JPH07107153B2 - Vulcanized adhesive composition and bonding method using the same - Google Patents
Vulcanized adhesive composition and bonding method using the sameInfo
- Publication number
- JPH07107153B2 JPH07107153B2 JP13061687A JP13061687A JPH07107153B2 JP H07107153 B2 JPH07107153 B2 JP H07107153B2 JP 13061687 A JP13061687 A JP 13061687A JP 13061687 A JP13061687 A JP 13061687A JP H07107153 B2 JPH07107153 B2 JP H07107153B2
- Authority
- JP
- Japan
- Prior art keywords
- adhesive composition
- vulcanized adhesive
- phenol
- metal
- 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
- 239000000853 adhesive Substances 0.000 title claims description 27
- 230000001070 adhesive effect Effects 0.000 title claims description 27
- 239000000203 mixture Substances 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 7
- -1 aromatic alkyl ether Chemical class 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 16
- 239000002184 metal Substances 0.000 claims description 16
- 229920000459 Nitrile rubber Polymers 0.000 claims description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000005011 phenolic resin Substances 0.000 claims description 9
- 239000011347 resin Substances 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 9
- 238000009833 condensation Methods 0.000 claims description 8
- 230000005494 condensation Effects 0.000 claims description 8
- 229920001971 elastomer Polymers 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000010680 novolac-type phenolic resin Substances 0.000 claims description 4
- 229920003986 novolac Polymers 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 9
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920001967 Metal rubber Polymers 0.000 description 4
- 239000004312 hexamethylene tetramine Substances 0.000 description 4
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000008399 tap water Substances 0.000 description 3
- 235000020679 tap water Nutrition 0.000 description 3
- 238000004073 vulcanization Methods 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000011812 mixed powder Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 229910001369 Brass Inorganic materials 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 238000005422 blasting Methods 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- YYDZNOUMWKJXMG-UHFFFAOYSA-N chloro(phenyl)phosphane Chemical compound ClPC1=CC=CC=C1 YYDZNOUMWKJXMG-UHFFFAOYSA-N 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GVYLCNUFSHDAAW-UHFFFAOYSA-N mirex Chemical compound ClC12C(Cl)(Cl)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C4(Cl)C1(Cl)Cl GVYLCNUFSHDAAW-UHFFFAOYSA-N 0.000 description 1
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N p-dimethylbenzene Natural products CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- FBEVECUEMUUFKM-UHFFFAOYSA-M tetrapropylazanium;chloride Chemical compound [Cl-].CCC[N+](CCC)(CCC)CCC FBEVECUEMUUFKM-UHFFFAOYSA-M 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、加硫接着剤配合物及びそれを用いる接着方法
に関する。更に詳しくは、金属とニトリルゴムとの間の
接着等に有効に用いられる加硫接着剤配合物及びそれを
用いる接着方法に関する。The present invention relates to a vulcanized adhesive composition and a bonding method using the same. More specifically, it relates to a vulcanized adhesive composition effectively used for adhesion between a metal and a nitrile rubber, and an adhesion method using the same.
従来、金属とニトリルゴムとの間の接着には、主として
フェノール樹脂系の接着剤が用いられているが、フェノ
ール樹脂系の加硫接着剤を用いた場合には、接着後の耐
水性に問題があり、水環境下例えば温水中では金属面か
らの剥れが発生することが多い。Conventionally, a phenol resin adhesive is mainly used for adhesion between metal and nitrile rubber, but when a phenol resin vulcanized adhesive is used, there is a problem in water resistance after adhesion. In a water environment, for example, in hot water, peeling from a metal surface often occurs.
そこで、本発明者等は、水環境下例えば温水中において
も十分な接着力が保持される様な接着剤配合物を求めて
種々検討の結果、以下の加硫接着剤配合物を見出し、又
それを用いることによりかかる目的を十分に満足させる
ものであることを見出し、本発明に至った。Therefore, the present inventors have found various vulcanized adhesive formulations below as a result of various investigations for adhesive formulations capable of retaining sufficient adhesive force even in a water environment, for example, in warm water, and It has been found that the use of it can sufficiently satisfy such an object, and the present invention has been completed.
従って、本発明は加硫接着剤配合物に係り、この加硫接
着剤配合物は、ノボラック型フェノール樹脂、芳香族ア
ルキルエーテルとフェノールとの縮合樹脂及び硬化剤を
含有してなる。Therefore, the present invention relates to a vulcanized adhesive composition, which comprises a novolac type phenolic resin, a condensation resin of aromatic alkyl ether and phenol, and a curing agent.
本発明は又、かかる加硫接着剤配合物を用いる金属とゴ
ムとの接着方法に係り、金属とゴムとの接着は、かかる
加硫接着剤配合物を金属に塗布し、焼付け処理を行った
後、未加硫のニトリルゴムを接触させ、加硫温度で加圧
加硫することにより行われる。The present invention also relates to a method for adhering a metal and a rubber using such a vulcanizing adhesive composition, and for adhering a metal and a rubber, such a vulcanizing adhesive composition is applied to a metal and baked. After that, it is carried out by bringing unvulcanized nitrile rubber into contact and pressurizing and vulcanizing at a vulcanizing temperature.
加硫接着剤配合物の一成分であるノボラック型フェノー
ル樹脂は、次のような一般式で表わされるものである。The novolac type phenolic resin, which is one component of the vulcanizing adhesive composition, is represented by the following general formula.
このように、ノボラック型フェノール樹脂は、フェノー
ルあるいはアルキル置換フェノールとホルムアルデヒド
とを酸触媒下で反応させることにより、アルコール、ケ
トンなどの有機溶剤に可溶な松やに状物として得られ、
これにアミン化合物あるいはリン化合物などの硬化剤を
加えて加熱することによって、不溶不融のフェノール樹
脂を形成する。本発明においては、融点が約100〜150℃
程度、分子量が約数100〜数1000程度のものが用いられ
る。 Thus, the novolac type phenol resin is obtained as a pine or a substance soluble in an organic solvent such as alcohol or ketone by reacting phenol or an alkyl-substituted phenol with formaldehyde under an acid catalyst,
An insoluble and infusible phenol resin is formed by adding a curing agent such as an amine compound or a phosphorus compound to this and heating it. In the present invention, the melting point is about 100 to 150 ° C.
Those having a molecular weight of about several hundreds to several thousands are used.
又、他の一成分である芳香族アルキルエーテルとフェノ
ールとの縮合樹脂は、次の様な一般式で表わされるもの
である。A condensed resin of an aromatic alkyl ether and phenol, which is another component, is represented by the following general formula.
芳香族アルキルエーテルとフェノールとの縮合樹脂は、
従来のノボラック型フェノール樹脂に比べ、メチレン結
合がパラキシレン結合となっている為耐熱性に優れてお
り、又構造上OH基が少ない為耐水性も優れている。 Condensation resin of aromatic alkyl ether and phenol,
Compared to conventional novolac type phenolic resins, the methylene bond is a para-xylene bond, so it has excellent heat resistance, and the structure has few OH groups, so it has excellent water resistance.
本発明においては、軟化点約80〜120℃、平均分子量約1
000〜5000程度のものが用いられる。In the present invention, the softening point is about 80 to 120 ° C and the average molecular weight is about 1
Something from 000 to 5000 is used.
硬化剤としては、アミン化合物またはリン化合物が一般
に用いられる。As the curing agent, amine compounds or phosphorus compounds are generally used.
アミン化合物としては、次の一般式で表わされるような
ものが用いられる。As the amine compound, those represented by the following general formula are used.
（ａ） Ｈ2Ｎ（ＣnＨ2nNH）m CnＨ2nNH2 m:0または25程度迄の正の整数 n:正の整数 （ｂ） Ｈ2Ｎ−Ｒ3‐NH2 Ｒ3： （ｃ） 複素環式アミン化合物 ヘキサメチレンテトラミンなど （ｄ） アンモニウム塩 テトラブチルアンモニウムブロミド、 テトラブチルアンモニウムヨージド、 テトラプロピルアンモニウムクロリドなど 又、リン化合物としては、例えばトリフェニルホスフィ
ンなどのホスフィン、ベンジルトリフェニルホスホニウ
ムクロリドなどのホスホニウム塩などが用いられる。こ
れらの硬化剤の中、ヘキサメチレンテトラミンが好んで
用いられる。 (A) H 2 N (C n H 2n NH) m C n H 2n NH 2 m: 0 or up to about 25 positive integer n: a positive integer (b) H 2 N-R 3 -NH 2 R 3 : (C) Heterocyclic amine compounds such as hexamethylenetetramine (d) Ammonium salts Tetrabutylammonium bromide, tetrabutylammonium iodide, tetrapropylammonium chloride, etc. Further, examples of the phosphorus compound include phosphines such as triphenylphosphine, benzyltrine and the like. Phosphonium salts such as phenylphosphonium chloride are used. Among these curing agents, hexamethylenetetramine is preferably used.
これらの各成分は、ノボラック型フェノール樹脂100重
量部に対して、芳香族アルキルエーテルとフェノールと
の縮合樹脂が約50〜150重量部の割合で、又硬化剤が約
５〜30重量部の割合でそれぞれ用いられる。上記縮合樹
脂の割合が50重量部未満の場合には耐水性が低下し、一
方150重量部を超える場合にはゴムとの反応性が低下す
る。又、上記硬化剤の割合が５重量部未満の場合には、
硬化速度が小さくなり、耐水性も低下し、逆に30重量部
を超える場合には硬化剤が残留し、耐水性が低下する。Each of these components is contained in a ratio of about 50 to 150 parts by weight of a condensation resin of an aromatic alkyl ether and a phenol and about 5 to 30 parts by weight of a curing agent with respect to 100 parts by weight of a novolac type phenol resin. Used in each. If the proportion of the above condensation resin is less than 50 parts by weight, the water resistance will decrease, while if it exceeds 150 parts by weight, the reactivity with rubber will decrease. When the proportion of the above curing agent is less than 5 parts by weight,
If the curing rate is low and the water resistance is low, on the contrary, if it exceeds 30 parts by weight, the curing agent remains and the water resistance is lowered.
以上の各成分を必須成分とする加硫接着剤配合物は、一
般に有機溶剤溶液として調製されて使用される。有機溶
剤としては、これらの各配合成分を溶解し得るものであ
れば任意のものを使用し得る。The vulcanized adhesive composition containing the above-mentioned components as essential components is generally prepared and used as an organic solvent solution. As the organic solvent, any solvent can be used as long as it can dissolve each of these components.
この加硫接着剤配合物を金属とニトリルゴムとの接着に
用いる場合には、この配合物を金属面に塗布し、室温で
約30〜60分間風乾させた後、好ましくは約100〜200℃で
約10〜30分間加熱して焼付け処理を行った後、金型内で
未加硫のニトリルゴムをその上に置きあるいは注入する
などして金属と接触させ、ニトリルゴムの加硫温度であ
る約150〜200℃で加圧加硫することにより接着が行われ
る。When this vulcanized adhesive formulation is used to bond metal and nitrile rubber, the formulation is applied to a metal surface and allowed to air dry at room temperature for about 30-60 minutes, preferably at about 100-200 ° C. After heating for about 10 to 30 minutes with a baking treatment, place the unvulcanized nitrile rubber on the mold or inject it into contact with the metal to reach the vulcanization temperature of the nitrile rubber. Adhesion is achieved by pressure vulcanization at about 150-200 ° C.
金属としては、軟鋼、ステンレススチール、アルミニウ
ム、アルミニウムダイキャスト、黄銅、亜鉛などが用い
られる。As the metal, mild steel, stainless steel, aluminum, aluminum die cast, brass, zinc and the like are used.
本発明に係る加硫接着剤配合物を用いて金属とニトリル
ゴムとの接着を行うと、従来のフェノール樹脂系の加硫
接着剤に比べ、耐水接着性を著しく向上させる効果があ
る。Adhesion between a metal and a nitrile rubber using the vulcanized adhesive composition according to the present invention has an effect of significantly improving water-resistant adhesiveness as compared with a conventional phenol resin-based vulcanized adhesive.
従って、本発明の加硫接着剤配合物は、この様な性質を
利用して、各種工業用のゴム部品例えばオイルシール、
ガスケット、パッキング、バルブ部品等と金属との接着
に有効に適用される。又金属とニトリルゴムとの接着以
外にも、金属とアクリルゴムとの接着にも適用出来る。Therefore, the vulcanized adhesive composition of the present invention utilizes such properties to make rubber parts for various industries, such as oil seals,
Effectively used for bonding gaskets, packing, valve parts, etc. to metal. In addition to bonding metal and nitrile rubber, it can be applied to bonding metal and acrylic rubber.
次に、実施例について本発明を説明する。 Next, the present invention will be described with reference to examples.
実施例 ノボラック型フェノール樹脂100重量部、芳香族アルキ
ルエーテルとフェノールとの縮合樹脂（三井東圧化学製
ミレックスXL-225）100重量部及びヘキサメチレンテ
トラミン20重量部の混合粉末を、メチルエチルケトン：
メタノール（重量比1:1）混合溶剤に溶解し、固形分濃
度10重量％の加硫接着剤配合物を調製した。Example A mixed powder of 100 parts by weight of a novolac-type phenol resin, 100 parts by weight of a condensation resin of aromatic alkyl ether and phenol (Mirei XL-225 manufactured by Mitsui Toatsu Chemicals) and 20 parts by weight of hexamethylenetetramine was added to methyl ethyl ketone:
It was dissolved in a mixed solvent of methanol (weight ratio 1: 1) to prepare a vulcanized adhesive composition having a solid content concentration of 10% by weight.
この加硫接着剤配合物中に、溶剤による脱脂処理及びシ
ョットブラスト処理による表面処理を施した軟鋼板を浸
漬塗布した。塗布済みの軟鋼板を室温条件下に60分間、
次いで180℃の温度条件下に10分間放置して焼付けを行
った。Into the vulcanized adhesive composition, a mild steel plate surface-treated by solvent degreasing and shot blasting was applied by dip coating. The coated mild steel sheet at room temperature for 60 minutes,
Then, baking was performed by leaving it for 10 minutes under the temperature condition of 180 ° C.
この塗布面に、下記表１に示される未加硫のニトリルゴ
ム配合物を4mmの厚さで載せ、180℃、60kg/cm2、４分間
の条件下で加熱加硫させた。次に、圧力容器中で、120
℃の水道水に100時間浸漬した。上記加硫接着物の水未
浸漬物及び水浸漬物を、JIS-K6301に従って90°剥離法
で剥離強度とゴム残り面積とを測定し、その結果を比較
例１〜２と共に、後記表２に示した。An unvulcanized nitrile rubber compound shown in Table 1 below was placed on the coated surface in a thickness of 4 mm, and heated and vulcanized under the conditions of 180 ° C., 60 kg / cm 2 , and 4 minutes. Then, in a pressure vessel, 120
It was immersed in tap water at ℃ for 100 hours. Peeling strength and rubber remaining area of the above vulcanized adhesives, which were not soaked in water and soaked in water, were measured by the 90 ° peeling method according to JIS-K6301, and the results are shown in Table 2 below together with Comparative Examples 1 and 2. Indicated.
表１ 配 合 成 分 配合量 ニトリルゴム（日本ゼオン製 ニポール1042） 100重量
部 FEFカーボンブラック 50 〃 酸化亜鉛 ５ 〃 ステアリン酸 １ 〃 イオウ 0.8 〃 加硫促進剤 TT ２ 〃 （テトラメチルチウラムジスルフィド） 加硫促進剤 CZ 2.5 〃 （Ｎ−シクロヘキシル−２− ベンゾチアジルスルフィンアミド） 比較例１ 市販のフェノール樹脂接着剤（アンカーケミカル社製
タイプライBN）に実施例と同様の処理を行った軟鋼板を
浸漬塗布した。塗布済みの軟鋼板を室温条件下に60分、
次いで80℃の温度条件下に10分間放置して焼付けを行っ
た。この塗布面に、前記表１に示される未加硫のニトリ
ルゴム配合物を4mmの厚さで載せ、180℃、60kg/cm2、４
分間の条件下で加熱加硫させた。Table 1 Constitutive Ingredients amount nitrile rubber (Nippon Zeon Nipol 1042) 100 parts by weight FEF carbon black 50 〃 Zinc oxide 5 〃 stearate 1 〃 sulfur 0.8 〃 vulcanization accelerator TT 2 〃 (tetramethylthiuram disulfide) pressure Sulfurization accelerator CZ 2.5〃 (N-cyclohexyl-2-benzothiazylsulfinamide) Comparative Example 1 Commercially available phenol resin adhesive (manufactured by Anchor Chemical Co.)
A type steel BN) was dip-coated with a mild steel sheet treated in the same manner as in the example. Apply mild steel sheet for 60 minutes at room temperature,
Then, it was left to stand for 10 minutes under the temperature condition of 80 ° C. for baking. On this coated surface, the unvulcanized nitrile rubber compound shown in Table 1 was placed in a thickness of 4 mm, and the temperature was 180 ° C., 60 kg / cm 2 , 4
It was heated and vulcanized under the condition of 1 minute.
その後、実施例と同条件で、水道水中に浸漬を行った。Then, it was immersed in tap water under the same conditions as in the example.
比較例２ 芳香族アルキルエーテルとフェノールとの縮合樹脂（三
井東圧化学製 ミレックスXL-225）100重量部及びヘキ
サメチレンテトラミン10重量部の混合粉末をメチルエチ
ルケトン：メタノール（重量比1:1）混合溶剤に溶解
し、固形分濃度10重量％の接着剤を調製した。Comparative Example 2 A mixed powder of 100 parts by weight of a condensation resin of aromatic alkyl ether and phenol (Mirex XL-225 manufactured by Mitsui Toatsu Chemicals) and 10 parts by weight of hexamethylenetetramine was mixed with methyl ethyl ketone: methanol (weight ratio 1: 1) as a mixed solvent. To prepare an adhesive having a solid content of 10% by weight.
この接着剤に、実施例と同様の処理を行った軟鋼板を浸
漬塗布した。塗布済みの軟鋼板を室温条件下に60分間、
次いで180℃の温度条件下に10分間放置して焼付けを行
った。この塗布面に、前記表１に示される未加硫のニト
リルゴム配合物を4mmの厚さで載せ、180℃、60kg/cm2、
４分間の条件下で加熱加硫させた。A mild steel plate treated in the same manner as in the example was dip-coated on this adhesive. The coated mild steel sheet at room temperature for 60 minutes,
Then, baking was performed by leaving it for 10 minutes under the temperature condition of 180 ° C. On this coated surface, the unvulcanized nitrile rubber compound shown in Table 1 was placed at a thickness of 4 mm, and the temperature was 180 ° C., 60 kg / cm 2 ,
It was heat-vulcanized under the condition of 4 minutes.
その後、実施例と同条件で、水道水中に浸漬を行った。Then, it was immersed in tap water under the same conditions as in the example.
Claims (4)
キルエーテルとフェノールとの縮合樹脂及び硬化剤を含
有してなる加硫接着剤配合物。1. A vulcanized adhesive composition comprising a novolac type phenol resin, a condensation resin of an aromatic alkyl ether and phenol, and a curing agent.
範囲第１項記載の加硫接着剤配合物。2. A vulcanized adhesive formulation according to claim 1 prepared as an organic solvent solution.
キルエーテルとフェノールとの縮合樹脂及び硬化剤を含
有してなる加硫接着剤配合物を金属に塗布し、焼付け処
理を行った後、未加硫のニトリルゴムを接触させ、加硫
温度で加圧加硫することを特徴とする金属とゴムとの接
着方法。3. A vulcanized adhesive composition containing a novolac type phenolic resin, a condensation resin of an aromatic alkyl ether and phenol, and a curing agent is applied to a metal, baked and then unvulcanized. A method for adhering a metal and rubber, which comprises contacting the nitrile rubber of 1. and vulcanizing under pressure at a vulcanizing temperature.
いられる特許請求の範囲第３項記載の接着方法。4. The bonding method according to claim 3, wherein the vulcanized adhesive composition is used as an organic solvent solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13061687A JPH07107153B2 (en) | 1987-05-26 | 1987-05-26 | Vulcanized adhesive composition and bonding method using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13061687A JPH07107153B2 (en) | 1987-05-26 | 1987-05-26 | Vulcanized adhesive composition and bonding method using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63295691A JPS63295691A (en) | 1988-12-02 |
| JPH07107153B2 true JPH07107153B2 (en) | 1995-11-15 |
Family
ID=15038481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13061687A Expired - Lifetime JPH07107153B2 (en) | 1987-05-26 | 1987-05-26 | Vulcanized adhesive composition and bonding method using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07107153B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100704928B1 (en) * | 2005-12-23 | 2007-04-09 | 고려제강 주식회사 | Non-contact analysis of the bonding interface between metal and rubber |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1593726B1 (en) * | 2003-02-12 | 2013-08-21 | Nok Corporation | Water-based vulcanizable adhesive composition |
| AU2003261749A1 (en) * | 2003-08-27 | 2005-03-29 | Nok Corporation | Vulcanizable adhesive composition |
| JP5097489B2 (en) * | 2007-09-21 | 2012-12-12 | Ｎｔｎ株式会社 | Magnetic encoder and rolling bearing |
| CN108753220B (en) * | 2018-06-26 | 2021-01-05 | 长春峰泰汽车胶业有限公司 | A high temperature and solvent resistant phenolic resin film |
-
1987
- 1987-05-26 JP JP13061687A patent/JPH07107153B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100704928B1 (en) * | 2005-12-23 | 2007-04-09 | 고려제강 주식회사 | Non-contact analysis of the bonding interface between metal and rubber |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63295691A (en) | 1988-12-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1443225A (en) | Two-component water-based metal protection treatment agent | |
| JP3057822B2 (en) | Vulcanized adhesive compound | |
| JPH07107153B2 (en) | Vulcanized adhesive composition and bonding method using the same | |
| JP2870118B2 (en) | Vulcanized adhesive compound | |
| JP3175338B2 (en) | Vulcanized adhesive compound | |
| CN108463532B (en) | vulcanized adhesive | |
| US8455106B2 (en) | Acrylic rubber-metal composite | |
| JP4085658B2 (en) | Vulcanized adhesive composition | |
| JP4192527B2 (en) | Vulcanized adhesive composition | |
| JPS62263271A (en) | Adhesive composition | |
| JP2000141538A (en) | Rubber-laminated metallic sheet md its manufacture | |
| JP3120481B2 (en) | Vulcanized adhesive compound | |
| JP3849309B2 (en) | Vulcanized adhesive composition | |
| JP3514121B2 (en) | Manufacturing method of rubber laminated metal sheet | |
| JP3867406B2 (en) | Vulcanized adhesive composition | |
| JP2979156B2 (en) | Laminate for rubber coated gasket | |
| JPS62141082A (en) | Vulcanizing adhesive composition and bonding by using it | |
| JPH0668102B2 (en) | Vulcanized adhesive compound | |
| JPH0791523B2 (en) | Vulcanized adhesive compound | |
| JPH0735499B2 (en) | NBR-based vulcanizing adhesive | |
| JP2004277435A (en) | Vulcanizing adhesive composition | |
| JPH08109247A (en) | One-pack type thermosetting epoxy resin composition | |
| RU2017775C1 (en) | Composition for metal coating | |
| JPH05239428A (en) | Adhesive for composite pipe and method for manufacturing composite pipe | |
| JPH07330873A (en) | Moisture-curing epoxy resin composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term | ||
| FPAY | Renewal fee payment (prs date is renewal date of database) |
Year of fee payment: 12 Free format text: PAYMENT UNTIL: 20071115 |