CN102666676B - 膜及其用途 - Google Patents
膜及其用途 Download PDFInfo
- Publication number
- CN102666676B CN102666676B CN201080050850.2A CN201080050850A CN102666676B CN 102666676 B CN102666676 B CN 102666676B CN 201080050850 A CN201080050850 A CN 201080050850A CN 102666676 B CN102666676 B CN 102666676B
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- CN
- China
- Prior art keywords
- film
- sulfydryl
- group
- compound
- ester
- 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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- 239000011347 resin Substances 0.000 claims abstract description 49
- 229920005989 resin Polymers 0.000 claims abstract description 49
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims abstract description 39
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- 239000005864 Sulphur Substances 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 98
- 150000001875 compounds Chemical class 0.000 claims description 90
- 230000003287 optical effect Effects 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 14
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 10
- 125000002723 alicyclic group Chemical group 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 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 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 238000002834 transmittance Methods 0.000 claims description 5
- 238000005286 illumination Methods 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 10
- 230000005540 biological transmission Effects 0.000 abstract description 7
- -1 therefore Substances 0.000 description 169
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 110
- 239000000178 monomer Substances 0.000 description 50
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 46
- 239000000243 solution Substances 0.000 description 46
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 43
- 238000000034 method Methods 0.000 description 31
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 31
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 30
- 239000012948 isocyanate Substances 0.000 description 30
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000011521 glass Substances 0.000 description 24
- 150000002148 esters Chemical class 0.000 description 19
- 239000000463 material Substances 0.000 description 19
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 150000002513 isocyanates Chemical class 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000001294 propane Substances 0.000 description 14
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 description 13
- 239000001301 oxygen Substances 0.000 description 13
- 229910052760 oxygen Inorganic materials 0.000 description 13
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 13
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 11
- 150000003568 thioethers Chemical class 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 10
- 229940059574 pentaerithrityl Drugs 0.000 description 10
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 10
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 9
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 9
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 238000005266 casting Methods 0.000 description 9
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 9
- 239000008164 mustard oil Substances 0.000 description 9
- FYUYRLHJQHDYFF-UHFFFAOYSA-N 1-[1-sulfanyl-2-(2-sulfanylethylsulfanyl)ethyl]sulfanylpropane-2-thiol Chemical compound CC(S)CSC(S)CSCCS FYUYRLHJQHDYFF-UHFFFAOYSA-N 0.000 description 8
- 239000004593 Epoxy Chemical class 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 8
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- GRHBQAYDJPGGLF-UHFFFAOYSA-N isothiocyanic acid Chemical compound N=C=S GRHBQAYDJPGGLF-UHFFFAOYSA-N 0.000 description 7
- 239000003607 modifier Substances 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 102000013563 Acid Phosphatase Human genes 0.000 description 6
- 108010051457 Acid Phosphatase Proteins 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 241000534944 Thia Species 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 125000001246 bromo group Chemical group Br* 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 239000005357 flat glass Substances 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 239000005056 polyisocyanate Substances 0.000 description 6
- 229920001228 polyisocyanate Polymers 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 5
- 239000003490 Thiodipropionic acid Substances 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 235000019303 thiodipropionic acid Nutrition 0.000 description 5
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 4
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 4
- GVEDOIATHPCYGS-UHFFFAOYSA-N 1-methyl-3-(3-methylphenyl)benzene Chemical group CC1=CC=CC(C=2C=C(C)C=CC=2)=C1 GVEDOIATHPCYGS-UHFFFAOYSA-N 0.000 description 4
- KRXAVBPUAIKSFF-UHFFFAOYSA-N 3,4-dihydrodithiine Chemical compound C1CC=CSS1 KRXAVBPUAIKSFF-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- 239000004641 Diallyl-phthalate Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 229960004012 amifampridine Drugs 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920006295 polythiol Polymers 0.000 description 4
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 4
- YGKHJWTVMIMEPQ-UHFFFAOYSA-N 1,2-propanedithiol Chemical compound CC(S)CS YGKHJWTVMIMEPQ-UHFFFAOYSA-N 0.000 description 3
- CNDCQWGRLNGNNO-UHFFFAOYSA-N 2-(2-sulfanylethoxy)ethanethiol Chemical compound SCCOCCS CNDCQWGRLNGNNO-UHFFFAOYSA-N 0.000 description 3
- AYJPJKZAZUEBCT-UHFFFAOYSA-N 2-(methylsulfanylmethyl)-1,3-dithietane Chemical compound CSCC1SCS1 AYJPJKZAZUEBCT-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 3
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 3
- 239000005388 borosilicate glass Substances 0.000 description 3
- LIMQQADUEULBSO-UHFFFAOYSA-N butyl isothiocyanate Chemical compound CCCCN=C=S LIMQQADUEULBSO-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 150000001718 carbodiimides Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000004386 diacrylate group Chemical group 0.000 description 3
- 238000006471 dimerization reaction Methods 0.000 description 3
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 3
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 3
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 3
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 238000005829 trimerization reaction Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- VSWMPZHJMCIQIC-UHFFFAOYSA-N (hydroxymethyldisulfanyl)methanol Chemical compound OCSSCO VSWMPZHJMCIQIC-UHFFFAOYSA-N 0.000 description 2
- JRNVQLOKVMWBFR-UHFFFAOYSA-N 1,2-benzenedithiol Chemical compound SC1=CC=CC=C1S JRNVQLOKVMWBFR-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 2
- WQADWIOXOXRPLN-UHFFFAOYSA-N 1,3-dithiane Chemical compound C1CSCSC1 WQADWIOXOXRPLN-UHFFFAOYSA-N 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- KYNFOMQIXZUKRK-UHFFFAOYSA-N 2,2'-dithiodiethanol Chemical compound OCCSSCCO KYNFOMQIXZUKRK-UHFFFAOYSA-N 0.000 description 2
- CXOWYJMDMMMMJO-UHFFFAOYSA-N 2,2-dimethylpentane Chemical compound CCCC(C)(C)C CXOWYJMDMMMMJO-UHFFFAOYSA-N 0.000 description 2
- DLLMHEDYJQACRM-UHFFFAOYSA-N 2-(carboxymethyldisulfanyl)acetic acid Chemical compound OC(=O)CSSCC(O)=O DLLMHEDYJQACRM-UHFFFAOYSA-N 0.000 description 2
- IYQVQZXLTJHEKZ-UHFFFAOYSA-N 2-(ethylsulfanyl)ethanethiol Chemical compound CCSCCS IYQVQZXLTJHEKZ-UHFFFAOYSA-N 0.000 description 2
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical compound CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 description 2
- CCXLOQVMDTWRSP-UHFFFAOYSA-N 2-cyclohexylpropan-2-ylcyclohexane Chemical compound C1CCCCC1C(C)(C)C1CCCCC1 CCXLOQVMDTWRSP-UHFFFAOYSA-N 0.000 description 2
- VHBFEIBMZHEWSX-UHFFFAOYSA-N 2-isothiocyanatopropane Chemical compound CC(C)N=C=S VHBFEIBMZHEWSX-UHFFFAOYSA-N 0.000 description 2
- ZMRFRBHYXOQLDK-UHFFFAOYSA-N 2-phenylethanethiol Chemical compound SCCC1=CC=CC=C1 ZMRFRBHYXOQLDK-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- OIHIYRYYEMJNPB-UHFFFAOYSA-N 3,6-dihydrodithiine Chemical compound C1SSCC=C1 OIHIYRYYEMJNPB-UHFFFAOYSA-N 0.000 description 2
- RXURJOBHVPLGQU-UHFFFAOYSA-N 3-(3-hydroxypropyldisulfanyl)propan-1-ol Chemical compound OCCCSSCCCO RXURJOBHVPLGQU-UHFFFAOYSA-N 0.000 description 2
- QRQVZZMTKYXEKC-UHFFFAOYSA-N 3-(3-hydroxypropylsulfanyl)propan-1-ol Chemical compound OCCCSCCCO QRQVZZMTKYXEKC-UHFFFAOYSA-N 0.000 description 2
- DGUJJOYLOCXENZ-UHFFFAOYSA-N 4-[2-[4-(oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenol Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 DGUJJOYLOCXENZ-UHFFFAOYSA-N 0.000 description 2
- CKDSFRWKHBYHHT-UHFFFAOYSA-N 4-bicyclo[2.2.1]heptanylmethanamine Chemical compound C1CC2CCC1(CN)C2 CKDSFRWKHBYHHT-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XMENXMPHLHKOCS-UHFFFAOYSA-N C1=CC=CC=C1.S1SCSC1 Chemical compound C1=CC=CC=C1.S1SCSC1 XMENXMPHLHKOCS-UHFFFAOYSA-N 0.000 description 2
- 239000004970 Chain extender Substances 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- CETBSQOFQKLHHZ-UHFFFAOYSA-N Diethyl disulfide Chemical compound CCSSCC CETBSQOFQKLHHZ-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C41/00—Shaping by coating a mould, core or other substrate, i.e. by depositing material and stripping-off the shaped article; Apparatus therefor
- B29C41/003—Shaping by coating a mould, core or other substrate, i.e. by depositing material and stripping-off the shaped article; Apparatus therefor characterised by the choice of material
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/0074—Production of other optical elements not provided for in B29D11/00009- B29D11/0073
- B29D11/00788—Producing optical films
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
- C08G18/7642—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the aromatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate groups, e.g. xylylene diisocyanate or homologues substituted on the aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- C—CHEMISTRY; METALLURGY
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Abstract
本发明的膜的特征在于,由具有硫代氨基甲酸酯键的树脂构成,该树脂中含有的硫与氮的摩尔比(S/N)为0.8以上、小于3。根据本申请的发明提供一种在高折射率、低双折射率及透光性的均衡性方面优异的膜,进而,该膜在韧性、刚性、尺寸稳定性等机械特性的均衡性方面优异,加工时的变形等的影响极小,另外在耐溶剂性方面也优异。
Description
技术领域
本发明涉及膜及其用途。
背景技术
专利文献1中记载了由硫代氨基甲酸酯类树脂形成的光学材料。此外,专利文献2中记载了由使用规定的催化剂制造的聚硫代氨基甲酸酯形成的光学材料。而且记载了这些树脂具有高折射率及高透明性等,在光学材料中可适合用于塑料透镜。
但是,没有公开将硫代氨基甲酸酯类树脂以1mm以下的厚度形成膜/膜状时的物性、以该薄膜形状与其他材料相接触来使用并作为整体控制光通过的用法。此外,当将这些树脂薄膜化时,从原料的反应性的观点考虑,涂布存在困难,对于得到稳定的膜/薄膜的方法也没有研究。
专利文献3中记载了具有将聚硫代氨基甲酸酯骨架引入聚硫代碳酸酯骨架而形成的结构的光学材料。记载了由该光学材料得到的膜的高折射率、高阿贝数等光学特性优异,而且拉伸特性、高伸缩性等力学特性也优异。而且,该文献中记载了利用树脂溶液的浇铸(溶液流延)法由上述光学材料形成膜的例子。
专利文献1:日本特开平2-270859号公报
专利文献2:国际公开2007/97116号说明书
专利文献3:日本特开2005-336476号公报
发明内容
但是,对于上述文献3记载的树脂来说,由于合成步骤多,所以在将其形成膜时,存在品质维持和成本上的问题,此外,从上述文献3记载的树脂形成膜的方法也存在如下问题:由于在完成聚合之后用溶液进行浇铸(溶液流延),所以在制造时需要额外的工作和成本来除去溶剂,而且难于控制聚合度和厚度,在形成的膜的折射率、双折射率、透光性的均衡性方面存在改善余地。
即,本发明如下所示。
(1)一种膜,其特征在于,由具有硫代氨基甲酸酯键的树脂构成,该树脂中含有的硫与氮的摩尔比(S/N)为0.8以上、小于3。
(2)如(1)所述的膜,其特征在于,钠D线中的折射率为1.6以上,波长590nm处的膜厚1~200μm的膜的正面双折射率Δnxy为1.0×10-2以下,厚度方向的双折射率Δnxz为1.0×10-3以下,相对于波长400~800nm的光的透光率的平均值为80%以上。
(3)如(1)或(2)所述的膜,其特征在于,具有硫代氨基甲酸酯键的树脂在结构中具有芳香族基团、杂环基团或脂环族基团。
(4)如(1)~(3)中任一项所述的膜,是通过浇铸(薄膜涂布-聚合固化)法得到的。
(5)如(1)~(3)中任一项所述的膜,是利用浇铸(薄膜涂布-聚合固化)法由具有异氰酸酯基的化合物及具有硫醇基的化合物的混合物得到的,所述混合物部分地具有硫代氨基甲酸酯键、而且可形成硫代氨基甲酸酯。
(6)如(1)~(3)中任一项所述的膜,是通过将具有异氰酸酯基的化合物及具有硫醇基的化合物的混合物注入到200μm以下间隔的面间并使其聚合固化而得到的,所述混合物部分地具有硫代氨基甲酸酯键、而且可形成硫代氨基甲酸酯。
(7)如(5)或(6)所述的膜,其中,上述具有硫醇的化合物至少包括一种具有3个以上巯基的化合物。
(8)一种光学膜,是由(1)~(7)中任一项所述的膜形成的。
(9)一种光学构件,使(8)所述的光学膜形成于其内部或外部。
(10)一种显示器,具备(8)所述的光学膜。
(11)一种发光设备,使(8)所述的光学膜形成于其内部或外部。
(12)一种照明装置,使用了(11)所述的发光设备。
(13)一种图像显示装置,使用了(11)所述的发光设备。
需要说明的是,本发明的膜还包括片层形状的膜,另外还包括在基材上进行薄膜涂布并使其固化、连同该基材一起直接使用的膜。
本发明的膜的高折射率、低双折射率及透光性的均衡性优异,而且,韧性、刚性、尺寸稳定性等机械特性的均衡性优异,加工时的变形等的影响极小,此外,耐溶剂性也优异,因此可作为多种光学膜使用。
具体实施方式
以下,详细地说明本发明。
[膜]
本发明的膜由具有硫代氨基甲酸酯键的树脂构成。对于构成本发明的膜的树脂来说,相对于作为聚合反应性键的硫代氨基甲酸酯键数目,可以具有相对少的硫原子数,从而聚合过程比较简便地完成。该树脂中含有的硫与氮的摩尔比(S/N)为0.8以上、小于3,优选0.8以上、2.8以下,更优选0.9以上、2.2以下。
通过使硫与氮的摩尔比(S/N)包含于上述范围内,本发明的膜的高折射率、低双折射率及透光性等的光学特性的均衡性优异,而且韧性等机械特性和耐溶剂性也优异。
具体而言,膜具有以下特性。
钠D线中的折射率为1.6以上,优选1.64以上。
波长590nm处的膜厚1~200μm的膜的正面双折射率Δnxy为1.0×10-2以下,优选为1.0×10-3以下,较优选为2.0×10-5以下,更优选为1.1×10-5以下。此外,厚度方向的双折射率Δnxz为1.0×10-3以下,更优选为8.0×10-4以下。
相对于波长400~800nm的光的平均透光率为80%以上,优选为85%以上,更优选为88%以上。
正面双折射率Δnxy定义为nx-ny,正面延迟(in-planeretardation)Re定义为Δnxy×d。
(nx:膜面内的滞相轴方向的折射率,ny:膜面内的进相轴方向的折射率,d为膜的厚度(单位:nm))
此外,厚度方向的双折射率Δnxz定义为(nx+ny)/2-nz,厚度方向的延迟Rth定义为Δnxz×d。
(nx:膜面内的滞相轴方向的折射率,ny:膜面内的进相轴方向的折射率,nz:膜厚度方向的折射率,d为膜的厚度(单位:nm))
本发明的膜由于高折射率、低双折射率及透光性的均衡性优异,所以可合适地用于光学用途。另外,本发明的膜的强韧性优异,由热固性树脂形成,因此,耐溶剂性也优异。需要说明的是,上述数值范围可任意组合。
本发明的膜的断裂伸长率为3~6%。另外,通过拉伸强度试验测定的拉伸弹性模量为3GPa以上。由于上述机械特性优异,所以使用了本发明的膜的产品的成品率提高,同时产品可靠性也提高。因此,可更合适地用于各种光学膜。
此外,对于本发明的膜来说,其厚度为0.1~1000μm,也可使用1~1000μm的膜。从低双折射率的观点考虑,优选为0.1~200μm,尤其是,在基材上进行薄膜涂布-聚合固化之后从基材剥离使用的、或在浇铸聚合后从模剥离使用的自支持膜(self-supportfilm)的情况,优选为10~200μm。
此外,水蒸气或氧等各种气体的阻隔性、尤其是水蒸气阻隔性优异,可用作液晶显示元件、太阳能电池、有机电致发光元件(organicelectroluminescencedevice)等的透明基材。
对于本发明的膜的水蒸气透过率来说,依照JISZ0208,在温度60℃、90%RH、膜厚100μm的条件下测定的值为10g/m2·24hr以下。
以下,对构成本发明的膜的、具有硫代氨基甲酸酯键的树脂进行说明。
<具有硫代氨基甲酸酯键的树脂>
本发明中使用的具有硫代氨基甲酸酯键的含有硫原子的树脂通过将以下的聚合性组合物聚合而得到。
聚合性组合物以选自异氰酸酯化合物及异硫氰酸酯化合物中的一种或两种以上的异氰酸酯类、和具有巯基的一种或两种以上的活性氢化合物为主成分形成,但为了将聚硫代氨基甲酸酯树脂改性,可以进一步加入羟基化合物。
本发明中,作为具有硫代氨基甲酸酯键的树脂的原料使用的、异氰酸酯化合物的优选的具体例子,可列举:异氰酸甲酯、异氰酸乙酯、异氰酸正丙酯、异氰酸异丙酯、异氰酸正丁酯、异氰酸仲丁酯、异氰酸叔丁酯、异氰酸戊酯、异氰酸己酯、异氰酸庚酯、异氰酸辛酯、异氰酸癸酯、异氰酸十二烷基酯、异氰酸肉豆蔻基酯、异氰酸十八烷基酯、异氰酸3-戊基酯、异氰酸2-乙基己基酯、异氰酸2,3-二甲基环己基酯、异氰酸2-甲氧基苯基酯、异氰酸4-甲氧基苯基酯、异氰酸α-甲基苄基酯、异氰酸苯乙基酯、异氰酸苯基酯、异氰酸邻、间、对甲苯基酯、异氰酸环己基酯、异氰酸苄基酯、异氰酸甲酯基双环庚烷等单官能异氰酸酯化合物;及
1,6-己二异氰酸酯、2,2-二甲基戊烷二异氰酸酯、2,2,4-三甲基己烷二异氰酸酯、丁烯二异氰酸酯、1,3-丁二烯-1,4-二异氰酸酯、2,4,4-三甲基1,6-己二异氰酸酯、1,6,11-十一烷三异氰酸酯、1,3,6-六亚甲基三异氰酸酯、1,8-二异氰酸酯基-4-异氰酸甲酯基辛烷、双(异氰酸乙酯基)碳酸酯、双(异氰酸乙酯基)醚、赖氨酸甲酯二异氰酸酯、赖氨酸三异氰酸酯等脂肪族多异氰酸酯化合物;及
异佛尔酮二异氰酸酯、1,3-双(异氰酸甲酯基)环己烷、1,4-双(异氰酸甲酯基)环己烷、二环己基甲烷二异氰酸酯、环己烷二异氰酸酯、甲基环己烷二异氰酸酯、二环己基二甲基甲烷异氰酸酯、2,2-二甲基二环己基甲烷异氰酸酯、2,5-双(异氰酸甲酯基)双环-[2,2,1]-庚烷、2,6-双(异氰酸甲酯基)双环-[2,2,1]-庚烷、3,8-双(异氰酸甲酯基)三环癸烷、3,9-双(异氰酸甲酯基)三环癸烷、4,8-双(异氰酸甲酯基)三环癸烷、4,9-双(异氰酸甲酯基)三环癸烷等脂环族多异氰酸酯化合物;及
苯二异氰酸酯、邻苯二甲撑二异氰酸酯、对苯二甲撑二异氰酸酯、间苯二甲撑二异氰酸酯、双(异氰酸乙酯基)苯、双(异氰酸丙酯基)苯、α,α,α′,α′-四甲基苯二甲撑二异氰酸酯、双(异氰酸丁酯基)苯、双(异氰酸甲酯基)萘、双(异氰酸甲酯基)二苯基醚、苯二异氰酸酯、甲苯二异氰酸酯、乙苯二异氰酸酯、异丙基苯二异氰酸酯、二甲基苯二异氰酸酯、二乙基苯二异氰酸酯、二异丙基苯二异氰酸酯、三甲基苯三异氰酸酯、苯三异氰酸酯、联苯二异氰酸酯、甲苯胺二异氰酸酯、4,4-二苯基甲烷二异氰酸酯、3,3-二甲基二苯基甲烷-4,4-二异氰酸酯、联苄基-4,4-二异氰酸酯、双(异氰酸苯酯基)乙烯、3,3-二甲氧基联苯-4,4-二异氰酸酯、苯基异氰酸乙酯基异氰酸酯、六氢苯二异氰酸酯、六氢二苯基甲烷-4,4-二异氰酸酯、双(异氰酸乙酯基)邻苯二甲酸酯、苯均三亚甲基三异氰酸酯(mesitylylenetriisocyanate)、2,6-二(异氰酸甲酯基)呋喃等芳香族多异氰酸酯化合物;及
双(异氰酸乙酯基)硫醚、双(异氰酸丙酯基)硫醚、双(异氰酸己酯基)硫醚、双(异氰酸甲酯基)砜、双(异氰酸甲酯基)二硫醚、双(异氰酸丙酯基)二硫醚、双(异氰酸甲酯基硫基)甲烷、双(异氰酸乙酯基硫基)甲烷、双(异氰酸乙酯基硫基)乙烷、双(异氰酸甲酯基硫基)乙烷、1,5-二异氰酸酯基-2-异氰酸甲酯基-3-硫杂戊烷等含硫脂肪族多异氰酸酯化合物;及
二苯基硫醚-2,4-二异氰酸酯、二苯基硫醚-4,4-二异氰酸酯、3,3-二甲氧基-4,4-二异氰酸酯基二苄基硫醚、双(4-异氰酸甲酯基苯)硫醚、4,4-甲氧基苯硫基乙二醇-3,3-二异氰酸酯、二苯基二硫醚-4,4-二异氰酸酯、2,2-二甲基二苯基二硫醚-5,5-二异氰酸酯、3,3-二甲基二苯基二硫醚-5,5-二异氰酸酯、3,3-二甲基二苯基二硫醚-6,6-二异氰酸酯、4,4-二甲基二苯基二硫醚-5,5-二异氰酸酯、3,3-二甲氧基二苯基二硫醚-4,4-二异氰酸酯、4,4-二甲氧基二苯基二硫醚-3,3-二异氰酸酯等含硫芳香族多异氰酸酯化合物;及
2,5-二异氰酸酯基噻吩、2,5-双(异氰酸甲酯基)噻吩、2,5-二异氰酸酯基四氢噻吩、2,5-双(异氰酸甲酯基)四氢噻吩、3,4-双(异氰酸甲酯基)四氢噻吩、2,5-二异氰酸酯基-1,4-二噻烷、2,5-双(异氰酸甲酯基)-1,4-二噻烷、4,5-二异氰酸酯基-1,3-二硫戊环、4,5-双(异氰酸甲酯基)-1,3-二硫戊环、4,5-双(异氰酸甲酯基)-2-甲基-1,3-二硫戊环等含硫杂环多异氰酸酯化合物等,但不限于这些示例化合物
也可以使用上述化合物的氯取代物、溴取代物等卤素取代物、烷基取代物、烷氧基取代物、硝基取代物、和多元醇的预聚物型改性体、碳二亚胺改性体、脲改性体、缩二脲改性体、二聚物化或三聚物化反应生成物等。上述异氰酸酯化合物可以单独使用,也可以混合2种以上进行使用。
本发明中,用作具有硫代氨基甲酸酯键的树脂的原料的异硫氰酸酯化合物选自异硫氰酸酯化合物及具有异氰酸酯基的异硫氰酸酯化合物。
作为本发明中使用的异硫氰酸酯化合物的优选的具体例子,可以举出异硫氰酸甲酯、异硫氰酸乙酯、异硫氰酸正丙酯、异硫氰酸异丙酯、异硫氰酸正丁酯、异硫氰酸仲丁酯、异硫氰酸叔丁酯、异硫氰酸戊酯、异硫氰酸己酯、异硫氰酸庚酯、异硫氰酸辛酯、异硫氰酸癸酯、异硫氰酸十二烷基酯、异硫氰酸十四烷基酯、异硫氰酸十八烷基酯、异硫氰酸3-戊基酯、异硫氰酸2-乙基己基酯、异硫氰酸2,3-二甲基环己基酯、异硫氰酸2-甲氧基苯基酯、异硫氰酸4-甲氧基苯基酯、异硫氰酸α-甲基苄基酯、异硫氰酸苯基乙基酯、异硫氰酸苯基酯、异硫氰酸邻、间、对甲苯基酯、异硫氰酸环己基酯、异硫氰酸苄基酯、异硫氰酸甲酯基双环庚烷等单官能异硫氰酸酯化合物;及
1,6-己二异硫氰酸酯、2,2-二甲基戊烷二异硫氰酸酯、2,2,4-三甲基己烷二异硫氰酸酯、丁烯二异硫氰酸酯、1,3-丁二烯-1,4-二异硫氰酸酯、2,4,4-三甲基1,6-己二异硫氰酸酯、1,6,11-十一烷三异硫氰酸酯、1,3,6-六亚甲基三异硫氰酸酯、1,8-二异硫氰酸酯基-4-异硫氰酸甲酯基辛烷、双(异硫氰酸乙酯基)碳酸酯、双(异硫氰酸乙酯基)醚、赖氨酸甲酯二异硫氰酸酯、赖氨酸三异硫氰酸酯、苯二甲撑二异硫氰酸酯、双(异硫氰酸乙酯基)苯、双(异硫氰酸丙酯基)苯、α,α,α′,α′-四甲基苯二甲撑二异硫氰酸酯、双(异硫氰酸丁酯基)苯、双(异硫氰酸甲酯基)萘、双(异硫氰酸甲酯基)二苯基醚、双(异硫氰酸乙酯基)邻苯二甲酸酯、苯均三亚甲基三异硫氰酸酯、2,6-二(异硫氰酸甲酯基)呋喃等脂肪族多异硫氰酸酯化合物;及
异佛尔酮二异硫氰酸酯、双(异硫氰酸甲酯基)环己烷、二环己基甲烷二异硫氰酸酯、环己烷二异硫氰酸酯、甲基环己烷二异硫氰酸酯、二环己基二甲基甲烷异硫氰酸酯、2,2-二甲基二环己基甲烷异硫氰酸酯、2,5-双(异硫氰酸甲酯基)双环-[2,2,1]-庚烷、2,6-双(异硫氰酸甲酯基)双环-[2,2,1]-庚烷、3,8-双(异硫氰酸甲酯基)三环癸烷、3,9-双(异硫氰酸甲酯基)三环癸烷、4,8-双(异硫氰酸甲酯基)三环癸烷、4,9-双(异硫氰酸甲酯基)三环癸烷等脂环族多异硫氰酸酯化合物;及
苯二异硫氰酸酯、甲苯二异硫氰酸酯、乙基苯二异硫氰酸酯、异丙基苯二异硫氰酸酯、二甲基苯二异硫氰酸酯、二乙基苯二异硫氰酸酯、二异硫基丙基苯二异硫氰酸酯、三甲基苯三异硫氰酸酯、苯三异硫氰酸酯、联苯二异硫氰酸酯、甲苯胺二异硫氰酸酯、4,4-二苯基甲烷二异硫氰酸酯、3,3-二甲基二苯基甲烷-4,4-二异硫氰酸酯、联苄基-4,4-二异硫氰酸酯、双(异硫氰酸苯酯基)乙烯、3,3-二甲氧基联苯基-4,4-二异硫氰酸酯、苯基异硫氰酸乙酯基异硫氰酸酯、六氢苯二异硫氰酸酯、六氢二苯基甲烷-4,4-二异硫氰酸酯等芳香族多异硫氰酸酯化合物;及
双(异硫氰酸乙酯基)硫醚、双(异硫氰酸丙酯基)硫醚、双(异硫氰酸己酯基)硫醚、双(异硫氰酸甲酯基)砜、双(异硫氰酸甲酯基)二硫醚、双(异硫氰酸丙酯基)二硫醚、双(异硫氰酸甲酯基硫基)甲烷、双(异硫氰酸乙酯基硫基)甲烷、双(异硫氰酸乙酯基硫基)乙烷、双(异硫氰酸甲酯基硫基)乙烷、1,5-二异硫氰酸酯基-2-异硫氰酸甲酯基-3-硫杂戊烷等含硫脂肪族多异硫氰酸酯化合物;及
二苯基硫醚-2,4-二异硫氰酸酯、二苯基硫醚-4,4-二异硫氰酸酯、3,3-二甲氧基-4,4-二异硫氰酸酯基二苄基硫醚、双(4-异硫氰酸甲酯基苯)硫醚、4,4-甲氧基苯硫基乙二醇-3,3-二异硫氰酸酯、二苯基二硫醚-4,4-二异硫氰酸酯、2,2-二甲基二苯基二硫醚-5,5-二异硫氰酸酯、3,3-二甲基二苯基二硫醚-5,5-二异硫氰酸酯、3,3-二甲基二苯基二硫醚-6,6-二异硫氰酸酯、4,4-二甲基二苯基二硫醚-5,5-二异硫氰酸酯、3,3-二甲氧基二苯基二硫醚-4,4-二异硫氰酸酯、4,4-二甲氧基二苯基二硫醚-3,3-二异硫氰酸酯等含硫芳香族多异硫氰酸酯化合物;及
2,5-二异硫氰酸酯基噻吩、2,5-双(异硫氰酸甲酯基)噻吩、2,5-二异硫氰酸酯基四氢噻吩、2,5-双(异硫氰酸甲酯基)四氢噻吩、3,4-双(异硫氰酸甲酯基)四氢噻吩、2,5-二异硫氰酸酯基-1,4-二噻烷、2,5-双(异硫氰酸甲酯基)-1,4-二噻烷、4,5-二异硫氰酸酯基-1,3-二硫戊环、4,5-双(异硫氰酸甲酯基)-1,3-二硫戊环、4,5-双(异硫氰酸甲酯基)-2-甲基-1,3-二硫戊环等含硫杂环多异硫氰酸酯化合物等,但并不限于这些列举的化合物。
也可以使用上述化合物的氯取代物、溴取代物等卤素取代物、烷基取代物、烷氧基取代物、硝基取代物或与多元醇的预聚物型改性体、碳二亚胺改性体、脲改性体、缩二脲改性体、二聚物化或三聚物化反应生成物等。上述异硫氰酸酯化合物可以单独使用,也可以混合2种以上进行使用。
作为本发明中用作原料的具有异氰酸酯基的异硫氰酸酯化合物,例如可以举出1-异氰酸酯基-3-异硫氰酸酯基丙烷、1-异氰酸酯基-5-异硫氰酸酯基戊烷、1-异氰酸酯基-6-异硫氰酸酯基己烷、异氰酸酯基羰基异硫氰酸酯、1-异氰酸酯基-4-异硫氰酸酯基环己烷等脂肪族或脂环族化合物;及
1-异氰酸酯基-4-异硫氰酸酯基苯、4-甲基-3-异氰酸酯基-1-异硫氰酸酯基苯等芳香族化合物;及
2-异氰酸酯基-4,5-二异硫氰酸酯基-1,3,5-三嗪等杂环式化合物;及
4-异氰酸酯基-4′-异硫氰酸酯基二苯基硫醚、2-异氰酸酯基-2′-异硫氰酸酯基二乙基二硫醚等异硫氰酸酯基,还可以举出上述化合物的硫取代化合物。
进而,也可以使用上述化合物的氯取代物、溴取代物等卤素取代物、烷基取代物、烷氧基取代物、硝基取代物或和多元醇的预聚物型改性体、碳二亚胺改性体、脲改性体、缩二脲改性体、二聚物化或三聚物化反应生成物等。
本发明中,从提高折射率或提高耐热性的观点考虑,优选具有硫代氨基甲酸酯键的树脂在结构中具有芳香族基团、杂环基团或脂环族基团。即,作为异氰酸酯类,优选使用具有芳香族基团、杂环基团或脂环族基团的化合物。
上述异氰酸酯类可以分别单独使用,还可以混合二种以上进行使用。作为异氰酸酯类,较优选苯二异氰酸酯、间苯二甲撑二异氰酸酯、2,5-双(异氰酸甲酯基)-双环[2.2.1]庚烷、2,6-双(异氰酸甲酯基)-双环〔2.2.1〕庚烷、1,3-双(异氰酸甲酯基)环己烷、1,4-双(异氰酸甲酯基)环己烷、1,6-己二异氰酸酯、甲苯二异氰酸酯、4,4-二苯基甲烷二异氰酸酯,特别优选苯二异氰酸酯、间苯二甲撑二异氰酸酯、甲苯二异氰酸酯、4,4-二苯基甲烷二异氰酸酯、2,5-双(异氰酸甲酯基)-双环[2.2.1]庚烷、2,6-双(异氰酸甲酯基)-双环〔2.2.1〕庚烷。
本发明中,从提高折射率的观点考虑,优选具有硫代氨基甲酸酯键的树脂在结构中具有芳香族基团、杂环基团或脂环族基团。即,作为异氰酸酯类,优选使用具有芳香族基团、杂环基团或脂环族基团的化合物。
本发明中,上述异氰酸酯类中,通过使用具有芳香环的异氰酸酯类,可以得到具有高折射率的树脂。
用作具有硫代氨基甲酸酯键的树脂的原料的具有巯基的活性氢化合物选自巯基化合物及具有羟基的巯基化合物。
作为本发明中使用的巯基化合物,例如可以举出甲二硫醇、1,2-乙二硫醇、1,1-丙二硫醇、1,2-丙二硫醇、1,3-丙二硫醇、2,2-丙二硫醇、1,4-丁二硫醇、2,3-丁二硫醇、1,5-戊二硫醇、1,6-己二硫醇、1,2,3-丙三硫醇、1,1-环己二硫醇、1,2-环己二硫醇、2,2-二甲基丙烷-1,3-二硫醇、3,4-二甲氧基丁烷-1,2-二硫醇、2-甲基环己烷-2,3-二硫醇、1,1-双(巯基甲基)环己烷、1,2-二巯基丙基甲基醚、2,3-二巯基丙基甲基醚、2,2-双(巯基甲基)-1,3-丙二硫醇、双(2-巯基乙基)醚、四(巯基甲基)甲烷等脂肪族多硫醇化合物;及
2,3-二巯基琥珀酸(2-巯基乙基酯)、硫代苹果酸双(2-巯基乙基酯)、2,3-二巯基-1-丙醇(2-巯基乙酸酯)、2,3-二巯基-1-丙醇(3-巯基丙酸酯)、3-巯基-1,2-丙二醇双(2-巯基乙酸酯)、3-巯基-1,2-丙二醇双(3-巯基丙酸酯)、二甘醇双(2-巯基乙酸酯)、二甘醇双(3-巯基丙酸酯)、乙二醇双(2-巯基乙酸酯)、乙二醇双(3-巯基丙酸酯)、三羟甲基丙烷三(2-巯基乙酸酯)、三羟甲基丙烷三(3-巯基丙酸酯)、三羟甲基乙烷三(2-巯基乙酸酯)、三羟甲基乙烷三(3-巯基丙酸酯)、季戊四醇四(2-巯基乙酸酯)、季戊四醇四(3-巯基丙酸酯)、丙三醇三(2-巯基乙酸酯)、丙三醇三(3-巯基丙酸酯)、1,4-环己二醇双(2-巯基乙酸酯)、1,4-环己二醇双(3-巯基丙酸酯)等含有酯键的脂肪族多硫醇化合物;及
1,2-二巯基苯、1,3-二巯基苯、1,4-二巯基苯、1,2-双(巯基甲基)苯、1,3-双(巯基甲基)苯、1,4-双(巯基甲基)苯、1,2-双(巯基乙基)苯、1,3-双(巯基乙基)苯、1,4-双(巯基乙基)苯、1,2-双(巯基亚甲基氧基)苯、1,3-双(巯基亚甲基氧基)苯、1,4-双(巯基亚甲基氧基)苯、1,2-双(巯基亚乙基氧基)苯、1,3-双(巯基亚乙基氧基)苯、1,4-双(巯基亚乙基氧基)苯、1,2,3-三巯基苯、1,2,4-三巯基苯、1,3,5-三巯基苯、1,2,3-三(巯基甲基)苯、1,2,4-三(巯基甲基)苯、1,3,5-三(巯基甲基)苯、1,2,3-三(巯基乙基)苯、1,2,4-三(巯基乙基)苯、1,3,5-三(巯基乙基)苯、1,2,3-三(巯基亚甲基氧基)苯、1,2,4-三(巯基亚甲基氧基)苯、1,3,5-三(巯基亚甲基氧基)苯、1,2,3-三(巯基亚乙基氧基)苯、1,2,4-三(巯基亚乙基氧基)苯、1,3,5-三(巯基亚乙基氧基)苯、2,5-甲苯二硫醇、3,4-甲苯二硫醇、1,3-二(对甲氧基苯基)丙烷-2,2-二硫醇、1,3-二苯基丙烷-2,2-二硫醇、苯基甲烷-1,1-二硫醇、2,4-二(对巯基苯基)戊烷、1,4-萘二硫醇、1,5-萘二硫醇、2,6-萘二硫醇、2,7-萘二硫醇、2,4-二甲苯-1,3-二硫醇、4,5-二甲苯-1,3-二硫醇、9,10-蒽二甲硫醇、1,2,3,4-四巯基苯、1,2,3,5-四巯基苯、1,2,4,5-四巯基苯、1,2,3,4-四(巯基甲基)苯、1,2,3,5-四(巯基甲基)苯、1,2,4,5-四(巯基甲基)苯、1,2,3,4-四(巯基乙基)苯、1,2,3,5-四(巯基乙基)苯、1,2,4,5-四(巯基乙基)苯、1,2,3,4-四(巯基亚甲基氧基)苯、1,2,3,5-四(巯基亚甲基氧基)苯、1,2,4,5-四(巯基亚甲基氧基)苯、1,2,3,4-四(巯基亚乙基氧基)苯、1,2,3,5-四(巯基亚乙基氧基)苯、1,2,4,5-四(巯基亚乙基氧基)苯、2,2′-二巯基联苯、4,4′-二巯基联苯、4,4′-二巯基联苄、2,5-二氯苯-1,3-二硫醇、1,3-二(对氯苯基)丙烷-2,2-二硫醇、3,4,5-三溴-1,2-二巯基苯、2,3,4,6-四氯-1,5-双(巯基甲基)苯等芳香族多硫醇化合物;及
2-甲基氨基-4,6-二硫醇-均三嗪、2-乙基氨基-4,6-二硫醇-均三嗪、2-氨基-4,6-二硫醇-均三嗪、2-吗啉基-4,6-二硫醇-均三嗪、2-环己基氨基-4,6-二硫醇-均三嗪、2-甲氧基-4,6-二硫醇-均三嗪、2-苯氧基-4,6-二硫醇-均三嗪、2-硫代苯氧基-4,6-二硫醇-均三嗪、2-硫代丁基氧基-4,6-二硫醇-均三嗪等杂环硫醇化合物及上述化合物的卤素取代化合物等,但并不仅限于这些列举的化合物。
进而,可以使用上述化合物的氯取代物、溴取代物等卤素取代物。上述巯基化合物可以单独使用,也可以混合2种以上进行使用。
作为1分子中具有1个以上硫醚键的巯基化合物,可以举出双(巯基甲基)硫醚、双(巯基甲基)二硫醚、双(巯基乙基)硫醚、双(巯基乙基)二硫醚、双(巯基丙基)硫醚、双(巯基甲硫基)甲烷、双(2-巯基乙硫基)甲烷、双(3-巯基丙硫基)甲烷、1,2-双(巯基甲硫基)乙烷、1,2-双(2-巯基乙硫基)乙烷、1,2-双(3-巯基丙硫基)乙烷、1,3-双(巯基甲硫基)丙烷、1,3-双(2-巯基乙硫基)丙烷、1,3-双(3-巯基丙硫基)丙烷、1,2,3-三(巯基甲硫基)丙烷、1,2,3-三(2-巯基乙硫基)丙烷、1,2,3-三(3-巯基丙硫基)丙烷、4-巯基甲基-1,8-二巯基-3,6-二硫杂辛烷、5,7-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷、4,7-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷、4,8-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷、四(巯基甲硫基甲基)甲烷、四(2-巯基乙硫基甲基)甲烷、四(3-巯基丙硫基甲基)甲烷、双(2,3-二巯基丙基)硫醚、2,5-二巯基-1,4-二噻烷、2,5-二巯基甲基-2,5-二甲基-1,4-二噻烷等脂肪族多硫醇化合物;及
上述化合物的巯基乙酸酯及巯基丙酸酯、羟基甲基硫醚双(2-巯基乙酸酯)、羟基甲基硫醚双(3-巯基丙酸酯)、羟基乙基硫醚双(2-巯基乙酸酯)、羟基乙基硫醚双(3-巯基丙酸酯)、羟基丙基硫醚双(2-巯基乙酸酯)、羟基丙基硫醚双(3-巯基丙酸酯)、羟基甲基二硫醚双(2-巯基乙酸酯)、羟基甲基二硫醚双(3-巯基丙酸酯)、羟基乙基二硫醚双(2-巯基乙酸酯)、羟基乙基二硫醚双(3-巯基丙酸酯)、羟基丙基二硫醚双(2-巯基乙酸酯)、羟基丙基二硫醚双(3-巯基丙酸酯)、2-巯基乙基醚双(2-巯基乙酸酯)、2-巯基乙基醚双(3-巯基丙酸酯)、1,4-二噻烷-2,5-二醇双(3-巯基丙酸酯)、亚硫基二乙酸双(2-巯基乙基酯)、亚硫基二丙酸双(2-巯基乙基酯)、4,4-硫代二丁酸双(2-巯基乙基酯)、亚二硫基二乙酸双(2-巯基乙基酯)、二亚硫基二丙酸双(2-巯基乙基酯)、4,4-亚二硫基二丁酸双(2-巯基乙基酯)、亚硫基二乙酸双(2,3-二巯基丙基酯)、亚硫基二丙酸双(2,3-二巯基丙基酯)、亚二硫基二乙酸双(2,3-二巯基丙基酯)、亚硫基二丙酸双(2,3-二巯基丙基酯)、亚二硫基二丙酸双(2,3-二巯基丙基酯)等含有酯键的脂肪族多硫醇及3,4-噻吩二硫醇、2,5-二巯基-1,3,4-噻二唑(bismuthiol)等杂环多硫醇化合物;及
1,1,3,3-四(巯基甲硫基)丙烷、1,1,2,2-四(巯基甲硫基)乙烷、4,6-双(巯基甲硫基)-1,3-二噻烷、1,1,5,5-四(巯基甲硫基)-3-硫杂戊烷、1,1,6,6-四(巯基甲硫基)-3,4-二硫杂己烷、2,2-双(巯基甲硫基)乙烷硫醇、2-(4,5-二巯基-2-硫杂戊基)-1,3-二硫杂环戊烷、2,5-双(4,4-双(巯基甲硫基)-2-硫杂丁基)-1,4-二噻烷、2,2-双(巯基甲硫基)-1,3-丙二硫醇、3-巯基甲硫基-1,7-二巯基-2,6-二硫杂庚烷、3,6-双(巯基甲硫基)-1,9-二巯基-2,5,8-三硫杂壬烷、3-巯基甲硫基-1,6-二巯基-2,5-二硫杂己烷、2-(2,2-双(巯基二甲硫基)乙基)-1,3-二硫杂环丁烷、1,1,9,9-四(巯基甲硫基)-5-(3,3-双(巯基甲硫基)-1-硫杂丙基)3,7-二硫杂壬烷、三(2,2-双(巯基甲硫基)乙基)甲烷、三(4,4-双(巯基甲硫基)-2-硫杂丁基)甲烷、四(2,2-双(巯基甲硫基)乙基)甲烷、四(4,4-双(巯基甲硫基)-2-硫杂丁基)甲烷、3,5,9,11-四(巯基甲硫基)-1,13-二巯基-2,6,8,12-四硫杂十三烷、3,5,9,11,15,17-六(巯基甲硫基)-1,19-二巯基-2,6,8,12,14,18-六硫杂十九烷、9-(2,2-双(巯基甲硫基)乙基)-3,5,13,15-四(巯基甲硫基)-1,17-二巯基-2,6,8,10,12,16-六硫杂十七烷、3,4,8,9-四(巯基甲硫基)-1,11-二巯基-2,5,7,10-四硫杂十一烷、3,4,8,9,13,14-六(巯基甲硫基)-1,16-二巯基-2,5,7,10,12,15-六硫杂十六烷、8-[双(巯基甲硫基)甲基]-3,4,12,13-四(巯基甲硫基)-1,15-二巯基-2,5,7,9,11,14-六硫杂十五烷、4,6-双[3,5-双(巯基甲硫基)-7-巯基-2,6-二硫杂庚基硫基]-1,3-二噻烷、4-[3,5-双(巯基甲硫基)-7-巯基-2,6-二硫杂庚基硫基]-6-巯基甲硫基-1,3-二噻烷、1,1-双[4-(6-巯基甲硫基)-1,3-二噻烷基硫基]-1,3-双(巯基甲硫基)丙烷、1-[4-(6-巯基甲硫基)-1,3-二噻烷基硫基]-3-[2,2-双(巯基甲硫基)乙基]-7,9-双(巯基甲硫基)-2,4,6,10-四硫杂十一烷、1,5-双[4-(6-巯基甲硫基)-1,3-二噻烷基硫基]-3-[2-(1,3-二硫杂环丁基)]甲基-2,4-二硫杂戊烷、4,6-双{3-[2-(1,3-二硫杂环丁基)]甲基-5-巯基-2,4-二硫杂戊基硫基}-1,3-二噻烷、4,6-双[4-(6-巯基甲硫基)-1,3-二噻烷基硫基]-6-[4-(6-巯基甲硫基)-1,3-二噻烷基硫基]-1,3-二噻烷、3-[2-(1,3-二硫杂环丁基)]甲基-7,9-双(巯基甲硫基)-1,11-二巯基一2,4,6,10-四硫杂十一烷、9-[2-(1,3-二硫杂环丁基)]甲基-3,5,13,15-四(巯基甲硫基)-1,17-二巯基-2,6,8,10,12,16-六硫杂十七烷、3-[2-(1,3-二硫杂环丁基)]甲基-7,9,13,15-四(巯基甲硫基)-1,17-二巯基-2,4,6,10,12,16-六硫杂十七烷、3,7-双[2-(1,3-二硫杂环丁基)]甲基-1,9-二巯基-2,4,6,8-四硫杂壬烷、4-[3,4,8,9-四(巯基甲硫基)-11-巯基-2,5,7,10-四硫杂十一烷基]-5-巯基甲硫基-1,3-二硫戊环、4,5-双[3,4-双(巯基甲硫基)-6-巯基-2,5-二硫杂己基硫基]-1,3-二硫戊环、4-[3,4-双(巯基甲硫基)-6-巯基-2,5-二硫杂己基硫基]-5-巯基甲硫基-1,3-二硫戊环、4-[3-双(巯基甲硫基)甲基-5,6-双(巯基甲硫基)-8-巯基-2,4,7-三硫杂辛基]-5-巯基甲硫基-1,3-二硫戊环、2-{双[3,4-双(巯基甲硫基)-6-巯基-2,5-二硫杂己基硫基]甲基}-1,3-二硫杂环丁烷、2-[3,4-双(巯基甲硫基)-6-巯基-2,5-二硫杂己基硫基]巯基甲硫基甲基-1,3-二硫杂环丁烷、2-[3,4,8,9-四(巯基甲硫基)-11-巯基-2,5,7,10-四硫杂十一烷基硫基]巯基甲硫基甲基-1,3-二硫杂环丁烷、2-[3-双(巯基甲硫基)甲基-5,6-双(巯基甲硫基)-8-巯基-2,4,7-三硫杂辛基]巯基甲硫基甲基-1,3-二硫杂环丁烷、4,5-双{1-[2-(1,3-二硫杂环丁基)]-3-巯基-2-硫杂丙硫基}-1,3-二硫戊环、4-{1-[2-(1,3-二硫杂环丁基)]-3-巯基-2-硫杂丙硫基}-5-[1,2-双(巯基甲硫基)-4-巯基-3-硫杂丁基硫基]-1,3-二硫戊环、2-{双[4-(5-巯基甲硫基-1,3-二硫戊环基)硫基]甲基}-1,3-二硫杂环丁烷、4-[4-(5-巯基甲硫基-1,3-二硫戊环基)硫基]-5-{1-[2-(1,3-二硫杂环丁基)]-3-巯基-2-硫杂丙硫基}-1,3-二硫戊环以及上述化合物的寡聚物等具有二硫缩醛或二硫缩酮骨架的多硫醇化合物;及
三(巯基甲硫基)甲烷、三(巯基乙硫基)甲烷、1,1,5,5-四(巯基甲硫基)-2,4-二硫杂戊烷、双[4,4-双(巯基甲硫基)-1,3-二硫杂丁基]-(巯基甲硫基)甲烷、三[4,4-双(巯基甲硫基)-1,3-二硫杂丁基]甲烷、2,4,6-三(巯基甲硫基)-1,3,5-三硫杂环己烷、2,4-双(巯基甲硫基)-1,3,5-三硫杂环己烷、1,1,3,3-四(巯基甲硫基)-2-硫杂丙烷、双(巯基甲基)甲硫基-1,3,5-三硫杂环己烷、三[(4-巯基甲基-2,5-二硫杂环己基-1-基)甲硫基]甲烷、2,4-双(巯基甲硫基)-1,3-二硫杂环戊烷、2-巯基乙硫基-4-巯基甲基-1,3-二硫杂环戊烷、2-(2,3-二巯基丙硫基)-1,3-二硫杂环戊烷、4-巯基甲基-2-(2,3-二巯基丙硫基)-1,3-二硫杂环戊烷、4-巯基甲基-2-(1,3-二巯基-2-丙硫基)-1,3-二硫杂环戊烷、三[2,2-双(巯基甲硫基)-2-硫杂丙基]甲烷、三[4,4-双(巯基甲硫基)-3-硫杂丁基]甲烷、2,4,6-三[3,3-双(巯基甲硫基)-2-硫杂丙基]-1,3,5-三硫杂环己烷、四[3,3-双(巯基甲硫基)-2-硫杂丙基]甲烷以及上述化合物的寡聚物等具有三硫代原甲酸酯骨架的多硫醇化合物等,但并不限于这些列举的化合物。进而,也可以使用上述化合物的氯取代物、溴取代物等卤素取代物。上述具有硫醚键的巯基化合物可以单独使用,也可以混合2种以上进行使用。
此外,作为具有羟基的巯基化合物,例如可以举出2-巯基乙醇、3-巯基-1,2-丙二醇、丙三醇二(巯基乙酸酯)、1-羟基-4-巯基环己烷、2,4-二巯基苯酚、2-巯基氢醌、4-巯基苯酚、1,3-二巯基-2-丙醇、2,3-二巯基-1-丙醇、1,2-二巯基-1,3-丁二醇、季戊四醇三(3-巯基丙酸酯)、季戊四醇单(3-巯基丙酸酯)、季戊四醇双(3-巯基丙酸酯)、季戊四醇三(巯基乙酸酯)、季戊四醇五(3-巯基丙酸酯)、羟基甲基-三(巯基乙硫基甲基)甲烷、1-羟基乙硫基-3-巯基乙硫基苯、4-羟基-4′-巯基二苯基砜、2-(2-巯基乙硫基)乙醇、二羟基乙基硫醚单(3-巯基丙酸酯)、二巯基乙烷单(水杨酸酯)、羟基乙硫基甲基-三(巯基乙硫基)甲烷等,但并不限于这些列举的化合物。进而,也可以使用上述化合物的氯取代物、溴取代物等卤素取代物。上述具有羟基的巯基化合物可以单独使用,也可以混合2种以上进行使用。
上述活性氢化合物可以分别单独使用或混合2种以上进行使用。作为活性氢化合物,优选为4-巯基甲基-1,8-二巯基-3,6-二硫杂辛烷、5,7-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷、4,7-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷、4,8-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷、季戊四醇四(3-巯基丙酸酯)、1,1,3,3-四(巯基甲硫基)丙烷、1,1,2,2-四(巯基甲硫基)乙烷、4,6-双(巯基甲硫基)-1,3-二噻烷或2-(2,2-双(巯基二甲硫基)乙基)-1,3-二硫杂环丁烷,更优选为4-巯基甲基-1,8-二巯基-3,6-二硫杂辛烷、5,7-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷、4,7-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷、4,8-二巯基甲基-1,11-二巯基-3,6,9-三硫杂十一烷、季戊四醇四(3-巯基丙酸酯)。
本发明中,活性氢化合物优选含有至少一种选自上述化合物的、具有3个以上巯基的化合物,较优选均为具有3个以上巯基的化合物。由此得到的树脂的折射率提高,难以产生光学各向异性,所以双折射率也降低,耐冲击性等机械物性提高。
与此相对,日本特开2005-336476号中,仅使用具有两个巯基的化合物,与含有至少一种具有3个以上巯基的化合物的本发明不同,得到的树脂在折射率等光学特性、耐冲击性等机械物性方面有改良余地。
具有硫代氨基甲酸酯键的树脂以选自异氰酸酯化合物及异硫氰酸酯化合物中的一种或两种以上的异氰酸酯类、及具有巯基的一种或两种以上的活性氢化合物作为主要成分形成,但为了将聚硫代氨基甲酸酯树脂改性,也可添加羟基化合物、胺化合物、环氧化合物、环硫化合物、有机酸及其酸酐、含有(甲基)丙烯酸酯化合物等的烯烃化合物等树脂改性剂。此处,所谓的树脂改性剂,为调节或提高聚硫代氨基甲酸酯树脂的折射率、阿贝数、耐热性、比重等物性或耐冲击性等机械强度等的化合物。
作为可作为树脂改性材料添加的羟基化合物,例如可以举出二甘醇、三甘醇、1,3-丙二醇、双丙甘醇、三丙甘醇、1,4-丁二醇、1,3-丁二醇、1,5-戊二醇、1,4-戊二醇、1,3-戊二醇、1,6-己二醇、1,5-己二醇、1,4-己二醇、1,3-己二醇、1,7-庚二醇、1,8-辛二醇、硫代二乙醇、二硫代二乙醇、硫代二丙醇、二硫代二丙醇、以及这些化合物的寡聚物等,但并不限于这些列举的化合物。上述醇化合物可以单独使用,或可以混合两种以上进行使用。
作为可作为树脂改性剂添加的胺化合物,可以举出乙胺、正丙胺、异丙胺、正丁胺、仲丁胺、叔丁胺、戊胺、己胺、庚胺、辛胺、癸胺、十二烷基胺、十四烷基胺、3-戊基胺、2-乙基己基胺、1,2-二甲基己基胺、烯丙基胺、氨基甲基双环庚烷、环戊基胺、环己基胺、2,3-二甲基环己基胺、氨基甲基环己烷、苯胺、苄胺、苯乙胺、2,3-、或4-甲基苄基胺、邻、间、或对甲基苯胺、邻、间、或对乙基苯胺、氨基吗啉、萘基胺、糠基胺、α-氨基二苯基甲烷、甲苯胺、氨基吡啶、氨基苯酚、氨基乙醇、1-氨基丙醇、2-氨基丙醇、氨基丁醇、氨基戊醇、氨基己醇、甲氧基乙基胺、2-(2-氨基乙氧基)乙醇、3-乙氧基丙基胺、3-丙氧基丙基胺、3-丁氧基丙基胺、3-异丙氧基丙基胺、3-异丁氧基丙基胺、2,2-二乙氧基乙基胺等单官能伯胺化合物;及
乙二胺、1,2-、或1,3-二氨基丙烷、1,2-、1,3-、或1,4-二氨基丁烷、1,5-二氨基戊烷、1,6-二氨基己烷、1,7-二氨基庚烷、1,8-二氨基辛烷、1,10-二氨基癸烷、1,2-、1,3-、或1,4-二氨基环己烷、邻、间、或对二氨基苯、3,4-、或4,4′-二氨基二苯甲酮、3,4-、或4,4′-二氨基二苯基醚、4,4′-二氨基二苯基甲烷、4,4′-二氨基二苯基硫醚、3,3′、或4,4′-二氨基二苯基砜、2,7-二氨基芴、1,5-、1,8-、或2,3-二氨基萘、2,3-、2,6-、或3,4-二氨基吡啶、2,4-、或2,6-二氨基甲苯、间、或对苯二甲撑二胺、异佛尔酮二胺、二氨基甲基双环庚烷、1,3-、或1,4-二氨基甲基环己烷、2-、或4-氨基哌啶、2-、或4-氨基甲基哌啶、2-、或4-氨基乙基哌啶、N-氨基乙基吗啉、N-氨基丙基吗啉等聚伯胺化合物;及
二乙胺、二丙胺、二正丁胺、二仲丁胺、二异丁胺、二正戊胺、二-3-戊基胺、二己胺、二辛胺、二(2-乙基己基)胺、甲基己基胺、二烯丙基胺、N-甲基烯丙基胺、哌啶、吡咯烷、二苯基胺、N-甲基胺、N-乙基胺、二苄基胺、N-甲基苄基胺、N-乙基苄基胺、二环己基胺、N-甲基苯胺、N-乙基苯胺、二萘基胺、1-甲基哌嗪、吗啉等单官能仲胺化合物;及
N,N′-二甲基乙二胺、N,N′-二甲基-1,2-二氨基丙烷、N,N′-二甲基-1,3-二氨基丙烷、N,N′-二甲基-1,2-二氨基丁烷、N,N′-二甲基-1,3-二氨基丁烷、N,N′-二甲基-1,4-二氨基丁烷、N,N′-二甲基-1,5-二氨基戊烷、N,N′-二甲基-1,6-二氨基己烷、N,N′-二甲基-1,7-二氨基庚烷、N,N′-二乙基乙二胺、N,N′-二乙基-1,2-二氨基丙烷、N,N′-二乙基-1,3-二氨基丙烷、N,N′-二乙基-1,2-二氨基丁烷、N,N′-二乙基-1,3-二氨基丁烷、N,N′-二乙基-1,4-二氨基丁烷、N,N′-二乙基-1,5-二氨基戊烷、N,N′-二乙基-1,6-二氨基己烷、N,N′-二乙基-1,7-二氨基庚烷、哌嗪、2-甲基哌嗪、2,5-二甲基哌嗪、2,6-二甲基哌嗪、高哌嗪、1,1-二-(4-哌啶基)甲烷、1,2-二-(4-哌啶基)乙烷、1,3-二-(4-哌啶基)丙烷、1,4-二-(4-哌啶基)丁烷、四甲基胍等聚仲胺化合物等,但并不限于这些列举的化合物。上述胺化合物可以单独使用,也可以混合2种以上进行使用。
作为可作为树脂改性剂添加的环氧化合物,可以举出由双酚A缩水甘油醚等多元酚化合物和表卤代醇化合物的缩合反应得到的酚类环氧化合物、由氢化双酚A缩水甘油醚等多元醇化合物和表卤代醇化合物的缩合得到的醇类环氧化合物、由3,4-环氧环己基甲基-3′,4′-环氧环己烷甲酸酯或1,2-六氢苯二甲酸二缩水甘油基酯等多元有机酸化合物和表卤代醇化合物的缩合得到的缩水甘油基酯类环氧化合物、由伯二胺及仲二胺化合物和表卤代醇化合物的缩合得到的胺类环氧化合物、以及乙烯基环己烯双环氧化物等脂肪族多元环氧化合物等,但并不限于这些列举的化合物。上述环氧化合物可以单独使用,也可以混合2种以上进行使用。
作为可作为树脂改性剂添加的环硫化合物,可以举出例如双(2,3-环硫丙硫基)硫醚、双(2,3-环硫丙硫基)二硫醚、双(2,3-环硫丙硫基)甲烷、1,2-双(2,3-环硫丙硫基)乙烷、1,5-双(2,3-环硫丙硫基)-3-硫杂戊烷等链状脂肪族的2,3-环硫丙硫基化合物;
1,3-双(2,3-环硫丙硫基)环己烷、2,5-双(2,3-环硫丙硫基甲基)-1,4-二噻烷等环状脂肪族、具有杂环的2,3-环硫丙硫基化合物;
1,3-双(2,3-环硫丙硫基)苯、1,4-双(2,3-环硫丙硫基)苯等芳香族2,3-环硫丙硫基化合物等,但并不限于这些列举的化合物。上述环硫化合物可以单独使用,也可以混合2种以上进行使用。
作为可作为树脂改性剂添加的有机酸及其酸酐,可以举出亚硫基二乙酸、亚硫基二丙酸、亚二硫基二丙酸、苯二甲酸酐、六氢苯二甲酸酐、甲基六氢苯二甲酸酐、甲基四氢苯二甲酸酐、甲基降冰片烯酸酐、甲基降冰片烯酸酐、马来酸酐、偏苯三酸酐、苯均四酸酐等,但并不限于这些列举的化合物。上述有机酸及其酸酐可以单独使用,也可以混合2种以上进行使用。
作为可作为树脂改性剂添加的烯烃化合物,可以举出丙烯酸苄酯、甲基丙烯酸苄酯、丙烯酸丁氧基乙基酯、甲基丙烯酸丁氧基甲基酯、丙烯酸环己基酯、甲基丙烯酸环己基酯、丙烯酸2-羟基乙基酯、甲基丙烯酸2-羟基甲基酯、丙烯酸缩水甘油基酯、甲基丙烯酸缩水甘油基酯、丙烯酸苯氧基乙基酯、甲基丙烯酸苯氧基乙基酯、甲基丙烯酸苯基酯、二丙烯酸乙二醇酯、二甲基丙烯酸乙二醇酯、二丙烯酸二甘醇酯、二甲基丙烯酸二甘醇酯、二丙烯酸三甘醇酯、二甲基丙烯酸三甘醇酯、二丙烯酸四甘醇酯、二甲基丙烯酸四甘醇酯、二丙烯酸聚乙二醇酯、二甲基丙烯酸聚乙二醇酯、二丙烯酸新戊二醇酯、二甲基丙烯酸新戊二醇酯、乙二醇二缩水甘油基丙烯酸酯、乙二醇二缩水甘油基甲基丙烯酸酯、双酚A二丙烯酸酯、双酚A二甲基丙烯酸酯、2,2-双(4-丙烯酰氧基乙氧基苯基)丙烷、2,2-双(4-甲基丙烯酰氧基乙氧基苯基)丙烷、2,2-双(4-丙烯酰氧基二乙氧基苯基)丙烷、2,2-双(4-甲基丙烯酰氧基二乙氧基苯基)丙烷、双酚F二丙烯酸酯、双酚F二甲基丙烯酸酯、1,1-双(4-丙烯酰氧基乙氧基苯基)甲烷、1,1-双(4-甲基丙烯酰氧基乙氧基苯基)甲烷、1,1-双(4-丙烯酰氧基二乙氧基苯基)甲烷、1,1-双(4-甲基丙烯酰氧基二乙氧基苯基)甲烷、二羟甲基三环癸烷二丙烯酸酯、三羟甲基丙烷三丙烯酸酯、三羟甲基丙烷三甲基丙烯酸酯、丙三醇二丙烯酸酯、丙三醇二甲基丙烯酸酯、季戊四醇三丙烯酸酯、季戊四醇四丙烯酸酯、季戊四醇四甲基丙烯酸酯、甲硫基丙烯酸酯、甲硫基甲基丙烯酸酯、苯基硫基丙烯酸酯、苄基硫基甲基丙烯酸酯、苯二甲撑二硫醇二丙烯酸酯、苯二甲撑二硫醇二甲基丙烯酸酯、巯基乙基硫醚二丙烯酸酯、巯基乙基硫醚二甲基丙烯酸酯等(甲基)丙烯酸酯化合物;及
烯丙基缩水甘油醚、邻苯二甲酸二烯丙基酯、对苯二甲酸二烯丙基酯、间苯二甲酸二烯丙基酯、碳酸二烯丙基酯、二甘醇双烯丙基碳酸酯等烯丙基化合物;及
苯乙烯、氯苯乙烯、甲基苯乙烯、溴苯乙烯、二溴苯乙烯、二乙烯基苯、3,9-二乙烯基螺双(间二氧杂环己烷)等乙烯基化合物等,但并不限于这些列举的化合物。上述烯烃化合物可以单独使用,也可以混合2种以上进行使用。
接下来对具有硫代氨基甲酸酯键的树脂的制造方法进行说明。
本发明中,对于含有用作原料的异氰酸酯类和活性氢化合物、进而还含有作为改性剂的羟基化合物的原料的使用比例来说,(NCO+NCS)/(SH+OH)的官能团摩尔比通常在0.5以上、3.0以下的范围内,优选在0.6以上、2.0以下的范围内,更优选在0.8以上、1.3以下的范围内。
成型具有硫代氨基甲酸酯键的树脂的膜时,也可根据目的,与公知的成型法中的方法相同地添加二丁基二氯化锡、二甲基二氯化锡等催化剂、苯并三唑类等紫外线吸收剂、外部或内部脱模剂、光稳定剂、扩链剂、交联剂、抗氧化剂、防着色剂、抗氧化剂、自由基反应引发剂等反应引发剂、扩链剂、交联剂、防着色剂、油溶染料、填充剂、密合性提高剂等各种物质。上述添加剂也可预先添加至聚合性组合物中。
在具有硫代氨基甲酸酯键的树脂的情况,由于具有硫原子或硒原子的无机化合物容易造成明显的色调恶化或浊化,所以聚合性组合物中的上述无机化合物的含量优选为1重量%以下。
接下来对单体的配制方法进行说明。本发明中,当在聚合前混合异氰酸酯类、活性氢化合物、反应催化剂、脱模剂、及其他添加剂制备聚合性组合物时,催化剂或脱模剂及其他添加剂的添加顺序也取决于在单体中的溶解性,可以预先使其添加溶解在异氰酸酯类中、或使其添加溶解在活性氢化合物中、或使其添加溶解在异氰酸酯类和活性氢化合物的混合物中。或者,也可以使其溶解在使用的单体的一部分中制备母液后,添加该母液。添加顺序不限于上述例举的方法,可以根据操作性、安全性、方便性等适当选择。
作为催化剂添加的形态,可以以催化剂本身的形状进行添加,也可以溶解在所使用的单体类的一部分中制备母液后添加该母液。
混合异氰酸酯类和活性氢化合物以及反应催化剂或脱模剂、及其他添加剂制备聚合性组合物时的温度通常为25℃以下。从组合物的贮存期的观点考虑,有时优选使其为更低的温度。但是,反应催化剂、脱模剂或添加剂在单体中的溶解性不良时,也可以预先加热,使其溶解在作为单体的异氰酸酯类或活性氢化合物、或单体混合物中。
[膜的制造方法]
本发明的膜可通过通常的方法制造,可使用上述聚合性组合物,通过浇铸(薄膜涂布-聚合固化)法、旋涂-聚合固化法、浇铸聚合法等得到。
浇铸法、旋涂-聚合固化法如下所述:将进行过粘度调节的聚合性组合物从模具挤出,并在基材上流延后,或者在使载有组合物的基材高速旋转而形成薄膜后,使其聚合、固化而得到膜,所述聚合性组合物为具有异氰酸酯基的化合物及具有硫醇基的化合物的混合物,所述混合物部分地具有硫代氨基甲酸酯键、而且可形成硫代氨基甲酸酯。需要说明的是,混合物的浇铸(涂布)时的粘度可根据涂布方法、其用途适当选择。
浇铸聚合法是将聚合性组合物注入到铸型面间并使其聚合而得到膜的方法,所述铸型由四边密封的一对无机玻璃、金属或树脂板形成,且具有200μm以下的间隔,所述聚合性组合物为具有异氰酸酯基的化合物及具有硫醇基的化合物的混合物,所述混合物部分地具有硫代氨基甲酸酯键、而且可形成硫代氨基甲酸酯。需要说明的是,混合物注入时的粘度可根据注入方法和固化过程等适当选择。
需要说明的是,本发明中,可对得到的膜进行退火处理。此外,可向聚合性组合物中混合金属氧化物等微粒、填料等而形成膜。
[膜的用途]
对于本发明的膜来说,由于高折射率、低双折射率及透光性的均衡性优异,而且韧性、刚性、尺寸稳定性等机械特性的均衡性优异,加工时的变形等的影响极小,此外,耐溶剂性也优异,所以,可用作多种光学膜。
作为光学膜,可以举出偏光膜及构成偏光膜的偏光元件和偏振片保护膜、相位差膜、取向膜(取向膜)、视角扩大(补偿)膜、漫射板(膜)、棱镜片、导光板、亮度提升膜、近红外吸收膜、反射膜、防反射(AR)膜、降反射(LR)膜、防反光(AG)膜、透明导电(ITO)膜、透明导电膜用基材、各向异性导电性膜(ACF)、电磁波屏蔽(EMI)膜、电极基板用膜、滤色片基板用膜、阻挡膜、滤色片层、黑底层(blackmatrixlayer)等。如上所述,本发明的光学膜可形成于液晶显示器、有机EL显示器、等离子体显示器、太阳能电池等各种光学构件的内部或外部,本发明提供上述光学构件。
此外,本发明的光学膜通过特别位于发光面或受光面的表面,可高效地透出和透入光,最适于要求上述作用的用途。例如,可提供下述发光设备:对本膜的一侧的面进行凹凸加工,而后将另一侧的面粘接于发光设备的发光面,从而将在发光体内部反射的光透出至外部,发光效率提高。还可以提供下述发光设备:将该膜自身作为基板,在其表面上直接形成发光元件,从而降低元件内的反射,发光效率提高。如上所述,根据本发明,可提供将光学膜形成于内部或外部的发光设备、以及使用了该发光设备的照明装置(LED灯、显示器的背光灯、照相机或移动电话等的闪光灯等)及图像显示装置(平板显示器等)。
本发明的光学膜可以是兼具两种以上上述光学膜的功能的1片膜,也可以构成具有两种以上上述光学膜的膜(复合膜)中的一部分或全部。上述光学膜也可如下使用:不剥离地使用在玻璃或其他树脂膜等基材上形成的膜,直接形成贴合构件、多层结构体。
实施例
以下,通过实施例具体地说明本发明。但本发明不受这些实施例的任何限制。
本实施例中得到的膜的性能通过以下试验法进行评价。
·折射率、阿贝数:使用ATAGO制多波长阿贝折射计,在20℃下进行测定(钠D线:589nm)。
·双折射率:使用王子计测器械制KOBRA-CCD/X,在590nm的波长下对正面延迟Re和正面双折射率Δnxy进行测定。此外,使用大塚电子制相位差测定装置RETS-100,利用旋转检偏振器法(rotationanalyzermethod),对于400~800nm波长,进行厚度方向的延迟Rth和厚度方向的双折射率Δnxz的测定。(表中的Rth及Δn为590nm下的值)
·线膨胀系数:使用热分析装置(TMA-50,岛津制作所公司制),使用加工成长度15mm、宽度5mm的试验片,在5℃/min的升温速度下进行测定。此外,从玻璃化温度前后的TMA曲线的切线的交点求出TMA软化温度。
·力学强度:使用万能材料试验机(201-5型,Intesco公司制),使用加工成长50mm、宽5mm的哑铃型试验片,从试验片两端以拉伸速度30mm/min进行拉伸。(厚80-100μm)
·冲击强度:使用膜冲击试验机(东洋精机制作所公司制)、顶端径1英寸的摆锤进行测定。
·总透光率(透过率-1):依照JIS-K7105,使用雾度计(NDH2000,日本电色工业制)进行测定。
·550nm透过率(透过率-2):使用分光光度计(U-3010,日立制)测定550nm波长下的透过率。
·透湿性:依照JISZ0208,在温度60℃、90%RH、膜厚100μm的条件下测定透湿量。
·耐溶剂性:分别在膜上滴加各溶剂(丙酮、乙醇、环己酮、甲苯),然后,用bemcot无尘擦拭纸擦掉,目视观察表面的溶解状态。
[制造例1]
按照日本特开平7-252207实施例1记载的方法,合成含有5,7-二巯基甲基-1,11-二巯基-3,6-三硫杂十一烷、4,7-二巯基甲基-1,11-二巯基-3,6-三硫杂十一烷、4,8-二巯基甲基-1,11-二巯基-3,6-三硫杂十一烷的多硫醇化合物(B-2)。
[制造例2]
按照日本特开2004-2820号公报的制造例2记载的方法,合成含有1,1,3,3-四(巯基甲硫基)丙烷、4,6-双(巯基甲硫基)-1,3-二噻烷、2-(2,2-双(巯基甲硫基)乙基)-1,3-二硫杂环丁烷的多硫醇化合物(B-3)。
[实施例1]
预先向间苯二甲撑二异氰酸酯36.4g中加入二丁基二氯化锡10.5mg作为催化剂、“ZelecUN”(商品名,Stepan公司制,酸性磷酸烷基酯)70mg作为内部脱模剂并将其溶解而形成单体混合溶液。然后加入4-巯基甲基-1,8-二巯基-3,6-二硫杂辛烷33.6g,充分混合,形成单体混合溶液。在减压下对该单体混合溶液脱气1小时。在蓝板玻璃(blueplateglass)的四边贴附80μm的聚酰亚胺胶带(Kaptontape)使其为框状来制作壁,在壁的内侧滴加单体混合溶液,进而,由上方放置相同尺寸的玻璃基板。确认聚酰亚胺胶带壁的内侧已被单体混合溶液充满后,用夹子(clip)夹持并固定两片玻璃。将其从20℃缓缓升温,加热至120℃,经20小时使其固化。在冷却后从玻璃剥离得到膜。得到的膜是无色透明的。
[实施例2]
预先向间苯二甲撑二异氰酸酯36.4g中加入二丁基二氯化锡10.5mg作为催化剂、“ZelecUN”(商品名,Stepan公司制酸性磷酸烷基酯)70mg作为内部脱模剂,并将其溶解而形成单体混合溶液。然后加入4-巯基甲基-1,8-二巯基-3,6-二硫杂辛烷33.6g,充分混合,形成单体混合溶液。在减压下对该单体混合溶液脱气1小时。然后,使用将涂布GAP设定为70μm以下的敷贴器(CoatingTesterIndustriesCo.,Ltd制),涂布在聚萘二甲酸乙二醇酯膜(帝人公司制:TeonexQ51)上。在基材上均匀地涂展单体混合溶液。将其从20℃缓缓升温,加热至120℃,经13小时使其固化。在冷却后从基材剥离得到膜。得到的膜是无色透明的。膜的各物性如下所述。
·折射率:1.66(钠D线:589nm)
·阿贝数:32
·透过率(波长400~800nm平均):88.7%(膜厚80μm)
需要说明的是,在波长430nm下为88.0%(膜厚80μm)。
·双折射率:正面延迟Re(波长590nm):0.8nm(膜厚80μm)
双折射率Δnxy(波长590nm):1.0×10-5
厚度方向延迟Rth(波长590nm):49nm
双折射率Δnxz(波长590nm):6.3×10-4
·透湿度:7g/m2·24hr(换算为膜厚100μm)
·耐溶剂性:对于丙酮、乙醇、环己酮、甲苯中任一溶剂,未确认到溶解。
·线膨胀系数:8×10-5/K(厚度80μm)
·力学强度:
拉伸弹性模量3.8~4.1GPa
最大点应力120MPa
断裂伸长率3.1~5.7%
·冲击强度:2~4kJ/m(厚度45-55μm)
[实施例3]
预先向2,4-甲苯二异氰酸酯6.1g中加入二丁基二氯化锡2.5mg作为催化剂、“ZelecUN”(商品名,Stepan公司制酸性磷酸烷基酯)12.4mg作为内部脱模剂,并将其溶解而形成单体混合溶液。然后加入4-巯基甲基-1,8-二巯基-3,6-二硫杂辛烷6.3g,充分混合,形成单体混合溶液。在减压下对该单体混合溶液脱气1小时。在蓝板玻璃的四边贴附80μm的聚酰亚胺胶带使其为框状来制作壁,在壁的内侧滴加单体混合溶液,进而,由上方放置相同尺寸的玻璃基板。确认聚酰亚胺胶带壁的内侧已被单体混合溶液充满后,用夹子夹持并固定两片玻璃。将其从20℃缓缓升温,加热至120℃,经13小时使其固化。在冷却后从玻璃剥离得到膜。得到的膜是无色透明的。
[实施例4]
预先向2,4-甲苯二异氰酸酯5.6g中加入二丁基二氯化锡2.4mg作为催化剂、“ZelecUN”(商品名,Stepan公司制,酸性磷酸烷基酯)11.9mg作为内部脱模剂,并将其溶解而形成单体混合溶液。然后加入用制造例1记载的方法合成的多硫醇化合物(B-2)6.3g,充分混合,形成单体混合溶液。在减压下对该单体混合溶液脱气1小时。在蓝板玻璃的四边贴附80μm的聚酰亚胺胶带使其为框状来制作壁,在壁的内侧滴加单体混合溶液,进而,由上方放置相同尺寸的玻璃基板。确认聚酰亚胺胶带壁内侧已被单体混合溶液充满后,用夹子夹持并固定两片玻璃。将其从20℃缓缓升温,加热至120℃,经13小时使其固化。在冷却后从玻璃剥离得到膜。得到的膜是无色透明的。
[实施例5]
在50℃的水浴下,预先向2,4-甲苯二异氰酸酯41.3g中加入二丁基二氯化锡10.0mg作为催化剂、“ZelecUN”(商品名,Stepan公司制酸性磷酸烷基酯)100mg作为内部脱模剂,并将其溶解而形成单体混合溶液。然后加入用制造例2记载的方法合成的多硫醇化合物(B-3)58.7g,充分混合,形成单体混合溶液。在50℃减压下对该单体混合溶液脱气15分钟。在蓝板玻璃的四边贴附80μm的聚酰亚胺胶带使其为框状来制作壁,在壁的内侧滴加单体混合溶液,进而,由上方放置相同尺寸的玻璃基板。确认聚酰亚胺胶带壁的内侧已被单体混合溶液充满后,用夹子夹持并固定两片玻璃。将其从50℃缓缓升温,加热至120℃,经22小时使其固化。在冷却后从玻璃剥离得到膜。得到的膜是无色透明的。
[实施例6]
在60℃的水浴下,预先向加热熔融的间苯二异氰酸酯35g中加入1,6-己二异氰酸酯2.3g、二丁基二氯化锡5mg作为催化剂、磷酸二丁酯225mg及磷酸一丁酯25mg作为内部脱模剂,并将其溶解而形成单体混合溶液。然后加入用制造例2记载的方法合成的多硫醇化合物(B-3)62.7g,充分混合,形成单体混合溶液。在60℃减压下对该单体混合溶液脱气5分钟。在蓝板玻璃的四边贴附80μm的聚酰亚胺胶带使其为框状来制作壁,在壁的内侧滴加单体混合溶液,进而,由上方放置相同尺寸的玻璃基板。确认聚酰亚胺胶带壁的内侧已被单体混合溶液充满后,用夹子夹持并固定两片玻璃。将其从50℃缓缓升温,加热至120℃,经24小时使其固化。在冷却后从玻璃剥离得到膜。得到的膜是无色透明的。
[实施例7]
向间苯二甲撑二异氰酸酯44.5g中加入二丁基二氯化锡10.0mg作为催化剂、“ZelecUN”(商品名,Stepan公司制酸性磷酸烷基酯)100mg作为内部脱模剂,并将其溶解而形成单体混合溶液。然后加入用制造例2记载的方法合成的多硫醇化合物(B-3)55.5g,充分混合,形成单体混合溶液。在减压下对该单体混合溶液脱气1小时。在蓝板玻璃的四边贴附80μm的聚酰亚胺胶带使其为框状来制作壁,在壁的内侧滴加单体混合溶液,进而,由上方放置相同尺寸的玻璃基板。确认聚酰亚胺胶带壁的内侧已被单体混合溶液充满后,用夹子夹持并固定两片玻璃。将其从20℃缓缓升温,加热至120℃,经22小时使其固化。在冷却后从玻璃剥离得到膜。得到的膜是无色透明的。
将得到的各膜的各物性归纳示于表1。
[表1]
*测定中使用5cm×5mm的长条形片
表1的单体组成中使用的缩写表示下述物质。
A-1:间苯二甲撑二异氰酸酯
A-2:2,4-甲苯二异氰酸酯
A-3:间苯二异氰酸酯
A-4:1,6-己二异氰酸酯
B-1:4-巯基甲基-1,8-二巯基-3,6-二硫杂辛烷
B-2:由制造例1合成的多硫醇化合物
B-3:由制造例2合成的多硫醇化合物
[实施例8]
除了使聚酰亚胺胶带的壁的高度为400μm之外,按照与实施例1相同的方法得到膜。得到的膜是无色透明的。
[实施例9]
除了使聚酰亚胺胶带的壁的高度为700μm之外,按照与实施例1相同的方法得到膜,得到的膜是无色透明的。
[实施例10]
除了使聚酰亚胺胶带的壁的高度为200μm之外,按照与实施例5相同的方法得到膜,得到的膜是无色透明的。
[实施例11]
除了使聚酰亚胺胶带的壁的高度为200μm之外,按照与实施例6相同的方法得到膜,得到的膜是无色透明的。
[表2]
[实施例12]
预先向间苯二甲撑二异氰酸酯36.4g中加入二丁基二氯化锡10.5mg作为催化剂,并将其溶解而形成单体混合溶液。然后加入4-巯基甲基-1,8-二巯基-3,6-二硫杂辛烷33.6g,充分混合,形成单体混合溶液。在减压下对该单体混合溶液脱气1小时。然后,使用将涂布GAP设定为60μm的敷贴器,涂布于使用UV臭氧清洗装置清洗过表面的硼硅酸盐玻璃上。在玻璃基材上均匀地涂展单体混合溶液。将其从20℃缓缓升温,加热至120℃,经13小时使其固化。固化后,在120℃氮气氛下退火2小时,在减压下放置一夜。固化树脂膜的厚度为50μm。然后,在固化树脂膜上形成ITO溅射膜。使用SnO2(10wt%)的靶,在氩和氧的混合气氛下,使基板温度为室温,在固化树脂膜上形成150nm厚的ITO膜(溅射薄膜形成装置,ULVAC制)。另外,还制作了在硼硅酸盐玻璃上直接形成ITO膜所得的产物。
[实施例13]
预先向间苯二甲撑二异氰酸酯36.4g中加入二丁基二氯化锡10.5mg作为催化剂,并将其溶解而形成单体混合溶液。然后加入4-巯基甲基-1,8-二巯基-3,6-二硫杂辛烷33.6g,充分混合,形成单体混合溶液。在减压下对该单体混合溶液脱气1小时。然后,使用将涂布GAP设定为120μm的敷贴器,涂布于用UV臭氧清洗装置清洗过的Tempax单面磨砂玻璃板(磨砂玻璃320#:凹凸高度1~4μm)的磨面上。在玻璃基材上均匀地涂展单体混合溶液。将其从20℃缓缓升温,加热至120℃,经13小时使其固化。固化后,在120℃氮气氛下退火2小时,在减压下放置一夜。固化树脂膜的厚度为120μm。然后,在固化树脂膜上形成ITO溅射膜。使用SnO2(10wt%)的靶,在氩和氧的混合气氛下,使基板温度为室温,在固化树脂膜上形成150nm厚的ITO膜(溅射薄膜形成装置,ULVAC制)。另外,还制作了在硼硅酸盐玻璃上直接形成ITO膜所得的产物。
本申请要求2009年11月13日提出申请的日本专利申请特愿2009-260449号及2010年3月24日提出申请的日本专利申请特愿2010-067563号为基础的优先权,并将其全部内容引入本说明书中。
本申请包括以下方案。
(1)一种膜,其特征在于,由具有硫代氨基甲酸酯键的树脂构成,该树脂中含有的硫与氮的摩尔比(S/N)为0.8以上、小于3。
(2)如(1)所述的膜,其特征在于,钠D线中的折射率为1.6以上,波长590nm处的膜厚1~200μm的膜的正面延迟Re为10nm以下,相对于波长400~800nm的光的透光率的平均值为80%以上。
(3)如(1)或(2)所述的膜,其特征在于,具有硫代氨基甲酸酯键的树脂在结构中具有芳香族基团、杂环基团或脂环族基团。
(4)如(1)~(3)中任一项所述的膜,是通过浇铸法得到的。
(5)一种光学膜,由(1)~(4)中任一项所述的膜形成。
(6)一种光学构件,具备(5)所述的光学膜。
(7)一种显示器,具备(5)所述的光学膜。
(8)一种发光设备,具备(5)所述的光学膜。
(9)一种照明装置,使用(8)所述的发光设备。
(10)一种图像显示装置,使用(8)所述的发光设备。
需要说明的是,本发明的膜也包括片状的膜。
Claims (12)
1.一种膜,其特征在于,由具有硫代氨基甲酸酯键的树脂构成,所述树脂中含有的硫与氮的摩尔比(S/N)为0.8以上、小于3,所述膜的厚度为0.1~1000μm,
所述膜由下述混合物得到,所述混合物含有具有异氰酸酯基的化合物和具有巯基的活性氢化合物,所述混合物可形成硫代氨基甲酸酯键,
所述具有巯基的活性氢化合物包括具有3个以上巯基的化合物。
2.如权利要求1所述的膜,其特征在于,钠D线中的折射率为1.6以上,波长590nm处的膜厚1~200μm的膜的正面双折射率Δn为1.0×10-2以下,厚度方向的双折射率Δn为1.0×10-3以下,相对于波长400~800nm的光的透光率的平均值为80%以上。
3.如权利要求1所述的膜,其特征在于,具有硫代氨基甲酸酯键的树脂在结构中具有芳香族基团、杂环基团或脂环族基团。
4.如权利要求1所述的膜,是通过浇铸法得到的。
5.如权利要求1所述的膜,是利用浇铸法由具有异氰酸酯基的化合物及具有巯基的活性氢化合物的混合物得到的,所述混合物部分地具有硫代氨基甲酸酯键、而且可形成硫代氨基甲酸酯。
6.如权利要求1所述的膜,是通过将具有异氰酸酯基的化合物及具有巯基的活性氢化合物的混合物注入到200μm以下间隔的面间并使其聚合固化而得到的,所述混合物部分地具有硫代氨基甲酸酯键、而且可形成硫代氨基甲酸酯。
7.一种光学膜,是由权利要求1~6中任一项所述的膜形成的。
8.一种光学构件,使权利要求7所述的光学膜形成于其内部或外部。
9.一种显示器,具备权利要求7所述的光学膜。
10.一种发光设备,使权利要求7所述的光学膜形成于其内部或外部。
11.一种照明装置,使用了权利要求10所述的发光设备。
12.一种图像显示装置,使用了权利要求10所述的发光设备。
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CN103842399B (zh) * | 2011-10-07 | 2015-10-14 | 三井化学株式会社 | 聚合性组合物及其用途 |
JP5942486B2 (ja) * | 2012-03-05 | 2016-06-29 | 富士ゼロックス株式会社 | ロール部材、帯電装置、画像形成装置、およびプロセスカートリッジ |
KR101919214B1 (ko) * | 2014-03-28 | 2018-11-15 | 호야 렌즈 타일랜드 리미티드 | 광학 부재용 폴리이소시아네이트 모노머 조성물, 광학 부재 및 그 제조 방법 |
JP6225066B2 (ja) * | 2014-04-18 | 2017-11-01 | 株式会社ブリヂストン | シート形成体、接着シート及び積層体 |
CN104804170A (zh) * | 2015-04-03 | 2015-07-29 | 江苏明月光电科技有限公司 | 一种高折射率、高阿贝数树脂镜片 |
EP3203271B1 (en) * | 2016-02-08 | 2021-01-27 | Essilor International | Blue light cutting optical material comprising a benzotriazole uv absorber |
WO2018124137A1 (ja) * | 2016-12-28 | 2018-07-05 | 日本ゼオン株式会社 | 光学フィルム及び偏光板 |
KR20190108578A (ko) * | 2017-02-02 | 2019-09-24 | 아레스 머티리얼스 인크. | 플렉시블 컬러 필터 및 제조 방법 |
KR20190132410A (ko) * | 2017-04-10 | 2019-11-27 | 닛토덴코 가부시키가이샤 | 광학 필름, 편광판, 및 화상표시장치 |
CN107092043B (zh) * | 2017-05-15 | 2020-11-24 | 上海伟星光学有限公司 | 具有防护蓝紫光性能的1.67聚氨酯镜片及其制造方法 |
CN108503794A (zh) * | 2018-04-14 | 2018-09-07 | 上海伟星光学有限公司 | 一种具有漫反射高透过率聚氨酯薄膜及其制备方法 |
CN114379178B (zh) | 2020-10-05 | 2023-05-12 | Skc株式会社 | 玻璃接合用薄膜、薄膜的制备方法以及透光层叠体 |
US20230399942A1 (en) * | 2022-06-08 | 2023-12-14 | Saudi Arabian Oil Company | Fluorescent dye oil tracer compositions |
CN115364684B (zh) * | 2022-10-25 | 2023-01-03 | 天津大学 | 一种高通量荷正电纳滤膜及其制备方法 |
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US20120225274A1 (en) | 2012-09-06 |
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