JPS61166814A - Production of unsaturated acryl urethane resin compound - Google Patents
Production of unsaturated acryl urethane resin compoundInfo
- Publication number
- JPS61166814A JPS61166814A JP27247785A JP27247785A JPS61166814A JP S61166814 A JPS61166814 A JP S61166814A JP 27247785 A JP27247785 A JP 27247785A JP 27247785 A JP27247785 A JP 27247785A JP S61166814 A JPS61166814 A JP S61166814A
- Authority
- JP
- Japan
- Prior art keywords
- inorganic material
- polymerizable monomer
- coupling agent
- silane coupling
- urethane 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
Landscapes
- Macromonomer-Based Addition Polymer (AREA)
- Reinforced Plastic Materials (AREA)
- Paints Or Removers (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、耐水性、耐蝕性に優れ、特に塗料およびライ
ニングに適する不飽和アクリルウレタン樹脂コン・ぐラ
ンドの製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a method for producing an unsaturated acrylic urethane resin compound that has excellent water resistance and corrosion resistance and is particularly suitable for paints and linings.
従来、塗膜の耐水性、耐蝕性を改良するために、不飽和
ポリエステル等の硬化性樹脂にガ゛ラス繊維あるいはフ
レーク状の無機質材料を添加したライニング用樹脂組成
物については知られている・かかる場合にライニング層
の特性は、樹脂とガラス繊維あるいはフレーク状の無機
質材料との結合状態によって左右される。すなわち、結
合力強化がライニング層の特性を改善することは云うま
でもない。Hitherto, lining resin compositions have been known in which glass fibers or flake-like inorganic materials are added to curable resins such as unsaturated polyester in order to improve the water resistance and corrosion resistance of coating films. In such a case, the properties of the lining layer depend on the bonding state between the resin and the glass fiber or flake-like inorganic material. That is, it goes without saying that strengthening the bonding strength improves the properties of the lining layer.
樹脂とガラス繊維あるいはフレーク状の無機質材料との
結合力を強化するために、樹脂と無機質材料を混合する
際に単にシランカップリング剤を同時に混合する方法（
°゛インテグラル法と云われる）が知られている。しか
し、その効果は常に安定して発揮されるまでに至ってい
ない。In order to strengthen the bond between the resin and the glass fiber or flake-like inorganic material, there is a method of simply mixing a silane coupling agent at the same time when mixing the resin and the inorganic material (
The ``integral method'' is known. However, the effect has not always been consistently demonstrated.
また、樹脂に添加する鱗片状の無機質材料を、予めシラ
ンカップリング剤の水またはアルコール希釈液で濡らし
て処理する方法についてもよく知られている。しかし、
この場合には乾燥工程において鱗片状無機質材料が凝集
するか、材料内に希釈液が残留して塗膜またはライニン
グ層の特性に悪影響を与え、また必要以上の乾燥はシラ
ンカップリング剤の飛散ロスを伴い実用的でない。Furthermore, a method is well known in which a scale-like inorganic material to be added to a resin is pre-wetted with a water or alcohol diluted solution of a silane coupling agent. but,
In this case, the scale-like inorganic material may aggregate during the drying process, or the diluted liquid may remain within the material, adversely affecting the properties of the coating film or lining layer, and excessive drying may result in loss of silane coupling agent scattering. This is not practical.
本発明者らは、前記情勢に鑑み、優れた性能を有する防
蝕性樹脂塗料およびライニングヲ得るべく鋭意検討を重
ねだ結果、特定方法で処理したフレーク状の無機質材料
を、不飽和アクリルウレタン樹脂に添加混合して樹脂コ
ン・ぞランドを製造することによって、耐水性および耐
蝕性に優れた塗料およびライニングが得られることを見
出し、本発明に到達した。In view of the above situation, the inventors of the present invention have made extensive studies to obtain a corrosion-resistant resin paint and lining with excellent performance. As a result, the inventors have developed an unsaturated acrylic urethane resin using a flake-like inorganic material treated using a specific method. The inventors have discovered that a coating material and lining with excellent water resistance and corrosion resistance can be obtained by producing a resin compound by adding and mixing them, and have arrived at the present invention.
本発明方法は、重合性単量体にシラノカップリング剤を
溶解または乳化分散させた１３０℃以下の溶液に浸漬し
て得られる、単量体が完全に乾燥飛散しない未だ湿潤状
態にある鱗片状の無機質材料を不飽和アクリルウレタン
と重合性単量体よりなる樹脂液に混合することを特徴と
する不飽和アクリルウレタン樹脂コン・２ウンドの製造
方法である。The method of the present invention is a scaly product obtained by immersing a polymerizable monomer in a solution at 130°C or lower in which a silano coupling agent is dissolved or emulsified and dispersed. This is a method for producing an unsaturated acrylic urethane resin compound, which is characterized by mixing an inorganic material of 2 to a resin liquid consisting of unsaturated acrylic urethane and a polymerizable monomer.
本発明方法においては、重合性単量体が完全に乾燥飛散
しない状態即ち湿潤状態にある鱗片状の無機質材料が樹
脂液と混合されるので、樹脂中での無機質材料の凝集が
防止され、まだ無機質材料中に吸着残留している０、１
％以下の微量の水分がカップリング反応を促進するもの
と考えられる。In the method of the present invention, the scale-like inorganic material in which the polymerizable monomer is not completely dried and scattered, that is, in a wet state, is mixed with the resin liquid, so that agglomeration of the inorganic material in the resin is prevented, and the inorganic material is still wet. 0, 1 adsorbed and remaining in inorganic materials
It is thought that a trace amount of water of less than 1% promotes the coupling reaction.
本発明に用いられるシラ／カップリング剤を溶解または
乳化分散させる重合性単量体と不飽和アクリルウレタン
を溶解するために用いられる重合性単量体とは同一物で
あることが望ましいが、別の重合性単量体を希釈剤とし
て併用することもできる。かかる単量体の例としては、
スチレ／が一般的テアルカ、クロルスチレン、ビニルト
ルエン、トリエチレングリコールジメタクリレートなど
も有用である。It is desirable that the polymerizable monomer for dissolving or emulsifying and dispersing the silica/coupling agent used in the present invention and the polymerizable monomer used for dissolving the unsaturated acrylic urethane are the same, but they are different. Polymerizable monomers can also be used together as a diluent. Examples of such monomers include:
Also useful are styrene, chlorostyrene, vinyltoluene, triethylene glycol dimethacrylate, and the like.
本発明に用いられるシラ／カップリング剤は。The silica/coupling agent used in the present invention is:
ビニルトリエトキシシラ／、ビニルトリス（β−メトキ
シエトキシ）シラン、ｒ−グリシドキシプ・ロピルトリ
メトキシシラン、γ−メタアグリロキシグロピルトリメ
トキシシラン、Ｎ−β（アミノエチル）γ−アミノプロ
ピルトリメトキシシランなどであり、処理する無機質材
料に応じて選択される。Vinyltriethoxysilane/, Vinyltris(β-methoxyethoxy)silane, r-glycidoxypropyltrimethoxysilane, γ-metaagryloxyglopyltrimethoxysilane, N-β(aminoethyl)γ-aminopropyltrimethoxysilane etc., and is selected depending on the inorganic material to be treated.
本発明に用いられる鱗片状の無機質材料は、無機質材料
としてガラスフレーク、雲母、タルク、グラファイト、
人工雲母、アルミナなどが挙げられ、また鱗片状として
はその径が３闇φ以下好適には１〜３ ｍｍφ、厚さが
１〜１０μ範囲のものが好ましい。The scaly inorganic material used in the present invention includes glass flakes, mica, talc, graphite,
Artificial mica, alumina, etc. may be mentioned, and the scale-like material preferably has a diameter of 3 mm or less, preferably 1 to 3 mm, and a thickness of 1 to 10 microns.
鱗片状の無機質材料を処理する際の重合性単量体とシラ
ンカップリング剤の量は、無機質材料の種類、大きさな
どにより異なるが、重合性単量体は無機質材料を浸漬す
るに足る量以上あればよく、またシラ／カップリング剤
は無機質材料の１００重量部当り０．５〜５重量部の範
囲で有効である。The amount of polymerizable monomer and silane coupling agent when treating scale-like inorganic material varies depending on the type and size of the inorganic material, but the amount of polymerizable monomer is sufficient to soak the inorganic material. The above amount is sufficient, and the sila/coupling agent is effective in a range of 0.5 to 5 parts by weight per 100 parts by weight of the inorganic material.
処理温度は１３０℃以下好適には６０〜１３０℃の範囲
が好ましく、６０℃以下では処理に長時間を要し、また
１３０℃以上では単量体とシランカップリング剤との反
応によるｒル化、シラ／カップリング剤の分解などを伴
い好ましくない。処理時間は室温の場合−週間、６０〜
１３０℃の場合５〜６０分間程度が必要である。The treatment temperature is preferably 130°C or lower, preferably in the range of 60 to 130°C. At 60°C or lower, the treatment takes a long time, and at 130°C or higher, the reaction between the monomer and the silane coupling agent may cause the reaction. , decomposition of the silica/coupling agent, etc., which is undesirable. Processing time at room temperature - weeks, 60~
In the case of 130°C, approximately 5 to 60 minutes are required.
本発明に用いられる不飽和アクリルウレタンは、ジヒド
ロキシ化合物全含むか、含まずにポリイソシャネート化
合物と末端ヒドロキシを有するアクリル又はメタクリレ
ート（例えばβヒドロキシエチル（ｆロピル）メタクリ
レート）と反応して製造され、又ジヒドロキシ、ポリヒ
ドロキシ化合物例えばヒドロキシ末端ポリブタノエ／や
ヒドロキシ基含有ビニル共重合体とインシャネートエチ
ルメタクリレートとの反応によっても製造出来る。The unsaturated acrylic urethane used in the present invention is prepared by reacting a polyisocyanate compound with an acrylic or methacrylate having a terminal hydroxyl (for example, β-hydroxyethyl (f-ropyl) methacrylate) with or without dihydroxy compounds. It can also be produced by reacting a dihydroxy or polyhydroxy compound such as hydroxy-terminated polybutanoe/or a hydroxy group-containing vinyl copolymer with insyanate ethyl methacrylate.
不飽和アクリルウレタンは重合性単量体に溶解して用い
られるが、この際に先にカップリング剤で処理された鱗
片状の無機質材料が添加される。重合性単量体を含む不
飽和アクリルウレタン樹脂と無機質材料の重電比は、８
０：２０〜５０：５０．好ましくは７５：２５〜６０：
４０の範囲で有効である。Unsaturated acrylic urethane is used after being dissolved in a polymerizable monomer, and at this time, a scale-like inorganic material that has been previously treated with a coupling agent is added. The heavy electric ratio of the unsaturated acrylic urethane resin containing the polymerizable monomer and the inorganic material is 8.
0:20~50:50. Preferably 75:25-60:
Valid in the range of 40.
不飽和アクリルウレタン樹脂に用いられる重合触媒は、
有機過酸化物たとえば過酸化ベンゾイル、メチルエチル
ケトン／Ｆ−オキサイド、キュメンハイドロＡ’−オキ
サイドなどであり、目的に応じて選択することができる
。The polymerization catalyst used for unsaturated acrylic urethane resin is
Organic peroxides include benzoyl peroxide, methyl ethyl ketone/F-oxide, cumene hydro A'-oxide, etc., and can be selected depending on the purpose.
その他の配合剤としては、商品価値を高めるために遥変
剤たとえば微粉シリカ、石綿粉末、有機アミンヲ配合し
た粘土質（ベーカ社製′”ベントンｎ）、脱水ヒマシ油
、ノルビトールとベンズアルデヒドの縮合アセタール化
合物、金属キレートや金属せっけんなど、まだ顔料たと
えばチタン白、補強材としてガラス繊維、合成繊維、硬
化促進剤たとえば金属石けん、ジメチルアニリン、アセ
チルアセトンなど、空気乾燥剤として・ぐラフイン、エ
チルセルロースなどを少量添加することができる。Other compounding agents to increase commercial value include fine powdered silica, asbestos powder, clay mixed with organic amines (Bentone N manufactured by Baker), dehydrated castor oil, and a condensed acetal compound of norbitol and benzaldehyde. Add a small amount of pigment such as titanium white, glass fiber, synthetic fiber as a reinforcing material, hardening accelerator such as metal soap, dimethylaniline, acetylacetone, etc., as an air drying agent, graphine, ethyl cellulose, etc. as an air drying agent. be able to.
次に本発明の理解を助けるために以下に実施例金示す。 Next, examples are shown below to help understand the present invention.
実施例１
温度計、滴下ロート、還流装置、攪拌機を具備シタガラ
スフラスコに、スチレンモノマー２２３Ｉ、ビス（βヒ
ドロキシエチルビル）テレフタレート２８２ｇ、重合禁
止剤としてトルノ・イドロキノン０．３６．９ （ｉｌ
−仕込み、６０℃に昇温する。この中に２，４）リレン
ジイノンャネート３４８．１ ｆ、乾燥空気全通しなが
ら滴下金続け、スチレンモノマー可溶性のインシャネー
トプレポリマーを約９０分かけて合成した。引続きこの
プレポリマーに２−ヒドロキシエチルメタクリレート２
６２ｇを滴下し、上記プレポリマー中のイノシャネート
が完全に消失するまで約２時間１０分反応して不飽和ア
クリルウレタン樹脂を合成した。Example 1 In a glass flask equipped with a thermometer, a dropping funnel, a reflux device, and a stirrer, 223 I of styrene monomer, 282 g of bis(β-hydroxyethylvyl) terephthalate, and 0.36.9 (il) of tornohydroquinone as a polymerization inhibitor were added.
- Charge and raise the temperature to 60°C. Into this, 348.1 f of 2,4) lylene diynonyanate was added dropwise while completely passing dry air, and a styrene monomer-soluble insyanate prepolymer was synthesized over about 90 minutes. Subsequently, 2-hydroxyethyl methacrylate 2 was added to this prepolymer.
62 g of the prepolymer was added dropwise, and the reaction was continued for about 2 hours and 10 minutes until the inocyanate in the prepolymer completely disappeared, thereby synthesizing an unsaturated acrylic urethane resin.
別に、日本板ガラス■製のガラスフレーク商品名ゞ”マ
イクロガラスフレークＣＣＦ −１５０”の６９５ｇを
、信越シリコン■のメタクリルシランカップリング剤で
ある（ｒ−メタクリロキシプロピルトリメトキシシラン
）”５０３”の１７．８５＋全とかしたスチレンモノマ
ーｉ１１！６９５ ｇＫ浸Ｌ、２５〜３０℃で７日間処
理した。この処理したスラリーを、上記樹脂に混ぜディ
ス／ぐ−にて５分間攪拌して一様に分散させた。このコ
ンノにンドｔ（Ａ）とする。 （実施例２
温度計、滴下ロート、還流装置、攪拌機を具備シたガラ
スフラスコにスチレンモノマー２００１．２−ヒドロキ
シエチルメタクリレート３９３ｇ、重合禁止剤としてハ
イドロキノン０．１６．９’に仕込み、４０℃に昇温す
る。この中にポリメチレンポリフェニルインシャネート
である日本ポリウレタン工業（掬商品名゛′ミリオネー
トＭＲ”（インシャネート含有率３１チ）の４０５ｇ’
を約２時間かけて滴下した。このままでは全インシャネ
ートの約２／３程度の反応にとどまる為、引続き３０分
かけて８０℃まで昇温し、引続き２時間３０分反応して
耐熱タイプの不飽和アクリルウレタン樹脂を合成した。Separately, 695 g of glass flakes manufactured by Nippon Sheet Glass ■ under the trade name "Micro Glass Flake CCF-150" were added to 17 g of methacrylic silane coupling agent (r-methacryloxypropyltrimethoxysilane) "503" manufactured by Shin-Etsu Silicon ■. .85 + Totally melted styrene monomer i11!695 gK Soaked L, treated for 7 days at 25-30°C. This treated slurry was mixed with the resin and stirred for 5 minutes using a disc/gun to uniformly disperse it. Let this node be t(A). (Example 2 A glass flask equipped with a thermometer, a dropping funnel, a reflux device, and a stirrer was charged with 393 g of styrene monomer 2001.2-hydroxyethyl methacrylate and 0.16.9' hydroquinone as a polymerization inhibitor, and the temperature was raised to 40°C. Into this, add 405 g of polymethylene polyphenyl insyanate (trade name: ``Millionate MR'' (Insyanate content: 31) from Nippon Polyurethane Industries).
was added dropwise over about 2 hours. At this rate, only about 2/3 of the total insyanate reacted, so the temperature was raised to 80° C. over 30 minutes, and the reaction continued for 2 hours and 30 minutes to synthesize a heat-resistant unsaturated acrylic urethane resin.
別に日本板ガラス■製のガラスフレーク商品名゛°マイ
クロガラスフレークＣＣＦ −０４８” ８６０ ＆を
、信越シリコン■のメタクリルシランカップリング剤（
γメタクリルキシプロピルトリメトキシシランである４
ｔ５０３） １６ Ｆ ｅ溶かしスチレンモノマー液６
１６ｇに浸し４０℃で３時間処理した。Separately, glass flakes manufactured by Nippon Sheet Glass ■ (product name: Micro Glass Flake CCF-048'' 860 &
4 which is γmethacryloxypropyltrimethoxysilane
t503) 16 Fe Dissolved styrene monomer liquid 6
It was immersed in 16g of water and treated at 40°C for 3 hours.
この処理しだガ゛ラスフレークスラリーに、上記樹脂に
混ぜ、マーラーで２０分すり合せ一様に分散させた。こ
のコン・ぞンドｔ（Ｂ）とする。This treated glass flake slurry was mixed with the above resin and rubbed with a mala for 20 minutes to uniformly disperse it. Let this be t(B).
実施例３
温度計、滴下ロート、還流装置、攪拌機を具備シたガラ
スフラスコに、スチレンモノマー２６５Ｆ、２．２ビス
（Ｐ−ヒドロキシフェニル）ｆ口・マンとプロピレンオ
キサイドの１：２反応物である日本油脂（（１製、商品
名［ユニオールＤＢ−３５０４３５０ｇ、重合禁止剤と
してハイドロキノン３０Ｉ、ウレタン化触媒としてオク
タン酸第−錫２．１９に仕込み、７０℃に加熱昇温する
。この中に乾燥空気を送りながらイノホロンジイノシャ
ネートの４４２ 、！７ｔ２時間かけて滴下し、その後
オクテン酸第−錫の１．０グをとかした２−ヒドロキシ
エチルメタクリレートの２６２ｇｋ８５〜９０℃に保っ
て１時間３０分滴下し、滴下後更ＶＣ１時間反応して不
飽和アクリルウレタン樹脂を得た。Example 3 A 1:2 reaction product of styrene monomer 265F, 2.2bis(P-hydroxyphenyl)fman and propylene oxide was placed in a glass flask equipped with a thermometer, dropping funnel, reflux device, and stirrer. Nihon Yushi (manufactured by 1, trade name: Uniol DB-3504, 350 g, hydroquinone 30I as a polymerization inhibitor, and 2.19 g of stannous octoate as a urethanization catalyst, and heated to 70°C. Dry air is added to the mixture. 442,!7t of inophorone diinocyanate was added dropwise over a period of 2 hours, and then 262g of 2-hydroxyethyl methacrylate, which had been dissolved with 1.0g of stannous octoate, was kept at 85 to 90°C for 1 hour and 30 minutes. After the dropwise addition, the mixture was further reacted for 1 hour under VC to obtain an unsaturated acrylic urethane resin.
別に日本板ガラス■製のガラスフレーク商品名°９マイ
クロがラスフレークＣＣＦ−１５０” ７００ ！！を
、信越シリコン−メタクリルシランカップリング剤（γ
メタクリロキシプロピルトリメトキシシラン）の２５！
！を溶かしたスチレンモノマー／ｆＬ８１５Ｉに浸し、
７０℃で１時間処理した。この処理したガラスフレーク
スラリーを上記樹脂液に混ぜてディス・ξ−にて７分攪
拌し、一様に分散させてこのコンバンドｆｔ（Ｃ）とす
る。Separately, glass flakes manufactured by Nippon Sheet Glass ■ (trade name: °9 Micro) were mixed with Shin-Etsu silicone-methacrylic silane coupling agent (γ
25 of methacryloxypropyltrimethoxysilane)!
! Soaked in dissolved styrene monomer/fL815I,
It was treated at 70°C for 1 hour. This treated glass flake slurry is mixed with the above resin liquid and stirred for 7 minutes using a dispersion device ξ- to uniformly disperse the mixture to obtain a combined ft (C).
比較例１
実施例１、実施例２、実施例３で得られた不飽和アクリ
ルウレタン樹脂に、それぞれスチレンモノマー６７７９
．６００ｇ、７９０ Ｆ？：、加えて希釈し、その中に
シランカップリング剤の゛”５０３”ｉそれぞれ１７．
８ｇ、１６．９．２５．！９を溶かした所謂るインテグ
ラルブレンドとした。その中にそれぞれの実施例に対応
するガラスフレーク１６９４Ｍ。Comparative Example 1 Styrene monomer 6779 was added to the unsaturated acrylic urethane resins obtained in Example 1, Example 2, and Example 3, respectively.
．． 600g, 790F? : Add and dilute 17.
8g, 16.9.25. ! 9 was dissolved to form a so-called integral blend. Glass flakes 1694M corresponding to each example therein.
８６０．９．７００Ｆ加えて同様の処理をして比較材料
とした。それぞれをコア・やンドＡ、Ｂ、Ｃに対してＡ
’ 、 Ｂ’ 、 Ｃ’とした。860.9.700F was added and treated in the same manner as a comparative material. A for each core and end A, B, and C
', B', and C'.
以上の実施例１〜３、比較例１のコアバンドＡ。Core band A of Examples 1 to 3 and Comparative Example 1 above.
Ｂ 、 Ｃ、Ａ’ 、 Ｂ’ 、 Ｃ’に化薬ヌーリー
社製のビニルエステル用専用触媒３２８をコン・ぐノド
１００重量部当り１．２部、ナフテン酸コバルト（コバ
ルト全質６条含有）をコン・ぞノド１Ｏ０，！量部当り
０．５部を配合して、厚み２〜２．５ ｗＲの板状成形
品全作り、常温でダル死後１夜放置し８０℃で６０分間
後硬化させテストピースを作った。このテストピースよ
り７ ｃｍ Ｘ ７ ｃｍのクーポンを作り８０℃にて
煮沸し、その吸水率を調べた結果を以下に示す。For B, C, A', B', and C', 1.2 parts of vinyl ester special catalyst 328 manufactured by Kayaku Nury Co., Ltd. per 100 parts by weight of Con-Gunodo, cobalt naphthenate (contains 6 strips of cobalt) Con Zonodo 100,! A total of 0.5 parts per volume was blended to make a plate-shaped molded product with a thickness of 2 to 2.5 wR, left overnight after the dal death at room temperature, and post-cured at 80° C. for 60 minutes to make a test piece. A 7 cm x 7 cm coupon was made from this test piece and boiled at 80°C, and its water absorption rate was investigated. The results are shown below.
吸水率
Ａ ：ｌ ンｚｆ ７ド１５日後 ８１ｎｑ／ｃｍ”
Ａ’ ｔｔ １５日後 ３４ ｒｎ９７ｃ
ｍ２Ｂ 〃 ５０日後 ８．５＃＋４７７ｚ
２Ｂ′ 〃 ５０日後 ３８ｍ９／ｃｍ２ＣＩ
３０日後 ７ｍ９／ｃｍ２Ｃ′ 〃
３０日後 ４４ｍ９／ｃｍ２〔発明の効果〕
本発明方法で得られる不飽和アクリルウレタン樹脂コン
・ぐランドは、耐水性および耐蝕性にすぐれた塗料およ
びライニングとして有用である。Water absorption rate A: 81 nq/cm after 7 days and 15 days
A' tt 15 days later 34 rn97c
m2B 〃 50 days later 8.5#+477z
2B' 〃 50 days later 38m9/cm2CI
After 30 days 7m9/cm2C'
After 30 days: 44 m9/cm2 [Effects of the Invention] The unsaturated acrylic urethane resin compound obtained by the method of the present invention is useful as a paint and lining with excellent water resistance and corrosion resistance.
Claims (1)
分散させた溶液に浸漬して得られる、未だ湿潤状態にあ
る鱗片状の無機質材料を、不飽和アクリルウレタンと重
合性単量体よりなる樹脂液に添加混合することを特徴と
する不飽和アクリルウレタン樹脂コンパウンドの製造方
法。A scale-like inorganic material, which is still in a wet state, obtained by immersing it in a solution in which a silane coupling agent is dissolved or emulsified in a polymerizable monomer, is then processed into a resin made of unsaturated acrylic urethane and a polymerizable monomer. A method for producing an unsaturated acrylic urethane resin compound, which comprises adding and mixing it to a liquid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27247785A JPS61166814A (en) | 1985-12-05 | 1985-12-05 | Production of unsaturated acryl urethane resin compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27247785A JPS61166814A (en) | 1985-12-05 | 1985-12-05 | Production of unsaturated acryl urethane resin compound |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10948376A Division JPS5335782A (en) | 1976-09-14 | 1976-09-14 | Preparation of resin compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61166814A true JPS61166814A (en) | 1986-07-28 |
| JPS6146502B2 JPS6146502B2 (en) | 1986-10-14 |
Family
ID=17514468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27247785A Granted JPS61166814A (en) | 1985-12-05 | 1985-12-05 | Production of unsaturated acryl urethane resin compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61166814A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0416369A2 (en) * | 1989-09-05 | 1991-03-13 | MERCK PATENT GmbH | Polymer coated plate-like substrate |
| JP2006307028A (en) * | 2005-04-28 | 2006-11-09 | Jsr Corp | Urethane (meth)acrylate, radiation-curable composition and its cured film |
| CN108559391A (en) * | 2018-04-20 | 2018-09-21 | 上海振华重工（集团）常州油漆有限公司 | A kind of polyaspartic ester finishing coat and its preparation method and application |
| CN109679498A (en) * | 2019-01-02 | 2019-04-26 | 华南理工大学 | A kind of nanometer alumina modified silane waterproofing agent and the preparation method and application thereof |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6415313A (en) * | 1987-07-09 | 1989-01-19 | Sonoike Mfg | Optical device in laser beam surface treating apparatus |
| JPS6415316A (en) * | 1987-07-09 | 1989-01-19 | Sonoike Mfg | Device for adjusting irradiating direction in laser beam surface treating apparatus |
-
1985
- 1985-12-05 JP JP27247785A patent/JPS61166814A/en active Granted
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0416369A2 (en) * | 1989-09-05 | 1991-03-13 | MERCK PATENT GmbH | Polymer coated plate-like substrate |
| JP2006307028A (en) * | 2005-04-28 | 2006-11-09 | Jsr Corp | Urethane (meth)acrylate, radiation-curable composition and its cured film |
| JP4572732B2 (en) * | 2005-04-28 | 2010-11-04 | Ｊｓｒ株式会社 | Urethane (meth) acrylate, radiation curable composition, and cured film thereof |
| CN108559391A (en) * | 2018-04-20 | 2018-09-21 | 上海振华重工（集团）常州油漆有限公司 | A kind of polyaspartic ester finishing coat and its preparation method and application |
| CN108559391B (en) * | 2018-04-20 | 2020-04-21 | 上海振华重工（集团）常州油漆有限公司 | Polyaspartic acid ester finish paint and preparation method and application thereof |
| CN109679498A (en) * | 2019-01-02 | 2019-04-26 | 华南理工大学 | A kind of nanometer alumina modified silane waterproofing agent and the preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6146502B2 (en) | 1986-10-14 |
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