JP4250116B2 - High refractive index episulfide compound - Google Patents
High refractive index episulfide compound Download PDFInfo
- Publication number
- JP4250116B2 JP4250116B2 JP2004145745A JP2004145745A JP4250116B2 JP 4250116 B2 JP4250116 B2 JP 4250116B2 JP 2004145745 A JP2004145745 A JP 2004145745A JP 2004145745 A JP2004145745 A JP 2004145745A JP 4250116 B2 JP4250116 B2 JP 4250116B2
- Authority
- JP
- Japan
- Prior art keywords
- bis
- mercaptomethylthio
- compound
- compounds
- group
- 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.)
- Expired - Lifetime
Links
- -1 episulfide compound Chemical class 0.000 title claims description 183
- 150000001875 compounds Chemical class 0.000 claims description 174
- 239000011347 resin Substances 0.000 claims description 101
- 229920005989 resin Polymers 0.000 claims description 101
- 239000000203 mixture Substances 0.000 claims description 60
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 32
- 239000007983 Tris buffer Substances 0.000 claims description 31
- 230000003287 optical effect Effects 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 229920006295 polythiol Polymers 0.000 claims description 21
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 18
- 150000002430 hydrocarbons Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- JRKRMWWBDZSDMT-UHFFFAOYSA-N 2-[(thiiran-2-ylmethyldisulfanyl)methyl]thiirane Chemical compound C1SC1CSSCC1CS1 JRKRMWWBDZSDMT-UHFFFAOYSA-N 0.000 claims description 10
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000001294 propane Substances 0.000 claims description 5
- BZIICVVDMWAHBB-UHFFFAOYSA-N CCCSSC[S+]1SC1 Chemical compound CCCSSC[S+]1SC1 BZIICVVDMWAHBB-UHFFFAOYSA-N 0.000 claims description 4
- CDISREWSQAIUEH-UHFFFAOYSA-N CCCSSC[S+]1[S+](C)S1 Chemical compound CCCSSC[S+]1[S+](C)S1 CDISREWSQAIUEH-UHFFFAOYSA-N 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 238000004140 cleaning Methods 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 239000000047 product Substances 0.000 description 35
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 22
- 238000006116 polymerization reaction Methods 0.000 description 22
- 239000003607 modifier Substances 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- 229910052717 sulfur Inorganic materials 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000000746 purification Methods 0.000 description 15
- 125000004434 sulfur atom Chemical group 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- 239000004593 Epoxy Chemical class 0.000 description 13
- 230000000704 physical effect Effects 0.000 description 13
- 125000003396 thiol group Chemical group [H]S* 0.000 description 13
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 12
- 125000001931 aliphatic group Chemical group 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 239000011593 sulfur Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 150000007524 organic acids Chemical class 0.000 description 9
- 235000005985 organic acids Nutrition 0.000 description 9
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 8
- WTSBJMAOQNCZBF-UHFFFAOYSA-N sulfanylmethylsulfanylmethanethiol Chemical compound SCSCS WTSBJMAOQNCZBF-UHFFFAOYSA-N 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 238000011282 treatment Methods 0.000 description 7
- XVNGTGZGWDPIRR-UHFFFAOYSA-N 1,2,2-tris(sulfanylmethylsulfanyl)ethylsulfanylmethanethiol Chemical group SCSC(SCS)C(SCS)SCS XVNGTGZGWDPIRR-UHFFFAOYSA-N 0.000 description 6
- YCLSOMLVSHPPFV-UHFFFAOYSA-N 3-(2-carboxyethyldisulfanyl)propanoic acid Chemical compound OC(=O)CCSSCCC(O)=O YCLSOMLVSHPPFV-UHFFFAOYSA-N 0.000 description 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000006082 mold release agent Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 239000002685 polymerization catalyst Substances 0.000 description 6
- 229920005862 polyol Polymers 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 5
- RHMKQRWOFRAOHS-UHFFFAOYSA-N (sulfanylmethyldisulfanyl)methanethiol Chemical compound SCSSCS RHMKQRWOFRAOHS-UHFFFAOYSA-N 0.000 description 4
- FDJWTMYNYYJBAT-UHFFFAOYSA-N 1,3,3-tris(sulfanylmethylsulfanyl)propylsulfanylmethanethiol Chemical group SCSC(SCS)CC(SCS)SCS FDJWTMYNYYJBAT-UHFFFAOYSA-N 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 4
- RLGIPUOXGLWSII-UHFFFAOYSA-N CCCOCCC1[S+](CCSCC)O1 Chemical compound CCCOCCC1[S+](CCSCC)O1 RLGIPUOXGLWSII-UHFFFAOYSA-N 0.000 description 4
- GSNNHDZPZSJRET-UHFFFAOYSA-N CCCOCCC1[S+](CCSCC)S1 Chemical compound CCCOCCC1[S+](CCSCC)S1 GSNNHDZPZSJRET-UHFFFAOYSA-N 0.000 description 4
- DKNMNCWIZCYVOL-UHFFFAOYSA-N CCCSCCC1[S+](CCSCC)O1 Chemical compound CCCSCCC1[S+](CCSCC)O1 DKNMNCWIZCYVOL-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- HBNYJWAFDZLWRS-UHFFFAOYSA-N ethyl isothiocyanate Chemical compound CCN=C=S HBNYJWAFDZLWRS-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- VUTVSWPVTJZPFU-UHFFFAOYSA-N propylsulfanylmethanethiol Chemical compound CCCSCS VUTVSWPVTJZPFU-UHFFFAOYSA-N 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 4
- 150000003457 sulfones Chemical class 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical group C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 description 3
- FWSRWHWKJYJTIO-UHFFFAOYSA-N 2-(propoxymethyl)thiirane Chemical compound CCCOCC1CS1 FWSRWHWKJYJTIO-UHFFFAOYSA-N 0.000 description 3
- WXOPUPSGODOWFX-UHFFFAOYSA-N 2-(propylsulfanylmethyl)-7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C(CC)SCC1=C2C(=CC=C1)O2 WXOPUPSGODOWFX-UHFFFAOYSA-N 0.000 description 3
- PVCDBHRSMZPIKR-UHFFFAOYSA-N 2-(propylsulfanylmethyl)oxirane Chemical compound CCCSCC1CO1 PVCDBHRSMZPIKR-UHFFFAOYSA-N 0.000 description 3
- IZXSANAAIPLUPZ-UHFFFAOYSA-N 2-(propylsulfanylmethyl)thiirane Chemical compound CCCSCC1CS1 IZXSANAAIPLUPZ-UHFFFAOYSA-N 0.000 description 3
- MSXKQPFWGYMZOL-UHFFFAOYSA-N 2-(thiiran-2-yldisulfanyl)thiirane Chemical compound C1SC1SSC1SC1 MSXKQPFWGYMZOL-UHFFFAOYSA-N 0.000 description 3
- URLQAIQRDQGWRZ-UHFFFAOYSA-N 2-(thiiran-2-ylsulfanyl)thiirane Chemical compound C1SC1SC1SC1 URLQAIQRDQGWRZ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- SDASEGSLVIVBPL-UHFFFAOYSA-N 2-[(propyldisulfanyl)methylsulfanylmethyl]thiirane Chemical compound C(CC)SSCSCC1CS1 SDASEGSLVIVBPL-UHFFFAOYSA-N 0.000 description 3
- MGRAAFCRDVYWNL-UHFFFAOYSA-N 2-propylsulfanyl-7-oxabicyclo[4.1.0]hepta-1(6),2,4-triene Chemical compound C(CC)SC1=C2C(=CC=C1)O2 MGRAAFCRDVYWNL-UHFFFAOYSA-N 0.000 description 3
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 3
- BBFKHUQFJBURJR-UHFFFAOYSA-N 5-(propoxymethyl)-7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound CCCOCC1=CC=CC2=C1O2 BBFKHUQFJBURJR-UHFFFAOYSA-N 0.000 description 3
- GRLCAHRUZPOHEH-UHFFFAOYSA-N 5-propoxy-7-oxabicyclo[4.1.0]hepta-1(6),2,4-triene Chemical compound CCCOC1=CC=CC2=C1O2 GRLCAHRUZPOHEH-UHFFFAOYSA-N 0.000 description 3
- LPRUSJNCTIKLBS-UHFFFAOYSA-N 5-propoxy-7-thiabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound CCCOC1=CC=CC2=C1S2 LPRUSJNCTIKLBS-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- BSTXZJILZFIDGI-UHFFFAOYSA-N CCCSCCC1[S+](CCSCCSCC)O1 Chemical compound CCCSCCC1[S+](CCSCCSCC)O1 BSTXZJILZFIDGI-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
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- QNSUVMHSJGIMDL-UHFFFAOYSA-N [6-(sulfanylmethylsulfanyl)-1,3-dithian-4-yl]sulfanylmethanethiol Chemical group SCSC1CC(SCS)SCS1 QNSUVMHSJGIMDL-UHFFFAOYSA-N 0.000 description 3
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- QWCNRESNZMCPJW-UHFFFAOYSA-N bis(sulfanylmethylsulfanyl)methylsulfanylmethanethiol Chemical compound SCSC(SCS)SCS QWCNRESNZMCPJW-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
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- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
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- 239000010452 phosphate Substances 0.000 description 3
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- 239000004033 plastic Substances 0.000 description 3
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- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- QMHKMLUVKWZPCH-UHFFFAOYSA-N sulfanylmethylsulfanyl-[3-[3-(sulfanylmethylsulfanyl)propylsulfanylmethylsulfanylmethylsulfanylmethylsulfanyl]propylsulfanyl]methanethiol Chemical compound SCSCCCSCSCSCSCCCSC(S)SCS QMHKMLUVKWZPCH-UHFFFAOYSA-N 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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Landscapes
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Description
本発明は、高い屈折率及び高い透明性が要求される光学材料等の樹脂分野に好適に使用されるエピスルフィド化合物及びその硬化した樹脂に関する。 The present invention relates to an episulfide compound suitably used in the field of resins such as optical materials that require high refractive index and high transparency, and a cured resin thereof.
プラスチックレンズは、無機レンズに比べ軽量で割れ難く、染色が可能なため近年、眼鏡レンズ、カメラレンズ等の光学素子に急速に普及してきている。
これらプラスチックレンズに要求され続けている性能は光学性能としては高屈折率、高アッベ数、物理的性質としては高耐熱性、低比重である。
In recent years, plastic lenses are rapidly spreading to optical elements such as spectacle lenses and camera lenses because they are lighter and harder to break than inorganic lenses and can be dyed.
The performance required for these plastic lenses is high refractive index and high Abbe number as optical performance, and high heat resistance and low specific gravity as physical properties.
現在、これらの要求性能をある程度満足した樹脂としては、樹脂中に硫黄原子を導入した、ポリチオウレタン樹脂が知られている。ポリチオウレタン樹脂は、高屈折率で耐衝撃性が良好である等、バランスの優れた樹脂である(例えば、特許文献1参照)。 Currently, polythiourethane resins in which sulfur atoms are introduced into the resin are known as resins that satisfy these required performances to some extent. The polythiourethane resin is a resin having an excellent balance such as a high refractive index and good impact resistance (see, for example, Patent Document 1).
しかしながら、更なる高屈折率化、高アッベ数化の要求がなされているものの、その反面、屈折率とアッベ数に関しては屈折率が上昇するほどアッベ数が低くなるという相反する物性であるため両方を同時に向上させることは非常に困難である。そこで、アッベ数の低下を抑えながら、高屈折率化を行う検討が盛んに行われている。 However, there is a demand for higher refractive index and higher Abbe number, but on the other hand, both the refractive index and Abbe number are contradictory properties that the Abbe number decreases as the refractive index increases. It is very difficult to improve at the same time. Therefore, studies for increasing the refractive index while suppressing the decrease in the Abbe number have been actively conducted.
これらの検討の中で最も代表的な提案は、エピスルフィド化合物を使用する方法である。(例えば、特許文献2、特許文献3参照)
また、更なる高屈折率化を図るために分子骨格内に硫黄を更に導入する方法が提案されている。(例えば、特許文献4参照)
In order to further increase the refractive index, a method of further introducing sulfur into the molecular skeleton has been proposed. (For example, see Patent Document 4)
特許文献4の方法によれば、比較的高いアッベ数を有しながら高い屈折率を実現できるものと思われる。しかしながら、特許文献4には、数多くの新規な化合物が例示されているものの、その製造方法については、公知化合物であるビス(β―エピチオプロピル)ジスルフィドについてのみ記載されており、当業者が実施できる程度に記載されておらず、本当に実現可能なものか不明である。また、エピジチオ基なる官能基を有する化合物が、エピスルフィド基を有する化合物と同等に重合可能なものであるかも不明である。その中で、硫黄を使用したエピスルフィド化合物の例では、得られた樹脂の屈折率は1.75程度であり、更なる高屈折率、高アッベ数を有する素材の提案に対する要求を満足していない。そこで、硫黄原子を使用して更なる高屈折率、高アッベ数を有する素材の開発が求められている。 According to the method of Patent Document 4, it is considered that a high refractive index can be realized while having a relatively high Abbe number. However, although Patent Document 4 exemplifies a number of novel compounds, the production method is described only for bis (β-epithiopropyl) disulfide, which is a known compound, and has been implemented by those skilled in the art. It is not described to the extent possible, and it is unclear whether it is really feasible. It is also unclear whether a compound having a functional group such as an epidithio group can be polymerized in the same manner as a compound having an episulfide group. Among them, in the case of an episulfide compound using sulfur, the obtained resin has a refractive index of about 1.75, which does not satisfy the requirement for a material having a higher refractive index and a higher Abbe number. . Therefore, development of materials having higher refractive index and higher Abbe number using sulfur atoms is required.
本発明者らは、上述の課題を解決するために鋭意検討した結果、式(1)で表される構造を有するエピスルフィド化合物の製造に成功した上に、該化合物を硬化させてなる樹脂の屈折率がより高い上に、アッベ数も高いといった優れた光学物性が得られることを見出し本発明に至った。 As a result of diligent studies to solve the above-mentioned problems, the present inventors have succeeded in producing an episulfide compound having a structure represented by the formula (1), and then refraction of a resin obtained by curing the compound. The inventors have found that excellent optical properties such as a higher rate and a higher Abbe number can be obtained, leading to the present invention.
即ち、本発明は、
[1] 下記式(1)で表される構造を有するエピスルフィド化合物に関する。
That is, the present invention
[1] The present invention relates to an episulfide compound having a structure represented by the following formula (1).
(式中、R1は、直鎖もしくは分岐の炭素数1〜4のチア化されていても良い炭化水素基、環状の炭素数3〜6のチア化されていても良い炭化水素基、1,4−ジチアン基、アリーレン基、または、アラルキレン基を表す。R1は置換されていても未置換でも良い。R2〜R9は水素原子、またはチア化されていても良い置換または未置換の直鎖もしくは分岐の炭素数1〜4の炭化水素基または環状の炭素数3〜6の炭化水素基を表す。a,b,cおよびdはそれぞれ0または1の整数を表し、2≦a+b+c+d≦4を満たす。)
また、以下[2]から[12]は、それぞれ本発明の好ましい実施態様の一つである。
(In the formula, R1 represents a linear or branched hydrocarbon group having 1 to 4 carbon atoms which may be thiated, a cyclic hydrocarbon group having 3 to 6 carbon atoms which may be thiated, 1, Represents a 4-dithian group, an arylene group, or an aralkylene group, R1 may be substituted or unsubstituted, and R2 to R9 may be a hydrogen atom, or a substituted or unsubstituted linear or Represents a branched hydrocarbon group having 1 to 4 carbon atoms or a cyclic hydrocarbon group having 3 to 6 carbon atoms, a, b, c and d each represents an integer of 0 or 1, satisfying 2 ≦ a + b + c + d ≦ 4 .)
[2] to [12] are each one of preferred embodiments of the present invention.
[2] 下記式(2)で表される構造を有する[1]に記載の化合物。 [2] The compound according to [1], which has a structure represented by the following formula (2).
(式中、R10は、直鎖もしくは分岐の炭素数1〜4のチア化されていても良い炭化水素基、環状の炭素数3〜6のチア化されていても良い炭化水素基、1,4−ジチアン基、アリーレン基、または、アラルキレン基を表す。R10は置換されていても未置換でも良い。。R11、R12は水素原子、またはチア化されていても良い置換または未置換の直鎖もしくは分岐の炭素数1〜4の炭化水素基または環状の炭素数3〜6の炭化水素基を表す。nは2〜4の整数を表す。) (Wherein R10 represents a linear or branched hydrocarbon group having 1 to 4 carbon atoms which may be thiated, a cyclic hydrocarbon group having 3 to 6 carbon atoms which may be thiated, 1, A 4-dithian group, an arylene group, or an aralkylene group, R10 may be substituted or unsubstituted, and R11 and R12 are hydrogen atoms, or a substituted or unsubstituted straight chain that may be thiated. Alternatively, it represents a branched hydrocarbon group having 1 to 4 carbon atoms or a cyclic hydrocarbon group having 3 to 6 carbon atoms, and n represents an integer of 2 to 4.
[3]上記エピスルフィド化合物がビス(2,3−エピチオプロピル)ジスルフィドとポリチオールとを原料として製造されたものである[1]乃至[2]のいずれか1項に記載の化合物。
[4]上記ポリチオールがメルカプトメチルチオ基を有する化合物である[3]に記載の化合物。
[5]上記エピスルフィド化合物が1,3−ビス(2,3−エピチオプロピルジチオ)−2−チアプロパン、1,4−ビス(2,3−エピチオプロピルジチオ)−2,3−ジチアブタン、1,1,1−トリス(2,3−エピチオプロピルジチオメチルチオ)メタン、1,1,2,2−テトラキス(2,3−エピチオプロピルジチオメチルチオ)エタン、1,1,3,3−テトラキス(2,3−エピチオプロピルジチオメチルチオ)プロパン、または、2−[1,1−ビス(2,3−エピチオプロピルジチオメチルチオ)メチル]−1,3−ジチエタンのいずれかである[1]乃至[4]に記載の化合物。
[6] [1]乃至[5]のいずれか1項に記載の化合物を含有する重合性組成物。
[7] [6]に記載の重合性組成物を硬化させて得られた樹脂。
[8] [7]に記載の樹脂を含有する光学材料。
[9] [6]に記載の重合性組成物を注型重合する工程を含む、樹脂の製造方法。
[10] ビス(2,3−エピチオプロピル)ジスルフィドとポリチオールとを原料として[1]乃至[5]のいずれか1項に記載の化合物を製造する方法。
[11] 上記ポリチオールがメルカプトメチルチオ基を有する化合物である[10]に記載の製造方法。
[12] 洗浄溶媒として、アルコール性水酸基を有する化合物を使用することを特徴とする[10]乃至[11]のいずれか1項に記載の製造方法。
[3] The compound according to any one of [1] to [2], wherein the episulfide compound is produced using bis (2,3-epithiopropyl) disulfide and polythiol as raw materials.
[4] The compound according to [3], wherein the polythiol is a compound having a mercaptomethylthio group.
[5] The episulfide compound is 1,3-bis (2,3-epithiopropyldithio) -2-thiapropane, 1,4-bis (2,3-epithiopropyldithio) -2,3-dithiabutane, , 1,1-tris (2,3-epithiopropyldithiomethylthio) methane, 1,1,2,2-tetrakis (2,3-epithiopropyldithiomethylthio) ethane, 1,1,3,3-tetrakis It is either (2,3-epithiopropyldithiomethylthio) propane or 2- [1,1-bis (2,3-epithiopropyldithiomethylthio) methyl] -1,3-dithietane [1] Thru | or a compound as described in [4].
[6] A polymerizable composition comprising the compound according to any one of [1] to [5].
[7] A resin obtained by curing the polymerizable composition according to [6].
[8] An optical material containing the resin according to [7].
[9] A method for producing a resin, comprising a step of cast polymerization of the polymerizable composition according to [6].
[10] A method for producing the compound according to any one of [1] to [5], using bis (2,3-epithiopropyl) disulfide and polythiol as raw materials.
[11] The production method according to [10], wherein the polythiol is a compound having a mercaptomethylthio group.
[12] The production method according to any one of [10] to [11], wherein a compound having an alcoholic hydroxyl group is used as the cleaning solvent.
本発明により、高屈折率分野における新規な光学材料の原料として有用な化合物が得られ、また、重合硬化して得られる樹脂の光学物性が非常に高く、特にメガネレンズの分野で高屈折率化、薄型化に貢献する。 According to the present invention, a compound useful as a raw material for a novel optical material in the field of high refractive index can be obtained, and the optical physical properties of the resin obtained by polymerization and curing are very high, particularly in the field of eyeglass lenses. Contributes to thinning.
以下、本発明を詳細に説明するが、まず、本発明のエピスルフィド化合物について記載する。 Hereinafter, the present invention will be described in detail. First, the episulfide compound of the present invention will be described.
本発明のエピスルフィド化合物は、下記一般式(1)で表されるものである。
下記式(1)で表される構造を有するエピスルフィド化合物。
The episulfide compound of the present invention is represented by the following general formula (1).
An episulfide compound having a structure represented by the following formula (1).
(式中、R1は、直鎖もしくは分岐の炭素数1〜4のチア化されていても良い炭化水素基、環状の炭素数3〜6のチア化されていても良い炭化水素基、1,4−ジチアン基、アリーレン基、または、アラルキレン基を表す。R1は置換されていても未置換でも良い。R2〜R9は水素原子、またはチア化されていても良い置換または未置換の直鎖もしくは分岐の炭素数1〜4の炭化水素基または環状の炭素数3〜6の炭化水素基を表す。a,b,cおよびdはそれぞれ0または1の整数を表し、2≦a+b+c+d≦4を満たす。) (Wherein R1 represents a linear or branched hydrocarbon group having 1 to 4 carbon atoms which may be thiated, a cyclic hydrocarbon group having 3 to 6 carbon atoms which may be thiated, 1, Represents a 4-dithian group, an arylene group, or an aralkylene group, R1 may be substituted or unsubstituted, and R2 to R9 may be a hydrogen atom, a substituted or unsubstituted linear or Represents a branched hydrocarbon group having 1 to 4 carbon atoms or a cyclic hydrocarbon group having 3 to 6 carbon atoms, a, b, c and d each represents an integer of 0 or 1, satisfying 2 ≦ a + b + c + d ≦ 4 .)
ここで、R1で表される置換または未置換の炭素数1〜4の炭化水素基には、直鎖、分岐または環状のアルキル基、直鎖、分岐又は環状のアルケニル基、アリール基およびアラルキル基が含まれる。R1は、好ましくは、メチレン基、エチレン基、またはプロピレン基である。 Here, the substituted or unsubstituted C1-C4 hydrocarbon group represented by R1 includes a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkenyl group, an aryl group, and an aralkyl group. Is included. R1 is preferably a methylene group, an ethylene group, or a propylene group.
R2〜R9で表される水素原子または置換または未置換の炭素数1〜4の炭化水素基には、直鎖、分岐又は環状のアルキレン基、直鎖、分岐又は環状のアルケニレン基、アリーレン基、アラルキレン基が含まれる。R2〜R9は好ましくは水素原子であり、炭化水素基の場合チア化されているとより好ましい。 The hydrogen atom represented by R2 to R9 or the substituted or unsubstituted hydrocarbon group having 1 to 4 carbon atoms includes a linear, branched or cyclic alkylene group, a linear, branched or cyclic alkenylene group, an arylene group, Aralkylene groups are included. R2 to R9 are preferably hydrogen atoms, and in the case of hydrocarbon groups, it is more preferable that they are thialated.
式(1)で表される構造を有する化合物の好ましいものの具体例としては、1,3−ビス(2,3−エピチオプロピルジチオ)−2−チアプロパン、1,4−ビス(2,3−エピチオプロピルジチオ)−2,3−ジチアブタン、1,1,1−トリス(2,3−エピチオプロピルジチオ)メタン、1,1,1−トリス(2,3−エピチオプロピルジチオメチルチオ)メタン、1,1,2,2−テトラキス(2,3−エピチオプロピルジチオ)エタン、1,1,2,2−テトラキス(2,3−エピチオプロピルジチオメチルチオ)エタン、1,1,3,3−テトラキス(2,3−エピチオプロピルジチオ)プロパン、1,1,3,3−テトラキス(2,3−エピチオプロピルジチオメチルチオ)プロパン、2−[1,1−ビス(2,3−エピチオプロピルジチオ)メチル]−1,3−ジチエタン、2−[1,1−ビス(2,3−エピチオプロピルジチオメチルチオ)メチル]−1,3−ジチエタン等を挙げることができるが、これらの例示化合物のみに限定されるものではない。 Specific examples of preferable compounds having the structure represented by the formula (1) include 1,3-bis (2,3-epithiopropyldithio) -2-thiapropane, 1,4-bis (2,3- Epithiopropyldithio) -2,3-dithiabutane, 1,1,1-tris (2,3-epithiopropyldithio) methane, 1,1,1-tris (2,3-epithiopropyldithiomethylthio) methane 1,1,2,2-tetrakis (2,3-epithiopropyldithio) ethane, 1,1,2,2-tetrakis (2,3-epithiopropyldithiomethylthio) ethane, 1,1,3, 3-tetrakis (2,3-epithiopropyldithio) propane, 1,1,3,3-tetrakis (2,3-epithiopropyldithiomethylthio) propane, 2- [1,1-bis (2,3- Epithio (Lopyldithio) methyl] -1,3-dithietane, 2- [1,1-bis (2,3-epithiopropyldithiomethylthio) methyl] -1,3-dithietane, and the like. It is not limited to only.
本発明の式(1)で表される構造を有する化合物を製造する方法としては、ジスルフィド結合を有する化合物とメルカプト基を有する化合物との間で起こるジスルフィド交換反応を利用する方法が挙げられる。このとき、無機塩基や有機塩基、無機酸や有機酸等を触媒として共存させるとよりきれいに目的物を製造できる場合がある。 Examples of the method for producing the compound having the structure represented by the formula (1) of the present invention include a method utilizing a disulfide exchange reaction that occurs between a compound having a disulfide bond and a compound having a mercapto group. At this time, in some cases, the target product can be more neatly produced by using an inorganic base, an organic base, an inorganic acid, an organic acid, or the like as a catalyst.
この反応を行う際に使用する反応溶媒としては、無溶媒または、極性溶媒単独もしくは、原料のジスルフィド化合物とメルカプト化合物が溶解可能であるものであればいずれでも良いが、極性溶媒と非極性溶媒との混合溶媒を用いることも可能である。ここでの極性溶媒とは具体的には、水、メタノール、エタノール等のアルコール類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、酢酸メチル、酢酸エチル、酢酸プロピル、酢酸ブチル等のエステル類、ジエチルエーテル、テトラヒドロフラン等のエーテル類、ジメチルホルムアミド、ジメチルイミダゾリジノン、ジメチルスルフォキシド等の非プロトン性極性溶媒類等が挙げられるが、例示化合物に限定されるわけではない。非極性溶媒の具体例としては、ベンゼン、トルエン、キシレン等の芳香族炭化水素類及びそのハロゲン置換体類、ヘキサン、シクロヘキサン等の脂肪族炭化水素類、ジクロロメタン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類等が挙げられるが、例示化合物に限定されるわけではない。 The reaction solvent used in carrying out this reaction may be any solvent, or a polar solvent alone, or any solvent that can dissolve the starting disulfide compound and mercapto compound. It is also possible to use a mixed solvent of Specific examples of the polar solvent here include alcohols such as water, methanol and ethanol, ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, esters such as methyl acetate, ethyl acetate, propyl acetate and butyl acetate, Examples include ethers such as diethyl ether and tetrahydrofuran, and aprotic polar solvents such as dimethylformamide, dimethylimidazolidinone, and dimethyl sulfoxide, but are not limited to the exemplified compounds. Specific examples of nonpolar solvents include aromatic hydrocarbons such as benzene, toluene and xylene and their halogen substitution products, aliphatic hydrocarbons such as hexane and cyclohexane, and halogenation such as dichloromethane, chloroform and carbon tetrachloride. Although hydrocarbons etc. are mentioned, it is not necessarily limited to an exemplary compound.
ここで使用を可能とする触媒としては、例えば、無機塩基としては、アルカリ金属又はアルカリ土類金属の水酸化物、アルカリ金属又はアルカリ土類金属の炭酸塩、アルカリ金属又はアルカリ土類金属の重炭酸塩、アンモニア等が挙げられ、有機塩基としては3級アミン、2級アミン、1級アミン、金属アルコキシド等が挙げられる。無機酸としては、塩酸、硫酸、硝酸、燐酸等が挙げられ、有機酸としては、蟻酸、酢酸、プロピオン酸、フタル酸等が挙げられる。これらの中で好ましいものとしては、3級アミン、2級アミン、1級アミンが挙げられるが、比較的塩基性の弱いものの方が好ましい。 Examples of the catalyst that can be used here include, as inorganic bases, alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal carbonates, alkali metal or alkaline earth metal heavy metals. Examples of the organic base include tertiary amines, secondary amines, primary amines, and metal alkoxides. Examples of inorganic acids include hydrochloric acid, sulfuric acid, nitric acid, and phosphoric acid, and examples of organic acids include formic acid, acetic acid, propionic acid, and phthalic acid. Among these, tertiary amines, secondary amines, and primary amines are preferred, but those having relatively weak basicity are preferred.
本発明においては、ジスルフィド結合を有する化合物としてビス(2,3−エピチオプロピル)ジスルフィドを使用すると好ましい。また、本発明においてメルカプト基を有する化合物としては、2官能以上のポリチオールを意味するが、該ポリチオールは、メルカプトメチルチオ基を有する化合物であると好ましい。 In the present invention, it is preferable to use bis (2,3-epithiopropyl) disulfide as the compound having a disulfide bond. In the present invention, the compound having a mercapto group means a polythiol having two or more functional groups, and the polythiol is preferably a compound having a mercaptomethylthio group.
本発明におけるポリチオールの好ましいものの具体例としては、ビス(メルカプトメチル)スルフィド、ビス(メルカプトメチル)ジスルフィド、ビス(メルカプトメチルチオ)メタン、1,2−ビス(メルカプトメチルチオ)エタン、1,2,3−トリス(メルカプトメチルチオ)プロパン、テトラキス(メルカプトメチルチオメチル)メタン等のメルカプト基以外に硫黄原子を含有する脂肪族ポリチオール化合物、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、2,2−ビス(メルカプトメチル)−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、4,6−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−ジチアニルチオ}−3,3−ビス(メルカプトメチルチオ)プロパン、1,3−ビス{4−(6−メルカプトメチルチオ)−1,3−ジチアニルチオ}−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−{4−(6−メルカプトメチルチオ)−1,3−ジチアニルチオ}−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)−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−ジチアニルチオ}−1,3−ジチアン、4−{4−(6−メルカプトメチルチオ)−1,3−ジチアニルチオ}−6−{4−(6−メルカプトメチルチオ)−1,3−ジチアニルチオ}−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化合物、 Specific examples of preferred polythiols in the present invention include bis (mercaptomethyl) sulfide, bis (mercaptomethyl) disulfide, bis (mercaptomethylthio) methane, 1,2-bis (mercaptomethylthio) ethane, 1,2,3- Aliphatic polythiol compounds containing sulfur atoms in addition to mercapto groups such as tris (mercaptomethylthio) propane and tetrakis (mercaptomethylthiomethyl) methane, 1,1,3,3-tetrakis (mercaptomethylthio) propane, 1,1,2 , 2-tetrakis (mercaptomethylthio) ethane, 4,6-bis (mercaptomethylthio) -1,3-dithiacyclohexane, 1,1,5,5-tetrakis (mercaptomethylthio) -3-thiapentane, 1,1, 6,6-tetrakis (Merka Tomethylthio) -3,4-dithiahexane, 2,2-bis (mercaptomethylthio) ethanethiol, 2- (4,5-dimercapto-2-thiapentyl) -1,3-dithiacyclopentane, 2,2-bis ( Mercaptomethyl) -1,3-dithiacyclopentane, 2,5-bis (4,4-bis (mercaptomethylthio) -2-thiabutyl) -1,4-dithiane, 2,2-bis (mercaptomethylthio)- 1,3-propanedithiol, 3-mercaptomethylthio-1,7-dimercapto-2,6-dithiaheptane, 3,6-bis (mercaptomethylthio) -1,9-dimercapto-2,5,8-trithianonane, 4, 6-bis (mercaptomethylthio) -1,9-dimercapto-2,5,8-trithianonane, 3-mercaptomethylthio-1 6-dimercapto-2,5-dithiahexane, 2- (2,2-bis (mercaptomethylthio) ethyl) -1,3-dithietane, 1,1,9,9-tetrakis (mercaptomethylthio) -5- (3 3-bis (mercaptomethylthio) -1-thiapropyl) 3,7-dithianonane, tris (2,2-bis (mercaptomethylthio) ethyl) methane, tris (4,4-bis (mercaptomethylthio) -2-thiabutyl) methane Tetrakis (2,2-bis (mercaptomethylthio) ethyl) methane, tetrakis (4,4-bis (mercaptomethylthio) -2-thiabutyl) methane, 3,5,9,11-tetrakis (mercaptomethylthio) -1, 13-dimercapto-2,6,8,12-tetrathiatridecane, 3,5,9,11,15,17- Hexakis (mercaptomethylthio) -1,19-dimercapto-2,6,8,12,14,18-hexathiononadecane, 9- (2,2-bis (mercaptomethylthio) ethyl) -3,5,13, 15-tetrakis (mercaptomethylthio) -1,17-dimercapto-2,6,8,10,12,16-hexathiaheptadecane, 3,4,8,9-tetrakis (mercaptomethylthio) -1,11-dimercapto 2,5,7,10-tetrathiaundecane, 3,4,8,9,13,14-hexakis (mercaptomethylthio) -1,16-dimercapto-2,5,7,10,12,15-hexa Thiahexadecane, 8- {bis (mercaptomethylthio) methyl} -3,4,12,13-tetrakis (mercaptomethylthio) -1,15- Mercapto-2,5,7,9,11,14-hexathiapentadecane, 4,6-bis {3,5-bis (mercaptomethylthio) -7-mercapto-2,6-dithiaheptylthio} -1, 3-dithiane, 4- {3,5-bis (mercaptomethylthio) -7-mercapto-2,6-dithiaheptylthio} -6-mercaptomethylthio-1,3-dithiane, 1,1-bis {4- (6-mercaptomethylthio) -1,3-dithianylthio} -3,3-bis (mercaptomethylthio) propane, 1,3-bis {4- (6-mercaptomethylthio) -1,3-dithianylthio} -1,3 -Bis (mercaptomethylthio) propane, 1- {4- (6-mercaptomethylthio) -1,3-dithianylthio} -3- {2,2-bis (mercaptomethylthio) L} -7,9-bis (mercaptomethylthio) -2,4,6,10-tetrathiaundecane, 1- {4- (6-mercaptomethylthio) -1,3-dithianylthio} -3- {2- ( 1,3-dithietanyl)} methyl-7,9-bis (mercaptomethylthio) -2,4,6,10-tetrathiaundecane, 1,5-bis {4- (6-mercaptomethylthio) -1,3- Dithianylthio} -3- {2- (1,3-dithietanyl)} methyl-2,4-dithiapentane, 4,6-bis [3- {2- (1,3-dithietanyl)} methyl-5-mercapto-2 , 4-dithiapentylthio] -1,3-dithiane, 4,6-bis {4- (6-mercaptomethylthio) -1,3-dithianylthio} -1,3-dithiane, 4- {4- (6 -Mercaptomethylthio) -1,3-dithianylthio} -6- {4- (6-mercaptomethylthio) -1,3-dithianylthio} -1,3-dithiane, 3- {2- (1,3-dithietanyl)} methyl-7, 9-bis (mercaptomethylthio) -1,11-dimercapto-2,4,6,10-tetrathiaundecane, 9- {2- (1,3-dithietanyl)} methyl-3,5,13,15-tetrakis (Mercaptomethylthio) -1,17-dimercapto-2,6,8,10,12,16-hexathiaheptadecane, 3- {2- (1,3-dithietanyl)} methyl-7,9,13,15 -Tetrakis (mercaptomethylthio) -1,17-dimercapto-2,4,6,10,12,16-hexathiaheptadecane, 3,7-bis {2- (1,3-dithietanyl)} methyl- , 9-dimercapto-2,4,6,8-tetrathianonane, 4- {3,4,8,9-tetrakis (mercaptomethylthio) -11-mercapto-2,5,7,10-tetrathiaundecyl } -5-mercaptomethylthio-1,3-dithiolane, 4,5-bis {3,4-bis (mercaptomethylthio) -6-mercapto-2,5-dithiahexylthio} -1,3-dithiolane, 4, -{3,4-bis (mercaptomethylthio) -6-mercapto-2,5-dithiahexylthio} -5-mercaptomethylthio-1,3-dithiolane, 4- {3-bis (mercaptomethylthio) methyl-5 , 6-Bis (mercaptomethylthio) -8-mercapto-2,4,7-trithiaoctyl} -5-mercaptomethylthio-1,3-dithiolane, 2- [bis {3 4-bis (mercaptomethylthio) -6-mercapto-2,5-dithiahexylthio} methyl] -1,3-dithietane, 2- {3,4-bis (mercaptomethylthio) -6-mercapto-2,5 -Dithiahexylthio} mercaptomethylthiomethyl-1,3-dithietane, 2- {3,4,8,9-tetrakis (mercaptomethylthio) -11-mercapto-2,5,7,10-tetrathiaundecylthio } Mercaptomethylthiomethyl-1,3-dithietane, 2- {3-bis (mercaptomethylthio) methyl-5,6-bis (mercaptomethylthio) -8-mercapto-2,4,7-trithiaoctyl} mercaptomethylthiomethyl -1,3-dithietane, 4,5-bis [1- {2- (1,3-dithietanyl)}-3-mercapto-2-thia Propylthio] -1,3-dithiolane, 4- [1- {2- (1,3-dithietanyl)}-3-mercapto-2-thiapropylthio] -5- {1,2-bis (mercaptomethylthio)- 4-mercapto-3-thiabutylthio} -1,3-dithiolane, 2- [bis {4- (5-mercaptomethylthio-1,3-dithiolanyl) thio}] methyl-1,3-dithietane, 4- {4- (5-mercaptomethylthio-1,3-dithiolanyl) thio} -5- [1- {2- (1,3-dithietanyl)}-3-mercapto-2-thiapropylthio] -1,3-dithiolane, etc. A compound having a dithioacetal or dithioketal skeleton,
トリス(メルカプトメチルチオ)メタン、トリス(メルカプトエチルチオ)メタン、1,1,5,5−テトラキス(メルカプトメチルチオ)−2,4−ジチアペンタン、ビス[4,4−ビス(メルカプトメチルチオ)−1,3−ジチアブチル](メルカプトメチルチオ)メタン、トリス[4,4−ビス(メルカプトメチルチオ)−1,3−ジチアブチル]メタン、2,4,6−トリス(メルカプトメチルチオ)−1,3,5−トリチアシクロヘキサン、2,4−ビス(メルカプトメチルチオ)−1,3,5−トリチアシクロヘキサン、1,1,3,3−テトラキス(メルカプトメチルチオ)−2−チアプロパン、ビス(メルカプトメチル)メチルチオ−1,3,5−トリチアシクロヘキサン、トリス[(4−メルカプトメチル−2,5−ジチアシクロヘキシル−1−イル)メチルチオ]メタン、2,4−ビス(メルカプトメチルチオ)−1,3−ジチアシクロペンタン、2−メルカプトエチルチオ−4−メルカプトメチル−1,3−ジチアシクロペンタン、2−(2,3−ジメルカプトプロピルチオ)−1,3−ジチアシクロペンタン、4−メルカプトメチル−2−(2,3−ジメルカプトプロピルチオ)−1,3−ジチアシクロペンタン、4−メルカプトメチル−2−(1,3−ジメルカプト−2−プロピルチオ)−1,3−ジチアシクロペンタン、トリス[2,2−ビス(メルカプトメチルチオ)−1−チアエチル]メタン、トリス[3,3−ビス(メルカプトメチルチオ)−2−チアプロピル]メタン、トリス[4,4−ビス(メルカプトメチルチオ)−3−チアブチル]メタン、2,4,6−トリス[3,3−ビス(メルカプトメチルチオ)−2−チアプロピル]−1,3,5−トリチアシクロヘキサン、テトラキス[3,3−ビス(メルカプトメチルチオ)−2−チアプロピル]メタン等のオルトトリチオ蟻酸エステル骨格を有する化合物、 Tris (mercaptomethylthio) methane, tris (mercaptoethylthio) methane, 1,1,5,5-tetrakis (mercaptomethylthio) -2,4-dithiapentane, bis [4,4-bis (mercaptomethylthio) -1,3 -Dithiabutyl] (mercaptomethylthio) methane, tris [4,4-bis (mercaptomethylthio) -1,3-dithiabutyl] methane, 2,4,6-tris (mercaptomethylthio) -1,3,5-trithiacyclohexane 2,4-bis (mercaptomethylthio) -1,3,5-trithiacyclohexane, 1,1,3,3-tetrakis (mercaptomethylthio) -2-thiapropane, bis (mercaptomethyl) methylthio-1,3 5-trithiacyclohexane, tris [(4-mercaptomethyl-2,5-dithi Cyclohexyl-1-yl) methylthio] methane, 2,4-bis (mercaptomethylthio) -1,3-dithiacyclopentane, 2-mercaptoethylthio-4-mercaptomethyl-1,3-dithiacyclopentane, 2 -(2,3-dimercaptopropylthio) -1,3-dithiacyclopentane, 4-mercaptomethyl-2- (2,3-dimercaptopropylthio) -1,3-dithiacyclopentane, 4- Mercaptomethyl-2- (1,3-dimercapto-2-propylthio) -1,3-dithiacyclopentane, tris [2,2-bis (mercaptomethylthio) -1-thiaethyl] methane, tris [3,3- Bis (mercaptomethylthio) -2-thiapropyl] methane, tris [4,4-bis (mercaptomethylthio) -3-thiabutyl] me 2,4,6-tris [3,3-bis (mercaptomethylthio) -2-thiapropyl] -1,3,5-trithiacyclohexane, tetrakis [3,3-bis (mercaptomethylthio) -2-thiapropyl ] A compound having an ortho trithioformate skeleton such as methane,
3,3’−ジ(メルカプトメチルチオ)−1,5−ジメルカプト−2,4−ジチアペンタン、2,2’−ジ(メルカプトメチルチオ)−1,3−ジチアシクロペンタン、2,7−ジ(メルカプトメチル)−1,4,5,9−テトラチアスピロ[4,4]ノナン、3,9−ジメルカプト−1,5,7,11−テトラチアスピロ[5,5]ウンデカン等のオルトテトラチオ炭酸エステル骨格を有する化合物等が挙げられるが、これらの例示化合物のみに限定されるものではない。これら例示化合物は、単独でも2種類以上混合して使用しても良い。 3,3′-di (mercaptomethylthio) -1,5-dimercapto-2,4-dithiapentane, 2,2′-di (mercaptomethylthio) -1,3-dithiacyclopentane, 2,7-di (mercapto) Orthotetrathiocarbonate such as methyl) -1,4,5,9-tetrathiaspiro [4,4] nonane, 3,9-dimercapto-1,5,7,11-tetrathiaspiro [5,5] undecane Examples include compounds having an ester skeleton, but are not limited to these exemplary compounds. These exemplary compounds may be used alone or in combination of two or more.
本発明の場合、ジスルフィド交換反応は、例えば、以下の式(3)ように進行する。 In the case of the present invention, the disulfide exchange reaction proceeds as, for example, the following formula (3).
ここで、Rは、直鎖もしくは分岐の炭素数1〜4のチア化されていても良い炭化水素基、環状の炭素数3〜6のチア化されていても良い炭化水素基、1,4−ジチアン基、アリーレン基、または、アラルキレン基を表す。Rは置換されていても未置換でも良い。 Here, R is a linear or branched hydrocarbon group having 1 to 4 carbon atoms which may be thiated, a cyclic hydrocarbon group having 3 to 6 carbon atoms which may be thiated, 1, 4 -Represents a dithiane group, an arylene group, or an aralkylene group. R may be substituted or unsubstituted.
本反応の場合、原料のジスルフィド結合とメルカプト基の反応は理論的には等モル反応であるが、目的物の生成率を向上させるためには、原料のビス(2,3−エピチオプロピル)ジスルフィドのモル数を、メルカプトメチルチオ基を有する化合物のメルカプト基のモル数よりも当量以上使用すると好ましい。2倍モル以上使用するとより好ましい。3倍モル以上使用すれば更に好ましい。経済性や精製負荷を考慮すれば、10倍モル以下が好ましい。 In the case of this reaction, the reaction between the disulfide bond of the raw material and the mercapto group is theoretically an equimolar reaction. The number of moles of disulfide is preferably used in an amount equal to or greater than the number of moles of mercapto groups in the compound having a mercaptomethylthio group. It is more preferable to use 2 times mole or more. It is more preferable to use 3 times mole or more. Considering economic efficiency and purification load, 10 times mole or less is preferable.
反応温度については、使用する触媒の性能により一概に限定できないが、高すぎる場合、エピスルフィド基の重合が進行する為好ましくなく、低すぎる場合、交換反応が進行しない為好ましくない。よって、0℃〜50℃の範囲であれば好ましく、10℃〜40℃の範囲であればより好ましい。 About reaction temperature, it cannot unconditionally limit by the performance of the catalyst to be used, but when too high, it is not preferable because polymerization of episulfide group proceeds, and when too low, it is not preferable because exchange reaction does not proceed. Therefore, it is preferably in the range of 0 ° C to 50 ° C, more preferably in the range of 10 ° C to 40 ° C.
交換反応終了後、過剰のジスルフィド結合を有する化合物と副生する1,2−エピチオ−3−メルカプトプロパンは、最終的に得られる化合物や重合硬化して得られる樹脂の物性を考慮すれば、除去した方が好ましい。 After completion of the exchange reaction, 1,2-epithio-3-mercaptopropane produced as a by-product with the compound having an excess disulfide bond is removed in consideration of the properties of the compound finally obtained and the resin obtained by polymerization and curing. Is preferable.
該化合物を除去する方法については、以下のように重合性組成物の取り扱いに関する記載の中で述べる。 The method for removing the compound will be described in the description regarding the handling of the polymerizable composition as follows.
次に、本発明の式(1)で表される構造を有するエピスルフィド化合物を含有する重合性組成物について記載する。本発明の重合性組成物の構成要件は、式(1)で表される構造を有するエピスルフィド化合物を含有することであるが、該重合性組成物を硬化してなる樹脂の屈折率、アッベ数等の光学物性の調整や、色相、耐光性や耐候性、耐熱性、耐衝撃性、硬度、比重、線膨張係数、重合収縮率、吸水性、吸湿性、耐薬品性、粘弾性等の諸物性を調整、透過率や透明性の調整、重合性組成物の粘度、その他保存や輸送方法の取扱い性を調整するためなど、樹脂の改良や取り扱い性を改良する目的で、精製や洗浄、保温、保冷、濾過、減圧処理などの有機化合物を合成する際に一般的に用いられる手法、操作を施したり、また、公知の化合物等を安定剤や樹脂改質剤として加えたりすることは良好な樹脂を得る目的で好ましい場合がある。長期の保存安定性や、重合安定性、熱安定性などの安定性向上のために加えられるものとしては、重合遅延剤や重合禁止剤、脱酸素剤、酸化防止剤などの化合物が挙げられるが、記載のものに限定されるわけではない。 Next, it describes about the polymeric composition containing the episulfide compound which has a structure represented by Formula (1) of this invention. A constituent requirement of the polymerizable composition of the present invention is to contain an episulfide compound having a structure represented by the formula (1), but the refractive index and Abbe number of a resin obtained by curing the polymerizable composition. Adjustment of optical properties such as hue, light resistance and weather resistance, heat resistance, impact resistance, hardness, specific gravity, linear expansion coefficient, polymerization shrinkage, water absorption, moisture absorption, chemical resistance, viscoelasticity, etc. For the purpose of improving the resin and handling properties, such as adjusting physical properties, adjusting the transmittance and transparency, adjusting the viscosity of the polymerizable composition, and other handling and transport methods, purification, washing, and heat retention. It is good to apply techniques and operations generally used when synthesizing organic compounds such as cold preservation, filtration, and decompression treatment, and to add known compounds as stabilizers and resin modifiers. It may be preferable for the purpose of obtaining a resin. Examples of compounds that can be added to improve stability such as long-term storage stability, polymerization stability, and thermal stability include compounds such as polymerization retarders, polymerization inhibitors, oxygen scavengers, and antioxidants. However, the present invention is not limited to those described.
重合性組成物を精製するのは、硬化して得られる樹脂の透明性を改良したり、色相を改良する為や純度を上げるために用いられる手法であるが、本発明の式(1)で表される構造を有するエピスルフィド化合物を含有する重合性組成物を精製する方法は、公知の方法、例えば、蒸留、再結晶、カラムクロマト法(シリカゲル法や活性炭法、イオン交換樹脂法など)、抽出などであればいかなる手法をいかなるタイミングで行っても良く、一般に精製して得られる組成物を硬化させて得られる樹脂の透明性や色相が改良されていれば良い。本発明においては、過剰量の原料や副生物が組成物中に存在するが、上記の方法などで精製したほうが好ましい。 Purifying the polymerizable composition is a technique used to improve the transparency of the resin obtained by curing, improve the hue, or increase the purity. In the formula (1) of the present invention, A method for purifying a polymerizable composition containing an episulfide compound having a structure represented can be a known method such as distillation, recrystallization, column chromatography (silica gel method, activated carbon method, ion exchange resin method, etc.), extraction, and the like. Any method may be used at any timing, as long as the transparency and hue of a resin obtained by curing a composition generally obtained by purification are generally improved. In the present invention, an excessive amount of raw materials and by-products are present in the composition, but it is preferable to purify by the above-described method.
重合性組成物を洗浄する方法は、硬化して得られる樹脂の透明性を改良したり、色相を改良するのに用いられる手法であるが、重合性組成物を合成して取り出す際または合成後の取り出した後などのタイミングで極性及び/または非極性溶媒で洗浄し、樹脂の物性を低下させる原因物質や樹脂の透明性を阻害する物質、例えば、重合性組成物を合成する際に使用される又は、副生する化合物などを取り除くまたは減量する方法が挙げられる。用いる溶媒は、洗浄される重合性組成物そのものや重合性組成物を含有する溶液の極性等により一概に限定は出来ないが、取り除きたい成分を溶解可能で、かつ、洗浄される重合性組成物そのものや重合性組成物を含有する溶液と相溶しにくいものが好ましく、一種類のみならず、2種類以上を混合して使用しても良い。本発明においては、アルコール性水酸基を有する化合物が好ましく、メタノール、エタノール、プロパノール、イソプロパノール、n−ブタノール、sec−ブタノール、tert−ブタノール等がより好ましい。ここで取り除く成分は目的や用途に応じて異なるが、なるべく少なくしておくことが好ましく、5000ppmとすると好ましい。1000ppm以下とすればより好ましい。100ppm以下とすれば更に好ましい。 The method of washing the polymerizable composition is a technique used to improve the transparency of the resin obtained by curing or to improve the hue, but when the polymerizable composition is synthesized and taken out or after the synthesis It is used to synthesize a causative substance that lowers the physical properties of the resin or a substance that impairs the transparency of the resin, such as a polymerizable composition, by washing with a polar and / or non-polar solvent at a timing such as after removal Or a method of removing or reducing the amount of by-produced compounds. The solvent to be used cannot be generally limited by the polymerizable composition itself to be washed or the polarity of the solution containing the polymerizable composition, but the component to be removed can be dissolved and the polymerizable composition to be washed is used. Those which are hardly compatible with itself or a solution containing a polymerizable composition are preferable, and not only one type but also two or more types may be mixed and used. In the present invention, a compound having an alcoholic hydroxyl group is preferable, and methanol, ethanol, propanol, isopropanol, n-butanol, sec-butanol, tert-butanol and the like are more preferable. The components removed here vary depending on the purpose and application, but are preferably as small as possible, preferably 5000 ppm. More preferably, it is 1000 ppm or less. More preferably, it is 100 ppm or less.
重合性組成物を保温・保冷・濾過する方法は、硬化して得られる樹脂の透明性を改良したり、色相を改良するのに用いられる手法であるが、重合性組成物を合成して取り出す際または合成後の取り出した後などのタイミングで行うのが一般的である。保温とは、例えば、重合性組成物が保管中に結晶化し、ハンドリングが悪くなった場合、重合性組成物及び重合性組成物を硬化させてなる樹脂の性能が低下しない範囲で加熱溶解する方法が挙げられる。加熱する温度範囲や加熱溶解する方法は、取り扱われる重合性組成物を構成する化合物の構造により一概に限定できないが、通常凝固点+50℃以内で行われ、+20℃以内でれば好ましい。その際、攪拌可能な装置で機械的に攪拌したり、組成物に不活性なガスでバブリングすることで内液を動かし溶解する方法などが挙げられる。保冷とは重合性組成物の保存安定性を高める目的で通常行われるが、融点が高く結晶化後の取り扱いに問題がある場合は、保管温度を考慮する必要がある。保冷温度は取り扱われる重合性組成物を構成する化合物の構造、保存安定性により一概に限定できないが、式(1)で表される構造を有する化合物を含有する重合性組成物の場合、20℃以下の低温で保管すると良く、10℃以下が好ましい。しかしながら、融点が高い場合には、通常凝固点より高い温度で行うと使用時の取り扱い性が良い場合がある。加熱溶解が容易に可能な場合は、凝固点以下で保存しても何ら問題ない。 The method of keeping, cooling, and filtering the polymerizable composition is a technique used to improve the transparency of the resin obtained by curing or to improve the hue. Generally, it is performed at a timing such as at the time of extraction or after removal after synthesis. For example, in the case where the polymerizable composition is crystallized during storage and handling becomes poor, the polymerizable composition and a method in which the polymerizable composition and the resin obtained by curing the polymerizable composition are heated and dissolved within a range that does not deteriorate. Is mentioned. The temperature range to be heated and the method of heating and dissolving cannot be generally limited depending on the structure of the compound constituting the polymerizable composition to be handled, but it is usually performed within the freezing point + 50 ° C., and preferably within + 20 ° C. In that case, the method etc. which move and melt | dissolve an internal solution by mechanically stirring with the apparatus which can be stirred, or bubbling with an inert gas to a composition, etc. are mentioned. The cold insulation is usually performed for the purpose of enhancing the storage stability of the polymerizable composition, but when the melting point is high and there is a problem in handling after crystallization, it is necessary to consider the storage temperature. Although the cold temperature cannot be generally limited by the structure and storage stability of the compound constituting the polymerizable composition to be handled, it is 20 ° C. in the case of the polymerizable composition containing the compound having the structure represented by the formula (1). It is good to store at the following low temperature, preferably 10 ° C. or less. However, when the melting point is high, handling at the time of use may be good if it is carried out at a temperature higher than the normal freezing point. If dissolution by heating is possible easily, there is no problem even if it is stored below the freezing point.
光学用途に用いる重合性組成物の場合、その非常に高い透明性を要求されることから、通常重合性組成物を孔径の小さいフィルターで濾過を行うとよい。ここで用いるフィルターの孔径は通常0.05〜10μmで行われるが、操作性や性能を考慮すれば0.05〜5μmが好ましい。0.1〜5μmであればより好ましい。本願発明のエピスルフィド化合物を含有する重合性組成物も例外なく濾過すると良い結果が得られる場合が多い。濾過する温度については、凝固点付近の低温で行うと更に好ましい結果が得られる場合があるが、濾過中に凝固が進行するような場合は、濾過作業に支障を来さない温度で行うと良い場合がある。 In the case of a polymerizable composition used for optical applications, since its very high transparency is required, it is usually preferable to filter the polymerizable composition with a filter having a small pore size. The pore size of the filter used here is usually 0.05 to 10 μm, but 0.05 to 5 μm is preferable in consideration of operability and performance. If it is 0.1-5 micrometers, it is more preferable. When the polymerizable composition containing the episulfide compound of the present invention is filtered without exception, good results are often obtained. As for the temperature at which filtration is performed, a more preferable result may be obtained if it is performed at a low temperature near the freezing point. However, if solidification proceeds during filtration, it may be performed at a temperature that does not hinder the filtration operation. There is.
減圧処理は、一般的に重合性組成物を硬化させてなる樹脂の性能を低下させる溶媒や溶存ガス、臭気を取り除くのに行われる手法である。溶存溶媒は一般に得られる樹脂の屈折率低下や耐熱性低下を招くため、可能な限り取り除く必要がある。溶存溶媒の許容値は取り扱われる重合性組成物を構成する化合物の構造、溶存する溶媒の構造により一概に限定できないが、通常1%以下とするのが好ましい。5000ppm以下とすればより好ましい。溶存ガスは重合阻害となるものや、得られる樹脂に気泡が混入する弊害があるため取り除く方が好ましい。特に、水蒸気などの水分を意味するガスについては、とりわけ乾燥ガスでバブリングするなどして除去した方が好ましい。溶存量については、重合性組成物を構成する化合物の構造、溶存するガスの物性及び構造、種類により一概に限定できないが、例えば、水分の場合、1000ppm以下とすると得られる樹脂の透明性の観点で好ましい。 The reduced pressure treatment is a technique generally used to remove a solvent, dissolved gas, and odor that lower the performance of a resin obtained by curing a polymerizable composition. The dissolved solvent generally causes a decrease in the refractive index and heat resistance of the resin obtained, so it is necessary to remove it as much as possible. The allowable value of the dissolved solvent cannot be generally limited by the structure of the compound constituting the polymerizable composition to be handled and the structure of the dissolved solvent, but it is usually preferably 1% or less. If it is 5000 ppm or less, it is more preferable. It is preferable to remove the dissolved gas because it has a detrimental effect on the polymerization of the gas or the bubbles in the resulting resin. In particular, it is preferable to remove a gas such as water vapor by bubbling with a dry gas. The dissolved amount cannot be unconditionally limited depending on the structure of the compound constituting the polymerizable composition, the physical property and structure of the dissolved gas, and the type. Is preferable.
続いて、樹脂改質剤について記載する。樹脂改質剤としては、公知のチエタン化合物、ジチエタン化合物、トリチエタン化合物、チオラン化合物、ジチオラン化合物、トリチオラン化合物、ジチアン化合物、トリチアン化合物、エピスルフィド化合物類及びエポキシ化合物類、アミン化合物類、チオール化合物類、フェノール化合物類を含むヒドロキシ化合物類、イソ(チオ)シアナート化合物類、メルカプト有機酸類、有機酸類及び無水物類、アミノ酸及びメルカプトアミン類、(メタ)アクリレート類等を含むオレフィン類、硫黄原子またはセレン原子を有する環状有機化合物や無機化合物類が挙げられる。これら樹脂改質剤の内、エポキシ化合物やイソ(チオ)シアナート化合物、(メタ)アクリレート類を含むオレフィン類は、得られる樹脂の脆さの克服や耐衝撃性の向上に対してより好ましい。アミン化合物類、チオール化合物類、フェノール化合物類は得られる樹脂の色相改善に対して好ましい。その中でも、SH基を1個以上有する化合物はより好ましい。SH基を2個以上有し、スルフィド結合を有する化合物であればさらに好ましい。硫黄原子またはセレン原子を有する環状有機化合物や無機化合物類は、樹脂の屈折率向上に対して好ましく、特に、硫黄を使用すると操作が平易な上に屈折率向上の効果が大きいことから特に好ましい。硫黄の添加量としては、重合性組成物全体に対して3〜30重量%使用すると良い。得られる樹脂の耐熱性や脆さを考慮すれば、5〜25重量%使用すると好ましい。 Subsequently, the resin modifier will be described. As resin modifiers, known thietane compounds, dithietane compounds, trithiethane compounds, thiolane compounds, dithiolane compounds, trithiolane compounds, dithiane compounds, trithiane compounds, episulfide compounds and epoxy compounds, amine compounds, thiol compounds, phenols Hydroxy compounds including compounds, iso (thio) cyanate compounds, mercapto organic acids, organic acids and anhydrides, amino acids and mercaptoamines, olefins including (meth) acrylates, sulfur atoms or selenium atoms Examples thereof include cyclic organic compounds and inorganic compounds. Among these resin modifiers, olefins including epoxy compounds, iso (thio) cyanate compounds, and (meth) acrylates are more preferable for overcoming the brittleness of the resulting resin and improving impact resistance. Amine compounds, thiol compounds, and phenol compounds are preferred for improving the hue of the resulting resin. Among these, a compound having one or more SH groups is more preferable. A compound having two or more SH groups and having a sulfide bond is more preferable. Cyclic organic compounds and inorganic compounds having a sulfur atom or a selenium atom are preferable for improving the refractive index of the resin, and particularly when sulfur is used, the operation is simple and the effect of increasing the refractive index is particularly preferable. As addition amount of sulfur, it is good to use 3 to 30 weight% with respect to the whole polymerizable composition. Considering the heat resistance and brittleness of the resulting resin, it is preferable to use 5 to 25% by weight.
ここで、樹脂改質剤として使用を可能とする化合物について具体的に記載する。 Here, a compound that can be used as a resin modifier will be specifically described.
本発明の樹脂改質剤としてのエピスルフィド化合物の具体例としては、ビス(1,2−エピチオエチル)スルフィド、ビス(1,2−エピチオエチル)ジスルフィド、ビス(エピチオエチルチオ)メタン、ビス(エピチオエチルチオ)ベンゼン、ビス[4−(エピチオエチルチオ)フェニル]スルフィド、ビス[4−(エピチオエチルチオ)フェニル]メタン等のエピチオエチル化合物、ビス(2,3−エピチオプロピル)スルフィド、ビス(2,3−エピチオプロピル)ジスルフィド、ビス(2,3−エピチオプロピルチオ)メタン、1,2−ビス(2,3−エピチオプロピルチオ)エタン、1,2−ビス(2,3−エピチオプロピルチオ)プロパン、1,3−ビス(2,3−エピチオプロピルチオ)プロパン、1,3−ビス(2,3−エピチオプロピルチオ)−2−メチルプロパン、1,4−ビス(2,3−エピチオプロピルチオ)ブタン、1,4−ビス(2,3−エピチオプロピルチオ)−2−メチルブタン、1,3−ビス(2,3−エピチオプロピルチオ)ブタン、1,5−ビス(2,3−エピチオプロピルチオ)ペンタン、1,5−ビス(2,3−エピチオプロピルチオ)−2−メチルペンタン、1,5−ビス(2,3−エピチオプロピルチオ)−3−チアペンタン、1,6−ビス(2,3−エピチオプロピルチオ)ヘキサン、1,6−ビス(2,3−エピチオプロピルチオ)−2−メチルヘキサン、3,8−ビス(2,3−エピチオプロピルチオ)−3,6−ジチアオクタン、1,2,3−トリス(2,3−エピチオプロピルチオ)プロパン、2,2−ビス(2,3−エピチオプロピルチオ)−1,3−ビス(2,3−エピチオプロピルチオメチル)プロパン、2,2−ビス(2,3−エピチオプロピルチオメチル)−1−(2,3−エピチオプロピルチオ)ブタン、1,5−ビス(2,3−エピチオプロピルチオ)−2−(2,3−エピチオプロピルチオメチル)−3−チアペンタン、1,5−ビス(2,3−エピチオプロピルチオ)−2,4−ビス(2,3−エピチオプロピルチオメチル)−3−チアペンタン、1−(2,3−エピチオプロピルチオ)−2,2−ビス(2,3−エピチオプロピルチオメチル)−4−チアヘキサン、1,5,6−トリス(2,3−エピチオプロピルチオ)−4−(2,3−エピチオプロピルチオメチル)−3−チアヘキサン、1,8−ビス(2,3−エピチオプロピルチオ)−4−(2,3−エピチオプロピルチオメチル)−3,6−ジチアオクタン、1,8−ビス(2,3−エピチオプロピルチオ)−4,5−ビス(2,3−エピチオプロピルチオメチル)−3,6−ジチアオクタン、1,8−ビス(2,3−エピチオプロピルチオ)−4,4−ビス(2,3−エピチオプロピルチオメチル)−3,6−ジチアオクタン、1,8−ビス(2,3−エピチオプロピルチオ)−2,5−ビス(2,3−エピチオプロピルチオメチル)−3,6−ジチアオクタン、1,8−ビス(2,3−エピチオプロピルチオ)−2,4,5−トリス(2,3−エピチオプロピルチオメチル)−3,6−ジチアオクタン、1,1,1−トリス[[2−(2,3−エピチオプロピルチオ)エチル]チオメチル]−2−(2,3−エピチオプロピルチオ)エタン、1,1,2,2−テトラキス[[2−(2,3−エピチオプロピルチオ)エチル]チオメチル]エタン、1,11−ビス(2,3−エピチオプロピルチオ)−4,8−ビス(2,3−エピチオプロピルチオメチル)−3,6,9−トリチアウンデカン、1,11−ビス(2,3−エピチオプロピルチオ)−4,7−ビス(2,3−エピチオプロピルチオメチル)−3,6,9−トリチアウンデカン、1,11−ビス(2,3−エピチオプロピルチオ)−5,7−ビス(2,3−エピチオプロピルチオメチル)−3,6,9−トリチアウンデカン等の鎖状脂肪族の2,3−エピチオプロピルチオ化合物、及び、 Specific examples of the episulfide compound as the resin modifier of the present invention include bis (1,2-epithioethyl) sulfide, bis (1,2-epithioethyl) disulfide, bis (epithioethylthio) methane, bis (epithio). Epithioethyl compounds such as ethylthio) benzene, bis [4- (epithioethylthio) phenyl] sulfide, bis [4- (epithioethylthio) phenyl] methane, bis (2,3-epithiopropyl) sulfide, bis (2,3-epithiopropyl) disulfide, bis (2,3-epithiopropylthio) methane, 1,2-bis (2,3-epithiopropylthio) ethane, 1,2-bis (2,3 -Epithiopropylthio) propane, 1,3-bis (2,3-epithiopropylthio) propane, 1,3-bis (2,3-e Thiopropylthio) -2-methylpropane, 1,4-bis (2,3-epithiopropylthio) butane, 1,4-bis (2,3-epithiopropylthio) -2-methylbutane, 1,3 -Bis (2,3-epithiopropylthio) butane, 1,5-bis (2,3-epithiopropylthio) pentane, 1,5-bis (2,3-epithiopropylthio) -2-methyl Pentane, 1,5-bis (2,3-epithiopropylthio) -3-thiapentane, 1,6-bis (2,3-epithiopropylthio) hexane, 1,6-bis (2,3-epi Thiopropylthio) -2-methylhexane, 3,8-bis (2,3-epithiopropylthio) -3,6-dithiaoctane, 1,2,3-tris (2,3-epithiopropylthio) propane , 2,2-bis (2,3- Pithiopropylthio) -1,3-bis (2,3-epithiopropylthiomethyl) propane, 2,2-bis (2,3-epithiopropylthiomethyl) -1- (2,3-epithio Propylthio) butane, 1,5-bis (2,3-epithiopropylthio) -2- (2,3-epithiopropylthiomethyl) -3-thiapentane, 1,5-bis (2,3-epi Thiopropylthio) -2,4-bis (2,3-epithiopropylthiomethyl) -3-thiapentane, 1- (2,3-epithiopropylthio) -2,2-bis (2,3-epi Thiopropylthiomethyl) -4-thiahexane, 1,5,6-tris (2,3-epithiopropylthio) -4- (2,3-epithiopropylthiomethyl) -3-thiahexane, 1,8- Bis (2,3-epithiopropylthio ) -4- (2,3-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (2,3-epithiopropylthio) -4,5-bis (2,3-epithio) Propylthiomethyl) -3,6-dithiaoctane, 1,8-bis (2,3-epithiopropylthio) -4,4-bis (2,3-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (2,3-epithiopropylthio) -2,5-bis (2,3-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (2,3-epi Thiopropylthio) -2,4,5-tris (2,3-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,1,1-tris [[2- (2,3-epithiopropylthio ) Ethyl] thiomethyl] -2- (2,3-epithio) Propylthio) ethane, 1,1,2,2-tetrakis [[2- (2,3-epithiopropylthio) ethyl] thiomethyl] ethane, 1,11-bis (2,3-epithiopropylthio) -4 , 8-bis (2,3-epithiopropylthiomethyl) -3,6,9-trithiaundecane, 1,11-bis (2,3-epithiopropylthio) -4,7-bis (2, 3-epithiopropylthiomethyl) -3,6,9-trithiaundecane, 1,11-bis (2,3-epithiopropylthio) -5,7-bis (2,3-epithiopropylthiomethyl) ) -3,6,9-trithiaundecane and other chain aliphatic 2,3-epithiopropylthio compounds, and
1,3−ビス(2,3−エピチオプロピルチオ)シクロヘキサン、1,4−ビス(2,3−エピチオプロピルチオ)シクロヘキサン、1,3−ビス(2,3−エピチオプロピルチオメチル)シクロヘキサン、1,4−ビス(2,3−エピチオプロピルチオメチル)シクロヘキサン、2,5−ビス(2,3−エピチオプロピルチオメチル)−1,4−ジチアン、2,5−ビス[[2−(2,3−エピチオプロピルチオ)エチル]チオメチル]−1,4−ジチアン、2,5−ビス(2,3−エピチオプロピルチオメチル)−2,5−ジメチル−1,4−ジチアン等の環状脂肪族の2,3−エピチオプロピルチオ化合物、及び、 1,3-bis (2,3-epithiopropylthio) cyclohexane, 1,4-bis (2,3-epithiopropylthio) cyclohexane, 1,3-bis (2,3-epithiopropylthiomethyl) Cyclohexane, 1,4-bis (2,3-epithiopropylthiomethyl) cyclohexane, 2,5-bis (2,3-epithiopropylthiomethyl) -1,4-dithiane, 2,5-bis [[ 2- (2,3-epithiopropylthio) ethyl] thiomethyl] -1,4-dithiane, 2,5-bis (2,3-epithiopropylthiomethyl) -2,5-dimethyl-1,4- Cycloaliphatic 2,3-epithiopropylthio compounds such as dithiane, and
1,2−ビス(2,3−エピチオプロピルチオ)ベンゼン、1,3−ビス(2,3−エピチオプロピルチオ)ベンゼン、1,4−ビス(2,3−エピチオプロピルチオ)ベンゼン、1,2−ビス(2,3−エピチオプロピルチオメチル)ベンゼン、1,3−ビス(2,3−エピチオプロピルチオメチル)ベンゼン、1,4−ビス(2,3−エピチオプロピルチオメチル)ベンゼン、ビス[4−(2,3−エピチオプロピルチオ)フェニル]メタン、2,2−ビス[4−(2,3−エピチオプロピルチオ)フェニル]プロパン、ビス[4−(2,3−エピチオプロピルチオ)フェニル]スルフィド、ビス[4−(2,3−エピチオプロピルチオ)フェニル]スルフォン、4,4’−ビス(2,3−エピチオプロピルチオ)ビフェニル等の芳香族2,3−エピチオプロピルチオ化合物、 1,2-bis (2,3-epithiopropylthio) benzene, 1,3-bis (2,3-epithiopropylthio) benzene, 1,4-bis (2,3-epithiopropylthio) benzene 1,2-bis (2,3-epithiopropylthiomethyl) benzene, 1,3-bis (2,3-epithiopropylthiomethyl) benzene, 1,4-bis (2,3-epithiopropyl) Thiomethyl) benzene, bis [4- (2,3-epithiopropylthio) phenyl] methane, 2,2-bis [4- (2,3-epithiopropylthio) phenyl] propane, bis [4- ( 2,3-epithiopropylthio) phenyl] sulfide, bis [4- (2,3-epithiopropylthio) phenyl] sulfone, 4,4′-bis (2,3-epithiopropylthio) biphenyl, etc. Aromatic , 3-epithiopropylthio compound,
エチレンスルフィド、プロピレンスルフィド、3−メルカプトプロピレンスルフィド、4−メルカプトブテンスルフィド、エピチオクロルヒドリン等の単官能エピスルフィド化合物、 Monofunctional episulfide compounds such as ethylene sulfide, propylene sulfide, 3-mercaptopropylene sulfide, 4-mercaptobutene sulfide, epithiochlorohydrin,
ビス(2,3−エピチオプロピル)エーテル、ビス(2,3−エピチオプロピルオキシ)メタン、1,2−ビス(2,3−エピチオプロピルオキシ)エタン、1,2−ビス(2,3−エピチオプロピルオキシ)プロパン、1,3−ビス(2,3−エピチオプロピルオキシ)プロパン、1,3−ビス(2,3−エピチオプロピルオキシ)−2−メチルプロパン、1,4−ビス(2,3−エピチオプロピルオキシ)ブタン、1,4−ビス(2,3−エピチオプロピルオキシ)−2−メチルブタン、1,3−ビス(2,3−エピチオプロピルオキシ)ブタン、1,5−ビス(2,3−エピチオプロピルオキシ)ペンタン、1,5−ビス(2,3−エピチオプロピルオキシ)−2−メチルペンタン、1,5−ビス(2,3−エピチオプロピルオキシ)−3−チアペンタン、1,6−ビス(2,3−エピチオプロピルオキシ)ヘキサン、1,6−ビス(2,3−エピチオプロピルオキシ)−2−メチルヘキサン、3,8−ビス(2,3−エピチオプロピルオキシ)−3,6−ジチアオクタン、1,2,3−トリス(2,3−エピチオプロピルオキシ)プロパン、2,2−ビス(2,3−エピチオプロピルオキシ)−1,3−ビス(2,3−エピチオプロピルオキシメチル)プロパン、2,2−ビス(2,3−エピチオプロピルオキシメチル)−1−(2,3−エピチオプロピルオキシ)ブタン、1,5−ビス(2,3−エピチオプロピルオキシ)−2−(2,3−エピチオプロピルオキシメチル)−3−チアペンタン、1,5−ビス(2,3−エピチオプロピルオキシ)−2,4−ビス(2,3−エピチオプロピルオキシメチル)−3−チアペンタン、1−(2,3−エピチオプロピルオキシ)−2,2−ビス(2,3−エピチオプロピルオキシメチル)−4−チアヘキサン、1,5,6−トリス(2,3−エピチオプロピルオキシ)−4−(2,3−エピチオプロピルオキシメチル)−3−チアヘキサン、1,8−ビス(2,3−エピチオプロピルオキシ)−4−(2,3−エピチオプロピルオキシメチル)−3,6−ジチアオクタン、1,8−ビス(2,3−エピチオプロピルオキシ)−4,5−ビス(2,3−エピチオプロピルオキシメチル)−3,6−ジチアオクタン、1,8−ビス(2,3−エピチオプロピルオキシ)−4,4−ビス(2,3−エピチオプロピルオキシメチル)−3,6−ジチアオクタン、1,8−ビス(2,3−エピチオプロピルオキシ)−2,5−ビス(2,3−エピチオプロピルオキシメチル)−3,6−ジチアオクタン、1,8−ビス(2,3−エピチオプロピルオキシ)−2,4,5−トリス(2,3−エピチオプロピルオキシメチル)−3,6−ジチアオクタン、1,1,1−トリス[[2−(2,3−エピチオプロピルオキシ)エチル]チオメチル]−2−(2,3−エピチオプロピルオキシ)エタン、1,1,2,2−テトラキス[[2−(2,3−エピチオプロピルオキシ)エチル]チオメチル]エタン、1,11−ビス(2,3−エピチオプロピルオキシ)−4,8−ビス(2,3−エピチオプロピルオキシメチル)−3,6,9−トリチアウンデカン、1,11−ビス(2,3−エピチオプロピルオキシ)−4,7−ビス(2,3−エピチオプロピルオキシメチル)−3,6,9−トリチアウンデカン、1,11−ビス(2,3−エピチオプロピルオキシ)−5,7−ビス(2,3−エピチオプロピルオキシメチル)−3,6,9−トリチアウンデカン等の鎖状脂肪族の2,3−エピチオプロピルオキシ化合物、及び、 Bis (2,3-epithiopropyl) ether, bis (2,3-epithiopropyloxy) methane, 1,2-bis (2,3-epithiopropyloxy) ethane, 1,2-bis (2, 3-epithiopropyloxy) propane, 1,3-bis (2,3-epithiopropyloxy) propane, 1,3-bis (2,3-epithiopropyloxy) -2-methylpropane, 1,4 -Bis (2,3-epithiopropyloxy) butane, 1,4-bis (2,3-epithiopropyloxy) -2-methylbutane, 1,3-bis (2,3-epithiopropyloxy) butane 1,5-bis (2,3-epithiopropyloxy) pentane, 1,5-bis (2,3-epithiopropyloxy) -2-methylpentane, 1,5-bis (2,3-epi Thiopropyloxy) 3-thiapentane, 1,6-bis (2,3-epithiopropyloxy) hexane, 1,6-bis (2,3-epithiopropyloxy) -2-methylhexane, 3,8-bis (2, 3-epithiopropyloxy) -3,6-dithiaoctane, 1,2,3-tris (2,3-epithiopropyloxy) propane, 2,2-bis (2,3-epithiopropyloxy) -1 , 3-bis (2,3-epithiopropyloxymethyl) propane, 2,2-bis (2,3-epithiopropyloxymethyl) -1- (2,3-epithiopropyloxy) butane, 1, 5-bis (2,3-epithiopropyloxy) -2- (2,3-epithiopropyloxymethyl) -3-thiapentane, 1,5-bis (2,3-epithiopropyloxy) -2, 4-bis (2, -Epithiopropyloxymethyl) -3-thiapentane, 1- (2,3-epithiopropyloxy) -2,2-bis (2,3-epithiopropyloxymethyl) -4-thiahexane, 1,5, 6-Tris (2,3-epithiopropyloxy) -4- (2,3-epithiopropyloxymethyl) -3-thiahexane, 1,8-bis (2,3-epithiopropyloxy) -4- (2,3-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,8-bis (2,3-epithiopropyloxy) -4,5-bis (2,3-epithiopropyloxymethyl) 3,6-dithiaoctane, 1,8-bis (2,3-epithiopropyloxy) -4,4-bis (2,3-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,8- Screw( 2,3-epithiopropyloxy) -2,5-bis (2,3-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,8-bis (2,3-epithiopropyloxy) -2 , 4,5-tris (2,3-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,1,1-tris [[2- (2,3-epithiopropyloxy) ethyl] thiomethyl]- 2- (2,3-epithiopropyloxy) ethane, 1,1,2,2-tetrakis [[2- (2,3-epithiopropyloxy) ethyl] thiomethyl] ethane, 1,11-bis (2 , 3-epithiopropyloxy) -4,8-bis (2,3-epithiopropyloxymethyl) -3,6,9-trithiaundecane, 1,11-bis (2,3-epithiopropyloxy) ) -4,7-Bis 2,3-epithiopropyloxymethyl) -3,6,9-trithiaundecane, 1,11-bis (2,3-epithiopropyloxy) -5,7-bis (2,3-epithiopropyl) Chain aliphatic 2,3-epithiopropyloxy compounds such as (oxymethyl) -3,6,9-trithiaundecane, and
1,3−ビス(2,3−エピチオプロピルオキシ)シクロヘキサン、1,4−ビス(2,3−エピチオプロピルオキシ)シクロヘキサン、1,3−ビス(2,3−エピチオプロピルオキシメチル)シクロヘキサン、1,4−ビス(2,3−エピチオプロピルオキシメチル)シクロヘキサン、2,5−ビス(2,3−エピチオプロピルオキシメチル)−1,4−ジチアン、2,5−ビス[[2−(2,3−エピチオプロピルオキシ)エチル]チオメチル]−1,4−ジチアン、2,5−ビス(2,3−エピチオプロピルオキシメチル)−2,5−ジメチル−1,4−ジチアン等の環状脂肪族の2,3−エピチオプロピルオキシ化合物、及び、 1,3-bis (2,3-epithiopropyloxy) cyclohexane, 1,4-bis (2,3-epithiopropyloxy) cyclohexane, 1,3-bis (2,3-epithiopropyloxymethyl) Cyclohexane, 1,4-bis (2,3-epithiopropyloxymethyl) cyclohexane, 2,5-bis (2,3-epithiopropyloxymethyl) -1,4-dithiane, 2,5-bis [[ 2- (2,3-epithiopropyloxy) ethyl] thiomethyl] -1,4-dithiane, 2,5-bis (2,3-epithiopropyloxymethyl) -2,5-dimethyl-1,4- Cycloaliphatic 2,3-epithiopropyloxy compounds such as dithiane, and
1,2−ビス(2,3−エピチオプロピルオキシ)ベンゼン、1,3−ビス(2,3−エピチオプロピルオキシ)ベンゼン、1,4−ビス(2,3−エピチオプロピルオキシ)ベンゼン、1,2−ビス(2,3−エピチオプロピルオキシメチル)ベンゼン、1,3−ビス(2,3−エピチオプロピルオキシメチル)ベンゼン、1,4−ビス(2,3−エピチオプロピルオキシメチル)ベンゼン、ビス[4−(2,3−エピチオプロピルオキシ)フェニル]メタン、2,2−ビス[4−(2,3−エピチオプロピルオキシ)フェニル]プロパン、ビス[4−(2,3−エピチオプロピルオキシ)フェニル]スルフィド、ビス[4−(2,3−エピチオプロピルオキシ)フェニル]スルフォン、4,4’−ビス(2,3−エピチオプロピルオキシ)ビフェニル等の芳香族2,3−エピチオプロピルオキシ化合物等を挙げることができるが、例示化合物のみに限定されるものではない。 1,2-bis (2,3-epithiopropyloxy) benzene, 1,3-bis (2,3-epithiopropyloxy) benzene, 1,4-bis (2,3-epithiopropyloxy) benzene 1,2-bis (2,3-epithiopropyloxymethyl) benzene, 1,3-bis (2,3-epithiopropyloxymethyl) benzene, 1,4-bis (2,3-epithiopropyl) Oxymethyl) benzene, bis [4- (2,3-epithiopropyloxy) phenyl] methane, 2,2-bis [4- (2,3-epithiopropyloxy) phenyl] propane, bis [4- ( 2,3-epithiopropyloxy) phenyl] sulfide, bis [4- (2,3-epithiopropyloxy) phenyl] sulfone, 4,4′-bis (2,3-epithiopropyloxy) It can be exemplified aromatic 2,3-epithiopropyl oxy compounds such biphenyl, but is not limited only to the exemplified compounds.
例示化合物のうち好ましい化合物としては、ビス(1,2−エピチオエチル)スルフィド、ビス(1,2−エピチオエチル)ジスルフィド、ビス(2,3−エピチオプロピル)スルフィド、ビス(2,3−エピチオプロピルチオ)メタン及びビス(2,3−エピチオプロピル)ジスルフィドであり、より好ましい化合物としてはビス(1,2−エピチオエチル)スルフィド、ビス(1,2−エピチオエチル)ジスルフィド、及びビス(2,3−エピチオプロピル)ジスルフィドである。 Among the exemplified compounds, preferred compounds are bis (1,2-epithioethyl) sulfide, bis (1,2-epithioethyl) disulfide, bis (2,3-epithiopropyl) sulfide, and bis (2,3-epithiopropyl). Thio) methane and bis (2,3-epithiopropyl) disulfide, and more preferred compounds are bis (1,2-epithioethyl) sulfide, bis (1,2-epithioethyl) disulfide, and bis (2,3- Epithiopropyl) disulfide.
本発明の樹脂改質剤としてのエポキシ化合物の具体例としては、ビスフェノールAグリシジルエーテル等の多価フェノール化合物とエピハロヒドリン化合物との縮合反応により得られるフェノール系エポキシ化合物、水添ビスフェノールAグリシジルエーテル等の多価アルコール化合物とエピハロヒドリン化合物との縮合により得られるアルコール系エポキシ化合物、3,4−エポキシシクロヘキシルメチル−3’,4’−エポキシシクロヘキサンカルボキシレートや1,2−ヘキサヒドロフタル酸ジグリシジルエステル等の多価有機酸化合物とエピハロヒドリン化合物との縮合により得られるグリシジルエステル系エポキシ化合物、二級アミン化合物とエピハロヒドリン化合物との縮合により得られるアミン系エポキシ化合物等その他、ビニルシクロヘキセンジエポキシド等脂肪族多価エポキシ化合物等を挙げることができる。 Specific examples of the epoxy compound as the resin modifier of the present invention include a phenolic epoxy compound obtained by a condensation reaction of a polyhydric phenol compound such as bisphenol A glycidyl ether and an epihalohydrin compound, a hydrogenated bisphenol A glycidyl ether, and the like. Alcohol-based epoxy compounds obtained by condensation of polyhydric alcohol compounds and epihalohydrin compounds, 3,4-epoxycyclohexylmethyl-3 ′, 4′-epoxycyclohexanecarboxylate, 1,2-hexahydrophthalic acid diglycidyl ester, etc. Glycidyl ester epoxy compounds obtained by condensation of polyvalent organic acid compounds and epihalohydrin compounds, amine epoxy compounds obtained by condensation of secondary amine compounds and epihalohydrin compounds, etc. And the like Le cyclohexene diepoxide and an aliphatic polyvalent epoxy compound.
スルフィド基含有エポキシド化合物とエーテル基含有エポキシド化合物の具体的化合物例としては、ビス(2,3−エポキシプロピル)スルフィド、ビス(2,3−エポキシプロピル)ジスルフィド、ビス(2,3−エポキシプロピルチオ)メタン、1,2−ビス(2,3−エポキシプロピルチオ)エタン、1,2−ビス(2,3−エポキシプロピルチオ)プロパン、1,3−ビス(2,3−エポキシプロピルチオ)プロパン、1,3−ビス(2,3−エポキシプロピルチオ)−2−メチルプロパン、1,4−ビス(2,3−エポキシプロピルチオ)ブタン、1,4−ビス(2,3−エポキシプロピルチオ)−2−メチルブタン、1,3−ビス(2,3−エポキシプロピルチオ)ブタン、1,5−ビス(2,3−エポキシプロピルチオ)ペンタン、1,5−ビス(2,3−エポキシプロピルチオ)−2−メチルペンタン、1,5−ビス(2,3−エポキシプロピルチオ)−3−チアペンタン、1,6−ビス(2,3−エポキシプロピルチオ)ヘキサン、1,6−ビス(2,3−エポキシプロピルチオ)−2−メチルヘキサン、3,8−ビス(2,3−エポキシプロピルチオ)−3,6−ジチアオクタン、1,2,3−トリス(2,3−エポキシプロピルチオ)プロパン、2,2−ビス(2,3−エポキシプロピルチオ)−1,3−ビス(2,3−エポキシプロピルチオメチル)プロパン、2,2−ビス(2,3−エポキシプロピルチオメチル)−1−(2,3−エポキシプロピルチオ)ブタン、1,5−ビス(2,3−エポキシプロピルチオ)−2−(2,3−エポキシプロピルチオメチル)−3−チアペンタン、1,5−ビス(2,3−エポキシプロピルチオ)−2,4−ビス(2,3−エポキシプロピルチオメチル)−3−チアペンタン、1−(2,3−エポキシプロピルチオ)−2,2−ビス(2,3−エポキシプロピルチオメチル)−4−チアヘキサン、1,5,6−トリス(2,3−エポキシプロピルチオ)−4−(2,3−エポキシプロピルチオメチル)−3−チアヘキサン、1,8−ビス(2,3−エポキシプロピルチオ)−4−(2,3−エポキシプロピルチオメチル)−3,6−ジチアオクタン、1,8−ビス(2,3−エポキシプロピルチオ)−4,5−ビス(2,3−エポキシプロピルチオメチル)−3,6−ジチアオクタン、1,8−ビス(2,3−エポキシプロピルチオ)−4,4−ビス(2,3−エポキシプロピルチオメチル)−3,6−ジチアオクタン、1,8−ビス(2,3−エポキシプロピルチオ)−2,5−ビス(2,3−エポキシプロピルチオメチル)−3,6−ジチアオクタン、1,8−ビス(2,3−エポキシプロピルチオ)−2,4,5−トリス(2,3−エポキシプロピルチオメチル)−3,6−ジチアオクタン、1,1,1−トリス[[2−(2,3−エポキシプロピルチオ)エチル]チオメチル]−2−(2,3−エポキシプロピルチオ)エタン、1,1,2,2−テトラキス[[2−(2,3−エポキシプロピルチオ)エチル]チオメチル]エタン、1,11−ビス(2,3−エポキシプロピルチオ)−4,8−ビス(2,3−エポキシプロピルチオメチル)−3,6,9−トリチアウンデカン、1,11−ビス(2,3−エポキシプロピルチオ)−4,7−ビス(2,3−エポキシプロピルチオメチル)−3,6,9−トリチアウンデカン、1,11−ビス(2,3−エポキシプロピルチオ)−5,7−ビス(2,3−エポキシプロピルチオメチル)−3,6,9−トリチアウンデカン等の鎖状脂肪族の2,3−エポキシプロピルチオ化合物、及び、 Specific examples of the sulfide group-containing epoxide compound and the ether group-containing epoxide compound include bis (2,3-epoxypropyl) sulfide, bis (2,3-epoxypropyl) disulfide, bis (2,3-epoxypropylthio). ) Methane, 1,2-bis (2,3-epoxypropylthio) ethane, 1,2-bis (2,3-epoxypropylthio) propane, 1,3-bis (2,3-epoxypropylthio) propane 1,3-bis (2,3-epoxypropylthio) -2-methylpropane, 1,4-bis (2,3-epoxypropylthio) butane, 1,4-bis (2,3-epoxypropylthio) ) -2-Methylbutane, 1,3-bis (2,3-epoxypropylthio) butane, 1,5-bis (2,3-epoxypropylthio) pen 1,5-bis (2,3-epoxypropylthio) -2-methylpentane, 1,5-bis (2,3-epoxypropylthio) -3-thiapentane, 1,6-bis (2,3 -Epoxypropylthio) hexane, 1,6-bis (2,3-epoxypropylthio) -2-methylhexane, 3,8-bis (2,3-epoxypropylthio) -3,6-dithiaoctane, 1, 2,3-tris (2,3-epoxypropylthio) propane, 2,2-bis (2,3-epoxypropylthio) -1,3-bis (2,3-epoxypropylthiomethyl) propane, 2, 2-bis (2,3-epoxypropylthiomethyl) -1- (2,3-epoxypropylthio) butane, 1,5-bis (2,3-epoxypropylthio) -2- (2,3-epoxy Propylchi Methyl) -3-thiapentane, 1,5-bis (2,3-epoxypropylthio) -2,4-bis (2,3-epoxypropylthiomethyl) -3-thiapentane, 1- (2,3-epoxy Propylthio) -2,2-bis (2,3-epoxypropylthiomethyl) -4-thiahexane, 1,5,6-tris (2,3-epoxypropylthio) -4- (2,3-epoxypropyl) Thiomethyl) -3-thiahexane, 1,8-bis (2,3-epoxypropylthio) -4- (2,3-epoxypropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (2, 3-epoxypropylthio) -4,5-bis (2,3-epoxypropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (2,3-epoxypropylthio) -4,4-bis ( 2, 3-epoxypropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (2,3-epoxypropylthio) -2,5-bis (2,3-epoxypropylthiomethyl) -3,6-dithiaoctane 1,8-bis (2,3-epoxypropylthio) -2,4,5-tris (2,3-epoxypropylthiomethyl) -3,6-dithiaoctane, 1,1,1-tris [[2 -(2,3-epoxypropylthio) ethyl] thiomethyl] -2- (2,3-epoxypropylthio) ethane, 1,1,2,2-tetrakis [[2- (2,3-epoxypropylthio) Ethyl] thiomethyl] ethane, 1,11-bis (2,3-epoxypropylthio) -4,8-bis (2,3-epoxypropylthiomethyl) -3,6,9-trithiaundecane, 1,11 Bis (2,3-epoxypropylthio) -4,7-bis (2,3-epoxypropylthiomethyl) -3,6,9-trithiaundecane, 1,11-bis (2,3-epoxypropylthio) ) -5,7-bis (2,3-epoxypropylthiomethyl) -3,6,9-trithiaundecane and the like chain aliphatic 2,3-epoxypropylthio compounds, and
1,3−ビス(2,3−エポキシプロピルチオ)シクロヘキサン、1,4−ビス(2,3−エポキシプロピルチオ)シクロヘキサン、1,3−ビス(2,3−エポキシプロピルチオメチル)シクロヘキサン、1,4−ビス(2,3−エポキシプロピルチオメチル)シクロヘキサン、2,5−ビス(2,3−エポキシプロピルチオメチル)−1,4−ジチアン、2,5−ビス[[2−(2,3−エポキシプロピルチオ)エチル]チオメチル]−1,4−ジチアン、2,5−ビス(2,3−エポキシプロピルチオメチル)−2,5−ジメチル−1,4−ジチアン等の環状脂肪族の2,3−エポキシプロピルチオ化合物、及び、 1,3-bis (2,3-epoxypropylthio) cyclohexane, 1,4-bis (2,3-epoxypropylthio) cyclohexane, 1,3-bis (2,3-epoxypropylthiomethyl) cyclohexane, 1 , 4-bis (2,3-epoxypropylthiomethyl) cyclohexane, 2,5-bis (2,3-epoxypropylthiomethyl) -1,4-dithiane, 2,5-bis [[2- (2, Cyclic epoxy such as 3-epoxypropylthio) ethyl] thiomethyl] -1,4-dithiane, 2,5-bis (2,3-epoxypropylthiomethyl) -2,5-dimethyl-1,4-dithiane A 2,3-epoxypropylthio compound, and
1,2−ビス(2,3−エポキシプロピルチオ)ベンゼン、1,3−ビス(2,3−エポキシプロピルチオ)ベンゼン、1,4−ビス(2,3−エポキシプロピルチオ)ベンゼン、1,2−ビス(2,3−エポキシプロピルチオメチル)ベンゼン、1,3−ビス(2,3−エポキシプロピルチオメチル)ベンゼン、1,4−ビス(2,3−エポキシプロピルチオメチル)ベンゼン、ビス[4−(2,3−エポキシプロピルチオ)フェニル]メタン、2,2−ビス[4−(2,3−エポキシプロピルチオ)フェニル]プロパン、ビス[4−(2,3−エポキシプロピルチオ)フェニル]スルフィド、ビス[4−(2,3−エポキシプロピルチオ)フェニル]スルホン、4,4’−ビス(2,3−エポキシプロピルチオ)ビフェニル等の芳香族2,3−エポキシプロピルチオ化合物、 1,2-bis (2,3-epoxypropylthio) benzene, 1,3-bis (2,3-epoxypropylthio) benzene, 1,4-bis (2,3-epoxypropylthio) benzene, 1, 2-bis (2,3-epoxypropylthiomethyl) benzene, 1,3-bis (2,3-epoxypropylthiomethyl) benzene, 1,4-bis (2,3-epoxypropylthiomethyl) benzene, bis [4- (2,3-epoxypropylthio) phenyl] methane, 2,2-bis [4- (2,3-epoxypropylthio) phenyl] propane, bis [4- (2,3-epoxypropylthio) Aromatic 2 such as phenyl] sulfide, bis [4- (2,3-epoxypropylthio) phenyl] sulfone, 4,4′-bis (2,3-epoxypropylthio) biphenyl 3-epoxypropyl thio compounds,
エチレンオキシド、プロピレンオキシド、グリシドール、エピクロルヒドリン等の単官能エポキシ化合物、 Monofunctional epoxy compounds such as ethylene oxide, propylene oxide, glycidol, epichlorohydrin,
ビス(2,3−エポキシプロピル)エーテル、ビス(2,3−エポキシプロピルオキシ)メタン、1,2−ビス(2,3−エポキシプロピルオキシ)エタン、1,2−ビス(2,3−エポキシプロピルオキシ)プロパン、1,3−ビス(2,3−エポキシプロピルオキシ)プロパン、1,3−ビス(2,3−エポキシプロピルオキシ)−2−メチルプロパン、1,4−ビス(2,3−エポキシプロピルオキシ)ブタン、1,4−ビス(2,3−エポキシプロピルオキシ)−2−メチルブタン、1,3−ビス(2,3−エポキシプロピルオキシ)ブタン、1,5−ビス(2,3−エポキシプロピルオキシ)ペンタン、1,5−ビス(2,3−エポキシプロピルオキシ)−2−メチルペンタン、1,5−ビス(2,3−エポキシプロピルオキシ)−3−チアペンタン、1,6−ビス(2,3−エポキシプロピルオキシ)ヘキサン、1,6−ビス(2,3−エポキシプロピルオキシ)−2−メチルヘキサン、3,8−ビス(2,3−エポキシプロピルオキシ)−3,6−ジチアオクタン、1,2,3−トリス(2,3−エポキシプロピルオキシ)プロパン、2,2−ビス(2,3−エポキシプロピルオキシ)−1,3−ビス(2,3−エポキシプロピルオキシメチル)プロパン、2,2−ビス(2,3−エポキシプロピルオキシメチル)−1−(2,3−エポキシプロピルオキシ)ブタン、1,5−ビス(2,3−エポキシプロピルオキシ)−2−(2,3−エポキシプロピルオキシメチル)−3−チアペンタン、1,5−ビス(2,3−エポキシプロピルオキシ)−2,4−ビス(2,3−エポキシプロピルオキシメチル)−3−チアペンタン、1−(2,3−エポキシプロピルオキシ)−2,2−ビス(2,3−エポキシプロピルオキシメチル)−4−チアヘキサン、1,5,6−トリス(2,3−エポキシプロピルオキシ)−4−(2,3−エポキシプロピルオキシメチル)−3−チアヘキサン、1,8−ビス(2,3−エポキシプロピルオキシ)−4−(2,3−エポキシプロピルオキシメチル)−3,6−ジチアオクタン、1,8−ビス(2,3−エポキシプロピルオキシ)−4,5−ビス(2,3−エポキシプロピルオキシメチル)−3,6−ジチアオクタン、1,8−ビス(2,3−エポキシプロピルオキシ)−4,4−ビス(2,3−エポキシプロピルオキシメチル)−3,6−ジチアオクタン、1,8−ビス(2,3−エポキシプロピルオキシ)−2,5−ビス(2,3−エポキシプロピルオキシメチル)−3,6−ジチアオクタン、1,8−ビス(2,3−エポキシプロピルオキシ)−2,4,5−トリス(2,3−エポキシプロピルオキシメチル)−3,6−ジチアオクタン、1,1,1−トリス[[2−(2,3−エポキシプロピルオキシ)エチル]チオメチル]−2−(2,3−エポキシプロピルオキシ)エタン、1,1,2,2−テトラキス[[2−(2,3−エポキシプロピルオキシ)エチル]チオメチル]エタン、1,11−ビス(2,3−エポキシプロピルオキシ)−4,8−ビス(2,3−エポキシプロピルオキシメチル)−3,6,9−トリチアウンデカン、1,11−ビス(2,3−エポキシプロピルオキシ)−4,7−ビス(2,3−エポキシプロピルオキシメチル)−3,6,9−トリチアウンデカン、1,11−ビス(2,3−エポキシプロピルオキシ)−5,7−ビス(2,3−エポキシプロピルオキシメチル)−3,6,9−トリチアウンデカン等の鎖状脂肪族の2,3−エポキシプロピルオキシ化合物、及び、 Bis (2,3-epoxypropyl) ether, bis (2,3-epoxypropyloxy) methane, 1,2-bis (2,3-epoxypropyloxy) ethane, 1,2-bis (2,3-epoxy) Propyloxy) propane, 1,3-bis (2,3-epoxypropyloxy) propane, 1,3-bis (2,3-epoxypropyloxy) -2-methylpropane, 1,4-bis (2,3 -Epoxypropyloxy) butane, 1,4-bis (2,3-epoxypropyloxy) -2-methylbutane, 1,3-bis (2,3-epoxypropyloxy) butane, 1,5-bis (2, 3-epoxypropyloxy) pentane, 1,5-bis (2,3-epoxypropyloxy) -2-methylpentane, 1,5-bis (2,3-epoxypropyloxy) 3-thiapentane, 1,6-bis (2,3-epoxypropyloxy) hexane, 1,6-bis (2,3-epoxypropyloxy) -2-methylhexane, 3,8-bis (2,3- Epoxypropyloxy) -3,6-dithiaoctane, 1,2,3-tris (2,3-epoxypropyloxy) propane, 2,2-bis (2,3-epoxypropyloxy) -1,3-bis ( 2,3-epoxypropyloxymethyl) propane, 2,2-bis (2,3-epoxypropyloxymethyl) -1- (2,3-epoxypropyloxy) butane, 1,5-bis (2,3- Epoxypropyloxy) -2- (2,3-epoxypropyloxymethyl) -3-thiapentane, 1,5-bis (2,3-epoxypropyloxy) -2,4-bis (2, -Epoxypropyloxymethyl) -3-thiapentane, 1- (2,3-epoxypropyloxy) -2,2-bis (2,3-epoxypropyloxymethyl) -4-thiahexane, 1,5,6-tris (2,3-epoxypropyloxy) -4- (2,3-epoxypropyloxymethyl) -3-thiahexane, 1,8-bis (2,3-epoxypropyloxy) -4- (2,3-epoxy Propyloxymethyl) -3,6-dithiaoctane, 1,8-bis (2,3-epoxypropyloxy) -4,5-bis (2,3-epoxypropyloxymethyl) -3,6-dithiaoctane, 1, 8-bis (2,3-epoxypropyloxy) -4,4-bis (2,3-epoxypropyloxymethyl) -3,6-dithiaoctane, 1,8-bis ( 2,3-epoxypropyloxy) -2,5-bis (2,3-epoxypropyloxymethyl) -3,6-dithiaoctane, 1,8-bis (2,3-epoxypropyloxy) -2,4 5-tris (2,3-epoxypropyloxymethyl) -3,6-dithiaoctane, 1,1,1-tris [[2- (2,3-epoxypropyloxy) ethyl] thiomethyl] -2- (2, 3-epoxypropyloxy) ethane, 1,1,2,2-tetrakis [[2- (2,3-epoxypropyloxy) ethyl] thiomethyl] ethane, 1,11-bis (2,3-epoxypropyloxy) -4,8-bis (2,3-epoxypropyloxymethyl) -3,6,9-trithiaundecane, 1,11-bis (2,3-epoxypropyloxy) -4,7-bis 2,3-epoxypropyloxymethyl) -3,6,9-trithiaundecane, 1,11-bis (2,3-epoxypropyloxy) -5,7-bis (2,3-epoxypropyloxymethyl) Chain aliphatic 2,3-epoxypropyloxy compounds such as -3,6,9-trithiaundecane, and
1,3−ビス(2,3−エポキシプロピルオキシ)シクロヘキサン、1,4−ビス(2,3−エポキシプロピルオキシ)シクロヘキサン、1,3−ビス(2,3−エポキシプロピルオキシメチル)シクロヘキサン、1,4−ビス(2,3−エポキシプロピルオキシメチル)シクロヘキサン、2,5−ビス(2,3−エポキシプロピルオキシメチル)−1,4−ジチアン、2,5−ビス[[2−(2,3−エポキシプロピルオキシ)エチル]チオメチル]−1,4−ジチアン、2,5−ビス(2,3−エポキシプロピルオキシメチル)−2,5−ジメチル−1,4−ジチアン等の環状脂肪族の2,3−エポキシプロピルオキシ化合物、及び、 1,3-bis (2,3-epoxypropyloxy) cyclohexane, 1,4-bis (2,3-epoxypropyloxy) cyclohexane, 1,3-bis (2,3-epoxypropyloxymethyl) cyclohexane, 1 , 4-bis (2,3-epoxypropyloxymethyl) cyclohexane, 2,5-bis (2,3-epoxypropyloxymethyl) -1,4-dithiane, 2,5-bis [[2- (2, Cycloepoxy such as 3-epoxypropyloxy) ethyl] thiomethyl] -1,4-dithiane, 2,5-bis (2,3-epoxypropyloxymethyl) -2,5-dimethyl-1,4-dithiane 2,3-epoxypropyloxy compounds, and
1,2−ビス(2,3−エポキシプロピルオキシ)ベンゼン、1,3−ビス(2,3−エポキシプロピルオキシ)ベンゼン、1,4−ビス(2,3−エポキシプロピルオキシ)ベンゼン、1,2−ビス(2,3−エポキシプロピルオキシメチル)ベンゼン、1,3−ビス(2,3−エポキシプロピルオキシメチル)ベンゼン、1,4−ビス(2,3−エポキシプロピルオキシメチル)ベンゼン、ビス[4−(2,3−エポキシプロピルオキシ)フェニル]メタン、2,2−ビス[4−(2,3−エポキシプロピルオキシ)フェニル]プロパン、ビス[4−(2,3−エポキシプロピルオキシ)フェニル]スルフィド、ビス[4−(2,3−エポキシプロピルオキシ)フェニル]スルホン、4,4’−ビス(2,3−エポキシプロピルオキシ)ビフェニル等の芳香族2,3−エポキシプロピルオキシ化合物等を挙げることができるが、例示化合物のみに限定されるものではない。これらの例示化合物のみに限定されるものではない。 1,2-bis (2,3-epoxypropyloxy) benzene, 1,3-bis (2,3-epoxypropyloxy) benzene, 1,4-bis (2,3-epoxypropyloxy) benzene, 1, 2-bis (2,3-epoxypropyloxymethyl) benzene, 1,3-bis (2,3-epoxypropyloxymethyl) benzene, 1,4-bis (2,3-epoxypropyloxymethyl) benzene, bis [4- (2,3-epoxypropyloxy) phenyl] methane, 2,2-bis [4- (2,3-epoxypropyloxy) phenyl] propane, bis [4- (2,3-epoxypropyloxy) Phenyl] sulfide, bis [4- (2,3-epoxypropyloxy) phenyl] sulfone, 4,4′-bis (2,3-epoxypropyloxy) Can be exemplified aromatic 2,3-epoxypropyloxy compounds such as phenyl, it is not limited only to the exemplified compounds. It is not limited only to these exemplary compounds.
樹脂改質剤として添加を可能とするアミン化合物の具体例としては、エチルアミン、n−プロピルアミン、イソプロピルアミン、n−ブチルアミン、sec−ブチルアミン、ter−ブチルアミン、ペンチルアミン、ヘキシルアミン、ヘプチルアミン、オクチルアミン、デシルアミン、ラウリルアミン、ミリスチルアミン、3−ペンチルアミン、2−エチルヘキシルアミン、1,2−ジメチルヘキシルアミン、アリルアミン、アミノメチルビシクロヘプタン、シクロペンチルアミン、シクロヘキシルアミン、2,3−ジメチルシクロヘキシルアミン、アミノメチルシクロヘキサン、アニリン、ベンジルアミン、フェネチルアミン、2,3−、あるいは4−メチルベンジルアミン、o−、m−、あるいはp−メチルアニリン、o−、m−、あるいはp−エチルアニリン、アミノモルホリン、ナフチルアミン、フルフリルアミン、α−アミノジフェニルメタン、トルイジン、アミノピリジン、アミノフェノール、アミノエタノール、1−アミノプロパノール、2−アミノプロパノール、アミノブタノール、アミノペンタノール、アミノヘキサノール、メトキシエチルアミン、2−(2−アミノエトキシ)エタノール、3−エトキシプロピルアミン、3−プロポキシプロピルアミン、3−ブトキシプロピルアミン、3−イソプロポキシプロピルアミン、3−イソブトキシプロピルアミン、2,2−ジエトキシエチルアミン等の単官能1級アミン化合物、 Specific examples of amine compounds that can be added as a resin modifier include ethylamine, n-propylamine, isopropylamine, n-butylamine, sec-butylamine, ter-butylamine, pentylamine, hexylamine, heptylamine, octyl Amine, decylamine, laurylamine, myristylamine, 3-pentylamine, 2-ethylhexylamine, 1,2-dimethylhexylamine, allylamine, aminomethylbicycloheptane, cyclopentylamine, cyclohexylamine, 2,3-dimethylcyclohexylamine, amino Methylcyclohexane, aniline, benzylamine, phenethylamine, 2,3-, or 4-methylbenzylamine, o-, m-, or p-methylaniline, o-, m- Is p-ethylaniline, aminomorpholine, naphthylamine, furfurylamine, α-aminodiphenylmethane, toluidine, aminopyridine, aminophenol, aminoethanol, 1-aminopropanol, 2-aminopropanol, aminobutanol, aminopentanol, aminohexanol, Methoxyethylamine, 2- (2-aminoethoxy) ethanol, 3-ethoxypropylamine, 3-propoxypropylamine, 3-butoxypropylamine, 3-isopropoxypropylamine, 3-isobutoxypropylamine, 2,2-di Monofunctional primary amine compounds such as ethoxyethylamine,
エチレンジアミン、1,2−、あるいは1,3−ジアミノプロパン、1,2−、1,3−、あるいは1,4−ジアミノブタン、1,5−ジアミノペンタン、1,6−ジアミノヘキサン、1,7−ジアミノヘプタン、1,8−ジアミノオクタン、1,10−ジアミノデカン、1,2−、1,3−、あるいは1,4−ジアミノシクロヘキサン、o−、m−あるいはp−ジアミノベンゼン、3,4−あるいは4,4’−ジアミノベンゾフェノン、3,4−あるいは4,4’−ジアミノジフェニルエーテル、4,4’−ジアミノジフェニルメタン、4,4’−ジアミノジフェニルスルフィド、3,3’−、あるいは4,4’−ジアミノジフェニルスルフォン、2,7−ジアミノフルオレン、1,5−、1,8−、あるいは2,3−ジアミノナフタレン、2,3−、2,6−、あるいは3,4−ジアミノピリジン、2,4−、あるいは2,6−ジアミノトルエン、m−、あるいはp−キシリレンジアミン、イソホロンジアミン、ジアミノメチルビシクロヘプタン、1,3−、あるいは1,4−ジアミノメチルシクロヘキサン、2−、あるいは4−アミノピペリジン、2−、あるいは4−アミノメチルピペリジン、2−、あるいは4−アミノエチルピペリジン、N−アミノエチルモルホリン、N−アミノプロピルモルホリン等の1級ポリアミン化合物、 Ethylenediamine, 1,2-, or 1,3-diaminopropane, 1,2-, 1,3-, or 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 1,7 -Diaminoheptane, 1,8-diaminooctane, 1,10-diaminodecane, 1,2-, 1,3-, or 1,4-diaminocyclohexane, o-, m- or p-diaminobenzene, 3,4 -Or 4,4'-diaminobenzophenone, 3,4- or 4,4'-diaminodiphenyl ether, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfide, 3,3'-, or 4,4 '-Diaminodiphenylsulfone, 2,7-diaminofluorene, 1,5-, 1,8-, or 2,3-diaminonaphthalene 2,3-, 2,6-, or 3,4-diaminopyridine, 2,4-, or 2,6-diaminotoluene, m-, or p-xylylenediamine, isophoronediamine, diaminomethylbicycloheptane, 1 , 3- or 1,4-diaminomethylcyclohexane, 2- or 4-aminopiperidine, 2- or 4-aminomethylpiperidine, 2- or 4-aminoethylpiperidine, N-aminoethylmorpholine, N- Primary polyamine compounds such as aminopropylmorpholine,
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、 Diethylamine, dipropylamine, di-n-butylamine, di-sec-butylamine, diisobutylamine, di-n-pentylamine, di-3-pentylamine, dihexylamine, dioctylamine, di (2-ethylhexyl) amine, methyl Hexylamine, diallylamine, N-methylallylamine, piperidine, pyrrolidine, diphenylamine, N-methylamine, N-ethylamine, dibenzylamine, N-methylbenzylamine, N-ethylbenzylamine, dicyclohexylamine, N-methylaniline, N -Monofunctional secondary amine compounds such as ethylaniline, dinaphthylamine, 1-methylpiperazine, morpholine,
N,N’−ジメチルエチレンジアミン、N,N’−ジメチル−1,2−ジアミノプロパン、N,N’−ジメチル−1,3−ジアミノプロパン、N,N’−ジメチル−1,2−ジアミノブタン、N,N’−ジメチル−1,3−ジアミノブタン、N,N’−ジメチル−1,4−ジアミノブタン、N,N’−ジメチル−1,5−ジアミノペンタン、N,N’−ジメチル−1,6−ジアミノヘキサン、N,N’−ジメチル−1,7−ジアミノヘプタン、N,N’−ジエチルエチレンジアミン、N,N’−ジエチル−1,2−ジアミノプロパン、N,N’−ジエチル−1,3−ジアミノプロパン、N,N’−ジエチル−1,2−ジアミノブタン、N,N’−ジエチル−1,3−ジアミノブタン、N,N’−ジエチル−1,4−ジアミノブタン、N,N’−ジエチル−1,5−ジアミノペンタン、N,N’−ジエチル−1,6−ジアミノヘキサン、N,N’−ジエチル−1,7−ジアミノヘプタン、ピペラジン、2−メチルピペラジン、2,5−ジメチルピペラジン、2,6−ジメチルピペラジン、ホモピペラジン、1,1−ジ−(4−ピペリジル)メタン、1,2−ジ−(4−ピペリジル)エタン、1,3−ジ−(4−ピペリジル)プロパン、1,4−ジ−(4−ピペリジル)ブタン、テトラメチルグアニジン等の2級ポリアミン化合物等を挙げることができるが、例示化合物のみに限定されるものではない。また、上記アミン化合物は単独でも、2種類以上を混合して使用してもかまわない。また、例示化合物の内、ベンジルアミン、ピペラジン類はより好ましい化合物である。 N, N′-dimethylethylenediamine, N, N′-dimethyl-1,2-diaminopropane, N, N′-dimethyl-1,3-diaminopropane, N, N′-dimethyl-1,2-diaminobutane, N, N′-dimethyl-1,3-diaminobutane, N, N′-dimethyl-1,4-diaminobutane, N, N′-dimethyl-1,5-diaminopentane, N, N′-dimethyl-1 , 6-diaminohexane, N, N′-dimethyl-1,7-diaminoheptane, N, N′-diethylethylenediamine, N, N′-diethyl-1,2-diaminopropane, N, N′-diethyl-1 , 3-diaminopropane, N, N′-diethyl-1,2-diaminobutane, N, N′-diethyl-1,3-diaminobutane, N, N′-diethyl-1,4-diaminobutane, N, N ' Diethyl-1,5-diaminopentane, N, N′-diethyl-1,6-diaminohexane, N, N′-diethyl-1,7-diaminoheptane, piperazine, 2-methylpiperazine, 2,5-dimethylpiperazine 2,6-dimethylpiperazine, homopiperazine, 1,1-di- (4-piperidyl) methane, 1,2-di- (4-piperidyl) ethane, 1,3-di- (4-piperidyl) propane, Secondary polyamine compounds such as 1,4-di- (4-piperidyl) butane and tetramethylguanidine can be exemplified, but are not limited to the exemplified compounds. Moreover, the said amine compound may be used individually or in mixture of 2 or more types. Of the exemplified compounds, benzylamine and piperazines are more preferred compounds.
また、樹脂改質剤として添加を可能とするチオール化合物としては、メルカプト基以外にも少なくとも1個の硫黄原子を含有するものも含まれる。これらの具体例としては、単官能チオール化合物としては、メチルメルカプタン、エチルメルカプタン、プロピルメルカプタン、ブチルメルカプタン、オクチルメルカプタン、ドデシルメルカプタン、tert−ドデシルメルカプタン、ヘキサデシルメルカプタン、オクタデシルメルカプタン、シクロヘキシルメルカプタン、ベンジルメルカプタン、エチルフェニルメルカプタン、2−メルカプトメチル−1,3−ジチオラン、2−メルカプトメチル−1,4−ジチアン等の脂肪族メルカプタン化合物、チオフェノール、メルカプトトルエン等の芳香族メルカプタン化合物、 The thiol compounds that can be added as a resin modifier include those containing at least one sulfur atom in addition to the mercapto group. Specific examples of these compounds include monofunctional thiol compounds such as methyl mercaptan, ethyl mercaptan, propyl mercaptan, butyl mercaptan, octyl mercaptan, dodecyl mercaptan, tert-dodecyl mercaptan, hexadecyl mercaptan, octadecyl mercaptan, cyclohexyl mercaptan, benzyl mercaptan, Aliphatic mercaptan compounds such as ethylphenyl mercaptan, 2-mercaptomethyl-1,3-dithiolane, 2-mercaptomethyl-1,4-dithiane, aromatic mercaptan compounds such as thiophenol and mercaptotoluene,
2官能以上のポリチオール化合物としては、例えば、1,1−メタンジチオール、1,2−エタンジチオール、1,1−プロパンジチオール、1,2−プロパンジチオール、1,3−プロパンジチオール、2,2−プロパンジチオール、1,6−ヘキサンジチオール、1,2,3−プロパントリチオール、1,1−シクロヘキサンジチオール、1,2−シクロヘキサンジチオール、2,2−ジメチルプロパン−1,3−ジチオール、3,4−ジメトキシブタン−1,2−ジチオール、2−メチルシクロヘキサン−2,3−ジチオール、1,1−ビス(メルカプトメチル)シクロヘキサン、チオリンゴ酸ビス(2−メルカプトエチルエステル)、2,3−ジメルカプト−1−プロパノール(2−メルカプトアセテート)、2,3−ジメルカプト−1−プロパノール(3−メルカプトプロピオネート)、ジエチレングリコールビス(2−メルカプトアセテート)、ジエチレングリコールビス(3−メルカプトプロピオネート)、1,2−ジメルカプトプロピルメチルエーテル、2,3−ジメルカプトプロピルメチルエーテル、2,2−ビス(メルカプトメチル)−1,3−プロパンジチオール、ビス(2−メルカプトエチル)エーテル、エチレングリコールビス(2−メルカプトアセテート)、エチレングリコールビス(3−メルカプトプロピオネート)、トリメチロールプロパンビス(2−メルカプトアセテート)、トリメチロールプロパンビス(3−メルカプトプロピオネート)、ペンタエリスリトールテトラキス(2−メルカプトアセテート)、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)、テトラキス(メルカプトメチル)メタン等の脂肪族ポリチオール化合物、 Examples of the bifunctional or higher polythiol compound include 1,1-methanedithiol, 1,2-ethanedithiol, 1,1-propanedithiol, 1,2-propanedithiol, 1,3-propanedithiol, 2,2- Propanedithiol, 1,6-hexanedithiol, 1,2,3-propanetrithiol, 1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, 2,2-dimethylpropane-1,3-dithiol, 3,4 -Dimethoxybutane-1,2-dithiol, 2-methylcyclohexane-2,3-dithiol, 1,1-bis (mercaptomethyl) cyclohexane, bis (2-mercaptoethyl ester) thiomalate, 2,3-dimercapto-1 -Propanol (2-mercaptoacetate), 2,3-dimercapto- 1-propanol (3-mercaptopropionate), diethylene glycol bis (2-mercaptoacetate), diethylene glycol bis (3-mercaptopropionate), 1,2-dimercaptopropyl methyl ether, 2,3-dimercaptopropyl methyl Ether, 2,2-bis (mercaptomethyl) -1,3-propanedithiol, bis (2-mercaptoethyl) ether, ethylene glycol bis (2-mercaptoacetate), ethylene glycol bis (3-mercaptopropionate), Trimethylolpropane bis (2-mercaptoacetate), trimethylolpropane bis (3-mercaptopropionate), pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetrakis ( - mercaptopropionate), tetrakis (mercaptomethyl) aliphatic such as methane polythiol compound,
1,2−ジメルカプトベンゼン、1,3−ジメルカプトベンゼン、1,4−ジメルカプトベンゼン、1,2−ビス(メルカプトメチル)ベンゼン、1,3−ビス(メルカプトメチル)ベンゼン、1,4−ビス(メルカプトメチル)ベンゼン、1,2−ビス(メルカプトエチル)ベンゼン、1,3−ビス(メルカプトエチル)ベンゼン、1,4−ビス(メルカプトエチル)ベンゼン、1,2,3−トリメルカプトベンゼン、1,2,4−トリメルカプトベンゼン、1,3,5−トリメルカプトベンゼン、1,2,3−トリス(メルカプトメチル)ベンゼン、1,2,4−トリス(メルカプトメチル)ベンゼン、1,3,5−トリス(メルカプトメチル)ベンゼン、1,2,3−トリス(メルカプトエチル)ベンゼン、1,2,4−トリス(メルカプトエチル)ベンゼン、1,3,5−トリス(メルカプトエチル)ベンゼン、2,5−トルエンジチオール、3,4−トルエンジチオール、1,3−ジ(p−メトキシフェニル)プロパン−2,2−ジチオール、1,3−ジフェニルプロパン−2,2−ジチオール、フェニルメタン−1,1−ジチオール、2,4−ジ(p−メルカプトフェニル)ペンタン等の芳香族ポリチオール、 1,2-dimercaptobenzene, 1,3-dimercaptobenzene, 1,4-dimercaptobenzene, 1,2-bis (mercaptomethyl) benzene, 1,3-bis (mercaptomethyl) benzene, 1,4- Bis (mercaptomethyl) benzene, 1,2-bis (mercaptoethyl) benzene, 1,3-bis (mercaptoethyl) benzene, 1,4-bis (mercaptoethyl) benzene, 1,2,3-trimercaptobenzene, 1,2,4-trimercaptobenzene, 1,3,5-trimercaptobenzene, 1,2,3-tris (mercaptomethyl) benzene, 1,2,4-tris (mercaptomethyl) benzene, 1,3,3 5-tris (mercaptomethyl) benzene, 1,2,3-tris (mercaptoethyl) benzene, 1,2,4-tris (mer Puttoethyl) benzene, 1,3,5-tris (mercaptoethyl) benzene, 2,5-toluenedithiol, 3,4-toluenedithiol, 1,3-di (p-methoxyphenyl) propane-2,2-dithiol, Aromatic polythiols such as 1,3-diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol, 2,4-di (p-mercaptophenyl) pentane,
1,2−ビス(メルカプトエチルチオ)ベンゼン、1,3−ビス(メルカプトエチルチオ)ベンゼン、1,4−ビス(メルカプトエチルチオ)ベンゼン、1,2,3−トリス(メルカプトメチルチオ)ベンゼン、1,2,4−トリス(メルカプトメチルチオ)ベンゼン、1,3,5−トリス(メルカプトメチルチオ)ベンゼン、1,2,3−トリス(メルカプトエチルチオ)ベンゼン、1,2,4−トリス(メルカプトエチルチオ)ベンゼン、1,3,5−トリス(メルカプトエチルチオ)ベンゼン等、及びこれらの核アルキル化物等のメルカプト基以外に硫黄原子を含有する芳香族ポリチオール化合物、 1,2-bis (mercaptoethylthio) benzene, 1,3-bis (mercaptoethylthio) benzene, 1,4-bis (mercaptoethylthio) benzene, 1,2,3-tris (mercaptomethylthio) benzene, 1 , 2,4-Tris (mercaptomethylthio) benzene, 1,3,5-tris (mercaptomethylthio) benzene, 1,2,3-tris (mercaptoethylthio) benzene, 1,2,4-tris (mercaptoethylthio) ) Aromatic polythiol compounds containing sulfur atoms in addition to mercapto groups such as benzene, 1,3,5-tris (mercaptoethylthio) benzene, and their nuclear alkylated products,
ビス(メルカプトメチル)スルフィド、ビス(メルカプトメチル)ジスルフィド、ビス(メルカプトエチル)スルフィド、ビス(メルカプトエチル)ジスルフィド、ビス(メルカプトプロピル)スルフィド、ビス(メルカプトメチルチオ)メタン、ビス(2−メルカプトエチルチオ)メタン、ビス(3−メルカプトプロピルチオ)メタン、1,2−ビス(メルカプトメチルチオ)エタン、1,2−ビス(2−メルカプトエチルチオ)エタン、1,2−ビス(3−メルカプトプロピル)エタン、1,3−ビス(メルカプトメチルチオ)プロパン、1,3−ビス(2−メルカプトエチルチオ)プロパン、1,3−ビス(3−メルカプトプロピルチオ)プロパン、1,2,3−トリス(メルカプトメチルチオ)プロパン、1,2,3−トリス(2−メルカプトエチルチオ)プロパン、1,2,3−トリス(3−メルカプトプロピルチオ)プロパン、1,2−ビス[(2−メルカプトエチル)チオ]−3−メルカプトプロパン、4,8−ジメルカプトメチル−1,11−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−メルカプト−3,6,9−トリチアウンデカン、5,7−ジメルカプトメチル−1,11−メルカプト−3,6,9−トリチアウンデカン、テトラキス(メルカプトメチルチオメチル)メタン、テトラキス(2−メルカプトエチルチオメチル)メタン、テトラキス(3−メルカプトプロピルチオメチル)メタン、ビス(2,3−ジメルカプトプロピル)スルフィド、ビス(1,3−ジメルカプトプロピル)スルフィド、2,5−ジメルカプト−1,4−ジチアン、2,5−ジメルカプトメチル−1,4−ジチアン、2,5−ジメルカプトメチル−2,5−ジメチル−1,4−ジチアン、ビス(メルカプトメチル)ジスルフィド、ビス(メルカプトエチル)ジスルフィド、ビス(メルカプトプロピル)ジスルフィド等のメルカプト基以外に硫黄原子を含有する脂肪族ポリチオール化合物、及びこれらのチオグリコール酸及びメルカプトプロピオン酸のエステル、 Bis (mercaptomethyl) sulfide, bis (mercaptomethyl) disulfide, bis (mercaptoethyl) sulfide, bis (mercaptoethyl) disulfide, bis (mercaptopropyl) sulfide, bis (mercaptomethylthio) methane, bis (2-mercaptoethylthio) Methane, bis (3-mercaptopropylthio) methane, 1,2-bis (mercaptomethylthio) ethane, 1,2-bis (2-mercaptoethylthio) ethane, 1,2-bis (3-mercaptopropyl) ethane, 1,3-bis (mercaptomethylthio) propane, 1,3-bis (2-mercaptoethylthio) propane, 1,3-bis (3-mercaptopropylthio) propane, 1,2,3-tris (mercaptomethylthio) Propane, 1,2,3-tris (2- Lucaptoethylthio) propane, 1,2,3-tris (3-mercaptopropylthio) propane, 1,2-bis [(2-mercaptoethyl) thio] -3-mercaptopropane, 4,8-dimercaptomethyl -1,11-mercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-mercapto-3,6,9-trithiaundecane, 5,7-dimercaptomethyl-1 , 11-mercapto-3,6,9-trithiaundecane, tetrakis (mercaptomethylthiomethyl) methane, tetrakis (2-mercaptoethylthiomethyl) methane, tetrakis (3-mercaptopropylthiomethyl) methane, bis (2,3 -Dimercaptopropyl) sulfide, bis (1,3-dimercaptopropyl) sulfide, 2,5-di Lucapto-1,4-dithiane, 2,5-dimercaptomethyl-1,4-dithiane, 2,5-dimercaptomethyl-2,5-dimethyl-1,4-dithiane, bis (mercaptomethyl) disulfide, bis (Mercaptoethyl) disulfide, aliphatic polythiol compounds containing sulfur atoms in addition to mercapto groups such as bis (mercaptopropyl) disulfide, and esters of these thioglycolic acid and mercaptopropionic acid,
ヒドロキシメチルスルフィドビス(2−メルカプトアセテート)、ヒドロキシメチルスルフィドビス(3−メルカプトプロピオネート)、ヒドロキシエチルスルフィドビス(2−メルカプトアセテート)、ヒドロキシエチルスルフィドビス(3−メルカプトプロピオネート)、ヒドロキシプロピルスルフィドビス(2−メルカプトアセテート)、ヒドロキシプロピルスルフィドビス(3−メルカプトプロピオネート)、ヒドロキシメチルジスルフィドビス(2−メルカプトアセテート)、ヒドロキシメチルジスルフィドビス(3−メルカプトプロピオネート)、ヒドロキシエチルジスルフィドビス(2−メルカプトアセテート)、ヒドロキシエチルジスルフィドビス(3−メルカプトプロピオネート)、ヒドロキシプロピルジスルフィドビス(2−メルカプトアセテート)、ヒドロキシプロピルジスルフィドビス(3−メルカプトプロピオネート)、2−メルカプトエチルエーテルビス(2−メルカプトアセテート)、2−メルカプトエチルエーテルビス(3−メルカプトプロピオネート)、1,4−ジチアン−2,5−ジオールビス(2−メルカプトアセテート)、1,4−ジチアン−2,5−ジオールビス(3−メルカプトプロピオネート)、チオジグリコール酸ビス(2−メルカプトエチルエステル)、チオジプロピオン酸ビス(2−メルカプトエチルエステル)、4,4−チオジブチル酸ビス(2−メルカプトエチルエステル)、ジチオジグリコール酸ビス(2−メルカプトエチルエステル)、ジチオジプロピオン酸ビス(2−メルカプトエチルエステル)、4,4−ジチオジブチル酸ビス(2−メルカプトエチルエステル)、チオジグリコール酸ビス(2,3−ジメルカプトプロピルエステル)、チオジプロピオン酸ビス(2,3−ジメルカプトプロピルエステル)、ジチオグリコール酸ビス(2,3−ジメルカプトプロピルエステル)、ジチオジプロピオン酸ビス(2,3−ジメルカプトプロピルエステル)等のその他のメルカプト基以外に硫黄原子とエステル結合を含有する脂肪族ポリチオール化合物、3,4−チオフェンジチオール、2,5−ジメルカプト−1,3,4−チアジアゾール等のメルカプト基以外に硫黄原子を含有する複素環化合物、 Hydroxymethyl sulfide bis (2-mercaptoacetate), hydroxymethyl sulfide bis (3-mercaptopropionate), hydroxyethyl sulfide bis (2-mercaptoacetate), hydroxyethyl sulfide bis (3-mercaptopropionate), hydroxypropyl Sulfide bis (2-mercaptoacetate), hydroxypropyl sulfide bis (3-mercaptopropionate), hydroxymethyl disulfide bis (2-mercaptoacetate), hydroxymethyl disulfide bis (3-mercaptopropionate), hydroxyethyl disulfide bis (2-mercaptoacetate), hydroxyethyl disulfide bis (3-mercaptopropionate), hydroxypropyl disulfide bis 2-mercaptoacetate), hydroxypropyl disulfide bis (3-mercaptopropionate), 2-mercaptoethyl ether bis (2-mercaptoacetate), 2-mercaptoethyl ether bis (3-mercaptopropionate), 1,4 Dithian-2,5-diol bis (2-mercaptoacetate), 1,4-dithian-2,5-diol bis (3-mercaptopropionate), thiodiglycolic acid bis (2-mercaptoethyl ester), thiodi Propionic acid bis (2-mercaptoethyl ester), 4,4-thiodibutyric acid bis (2-mercaptoethyl ester), dithiodiglycolic acid bis (2-mercaptoethyl ester), dithiodipropionic acid bis (2-mercaptoethyl ester) ), 4,4-dithio Dibutyl acid bis (2-mercaptoethyl ester), thiodiglycolic acid bis (2,3-dimercaptopropyl ester), thiodipropionic acid bis (2,3-dimercaptopropyl ester), dithioglycolic acid bis (2, 3-dimercaptopropyl ester), dithiodipropionic acid bis (2,3-dimercaptopropyl ester) and other mercapto groups, aliphatic polythiol compounds containing a sulfur atom and an ester bond, and 3,4-thiophenedithiol , Heterocyclic compounds containing a sulfur atom in addition to a mercapto group such as 2,5-dimercapto-1,3,4-thiadiazole,
2−メルカプトエタノール、3−メルカプト−1,2−プロパンジオール、グリセリンジ(メルカプトアセテート)、1−ヒドロキシ−4−メルカプトシクロヘキサン、2,4−ジメルカプトフェノール、2−メルカプトハイドロキノン、4−メルカプトフェノール、3,4−ジメルカプト−2−プロパノール、1,3−ジメルカプト−2−プロパノール、2,3−ジメルカプト−1−プロパノール、1,2−ジメルカプト−1,3−ブタンジオール、ペンタエリスリトールトリス(3−メルカプトプロピオネート)、ペンタエリスリトールモノ(3−メルカプトプロピオネート)、ペンタエリスリトールビス(3−メルカプトプロピオネート)、ペンタエリスリトールトリス(チオグリコレート)、ジペンタエリスリトールペンタキス(3−メルカプトプロピオネート)、ヒドロキシメチル−トリス(メルカプトエチルチオメチル)メタン、1−ヒドロキシエチルチオ−3−メルカプトエチルチオベンゼン等のメルカプト基以外にヒドロキシ基を含有する化合物、 2-mercaptoethanol, 3-mercapto-1,2-propanediol, glycerol di (mercaptoacetate), 1-hydroxy-4-mercaptocyclohexane, 2,4-dimercaptophenol, 2-mercaptohydroquinone, 4-mercaptophenol, 3,4-dimercapto-2-propanol, 1,3-dimercapto-2-propanol, 2,3-dimercapto-1-propanol, 1,2-dimercapto-1,3-butanediol, pentaerythritol tris (3-mercapto Propionate), pentaerythritol mono (3-mercaptopropionate), pentaerythritol bis (3-mercaptopropionate), pentaerythritol tris (thioglycolate), dipentaerythritol pentakis (3 Mercaptopropionate), hydroxymethyl - tris (mercaptoethylthiomethyl) methane, compounds containing 1-hydroxyethyl-thio-3-mercaptoethyl hydroxy group other than the mercapto group of thio benzene,
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、2,2−ビス(メルカプトメチル)−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、4,6−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−ジチアニルチオ}−3,3−ビス(メルカプトメチルチオ)プロパン、1,3−ビス{4−(6−メルカプトメチルチオ)−1,3−ジチアニルチオ}−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−{4−(6−メルカプトメチルチオ)−1,3−ジチアニルチオ}−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)−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−ジチアニルチオ}−1,3−ジチアン、4−{4−(6−メルカプトメチルチオ)−1,3−ジチアニルチオ}−6−{4−(6−メルカプトメチルチオ)−1,3−ジチアニルチオ}−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、更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化合物、 1,1,3,3-tetrakis (mercaptomethylthio) propane, 1,1,2,2-tetrakis (mercaptomethylthio) ethane, 4,6-bis (mercaptomethylthio) -1,3-dithiacyclohexane, 1, 1,5,5-tetrakis (mercaptomethylthio) -3-thiapentane, 1,1,6,6-tetrakis (mercaptomethylthio) -3,4-dithiahexane, 2,2-bis (mercaptomethylthio) ethanethiol, 2- (4,5-Dimercapto-2-thiapentyl) -1,3-dithiacyclopentane, 2,2-bis (mercaptomethyl) -1,3-dithiacyclopentane, 2,5-bis (4,4- Bis (mercaptomethylthio) -2-thiabutyl) -1,4-dithiane, 2,2-bis (mercaptomethylthio) -1,3-propa Dithiol, 3-mercaptomethylthio-1,7-dimercapto-2,6-dithiaheptane, 3,6-bis (mercaptomethylthio) -1,9-dimercapto-2,5,8-trithianonane, 4,6-bis (mercapto) Methylthio) -1,9-dimercapto-2,5,8-trithianonane, 3-mercaptomethylthio-1,6-dimercapto-2,5-dithiahexane, 2- (2,2-bis (mercaptomethylthio) ethyl) -1 , 3-dithietane, 1,1,9,9-tetrakis (mercaptomethylthio) -5- (3,3-bis (mercaptomethylthio) -1-thiapropyl) 3,7-dithianonane, tris (2,2-bis ( Mercaptomethylthio) ethyl) methane, tris (4,4-bis (mercaptomethylthio) -2-thiabutyl) me , Tetrakis (2,2-bis (mercaptomethylthio) ethyl) methane, tetrakis (4,4-bis (mercaptomethylthio) -2-thiabutyl) methane, 3,5,9,11-tetrakis (mercaptomethylthio) -1 , 13-dimercapto-2,6,8,12-tetrathiatridecane, 3,5,9,11,15,17-hexakis (mercaptomethylthio) -1,19-dimercapto-2,6,8,12, 14,18-hexathiononadecane, 9- (2,2-bis (mercaptomethylthio) ethyl) -3,5,13,15-tetrakis (mercaptomethylthio) -1,17-dimercapto-2,6,8, 10,12,16-hexathiaheptadecane, 3,4,8,9-tetrakis (mercaptomethylthio) -1,11-dimercapto-2 , 5,7,10-tetrathiaundecane, 3,4,8,9,13,14-hexakis (mercaptomethylthio) -1,16-dimercapto-2,5,7,10,12,15-hexathiahexadecane 8- {bis (mercaptomethylthio) methyl} -3,4,12,13-tetrakis (mercaptomethylthio) -1,15-dimercapto-2,5,7,9,11,14-hexathiapentadecane, 4, 6-bis {3,5-bis (mercaptomethylthio) -7-mercapto-2,6-dithiaheptylthio} -1,3-dithiane, 4- {3,5-bis (mercaptomethylthio) -7-mercapto -2,6-dithiaheptylthio} -6-mercaptomethylthio-1,3-dithiane, 1,1-bis {4- (6-mercaptomethylthio) -1,3-dithi Nilthio} -3,3-bis (mercaptomethylthio) propane, 1,3-bis {4- (6-mercaptomethylthio) -1,3-dithianylthio} -1,3-bis (mercaptomethylthio) propane, 1- { 4- (6-Mercaptomethylthio) -1,3-dithianylthio} -3- {2,2-bis (mercaptomethylthio) ethyl} -7,9-bis (mercaptomethylthio) -2,4,6,10-tetra Thiaundecane, 1- {4- (6-mercaptomethylthio) -1,3-dithianylthio} -3- {2- (1,3-dithietanyl)} methyl-7,9-bis (mercaptomethylthio) -2,4 , 6,10-tetrathiaundecane, 1,5-bis {4- (6-mercaptomethylthio) -1,3-dithianylthio} -3- {2- (1,3-dithieta L)} methyl-2,4-dithiapentane, 4,6-bis [3- {2- (1,3-dithietanyl)} methyl-5-mercapto-2,4-dithiapentylthio] -1,3- Dithiane, 4,6-bis {4- (6-mercaptomethylthio) -1,3-dithianylthio} -1,3-dithiane, 4- {4- (6-mercaptomethylthio) -1,3-dithianylthio} -6 -{4- (6-mercaptomethylthio) -1,3-dithianylthio} -1,3-dithiane, 3- {2- (1,3-dithietanyl)} methyl-7,9-bis (mercaptomethylthio) -1 , 11-dimercapto-2,4,6,10-tetrathiaundecane, 9- {2- (1,3-dithietanyl)} methyl-3,5,13,15-tetrakis (mercaptomethylthio) -1,17- Zimmerka Put-2,6,8,10,12,16-hexathiaheptadecane, 3- {2- (1,3-dithietanyl)} methyl-7,9,13,15-tetrakis (mercaptomethylthio) -1, 17-dimercapto-2,4,6,10,12,16-hexathiaheptadecane, 3,7-bis {2- (1,3-dithietanyl)} methyl-1,9-dimercapto-2,4,6 , 8-tetrathianonane, 4- {3,4,8,9-tetrakis (mercaptomethylthio) -11-mercapto-2,5,7,10-tetrathiaundecyl} -5-mercaptomethylthio-1,3 -Dithiolane, 4,5-bis {3,4-bis (mercaptomethylthio) -6-mercapto-2,5-dithiahexylthio} -1,3-dithiolane, 4- {3,4-bis (mercaptomethyl) H ) -6-mercapto-2,5-dithiahexylthio} -5-mercaptomethylthio-1,3-dithiolane, 4- {3-bis (mercaptomethylthio) methyl-5,6-bis (mercaptomethylthio) -8 -Mercapto-2,4,7-trithiaoctyl} -5-mercaptomethylthio-1,3-dithiolane, 2- [bis {3,4-bis (mercaptomethylthio) -6-mercapto-2,5-dithia Hexylthio} methyl] -1,3-dithietane, 2- {3,4-bis (mercaptomethylthio) -6-mercapto-2,5-dithiahexylthio} mercaptomethylthiomethyl-1,3-dithietane, 2- {3,4,8,9-tetrakis (mercaptomethylthio) -11-mercapto-2,5,7,10-tetrathiaundecylthio} mercapto Tylthiomethyl-1,3-dithietane, 2- {3-bis (mercaptomethylthio) methyl-5,6-bis (mercaptomethylthio) -8-mercapto-2,4,7-trithiaoctyl} mercaptomethylthiomethyl-1, 3-dithietane, 4,5-bis [1- {2- (1,3-dithietanyl)}-3-mercapto-2-thiapropylthio] -1,3-dithiolane, 4- [1- {2- ( 1,3-dithietanyl)}-3-mercapto-2-thiapropylthio] -5- {1,2-bis (mercaptomethylthio) -4-mercapto-3-thiabutylthio} -1,3-dithiolane, 2- [ Bis {4- (5-mercaptomethylthio-1,3-dithiolanyl) thio}] methyl-1,3-dithietane, 4- {4- (5-mercaptomethylthio-1,3-dithio Ranyl) thio} -5- [1- {2- (1,3-dithietanyl)}-3-mercapto-2-thiapropylthio] -1,3-dithiolane and dithioacetal or dithioketal skeletons of these oligomers A compound having
トリス(メルカプトメチルチオ)メタン、トリス(メルカプトエチルチオ)メタン、1,1,5,5−テトラキス(メルカプトメチルチオ)−2,4−ジチアペンタン、ビス[4,4−ビス(メルカプトメチルチオ)−1,3−ジチアブチル](メルカプトメチルチオ)メタン、トリス[4,4−ビス(メルカプトメチルチオ)−1,3−ジチアブチル]メタン、2,4,6−トリス(メルカプトメチルチオ)−1,3,5−トリチアシクロヘキサン、2,4−ビス(メルカプトメチルチオ)−1,3,5−トリチアシクロヘキサン、1,1,3,3−テトラキス(メルカプトメチルチオ)−2−チアプロパン、ビス(メルカプトメチル)メチルチオ−1,3,5−トリチアシクロヘキサン、トリス[(4−メルカプトメチル−2,5−ジチアシクロヘキシル−1−イル)メチルチオ]メタン、2,4−ビス(メルカプトメチルチオ)−1,3−ジチアシクロペンタン、2−メルカプトエチルチオ−4−メルカプトメチル−1,3−ジチアシクロペンタン、2−(2,3−ジメルカプトプロピルチオ)−1,3−ジチアシクロペンタン、4−メルカプトメチル−2−(2,3−ジメルカプトプロピルチオ)−1,3−ジチアシクロペンタン、4−メルカプトメチル−2−(1,3−ジメルカプト−2−プロピルチオ)−1,3−ジチアシクロペンタン、トリス[2,2−ビス(メルカプトメチルチオ)−1−チアエチル]メタン、トリス[3,3−ビス(メルカプトメチルチオ)−2−チアプロピル]メタン、トリス[4,4−ビス(メルカプトメチルチオ)−3−チアブチル]メタン、2,4,6−トリス[3,3−ビス(メルカプトメチルチオ)−2−チアプロピル]−1,3,5−トリチアシクロヘキサン、テトラキス[3,3−ビス(メルカプトメチルチオ)−2−チアプロピル]メタン等、さらにこれらのオリゴマー等のオルトトリチオ蟻酸エステル骨格を有する化合物、 Tris (mercaptomethylthio) methane, tris (mercaptoethylthio) methane, 1,1,5,5-tetrakis (mercaptomethylthio) -2,4-dithiapentane, bis [4,4-bis (mercaptomethylthio) -1,3 -Dithiabutyl] (mercaptomethylthio) methane, tris [4,4-bis (mercaptomethylthio) -1,3-dithiabutyl] methane, 2,4,6-tris (mercaptomethylthio) -1,3,5-trithiacyclohexane 2,4-bis (mercaptomethylthio) -1,3,5-trithiacyclohexane, 1,1,3,3-tetrakis (mercaptomethylthio) -2-thiapropane, bis (mercaptomethyl) methylthio-1,3 5-trithiacyclohexane, tris [(4-mercaptomethyl-2,5-dithi Cyclohexyl-1-yl) methylthio] methane, 2,4-bis (mercaptomethylthio) -1,3-dithiacyclopentane, 2-mercaptoethylthio-4-mercaptomethyl-1,3-dithiacyclopentane, 2 -(2,3-dimercaptopropylthio) -1,3-dithiacyclopentane, 4-mercaptomethyl-2- (2,3-dimercaptopropylthio) -1,3-dithiacyclopentane, 4- Mercaptomethyl-2- (1,3-dimercapto-2-propylthio) -1,3-dithiacyclopentane, tris [2,2-bis (mercaptomethylthio) -1-thiaethyl] methane, tris [3,3- Bis (mercaptomethylthio) -2-thiapropyl] methane, tris [4,4-bis (mercaptomethylthio) -3-thiabutyl] me 2,4,6-tris [3,3-bis (mercaptomethylthio) -2-thiapropyl] -1,3,5-trithiacyclohexane, tetrakis [3,3-bis (mercaptomethylthio) -2-thiapropyl ] Compounds having an ortho trithioformate skeleton such as methane and further oligomers thereof,
3,3’−ジ(メルカプトメチルチオ)−1,5−ジメルカプト−2,4−ジチアペンタン、2,2’−ジ(メルカプトメチルチオ)−1,3−ジチアシクロペンタン、2,7−ジ(メルカプトメチル)−1,4,5,9−テトラチアスピロ[4,4]ノナン、3,9−ジメルカプト−1,5,7,11−テトラチアスピロ[5,5]ウンデカン、更にこれらのオリゴマー等オルトテトラチオ炭酸エステル骨格を有する化合物等が挙げられるが、これらの例示化合物のみに限定されるものではない。これら例示化合物は、単独でも2種類以上混合して使用しても良い。 3,3′-di (mercaptomethylthio) -1,5-dimercapto-2,4-dithiapentane, 2,2′-di (mercaptomethylthio) -1,3-dithiacyclopentane, 2,7-di (mercapto) Methyl) -1,4,5,9-tetrathiaspiro [4,4] nonane, 3,9-dimercapto-1,5,7,11-tetrathiaspiro [5,5] undecane, and oligomers thereof Examples include compounds having an orthotetrathiocarbonate skeleton, but are not limited to these exemplary compounds. These exemplary compounds may be used alone or in combination of two or more.
これら化合物の内、得られる樹脂の光学物性、特にアッベ数を考慮すれば、芳香族系よりも脂肪族系のポリチオール化合物を選択する方が好ましい。更に、光学物性、特に屈折率の要求を考慮すれば、スルフィド結合及び/またはジスルフィド結合等のチオール基以外に硫黄原子を有する化合物を選択するとより好ましく、ジチオアセタール骨格、ジチオケタール骨格、オルトトリチオ蟻酸エステル骨格、オルトテトラチオ炭酸エステル骨格を有する化合物を選択すると更に好ましい。得られる樹脂の耐熱性を考慮し3次元架橋性を上げる為には、3官能以上のポリチオール化合物を1種以上選択すると特に好ましい。以上の点で最も好ましいポリチオールとしては、2,5−ビス(メルカプトメチル)−1,4−ジチアン、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、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、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、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、1,1,1,1−テトラキス(メルカプトメチル)メタン、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、2−(2,2−ビス(メルカプトメチルチオ)エチル)−1,3−ジチエタンからなる化合物群から3官能以上の場合少なくとも1種選択、2官能以上の場合少なくとも1種と3官能以上の化合物を少なくとも1種選択された化合物が挙げられる。 Of these compounds, it is preferable to select an aliphatic polythiol compound rather than an aromatic one in consideration of the optical properties of the resulting resin, particularly the Abbe number. Further, in view of optical properties, particularly refractive index requirements, it is more preferable to select a compound having a sulfur atom in addition to a thiol group such as a sulfide bond and / or a disulfide bond. A dithioacetal skeleton, a dithioketal skeleton, an orthotrithioformate skeleton More preferably, a compound having an orthotetrathiocarbonate skeleton is selected. In order to increase the three-dimensional crosslinkability in consideration of the heat resistance of the resulting resin, it is particularly preferable to select one or more polythiol compounds having three or more functions. As the most preferred polythiol in the above points, 2,5-bis (mercaptomethyl) -1,4-dithiane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 4,8-dimercaptomethyl -1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 5,7-dimercaptomethyl-1 , 11-dimercapto-3,6,9-trithiaundecane, 1,1,1,1-tetrakis (mercaptomethyl) methane, 1,1,3,3-tetrakis (mercaptomethylthio) propane, 1,1,2 , 2-tetrakis (mercaptomethylthio) ethane, 4,6-bis (mercaptomethylthio) -1,3-dithiane, 2- (2,2-bis (me Captomethylthio) ethyl) -1,3-dithietane is a compound selected from at least one compound in the case of three or more functional groups and at least one compound selected from at least one compound and three or more functional compounds in the case of two or more functional groups. It is done.
本発明の樹脂改質剤としてのフェノール化合物類を含むヒドロキシ化合物類の具体例としては、単官能以上のモノまたはポリオールでありフェノール性水酸基も含む。分子内に硫黄原子を含有しているものも含まれる。具体的に単官能化合物としては、メタノール、エタノール、n−プロパノール、イソプロパノール、n−ブタノール、sec−ブタノール、tert−ブタノール、ペンタノール、イソアミルアルコール、ヘキサノール、ヘプタノール、オクタノール、ノニルアルコール、デカノール、ドデシルアルコール、セチルアルコール、イソトリデシルアルコール、ステアリルアルコール、2−エチル−1−ヘキサノール、アリルアルコール、メトキシエタノール、エトキシエタノール、フェノキシエタノール、シクロプロパノール、シクロブタノール、シクロペンタノール、シクロヘキサノール、シクロオクタノール、ベンジルアルコール、フェニルエチルアルコール、メチルシクロヘキサノール、フルフリルアルコール、テトラヒドロフルフリルアルコール、乳酸メチル、乳酸エチル、乳酸ブチル等の脂肪族単官能アルコール化合物、 Specific examples of hydroxy compounds containing phenol compounds as the resin modifier of the present invention are monofunctional or higher mono- or polyols and also include phenolic hydroxyl groups. Those containing a sulfur atom in the molecule are also included. Specific examples of monofunctional compounds include methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, tert-butanol, pentanol, isoamyl alcohol, hexanol, heptanol, octanol, nonyl alcohol, decanol, dodecyl alcohol. Cetyl alcohol, isotridecyl alcohol, stearyl alcohol, 2-ethyl-1-hexanol, allyl alcohol, methoxyethanol, ethoxyethanol, phenoxyethanol, cyclopropanol, cyclobutanol, cyclopentanol, cyclohexanol, cyclooctanol, benzyl alcohol, Phenylethyl alcohol, methylcyclohexanol, furfuryl alcohol, tetrahydrofurfuryl Alcohol, methyl lactate, ethyl lactate, aliphatic, such as butyl lactate monofunctional alcohol compounds,
フェノール、クレゾール、エチルフェノール、メトキシフェノール、エトキシフェノール、メトキシエチルフェノール、クミルフェノール、フェノキシフェノール、tert−ブチルフェノール、ナフトール等の芳香族単官能フェノール化合物、 Aromatic monofunctional phenolic compounds such as phenol, cresol, ethylphenol, methoxyphenol, ethoxyphenol, methoxyethylphenol, cumylphenol, phenoxyphenol, tert-butylphenol, naphthol,
2官能以上のポリオール化合物としては、例えば、エチレングリコール、ジエチレングリコール、プロピレングリコール、ジプロピレングリコール、ブチレングリコール、ネオペンチルグリコール、グリセリン、トリメチロールエタン、トリメチロールプロパン、ブタントリオール、1,2−メチルグリコサイド、ペンタエリスリトール、ジペンタエリスリトール、トリペンタエリスリトール、ソルビトール、エリスリトール、スレイトール、マニトール、リビトール、アラビニトール、キシリトール、アリトール、ドルシトール、グリコール、イノシトール、ヘキサントリオール、トリグリセロール、トリエチレングリコール、ポリエチレヌリコール、トリス(2−ヒドロキシエチル)イソシアヌレート、シクロブタンジオール、シクロペンタンジオール、シクロヘキサンジオール、シクロヘプタンジオール、シクロオクタンジオール、シクロヘキサンジメタノール、ヒドロキシプロピルシクロヘキサノール、ビシクロ[4,3,0]−ノナンジオール、ジシクロヘキサンジオール、トリシクロ[5,3,1,1]ドデカンジオール、ビシクロ[4,3,0]−ノナンジメタノール、ジシクロヘキサンジオール、トリシクロ[5,3,1,1]ドデカンジエタノール、スピロ[3,4]オクタンジオール、ブチルシクロヘキサンジオール、1,1−ビシクロヘキシリデンジオール、シクロヘキサントリオール、マルチトール、ラクチトール、ジヒドロキシナフタレン、トリヒドロキシナフタレン、テトラヒドロキシナフタレン、ジヒドロキシベンゼン、ベンゼントリオール、ビフェニルテトラオール、トリヒドロキシフェナントレン、ビスフェノールA、ビスフェノールF、キシリレングリコール、ビス(2−ヒドロキシエトキシ)ベンゼン、ビスフェノールA−ビス(2−ヒドロキシエチルエーテル)、テトラブロモビスフェノールA、テトラブロモビスフェノールA−ビス(2−ヒドロキシエチルエーテル)、ジブロモネオペンチルグリコール等のポリオール、 Examples of the bifunctional or higher polyol compound include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, neopentyl glycol, glycerin, trimethylol ethane, trimethylol propane, butane triol, and 1,2-methyl glycoside. , Pentaerythritol, dipentaerythritol, tripentaerythritol, sorbitol, erythritol, threitol, mannitol, ribitol, arabinitol, xylitol, allitol, dolcitol, glycol, inositol, hexanetriol, triglycerol, triethylene glycol, polyethylene glycol, tris ( 2-hydroxyethyl) isocyanurate, cyclobutanediol, cyclope Tandiol, cyclohexanediol, cycloheptanediol, cyclooctanediol, cyclohexanedimethanol, hydroxypropylcyclohexanol, bicyclo [4,3,0] -nonanediol, dicyclohexanediol, tricyclo [5,3,1,1] dodecanediol , Bicyclo [4,3,0] -nonanedimethanol, dicyclohexanediol, tricyclo [5,3,1,1] dodecanediethanol, spiro [3,4] octanediol, butylcyclohexanediol, 1,1-bicyclohexene Silidenediol, cyclohexanetriol, maltitol, lactitol, dihydroxynaphthalene, trihydroxynaphthalene, tetrahydroxynaphthalene, dihydroxybenzene, benzenetriol, bif Nyltetraol, trihydroxyphenanthrene, bisphenol A, bisphenol F, xylylene glycol, bis (2-hydroxyethoxy) benzene, bisphenol A-bis (2-hydroxyethyl ether), tetrabromobisphenol A, tetrabromobisphenol A-bis (2-hydroxyethyl ether), polyols such as dibromoneopentyl glycol,
このほかにシュウ酸、グルタミン酸、アジピン酸、酢酸、プロピオン酸、フタル酸、イソフタル酸、サリチル酸、ピロメリット酸、3−ブロモプロピオン酸、2−ブロモグリコール酸、ジカルボキシシクロヘキサン、ブタンテトラカルボン酸、ブロモフタル酸等の有機多塩基酸と前記ポリオールの縮合反応生成物、前記ポリオールとエチレンオキサイドやプロピレンオキサイドなどアルキレンオキサイドとの付加反応生成物等が挙げられるが、例示化合物に限定されるものではない。さらには、これらの塩素置換体、臭素置換体等のハロゲン置換体を使用してもよい。 In addition, oxalic acid, glutamic acid, adipic acid, acetic acid, propionic acid, phthalic acid, isophthalic acid, salicylic acid, pyromellitic acid, 3-bromopropionic acid, 2-bromoglycolic acid, dicarboxycyclohexane, butanetetracarboxylic acid, bromophthalate Examples include condensation reaction products of an organic polybasic acid such as an acid and the polyol, and addition reaction products of the polyol and an alkylene oxide such as ethylene oxide and propylene oxide, but are not limited to the exemplified compounds. Furthermore, you may use halogen substituted bodies, such as these chlorine substituted bodies and bromine substituted bodies.
また、硫黄原子を含有するモノまたはポリオール化合物としては、例えばビス[4−(ヒドロキシエトキシ)フェニル]スルフィド、ビス[4−(2−ヒドロキシプロポキシ)フェニル]スルフィド、ビス[4−(2,3−ジヒドロキシプロポキシ)フェニル]スルフィド、ビス[4−(4−ヒドロキシシクロヘキシロキシ)フェニル]スルフィド、ビス[2−メチル−4−(ヒドロキシエトキシ)−6−ブチルフェニル]スルフィドおよびこれらの化合物に水酸基あたり平均3分子以下のエチレンオキシドおよび/またはプロピレンオキシドが付加された化合物、ビス(2−ヒドロキシエチル)スルフィド、1,2−ビス(2−ヒドロキシエチルメルカプト)エタン、ビス(2−ヒドロキシエチル)ジスルフィド、1,4−ジチアン−2,5−ジオール、ビス(2,3−ジヒドロキシプロピル)スルフィド、テトラキス(4−ヒドロキシ−2−チアブチル)メタン、ビス(4−ヒドロキシフェニル)スルホン(ビスフェノールS)、テトラブロモビスフェノールS、テトラメチルビスフェノールS、4,4−チオビス(6−tert−ブチル−3−メチルフェノール)、1,3−ビス(2−ヒドロキシエチルチオエチル)シクロヘキサン等が挙げられるが、例示化合物に限定されるものではない。さらには、これらの塩素置換体、臭素置換体等のハロゲン置換体を使用してもよい。 Examples of the mono- or polyol compound containing a sulfur atom include bis [4- (hydroxyethoxy) phenyl] sulfide, bis [4- (2-hydroxypropoxy) phenyl] sulfide, and bis [4- (2,3- Dihydroxypropoxy) phenyl] sulfide, bis [4- (4-hydroxycyclohexyloxy) phenyl] sulfide, bis [2-methyl-4- (hydroxyethoxy) -6-butylphenyl] sulfide and these compounds on average 3 per hydroxyl group Compounds having an ethylene oxide and / or propylene oxide added thereto, bis (2-hydroxyethyl) sulfide, 1,2-bis (2-hydroxyethylmercapto) ethane, bis (2-hydroxyethyl) disulfide, 1,4 -Dithian-2, -Diol, bis (2,3-dihydroxypropyl) sulfide, tetrakis (4-hydroxy-2-thiabutyl) methane, bis (4-hydroxyphenyl) sulfone (bisphenol S), tetrabromobisphenol S, tetramethylbisphenol S, 4 , 4-thiobis (6-tert-butyl-3-methylphenol), 1,3-bis (2-hydroxyethylthioethyl) cyclohexane and the like, but are not limited to the exemplified compounds. Furthermore, you may use halogen substituted bodies, such as these chlorine substituted bodies and bromine substituted bodies.
本発明の樹脂改質剤としてのイソ(チオ)シアナート化合物類の具体例としては、メチルイソシアナート、エチルイソシアナート、n−プロピルイソシアナート、イソプロピルイソシアナート、n−ブチルイソシアナート、sec−ブチルイソシアナート、tert−ブチルイソシアナート、ペンチルイソシアナート、ヘキシルイソシアナート、ヘプチルイソシアナート、オクチルイソシアナート、デシルイソシアナート、ラウリルイソシアナート、ミリスチルイソシアナート、オクタデシルイソシアナート、3−ペンチルイソシアナート、2−エチルヘキシルイソシアナート、2,3−ジメチルシクロヘキシルイソシアナート、2−メトキシフェニルイソシアナート、4−メトキシフェニルイソシアナート、α−メチルベンジルイソシアナート、フェニルエチルイソシアナート、フェニルイソシアナート、o−、m−、あるいはp−トリルイソシアナート、シクロヘキシルイソシアナート、ベンジルイソシアナート、イソシアナートメチルビシクロヘプタン等の単官能イソシアナート化合物、 Specific examples of the iso (thio) cyanate compounds as the resin modifier of the present invention include methyl isocyanate, ethyl isocyanate, n-propyl isocyanate, isopropyl isocyanate, n-butyl isocyanate, sec-butyl isocyanate. Nert, tert-butyl isocyanate, pentyl isocyanate, hexyl isocyanate, heptyl isocyanate, octyl isocyanate, decyl isocyanate, lauryl isocyanate, myristyl isocyanate, octadecyl isocyanate, 3-pentyl isocyanate, 2-ethylhexyl isocyanate Narate, 2,3-dimethylcyclohexyl isocyanate, 2-methoxyphenyl isocyanate, 4-methoxyphenyl isocyanate, α-methylbenzyl isocyanate DOO, phenylethyl isocyanate, phenyl isocyanate, o-, m-, or p- tolyl isocyanate, cyclohexyl isocyanate, benzyl isocyanate, monofunctional isocyanate compounds such as isocyanate methyl bicycloheptane,
ヘキサメチレンジイソシアナート、2,2−ジメチルペンタンジイソシアナート、2,2,4−トリメチルヘキサンジイソシアナート、ブテンジイソシアナート、1,3−ブタジエン−1,4−ジイソシアナート、2,4,4−トリメチルヘキサメチレンジイソシアナート、1,6,11−ウンデカトリイソシアナート、1,3,6−ヘキサメチレントリイソシアナート、1,8−ジイソシアナト−4−イソシアナトメチルオクタン、ビス(イソシアナトエチル)カーボネート、ビス(イソシアナトエチル)エーテル、リジンジイソシアナトメチルエステル、リジントリイソシアナート、キシリレンジイソシアナート、ビス(イソシアナトエチル)ベンゼン、ビス(イソシアナトプロピル)ベンゼン、α,α,α’,α’−テトラメチルキシリレンジイソシアナート、ビス(イソシアナトブチル)ベンゼン、ビス(イソシアナトメチル)ナフタリン、ビス(イソシアナトメチル)ジフェニルエーテル、ビス(イソシアナトエチル)フタレート、メシチリレントリイソシアナート、2,6−ジ(イソシアナトメチル)フラン等の脂肪族ポリイソシアナート化合物、 Hexamethylene diisocyanate, 2,2-dimethylpentane diisocyanate, 2,2,4-trimethylhexane diisocyanate, butene diisocyanate, 1,3-butadiene-1,4-diisocyanate, 2,4 , 4-trimethylhexamethylene diisocyanate, 1,6,11-undecatriisocyanate, 1,3,6-hexamethylene triisocyanate, 1,8-diisocyanato-4-isocyanatomethyloctane, bis (isocyanato Ethyl) carbonate, bis (isocyanatoethyl) ether, lysine diisocyanate methyl ester, lysine triisocyanate, xylylene diisocyanate, bis (isocyanatoethyl) benzene, bis (isocyanatopropyl) benzene, α, α, α ', Α'-tetramethylxylyl Diisocyanate, bis (isocyanatobutyl) benzene, bis (isocyanatomethyl) naphthalene, bis (isocyanatomethyl) diphenyl ether, bis (isocyanatoethyl) phthalate, mesityrylene triisocyanate, 2,6-di (isocyanate) Aliphatic polyisocyanate compounds such as natomethyl) furan,
イソホロンジイソシアナート、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ナート、シクロヘキサンジイソシアナート、メチルシクロヘキサンジイソシアナート、ジシクロヘキシルジメチルメタンジイソシアナート、2,2−ジメチルジシクロヘキシルメタンジイソシアナート、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ナート化合物、 Isophorone diisocyanate, bis (isocyanatomethyl) cyclohexane, dicyclohexylmethane diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, dicyclohexyldimethylmethane diisocyanate, 2,2-dimethyldicyclohexylmethane diisocyanate, 2, 5-bis (isocyanatomethyl) bicyclo- [2,2,1] -heptane, 2,6-bis (isocyanatomethyl) bicyclo- [2,2,1] -heptane, 3,8-bis (isocyanato Fats such as methyl) tricyclodecane, 3,9-bis (isocyanatomethyl) tricyclodecane, 4,8-bis (isocyanatomethyl) tricyclodecane, 4,9-bis (isocyanatomethyl) tricyclodecane Cyclic polyisocyanate compounds,
フェニレンジイソシアナート、トリレンジイソシアナート、エチルフェニレンジイソシアナート、イソプロピルフェニレンジイソシアナート、ジメチルフェニレンジイソシアナート、ジエチルフェニレンジイソシアナート、ジイソプロピルフェニレンジイソシアナート、トリメチルベンゼントリイソシアナート、ベンゼントリイソシアナート、ビフェニルジイソシアナート、トルイジンジイソシアナート、4,4−ジフェニルメタンジイソシアナート、3,3−ジメチルジフェニルメタン−4,4−ジイソシアナート、ビベンジル−4,4−ジイソシアナート、ビス (イソシアナトフェニル)エチレン、3,3−ジメトキシビフェニル−4,4−ジイソシアナート、フェニルイソシアナトエチルイソシアナート、ヘキサヒドロベンゼンジイソシアナート、ヘキサヒドロジフェニルメタン−4,4−ジイソシアナート等の芳香族ポリイソシアナート化合物、 Phenylene diisocyanate, tolylene diisocyanate, ethylphenylene diisocyanate, isopropylphenylene diisocyanate, dimethylphenylene diisocyanate, diethylphenylene diisocyanate, diisopropylphenylene diisocyanate, trimethylbenzene triisocyanate, benzene triisocyanate , Biphenyl diisocyanate, toluidine diisocyanate, 4,4-diphenylmethane diisocyanate, 3,3-dimethyldiphenylmethane-4,4-diisocyanate, bibenzyl-4,4-diisocyanate, bis (isocyanatophenyl ) Ethylene, 3,3-dimethoxybiphenyl-4,4-diisocyanate, phenylisocyanatoethyl isocyanate, hexahydrobenzene diiso Annatto, aromatic polyisocyanate compound such as hexahydroterephthalic diphenylmethane-4,4-diisocyanate,
ビス(イソシアナトメチル)スルフィド、ビス(イソシアナトエチル)スルフィド、ビス(イソシアナトプロピル)スルフィド、ビス(イソシアナトヘキシル)スルフィド、ビス(イソシアナトメチル)スルホン、ビス(イソシアナトメチル)ジスルフィド、ビス(イソシアナトエチル)ジスルフィド、ビス(イソシアナトプロピル)ジスルフィド、ビス(イソシアナトメチルチオ)メタン、ビス(イソシアナトエチルチオ)メタン、ビス(イソシアナトエチルチオ)エタン、ビス(イソシアナトメチルチオ)エタン、1,5−ジイソシアナト−2−イソシアナトメチル−3−チアペンタン等の含硫脂肪族イソシアナート化合物、 Bis (isocyanatomethyl) sulfide, bis (isocyanatoethyl) sulfide, bis (isocyanatopropyl) sulfide, bis (isocyanatohexyl) sulfide, bis (isocyanatomethyl) sulfone, bis (isocyanatomethyl) disulfide, bis ( Isocyanatoethyl) disulfide, bis (isocyanatopropyl) disulfide, bis (isocyanatomethylthio) methane, bis (isocyanatoethylthio) methane, bis (isocyanatoethylthio) ethane, bis (isocyanatomethylthio) ethane, 1, Sulfur-containing aliphatic isocyanate compounds such as 5-diisocyanato-2-isocyanatomethyl-3-thiapentane,
ジフェニルスルフィド−2,4−ジイソシアナート、ジフェニルスルフィド−4,4−ジイソシアナート、3,3−ジメトキシ−4,4−ジイソシアナトジベンジルチオエーテル、ビス(4−イソシアナトメチルベンゼン)スルフィド、4,4−メトキシベンゼンチオエチレングリコール−3,3−ジイソシアナートなどの芳香族スルフィド系イソシアナート化合物、 Diphenyl sulfide-2,4-diisocyanate, diphenyl sulfide-4,4-diisocyanate, 3,3-dimethoxy-4,4-diisocyanatodibenzylthioether, bis (4-isocyanatomethylbenzene) sulfide, Aromatic sulfide isocyanate compounds such as 4,4-methoxybenzenethioethylene glycol-3,3-diisocyanate,
ジフェニルジスルフィド−4,4−ジイソシアナート、2,2−ジメチルジフェニルジスルフィド−5,5−ジイソシアナート、3,3−ジメチルジフェニルジスルフィド−5,5−ジイソシアナート、3,3−ジメチルジフェニルジスルフィド−6,6−ジイソシアナート、4,4−ジメチルジフェニルジスルフィド−5,5−ジイソシアナート、3,3−ジメトキシジフェニルジスルフィド−4,4−ジイソシアナート、4,4−ジメトキシジフェニルジスルフィド−3,3−ジイソシアナートなどの芳香族ジスルフィド系イソシアナート化合物、2,5−ジイソシアナトチオフェン、2,5−ビス(イソシアナトメチル)チオフェン等の含硫複素環化合物、 Diphenyl disulfide-4,4-diisocyanate, 2,2-dimethyldiphenyl disulfide-5,5-diisocyanate, 3,3-dimethyldiphenyl disulfide-5,5-diisocyanate, 3,3-dimethyldiphenyl disulfide 6,6-diisocyanate, 4,4-dimethyldiphenyl disulfide-5,5-diisocyanate, 3,3-dimethoxydiphenyl disulfide-4,4-diisocyanate, 4,4-dimethoxydiphenyl disulfide-3 Aromatic disulfide-based isocyanate compounds such as 1,3-diisocyanate, sulfur-containing heterocyclic compounds such as 2,5-diisocyanatothiophene, 2,5-bis (isocyanatomethyl) thiophene,
その他にも、2,5−ジイソシアナトテトラヒドロチオフェン、2,5−ビス(イソシアナトメチル)テトラヒドロチオフェン、3,4−ビス(イソシアナトメチル)テトラヒドロチオフェン、2,5−ジイソシアナト−1,4−ジチアン、2,5−ビス(イソシアナトメチル)−1,4−ジチアン、4,5−ジイソシアナト−1,3−ジチオラン、4,5−ビス(イソシアナトメチル)−1,3−ジチオラン、4,5−ビス(イソシアナトメチル)−2−メチル−1,3−ジチオランなどが挙げられるが、例示化合物に限定されるものではない。また、これらの塩素置換体、臭素置換体等のハロゲン置換体、アルキル置換体、アルコキシ置換体、ニトロ置換体や多価アルコールとのプレポリマー型変性体、カルボジイミド変性体、ウレア変性体、ビュレット変性体、ダイマー化あるいはトリマー化反応生成物等も使用できる。 In addition, 2,5-diisocyanatotetrahydrothiophene, 2,5-bis (isocyanatomethyl) tetrahydrothiophene, 3,4-bis (isocyanatomethyl) tetrahydrothiophene, 2,5-diisocyanato-1,4- Dithiane, 2,5-bis (isocyanatomethyl) -1,4-dithiane, 4,5-diisocyanato-1,3-dithiolane, 4,5-bis (isocyanatomethyl) -1,3-dithiolane, 4, Examples thereof include 5-bis (isocyanatomethyl) -2-methyl-1,3-dithiolane, but are not limited to the exemplified compounds. In addition, halogen-substituted products such as chlorine-substituted products, bromine-substituted products, alkyl-substituted products, alkoxy-substituted products, nitro-substituted products, prepolymer-modified products with polyhydric alcohols, carbodiimide-modified products, urea-modified products, and burette-modified products. Bodies, dimerization or trimerization reaction products and the like can also be used.
更に、イソチオシアナート化合物の具体例としては、メチルイソチオシアナート、エチルイソチオシアナート、n−プロピルチオイソシアナート、イソプロピルイソチオシアナート、n−ブチルイソチオシアナート、sec−ブチルイソチオシアナート、tert−ブチルイソチオシアナート、ペンチルイソチオシアナート、ヘキシルイソチオシアナート、ヘプチルイソチオシアナート、オクチルイソチオシアナート、デシルイソチオシアナート、ラウリルイソチオシアナート、ミリスチルイソチオシアナート、オクタデシルイソチオシアナート、3−ペンチルイソチオシアナート、2−エチルヘキシルイソチオシアナート、2,3−ジメチルシクロヘキシルイソチオシアナート、2−メトキシフェニルイソチオシアナート、4−メトキシフェニルイソチオシアナート、α−メチルベンジルイソチオシアナート、フェニルエチルイソチオシアナート、フェニルイソチオシアナート、o−、m−、あるいはp−トリルイソチオシアナート、シクロヘキシルイソチオシアナート、ベンジルイソチオシアナート、イソチオシアナートメチルビシクロヘプタン等の単官能イソチオシアナート化合物、 Specific examples of the isothiocyanate compound include methyl isothiocyanate, ethyl isothiocyanate, n-propyl thioisocyanate, isopropyl isothiocyanate, n-butyl isothiocyanate, sec-butyl isothiocyanate, tert- Butyl isothiocyanate, pentyl isothiocyanate, hexyl isothiocyanate, heptyl isothiocyanate, octyl isothiocyanate, decyl isothiocyanate, lauryl isothiocyanate, myristyl isothiocyanate, octadecyl isothiocyanate, 3-pentyl isothiocyanate Narate, 2-ethylhexyl isothiocyanate, 2,3-dimethylcyclohexyl isothiocyanate, 2-methoxyphenyl isothiocyanate, 4-methoxyphenyl Nyl isothiocyanate, α-methylbenzyl isothiocyanate, phenylethyl isothiocyanate, phenyl isothiocyanate, o-, m-, or p-tolyl isothiocyanate, cyclohexyl isothiocyanate, benzyl isothiocyanate, isothiocyan Monofunctional isothiocyanate compounds such as natomethylbicycloheptane,
1,6−ジイソチオシアナトヘキサン、p−フェニレンイソプロピリデンジイソチオシアナート等の脂肪族ポリイソチオシアナート化合物、 Aliphatic polyisothiocyanate compounds such as 1,6-diisothiocyanatohexane, p-phenyleneisopropylidenediisothiocyanate,
シクロヘキサンジイソチオシアナート、ジイソチオシアナトメチルビシクロヘプタン等の脂環族ポリイソチオシアナート化合物、 Cycloaliphatic diisothiocyanate, alicyclic polyisothiocyanate compounds such as diisothiocyanatomethylbicycloheptane,
1,2−ジイソチオシアナトベンゼン、1,3−ジイソチオシアナトベンゼン、1,4−ジイソチオシアナトベンゼン、2,4−ジイソチオシアナトトルエン、2,5−ジイソチオシアナト−m−キシレン、4,4−ジイソチオシアナト−1,1−ビフェニル、1,1−メチレンビス(4−イソチオシアナトベンゼン)、1,1−メチレンビス(4−イソチオシアナト−2−メチルベンゼン)、1,1−メチレンビス(4−イソチオシアナト−3−メチルベンゼン)、1,1−(1,2−エタンジイル)ビス(イソチオシアナトベンゼン)、4,4−ジイソチオシアナトベンゾフェノン、4,4−ジイソチオシアナト−3,3−ジメチルベンゾフェノン、ジフェニルエーテル−4,4−ジイソチオシアナート、ジフェニルアミン−4,4−ジイソチオシアナート等の芳香族イソチオシアナート化合物、さらには、1,3−ベンゼンジカルボニルジイソチオシアナート、1,4−ベンゼンジカルボニルジイソチオシアナート、(2,2−ピリジン)−4,4−ジカルボニルジイソチオシアナート等のカルボニルイソチオシアナート化合物等が挙げられるが、例示化合物に限定されるものではない。 1,2-diisothiocyanatobenzene, 1,3-diisothiocyanatobenzene, 1,4-diisothiocyanatobenzene, 2,4-diisothiocyanatotoluene, 2,5-diisothiocyanato-m Xylene, 4,4-diisothiocyanato-1,1-biphenyl, 1,1-methylenebis (4-isothiocyanatobenzene), 1,1-methylenebis (4-isothiocyanato-2-methylbenzene), 1, 1-methylenebis (4-isothiocyanato-3-methylbenzene), 1,1- (1,2-ethanediyl) bis (isothiocyanatobenzene), 4,4-diisothiocyanatobenzophenone, 4,4-diisothiocyana -3,3-dimethylbenzophenone, diphenyl ether-4,4-diisothiocyanate, diphenylamine-4,4-di Aromatic isothiocyanate compounds such as soothiocyanate, further 1,3-benzenedicarbonyldiisothiocyanate, 1,4-benzenedicarbonyldiisothiocyanate, (2,2-pyridine) -4,4-di Examples include carbonyl isothiocyanate compounds such as carbonyl diisothiocyanate, but are not limited to the exemplified compounds.
また、イソチオシアナト基のほかに1個以上の硫黄原子を含有するイソチオシアナート化合物の具体例としては、チオビス(3−イソチオシアナトプロパン)、チオビス(2−イソチオシアナトエタン)、ジチオビス(2−イソチオシアナトエタン)等の含硫脂肪族イソチオシアナート化合物、1−イソチオシアナト−4−[(2−イソチオシアナト)スルホニル]ベンゼン、チオビス(4−イソチオシアナトベンゼン)、スルホニルビス(4−イソチオシアナトベンゼン)、ジチオビス(4−イソチオシアナトベンゼン)等の含硫芳香族イソチオシアナート化合物、2,5−ジイソチオシアナトチオフェン、2,5−ジイソチオシアナト−1,4−ジチアン等の含硫複素環化合物等が挙げられるが、例示化合物に限定されるものではない。さらに、これらの塩素置換体、臭素置換体等のハロゲン置換体、アルキル置換体、アルコキシ置換体、ニトロ置換体や多価アルコールとのプレポリマー型変性体、カルボジイミド変性体、ウレア変性体、ビュレット変性体、ダイマー化あるいはトリマー化反応生成物等も使用できる。 Specific examples of the isothiocyanate compound containing one or more sulfur atoms in addition to the isothiocyanato group include thiobis (3-isothiocyanatopropane), thiobis (2-isothiocyanatoethane), dithiobis (2- Sulfur-containing aliphatic isothiocyanate compounds such as isothiocyanatoethane), 1-isothiocyanato-4-[(2-isothiocyanato) sulfonyl] benzene, thiobis (4-isothiocyanatobenzene), sulfonylbis (4-isothiocyanato) Benzene), sulfur-containing aromatic isothiocyanate compounds such as dithiobis (4-isothiocyanatobenzene), 2,5-diisothiocyanatothiophene, 2,5-diisothiocyanato-1,4-dithiane, etc. Although sulfur heterocyclic compounds etc. are mentioned, it is not limited to an exemplary compound. Furthermore, halogen-substituted products such as chlorine-substituted products and bromine-substituted products, alkyl-substituted products, alkoxy-substituted products, nitro-substituted products, prepolymer-modified products with polyhydric alcohols, carbodiimide-modified products, urea-modified products, and burette-modified products. Bodies, dimerization or trimerization reaction products can also be used.
更に、イソシアナト基を有するイソチオシアナート化合物も挙げられる。1−イソシアナト−6−イソチオシアナトヘキサン、1−イソシアナト−4−イソチオシアナトシクロヘキサン等の脂肪族、脂環族化合物、1−イソシアナト−4−イソチオシアナトベンゼン、4−メチル−3−イソシアナト−1−イソチオシアナトベンゼン等の芳香族化合物、2−イソシアナト−4,6−ジイソチオシアナト−1,3,5−トリアジン等の複素環式化合物、さらには、4−イソシアナト−4’−イソチオシアナトジフェニルスルフィド、2−イソシアナト−2’−イソチオシアナトジエチルジスルフィド等のイソチオシアナト基以外にも硫黄原子を含有する化合物等であるが、例示化合物に限定されるものではない。さらに、これらの塩素置換体、臭素置換体等のハロゲン置換体、アルキル置換体、アルコキシ置換体、ニトロ置換体や多価アルコールとのプレポリマー型変性体、カルボジイミド変性体、ウレア変性体、ビュレット変性体、ダイマー化あるいはトリマー化反応生成物等も使用できる。 Furthermore, the isothiocyanate compound which has an isocyanato group is also mentioned. Aliphatic and alicyclic compounds such as 1-isocyanato-6-isothiocyanatohexane, 1-isocyanato-4-isothiocyanatocyclohexane, 1-isocyanato-4-isothiocyanatobenzene, 4-methyl-3-isocyanato- Aromatic compounds such as 1-isothiocyanatobenzene, heterocyclic compounds such as 2-isocyanato-4,6-diisothiocyanato-1,3,5-triazine, and 4-isocyanato-4′-isothi In addition to isothiocyanato groups such as isocyanatodiphenyl sulfide and 2-isocyanato-2′-isothiocyanatodiethyl disulfide, compounds containing sulfur atoms are not limited to the exemplified compounds. Furthermore, halogen-substituted products such as chlorine-substituted products and bromine-substituted products, alkyl-substituted products, alkoxy-substituted products, nitro-substituted products, prepolymer-modified products with polyhydric alcohols, carbodiimide-modified products, urea-modified products, and burette-modified products. Bodies, dimerization or trimerization reaction products can also be used.
本発明の樹脂改質剤としてのメルカプト有機酸化合物の好ましいものの具体例としては、チオグリコール酸、3−メルカプトプロピオン酸、チオ酢酸、チオ乳酸、チオリンゴ酸、チオサリチル酸等が挙げられるが、例示化合物のみに限定されるものではない。また、上記メルカプト有機酸化合物は単独でも、2種類以上を混合して使用してもかまわない。 Specific examples of preferred mercapto organic acid compounds as the resin modifier of the present invention include thioglycolic acid, 3-mercaptopropionic acid, thioacetic acid, thiolactic acid, thiomalic acid, thiosalicylic acid, and the like, but exemplary compounds It is not limited to only. Moreover, the said mercapto organic acid compound may be used individually or in mixture of 2 or more types.
有機酸及びその無水物の好ましいものの具体例としては、蟻酸、酢酸、プロピオン酸、酪酸、安息香酸、p−トルエンスルホン酸、メタンスルホン酸等の炭化水素系有機酸及びそのハロゲン、ニトロ、シアノ化体等の単官能有機酸および、トリフルオロ酢酸無水物、クロロ酢酸無水物、ジクロロ酢酸無水物、トリクロロ酢酸無水物、無水フタル酸、ヘキサヒドロ無水フタル酸、メチルヘキサヒドロ無水フタル酸、メチルテトラヒドロ無水フタル酸、メチルノルボルネン酸無水物、メチルノルボルナン酸無水物、無水マレイン酸、無水トリメリット酸、無水ピロメリット酸等の酸無水物、フタル酸、コハク酸等の2官能有機酸、チオジグリコール酸、チオジプロピオン酸、ジチオジプロピオン酸等の含硫有機酸等が挙げられるが、例示化合物のみに限定されるものではない。 Specific examples of preferred organic acids and their anhydrides include hydrocarbon-based organic acids such as formic acid, acetic acid, propionic acid, butyric acid, benzoic acid, p-toluenesulfonic acid, methanesulfonic acid, and their halogens, nitro, cyanation Monofunctional organic acids such as trifluoroacetic anhydride, chloroacetic anhydride, dichloroacetic anhydride, trichloroacetic anhydride, phthalic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, methyltetrahydrophthalic anhydride Acid, methylnorbornenoic anhydride, methylnorbornanoic anhydride, maleic anhydride, trimellitic anhydride, pyromellitic anhydride, etc., bifunctional organic acids such as phthalic acid, succinic acid, thiodiglycolic acid, Examples include sulfur-containing organic acids such as thiodipropionic acid and dithiodipropionic acid. The present invention is not limited to.
オレフィン類の好ましいものの具体例としては、ベンジルアクリレート、ベンジルメタクリレート、ブチキシエチルアクリレート、ブトキシメチルメタクリレート、シクロヘキシルアクリレート、シクロヘキシルメタクリレート、2−ヒドロキシエチルアクリレート、2−ヒドロキシメチルメタクリレート、グリシジルアクリレート、グリシジルメタクリレート、フェノキシエチルアクリレート、フェノキシエチルメタクリレート、フェニルメタクリレート、エチレングリコールジアクリレート、エチレングリコールジメタクリレート、ジエチレングリコールジアクリレート、ジエチレングリコールジメタクリレート、トリエチレングリコールジアクリレート、トリエチレングリコールジメタクリレート、テトラエチレングリコールジアクリレート、テトラエチレングリコールジメタクリレート、ポリエチレングリコールジアクリレート、ポリエチレングリコールジメタクリレート、ネオペンチルグリコールジアクリレート、ネオペンチルグリコールジメタクリレート、エチレングリコールビスグリシジルアクリレート、エチレングリコールビスグリシジルメタクリレート、ビスフェノールAジアクリレート、ビスフェノールAジメタクリレート、2,2−ビス(4−アクロキシエトキシフェニル)プロパン、2,2−ビス(4−メタクロキシエトキシフェニル)プロパン、2,2−ビス(4−アクロキシジエトキシフェニル)プロパン、2,2−ビス(4−メタクロキシジエトキシフェニル)プロパン、ビスフェノールFジアクリレート、ビスフェノールFジメタクリレート、1,1−ビス(4−アクロキシエトキシフェニル)メタン、1,1−ビス(4−メタクロキシエトキシフェニル)メタン、1,1−ビス(4−アクロキシジエトキシフェニル)メタン、1,1−ビス(4−メタクロキシジエトキシフェニル)メタン、ジメチロールトリシクロデカンジアクリレート、トリメチロールプロパントリアクリレート、トリメチロールプロパントリメタクリレート、グリセロールジアクリレート、グリセロールジメタクリレート、ペンタエリスリトールトリアクリレート、ペンタエリスリトールテトラアクリレート、ペンタエリスリトールテトラメタクリレート、メチルチオアクリレート、メチルチオメタクリレート、フェニルチオアクリレート、ベンジルチオメタクリレート、キシリレンジチオールジアクリレート、キシリレンジチオールジメタクリレート、メルカプトエチルスルフィドジアクリレート、メルカプトエチルスルフィドジメタクリレート等の(メタ)アクリレート化合物、 Specific examples of preferred olefins include benzyl acrylate, benzyl methacrylate, butoxyethyl acrylate, butoxymethyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxymethyl methacrylate, glycidyl acrylate, glycidyl methacrylate, phenoxy. Ethyl acrylate, phenoxyethyl methacrylate, phenyl methacrylate, ethylene glycol diacrylate, ethylene glycol dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, tetraethylene glycol diacrylate , Tetraethylene glycol dimethacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, ethylene glycol bisglycidyl acrylate, ethylene glycol bisglycidyl methacrylate, bisphenol A diacrylate, bisphenol A Dimethacrylate, 2,2-bis (4-acryloxyethoxyphenyl) propane, 2,2-bis (4-methacryloxyethoxyphenyl) propane, 2,2-bis (4-acryloxyethoxyphenyl) propane, 2 , 2-bis (4-methacryloxydiethoxyphenyl) propane, bisphenol F diacrylate, bisphenol F dimethacrylate, 1 1-bis (4-acryloxyethoxyphenyl) methane, 1,1-bis (4-methacryloxyethoxyphenyl) methane, 1,1-bis (4-acryloxyethoxyphenyl) methane, 1,1-bis ( 4-methacryloxydiethoxyphenyl) methane, dimethyloltricyclodecane diacrylate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, glycerol diacrylate, glycerol dimethacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, pentaerythritol Tetramethacrylate, methylthioacrylate, methylthiomethacrylate, phenylthioacrylate, benzylthiomethacrylate, xylylenedithiol diacrylate, key (Meth) acrylate compounds such as silylenedithiol dimethacrylate, mercaptoethyl sulfide diacrylate, mercaptoethyl sulfide dimethacrylate,
アリルグリシジルエーテル、ジアリルフタレート、ジアリルテレフタレート、ジアリルイソフタレート、ジアリルカーボネート、ジエチレングリコールビスアリルカーボネート等のアリル化合物、スチレン、クロロスチレン、メチルスチレン、ブロモスチレン、ジブロモスチレン、ジビニルベンゼン、3,9−ジビニルスピロビ(m−ジオキサン)、ジビニルスルフィド、ジビニルジスルフィド等のビニル化合物、ジイソプロペニルベンゼン等が挙げられるが、例示化合物のみに限定されるものではない。 Allyl compounds such as allyl glycidyl ether, diallyl phthalate, diallyl terephthalate, diallyl isophthalate, diallyl carbonate, diethylene glycol bisallyl carbonate, styrene, chlorostyrene, methylstyrene, bromostyrene, dibromostyrene, divinylbenzene, 3,9-divinylspirobi (m -Dioxane), vinyl compounds such as divinyl sulfide and divinyl disulfide, and diisopropenylbenzene are exemplified, but the compound is not limited to the exemplified compounds.
更に上記数種の樹脂改質剤はいずれも単独種でも2種類以上を混合して使用しても良い。樹脂改質剤の添加量としては、重合性組成物を構成する化合物の構造により異なり、一概に限定することは出来ないが、通常重合性組成物に対して、0.001wt%〜50wt%の範囲で添加することが可能である。得られる樹脂の光学物性を考慮すれば、添加量が0.005wt%〜25wt%であれば好ましい。0.01wt%〜15wt%であれば、より好ましい。 Furthermore, the above-mentioned several types of resin modifiers may be used alone or in combination of two or more. The amount of the resin modifier added varies depending on the structure of the compound constituting the polymerizable composition and cannot be generally limited, but is usually 0.001 wt% to 50 wt% with respect to the polymerizable composition. It is possible to add in a range. Considering optical properties of the obtained resin, it is preferable that the addition amount is 0.005 wt% to 25 wt%. If it is 0.01 wt%-15 wt%, it is more preferable.
本発明の式(1)で表される構造を有するエピスルフィド化合物を含有する重合性組成物は、通常、公知のエピスルフィド化合物を重合する際の方法を用いて硬化させることが可能であり、硬化樹脂を得るための硬化触媒等の種類や量、単量体の種類や割合は重合性組成物を構成する化合物の構造により異なり、一概に限定する事はできないが、硬化触媒の種類としては本発明の樹脂改質剤以外のアミン類、ホスフィン類、有機酸およびその塩、エステル、無水物類、無機酸、4級アンモニウム塩類、4級ホスホニウム塩類、3級スルホニウム塩類、2級ヨードニウム塩類、ルイス酸類、ラジカル重合触媒類、カチオン重合触媒類等が通常用いられる。 The polymerizable composition containing an episulfide compound having a structure represented by the formula (1) of the present invention can be usually cured using a method for polymerizing a known episulfide compound, and is a cured resin. The type and amount of the curing catalyst and the like, and the type and ratio of the monomer differ depending on the structure of the compound constituting the polymerizable composition and cannot be generally limited. Other than the above resin modifiers, amines, phosphines, organic acids and salts thereof, esters, anhydrides, inorganic acids, quaternary ammonium salts, quaternary phosphonium salts, tertiary sulfonium salts, secondary iodonium salts, Lewis acids , Radical polymerization catalysts, cationic polymerization catalysts and the like are usually used.
硬化触媒の具体例としては、トリエチルアミン、トリn−ブチルアミン、トリn−ヘキシルアミン、N,N−ジイソプロピルエチルアミン、トリエチレンジアミン、トリフェニルアミン、N,N−ジメチルエタノールアミン、N,N−ジエチルエタノールアミン、N,N−ジブチルエタノールアミン、トリエタノールアミン、N−エチルジエタノールアミン、N,N−ジメチルベンジルアミン、N,N−ジエチルベンジルアミン、トリベンジルアミン、N−メチルジベンジルアミン、N,N−ジメチルシクロヘキシルアミン、N,N−ジエチルシクロヘキシルアミン、N,N−ジメチルブチルアミン、N−メチルジシクロヘキシルアミン、N−メチルモルホリン、N−イソプロピルモルホリン、ピリジン、キノリン、N,N−ジメチルアニリン、N,N−ジエチルアニリン、α−、β−、あるいはγ−ピコリン、2,2’−ビピリジル、1,4−ジメチルピペラジン、ジシアンジアミド、テトラメチルエチレンジアミン、ヘキサメチレンテトラミン、1,8−ジアザビシクロ(5,4,0)−7−ウンデセン、2,4,6−トリス(N,N−ジメチルアミノメチル)フェノール等の脂肪族及び芳香族3級アミン類、 Specific examples of the curing catalyst include triethylamine, tri-n-butylamine, tri-n-hexylamine, N, N-diisopropylethylamine, triethylenediamine, triphenylamine, N, N-dimethylethanolamine, N, N-diethylethanolamine. N, N-dibutylethanolamine, triethanolamine, N-ethyldiethanolamine, N, N-dimethylbenzylamine, N, N-diethylbenzylamine, tribenzylamine, N-methyldibenzylamine, N, N-dimethyl Cyclohexylamine, N, N-diethylcyclohexylamine, N, N-dimethylbutylamine, N-methyldicyclohexylamine, N-methylmorpholine, N-isopropylmorpholine, pyridine, quinoline, N, N-dimethylanily N, N-diethylaniline, α-, β-, or γ-picoline, 2,2′-bipyridyl, 1,4-dimethylpiperazine, dicyandiamide, tetramethylethylenediamine, hexamethylenetetramine, 1,8-diazabicyclo (5 , 4,0) -7-undecene, aliphatic and aromatic tertiary amines such as 2,4,6-tris (N, N-dimethylaminomethyl) phenol,
トリメチルホスフィン、トリエチルホスフィン、トリn−プロピルホスフィン、トリイソプロピルホスフィン、トリn−ブチルホスフィン、トリフェニルホスフィン、トリベンジルホスフィン、1,2−ビス(ジフェニルホスフィノ)エタン、1,2−ビス(ジメチルホスフィノ)エタン等のホスフィン類、 Trimethylphosphine, triethylphosphine, tri-n-propylphosphine, triisopropylphosphine, tri-n-butylphosphine, triphenylphosphine, tribenzylphosphine, 1,2-bis (diphenylphosphino) ethane, 1,2-bis (dimethylphosphine) Fino) phosphines such as ethane,
トリフルオロ酢酸、トリクロロ酢酸、トリフルオロ酢酸無水物、トリフルオロ酢酸エチル、トリフルオロ酢酸ソーダ、トリハロゲノ酢酸及びそのエステル、無水物、塩、p−トルエンスルホン酸、メタンスルホン酸、トリフルオロメタンスルホン酸、トリフルオロメタンスルホン酸無水物、トリフルオロメタンスルホン酸エチル、トリフルオロメタンスルホン酸ソーダ等のトリハロゲノメタンスルホン酸及びそのエステル、無水物、塩、塩酸、硫酸、硝酸等の無機酸、 Trifluoroacetic acid, trichloroacetic acid, trifluoroacetic anhydride, ethyl trifluoroacetate, sodium trifluoroacetate, trihalogenoacetic acid and its ester, anhydride, salt, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, trifluoro Trihalogenomethanesulfonic acid and its esters, anhydrides, salts, hydrochloric acid, sulfuric acid, nitric acid and the like, such as lomethanesulfonic anhydride, ethyl trifluoromethanesulfonate, sodium trifluoromethanesulfonate,
テトラメチルアンモニウムクロライド、テトラブチルアンモニウムクロライド、テトラブチルアンモニウムブロマイド等の4級アンモニウム塩、 Quaternary ammonium salts such as tetramethylammonium chloride, tetrabutylammonium chloride, tetrabutylammonium bromide,
テトラメチルホスホニウムクロライド、テトラブチルホスホニウムクロライド、テトラブチルホスホニウムブロマイド等の4級ホスホニウム塩、 Quaternary phosphonium salts such as tetramethylphosphonium chloride, tetrabutylphosphonium chloride, tetrabutylphosphonium bromide,
トリメチルスルホニウムブロマイド、トリブチルスルホニウムブロマイド等の3級スルホニウム塩、ジフェニルヨードニウムブロマイド等の2級ヨード二ウム塩、ジメチル錫ジクロライド、ジブチル錫ジクロライド、ジブチル錫ジラウレート、ジブチル錫ジアセテート、テトラクロロ錫、ジブチル錫オキサイド、ジアセトキシテトラブチルジスタノキサン、塩化亜鉛、アセチルアセトン亜鉛、塩化アルミ、フッ化アルミ、トリフェニルアルミ、アセチルアセトンアルミ、イソプロポキシドアルミ、テトラクロロチタン及びその錯体、テトラヨードチタン、ジクロロチタニウムジイソプロポキシド、チタニウムイソプロポキシド等のチタン系アルコキシド、酢酸カルシウム、三フッ化硼素、三フッ化硼素ジエチルエーテル錯体、三フッ化硼素ピペリジン錯体、三フッ化硼素エチルアミン錯体、三フッ化硼素酢酸錯体、三フッ化硼素リン酸錯体、三フッ化硼素t−ブチルメチルエーテル錯体、三フッ化硼素ジブチルエーテル錯体、三フッ化硼素THF錯体、三フッ化硼素メチルスルフィド錯体、三フッ化硼素フェノール錯体等の三フッ化硼素の各種錯体及び三塩化硼素の各種錯体等のトリハロゲン化硼素化合物及びそのコンプレックスなどのルイス酸、 Tertiary sulfonium salts such as trimethylsulfonium bromide and tributylsulfonium bromide, secondary iodium salts such as diphenyliodonium bromide, dimethyltin dichloride, dibutyltin dichloride, dibutyltin dilaurate, dibutyltin diacetate, tetrachlorotin, dibutyltin oxide , Diacetoxytetrabutyl distanoxane, zinc chloride, acetylacetone zinc, aluminum chloride, aluminum fluoride, triphenylaluminum, acetylacetone aluminum, isopropoxide aluminum, tetrachlorotitanium and its complex, tetraiodotitanium, dichlorotitanium diisopropoxy , Titanium-based alkoxides such as titanium isopropoxide, calcium acetate, boron trifluoride, boron trifluoride diethyl ether complex, boron trifluoride Lysine complex, boron trifluoride ethylamine complex, boron trifluoride acetic acid complex, boron trifluoride phosphate complex, boron trifluoride t-butylmethyl ether complex, boron trifluoride dibutyl ether complex, boron trifluoride THF complex Lewis acids such as boron trifluoride methylsulfide complexes, boron trifluoride phenol complexes, etc., boron trifluoride complexes and boron trichloride complexes, etc.
2,2’−アゾビス(2−シクロプロピルプロピオニトリル)、2,2’−アゾビス(4−メトキシ−2,4−ジメチルバレロニトリル)、2,2’−アゾビス(2,4−ジメチルバレロニトリル)、t−ブチルパーオキシ−2−エチルヘキサノエート、n−ブチル−4,4’−ビス(t−ブチルパーオキシ)バレレート、t−ブチルパーオキシベンゾエート等のラジカル重合触媒、 2,2′-azobis (2-cyclopropylpropionitrile), 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile), 2,2′-azobis (2,4-dimethylvaleronitrile) ), Radical polymerization catalysts such as t-butylperoxy-2-ethylhexanoate, n-butyl-4,4′-bis (t-butylperoxy) valerate, t-butylperoxybenzoate,
ジフェニルヨードニウムヘキサフルオロ燐酸、ジフェニルヨードニウムヘキサフルオロ砒酸、ジフェニルヨードニウムヘキサフルオロアンチモン、トリフェニルスルフォニウムテトラフルオロ硼酸、トリフェニルスルフォニウムヘキサフルオロ燐酸、トリフェニルスルフォニウムヘキサフルオロ砒酸、(トリルクミル)ヨードニウムテトラキス(ペンタフルオロフェニル)ボレート等のカチオン重合触媒が挙げられるが、例示化合物のみに限定されるものではない。 Diphenyliodonium hexafluorophosphoric acid, diphenyliodonium hexafluoroarsenic acid, diphenyliodonium hexafluoroantimony, triphenylsulfonium tetrafluoroboric acid, triphenylsulfonium hexafluorophosphoric acid, triphenylsulfonium hexafluoroarsenic acid, (tolylcumyl) iodonium tetrakis (pentafluoro) Examples thereof include cationic polymerization catalysts such as phenyl) borate, but are not limited to the exemplified compounds.
上記硬化触媒は単独でも2種以上を混合して用いても良く、これら硬化触媒の内、反応性の異なる2種以上のものを併用すると、モノマーのハンドリング性、得られる樹脂の光学物性、色相、透明性、光学ひずみ(脈離)が向上する場合があるため、好ましい。 The above curing catalysts may be used singly or in combination of two or more. When two or more of these curing catalysts having different reactivity are used in combination, the handling property of the monomer, the optical properties of the resulting resin, the hue It is preferable because transparency and optical distortion (pulse separation) may be improved.
上記化合物のうち好ましいものは、3級アミン化合物類及びホスフィン化合物類、4級アンモニウム塩類、4級ホスホニウム塩類、ジメチル錫ジクロライド、ジブチル錫ジクロライド、ジブチル錫ジラウレート、ジブチル錫ジアセテート、テトラクロロ錫、ジブチル錫オキサイド、ジアセトキシテトラブチルジスタノキサン等の有機錫化合物類、ジフェニルヨードニウムヘキサフルオロ燐酸、ジフェニルヨードニウムヘキサフルオロ砒酸、ジフェニルヨードニウムヘキサフルオロアンチモン、トリフェニルスルフォニウムテトラフルオロ硼酸、トリフェニルスルフォニウムヘキサフルオロ燐酸、トリフェニルスルフォニウムヘキサフルオロ砒酸、(トリルクミル)ヨードニウムテトラキス(ペンタフルオロフェニル)ボレート等のカチオン重合触媒類である。 Among the above compounds, preferred are tertiary amine compounds and phosphine compounds, quaternary ammonium salts, quaternary phosphonium salts, dimethyltin dichloride, dibutyltin dichloride, dibutyltin dilaurate, dibutyltin diacetate, tetrachlorotin, dibutyl. Organotin compounds such as tin oxide, diacetoxytetrabutyl distanoxane, diphenyliodonium hexafluorophosphoric acid, diphenyliodonium hexafluoroarsenic acid, diphenyliodonium hexafluoroantimony, triphenylsulfonium tetrafluoroboric acid, triphenylsulfonium hexafluorophosphoric acid Cation weights such as triphenylsulfonium hexafluoroarsenate, (tolylcumyl) iodonium tetrakis (pentafluorophenyl) borate Is the catalysts.
硬化触媒の添加量は、重合性組成物の総重量に対して0.001〜10wt%の範囲で用いられるが、0.005〜5wt%で用いると好ましい。0.01〜1wt%の範囲で使用すればより好ましい。硬化触媒の添加量がこの範囲内であれば、良好に硬化した樹脂の製造が可能であり、ポットライフが保たれ、また、得られる樹脂の透明性、光学物性が良好なものが得られる場合がある。硬化触媒は、本発明のエピスルフィド化合物に直接添加しても、重合性組成物を構成する他の化合物に溶解または分散させてから添加しても良いが、他の化合物に溶解または分散させてから添加した方が好ましい結果を与える場合がある。更には、硬化触媒を添加する場合、窒素雰囲気下または乾燥ガス雰囲気下で行うと好ましい結果を与える場合がある。更に得られる樹脂の性能をより引き出すためには、樹脂中に残存する未反応官能基の量を、樹脂総重量に対して0.5wt%以下とすると好ましい。0.3wt%以下とするとより好ましい。 The addition amount of the curing catalyst is used in the range of 0.001 to 10 wt% with respect to the total weight of the polymerizable composition, but is preferably used in the range of 0.005 to 5 wt%. More preferably, it is used in the range of 0.01 to 1 wt%. When the addition amount of the curing catalyst is within this range, it is possible to produce a resin that is cured well, the pot life is maintained, and the resin obtained has good transparency and optical properties. There is. The curing catalyst may be added directly to the episulfide compound of the present invention, or may be added after being dissolved or dispersed in another compound constituting the polymerizable composition, but after being dissolved or dispersed in another compound. The addition may give a preferable result. Furthermore, when a curing catalyst is added, a favorable result may be obtained if it is carried out in a nitrogen atmosphere or a dry gas atmosphere. Furthermore, in order to further draw out the performance of the obtained resin, it is preferable that the amount of unreacted functional groups remaining in the resin is 0.5 wt% or less with respect to the total weight of the resin. More preferably, it is 0.3 wt% or less.
本発明の式(1)で表される構造を有するエピスルフィド化合物を含有する重合性組成物を硬化し樹脂を成形する際には、目的に応じて公知の成形法におけると同様に、前記以外の安定剤、樹脂改質剤、鎖延長剤、架橋剤、HALS系を代表とする光安定剤、ベンゾトリアゾール系を代表とする紫外線吸収剤、ヒンダードフェノール系を代表とする酸化防止剤、着色防止剤、アントラキノン系分散染料を代表とする染料、充填剤、シリコーン系を代表とする外部離型剤または内部離型剤、密着性向上剤などの種々の物質を添加してもよい。 When a polymerizable composition containing an episulfide compound having a structure represented by the formula (1) of the present invention is cured and a resin is molded, other than the above, as in a known molding method, depending on the purpose Stabilizers, resin modifiers, chain extenders, crosslinking agents, light stabilizers typified by HALS, UV absorbers typified by benzotriazole, antioxidants typified by hindered phenols, anti-coloring Various substances such as an agent, a dye represented by an anthraquinone-based disperse dye, a filler, an external mold release agent represented by a silicone series or an internal mold release agent, and an adhesion improver may be added.
本発明において用いられる上記内部離型剤の例としては、離型性の効果があり樹脂の透明性などの物性を損なわないものであればなんでも使用可能であるが、好ましくは、界面活性剤が使用される。離型剤として好ましく用いられる界面活性剤は、イオン型界面活性剤、非イオン型界面活性剤に大別され、イオン型界面活性剤は、アニオン型界面活性剤、カチオン型界面活性剤に分類される。アニオン型界面活性剤の例として、硫酸エステル系、スルホン酸エステル系、リン酸エステル系があげられるが、この中でリン酸エステル系界面活性剤が好ましく、特に酸性リン酸エステル系アニオン界面活性剤が好ましい。
これら内部離型剤は、単独で使用してもよく、2種以上とを混合して使用してもよい。これらはモノマー組合せ、重合条件、経済性、取り扱いの容易さより適宜選ばれる。内部離型剤の使用量は単独または2種以上の混合物として、通常、銃合成組成物の総重量に対して1〜10000ppmの範囲である。添加量が1ppm以上であると離型能が良好であり、10000ppm以下であると注型重合中のモールドから離型が抑制され、レンズ表面の面精度の悪化や得られるレンズの白濁を防ぐことができる。
As an example of the internal release agent used in the present invention, any material can be used as long as it has a releasability effect and does not impair physical properties such as transparency of the resin. Preferably, a surfactant is used. used. Surfactants that are preferably used as mold release agents are broadly classified into ionic surfactants and nonionic surfactants, and ionic surfactants are classified into anionic surfactants and cationic surfactants. The Examples of the anionic surfactant include sulfate ester, sulfonate ester, and phosphate ester. Among these, phosphate ester surfactants are preferable, and acidic phosphate ester anionic surfactants are particularly preferable. Is preferred.
These internal mold release agents may be used alone or in combination of two or more. These are appropriately selected from the monomer combination, polymerization conditions, economy, and ease of handling. The amount of the internal mold release agent used is usually in the range of 1 to 10,000 ppm based on the total weight of the gun composition, either alone or as a mixture of two or more. When the addition amount is 1 ppm or more, the release performance is good, and when it is 10000 ppm or less, release from the mold during the casting polymerization is suppressed, thereby preventing deterioration of the surface accuracy of the lens surface and white turbidity of the obtained lens. Can do.
上記添加を可能とする内部離型剤以外の各種添加剤の添加量は、それぞれの添加剤の種類、構造、効果により異なり一概に限定することは出来ないが、通常、重合性組成物の総重量に対して0.001〜10wt%の範囲で用いられるが、0.01〜5wt%の範囲で使用すると好ましい。染料については、この範囲ではなく、1ppb〜100ppmの範囲で使用すると好ましい。これらの範囲内であれば、良好に硬化した樹脂の製造が可能であり、得られる樹脂の透明性、光学物性が良好なものが得られる場合がある。 The addition amount of various additives other than the internal mold release agent that enables the above addition varies depending on the type, structure, and effect of each additive and cannot be generally limited. It is used in the range of 0.001 to 10 wt% with respect to the weight, but is preferably used in the range of 0.01 to 5 wt%. The dye is preferably used in the range of 1 ppb to 100 ppm instead of this range. Within these ranges, a well-cured resin can be produced, and a resin having good transparency and optical properties may be obtained.
本発明の組成物を硬化してなる樹脂(例えば、プラスチックレンズ)を得る際の代表的な重合方法としては、注型重合が挙げられる。即ち、ガスケットまたはテープ等で保持された成型モールド間に、本発明の重合性組成物を注入する。注入操作は、特に問題のない限り通常の雰囲気下で行うと良いが、窒素雰囲気下または、乾燥ガス雰囲気下で行うとより良い結果を与える場合がある。モールド内を予め窒素ガスまたは乾燥ガスで置換しておいても良い。ここで重合性組成物には必要に応じて硬化触媒および樹脂改質剤を混合したり、脱泡操作などの10kPa以下での減圧処理、フィルター濾過等の操作を予め行っておいてもよい。次いで、オーブン中や水中など加熱可能装置内で加熱することにより硬化させ、樹脂を取り出すことができる。 A typical polymerization method for obtaining a resin (for example, a plastic lens) obtained by curing the composition of the present invention is cast polymerization. That is, the polymerizable composition of the present invention is injected between molding molds held by a gasket or a tape. The injection operation is preferably performed in a normal atmosphere as long as there is no particular problem, but better results may be obtained if it is performed in a nitrogen atmosphere or a dry gas atmosphere. The inside of the mold may be replaced with nitrogen gas or dry gas in advance. Here, if necessary, the polymerizable composition may be mixed with a curing catalyst and a resin modifier, or may be preliminarily subjected to operations such as depressurization at 10 kPa or less such as a defoaming operation, filter filtration and the like. Then, it can be cured by heating in a heatable apparatus such as an oven or water, and the resin can be taken out.
本発明の組成物を硬化してなる樹脂を得るための重合法、重合条件等は、用いる硬化触媒等の種類や量、単量体の種類や割合によって、一概に限定する事はできない。 The polymerization method for obtaining the resin obtained by curing the composition of the present invention, the polymerization conditions, etc. cannot be generally limited by the type and amount of the curing catalyst used and the type and ratio of the monomer.
成型モールドに注入された本発明の重合性組成物の加熱重合条件は、本発明の式(1)で表される構造を有する化合物を含有する重合性組成物の組成及び構造により異なり一概に限定できず、また、樹脂改質剤の種類、硬化触媒の種類、成型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できないが、重合温度はおよそ−50〜200℃で行われるが、−20℃〜150℃が好ましい。0℃〜130℃の温度範囲では更に好ましい。重合時間は0.01〜100時間で行われるが、0.05〜50時間で行うと好ましい。0.1〜25時間かけて行えばより好ましい。場合によっては、温度条件を低温や昇温、降温などのプログラムを組み重合することも可能である。 The heating polymerization conditions of the polymerizable composition of the present invention injected into the molding mold differ depending on the composition and structure of the polymerizable composition containing the compound having the structure represented by the formula (1) of the present invention and are generally limited. The polymerization temperature is about −50 to 200 ° C., but the temperature is about −50 to 200 ° C., but the conditions are largely different depending on the type of resin modifier, the type of curing catalyst, the shape of the molding mold, etc. 150 ° C. is preferred. It is more preferable in the temperature range of 0 ° C to 130 ° C. The polymerization time is 0.01 to 100 hours, preferably 0.05 to 50 hours. More preferably, it is performed for 0.1 to 25 hours. In some cases, it is possible to perform polymerization by combining the temperature conditions with programs such as low temperature, temperature increase, and temperature decrease.
更には、本発明の重合性組成物は、電子線や紫外線等のエネルギー線を照射することにより重合時間の短縮を図ることも可能である。この際には、前述の硬化触媒として記載したラジカル重合触媒やカチオン重合触媒等の硬化触媒等を添加しても良い。また、取り出した硬化樹脂については、必要に応じて、アニール等の処理を行ってもよい。アニール条件としては、硬化する重合性組成物を構成する化合物の構造、得られる樹脂の構造などにより異なり、一概に限定できないが、通常30℃〜200℃で行われるが、50℃〜150℃で行うと好ましい。70℃〜130℃で行えばより好ましい。 Furthermore, the polymerizable composition of the present invention can shorten the polymerization time by irradiating an energy beam such as an electron beam or an ultraviolet ray. In this case, a curing catalyst such as a radical polymerization catalyst or a cationic polymerization catalyst described as the above-described curing catalyst may be added. Moreover, about the cured resin taken out, you may perform processes, such as annealing, as needed. The annealing condition varies depending on the structure of the compound constituting the polymerizable composition to be cured, the structure of the resin to be obtained, and the like, and cannot be generally limited, but is usually performed at 30 to 200 ° C, but at 50 to 150 ° C Preferably it is done. More preferably, it is carried out at 70 ° C to 130 ° C.
更に、本発明の樹脂は、注型重合時の成型モールドを変えることにより種々の形態の成形体として得ることができ、眼鏡レンズ、カメラレンズ、発光ダイオード(LED)等の高屈折率や透明性の特長を生かした樹脂が要求される各種の用途に使用することができる。特に、眼鏡レンズ、カメラレンズ等の光学材料として好適である。 Furthermore, the resin of the present invention can be obtained as a molded product of various forms by changing the molding mold at the time of casting polymerization. It can be used for various applications that require a resin that takes advantage of In particular, it is suitable as an optical material such as a spectacle lens and a camera lens.
このようにして得られた本発明の光学材料を用いたレンズでは、必要に応じ、反射防止、高硬度付与、耐摩耗性向上、耐薬品性向上、防曇性付与、あるいは、ファッション性付与等の改良を行うため、表面研磨、帯電防止処理、ハードコート処理、無反射コート処理、染色処理等の物理的あるいは化学的処理を施すことができる。 In the lens using the optical material of the present invention thus obtained, if necessary, antireflection, imparting high hardness, improving abrasion resistance, improving chemical resistance, imparting antifogging, imparting fashion, etc. Therefore, physical or chemical treatments such as surface polishing, antistatic treatment, hard coat treatment, non-reflective coating treatment, and dyeing treatment can be performed.
以下、本発明を実施例により具体的に説明する。本発明は以下の実施例に限定されるものではない。尚、得られた硬化樹脂の性能試験のうち、光学物性、耐衝撃性試験は以下の試験法により評価した。 Hereinafter, the present invention will be specifically described by way of examples. The present invention is not limited to the following examples. Of the performance tests of the obtained cured resin, the optical properties and impact resistance tests were evaluated by the following test methods.
・ 屈折率(ne)アッベ数(νe): プルフリッヒ屈折計を用いて、20℃で測定した。
・ 耐熱性: TMAペネトレーション法(50g荷重、ピン先0.5mmφ)でのTgを耐熱性とした。TMA曲線を解析した際に変極点のなかったものは、便宜的に>130℃とした。
・ 樹脂透明性 : 高圧水銀灯下目視で観察した。濁りのあるものを×、透明性に優れたものを○とした。
Refractive index (ne) Abbe number (νe): Measured at 20 ° C. using a Purfrich refractometer.
-Heat resistance: Tg in the TMA penetration method (50 g load, pin tip 0.5 mmφ) was regarded as heat resistance. Those having no inflection point when the TMA curve was analyzed were set to> 130 ° C. for convenience.
-Resin transparency: Observed visually under a high-pressure mercury lamp. Cloudy ones were marked with x, and ones with excellent transparency were marked with ◯.
[実施例1]
攪拌機と温度計を備えた反応器中にビス(メルカプトメチル)スルフィド63gとビス(2,3−エピチオプロピル)ジスルフィド420g、トルエン500gを装入し、触媒としてN,N−ジイソプロピルエチルアミン0.5gを添加した後、30℃にて20時間攪拌しながら反応を行った。反応終了後、減圧下トルエンを留去した。続いてイソプロピルアルコール500gを装入し、30分間攪拌した後、静置して分液させた。上層のイソプロピルアルコール層を除去した。同様の洗浄操作を2回繰り返し得られた下層を取り出した後、トッピングして溶存したイソプロピルアルコールを除去した。続いて、トッピングの後に得られた残渣をヘキサン、クロロホルムを展開溶媒とするシリカゲルカラムに通すことで精製を行った。精製により得られた化合物の構造を確認する為に分析を行った結果、1,3−ビス(2,3−エピチオプロピルジチオ)−2−チアプロパン(以下、化合物(a)と略す)であった。
ここで、得られた化合物についてその同定データーを以下に示す。
[Example 1]
A reactor equipped with a stirrer and a thermometer was charged with 63 g of bis (mercaptomethyl) sulfide, 420 g of bis (2,3-epithiopropyl) disulfide and 500 g of toluene, and 0.5 g of N, N-diisopropylethylamine as a catalyst. Then, the reaction was carried out with stirring at 30 ° C. for 20 hours. After completion of the reaction, toluene was distilled off under reduced pressure. Subsequently, 500 g of isopropyl alcohol was charged, stirred for 30 minutes, and allowed to stand for liquid separation. The upper isopropyl alcohol layer was removed. After removing the lower layer obtained by repeating the same washing operation twice, the isopropyl alcohol dissolved by topping was removed. Subsequently, purification was performed by passing the residue obtained after topping through a silica gel column using hexane and chloroform as developing solvents. As a result of analysis to confirm the structure of the compound obtained by purification, it was 1,3-bis (2,3-epithiopropyldithio) -2-thiapropane (hereinafter abbreviated as compound (a)). It was.
Here, the identification data of the obtained compound is shown below.
[実施例2]
ビス(メルカプトメチル)スルフィド63gの代わりにビス(メルカプトメチル)ジスルフィド79gを用いたこと以外は実施例1と同様にして反応、洗浄、取出し、精製を行った。精製により得られた化合物の構造を確認する為に分析を行った結果、1,4−ビス(2,3−エピチオプロピルジチオ)−2,3−ジチアブタン(以下、化合物(b)と略す)であった。
ここで、得られた化合物についてその同定データーを以下に示す。
[Example 2]
The reaction, washing, removal and purification were carried out in the same manner as in Example 1 except that 79 g of bis (mercaptomethyl) disulfide was used instead of 63 g of bis (mercaptomethyl) sulfide. As a result of analysis to confirm the structure of the compound obtained by purification, 1,4-bis (2,3-epithiopropyldithio) -2,3-dithiabutane (hereinafter abbreviated as compound (b)) Met.
Here, the identification data of the obtained compound is shown below.
[実施例3]
ビス(メルカプトメチル)スルフィド63gの代わりに1,1,1−トリス(メルカプトメチルチオ)メタン84gを用いたこと以外は実施例1と同様にして反応、洗浄、取出し、精製を行った。精製により得られた化合物の構造を確認する為に分析を行った結果、1,1,1−トリス(2,3−エピチオプロピルジチオメチルチオ)メタン(以下、化合物(c)と略す)であった。
ここで、得られた化合物についてその同定データーを以下に示す。
[Example 3]
The reaction, washing, removal and purification were carried out in the same manner as in Example 1 except that 84 g of 1,1,1-tris (mercaptomethylthio) methane was used instead of 63 g of bis (mercaptomethyl) sulfide. As a result of analysis to confirm the structure of the compound obtained by purification, it was 1,1,1-tris (2,3-epithiopropyldithiomethylthio) methane (hereinafter abbreviated as compound (c)). It was.
Here, the identification data of the obtained compound is shown below.
[実施例4]
ビス(メルカプトメチル)スルフィド63gの代わりに1,1,2,2−テトラキス(メルカプトメチルチオ)エタン86gを用いたこと以外は実施例1と同様にして反応、洗浄、取出し、精製を行った。精製により得られた化合物の構造を確認する為に分析を行った結果、1,1,2,2−テトラキス(2,3−エピチオプロピルジチオメチルチオ)エタン(以下、化合物(d)と略す)であった。
ここで、得られた化合物についてその同定データーを以下に示す。
[Example 4]
The reaction, washing, removal and purification were carried out in the same manner as in Example 1 except that 86 g of 1,1,2,2-tetrakis (mercaptomethylthio) ethane was used instead of 63 g of bis (mercaptomethyl) sulfide. As a result of analysis to confirm the structure of the compound obtained by purification, 1,1,2,2-tetrakis (2,3-epithiopropyldithiomethylthio) ethane (hereinafter abbreviated as compound (d)) Met.
Here, identification data of the obtained compound is shown below.
[実施例5]
ビス(メルカプトメチル)スルフィド63gの代わりに1,1,3,3−テトラキス(メルカプトメチルチオ)プロパン89gを用いたこと以外は実施例1と同様にして反応、洗浄、取出し、精製を行った。精製により得られた化合物の構造を確認する為に分析を行った結果、1,1,3,3−テトラキス(2,3−エピチオプロピルジチオメチルチオ)プロパン(以下、化合物(e)と略す)であった。
ここで、得られた化合物についてその同定データーを以下に示す。
[Example 5]
The reaction, washing, removal and purification were carried out in the same manner as in Example 1 except that 89 g of 1,1,3,3-tetrakis (mercaptomethylthio) propane was used instead of 63 g of bis (mercaptomethyl) sulfide. As a result of analysis to confirm the structure of the compound obtained by purification, 1,1,3,3-tetrakis (2,3-epithiopropyldithiomethylthio) propane (hereinafter abbreviated as compound (e)) Met.
Here, the identification data of the obtained compound is shown below.
[実施例6]
ビス(メルカプトメチル)スルフィド63gの代わりに2−[1,1−ビス(メルカプトメチルチオ)メチル]−1,3−ジチエタン130gを用いたこと以外は実施例1と同様にして反応、洗浄、取出し、精製を行った。精製により得られた化合物の構造を確認する為に分析を行った結果、2−[1,1−ビス(2,3−エピチオプロピルジチオメチルチオ)メチル]−1,3−ジチエタン(以下、化合物(f)と略す)であった。
ここで、得られた化合物についてその同定データーを以下に示す。
[Example 6]
In the same manner as in Example 1 except that 130 g of 2- [1,1-bis (mercaptomethylthio) methyl] -1,3-dithietane was used instead of 63 g of bis (mercaptomethyl) sulfide, Purification was performed. As a result of analysis to confirm the structure of the compound obtained by purification, 2- [1,1-bis (2,3-epithiopropyldithiomethylthio) methyl] -1,3-dithietane (hereinafter referred to as compound) (Abbreviated as (f)).
Here, the identification data of the obtained compound is shown below.
[実施例7]
室温20℃にてビーカーに化合物(a)30gと紫外線吸収剤としてバイオソーブ583(共同薬品社製)0.03gを混合し溶解した後、硬化触媒としてN,N−ジメチルシクロヘキシルアミン0.06gを添加後混合したものを減圧下で0.4時間脱泡した後、ガラスモールドとガスケットよりなるモールド型に注入した。このモールドを30℃から120℃まで徐々に昇温し、24時間で重合を行った。重合終了後、徐々に冷却し、樹脂をモールドから取り出した。得られた樹脂は、透明性に優れ、歪みのない外観良好なものであった。
[Example 7]
30 g of compound (a) and 0.03 g of Biosorb 583 (manufactured by Kyodo Yakuhin Co., Ltd.) are mixed and dissolved in a beaker at room temperature of 20 ° C., and 0.06 g of N, N-dimethylcyclohexylamine is added as a curing catalyst. The post-mixed product was degassed for 0.4 hours under reduced pressure, and then poured into a mold comprising a glass mold and a gasket. The mold was gradually heated from 30 ° C. to 120 ° C. and polymerized in 24 hours. After the polymerization was completed, the mixture was gradually cooled and the resin was taken out from the mold. The obtained resin was excellent in transparency and good in appearance without distortion.
得られた樹脂の光学物性を測定したところ、屈折率ne=1.77、νe=30であった。結果を表7にまとめた。 When the optical properties of the obtained resin were measured, the refractive index was ne = 1.77 and νe = 30. The results are summarized in Table 7.
[実施例8]
化合物(a)の代わりに化合物(b)を30g使用する以外は、実施例2と同様にして樹脂を得た。得られた樹脂はいずれ透明性に優れ、歪みのない外観良好なものであった。得られた樹脂の光学物性を測定したところ、屈折率ne=1.80、νe=29であった。得られた物性を表7にまとめた。
[Example 8]
A resin was obtained in the same manner as in Example 2 except that 30 g of compound (b) was used instead of compound (a). The obtained resin eventually had excellent transparency and good appearance without distortion. When the optical properties of the obtained resin were measured, the refractive index was ne = 1.80 and νe = 29. The physical properties obtained are summarized in Table 7.
[実施例9]
化合物(a)の代わりに化合物(c)を30g使用する以外は、実施例2と同様にして樹脂を得た。得られた樹脂はいずれ透明性に優れ、歪みのない外観良好なものであった。得られた樹脂の光学物性を測定したところ、屈折率ne=1.78、νe=30であった。得られた物性を表7にまとめた。
[Example 9]
A resin was obtained in the same manner as in Example 2 except that 30 g of compound (c) was used instead of compound (a). The obtained resin eventually had excellent transparency and good appearance without distortion. When the optical properties of the obtained resin were measured, the refractive index was ne = 1.78 and νe = 30. The physical properties obtained are summarized in Table 7.
[実施例10]
化合物(a)の代わりに化合物(d)を30g使用する以外は、実施例2と同様にして樹脂を得た。得られた樹脂はいずれ透明性に優れ、歪みのない外観良好なものであった。得られた樹脂の光学物性を測定したところ、屈折率ne=1.78、νe=30であった。得られた物性を表7にまとめた。
[Example 10]
A resin was obtained in the same manner as in Example 2 except that 30 g of compound (d) was used instead of compound (a). The obtained resin eventually had excellent transparency and good appearance without distortion. When the optical properties of the obtained resin were measured, the refractive index was ne = 1.78 and νe = 30. The physical properties obtained are summarized in Table 7.
[実施例11]
化合物(a)の代わりに化合物(e)を30g使用する以外は、実施例2と同様にして樹脂を得た。得られた樹脂はいずれ透明性に優れ、歪みのない外観良好なものであった。得られた樹脂の光学物性を測定したところ、屈折率ne=1.77、νe=30であった。得られた物性を表7にまとめた。
[Example 11]
A resin was obtained in the same manner as in Example 2 except that 30 g of compound (e) was used instead of compound (a). The obtained resin eventually had excellent transparency and good appearance without distortion. When the optical properties of the obtained resin were measured, the refractive index was ne = 1.77 and νe = 30. The physical properties obtained are summarized in Table 7.
[実施例12]
化合物(a)の代わりに化合物(f)を30g使用する以外は、実施例2と同様にして樹脂を得た。得られた樹脂はいずれ透明性に優れ、歪みのない外観良好なものであった。得られた樹脂の光学物性を測定したところ、屈折率ne=1.78、νe=30であった。得られた物性を表7にまとめた。
[Example 12]
A resin was obtained in the same manner as in Example 2 except that 30 g of compound (f) was used instead of compound (a). The obtained resin eventually had excellent transparency and good appearance without distortion. When the optical properties of the obtained resin were measured, the refractive index was ne = 1.78 and νe = 30. The physical properties obtained are summarized in Table 7.
[実施例13〜18]
化合物(a)〜(f)をそれぞれ30g使用し、樹脂改質剤として1,1,2,2−テトラキス(メルカプトメチルチオ)エタン3.0gを添加する以外は、実施例7と同様にして樹脂を得た。得られた樹脂はいずれ透明性に優れ、歪みのない外観良好なものであった。得られた物性を表7にまとめた。
[Examples 13 to 18]
Resin in the same manner as in Example 7, except that 30 g of each of compounds (a) to (f) was used and 3.0 g of 1,1,2,2-tetrakis (mercaptomethylthio) ethane was added as a resin modifier. Got. The obtained resin eventually had excellent transparency and good appearance without distortion. The physical properties obtained are summarized in Table 7.
[実施例19]
化合物(d)を30g使用し、樹脂改質剤として1,1,2,2−テトラキス(メルカプトメチルチオ)エタン3.0gと硫黄3.0gを添加する以外は、実施例7と同様にして樹脂を得た。得られた樹脂はいずれ透明性に優れ、歪みのない外観良好なものであった。得られた物性を表7にまとめた。
[Example 19]
Resin in the same manner as in Example 7 except that 30 g of compound (d) was used and 3.0 g of 1,1,2,2-tetrakis (mercaptomethylthio) ethane and 3.0 g of sulfur were added as a resin modifier. Got. The obtained resin eventually had excellent transparency and good appearance without distortion. The physical properties obtained are summarized in Table 7.
[比較例1]
エピスルフィド化合物として、特開2000−281787号公報に記載の2,5−ビス(β−エピチオプロピルジチオメチル)−1,4−ジチアンを合成し、実施例7と同様にして樹脂を得た。
[Comparative Example 1]
As an episulfide compound, 2,5-bis (β-epithiopropyldithiomethyl) -1,4-dithiane described in JP-A No. 2000-281787 was synthesized, and a resin was obtained in the same manner as in Example 7.
得られた樹脂の光学物性及び耐熱性を測定したところ、屈折率ne=1.73、νe=33であった。実施例7〜12と比較すると屈折率が大きく劣っていた。 When the optical properties and heat resistance of the obtained resin were measured, the refractive index was ne = 1.73 and νe = 33. Compared with Examples 7-12, the refractive index was greatly inferior.
Claims (12)
(式中、R1は、直鎖もしくは分岐の炭素数1〜4のチア化されていても良い炭化水素基、環状の炭素数3〜6のチア化されていても良い炭化水素基、1,4−ジチアン基、アリーレン基、または、アラルキレン基を表す。R1は置換されていても未置換でも良い。R2〜R9は水素原子、またはチア化されていても良い置換または未置換の直鎖もしくは分岐の炭素数1〜4の炭化水素基または環状の炭素数3〜6の炭化水素基を表す。a,b,cおよびdはそれぞれ0または1の整数を表し、2≦a+b+c+d≦4を満たす。) An episulfide compound having a structure represented by the following formula (1).
(In the formula, R1 represents a linear or branched hydrocarbon group having 1 to 4 carbon atoms which may be thiated, a cyclic hydrocarbon group having 3 to 6 carbon atoms which may be thiated, 1, Represents a 4-dithian group, an arylene group, or an aralkylene group, R1 may be substituted or unsubstituted, and R2 to R9 may be a hydrogen atom, or a substituted or unsubstituted linear or Represents a branched hydrocarbon group having 1 to 4 carbon atoms or a cyclic hydrocarbon group having 3 to 6 carbon atoms, a, b, c and d each represents an integer of 0 or 1, satisfying 2 ≦ a + b + c + d ≦ 4 .)
(式中、R10は、直鎖もしくは分岐の炭素数1〜4のチア化されていても良い炭化水素基、環状の炭素数3〜6のチア化されていても良い炭化水素基、1,4−ジチアン基、アリーレン基、または、アラルキレン基を表す。R10は置換されていても未置換でも良い。R11、R12は水素原子、またはチア化されていても良い置換または未置換の直鎖もしくは分岐の炭素数1〜4の炭化水素基または環状の炭素数3〜6の炭化水素基を表す。nは2〜4の整数を表す。) The compound of Claim 1 which has a structure represented by following formula (2).
(Wherein R10 represents a linear or branched hydrocarbon group having 1 to 4 carbon atoms which may be thiated, a cyclic hydrocarbon group having 3 to 6 carbon atoms which may be thiated, 1, Represents a 4-dithian group, an arylene group, or an aralkylene group, R10 may be substituted or unsubstituted, and R11 and R12 may be a hydrogen atom, or a substituted or unsubstituted linear or A branched hydrocarbon group having 1 to 4 carbon atoms or a cyclic hydrocarbon group having 3 to 6 carbon atoms, and n represents an integer of 2 to 4)
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US10132961B2 (en) * | 2015-03-31 | 2018-11-20 | Mitsubishi Gas Chemical Company, Inc. | Episulfide compound and optical material composition including same |
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