JPH0221406B2 - - Google Patents
Info
- Publication number
- JPH0221406B2 JPH0221406B2 JP57088525A JP8852582A JPH0221406B2 JP H0221406 B2 JPH0221406 B2 JP H0221406B2 JP 57088525 A JP57088525 A JP 57088525A JP 8852582 A JP8852582 A JP 8852582A JP H0221406 B2 JPH0221406 B2 JP H0221406B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- curing agent
- polyamine
- epichlorohydrin
- epoxy 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.)
- Expired - Lifetime
Links
- 229920000768 polyamine Polymers 0.000 claims description 28
- 239000003822 epoxy resin Substances 0.000 claims description 21
- 229920000647 polyepoxide Polymers 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 claims description 16
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 3
- 238000001723 curing Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 15
- 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 9
- -1 amine compounds Chemical class 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 230000002087 whitening effect Effects 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- KOGSPLLRMRSADR-UHFFFAOYSA-N 4-(2-aminopropan-2-yl)-1-methylcyclohexan-1-amine Chemical compound CC(C)(N)C1CCC(C)(N)CC1 KOGSPLLRMRSADR-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000010960 cold rolled steel Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000003085 diluting agent Substances 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
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000013035 low temperature curing Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は、エポキシ樹脂用硬化剤に関するもの
である。さらに詳しくは、メタキシリレンジアミ
ンとエピクロルヒドリンとの反応によつて得られ
るポリアミン化合物を有効成分として含有するエ
ポキシ樹脂用硬化剤に関する。
従来より各種ポリアミン化合物がエポキシ樹脂
の硬化剤あるいはその原料として広く用いられて
いることはよく知られている。
その中で、代表的なポリアミン化合物として
は、脂肪族ポリアミン、例えばエチレンジアミ
ン、ジエチレントリアミン、トリエチレンテトラ
ミン、テトラエチレンペンタミン、ペンタエチレ
ンヘキサミン、ヘキサメチレンジアミン；芳香族
ポリアミン、例えばフエニレンジアミン、ジアミ
ノジフエニルメタン、ジアミノジフエニルスルホ
ン；芳香環をもつた脂肪族ポリアミン、例えばキ
シリレンジアミン；あるいは脂環式ポリアミン、
例えばイソホロンジアミン、メンタンジアミン、
ビスアミノメチルシクロヘキサンなどをあげるこ
とができる。これらのポリアミン化合物は、それ
ぞれアミノ基の反応性、すなわち活性水素に起因
する固有の特徴を有し、これらのポリアミン化合
物をそのままであるいはそれぞれのポリアミン化
合物に適した変性を加えたのち、エポキシ樹脂硬
化剤として用いられている。
これらポリアミン化合物のうち、キシリレンジ
アミン、特にメタキシリレンジアミンを主成分と
する硬化剤は低温硬化に適し、硬化が速く、その
硬化物は光沢があり、硬度が高く、耐薬品性にす
ぐれているなどの特徴を有している。しかしなが
ら、この硬化剤およびその硬化物は、大気中の炭
酸ガス吸収に起因する白化現象があり、その硬化
物はかたく可撓性がない、密着性及び耐衝撃性が
劣るなどの欠点を有している。
本発明者らは、メタキシリレンジアミンが持つ
長所を失うことなく、かつメタキシリレンジアミ
ンが持つ上記欠点を改善したエポキシ樹脂用硬化
剤を見出すべく鋭意研究の結果、メタキシリレン
ジアミンとエピクロルヒドリンとの反応におい
て、メタキシリレンジアミン６〜20モルに対し、
エピクロルヒドリン１モルを添加することによつ
て得られる一般式（）
（式中、ｎはくり返し単位の数であつて、１ま
たは２の整数を表わす。）
で表わされるポリアミン化合物が、エポキシ樹脂
用硬化剤としてすぐれた性能を発揮することを見
いだして本発明に到達した。
本発明のポリアミン化合物は、メタキシリレン
ジアミンとエピクロルヒドリンとをアルカリ金属
水酸化物の存在下に反応させ、得られた反応混合
物から反応によつて生成する水とアルカリ金属塩
化物を除去することによつて得られる。メタキシ
リレンジアミンとエピクロルヒドリンとの反応モ
ル比は、通常、後者１モルに対して前者620モル
の範囲で選択される。このモル比を変えることに
よつて前記一般式中のｎの値を変えることがで
き、ｎの値は平均値として２以下であることを意
味し、その限りにおいて式（）で表わされるポ
リアミン化合物の中にｎの値が２以上に相当する
化合物が含まれていてもよい。ｎが２以上のポリ
アミン化合物であつても硬化物の硬化特性などに
は実質的に影響はないが、粘度が高くなり、作業
上好ましくない。アルカリ金属水酸化物として
は、通常、水酸化ナトリウムか水酸化カリウムの
いずれかが用いられ、その使用量は、エピクロル
ヒドリンに対して化学量論量以上、通常は若干過
剰となる範囲で選ばれる。メタキシリレンジアミ
ンとエピクロルヒドリンとの反応時間は５時間以
内でよく、反応温度は40〜100℃の範囲で選ばれ
るが、好ましくは60℃である。上述の反応条件の
もとで反応して得られた反応混合物は、次の操作
に付され、目的とするポリアミン化合物を得る。
すなわち、反応混合物を加熱と減圧のもとで処理
して反応生成水を留去した後、反応混合物中に析
出したアルカリ金属塩化物を別し、液をさら
に加熱と減圧下で処理して過剰の未反応メタキシ
リレンジアミンを留去し、釜残物として本発明の
ポリアミン化合物を得る。
本発明のエポキシ樹脂硬化剤は、前記式（）
で表わされるポリアミン化合物を有効成分として
含有していればよく、このポリアミン化合物を単
独で用いることもできるし、他のアミン化合物と
混合して用いることもできる。ここで用い得る他
のアミン化合物としては、脂肪族ポリアミン；芳
香族ポリアミン；芳香環をもつた脂肪族ポリアミ
ン；及び脂環式ポリアミンを挙げることができ、
これらは１種または２種以上を混合して用いても
よい。これらの他のアミン化合物の例示は、先の
記載を援用するが、これらのうち、特に好ましく
はメタキシリレンジアミンが挙げられる。本発明
の硬化剤において、他のアミン化合物は式（）
で表わされるポリアミン化合物に対して10重量％
以下の量で用いられるのが好ましい。さらに所望
によつて、他の公知のエポキシ樹脂用硬化剤、例
えばアクリロニトリル変性ポリアミン化合物、ポ
リアミドアミン化合物、ポリアミン／エポキシ化
合物付加反応生成物、ポリアミン／フエノール化
合物／ホルムアルデヒド縮合生成物などが併用さ
れてもよい。
本発明の硬化剤を用いて硬化させる対象のエポ
キシ樹脂は、公知のものが用いられる。これらの
エポキシ樹脂は、１分子当り少くとも２個のエポ
キシ基を有し、多価アルコール、多価フエノー
ル、多価カルボン酸あるいは多価アミンなどのグ
リシジル化合物であるグリシジル型エポキシ樹脂
や非グリシジル型エポキシ樹脂である。
本発明の硬化剤とエポキシ樹脂との配合比は、
本発明の硬化剤の活性水素当量とエポキシ樹脂の
エポキシ当量との比率で配合するのが通常である
が、多少当量比がすぐれても所期の性能は十分発
揮されるので特に配合比を限定する必要はない。
硬化に際し、その用途に応じて希釈剤、充填剤、
顔料などの種々の添加剤を加えて使用することも
可能である。
本発明の硬化剤はエポキシ樹脂との相容性がよ
く、大気中の炭酸ガス吸収に起因する白化現象が
なく、これとエポキシ樹脂との硬化物は、透明性
及び光沢がよく、可撓性に富み、接着性が強力で
はくり強度が高く、耐衝撃性及び耐薬品性が良好
であるなど種々のすぐれた性能を発揮する。
以下に本発明の態様を一層明確にするために実
施例によつて説明する。
実施例 １
メタキシリレンジアミン1088ｇと50％濃度のカ
セイソーダ水溶液82ｇとを撹拌機、滴下ロート、
温度計およびコンデンサーを備えた４つ口フラス
コ中に仕込み、これに窒素雰囲気下で撹拌しなが
らエピクロルヒドリン97ｇを滴下した。滴下中の
反応温度は60℃に保ち、滴下終了後も同温度で２
時間反応させた。次いで、フラスコ内容物の温度
を90〜100℃に保ち、100mmHgの減圧下に反応混
合物から水を留去した。水の留去後析出した塩化
ナトリウムは別し、得られた母液を130℃に保
つて2.5mmHgの減圧下でメタキシリレンジアミン
の留去を行なつた（「生成物Ａ」）。
得られた反応生成物を高真空蒸留にかけ、沸点
165〜170℃／４×10-3mmHgの留分を得た（「生成
物Ｂ」）。
さらに、「生成物Ａ」100ｇにメタキシリレンジ
アミンを2.42ｇ及び8.11ｇを添加し、それぞれ
「生成物Ｃ」及び「生成物Ｄ」を得た。
得られた硬化剤、「生成物Ａ〜Ｄ」の性能を第
１表に示す。
The present invention relates to a curing agent for epoxy resin. More specifically, the present invention relates to a curing agent for epoxy resins containing as an active ingredient a polyamine compound obtained by a reaction between metaxylylene diamine and epichlorohydrin. It is well known that various polyamine compounds have been widely used as curing agents for epoxy resins or raw materials thereof. Among them, typical polyamine compounds include aliphatic polyamines such as ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, hexamethylenediamine; aromatic polyamines such as phenylenediamine, diaminodiphenyl Methane, diaminodiphenylsulfone; aliphatic polyamines with aromatic rings, such as xylylene diamine; or alicyclic polyamines,
For example, isophoronediamine, menthanediamine,
Examples include bisaminomethylcyclohexane. Each of these polyamine compounds has unique characteristics due to the reactivity of the amino group, that is, active hydrogen, and these polyamine compounds can be cured with epoxy resin either as they are or after adding appropriate modification to each polyamine compound. It is used as an agent. Among these polyamine compounds, curing agents mainly containing xylylene diamine, especially metaxylylene diamine, are suitable for low-temperature curing, cure quickly, and the cured product is glossy, has high hardness, and has excellent chemical resistance. It has characteristics such as: However, this curing agent and its cured product suffer from a whitening phenomenon due to the absorption of carbon dioxide gas in the atmosphere, and the cured product has drawbacks such as being hard and not flexible, and having poor adhesion and impact resistance. ing. The present inventors have conducted intensive research to find a curing agent for epoxy resins that improves the above-mentioned drawbacks of metaxylylene diamine without losing the advantages of metaxylylene diamine. In the reaction, for 6 to 20 moles of metaxylylenediamine,
General formula () obtained by adding 1 mole of epichlorohydrin (In the formula, n is the number of repeating units and represents an integer of 1 or 2.) The present invention was achieved by discovering that a polyamine compound represented by the following formula exhibits excellent performance as a curing agent for epoxy resins. did. The polyamine compound of the present invention can be obtained by reacting metaxylylene diamine and epichlorohydrin in the presence of an alkali metal hydroxide, and removing water and alkali metal chloride produced by the reaction from the resulting reaction mixture. You can get it by twisting it. The reaction molar ratio of metaxylylene diamine and epichlorohydrin is usually selected in the range of 1 mole of the latter to 620 moles of the former. By changing this molar ratio, the value of n in the above general formula can be changed, and the value of n means that the average value is 2 or less, and as long as the value of n is 2 or less, the polyamine compound represented by the formula () may include a compound in which the value of n corresponds to 2 or more. A polyamine compound in which n is 2 or more does not substantially affect the curing characteristics of the cured product, but it increases the viscosity, which is unfavorable in terms of workability. As the alkali metal hydroxide, either sodium hydroxide or potassium hydroxide is usually used, and the amount used is selected within the range of a stoichiometric amount or more, usually a slight excess, relative to epichlorohydrin. The reaction time between metaxylylene diamine and epichlorohydrin may be within 5 hours, and the reaction temperature is selected within the range of 40 to 100°C, preferably 60°C. The reaction mixture obtained by the reaction under the above reaction conditions is subjected to the following operation to obtain the desired polyamine compound.
That is, after the reaction mixture is treated under heat and reduced pressure to distill off the reaction product water, the alkali metal chloride precipitated in the reaction mixture is separated, and the liquid is further treated under heat and reduced pressure to remove the excess. The unreacted metaxylylene diamine is distilled off to obtain the polyamine compound of the present invention as a residue in the pot. The epoxy resin curing agent of the present invention has the above formula ()
It is sufficient that the polyamine compound represented by the following formula is contained as an active ingredient, and this polyamine compound can be used alone or mixed with other amine compounds. Other amine compounds that can be used here include aliphatic polyamines; aromatic polyamines; aliphatic polyamines having an aromatic ring; and alicyclic polyamines,
These may be used alone or in combination of two or more. Examples of these other amine compounds refer to the previous description, and among these, metaxylylene diamine is particularly preferred. In the curing agent of the present invention, the other amine compound has the formula ()
10% by weight based on the polyamine compound represented by
Preferably, the following amounts are used: Furthermore, if desired, other known curing agents for epoxy resins, such as acrylonitrile-modified polyamine compounds, polyamide amine compounds, polyamine/epoxy compound addition reaction products, polyamine/phenol compounds/formaldehyde condensation products, etc., may be used in combination. good. As the epoxy resin to be cured using the curing agent of the present invention, known epoxy resins can be used. These epoxy resins have at least two epoxy groups per molecule, and include glycidyl-type epoxy resins that are glycidyl compounds such as polyhydric alcohols, polyhydric phenols, polyhydric carboxylic acids, or polyhydric amines, and non-glycidyl epoxy resins. It is an epoxy resin. The compounding ratio of the curing agent and epoxy resin of the present invention is:
Usually, the ratio of the active hydrogen equivalent of the curing agent of the present invention to the epoxy equivalent of the epoxy resin is blended, but even if the equivalent ratio is slightly superior, the desired performance can be sufficiently exhibited, so the blending ratio is particularly limited. do not have to.
During curing, diluents, fillers,
It is also possible to add and use various additives such as pigments. The curing agent of the present invention has good compatibility with epoxy resins, and there is no whitening phenomenon caused by carbon dioxide absorption in the atmosphere, and the cured product of this and epoxy resin has good transparency, gloss, and flexibility. It exhibits a variety of excellent properties, including strong adhesive properties, high peeling strength, and good impact resistance and chemical resistance. EXAMPLES Below, embodiments of the present invention will be explained by way of examples in order to further clarify aspects of the present invention. Example 1 1088 g of metaxylylene diamine and 82 g of a 50% caustic soda aqueous solution were mixed using a stirrer, a dropping funnel,
The mixture was placed in a four-necked flask equipped with a thermometer and a condenser, and 97 g of epichlorohydrin was added dropwise thereto while stirring under a nitrogen atmosphere. The reaction temperature during the dropwise addition was maintained at 60℃, and the temperature was maintained at the same temperature for 2 hours after the dropwise addition.
Allowed time to react. Then, water was distilled off from the reaction mixture under reduced pressure of 100 mmHg while maintaining the temperature of the flask contents at 90-100°C. After the water was distilled off, the precipitated sodium chloride was separated, and the resulting mother liquor was kept at 130°C, and metaxylylenediamine was distilled off under a reduced pressure of 2.5 mmHg ("Product A"). The resulting reaction product is subjected to high vacuum distillation to
A fraction of 165-170° C./4×10 −3 mmHg was obtained (“Product B”). Furthermore, 2.42 g and 8.11 g of metaxylylene diamine were added to 100 g of "Product A" to obtain "Product C" and "Product D", respectively. Table 1 shows the performance of the obtained curing agents, "Products A to D".
【表】
＊ メタキシリレンジアミンの略
実施例 ２
実施例１で調製した硬化剤、「生成物Ａ〜Ｄ」
を用いてエポキシ樹脂の硬化物物性及び耐薬品性
試験を行なつた。
エポキシ樹脂として「エピコート＃1001−Ｘ−
75」（商品名、油化シエルエポキシ株式会社製）
を用い、「生成物Ａ〜Ｄ」をそれぞれ9phrの割合
で配合し、これを冷間圧延鋼板に200μの膜厚に
塗布し、20℃で７日間をかけて硬化したものにつ
いて硬化物物性を測定した。結果を第２表に示
し、耐薬品性試験結果は第３表に示す。[Table] *Simplified example of metaxylylenediamine 2 Curing agent prepared in Example 1, "Products A to D"
The physical properties and chemical resistance of the cured epoxy resin were tested using this method. As an epoxy resin, “Epicote #1001-X-”
75” (product name, manufactured by Yuka Ciel Epoxy Co., Ltd.)
"Products A to D" were mixed at a ratio of 9phr each, and this was applied to a cold rolled steel plate to a film thickness of 200μ, and cured at 20℃ for 7 days.The physical properties of the cured product were then evaluated. It was measured. The results are shown in Table 2, and the chemical resistance test results are shown in Table 3.
【表】【table】
【表】【table】
【表】【table】
Claims (1)
ンとの反応において、メタキシリレンジアミン６
〜20モルに対し、エピクロルヒドリン１モルを添
加することによつて得られる一般式 （式中、ｎはくり返し単位の数であつて、１ま
たは２の整数を表す） で表されるポリアミン化合物を有効成分として含
有するエポキシ樹脂硬化剤。[Claims] 1. In the reaction between metaxylylene diamine and epichlorohydrin, metaxylylene diamine 6
General formula obtained by adding 1 mol of epichlorohydrin to ~20 mol (In the formula, n is the number of repeating units and represents an integer of 1 or 2.) An epoxy resin curing agent containing a polyamine compound represented by the following as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8852582A JPS58204022A (en) | 1982-05-25 | 1982-05-25 | Curing agent for epoxy resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8852582A JPS58204022A (en) | 1982-05-25 | 1982-05-25 | Curing agent for epoxy resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58204022A JPS58204022A (en) | 1983-11-28 |
| JPH0221406B2 true JPH0221406B2 (en) | 1990-05-14 |
Family
ID=13945246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8852582A Granted JPS58204022A (en) | 1982-05-25 | 1982-05-25 | Curing agent for epoxy resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58204022A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2013229697B2 (en) * | 2012-03-09 | 2015-12-17 | Construction Research & Technology Gmbh | Amine curable epoxy resin composition |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52111999A (en) * | 1976-03-17 | 1977-09-20 | Sanyo Chem Ind Ltd | Hardeners for epoxy resins |
-
1982
- 1982-05-25 JP JP8852582A patent/JPS58204022A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52111999A (en) * | 1976-03-17 | 1977-09-20 | Sanyo Chem Ind Ltd | Hardeners for epoxy resins |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58204022A (en) | 1983-11-28 |
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