CN108276543A - 塑料镜片用聚硫醇组合物 - Google Patents
塑料镜片用聚硫醇组合物 Download PDFInfo
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- CN108276543A CN108276543A CN201810098908.9A CN201810098908A CN108276543A CN 108276543 A CN108276543 A CN 108276543A CN 201810098908 A CN201810098908 A CN 201810098908A CN 108276543 A CN108276543 A CN 108276543A
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- Prior art keywords
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- polymerizable composition
- polythiourethane
- eyeglass
- bis
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- 239000000203 mixture Substances 0.000 title claims abstract description 118
- 229920006295 polythiol Polymers 0.000 title claims abstract description 31
- 239000011521 glass Substances 0.000 title abstract description 33
- -1 poly-thiol compound Chemical class 0.000 claims abstract description 95
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 claims abstract description 28
- 239000012948 isocyanate Substances 0.000 claims abstract description 18
- 230000000694 effects Effects 0.000 claims abstract description 16
- 230000001678 irradiating effect Effects 0.000 claims abstract description 9
- 229920002578 polythiourethane polymer Polymers 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 30
- 239000000126 substance Substances 0.000 claims description 16
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- KYLIZBIRMBGUOP-UHFFFAOYSA-N Anetholtrithion Chemical group C1=CC(OC)=CC=C1C1=CC(=S)SS1 KYLIZBIRMBGUOP-UHFFFAOYSA-N 0.000 claims description 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 8
- 239000005077 polysulfide Substances 0.000 claims description 8
- 229920001021 polysulfide Polymers 0.000 claims description 8
- 150000008117 polysulfides Polymers 0.000 claims description 8
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 claims description 8
- 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 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 7
- 238000013007 heat curing Methods 0.000 claims description 7
- 230000035699 permeability Effects 0.000 claims description 7
- 239000001294 propane Substances 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 7
- 150000002513 isocyanates Chemical class 0.000 abstract description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 20
- 238000000034 method Methods 0.000 description 13
- 230000003287 optical effect Effects 0.000 description 11
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 10
- 235000010290 biphenyl Nutrition 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 235000013849 propane Nutrition 0.000 description 9
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- RSJKGSCJYJTIGS-UHFFFAOYSA-N N-undecane Natural products CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- VSSFYDMUTATOHG-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)-3-[3-sulfanyl-2-(2-sulfanylethylsulfanyl)propyl]sulfanylpropane-1-thiol Chemical compound SCCSC(CS)CSCC(CS)SCCS VSSFYDMUTATOHG-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- CEUQYYYUSUCFKP-UHFFFAOYSA-N 2,3-bis(2-sulfanylethylsulfanyl)propane-1-thiol Chemical compound SCCSCC(CS)SCCS CEUQYYYUSUCFKP-UHFFFAOYSA-N 0.000 description 4
- RFMXKZGZSGFZES-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-sulfanylacetic acid Chemical compound OC(=O)CS.OC(=O)CS.OC(=O)CS.CCC(CO)(CO)CO RFMXKZGZSGFZES-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000007872 degassing Methods 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
- 150000004820 halides Chemical class 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-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 3
- QRNATDQRFAUDKF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate Chemical compound NC(=S)SCCSC(N)=S QRNATDQRFAUDKF-UHFFFAOYSA-N 0.000 description 3
- OCGYTRZLSMAPQC-UHFFFAOYSA-N 3-(2-sulfanylethylsulfanyl)-2-[1-sulfanyl-3-(2-sulfanylethylsulfanyl)propan-2-yl]sulfanylpropane-1-thiol Chemical compound SCCSCC(CS)SC(CS)CSCCS OCGYTRZLSMAPQC-UHFFFAOYSA-N 0.000 description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 241000534944 Thia Species 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- JOBBTVPTPXRUBP-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS JOBBTVPTPXRUBP-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000005283 ground state Effects 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical class CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 2
- LUYHWJKHJNFYGV-UHFFFAOYSA-N 1,2-diisocyanato-3-phenylbenzene Chemical compound O=C=NC1=CC=CC(C=2C=CC=CC=2)=C1N=C=O LUYHWJKHJNFYGV-UHFFFAOYSA-N 0.000 description 2
- HMDXXHVBUMKDQL-UHFFFAOYSA-N 1,2-diisocyanato-3-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC(N=C=O)=C1N=C=O HMDXXHVBUMKDQL-UHFFFAOYSA-N 0.000 description 2
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 2
- AXIWPQKLPMINAT-UHFFFAOYSA-N 1-ethyl-2,3-diisocyanatobenzene Chemical compound CCC1=CC=CC(N=C=O)=C1N=C=O AXIWPQKLPMINAT-UHFFFAOYSA-N 0.000 description 2
- QLOQTKGUQKAAAB-UHFFFAOYSA-N 1-isocyanato-2-(2-isocyanatoethoxy)ethane Chemical compound O=C=NCCOCCN=C=O QLOQTKGUQKAAAB-UHFFFAOYSA-N 0.000 description 2
- QUVLJNYSCQAYLV-UHFFFAOYSA-N 1-isocyanato-2-(2-isocyanatoethylsulfanyl)ethane Chemical compound O=C=NCCSCCN=C=O QUVLJNYSCQAYLV-UHFFFAOYSA-N 0.000 description 2
- DCQWACSEFXBOCJ-UHFFFAOYSA-N 1-isocyanato-6-(6-isocyanatohexylsulfanyl)hexane Chemical compound O=C=NCCCCCCSCCCCCCN=C=O DCQWACSEFXBOCJ-UHFFFAOYSA-N 0.000 description 2
- FLVFPAIGVBQGET-UHFFFAOYSA-N 1-methylpyrrolidin-3-ol Chemical compound CN1CCC(O)C1 FLVFPAIGVBQGET-UHFFFAOYSA-N 0.000 description 2
- FALCMQXTWHPRIH-UHFFFAOYSA-N 2,3-dichloroprop-1-ene Chemical class ClCC(Cl)=C FALCMQXTWHPRIH-UHFFFAOYSA-N 0.000 description 2
- JJSYPAGPNHFLML-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;3-sulfanylpropanoic acid Chemical compound OC(=O)CCS.OC(=O)CCS.OC(=O)CCS.CCC(CO)(CO)CO JJSYPAGPNHFLML-UHFFFAOYSA-N 0.000 description 2
- WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 description 2
- NXYWIOFCVGCOCB-UHFFFAOYSA-N 3-(2-sulfanylethylsulfanyl)-2-[3-sulfanyl-2-(2-sulfanylethylsulfanyl)propyl]sulfanylpropane-1-thiol Chemical compound SCCSCC(CS)SCC(CS)SCCS NXYWIOFCVGCOCB-UHFFFAOYSA-N 0.000 description 2
- KZPQYIBJZXONAE-UHFFFAOYSA-N 4,5-bis(isocyanatomethyl)-1,3-dithiolane Chemical class O=C=NCC1SCSC1CN=C=O KZPQYIBJZXONAE-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- JRANNTKZJNTXAU-UHFFFAOYSA-N CC1=C(C)C(C)=CC=C1.N=C=O.N=C=O.N=C=O Chemical compound CC1=C(C)C(C)=CC=C1.N=C=O.N=C=O.N=C=O JRANNTKZJNTXAU-UHFFFAOYSA-N 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 2
- OQSSNGKVNWXYOE-UHFFFAOYSA-N N=C=O.N=C=O.CCC(C)CC(C)(C)C Chemical class N=C=O.N=C=O.CCC(C)CC(C)(C)C OQSSNGKVNWXYOE-UHFFFAOYSA-N 0.000 description 2
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- YAAUVJUJVBJRSQ-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2-[[3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propoxy]methyl]-2-(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS YAAUVJUJVBJRSQ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
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- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- WFLLPKDDXLHZLQ-UHFFFAOYSA-N dibutoxy(dioctyl)stannane Chemical compound CCCCCCCC[Sn](OCCCC)(OCCCC)CCCCCCCC WFLLPKDDXLHZLQ-UHFFFAOYSA-N 0.000 description 2
- JJPZOIJCDNHCJP-UHFFFAOYSA-N dibutyl(sulfanylidene)tin Chemical compound CCCC[Sn](=S)CCCC JJPZOIJCDNHCJP-UHFFFAOYSA-N 0.000 description 2
- PKKGKUDPKRTKLJ-UHFFFAOYSA-L dichloro(dimethyl)stannane Chemical compound C[Sn](C)(Cl)Cl PKKGKUDPKRTKLJ-UHFFFAOYSA-L 0.000 description 2
- SDTDHTCWRNVNAJ-UHFFFAOYSA-L dimethyltin(2+);diacetate Chemical compound CC(=O)O[Sn](C)(C)OC(C)=O SDTDHTCWRNVNAJ-UHFFFAOYSA-L 0.000 description 2
- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 2
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- 229940093495 ethanethiol Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 239000012760 heat stabilizer Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- OFUBORBAMWUXTI-UHFFFAOYSA-N isocyanato-(isocyanatomethyldisulfanyl)methane Chemical compound O=C=NCSSCN=C=O OFUBORBAMWUXTI-UHFFFAOYSA-N 0.000 description 2
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- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- UOORRWUZONOOLO-OWOJBTEDSA-N (E)-1,3-dichloropropene Chemical compound ClC\C=C\Cl UOORRWUZONOOLO-OWOJBTEDSA-N 0.000 description 1
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- OWHDOWQWLQLUEQ-UHFFFAOYSA-N 1,2,3-trichloropropane Chemical compound ClCC(CCl)Cl.ClCC(CCl)Cl OWHDOWQWLQLUEQ-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- GHXPTDPKJYFMOE-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCCC1CN=C=O GHXPTDPKJYFMOE-UHFFFAOYSA-N 0.000 description 1
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- DGJUONISEWDPFO-UHFFFAOYSA-N dodecyl(triethyl)azanium Chemical class CCCCCCCCCCCC[N+](CC)(CC)CC DGJUONISEWDPFO-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical class CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- KFGJUQRJVQDJHL-UHFFFAOYSA-N ethanethiol Chemical compound CCS.CCS KFGJUQRJVQDJHL-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 125000001153 fluoro group Chemical class F* 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- IVTWEBSTMUFDIA-UHFFFAOYSA-N heptadecane-1,17-dithiol Chemical compound SCCCCCCCCCCCCCCCCCS IVTWEBSTMUFDIA-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- CNIQRWPMYHDBNS-UHFFFAOYSA-N isocyanato(isocyanatomethylsulfonyl)methane Chemical compound O=C=NCS(=O)(=O)CN=C=O CNIQRWPMYHDBNS-UHFFFAOYSA-N 0.000 description 1
- 150000002527 isonitriles Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- IXBUFAUQDFHNGI-UHFFFAOYSA-N methylsulfanylmethanethiol Chemical group CSCS IXBUFAUQDFHNGI-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical compound O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N p-dimethylbenzene Natural products CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Chemical class 0.000 description 1
- 230000036314 physical performance Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 229940071127 thioglycolate Drugs 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical class CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 description 1
- FYGHSUNMUKGBRK-UHFFFAOYSA-N trimethylbenzene Natural products CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
-
- 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
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
- C07C321/14—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
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- 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
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Abstract
实施方案涉及一种塑料镜片用聚硫醇组合物,实施方案所涉及的塑料镜片用聚硫醇组合物在聚合聚硫醇化合物、异氰酸酯、光活性色相修正剂等原料物质后,通过照射紫外线这样的简单的后续工序,就可以制造出清晰透明的塑料镜片。此外,上述镜片的制造工序简单且经济,因此能够有效使用于眼镜镜片、相机镜片等各种塑料镜片的制造中。
Description
技术领域
实施方案涉及一种塑料镜片用聚硫醇组合物(polythiol composition forplastic lens)。此外,实施方案涉及一种包含上述组合物的聚合性组合物、由 此所得的聚硫氨酯(polythiourethane)类化合物以及塑料镜片。
背景技术
相比由玻璃等无机材料构成的光学材料,塑料光学材料轻量、不易碎、 染色性优秀,因此各种树脂的塑料材料作为眼镜镜片、相机镜片等的光学材 料被广泛应用。近年来,进一步要求光学材料的高性能化,具体地,要求高 透明性、高折射率、低比重、高耐热性、高耐冲击性等。
聚硫氨酯类化合物因其优秀的光学特性及机械物理性能而作为光学材料 被广泛应用。聚硫氨酯类化合物是让聚硫醇化合物(polythiol compound)和 异氰酸酯化合物(isocyanate compound)反应而制得,上述聚硫醇化合物的物 理性能将大大影响所制得的聚硫氨酯类化合物的物理性能。
用聚硫氨酯类化合物制造的镜片由于折射率高、轻量、耐冲击性较高而 被广泛应用。但是,上述聚硫氨酯类镜片与玻璃镜片相比具有如下缺点,由 于阿贝数低导致清晰度低,从而佩戴镜片时眼镜的疲劳度大,并且相比玻璃 镜片耐热性低。
最近为了获得玻璃水准的透明度而努力的结果,介绍有如下方法,提高 原料自身的纯度或调节反应,从而提高透明性、折射率等光学特性。
作为一个例子,韩国公告专利第10-1338568号揭示了一种通过水解异硫 脲盐(isothiuronium salt)来制造聚硫醇化合物的方法,异硫脲盐(isothiuronium salt)通过让(聚)卤代化合物或(聚)醇类合物和硫脲(thiourea)反应所得, 上述硫脲中的钙含量在1.0重量%以下,因此能够获得无色透明的(聚)硫醇 化合物。此外,韩国公告专利第10-1464942号揭示了一种光学材料用聚硫醇 化合物的制造方法,包含让表氯醇(epichlorohydrin)化合物和2-巯基乙醇 (2-mercaptoethanol)反应的步骤,该聚硫醇化合物的制造方法中,上述表氯 醇化合物中的由丙烯醛(acrolein)、丙烯基氯(allylchloride)、1,2-二氯丙烷 (1,2-dichloro propane)、2,3-二氯丙烯(2,3-dichloropropene)、2-甲基-2- 戊醇(2-methyl-2-pentanol)、2-氯烯丙基醇(2-chloroallylalcohol)、顺式-1, 3-二氯丙烯(cis-1,3-dichloro propene)、反式-1,3-二氯丙烯(trans-1,3-dichloro propene)、1,3-二氯异丙醇(1,3-dichloro isopropanol)、1,2,3-三氯丙烷 (1,2,3-trichloro propane)及2,3-二氯丙醇(2,3-dichloropropanol)构成 的不纯物(杂质)的总含量在0.45重量%以下。
现有技术文献
专利文献
专利文献1:韩国公告专利第10-1338568号
专利文献2:韩国公告专利第10-1464942号
发明要解决的课题
然而,上述韩国公告专利第10-1338568号所揭示的技术是,调节作为聚 硫醇化合物的原料的硫脲的纯度,上述韩国公告专利第10-1464942号所揭示 的技术是,调节作为聚硫醇化合物的原料的表氯醇的纯度,因此体现玻璃水 准的透明度,即制造清晰透明的镜片有一定限度。此外,如果只管理原料物 质的纯度,不仅难以防止制造镜片时发生变黄的情况,而且不利于由此所得 镜片的质量、工艺性、经济方面。
于是,实施方案欲提供一种保持聚硫氨酯类塑料镜片的优点的同时具有 作为玻璃镜片的优点的高透明度的塑料镜片用聚硫醇组合物、由此得到的聚 硫氨酯类化合物以及塑料镜片。
发明内容
实施方案提供一种聚硫醇组合物,其包含有两个以上的官能团的聚硫醇 化合物及以下化学式1所示的化合物:
[化学式1]
上述式中,R1为C1-10烷基、C1-10烷氧基、苯基、或者被卤素置换的C1-10烷基;X为C1-10烷基、C1-10烷氧基、被卤素置换的硝基、C1-10二烷基氨基或 氰基;l及m分别独立为1或2,并且l+m=3;n为0到3的整数;l为2时, R1可以相同,也可以不相同,n为2或3时,X可以相同,也可以不相同。
进一步,实施方案提供一种聚硫氨酯类镜片用聚合性组合物,其包含有 异氰酸酯化合物、聚硫醇化合物及光活性色相修正剂。
此外,实施方案提供一种聚硫氨酯类镜片的制造方法,其包括:(1)提 供包含异氰酸酯化合物、聚硫醇化合物及光活性色相修正剂的聚合性组合物 的步骤;(2)将上述聚合性组合物热固化来制造聚硫氨酯类树脂的步骤;以 及(3)对上述聚硫氨酯类树脂照射紫外线而减少上述聚硫氨酯类树脂的黄色 指数的步骤。
发明效果
实施方案所涉及的塑料镜片用聚硫醇组合物在聚合聚硫醇化合物、异氰 酸酯等原料物质后,通过照射紫外线这样的简单的后续工序,就可以制造出 清晰透明的塑料镜片。此外,上述镜片的制造工序简单且经济,因此能够有 效使用于眼镜镜片、相机镜片等各种塑料镜片的制造中。
附图说明
图1是表示一实施例所涉及的聚硫醇组合物在照射紫外线前后的分子结 构的状态的示意图。
具体实施方式
一个实施方案提供一种聚硫醇组合物,其包含有两个以上官能团的聚硫 醇化合物及如下化学式1所示的化合物。
[化学式1]
上述式中,R1为C1-10烷基(alkyl)、C1-10烷氧基(alkoxy)、苯基(phenyl) 或被卤素置换的C1-10烷基;X为C1-10烷基、C1-10烷氧基、被卤素置换的硝基 (nitro)、C1-10二烷基氨基(dialkylamino)或氰基(cyano);l及m分别独立 为1或2,并且l+m=3;n为0到3的整数;l为2时,R1可以相同,也可 以不相同;n为2或3时,X可以相同,也可以不相同。
上述聚硫醇组合物可以包含上述化学式1所示的化合物和有两个以上官 能团的聚硫醇化合物,具体为有三个以上官能团的聚硫醇化合物。
上述化学式1所示的化合物可以是氧化膦(phosphine oxide)类化合物。 例如,可以是苯基二(2,4,6-三甲基苯甲酰基)氧化膦(bis(2,4,6-trimethyl benzoyl)phenylphosphine oxide)、苯基2,4,5-三甲基苯甲酰基亚磷酸盐(2, 4,5-trimethyl benzoyl)phenyl phosphine eate)、乙基2,4,6-三甲基苯甲酰 基苯基亚磷酸盐(ethyl 2,4,6-trimethylbenzoyl phenyl phosphine eate),具体 地,可以是苯基二(2,4,6-三甲基苯甲酰基)氧化膦或者苯基2,4,5-三 甲基苯甲酰基亚磷酸盐。
对于上述组合物,上述化学式1所示的化合物的含量可以是 50~40000ppm,具体为55~30000ppm。用上述组合物制造塑料镜片时,如果在 上述范围内,在照射紫外线后,就可以确保并维持色相更清晰透明。
上述有两个以上官能团的聚硫醇化合物可以是有机聚硫醇。
上述有机聚硫醇可以选自由1,2-二[(2-巯基乙基)硫基]-3-巯基丙烷(1, 2-bis[(2-mercapto ethyl)thio]-3-mercapto propane)、4,8-二巯基甲基-1,11- 二巯基-3,6,9-三硫代十一烷(4,8-dimercapto methyl-1,11-dimercapto-3, 6,9-trithiaundecane)、4,7-二巯基甲基-1,11-二巯基-3,6,9-三硫代十一 烷(4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithia undecane)、5, 7-二巯基甲基-1,11-二巯基-3,6,9-三硫代十一烷(5,7-dimercapto methyl-1, 11-dimercapto-3,6,9-trithiaundecane)、2,5-二甲基巯基-1,4-二噻烷(2, 5-bis(mercapto methyl)-1,4-dithiane)、季戊四醇四(巯基乙酸酯) (pentaerythritol tetra(mercapto acetate))、季戊四醇四(3-巯基丙酸酯) (pentaerythritol tetra(3-mercapto propionate))、三羟甲基丙烷三(巯基乙酸 酯)(trimethylolpropane tri(mercapto acetate))、三羟甲基丙烷三(3-巯基丙酸 酯)(trimethylolpropane tri(3-mercapto propionate))、二季戊四醇六(巯基乙酸酯)(dipentaerythritol hexa(mercapto acetate))、二季戊四醇六(3-巯基乙酸 酯)(dipentaerythritol hexa(3-mercapto propionate))、二(2-(2-巯基乙基硫 代)-3-巯基丙基)硫化物(bis(2-(2-mercapto ethyl thio)-3-mercapto propyl) sulfide)、4-巯基甲基-1,8-二巯基-3,6-二硫代辛烷(4-mercapto methyl-1, 8-dimercapto-3,6-dithiaoctane)、2,3-二(2-巯基乙基硫代)丙烷-1-硫醇(2, 3-bis(2-mercapto ethyl thio)propane-1-thiol)、2,2-二(巯基甲基)-1,3-丙 烷二硫醇(2,2-bis(mercapto methyl)-1,3-propane dithiol)、二(2-巯基乙 基)硫化物(bis(2-mercapto ethyl)sulfide)、四(巯基甲基)甲烷(tetrakis (mercapto methyl)methane)、2-(2-巯基乙基硫代)丙烷-1,3-二硫醇(2- (2-mercapto ethyl thio)propane-1,3-dithiol)、2-(2,3-二(2-巯基乙基硫代)丙基硫代)乙烷硫醇(2-(2,3-bis(2-mercapto ethyl thio)propyl thio)ethane thiol)、二(2,3-二巯基丙醇)硫化物(bis(2,3-dimercapto propanol)sulfide)、 二(2,3-二巯基丙醇)二硫化物(bis(2,3-dimercapto propanol)disulfid)、 1,2-二(2-(2-巯基乙基硫代)-3-巯基丙基硫代)乙烷(1,2-bis(2-(2-mercapto ethyl thio)-3-mercapto propylthio)ethane)、2-(2-巯基乙基硫代)-3-2-巯基 -3-[3-巯基-2-(2-巯基乙基硫代)-丙基硫代]丙基硫代-丙烷-1-硫醇(2- (2-mercapto ethyl thio)-3-2-mercapto-3-[3-mercapto-2-(2-mercapto ethyl thio) -propyl thio]propyl thio-propane-1-thiol)、2,2-二-(3-巯基-丙酰氧甲基)-丁酯 (2,2-bis-(3-mercapto-propionyl oxymethyl)-butyl ester)、2-(2-巯基乙基硫 代)-3-(2-(2-[3-巯基-2-(2-巯基乙基硫代)-丙基硫代]乙基硫代)乙基硫代) 丙烷-1-硫醇(2-(2-mercapto ethyl thio)-3-(2-(2-[3-mercapto-2-(2-mercapto ethyl thio)-propyl thio]ethyl thio)ethyl thio)propane-1-thiol)、(4R,11S)-4, 11-二(巯基甲基)-3,6,9,12-四硫代四癸烷-1,14-二硫醇((4R,11S)-4, 11-bis(mercapto methyl)-3,6,9,12-tetra thia tetra decane-1,14-dithiol)、 (S)-3-((R-2,3-二巯基丙基)硫代)丙烷-1,2-二硫醇((S)-3-((R-2, 3-dimercapto propyl)thio)propane-1,2-dithiol)、(4R,14R)-4,14-二(巯 基甲基)-3,6,9,12,15-五硫代庚烷-1,17-二硫醇((4R,14R)-4,14-bis (mercapto methyl)-3,6,9,12,15-penta thiaheptane-1,17-dithiol)、(S) -3-((R-3-巯基-2-((2-巯基乙基)硫代)丙基硫代)丙基硫代)-2-((2-巯基 乙基)硫代)丙烷-1-硫醇((S)-3-((R-3-mercapto-2-((2-mercaptoethyl)thio) propylthio)propylthio)-2-((2-mercapto ethyl)thio)propane-1-thiol)、3,3'- 二硫代二(丙烷-1,2-二硫醇)(3,3'-dithio bis(propane-1,2-dithiol))、(7R, 11S)-7,11-二(巯基甲基)-3,6,9,12,15-五硫代十七烷一百烷-1,17- 二硫醇((7R,11S)-7,11-bis(mercapto methyl)-3,6,9,12,15-penta thia heptadecane-1,17-dithiol)、(7R,12S)-7,12-二(巯基甲基)-3,6,9,10, 13,16-六硫代十八烷-1,18-二硫醇((7R,12S)-7,12-bis(mercapto methyl) -3,6,9,10,13,16-hexa thia octadecane-1,18-dithiol)、季戊四醇四(3- 巯基丙酸酯)(penta erythritol tetrakis(3-mercaptopropionate))、三亚甲醇丙 烷三(3-巯基丙酸酯)(trimethylol propane tris(3-mercapto propionate))、季 戊四醇四(2-巯基乙酸盐)(pentaerythritol tetrakis(2-mercapto acetate))、二 季戊四醇-***-苯丙锡(3-巯基丙酸酯)(bispenta erythritol-ether-hexakis (3-mercapto propionate))、1,1,3,3-四(巯基甲基硫代)丙烷(1,1,3,3-tetrakis(mercapto methyl thio)propane)、1,1,2,2-四(巯基甲基硫代) 乙烷(1,1,2,2-tetrakis(mercapto methyl thio)ethane)、4,6-二(巯基甲 基硫代)-1,3-二噻烷(4,6-bis(mercapto methyl thio)-1,3-dithiane)、2- (2,2-二(巯基二甲基硫代)乙基)-1,3-二噻烷(2-(2,2-bis(mercapto dimethyl thio)ethyl)-1,3-dithiane)及这些的混合物构成的群。
具体地,可以是1,2-二[(2-巯基乙基)硫基]-3-巯基丙烷(1, 2-bis[(2-mercaptoethyl)thio]-3-mercapto propane)、4,8-二巯基甲基-1,11- 二巯基-3,6,9-三硫代十一烷(4,8-dimercapto methyl-1,11-dimercapto-3, 6,9-trithia undecane)、4,7-二巯基甲基-1,11-二巯基-3,6,9-三硫代十一 烷(4,7-dimercapto methyl-1,11-dimercapto-3,6,9-trithia undecane)、5, 7-二巯基甲基-1,11-二巯基-3,6,9-三硫代十一烷(5,7-dimercapto methyl-1, 11-dimercapto-3,6,9-trithia undecane)、2,5-二甲基巯基-1,4-二噻烷(2, 5-bis(mercapto methyl)-1,4-dithiane)、季戊四醇四(巯基乙酸酯)(pentaerythritol tetra(mercapto acetate))、季戊四醇四(3-巯基丙酸酯)(pentaerythritol tetra(3-mercapto propionate))、三羟甲基丙烷三(巯基乙酸 酯)(trimethylolpropane tri(mercapto acetate))、三羟甲基丙烷三(3-巯基丙酸 酯)(trimethylolpropane tri(3-mercapto propionate))、二季戊四醇六(巯基 乙酸酯)(dipentaerythritol hexa(mercapto acetate))、二季戊四醇六(3-巯基丙 酸酯)(dipentaerythritol hexa(3-mercapto propionate))或这些的混合物。
更具体地,可以是1,2-二[(2-巯基乙基)硫基]-3-巯基丙烷(1, 2-bis[(2-mercapto ethyl)thio]-3-mercapto propane)、4,8-二巯基甲基-1,11- 二巯基-3,6,9-三硫代十一烷(4,8-dimercapto methyl-1,11-dimercapto-3, 6,9-trithia undecane)、4,7-二巯基甲基-1,11-二巯基-3,6,9-三硫代十一 烷(4,7-dimercapto methyl-1,11-dimercapto-3,6,9-trithia undecane)、5, 7-二巯基甲基-1,11-二巯基-3,6,9-三硫代十一烷(5,7-dimercapto methyl-1, 11-dimercapto-3,6,9-trithia undecane)、2,5-二甲基巯基-1,4-二噻烷(2, 5-bis(mercapto methyl)-1,4-dithiane)或这些的混合物。
对于上述组合物,光谱(optical spectrum)中400nm处的透过度为T400 (%),450nm处的透过度为T450(%)时,满足如下数学式1:
[数学式1]
30<A=(T450%)-(T400%)<95。
此时,上述A表示400nm及450nm处的透过度的差值,上述A值越小, 黄色指数(yellow index:Y.I.)就越低。上述Y.I.值可以利用能够测出色度坐 标的仪器来测得。将上述聚硫醇组合物以[L*a*b*色坐标](Lab色空间)表示 时,b*可以是1.0以上、1.5以上、或者2.0以上。上述Y.I.及b*是在本领域 中广为人知的色相评价方法的参数,Y.I.适用于固体的色相评价,b*适用于液 体的色相评价。
实施方案提供一种包含异氰酸酯(isocyanate)化合物、聚硫醇化合物及 光活性色相修正剂的聚硫氨酯类镜片用聚合性组合物。
上述光活性色相修正剂可包含上述化学式1所示的化合物。
上述聚合性组合物包含上述光活性色相修正剂,因此照射紫外线使聚合 性组合物固化而形成的聚硫氨酯类树脂的黄色指数可以更低。此时,上述紫 外线可以在395nm~445nm的UVV区域的波长中以1J~3J的光量照射5分钟 ~50分钟、10分钟~50分钟、5分钟~45分钟、或者10分钟~45分钟。
具体地,上述聚合性组合物热固化后形成的聚硫氨酯类树脂的黄色指数 称为第一黄色指数,对上述聚硫氨酯类树脂照射紫外线后的黄色指数称为第 二黄色指数,此时上述第一黄色指数大于第二黄色指数。
更具体地,上述第二黄色指数可以是0.1~5.5、0.1~5.4、0.5~5.4、或者 1.0~5.4。此时,上述第一黄色指数可以具有比上述第二黄色指数大一定量的 值。例如,上述第一黄色指数及上述第二黄色指数的差值可以是0.11以上, 更具体地,上述第一黄色指数及上述第二黄色指数的差值可以是0.2以上。
上述异氰酸酯化合物可以使用聚硫氨酯的合成中普遍使用的化合物。
具体地,上述异氰酸酯化合物可以选自由包含异佛尔酮二异氰酸酯 (isophoronediisocyanate)、二环己基甲烷-4,4-二异氰酸酯 (dicyclohexylmethane-4,4-diisocyanate)、六亚甲基二异氰酸酯(hexa methylene diisocyanate)、2,2-二甲基戊烷二异氰酸酯(2,2-dimethyl pentane diisocyanate)、2,2,4-三甲基己烷二异氰酸酯(2,2,4-trimethyl hexane diisocyanate)、丁烯二异氰酸酯(butene diisocyanate)、1,3-丁二烯-1,4-二 异氰酸酯(1,3-butadiene-1,4-diisocyanate)、2,4,4-三甲基六亚甲基二异氰酸酯(2,4,4-trimethyl hexa methylene diisocyanate)、1,6,11-十一烷三 异氰酸酯(1,6,11-undecane triisocyanate)、1,3,6-六亚甲基三异氰酸酯 (1,3,6-hexamethylene triisocyanate)、1,8-二异氰酸酯-4-异氰酸基甲基辛 烷(1,8-diisocyanate-4-isocyanato methyl octane)、二(异氰酸基乙基)碳酸 酯(bis(isocyanato ethyl)carbonate)、二(异氰酸基乙基)***(bis(isocyanato ethyl)ether)、1,2-二(异氰酸基甲基)环己烷(1,2-bis(isocyanato methyl) cyclo hexane)、1,3-二(异氰酸基甲基)环己烷(1,3-bis(isocyanato methyl) cyclo hexane)、1,4-二(异氰酸基甲基)环己烷(1,4-bis(isocyanato methyl) cyclo hexane)、二环己基甲烷二异氰酸酯(dicyclo hexylmethane diisocyanate)、 环己烷二异氰酸酯(cyclo hexane diisocyanate)、甲基环己烷二异氰酸酯(methyl cyclo hexane diisocyanate)、二环己基二甲基甲烷异氰酸酯(dicyclo hexyl dimethyl methane isocyanate)、2,2-二甲基二环己基甲烷异氰酸酯(2,2-dimethyl dicyclo hexyl methane isocyanate)、二(异氰酸基乙基)硫化物(bis(isocyanato ethyl)sulphide)、二(异氰酸基丙基)硫化物(bis(isocyanato propyl)sulphide)、 二(异氰酸基己基)硫化物(bis(isocyanato hexyl)sulphide)、二(异氰酸基甲基)砜(bis(isocyanato methyl)sulfone)、二(异氰酸基甲基)二硫化物 (bis(isocyanato methyl)disulphide)、二(异氰酸基丙基)二硫化物(bis (isocyanatopropyl)disulphide)、二(异氰酸基甲基硫代)甲烷(bis(isocyanato methyl thio)methane)、二(异氰酸基乙基硫代)甲烷(bis(isocyanato ethyl thio) methane)、二(异氰酸基乙基硫代)乙烷(bis(isocyanato ethyl thio)ethane)、 二(异氰酸基甲基硫代)乙烷(bis(isocyanato methyl thio)ethane)、1,5- 二异氰酸基-2-异氰酸基甲基-3-硫代戊烷(1,5-diisocyanato-2-isocyanato methyl-3-thia pentane)、2,5-二异氰酸基噻吩(2,5-diisocyanato thiophene)、 2,5-二(异氰酸基甲基)噻吩(2,5-bis(isocyanato methyl)thiophene)、2, 5-二异氰酸基四氢噻吩(2,5-diisocyanato tetra hydrothiophene),2,5-二(异 氰酸基甲基)四氢噻吩(2,5-bis(isocyanato methyl)tetra hydrothiophene)、3,4-二(异氰酸基甲基)四氢噻吩(3,4-bis(isocyanato methyl)tetra hydrothiophene)、2,5-二异氰酸基-1,4-二噻烷(2,5-diisocyanato-1,4-dithiane)、 2,5-二(异氰酸基甲基)-1,4-二噻烷(2,5-bis(isocyanato methyl)-1,4-dithiane)、 4,5-二异氰酸基-1,3-二噻茂烷(4,5-diisocyanato-1,3-dithiolane)、4,5- 二(异氰酸基甲基)-1,3-二噻茂烷(4,5-bis(isocyanato methyl)-1,3-dithiolane)、 4,5-二(异氰酸基甲基)-2-甲基-1,3-二噻茂烷(4,5-bis(isocyanato methyl) -2-methyl-1,3-dithiolane)等的脂肪族异氰酸酯类化合物;包含二(异氰酸基 乙基)苯(bis(isocyanatoethyl)benzene)、二(异氰酸基丙基)苯(bis(isocyanato propyl)benzene)、二(异氰酸基丁基)苯(bis(isocyanato butyl)benzene)、 二(异氰酸基甲基)萘(bis(isocyanato methyl)naphthalene)、二(异氰酸基甲基)二苯基***(bis(isocyanato methyl)diphenyl ether)、亚苯基二异氰酸 酯(phenylene diisocyanate)、乙基亚苯基二异氰酸酯(ethyl phenylene diisocyanate)、异丙基亚苯基二异氰酸酯(isopropyl phenylene diisocyanate)、 二甲基亚苯基二异氰酸酯(dimethyl phenylene diisocyanate)、二乙基亚苯基二 异氰酸酯(diethylphenylene diisocyanate)、二异丙基亚苯基二异氰酸酯 (diisopropyl phenylenediisocyanate)、三甲基苯三异氰酸酯(trimethyl benzene triisocyanate)、苯三异氰酸酯(benzene triisocyanate)、联苯二异氰酸酯(biphenyl diisocyanate)、甲苯二异氰酸酯(toluene diisocyanate)、甲苯胺二异氰酸酯 (toluidine diisocyanate)、4,4-二苯基甲烷二异氰酸酯(4,4-diphenyl methane diisocyanate)、3,3-二甲基二苯基甲烷-4,4-二异氰酸酯(3,3-dimethyl diphenyl methane-4,4-diisocyanate)、联苄-4,4-二异氰酸酯(bibenzyl-4,4-diisocyanate)、 二(异氰酸基苯基)乙烯(bis(isocyanato phenyl)ethylene)、3,3-二甲氧 基联苯-4,4-二异氰酸酯(3,3-dimethoxy biphenyl-4,4-diisocyanate)、六氢 苯二异氰酸酯(hexa hydrobenzene diisocyanate)、六氢二苯基甲烷-4,4-二异 氰酸酯(hexa hydro diphenyl methane-4,4-diisocyanate)、邻二甲苯二异氰酸 酯(o-xylene diisocyanate)、间苯二甲基二异氰酸酯(m-xylene diisocyanate)、对二甲苯二异氰酸酯(p-xylene diisocyanate)、二甲苯二异氰酸酯(xylenediisocyanate)、焦化二甲苯二异氰酸酯(X-xylene diisocyanate)、1,3-二(异 氰酸基甲基)环乙烷(1,3-bis(isocyanato methyl)cyclohexane)、二苯基硫 化物-2,4-二异氰酸酯(diphenyl sulphide-2,4-diisocyanate)、二苯基硫化物-4,4-二异氰酸酯(diphenylsulphide-4,4-diisocyanate)、3,3-二甲氧基-4, 4-二异氰酸基二苯甲基硫代***(3,3-dimethoxy-4,4-diisocyanato dibenzyl thio ether)、二(4-异氰酸基甲基苯)硫化物(bis(4-isocyanato methyl benzene) sulphide)、4,4-甲氧基苯硫代乙烯乙二醇-3,3-二异氰酸酯(4,4-methoxy benzene thio ethylene glycol-3,3-diisocyanate)、二苯基二硫化物-4,4-二异氰 酸酯(diphenyl disulphide-4,4-diisocyanate)、2,2-二甲基二苯基二硫化物-5, 5-二异氰酸酯(2,2-dimethyl diphenyl disulphide-5,5-diisocyanate)、3,3-二 甲基二苯基二硫化物-5,5-二异氰酸酯(3,3-dimethyl diphenyl disulphide-5,5-diisocyanate)、3,3-二甲基二苯基二硫化物-6,6-二异氰酸酯(3,3-dimethyl diphenyldisulphide-6,6-diisocyanate)、4,4-二甲基二苯基二硫化物-5,5-二 异氰酸酯(4,4-dimethyl diphenyl disulphide-5,5-diisocyanate)、3,3-二甲氧 基二苯基二硫化物-4,4-二异氰酸酯(3,3-dimethoxy diphenyl disulphide-4, 4-diisocyanate)、4,4-二甲氧基二苯基二硫化物-3,3-二异氰酸酯(4, 4-dimethoxy diphenyl disulphide-3,3-diisocyanate)等的芳香族异氰酸酯类化 合物以及这些的混合物所构成的群。
具体地,可以使用1,3-二(异氰酸基甲基)环乙烷(1,3-bis(isocyanato methyl)cyclohexane)、六亚甲基二异氰酸酯(hexa methylene diisocyanate)、 异佛尔酮二异氰酸酯(isophorone diisocyanate)、二甲苯二异氰酸酯(xylene diisocyanate)、甲苯二异氰酸酯(toluene diisocyanate)等。
根据目的,上述聚合性组合物还可以包含内部脱模剂、热稳定剂、反应 催化剂、紫外线吸收剂、上蓝剂(blueing agent)等添加剂。
上述内部脱模剂可以从具有全氟烷基(perfluoroalkyl group)、羟烷基(hydroxyalkyl group)、或者磷酸酯基(phosphate ester group)的氟系列非离 子界面活性剂;具有二甲基聚硅氧烷基(dimethylpolysiloxane group)、羟烷基 (hydroxyalkylgroup)、或者磷酸酯基(phosphate ester group)的硅胶系列非 离子界面活性剂;如三甲基十六烷基铵盐(trimethylcetyl ammonium salt)、三 甲基十八烷基铵盐(trimethylstearyl ammonium salt)、二甲基乙基十六烷基铵 盐(dimethylethylcetylammonium salt)、三乙基十二烷基铵盐(triethyldodecyl ammonium salt)、三辛基甲基铵盐(trioctylmethyl ammonium salt)、二乙基环 己基十二烷基铵盐(diethylcyclohexadodecyl ammonium salt)等烷基季铵盐 (alkyl quaternaryammonium salts);以及酸性磷酸酯中选择,其成分可以单独 或混合2种以上一起使用。
上述热稳定剂可使用金属脂肪酸盐类、磷类、铅类、有机锡类等中的1 种或者2种以上。
作为上述反应催化剂,可适当添加制造聚硫氨酯类树脂时所使用的公知 的反应催化剂。例如,可以选自由二丁基二氯化锡(dibutyltin dichloride)、二 甲基二氯化锡(dimethyltin dichloride)等二烷基锡卤化物(dialkyltin halide) 类;二乙酸二甲基锡(dimethyltin diacetate)、二辛酸二丁基锡(dibutyltin dioctanoate)、二月桂酸二丁基锡(dibutyltin dilaurate)等二烷基锡二羧酸 (dialkyltin dicarboxylate)类;二丁氧基二丁基锡(dibutyltin dibutoxide)、二 丁氧基二辛基锡(dioctyltin dibutoxide)等二烷基锡二醇盐(dialkyltin dialkoxide)类;二丁基二(硫醚)(dibutyltin di(thiobutoxide))等二烷基锡 二硫醇盐(dialkyltin dithioalkoxide)类;二(2-乙基己基)锡氧化物(di (2-ethylhexyl)tin oxide)、二辛基锡氧化物(dioctyl tin oxide)、二(丁氧基二丁基锡)氧化物(bis(butoxy dibutyle tin)oxide)等二烷基锡氧化物(dialkyltinoxide)类;二丁基锡硫化物(dibutyltin sulfide)等二烷基锡硫化物(dialkyltinsulfide)类构成的群。具体地,可以选自由二丁基二氯化锡(dibutyltin dichloride)、二甲基二氯化锡(dimethyltin dichloride)等二烷基锡卤化物 (dialkyltin halide)类构成的群。
上述紫外线吸收剂可使用苯甲酮(benzophenone)类、苯并*** (benzotriazole)类、水杨酸(salicylate)类、氰基丙烯酸酯(cyanoacrylate) 类、草酰替苯胺(oxanilide)类等。
上述上蓝剂对可见光区域中的橙色至黄色的波域具有吸收带,并具有对 由树脂制成的光学材料的色相进行调整的功能。上述上蓝剂具体可包含表示 蓝色至紫色的物质,但并不限定于此。此外,上述上蓝剂可例举染料、荧光 增白剂、荧光颜料、无机颜料等,但是可以配合所要制造的光学部件要求的 物理性能、树脂色相等适当选择。上述上蓝剂可以分别单独使用或者组合两 种以上来使用。
从对聚合性组合物的溶解性的观点以及所获得的光学材料的透明性的观 点来看,上述上蓝剂优选染料。关于上述染料,从吸收波长的观点来看,具 体可为极大吸收波长为520~600nm的染料,更加具体地,可为极大吸收波长 为540~580nm的染料。此外,从化合物结构的观点来看,上述染料优选蒽醌 (anthraquinone)类染料。上蓝剂的添加方法并没有特别限定,可以事先添加 至单体(monomer)系列中。具体地,上述上蓝剂的添加方法可使用如下多种 方法:溶解于单体中的方法;或者,制造出含有高浓度上蓝剂的母液(mastersolution),并用使用上述母液的单体或者其他添加剂稀释后添加的方法等。
实施方案提供一种在模具中热固化如上上述的聚合性组合物来制造聚硫 氨酯类塑料镜片的方法。根据一个实施方式,上述聚硫氨酯类塑料镜片可通 过以下步骤制造出来:(1)提供包含异氰酸酯化合物、聚硫醇化合物及光活 性色相修正剂的聚合性组合物的步骤;(2)通过热固化上述聚合性组合物来 制造聚硫氨酯类树脂的步骤;以及(3)对上述聚硫氨酯类树脂照射紫外线以 减少上述聚硫氨酯类树脂的黄色指数的步骤。进而,实施方案提供一种使用 上述制造方法得到的聚硫氨酯类塑料镜片。
具体地,在上述步骤(1)中,准备如上上述的聚合性组合物。
接着,在上述步骤(2)中,在减压下对上述聚合性组合物进行脱气 (degassing)后,注入到镜片成形用模具中。像这样的脱气及模具内的注入, 例如可以在20~40℃的温度范围内进行。注入到模具中后,通常从低温逐渐加 热至高温而进行聚合。上述聚合反应的温度,例如可以是20~150℃,具体地, 可以是25~120℃。
此时,上述模具的形状可以根据用途进行多种变更。例如,根据眼镜镜 片、相机镜片等用途,可使用不同形状的模具。
此外,在上述步骤(2)中,能够从约0~30℃之间的初始温度以1℃/分钟 ~10℃/分钟的速度进行加热。进而,上述聚合性组合物在热固化阶段以上述速 度被加热至约100~150℃的温度后,可以维持5小时~30小时。
在上述步骤(3)中,热固化后马上对所形成的聚硫氨酯类树脂照射在 395nm~445nmUVV区域的波长中的1J~3J的光量的紫外线,从而可以减少上 述树脂的黄色指数。具体地,就上述聚合性组合物而言,通过后续工序对聚 合后所形成的聚合体(即聚硫氨酯类树脂)照射紫外线,可以制造出清晰透 明的塑料镜片。更具体地,上述聚硫氨酯类树脂被紫外线照射后,上述黄色 指数可以减少0.11以上或0.2以上。上述紫外线可以照射5分钟~50分钟、10 分钟~50分钟、5分钟~45分钟、或者10分钟~45分钟。此时,光量可利用 EIT公司的光量计(UV Power PUCK)来测量。
上述聚合性组合物通过混合和聚合上述异氰酸酯化合物、聚硫醇化合物、 光活性色相修正剂、催化剂、脱模剂等而获得,进而制造塑料镜片,并利用 以上述UVV区域为主波长的紫外灯(UV lamp)照射紫外线(UV)来消除固 有的色相,从而能够制造出更透明的镜片。
此时,如上所述,上述光活性色相修正剂可以是上述化学式1所示的化 合物。上述化学式1所示的化合物、例如氧化膦(phosphine oxide)类化合物 在UVA区域和UVV区域具有吸收波长,因此初期的聚硫醇组合物的色相呈 黄色。但是,制造镜片后如果利用以UVV区域为主波长带的UV灯(例如 TL灯、黑光灯等)以1J~3J的光量照射紫外线的话,呈固有的黄色的氧化膦 类化合物被紫外线(UV)分解,固有的黄色可以被消除。这种现象被称之为 光漂白(photo-bleaching)。
进一步,上述氧化膦类化合物因照射紫外线而被分解,并作为分解物产 生自由基(radical)。此时,聚硫氨酯类树脂的分子结构中也生成自由基,但 是该自由基与氧结合之前先与上述氧化膦类化合物的分解物结合。因此,上 述氧化膦类化合物能够防止上述聚硫氨酯类树脂的氧化(参见图1)。
此外,由于聚硫氨酯类树脂的分子结构在热固化后并非是完整的基态 (groundstate),所以通过照射紫外线变成激发态(exited state)时,容易回 到基态(groundstate),从而镜片的色相变得更透明清晰(参见图1)。
根据需要,为了防止反射、赋予高硬度、提高耐磨耗性、提高耐药性、 赋予防雾性(anti-fogging)、或者赋予时尚性(fashionity),可以对通过这种 方法制造的塑料镜片实施表面研磨、防带电处理、硬涂层处理、防反射涂层 处理、染色处理、调光处理等物理性、化学性处理进行改良。
如此,关于实施方案所涉及的塑料镜片用聚硫醇组合物,使聚硫醇化合 物、异氰酸酯化合物、光活性色相修正剂等原料物质聚合后,通过照射紫外 线这样的简单的后续工序,可以制造出清晰透明的塑料镜片。此外,上述镜 片的制造工序简单且经济,因此能够有效使用于眼镜镜片、相机镜片等各种 塑料镜片的制造中。
下面,根据下述实施例,对本发明作更加详细的说明。但是,下述实施 例仅仅是为了例示本发明而已,本发明的范围并不限定于这些实施例。
实施例1:聚硫醇组合物的制造
通过日本特开平7-252207号公报的实施例1所记载的方法获得包含4, 8-二巯基甲基-1,11-二巯基-3,6,9-三硫代十一烷(4,8-dimercapto methyl-1, 11-dimercapto-3,6,9-trithia undecane)、4,7-二巯基甲基-1,11-二巯基-3, 6,9-三硫代十一烷(4,7-dimercapto methyl-1,11-dimercapto-3,6,9-trithia undecane)及5,7-二巯基甲基-1,11-二巯基-3,6,9-三硫代十一烷(5, 7-dimercapto methyl-1,11-dimercapto-3,6,9-trithia undecane)的有四个官能 团的聚硫醇化合物的混合物。此时,包含在上述混合物中的各聚硫醇化合物 是结构异构体(structural isomer)关系。混合上述聚硫醇混合物与作为化学式 1所示的化合物的苯基二(2,4,6-三甲基苯甲酰基)氧化膦(bis(2,4, 6-trimethylbenzoyl)phenylphosphine oxide)(光起始剂819(Irgacure819), BASF公司)60ppm,从而制造出聚硫醇组合物。
实施例2~9及比较例1:聚硫醇组合物的制造
如下述表1所记载,除了改变化学式1所示的化合物的种类及含量以外, 实施与实施例1相同的方法,从而制得聚硫醇组合物。
【表1】
光起始剂819及光起始剂TPO-L:BASF公司
实施例10:聚合性组合物的制造
将上述实施例1的聚硫醇组合物49.3重量部、二甲苯二异氰酸酯(xylenediisocyanate)50.7重量部、作为聚合催化剂的二丁基氯化锡(dibutyltin chloride)0.01重量部及作为内部脱模剂的UN(酸性磷酸烷基酯(phosphoric alkyl ester)脱模剂,Stepan公司)0.1重量部均匀混合,从而制得聚合性组合物。
实施例11~18及比较例2:聚合性组合物的制造
如下述表1所记载,除了分别使用实施例2~9及比较例1的聚硫醇组合 物以外,实施与实施例10相同的方法,从而分别制得实施例11~18及比较例 2的聚合性组合物。
实验例:确认物理性质
将上述实施例1~9及比较例1中所制得的聚硫醇组合物、以及上述实施 例10~18及比较例2中所制得的聚合性组合物作为对象,如下述那样测量物 理性质,测量结果如下表2及表3所示。
(1)测量b*
在内部厚度为10mm的石英试池(quartz cell)中注入在上述实施例1~9 及比较例1中所制得的聚硫醇组合物,并利用分光测色计(CM-3700A,美能 达公司)求得b*。b*值越大,则评价液相的组合物越透明。其结果如下面表 2所示。
(2)黄色指数(Yellow Index,Y.I.)
将上述实施例10~18及比较例2的聚合性组合物在600Pa下进行1小时 的脱气(degassing)后,用3μm的聚四氟乙烯过滤器(Teflon filter)进行过 滤。将过滤后的聚合性组合物注入至用胶带组装的玻璃铸模中。将上述铸模 从25℃以5℃/分钟的速度升温至120℃,在120℃下进行18小时的聚合。接 着,将玻璃铸模中的固化树脂在130℃下进一步固化4小时之后,使成形体(塑 料镜片)从玻璃铸模中脱模。此时,上述镜片是用厚度为9mm、φ为75mm 的圆形镜片平板铸模制得。对所制得的镜片,利用分光测色计(CM-3700A, 美能达公司)测量400nm下的透过度(T400%)及450nm下的透过度(T450%), 并求得它们的差值(A=T450%-T400%)。
使用相同的仪器在固化后马上测量Y.I.值,然后利用TL灯(飞利浦公司) 再对同一个镜片照射10分钟,使UVV的光量达到1.5J,之后利用分光测色 计测量UV照射后的Y.I.值。其结果如下面表3所示。
【表2】
【表3】
如上述表2所示,相比比较例1的聚硫醇组合物,实施例1~9的聚硫醇 组合物的b*值大,从而可知其为透明的液相。进一步,从上述表3可知,在 实施例10~18中制得的镜片与在比较例2中制得的镜片进行比较时,透过度 的差异大,且刚刚固化后的Y.I.值虽然较大,但UV照射后的Y.I.值显著减少。 因此,可以预想到通过本实施例制造的塑料镜片更透明且能形成清晰的图像, 从而可被有效使用。
Claims (18)
1.一种聚硫醇组合物,其包含有两个以上的官能团的聚硫醇化合物及以下化学式1所示的化合物:
[化学式1]
上述式中,
R1为C1-10烷基、C1-10烷氧基、苯基或被卤素置换的C1-10烷基,
X为C1-10烷基、C1-10烷氧基、被卤素置换的硝基、C1-10二烷基氨基或氰基,
l及m分别独立为1或2,
l+m=3,
n为0到3的整数,
l为2时,R1可以相同,也可以不相同,n为2或3时,X可以相同,也可以不相同。
2.如权利要求1所述的聚硫醇组合物,其特征在于,
对于上述组合物,上述化学式1所示的化合物的含量为55~30,000ppm。
3.如权利要求1所述的聚硫醇组合物,其特征在于,
上述有两个以上的官能团的聚硫醇化合物选自由1,2-二[(2-巯基乙基)硫基]-3-巯基丙烷、4,8-二巯基甲基-1,11-二巯基-3,6,9-三硫代十一烷、4,7-二巯基甲基-1,11-二巯基-3,6,9-三硫代十一烷、5,7-二巯基甲基-1,11-二巯基-3,6,9-三硫代十一烷、2,5-二甲基巯基-1,4-二噻烷、季戊四醇四(巯基乙酸酯)、季戊四醇四(3-巯基丙酸酯)、三羟甲基丙烷三(巯基乙酸酯)、三羟甲基丙烷三(3-巯基丙酸酯)、二季戊四醇六(巯基乙酸酯)、二季戊四醇六(3-巯基乙酸酯)及这些的混合物构成的群。
4.如权利要求1所述的聚硫醇组合物,其特征在于,
用L*a*b*色坐标表示上述组合物时,液相b*为2.0以上。
5.如权利要求1所述的聚硫醇组合物,其特征在于,
上述组合物在400nm处的透过度为T400(%),在450nm处的透过度为T450(%)时,满足如下数学式1:
[数学式1]
30<A=(T450%)-(T400%)<95。
6.一种聚硫氨酯类镜片用聚合性组合物,其包含:
异氰酸酯化合物;
聚硫醇化合物;以及
光活性色相修正剂。
7.如权利要求6所述的聚硫氨酯类镜片用聚合性组合物,其特征在于,
上述光活性色相修正剂包含以下化学式1所示的化合物:
[化学式1]
上述式中,
R1为C1-10烷基、C1-10烷氧基、苯基或被卤素置换的C1-10烷基,
X为C1-10烷基、C1-10烷氧基、被卤素置换的硝基、C1-10二烷基氨基或氰基,
l及m分别独立为1或2,
l+m=3,
n为0到3的整数,
l为2时,R1可以相同,也可以不相同,n为2或3时,X可以相同,也可以不相同。
8.如权利要求6所述的聚硫氨酯类镜片用聚合性组合物,其特征在于,
上述聚合性组合物热固化后形成的聚硫氨酯类树脂的第一黄色指数大于对上述聚硫氨酯类树脂照射紫外线后的第二黄色指数。
9.如权利要求8所述的聚硫氨酯类镜片用聚合性组合物,其特征在于,
上述第一黄色指数及上述第二黄色指数的差值为0.11以上。
10.如权利要求9所述的聚硫氨酯类镜片用聚合性组合物,其特征在于,
上述第一黄色指数及上述第二黄色指数的差值为0.2以上。
11.如权利要求8所述的聚硫氨酯类镜片用聚合性组合物,其特征在于,
上述紫外线在395nm~445nmUVV区域的波长中以1J~3J的光量进行照射。
12.如权利要求8所述的聚硫氨酯类镜片用聚合性组合物,其特征在于,
上述第二黄色指数为0.1~5.5。
13.一种聚硫氨酯类镜片的制造方法,其包括:
(1)提供包含异氰酸酯化合物、聚硫醇化合物及光活性色相修正剂的聚合性组合物的步骤;
(2)将上述聚合性组合物热固化来制造聚硫氨酯类树脂的步骤;以及
(3)对上述聚硫氨酯类树脂照射紫外线而减少上述聚硫氨酯类树脂的黄色指数的步骤。
14.如权利要求13所述的聚硫氨酯类镜片的制造方法,其特征在于,
在上述步骤(2)中,上述聚合性组合物从0~30℃之间的初始温度以1℃/分钟~10℃/分钟的速度进行加热。
15.如权利要求14所述的聚硫氨酯类镜片的制造方法,其特征在于,
在上述步骤(2)中,上述聚合性组合物被加热至100~150℃的温度后,维持5小时~30小时。
16.如权利要求13所述的聚硫氨酯类镜片的制造方法,其特征在于,
在上述步骤(3)中,照射紫外线后,上述聚硫氨酯类树脂的黄色指数减少0.11以上。
17.如权利要求13所述的聚硫氨酯类镜片的制造方法,其特征在于,
在上述步骤(3)中,上述紫外线在395nm~445nmUVV区域的波长中以1J~3J的光量进行照射。
18.如权利要求17所述的聚硫氨酯类镜片的制造方法,其特征在于,
上述紫外线照射5分钟~50分钟。
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