JP2573837B2 - Flexibility imparting agent for epoxy resin and method for producing the same - Google Patents
Flexibility imparting agent for epoxy resin and method for producing the sameInfo
- Publication number
- JP2573837B2 JP2573837B2 JP62100565A JP10056587A JP2573837B2 JP 2573837 B2 JP2573837 B2 JP 2573837B2 JP 62100565 A JP62100565 A JP 62100565A JP 10056587 A JP10056587 A JP 10056587A JP 2573837 B2 JP2573837 B2 JP 2573837B2
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- producing
- acid
- imparting agent
- same
- 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 - Fee Related
Links
- 239000003822 epoxy resin Substances 0.000 title claims description 19
- 229920000647 polyepoxide Polymers 0.000 title claims description 19
- 239000003795 chemical substances by application Substances 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 6
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 5
- 229960003656 ricinoleic acid Drugs 0.000 description 5
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 5
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 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
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 4
- -1 laminates Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229940066675 ricinoleate Drugs 0.000 description 3
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 3
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
- VDPWYLLVHRYGOQ-UHFFFAOYSA-N 7-ethyloctadecane Chemical compound CCCCCCCCCCCC(CC)CCCCCC VDPWYLLVHRYGOQ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- SXNBVULTHKFMNO-UHFFFAOYSA-N 2,2-dihydroxyoctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)(O)C(O)=O SXNBVULTHKFMNO-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
Description
【発明の詳細な説明】 ［産業上の利用分野］ 本発明は、耐水性及び可撓性に優れた硬化物を与える
エポキシ樹脂組成物に関するものである。さらに詳しく
は、一般式（Ｉ）で表される化合物、好ましくは、リシ
ノール酸または12−ヒドロキシステアリン酸より誘導さ
れるグリシジルエーテル・エステル型エポキシ樹脂（構
造式（Ａ）及び（Ｂ））を使用することを特徴とする可
撓性エポキシ樹脂組成物に関するものである。Description: TECHNICAL FIELD The present invention relates to an epoxy resin composition which gives a cured product having excellent water resistance and flexibility. More specifically, a compound represented by the general formula (I), preferably a glycidyl ether / ester type epoxy resin derived from ricinoleic acid or 12-hydroxystearic acid (structural formulas (A) and (B)) is used. The present invention relates to a flexible epoxy resin composition.
［従来の技術及び問題点］ 一般にエポキシ樹脂は、その硬化物が優れた物理的、
機械的、あるいは電気的性質を有しているため、塗料、
接着剤、積層板、封止剤、注型剤等の広範な用途で用い
られている。 [Prior art and problems] In general, epoxy resin has excellent cured physical properties,
Due to its mechanical or electrical properties, paints,
It is used in a wide range of applications such as adhesives, laminates, sealants, and casting agents.
しかしながら、諸性能のバランスが最も優れた汎用の
ビスフェノールＡ型エポキシ樹脂にしても、封止剤の主
流となっているｏ−クレゾールノボラック型エポキシ樹
脂にしても、硬化物がかたいために、剥離あるいは亀裂
が発生したりまた、注型、封止剤においては素子を痛め
る等の問題点が常につきまとっている。このため種々の
改良法がいままでに考案されてきた。However, even if the epoxy resin is a general-purpose bisphenol A type epoxy resin with the best balance of various properties, or the o-cresol novolac type epoxy resin which is the mainstream of the encapsulant, the cured product is hard. In addition, cracks occur, and casting and sealing agents are always accompanied by problems such as damage to elements. For this reason, various improvements have been devised.
そのうち、最も一般的な方法は、ブチルグリシジルエ
ーテル等のモノエポキシを用いる方法、及び、ポリプロ
ピレングリコールジグリシジルエーテルなどの分子内に
可撓性を持った基を持つエポキシ樹脂を用いる方法であ
る。しかし、これらの方法は、耐熱性及び耐水性を著し
く低下させるという欠点を持っている。このうち耐熱性
の低下については可撓性材料の宿命とも言えるもので、
どの程度に抑えられるかが課題となっている。一方、耐
水性に付いては、水酸基、エーテル基、エステル基など
の極性基を少なくすることである程度改良されることが
既知の事実である。そのため、耐水性を持った可撓性エ
ポキシ樹脂として、長鎖二塩基酸のジグリシジルエステ
ルが比較的よく用いられている。これらは疎水性の長鎖
アルキレン基をもつため、耐水性があまり低下しないと
されている。例えばエピコート871（ダイマー酸ジグリ
シジルエステル、シェル社製）、SB−20G（７−エチル
オクタデカン二酸ジグリシジルエステル、岡村製油社
製）などが商品化されている。しかし、前者は、比較的
高粘稠な上に、長鎖基が長すぎるため、可撓性と機械
的、熱的特性のバランスが必ずしもよいとは言えない。
また、相溶性が悪いため、相分離を起こし、使用できな
い場合もある。一方、後者は、これらのバランスが良好
なため注目を集めている。しかしながら、その原料とな
る合成二塩基酸の製造が必ずしも容易ではない。Among them, the most common methods are a method using a monoepoxy such as butyl glycidyl ether, and a method using an epoxy resin having a flexible group in a molecule such as polypropylene glycol diglycidyl ether. However, these methods have the drawback of significantly reducing heat resistance and water resistance. Of these, the decline in heat resistance can be said to be the fate of flexible materials,
The issue is how much can be suppressed. On the other hand, it is a known fact that the water resistance can be improved to some extent by reducing the number of polar groups such as a hydroxyl group, an ether group and an ester group. Therefore, diglycidyl esters of long-chain dibasic acids are relatively frequently used as flexible epoxy resins having water resistance. Since these have a hydrophobic long-chain alkylene group, it is said that the water resistance does not decrease so much. For example, Epikote 871 (diglycidyl dimer acid, manufactured by Shell), SB-20G (diglycidyl ester of 7-ethyloctadecane diacid, manufactured by Okamura Oil Co., Ltd.) and the like are commercially available. However, the former has a relatively high viscosity and a long-chain group is too long, so that the balance between flexibility and mechanical and thermal properties is not always good.
In addition, due to poor compatibility, phase separation may occur and use may not be possible. On the other hand, the latter attracts attention because of their good balance. However, it is not always easy to produce a synthetic dibasic acid as a raw material.
［問題点を解決するための手段］ 本発明では、これらの事情を鑑み、鋭意検討を重ねた
結果、一般式（Ｉ）で表される可撓性付与剤を使用する
ことで、これらの問題点を解決するのに充分であること
を見いだした。[Means for Solving the Problems] In the present invention, in view of these circumstances, as a result of intensive studies, these problems have been solved by using the flexibility imparting agent represented by the general formula (I). Found that it was enough to solve the point.
（式中R1は炭素数が17の分枝していてもよいアルキレン
基、またはアルケニレン基を表し、ｎは０〜40の整数を
表す。） 即ち、本発明における一般式（Ｉ）の化合物の代表例
として好ましくは、リシノール酸、または12−ヒドロキ
システアリン酸より誘導されるグリシジルエーテル・エ
ステル型エポキシ樹脂が上げられる。その特性は、可撓
性、耐水性が非常に良好で、しかも低粘度のためハンド
リング上のメリットもある。さらに、原料となるリシノ
ール酸がひまし油より得られるため、非常に安価である
という経済上のメリットも合わせ持つものである。 (Wherein R 1 represents an optionally branched alkylene group or an alkenylene group having 17 carbon atoms, and n represents an integer of 0 to 40) That is, the compound of the general formula (I) in the present invention. As a typical example, glycidyl ether / ester type epoxy resin derived from ricinoleic acid or 12-hydroxystearic acid is preferable. Its properties are very good flexibility and water resistance, and there is also an advantage in handling due to its low viscosity. Furthermore, since ricinoleic acid as a raw material is obtained from castor oil, it also has the economical advantage of being extremely inexpensive.
なお、ここで言うリシノール酸とはひまし油のケン化
分解により得られる脂肪酸を示し、オレイン酸、リノー
ル酸、ジヒドロキシステアリン酸、ステアリン酸、パル
ミチン酸などの脂肪酸を含有していてもよく、また、分
子間脱水による縮合物を含有していてもよい。12−ヒド
ロキシステアリン酸はその水添物で、同様の不純物を含
有していてもよい。Note that ricinoleic acid here refers to a fatty acid obtained by saponification decomposition of castor oil, and may contain fatty acids such as oleic acid, linoleic acid, dihydroxystearic acid, stearic acid, and palmitic acid, and It may contain a condensate obtained by dehydration. 12-Hydroxystearic acid is a hydrogenated product thereof and may contain similar impurities.
上記一般式（Ｉ）で表される本発明化合物は、以下の
方法により合成される。即ち、まず、不活性溶媒中又は
無溶媒下、三フッ化ホウ素エーテル錯塩、四塩化錫等の
ルイス酸触媒存在下、アルコール性水酸基にエピクロル
ヒドリンをほぼ選択的に付加させる。なお、この反応で
は付加異性体も若干生成する。次いで触媒を水酸化アル
カリなどで中和し、大過剰のエピクロルヒドリン存在
下、第４級アンモニウム塩触媒などでカルボキシル基に
エピクロルヒドリンを付加させる。さらに生成したクロ
ルヒドリン化合物を水酸化アルカリを用いてエポキシ基
とする。そして、公知の方法により脱塩、脱エピクロル
ヒドリンを行い、本発明のエポキシ樹脂を得ることがで
きる。The compound of the present invention represented by the above general formula (I) is synthesized by the following method. That is, first, epichlorohydrin is almost selectively added to an alcoholic hydroxyl group in an inert solvent or in the absence of a solvent in the presence of a Lewis acid catalyst such as a boron trifluoride ether complex salt or tin tetrachloride. In this reaction, some addition isomers are also formed. Next, the catalyst is neutralized with an alkali hydroxide or the like, and epichlorohydrin is added to the carboxyl group with a quaternary ammonium salt catalyst or the like in the presence of a large excess of epichlorohydrin. Further, the formed chlorohydrin compound is converted into an epoxy group using an alkali hydroxide. Then, desalting and de-epichlorohydrin are performed by a known method to obtain the epoxy resin of the present invention.
反応式 本発明におけるエポキシ樹脂組成物とは、一般式
（Ｉ）で表されるグリシジルエーテル・エステル型エポ
キシ樹脂以外に、ビスフェノールＡ型エポキシ樹脂をは
じめ種々のエポキシ樹脂、あるいは反応性希釈剤との組
合せが可能である。また、硬化剤もポリアミン系、ポリ
アミド系、酸無水物系、フェノールノボラック系、イミ
ダゾール系など一般に用いられているものはすべて使用
可能である。また、溶剤、充填剤、難燃剤、離型剤、着
色剤などの添加物も必要に応じて用いることができる。
以上、エポキシ樹脂として、用いられる場合の例を示し
たが、一般的な方法であれば、特に限定するものではな
い。Reaction formula The epoxy resin composition according to the present invention includes, in addition to the glycidyl ether / ester type epoxy resin represented by the general formula (I), a combination with various epoxy resins including a bisphenol A type epoxy resin, or a reactive diluent. It is possible. As the curing agent, those generally used such as polyamines, polyamides, acid anhydrides, phenol novolaks, and imidazoles can all be used. In addition, additives such as a solvent, a filler, a flame retardant, a release agent, and a coloring agent can be used as needed.
As described above, an example in which the epoxy resin is used as an epoxy resin has been described.
［実施例］ 以下、本発明の実施例について説明するが、本発明は
これらの実施例に限定されるものではない。[Examples] Hereinafter, examples of the present invention will be described, but the present invention is not limited to these examples.
実施例１ エピコート828（シェル社製）80部に対し、リシノー
ル酸グリシジルエーテル・エステル20部を配合し、硬化
剤として、トリエチレンテトラミン12部を配合する。室
温で１日硬化後、100℃で１時間硬化させた。この硬化
物特性を機械的強度および吸水率で評価し、その結果を
表１に示す。以下の実施例も同様である。Example 1 20 parts of glycidyl ether ricinoleate / ester was mixed with 80 parts of Epicoat 828 (manufactured by Shell), and 12 parts of triethylenetetramine was mixed as a curing agent. After curing at room temperature for 1 day, it was cured at 100 ° C. for 1 hour. The properties of the cured product were evaluated by mechanical strength and water absorption, and the results are shown in Table 1. The same applies to the following embodiments.
実施例２ エピコート828、60部に対し、リシノール酸グリシジ
ルエーテル・エステル40部を配合し、硬化剤として、ト
リエチレンテトラミン11部を配合する。室温で１日硬化
後、100℃で１時間硬化させた。 Example 2 40 parts of glycidyl ether ricinoleate / ester was mixed with 60 parts of Epicoat 828, and 11 parts of triethylenetetramine was mixed as a curing agent. After curing at room temperature for 1 day, it was cured at 100 ° C. for 1 hour.
実施例３ エピコート828、80部に対し、12−ヒドロキシステア
リン酸グリシジルエーテル・エステル20部を配合し、硬
化剤として、トリエチレンテトラミン12部を配合する。
室温で１日硬化後、100℃で１時間硬化させた。Example 3 20 parts of 12-hydroxystearic acid glycidyl ether / ester was blended with 80 parts of Epicoat 828, and 12 parts of triethylenetetramine was blended as a curing agent.
After curing at room temperature for 1 day, it was cured at 100 ° C. for 1 hour.
比較例１〜４ エピコート828単独、あるいは実施例１においてリシ
ノール酸グリシジルエーテル・エステルの代わりにエピ
コート871（ダイマー酸ジグリシジルエステル）、SB−2
0G（７−エチルオクタデカン二酸ジグリシジルエステ
ル）、SR−4PG（ポリプロピレングリコールジグリシジ
ルエーテル、阪本薬品工業社製）20部を配合し、トリエ
チレンテトラミンで同様に硬化させ、硬化物特性を評価
した。Comparative Examples 1-4 Epicoat 828 alone (or epicoat 871 (diglycidyl dimer acid) in Example 1 instead of glycidyl ether ricinoleate in Example 1), SB-2
0G (7-ethyloctadecane diacid diglycidyl ester) and 20 parts of SR-4PG (polypropylene glycol diglycidyl ether, manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.) were blended, similarly cured with triethylenetetramine, and the properties of the cured product were evaluated. .
［発明の効果］ リシノール酸グリシジルエーテル・エステル及び12−
ヒドロキシステアリン酸グリシジルエーテル・エステル
は可撓性、耐水性ともに良好であり、希釈性能、経済性
などを総合すれば従来のものより優れている。[Effect of the Invention] Ricinoleic acid glycidyl ether ester and 12-
Hydroxystearic acid glycidyl ether / ester is excellent in both flexibility and water resistance, and is superior to the conventional one in terms of dilution performance, economic efficiency and the like.
Claims (2)
基、またはアルケニレン基を表し、ｎは０〜40の整数を
表す。） で表されるエポキシ樹脂用の可撓性付与剤。1. The compound of the general formula (I) (Wherein R 1 represents an optionally branched alkylene group having 17 carbon atoms or an alkenylene group, and n represents an integer of 0 to 40). Agent.
に１個以上のアルコール性水酸基と１個以上のカルボキ
シル基を持つ化合物に対し、ルイス酸触媒を用いてアル
コール性水酸基にほぼ選択的にエピクロルヒドリンを付
加させる工程を含むことを特徴とする一般式（Ｉ）で表
されるエポキシ樹脂用の可撓性付与剤の製造方法。 （式中R1は炭素数が17の分枝していてもよいアルキレン
基、またはアルケニレン基を表し、ｎは０〜40の整数を
表す。）2. A compound having one or more alcoholic hydroxyl groups and one or more carboxyl groups in one molecule in an inert solvent or in the absence of a solvent. A method for producing a flexibility imparting agent for an epoxy resin represented by the general formula (I), comprising a step of selectively adding epichlorohydrin. (In the formula, R 1 represents an optionally branched alkylene group or alkenylene group having 17 carbon atoms, and n represents an integer of 0 to 40.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62100565A JP2573837B2 (en) | 1987-04-22 | 1987-04-22 | Flexibility imparting agent for epoxy resin and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62100565A JP2573837B2 (en) | 1987-04-22 | 1987-04-22 | Flexibility imparting agent for epoxy resin and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63265915A JPS63265915A (en) | 1988-11-02 |
| JP2573837B2 true JP2573837B2 (en) | 1997-01-22 |
Family
ID=14277441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62100565A Expired - Fee Related JP2573837B2 (en) | 1987-04-22 | 1987-04-22 | Flexibility imparting agent for epoxy resin and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2573837B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5045387A (en) * | 1989-07-28 | 1991-09-03 | Hercules Incorporated | Rewettable polyolefin fiber and corresponding nonwovens |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5372095A (en) * | 1976-12-08 | 1978-06-27 | Kanebo Ltd | Preparation of cationic polymeric flocculant |
-
1987
- 1987-04-22 JP JP62100565A patent/JP2573837B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63265915A (en) | 1988-11-02 |
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