CN117304082A - Polythiol compound for optical resin lens, optical resin lens and preparation method of optical resin lens - Google Patents
Polythiol compound for optical resin lens, optical resin lens and preparation method of optical resin lens Download PDFInfo
- Publication number
- CN117304082A CN117304082A CN202311269923.2A CN202311269923A CN117304082A CN 117304082 A CN117304082 A CN 117304082A CN 202311269923 A CN202311269923 A CN 202311269923A CN 117304082 A CN117304082 A CN 117304082A
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- CN
- China
- Prior art keywords
- bis
- optical resin
- resin lens
- diisocyanate
- compound
- 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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- 230000003287 optical effect Effects 0.000 title claims abstract description 144
- 239000011347 resin Substances 0.000 title claims abstract description 142
- 229920005989 resin Polymers 0.000 title claims abstract description 142
- 150000001875 compounds Chemical class 0.000 title claims abstract description 71
- 229920006295 polythiol Polymers 0.000 title claims abstract description 59
- 238000002360 preparation method Methods 0.000 title claims description 13
- -1 epichlorohydrin compound Chemical class 0.000 claims abstract description 58
- 239000012535 impurity Substances 0.000 claims abstract description 38
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000002994 raw material Substances 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims description 45
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 30
- 238000006116 polymerization reaction Methods 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 13
- 125000005442 diisocyanate group Chemical group 0.000 claims description 12
- 239000005056 polyisocyanate Substances 0.000 claims description 12
- 229920001228 polyisocyanate Polymers 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 11
- 239000012752 auxiliary agent Substances 0.000 claims description 10
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 10
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 8
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 claims description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 6
- COYTVZAYDAIHDK-UHFFFAOYSA-N [5-(sulfanylmethyl)-1,4-dithian-2-yl]methanethiol Chemical compound SCC1CSC(CS)CS1 COYTVZAYDAIHDK-UHFFFAOYSA-N 0.000 claims description 6
- INBDPOJZYZJUDA-UHFFFAOYSA-N methanedithiol Chemical compound SCS INBDPOJZYZJUDA-UHFFFAOYSA-N 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 6
- 239000011148 porous material Substances 0.000 claims description 6
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims description 6
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 claims description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- JRNVQLOKVMWBFR-UHFFFAOYSA-N 1,2-benzenedithiol Chemical compound SC1=CC=CC=C1S JRNVQLOKVMWBFR-UHFFFAOYSA-N 0.000 claims description 3
- YRVDWKARENSLCA-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)adamantane Chemical compound C1C(C2)CC3CC1C(CN=C=O)C2(CN=C=O)C3 YRVDWKARENSLCA-UHFFFAOYSA-N 0.000 claims description 3
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 claims description 3
- YGKHJWTVMIMEPQ-UHFFFAOYSA-N 1,2-propanedithiol Chemical compound CC(S)CS YGKHJWTVMIMEPQ-UHFFFAOYSA-N 0.000 claims description 3
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 claims description 3
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 claims description 3
- WNPSAOYKQQUALV-UHFFFAOYSA-N 1,3-bis(sulfanyl)propan-2-ol Chemical compound SCC(O)CS WNPSAOYKQQUALV-UHFFFAOYSA-N 0.000 claims description 3
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 claims description 3
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 claims description 3
- SRZXCOWFGPICGA-UHFFFAOYSA-N 1,6-Hexanedithiol Chemical compound SCCCCCCS SRZXCOWFGPICGA-UHFFFAOYSA-N 0.000 claims description 3
- BQFHAWXWURJCJM-UHFFFAOYSA-N 2,2-bis(isocyanatomethyl)thiolane Chemical compound O=C=NCC1(CN=C=O)CCCS1 BQFHAWXWURJCJM-UHFFFAOYSA-N 0.000 claims description 3
- MTZVWTOVHGKLOX-UHFFFAOYSA-N 2,2-bis(sulfanylmethyl)propane-1,3-dithiol Chemical compound SCC(CS)(CS)CS MTZVWTOVHGKLOX-UHFFFAOYSA-N 0.000 claims description 3
- IOMBOXJZZQRKSD-UHFFFAOYSA-N 2,6-bis(isocyanatomethyl)naphthalene Chemical compound C1=C(CN=C=O)C=CC2=CC(CN=C=O)=CC=C21 IOMBOXJZZQRKSD-UHFFFAOYSA-N 0.000 claims description 3
- CNDCQWGRLNGNNO-UHFFFAOYSA-N 2-(2-sulfanylethoxy)ethanethiol Chemical compound SCCOCCS CNDCQWGRLNGNNO-UHFFFAOYSA-N 0.000 claims description 3
- KSJBMDCFYZKAFH-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)ethanethiol Chemical compound SCCSCCS KSJBMDCFYZKAFH-UHFFFAOYSA-N 0.000 claims description 3
- NQLQMVQEQFIDQB-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)propane-1,3-dithiol Chemical compound SCCSC(CS)CS NQLQMVQEQFIDQB-UHFFFAOYSA-N 0.000 claims description 3
- HAQZWTGSNCDKTK-UHFFFAOYSA-N 2-(3-sulfanylpropanoyloxy)ethyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCCOC(=O)CCS HAQZWTGSNCDKTK-UHFFFAOYSA-N 0.000 claims description 3
- VGEOIVXAFNNZKM-UHFFFAOYSA-N 2-(sulfanylmethyl)butane-1,4-dithiol Chemical compound SCCC(CS)CS VGEOIVXAFNNZKM-UHFFFAOYSA-N 0.000 claims description 3
- FOBHCEPKFIUKPH-UHFFFAOYSA-N 2-(sulfanylmethyl)propane-1,3-dithiol Chemical compound SCC(CS)CS FOBHCEPKFIUKPH-UHFFFAOYSA-N 0.000 claims description 3
- LOSJLAVLYJUGJO-UHFFFAOYSA-N 2-[1,3-bis(sulfanyl)propan-2-ylsulfanyl]propane-1,3-dithiol Chemical compound SCC(CS)SC(CS)CS LOSJLAVLYJUGJO-UHFFFAOYSA-N 0.000 claims description 3
- ISGHUYCZFWLBRU-UHFFFAOYSA-N 2-[2-(2-sulfanylacetyl)oxyethoxy]ethyl 2-sulfanylacetate Chemical compound SCC(=O)OCCOCCOC(=O)CS ISGHUYCZFWLBRU-UHFFFAOYSA-N 0.000 claims description 3
- HCZMHWVFVZAHCR-UHFFFAOYSA-N 2-[2-(2-sulfanylethoxy)ethoxy]ethanethiol Chemical compound SCCOCCOCCS HCZMHWVFVZAHCR-UHFFFAOYSA-N 0.000 claims description 3
- ZQLHFUHXRDOCBC-UHFFFAOYSA-N 2-[2-(3-sulfanylpropanoyloxy)ethoxy]ethyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCCOCCOC(=O)CCS ZQLHFUHXRDOCBC-UHFFFAOYSA-N 0.000 claims description 3
- WVWWFRBCDIXMGT-UHFFFAOYSA-N 2-[[5-(2-sulfanylethylsulfanylmethyl)-1,4-dithian-2-yl]methylsulfanyl]ethanethiol Chemical compound SCCSCC1CSC(CSCCS)CS1 WVWWFRBCDIXMGT-UHFFFAOYSA-N 0.000 claims description 3
- JSOVZQSFWPMPKN-UHFFFAOYSA-N 4-(3-sulfanylpropanoyloxy)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCCCCOC(=O)CCS JSOVZQSFWPMPKN-UHFFFAOYSA-N 0.000 claims description 3
- WREGWRFRXHKFGE-UHFFFAOYSA-N 4-(4-sulfanylphenoxy)benzenethiol Chemical compound C1=CC(S)=CC=C1OC1=CC=C(S)C=C1 WREGWRFRXHKFGE-UHFFFAOYSA-N 0.000 claims description 3
- GECFNYKBZPHYBN-UHFFFAOYSA-N 4-(4-sulfanylphenyl)sulfonylbenzenethiol Chemical compound C1=CC(S)=CC=C1S(=O)(=O)C1=CC=C(S)C=C1 GECFNYKBZPHYBN-UHFFFAOYSA-N 0.000 claims description 3
- RYXFMCKXOQMCSM-UHFFFAOYSA-N 4-[(4-sulfanylphenyl)methyl]benzenethiol Chemical compound C1=CC(S)=CC=C1CC1=CC=C(S)C=C1 RYXFMCKXOQMCSM-UHFFFAOYSA-N 0.000 claims description 3
- DIFMOXDTKAEVHX-UHFFFAOYSA-N 4-[2-(4-sulfanylphenyl)propan-2-yl]benzenethiol Chemical compound C=1C=C(S)C=CC=1C(C)(C)C1=CC=C(S)C=C1 DIFMOXDTKAEVHX-UHFFFAOYSA-N 0.000 claims description 3
- JLLMOYPIVVKFHY-UHFFFAOYSA-N Benzenethiol, 4,4'-thiobis- Chemical compound C1=CC(S)=CC=C1SC1=CC=C(S)C=C1 JLLMOYPIVVKFHY-UHFFFAOYSA-N 0.000 claims description 3
- WHQBUJCBZGKMIN-UHFFFAOYSA-N C=C.C=C.N=C=O.N=C=O Chemical compound C=C.C=C.N=C=O.N=C=O WHQBUJCBZGKMIN-UHFFFAOYSA-N 0.000 claims description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 claims 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 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- IDMCXJRWHDUNRT-UHFFFAOYSA-N [3-(sulfanylmethyl)cyclohexyl]methanethiol Chemical compound SCC1CCCC(CS)C1 IDMCXJRWHDUNRT-UHFFFAOYSA-N 0.000 claims description 3
- JSNABGZJVWSNOB-UHFFFAOYSA-N [3-(sulfanylmethyl)phenyl]methanethiol Chemical compound SCC1=CC=CC(CS)=C1 JSNABGZJVWSNOB-UHFFFAOYSA-N 0.000 claims description 3
- HRPVDGZEKVNVQW-UHFFFAOYSA-N [4-(sulfanylmethyl)cyclohexyl]methanethiol Chemical compound SCC1CCC(CS)CC1 HRPVDGZEKVNVQW-UHFFFAOYSA-N 0.000 claims description 3
- IYPNRTQAOXLCQW-UHFFFAOYSA-N [4-(sulfanylmethyl)phenyl]methanethiol Chemical compound SCC1=CC=C(CS)C=C1 IYPNRTQAOXLCQW-UHFFFAOYSA-N 0.000 claims description 3
- MSILJOYZYPRFDK-UHFFFAOYSA-N [4-[4-(sulfanylmethyl)phenoxy]phenyl]methanethiol Chemical compound C1=CC(CS)=CC=C1OC1=CC=C(CS)C=C1 MSILJOYZYPRFDK-UHFFFAOYSA-N 0.000 claims description 3
- WMOSGVRFIUEZSX-UHFFFAOYSA-N [4-[4-(sulfanylmethyl)phenyl]sulfanylphenyl]methanethiol Chemical compound C1=CC(CS)=CC=C1SC1=CC=C(CS)C=C1 WMOSGVRFIUEZSX-UHFFFAOYSA-N 0.000 claims description 3
- UZDQMYFEXFNUFJ-UHFFFAOYSA-N [4-[[4-(sulfanylmethyl)phenyl]methyl]phenyl]methanethiol Chemical compound C1=CC(CS)=CC=C1CC1=CC=C(CS)C=C1 UZDQMYFEXFNUFJ-UHFFFAOYSA-N 0.000 claims description 3
- DHHJQXAJIIVBES-UHFFFAOYSA-N [5-(sulfanylmethyl)thiophen-2-yl]methanethiol Chemical compound SCC1=CC=C(CS)S1 DHHJQXAJIIVBES-UHFFFAOYSA-N 0.000 claims description 3
- ZWOASCVFHSYHOB-UHFFFAOYSA-N benzene-1,3-dithiol Chemical compound SC1=CC=CC(S)=C1 ZWOASCVFHSYHOB-UHFFFAOYSA-N 0.000 claims description 3
- WYLQRHZSKIDFEP-UHFFFAOYSA-N benzene-1,4-dithiol Chemical compound SC1=CC=C(S)C=C1 WYLQRHZSKIDFEP-UHFFFAOYSA-N 0.000 claims description 3
- JGCWKVKYRNXTMD-UHFFFAOYSA-N bicyclo[2.2.1]heptane;isocyanic acid Chemical compound N=C=O.N=C=O.C1CC2CCC1C2 JGCWKVKYRNXTMD-UHFFFAOYSA-N 0.000 claims description 3
- SMTOKHQOVJRXLK-UHFFFAOYSA-N butane-1,4-dithiol Chemical compound SCCCCS SMTOKHQOVJRXLK-UHFFFAOYSA-N 0.000 claims description 3
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 claims description 3
- UMSNERSLSHPBNT-UHFFFAOYSA-N cyclohexane-1,3-dithiol Chemical compound SC1CCCC(S)C1 UMSNERSLSHPBNT-UHFFFAOYSA-N 0.000 claims description 3
- QQKBIYRSRXCROF-UHFFFAOYSA-N cyclohexane-1,4-dithiol Chemical compound SC1CCC(S)CC1 QQKBIYRSRXCROF-UHFFFAOYSA-N 0.000 claims description 3
- XXKOQQBKBHUATC-UHFFFAOYSA-N cyclohexylmethylcyclohexane Chemical compound C1CCCCC1CC1CCCCC1 XXKOQQBKBHUATC-UHFFFAOYSA-N 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims 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 claims description 3
- WNIMPVMSRDFHTD-UHFFFAOYSA-N methanetrithiol Chemical compound SC(S)S WNIMPVMSRDFHTD-UHFFFAOYSA-N 0.000 claims description 3
- UWHMFGKZAYHMDJ-UHFFFAOYSA-N propane-1,2,3-trithiol Chemical compound SCC(S)CS UWHMFGKZAYHMDJ-UHFFFAOYSA-N 0.000 claims description 3
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 claims description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 3
- GNDOBZLRZOCGAS-JTQLQIEISA-N 2-isocyanatoethyl (2s)-2,6-diisocyanatohexanoate Chemical compound O=C=NCCCC[C@H](N=C=O)C(=O)OCCN=C=O GNDOBZLRZOCGAS-JTQLQIEISA-N 0.000 claims description 2
- JCELWOGDGMAGGN-UHFFFAOYSA-N N=C=O.N=C=O.C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound N=C=O.N=C=O.C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 JCELWOGDGMAGGN-UHFFFAOYSA-N 0.000 claims description 2
- SERCPQYXEUPQHB-UHFFFAOYSA-N 5,6-diisocyanato-5-methylcyclohexa-1,3-diene Chemical compound O=C=NC1(C)C=CC=CC1N=C=O SERCPQYXEUPQHB-UHFFFAOYSA-N 0.000 claims 1
- 239000006082 mold release agent Substances 0.000 claims 1
- 238000002834 transmittance Methods 0.000 abstract description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 230000000052 comparative effect Effects 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000011156 evaluation Methods 0.000 description 16
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000011521 glass Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 3
- DAUUORKACOSESW-UHFFFAOYSA-N 2-[2-[2-(2-sulfanylethylsulfanyl)ethylsulfanyl]ethylsulfanylmethyl]propane-1,2,3-trithiol Chemical compound SCCSCCSCCSCC(S)(CS)CS DAUUORKACOSESW-UHFFFAOYSA-N 0.000 description 3
- 239000002390 adhesive tape Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- YRHRHYSCLREHLE-UHFFFAOYSA-N 2,5-bis(isocyanatomethyl)-1,4-dithiane Chemical compound O=C=NCC1CSC(CN=C=O)CS1 YRHRHYSCLREHLE-UHFFFAOYSA-N 0.000 description 2
- BDLJDZLEOKUVHM-UHFFFAOYSA-N 2,5-bis(isocyanatomethyl)thiophene Chemical compound O=C=NCC1=CC=C(CN=C=O)S1 BDLJDZLEOKUVHM-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000007496 glass forming Methods 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 238000011085 pressure filtration Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- PTZQVBCTRCXDFM-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C(C=C1)=CC=C1OC1=CC=CC=C1 Chemical compound N=C=O.N=C=O.N=C=O.C(C=C1)=CC=C1OC1=CC=CC=C1 PTZQVBCTRCXDFM-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000002929 anti-fatigue Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000003670 easy-to-clean Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000000752 ionisation method Methods 0.000 description 1
- 150000002541 isothioureas Chemical class 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000005304 optical glass Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide 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
- C08G18/28—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
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention provides a polythiol compound for optical resin lenses, which is prepared by reacting 2-mercaptoethanol with an epichlorohydrin compound, wherein the impurity content shown in a formula (I) in the epichlorohydrin compound is below 30 ppm. Compared with the prior art, the polythiol compound for optical resin lenses can be obtained by strictly controlling the content of specific impurities in the raw material epichlorohydrin compound, namely, limiting the content of the impurities shown in the formula (I) in the epichlorohydrin compound to below 30 ppm; the polythiol compound provided by the invention is used for the optical resin lens, and can improve the haze and the light transmittance of the optical resin lens, so that the low-haze high-light transmittance optical resin lens is obtained.
Description
Technical Field
The invention relates to the technical field of optical resin lenses, in particular to a polythiol compound for an optical resin lens, an optical resin lens and a preparation method thereof.
Background
Compared with the optical glass lens, the resin lens has the advantages of light weight, toughness, dyeing capability, strong antifogging property, dent prevention and the like. The properties particularly required in the optical field for resin lens applications are: low haze, high light transmittance, low yellowness, high heat resistance, high strength, high refractive index, high abbe number, and the like; in particular, the haze and the light transmittance are important performance parameters for the optical resin lens as the spectacle lens, and the spectacle lens with low haze and high light transmittance can enable people to observe objects clearly and truly.
Currently, in the prior art, an optical resin lens is obtained by further polymerizing and curing a composition for an optical resin lens obtained by mixing and dissolving a polythiol compound and a polyisocyanate compound. During the course of the study, researchers have found that the optical resin lenses obtained from the composition for optical resin lenses comprising a polythiol compound exhibit fogging, unclear or even opaque phenomena, and when used as spectacle lenses, the visibility affects the observation with no clarity, resulting in reduced comfort for the user wearing the spectacles. Therefore, how to improve the haze and transmittance of the optical resin lens is a technical problem to be solved by those skilled in the art.
Disclosure of Invention
In view of the above, an object of the present invention is to provide a polythiol compound for an optical resin lens, and a method for producing the same, wherein the use of the polythiol compound for an optical resin lens can improve the haze and light transmittance of the optical resin lens, and can provide a low-haze high-light transmittance optical resin lens.
The invention provides a polythiol compound for optical resin lenses, which is prepared by reacting 2-mercaptoethanol with an epichlorohydrin compound, wherein the impurity content shown in a formula (I) of the epichlorohydrin compound is below 30 ppm;
preferably, the purity of the 2-mercaptoethanol is more than 99.5 wt%; the purity of the epichlorohydrin is above 99.5 wt%.
The invention also provides an optical resin lens which is prepared from the raw materials comprising the composition for the optical resin lens; the composition for an optical resin lens comprises a polyisocyanate compound and the polythiol compound for an optical resin lens described in the above-mentioned embodiments.
Preferably, the composition for an optical resin lens further comprises another polythiol compound; the other polythiol compound is selected from pentaerythritol tetrasulfocyanurate, diethylene glycol bis (3-mercaptopropionate), pentaerythritol tetrasulfocyanurate, 1, 2-dimercaptocyanune, 1-tris (mercaptomethyl) propane, 1, 4-butanediol bis (3-mercaptopropionate), methane dithiol, methane trithiol, bis (2-mercaptoethyl) ether, tetrakis (mercaptomethyl) methane, 1, 2-dimercaptopropane, 1, 3-dimercaptopropane, 1, 4-dimercaptobutane, 1, 6-dimercaptohexane, 2-dimercaptopropane, 1, 2-bis (2-mercaptoethoxy) ethane, 1, 2-bis (2-mercaptoethylthio) ethane 2, 3-dimercapto-1-propanol, 1, 2-dimercaptoethane, 1, 3-dimercapto-2-propanol, 2-mercaptomethyl-1, 3-dimercaptopropane, 2-mercaptomethyl-1, 4-dimercaptobutane, 1,2, 3-trismercaptopropane, 2- (2-mercaptoethylthio) -1, 3-dimercaptopropane, 2, 4-dimercaptomethyl-1, 5-dimercapto-3-thiapentane, 1, 2-dimercaptobenzene, 1, 3-dimercaptobenzene, 1, 4-dimercaptobenzene, 1, 3-bis (mercaptomethyl) benzene, 2, 5-dimercaptomethyl-1, 4-dithiane, 1, 4-bis (mercaptomethyl) benzene, 2' -dimercaptobiphenyl, bis (4-mercaptophenyl) methane, 2, 2-bis (4-mercaptophenyl) propane, 4' -dimercaptobiphenyl, bis (4-mercaptophenyl) ether, bis (4-mercaptomethylphenyl) methane, 1, 3-tetrakis (mercaptomethylthio) propane 2, 2-bis (4-mercaptomethylphenyl) propane, bis (4-mercaptomethylphenyl) ether, bis (4-mercaptomethylphenyl) thioether, 2, 5-dimercapto-1, 3, 4-thiadiazole, 3, 4-thiophenedichiol, bis (2-mercaptoethyl) thioether, ethylene glycol bis (3-mercaptopropionate), diethylene glycol bis (2-mercaptoacetate), ethylene glycol bis (2-mercaptoacetate) 1, 4-butanediol bis (2-mercaptoacetate), trimethylolpropane trimercaptan-yl propionate, 1, 3-dimercaptocyclohexane, trimethylolpropane trimercaptan-yl acetate, 1, 4-dimercaptocyclohexane, 1, 3-bis (mercaptomethyl) cyclohexane, 1, 4-bis (mercaptomethyl) cyclohexane, bis (4-mercaptophenyl) sulfone, 2, 5-dimercaptomethyl-1, 4-dithiane, 2, 5-bis (2-mercaptoethylthiomethyl) -1, 4-dithiane, 2, 5-dimercaptomethyl-1-thiane, 2, 5-dimercaptoethyl-1-thiane, 2, 5-dimercaptomethyl thiophene, one or more of bis (4-mercaptophenyl) sulfide.
Preferably, the polyisocyanate compound is selected from one or more of tetramethylene diisocyanate, hexamethylene diisocyanate, cyclohexane diisocyanate, 4' -diisocyanate dicyclohexylmethane, isophorone diisocyanate, norbornane diisocyanate, xylylene diisocyanate, hydrogenated xylylene diisocyanate, tetramethylm-xylylene diisocyanate, dithiodipropylene diisocyanate, dithiodiethyl diisocyanate, 2, 5-diisocyanatomethylthiophene, 2, 5-diisocyanatomethyl-1, 4-dithiane, 2, 5-diisocyanate-1, 4-dithiane, thiodihexyl diisocyanate, thiodipropyl diisocyanate, bis (isocyanatomethyl) adamantane, bis (isocyanatomethyl) tetrahydrothiophene, 2, 6-bis (isocyanatomethyl) naphthalene, 1, 5-naphthalene diisocyanate, diethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine triisocyanate, toluene diisocyanate, o-tolidine diisocyanate, diphenylmethane diisocyanate, diphenyl ether triisocyanate.
Preferably, the composition is prepared from the following raw materials:
100 parts by weight of a composition for an optical resin lens;
0.001 to 0.3 weight portion of catalyst;
0.1 to 1 weight part of auxiliary agent.
Preferably, the auxiliary agent is selected from one or more of a release agent, an ultraviolet absorber and a toner.
The invention also provides a preparation method of the optical resin lens, which comprises the following steps:
uniformly mixing the raw materials to obtain a mixed solution;
the mixed solution is filtered after defoamation to obtain a mixture;
and (3) injecting the mixture into a forming die, performing polymerization curing reaction, and demolding to obtain the optical resin lens.
Preferably, the vacuum degree of the deaeration is 10 Pa-500 Pa, and the time is 0.5 h-2 h; the filtration is performed by using a polytetrafluoroethylene filter with a pore size of 1-10 mu m.
Preferably, the polymerization and curing reaction process specifically comprises the following steps:
placing the forming die filled with the mixture into an oven, heating from 10 ℃ to 30 ℃ to 110 ℃ to 130 ℃ for 20 hours to 30 hours, and maintaining for 2 hours to 6 hours to carry out polymerization curing reaction.
The invention provides a polythiol compound for optical resin lenses, which is prepared by reacting 2-mercaptoethanol with an epichlorohydrin compound, wherein the impurity content shown in a formula (I) of the epichlorohydrin compound is below 30 ppm;
compared with the prior art, the polythiol compound for optical resin lenses can be obtained by strictly controlling the content of specific impurities in the raw material epichlorohydrin compound, namely, limiting the content of the impurities shown in the formula (I) in the epichlorohydrin compound to below 30 ppm; the polythiol compound provided by the invention is used for the optical resin lens, and can improve the haze and the light transmittance of the optical resin lens, so that the low-haze high-light transmittance optical resin lens is obtained.
Detailed Description
The technical solutions of the present invention will be clearly and completely described in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The invention provides a polythiol compound for optical resin lenses, which is prepared by reacting 2-mercaptoethanol with an epichlorohydrin compound, wherein the impurity content shown in a formula (I) of the epichlorohydrin compound is below 30 ppm;
the applicant of the present invention has obtained the following technical contents, which have never been disclosed in the prior art, through a great deal of experiments and intensive studies: the content of a specific impurity contained in an epichlorohydrin compound used for synthesizing a polythiol compound as one of compositions for optical resin lenses can significantly affect the haze and light transmittance of the optical resin lenses. Based on the technical content, the invention provides a technical scheme for enabling the haze of an optical resin lens prepared from a synthesized polythiol compound to be lower and the light transmittance to be higher by controlling the content of specific impurities in an epichlorohydrin compound, and comprises the polythiol compound for the optical resin lens, the optical resin lens and a preparation method thereof.
The present invention provides a polythiol compound having suppressed haze, which is obtained by controlling the content of a specific impurity in an epichlorohydrin compound used as a raw material for synthesizing the polythiol compound, based on the polythiol compound for an optical resin lens; the specific impurity in the epichlorohydrin compound is specifically an impurity represented by the formula (I), and when the impurity content represented by the formula (I) is 30ppm or less, a polythiol compound for an optical resin lens can be obtained.
In the present invention, the purity of the 2-mercaptoethanol is preferably 99.5% by weight or more; the purity of the epichlorohydrin is preferably 99.5wt% or more.
The method for preparing the polythiol compound for the optical resin lens is not particularly limited, and the polythiol compound can be synthesized by adopting a well-known preparation method of the polythiol compound which is well known to a person skilled in the art; the preparation method comprises the steps of reacting 2-mercaptoethanol with an epichlorohydrin compound; namely, a step of reacting 2-mercaptoethanol with an epichlorohydrine compound to obtain a polyol compound, a step of reacting the polyol compound with thiourea to obtain a thiouronium salt, and a step of hydrolyzing the thiouronium salt to obtain a polythiol compound, by which the desired polythiol compound can be produced. In addition, the polythiol compound of the present invention may further comprise a hydroxyl compound which is an unreacted product in which a part of the above-mentioned substances is mixed.
In a preferred embodiment of the present invention, the preparation method of the polythiol compound for optical resin lenses specifically comprises:
2-mercaptoethanol is put into a reactor, sodium hydroxide aqueous solution with the concentration of 30 to 37 weight percent is dripped for 10 to 60 minutes at the temperature of 30 to 60 ℃, epichlorohydrin is dripped for 1.0 to 2.5 hours, and the temperature is kept for 10 to 60 minutes; then adding 30-40 wt% hydrochloric acid and thiourea, and refluxing at 100-160 ℃ for 3-6 h to obtain isothiourea salt; cooling to room temperature, adding ammonia water with the concentration of 15-20wt% to react for 2-6 h at 50-90 ℃, standing for layering, separating a lower organic phase to obtain a polythiol compound crude product taking 2, 3-dithio (2-mercapto) -1-propane thiol as a main component, adding hydrochloric acid to adjust the pH value to 5.5-6.5, adding water to wash for 1-3 times, heating and decompressing for dehydration to obtain the 2, 3-dithio (2-mercapto) -1-propane thiol.
In another preferred embodiment of the present invention, the preparation method of the polythiol compound for optical resin lenses specifically comprises:
2-mercaptoethanol, deaerated water and 45-55wt% sodium hydroxide aqueous solution are put into a reactor, epichlorohydrine is added dropwise for 6-7 h at 9-11 ℃, and then stirring is carried out for 50-70 min; then dropwise adding 10-20wt% sodium sulfide aqueous solution at 7-37 ℃ for 5-6 h, and stirring for 100-150 min; then adding 30-40 wt% of hydrochloric acid and thiourea, and stirring for 2-4 hours at 100-120 ℃ under reflux to carry out thiourea onium salinization reaction; cooling to 40-50 ℃, adding toluene, cooling to 20-30 ℃, adding 20-30wt% ammonia water solution at 26-50 ℃ for 20-40 min, stirring at 50-65 ℃ for 0.5-1.5 h, and performing hydrolysis reaction to obtain a toluene solution of polythiol with bis (mercaptomethyl) -3,6, 9-trithia-1, 11-undecanedithiol as a main component; then adding 30-40 wt% hydrochloric acid, and performing acid washing on the toluene solution for 20-40 min at 34-39 ℃ for 1-3 times; adding deaerated water, washing for 20-40 min at 35-45 ℃ and implementing for 4-6 times; toluene and a small amount of water were removed under reduced pressure by heating, and then reduced pressure filtration was performed with a 1 to 1.5 μm PTFE membrane filter to obtain bis (mercaptomethyl) -3,6, 9-trithio-1, 11-undecanedithiol.
The invention also provides an optical resin lens which is prepared from the raw materials comprising the composition for the optical resin lens; the composition for an optical resin lens comprises a polyisocyanate compound and the polythiol compound for an optical resin lens described in the above-mentioned embodiments.
In the present invention, the composition for an optical resin lens comprises the polythiol compound for an optical resin lens according to the above-described aspect; the composition for an optical resin lens can be obtained by mixing the polythiol compound for an optical resin lens with the polyisocyanate compound.
In the present invention, the composition for an optical resin lens preferably further comprises another polythiol compound; the other polythiol compound is selected from pentaerythritol tetrasulfocyanurate, diethylene glycol bis (3-mercaptopropionate), pentaerythritol tetrasulfocyanurate, 1, 2-dimercaptocyanune, 1-tris (mercaptomethyl) propane, 1, 4-butanediol bis (3-mercaptopropionate), methane dithiol, methane trithiol, bis (2-mercaptoethyl) ether, tetrakis (mercaptomethyl) methane, 1, 2-dimercaptopropane, 1, 3-dimercaptopropane, 1, 4-dimercaptobutane, 1, 6-dimercaptohexane, 2-dimercaptopropane, 1, 2-bis (2-mercaptoethoxy) ethane, 1, 2-bis (2-mercaptoethylthio) ethane 2, 3-dimercapto-1-propanol, 1, 2-dimercaptoethane, 1, 3-dimercapto-2-propanol, 2-mercaptomethyl-1, 3-dimercaptopropane, 2-mercaptomethyl-1, 4-dimercaptobutane, 1,2, 3-trismercaptopropane, 2- (2-mercaptoethylthio) -1, 3-dimercaptopropane, 2, 4-dimercaptomethyl-1, 5-dimercapto-3-thiapentane, 1, 2-dimercaptobenzene, 1, 3-dimercaptobenzene, 1, 4-dimercaptobenzene, 1, 3-bis (mercaptomethyl) benzene, 2, 5-dimercaptomethyl-1, 4-dithiane, 1, 4-bis (mercaptomethyl) benzene, 2' -dimercaptobiphenyl, bis (4-mercaptophenyl) methane, 2, 2-bis (4-mercaptophenyl) propane, 4' -dimercaptobiphenyl, bis (4-mercaptophenyl) ether, bis (4-mercaptomethylphenyl) methane, 1, 3-tetrakis (mercaptomethylthio) propane 2, 2-bis (4-mercaptomethylphenyl) propane, bis (4-mercaptomethylphenyl) ether, bis (4-mercaptomethylphenyl) thioether, 2, 5-dimercapto-1, 3, 4-thiadiazole, 3, 4-thiophenedichiol, bis (2-mercaptoethyl) thioether, ethylene glycol bis (3-mercaptopropionate), diethylene glycol bis (2-mercaptoacetate), ethylene glycol bis (2-mercaptoacetate) 1, 4-butanediol bis (2-mercaptoacetate), trimethylolpropane trimercaptan-yl propionate, 1, 3-dimercaptocyclohexane, trimethylolpropane trimercaptan-yl acetate, 1, 4-dimercaptocyclohexane, 1, 3-bis (mercaptomethyl) cyclohexane, 1, 4-bis (mercaptomethyl) cyclohexane, bis (4-mercaptophenyl) sulfone, 2, 5-dimercaptomethyl-1, 4-dithiane, 2, 5-bis (2-mercaptoethylthiomethyl) -1, 4-dithiane, 2, 5-dimercaptomethyl-1-thiane, 2, 5-dimercaptoethyl-1-thiane, 2, 5-dimercaptomethyl thiophene, one or more of bis (4-mercaptophenyl) sulfide. The source of the other polythiol compound is not particularly limited in the present invention, and commercially available products or self-products known to those skilled in the art may be used.
In the present invention, the polyisocyanate compound is preferably selected from the group consisting of tetramethylene diisocyanate, hexamethylene diisocyanate, cyclohexane diisocyanate, 4 '-diisocyanate dicyclohexylmethane, isophorone diisocyanate, norbornane diisocyanate, xylylene diisocyanate, hydrogenated xylylene diisocyanate, tetramethylm-xylylene diisocyanate, dithiodipropylene diisocyanate, dithiodiethyl diisocyanate, 2, 5-diisocyanatomethylthiophene, 2, 5-diisocyanatomethyl-1, 4-dithiane, 2, 5-diisocyanate-1, 4-dithiane, thiodihexyl diisocyanate, thiodipropyl diisocyanate, bis (isocyanatomethyl) adamantane, bis (isocyanatomethyl) tetrahydrothiophene, 2, 6-bis (isocyanatomethyl) naphthalene, 1, 5-naphthalene diisocyanate, diethylene diisocyanate, trimethylhexamethylene diisocyanate, triisocyanate, toluene diisocyanate, o-tolidine diisocyanate, diphenylmethane diisocyanate, diphenyl ether, triphenylmethane diisocyanate, trimethylhexamethylene diisocyanate, hexamethylene diisocyanate, or more preferably, 4' -xylylene diisocyanate, and m-xylylene diisocyanate. The source of the polyisocyanate compound is not particularly limited in the present invention, and any commercially available or self-made product of the above-mentioned compound having at least 1 isocyanate group, which is well known to those skilled in the art, may be used.
The composition for an optical resin lens can be prepared by mixing the polythiol compound with a polyisocyanate compound; the mixing ratio of the polythiol compound and the polyisocyanate compound in the composition for an optical resin lens is not particularly limited, and for example, the molar ratio of the mercapto group contained in the polythiol compound to the isocyanate group contained in the polyisocyanate compound may be in the range of 0.5 to 3.0, preferably 0.6 to 2.0, more preferably 0.8 to 1.3; when the mixing ratio is within the above range, various physical properties such as refractive index and heat resistance required for an optical resin lens can be obtained.
In a preferred embodiment of the present invention, the content of the polythiol compound in the composition for an optical resin lens may be 40wt% or more, for example, 40wt% to 80wt%.
In order to make the optical resin lens of the invention have better physical properties, operability, polymerization reactivity and the like, a catalyst and an auxiliary agent are added according to requirements; on this basis, the optical resin lens is preferably prepared from the following raw materials:
100 parts by weight of a composition for an optical resin lens;
0.001 to 0.3 weight portion of catalyst;
0.1 to 1 weight part of auxiliary agent;
more preferably, the composition is prepared from the following raw materials:
100 parts by weight of a composition for an optical resin lens;
0.01 to 0.1 weight part of catalyst;
0.5 to 0.6 weight portion of auxiliary agent.
In the present invention, the catalyst is preferably one or more selected from the group consisting of dibutyltin dilaurate, dibutyltin dichloride, dibutyltin oxide and stannous octoate, and more preferably dibutyltin dilaurate or dibutyltin dichloride. The source of the catalyst is not particularly limited in the present invention, and commercially available products known to those skilled in the art may be used.
In the present invention, the catalyst is preferably added in an amount of 0.001wt% to 0.3wt%, more preferably 0.01wt% to 0.1wt%. When the catalyst addition amount is less than 0.001wt%, the polymerization curing reaction is incomplete, resulting in poor mechanical properties of the optical resin lens; when the catalyst addition amount is more than 0.3wt%, the polymerization speed is too high, and the explosion polymerization phenomenon occurs.
In order to further improve the application performance of the optical resin lens, the invention also adds an auxiliary agent; the auxiliary agent is preferably one or more selected from a release agent, an ultraviolet absorber and a toner, and more preferably a release agent or an ultraviolet absorber. The source of the auxiliary agent is not particularly limited in the present invention, and commercially available products known to those skilled in the art may be used.
The invention also provides a preparation method of the optical resin lens, which comprises the following steps:
uniformly mixing the raw materials to obtain a mixed solution;
the mixed solution is filtered after defoamation to obtain a mixture;
and (3) injecting the mixture into a glass forming die, performing polymerization curing reaction, and demolding to obtain the optical resin lens.
In the present invention, the raw materials, that is, the raw materials for producing an optical resin lens described in the above-mentioned embodiments, include a composition for an optical resin lens, and preferably further include other polythiol compounds, catalysts, and auxiliaries. The present invention provides an optical resin lens obtained by curing the composition for an optical resin lens, and the obtained resin lens is suitable for use as a material for optical members such as spectacle lenses.
In the present invention, the vacuum degree of the deaeration is preferably 10Pa to 500Pa, more preferably 100Pa to 300Pa, and the time is preferably 0.5h to 2h, more preferably 1h; the filtration is preferably performed by using a polytetrafluoroethylene filter having a pore size of 1 μm to 10. Mu.m, more preferably by using a polytetrafluoroethylene filter having a pore size of 5. Mu.m.
In the present invention, the polymerization curing reaction process is preferably specifically:
placing the glass forming die filled with the mixture into an oven, heating from 10 ℃ to 30 ℃ to 110 ℃ to 130 ℃ for 20 hours to 30 hours, and keeping for 2 hours to 6 hours for polymerization and curing reaction;
more preferably:
and (3) placing the forming die filled with the mixture into an oven, heating the forming die from 20 ℃ to 120 ℃ for 24 hours, and maintaining the forming die for 3 to 5 hours to carry out polymerization curing reaction.
The invention is to inject the mixture (comprising the composition for the optical resin lens) into a glass mold sealed by an adhesive tape, then, preferably, polymerize and solidify by a heating mode, and after solidification, the temperature is reduced to release the optical resin lens in the glass mold from the mold, thereby obtaining the optical resin lens with the inner shape of the glass mold; the released optical resin lens is preferably used as a lens base material for an eyeglass lens. The optical resin lens after demolding may be changed into a progressive addition lens, an anti-fatigue lens, a special-strength lens, or the like having various functions by polishing, etching, cutting, and grinding steps using a precise automated numerical control machine. The lenses with various functions are cleaned, hardened, coated and inspected to obtain qualified lenses which are radiation-proof, static-resistant, scratch-resistant, pollution-proof and easy to clean, and the lenses can be mounted in a glasses frame to obtain glasses.
The invention provides a polythiol compound for optical resin lenses, which is prepared by reacting 2-mercaptoethanol with an epichlorohydrin compound, wherein the impurity content shown in a formula (I) of the epichlorohydrin compound is below 30 ppm; the purity of the mercaptoethanol and epichlorohydrin is not particularly limited.
Compared with the prior art, the polythiol compound for optical resin lenses can be obtained by strictly controlling the content of specific impurities in the raw material epichlorohydrin compound, namely, limiting the content of the impurities shown in the formula (I) in the epichlorohydrin compound to below 30 ppm; the polythiol compound provided by the invention is used for the optical resin lens, and can improve the haze and the light transmittance of the optical resin lens, so that the low-haze high-light transmittance optical resin lens is obtained.
In order to further illustrate the present invention, the following examples are provided. In the following examples and comparative examples, epichlorohydrin was used in a purity of 99.5% by weight or more, and the content of the specific impurity represented by the formula (I) was obtained by:
5kg of an epichlorohydrin compound having a purity of 99.5% by weight, which was purchased from the market, was collected and purified by concentration by distillation to obtain 4.95kg of the purified epichlorohydrin compound and 50g of a heavy component. The purchased epichlorohydrin compound, the purified epichlorohydrin compound and the heavy component are detected by a liquid chromatograph, and the result shows that the impurity content of the epichlorohydrin compound shown in the formula (I) is 133.21ppm, the purified epichlorohydrin compound does not contain the impurity shown in the formula (I), and the impurity content of the heavy component shown in the formula (I) is 13246ppm. The purity of the purified epichlorohydrin was 99.6wt% as measured by gas chromatograph.
The heavy components are taken 1g respectively, 150g, 250g, 350g, 450g, 550g, 750g, 1050g and 1550g of the purified epichlorohydrin compounds with the purity of 99.6wt percent are added respectively to obtain the epichlorohydrin compounds with different specific impurity contents shown in the formula (I), and the epichlorohydrin compounds with different specific impurity contents shown in the formula (I) have the impurity contents shown in the formula (I) of 79.13ppm, 53.29ppm, 37.30ppm, 29.31ppm, 23.20ppm, 17.76ppm, 10.62ppm and 8.85ppm respectively after being detected by a liquid chromatography-mass spectrometer.
The evaluation method comprises the following steps:
the impurity content of formula (I) in the epichlorohydrine compound was measured by ionization method using an Agilent 6530Q-TOF LC/MS liquid chromatography-mass spectrometer with an accuracy of 2 ppm.
Purity evaluation of the purified epichlorohydrin compound:
agilent 7890 gas chromatograph was used to determine the purity of the purified epichlorohydrin.
Haze evaluation of optical resin lenses:
the haze of the optical resin lenses obtained in examples and comparative examples was measured using an UltraScan PRO spectrocolorimeter. The lower the haze, the better the transparency of the optical resin lens.
Evaluation of light transmittance of the optical resin lens:
the transmittance of the optical resin lenses obtained in examples and comparative examples was measured using an UltraScan PRO spectrocolorimeter. The higher the light transmittance, the better the light transmittance of the optical resin lens.
Example 1
(1) Synthesis of 2, 3-dithio (2-mercapto) -1-propanethiol:
2-mercaptoethanol having a purity of 99.50% by weight was stored in a glass vessel under a nitrogen stream, 87.1g of 2-mercaptoethanol was charged into a 1 liter four-necked flask equipped with a stirrer, a nitrogen purge tube and a thermometer, 77.5g of 36% by weight aqueous sodium hydroxide solution was dropwise added at 50℃over 40 minutes, and then 56.5g of epichlorohydrin was dropwise added over 1.5 hours, followed by heat preservation for 1 hour; the purity of epichlorohydrin used was 99.6wt%, and the content of specific impurities represented by the formula (I) was 10.62ppm; then 260g of 37wt% hydrochloric acid and 165g of thiourea of 99.30wt% purity were added and refluxed at 130℃for 4 hours to obtain isothiouronium salt. Cooling to room temperature, adding 300g of 18wt% ammonia water, reacting for 4 hours at 75 ℃, standing for layering, separating a lower organic phase to obtain a polythiol compound crude product which takes 2, 3-dithio (2-mercapto) -1-propane thiol as a main component, adding hydrochloric acid to adjust pH to about 6, adding water for washing twice, heating and decompressing for dehydration to obtain 2, 3-dithio (2-mercapto) -1-propane thiol.
(2) Manufacturing an optical resin lens:
52 parts by mass of m-xylylene diisocyanate, 0.01 part by mass of dibutyltin dichloride as a catalyst, 0.08 part by mass of acid phosphate as a release agent, and 0.50 part by mass of an ultraviolet absorber (UV 329) were mixed and dissolved; further, 48 parts by mass of 2, 3-dithio (2-mercapto) -1-propanethiol obtained in the above step (1) was added and mixed to obtain a mixture. The mixture was defoamed at 200Pa for 1 hour, and then filtered with a PTFE (polytetrafluoroethylene) filter having a pore size of 5.0 μm; injecting the filtered mixture into a molding die for a lens comprising a glass mold having a diameter of 75mm and 0.00D and an adhesive tape; placing the forming die in an oven, slowly heating from 20 ℃ to 120 ℃ for 24 hours, and keeping for 4 hours to perform polymerization curing reaction; after the polymerization curing, the mold was taken out of the oven, and the optical resin lens was obtained by demolding.
Haze and light transmittance were evaluated for the optical resin lenses obtained in example 1; the evaluation results are shown in Table 1.
Example 2
(1) Synthesis of bis (mercaptomethyl) -3,6, 9-trithia-1, 11-undecanedithiol:
into the reactor were charged 80.0g of 2-mercaptoethanol having a purity of 99.60% by weight, 41.5g of deaerated water (dissolved oxygen concentration 2 ppm) and 0.25g of 49% by weight aqueous sodium hydroxide solution; 97.4g of epichlorohydrin was added dropwise thereto at 10℃over 6.5 hours, followed by stirring for 60 minutes; the purity of epichlorohydrin used was 99.6wt%, and the content of specific impurities represented by the formula (I) was 10.62ppm; subsequently, 234.8g of a 17.3wt% sodium sulfide aqueous solution was added dropwise thereto at 22℃over 5.5 hours, and stirring was carried out for 120 minutes; then, 436.8g of 35.5wt% hydrochloric acid was charged, and 198.1g of thiourea having a purity of 99.30wt% was charged, followed by stirring at 110℃under reflux for 3 hours, to thereby effect a thiouronium salt reaction; after cooling to 45℃again, 335.0g of toluene was added, cooled to 26℃and 322.8g of 25wt% aqueous ammonia solution was charged at 38℃for 30 minutes, and the mixture was stirred at 58℃for 1 hour to thereby carry out hydrolysis reaction, thereby obtaining a toluene solution of polythiol mainly composed of bis (mercaptomethyl) -3,6, 9-trithial-1, 11-undecanedithiol. Then 93.0g of 36wt% hydrochloric acid was added, and the toluene solution was subjected to acid washing at 36℃for 30 minutes, followed by 2 times; 185.8g of deaerated water (dissolved oxygen concentration 2 ppm) was added, and the mixture was washed at 40℃for 30 minutes and then carried out 5 times; toluene and a small amount of water were removed under reduced pressure by heating, and then reduced pressure filtration was performed with a 1.2 μm PTFE membrane filter to obtain bis (mercaptomethyl) -3,6, 9-trithio-1, 11-undecanedithiol.
(2) Manufacturing an optical resin lens:
52 parts by mass of m-xylylene diisocyanate, 0.01 part by mass of dibutyltin dichloride as a catalyst, 0.08 part by mass of acid phosphate as a release agent, and 0.50 part by mass of an ultraviolet absorber (UV 329) were mixed and dissolved; further, 48 parts by mass of bis (mercaptomethyl) -3,6, 9-trithia-1, 11-undecanedithiol obtained in the above step (1) was added and mixed to obtain a mixture. The mixture was defoamed at 200Pa for 1 hour, and then filtered with a PTFE (polytetrafluoroethylene) filter having a pore size of 5.0 μm; injecting the filtered mixture into a molding die for a lens comprising a glass mold having a diameter of 75mm and 0.00D and an adhesive tape; placing the forming die in an oven, slowly heating from 20 ℃ to 120 ℃ for 24 hours, and keeping for 4 hours to perform polymerization curing reaction; after the polymerization curing, the mold was taken out of the oven, and the optical resin lens was obtained by demolding.
Haze and light transmittance were evaluated for the optical resin lenses obtained in example 2; the evaluation results are shown in Table 1.
Example 3
2, 3-dithio (2-mercapto) -1-propanethiol was prepared in the same manner as in example 1 except that epichlorohydrin having a specific impurity content of 8.85ppm as shown in formula (I) was used; an optical resin lens was further prepared in the same manner as in example 1.
Haze and light transmittance were evaluated for the optical resin lenses obtained in example 3; the evaluation results are shown in Table 1.
Example 4
2, 3-dithio (2-mercapto) -1-propanethiol was prepared in the same manner as in example 1 except that epichlorohydrin having a specific impurity content of 17.76ppm as shown in formula (I) was used; an optical resin lens was further prepared in the same manner as in example 1.
Haze and light transmittance were evaluated for the optical resin lenses obtained in example 4; the evaluation results are shown in Table 1.
Example 5
2, 3-dithio (2-mercapto) -1-propanethiol was prepared in the same manner as in example 1 except that epichlorohydrin having a specific impurity content of 23.20ppm as shown in formula (I) was used; an optical resin lens was further prepared in the same manner as in example 1.
Haze and light transmittance were evaluated for the optical resin lenses obtained in example 5; the evaluation results are shown in Table 1.
Example 6
2, 3-dithio (2-mercapto) -1-propanethiol was prepared in the same manner as in example 1 except that epichlorohydrin having a specific impurity content of 29.31ppm as shown in formula (I) was used; an optical resin lens was further prepared in the same manner as in example 1.
Haze and light transmittance were evaluated for the optical resin lenses obtained in example 6; the evaluation results are shown in Table 1.
Comparative example 1
2, 3-dithio (2-mercapto) -1-propanethiol was prepared in the same manner as in example 1 except that epichlorohydrin having a specific impurity content of the formula (I) of 37.30ppm was used; an optical resin lens was further prepared in the same manner as in example 1.
Haze and light transmittance were evaluated for the optical resin lenses obtained in comparative example 1; the evaluation results are shown in Table 1.
Comparative example 2
2, 3-dithio (2-mercapto) -1-propanethiol was prepared in the same manner as in example 1 except that epichlorohydrine having a specific impurity content of 53.29ppm as shown in formula (I) was used; an optical resin lens was further prepared in the same manner as in example 1.
Haze and light transmittance were evaluated for the optical resin lenses obtained in comparative example 2; the evaluation results are shown in Table 1.
Comparative example 3
2, 3-dithio (2-mercapto) -1-propanethiol was prepared in the same manner as in example 1 except that epichlorohydrin having a specific impurity content of the formula (I) of 79.13ppm was used; an optical resin lens was further prepared in the same manner as in example 1.
Haze and light transmittance were evaluated for the optical resin lenses obtained in comparative example 3; the evaluation results are shown in Table 1.
Comparative example 4
2, 3-dithio (2-mercapto) -1-propanethiol was prepared in the same manner as in example 1 except that epichlorohydrin was used as a commercially available epichlorohydrine stock having a purity of 99.5 wt%; an optical resin lens was further prepared in the same manner as in example 1.
Haze and light transmittance were evaluated for the optical resin lenses obtained in comparative example 3; the evaluation results are shown in Table 1.
Comparative example 5
2, 3-dithio (2-mercapto) -1-propanethiol was prepared in the same manner as in example 1 except that epichlorohydrin having a purity of 99.6wt% after purification was used as epichlorohydrin; an optical resin lens was further prepared in the same manner as in example 1.
Haze and light transmittance were evaluated for the optical resin lenses obtained in comparative example 3; the evaluation results are shown in Table 1.
Table 1 shows the results of evaluation of haze and transmittance of the obtained optical resin lenses
As can be seen from a comparison of the optical resin lenses obtained in examples and comparative examples, the optical resin lenses of comparative examples exhibited more fogging, higher haze, and poorer light transmittance than the examples.
As is clear from the results of the examples and comparative examples, when the content of specific impurities in epichlorohydrin exceeds a certain amount or more, the haze of the optical resin lens prepared from the finally obtained polythiol compound becomes high and the light transmittance becomes poor. In particular, when the content of specific impurities in epichlorohydrin exceeds 30ppm, the haze of the optical resin lens is remarkably increased. Thus, when the content of the specific impurity contained in epichlorohydrin is 30ppm or less, an optical resin lens with high light transmittance in which haze is suppressed can be obtained.
Since the above-described examples and comparative examples further demonstrate the process for producing a polythiol compound of the present invention and the process for producing an optical resin lens comprising the compound, it is possible to provide an optical resin lens having stable low haze (e.g., haze of 0.10 to 0.31%); the whole technical scheme provided by the invention has a good application prospect in the field of preparation of various optical components such as spectacle lenses.
The present invention can obtain an optical resin lens with high light transmittance, in which haze is suppressed. The optical lens with low haze and high light transmittance obtained by the invention can replace the prior optical lens, can be widely applied to various fields, and can be particularly used as a spectacle lens base material.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (11)
1. A polythiol compound for an optical resin lens, which is produced by reacting 2-mercaptoethanol with an epichlorohydrin compound, wherein the epichlorohydrin compound has an impurity content represented by formula (I) of 30ppm or less;
2. the polythiol compound for an optical resin lens according to claim 1, wherein the purity of the 2-mercaptoethanol is 99.5% by weight or more; the purity of the epichlorohydrin is above 99.5 wt%.
3. An optical resin lens, characterized by being prepared from raw materials comprising a composition for an optical resin lens; the composition for an optical resin lens comprises a polyisocyanate compound and the polythiol compound for an optical resin lens according to any one of claims 1 to 2.
4. The optical resin lens according to claim 3, wherein the composition for an optical resin lens further comprises another polythiol compound; the other polythiol compound is selected from pentaerythritol tetrasulfocyanurate, diethylene glycol bis (3-mercaptopropionate), pentaerythritol tetrasulfocyanurate, 1, 2-dimercaptocyanune, 1-tris (mercaptomethyl) propane, 1, 4-butanediol bis (3-mercaptopropionate), methane dithiol, methane trithiol, bis (2-mercaptoethyl) ether, tetrakis (mercaptomethyl) methane, 1, 2-dimercaptopropane, 1, 3-dimercaptopropane, 1, 4-dimercaptobutane, 1, 6-dimercaptohexane, 2-dimercaptopropane, 1, 2-bis (2-mercaptoethoxy) ethane, 1, 2-bis (2-mercaptoethylthio) ethane 2, 3-dimercapto-1-propanol, 1, 2-dimercaptoethane, 1, 3-dimercapto-2-propanol, 2-mercaptomethyl-1, 3-dimercaptopropane, 2-mercaptomethyl-1, 4-dimercaptobutane, 1,2, 3-trismercaptopropane, 2- (2-mercaptoethylthio) -1, 3-dimercaptopropane, 2, 4-dimercaptomethyl-1, 5-dimercapto-3-thiapentane, 1, 2-dimercaptobenzene, 1, 3-dimercaptobenzene, 1, 4-dimercaptobenzene, 1, 3-bis (mercaptomethyl) benzene, 2, 5-dimercaptomethyl-1, 4-dithiane, 1, 4-bis (mercaptomethyl) benzene, 2' -dimercaptobiphenyl, bis (4-mercaptophenyl) methane, 2, 2-bis (4-mercaptophenyl) propane, 4' -dimercaptobiphenyl, bis (4-mercaptophenyl) ether, bis (4-mercaptomethylphenyl) methane, 1, 3-tetrakis (mercaptomethylthio) propane 2, 2-bis (4-mercaptomethylphenyl) propane, bis (4-mercaptomethylphenyl) ether, bis (4-mercaptomethylphenyl) thioether, 2, 5-dimercapto-1, 3, 4-thiadiazole, 3, 4-thiophenedichiol, bis (2-mercaptoethyl) thioether, ethylene glycol bis (3-mercaptopropionate), diethylene glycol bis (2-mercaptoacetate), ethylene glycol bis (2-mercaptoacetate) 1, 4-butanediol bis (2-mercaptoacetate), trimethylolpropane trimercaptan-yl propionate, 1, 3-dimercaptocyclohexane, trimethylolpropane trimercaptan-yl acetate, 1, 4-dimercaptocyclohexane, 1, 3-bis (mercaptomethyl) cyclohexane, 1, 4-bis (mercaptomethyl) cyclohexane, bis (4-mercaptophenyl) sulfone, 2, 5-dimercaptomethyl-1, 4-dithiane, 2, 5-bis (2-mercaptoethylthiomethyl) -1, 4-dithiane, 2, 5-dimercaptomethyl-1-thiane, 2, 5-dimercaptoethyl-1-thiane, 2, 5-dimercaptomethyl thiophene, one or more of bis (4-mercaptophenyl) sulfide.
5. The optical resin lens according to claim 3, wherein the polyisocyanate compound is selected from the group consisting of tetramethylene diisocyanate, hexamethylene diisocyanate, cyclohexane diisocyanate, 4' -diisocyanate dicyclohexylmethane, isophorone diisocyanate, norbornane diisocyanate, xylylene diisocyanate, hydrogenated xylylene diisocyanate, tetramethylm-xylylene diisocyanate, dithiodipropylene diisocyanate, dithiodiethyl diisocyanate, 2, 5-diisocyanatothiomethyl thiophene, 2, 5-diisocyanatothiomethyl-1, 4-dithiane, 2, 5-diisocyanate-1, 4-dithiane, thiodihexyl diisocyanate, thiodipropyl diisocyanate, bis (isocyanatomethyl) adamantane, bis (isocyanatomethyl) tetrahydrothiophene, 2, 6-bis (isocyanatomethyl) naphthalene, 1, 5-naphthalene diisocyanate, diethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine triisocyanate, toluene diisocyanate, o-tolylene diisocyanate, diphenyl ether, triphenylmethane diisocyanate, and triphenylether.
6. An optical resin lens according to claim 3, which is prepared from the following raw materials:
100 parts by weight of a composition for an optical resin lens;
0.001 to 0.3 weight portion of catalyst;
0.1 to 1 weight part of auxiliary agent.
7. The optical resin lens according to claim 6, wherein the auxiliary agent is one or more selected from a mold release agent, an ultraviolet absorber, and a toner.
8. The preparation method of the optical resin lens is characterized by comprising the following steps of:
uniformly mixing the raw materials to obtain a mixed solution;
the mixed solution is filtered after defoamation to obtain a mixture;
and (3) injecting the mixture into a forming die, performing polymerization curing reaction, and demolding to obtain the optical resin lens.
9. The method according to claim 8, wherein the deaeration is performed at a vacuum of 10Pa to 500Pa for 0.5h to 2h; the filtration is performed by using a polytetrafluoroethylene filter with a pore size of 1-10 mu m.
10. The preparation method according to claim 8, wherein the polymerization and curing reaction process specifically comprises:
placing the forming die filled with the mixture into an oven, heating from 10 ℃ to 30 ℃ to 110 ℃ to 130 ℃ for 20 hours to 30 hours, and maintaining for 2 hours to 6 hours to carry out polymerization curing reaction.
11. An optical resin material prepared using the polythiol compound for an optical resin lens according to any one of claims 1 to 2.
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