JPH0211611A - Resin composition and coating material for optical glass fiber - Google Patents
Resin composition and coating material for optical glass fiberInfo
- Publication number
- JPH0211611A JPH0211611A JP63159380A JP15938088A JPH0211611A JP H0211611 A JPH0211611 A JP H0211611A JP 63159380 A JP63159380 A JP 63159380A JP 15938088 A JP15938088 A JP 15938088A JP H0211611 A JPH0211611 A JP H0211611A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- coating material
- optical glass
- resin composition
- coating
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000576 coating method Methods 0.000 title claims abstract description 39
- 239000011248 coating agent Substances 0.000 title claims abstract description 38
- 239000000463 material Substances 0.000 title claims abstract description 32
- 239000005304 optical glass Substances 0.000 title claims abstract description 17
- 239000000835 fiber Substances 0.000 title claims abstract description 16
- 239000011342 resin composition Substances 0.000 title claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 11
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims description 3
- -1 acrylate compound Chemical class 0.000 abstract description 13
- 230000005540 biological transmission Effects 0.000 abstract description 5
- 239000007795 chemical reaction product Substances 0.000 abstract description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 2
- 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 abstract 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 abstract 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 239000003822 epoxy resin Substances 0.000 description 5
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 2
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 2
- 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 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000007607 die coating method Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 239000013307 optical fiber Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 2
- PJAKWOZHTFWTNF-UHFFFAOYSA-N (2-nonylphenyl) prop-2-enoate Chemical compound CCCCCCCCCC1=CC=CC=C1OC(=O)C=C PJAKWOZHTFWTNF-UHFFFAOYSA-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
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- PHPRWKJDGHSJMI-UHFFFAOYSA-N 1-adamantyl prop-2-enoate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)C=C)C3 PHPRWKJDGHSJMI-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-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
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- DPNXHTDWGGVXID-UHFFFAOYSA-N 2-isocyanatoethyl prop-2-enoate Chemical compound C=CC(=O)OCCN=C=O DPNXHTDWGGVXID-UHFFFAOYSA-N 0.000 description 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- YNTQTLGBCMXNFX-UHFFFAOYSA-N [5-ethyl-2-(2-methyl-1-prop-2-enoyloxypropan-2-yl)-1,3-dioxan-5-yl]methyl prop-2-enoate Chemical compound C=CC(=O)OCC1(CC)COC(C(C)(C)COC(=O)C=C)OC1 YNTQTLGBCMXNFX-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 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 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 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 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Macromonomer-Based Addition Polymer (AREA)
- Surface Treatment Of Glass Fibres Or Filaments (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、樹脂組成物、特に光伝送用の光学ガラスファ
イバを被覆するのに適する被覆材料に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a resin composition, particularly a coating material suitable for coating an optical glass fiber for light transmission.
（従来の技術）
光ファイバは、もろ（傷がつきやすい上に可と５性にと
ぼしく、わずか−な外力によって容易に破断し、又力学
的側圧が加わるとマイクロベンディングにより伝送され
る光は弱められ、伝送損失を生ずる。このためガラス表
面には、マイクロベンディングを最低に抑えるためにき
わめて低い弾性率を有する材料で１次被覆を行ったのち
、可と５性を有しかつ高い弾性率を有する材料で２次被
覆が行われており、い（つかの提案もなされている。例
えば、特開昭５８−２２３６３８、特開昭５９−１７０
１５４など。(Prior art) Optical fibers are fragile and easily damaged, and easily break due to the slightest external force, and when mechanical lateral pressure is applied, the light transmitted by microbending weakens. Therefore, to minimize microbending, the glass surface is first coated with a material that has an extremely low modulus of elasticity, and then coated with a material that has a flexible and high modulus of elasticity. Secondary coating has been carried out with materials that have
154 etc.
（発明が解決しようとする課題）
伝送損失を生ずる原因としては、前記のマイクロベンデ
ィングと水素ガス等が挙げられる。(Problems to be Solved by the Invention) Causes of transmission loss include the aforementioned microbending and hydrogen gas.
マイクロベンディングは、低い弾性率を有する杓科で被
覆を行うことによって、抑えることができるが水素の問
題は、十分に解決されていない。従来の紫外線硬化型被
覆材料でも高温下におし・た場合や螢光灯の下に長期間
貯蔵後、高温下におし・た場合等に多量に発生し、伝送
損失の原因となって見・る。この発明は、螢光灯の下に
長期間貯蔵しても、水素の発生量が小さく、硬ｆヒ性に
すぐれた光学ガラスファイバ用被覆材料に適する樹脂組
成物を提供しようとするもである。Although microbending can be suppressed by coating with a locustide material having a low elastic modulus, the hydrogen problem has not been satisfactorily resolved. Even with conventional UV-curable coating materials, large amounts of UV rays are generated when exposed to high temperatures, stored under fluorescent lights for long periods of time, and exposed to high temperatures, causing transmission loss. look. This invention aims to provide a resin composition suitable for a coating material for optical glass fibers, which generates a small amount of hydrogen even when stored under a fluorescent lamp for a long period of time, and has excellent hardness and arsenic properties. .
（課題を解決するための手段）
本発明者らは、上記の目的を達成するために鋭意検討し
た結果、特定のアクリレート化合物（■３）と酸化防止
剤（Ｃｌを添加することによって、水素の発生量が小さ
く、硬化速度が速し・光学ガラスファイバ用被覆材料に
適する樹脂組成物を提供することに成功し本発明を完成
した。(Means for Solving the Problems) As a result of intensive studies to achieve the above object, the present inventors discovered that by adding a specific acrylate compound (■3) and an antioxidant (Cl), hydrogen The present invention has been completed by successfully providing a resin composition that generates a small amount, has a fast curing speed, and is suitable as a coating material for optical glass fibers.
すなわち、本発明は（１）エチレン性不飽和基を有する
化合物Ｇ〜）と−数式Ｅｌ）
（式中、Ｒ１はＨ又はＣＦＬを、Ｒ２はＩ−１又は低級
アルキル基を、Ｒ３，Ｉｔ、ｌ、 Ｒ５＋ Ｒｓはそれ
ぞれ、メチル基、エチル基、プロピル基等の低級アルキ
ル基を示す。）
を有する化合物（Ｂｌと酸化防止剤（Ｃ）を含むことを
特徴とする樹脂組成物、及び
に） エチレン性不飽和基を有する化合物置と一般式〔
ｌ）を有する化合物ｆＢ］と酸化防止剤（Ｃ１を含むこ
とを特徴とする光学ガラスファイバ用被覆材料に関する
ものである。That is, the present invention provides (1) a compound G~) having an ethylenically unsaturated group and -formula El) (wherein, R1 is H or CFL, R2 is I-1 or a lower alkyl group, R3, It, 1, R5+ Rs each represent a lower alkyl group such as a methyl group, an ethyl group, a propyl group, etc.) (A resin composition characterized by containing Bl and an antioxidant (C), and Compound position and general formula with ethylenically unsaturated group [
The present invention relates to a coating material for an optical glass fiber, characterized in that it contains a compound fB] having a compound fB] and an antioxidant (C1).
本発明において使用する（Ａ）成分としてのエチレン性
不飽和基を有する化合物としては、例えば、ウレタンア
クリレート〔ポリエチレングリコール、ポリプロピレン
グリコール、ポリテトラメチレングリコール等の分子中
にエーテル基を持つポリエーテルポリオール、エチレン
グリコール プロピレングリコール ジエチレングリコ
ール、１，５−ベンタンジオール、１．６−ヘキサンジ
オール等のジオール化合物とコハク酸、アン７ピン酸、
フタル酸、ヘキサヒドロフタル酸等の２塩基酸の反応物
あるいは前記ジオール化合物と前記２塩基酸とε−カプ
ロラクトン等のラクトン化合物との反応物あるいは前記
、ジオール化合物とε−カプロラクトンあるいはβ−メ
チル−δ−バレロラクトン等のラクトン化合物との反応
物等の分子中にエステル基を持つポリエステルポリオー
ル、分子中にカーボネート基を持つカーボネートポリオ
ール、分子中にエーテル基及びエステル基の両方を゛も
つポリオール、ポリマーポリオール等のポリオールとポ
リイソシアネート（例えば、トリレンジイソシアネート
、ヘキサメチレンジイノシアネート、トリメチルへキサ
メチレンジイソシアネート、ジンクロヘキシルメタンジ
イノシアネ−１・、イノホロンジイソシアメート、ジフ
ェニルメタンジイノシアネート等）とモノヒドロキシ含
有アクリレート（例えば、２−ヒドロキシエチルアクリ
レート、２−ヒドロキシプロピルアクリし・−ト、１−
ヒドロキシブチルアクリレ−１，，２−ヒドロキシエチ
ルアクリレートのε−カフロラクトン付加物等）とを反
応させて得られろ。〕エポキシアクリレート〔ビスフェ
ノールＡ 型エポキシ樹脂、フェノールノボラック型エ
ポキシ樹脂、クレゾールノボラック型エポキシ樹脂、ビ
スフェノールＦ型エポキシ樹脂等のエポキシ樹脂とアク
リル酸との反応物〕、フェノキシエチルアクリレート、
テトラヒドロフルフリルアクリレート、Ｎ−ビニルピロ
リドン、アクリロイルモルホリン、Ｎ−ビニル力グロラ
クタム、テトラヒドロフルフリルアルコールのε−カフ
ロラクトン付加物のアクリレート、ノニルフェノールの
エチレンオキザイド付加物のアクリレート、ノニルフェ
ノールのエチレンオキサイド付加物のε−カプロラクト
ン付加物のアクリレート、トリシクロデカノールのアク
リレート、イソボルニルアクリレート、アダマンチルア
クリレート、トリシクロデカンジメチロールのジアクリ
レート、ジオキサングリコールジアクリレート（日本化
薬■製、ＫＡＹＡＲＡＤ Ｒ−６０４）、トリスアク
リロイルオキシエチルインシアネート、トリメチロール
プロパントリアクリレート、ジペンタエリスリトールペ
ンタ（又はへキサ）アクリレート等を挙げることができ
る。エチレン性不飽和基を有する化合動因の使用量は、
樹脂組成物又は被覆材料中好ましくは７５〜９９重景％
、重量好ましくは９０〜９８重量％である。Examples of the compound having an ethylenically unsaturated group as component (A) used in the present invention include urethane acrylate [polyether polyol having an ether group in the molecule such as polyethylene glycol, polypropylene glycol, and polytetramethylene glycol; Ethylene glycol Propylene glycol Diol compounds such as diethylene glycol, 1,5-bentanediol, 1,6-hexanediol, succinic acid, ampeptapic acid,
A reaction product of a dibasic acid such as phthalic acid or hexahydrophthalic acid, or a reaction product of the diol compound and the dibasic acid and a lactone compound such as ε-caprolactone, or a reaction product of the diol compound and ε-caprolactone or β-methyl- Polyester polyols with ester groups in the molecule, such as reactants with lactone compounds such as δ-valerolactone, carbonate polyols with carbonate groups in the molecule, polyols and polymers with both ether groups and ester groups in the molecule. Polyols such as polyols, polyisocyanates (e.g., tolylene diisocyanate, hexamethylene diinocyanate, trimethylhexamethylene diisocyanate, zinclohexylmethane diinocyane-1, inophorone diisocyanate, diphenylmethane diinocyanate, etc.) and monomers. Hydroxy-containing acrylates (e.g., 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 1-
It can be obtained by reacting hydroxybutyl acrylate-1,,2-hydroxyethyl acrylate with ε-cafrolactone adduct, etc.). ] Epoxy acrylate [reactant of acrylic acid and epoxy resin such as bisphenol A type epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, bisphenol F type epoxy resin], phenoxyethyl acrylate,
Tetrahydrofurfuryl acrylate, N-vinylpyrrolidone, acryloylmorpholine, N-vinyl glolactam, acrylate of ε-cafrolactone adduct of tetrahydrofurfuryl alcohol, acrylate of ethylene oxide adduct of nonylphenol, ε of ethylene oxide adduct of nonylphenol -Acrylate of caprolactone adduct, acrylate of tricyclodecanol, isobornyl acrylate, adamantyl acrylate, diacrylate of tricyclodecane dimethylol, dioxane glycol diacrylate (manufactured by Nippon Kayaku, KAYARAD R-604), trisacryloyl Examples include oxyethyl incyanate, trimethylolpropane triacrylate, dipentaerythritol penta (or hexa) acrylate, and the like. The amount used of the compound moiety having an ethylenically unsaturated group is
Preferably 75 to 99% by weight in the resin composition or coating material
, preferably 90 to 98% by weight.
本発明において［Ｆ］）成分として用いられる一般式（
１）で表わされる化合物（Ｄは、市場より容易に人手す
ることができる。例えば、日立化成工業■製、ファンク
リルＦＡ−７１１ＭＡ 、 ＦＡ −７１１ＭＭ、ＦＡ
−７１２ＨＭ、ＦＡ−７１２ＨＡ等である。In the present invention, the general formula (
The compound (D) represented by 1) can be easily obtained manually from the market.For example, FANCRIL FA-711MA, FA-711MM, FA manufactured by Hitachi Chemical Co., Ltd.
-712HM, FA-712HA, etc.
−数式（１〕で表わされる化合物ＩＢＩと酸化防止剤（
０を添加することによって、樹脂組成物及び光学ガラス
ファイバ被覆材料（以後いずれも組成物という。）を螢
光打丁に長期間貯蔵後、高温（１００〜１５０℃）に加
熱しても、水素の発生量を小さくおさえることができる
。化合物（Ｂｌの使用量は、組成物中好ましくは０．０
１〜２５重量％、特に好ましくは０．０５〜１０重量％
である。- Compound IBI represented by formula (1) and antioxidant (
By adding 0, even if the resin composition and the optical glass fiber coating material (hereinafter referred to as the composition) are stored in a fluorescent knife for a long period of time and heated to high temperatures (100 to 150°C), hydrogen will not be released. The amount of generation can be kept small. The amount of compound (Bl used is preferably 0.0 in the composition)
1-25% by weight, particularly preferably 0.05-10% by weight
It is.
次に酸化防止剤（０としては、例えばフェノール系酸化
防止剤である２、６−ジ−ターシャリ−ブチル−４−フ
ェノールやイオウ系酸化防止剤であるジラウリル−８，
８′−チオジプロピオネート、シミリスチル−８，８′
−チオジプロピオネート、２−メルカプトベンズイミダ
ゾール等を挙げることができる。その使用量は組成物中
好ましくは０．１〜５重量％、特に好ましくは０．５〜
３重量％である。Next, an antioxidant (for example, phenolic antioxidant 2,6-di-tert-butyl-4-phenol, sulfur antioxidant dilauryl-8,
8'-thiodipropionate, cimiristyl-8,8'
-thiodipropionate, 2-mercaptobenzimidazole and the like. The amount used is preferably 0.1 to 5% by weight, particularly preferably 0.5 to 5% by weight in the composition.
It is 3% by weight.
本発明の組成物は、紫外線で硬化するのが好ましく、そ
の場合、光重合開始剤を添加するのが好ましい。光重合
開始剤としては１例えば、１−ヒドロキシシクロへキシ
ルフェニルケトン、２、４．６− ）リメチルベンゾイ
ルージフエノイルフォスフィンオキシド（ＢＡＳＦ製、
ルシリンＬＲ８７２８）、ベンジルジエチルケタール、
ジクロロアセトフェノン、ジェトキシアセトフェノン、
ベンゾフェノン等が挙げられる。光重合開始剤を使用す
る場合、その使用量は組成物中０．１〜１０重量％が好
ましく、特に１〜５重量％が好ましい。更に必要に応じ
て、シランカップリング剤、ノ・クリ剤、酸化防止剤、
重合禁止剤等を配合することができる。The composition of the invention is preferably cured by ultraviolet light, in which case it is preferable to add a photopolymerization initiator. Examples of photopolymerization initiators include 1-hydroxycyclohexylphenylketone, 2,4,6-)limethylbenzoyl-diphenoylphosphine oxide (manufactured by BASF,
Lucirin LR8728), benzyl diethyl ketal,
dichloroacetophenone, jetoxyacetophenone,
Examples include benzophenone. When a photopolymerization initiator is used, the amount used is preferably 0.1 to 10% by weight, particularly preferably 1 to 5% by weight in the composition. Furthermore, if necessary, add a silane coupling agent, a chemical agent, an antioxidant,
A polymerization inhibitor and the like can be added.
本発明の光学ガラスファイバ用被覆材料を用いて光学ガ
ラスファイバを被覆する場合、光学ガラス母材を例えば
１〜５ｍ／秒の速度で線弓きし、被覆材料（１次被覆用
）を被覆し、紫外線照射により硬化し、次いで、被覆材
料（２次被覆用）を被覆する。被覆材料を被覆する場合
のコーティング法としては、ダイスコーティング法が適
当である。When coating an optical glass fiber using the coating material for optical glass fiber of the present invention, the optical glass base material is wire bowed at a speed of, for example, 1 to 5 m/sec, and the coating material (for primary coating) is coated. , cured by ultraviolet irradiation, and then coated with a coating material (for secondary coating). As a coating method for coating the coating material, a die coating method is suitable.
本発明の被覆材料は、紫外線照射により容易に硬化する
。本発明の被覆材料の紫外線照射による硬化は常法によ
り行うことができる。例えば、低圧又は高圧水銀灯、キ
セノン灯を用い紫外線を照射すればよい。本発明の樹脂
組成物は光学ガラスファイバ用被覆材料として有用であ
るが、その他に、プラスチック、ガラス、セラミック等
の被覆材料としても使用できる。The coating material of the present invention is easily cured by ultraviolet irradiation. Curing of the coating material of the present invention by ultraviolet irradiation can be carried out by a conventional method. For example, ultraviolet rays may be irradiated using a low-pressure or high-pressure mercury lamp or a xenon lamp. The resin composition of the present invention is useful as a coating material for optical glass fibers, but can also be used as a coating material for plastics, glass, ceramics, and the like.
（実施例）
以下本発明を実施例によって更に詳細忙説明するが、本
発明は、実施例に限定されるものでない。(Examples) The present invention will be explained in more detail below with reference to Examples, but the present invention is not limited to the Examples.
実施例１゜
平均分子１２ｏｏｏのポリプロピレングリコール２００
ｇ、平均分子量２０００のε−カプロラクトン変性ポリ
エステルジオール（ダイセル化学工業■、プラクセルＬ
−２２０ＡＬ （２００ｇ。Example 1 Polypropylene glycol 200 with an average molecular weight of 12ooo
g, ε-caprolactone-modified polyester diol with an average molecular weight of 2000 (Daicel Chemical Industry ■, Plaxel L
-220AL (200g.
インホロンジイノシアネート６６．７ｇとを仕込み８０
℃で８時間反応させたのち、２−ヒドロキシエチルアク
リレ−）２３．９ｇを加え８０°Ｃで１０時間反応させ
冷却後４９０ｇのウレタンアクリレートを得た。得られ
たウレタンアクリレート４７ｇ、テトラヒドロフルフリ
ルアルコールのε−カプロラクトン付加物のアクリレー
ト（日本化薬■製、ＫＡＹＡＲＡＤ ＴＣ−１１Ｏ８
）５０ｇ、構造式
（日立化成工業■、ファンクリルＦ Ａ −７１１ＭＡ
）で表わされる化合物０５ｇ、２，６−ジ−ターシャリ
−ブチル−４−メチルフェノール２ｇ、２゜４６−ドリ
メチルベンゾイルジフエノイルフオスフインオキシド（
ＢＡＳＦ製、ルシリンＬＲ８７２８）２．５ｇを溶解、
混合し、目的の被覆材もト（１次被覆用）を得た。この
被覆材料をガラス板上に５０μｍの厚さで塗布したのち
、８０Ｗ／ＣＩｎのメタルハライドランプを用いてコン
ベアスピー ド２０ｍ／′分で硬化させた。その硬化皮
膜の物性測定結果を表−１に示す。Prepared with 66.7g of inphoron diinocyanate and 80
After reacting at 80° C. for 8 hours, 23.9 g of 2-hydroxyethyl acrylate was added, and the mixture was allowed to react at 80° C. for 10 hours. After cooling, 490 g of urethane acrylate was obtained. 47 g of the obtained urethane acrylate, acrylate of ε-caprolactone adduct of tetrahydrofurfuryl alcohol (manufactured by Nippon Kayaku ■, KAYARAD TC-11O8)
) 50g, structural formula (Hitachi Chemical ■, Fancryl FA-711MA
), 05 g of the compound represented by
Dissolve 2.5g of Lucirin LR8728 (manufactured by BASF),
The mixture was mixed to obtain the desired coating material (for primary coating). This coating material was applied onto a glass plate to a thickness of 50 μm, and then cured using an 80 W/CIn metal halide lamp at a conveyor speed of 20 m/min. Table 1 shows the results of measuring the physical properties of the cured film.
実施例２゜
平均分子［２０００のポリテトラメチレンエーテルグリ
コール２０ｇ１．エチレンクリコール２４．８ｇ、イソ
ホロンジインシアネート２２２、３ ｇとを仕込み、８
０℃で８時間反応させたのち、２−ヒドロギシエチルア
クリレート１１９ｇを加え、８０℃で１０時間反応させ
た。Example 2 Polytetramethylene ether glycol with average molecular weight of 2000 g 1. Prepare 24.8 g of ethylene glycol and 222.3 g of isophorone diincyanate,
After reacting at 0°C for 8 hours, 119 g of 2-hydroxyethyl acrylate was added and reacting at 80°C for 10 hours.
冷却後５６６ｇのウレタンアクリレートを得た。After cooling, 566 g of urethane acrylate was obtained.
得られたウレタンアクリレート４０ｇ、）リスアクリロ
イルオキシエチルイソシアネート１５ｇ、トリシクロデ
カンジメチロールジアクリレ−）１５ｇ、アクリロイル
モルホリン１０ｇ。40 g of the obtained urethane acrylate, 15 g of lith acryloyloxyethyl isocyanate, 15 g of tricyclodecane dimethylol diacrylate, and 10 g of acryloylmorpholine.
インボルニルアクリレート１７ｇ及び、構造式（日立化
成工業■製、ファンクリルＦＡ−７１２１１Ａ）で示さ
れる化合物０．５ｇ、２，６−ジ−ターシャリ−ブチル
−４−フェノール２ｇ、２，４．６トリメチルペンゾイ
ルジフエノイルフオスフインオキシド（ＢＡＳＦ製、ル
シリンＬＲ８７２８）２．５ｇを混合し目的の被覆材料
（２次被覆用）を得た。この被覆材料をガラス板上に５
トタｍの厚さで塗布したのち、硬化させた。その硬化皮
膜の物性測定結果を表−１に示す。17 g of inbornyl acrylate, 0.5 g of a compound represented by the structural formula (Fancryl FA-71211A, manufactured by Hitachi Chemical Co., Ltd.), 2 g of 2,6-di-tert-butyl-4-phenol, 2,4.6 2.5 g of trimethylpenzoyldiphenoylphosphine oxide (manufactured by BASF, Lucirin LR8728) was mixed to obtain a desired coating material (for secondary coating). Spread this coating material on the glass plate for 5 minutes.
After coating to a thickness of 100 m, it was cured. Table 1 shows the results of measuring the physical properties of the cured film.
実施例３゜
実施例１の中で、構造式
で示される化合物と変えた以外は、実施例１と同様にし
て被覆材料を作り、同様にして、硬化皮膜の物性測定結
果を表−１に示す。Example 3 A coating material was prepared in the same manner as in Example 1, except that the compound represented by the structural formula was changed, and the physical property measurement results of the cured film are shown in Table 1. show.
比較例１゜
実施例１の中で、構造式
で示される化合物を、構造式
で示される化合物０．５ｇをのぞいて被覆材料を作り同
様にして、硬化皮膜の物性測定結果を表−１に示す。Comparative Example 1 In Example 1, a coating material was prepared using the compound represented by the structural formula except for 0.5 g of the compound represented by the structural formula, and the results of measuring the physical properties of the cured film are shown in Table-1. show.
比較例２゜
実施例１の中で、２，６−ジ−ターシャリ−フチルー４
−メチルフェノール２ｇをのぞいて被覆材料を作り、同
様にして、硬化皮膜の物性測定結果を表−１に示す。Comparative Example 2゜In Example 1, 2,6-di-tertiary-phthyl-4
- A coating material was prepared except for 2 g of methyl phenol, and the physical properties of the cured film were measured in the same manner as shown in Table 1.
（、’ｌ１３ＣＨ３
上記衣−１において、
水素発生量（ｃｃ／ｇ”）の測定：硬化皮膜を螢光打丁
３ Ｑ ｃｍの所に室温で１０日間放置し、次いでヘッ
ドスペースボトルに入れ１２０’ＧＫ加熱し、２４時間
放置後、ガスクロマトグラフィーで測定した。(,'l13CH3 In the above coating-1, measurement of hydrogen generation amount (cc/g''): The cured film was left at room temperature for 10 days at a fluorescent coating 3 Q cm, then placed in a headspace bottle for 120' After heating with GK and standing for 24 hours, measurement was performed by gas chromatography.
実施例４゜
光学ガラスファイバ用母材を約２０００℃に加熱し、５
ｍ／秒の速度で外径１２５ミクロンの光学ガラスファイ
バを紡糸した。連続する次の工程で、ダイスコーティン
グ法により実施例１、３の樹脂組成物をそれぞれ被覆し
、紫外線を照射して硬化した。次いで実施例２の樹脂組
成物を被覆し、紫外線を照射して硬化した。得られた被
覆光学ガラスファイバは、いづれも、４０℃まで伝送損
失の変化は認められなかった。Example 4 A base material for optical glass fiber was heated to about 2000°C, and
An optical glass fiber with an outer diameter of 125 microns was spun at a speed of m/sec. In the next successive step, the resin compositions of Examples 1 and 3 were coated using a die coating method, and cured by irradiation with ultraviolet rays. Next, the resin composition of Example 2 was coated and cured by irradiation with ultraviolet rays. In all of the obtained coated optical glass fibers, no change in transmission loss was observed up to 40°C.
（発明の効果）
本発明の樹脂組成物及び光学ガラスファイバ用被覆材料
は、硬化速度が速く、螢光打丁に放置しても水素の発生
量が小さく、光ファイバの長期信頼性の向上に有用であ
る。(Effects of the Invention) The resin composition and the coating material for optical glass fibers of the present invention have a fast curing speed, generate a small amount of hydrogen even when left on a fluorescent knife, and can improve the long-term reliability of optical fibers. Useful.
Claims (1)
〔 I 〕 ▲数式、化学式、表等があります▼〔 I 〕 （式中、Ｒ＿１はＨ又はＣＨ＿３を、Ｒ＿２はＨ又は低
級アルキル基を、Ｒ＿３、Ｒ＿４、Ｒ＿５、Ｒ＿６はそ
れぞれ低級アルキル基を示す。） を有する化合物（Ｂ）と酸化防止剤（Ｃ）を含むことを
特徴とする樹脂組成物。 ２、エチレン性不飽和基を有する化合物（Ａ）と第１項
記載の一般式〔 I 〕を有する化合物（Ｂ）と酸化防止
剤（Ｃ）を含むことを特徴とする光学ガラスファイバ用
被覆材料。[Claims] 1. Compound (A) having an ethylenically unsaturated group and general formula [I] ▲ Numerical formulas, chemical formulas, tables, etc. ▼ [I] (In the formula, R_1 is H or CH_3, R_2 represents H or a lower alkyl group, and R_3, R_4, R_5, and R_6 each represent a lower alkyl group.) A resin composition comprising a compound (B) having the following formula and an antioxidant (C). 2. A coating material for optical glass fibers, comprising a compound (A) having an ethylenically unsaturated group, a compound (B) having the general formula [I] according to item 1, and an antioxidant (C). .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63159380A JP2579531B2 (en) | 1988-06-29 | 1988-06-29 | Resin composition and coating material for optical glass fiber |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63159380A JP2579531B2 (en) | 1988-06-29 | 1988-06-29 | Resin composition and coating material for optical glass fiber |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0211611A true JPH0211611A (en) | 1990-01-16 |
| JP2579531B2 JP2579531B2 (en) | 1997-02-05 |
Family
ID=15692549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63159380A Expired - Lifetime JP2579531B2 (en) | 1988-06-29 | 1988-06-29 | Resin composition and coating material for optical glass fiber |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2579531B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6075065A (en) * | 1996-12-20 | 2000-06-13 | Takeda Chemical Industries, Ltd. | Photocurable resin composition and a method for producing the same |
| JP2007167894A (en) * | 2005-12-21 | 2007-07-05 | Showa Denko Kk | Method and device for guiding front end of extruded product |
| WO2019138968A1 (en) * | 2018-01-12 | 2019-07-18 | 住友電気工業株式会社 | Ultraviolet-curable resin composition and optical fiber |
-
1988
- 1988-06-29 JP JP63159380A patent/JP2579531B2/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6075065A (en) * | 1996-12-20 | 2000-06-13 | Takeda Chemical Industries, Ltd. | Photocurable resin composition and a method for producing the same |
| JP2007167894A (en) * | 2005-12-21 | 2007-07-05 | Showa Denko Kk | Method and device for guiding front end of extruded product |
| WO2019138968A1 (en) * | 2018-01-12 | 2019-07-18 | 住友電気工業株式会社 | Ultraviolet-curable resin composition and optical fiber |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2579531B2 (en) | 1997-02-05 |
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