JP2006099030A - 光ファイバアップジャケット用液状硬化性樹脂組成物 - Google Patents
光ファイバアップジャケット用液状硬化性樹脂組成物 Download PDFInfo
- Publication number
- JP2006099030A JP2006099030A JP2004347422A JP2004347422A JP2006099030A JP 2006099030 A JP2006099030 A JP 2006099030A JP 2004347422 A JP2004347422 A JP 2004347422A JP 2004347422 A JP2004347422 A JP 2004347422A JP 2006099030 A JP2006099030 A JP 2006099030A
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- Prior art keywords
- meth
- acrylate
- polyol
- mass
- optical fiber
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000011342 resin composition Substances 0.000 title claims abstract description 35
- 239000013307 optical fiber Substances 0.000 title claims abstract description 33
- 239000007788 liquid Substances 0.000 title claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 22
- 239000000463 material Substances 0.000 claims abstract description 15
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 9
- 239000003085 diluting agent Substances 0.000 claims abstract description 5
- 229920005862 polyol Polymers 0.000 claims description 111
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 109
- -1 polyol compounds Chemical class 0.000 claims description 59
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000011247 coating layer Substances 0.000 abstract description 15
- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003077 polyols Chemical class 0.000 description 91
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 41
- 239000010410 layer Substances 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
- 239000004721 Polyphenylene oxide Substances 0.000 description 20
- 229920000570 polyether Polymers 0.000 description 20
- 125000002947 alkylene group Chemical group 0.000 description 19
- 229920001577 copolymer Polymers 0.000 description 17
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 16
- 239000011248 coating agent Substances 0.000 description 15
- 238000000576 coating method Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 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 14
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 125000005442 diisocyanate group Chemical group 0.000 description 11
- 239000004205 dimethyl polysiloxane Substances 0.000 description 11
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 11
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 11
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 10
- 150000001923 cyclic compounds Chemical class 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 9
- 239000003063 flame retardant Substances 0.000 description 9
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 229920001451 polypropylene glycol Polymers 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 6
- 239000004417 polycarbonate Substances 0.000 description 6
- 229920000515 polycarbonate Polymers 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 5
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 5
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 4
- LJPCNSSTRWGCMZ-UHFFFAOYSA-N 3-methyloxolane Chemical compound CC1CCOC1 LJPCNSSTRWGCMZ-UHFFFAOYSA-N 0.000 description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 229920001610 polycaprolactone Polymers 0.000 description 4
- 239000004632 polycaprolactone Substances 0.000 description 4
- 229920005906 polyester polyol Polymers 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000012719 thermal polymerization Methods 0.000 description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 3
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- ZZXXBDPXXIDUBP-UHFFFAOYSA-N hydroxymethyl prop-2-enoate Chemical compound C(C=C)(=O)OCO.C(C=C)(=O)OCO ZZXXBDPXXIDUBP-UHFFFAOYSA-N 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- BJZYYSAMLOBSDY-QMMMGPOBSA-N (2s)-2-butoxybutan-1-ol Chemical compound CCCCO[C@@H](CC)CO BJZYYSAMLOBSDY-QMMMGPOBSA-N 0.000 description 2
- UYVWNPAMKCDKRB-UHFFFAOYSA-N 1,2,4,5-tetraoxane Chemical compound C1OOCOO1 UYVWNPAMKCDKRB-UHFFFAOYSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 2
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- UFAKDGLOFJXMEN-UHFFFAOYSA-N 2-ethenyloxetane Chemical compound C=CC1CCO1 UFAKDGLOFJXMEN-UHFFFAOYSA-N 0.000 description 2
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- CXURGFRDGROIKG-UHFFFAOYSA-N 3,3-bis(chloromethyl)oxetane Chemical compound ClCC1(CCl)COC1 CXURGFRDGROIKG-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
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- XAYDWGMOPRHLEP-UHFFFAOYSA-N 6-ethenyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2OC21C=C XAYDWGMOPRHLEP-UHFFFAOYSA-N 0.000 description 2
- PCFMUWBCZZUMRX-UHFFFAOYSA-N 9,10-Dihydroxyanthracene Chemical compound C1=CC=C2C(O)=C(C=CC=C3)C3=C(O)C2=C1 PCFMUWBCZZUMRX-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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- 229910019142 PO4 Inorganic materials 0.000 description 2
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
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- 125000000217 alkyl group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- 239000007795 chemical reaction product Substances 0.000 description 2
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- 230000000052 comparative effect Effects 0.000 description 2
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- 150000004292 cyclic ethers Chemical class 0.000 description 2
- FWQJLFDJWHTPCJ-UHFFFAOYSA-N cyclodecane;methanol Chemical compound OC.OC.C1CCCCCCCCC1.C1CCCCCCCCC1.C1CCCCCCCCC1 FWQJLFDJWHTPCJ-UHFFFAOYSA-N 0.000 description 2
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- 238000010586 diagram Methods 0.000 description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
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- 239000003999 initiator Substances 0.000 description 2
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- 150000003951 lactams Chemical class 0.000 description 2
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- SIOJEWHPHRFDAX-UHFFFAOYSA-N methanol;pentadecane Chemical compound OC.OC.CCCCCCCCCCCCCCC SIOJEWHPHRFDAX-UHFFFAOYSA-N 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 description 2
- XRQKARZTFMEBBY-UHFFFAOYSA-N oxiran-2-ylmethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1CO1 XRQKARZTFMEBBY-UHFFFAOYSA-N 0.000 description 2
- WEVYNWIJRMVEMS-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enyl carbonate Chemical compound C=CCOC(=O)OCC1CO1 WEVYNWIJRMVEMS-UHFFFAOYSA-N 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- FSPSELPMWGWDRY-UHFFFAOYSA-N m-Methylacetophenone Chemical compound CC(=O)C1=CC=CC(C)=C1 FSPSELPMWGWDRY-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UQIQLMWVCFRJKB-UHFFFAOYSA-N nonoxybenzene;prop-2-enoic acid Chemical compound OC(=O)C=C.CCCCCCCCCOC1=CC=CC=C1 UQIQLMWVCFRJKB-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- PWGIEBRSWMQVCO-UHFFFAOYSA-N phosphono prop-2-enoate Chemical compound OP(O)(=O)OC(=O)C=C PWGIEBRSWMQVCO-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002523 polyethylene Glycol 1000 Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000007779 soft material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- KVMPUXDNESXNOH-UHFFFAOYSA-N tris(1-chloropropan-2-yl) phosphate Chemical compound ClCC(C)OP(=O)(OC(C)CCl)OC(C)CCl KVMPUXDNESXNOH-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
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- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
- C03C25/10—Coating
- C03C25/104—Coating to obtain optical fibres
- C03C25/106—Single coatings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/81—Unsaturated isocyanates or isothiocyanates
- C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
- C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen
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Abstract
【解決手段】 下記成分(A)、(B)及び(C)の合計量100質量%に対して、
(A)ウレタン(メタ)アクリレート 30〜90質量%、
(B)反応性希釈剤 1〜70質量%、
(C)重合開始剤 0.1〜10質量%
および
(D)平均分子量1,500〜35,000のシリコーン化合物 1〜50質量%
を含有する光ファイバアップジャケット用液状硬化性樹脂組成物。
【選択図】 なし
Description
本発明の目的は、光ファイバ被覆材としての機能に優れ、かつ隣接被覆層との剥離性に優れた光ファイバアップジャケット用液状硬化性樹脂組成物を提供することにある。
(A)ウレタン(メタ)アクリレート 30〜90質量%、
(B)反応性希釈剤 1〜70質量%、
(C)重合開始剤 0.1〜10質量%
および
(D)平均分子量1,500〜35,000のシリコーン化合物 1〜50質量%
を含有する光ファイバアップジャケット用液状硬化性樹脂組成物を提供する。
また、本発明は当該光ファイバアップジャケット用液状硬化性樹脂組成物の硬化物からなる光ファイバアップジャケット層を提供する。
さらに本発明は、当該光ファイバアップジャケット層を有する光ファイバアップジャケット素線を提供する。
また、(A)成分は、ジイソシアネート1モルに対して水酸基含有(メタ)アクリレート化合物2モルを反応させることにより製造することもできる。かかるウレタン(メタ)アクリレートとしては、例えば、ヒドロキシエチル(メタ)アクリレートと2,4−トリレンジイソシアネートの反応物、ヒドロキシエチル(メタ)アクリレートと2,5(または2,6)−ビス(イソシアネートメチル)−ビシクロ[2.2.1]ヘプタンの反応物、ヒドロキシエチル(メタ)アクリレートとイソフォロンジイソシアネートの反応物、ヒドロキシプロピル(メタ)アクリレートと2,4−トリレンジイソシアネートの反応物、ヒドロキシプロピル(メタ)アクリレートとイソフォロンジイソシアネートの反応物が挙げられる。
で表される(メタ)アクリレート等が挙げられる。また、アルキルグリシジルエーテル、アリルグリシジルエーテル、グリシジル(メタ)アクリレート等のグリシジル基含有化合物と、(メタ)アクリル酸との付加反応により得られる化合物を使用することもできる。これら水酸基含有(メタ)アクリレートのうち、特に、2−ヒドロキシエチル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート等が好ましい。
で表わされる化合物等が挙げられる。
アローニックスTO−1210(東亞合成製)を使用することが出来る。
また、分岐構造を有するポリオールの市販品としては、例えば、第一工業製薬(株)製、旭硝子ウレタン(株)製三洋化成工業(株)製の「サニックスTP−400」、「サニックスGL−3000」、「サニックスGP−250」、「サニックスGP−400」、「サニックスGP−600」、「サニックスGP−1000」、「サニックスGP−3000」、「サニックスGP−3700M」、「サニックスGP−4000」、「サニックスGEP−2800」、「ニューポールTL4500N」等が挙げられる。
撹拌機を備えた反応容器に、テトラエチレンノニルフェニルエーテルアクリレート15.381g、2,6−ジ−t−ブチル−p−クレゾール0.015g、トルエンジイソシアナート7.80g、ジブチル錫ジラウレート0.023gを仕込み、これらを撹拌しながら液温度が20℃〜15℃になるまで氷冷した。ヒドロキシエチルアクリレート6.00gを加え、液温が35℃以下になるように制御しながら2時間攪拌して反応させた。次に、上記の混合物に数平均分子量2000のポリテトラメチレングリコール28.341g、数平均分子量400のポリエチレンビスフェノールAエーテル1.790g、ジブチル錫ジラウレート0.022gを加え、1時間室温で攪拌後、油浴にて65℃で2時間拡販した。残留イソシアネートが0.1重量%以下になった時を反応終了とした。以上により、表1に示す3種類のウレタン(メタ)アクリレートオリゴマーの混合溶液を得た。
この混合溶液を室温にし、そこへIrgacure184(チバ・スペシャルティ・ケミカルズ株式会社製)を2.90g、Irganox1035(チバ・スペシャルティ・ケミカルズ株式会社製)を0.30g、N−ビニル−2−ピロリドン5.770g、ポリオキシエチレンノニルフェニルエーテルアクリレート(M113;東亜合成化学工業株式会社)を15.4g、トリシクロデカンジメチロールジアクリレート(SA1002;三菱油化株式会社製)を2.275g、トリメチロールプロパンエトキシトリアクリレート(photomer4149;大阪有機工業株式会社製)を28.90入れ、50℃で1時間攪拌し目的の硬化性樹脂組成物を得た。
表1に示す組成の各成分を攪拌機を備えた反応容器に仕込み、液温度を50℃に制御しながら1時間攪拌し、液状硬化性樹脂組成物を得た。
前記実施例及び比較例で得た液状硬化性樹脂組成物を以下のような方法で硬化させ、試験片を作製し、下記の各評価を行った。
ガラスファイバに、一次被覆材(R1164;JSR株式会社製)、二次被覆材(R3180;JSR株式会社製)、インキ材(FS青インキ;株式会社ティーアンドケイ東華)をリワインダーモデル(吉田工業株式会社製)を用いて塗布及び紫外線硬化した作製した外径250μmの光ファイバ素線に対して、表1に示した各硬化性組成物を同装置を用いてさらに塗布及び紫外線硬化してアップジャケット層を被覆し、外径500μmのアップジャケット素線を作製してこれを測定試料とした。
図1に示すように、アップジャケット素線の末端から3cmの個所をホットストリッパー(古河電気工業株式会社製)で保持し、引っ張り試験機(島津製作所株式会社製)を用いて速度50m/minで引っ張り、アップジャケット層を引き抜く際の被覆除去応力(図2に示す最大応力)を測定した。測定は、アップジャケット素線の製造直後(「製造直後の被覆除去応力」という。)及び85℃・相対湿度85%環境下に7日間放置した後(「高温高湿試験後の被覆除去応力」という。)にそれぞれ測定した。
SH28PA;ジメチルポリシロキサンポリオキシアルキレン共重合体、東レ・ダウコーニング株式会社
FM0411;ジメチルポリシロキサンポリオキシアルキレン共重合体、チッソ株式会社
SF8428;ジメチルポリシロキサンポリオキシアルキレン共重合体、東レ・ダウコーニング株式会社
SH190;ジメチルポリシロキサンポリオキシアルキレン共重合体、東レ・ダウコーニング株式会社
ペインタッド19;ジメチルポリシロキサンポリオキシアルキレン共重合体、東レダウコーニング社
ペインタッド54;ジメチルポリシロキサンポリオキシアルキレン共重合体、東レダウコーニング社
Claims (5)
- 下記成分(A)、(B)及び(C)の合計量100質量%に対して、
(A)ウレタン(メタ)アクリレート 30〜90質量%、
(B)反応性希釈剤 1〜70質量%、
(C)重合開始剤 0.1〜10質量%
および
(D)平均分子量1,500〜35,000のシリコーン化合物 1〜50質量%
を含有する光ファイバアップジャケット用液状硬化性樹脂組成物。 - (D)シリコーン化合物が、ポリエーテル変性シリコーンである請求項1記載の光ファイバアップジャケット用液状硬化性樹脂組成物。
- 前記成分(A)、(B)及び(C)の合計量100質量%に対して、
(F)分子量1500以上のポリオール化合物を、0.1〜50質量
を含有する請求項1又は2に記載の光ファイバアップジャケット用液状硬化性樹脂組成物。 - 請求項1〜3のいずれか1項に記載の光ファイバアップジャケット用液状硬化性樹脂組成物の硬化物からなる光ファイバアップジャケット層。
- 請求項4に記載の光ファイバアップジャケット層を有する光ファイバアップジャケット素線。
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PCT/NL2005/000626 WO2006025733A1 (en) | 2004-08-30 | 2005-08-30 | Curable liquid resin optical fiber upjacket compositon |
EP05775184A EP1794243A1 (en) | 2004-08-30 | 2005-08-30 | Curable liquid resin optical fiber upjacket compositon |
US11/660,582 US20070246687A1 (en) | 2004-08-30 | 2005-08-30 | Curable Liquid Resin Optical Fiber Up Jacket Composition |
KR1020077007254A KR20070073760A (ko) | 2004-08-30 | 2005-08-30 | 경화성 액체 수지 광섬유 업자켓 조성물 |
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US (1) | US20070246687A1 (ja) |
EP (1) | EP1794243A1 (ja) |
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Cited By (6)
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JP2008233273A (ja) * | 2007-03-16 | 2008-10-02 | Sumitomo Electric Ind Ltd | 光ファイバケーブル |
JP2008249788A (ja) * | 2007-03-29 | 2008-10-16 | Jsr Corp | 光ファイバ素線の最外層被覆用液状硬化性樹脂組成物 |
JP2009168864A (ja) * | 2008-01-11 | 2009-07-30 | Jsr Corp | 光ファイバアップジャケット用液状硬化性樹脂組成物 |
JP2011158580A (ja) * | 2010-01-29 | 2011-08-18 | Jsr Corp | 光ファイバテープ層形成用液状硬化性樹脂組成物および光ファイバテープ心線 |
JP2012057124A (ja) * | 2010-09-13 | 2012-03-22 | Jsr Corp | 光ファイバ素線の最外層被覆用液状硬化性樹脂組成物及び光ファイバ素線 |
JP2019512034A (ja) * | 2016-03-02 | 2019-05-09 | アルケマ フランス | 二重硬化ソフトタッチコーティング |
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Publication number | Priority date | Publication date | Assignee | Title |
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JP2008247965A (ja) * | 2007-03-29 | 2008-10-16 | Jsr Corp | 液状硬化性樹脂組成物 |
WO2009084386A1 (ja) | 2007-12-27 | 2009-07-09 | Bridgestone Corporation | 接着性樹脂組成物 |
WO2009108056A1 (en) * | 2008-02-28 | 2009-09-03 | Dsm Ip Assets B.V. | Optical fiber tape with epoxy modified silicone additive |
JP2012056823A (ja) * | 2010-09-13 | 2012-03-22 | Jsr Corp | 光ファイバ素線の最外層被覆用液状硬化性樹脂組成物及び光ファイバ素線 |
US9442264B1 (en) | 2014-12-23 | 2016-09-13 | Superior Essex International LP | Tight buffered optical fibers and optical fiber cables |
JP2018077303A (ja) | 2016-11-08 | 2018-05-17 | 住友電気工業株式会社 | 光ファイバ心線 |
US10031303B1 (en) | 2017-08-29 | 2018-07-24 | Superior Essex International LP | Methods for forming tight buffered optical fibers using compression to facilitate subsequent loosening |
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-
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- 2005-08-30 WO PCT/NL2005/000626 patent/WO2006025733A1/en active Application Filing
- 2005-08-30 KR KR1020077007254A patent/KR20070073760A/ko not_active Application Discontinuation
- 2005-08-30 EP EP05775184A patent/EP1794243A1/en not_active Withdrawn
- 2005-08-30 US US11/660,582 patent/US20070246687A1/en not_active Abandoned
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JP2000231044A (ja) * | 1999-02-12 | 2000-08-22 | Sumitomo Electric Ind Ltd | 光ファイバテープ心線 |
JP2006010717A (ja) * | 2004-04-28 | 2006-01-12 | Dainippon Ink & Chem Inc | 活性エネルギー線硬化型樹脂組成物及びそれを用いた光ファイバー単心線 |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008233273A (ja) * | 2007-03-16 | 2008-10-02 | Sumitomo Electric Ind Ltd | 光ファイバケーブル |
JP2008249788A (ja) * | 2007-03-29 | 2008-10-16 | Jsr Corp | 光ファイバ素線の最外層被覆用液状硬化性樹脂組成物 |
JP2009168864A (ja) * | 2008-01-11 | 2009-07-30 | Jsr Corp | 光ファイバアップジャケット用液状硬化性樹脂組成物 |
JP2011158580A (ja) * | 2010-01-29 | 2011-08-18 | Jsr Corp | 光ファイバテープ層形成用液状硬化性樹脂組成物および光ファイバテープ心線 |
JP2012057124A (ja) * | 2010-09-13 | 2012-03-22 | Jsr Corp | 光ファイバ素線の最外層被覆用液状硬化性樹脂組成物及び光ファイバ素線 |
JP2019512034A (ja) * | 2016-03-02 | 2019-05-09 | アルケマ フランス | 二重硬化ソフトタッチコーティング |
JP7159051B2 (ja) | 2016-03-02 | 2022-10-24 | アルケマ フランス | 二重硬化ソフトタッチコーティング |
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EP1794243A1 (en) | 2007-06-13 |
KR20070073760A (ko) | 2007-07-10 |
US20070246687A1 (en) | 2007-10-25 |
JP4490798B2 (ja) | 2010-06-30 |
WO2006025733A1 (en) | 2006-03-09 |
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