JP7157810B2 - 安定性および反応性が改善されたイソシアネート組成物、並びにこれを用いた光学レンズ - Google Patents
安定性および反応性が改善されたイソシアネート組成物、並びにこれを用いた光学レンズ Download PDFInfo
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- JP7157810B2 JP7157810B2 JP2020531638A JP2020531638A JP7157810B2 JP 7157810 B2 JP7157810 B2 JP 7157810B2 JP 2020531638 A JP2020531638 A JP 2020531638A JP 2020531638 A JP2020531638 A JP 2020531638A JP 7157810 B2 JP7157810 B2 JP 7157810B2
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- 239000000203 mixture Substances 0.000 title claims description 246
- 239000012948 isocyanate Substances 0.000 title claims description 131
- 150000002513 isocyanates Chemical class 0.000 title claims description 131
- 230000003287 optical effect Effects 0.000 title claims description 52
- 230000009257 reactivity Effects 0.000 title description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 124
- 239000000460 chlorine Substances 0.000 claims description 124
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 121
- 238000003860 storage Methods 0.000 claims description 59
- 239000003381 stabilizer Substances 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 31
- -1 alkanoyl chloride Chemical compound 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 23
- 150000003573 thiols Chemical class 0.000 claims description 21
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 claims description 20
- 239000003755 preservative agent Substances 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 12
- 229920002578 polythiourethane polymer Polymers 0.000 claims description 12
- 230000002335 preservative effect Effects 0.000 claims description 12
- 239000002244 precipitate Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000002834 transmittance Methods 0.000 claims description 8
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 claims description 7
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 7
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 7
- 229940073608 benzyl chloride Drugs 0.000 claims description 7
- 230000009477 glass transition Effects 0.000 claims description 7
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 3
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 46
- 238000006243 chemical reaction Methods 0.000 description 22
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 16
- 239000000126 substance Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 13
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
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- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
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- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
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- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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- 206010040925 Skin striae Diseases 0.000 description 4
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- CEUQYYYUSUCFKP-UHFFFAOYSA-N 2,3-bis(2-sulfanylethylsulfanyl)propane-1-thiol Chemical compound SCCSCC(CS)SCCS CEUQYYYUSUCFKP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000004809 Teflon Substances 0.000 description 3
- 229920006362 Teflon® Polymers 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
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- MTZVWTOVHGKLOX-UHFFFAOYSA-N 2,2-bis(sulfanylmethyl)propane-1,3-dithiol Chemical compound SCC(CS)(CS)CS MTZVWTOVHGKLOX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- RUDUCNPHDIMQCY-UHFFFAOYSA-N [3-(2-sulfanylacetyl)oxy-2,2-bis[(2-sulfanylacetyl)oxymethyl]propyl] 2-sulfanylacetate Chemical compound SCC(=O)OCC(COC(=O)CS)(COC(=O)CS)COC(=O)CS RUDUCNPHDIMQCY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 125000005910 alkyl carbonate group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
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- ZYFMFBIJUSAVNV-BETUJISGSA-N (2R)-2-(2-sulfanylethylsulfanyl)-3-[3-[(2S)-3-sulfanyl-2-(2-sulfanylethylsulfanyl)propyl]sulfanylpropylsulfanyl]propane-1-thiol Chemical compound SC[C@H](CSCCCSC[C@H](CS)SCCS)SCCS ZYFMFBIJUSAVNV-BETUJISGSA-N 0.000 description 1
- KPLNSCKRXRCEIQ-TXEJJXNPSA-N (2r)-2-(2-sulfanylethylsulfanyl)-3-[2-[(2s)-3-sulfanyl-2-(2-sulfanylethylsulfanyl)propyl]sulfanylethylsulfanyl]propane-1-thiol Chemical compound SCCS[C@@H](CS)CSCCSC[C@@H](CS)SCCS KPLNSCKRXRCEIQ-TXEJJXNPSA-N 0.000 description 1
- KHLYDKDUYMXJCZ-OKILXGFUSA-N (2r)-2-[2-(2-sulfanylethylsulfanyl)ethylsulfanyl]-3-[[(2s)-3-sulfanyl-2-[2-(2-sulfanylethylsulfanyl)ethylsulfanyl]propyl]disulfanyl]propane-1-thiol Chemical compound SCCSCCS[C@@H](CS)CSSC[C@@H](CS)SCCSCCS KHLYDKDUYMXJCZ-OKILXGFUSA-N 0.000 description 1
- SQTMWMRJFVGAOW-OLQVQODUSA-N (2s)-3-[(2r)-2,3-bis(sulfanyl)propyl]sulfanylpropane-1,2-dithiol Chemical compound SC[C@H](S)CSC[C@H](S)CS SQTMWMRJFVGAOW-OLQVQODUSA-N 0.000 description 1
- XVNGTGZGWDPIRR-UHFFFAOYSA-N 1,2,2-tris(sulfanylmethylsulfanyl)ethylsulfanylmethanethiol Chemical compound SCSC(SCS)C(SCS)SCS XVNGTGZGWDPIRR-UHFFFAOYSA-N 0.000 description 1
- FDJWTMYNYYJBAT-UHFFFAOYSA-N 1,3,3-tris(sulfanylmethylsulfanyl)propylsulfanylmethanethiol Chemical compound SCSC(SCS)CC(SCS)SCS FDJWTMYNYYJBAT-UHFFFAOYSA-N 0.000 description 1
- RRPZHYWZRCTYBG-UHFFFAOYSA-N 18,18-dimethylnonadecan-1-amine Chemical class CC(C)(C)CCCCCCCCCCCCCCCCCN RRPZHYWZRCTYBG-UHFFFAOYSA-N 0.000 description 1
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-UHFFFAOYSA-N 0.000 description 1
- HKJDFSNCHROEEB-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)-3-[2-[2-[3-sulfanyl-2-(2-sulfanylethylsulfanyl)propyl]sulfanylethylsulfanyl]ethylsulfanyl]propane-1-thiol Chemical compound SCCSC(CS)CSCCSCCSCC(CS)SCCS HKJDFSNCHROEEB-UHFFFAOYSA-N 0.000 description 1
- KPLNSCKRXRCEIQ-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)-3-[2-[3-sulfanyl-2-(2-sulfanylethylsulfanyl)propyl]sulfanylethylsulfanyl]propane-1-thiol Chemical compound SCCSC(CS)CSCCSCC(CS)SCCS KPLNSCKRXRCEIQ-UHFFFAOYSA-N 0.000 description 1
- KSJBMDCFYZKAFH-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)ethanethiol Chemical compound SCCSCCS KSJBMDCFYZKAFH-UHFFFAOYSA-N 0.000 description 1
- NQLQMVQEQFIDQB-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)propane-1,3-dithiol Chemical compound SCCSC(CS)CS NQLQMVQEQFIDQB-UHFFFAOYSA-N 0.000 description 1
- QTEWPHJCEXIMRJ-UHFFFAOYSA-N 2-[2,3-bis(2-sulfanylethylsulfanyl)propylsulfanyl]ethanethiol Chemical compound SCCSCC(SCCS)CSCCS QTEWPHJCEXIMRJ-UHFFFAOYSA-N 0.000 description 1
- NTRMNYKTDJIULH-UHFFFAOYSA-N 3-[2,3-bis(sulfanyl)propyldisulfanyl]propane-1,2-dithiol Chemical compound SCC(S)CSSCC(S)CS NTRMNYKTDJIULH-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-M 3-mercaptopropionate Chemical compound [O-]C(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-M 0.000 description 1
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- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 1
- AQFDQKHIHPQLBK-UHFFFAOYSA-N S-[2,3-bis(sulfanyl)propanoyl] 2,3-bis(sulfanyl)propanethioate Chemical compound SC(C(=O)SC(C(CS)S)=O)CS AQFDQKHIHPQLBK-UHFFFAOYSA-N 0.000 description 1
- JHXCBYAWHFDMGZ-UHFFFAOYSA-N S-[2,3-bis(sulfanyl)propanoylsulfanyl] 2,3-bis(sulfanyl)propanethioate Chemical compound SC(C(=O)SSC(C(CS)S)=O)CS JHXCBYAWHFDMGZ-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- QNSUVMHSJGIMDL-UHFFFAOYSA-N [6-(sulfanylmethylsulfanyl)-1,3-dithian-4-yl]sulfanylmethanethiol Chemical compound SCSC1CC(SCS)SCS1 QNSUVMHSJGIMDL-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 150000004982 aromatic amines Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
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- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical class CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- VCAVAURZPNANDQ-UHFFFAOYSA-N ethyl-hexadecyl-dimethylazanium Chemical class CCCCCCCCCCCCCCCC[N+](C)(C)CC VCAVAURZPNANDQ-UHFFFAOYSA-N 0.000 description 1
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
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- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical class CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Description
[化2]
前記式において、nは1~3の整数であり、R1はハロゲン、ヒドロキシ、またはアミノで置換または非置換されたC6-10アリールであり、R2はC1-10アルキレンであり、R3はハロゲン、ヒドロキシ、またはアミノで置換または非置換されたC6-10アリール、もしくはハロゲン、ヒドロキシ、またはアミノで置換または非置換されたC1-10アルキルである。
具体的に、前記光学レンズは、ガラス転移温度(Tg)に優れている。例えば、前記光学レンズは、ガラス転移温度(Tg)が75℃以上、80℃以上、85℃以上、または88℃以上であり得る。具体的に、75℃~120℃の範囲、80℃~120℃の範囲、95℃~120℃の範囲、80℃~100℃の範囲、85℃~100℃の範囲、または85℃~90℃の範囲であり得る。
前記内容を以下の実施例により、さらに詳細に説明する。但し、下記実施例は、本発明を例示するためのものであるのみ、実施例の範囲はこれらにのみ限定されるものではない。
(1)材料の準備
[3-(アミノメチル)シクロヘキシル]メタンアミン5重量部をo-ジクロロベンゼン78重量部に溶解してアミン溶液を調製した。以降、o-ジクロロベンゼン52重量部にホスゲン44重量部を溶解した溶液をブラインコンデンサにより10℃に冷却して反応容器に入れ、これに前記調製したアミン溶液を50℃以下の温度にて徐々に添加した。この際、アミン溶液の添加量は、アミン1モルに対してホスゲン5モルとなるようにした。その後、反応容器を密封して2時間反応溶液を撹拌した。140℃の温度および3kg/cm2の圧力条件で3時間さらに反応を行った後、反応で生成された塩酸ガスを放出した。反応が完了した後、過量のホスゲンを蒸留工程により除去した。生成物を減圧下における分別蒸留により精製してH6XDI含有組成物を得た。
前記で得られたH6XDI含有組成物に、下記表1に示すような塩素系保存安定剤を添加して、塩素含有量が多様に調節されたイソシアネート組成物1~7を調製した。
前記実施例1と同様の方法によりイソシアネート組成物を調製するが、下記評価例1に記載のような塩素系保存安定剤を使用した。
<評価例1:イソシアネート組成物の評価>
前記実施例1で調製したイソシアネート組成物について、以下のような方法で保存安定性を評価した。その結果を下記表1~3に示した。
前記実施例1において塩素含有量が多様に調節されたイソシアネート組成物1~7について、組成物内の初期NCO基の含有量(NCO%)を逆滴定(back titration)法により測定した。まず、理論的NCOに対して過量のn-ブチルアミンを投入して反応させ、残留する過量のn-ブチルアミンを0.1N濃度の塩酸試薬で分析した。その結果を表1にまとめた。
前記実施例1において、塩素含有量が多様に調節されたイソシアネート組成物1~7について、これらの初期金属イオン濃度を分析した後、互いに異なる材質の容器に80℃の温度条件で6ヶ月間保管した後、残留金属イオンの濃度を分析した。
前記実施例2において製造した光学レンズについて、以下のような方法により物性を評価した。その結果を下記表4に示した。
光学レンズについて、Atago社製のアッベ屈折計であるDR-M4モデルを使用して、20℃における屈折率およびアッベ数を測定した。
光学レンズについて、ミノルタ社の色彩色差計CT-210を使用して色度座標xおよびyを測定した後、測定値を下記の数学式1に適用して黄色度を計算した。また、同一機器を使用して得たスペクトルで550nm波長における透過度を透過率として示した。
[数1]
Y.I.=(234x+106y+106)/y
光学レンズについて、熱機械分析装置(TMA Q400、TA Instruments社)を用いたペネトレーションテスト(50g荷重、ピン先端0.5mmΦ、加熱速度10℃/分)によりガラス転移温度を測定した。
光学レンズ100枚を水銀ランプの下で肉眼により観察し、不均一相が確認されたレンズは脈理があるものと分類して百分率を算出した。その結果、脈理の発生率が5%未満の場合に良好と判定し、5%以上の場合に不良と判定した。
Claims (9)
- 塩素系保存安定剤および水添キシリレンジイソシアネート(H6XDI)を含み、
イソシアネート組成物に含まれる塩素の含有量が22ppm~370ppmであり、
全体の組成物中に含まれているNCO基の含有量が42重量%~45重量%であり、
前記塩素系保存安定剤が塩素イオンを含み、
前記塩素系保存安定剤が、ベンゾトリクロリド、ベンジルクロリド、ベンゾイルクロリド、およびC1-10アルカノイルクロリドからなる群より選択される1種以上を含み、
前記イソシアネート組成物が80℃の温度で6ヶ月間放置される際、発生する沈殿物の量が組成物の総重量を基準に1重量%以下であり、
初期組成物内のNCO基の含有量と、80℃の温度で6ヶ月間放置された後の組成物内のNCO基の含有量との差が5重量%以下である、イソシアネート組成物。 - 前記イソシアネート組成物が、前記組成物と接触する部位が塩素と反応性のない容器に密封され、80℃の温度で6ヶ月間放置される際、初期組成物内のNCO基の含有量と、前記条件で6ヶ月間放置された後の組成物内のNCO基の含有量との差が4重量%以下である、請求項1に記載のイソシアネート組成物。
- (1)ジメチルシクロヘキシルアミンからイソシアネート合成工程により水添キシリレンジイソシアネート(H6XDI)を含有する組成物を調製する段階と、
(2)前記水添キシリレンジイソシアネートを含有する組成物に含まれている塩素の含有量を22ppm~370ppmになるように調節する段階とを含み、
前記段階(2)は、前記水添キシリレンジイソシアネートを含有する組成物にベンゾトリクロリド、ベンジルクロリド、ベンゾイルクロリド、およびC1-10アルカノイルクロリドからなる群より選択される1種以上、又は塩素イオンを含む塩素系保存安定剤を添加して行われ、
前記組成物が80℃の温度で6ヶ月間放置される際、発生する沈殿物の量が組成物の総重量を基準に1重量%以下であり、
初期組成物内のNCO基の含有量と、80℃の温度で6ヶ月間放置された後の組成物内のNCO基の含有量との差が5重量%以下である、イソシアネート組成物の調製方法。 - 前記段階(2)が、前記H6XDI含有組成物を加熱蒸留する段階をさらに含む、請求項3に記載のイソシアネート組成物の調製方法。
- イソシアネート組成物およびチオール系化合物を含み、
前記イソシアネート組成物は、塩素系保存安定剤および水添キシリレンジイソシアネート(H6XDI)を含み、
前記イソシアネート組成物に含まれる塩素の含有量が22ppm~370ppmであり、前記イソシアネート組成物内に含まれているNCO基の含有量が42重量%~45重量%であり、
前記塩素系保存安定剤が塩素イオンを含み、
前記塩素系保存安定剤が、ベンゾトリクロリド、ベンジルクロリド、ベンゾイルクロリド、およびC1-10アルカノイルクロリドからなる群より選択され、
前記イソシアネート組成物が80℃の温度で6ヶ月間放置される際、発生する沈殿物の量が組成物の総重量を基準に1重量%以下であり、
初期組成物内のNCO基の含有量と、80℃の温度で6ヶ月間放置された後の組成物内のNCO基の含有量との差が5重量%以下である、重合性組成物。 - イソシアネート組成物およびチオール系化合物を含む重合性組成物が硬化して形成されたポリチオウレタンを含み、
前記イソシアネート組成物は、塩素系保存安定剤および水添キシリレンジイソシアネート(H6XDI)を含み、
前記イソシアネート組成物に含まれる塩素含有量が22ppm~370ppmであり、前記イソシアネート組成物内に含まれているNCO基の含有量が42重量%~45重量%であり、
前記塩素系保存安定剤が塩素イオンを含み、
前記塩素系保存安定剤が、ベンゾトリクロリド、ベンジルクロリド、ベンゾイルクロリド、およびC1-10アルカノイルクロリドからなる群より選択され、
前記イソシアネート組成物が80℃の温度で6ヶ月間放置される際、発生する沈殿物の量が組成物の総重量を基準に1重量%以下であり、
前記イソシアネート組成物は、初期組成物内のNCO基の含有量と、80℃の温度で6ヶ月間放置された後の組成物内のNCO基の含有量との差が5重量%以下である、光学レンズ。 - 前記光学レンズが、1~20の黄色度(YI)および550nmの波長で85.0%~99.9%の光透過率を有する、請求項6に記載の光学レンズ。
- 前記光学レンズが、30~45のアッベ数および75℃~120℃のガラス転移温度を有する、請求項6に記載の光学レンズ。
- (A)イソシアネート組成物を提供する段階と、
(B)チオール系化合物を提供する段階と、
(C)前記イソシアネート組成物と前記チオール系化合物とを含む重合性組成物を提供する段階と、
(D)前記重合性組成物を硬化させる段階とを含み、
前記イソシアネート組成物は、塩素系保存安定剤および水添キシリレンジイソシアネート(H6XDI)を含み、
前記イソシアネート組成物に含まれる塩素含有量が22ppm~370ppmであり、前記イソシアネート組成物内に含まれているNCO基の含有量が42重量%~45重量%であり、
前記塩素系保存安定剤が塩素イオンを含み、
前記塩素系保存安定剤が、ベンゾトリクロリド、ベンジルクロリド、ベンゾイルクロリド、およびC1-10アルカノイルクロリドからなる群より選択され、
前記イソシアネート組成物が80℃の温度で6ヶ月間放置される際、発生する沈殿物の量が組成物の総重量を基準に1重量%以下であり、
前記イソシアネート組成物は、初期組成物内のNCO基の含有量と、80℃の温度で6ヶ月間放置された後の組成物内のNCO基の含有量との差が5重量%以下である、光学レンズの製造方法。
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KR102364914B1 (ko) * | 2019-12-06 | 2022-02-18 | 에스케이씨 주식회사 | 디이소시아네이트 조성물 및 광학 렌즈의 제조방법 |
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US11518737B2 (en) | 2019-12-05 | 2022-12-06 | Skc Co., Ltd. | Method of preparing diisocyanate composition and optical lens |
JP7307440B2 (ja) | 2019-12-06 | 2023-07-12 | エスケイシー・カンパニー・リミテッド | 光学レンズ用ジイソシアネート組成物およびその調製方法 |
KR20210071798A (ko) * | 2019-12-06 | 2021-06-16 | 에스케이씨 주식회사 | 디이소시아네이트 조성물, 이의 제조방법 및 이를 이용한 광학 재료 |
US11339121B2 (en) * | 2019-12-06 | 2022-05-24 | Skc Co., Ltd. | Method of preparing diisocyanate composition |
US11731936B2 (en) * | 2019-12-06 | 2023-08-22 | Skc Co., Ltd. | Diisocyanate composition, preparation method thereof and optical material using same |
KR102639515B1 (ko) * | 2019-12-06 | 2024-02-22 | 에스케이피유코어 주식회사 | 디이소시아네이트 조성물, 이의 제조방법 및 이를 이용한 광학 재료 |
US11932591B2 (en) | 2019-12-06 | 2024-03-19 | Skc Co., Ltd. | Method of preparing diisocyanate composition and optical lens |
KR102456421B1 (ko) * | 2019-12-06 | 2022-10-19 | 에스케이씨 주식회사 | 디이소시아네이트 조성물 및 광학 렌즈의 제조방법 |
JP2021167398A (ja) * | 2020-04-13 | 2021-10-21 | ホヤ レンズ タイランド リミテッドHOYA Lens Thailand Ltd | 光学材料用重合性組成物およびその製造方法、透明樹脂の製造方法、ならびにレンズ基材の製造方法 |
CN115989258A (zh) * | 2020-09-03 | 2023-04-18 | Skc株式会社 | 苯二亚甲基二异氰酸酯组合物和包括其的光学聚合性组合物 |
CN112062786A (zh) * | 2020-09-15 | 2020-12-11 | 江苏华盛锂电材料股份有限公司 | 异氰酸酯硅烷偶联剂的提纯方法及异氰酸酯硅烷偶联剂 |
CN113265037B (zh) * | 2021-05-17 | 2023-03-24 | 万华化学(宁波)有限公司 | 一种多异氰酸酯组合物及其制备方法和应用 |
KR20230033888A (ko) | 2021-09-02 | 2023-03-09 | 에스케이씨 주식회사 | 자일릴렌디이소시아네이트 조성물 및 이를 포함하는 광학용 중합성 조성물 |
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US11673992B2 (en) | 2023-06-13 |
TW201930260A (zh) | 2019-08-01 |
WO2019132491A1 (ko) | 2019-07-04 |
TWI707838B (zh) | 2020-10-21 |
CN111601835B (zh) | 2022-08-26 |
CN111601835A (zh) | 2020-08-28 |
KR101954346B1 (ko) | 2019-03-05 |
PH12020550997A1 (en) | 2021-04-26 |
JP2021505632A (ja) | 2021-02-18 |
US20210163669A1 (en) | 2021-06-03 |
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