JP2008074958A - ポリチオウレタン重合触媒、それを含む重合性組成物及びそれより得られる光学材料及びその製造方法 - Google Patents
ポリチオウレタン重合触媒、それを含む重合性組成物及びそれより得られる光学材料及びその製造方法 Download PDFInfo
- Publication number
- JP2008074958A JP2008074958A JP2006255639A JP2006255639A JP2008074958A JP 2008074958 A JP2008074958 A JP 2008074958A JP 2006255639 A JP2006255639 A JP 2006255639A JP 2006255639 A JP2006255639 A JP 2006255639A JP 2008074958 A JP2008074958 A JP 2008074958A
- Authority
- JP
- Japan
- Prior art keywords
- bis
- group
- mercaptomethylthio
- compounds
- phosphoric acid
- 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.)
- Granted
Links
- 229920002578 polythiourethane polymer Polymers 0.000 title claims abstract description 36
- 230000003287 optical effect Effects 0.000 title claims abstract description 35
- 239000002685 polymerization catalyst Substances 0.000 title claims abstract description 24
- 239000000203 mixture Substances 0.000 title claims description 50
- 239000000463 material Substances 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- -1 amine compound Chemical class 0.000 claims abstract description 125
- 229920005989 resin Polymers 0.000 claims abstract description 76
- 239000011347 resin Substances 0.000 claims abstract description 76
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 88
- 229920003023 plastic Polymers 0.000 claims description 19
- 239000004033 plastic Substances 0.000 claims description 19
- 229920006295 polythiol Polymers 0.000 claims description 17
- 239000012948 isocyanate Substances 0.000 claims description 14
- 150000002513 isocyanates Chemical class 0.000 claims description 14
- 239000005056 polyisocyanate Substances 0.000 claims description 13
- 229920001228 polyisocyanate Polymers 0.000 claims description 13
- 150000003573 thiols Chemical class 0.000 claims description 11
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 claims description 10
- CEUQYYYUSUCFKP-UHFFFAOYSA-N 2,3-bis(2-sulfanylethylsulfanyl)propane-1-thiol Chemical compound SCCSCC(CS)SCCS CEUQYYYUSUCFKP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- GXELTROTKVKZBQ-UHFFFAOYSA-N n,n-dibenzylhydroxylamine Chemical compound C=1C=CC=CC=1CN(O)CC1=CC=CC=C1 GXELTROTKVKZBQ-UHFFFAOYSA-N 0.000 claims description 6
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims description 5
- FDJWTMYNYYJBAT-UHFFFAOYSA-N 1,3,3-tris(sulfanylmethylsulfanyl)propylsulfanylmethanethiol Chemical compound SCSC(SCS)CC(SCS)SCS FDJWTMYNYYJBAT-UHFFFAOYSA-N 0.000 claims description 4
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 claims description 4
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 claims description 4
- LEAAXJONQWQISB-UHFFFAOYSA-N 2,5-bis(isocyanatomethyl)bicyclo[2.2.1]heptane Chemical compound C1C2C(CN=C=O)CC1C(CN=C=O)C2 LEAAXJONQWQISB-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 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 claims description 4
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 claims description 4
- 229920001174 Diethylhydroxylamine Polymers 0.000 claims description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 4
- 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 claims description 4
- QNSUVMHSJGIMDL-UHFFFAOYSA-N [6-(sulfanylmethylsulfanyl)-1,3-dithian-4-yl]sulfanylmethanethiol Chemical compound SCSC1CC(SCS)SCS1 QNSUVMHSJGIMDL-UHFFFAOYSA-N 0.000 claims description 4
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 claims description 4
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 4
- IXBUFAUQDFHNGI-UHFFFAOYSA-N methylsulfanylmethanethiol Chemical group CSCS IXBUFAUQDFHNGI-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 abstract description 9
- 239000006082 mold release agent Substances 0.000 abstract description 9
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- 230000009471 action Effects 0.000 abstract description 3
- 125000002723 alicyclic group Chemical group 0.000 abstract description 2
- 150000003606 tin compounds Chemical class 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 52
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- 239000010410 layer Substances 0.000 description 34
- 239000000047 product Substances 0.000 description 29
- 238000004043 dyeing Methods 0.000 description 26
- 239000000975 dye Substances 0.000 description 21
- 239000003054 catalyst Substances 0.000 description 18
- 229910019142 PO4 Inorganic materials 0.000 description 15
- 235000021317 phosphate Nutrition 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000011247 coating layer Substances 0.000 description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 14
- 239000003607 modifier Substances 0.000 description 12
- 239000010452 phosphate Substances 0.000 description 12
- 235000011007 phosphoric acid Nutrition 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 235000010290 biphenyl Nutrition 0.000 description 11
- 239000004305 biphenyl Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000005871 repellent Substances 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 7
- 239000006096 absorbing agent Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 230000002940 repellent Effects 0.000 description 7
- YCLSOMLVSHPPFV-UHFFFAOYSA-N 3-(2-carboxyethyldisulfanyl)propanoic acid Chemical compound OC(=O)CCSSCCC(O)=O YCLSOMLVSHPPFV-UHFFFAOYSA-N 0.000 description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 125000006267 biphenyl group Chemical group 0.000 description 6
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 6
- 238000001723 curing Methods 0.000 description 6
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 6
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- 239000011259 mixed solution Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 239000004810 polytetrafluoroethylene Substances 0.000 description 6
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 5
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- KVZJLSYJROEPSQ-UHFFFAOYSA-N 1,2-dimethylcyclohexane Chemical compound CC1CCCCC1C KVZJLSYJROEPSQ-UHFFFAOYSA-N 0.000 description 4
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- QRMPKOFEUHIBNM-UHFFFAOYSA-N 1,4-dimethylcyclohexane Chemical compound CC1CCC(C)CC1 QRMPKOFEUHIBNM-UHFFFAOYSA-N 0.000 description 4
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- 238000000137 annealing Methods 0.000 description 4
- 230000003373 anti-fouling effect Effects 0.000 description 4
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 4
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- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 4
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- ZJVHUSCHGQGVCC-UHFFFAOYSA-N P(=O)(OCCCC)(OCCCC)O.C1(=CC=CC=C1)N(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound P(=O)(OCCCC)(OCCCC)O.C1(=CC=CC=C1)N(C1=CC=CC=C1)C1=CC=CC=C1 ZJVHUSCHGQGVCC-UHFFFAOYSA-N 0.000 description 3
- VGXPZBTXYASMSE-UHFFFAOYSA-N P(=O)(OCCCC)(OCCCC)O.NO Chemical compound P(=O)(OCCCC)(OCCCC)O.NO VGXPZBTXYASMSE-UHFFFAOYSA-N 0.000 description 3
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- 229910052718 tin Inorganic materials 0.000 description 1
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 229910052726 zirconium Inorganic materials 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
[1] 一般式(1)で表されるアミン化合物と、一般式(2)で表されるリン酸からなる塩であるポリチオウレタン系光学材料用重合触媒に関する。
[2] 一般式(1)で表されるアミン化合物のR2、R3が炭素数1から8のアルキル基であることを特徴とする、[1]記載の重合触媒。
[3] 一般式(1)で表されるアミン化合物がトリフェニルアミン、N,N−ジエチルヒドロキシルアミンまたはN,N−ジベンジルヒドロキシルアミンであることを特徴とする、[2]記載の重合触媒。
[4] 一般式(2)で表されるリン酸のnが0〜2の整数を示し、R4が炭素数1〜10のアルキル基であることを特徴とする、[1]から[3]のいずれかに記載の重合触媒。
[5] 一般式(2)で表されるリン酸がジブチルリン酸またはジオクチルリン酸であることを特徴とする、[4]記載の重合触媒。
[6] [1]から[5]のいずれかに記載の重合触媒と、ポリイソシアネート化合物、ポリイソチオシアネート化合物、イソシアナト基を有するポリイソチオシアネート化合物より選ばれる一種または二種以上のイソシアネート類及び、ポリチオール化合物より選ばれる一種または二種以上のチオール類を含有するポリチオウレタン系光学材料用重合性組成物。
[8] [6]または[7]のいずれかに記載の重合性組成物を硬化させて得られるポリチオウレタン樹脂。
[9] [8]記載のポリチオウレタン樹脂からなる光学材料。
[10] [9]記載の光学材料からなるプラスチックレンズ。
[11] [6]または[7]のいずれかに記載の重合性組成物を注型重合することを特徴とする、ポリチオウレタン樹脂の製造方法。
本発明は、一般式(1)で表されるアミン化合物と、一般式(2)で表されるリン酸からなる塩であるポリチオウレタン系光学材料用重合触媒に関する。
フェニル基及び、ベンゼン、トルエン、o−キシレン、m−キシレン、p−キシレン、ナフタレン、ビフェニ−ル、アントラセン、ペリレン、スチレン、エチルベンゼン等の芳香族化合物から誘導される1価以上の置換フェニル基等を挙げることができるが、これら例示化合物のみに限定されるものではない。
2−メチルプロパン、2−メチルブタン、2−メチルペンタン、3−メチルペンタン、3−エチルペンタン、2−メチルヘキサン、3−メチルヘキサン、3−エチルヘキサン、2−メチルへプタン、3−メチルへプタン、4−メチルへプタン、3−エチルへプタン、4−エチルへプタン、4−プロピルへプタン、2−メチルオクタン、3−メチルオクタン、4−メチルオクタン、3−エチルオクタン、4−エチルオクタン、4−プロピルオクタン、2−メチル−1−ブテン、3−メチル−1−ブテン、2−メチル−2−ブテン、2−メチル−ブタジエン、2,3−ジメチルブタジエン等の分岐状脂肪族化合物から誘導される1価以上の有機残基及び、
上記R2、R3が、炭素数1から8のアルキル基であることはより好ましい。
上記nが0〜2の整数を示し、R4が炭素数1〜10のアルキル基であることはより好ましい。
N−メチルヒドロキシルアミン、N−エチルヒドロキシルアミン、N−プロピルヒドロキシルアミン、N−ブチルヒドロキシルアミン、N−ペンチルヒドロキシルアミン、N−ヘキシルヒドロキシルアミン、N−オクチルヒドロキシルアミン、N−(2−エチルヘキシル)ヒドロキシルアミン、N−シクロペンチルヒドロキシルアミン、N−シクロヘキシルヒドロキシルアミン、N−フェニルヒドロキシルアミン、N−ベンジルヒドロキシルアミン等のN−モノ置換ヒドロキシルアミン及びその誘導体及び、
これらアミンリン酸塩は単独でも、2種類以上を混合しても使用することができる。
イソホロンジイソシアネート、1,2−ビス(イソシアナトメチル)シクロヘキサン、1,3−ビス(イソシアナトメチル)シクロヘキサン、1,4−ビス(イソシアナトメチル)シクロヘキサン、ジシクロヘキシルメタンジイソシアネート、シクロヘキサンジイソシアネート、メチルシクロヘキサンジイソシアネート、ジシクロヘキシルジメチルメタンイソシアネート、2,2−ジメチルジシクロヘキシルメタンイソシアネート、2,5−ビス(イソシアナトメチル)ビシクロ−[2,2,1]−ヘプタン、2,6−ビス(イソシアナトメチル)ビシクロ−[2,2,1]−ヘプタン、3,8−ビス(イソシアナトメチル)トリシクロデカン、3,9−ビス(イソシアナトメチル)トリシクロデカン、4,8−ビス(イソシアナトメチル)トリシクロデカン、4,9−ビス(イソシアナトメチル)トリシクロデカン等の脂環族ポリイソシアネート化合物及び、
1,1,3,3−テトラキス(メルカプトメチルチオ)プロパン、1,1,2,2−テトラキス(メルカプトメチルチオ)エタン、4,6−ビス(メルカプトメチルチオ)−1,3−ジチアシクロヘキサン、1,1,5,5−テトラキス(メルカプトメチルチオ)−3−チアペンタン、1,1,6,6−テトラキス(メルカプトメチルチオ)−3,4−ジチアヘキサン、2,2−ビス(メルカプトメチルチオ)エタンチオール、2−(4,5−ジメルカプト−2−チアペンチル)−1,3−ジチアシクロペンタン、2,5−ビス(4,4−ビス(メルカプトメチルチオ)−2−チアブチル)−1,4−ジチアン、2,2−ビス(メルカプトメチルチオ)−1,3−プロパンジチオール、3−メルカプトメチルチオ−1,7−ジメルカプト−2,6−ジチアヘプタン、3,6−ビス(メルカプトメチルチオ)−1,9−ジメルカプト−2,5,8−トリチアノナン、3−メルカプトメチルチオ−1,6−ジメルカプト−2,5−ジチアヘキサン、2−(2,2−ビス(メルカプトジメチルチオ)エチル)−1,3−ジチエタン、1,1,9,9−テトラキス(メルカプトメチルチオ)−5−(3,3−ビス(メルカプトメチルチオ)−1−チアプロピル)3,7−ジチアノナン、トリス(2,2−ビス(メルカプトメチルチオ)エチル)メタン、トリス(4,4−ビス(メルカプトメチルチオ)−2−チアブチル)メタン、テトラキス(2,2−ビス(メルカプトメチルチオ)エチル)メタン、テトラキス(4,4−ビス(メルカプトメチルチオ)−2−チアブチル)メタン、3,5,9,11−テトラキス(メルカプトメチルチオ)−1,13−ジメルカプト−2,6,8,12−テトラチアトリデカン、3,5,9,11,15,17−ヘキサキス(メルカプトメチルチオ)−1,19−ジメルカプト−2,6,8,12,14,18−ヘキサチアノナデカン、9−(2,2−ビス(メルカプトメチルチオ)エチル)−3,5,13,15−テトラキス(メルカプトメチルチオ)−1,17−ジメルカプト−2,6,8,10,12,16−ヘキサチアヘプタデカン、3,4,8,9−テトラキス(メルカプトメチルチオ)−1,11−ジメルカプト−2,5,7,10−テトラチアウンデカン、3,4,8,9,13,14−ヘキサキス(メルカプトメチルチオ)−1,16−ジメルカプト−2,5,7,10,12,15−ヘキサチアヘキサデカン、8−[ビス(メルカプトメチルチオ)メチル]−3,4,12,13−テトラキス(メルカプトメチルチオ)−1,15−ジメルカプト−2,5,7,9,11,14−ヘキサチアペンタデカン、4,6−ビス[3,5−ビス(メルカプトメチルチオ)−7−メルカプト−2,6−ジチアヘプチルチオ]−1,3−ジチアン、4−[3,5−ビス(メルカプトメチルチオ)−7−メルカプト−2,6−ジチアヘプチルチオ]−6−メルカプトメチルチオ−1,3−ジチアン、1,1−ビス[4−(6−メルカプトメチルチオ)−1,3−ジチアニールチオ]−1,3−ビス(メルカプトメチルチオ)プロパン、1−[4−(6−メルカプトメチルチオ)−1,3−ジチアニールチオ]−3−[2,2−ビス(メルカプトメチルチオ)エチル]−7,9−ビス(メルカプトメチルチオ)−2,4,6,10−テトラチアウンデカン、1,5−ビス[4−(6−メルカプトメチルチオ)−1,3−ジチアニールチオ]−3−[2−(1,3−ジチエタニル)]メチル−2,4−ジチアペンタン、4,6−ビス{3−[2−(1,3−ジチエタニル)]メチル−5−メルカプト−2,4−ジチアペンチルチオ}−1,3−ジチアン、4,6−ビス[4−(6−メルカプトメチルチオ)−1,3−ジチアニールチオ]−6−[4−(6−メルカプトメチルチオ)−1,3−ジチアニールチオ]−1,3−ジチアン、3−[2−(1,3−ジチエタニル)]メチル−7,9−ビス(メルカプトメチルチオ)−1,11−ジメルカプト−2,4,6,10−テトラチアウンデカン、9−[2−(1,3−ジチエタニル)]メチル−3,5,13,15−テトラキス(メルカプトメチルチオ)−1,17−ジメルカプト−2,6,8,10,12,16−ヘキサチアヘプタデカン、3−[2−(1,3−ジチエタニル)]メチル−7,9,13,15−テトラキス(メルカプトメチルチオ)−1,17−ジメルカプト−2,4,6,10,12,16−ヘキサチアヘプタデカン、3,7−ビス[2−(1,3−ジチエタニル)]メチル−1.9−ジメルカプト−2,4,6,8−テトラチアノナン、4−[3,4,8,9−テトラキス(メルカプトメチルチオ)−11−メルカプト−2,5,7,10−テトラチアウンデシル]−5−メルカプトメチルチオ−1,3−ジチオラン、4,5−ビス[3,4−ビス(メルカプトメチルチオ)−6−メルカプト−2,5−ジチアヘキシルチオ]−1,3−ジチオラン、4−[3,4−ビス(メルカプトメチルチオ)−6−メルカプト−2,5−ジチアヘキシルチオ]−5−メルカプトメチルチオ−1,3−ジチオラン、4−[3−ビス(メルカプトメチルチオ)メチル−5,6−ビス(メルカプトメチルチオ)−8−メルカプト−2,4,7−トリチアオクチル]−5−メルカプトメチルチオ−1,3−ジチオラン、2−{ビス[3,4−ビス(メルカプトメチルチオ)−6−メルカプト−2,5−ジチアヘキシルチオ]メチル}−1,3−ジチエタン、2−[3,4−ビス(メルカプトメチルチオ)−6−メルカプト−2,5−ジチアヘキシルチオ]メルカプトメチルチオメチル−1,3−ジチエタン、2−[3,4,8,9−テトラキス(メルカプトメチルチオ)−11−メルカプト−2,5,7,10−テトラチアウンデシルチオ]メルカプトメチルチオメチル−1,3−ジチエタン、2−[3−ビス(メルカプトメチルチオ)メチル−5,6−ビス(メルカプトメチルチオ)−8−メルカプト−2,4,7−トリチアオクチル]メルカプトメチルチオメチル−1,3−ジチエタン、4,5−ビス{1−[2−(1,3−ジチエタニル)]−3−メルカプト−2−チアプロピルチオ}−1,3−ジチオラン、4−{1−[2−(1,3−ジチエタニル)]−3−メルカプト−2−チアプロピルチオ}−5−[1,2−ビス(メルカプトメチルチオ)−4−メルカプト−3−チアブチルチオ]−1,3−ジチオラン、2−{ビス[4−(5−メルカプトメチルチオ−1,3−ジチオラニル)チオ]メチル}−1,3−ジチエタン、4−[4−(5−メルカプトメチルチオ−1,3−ジチオラニル)チオ]−5−{1−[2−(1,3−ジチエタニル)]−3−メルカプト−2−チアプロピルチオ}−1,3−ジチオラン、さらにこれらのオリゴマー等のジチオアセタールもしくはジチオケタール骨格を有するポリチオール化合物及び、
ジエチルアミン、ジプロピルアミン、ジ−n−ブチルアミン、ジ−sec−ブチルアミン、ジイソブチルアミン、ジ−n−ペンチルアミン、ジ−3−ペンチルアミン、ジヘキシルアミン、ジオクチルアミン、ジ(2−エチルヘキシル)アミン、メチルヘキシルアミン、ジアリルアミン、N−メチルアリルアミン、ピペリジン、ピロリジン、ジフェニルアミン、N−メチルアミン、N−エチルアミン、ジベンジルアミン、N−メチルベンジルアミン、N−エチルベンジルアミン、ジシクロヘキシルアミン、N−メチルアニリン、N−エチルアニリン、ジナフチルアミン、1−メチルピペラジン、モルホリン等の単官能2級アミン化合物及び、
重合条件については、重合性組成物、触媒の種類と使用量、モールドの形状等によって大きく条件が異なるため限定されるものではないが、およそ、−50〜150℃の温度で1〜50時間かけて行われる。場合によっては、10〜150℃の温度範囲で保持または徐々に昇温して、1〜25時間で硬化させることが好ましい。
レンズの染色は公知の染色方法で実施可能であるが、通常、以下に示す方法で実施される。
屈折率(ne)、アッベ数(νe):プルフリッヒ屈折計を用い、20℃で測定した。
耐熱性:TMAペネートレーション法(50g荷重、ピン先0.5mmφ、昇温速度10℃/min)でのガラス転移温度(Tg)(℃)を耐熱性とした。
m−キシリレンジイソシアネート36.4g、4−メルカプトメチル−1,8−ジメルカプト−3,6−ジチアオクタン33.6g、ジ−n−ブチルスズジクロリド0.0105g(重合性組成物総重量に対して150ppm)、内部離型剤(STEPAN社、商品名、ゼレックUN)0.070g(重合性組成物総重量に対して1000ppm)、紫外線吸収剤(共同薬品株式会社、商品名バイオソーブ583)0.035g(重合性組成物総重量に対して500ppm)を20℃にて混合溶解し、均一溶液とした。この混合溶液を400Paにて1時間脱泡を行った後、1μmPTFE製フィルターでろ過を行い、ガラスモールドとテープからなるモールド型へ注入した。このモールド型を重合オーブンへ投入、25℃〜120℃まで21時間かけて徐々に昇温して重合した。重合終了後、オーブンからモールド型を取り出した。モールド型からの離型性は良好であった。得られた樹脂をさらに130℃で4時間アニール処理を行った。得られた樹脂は透明性があり、屈折率(ne)1.665、アッベ数(νe)32、耐熱性(Tg)89℃と、光学用透明樹脂として好適であった。しかし一般に毒性が高いとされている有機スズ化合物や、構成している組成により得られる樹脂や作業性に問題が生じる可能性のあるリン酸エステル系内部離型剤を使用している。また触媒、内部離型剤の2成分を添加する必要があり、作業が煩雑である。評価結果を[表1]に示した。
m−キシリレンジイソシアネート36.4g、4−メルカプトメチル−1,8−ジメルカプト−3,6−ジチアオクタン33.6g、ジ−n−ブチルスズジクロリド0.0105g(重合性組成物総重量に対して150ppm)、内部離型剤(STEPAN社、商品名、ゼレックUN)0.21g(重合性組成物総重量に対して3000ppm)、紫外線吸収剤(共同薬品株式会社、商品名バイオソーブ583)0.035g(重合性組成物総重量に対して500ppm)を20℃にて混合溶解し、均一溶液とした。この混合溶液を400Paにて1時間脱泡を行った後、1μmPTFE製フィルターでろ過を行い、ガラスモールドとテープからなるモールド型へ注入した。このモールド型を重合オーブンへ投入、25℃〜120℃まで21時間かけて徐々に昇温して重合した。重合終了後、オーブンからモールド型を取り出した。モールド型からの離型性は良好であった。得られた樹脂をさらに130℃で4時間アニール処理を行った。得られた樹脂は透明性があり、屈折率(ne)1.665、アッベ数(νe)32、耐熱性(Tg)89℃と、光学用透明樹脂として好適であった。しかしリン酸エステル系内部離型剤を増量することで、樹脂に白濁が見られ、光学用透明樹脂としては適さなかった。評価結果を[表1]に示した。
m−キシリレンジイソシアネート36.4g、4−メルカプトメチル−1,8−ジメルカプト−3,6−ジチアオクタン33.6g、トリブチルアミンジブチルリン酸塩0.007g(重合性組成物総重量に対して100ppm)、紫外線吸収剤(共同薬品株式会社、商品名バイオソーブ583)0.035g(重合性組成物総重量に対して500ppm)を20℃にて混合溶解し、均一溶液とした。この混合溶液を400Paにて1時間脱泡を行った後、1μmPTFE製フィルターでろ過を行い、ガラスモールドとテープからなるモールド型へ注入した。このモールド型を重合オーブンへ投入、25℃〜120℃まで21時間かけて徐々に昇温して重合した。重合終了後、オーブンからモールド型を取り出した。冷却後、モールド型からの離型を試みたが、離型はしなかった。評価結果を[表1]に示した。
Claims (11)
- 一般式(1)で表されるアミン化合物のR2、R3が炭素数1から8のアルキル基であることを特徴とする、請求項1記載の重合触媒。
- 一般式(1)で表されるアミン化合物がトリフェニルアミン、N,N−ジエチルヒドロキシルアミンまたはN,N−ジベンジルヒドロキシルアミンであることを特徴とする、請求項2記載の重合触媒。
- 一般式(2)で表されるリン酸のnが0〜2の整数を示し、R4が炭素数1〜10のアルキル基であることを特徴とする、請求項1から3のいずれかに記載の重合触媒。
- 一般式(2)で表されるリン酸がジブチルリン酸またはジオクチルリン酸であることを特徴とする、請求項4記載の重合触媒。
- 請求項1から5のいずれかに記載の重合触媒と、ポリイソシアネート化合物、ポリイソチオシアネート化合物、イソシアナト基を有するポリイソチオシアネート化合物より選ばれる一種または二種以上のイソシアネート類及び、ポリチオール化合物より選ばれる一種または二種以上のチオール類を含有するポリチオウレタン系光学材料用重合性組成物。
- イソシアネート類がm−キシリレンジイソシアネート、2,5−ビス(イソシアナトメチル)−ビシクロ−[2.2.1]−ヘプタン、2,6−ビス(イソシアナトメチル)−ビシクロ−[2.2.1]−ヘプタン、1,3−ビス(イソシアナトメチル)シクロヘキサン、1,4−ビス(イソシアナトメチル)シクロヘキサンおよびヘキサメチレンジイソシアネートからなる群から選択される一または二以上の化合物であり、チオール類が4−メルカプトメチル−1,8−ジメルカプト−3,6−ジチアオクタン、5,7−ジメルカプトメチル−1,11−ジメルカプト−3,6,9−トリチアウンデカン、4,7−ジメルカプトメチル−1,11−ジメルカプト−3,6,9−トリチアウンデカン、4,8−ジメルカプトメチル−1,11−ジメルカプト−3,6,9−トリチアウンデカン、ペンタエリスリトールテトラキス(3−メルカプトプロピオネート)、1,1,3,3−テトラキス(メルカプトメチルチオ)プロパン、1,1,2,2−テトラキス(メルカプトメチルチオ)エタン、4,6−ビス(メルカプトメチルチオ)−1,3−ジチアンおよび2−(2,2−ビス(メルカプトジメチルチオ)エチル)−1,3−ジチエタンからなる群から選択される一または二以上の化合物であることを特徴とする、請求項6記載の重合性組成物。
- 請求項6または7のいずれかに記載の重合性組成物を硬化させて得られるポリチオウレタン樹脂。
- 請求項8記載のポリチオウレタン樹脂からなる光学材料。
- 請求項9記載の光学材料からなるプラスチックレンズ。
- 請求項6または7のいずれかに記載の重合性組成物を注型重合することを特徴とする、ポリチオウレタン樹脂の製造方法。
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