、(甲基)丙烯酸環氧丙酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸硬脂酯、(甲基)丙烯酸四氫糠酯、己內酯改質四氫糠基(甲基)丙烯酸酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸二環戊酯、(甲基)丙烯酸二環戊烯酯、(甲基)丙烯酸二環戊烯氧酯、(甲基)丙烯酸異莰酯、(甲基)丙烯酸金剛烷酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸苯酯、(甲基)丙烯酸苯氧基乙酯、(甲基)丙烯酸苯氧基二乙二醇酯、(甲基)丙烯酸苯氧基四乙二醇酯、(甲基)丙烯酸壬基苯氧基乙酯、(甲基)丙烯酸丁氧基乙酯、(甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸2-
羥基丙酯、(甲基)丙烯酸4-羥基丁酯、(甲基)丙烯酸甘油酯、(甲基)丙烯酸三氟乙酯、甲基丙烯醯氧基乙基酸性磷酸酯、磷酸2-羥基乙基甲基丙烯酸酯、γ-甲基丙烯醯氧基丙基三甲氧基矽烷、γ-丙烯醯氧基丙基三甲氧基矽烷等。從本發明之(A)成分及(B)成分之互溶性及硬化性優異之觀點,以(甲基)丙烯酸環己酯、(甲基)丙烯酸二環戊酯、(甲基)丙烯酸二環戊烯酯、(甲基)丙烯酸二環戊烯氧酯、(甲基)丙烯酸異莰酯、(甲基)丙烯酸金剛烷酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸苯酯、(甲基)丙烯酸苯氧基乙酯、(甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸2-羥基丙酯及(甲基)丙烯酸4-羥基丁酯等為佳。
上述二官能性單體之例可列舉如:乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、四乙二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、1,9-壬二醇二(甲基)丙烯酸酯、甘油二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、硬脂酸改質新戊四醇二(甲基)丙烯酸酯、二環戊烯二丙烯酸酯、二(甲基)丙烯醯基異氰脲酸酯、環氧烷改質雙酚二(甲基)丙烯酸酯及二羥甲基-三環癸烷二丙烯酸酯等。
上述三官能性單體之例可列舉如:三羥甲基丙烷三(甲基)丙烯酸酯、新戊四醇三(甲基)丙烯酸酯、三(丙烯醯氧乙基)異氰脲酸酯等。
上述多官能性單體之例可列舉如:二-三羥甲基丙烷四(甲基)丙烯酸酯、新戊四醇四(甲基)丙烯酸酯、二新戊四醇單羥基五(甲基)丙烯酸酯、烷基改質二新戊四醇五丙烯酸
酯、二新戊四醇六(甲基)丙烯酸酯、氰脲酸EO改質二及三丙烯酸酯等。
該等單官能性、二官能性、三官能性及多官能性單體可單獨使用或以2種以上(包含2種)之混合物使用。
上述寡聚物之例可列舉如:聚丁二烯骨架之胺甲酸乙酯(甲基)丙烯酸酯、氫化聚丁二烯骨架之胺甲酸乙酯(甲基)丙烯酸酯、聚碳酸酯骨架之胺甲酸乙酯(甲基)丙烯酸酯、聚醚骨架之胺甲酸乙酯(甲基)丙烯酸酯、聚酯骨架之胺甲酸乙酯(甲基)丙烯酸酯、蓖麻油骨架之胺甲酸乙酯(甲基)丙烯酸酯、異戊二烯系(甲基)丙烯酸酯、氫化異戊二烯系(甲基)丙烯酸酯、環氧基(甲基)丙烯酸酯、含(甲基)丙烯酸基之丙烯酸聚合物等。
本發明中作為(D)成分使用之光自由基聚合起始劑,如為藉由活性能量射線照射而產生自由基的化合物即可而無特別限定。而且,從可兼具硬化物之遮蔽性及光硬化性樹脂組成物之膜厚硬化性的觀點,以在365nm以上(包含365nm)之波長區域具有吸收之光自由基聚合起始劑為佳。而且,(D)成分之例可列舉如:苯乙酮系光自由基聚合起始劑、安息香系光自由基聚合起始劑、二苯基酮系光自由基聚合起始劑、硫雜蒽酮系光自由基聚合起始劑、醯基膦氧化物系光
自由基聚合起始劑及二茂鈦系光自由基聚合起始劑等,該等之中,從光硬化性樹脂組成物之膜厚硬化性及硬化物之遮蔽性優異的觀點,以包含苯乙酮系光自由基聚合起始劑及醯基膦氧化物系光自由基聚合起始劑之至少1種為佳。而且,該等可單獨使用,亦可併用2種以上(包含2種)。
上述苯乙酮系光自由基聚合起始劑之例可列舉如:二乙氧基苯乙酮、2-羥基-2-甲基-1-苯基-丙烷-1-酮、苄基二甲基縮酮、4-(2-羥基乙氧基)苯基-(2-羥基-2-丙基)酮、1-羥基-環己基-苯基-酮、2-甲基-2-N-嗎福林基(4-硫甲基苯基)丙-1-酮、2-苄基-2-二甲基胺基-1-(4-嗎福林基苯基)丁酮、2-羥基-2-甲基-1-[4-(1-甲基乙烯基)苯基]丙酮寡聚物等,惟並不限於此。上述苯乙酮系光自由基聚合起始劑之市售品,可列舉如:IRGACURE 184、DAROCUR 1173、IRGACURE 2959、IRGACURE 127(BASF股份有限公司製造);ESACURE KIP-150(Lamberti s.p.a.股份有限公司製造)等。
上述醯基膦氧化物系光自由基聚合起始劑之例可列舉如:雙(2,4,6-三甲基苄醯基)-苯基-膦氧化物、2,4,6-三甲基苄醯基-二苯基-膦氧化物等,惟並不限於此。上述醯基膦氧化物系光自由基聚合起始劑之市售品,可列舉如:LUCIRIN TPO、IRGACURE 819、IRGACURE 819DW(BASF公司製造)等。
本發明之(D)成分的調配量,相對於(C)成分100質量份係以0.1至15質量份為佳,以1至10質量份更佳。上述(D)成分在0.1質量份以上(包含0.1質量份)時,因活性能量
射線而可提高光硬化性樹脂組成物的膜厚硬化性,在15質量份以下(包含15質量份)時,可提高光硬化性樹脂組成物的保存安定性。
本發明之(E)成分的3級胺化合物,藉由本發明之(A)至(D)成分之組合,即可提供兼具有優異之貯存安定性及膜厚硬化性之光硬化性樹脂組成物。上述(E)成分,從光硬化性樹脂組成物之貯存安定性之觀點,以不含1級或2級胺基而僅具有3級胺基之化合物為佳。而且,藉由上述(E)成分而提高光硬化性樹脂組成物之膜厚硬化性的原理雖不明確,惟可推測其係由於(E)成分可將經酸而使無色染料的顯色延緩,在形成膜時可使光穿透至深部之原因。而且,藉由上述(E)成分而提高光硬化性樹脂組成物之貯存安定性的原理雖不明確,惟可認為其係在1級或2級胺化合物與(C)成分之間產生邁克爾加成反應,故為光硬化性樹脂組成物之貯存安定性低劣者。而且,如為本發明之(E)成分時,推測因不與(C)成分產生邁克爾加成反應,故光硬化性樹脂組成物之貯存安定性得到改進。然而,本發明的技術範圍並不受上述推理的限制。
上述(E)成分並無特別限定,其例可列舉如:N-苯基二乙醇胺、N-甲基二乙醇胺、對甲基苯基二乙醇胺、N-乙基二乙醇胺、N-丙基二乙醇胺、N-丁基二乙醇胺、三乙醇胺、三丁醇胺,三異丙醇胺、N-甲基二乙醇胺或N-甲基二甲醇胺等之取代基的至少1者為碳數1至8之直鏈狀或分枝狀
的羥烷基之3級胺化合物;三甲胺、三乙胺、三丁胺、N,N-二甲基-對甲苯胺、N,N-二甲基-苯胺、N,N-(二甲基胺基)乙基-甲基丙烯酸酯、N,N-二甲基胺基苯乙酮、N,N-二甲基胺基二苯基酮、N,N-二乙基胺基二苯基酮、N-甲基哌啶、N-乙基哌啶、N,N-二甲基苄胺、N,N-二甲基環己胺、丙烯醯基嗎福林、N-嗎福林基乙基(甲基)丙烯酸酯、N,N-二甲基胺基乙基(甲基)丙烯酸酯、N,N-二乙基胺基乙基(甲基)丙烯酸酯、N,N-二甲基胺基乙基(甲基)丙烯酸酯及N,N-二甲基胺基丙基(甲基)丙烯酸酯等。該等可使用1種或將2種以上(包含2種)混合使用。該等之中,由於光硬化性樹脂組成物之貯存安定性優異、硬化物之遮蔽性及光硬化性樹脂組成物之膜厚硬化性優異,故(E)成分係以上述取代基的至少1者為碳數1至8之直鏈狀或分枝狀的羥烷基之3級胺化合物;選自丙烯醯基嗎福林、N-嗎福林基乙基(甲基)丙烯酸酯、二甲基胺基乙基(甲基)丙烯酸酯、二乙基胺基乙基(甲基)丙烯酸酯、N,N-二甲基胺基乙基(甲基)丙烯酸酯及N,N-二甲基胺基丙基(甲基)丙烯酸酯所成群組中之至少1種為佳。而且,除了上述觀點以外,從可減少相對於上述(C)成分之(E)成分的調配量之觀點,(E)成分係以包含取代基的至少1者為碳數1至8之直鏈狀或分枝狀的羥烷基之3級胺化合物的至少1種更佳。
本發明之(E)成分的調配量,相對於(C)成分100質量份,以0.01至200質量份為佳,以0.05至150質量份更佳,以0.1至100質量份為特佳。(E)成分的調配量在0.01質量份以上(包含0.01質量份)時,由活性能量射線而可提高光
硬化性樹脂組成物之膜厚硬化性,如在200質量份以下(包含200質量份)時,即可提高硬化物之遮蔽性。而且,(E)成分包含取代基的至少1者為碳數1至8之直鏈狀或分枝狀的羥烷基之3級胺化合物之至少1種時,可減少相對於(C)成分之(E)成分的調配量,相對於(C)成分100質量份為0.01至20質量份,以0.05至15質量份為佳,以0.1至10質量份更佳。
而且,(E)成分及(B)成分之調配量,從可兼具高的遮蔽性與膜厚硬化性之觀點,相對於(C)成分100質量份,以含有上述(E)成分0.01至100質量份及上述(B)成分0.01至10質量份為佳。
對於本發明,在無損本發明之目的的範圍下,可使用:苯乙烯系共聚物等之各種彈性體、聚硫醇化合物、增敏劑、填充材、保存安定劑、抗氧化劑、光安定劑、保存安定劑、重金屬惰性劑、密著賦予劑、塑化劑、消泡劑、顏料、防鏽劑、勻染劑、分散劑、流變調節劑、阻燃劑及界面活性劑等之添加劑。
對本發明,以提高光硬化性之目的可添加聚硫醇化合物。聚硫醇化合物係可列舉如:三羥甲基丙烷三(3-巰基丙酸酯)、新戊四醇四(3-巰基丙酸酯)、三羥甲基丙烷三(3-巰基丁酸酯)、三羥甲基乙烷三(3-巰基丁酸酯)、乙二醇雙(3-巰基乙醇酸酯)、丁二醇雙(3-巰基乙醇酸酯)、三羥甲基丙烷三(3-巰基乙醇酸酯)、新戊四醇四(3-巰基乙醇酸酯)、三-[(3-巰基丙醯氧基)-乙基]-異氰脲酸酯、新戊四醇四(3-巰基丙酸酯)、四乙二醇雙(3-巰基丙酸酯)、二新戊四醇六(3-巰基丙酸酯)、
新戊四醇四(3-巰基丁酸酯)、1,4-雙(3-巰基丁醯氧基)丁烷及1,3,5-三(3-巰基丁基氧基乙基)-1,3,5-三嗪-2,4,6-(1H,3H,5H)-三酮等。
對本發明,以提高光硬化性之目的可添加增敏劑。增敏劑之例可列舉如:蒽、芘、苝、氧葱酮、硫雜蒽酮、曙紅、酮基香豆素、香豆素及異苯并呋喃等。
對本發明,以改善硬化物之彈性模量、流動性的等之目的,可添加無損光硬化性樹脂組成物之膜厚硬化性及貯存安定性之程度的填充材。具體上可列舉如:有機質粉體、無機質粉體及金屬質粉體等。
上述無機質粉體之填充材可列舉如:玻璃、氣相二氧化矽、氧化鋁、雲母、陶瓷、矽橡膠粉、碳酸鈣、氮化鋁、碳粉、高嶺土、乾燥黏土礦物及乾燥矽藻土等。無機粉末之調配量,相對於(A)成分100質量份,以0.1至100質量份為佳。在0.1質量份以上(包含0.1質量份)時,可得到硬化物之彈性模量、流動性等之改善效果,在100質量份以下(包含100質量份)時,光硬化性樹脂組成物之流動性優異,提高操作性。
上述氣相二氧化矽係以調整光硬化性樹脂組成物的黏度或改善硬化物之機械強度之目的而可調配。較佳者係使用表面經二甲基矽烷、三甲基矽烷、烷基矽烷、甲基丙烯醯氧基矽烷、有機氯矽烷、聚二甲基矽氧烷及六甲基二矽氮烷等處理之氣相二氧化矽。氣相二氧化矽之市售品,可列舉如:AEROSIL(註冊商標)R972、R972V、R972CF、R974、
R976、R976S、R9200、RX50、NAX50、NX90、RX200、RX300、R812、R812S、R8200、RY50、NY50、RY200S、RY200、RY300、R104、R106、R202、R805、R816、T805、R711、RM50及R7200(日本Aerosil股份有限公司製造)等。
上述有機質粉體之填充材之例可列舉如:聚乙烯、聚丙烯、尼龍、交聯丙烯酸、交聯聚苯乙烯、聚酯、聚乙烯醇、聚乙烯醇縮丁醛及聚碳酸酯等。有機質粉體之調配量,相對於(A)成分100質量份,以0.1至100質量份為佳。如為0.1質量份以上(包含0.1質量份),即可得到硬化物之彈性模數、流動性等之改良效果,如為100質量份以下(包含100質量份),則光硬化性樹脂組成物之流動性優異,作業性提高。
對本發明可添加保存安定劑。作為上述保存安定劑係可添加:苯醌、氫醌、氫醌單甲基醚等自由基吸收劑;乙二胺四乙酸或其2-鈉鹽、草酸、乙醯丙酮、鄰胺酚等金屬螯合劑等。
對本發明可添加抗氧化劑。上述抗氧化劑之例可列舉如:β-萘醌、2-甲氧基-1,4-萘醌、甲基氫醌、氫醌、氫醌單甲基醚、單三級丁基氫醌、2,5-二-三級丁基氫醌、對苯醌、2,5-二苯基-對苯醌,2,5-二-三級丁基對苯醌等之醌系化合物;酚噻嗪、2,2-亞甲基-雙(4-甲基-6-三級丁基酚)、兒茶酚、三級丁基兒茶酚、2-丁基-4-羥基苯甲醚、2,6-二-三級丁基對甲酚、2-三級丁基-6-(3-三級丁基-2-羥基-5-甲基苄基)-4-甲基苯基丙烯酸酯、2-[1-(2-羥基-3,5-二-三級戊基苯基)乙基]-4,6-二-三級戊基苯基丙烯酸酯、4,4'-亞丁基雙(6-三級丁基-3-甲基
酚)、4,4'-硫雙(6-三級丁基-3-甲基酚)、3,9-雙[2-[3-(3-三級丁基-4-羥基-5-甲基苯基)丙醯氧基]-1,1-二甲基乙基]-2,4,8,10-四氧雜螺[5,5]十一烷、新戊四醇四[3-(3,5-二-三級丁基-4-羥基苯基)丙酸酯]、硫二伸乙基雙[3-(3,5-二-三級丁基-4-羥基苯基)丙酸酯]、十八烷基-3-(3,5-二-三級丁基-4-羥基苯基)丙酸酯、N,N'-己烷-1,6-二基雙[3-(3,5-二-三級丁基-4-羥基苯基)丙醯胺]、苯丙酸、3,5-雙(1,1-二甲基乙基)-4-羥基,C7至C9側鏈烷酯、2,4-二甲基-6-(1-甲基十五烷基)酚、二乙基[[3,5-雙(1,1-二甲基乙基)-4-羥基苯基]甲基]膦酸酯、3,3',3“,5,5',5”-六-三級丁基-a,a',a“-(均三甲苯-2,4,6-甲苯基)三-對甲酚、鈣二乙基雙[[3,5-雙(1,1-二甲基乙基)-4-羥基苯基]甲基]膦酸酯、4,6-雙(辛基硫甲基)鄰甲酚、伸乙基雙(氧伸乙基)雙[3-(5-三級丁基-4-羥基-間甲苯基)丙酸酯]、六亞甲基雙[3-(3,5-二-三級丁基-4-羥基苯基)丙酸酯、1,3,5-三(3,5-二-三級丁基-4-羥基苄基)-1,3,5-三嗪-2,4,6-(1H,3H,5H)-三酮、1,3,5-三[(4-三級丁基-3-羥基-2,6-二甲苯基)甲基]-1,3,5-三嗪-2,4,6-(1H,3H,5H)-三酮、N-苯基苯胺與2,4,6-三甲基戊烯之反應產物、2,6-二-三級丁基-4-(4,6-雙(辛硫基)-1,3,5-三嗪-2-基胺基)酚及苦味酸等之酚系化合物;三(2,4-二-三級丁基苯基)亞磷酸酯、三[2-[[2,4,8,10-四-三級丁基二苯并[d,f][1,3,2]二氧雜膦-6-基]氧基]乙基]胺、雙(2,4-二-三級丁基苯基)新戊四醇二亞磷酸酯、雙[2,4-雙(1,1-二甲基乙基)-6-甲基苯基]乙基酯亞磷酸、四(2,4-二-三級丁基苯基)[1,1-雙苯基]-4,4'-二基雙亞磷酸酯、6-[3-(3-三級丁基-4-羥基-5-甲基苯基)丙氧基]-2,4,8,10-四-三級
丁基二苯並[d,f][1,3,2]二氧雜磷雜環庚烯等磷系化合物;二月桂基-3,3'-硫二丙酸酯、二肉荳蔻基-3,3'-硫二丙酸酯、二硬脂基-3,3'-硫二丙酸酯、新戊四醇基四(3-月桂基硫丙酸酯)、內酯系化合物;維生素E系化合物等。其中,以酚系化合物為佳。
對本發明可添加密著賦予劑。上述密著賦予劑係可列舉如:γ-氯丙基三甲氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三氯矽烷、乙烯基三乙氧基矽烷、乙烯基-三(β-甲氧基乙氧基)矽烷、β-(3,4-環氧環己基)乙基三甲氧基矽烷、γ-環氧丙氧基丙基三甲氧基矽烷、γ-巰基丙基三甲氧基矽烷、γ-脲基丙基三乙氧基矽烷等。密著賦予劑之調配量,相對於(C)成分100質量份,以0.05至30質量份為佳,以0.2至10質量份更佳。
本發明之光硬化性樹脂組成物可依習知方法製造。例如:調配(A)至(E)成分的預定量,使用攪拌機等之混合裝置,藉由在10至70℃之溫度下混合0.1至5小時即可製造。
本發明之光硬化性樹脂組成物藉由紫外線、可見光等光的照射使其硬化時的光源並無特別限定,其例可列舉如:低壓汞燈、中壓汞燈、高壓汞燈、超高壓汞燈、黑光燈、微波激發汞燈、金屬鹵素燈、鈉燈、鹵素燈、氙燈、LED、螢光燈、日光及電子束照射裝置等。光照射之照射量,從硬化物的特性之觀點,係以10KJ/m2以上(包含10KJ/m2)為佳,以20KJ/m2以上(20KJ/m2)更佳。上述光照射之照射量的上限係以1000KJ/m2以下(包含1000KJ/m2)為佳。
本發明之光硬化性樹脂組成物係以作為(A)成分
之無色染料與酸的接觸而顯色,上述光硬化性樹脂組成物硬化而得的硬化物可顯色為黑色、藍色、綠色及紅色等。從遮蔽性優異之觀點上,上述硬化物係以黑色為佳。
本發明之光硬化性樹脂組成物適當地使用之用途係可列舉如:澆注用樹脂、密封劑、密封材料、灌封劑、接著劑、被覆材料、內襯材料及印墨等。其中上述用途方面,由於本發明之光硬化性樹脂組成物之貯存安定性優異、硬化物具有高的遮蔽性與優異之膜厚硬化性,故以澆注用樹脂、密封劑、灌封劑、接著劑或被覆材料之用途為佳。另外,在如此用途中使用時,本發明之光硬化性樹脂組成物以在25℃下為液態者為佳。
本發明之光硬化性樹脂組成物的特佳用途係可列舉如:撓性配線板用之被覆材料、澆注用樹脂、透鏡的黑色條紋、影像顯示裝置、光學構件、CMOS感測器、外殼及透鏡等之組裝用接著劑等。
以下,列舉實施例以更詳細地說明本發明,惟本發明並不限於該等實施例。
以表1所示之質量份取用各成分,在室溫(25℃)下以行星式攪拌機混合60分鐘,調製光硬化性樹脂組成物。另外,詳細的調製量係根據表1,數值全部以質量份表示。
a1:3-二丁基胺基-6-甲基-7-苯胺基螢光黃母體(ODB-2;山本化成股份有限公司製造)
a2:3-二乙基胺基-6-甲基-7-苯胺基螢光黃母體(ODB;山本化成股份有限公司製造)
a'1:碳黑(SRB黑色T-04;MIKUNI COLOR股份有限公司製造)
b1:三芳基鋶-六氟磷酸鹽(CPI-100P;SAN-APRO股份有限公司製造)
c1:胺基甲酸酯(甲基)丙烯酸酯(UV-3000B;日本合成化學工業股份有限公司製造)
c2:異氰脲酸EO改質二及三丙烯酸酯(M-313;東亞合成股份有限公司製造)
c3:二羥甲基-三環癸烷二丙烯酸酯(DCP-A;共榮社化學股份有限公司製造)
c4:丙烯酸異莰酯(Light Acrylate IBX-A;共榮社化學股份有限公司製造)
d1:2-羥基-2-甲基-1-苯基-丙-1-酮(DAROCUR1173;BASF公司製造)
d2:2,4,6-三甲基苄醯基-二苯基-膦氧化物(LUCIRIN TPO;BASF公司製造)
e1:丙烯醯基嗎福啉(ACMO;KJ Chemicals股份有限公司製造)
e2:三異丙醇胺(東京化成工業股份有限公司製造)
e3:三乙醇胺(東京化成工業股份有限公司製造)
e4:N-苯基二乙醇胺(東京化成工業股份有限公司製造)
e'1:N-羥甲基丙烯醯胺
e'2:甲基丙烯醯胺
e'3:1,3-雙胺基甲基環己烷(1,3-BAC;三菱瓦斯化學股份有限公司製造)
e'4:3,3'-二乙基-4,4'-二胺基二苯基甲烷(KAYAHARD A-A;日本化藥股份有限公司製造)
e'5:聚氧伸丙二胺(Jeffamine D-230)
e'6:間茬二胺(MXDA;三菱瓦斯化學股份有限
公司製造)。
實施例及比較例中使用之試驗方法係如下所述。
使光硬化性樹脂組成物之厚度成為0.5mm之方式,作成表面平滑之試驗片,使用LED照射機(波長365nm),在100mW/cm2×120秒的條件下照射紫外光,得到硬化物。該硬化物的外觀以肉眼觀察,將該結果彙整於表1。
使硬化性樹脂組成物之厚度成為0.5mm之方式,作成表面平滑之試驗片,使用LED照射機(波長365nm),在100mW/cm2×120秒的條件下照射紫外光,得到硬化物。在描有黑點之紙上放置所得之硬化物,以肉眼檢查黑點,並以下述基準進行評定。將該結果彙整於表1。
○:黑點的輪廓不清楚,可確認遮蔽性之情形。
×:黑點的輪廓清楚時而可確認。
將光硬化性樹脂組成物放入深度5mm之金屬管中,使用LED照射機(波長365nm),在100mW/cm2×120秒的條件下照射紫外光,使光硬化而得到硬化物。然後,藉由將未硬化部分以溶劑去除並將硬化部分以游標尺測定,求出膜
厚硬化性。將該結果彙整於表1。
另外,為使用在澆注用樹脂,係以1mm以上之膜厚硬化性為佳。
將硬化性樹脂組成物5g在25℃室內放入遮光容器中,密閉保存1個月,然後,根據以下標準以肉眼評定。將該結果彙整於表1。
○:保持液態,貯存安定性良好。
×:確認凝膠化。
如依表1,可知實施例1至7係含有(E)成分之3級胺化合物的光硬化性樹脂組成物,具有優異之膜厚硬化性,且硬化性具有高的遮蔽性,並具有優異之貯存安定性。
並且,比較例1係不具有本發明之(E)成分的光硬化性樹脂組成物,可知相較於實施例1至7,膜厚硬化性較差。並且,比較例2及3含有非為本發明之(E)成分的e'1、e'2成分之光硬化性樹脂組成物,惟無法溶解於本發明之(C)成分。而且,比較例4至7係含有非為本發明之(E)成分的1級或2級胺化合物之e'3至6的任一者之光硬化性樹脂組成物,惟在製造組成物時觀察到凝膠化,而有貯存安定性低劣之結果。而且,比較例8係含有非為本發明之(A)成分的碳黑之光硬化性樹脂組成物,由於碳黑吸收紫外光,故光硬化性樹脂組成物之膜厚硬化性有明顯惡化之結果。
使實施例1至7之各硬化性樹脂組成物之厚度成為150μm之方式,作成表面平滑之試驗片,在100mW/cm2×120秒的條件下照射紫外光而得到硬化物。將該硬化物之透過率於分光光度計UV-2450(島津製作所製造)測定(表1中並未記載)。實施例1至7之各硬化性樹脂組成物的硬化物之評定結果在550nm波長之透過率均為3%以下(包含3%),確認有優異之遮蔽性。
本發明之光硬化性樹脂組成物係貯存安定性優異,且具有高的遮蔽性與膜厚硬化性,故可應用在各種接著用途。具體而言,作為被覆材料、澆注用樹脂、密封劑、密封材料、灌封劑、接著劑、被覆材料、內襯材料及印墨等極為有效,可應用在廣泛的領域中。
順便提及,本發明的應用不限於上述實施形態,在不脫離本發明的主旨的範圍內可作適當地變更。
本申請案是依據2014年9月29日提出日本專利申請號2014-197803號,參照其揭示內容並將全部內容納入。
Claims (9)
- 一種光硬化性樹脂組成物,其含有下述(A)至(E)成分:(A)成分:無色染料(leuco dye)(B)成分:光酸產生劑(PAG:photo-acid generator)(C)成分:自由基聚合性化合物(具有3級胺骨架之(甲基)丙烯酸酯除外)(D)成分:光自由基聚合起始劑(E)成分:3級胺化合物;其中上述(E)成分係選自:N-苯基二乙醇胺、N-甲基二乙醇胺、p-甲基苯基二乙醇胺、N-乙基二乙醇胺、N-丙基二乙醇胺、N-丁基二乙醇胺、三乙醇胺、三丁醇胺、三異丙醇胺、N-甲基-二乙醇胺、N-甲基-二甲醇胺、三甲胺、三乙胺、三丁胺、N,N-二甲基-p-甲苯胺、N,N-二甲基-苯胺、N,N-(二甲基胺基)乙基-甲基丙烯酸酯、N,N-二甲基胺基苯乙酮、N,N-二甲基二苯基酮、N,N-二乙基胺基二苯基酮、N-甲基哌啶、N-乙基哌啶、N,N-二甲基苄基胺、N,N-二甲基環己基胺、丙烯醯基嗎福林、N-嗎福林基乙基(甲基)丙烯酸酯、N,N-二甲基胺基乙基(甲基)丙烯酸酯、N,N-二乙基胺基乙基(甲基)丙烯酸酯、N,N-二甲基胺基乙基(甲基)丙烯酸酯及N,N-二甲基胺基丙基(甲基)丙烯酸酯所成群組中之至少1種。
- 如請求項1之光硬化性樹脂組成物,其中相對於上述(C)成分100質量份,含有上述(E)成分0.01至200質量份。
- 如請求項1之光硬化性樹脂組成物,其中相對於上述(C)成分100質量份,含有上述(E)成分0.01至100質量份及(B)成分0.01至10質量份。
- 如請求項1之光硬化性樹脂組成物,其中上述(C)成分包含寡聚物與單體。
- 如請求項1之光硬化性樹脂組成物,其中上述(D)成分包含苯乙酮系光自由基聚合起始劑及醯基膦氧化物系光自由基聚合起始劑之至少1者。
- 如請求項1之光硬化性樹脂組成物,其中上述(B)成分係鎓鹽系光酸產生劑。
- 如請求項1之光硬化性樹脂組成物,其中上述(B)成分係芳基鋶鹽。
- 如請求項1之光硬化性樹脂組成物,其中之硬化物為黑色。
- 如請求項1至8中任一項之光硬化性樹脂組成物,其係澆注用樹脂、密封劑、灌封劑、接著劑或被覆材用光硬化性樹脂組成物。
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US10240026B2 (en) | 2019-03-26 |
US20170283584A1 (en) | 2017-10-05 |
WO2016051914A1 (ja) | 2016-04-07 |
KR20170065507A (ko) | 2017-06-13 |
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