JPS6072878A - Epoxy resin - Google Patents
Epoxy resinInfo
- Publication number
- JPS6072878A JPS6072878A JP18063583A JP18063583A JPS6072878A JP S6072878 A JPS6072878 A JP S6072878A JP 18063583 A JP18063583 A JP 18063583A JP 18063583 A JP18063583 A JP 18063583A JP S6072878 A JPS6072878 A JP S6072878A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- formula
- diaminodiphenylsulfone
- epichlorohydrin
- resin
- 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
- 239000003822 epoxy resin Substances 0.000 title description 13
- 229920000647 polyepoxide Polymers 0.000 title description 13
- 150000003457 sulfones Chemical class 0.000 claims abstract description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 4
- 229920005989 resin Polymers 0.000 abstract description 4
- 239000011347 resin Substances 0.000 abstract description 4
- 239000002131 composite material Substances 0.000 abstract description 3
- 229920000049 Carbon (fiber) Polymers 0.000 abstract description 2
- 239000000853 adhesive Substances 0.000 abstract description 2
- 230000001070 adhesive effect Effects 0.000 abstract description 2
- 239000003513 alkali Substances 0.000 abstract description 2
- 239000004917 carbon fiber Substances 0.000 abstract description 2
- 230000005684 electric field Effects 0.000 abstract description 2
- 239000011159 matrix material Substances 0.000 abstract description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract description 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 abstract 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 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
- 239000010410 layer Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- -1 aliphatic amines Chemical class 0.000 description 1
- 239000004844 aliphatic epoxy resin Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000004845 glycidylamine epoxy resin Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000004843 novolac epoxy resin Substances 0.000 description 1
- 239000000088 plastic resin Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
Landscapes
- Epoxy Compounds (AREA)
- Epoxy Resins (AREA)
Abstract
Description
【発明の詳細な説明】 本発明は新規なエポキシ樹脂、すなわちＮ。[Detailed description of the invention] The present invention is a novel epoxy resin, namely N.
Ｎ、Ｎ′、Ｎ′テトラグリシジル−ビス（アミノフェニ
ル）スルホンまｌｃは／およびその縮合物に関する。N, N', N' tetraglycidyl-bis(aminophenyl)sulfone or lc relates to condensates thereof.
本発明のエポキシ樹脂は下記構造式に関する。The epoxy resin of the present invention relates to the following structural formula.
を有するものであり、またこの縮合物である。and a condensate thereof.
本発明エポキシ樹脂は、耐熱性、耐水性および貯蔵安定
性に優れ電気分野の材料として、接着剤として、また複
合材料特に炭素ａｍ、ガラス繊維、芳香族ポリアミド繊
維等からなる繊維強化樹脂におけるマトリックス樹脂等
として有用である。The epoxy resin of the present invention has excellent heat resistance, water resistance, and storage stability, and can be used as a material in the electrical field, as an adhesive, and as a matrix resin in composite materials, especially fiber-reinforced resins made of carbon am, glass fiber, aromatic polyamide fiber, etc. It is useful as such.
本発明エポキシ樹脂は、他のエポキシ樹脂例えばビスフ
ェノールＡ型エポキシ樹脂、ノボラック型エポキシ樹脂
、脂環式エポキシ樹脂、脂肪族エポキシ樹脂、グリシジ
ルアミン型エポキシ樹脂等と混合して用いることができ
、さらに熱可塑性樹脂を配合して用いることもできる。The epoxy resin of the present invention can be used by mixing with other epoxy resins such as bisphenol A epoxy resin, novolac epoxy resin, alicyclic epoxy resin, aliphatic epoxy resin, glycidylamine epoxy resin, etc. A plastic resin may also be blended and used.
熱可塑性樹脂としてはポリナルボン、ポリエーテルサル
ホン、ポリカーボネート、ボリアリレート、ポリアミド
なとが挙げられる。Examples of the thermoplastic resin include polynarbon, polyethersulfone, polycarbonate, polyarylate, and polyamide.
本発明エポキシ樹脂に対し使用される硬化剤としてはジ
アミノジフェニルスルホン、ジアミノジフェニルメタン
、ジアミノジフェニルエーテル、フェニレンジアミン等
の芳香族ジアミン類、イミダゾール類、脂肪族アミン類
、酸無水物、ジシアンジアミド、三フッ化ホウ素アミン
鉗体、等一般のエポキシ樹脂用硬化剤が挙げられる。Curing agents used for the epoxy resin of the present invention include diaminodiphenylsulfone, diaminodiphenylmethane, diaminodiphenyl ether, aromatic diamines such as phenylenediamine, imidazoles, aliphatic amines, acid anhydrides, dicyandiamide, and boron trifluoride. Examples include general curing agents for epoxy resins such as amine forceps.
本発明エポキシ樹脂は例えばアルカリの存在下３．３′
−ジアミノジフェニルスルホンあるいは４．４′ −
ジアミノジフェニルスルホンとエピクロルヒドリンとの
下記反応によって得ることができる。For example, the epoxy resin of the present invention can be prepared at 3.3' in the presence of an alkali.
-Diaminodiphenylsulfone or 4.4'-
It can be obtained by the following reaction between diaminodiphenylsulfone and epichlorohydrin.
実施例１
３．３′ −ジアミノジフェニルスルホン（ＤＤＳ ）
１２４ｏ （０，５モル）とエピクロルヒドリン４０
０００とを反応缶に仕込み、３０％水酸ナトリウム水溶
液１００９を徐々に加え反応させた。反応終了後水５０
００（］を徐々に加え系を攪拌した。Example 1 3.3'-diaminodiphenylsulfone (DDS)
124o (0.5 mol) and epichlorohydrin 40
000 was placed in a reaction vessel, and a 30% aqueous sodium hydroxide solution 1009 was gradually added to react. After the reaction, 50% water
00() was gradually added and the system was stirred.
次に有機層を水層から分離し、さらに３回有機層の水洗
、分離を繰返した。Next, the organic layer was separated from the aqueous layer, and the washing and separation of the organic layer with water was repeated three more times.
次いで未反応のエピクロルヒドリンを有機層から減圧蒸
溜にて除去した。得られたエポキシ樹脂は、エポキシ当
量１３２、軟化点４０℃であり、実施例２
４．４′ −ジアミノジフェニルスルホン（ＤＤＳ ）
１２４（］ （００，５モルとエピクロルヒドリン４
００００とを反応缶に仕込み、３０％水酸ナトリウム水
溶液１０００を徐々に加え反応させた。反応終了後水５
０００（ｌを徐々に加え系を攪拌した。Then, unreacted epichlorohydrin was removed from the organic layer by distillation under reduced pressure. The obtained epoxy resin had an epoxy equivalent of 132 and a softening point of 40°C.
124 (] (00,5 mol and epichlorohydrin 4
0000 was placed in a reaction vessel, and 30% aqueous sodium hydroxide solution 1000 was gradually added to react. After the reaction is complete, water 5
000 (l) was gradually added and the system was stirred.
次に有機層を水層から分離し、さらに３回有機層の水洗
、分離を繰返した。Next, the organic layer was separated from the aqueous layer, and the washing and separation of the organic layer with water was repeated three more times.
次いで未反応のエピクロルヒドリンを有機層から減圧蒸
溜にて除去した。得られたエポキシ樹脂は、エポキシ当
」１６９、軟化点５０℃であり、またＤＤＳのアミノ基
水素は全て消滅していることをＮＭ、Ｒざｉ認した。Then, unreacted epichlorohydrin was removed from the organic layer by distillation under reduced pressure. The obtained epoxy resin had an epoxy weight of 169 and a softening point of 50°C, and it was confirmed by NM and RZ that all the hydrogen atoms in the amino groups of DDS had disappeared.
使用例
フェノールノボラック型エポキシ樹脂エピコート １５
２ ５０Ｑ 、硬化剤として４．４′ −ジアミノジフ
ェニルスルホン２０Ｑをアセトンに溶かし３０重量％溶
液とした。これを炭素繊維（東邦ベスロン社製■ＨＴＡ
）に含浸させ乾燥して一方向性プリプレグを作った。こ
れを１８０℃で２時間、６ｋＯ／Ｃｍ２の圧力で硬化さ
せ一方向の成形板を作った。このもののコンポジット特
性は次の如くであった。Usage example: Phenol novolac type epoxy resin Epicoat 15
250Q, 4.4'-diaminodiphenylsulfone 20Q as a curing agent was dissolved in acetone to make a 30% by weight solution. This is carbon fiber (HTA manufactured by Toho Bethlon Co., Ltd.)
) and dried to make a unidirectional prepreg. This was cured at 180° C. for 2 hours at a pressure of 6 kO/Cm 2 to produce a unidirectional molded plate. The composite properties of this material were as follows.
曲げ 強度 １８７ｋｏ ／ｍｍ’ 〃 弾性率 １２．９Ｔ／ｍｓ ５一 層間剪断強度 １２．８ｋＯ／ ｉｍ’６一Bending strength 187ko/mm’ 〃 Elastic modulus 12.9T/ms 5-1 Interlaminar shear strength 12.8kO/im'61
Claims (1)
ス（アミノフェニル）スルホンまたは／およびその縮合
物。(1) N, N, N', N-tetraglycidyl-bis(aminophenyl)sulfone or/and a condensate thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18063583A JPS6072878A (en) | 1983-09-30 | 1983-09-30 | Epoxy resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18063583A JPS6072878A (en) | 1983-09-30 | 1983-09-30 | Epoxy resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6072878A true JPS6072878A (en) | 1985-04-24 |
| JPH0428267B2 JPH0428267B2 (en) | 1992-05-13 |
Family
ID=16086640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18063583A Granted JPS6072878A (en) | 1983-09-30 | 1983-09-30 | Epoxy resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6072878A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007120150A (en) * | 2005-10-28 | 2007-05-17 | Tostem Corp | Rain shutter door device |
| JP2008208683A (en) * | 2007-02-28 | 2008-09-11 | Sumitomo Forestry Co Ltd | Guide structure of sliding door |
| CN111303081A (en) * | 2020-03-27 | 2020-06-19 | 中国科学院化学研究所 | High-strength high-modulus epoxy resin composition and preparation method and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6058424A (en) * | 1983-08-01 | 1985-04-04 | アメリカン・サイアナミド・カンパニ− | Curable epoxy resin composition |
-
1983
- 1983-09-30 JP JP18063583A patent/JPS6072878A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6058424A (en) * | 1983-08-01 | 1985-04-04 | アメリカン・サイアナミド・カンパニ− | Curable epoxy resin composition |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007120150A (en) * | 2005-10-28 | 2007-05-17 | Tostem Corp | Rain shutter door device |
| JP2008208683A (en) * | 2007-02-28 | 2008-09-11 | Sumitomo Forestry Co Ltd | Guide structure of sliding door |
| CN111303081A (en) * | 2020-03-27 | 2020-06-19 | 中国科学院化学研究所 | High-strength high-modulus epoxy resin composition and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0428267B2 (en) | 1992-05-13 |
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