JPH038671B2 - - Google Patents
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- Publication number
- JPH038671B2 JPH038671B2 JP60292453A JP29245385A JPH038671B2 JP H038671 B2 JPH038671 B2 JP H038671B2 JP 60292453 A JP60292453 A JP 60292453A JP 29245385 A JP29245385 A JP 29245385A JP H038671 B2 JPH038671 B2 JP H038671B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- group
- general formula
- formula
- alkyl group
- 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
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- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
Description
〔発明の技術分野〕
本発明はコーテイング剤組成物に関し、各種合
成樹脂、スレート基板、コンクリート、金属等に
塗布することにより透明で、高硬度の耐熱性被膜
を与えるコーテイング組成物に関する。
〔従来技術〕
従来、透明なコート材は数多く提案され、代表
的なものとして、アクリル系やウレタン系のもの
があるが、ウレタン系はソフトであり、風合が良
いという長所はあるが、耐水性に乏しい欠点があ
る。
又、アクリル系は透明性が高く、化粧塗料とし
てすぐれているが、柔らかいため傷がつきやす
く、かつ、耐熱性が不足するという欠点がある。
又、これらの欠点を補う目的で、例えば特公昭60
−31863では、或る種の不飽和グリシジルエーテ
ルの単量体と或る種のシラン化合物の混合組成物
を電離性放射線照射によつて共重合せしめるコー
テイング組成物が提案されている。
この組成物は耐擦傷性、耐温水性、表面硬度等
にすぐれているが、高分子化が難かしく、かつ、
被膜が硬いため、表面の化粧性を目的として数十
ミクロン以上の厚膜を形成する必要がある場合、
ヒビ割れ等の不都合を生じる。
また、シリコーン系不飽和化合物とビニルモノ
マーとの共重合体組成物の混合物を用いたコーテ
イング膜の製造方法について、例えば特開昭57−
26419号に提案されているが、これらは接着性、
耐熱性に欠け、高温で亀裂や収縮を起し易い欠点
がある。
〔発明の目的〕
本発明は、上述の従来技術の欠点を改良すべく
なされたものである。
すなわち、本発明の目的は、耐温水性、厚塗り
可能性、耐アルカリ性、表面硬度、耐熱性にすぐ
れ、かつ、各種基材との密着性にすぐれたコーテ
イング組成物を提供することにある。
〔発明の構成〕
上記目的を達成する本発明のコーテイング剤組
成物は、
(イ) 一般式
（R1：C1〜C20のアルキル基、シクロアルキ
ル基、フエニルアルキル基、アルキル基エーテ
ル基、Ｘ；Ｈ，CH3又はハロゲン）
で表わされるアクリル酸エステル化合物50〜95
重量％と、
(ロ) 一般式
[Technical Field of the Invention] The present invention relates to a coating composition, and more particularly, to a coating composition that provides a transparent, highly hard, heat-resistant coating when applied to various synthetic resins, slate substrates, concrete, metals, etc. [Prior art] Many transparent coating materials have been proposed in the past, and acrylic and urethane-based materials are typical examples.Urethane-based materials have the advantage of being soft and have a good texture, but they are not waterproof. It has the disadvantage of lacking in sexuality. Furthermore, acrylic paints have high transparency and are excellent as decorative paints, but they have the drawbacks of being soft and easily scratched, and lacking in heat resistance.
In addition, for the purpose of compensating for these shortcomings, for example,
No. 31863 proposes a coating composition in which a mixed composition of a certain type of unsaturated glycidyl ether monomer and a certain type of silane compound is copolymerized by irradiation with ionizing radiation. This composition has excellent scratch resistance, hot water resistance, surface hardness, etc., but it is difficult to polymerize, and
Because the film is hard, if it is necessary to form a thick film of several tens of microns or more for the purpose of surface cosmetics,
This may cause inconveniences such as cracks. In addition, regarding a method for manufacturing a coating film using a mixture of a copolymer composition of a silicone-based unsaturated compound and a vinyl monomer, for example,
26419, these are adhesive,
It lacks heat resistance and tends to crack or shrink at high temperatures. [Object of the Invention] The present invention has been made to improve the above-mentioned drawbacks of the prior art. That is, an object of the present invention is to provide a coating composition that has excellent hot water resistance, thick coating ability, alkali resistance, surface hardness, and heat resistance, and has excellent adhesion to various substrates. [Structure of the Invention] The coating agent composition of the present invention that achieves the above object has the following formula: (a) General formula (R 1 : C 1 to C 20 alkyl group, cycloalkyl group, phenyl alkyl group, alkyl group ether group, X: H, CH 3 or halogen) Acrylic acid ester compound 50 to 95
Weight% and (b) General formula
【式】又
は
（R2；C1〜C6のアルキレン基、Ｘ；上記の
とおり）
で表わされるエポキシ基含有ビニル化合物50〜
５重量％との共重合体100重量部に対して
(ハ) 一般式[Formula] or (R 2 ; C 1 to C 6 alkylene group, X; as above) Epoxy group-containing vinyl compound 50 to
(c) General formula for 100 parts by weight of copolymer with 5% by weight
【式】又
は
（R2；上記のとおり、R3；C1〜C6のアルキ
ル基、R4；OR3か又はC1〜C6のアルキル基）
で表わされるエポキシ基含有シラン化合物５〜
20重量部および
(ニ) 一般式[Formula] or (R 2 ; as above, R 3 ; C 1 to C 6 alkyl group, R 4 ; OR 3 or C 1 to C 6 alkyl group)
Epoxy group-containing silane compound 5 represented by
20 parts by weight and (d) General formula
以上述べたように本発明のコーテイング剤組成
物によれば、次のようなすぐれた効果を発揮す
る。
(1) 透明性に優れ、耐アルカリ性が良好である。
(2) 鉛筆硬度7H以上の高硬度の被膜が得られる。
(3) 適当な顔料を加えることにより耐蝕性にすぐ
れた美粧性の高い塗膜となる。
(4) 厚塗りが可能であり、各種プラスチツクの他
スレート板、セメント、コンクリート面に塗布
することができる。
(5) アクリル酸エステル化合物を共重合体成分と
しているので、塗膜が固く脆くなることを防止
することができ、またアクリル酸エステル化合
物の選択によつて塗膜の特性、たとえば靭性、
伸び等を調整することができる。
なお、本発明において採用した被膜性能の測定
方法を以下に説明する。
(1) 表面硬度；鉛筆硬度試験法によつた。
(2) 基材への接着性；１mm間隔で、カミソリを用
いて基材に達する迄の切り傷をつけ、１mm2のマ
スを100個作り、セロハンテープをはり、90゜方
向へ強く引つぱつた時の残存数で表わすいわゆ
るゴバン目剥離試験であり、全く剥離しない場
合は100/100で表わす。
(3) 耐水性；60℃の温水に塗布試験片を96時間浸
漬し被膜の外観を調べた。
(4) 耐アルカリ性；５％NaOH水溶液を40℃に
保ち、これに塗布試験片を96時間浸漬し、被膜
の外観を調べた。
(5) 耐熱性；150℃の空気循環式オーブンに５時
間放置後の被膜外観を調べた。
以下、本発明の実施例を述べる。
〔実施例〕
実施例１〜３及び比較例１
メチルメタクリレート80部（重量部、以下同
じ）、アリールグリシジルエーテル20部をトルエ
ン100部に溶解し、１部のベンゾイルパーオキサ
イドを添加して、90℃で10時間反応させ、粘調透
明なワニスを得た。このワニスにβ−（３，４−
エポキシシクロヘキシル）エチルトリメトキシシ
ラン６部を加え、更にγ−アミノプロピルトリメ
トキシシランを表１に示す部数だけ添加して均一
な溶液を得た。この溶液をアルミ板に塗布後150
℃で１時間熱処理を行い硬化被膜を得た。
実施例１〜３で得られた被膜はいずれも透明な
ものであつたが、比較例１は耐アルカリ性不良と
なり、被膜が膨潤して１部ふくれが発生した。
実施例 ４〜５
実施例１と同様にメチルメタクリレート80部、
アリールグリシジルエーテル20部のトルエン溶液
を作製し、これにγ−グリシドキシプロピルトリ
メトキシシランを10部加え、溶液(A)を調整した。
この溶液に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を表２に示す量だけ添
加して撹拌混合直後にポリカーボネート板に塗布
し、120℃で１時間熱処理して透明被膜のコート
試験片を得た。被膜特性は表２に示すごとく良好
なものであつた。
As described above, the coating agent composition of the present invention exhibits the following excellent effects. (1) Excellent transparency and good alkali resistance. (2) A highly hard coating with a pencil hardness of 7H or higher can be obtained. (3) By adding appropriate pigments, a coating film with excellent corrosion resistance and high cosmetic properties can be obtained. (4) Thick coating is possible, and it can be applied to various plastics, slate boards, cement, and concrete surfaces. (5) Since the acrylic ester compound is used as a copolymer component, the coating film can be prevented from becoming hard and brittle, and the selection of the acrylic ester compound can improve the properties of the coating film, such as toughness,
Elongation etc. can be adjusted. The method for measuring film performance adopted in the present invention will be explained below. (1) Surface hardness: Based on the pencil hardness test method. (2) Adhesion to the base material: Use a razor to make cuts at 1 mm intervals until reaching the base material, make 100 squares of 1 mm square, apply cellophane tape, and pull strongly in a 90° direction. This is a so-called cross-cut peeling test, which is expressed in terms of the number remaining when peeling.If no peeling occurs at all, it is expressed as 100/100. (3) Water resistance: The coated test piece was immersed in warm water at 60°C for 96 hours, and the appearance of the film was examined. (4) Alkali resistance: A coated test piece was immersed in a 5% NaOH aqueous solution at 40°C for 96 hours, and the appearance of the film was examined. (5) Heat resistance: The appearance of the film was examined after being left in an air circulation oven at 150°C for 5 hours. Examples of the present invention will be described below. [Example] Examples 1 to 3 and Comparative Example 1 80 parts of methyl methacrylate (parts by weight, same hereinafter) and 20 parts of aryl glycidyl ether were dissolved in 100 parts of toluene, 1 part of benzoyl peroxide was added, and 90 parts of benzoyl peroxide was added. The reaction was carried out at ℃ for 10 hours to obtain a viscous and transparent varnish. β-(3,4-
6 parts of epoxycyclohexyl)ethyltrimethoxysilane were added, and further γ-aminopropyltrimethoxysilane was added in the amount shown in Table 1 to obtain a homogeneous solution. 150 minutes after applying this solution to the aluminum plate
Heat treatment was performed at ℃ for 1 hour to obtain a cured film. The coatings obtained in Examples 1 to 3 were all transparent, but Comparative Example 1 had poor alkali resistance, and the coating swelled and blistered in some areas. Examples 4-5 80 parts of methyl methacrylate as in Example 1,
A toluene solution of 20 parts of aryl glycidyl ether was prepared, and 10 parts of γ-glycidoxypropyltrimethoxysilane was added thereto to prepare a solution (A).
N-β (aminoethyl-γ-aminopropyltrimethoxysilane) was added to this solution in the amount shown in Table 2, and immediately after stirring and mixing, it was coated on a polycarbonate plate, heat-treated at 120°C for 1 hour, and a transparent film coating test was performed. A piece was obtained.The coating properties were good as shown in Table 2.
【表】【table】
【表】
実施例 ６〜９
メチルメタクリレートとｎ−ブチルメタクリレ
ートとグリシジルメタクリレートを表３のごとく
組成を決め、アゾビスイソブチロニトリルを0.5
部加えて、70℃で５時間反応させて透明で粘調な
溶液を作製した。この溶液にβ−（３，４−エポ
キシシクロヘキシルエチルトリメトキシシランお
よびγ−アミノプロピルトリメトキシシランを
夫々加えてストレート板に塗布し、150℃で30分
熱処理してコーテイング板を得た。
得られた塗板は撥水性の高く、表面硬度の高い
美粧性あるものとなつた。[Table] Examples 6 to 9 The compositions of methyl methacrylate, n-butyl methacrylate, and glycidyl methacrylate were determined as shown in Table 3, and azobisisobutyronitrile was added to 0.5
A clear and viscous solution was prepared by adding 50% of the solution and reacting at 70°C for 5 hours. β-(3,4-epoxycyclohexylethyltrimethoxysilane and γ-aminopropyltrimethoxysilane) were respectively added to this solution and applied to a straight plate, and heat treated at 150°C for 30 minutes to obtain a coated plate. The coated plates were highly water repellent and had a high surface hardness, making them aesthetically pleasing.
Claims (1)
ル基、フエニルアルキル基、アルキルエーテル
基、Ｘ；Ｈ，CH3又はハロゲン） で表わされるアクリル酸エステル化合物50〜95
重量％と、 (ロ) 一般式【式】又 は （R2；C1〜C6のアルキレン基、Ｘ；上記の
とおり） で表わされるエポキシ基含有ビニル化合物50〜
５重量％との共重合体100重量部に対して (ハ) 一般式【式】又 は （R2；上記のとおり、R3；C1〜C6のアルキ
ル基、R4；OR3か又はC1〜C6のアルキル基）
で表わされるエポキシ基含有シラン化合物５〜
20重量部および (ニ) 一般式【式】又は （R2，R3およびR3は上記のとおり）で表わ
されるアミノシラン化合物をアミノ基のモル数
SAが１≦SA／PE＋SE≦1.3となるように加えてな るコーテイング剤組成物。ただしPEは上記化
合物(イ)と化合物(ロ)との共重合体中に含まれるエ
ポキシ基のモル数を表わし、SEは上記化合物
(ハ)のエポキシ基のモル数を表わす。[Claims] 1 (a) General formula (R 1 : C 1 to C 20 alkyl group, cycloalkyl group, phenyl alkyl group, alkyl ether group, X; H, CH 3 or halogen) Acrylic acid ester compound 50 to 95
Weight% and (b) General formula [formula] or (R 2 ; C 1 to C 6 alkylene group, X; as above) Epoxy group-containing vinyl compound 50 to
(c) General formula [formula] or (R 2 ; as above, R 3 ; C 1 to C 6 alkyl group, R 4 ; OR 3 or C 1 to C 6 alkyl group)
Epoxy group-containing silane compound 5 represented by
20 parts by weight and (d) General formula [formula] or (R 2 , R 3 and R 3 are as above) with the number of moles of amino groups
A coating agent composition in which SA is added so that 1≦SA/PE+SE≦1.3. However, PE represents the number of moles of epoxy groups contained in the copolymer of the above compound (a) and compound (b), and SE represents the number of moles of epoxy groups contained in the copolymer of the above compound (a) and compound (b).
It represents the number of moles of the epoxy group in (c).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29245385A JPS62153359A (en) | 1985-12-27 | 1985-12-27 | Coating composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29245385A JPS62153359A (en) | 1985-12-27 | 1985-12-27 | Coating composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62153359A JPS62153359A (en) | 1987-07-08 |
| JPH038671B2 true JPH038671B2 (en) | 1991-02-06 |
Family
ID=17781995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP29245385A Granted JPS62153359A (en) | 1985-12-27 | 1985-12-27 | Coating composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62153359A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4988759A (en) * | 1989-09-26 | 1991-01-29 | E. I. Du Pont De Nemours And Company | Coating composition of acrylic polymers containing reactive groups and an epoxy organosilane |
| US5064719A (en) * | 1989-09-26 | 1991-11-12 | E. I. Du Pont De Nemours And Company | Coating composition of acrylic polymers containing reactive groups and an epoxy organosilane |
| DE102007023282A1 (en) | 2007-05-18 | 2008-11-20 | Bayer Materialscience Ag | Silane coatings of aminosilanes and epoxy-functional polyacrylates |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6031863B2 (en) * | 1977-10-26 | 1985-07-24 | 日本原子力研究所 | Composition for polycarbonate resin coating |
-
1985
- 1985-12-27 JP JP29245385A patent/JPS62153359A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62153359A (en) | 1987-07-08 |
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