WO2009108056A1 - Optical fiber tape with epoxy modified silicone additive - Google Patents
Optical fiber tape with epoxy modified silicone additive Download PDFInfo
- Publication number
- WO2009108056A1 WO2009108056A1 PCT/NL2009/050090 NL2009050090W WO2009108056A1 WO 2009108056 A1 WO2009108056 A1 WO 2009108056A1 NL 2009050090 W NL2009050090 W NL 2009050090W WO 2009108056 A1 WO2009108056 A1 WO 2009108056A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- meth
- acrylate
- resin composition
- modified silicone
- liquid resin
- Prior art date
Links
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 35
- 239000013307 optical fiber Substances 0.000 title claims abstract description 15
- 239000004593 Epoxy Substances 0.000 title description 3
- 239000000654 additive Substances 0.000 title description 3
- 230000000996 additive effect Effects 0.000 title description 2
- 239000007788 liquid Substances 0.000 claims abstract description 45
- 239000011342 resin composition Substances 0.000 claims abstract description 40
- 239000000463 material Substances 0.000 claims abstract description 28
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 238000005253 cladding Methods 0.000 claims description 12
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 7
- 230000003252 repetitive effect Effects 0.000 claims description 6
- 238000005227 gel permeation chromatography Methods 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 238000003491 array Methods 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 111
- 239000000203 mixture Substances 0.000 abstract description 5
- 229920005862 polyol Polymers 0.000 description 60
- 150000003077 polyols Chemical class 0.000 description 56
- -1 polytetramethylene Polymers 0.000 description 44
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 28
- 239000004721 Polyphenylene oxide Substances 0.000 description 20
- 229920000570 polyether Polymers 0.000 description 20
- 125000005442 diisocyanate group Chemical group 0.000 description 19
- 125000002947 alkylene group Chemical group 0.000 description 17
- 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 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000003505 polymerization initiator Substances 0.000 description 8
- 229920001451 polypropylene glycol Polymers 0.000 description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- 150000001923 cyclic compounds Chemical class 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 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
- 239000005058 Isophorone diisocyanate Substances 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 4
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 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
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 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
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-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
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-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
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical group C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 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
- 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
- 229940095095 2-hydroxyethyl acrylate Drugs 0.000 description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 2
- LJPCNSSTRWGCMZ-UHFFFAOYSA-N 3-methyloxolane Chemical compound CC1CCOC1 LJPCNSSTRWGCMZ-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 206010034962 Photopsia Diseases 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
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 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
- PODOEQVNFJSWIK-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 PODOEQVNFJSWIK-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 150000003951 lactams Chemical group 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229910000065 phosphene Inorganic materials 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- 230000001235 sensitizing effect Effects 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229940086542 triethylamine Drugs 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 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 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- UYVWNPAMKCDKRB-UHFFFAOYSA-N 1,2,4,5-tetraoxane Chemical compound C1OOCOO1 UYVWNPAMKCDKRB-UHFFFAOYSA-N 0.000 description 1
- CYIGRWUIQAVBFG-UHFFFAOYSA-N 1,2-bis(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOCCOC=C CYIGRWUIQAVBFG-UHFFFAOYSA-N 0.000 description 1
- GJZFGDYLJLCGHT-UHFFFAOYSA-N 1,2-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(CC)C(CC)=CC=C3SC2=C1 GJZFGDYLJLCGHT-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 1
- LAYAKLSFVAPMEL-UHFFFAOYSA-N 1-ethenoxydodecane Chemical compound CCCCCCCCCCCCOC=C LAYAKLSFVAPMEL-UHFFFAOYSA-N 0.000 description 1
- UKDKWYQGLUUPBF-UHFFFAOYSA-N 1-ethenoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOC=C UKDKWYQGLUUPBF-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- SDXHBDVTZNMBEW-UHFFFAOYSA-N 1-ethoxy-2-(2-hydroxyethoxy)ethanol Chemical compound CCOC(O)COCCO SDXHBDVTZNMBEW-UHFFFAOYSA-N 0.000 description 1
- CSCSROFYRUZJJH-UHFFFAOYSA-N 1-methoxyethane-1,2-diol Chemical compound COC(O)CO CSCSROFYRUZJJH-UHFFFAOYSA-N 0.000 description 1
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 1
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WAVKEPUFQMUGBP-UHFFFAOYSA-N 2-(3-nitrophenyl)acetonitrile Chemical compound [O-][N+](=O)C1=CC=CC(CC#N)=C1 WAVKEPUFQMUGBP-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- JJRUAPNVLBABCN-UHFFFAOYSA-N 2-(ethenoxymethyl)oxirane Chemical compound C=COCC1CO1 JJRUAPNVLBABCN-UHFFFAOYSA-N 0.000 description 1
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- XIXWTBLGKIRXOP-UHFFFAOYSA-N 2-ethenyloxolane Chemical compound C=CC1CCCO1 XIXWTBLGKIRXOP-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- CXURGFRDGROIKG-UHFFFAOYSA-N 3,3-bis(chloromethyl)oxetane Chemical compound ClCC1(CCl)COC1 CXURGFRDGROIKG-UHFFFAOYSA-N 0.000 description 1
- DSSAWHFZNWVJEC-UHFFFAOYSA-N 3-(ethenoxymethyl)heptane Chemical compound CCCCC(CC)COC=C DSSAWHFZNWVJEC-UHFFFAOYSA-N 0.000 description 1
- YDIYEOMDOWUDTJ-UHFFFAOYSA-M 4-(dimethylamino)benzoate Chemical compound CN(C)C1=CC=C(C([O-])=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-M 0.000 description 1
- UGVRJVHOJNYEHR-UHFFFAOYSA-N 4-chlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 UGVRJVHOJNYEHR-UHFFFAOYSA-N 0.000 description 1
- HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical compound OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- XAYDWGMOPRHLEP-UHFFFAOYSA-N 6-ethenyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2OC21C=C XAYDWGMOPRHLEP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GZSUIHUAFPHZSU-UHFFFAOYSA-N 9-ethyl-2,3-dihydro-1h-carbazol-4-one Chemical compound C12=CC=CC=C2N(CC)C2=C1C(=O)CCC2 GZSUIHUAFPHZSU-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- XVZXOLOFWKSDSR-UHFFFAOYSA-N Cc1cc(C)c([C]=O)c(C)c1 Chemical group Cc1cc(C)c([C]=O)c(C)c1 XVZXOLOFWKSDSR-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
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- 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
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/065—Polyamides; Polyesteramides; Polyimides
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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
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- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/067—Polyurethanes; Polyureas
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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
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- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/068—Polysiloxanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/40—High-molecular-weight compounds
- C08G18/61—Polysiloxanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- 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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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
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- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
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- G—PHYSICS
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- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
- G02B6/44—Mechanical structures for providing tensile strength and external protection for fibres, e.g. optical transmission cables
- G02B6/4479—Manufacturing methods of optical cables
- G02B6/448—Ribbon cables
Definitions
- the present invention relates to a curable liquid resin composition that is optimal for use as an optical fiber tape material.
- the structure of optical fibers includes a resin cladding which is used to protect and reinforce the glass fibers produced from molten filaments. This process is called fiber pulling, and the cladding on the surface of the optical fibers known to the art includes a soft primary cladding layer, outside of which is a high strength secondary cladding layer. Further, structures are known to the art for practical application of such fibers wherein a plurality of these resin clad optical fibers are laid out on a flat surface and bound in parallel in bundles with a curable tape cladding layer.
- the resin composition used to form this first cladding layer is called the primary material
- the resin composition used to form the secondary cladding layer is called the secondary material
- resin composition used to form the tape cladding is called the tape material.
- a widely used cladding method is to apply a coating of a curable liquid resin composition, and then cure it using heat or light, especially using ultraviolet light to perform the curing.
- Excellent physical properties are required of the secondary material and tape material; they must have a relatively high modulus of elasticity and a high elongation to breakage value. Further, since raw fibers after application of the secondary material, tape, etc. and the tape and resulting cables, etc., must be wound around spools for storage and transport, they must have excellent surface properties so that the surfaces of the secondary material and tape do not stick to each other. Further, for identification purposes, ink should be adherent to the surfaces of the secondary material or tape material to allow them to be printed with characters that will not peel off.
- Curable liquid resin compositions that contain a number of different silicone compounds have been evaluated in attempts to improve the surface slidability of the cured material as well as ink adhesion (see Japanese
- the objective of the present invention is to provide a curable liquid resin composition that is optimal as an optical fiber material having excellent surface slidability and printability when cured.
- the invention is directed to a curable liquid resin composition that contains the following components, (A), (B) and (C):
- the invention is directed to the curable liquid resin composition of the first aspect of the invention used as optical fiber tape material.
- the invention is directed to a curable liquid resin composition that contains the following components, (A), (B) and (C): (A) urethane (meth) aery late;
- urethane (meth)acrylate employed as the (A) component in the curable liquid resin composition of the present invention
- a polyol can be reacted with a (meth) aery late containing diisocyanate and hydroxyl groups to produce a urethane (meth) aery late (Al).
- a polyol can be reacted with a (meth) aery late containing diisocyanate and hydroxyl groups to produce a urethane (meth) aery late (Al).
- it can be prepared by reacting the isocyanate group of a diisocyanate with the hydroxyl group of the polyol and the hydroxyl group of a (meth)acrylate that contains a hydroxyl group.
- polyols examples include polyether polyols, polyester polyols, polycarbonate polyols, polycaprolactone polyols or other polyols. There are no particular restrictions upon the polymer structural units of these polyols, they may be random polymers, block polymers or graft polymers.
- polyether polyols include polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polyhexamethylene glycol, polybutamethylene glycol, polydecamethylene glycol or aliphatic polyether polyols obtained by ring-opening polymerization of two or more types of ion polymerizable cyclic compounds.
- Examples of such ion polymerizable cyclic compounds include cyclic ethers such as ethylene oxide, propylene oxide, butene-1-oxide, isobutene oxide, 3,3-bis chloro methyl oxetane, tetrahydrofuran, 2 -methyl tetrahydrofuran, 3 -methyl tetrahydrofuran, dioxane, trioxane, tetraoxane, cyclohexene oxide, styrene oxide, epichlorohydrin, glycidyl methacrylate, allyl glycidyl ether, allyl glycidyl carbonate, butadiene monoxide, isoprene monoxide, vinyl oxytane, vinyl tetrahydrofuran, vinyl cyclohexene oxide, vinyl glycidyl ether, butyl glycidyl ether, glycidyl benzoate esters
- polyether polyols may be obtained by ring opening polymerization between the foregoing ion-polymerizable cyclic compounds and cyclic imines such as ethylene imine, or cyclic lactones such as ⁇ -propiolactone, glycolic acid lactone, etc.
- ion polymerizable cyclic compounds include tetrahydrofuran and propylene oxide, tetrahydrofuran and 2-methyl tetrahydrofuran, tetrahydrofuran and 3-methyl tetrahydrofuran, tetrahydrofuran and ethylene oxide, propylene oxide and ethylene oxide, butane- 1-oxide and ethylene oxide and 3-element polymers such as tetrahydrofuran, butane- 1-oxide, and ethylene oxide.
- These ion-polymerizable cyclic compounds may be ring opening polymerized to produce either random or block form.
- aliphatic polyether polyols may be obtained as commercial products. Examples include PTMG650, PTMGlOOO, PTMG2000 (all by Mitsubishi Chemical Co..); PPG-400, PPGlOOO, PPG2000, PPG3000, EXCENOL720, 1020 and 2020 (all by Asahi Glass-Urethane Co..); PEGlOOO, UNICEF DCIlOO, DC1800 (all by Nippon Yushi Co..), PPTG 2000, PPTGlOOO, PTG400, PTGL 2000 (all by Hodotani Chemical Co..) Z-3001-4, Z-3001-5, PBG2000A, PBG2000B (all by Daiichi Kogyo Seiyaku Co..), etc.
- cyclic polyether polyols include alkylene oxide adduct polyol of bisphenol A, alkylene oxide adduct polyol of bisphenol F, hydrogenated bisphenol A, alkylene oxide adduct polyol of hydrogenated bisphenol A, alkylene oxide adduct polyol of bisphenol F, alkylene oxide adduct polyol of hydroquinone, alkylene oxide adduct polyol of naphtohydroquinone, alkylene oxide adduct polyol of anthrahydroquinone, 1,4-cyclohexane polyol and its alkylene oxide adduct polyol, tricyclodecane polyol, tricyclodecane dimethanol, pentacyclo pentadecane polyol, pentacyclo pentadecane dimethanol, etc.
- alkylene oxide adduct polyol of bisphenol A and tricyclodecane dimethanol Preferred among them are the alkylene oxide adduct polyol of bisphenol A and tricyclodecane dimethanol.
- these polyols are commercially available, such as Uniol DA 400, DA 700, DA 1000, DB 400 (all from Nippon Yushi Co.), tricyclodecane dimethanol (Mitsubishi Chemical Co..), etc.
- Examples of other cyclic poly ether polyols include xylene oxide aduct polyol, alkylene oxide adduct polyol of bisphenol F, alkylene oxide adduct polyol of 1,4-cyclohexane polyol, etc.
- polyether polyols especially aliphatic polyether polyols or cyclic polyether polyols.
- preferred examples of aliphatic polyether polyols include polypropylene glycol and butane- 1-oxide and ethylene oxide copolymer, with polypropylene glycol being especially preferred.
- These polyols may be commercially obtained as PPG- 400, PPGlOOO, PPG2000, PPG3000, EXCENOL 720, 1020, and 2020 (all by Asahi Glass-Urethane Co..).
- Diol copolymers of butane- 1-oxide and ethylene oxide that may be obtained commercially include EO/BO500, EO/BO1000, EO/BO2000, EO/BO3000, EO/BO4000 (all by Daiichi Kogyo Seiyaku Co..), etc.
- Preferred cyclic polyether polyols include alkylene oxide adduct polyol of bisphenol A and alkylene oxide adduct polyol of bisphenol F, with the alkylene oxide adduct polyol of bisphenol A being especially preferred.
- These polyether polyols may be obtained commercially as Uniol DA400, DA700, DAlOOO, DB400 (all by Nippon Yushi Co..), etc.
- a combination of an aliphatic polyether polyol and cyclic polyether polyol as the polyols.
- Such combinations have the advantage of offering both the aliphatic polyether polyol with its relatively pliable structure and the cyclic polyether polyol with its relatively rigid structure to enable the optimal control of the Young's modulus of the cured material.
- the number-averaged molecular weight of the aliphatic polyether polyol should range between 1000 and 4000, with a range of 1000 to 2000 being especially preferred.
- the number-averaged molecular weight of the cyclic polyether polyol should range from 400 to 1000, with 400 to 800 being especially preferred.
- the number-averaged molecular weight may be determined by gel permeation chromatography (the GPC method) using a polystyrene standard for molecular weight.
- diisocyanates examples include 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 1,3-xylene diisocyanate, 1,4-xylene diisocyanate, 1,5 -naphthalene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, 3,3'-dimethyl, 4,4'-diphenyl methane diisocyanate, 4,4'-diphenyl methane diisocyanate, 3,3'-dimethyl phenylene diisocyanate, 4,4'-biphenylene diisocyanate, 1,6-hexane diisocyanate, isophorone diisocyanate, methylene bis(4-cyclohexyl isocyanate), 2,2,4-trimethyl hexamethylene diisocyanate, bis(2-isocyanate ethyl) fumarate, 6-isopropyl-l,3-phen
- diisocyanates may be used singly or in combinations of two or more types.
- hydroxyl group-containing (meth)acrylates include, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 2-hydroxy-3-phenyl oxypropyl (meth)acrylate, 1,4-butane polyol mono(meth)acrylate, 2-hydroxyalkyl (meth)acryloyl phosphate, 4-hydroxy cyclohexyl (meth)acrylate, 1,6-hexa polyol mono(meth)acrylate, neopentyl glycol mono(meth)acrylate, trimethylol propane di(meth)acrylate, trimethylol ethane di(meth)acrylate, pentaerythritol tri(meth) aery late, dipentaerythritol penta(meth)acrylate, the (meth)acrylates expressed by formulas (4) and (5) below, etc.).
- R 1 represents a hydrogen atom or methyl group
- n is a number from 1 to 15.
- glycidyl group-containing compounds such as alkyl glycidyl ethers, allyl glycidyl ethers, glycidyl (meth)acrylate, etc. and a (meth)acrylate.
- hydroxyl group-containing (meth) acrylates are 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, etc.
- a urethaning catalyst such as copper naphthenate, cobalt naphthenate, zinc naphthenate, dibutyl tin dilaurate, triethyl amine, l,4-diazabicyclo[2.2.2]octane, 2,6,7-trimethyl-l,4-diazabicyclo[2.2.2]octane, per 100 parts by mass of the total of reactants.
- the reaction temperature normally ranges from 10 to 90 °C, with 30 to 80 °C being the preferred range.
- the diisocyanates and the hydroxyl group-containing (meth)acrylate used for the synthesis of the (A2) component are respectively similar to the diisocyanates and the hydroxyl group-containing (meth)acrylates used for the synthesis of the (Al) component.
- Examples of the (Bl) mono-functional compounds include vinyl group-containing lactams such as N- vinyl pyrolidone, N- vinyl caprolactam; alicyclic structure-containing (meth)acrylates such as 2-ethylhexyl (meth)acrylate, isobornyl (meth)acrylate, bornyl (meth)acrylate, tricyclodecanyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclo pentanyl (meth)acrylate, cyclohexyl (meth)acrylate; and benzyl (meth)acrylate, 4-butylcyclohexyl (meth) aery late, (meth)acryloyl morpholine, vinyl imidazole, vinyl pyridine, etc.
- lactams such as N- vinyl pyrolidone, N- vinyl caprolactam
- alicyclic structure-containing (meth)acrylates such as 2-ethylhexyl
- mono-functional ethylenically unsaturated group-containing compounds include Aronix Mill, M113, M114, M117 (all by Toa Gosei Co.): KAYARAD, TClIOS, R629, R644 (all by Nippon Kayaku Co.); IBXA, Biscoat 3700 (by Osaka Organic Chemical Industries Co..), etc.
- examples of light sensitizing agent include triethyl amine, diethyl amine, n-methyl diethanol amine, ethanol amine, 4-dimethyl aminobenzoate, 4-dimethyl amino methyl benzoate, 4-dimethyl amino ethyl benzoate, 4-dimethyl amino isoamyl benzoate, Ebecryl P102, 103, 104, 105 (all from UBC Co.), etc.
- Preparation Example 1 Synthesis of the (A) Urethane (meth) Acrvlate 16.640 g of isobornyl acrylate, 0.016 g of 2,6-di-t-butyl-p-cresol, 19.173 g of trilene diisocyanate, 19.345 g of polypropylene glycol with a number-averaged molecular weight of 2000, and 9.051 g of polypropylene glycol with a number-averaged molecular weight of 400 were added to a reaction vessel equipped with a stirrer, which was then cooled to a liquid temperature of 15 °C.
- HEA- TDI- HEA 13
- HEA represents a structure derived from hydroxyl ethyl acrylate
- TDI a structure derived from toluene diisocyanate
- PPG2000 a structure derived from polypropylene glycol with a number-averaged molecular weight of 2000
- DA400 a structure derived from polyethylene bisphenol A ether having a number-averaged molecular weight of 400.
- the resulting acryloyl group -modified silicone was labeled as acryloyl group -modified silicone 1.
- Example 1 The components listed in Table 1 were added to a reaction vessel equipped with a stirrer and stirred to a uniform solution at 50 °C to obtain the curable liquid resin composition.
- An applicator bar 380 ⁇ m thick was used to apply a coating of the curable liquid resin compositions atop a glass plate, and then the coating was cured in an air environment by irradiation with 1 J/cm 2 of ultraviolet light energy to obtain a film, which was used for a Young's modulus measurement.
- the film sample was prepared into short slips measuring 6 mm wide and 25 mm long in the stretch area, and these were pulled under a temperature of 23 °C and humidity of 50 % at a pulling rate of 1 mm/minute while the Young's modulus was determined from the tensile strength at a 2.5 % strain.
- An applicator bar 250 ⁇ m thick was used to apply a coating of the curable liquid resin compositions atop a glass plate, and then the coating was cured in a nitrogen environment by irradiation with 0.5 J/cm 2 of ultraviolet light energy.
- the cured material was allowed to stand at 23 °C in a 50 % humidity environment for 13 hours before preparing the test samples.
- the cured films obtained in the above- described manner were peeled away from the glass plates and cut into 3 cm widths, and oriented with the top surface as the one that was irradiated with the ultraviolet light, before taping them to both surfaces of an aluminum plate.
- Two sheets of the test samples were used with the cured surfaces stacked against each other, the sandwich being held together with double clips for the surface sliding test.
- the test was conducted at a pulling rate of 50 mm/min, a contact surface area of 5.4 cm 2 between the cured material surfaces, and a pressure of 4.7 N/cm 2 exerted by the double clips.
- the load was used to calculate the shear sliding force (units: N/cm 2 ).
- SH190 dimethyl polysiloxane polyoxyalkylene copolymer (by Toray Dow-Corning Co.)
- SH28PA dimethyl polysiloxane polyoxyalkylene copolymer (by Toray Dow-Corning Co.)
- Irgacure 184 1-hydroxy-cyclohexyl-phenyl-ketone (by Ciba Specialty Chemical
- Irgacure 907 2-methyl-l-(4-methyl thiophenyl)-2-morpholino-propane-l-one
- Lucirin TPO 2,4,6-trimethyl benzoyl diphenyl phosphine oxide (by Ciba Specialty Chemical Co.)
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Abstract
The invention is a curable liquid resin composition that is optimal for use as an optical fiber tape material providing excellent surface slidability and printability when cured. In order to achieve the desired result the composition was formulated using an epoxy- modified silicone to deliver the desired surface slidability and printability in the cured material. The curable liquid resin composition contains urethane (meth)acrylate, a compound containing an ethylenically unsaturated group and an epoxy- modified silicone.
Description
Title: Optical Fiber Tape with Epoxy Modified Silicone Additive
Field of the invention
The present invention relates to a curable liquid resin composition that is optimal for use as an optical fiber tape material.
Background of the invention
The structure of optical fibers includes a resin cladding which is used to protect and reinforce the glass fibers produced from molten filaments. This process is called fiber pulling, and the cladding on the surface of the optical fibers known to the art includes a soft primary cladding layer, outside of which is a high strength secondary cladding layer. Further, structures are known to the art for practical application of such fibers wherein a plurality of these resin clad optical fibers are laid out on a flat surface and bound in parallel in bundles with a curable tape cladding layer. The resin composition used to form this first cladding layer is called the primary material, the resin composition used to form the secondary cladding layer is called the secondary material, and resin composition used to form the tape cladding is called the tape material. A widely used cladding method is to apply a coating of a curable liquid resin composition, and then cure it using heat or light, especially using ultraviolet light to perform the curing.
Excellent physical properties are required of the secondary material and tape material; they must have a relatively high modulus of elasticity and a high elongation to breakage value. Further, since raw fibers after application of the secondary material, tape, etc. and the tape and resulting cables, etc., must be wound around spools for storage and transport, they must have excellent surface properties so that the surfaces of the secondary material and tape do not stick to each other. Further, for identification purposes, ink should
be adherent to the surfaces of the secondary material or tape material to allow them to be printed with characters that will not peel off.
Curable liquid resin compositions that contain a number of different silicone compounds have been evaluated in attempts to improve the surface slidability of the cured material as well as ink adhesion (see Japanese
Unexamined Patent Application Publication 2005-255946). Yet, a demand remains for an excellent curable liquid resin composition that exhibits both surface slidability and good printability.
Summary of the invention
The objective of the present invention is to provide a curable liquid resin composition that is optimal as an optical fiber material having excellent surface slidability and printability when cured. After evaluating numerous compositions for curable liquid resin compositions containing urethane
(meth)acrylate, we discovered that the foregoing objective could be achieved by employing an epoxy-modified silicone to deliver the desired surface slidability and printability in the cured material.
In a first aspect the invention is directed to a curable liquid resin composition that contains the following components, (A), (B) and (C):
(A) urethane (meth) acrylate;
(B) a compound containing an ethylenically unsaturated group; and
(C) epoxy-modified silicone.
In a second aspect the invention is directed to the curable liquid resin composition of the first aspect of the invention used as optical fiber tape material.
Cladding obtained from the curable liquid resin composition according to the present invention exhibits excellent surface slidability and printability. It is optimal for use as an optical fiber tape material.
Detailed description of the invention
In a first aspect the invention is directed to a curable liquid resin composition that contains the following components, (A), (B) and (C): (A) urethane (meth) aery late;
(B) a compound containing an ethylenically unsaturated group; and
(C) epoxy-modified silicone.
There are no particular limitations on the urethane (meth)acrylate employed as the (A) component in the curable liquid resin composition of the present invention; for example, a polyol can be reacted with a (meth) aery late containing diisocyanate and hydroxyl groups to produce a urethane (meth) aery late (Al). To wit, it can be prepared by reacting the isocyanate group of a diisocyanate with the hydroxyl group of the polyol and the hydroxyl group of a (meth)acrylate that contains a hydroxyl group. The method for this reaction may be one wherein the polyol, diisocyanate, and the hydroxyl group-containing (meth)acrylate are all reacted together; wherein the polyol and diisocyanate are first reacted, and then reacted with the hydroxyl group-containing (meth)acrylate; wherein the diisocyanate and the hydroxyl group-containing (meth) aery late are first reacted, followed by a reaction with the polyol; and wherein the diisocyanate and the hydroxyl group-containing (meth)acrylate are first reacted, then reacted with the polyol, and finally reacted with a hydroxyl group-containing (meth) aery late.
Examples of polyols that can be used include polyether polyols, polyester polyols, polycarbonate polyols, polycaprolactone polyols or other polyols. There are no particular restrictions upon the polymer structural units of these polyols, they may be random polymers, block polymers or graft polymers. Examples of polyether polyols include polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polyhexamethylene glycol, polybutamethylene glycol, polydecamethylene glycol or aliphatic polyether
polyols obtained by ring-opening polymerization of two or more types of ion polymerizable cyclic compounds. Examples of such ion polymerizable cyclic compounds include cyclic ethers such as ethylene oxide, propylene oxide, butene-1-oxide, isobutene oxide, 3,3-bis chloro methyl oxetane, tetrahydrofuran, 2 -methyl tetrahydrofuran, 3 -methyl tetrahydrofuran, dioxane, trioxane, tetraoxane, cyclohexene oxide, styrene oxide, epichlorohydrin, glycidyl methacrylate, allyl glycidyl ether, allyl glycidyl carbonate, butadiene monoxide, isoprene monoxide, vinyl oxytane, vinyl tetrahydrofuran, vinyl cyclohexene oxide, vinyl glycidyl ether, butyl glycidyl ether, glycidyl benzoate esters, etc. Furthermore, polyether polyols may be obtained by ring opening polymerization between the foregoing ion-polymerizable cyclic compounds and cyclic imines such as ethylene imine, or cyclic lactones such as β-propiolactone, glycolic acid lactone, etc. Specific examples of combinations of two or more types of ion polymerizable cyclic compounds include tetrahydrofuran and propylene oxide, tetrahydrofuran and 2-methyl tetrahydrofuran, tetrahydrofuran and 3-methyl tetrahydrofuran, tetrahydrofuran and ethylene oxide, propylene oxide and ethylene oxide, butane- 1-oxide and ethylene oxide and 3-element polymers such as tetrahydrofuran, butane- 1-oxide, and ethylene oxide. These ion-polymerizable cyclic compounds may be ring opening polymerized to produce either random or block form.
These aliphatic polyether polyols may be obtained as commercial products. Examples include PTMG650, PTMGlOOO, PTMG2000 (all by Mitsubishi Chemical Co..); PPG-400, PPGlOOO, PPG2000, PPG3000, EXCENOL720, 1020 and 2020 (all by Asahi Glass-Urethane Co..); PEGlOOO, UNICEF DCIlOO, DC1800 (all by Nippon Yushi Co..), PPTG 2000, PPTGlOOO, PTG400, PTGL 2000 (all by Hodotani Chemical Co..) Z-3001-4, Z-3001-5, PBG2000A, PBG2000B (all by Daiichi Kogyo Seiyaku Co..), etc.
Further examples of cyclic polyether polyols include alkylene oxide adduct polyol of bisphenol A, alkylene oxide adduct polyol of bisphenol F,
hydrogenated bisphenol A, alkylene oxide adduct polyol of hydrogenated bisphenol A, alkylene oxide adduct polyol of bisphenol F, alkylene oxide adduct polyol of hydroquinone, alkylene oxide adduct polyol of naphtohydroquinone, alkylene oxide adduct polyol of anthrahydroquinone, 1,4-cyclohexane polyol and its alkylene oxide adduct polyol, tricyclodecane polyol, tricyclodecane dimethanol, pentacyclo pentadecane polyol, pentacyclo pentadecane dimethanol, etc. Preferred among them are the alkylene oxide adduct polyol of bisphenol A and tricyclodecane dimethanol. Many of these polyols are commercially available, such as Uniol DA 400, DA 700, DA 1000, DB 400 (all from Nippon Yushi Co.), tricyclodecane dimethanol (Mitsubishi Chemical Co..), etc. Examples of other cyclic poly ether polyols include xylene oxide aduct polyol, alkylene oxide adduct polyol of bisphenol F, alkylene oxide adduct polyol of 1,4-cyclohexane polyol, etc.
Preferred among these polyols are polyether polyols, especially aliphatic polyether polyols or cyclic polyether polyols. Specifically, preferred examples of aliphatic polyether polyols include polypropylene glycol and butane- 1-oxide and ethylene oxide copolymer, with polypropylene glycol being especially preferred. These polyols may be commercially obtained as PPG- 400, PPGlOOO, PPG2000, PPG3000, EXCENOL 720, 1020, and 2020 (all by Asahi Glass-Urethane Co..). Diol copolymers of butane- 1-oxide and ethylene oxide that may be obtained commercially include EO/BO500, EO/BO1000, EO/BO2000, EO/BO3000, EO/BO4000 (all by Daiichi Kogyo Seiyaku Co..), etc. Preferred cyclic polyether polyols include alkylene oxide adduct polyol of bisphenol A and alkylene oxide adduct polyol of bisphenol F, with the alkylene oxide adduct polyol of bisphenol A being especially preferred. These polyether polyols may be obtained commercially as Uniol DA400, DA700, DAlOOO, DB400 (all by Nippon Yushi Co..), etc.
It is further preferable to use a combination of an aliphatic polyether polyol and cyclic polyether polyol as the polyols. Such combinations have the advantage of offering both the aliphatic polyether polyol with its relatively
pliable structure and the cyclic polyether polyol with its relatively rigid structure to enable the optimal control of the Young's modulus of the cured material.
Further, the number-averaged molecular weight of the aliphatic polyether polyol should range between 1000 and 4000, with a range of 1000 to 2000 being especially preferred. The number-averaged molecular weight of the cyclic polyether polyol should range from 400 to 1000, with 400 to 800 being especially preferred. The number-averaged molecular weight may be determined by gel permeation chromatography (the GPC method) using a polystyrene standard for molecular weight.
Examples of diisocyanates include 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 1,3-xylene diisocyanate, 1,4-xylene diisocyanate, 1,5 -naphthalene diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, 3,3'-dimethyl, 4,4'-diphenyl methane diisocyanate, 4,4'-diphenyl methane diisocyanate, 3,3'-dimethyl phenylene diisocyanate, 4,4'-biphenylene diisocyanate, 1,6-hexane diisocyanate, isophorone diisocyanate, methylene bis(4-cyclohexyl isocyanate), 2,2,4-trimethyl hexamethylene diisocyanate, bis(2-isocyanate ethyl) fumarate, 6-isopropyl-l,3-phenyl diisocyanate, 4-diphenyl propane diisocyanate, lysine diisocyanate, hydrogenated diphenyl methane diisocyanate, hydrogenated xylene diisocyanate, tetramethylxylene diisocyanate, 2,5 (or 2,6)-bis(isocyanate methyl)-bicyclo[2.2.1]heptane, etc. Preferred among them are 2,4-tolylene diisocyanate, isophorone diisocyanate, xylene diisocyanate, methylene bis(4-cyclohexyl isocyanate), etc.
These diisocyanates may be used singly or in combinations of two or more types.
Examples of hydroxyl group-containing (meth)acrylates include, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 2-hydroxy-3-phenyl oxypropyl (meth)acrylate, 1,4-butane polyol mono(meth)acrylate, 2-hydroxyalkyl (meth)acryloyl phosphate, 4-hydroxy cyclohexyl (meth)acrylate, 1,6-hexa polyol
mono(meth)acrylate, neopentyl glycol mono(meth)acrylate, trimethylol propane di(meth)acrylate, trimethylol ethane di(meth)acrylate, pentaerythritol tri(meth) aery late, dipentaerythritol penta(meth)acrylate, the (meth)acrylates expressed by formulas (4) and (5) below, etc.).
CH2=C(R1)- COOCH2CH2-(OCOCH2CH2CH2CH2CH2)- n OH (4)
In the formula, R1 represents a hydrogen atom or methyl group, n is a number from 1 to 15.
It is further possible to use compounds obtained through adduct reactions between glycidyl group-containing compounds such as alkyl glycidyl ethers, allyl glycidyl ethers, glycidyl (meth)acrylate, etc. and a (meth)acrylate. Preferred among such hydroxyl group-containing (meth) acrylates are 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, etc.
These hydroxyl group-containing (meth)acrylate compounds may be used singly or in combinations of two or more types. The preferred usage ratios for the polyol, diisocyanate, and the hydroxyl group-containing (meth)acrylate are, 1.1 to 3 equivalent isocyanate groups from the diisocyanate per 1 equivalent hydroxyl group contained in the polyol, and from 0.2 to 1.5 equivalent hydroxyl groups from the hydroxyl group-containing (meth) aery late. In reacting these compounds, it is preferable to add from 0.01 to 1 part by mass of a urethaning catalyst, such as copper naphthenate, cobalt naphthenate, zinc naphthenate, dibutyl tin dilaurate, triethyl amine, l,4-diazabicyclo[2.2.2]octane, 2,6,7-trimethyl-l,4-diazabicyclo[2.2.2]octane, per 100 parts by mass of the total of reactants. The reaction temperature normally ranges from 10 to 90 °C, with 30 to 80 °C being the preferred range.
It is possible to use a part of the hydroxyl group-containing (meth)acrylate as a substituent functional group that can be added to the isocyanate groups. Examples include γ-mercapto trimethoxy silane, γ-amino trimethoxy silane, etc. The use of such compounds enhances the binding to the glass or other substrate.
In addition to the urethane (meth)acrylate (Al) obtained from the reaction of a polyol with diisocyanate and a hydroxyl group-containing (meth) aery late as the component (A), it is possible to use it in combination with the reaction product from diisocyanate and a hydroxyl group-containing (meth)acrylate, urethane (meth)acrylate (A2), which does not have a polyol-derived structure. Since urethane (meth) aery late (A2) has a rigid structure, the combination of the urethane (meth)acrylate (Al) with the urethane (meth)acrylate (A2) provides the ability to adjust the Young's modulus of the cured material over a broad range. Urethane (meth)acrylate (A2) may be produced by reacting a diisocyanate with a hydroxyl group-containing (meth)acrylate. To wit, it derives from reacting isocyanate groups from the diisocyanate with the hydroxyl group of the hydroxyl group-containing (meth) aery late. The diisocyanates and the hydroxyl group-containing (meth)acrylate used for the synthesis of the (A2) component are respectively similar to the diisocyanates and the hydroxyl group-containing (meth)acrylates used for the synthesis of the (Al) component.
More specifically, the (A2) component may be obtained by reacting 1 mole of diisocyanate with 2 moles of hydroxyl group-containing (meth)acrylate. The resulting urethane (meth)acrylates are, for example, the reaction product of hydroxyethyl (meth)acrylate and 2,4-tolylene diisocyanate, the reaction product of hydroxyethyl (meth)acrylate and 2,5 (or 2,6)-bis(isocyanate methyl)-bicyclo[2.2.1]heptane, the reaction product of hydroxyethyl (meth)acrylate and isophorone diisocyanate, the reaction product of
hydroxypropyl (meth)acrylate and 2,4-tolylene diisocyanate, and the reaction product of hydroxypropyl (meth)acrylate and isophorone diisocyanate.
It is further possible to prepare the (Al) component of urethane (meth)acrylate and the (A2) component of urethane (meth)acrylate simultaneously. Specifically, after reacting more than 2 moles of diisocyanate per each mole of hydroxyl groups in the polyol, the unreacted diisocyanate groups are reacted with a molar equivalent of hydroxyl group-containing (meth) aery late to complete the preparation.
The overall content of the component (A) urethane (meth)acrylate in the curable liquid resin composition according to the present invention should range from 30 to 80 % by mass, preferably from 50 to 80 % by mass in order to prepare a composition with a viscosity suitable for easy coating, and to obtain an optimal Young's modulus in the cured material for the optical fiber tape. Here, the amount of the component (Al) urethane (meth)acrylate, with respect to 100 % by mass of the total of the (A) component, should range from 50 to 90 % by mass, preferably 60 to 80 % by mass. The remainder, by mass of the total of the (A) component, being the (A2) component urethane (meth) aery late.
The (B) component, the ethylenically unsaturated group-containing compound used in the present invention, may consist of (Bl) components
(mono-functional compounds) having a single ethylenically unsaturated group and (B2) components (multi-functional compounds) having two or more ethylenically unsaturated groups.
Examples of the (Bl) mono-functional compounds include vinyl group-containing lactams such as N- vinyl pyrolidone, N- vinyl caprolactam; alicyclic structure-containing (meth)acrylates such as 2-ethylhexyl (meth)acrylate, isobornyl (meth)acrylate, bornyl (meth)acrylate, tricyclodecanyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclo pentanyl (meth)acrylate, cyclohexyl (meth)acrylate; and benzyl (meth)acrylate,
4-butylcyclohexyl (meth) aery late, (meth)acryloyl morpholine, vinyl imidazole, vinyl pyridine, etc.
Additional examples include 2 -hydroxy ethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, amyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, pentyl (meth)acrylate, isoamyl (meth)acrylate, hexyl (meth)acrylate, heptyl (meth)acrylate, octyl (meth)acrylate, isooctyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, isodecyl (meth)acrylate, undecyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, isostearyl (meth)acrylate, tetrahydrofurfyl (meth)acrylate, butoxyethyl (meth)acrylate, ethoxydiethylene glycol (meth)acrylate, benzyl (meth)acrylate, phenoxyethyl (meth)acrylate, polyethylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, methoxyethylene glycol (meth)acrylate, ethoxyethyl (meth)acrylate, methoxy polyethylene glycol (meth) aery late, methoxy polypropylene glycol (meth)acrylate, diacetone (meth)acrylamide, isobutoxy methyl (meth)acrylamide, 7-amino-3,7-dimethyl octyl (meth)acrylate, N,N-diethyl (meth)acrylamide, N,N-dimethyl (meth)acrylamide, t-octyl (meth)acrylamide, dimethyl aminoethyl (meth)acrylate, diethyl aminoethyl (meth)acrylate, N,N-diethyl (meth)acrylamide, N,N-dimethyl aminopropyl (meth)acrylamide, hydroxybutyl vinyl ether, lauryl vinyl ether, cetyl vinyl ether, 2-ethylhexyl vinyl ether, and the compounds expressed by formulas (6) through (9) below.
wherein, R5 represents a hydrogen atom or methyl group, R6 represents an alkylene group with from 2 to 8, preferably from 2 to 5 carbon atoms, R7 represents a hydrogen atom or methyl group, and p is a number, preferably from 1 to 4.
CH2= (9)
wherein R8, R9, R10, and R11 each independently represent a hydrogen atom or a methyl group, and q is an integer of from 1 to 5.
Preferred among the compounds containing one ethylenically unsaturated group are vinyl-containing lactams such as N- vinyl pyrolidone, N- vinyl caprolactam, as well as isobornyl (meth) aery late and lauryl acrylate.
Commercially available mono-functional ethylenically unsaturated group-containing compounds include Aronix Mill, M113, M114, M117 (all by Toa Gosei Co.): KAYARAD, TClIOS, R629, R644 (all by Nippon Kayaku Co.); IBXA, Biscoat 3700 (by Osaka Organic Chemical Industries Co..), etc.
Further, examples of the multi-functional (B2) compounds include: trimethylol propane tri (meth)acrylate, trimethylol propane trioxyethyl
(meth) aery late, pentaerythritol tri(meth)acrylate, ethylene glycol di(meth)acrylate, triethylene glycol diacrylate, tetraethylene glycol di(meth)acrylate, bis((meth)acryloyl oxymethyl) tricycle[5.2.1.0.2.6]decane (also called "tricyclodecane di-il dimethanol di(meth)acrylate"), polyethylene glycol di(meth)acrylate, 1,4-butadiol di(meth)acrylate, 1,6-hexane diol di(meth)acrylate, neopentyl glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, bisphenol A diglycidyl ether with terminal (meth) acrylic acid adduct at both ends, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, polyester di(meth)acrylate, tris(2-hydroxyethyl)isocyanurate tri(meth)acrylate, tris(2-hydroxyethyl) isocyanurate di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, bisphenol A diol di(meth) aery late with ethylene oxide or propylene oxide adduct, hydrogenated bisphenol A diol di(meth)acrylate with ethylene oxide or propylene oxide adduct, bisphenol A diglycidyl ether (meth)acrylate to which epoxy (meth)acrylate has been added, triethylene glycol divinyl ether, etc.
Examples of commercially available products which can be used for these include NK Ester, A-DCP Yupimer UV (by Shin Nakamura Chemical Co.), SA-1002 (by Mitsubishi Chemical Co.), Alonix M-215, M-315, M-325, TO-1210 (all by Toa Gosei Co.), etc.
One type or two or more types of the ethylenically unsaturated group-containing compound may be used as the (B) component, and it should comprise from 10 to 60 % by mass, preferably from 10 to 40 % by mass of the curable liquid resin composition of the present invention in order to achieve a Young's modulus of the cured material that is optimal for optical fiber tape.
Also, the amount of the (Bl) mono-functional compound should range from 50 to 100 % by mass with respect to 100 % by mass of the total of the (B) component, preferably from 80 to 100 % by mass, and even more preferably 100 % by mass. Using more of the mono-functional component (Bl)
in relation to the multi-functional component (B2) prevents excessive rigidity in the cured material.
There are no particular restrictions upon the epoxy-modified silicone used as the (C) component in the present invention so long as it includes epoxy groups in its molecules, but the preferred epoxy-modified silicone is one which has an epoxy group substituted for a methyl group on the dimethyl polysiloxane side chain. The (C) component improves the surface slidability of the cured material and further lends good printability.
Specific examples of the (C) component include epoxy-modified silicones that have the repetitive structures shown in the below listed formula (1) and below listed formula (2).
CH3
-Si-O- (!)
CH3
CH3
—si-o— (2)
ROCH2CH-CH2 O
wherein R represents any desired valence 2 organic group, with alkylene groups or allylene groups being preferred. Further, epoxy-modified silicones having the structure shown in the below listed formula (3) are preferred.
wherein R is the same as it was in formula (2). m and n express the mole% of the repetitive units, m ranges from 10 to 90 mole% and n ranges from 90 to 10
mole% (wherein M + n = 100 mole%, and it is preferable that the theoretical molecular weight of the epoxy-modifide silicone expressed by formula (3) range from 5000 to 15 000.).
It is preferable that the epoxy group modification rate be one group per 1000 to 10 000 equivalents of the dimethyl siloxane structural units contained in the epoxy-modified silicone.
The average molecular weight of the silicone should range from 3000 to 20 000, preferably from 5000 to 10 000.
Commercial examples of this kind of epoxy-modified silicone include SF8411, SF8413 (by Toray Dow-Corning Co.), etc.
Component (C), the epoxy-modified silicone, should comprise from 0.1 to 5 % by mass, preferably from 0.3 to 3 % by mass of the total components of the curable liquid resin composition according to the present invention. A (D) component, a modified silicone other than that of the (C) component, may be included in the curable liquid resin composition according to the present invention. The combined use of the (D) component with the (C) component serves to improve the solubility of the (C) component in the composition.
Examples of such modified silicone include polyether-modified silicone, alky 1- modified silicone, polyether alkyl-modified silicone, and
(meth)acryloyl group -modified silicone, etc. The (meth)acryloyl group -modified silicone is preferred due to its ability to prevent the precipitation from the cured material.
Commercial products may be used for these modified silicones, including SH190, SH3711, SH8427, SH203, SH230 (all by Toray Dow-Corning Co.), Paintad 8586 (by Dow-Corning Co.), etc.
One or two or more types in combination of the (D) component modified silicone may be used. The amount formulated should range from 0.1 to 5 % by mass, preferably, from 0.5 to 3 % by mass per the total of the curable liquid resin composition according to this invention from the perspective of
achieving adequate dissolution of the (C) component, surface slidability and printability of the cured material.
Further, a polymerization initiator may be used as the (E) component in the curable liquid resin composition according to the present invention. Such polymerization initiators may be of the heat or light initiation type.
When the curable liquid resin composition of this invention is to be cured by heating, a peroxide compound, azo compound or other type heat polymerization initiator should be used. Specific examples include benzoyl peroxide, t-butyl oxybenzoate, azobis isobutyronitrile, etc.
When the curable liquid resin composition of this invention is to be cured with light, a photo polymerization initiator would be used, optionally with further addition of a light sensitizing agent. Examples of such photo polymerization initiators include 1 -hydroxy cyclohexyl phenyl ketone, 2,2-dimethoxy-2-phenyl acetophenone, xanthone, fluorenone, benzaldehyde, fluorolene, anthraquinone, triphenyl amine, carbazol, 3-methyl acetophenone, 4-chloro benzophenone, 4,4'-dimethoxy benzophenone, 4,4'-diamino benzophenone, Mihira ketone, benzo isopropyl ether, benzoin ethyl ether, benzyl dimethyl ketal, l-(4-isopropyl phenyl) -2 -hydroxy- 2 -methyl propane-1-one, 2-hydroxy-2-methyl-l-phenyl propane- 1-one, thioxanthone, diethyl thioxanthone, 2-chloro thioxanthone, 2-methyl-l- [4- (methyl thio) phenyl] -2-morpholino-propane- 1-one, 2,4,6-trimethyl benzoyl diphenyl phosphene oxide, bis-(2,6-dimethoxy benzoyl)-2,4,4-trimethyl pentyl phosphene oxide, IRGACURE184, 369, 651, 500, 907, CG11700, CG11750, CG11850, CG24-61; Darocurell 16, 1173 (all by Ciba Specialty Chemicals Co.); Lucirin TPO (BASF Co.); Ubequil P36 (UBC Co.), etc.
Further, examples of light sensitizing agent include triethyl amine, diethyl amine, n-methyl diethanol amine, ethanol amine, 4-dimethyl aminobenzoate, 4-dimethyl amino methyl benzoate, 4-dimethyl amino ethyl
benzoate, 4-dimethyl amino isoamyl benzoate, Ebecryl P102, 103, 104, 105 (all from UBC Co.), etc.
When both heat and ultraviolet light are used to cure the curable liquid resin composition according to the present invention, the foregoing heat polymerization initiator may be used in combination with the photo polymerization initiator. The amount of the (E) component polymerization initiator used should range from 0.1 to 10 % by mass, preferably from 0.3 to 7 % by mass.
Other additives, such as antioxidants, dyes, ultraviolet light absorbents, photo stabilizers, silane coupling agents, heat polymerization inhibitors, leveling agents, surfactants, preservatives and stabilizers, plasticizers, lubricants, solvents, fillers, anti-aging agents, wetting agents, coating surface modifiers, etc. may be used as required in the curable liquid resin composition of the present invention so long as they do not detract from the properties of the invention.
The curable liquid resin composition according to this invention may be cured by heat and/or irradiation. What is meant by "irradiation" is with infrared light, visible light, ultraviolet light, X-rays, electron beam, α-radiation, β-radiation, γ-radiation, etc. Preferably, the cured film from the curable liquid resin composition of this invention should exhibit a Young's modulus that ranges from 700 to 1200 MPa.
Examples
Next, examples shall be presented to explain this invention in further detail, however, the invention is not limited to these examples.
Preparation Example 1: Synthesis of the (A) Urethane (meth) Acrvlate
16.640 g of isobornyl acrylate, 0.016 g of 2,6-di-t-butyl-p-cresol, 19.173 g of trilene diisocyanate, 19.345 g of polypropylene glycol with a number-averaged molecular weight of 2000, and 9.051 g of polypropylene glycol with a number-averaged molecular weight of 400 were added to a reaction vessel equipped with a stirrer, which was then cooled to a liquid temperature of 15 °C. Then, after adding 0.053 g of dibutyl tin laurate, the liquid temperature was increased to 40 °C or greater and it was stirred for an hour. While still stirring, the system was cooled to a liquid temperature of 15 °C or under. Then, 18.067 g of 2 -hydroxy ethyl acrylate was added slowly, dropwise while maintaining the liquid temperature at 20 °C or below. After stirring and reacting for an additional hour, the temperature was increased to 70-75 °C and stirring continued for an additional 3 hours, and the reaction was halted when the residual isocyanate fell below 0.1 % by mass. The resulting (A) urethane (meth) acrylate was labeled UA-I. This UA-I was combined, respectively, with the urethane (meth) acrylate having the structure expressed in the below-listed formulas (11)-(13), to prepare mixtures in which its respective content was 25.32 % by mass, 21.70 % by mass, and 18.08 % by mass. HEA- TDI- PPG2000— TDI- HEA (11) HEA- TDI- DA400-TDI— HEA (12)
HEA- TDI- HEA (13), wherein HEA represents a structure derived from hydroxyl ethyl acrylate, TDI a structure derived from toluene diisocyanate, PPG2000 a structure derived from polypropylene glycol with a number-averaged molecular weight of 2000, and DA400 a structure derived from polyethylene bisphenol A ether having a number-averaged molecular weight of 400.
Synthesis of Acryloyl Group -Modified Silicone
64.530 g of polydimethyl siloxane (FM0411 made by Ciba Specialty Chemicals Co.) having a hydroxyl group on one terminal end and 11.238 g of
trilene diisocyanate were added to a reaction vessel equipped with a stirrer and the contents were chilled to a liquid temperature of 15 °C. After adding 0.067 g of dibutyl tin laurate, the liquid temperature was prevented from exceeding 40 °C while stirring for 2 hours. While continuing the stirring, the reaction was then chilled to maintain a liquid temperature of 15 °C or under. After confirming that the liquid temperature was 15 °C or under, 7.493 g of 2-hydroxyethyl acrylate was added dropwise, after which, it was confirmed that the temperature had not increased, and then the liquid temperature was maintained at from 65 to 70 °C while stirring for 2 hours, until the reaction was halted when the residual isocyanate fell below 0.1 % by mass.
The resulting acryloyl group -modified silicone was labeled as acryloyl group -modified silicone 1.
Example 1 The components listed in Table 1 were added to a reaction vessel equipped with a stirrer and stirred to a uniform solution at 50 °C to obtain the curable liquid resin composition.
Experimental Example The Examples and Comparative Examples of curable liquid resin compositions were cured using the below described methods and test samples were made and evaluated as described below. Those results also appear in Table 1.
(1) Young's Modulus
An applicator bar 380 μm thick was used to apply a coating of the curable liquid resin compositions atop a glass plate, and then the coating was cured in an air environment by irradiation with 1 J/cm2 of ultraviolet light energy to obtain a film, which was used for a Young's modulus measurement. The film sample was prepared into short slips measuring 6 mm wide and 25
mm long in the stretch area, and these were pulled under a temperature of 23 °C and humidity of 50 % at a pulling rate of 1 mm/minute while the Young's modulus was determined from the tensile strength at a 2.5 % strain.
(2) Test Sample Preparation
An applicator bar 250 μm thick was used to apply a coating of the curable liquid resin compositions atop a glass plate, and then the coating was cured in a nitrogen environment by irradiation with 0.5 J/cm2 of ultraviolet light energy. The cured material was allowed to stand at 23 °C in a 50 % humidity environment for 13 hours before preparing the test samples.
(3) Surface slidability
The cured films obtained in the above- described manner were peeled away from the glass plates and cut into 3 cm widths, and oriented with the top surface as the one that was irradiated with the ultraviolet light, before taping them to both surfaces of an aluminum plate. Two sheets of the test samples were used with the cured surfaces stacked against each other, the sandwich being held together with double clips for the surface sliding test. The test was conducted at a pulling rate of 50 mm/min, a contact surface area of 5.4 cm2 between the cured material surfaces, and a pressure of 4.7 N/cm2 exerted by the double clips. Upon the onset of sliding, the load was used to calculate the shear sliding force (units: N/cm2).
(4) Printability The cured surfaces of the test samples obtained through the above described method were coated with inkjet printer ink (INK7110 (black), by IMAJE Co.) using a spin coater operated at 8000 RPM for 20 seconds to obtain a uniform coating on the cured surface. After allowing the test samples to stand at 23 °C and 50 % humidity for 12 or more hours, the printability was
evaluated under the cross-hatch and tape method according to JIS K5400, on the basis of the number of squares remaining.
Table 1
In Table 1,
SH190: dimethyl polysiloxane polyoxyalkylene copolymer (by Toray Dow-Corning Co.)
SH28PA: dimethyl polysiloxane polyoxyalkylene copolymer (by Toray Dow-Corning Co.)
Irgacure 184: 1-hydroxy-cyclohexyl-phenyl-ketone (by Ciba Specialty Chemical
Co.)
Irgacure 907: 2-methyl-l-(4-methyl thiophenyl)-2-morpholino-propane-l-one
(by Ciba Specialty Chemical Co.)
Lucirin TPO: 2,4,6-trimethyl benzoyl diphenyl phosphine oxide (by Ciba Specialty Chemical Co.)
As is clear from Table 1, the cured film from the resin composition according to this invention has a high Young's modulus, and excellent surface slidability and printability.
All references, including publications, patent applications, and patents, cited herein are hereby incorporated by reference to the same extent as if each reference were individually and specifically indicated to be incorporated by reference and were set forth in its entirety herein.
The use of the terms "a" and "an" and "the" and similar referents in the context of describing the invention (especially in the context of the following claims) are to be construed to cover both the singular and the plural, unless otherwise indicated herein or clearly contradicted by context. The terms "comprising," "having," "including," and "containing" are to be construed as open-ended terms (i.e., meaning "including, but not limited to,") unless otherwise noted. Recitation of ranges of values herein are merely intended to serve as a shorthand method of referring individually to each separate value falling within the range, unless otherwise indicated herein, and each separate value is incorporated into the specification as if it were individually recited herein. All methods described herein can be performed in any suitable order unless otherwise indicated herein or otherwise clearly contradicted by context. The use of any and all examples, or exemplary language (e.g., "such as") provided herein, is intended merely to better illuminate the invention and does not pose a limitation on the scope of the invention unless otherwise claimed. No language in the specification should be construed as indicating any non-claimed element as essential to the practice of the invention.
Preferred embodiments of this invention are described herein, including the best mode known to the inventors for carrying out the invention. Variations of those preferred embodiments may become apparent to those of
ordinary skill in the art upon reading the foregoing description. The inventors expect skilled artisans to employ such variations as appropriate, and the inventors intend for the invention to be practiced otherwise than as specifically described herein. Accordingly, this invention includes all modifications and equivalents of the subject matter recited in the claims appended hereto as permitted by applicable law. Moreover, any combination of the above -de scribed elements in all possible variations thereof is encompassed by the invention unless otherwise indicated herein or otherwise clearly contradicted by context.
Claims
1. A curable liquid resin composition that contains the following components, (A), (B) and (C):
(A) urethane (meth) aery late;
(B) a compound containing an ethylenically unsaturated group; and (C) epoxy-modified silicone.
2. The curable liquid resin composition according to claim 1, wherein the (C) component contains the repetitive structure expressed by formula (1) below and the repetitive structure expressed by formula (2) below, wherein in the formula, R represents any desired valence 2 organic group
CH3
— si-o— (D
CH ■3
CH3
-si-o— (2)
ROCH2CH-CH2 O
3. The curable liquid resin composition according to claim 2, wherein the (C) component is expressed by formula (3) below, wherein in the formula, R represents any desired valence 2 organic group, m is 10-90 mole%, n is 90-10 mole%; wherein, m + n = 100 mole% and the average molecular weight of the epoxy-modified silicone expressed by formula (3) ranges from 5000 to 15 000 as calculated based on polystyrene when measured by gel permeation chromatography; and wherein the repetitive structure according to formula (1) and the repetitive structure according to formula (2) that appear in the formula may be in random arrays or block structures, respectively:
4. The curable liquid resin composition according to any one or all of claims 1 through 3 that further includes a (D) component of a modified silicone other than that of the (C) component.
5. The curable liquid resin composition according to claim 4, wherein the (D) component may be selected from polyether-modified silicon, alky 1- modified silicone, polyether-alkyl-modified silicone and acryloyl group -modified silicone.
6. The curable liquid resin composition according to any one or all of claims 1 through 5 used as optical fiber tape material.
7. The curable liquid resin composition according to any one or all of claims 1 through 6 employed as an optical fiber cladding layer when cured.
8. An optical fiber tape with the cladding layer according to claim 7.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008047456 | 2008-02-28 | ||
| JP2008-47456 | 2008-02-28 |
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ID=40585572
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/NL2009/050090 WO2009108056A1 (en) | 2008-02-28 | 2009-02-27 | Optical fiber tape with epoxy modified silicone additive |
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| Country | Link |
|---|---|
| JP (1) | JP2009227988A (en) |
| WO (1) | WO2009108056A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2428498A1 (en) * | 2010-09-13 | 2012-03-14 | DSM IP Assets B.V. | Curable liquid resin composition for outermost covering layers of optical fiber line |
| CN111234136A (en) * | 2020-03-23 | 2020-06-05 | 佛山市天宝利硅工程科技有限公司 | Preparation method of photocuring organic silicon resin system and photocuring film |
| CN111603716A (en) * | 2020-05-21 | 2020-09-01 | 北京凌天智能装备集团股份有限公司 | Naturally degradable high-molecular gel water-based extinguishing agent |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5420272B2 (en) * | 2008-02-28 | 2014-02-19 | Ｊｓｒ株式会社 | Liquid curable resin composition |
| WO2021145101A1 (en) * | 2020-01-14 | 2021-07-22 | 住友電気工業株式会社 | Resin composition, optical fiber, and method for producing optical fiber |
| WO2021145104A1 (en) * | 2020-01-14 | 2021-07-22 | 住友電気工業株式会社 | Resin composition, optical fiber, and method for producing optical fiber |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070246687A1 (en) * | 2004-08-30 | 2007-10-25 | Hiroshi Yamaguchi | Curable Liquid Resin Optical Fiber Up Jacket Composition |
| WO2008120982A1 (en) * | 2007-03-30 | 2008-10-09 | Dsm Ip Assets B.V. | Radiation curable resin compositions for electric wire coatings |
-
2009
- 2009-02-27 WO PCT/NL2009/050090 patent/WO2009108056A1/en active Application Filing
- 2009-02-27 JP JP2009045626A patent/JP2009227988A/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070246687A1 (en) * | 2004-08-30 | 2007-10-25 | Hiroshi Yamaguchi | Curable Liquid Resin Optical Fiber Up Jacket Composition |
| WO2008120982A1 (en) * | 2007-03-30 | 2008-10-09 | Dsm Ip Assets B.V. | Radiation curable resin compositions for electric wire coatings |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2428498A1 (en) * | 2010-09-13 | 2012-03-14 | DSM IP Assets B.V. | Curable liquid resin composition for outermost covering layers of optical fiber line |
| WO2012036546A1 (en) * | 2010-09-13 | 2012-03-22 | Dsm Ip Assets B.V. | Curable liquid resin composition for outermost covering layers of optical fiber line |
| CN111234136A (en) * | 2020-03-23 | 2020-06-05 | 佛山市天宝利硅工程科技有限公司 | Preparation method of photocuring organic silicon resin system and photocuring film |
| CN111603716A (en) * | 2020-05-21 | 2020-09-01 | 北京凌天智能装备集团股份有限公司 | Naturally degradable high-molecular gel water-based extinguishing agent |
| CN111603716B (en) * | 2020-05-21 | 2021-07-27 | 北京凌天智能装备集团股份有限公司 | Naturally degradable high-molecular gel water-based extinguishing agent |
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| JP2009227988A (en) | 2009-10-08 |
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