JPH0657143A - Ultraviolet-curable composition - Google Patents
Ultraviolet-curable compositionInfo
- Publication number
- JPH0657143A JPH0657143A JP25181392A JP25181392A JPH0657143A JP H0657143 A JPH0657143 A JP H0657143A JP 25181392 A JP25181392 A JP 25181392A JP 25181392 A JP25181392 A JP 25181392A JP H0657143 A JPH0657143 A JP H0657143A
- Authority
- JP
- Japan
- Prior art keywords
- ultraviolet
- composition
- curable composition
- pts
- parts
- 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.)
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Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、紫外線硬化樹脂組成物
に関し、特に液状ガスケット即ち自動車部品、電気電子
部品等の組立工程において、ＦＩＰＧ（Ｆｏｒｍｅｄ
Ｉｎ Ｐｌａｃｅ Ｇａｓｋｅｔ＝現場成形ガスケッ
ト）として用いるのに適し、紫外線を照射することによ
って速やかに増粘し、かつ作業性が良好で、特に組み付
け時の初期耐圧性の優れた紫外線硬化性組成物に関す
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an ultraviolet curable resin composition, and more particularly to a FIPG (Formed) in the process of assembling liquid gaskets, that is, automobile parts, electric / electronic parts and the like.
The present invention relates to an ultraviolet-curable composition suitable for use as an In Place Gasket (in-situ molded gasket), which rapidly increases in viscosity by irradiation with ultraviolet rays, has good workability, and is particularly excellent in initial pressure resistance during assembly.
【０００２】[0002]
【従来の技術とその課題】紫外線硬化組成物をガスケッ
ト用途に用いる際、組み付け時の初期耐圧性を得るため
に、従来、オルガノシロキサンを主成分とする一液性の
縮合硬化型組成物の湿気硬化性ＲＴＶシリコーンにおい
て、ポリシロキサンの分子量を大きくするか又は無機充
填剤の配合量を多くする方法で高粘度化させたり、嫌気
性接着剤において、紫外線を照射して部分硬化させ、そ
の後嫌気性硬化させたり（特開昭５８−１０４９７６号
公報）、あるいは紫外線硬化性樹脂をフランジの界面で
完全硬化させてガスケット層を形成させた後、もう片方
のフランジを組み付ける（特開昭６２−７７５９７号公
報）等の手段がとられていた。2. Description of the Related Art When an ultraviolet curable composition is used for a gasket, moisture of a one-component condensation curable composition containing an organosiloxane as a main component has hitherto been used in order to obtain initial pressure resistance during assembly. In the curable RTV silicone, the viscosity of the polysiloxane is increased by increasing the molecular weight of the polysiloxane or increasing the blending amount of the inorganic filler, and the anaerobic adhesive is partially cured by irradiation with ultraviolet rays and then anaerobic. It is cured (JP-A-58-104976) or an ultraviolet-curable resin is completely cured at the interface of the flange to form a gasket layer, and then the other flange is assembled (JP-A-62-77597). (Gazette) etc. were taken.
【０００３】しかし、第１の優れた初期耐圧性を得るた
めに高粘度化されたシール材料は、塗布機の吐出ポン
プ、ディスペンサーに無理がかかり精密な塗布ビートを
能率よく成形させることが困難である。However, a sealing material having a high viscosity in order to obtain the first excellent initial pressure resistance makes it difficult to efficiently form a precise coating beat because the discharge pump and dispenser of the coating machine are overloaded. is there.
【０００４】また第２の特開昭５８−１０４９７６号公
報の方法では接着剤が嫌気性接着剤であるため、厚膜硬
化しない、フランジ部からのはみ出し部分が硬化しな
い、金属以外のフランジでは硬化しにくい（プラスチッ
ク部品）等の問題がある。Further, in the method of the second Japanese Unexamined Patent Publication No. 58-104976, since the adhesive is an anaerobic adhesive, the thick film does not cure, the protruding portion from the flange does not cure, and the flange other than metal cures. It is difficult to do (plastic parts).
【０００５】また第３の特開昭６２−７７５９７号公報
のフランジ界面に前もって成形されたガスケット層は、
もう片方のフランジと接着していないので強く締めなけ
れば耐圧性が得られず、他方強くしめつけすぎるとガス
ケット層が応力で割れる場合があるという問題がある。The gasket layer formed in advance at the flange interface of the third Japanese Patent Laid-Open No. 62-77597 is
Since it is not bonded to the other flange, pressure resistance cannot be obtained unless it is strongly tightened, while there is a problem that the gasket layer may be cracked by stress if it is tightened too strongly.
【０００６】本発明の目的は上記した従来技術の問題点
を解決することにある。An object of the present invention is to solve the above-mentioned problems of the prior art.
【０００７】[0007]
【課題を解決するための手段】本発明の紫外線硬化性組
成物は（ａ）式The ultraviolet curable composition of the present invention has the formula (a).
【化２】 （式中、ＲはＨまたはＣＨ３を示し、Ｘはイソボニル、
ジシクロペンテニル、トリシクロ〔５，２，１，０
２．６〕デカニルまたは１，２，２，６，６−ペンタメ
チルピペリジニルを示す）で表される（メタ）アクリレ
ートモノマー、（ｂ）分子両末端にシラノール基を有す
るポリオルガノシロキサン、（ｃ）１分子中に加水分解
性の基を少なくとも１つ以上もつオルガノシラン及び
（ｄ）光重合触媒と縮合触媒を含有してなることを特徴
とする。[Chemical 2] (In the formula, R represents H or CH 3 , X is isobornyl,
Dicyclopentenyl, tricyclo [5,2,1,0
(2.6 ) decanyl or 1,2,2,6,6-pentamethylpiperidinyl), a (meth) acrylate monomer, (b) a polyorganosiloxane having silanol groups at both ends of the molecule, ( It is characterized by containing c) an organosilane having at least one hydrolyzable group in one molecule, and (d) a photopolymerization catalyst and a condensation catalyst.
【０００８】本発明の紫外線硬化性組成物をガスケット
用途に用いる際、フランジ部に塗布後、紫外線を照射す
ると、組成物の粘度が極度に上昇し優れた初期耐圧性が
得られる。また本発明の紫外線硬化組成物の紫外線照射
前の粘度は小さいので、塗布機の吐出圧力は小さくな
り、ポンプ、ディスペンサーに無理な圧力がかからず、
また精密なビート塗布が可能になるなどの作業性が優れ
る。さらに、紫外線照射で増粘した組成物はフランジを
組み立てた後でも、湿気で重合反応が起こり、従来のシ
リコーンゴムのガスケット材料と同様な耐熱性のゴム弾
性体の硬化物になり、過酷な条件にも使用できるガスケ
ット材料になる。When the ultraviolet curable composition of the present invention is used for a gasket, when the flange portion is coated and then irradiated with ultraviolet rays, the viscosity of the composition is extremely increased and excellent initial pressure resistance is obtained. Further, since the viscosity of the ultraviolet curable composition of the present invention before irradiation with ultraviolet rays is small, the discharge pressure of the coating machine becomes small, and an unreasonable pressure is not applied to the pump and the dispenser,
It also excels in workability such as precise beat application. Furthermore, even after assembling the flange, the composition thickened by UV irradiation undergoes a polymerization reaction due to moisture, and becomes a cured product of a heat-resistant rubber elastic body similar to the conventional silicone rubber gasket material. It becomes a gasket material that can also be used.
【０００９】本発明の組成物を構成する（ａ）成分の
（メタ）アクリレートモノマーは前記一般式で示される
少なくとも１の化合物を必須成分とするが、さらに通常
の（メタ）アクリレートモノマー例えばメチルメタクリ
レート、２−エチルヘキシルメタクリレート、テトラヒ
ドロフルフリルアクリレート、２−ヒドロキシプロピル
メタクリレート等を含んでいてもよい。（ａ）成分の添
加量は（ｂ）成分の末端シラノール基を有するポリシロ
キサン１００重量部に対して５〜１００重量部、より好
ましくは１０〜３０重量部である。The (meth) acrylate monomer of the component (a) which constitutes the composition of the present invention contains at least one compound represented by the above general formula as an essential component, and further, a usual (meth) acrylate monomer such as methyl methacrylate is used. , 2-ethylhexyl methacrylate, tetrahydrofurfuryl acrylate, 2-hydroxypropyl methacrylate, etc. may be included. The added amount of the component (a) is 5 to 100 parts by weight, and more preferably 10 to 30 parts by weight, based on 100 parts by weight of the polysiloxane having a terminal silanol group of the component (b).
【００１０】（ｂ）成分の分子の両末端にシラノール基
を有するポリシロキンの典型例は次の一般式で表され
る。A typical example of polysiroquine having a silanol group at both ends of the molecule of component (b) is represented by the following general formula.
【化３】 （式中、Ｒ１は互いに同じかまたは異なるアルキル基ま
たはアリール基であり、好ましくはメチル、置換アルキ
ル、アリル、置換アリル、アルコキシ、フェニルであ
り、またｎはこのポリシロキサンが２５℃において１０
０〜１，０００，０００ｃｐｓ、好ましくは１，０００
〜５０，０００ｃｐｓの粘度を有するような重合度にな
る整数である）[Chemical 3] (Wherein R 1 is the same or different alkyl group or aryl group, preferably methyl, substituted alkyl, allyl, substituted allyl, alkoxy, phenyl, and n is 10 at 25 ° C. of the polysiloxane.
0 to 1,000,000 cps, preferably 1,000
Is an integer that gives a degree of polymerization such that it has a viscosity of ~ 50,000 cps)
【００１１】（ｃ）成分の１分子中に加水分解性の基を
少なくとも１つ以上もつオルガノシランの典型例は、次
の一般式で表される。 Ｒ２−ＳｉＲ２ ａＹ３−ａ （式中、Ｒ２は炭素数１〜３のアルキル基であり、好ま
しくはメチル、置換アルキルであり、Ｙはアルコキシ
基、オルガノケトオキシム基、オルガノアミノ基、オル
ガノアミド基、アルケニルオキシ基などの公知の加水分
解性官能基である。）A typical example of the organosilane having at least one hydrolyzable group in one molecule of the component (c) is represented by the following general formula. R 2 -SiR in 2 a Y 3-a (wherein, R 2 is an alkyl group having 1 to 3 carbon atoms, preferably methyl, substituted alkyl, Y is an alkoxy group, organo ketoxime group, organoamino group , And known hydrolyzable functional groups such as an organoamide group and an alkenyloxy group.)
【００１２】このようなオルガノシランとしては、メチ
ルトリメトキシシラン、ビニルトリメトキシシラン、メ
チルトリエトキシシラン、ビニルトリエトキシシラン等
のアルコキシ系化合物、メチルトリプロペノキシシラ
ン、ビニルトリイソプロペノキシシランなどのエノキシ
系化合物、メチルトリス（アセトンオキシム）シラン、
メチルトリス（ブタノンオキシム）シラン等のオキシム
系化合物、メチルトリス（ジメチルアミノ）シラン、メ
チルトリス（Ｎ−メチルアセトアミド）シラン、ビニル
トリス（Ｎ−メチルアセトアミド）シラン等のアミド系
化合物、メチルトリス（ジメチルアミノキシ）シラン、
メチルトリス（ジエチルアミノキシ）シラン等のアミノ
キシ系化合物、メチルトリビニロキシシラン、メチルト
リス（イソプロペニルオキシ）シラン等のビニロキシ系
化合物などの公知のオルガノシランがあり、本発明では
その種類は特に限定されない。Examples of such organosilanes include alkoxy compounds such as methyltrimethoxysilane, vinyltrimethoxysilane, methyltriethoxysilane and vinyltriethoxysilane, methyltripropenoxysilane and vinyltriisopropenoxysilane. Enoxy compounds, methyltris (acetone oxime) silane,
Oxime compounds such as methyltris (butanone oxime) silane, amide compounds such as methyltris (dimethylamino) silane, methyltris (N-methylacetamido) silane, vinyltris (N-methylacetamido) silane, methyltris (dimethylaminoxy) silane,
There are known organosilanes such as aminoxy compounds such as methyltris (diethylaminoxy) silane, methyltrivinyloxysilane, vinyloxy compounds such as methyltris (isopropenyloxy) silane, and the type thereof is not particularly limited in the present invention.
【００１３】（ｂ）のシラノール末端ポリシロキサンと
（ｃ）のオルガノシランを湿気で縮合重合させる触媒
は、有機カルボン酸の金属塩、有機チタン酸エステル、
有機チタン化合物、アルコキシアルミ化合物、アミノア
ルキル基置換アルコキシシラン、アミン化合物もしくは
その塩、アルカリ金属の低級脂肪酸塩、ジアルキルヒド
ロキシルアミン、グアニジン化合物もしくはグアニジル
基含有シランもしくはシロキサン等の公知の触媒であ
り、本発明ではその種類は特に限定されない。（ｃ）成
分の添加量はシラノール末端ポリシロキサン１００重量
部に対して０．０１〜５重量部、好ましくは０．１〜３
重量部である。The catalyst for condensation-polymerizing the silanol-terminated polysiloxane (b) and the organosilane (c) with moisture is a metal salt of an organic carboxylic acid, an organic titanate ester,
Known catalysts such as organotitanium compounds, alkoxyaluminum compounds, aminoalkyl group-substituted alkoxysilanes, amine compounds or salts thereof, lower fatty acid salts of alkali metals, dialkylhydroxylamine, guanidine compounds or guanidyl group-containing silanes or siloxanes. In the invention, the type is not particularly limited. The amount of the component (c) added is 0.01 to 5 parts by weight, preferably 0.1 to 3 parts by weight, based on 100 parts by weight of the silanol-terminated polysiloxane.
Parts by weight.
【００１４】重合触媒としては紫外線照射によりラジカ
ルを生成する公知の光増感剤、例えばアセトフェノン、
ベンゾフェノン、４−ヒドロキシジフェニル、４−ニト
ロアニリン等が適宜用いられる。重合触媒の添加量は紫
外線照射で重合する（メタ）アクリレート１００重量部
に対して０．１〜５重量部である。As the polymerization catalyst, known photosensitizers which generate radicals upon irradiation with ultraviolet rays, such as acetophenone,
Benzophenone, 4-hydroxydiphenyl, 4-nitroaniline and the like are used as appropriate. The addition amount of the polymerization catalyst is 0.1 to 5 parts by weight with respect to 100 parts by weight of the (meth) acrylate polymerized by irradiation with ultraviolet rays.
【００１５】本発明において、紫外線で硬化する（ａ）
の（メタ）アクリレートは全組成中通常５〜３０％用い
られる。５％以下では紫外線を照射しても系の粘度があ
まり上昇せず初期耐圧性が得られない。３０％以上で
は、紫外線を照射したとき、粘度上昇が大きく、時には
表面層が固くなりすぎ、フランジを組み付けるときに表
面被膜が破れたり、片方のフランジの界面と接着せず耐
圧性が低下する。In the present invention, it is cured by ultraviolet rays (a).
The (meth) acrylate is usually used in an amount of 5 to 30% in the entire composition. If it is 5% or less, the viscosity of the system does not increase so much even if it is irradiated with ultraviolet rays, and the initial pressure resistance cannot be obtained. If it is 30% or more, the viscosity increases largely when irradiated with ultraviolet rays, sometimes the surface layer becomes too hard, the surface coating is broken when the flange is assembled, and the pressure resistance is lowered because the surface coating does not adhere to the interface of one flange.
【００１６】本発明においては、便宜、公知の充填剤例
えば煙霧質シリカ、疎水性シリカ、炭酸カルシウム等を
所定量配合してもよい。In the present invention, known fillers such as fumed silica, hydrophobic silica, calcium carbonate and the like may be added in a predetermined amount for convenience.
【００１７】[0017]
【発明の効果】本発明の紫外線硬化性組成物は、液状ガ
スケット組成物として次のような効果を示す。 塗布時は低粘度であるため塗布機のポンプ圧が小さく
ても塗布が可能である。 紫外線照射で当該組成物を増粘させると初期耐圧性が
得られる。よって、もう片方のフランジを組み付けてす
ぐに耐圧性試験を行うことができる。 フランジを組み付けるとき、当該組成物は増粘してい
るが未硬化なので、一対のフランジの界面に接着して硬
化するので、優れた耐圧性が得られる。 当該組成物はフランジ界面間で湿気硬化するので、ガ
スケット層が厚い場合やフランジ部のはみ出し部や、プ
ラスチックや塗装されたフランジ間でも、完全硬化する
ことができる。The ultraviolet-curable composition of the present invention exhibits the following effects as a liquid gasket composition. Since the viscosity is low at the time of coating, the coating can be performed even if the pump pressure of the coating machine is small. When the composition is thickened by UV irradiation, initial pressure resistance is obtained. Therefore, the pressure resistance test can be performed immediately after the other flange is assembled. When the flange is assembled, the composition is thickened but uncured, so that it adheres to the interface of the pair of flanges and hardens, so that excellent pressure resistance is obtained. Since the composition is moisture-cured between the flange interfaces, it can be completely cured even when the gasket layer is thick, the protruding portion of the flange portion, or between the plastic and the coated flange.
【００１８】[0018]
【実施例】表１に示す処方で組成物を調製し、紫外線照
射後の初期耐水圧と湿気硬化後の耐水圧を評価した。結
果を表１に示す。尚、部数は重量部で示す。Example A composition was prepared according to the formulation shown in Table 1, and the initial water pressure resistance after ultraviolet irradiation and the water pressure resistance after moisture curing were evaluated. The results are shown in Table 1. The number of parts is shown by weight.
【表１】 [Table 1]
【００１９】次にポリアセタール樹脂板及び鋼板による
膜厚硬化性を実施例１のイソボロニルアクリレート含有
ポリシロキサン組成物と市販の紫外線硬化性嫌気性ガス
ケット組成物について評価した。結果を表２に示す。Next, the film-hardening properties of the polyacetal resin plate and the steel plate were evaluated for the isobornyl acrylate-containing polysiloxane composition of Example 1 and the commercially available UV-curable anaerobic gasket composition. The results are shown in Table 2.
【表２】 [Table 2]
Claims (2)
ジシクロペンテニル、トリシクロ〔５，２，１，０
２．６〕デカニルまたは１，２，２，６，６−ペンタメ
チルピペリジニルを示す）で表される（メタ）アクリレ
ートモノマー、（ｂ）分子両末端にシラノール基を有す
るポリオルガノシロキサン、（ｃ）１分子中に加水分解
性の基を少なくとも１つ以上もつオルガノシラン及び
（ｄ）光重合触媒と縮合触媒を含有してなることを特徴
とする紫外線硬化性組成物。1. A formula (a): (In the formula, R represents H or CH 3 , X is isobornyl,
Dicyclopentenyl, tricyclo [5,2,1,0
(2.6 ) decanyl or 1,2,2,6,6-pentamethylpiperidinyl), a (meth) acrylate monomer, (b) a polyorganosiloxane having silanol groups at both ends of the molecule, ( (c) An ultraviolet-curable composition comprising an organosilane having at least one hydrolyzable group in one molecule and (d) a photopolymerization catalyst and a condensation catalyst.
成分を５〜１００重量部含有してなることを特徴とする
請求項１記載の紫外線硬化性組成物。2. The amount of component (a) relative to 100 parts by weight of component (b).
The ultraviolet curable composition according to claim 1, which comprises 5 to 100 parts by weight of the components.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25181392A JPH0657143A (en) | 1992-08-07 | 1992-08-07 | Ultraviolet-curable composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25181392A JPH0657143A (en) | 1992-08-07 | 1992-08-07 | Ultraviolet-curable composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0657143A true JPH0657143A (en) | 1994-03-01 |
Family
ID=17228305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25181392A Pending JPH0657143A (en) | 1992-08-07 | 1992-08-07 | Ultraviolet-curable composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0657143A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4903502A (en) * | 1988-08-26 | 1990-02-27 | Thermo King Corporation | Rate of change temperature control for transport refrigeration systems |
| EP0776943A1 (en) | 1995-11-30 | 1997-06-04 | Dow Corning Toray Silicone Company, Limited | Curing catalyst for organopolysiloxane compositions and curable organopolysiloxane compositions |
| EP0781813A2 (en) | 1995-12-28 | 1997-07-02 | Dow Corning Toray Silicone Company Ltd. | Curable organopolysiloxane composition and method for bonding objects using said composition |
| EP0781814A2 (en) | 1995-12-28 | 1997-07-02 | Dow Corning Toray Silicone Co., Ltd. | Curable organopolysiloxane composition and method for bonding objects using said composition |
| US5753720A (en) * | 1996-01-31 | 1998-05-19 | Dow Corning Toray Silicone Co., Ltd. | Hardenable organopolysiloxane compositions |
| JP2008057849A (en) * | 2006-08-31 | 2008-03-13 | Denso Corp | Manufacturing method of heat exchanger |
| JP2008057850A (en) * | 2006-08-31 | 2008-03-13 | Denso Corp | Manufacturing method of heat exchanger, and heat exchanger |
-
1992
- 1992-08-07 JP JP25181392A patent/JPH0657143A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4903502A (en) * | 1988-08-26 | 1990-02-27 | Thermo King Corporation | Rate of change temperature control for transport refrigeration systems |
| EP0776943A1 (en) | 1995-11-30 | 1997-06-04 | Dow Corning Toray Silicone Company, Limited | Curing catalyst for organopolysiloxane compositions and curable organopolysiloxane compositions |
| EP0781813A2 (en) | 1995-12-28 | 1997-07-02 | Dow Corning Toray Silicone Company Ltd. | Curable organopolysiloxane composition and method for bonding objects using said composition |
| EP0781814A2 (en) | 1995-12-28 | 1997-07-02 | Dow Corning Toray Silicone Co., Ltd. | Curable organopolysiloxane composition and method for bonding objects using said composition |
| US5684113A (en) * | 1995-12-28 | 1997-11-04 | Dow Corning Toray Silicone Co., Ltd. | Curable organopolysiloxane composition and method for adhering a substrate to an adherend using the composition |
| US5753720A (en) * | 1996-01-31 | 1998-05-19 | Dow Corning Toray Silicone Co., Ltd. | Hardenable organopolysiloxane compositions |
| JP2008057849A (en) * | 2006-08-31 | 2008-03-13 | Denso Corp | Manufacturing method of heat exchanger |
| JP2008057850A (en) * | 2006-08-31 | 2008-03-13 | Denso Corp | Manufacturing method of heat exchanger, and heat exchanger |
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