JPH04509B2 - - Google Patents
Info
- Publication number
- JPH04509B2 JPH04509B2 JP61134669A JP13466986A JPH04509B2 JP H04509 B2 JPH04509 B2 JP H04509B2 JP 61134669 A JP61134669 A JP 61134669A JP 13466986 A JP13466986 A JP 13466986A JP H04509 B2 JPH04509 B2 JP H04509B2
- Authority
- JP
- Japan
- Prior art keywords
- adhesive
- isophorone diamine
- epoxy
- light transmitting
- fibers
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000853 adhesive Substances 0.000 claims description 21
- 230000001070 adhesive effect Effects 0.000 claims description 21
- 239000000835 fiber Substances 0.000 claims description 10
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- -1 amine compound Chemical class 0.000 claims description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- 239000000306 component Substances 0.000 description 5
- 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 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 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
- 239000008358 core component Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000013307 optical fiber Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920006295 polythiol Polymers 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
- URFNSYWAGGETFK-UHFFFAOYSA-N 1,2-bis(4-hydroxyphenyl)ethane Natural products C1=CC(O)=CC=C1CCC1=CC=C(O)C=C1 URFNSYWAGGETFK-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
Landscapes
- Optical Fibers, Optical Fiber Cores, And Optical Fiber Bundles (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
<産業上の利用分野>
本発明は常温で迅速に硬化し、耐環境特性に優
れた光伝送性繊維用接着剤に関する。
<従来の技術>
ポリメチルメタクリレート、ポリスチレン、ガ
ラス等の透明な素材を高速延伸して得られた光伝
送性繊維は、通信産業、装飾用デイスプレー等に
広汎に使用されている。これら素材の光伝送性繊
維の中でもポリメチルメタクリレートを芯とし、
これよりも屈折率の低い弗素樹脂を鞘として、芯
−鞘構造を有する繊維は良好な光伝送性を示す
他、軽量、安価、加工性が良好である等の特長が
確認され、広汎に使用されている。
従来、光伝送性繊維を結束する接着剤としてガ
ラス光伝送性繊維には、ポリエポキシ化合物にト
リエチレンテトラミン、メタキシリレンジアミン
等のアミン系の硬化剤を配合したエポキシ樹脂接
着剤が用いられているが、この接着剤を弗素樹脂
を鞘とし、ポリメチルメタクリレートを芯成分と
する光伝送性繊維に用いた場合、アミンにより接
着部分が茶褐色に変色し、光伝送性が低下すると
いう欠点が指摘されている。(特開昭56−161485
号、特開昭59−78230号)
該着色を惹起しない接着剤として、(1)エポキシ
(メタ)アクリレートを主体とするラジカル重合
硬化型接着剤(特開昭56−161485号)と(2)硬化剤
にポリチオールアルキル酸エステルを用いるエポ
キシ・チオール系接着剤(特開昭59−78230号)
が提案されている。
しかし、(1)のラジカル重合型接着剤は、空気中
の酸素による重合禁止作用のため、接着部分に粘
着性が残り汚染されやすいという欠点がある。ま
た、(2)のエポキシ・チオール系接着剤は硬化剤の
ポリチオールアルキル酸エステルが極めて強い不
快臭を発するという作業上の問題に加えて、硬化
物の耐水性がエポキシ・アミン系接着剤に比べ大
幅に低下するという問題がある。
<発明の構成>
そこで、本発明者らはかかる従来の光伝送性繊
維用接着剤の欠点を克服した常温硬化性接着剤を
開発すべく鋭意検討の結果本発明に到達した。
すなわち、本発明は、
(A) ポリエポキシ化合物、
(B) イソホロンジアミンおよびイソホロンジアミ
ンから誘導されるアミン化合物から選ばれる少
なくとも1種
を含有することを特徴とする光伝送性繊維用接着
剤を提供するものである。
本発明において、(A)成分のポリエポキシ化合物
は、分子内に少なくとも2個以上のエポキシ基を
有する化合物である。中でも20℃で液状のものが
作業性面で好ましい。具体的には(a)多価フエノー
ルのグリシジルエーテル:たとえば2,2−ビス
−(4−ヒドロキシフエニル)プロパン、1,1
−ビス(4−ヒドロキシフエニル)エタン及びビ
ス(4−ヒドロキシフエニル)メタンのごときジ
フエニロールアルカンのグリシジルエーテル:
4,4´−ジヒドロキシジフエニルスルホン、ハイ
ドロキノン、レゾルシン、ジヒドロキシジフエニ
ル又はジヒドロキシナフタリンのグリシジルエー
テル;フエノール又はクレゾールとホルムアルテ
ヒドとの縮合物のノボラツク、ルゾールのグリシ
ジルエーテルのごとき多価フエノールより誘導さ
れるエポキシ化合物;(b)脂肪族ポリヒドロキシ化
合物のポリ(エポキシアルキル)エーテル:たと
えばエチレングリコール、グリセロール、トリメ
チロールプロパン等により誘導されるエポキシ化
合物、(c)ポリカルボン酸のポリグリシジルエステ
ル;たとえばフタル酸、イソフタル酸、アジピン
酸、テトラヒドロフタル酸のジグリシジルエステ
ルその他のエポキシ化したジエン、ポリグリシジ
ルイソシアヌレート、ヒドロキシ安息香酸のグリ
シジルエーテル・エステル等が目的に応じて単
独、または併用して用いられる。この中でも単独
で用いるのに特に好ましいものは、2,2−ビス
−(4−ヒドロキシフエニル)プロパンのジグリ
シジルエーテルとp−ヒドロキシ安息香酸のジグ
リシジルエーテル・エステルである。
次に(B)成分のイソホロンジアミンおよび該ジア
ミンから誘導されるアミン化合物は、いずれも光
伝送性繊維に前述の悪影響を及ぼすことがなく、
(A)成分と併用して用いられる接着剤は優れた硬化
性、耐水性、耐環境性の接着硬化物と提供するこ
とできる。イソホロンジアミンから誘導されるア
ミン化合物としては、イソホロンジアミンとポリ
エポキシ化合物とのアダクト、イソホロンジアミ
ンとアルキレンオキサイド、たとえばエチレンオ
キサイド、プロピレンオキサイドとのアダクト等
があげられる。
これら(A)成分乃至(B)成分の他に用途に応じて有
機溶剤、無機充填剤、顔料、反応性希釈剤、可塑
剤、紫外線吸収剤を配合することができる。以
下、実施例により本発明を説明する。以下、部は
重量部を表わす。
実施例1〜3、比較例1〜2
芯成分としてポリメチルメタクリレート、鞘成
分として弗素樹脂を被覆した0.25mm径の光伝送性
繊維を100本束ねて端部3cmの部分に第1表に示
すような各種接着剤を塗布し、室温にて放置し硬
化させた。
得られた結果を第1表に示す。
<Industrial Application Field> The present invention relates to an adhesive for light transmitting fibers that cures rapidly at room temperature and has excellent environmental resistance properties. <Prior Art> Light transmitting fibers obtained by drawing transparent materials such as polymethyl methacrylate, polystyrene, and glass at high speed are widely used in the communication industry, decorative displays, and the like. Among the light transmitting fibers made of these materials, polymethyl methacrylate is used as the core.
Fibers with a core-sheath structure using a fluororesin with a lower refractive index as a sheath have been found to have good optical transmission properties, as well as being lightweight, inexpensive, and easy to process, and are widely used. has been done. Conventionally, epoxy resin adhesives containing polyepoxy compounds and amine-based curing agents such as triethylenetetramine and meta-xylylene diamine have been used for glass optical fibers to bind optical fibers together. However, when this adhesive is used for optically transmitting fibers with a fluororesin sheath and polymethyl methacrylate as a core component, it has been pointed out that the adhesive part turns brown due to the amine, resulting in a decrease in optical transmittance. has been done. (Unexamined Japanese Patent Publication No. 56-161485
(Japanese Patent Application Laid-Open No. 56-161485) As adhesives that do not cause coloration, (1) a radical polymerization curing adhesive mainly composed of epoxy (meth)acrylate (Japanese Patent Application Laid-open No. 56-161485); Epoxy thiol adhesive using polythiol alkyl ester as a curing agent (Japanese Patent Application Laid-open No. 78230/1983)
is proposed. However, the radical polymerization type adhesive (1) has the disadvantage that the adhesive remains sticky and easily contaminated due to the polymerization inhibiting effect of oxygen in the air. In addition, the epoxy/thiol adhesive mentioned in (2) has the problem of the curing agent, polythiol alkyl ester, which emits an extremely strong unpleasant odor, and the water resistance of the cured product is lower than that of the epoxy/amine adhesive. The problem is that it drops significantly. <Structure of the Invention> Therefore, the present inventors have conducted intensive studies to develop a room temperature curable adhesive that overcomes the drawbacks of the conventional adhesives for optically transmitting fibers, and have finally arrived at the present invention. That is, the present invention provides an adhesive for optically transmitting fibers, characterized in that it contains at least one selected from (A) a polyepoxy compound, (B) isophorone diamine, and an amine compound derived from isophorone diamine. It is something to do. In the present invention, the polyepoxy compound as component (A) is a compound having at least two or more epoxy groups in the molecule. Among these, those that are liquid at 20°C are preferred in terms of workability. Specifically, (a) glycidyl ethers of polyhydric phenols: for example, 2,2-bis-(4-hydroxyphenyl)propane, 1,1
- glycidyl ethers of diphenyloalkanes such as bis(4-hydroxyphenyl)ethane and bis(4-hydroxyphenyl)methane:
Glycidyl ether of 4,4'-dihydroxydiphenyl sulfone, hydroquinone, resorcinol, dihydroxydiphenyl or dihydroxynaphthalene; derived from polyhydric phenols such as glycidyl ether of phenol or condensates of cresol and formaltehyde, novolak, and lusol. (b) poly(epoxyalkyl) ethers of aliphatic polyhydroxy compounds; for example, epoxy compounds derived from ethylene glycol, glycerol, trimethylolpropane, etc.; (c) polyglycidyl esters of polycarboxylic acids; for example, phthal Acids, diglycidyl esters of isophthalic acid, adipic acid, tetrahydrophthalic acid, other epoxidized dienes, polyglycidyl isocyanurate, glycidyl ether esters of hydroxybenzoic acid, etc. are used alone or in combination depending on the purpose. Among these, particularly preferred for use alone are diglycidyl ether of 2,2-bis-(4-hydroxyphenyl)propane and diglycidyl ether/ester of p-hydroxybenzoic acid. Next, neither the isophorone diamine of component (B) nor the amine compound derived from the diamine has the above-mentioned adverse effect on the light transmitting fiber.
The adhesive used in combination with component (A) can provide a cured adhesive with excellent curability, water resistance, and environmental resistance. Examples of amine compounds derived from isophorone diamine include adducts between isophorone diamine and polyepoxy compounds, and adducts between isophorone diamine and alkylene oxides such as ethylene oxide and propylene oxide. In addition to these components (A) to (B), organic solvents, inorganic fillers, pigments, reactive diluents, plasticizers, and ultraviolet absorbers can be blended depending on the purpose. The present invention will be explained below with reference to Examples. Hereinafter, parts represent parts by weight. Examples 1 to 3, Comparative Examples 1 to 2 100 light transmitting fibers with a diameter of 0.25 mm coated with polymethyl methacrylate as a core component and fluororesin as a sheath component were bundled and placed at a 3 cm end portion as shown in Table 1. Various adhesives such as these were applied and left to harden at room temperature. The results obtained are shown in Table 1.
【表】【table】
【表】
<発明の効果>
以上述べたように、本発明の接着剤は空気中で
迅速に常温硬化し、優れた接着力及び光透過率を
有し、かつ接着剤層の変色も生じないことから光
伝送性接着剤として優れた効果を発揮するもので
ある。[Table] <Effects of the Invention> As stated above, the adhesive of the present invention cures rapidly in the air at room temperature, has excellent adhesive strength and light transmittance, and does not cause discoloration of the adhesive layer. Therefore, it exhibits excellent effects as a light transmitting adhesive.
Claims (1)
ンから誘導されるアミン化合物から選ばれる少
なくとも1種 を含有することを特徴とする光伝送性繊維用接着
剤。[Scope of Claims] 1. An adhesive for light transmitting fibers, comprising at least one selected from (A) a polyepoxy compound, (B) isophorone diamine, and an amine compound derived from isophorone diamine.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61134669A JPS62290783A (en) | 1986-06-10 | 1986-06-10 | Adhesive for optical fiber |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61134669A JPS62290783A (en) | 1986-06-10 | 1986-06-10 | Adhesive for optical fiber |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS62290783A JPS62290783A (en) | 1987-12-17 |
JPH04509B2 true JPH04509B2 (en) | 1992-01-07 |
Family
ID=15133791
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP61134669A Granted JPS62290783A (en) | 1986-06-10 | 1986-06-10 | Adhesive for optical fiber |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS62290783A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4300790B2 (en) | 2002-07-18 | 2009-07-22 | 住友金属鉱山株式会社 | Thermosetting optical adhesive, optical isolator element and optical isolator to which this adhesive is applied |
JP2011039366A (en) * | 2009-08-17 | 2011-02-24 | Shin-Etsu Chemical Co Ltd | Laminated body for optical isolator, optical isolator and method of manufacturing those |
-
1986
- 1986-06-10 JP JP61134669A patent/JPS62290783A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS62290783A (en) | 1987-12-17 |
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