JPH0222371A - Coating composition for optical fiber - Google Patents
Coating composition for optical fiberInfo
- Publication number
- JPH0222371A JPH0222371A JP63172366A JP17236688A JPH0222371A JP H0222371 A JPH0222371 A JP H0222371A JP 63172366 A JP63172366 A JP 63172366A JP 17236688 A JP17236688 A JP 17236688A JP H0222371 A JPH0222371 A JP H0222371A
- Authority
- JP
- Japan
- Prior art keywords
- acrylate
- meth
- compound
- weight
- coating composition
- 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.)
- Pending
Links
- 239000008199 coating composition Substances 0.000 title claims description 13
- 239000013307 optical fiber Substances 0.000 title claims description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- -1 polyol compound Chemical class 0.000 claims abstract description 14
- 229920005862 polyol Polymers 0.000 claims abstract description 9
- 229920000193 polymethacrylate Polymers 0.000 claims abstract description 8
- 239000004814 polyurethane Substances 0.000 claims abstract description 7
- 229920002635 polyurethane Polymers 0.000 claims abstract description 7
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 5
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 12
- 239000000203 mixture Substances 0.000 abstract description 9
- 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 abstract description 2
- 239000003505 polymerization initiator Substances 0.000 abstract 2
- 239000011248 coating agent Substances 0.000 description 14
- 238000000576 coating method Methods 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000001294 propane Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 230000000704 physical effect Effects 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
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 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 3
- 239000000654 additive Substances 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- MUHNBZQOTATUGE-UHFFFAOYSA-N 2-[4-[2-[4-(2-hydroxyethoxy)cyclohexyl]propan-2-yl]cyclohexyl]oxyethanol Chemical compound C1CC(OCCO)CCC1C(C)(C)C1CCC(OCCO)CC1 MUHNBZQOTATUGE-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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000007423 decrease Effects 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
- 239000003085 diluting agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 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 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-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
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 208000000474 Poliomyelitis Diseases 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- KGQLBLGDIQNGSB-UHFFFAOYSA-N benzene-1,4-diol;methoxymethane Chemical compound COC.OC1=CC=C(O)C=C1 KGQLBLGDIQNGSB-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 1
- BZPMAESXYLPUEB-UHFFFAOYSA-N fluoren-1-one xanthen-9-one Chemical compound C1(C=CC=C2C3=CC=CC=C3C=C12)=O.C1=CC=CC=2OC3=CC=CC=C3C(C12)=O BZPMAESXYLPUEB-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- FSPSELPMWGWDRY-UHFFFAOYSA-N m-Methylacetophenone Chemical compound CC(=O)C1=CC=CC(C)=C1 FSPSELPMWGWDRY-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000005304 optical glass Substances 0.000 description 1
- BTLSLHNLDQCWKS-UHFFFAOYSA-N oxocan-2-one Chemical compound O=C1CCCCCCO1 BTLSLHNLDQCWKS-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005028 tinplate Substances 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
- 239000002023 wood Substances 0.000 description 1
Landscapes
- Optical Fibers, Optical Fiber Cores, And Optical Fiber Bundles (AREA)
- Paints Or Removers (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、耐熱水性に優れ、かつ強伸度等の性能に優れ
た光伝送用の光ファイバー用コーティング組成物に関す
る。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a coating composition for optical fibers for light transmission, which has excellent hot water resistance and excellent properties such as strength and elongation.
従来、光学ガラスファイバーは表面に傷がつくと光伝送
性能等の問題が生じることから、ファイバー表面を保護
するために各種コーテイング材で被覆して用いられてい
る。Conventionally, optical glass fibers have been used by being coated with various coating materials to protect the fiber surface, since scratches on the surface cause problems such as optical transmission performance.
該光ファイバー用コーテイング材として、ウレタンアク
リレート系のＵＶ硬化性コーテイング材が生産性及び強
伸度等の各種性能に優九ていることから数多く検討され
てきている。（特開昭６０−１８１１７０号、特開昭６
．１−２６５３６号、４？開昭６１−２９１６１１号、
特開昭６２−３０６４０号、特開昭６２−３０６４１号
、特開昭６２−５０６４２号各公報）しかし々から、従
来の本のは耐熱水性が充分とは言えず、長期的信頼性の
点で満足できるものではなりのが現状である。又、耐熱
水性を改善しようとすると、伸度が低下すると論う問題
点を有しておシ、耐熱水性に優れ、かつ強伸度等に優れ
たコーティング用組成物は現在までのところ見い出され
て論ない。As a coating material for optical fibers, many urethane acrylate-based UV curable coating materials have been studied because they are superior in various performances such as productivity and strength and elongation. (JP-A-60-181170, JP-A-60-181170,
．． No. 1-26536, 4? Kaisho 61-291611,
(Japanese Unexamined Patent Publications No. 62-30640, No. 62-30641, and No. 62-50642) However, conventional books cannot be said to have sufficient hot water resistance, and have poor long-term reliability. The current situation is that we cannot be satisfied with this. In addition, when trying to improve hot water resistance, there is a problem in that elongation decreases, and to date no coating composition that has excellent hot water resistance and excellent strength and elongation has been found. There's no argument.
本発明の目的は、耐熱水性に優れ、かつ弾伸度等の性能
に優れた光伝送用の光ファイバー用コーティング組成物
を提供することにある。An object of the present invention is to provide a coating composition for optical fibers for light transmission, which has excellent hot water resistance and excellent performance such as elastic elongation.
本発明の要Ｗとするところは、ポリイソシアネート化合
物（ａ）と水添ビスフェノール系アＶキレンオキサイド
付加物を主成分とするポリオール化合物（ｂ）とヒドロ
キシエチルキル（メタ）アクリレート（ｃ）とをａ ／
ｂ ／ ｃ ＝ １ ／ ａ ５〜Ｑ−９／１２〜１
．１の七ル比率で反応させて得られるポリウレタンポリ
（メタ）アクリレート（Ａ）２０〜９５重量部
モノビニル化合物（Ｂ４ ５〜８０重量部及び光重合
開始剤（Ｃ）
からなる光ファイバー用コーティング組成物にある。The key W of the present invention is that a polyisocyanate compound (a), a polyol compound (b) containing a hydrogenated bisphenol-based ethylene oxide adduct as a main component, and a hydroxyethylkyl (meth)acrylate (c) are combined. a /
b/c=1/a 5~Q-9/12~1
．． An optical fiber coating composition comprising 20 to 95 parts by weight of a polyurethane poly(meth)acrylate (A) obtained by reacting at a ratio of 1 to 1, 5 to 80 parts by weight of a monovinyl compound (B4) and a photopolymerization initiator (C). be.
発明に用いられるポリ１ウレタンポリ（メタ）アクリレ
ート（４）は、ポリイソシアネート化合物（ａ）とポリ
オール化合物（ｂ）とヒドロキンアルキＭ（メタ）アク
リレート（Ｃ）とを反応させて得られるものであるが、
ポリオール化合物（ｂ）としては例えば下式
（Ｒｓ ＋馬は水素又はメチル基、”＊ ｅ Ｒ４はア
ンキレン基、ｍ、ｎ＝１〜１０の整数）
で表わされる化合物等が挙げられる。具体的には、２．
２−ビス〔４（２−ヒドロキシエトキシ）Ｖクロヘキシ
Ｖ〕プロパン、２．２−ビＸ ［４（２−とドロキンエ
トキシ）シクロヘキＶル〕プロパン、ｚ２−ビス（４（
２−ヒドロキシプロポキシ）シクロヘキシル〕プロパン
、２．２−ビス（４（２−ヒ）’ロキシプロポキシ）シ
クロヘキシ〃〕プロパン等が挙げられる。The poly-1-urethane poly(meth)acrylate (4) used in the invention is obtained by reacting a polyisocyanate compound (a), a polyol compound (b), and a hydroquine alkyl M(meth)acrylate (C). Yes, but
Examples of the polyol compound (b) include compounds represented by the following formula (Rs + horse is hydrogen or methyl group, "*e R4 is ankylene group, m, n = an integer of 1 to 10). Specifically, 2.
2-bis[4(2-hydroxyethoxy)VchlorohexyV]propane, 2.2-biX[4(2- and droquinethoxy)cyclohexyl]propane, z2-bis(4(
Examples thereof include 2-hydroxypropoxy)cyclohexyl]propane, 2,2-bis(4(2-hi)'roxypropoxy)cyclohexy]propane, and the like.
上記の化合物をポリオール成分として用いると、得られ
るコーティング組成物の硬化物の耐熱水性の性能が向上
し、好ましい。It is preferable to use the above-mentioned compound as a polyol component because it improves the hot water resistance performance of the cured product of the resulting coating composition.
又、目的に応じて他のポリオール化合物と混合して用い
るととも可能であ石。また上記ポリオールと反応させる
ポリイソシアネート化合物（ａ）としては特に限定され
るものではなく、目的に応じて任意に選べばより０具体
例としては、例えば、トリレンジイソシアネート、ジフ
ェニルメタンジイソシアネート、ナフタレンジイソシア
ネート、イソホロンジイソンアネート、ビス（イソシア
ネートメチ／Ｌ／）シクロヘキサン、ジシクロヘキシル
メタン−４，４′−ジイソシアネ−）、１．６−ヘキサ
ンジイソシアネート、ジフェニルメタン−４，４′−ジ
イソシアネートなどが挙げられる。It is also possible to mix it with other polyol compounds depending on the purpose. The polyisocyanate compound (a) to be reacted with the polyol is not particularly limited, and may be selected arbitrarily depending on the purpose.Specific examples include tolylene diisocyanate, diphenylmethane diisocyanate, naphthalene diisocyanate, isophorone. Examples include diisonanate, bis(isocyanatomethane/L/)cyclohexane, dicyclohexylmethane-4,4'-diisocyanate), 1,6-hexane diisocyanate, diphenylmethane-4,4'-diisocyanate, and the like.
本発明においてはポリウレタンポリ（メタ）アクリレー
ト（んの構成成分の１つであるヒドロキシエチルキ７Ｌ
／（メタ）アクリレート（Ｃ）の具体例トしては、２−
ヒドロキシエチル（メタ）アクリレート、２−１ニトロ
キシプロビル（メタ）アクリレート、４−ヒドロキシブ
チＡ／（メタ）アクリレートなどの化合物が挙げられる
。該ポリウレタンポリ（メタ）アクリｖ−）の構成成分
（ａ） 、 （ｂ） 、 （ｃｌの添加モ〃比率として
は、ａ ／ ｂ／ ｃ ＝ ｊ ／α５〜１１９／α２
〜１．１であることが必要である。ポリオールの比率が
この範囲より低くなると、強伸度等の性能が劣化したう
、８０℃の熱水処理後のブリードアウト物が多くなった
シして好ましくな込。またポリオ−〃の比率がこの範囲
よシ高くなると、粘度が高くなシ作業性が悪くな夛、好
ましくない。In the present invention, hydroxyethyl chloride 7L, which is one of the constituent components of polyurethane poly(meth)acrylate
Specific examples of /(meth)acrylate (C) include 2-
Compounds such as hydroxyethyl (meth)acrylate, 2-1 nitroxyprobyl (meth)acrylate, and 4-hydroxybutyA/(meth)acrylate are mentioned. The addition ratio of constituent components (a), (b), (cl) of the polyurethane poly(meth)acrylic v-) is a/b/c=j/α5~119/α2
~1.1. If the ratio of polyol is lower than this range, performance such as strength and elongation deteriorates, and more bleed-out products occur after hot water treatment at 80° C., which is undesirable. Moreover, if the ratio of polio is higher than this range, the viscosity will be high and the workability will be poor, which is not preferable.
又、【Ｃ）成分の比率がこの範囲よシ低くなると未夏応
のイソシアネートが残シ、ゲル化することがあシ好まし
くない。度対に（Ｃ）成分がこの範囲よシ高くなると、
硬化性が低下し好ましくない。Furthermore, if the ratio of component (C) is lower than this range, undesirable isocyanate may remain and gel. When the (C) component becomes higher than this range,
It is not preferable because the curability decreases.
本発明に用いられるモノビニル化合物（Ｂ］ｔｉ１分子
中に重合性二重結合を１個有する化合物であ）、目的に
応じて任意に選択することが可能である。具体例として
は、テトラヒドロフルフリル（メタ）アクリレート、ヒ
ドロキシエチル／（メタ）アクリレート、フエノキシェ
チＶ（メタ）アクリレート、イソデシＡ／（メタ）アク
リレート、ラクリル（メタ）アクリレート、ベンジ／Ｌ
／（メタ）アクリレート、イソボロニル（メタ）アクリ
レート、シクロヘキシＡ／（メタ）アクリレート、ジシ
クロペンタジェニル（メタ）アクリレート、２−ヒドロ
キシエチＡ／（メタ）アクリレート、４−ヒドロキシブ
チル（メタ）アクリレート、ビニルピロリドン、テトラ
ヒドロフルフリルアセコールとＣカプロラクタム付加物
との合成物に（メタ）アクロイル基を導入した化合物、
２−エチルヘキシ／Ｌ／（メタ）アクリレート、下記一
般式（１）の化合物等が挙げられるが、強伸度のバラン
スの点から構造式ＣＩ）の化合物が好ましい。The monovinyl compound (B]ti, which is a compound having one polymerizable double bond in one molecule) used in the present invention can be arbitrarily selected depending on the purpose. Specific examples include tetrahydrofurfuryl (meth)acrylate, hydroxyethyl/(meth)acrylate, phenoxycetyl V(meth)acrylate, isodecy A/(meth)acrylate, lacryl(meth)acrylate, benzi/L
/ (meth)acrylate, isobornyl (meth)acrylate, cyclohexy A/(meth)acrylate, dicyclopentagenyl (meth)acrylate, 2-hydroxyethy A/(meth)acrylate, 4-hydroxybutyl (meth)acrylate, A compound in which a (meth)acroyl group is introduced into a compound of vinylpyrrolidone, tetrahydrofurfuryl acecol and C-caprolactam adduct,
Examples include 2-ethylhexy/L/(meth)acrylate, a compound represented by the following general formula (1), and a compound represented by the structural formula CI) is preferred from the viewpoint of balance in strength and elongation.
構造式［１） ｃ％＝＝ｃＨ−ｃｏ（−ｏｃ２山→−〇
ＣＨｚＣＦｌ（ＱｘＨｓ ）（Ｏ１’ｂ）ｉ−Ｃ馬
（ｎ−１〜５）
本発明においてはポリウレタンポリ（メタ）アクリレー
ト（Ａ）とモノビニル化合物（Ｂ）はＡ：Ｂが重量比で
２０：８０〜９５：５の範囲で配合することが必要であ
る。Ａがこの範囲よシも少なくなると、強伸度等の性能
が劣化したり、８０℃の熱水処理後のブリードアウト物
が多くなったシして光ファイバー用としては好ましくな
−。Structural formula [1] c% = = cH-co (-oc2 mountain → -〇CHzCFl(QxHs) (O1'b) i-C horse (n-1 to 5) In the present invention, polyurethane poly(meth)acrylate ( A) and the monovinyl compound (B) must be blended in a weight ratio of A:B in the range of 20:80 to 95:5.If A is less than this range, performance such as strength and elongation will deteriorate. It is not preferable for use in optical fibers because it deteriorates and bleeds out in large quantities after hot water treatment at 80°C.
また、Ａがこの範囲よシも多くなると、粘度が腐〈なり
、作業性が悪くなり、好ましく々い。Moreover, if A exceeds this range, the viscosity will become rotten and workability will deteriorate, which is not desirable.
又、特に好ましｂ範囲はム：Ｂ＝４０：６０〜６０ ：
４０である。Also, a particularly preferred range of b is: B=40:60-60:
It is 40.
本発明においては、光重合開始剤が必要である。ここで
用いる光とは波長領域２５０ ｎｍ〜４５０ ｎｍ に
属する紫外線である。In the present invention, a photopolymerization initiator is required. The light used here is ultraviolet light belonging to a wavelength range of 250 nm to 450 nm.
本発明で用いられる光重合開始剤の具体例としては１例
えば、２．２−ジメトキシ−２−フェニルアセトフェノ
ン、アセトフェノン、ベンゾフェノン、キサントンフル
オレノン、ベンズアＶデヒド、アントラキノン、３−メ
チルアセトフェノン、４−クロロベンゾフェノン、４．
４’−ジアミノベンゾフェノン、ベンゾイソプロヒルエ
ーテル、ベンゾインエチルエーテル、ベンジルジメチル
ケタール、１−（４−イソプロヒｖフェニル）−２−ヒ
ドロキシ−２−メチルプロパン−１−オン、２−ヒドロ
キシ−２−メチル−１−フェニルプロパン−１−オン、
４−オキサントン、カンファーキノン、２−メチル−１
−（４（メチＶチオ）フェニルツー２−七ルホリノープ
ロパン−１−オン等が挙げられる。これらの光重合開始
剤は単独又は二種以上の混合物で使用することができる
。又、使用量としては２通常（１１〜１０重量部であり
、好ましくは１〜５Ｍ量部である。Specific examples of the photopolymerization initiator used in the present invention include 2,2-dimethoxy-2-phenylacetophenone, acetophenone, benzophenone, xanthone fluorenone, benzua V dehyde, anthraquinone, 3-methylacetophenone, 4-chlorobenzophenone. ,4.
4'-Diaminobenzophenone, benzoisoproyl ether, benzoin ethyl ether, benzyl dimethyl ketal, 1-(4-isoprohyphenyl)-2-hydroxy-2-methylpropan-1-one, 2-hydroxy-2-methyl- 1-phenylpropan-1-one,
4-oxanthone, camphorquinone, 2-methyl-1
Examples include -(4(methyVthio)phenyl-2-7ulfolinopropan-1-one).These photopolymerization initiators can be used alone or in a mixture of two or more. The amount is usually 2 (11 to 10 parts by weight, preferably 1 to 5 M parts).
本発明においては更に必要で応じて二官能以上の重合性
モノマー 例えばポリエチレングリコールジ（メタ）ア
クリレート、ボリデロピレングリコールジ（メタ）アク
リレート、トリメチロールプロパントリ（メタ）アクリ
レート等の多官能（メタ）アクリレート化合物及びエポ
キシポリ（メタ）アクリレート、ポリエステＶ（メタ）
アクリレート等を更に加えて用いる事ができる。また所
望によシリコン樹脂、ポリウレタン樹脂、ポリゲタジエ
ン樹脂、シリコン樹脂等の変性樹脂やシリコン系添加剤
、フッ素添加剤等の添加剤も使用できる。In the present invention, if necessary, a polymerizable monomer having a bifunctional or higher functionality may be used, such as a polyfunctional (meth)acrylate such as polyethylene glycol di(meth)acrylate, boridelopylene glycol di(meth)acrylate, or trimethylolpropane tri(meth)acrylate. Compounds and epoxy poly(meth)acrylates, polyester V(meth)
Acrylate etc. can be further added and used. If desired, modified resins such as silicone resin, polyurethane resin, polygetadiene resin, and silicone resin, and additives such as silicone additives and fluorine additives may also be used.
次に本発明を実施例を用いて説明する。Next, the present invention will be explained using examples.
〔実施例１〕
ジシクロヘキシルメタン−４，４′−ジイソシアネー）
５４４２９ （１，３モル）、ポリエチレングリコ−
１Ｌ／（２−エチルヘキシル）エーテルアクリレ−）５
１＆３ｆ、重合禁止剤としてＭＥＨＱ（モノメチルエー
テルハイドロキノン）１、０５ ｆ、触媒としてジブチ
ルチンシラウリレートα２１１Ｆをフラスコに秤量投入
し、攪拌しながら４０℃で２．２−ビス〔４（２−ヒド
ロキシエトキン）Ｖクロヘキシル〕プロパン２２１９ｆ
（α６５モ／Ｌ／）を滴下して、フラスコヲ徐々に６５
℃に昇温させ、計４時間かけて反応させた。さらに７０
℃に昇温し、２−ヒドロキシエチルアクリレート１６ｔ
ａｔ（１，ａｓモル）を滴下し、更に７５℃に昇温し、
ＮｃＯ反応率が９８チ以上になったところで反応を終了
し、ウレタンアクリレ−トラ得た。[Example 1] Dicyclohexylmethane-4,4'-diisocyanate)
54429 (1,3 mol), polyethylene glycol
1L/(2-ethylhexyl)ether acrylate)5
1&3f, MEHQ (monomethyl ether hydroquinone) 1,05f as a polymerization inhibitor, and dibutyltin silaurylate α211F as a catalyst were weighed into a flask, and 2,2-bis[4(2-hydroxyethyl)] was added at 40°C while stirring. Kin) V chlorhexyl] propane 2219f
(α65 mo/L/) and gradually raise the flask to 65 liters.
The temperature was raised to 0.degree. C., and the reaction took place for a total of 4 hours. Another 70
The temperature was raised to ℃, and 16t of 2-hydroxyethyl acrylate was added.
At (1, as mol) was added dropwise, and the temperature was further raised to 75°C.
The reaction was terminated when the NcO reaction rate reached 98% or more, and a urethane acrylate was obtained.
次に反応生成物７０重量部に希釈剤としてポリエチレン
グリコ−１ｖ（２−エチルヘキシル）エーテルアクリレ
−） ３０３重量部、ベンゾフェノンエチルエーテル４
重量部を配合し、混合溶解して粘度１４００ ａｐｅ
（２５℃）の光ファイバー用コーティング組成物を作成
し、下記評価方法によシ硬化塗膜物性を評価し九。得ら
れた結果を表１１Ｃ示した。Next, to 70 parts by weight of the reaction product, 303 parts by weight of polyethylene glyco-1v(2-ethylhexyl)ether acrylate) and 4 parts by weight of benzophenone ethyl ether were added as diluents.
parts by weight, mixed and dissolved to obtain a viscosity of 1400 ape.
(25° C.) A coating composition for optical fiber was prepared, and the physical properties of the cured coating film were evaluated using the following evaluation method. The results obtained are shown in Table 11C.
〔実施例２〕
実施例１と同様の方法で、シンクロヘキクＶメタンー４
４′−ジイソシアネートと２．２−ビス（４（２−ヒド
ロキシエトキシ）シクロヘキシル〕プロパンと２−ヒド
ロキクエチルアクリレートをモル比で５：２：２となる
比率で反応させた。[Example 2] Synchrohekiku Vmethane-4 was prepared in the same manner as in Example 1.
4'-diisocyanate, 2,2-bis(4(2-hydroxyethoxy)cyclohexyl)propane, and 2-hydroxyethyl acrylate were reacted in a molar ratio of 5:2:2.
次に該反応生成物を実施例１と同様にして光ファイバー
用コーティング組成物を得た。又、実施例１と同様にし
て硬化塗膜物性を評価した。Next, the reaction product was treated in the same manner as in Example 1 to obtain a coating composition for optical fibers. Further, the physical properties of the cured coating film were evaluated in the same manner as in Example 1.
得られた結果を表１に示した。The results obtained are shown in Table 1.
〔比較例１〕
実施例１と同様の方法でジシクロヘキシルメタン−４，
４１−ジイソシアネートと２．２−ビス〔４（２−ヒド
ロキシエトキシ）シクロヘキシル〕プロパンと２−ヒド
ロキクエチルアクリレートを七Ｖ比で１：ＣＬ９５：α
１となる比率で反応させたが、高粘度のため使用できな
かった。[Comparative Example 1] Dicyclohexylmethane-4,
41-diisocyanate, 2,2-bis[4(2-hydroxyethoxy)cyclohexyl]propane and 2-hydroxyethyl acrylate in a 7V ratio of 1:CL95:α
Although the reaction was carried out at a ratio of 1, it could not be used due to the high viscosity.
〔比較例２〕
実施例１で得られた反応生成物１５重量部、ポリエチレ
ングリコール（２−エチＶヘキシｌＬ／）エーテルアク
リレート８５重量部、ベンゾインエチルエーテル４重量
部を混合溶解して光ファイバー用コーティング組成物を
得た。又、実施例１と同様にして硬化塗膜物性を評価し
た。得られた結果を表１に示した。[Comparative Example 2] Optical fiber coating was prepared by mixing and dissolving 15 parts by weight of the reaction product obtained in Example 1, 85 parts by weight of polyethylene glycol (2-ethyVhexyl/) ether acrylate, and 4 parts by weight of benzoin ethyl ether. A composition was obtained. Further, the physical properties of the cured coating film were evaluated in the same manner as in Example 1. The results obtained are shown in Table 1.
〔比較例３〕
実施例１で得られた反応生成物９８重散部に希釈剤とし
てポリエチレングリコール（２−エチルへキシ／Ｌ／）
エーテルアクリレート２重墓部、ベンゾインエチルエー
テル４重量部を混合溶解して粘度１００００ Ｑ ａｐ
ｅ以上の組成物を得たが高粘度のため使用できなかった
。[Comparative Example 3] Polyethylene glycol (2-ethylhexy/L/) was added as a diluent to 98 parts of the reaction product obtained in Example 1.
Mix and dissolve ether acrylate double layer and 4 parts by weight of benzoin ethyl ether to obtain a viscosity of 10,000 Q ap.
Although a composition with a rating of e or higher was obtained, it could not be used due to its high viscosity.
〔比較例４〕
実施例１と同様の方法でジシクロヘキシルメタン−４，
４Ｉ−ジイソシアネートと２．２−ビス〔４（２−ヒド
ロキシエトキシ）シクロヘキＶル〕プロパンと２−ヒド
ロキシエチルアクリレートをモル比で１： ０．２ ：
ｔ ２と々る比率で反応させた。[Comparative Example 4] Dicyclohexylmethane-4,
4I-diisocyanate, 2.2-bis[4(2-hydroxyethoxy)cyclohexyl]propane, and 2-hydroxyethyl acrylate in a molar ratio of 1:0.2:
The reaction was carried out at a ratio of t2.
次に実施例１と同様にして混合溶解して光ファイバー用
コーティング組成物を得た。又、実施例１と同様にして
硬化塗膜物性を評価した。Next, the mixture was mixed and dissolved in the same manner as in Example 1 to obtain an optical fiber coating composition. Further, the physical properties of the cured coating film were evaluated in the same manner as in Example 1.
得られた結果を表ＩＫ示した。The results obtained are shown in Table IK.
く硬化塗膜の評価方法〉
上記実施例１，２、比較例２．４で得られたコーティン
グ組成物を用いて下記のようにして評価を行った。各コ
ーティング組成物をブリキ板上に０．２重厚になるよう
に塗布して試験片を作製し、水銀ランデ１６０ Ｗ／Ｌ
ｙｎ２木で６１５０ｍＪ／ｃｍ”の照射強度、コンベア
速度２ ｍ ／閣の条件で紫外線を照射し硬化させた。Evaluation method of cured coating film> The coating compositions obtained in Examples 1 and 2 and Comparative Examples 2 and 4 were evaluated as follows. Each coating composition was coated on a tin plate to a thickness of 0.2 to prepare a test piece.
UV rays were irradiated on yn2 wood at an irradiation intensity of 6150 mJ/cm and a conveyor speed of 2 m/cm for curing.
次に硬化塗膜の物性を下記の方法で測定した。Next, the physical properties of the cured coating film were measured by the following method.
ゲル分率（チ）：塗膜を沸点温度に保ったアセトン中で
試験片を２時間処理し、乾燥し、下式を用いてゲル分率
を測定した。Gel fraction (ch): The test piece was treated for 2 hours in acetone kept at the boiling point temperature, dried, and the gel fraction was measured using the following formula.
ゲル分率＝（処理後の重量）／（処理前の重量）Ｘ１０
０強伸度（ｋｌＦ／ｃｍ” ） ：テンシロンを用い、
引張速度５０ ｗｍ ／ ｍｉｎで２号ダンペＶ使用し
１．Ｔ工ＥＩＫ−７１１３に基づいて測定した。Gel fraction = (weight after treatment) / (weight before treatment) x 10
0 strength elongation (klF/cm”): using Tensilon,
1. Using a No. 2 damper V at a tensile speed of 50 wm/min. Measured based on T Engineering EIK-7113.
重量減帳）：塗膜を８０℃の熱水中で３０日間処理後乾
燥し下式によシ重量減を測定した。Weight loss): The coating film was treated in hot water at 80° C. for 30 days and then dried, and the weight loss was measured using the following formula.
重量減＝ＣＩ−（処理後の重量）／（処理前の重ｆ＃：
）〕×１００表 １
上記の表から明らか々ように本発明のコーティング組成
物は８０℃の耐熱水性においてブリードアウト物が少な
く、また強伸度の性能にかいて本劣化がなく、光ファイ
バー用コーティング組成物として優れていることがわか
る。Weight loss = CI - (weight after treatment) / (weight before treatment f#:
)] x 100 Table 1 As is clear from the table above, the coating composition of the present invention has little bleed-out matter in hot water resistance at 80°C, and there is no major deterioration in strength and elongation performance, making it suitable for coating for optical fibers. It can be seen that the composition is excellent.
以上詳述したように、本発明の組成物を硬化して得られ
る塗膜は耐熱水性に優れ、かつ強伸度等の諸性能に優れ
ていることから、光伝送用光ファイバーのコーディング
材として優れた効果を発揮することができるものである
。As detailed above, the coating film obtained by curing the composition of the present invention has excellent hot water resistance and various properties such as strength and elongation, making it an excellent coating material for optical fibers for light transmission. It is possible to exert a certain effect.
Claims (1)
系アルキレンオキサイド付加物を主成分とするポリオー
ル化合物（ｂ）とヒドロキシアルキル（メタ）アクリレ
ート（ｃ）とをａ／ｂ／ｃ＝１．０／０．５〜０．９／
０．２〜１．１のモル比率で反応させて得られるポリウ
レタンポリ（メタ）アクリレート（Ａ）２０〜９５重量
部 モノビニル化合物（Ｂ）５〜８０重量部及び光重合開始
剤（Ｃ） からなる光ファイバー用コーティング組成物。[Claims] A polyisocyanate compound (a), a polyol compound (b) containing a hydrogenated bisphenol-based alkylene oxide adduct as a main component, and a hydroxyalkyl (meth)acrylate (c) with a/b/c=1 .0/0.5~0.9/
Consisting of 20 to 95 parts by weight of polyurethane poly(meth)acrylate (A) obtained by reaction at a molar ratio of 0.2 to 1.1, 5 to 80 parts by weight of monovinyl compound (B), and a photopolymerization initiator (C). Coating composition for optical fiber.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63172366A JPH0222371A (en) | 1988-07-11 | 1988-07-11 | Coating composition for optical fiber |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63172366A JPH0222371A (en) | 1988-07-11 | 1988-07-11 | Coating composition for optical fiber |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0222371A true JPH0222371A (en) | 1990-01-25 |
Family
ID=15940574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63172366A Pending JPH0222371A (en) | 1988-07-11 | 1988-07-11 | Coating composition for optical fiber |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0222371A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6562881B2 (en) * | 2001-05-30 | 2003-05-13 | Henkel Loctite Corporation | Liquified polyols, urethane acrylate resins prepared therewith and curable compositions employing such resins |
| WO2012036696A1 (en) * | 2010-09-17 | 2012-03-22 | Empire Technology Development Llc | Hydrogenated bisphenol-a-based polymers as substitutes for bisphenol-a-based polymers |
| US8802792B2 (en) | 2010-09-17 | 2014-08-12 | Empire Technology Development Llc | Partially hydrogenated bisphenol-A-based polymers as substitutes for bisphenol-A-based polymers |
| CN104497926A (en) * | 2015-01-26 | 2015-04-08 | 温州泓呈祥科技有限公司 | Waterproof environment-friendly binder |
-
1988
- 1988-07-11 JP JP63172366A patent/JPH0222371A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6562881B2 (en) * | 2001-05-30 | 2003-05-13 | Henkel Loctite Corporation | Liquified polyols, urethane acrylate resins prepared therewith and curable compositions employing such resins |
| WO2012036696A1 (en) * | 2010-09-17 | 2012-03-22 | Empire Technology Development Llc | Hydrogenated bisphenol-a-based polymers as substitutes for bisphenol-a-based polymers |
| US8802792B2 (en) | 2010-09-17 | 2014-08-12 | Empire Technology Development Llc | Partially hydrogenated bisphenol-A-based polymers as substitutes for bisphenol-A-based polymers |
| CN104497926A (en) * | 2015-01-26 | 2015-04-08 | 温州泓呈祥科技有限公司 | Waterproof environment-friendly binder |
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