JPS606381B2 - Anaerobic adhesive composition - Google Patents
Anaerobic adhesive compositionInfo
- Publication number
- JPS606381B2 JPS606381B2 JP8568577A JP8568577A JPS606381B2 JP S606381 B2 JPS606381 B2 JP S606381B2 JP 8568577 A JP8568577 A JP 8568577A JP 8568577 A JP8568577 A JP 8568577A JP S606381 B2 JPS606381 B2 JP S606381B2
- Authority
- JP
- Japan
- Prior art keywords
- anaerobic adhesive
- polymerizable unsaturated
- adhesive composition
- aromatic
- secondary amine
- 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
- 239000000203 mixture Substances 0.000 title claims description 19
- 239000000853 adhesive Substances 0.000 title claims description 9
- 230000001070 adhesive effect Effects 0.000 title claims description 9
- -1 aromatic imide Chemical class 0.000 claims description 17
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 7
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 7
- 239000003112 inhibitor Substances 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000007259 addition reaction Methods 0.000 claims description 4
- 125000000151 cysteine group Chemical class N[C@@H](CS)C(=O)* 0.000 claims 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 150000001945 cysteines Chemical class 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000003335 secondary amines 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
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 2
- 235000018417 cysteine Nutrition 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 229940079877 pyrogallol Drugs 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- JGBAASVQPMTVHO-UHFFFAOYSA-N 2,5-dihydroperoxy-2,5-dimethylhexane Chemical compound OOC(C)(C)CCC(C)(C)OO JGBAASVQPMTVHO-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 150000004075 acetic anhydrides Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- VIJMMQUAJQEELS-UHFFFAOYSA-N n,n-bis(ethenyl)ethenamine Chemical compound C=CN(C=C)C=C VIJMMQUAJQEELS-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
【発明の詳細な説明】 本発明は嫌気性接着剤組成物に関する。[Detailed description of the invention] The present invention relates to anaerobic adhesive compositions.
嫌気性接着剤は、空気（酸素）の存在下では容易に硬化
しないが、金属の間隙などに流し込まれ、空気との接触
を断たれると速やかに硬化する性質を有するので、ボル
ト・ナットの固定、ベアリングシャフトの固定など、広
く産業界において利用されている。Anaerobic adhesives do not harden easily in the presence of air (oxygen), but when they are poured into gaps between metals and are no longer in contact with air, they quickly harden, so they are suitable for bolts and nuts. It is widely used in industry for fixing, fixing bearing shafts, etc.
しかし、嫌気性接着剤に関する技術的課題は多い。However, there are many technical challenges regarding anaerobic adhesives.
たとえば、表面に防錆油を施したボルト・ナットへの接
着性、より多種類の金属への適用性、遠硬化性への改良
、そして構造的接着性能の改良などが課題となっている
。これらの課題についてより詳細に検討してみると、嫌
気性接着剤組成物の最優先されるべき改良点は速硬化性
にあることが明らかになった。For example, issues include adhesion to bolts and nuts whose surfaces are coated with anti-rust oil, applicability to a wider variety of metals, improved long-distance curing properties, and improved structural adhesion performance. When these issues were examined in more detail, it became clear that the most important improvement point for anaerobic adhesive compositions was rapid curing.
従来、かかる速硬化性の嫌気性接着剤組成物としては、
重合禁止剤を含むアクリレートプレポリマ−またはメタ
クリレートプレポリマーに、ラジカル開始剤として有機
過酸化物、有機アミン類、有機ィミド類、サルフアィド
、メルカプタン、フオスフアィトなどを加えてなる所謂
レックス系の組成物がある。また、同様のプレポリマー
に、有機過酸化物、サッカＩＪン、芳香族第３級アミン
または水添されたへテロサィクリックな第２級アミンを
配合してなる組成物も知られている。Conventionally, such fast-curing anaerobic adhesive compositions include:
There are so-called Rex-based compositions made by adding organic peroxides, organic amines, organic imides, sulfides, mercaptans, phosphere, etc. as radical initiators to acrylate prepolymers or methacrylate prepolymers containing polymerization inhibitors. . Also known are compositions in which a similar prepolymer is blended with an organic peroxide, saccharide, an aromatic tertiary amine, or a hydrogenated heterocyclic secondary amine.
しかし、かかる組成物も上記の技術的課題を十分に解決
し得たものではなく、なお、その硬化性と硬化物の強度
あるいは樹脂としての貯蔵安定性などに問題点を残して
いる。However, such a composition has not been able to fully solve the above technical problems, and still has problems with its curability, the strength of the cured product, and its storage stability as a resin.
本発明者らは、かかる状況に対応して鋭意検討を重ねた
結果、ジアリリデンベンタェリスリットとヒドロキシェ
チルメタクリレートの付加反応により得られる重合性不
飽和シクロアセタールと重合禁止剤およびハイドロパー
オキサィドからなる組成に反応促進剤として芳香族ィミ
ドと芳香族第２級ァミンまたはピロリジンおよび酸で中
和して得られるシスティン塩を併用してなる樹脂組成物
が嫌気性接着剤として優れた特性を有することを知り、
本発明を完成するに至った。As a result of intensive studies in response to this situation, the present inventors have discovered that a polymerizable unsaturated cycloacetal obtained by the addition reaction of diarylidene bentaeri slit and hydroxyethyl methacrylate, a polymerization inhibitor and a hydroper A resin composition consisting of a composition consisting of an oxide in combination with an aromatic imide, an aromatic secondary amine or pyrrolidine, and a cysteine salt obtained by neutralization with an acid as a reaction accelerator is excellent as an anaerobic adhesive. Knowing that it has characteristics,
The present invention has now been completed.
本発明に用いられる重合性不飽和シクロアセタールは、
ジアリリデンベンタエリスリツトとヒドロキシェチルメ
タクリレートの付加反応により得られるものである。The polymerizable unsaturated cycloacetal used in the present invention is
It is obtained by the addition reaction of diarylidene bentaerythrite and hydroxyethyl methacrylate.
この重合性不飽和シクロアセタールは貯蔵安定性に欠け
るため、一般にはハイドロキノン、ベンゾキノン、ある
いはフエノチアジンなどの酸化防止剤を添加する必要が
あり、またラジカル重合開始剤、反応促進剤の存在下で
は重合禁止剤、過酸化分解抑制剤などを樹脂の遠硬化性
を損わない範囲内で添加することができる。また、増粘
を目的として重合性不飽和シクロアセタールに、他のポ
リマーを併用したり、あるいは粘性希釈を目的としてア
クリルまたはメタクリル系のモノマ−、たとえばセルソ
ルブメタクリレ−ト、ヒドロキシエチルメタクリレート
などの、モノェポキシ化合物とメタクリル酸との付加反
応物を併用することもできる。本発明において、ラジカ
ル重合開始剤としては、安定性のよいハイドロパーオキ
サィドが用いられ、その代表例としては、キュメンハィ
ドロパオキサイド、夕一シヤリブチルハイドロパーオキ
サイド、ジプロピルベンゼーンハイド０／ぐーオキサイ
ド、／ぐラメンタンハイドロ／ぐーオキサイド、２，５
−ジメチルヘキサンー２，５ージハイドロパーオキサイ
ドなどである。Since this polymerizable unsaturated cycloacetal lacks storage stability, it is generally necessary to add an antioxidant such as hydroquinone, benzoquinone, or phenothiazine, and polymerization is inhibited in the presence of a radical polymerization initiator or reaction promoter. Agents, peroxide decomposition inhibitors, etc. can be added within a range that does not impair the far-curing properties of the resin. In addition, other polymers may be used in combination with the polymerizable unsaturated cycloacetal for the purpose of thickening, or acrylic or methacrylic monomers such as cellosolve methacrylate and hydroxyethyl methacrylate may be used for the purpose of thinning the viscosity. , an addition reaction product of a monoepoxy compound and methacrylic acid can also be used in combination. In the present invention, a hydroperoxide with good stability is used as the radical polymerization initiator, and representative examples thereof include cumene hydroperoxide, yauichi siyabutyl hydroperoxide, and dipropyl benzene hydride. 0/gu oxide,/gu ramenthan hydro/gu oxide, 2,5
-dimethylhexane-2,5-dihydroperoxide, etc.
本発明に用いられる反応促進剤は、芳香族イミドと芳香
族第２級アミンまたはピロリジンおよび酸で中和して得
られるシスティン塩の併用を特徴とするが、芳香族イミ
ドとしては○−ベンツスルフィミドが好ましく、第２級
アミンとしては芳香族第２級アミンまたはピロリジンが
用いられ、これらのうちでも特にモノ置換芳香族ァミン
が好ましく、その代表例はＮ−メチルアニリンである。The reaction accelerator used in the present invention is characterized by the combination of an aromatic imide and an aromatic secondary amine or a cysteine salt obtained by neutralizing with pyrrolidine and an acid. Rufimide is preferred, and the secondary amine used is an aromatic secondary amine or pyrrolidine, and among these, monosubstituted aromatic amines are particularly preferred, with N-methylaniline being a typical example.
，また、システィン塩は反応系への溶解性良好なものが
よく、代表例として無水酢酸による塩が特に好ましい。
本発明の組成物は、重合性不飽和シクロアセタール１０
の重量部に、ハイドロパーオキサイド０．５〜１０．の
重量部好ましくは２．０〜８．の重量部、芳香族ィミド
０．００５〜０．０４モル好ましくは０．００１〜０．
０３モル、芳香族ィミドと当モルの芳香第２級アミンま
たはピロリジンおよび酸で中和して得られるシスティン
塩０．１〜３．の重量部からなる。以下に実施例および
比較例を示すが、ここに用いられる重合性不飽和シクロ
アセタールはジアリリデンベンタエリスリツトとヒドロ
キシエチルメタクリレートをパラトルェンスルホン酸を
触媒とし、重合禁止剤としてペンゾキノンの存在下に反
応させて得られる重合性不飽和シクロアセタールにトリ
ェチレンアミンを加えて中和したる状態で用いられる。The cysteine salt preferably has good solubility in the reaction system, and as a typical example, acetic anhydride salt is particularly preferred.
The composition of the present invention comprises polymerizable unsaturated cycloacetal 10
0.5 to 10. parts by weight of hydroperoxide. Parts by weight of preferably 2.0 to 8. parts by weight, 0.005 to 0.04 mol of aromatic imide, preferably 0.001 to 0.04 mol.
0.3 mol, cysteine salt obtained by neutralizing aromatic imide with equimolar amount of aromatic secondary amine or pyrrolidine and acid. Consisting of parts by weight. Examples and comparative examples are shown below, and the polymerizable unsaturated cycloacetal used here was prepared using diarylidene bentaerythritate and hydroxyethyl methacrylate in the presence of penzoquinone as a polymerization inhibitor using paratoluene sulfonic acid as a catalyst. It is used after being neutralized by adding triethyleneamine to the polymerizable unsaturated cycloacetal obtained by reacting with cycloacetal.
次に重合性不飽和シクロアセタールの構造式を示す。Next, the structural formula of the polymerizable unsaturated cycloacetal is shown.
（重合性不飽和シクロアセタール）
比較例 １
上記重合性不飽和シクロアセタール（以下、ＤＡＰＥ−
Ｍと略称する）１０の重量部に、キュメンハイドロパー
オキサイド粥ＨＲ，０−ベンツスルフイミドのヒドロキ
シエチルメタクリレート５％蝕和溶液、およびジメチル
パラトルイジンをそれぞれ０．０２モル加えた嫌気性接
着剤組成物を用い、脱脂された３／８”少ＵＮＦ細目ネ
ジの固定を行った。(Polymerizable unsaturated cycloacetal) Comparative example 1 The above polymerizable unsaturated cycloacetal (hereinafter referred to as DAPE-
An anaerobic adhesive consisting of 10 parts by weight of cumene hydroperoxide porridge HR, 5% erodible solution of hydroxyethyl methacrylate of 0-benzsulfimide, and 0.02 mol of dimethyl para-toluidine, respectively. The composition was used to fix a degreased 3/8" small UNF fine screw.
固定時間は２０００で７〜８分間であった。このネジの
脱出トルク強度は３０分後に１５０ｋｇ・抑以上、２時
間後に３００ｋ９・ｃｍ以上であった。貯蔵安定性は、
空気層を半容にした２０ｃｃポリエチレン容器を用い、
室温保存で６ケ月以上、５０ｑｏで１０日以上であった
。この場合、ジメチルパラトルィジンの代りにＮ−メチ
ルアニリンを用いると固定時間は１０〜１５分遅れ、脱
出トルク強度は３び分後に０〜６０ｋ９・ｃの、２時間
後に３００ｋ９・伽であった。比較例 ２ＤＡＰＥ−Ｍ
を用いた種々の組成物について、０ーベンツスルフイミ
ド、ジメチル／ぐラトルイジン系での促進剤としての有
機メルカプト類、システインおよびシスティン塩の効果
を試験した。Fixation time was 2000 for 7-8 minutes. The escape torque strength of this screw was 150 kg·cm or more after 30 minutes, and 300 kg·cm or more after 2 hours. Storage stability is
Using a 20cc polyethylene container with half the air space,
It was stored at room temperature for more than 6 months, and stored at 50 qo for more than 10 days. In this case, when N-methylaniline was used instead of dimethylparatoluidine, the fixation time was delayed by 10 to 15 minutes, and the escape torque strength was 0 to 60 k9·c after 3 minutes and 300 k9·c after 2 hours. . Comparative example 2DAPE-M
The effects of organic mercapto compounds, cysteine and cysteine salts as accelerators in the O-benzsulfimide, dimethyl/glatluidine system were tested for various compositions using 0-benzsulfimide.
組成物の他の配合は、ＤＡＰＥ−ＭＩＯＯ重量部当り、
キュメンハィドロパーオキサィド（ＣＨＰと略記する）
４〜６重量部、ジメチルパラトルィジン（ＤＭＴと略記
する）０．０１〜０．０２モル、０ーベンツスルフイミ
ドの５％ヒドロキシエチルメタクリレート（ＯＢＳＩと
略記する）０．０１〜０．０２モル、重合防止剤として
ピロガロール１０の血である。組成物の固定時間、脱出
トルク強度および貯蔵安定曲こ関する試験結果を第１表
に示す。第１表
えゞし、貯蔵安定性は、観察にょり８０Ｃで６０分以上
おょび常温で１週間以−ヒ安定をものを○Ｅ０、他を無
印とした。Other formulations of the composition are: per part by weight of DAPE-MIOO;
Cumene hydroperoxide (abbreviated as CHP)
4 to 6 parts by weight, 0.01 to 0.02 mol of dimethyl paratoluidine (abbreviated as DMT), 0.01 to 0.02 mol of 5% hydroxyethyl methacrylate (abbreviated as OBSI) of 0-benzsulfimide Mol, pyrogallol 10 blood as a polymerization inhibitor. The test results regarding fixation time, escape torque strength and storage stability of the composition are shown in Table 1. In the first table, the storage stability was determined as ○E0 if it was stable at 80C for 60 minutes or more and at room temperature for 1 week or more, and the others were not marked.
この実験から、有機メルヵフ。ヌン化合物は促進効果は
あるが「 貯蔵安定性に欠けている。実施例 １ＤＡＰ
Ｅ−ＭＩＯの重量部当り、ピロガロール２００脚，０‐
ベンツスルフィミド（０醜１と略称する）０．０２モル
、第２級アミン０．０２モル、無水酢酸で処理したシス
ティン塩（システィン／無水酢酸／水＝２／３／７部）
を加えた組成物について、比較例２と同様の試験を行っ
た。From this experiment, organic merkaf. Although the Nun compound has a promoting effect, it lacks storage stability.Example 1DAP
Per weight part of E-MIO, 200 units of pyrogallol, 0-
0.02 mol of benzosulfimide (abbreviated as 0ugly 1), 0.02 mol of secondary amine, cysteine salt treated with acetic anhydride (cysteine/acetic anhydride/water = 2/3/7 parts)
The same test as in Comparative Example 2 was conducted on the composition containing the following.
その結果を第２表に示す。比較例 ３
実施例１の組成物の第２級アミンの代物こ第３級アミン
を同モル配合し、０−ベンツスルフィミドを配合するか
またはせずして得られる組成物について、実施例１と同
様の試験を行った。The results are shown in Table 2. Comparative Example 3 Examples were prepared for compositions obtained by blending the secondary amine substitute and tertiary amine in the composition of Example 1 in equal moles, with or without blending 0-benzsulfimide. A test similar to 1 was conducted.
その結果を第３表に示す。第２表
第３表
実施例 ２
実施例１の試料Ｎｏ．１の組成物について、その成分の
配合比を変え、実施例１と同様の試験を行った。The results are shown in Table 3. Table 2 Table 3 Example 2 Sample No. of Example 1. Regarding composition No. 1, the same test as in Example 1 was conducted by changing the blending ratio of the components.
その結果を第４表に示す。第４表The results are shown in Table 4. Table 4
Claims (1)
とヒドロキシエチルメタクリレートの付加反応により得
られる重合性不飽和シクロアセタールに、ハイドロパー
オキサイド、芳香族イミド、芳香族第２級アミンまたは
ピロリジンおよび酸で中和して得られるシステイン塩を
配合してなる嫌気性接着剤組成物。1 Polymerizable unsaturated cycloacetal obtained by addition reaction of diarylidene pentaerythrite containing a polymerization inhibitor and hydroxyethyl methacrylate is neutralized with hydroperoxide, aromatic imide, aromatic secondary amine or pyrrolidine, and acid. An anaerobic adhesive composition containing cysteine salt obtained by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8568577A JPS606381B2 (en) | 1977-07-19 | 1977-07-19 | Anaerobic adhesive composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8568577A JPS606381B2 (en) | 1977-07-19 | 1977-07-19 | Anaerobic adhesive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5421441A JPS5421441A (en) | 1979-02-17 |
| JPS606381B2 true JPS606381B2 (en) | 1985-02-18 |
Family
ID=13865691
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8568577A Expired JPS606381B2 (en) | 1977-07-19 | 1977-07-19 | Anaerobic adhesive composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS606381B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016018553A1 (en) * | 2014-07-30 | 2016-02-04 | Henkel IP & Holding GmbH | Cure accelerators for anaerobic curable compositions |
-
1977
- 1977-07-19 JP JP8568577A patent/JPS606381B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5421441A (en) | 1979-02-17 |
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