JPH0586307A - Radiation-curable coating composition - Google Patents
Radiation-curable coating compositionInfo
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- JPH0586307A JPH0586307A JP25149591A JP25149591A JPH0586307A JP H0586307 A JPH0586307 A JP H0586307A JP 25149591 A JP25149591 A JP 25149591A JP 25149591 A JP25149591 A JP 25149591A JP H0586307 A JPH0586307 A JP H0586307A
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Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、放射線硬化型塗工剤に
関する。FIELD OF THE INVENTION The present invention relates to a radiation curable coating agent.
【０００２】[0002]
【従来の技術】近年、放射線硬化型塗工剤は、プラスチ
ックや紙、金属等への印刷および表面保護コーティング
剤として、あらゆる分野において利用されるに至ってい
る。広く利用されている理由として、瞬時硬化特性によ
り生産性に優れている、有機溶剤を必ずしも必要としな
いため環境保全に役立つ、耐水・耐薬品性等の化学的耐
性に優れている、そして表面耐擦傷性等の物理的耐性に
優れている、などがあげられる。2. Description of the Related Art In recent years, radiation-curable coating agents have come to be used in all fields as printing and surface protection coating agents on plastic, paper, metal and the like. It is widely used because it has excellent productivity due to the instant curing property, it is useful for environmental protection because it does not necessarily require an organic solvent, it has excellent chemical resistance such as water resistance and chemical resistance, and surface resistance. It has excellent physical resistance such as scratch resistance.
【０００３】表面保護性に優れた硬い塗膜を得る場合、
硬化塗膜の架橋密度を上げるために、放射線硬化型塗工
剤の官能基濃度を高くすることが通常行われている。To obtain a hard coating film excellent in surface protection,
In order to increase the crosslink density of the cured coating film, it is usual to increase the functional group concentration of the radiation curable coating agent.
【０００４】しかしながら、ただ単に官能基濃度を高く
して架橋密度の高い塗膜とすると、硬化時の収縮も大き
くなり、そのため硬化塗膜の可撓性および強靱性に劣
り、塗膜にクラックが入りやすくなる欠点がある。However, when a coating having a high crosslink density is simply prepared by increasing the concentration of functional groups, the shrinkage at the time of curing also becomes large, so that the flexibility and toughness of the cured coating are inferior and the coating has cracks. There is a drawback that it is easy to enter.
【０００５】[0005]
【発明が解決しようとする課題】本発明はこのような問
題点を解決するためになされたもので、その課題とする
ところは、表面保護性に優れ、可撓性および強靱性に優
れた放射線硬化型塗工剤を提供することにある。SUMMARY OF THE INVENTION The present invention has been made to solve the above problems, and its object is to provide radiation having excellent surface protection, flexibility and toughness. It is to provide a curable coating agent.
【０００６】[0006]
【課題を解決するための手段】本発明は以上の課題を解
決するために、成分１として、両末端に少なくとも２つ
以上のアクリロイル基を、さらに好ましくは３つ以上の
アクリロイル基を有し、主鎖構造として側鎖を持たない
直鎖脂肪族よりなるモノマーまたはオリゴマー、成分２
として、両末端に１つずつのアクリロイル基を有し、主
鎖構造として側鎖を持たない直鎖脂肪族よりなるモノマ
ーまたはオリゴマー、以上の２つの主成分の比が好まし
くは８：２〜２：８の範囲であることを特徴とする放射
線硬化型塗工剤を提供する。In order to solve the above problems, the present invention has, as the component 1, at least two acryloyl groups at both ends, and more preferably three or more acryloyl groups, Monomers or oligomers of straight-chain aliphatic having no side chain as main chain structure, component 2
As a monomer or oligomer having a single acryloyl group at both ends and a linear aliphatic chain having no side chain as a main chain structure, the ratio of the above two main components is preferably 8: 2 to 2 The radiation-curable coating agent is provided in the range of: 8.
【０００７】成分１の両末端に少なくとも２つ以上のア
クリロイル基を、さらに好ましくは３つ以上のアクリロ
イル基を有し、主鎖構造として側鎖を持たない直鎖脂肪
族よりなるモノマー又はオリゴマーとして考えられる分
子構造は、特に限定はしないが、例えば以下のようなも
のがあげられる。As a monomer or oligomer comprising a straight-chain aliphatic group having at least two or more acryloyl groups at both ends of the component 1, more preferably three or more acryloyl groups and having no side chain as a main chain structure. The conceivable molecular structure is not particularly limited, but examples thereof include the following.
【０００８】[0008]
【化１】 [Chemical 1]
【０００９】[0009]
【化２】 [Chemical 2]
【００１０】[0010]
【化３】 [Chemical 3]
【００１１】[0011]
【化４】 [Chemical 4]
【００１２】[0012]
【化５】 [Chemical 5]
【００１３】[0013]
【化６】 [Chemical 6]
【００１４】成分２の両末端に１つずつのアクリロイル
基を有し、主鎖構造として側鎖を持たない直鎖脂肪族よ
りなるモノマー又はオリゴマーとして考えられる分子構
造は、特に限定はしないが、例えば以下のようなものが
あげられる。There is no particular limitation on the molecular structure of Component 2 which is considered as a linear aliphatic monomer or oligomer having one acryloyl group at both ends and having no side chain as the main chain structure. Examples include the following.
【００１５】[0015]
【化７】ａ−Ｏ− (ＣＨ2)n −Ｏ−ａEmbedded image a-O- (CH 2) n -O-a
【００１６】[0016]
【化８】ａ− (ＯＣＨ2 ＣＨ2)n −Ｏ−ａEmbedded image a- (OCH 2 CH 2 ) n- O-a
【００１７】ａ：アクリロイル基 ｎ≧１A: acryloyl group n ≧ 1
【００１８】[0018]
【作用】以上に示したように、成分１、成分２ともに、
主鎖が直鎖型の高分子である。これら２成分を成分比が
２：８〜８：２の範囲内で混合すると、両成分とも直鎖
脂肪族なので互いによく絡み合い、表面にかかる応力に
対し強い構造になり、耐擦傷性が向上する。As described above, both component 1 and component 2
The main chain is a linear polymer. When these two components are mixed in a ratio of 2: 8 to 8: 2, both components are straight-chain aliphatic and thus are entangled well with each other, resulting in a structure strong against stress applied to the surface and improving scratch resistance. .
【００１９】[0019]
＜実施例１＞厚さ３００μｍのポリエチレンテレフタレ
ートのシートの片面に、下記組成からなる放射線硬化型
塗工剤を、グラビアコートにより、硬化後の膜厚が約２
〜３μｍになるように塗工した。<Example 1> A radiation-curable coating agent having the following composition was gravure coated on one side of a polyethylene terephthalate sheet having a thickness of 300 µm to give a film thickness of about 2 after curing.
It was coated so as to have a thickness of ˜3 μm.
【００２０】 成分１ （化１） ５３重量部 成分２ （化７）（ｎ＝９） ４７重量部 計 １００重量部Component 1 (Chemical Formula 1) 53 parts by weight Component 2 (Chemical Formula 7) (n = 9) 47 parts by weight Total 100 parts by weight
【００２１】塗工後引き続き、電子線照射装置（日新ハ
イボルテージ（株）製：「キュアトロン」）の照射下を
通過させ、照射線量約５．０Ｍｒａｄのエネルギーで塗
膜を硬化させた。After coating, the coating film was passed under irradiation of an electron beam irradiation device ("Curetron" manufactured by Nisshin High Voltage Co., Ltd.) to cure the coating film with an energy of irradiation dose of about 5.0 Mrad.
【００２２】＜実施例２＞実施例１において、放射線硬
化型塗工剤の組成が以下であること以外は、実施例１と
同様の方法で塗膜を硬化させた。Example 2 A coating film was cured in the same manner as in Example 1 except that the composition of the radiation-curable coating agent was the following.
【００２３】 成分１ （化１） ６０重量部 成分２ （化８）（ｎ＝１８） ４０重量部 計 １００重量部Component 1 (Chemical Formula 1) 60 parts by weight Component 2 (Chemical Formula 8) (n = 18) 40 parts by weight Total 100 parts by weight
【００２４】＜実施例３＞実施例１において、放射線硬
化型塗工剤の組成が以下であること以外は、実施例１と
同様の方法で塗膜を硬化させた。Example 3 The coating film was cured in the same manner as in Example 1 except that the composition of the radiation-curable coating agent was the following.
【００２５】 成分１ （化２） ５９重量部 成分２ （化７）（ｎ＝９） ４１重量部 計 １００重量部Component 1 (Chemical Formula 2) 59 parts by weight Component 2 (Chemical Formula 7) (n = 9) 41 parts by weight Total 100 parts by weight
【００２６】＜実施例４＞実施例１において、放射線硬
化型塗工剤の組成が以下であること以外は、実施例１と
同様の方法で塗膜を硬化させた。<Example 4> A coating film was cured in the same manner as in Example 1 except that the composition of the radiation-curable coating agent was the following.
【００２７】 成分１ （化４）（ｎ＝３） ４９重量部 成分２ （化７）（ｎ＝９） ５１重量部 計 １００重量部Component 1 (Chemical Formula 4) (n = 3) 49 parts by weight Component 2 (Chemical Formula 7) (n = 9) 51 parts by weight Total 100 parts by weight
【００２８】＜実施例５＞実施例１において、放射線硬
化型塗工剤の組成が以下であること以外は、実施例１と
同様の方法で塗膜を硬化させた。<Example 5> A coating film was cured in the same manner as in Example 1 except that the composition of the radiation-curable coating agent was the following.
【００２９】 成分１ （化４）（ｎ＝６） ５１重量部 成分２ （化７）（ｎ＝９） ４９重量部 計１００重量部Component 1 (Chemical Formula 4) (n = 6) 51 parts by weight Component 2 (Chemical Formula 7) (n = 9) 49 parts by weight Total 100 parts by weight
【００３０】＜実施例６＞実施例１において、放射線硬
化型塗工剤の組成が以下であること以外は同様のもの
を、紫外線照射装置（アイグラフィックス（株）製：メ
タルハライドランプ１２０W/cm、２灯）の照射下を通過
させ、照射線量約４００mJ/cm2のエネルギーで塗膜を硬
化させた。<Example 6> The same example as in Example 1 was used except that the composition of the radiation-curable coating agent was as follows. (2 lights), and the coating film was cured with the energy of the irradiation dose of about 400 mJ / cm 2 .
【００３１】 成分１ （化１） ５３重量部 成分２ （化７）（ｎ＝９） ４７重量部 光開始剤 （メルク社製：「ダロキュアー1173」） ５重量部 計 １０５重量部Component 1 (Chemical Formula 1) 53 parts by weight Component 2 (Chemical Formula 7) (n = 9) 47 parts by weight Photoinitiator (Merck & Co .: “Darocurer 1173”) 5 parts by weight Total 105 parts by weight
【００３２】＜実施例７＞実施例６において、放射線硬
化型塗工剤の組成が以下であること以外は、実施例６と
同様の方法で塗膜を硬化させた。<Example 7> A coating film was cured in the same manner as in Example 6 except that the composition of the radiation-curable coating agent in Example 6 was as follows.
【００３３】 成分１ （化１） ６０重量部 成分２ （化８）（ｎ＝１８） ４０重量部 光開始剤 （メルク社製：「ダロキュアー1173」） ５重量部 計 １０５重量部Component 1 (Chemical Formula 1) 60 parts by weight Component 2 (Chemical Formula 8) (n = 18) 40 parts by weight Photoinitiator (Merck & Co., Inc .: “Darocurure 1173”) 5 parts by weight Total 105 parts by weight
【００３４】＜実施例８＞実施例６において、放射線硬
化型塗工剤の組成が以下であること以外は、実施例６と
同様の方法で塗膜を硬化させた。Example 8 A coating film was cured in the same manner as in Example 6 except that the composition of the radiation curable coating agent was the following.
【００３５】 成分１ （化２） ５９重量部 成分２ （化７）（ｎ＝９） ４１重量部 光開始剤 （メルク社製：「ダロキュアー1173」） ５重量部 計 １０５重量部Component 1 (Chemical Formula 2) 59 parts by weight Component 2 (Chemical Formula 7) (n = 9) 41 parts by weight Photoinitiator (Merck & Co., Inc .: “Darocurure 1173”) 5 parts by weight Total 105 parts by weight
【００３６】＜実施例９＞実施例６において、放射線硬
化型塗工剤の組成が以下であること以外は、実施例６と
同様の方法で塗膜を硬化させた。<Example 9> A coating film was cured in the same manner as in Example 6 except that the composition of the radiation-curable coating agent was the following.
【００３７】 成分１ （化４）（ｎ＝３） ４９重量部 成分２ （化７）（ｎ＝９） ５１重量部 光開始剤 （メルク社製：「ダロキュアー1173」） ５重量部 計 １０５重量部Component 1 (Chemical Formula 4) (n = 3) 49 parts by weight Component 2 (Chemical Formula 7) (n = 9) 51 parts by weight Photoinitiator (Merck & Co .: “Darocurer 1173”) 5 parts by weight Total 105 parts by weight Department
【００３８】＜実施例１０＞実施例６において、放射線
硬化型塗工剤の組成が以下であること以外は、実施例６
と同様の方法で塗膜を硬化させた。<Example 10> Example 6 is the same as Example 6 except that the composition of the radiation curable coating agent is as follows.
The coating film was cured in the same manner as in.
【００３９】 成分１ （化４）（ｎ＝６） ５１重量部 成分２ （化７）（ｎ＝９） ４９重量部 光開始剤 （メルク社製：「ダロキュアー1173」） ５重量部 計 １０５重量部Component 1 (Chemical Formula 4) (n = 6) 51 parts by weight Component 2 (Chemical Formula 7) (n = 9) 49 parts by weight Photoinitiator (Merck & Co .: “Darocurer 1173”) 5 parts by weight Total 105 parts by weight Department
【００４０】＜比較例１＞実施例１において、放射線硬
化型塗工剤の組成が以下であること以外は、実施例１と
同様の方法で塗膜を硬化させた。Comparative Example 1 A coating film was cured in the same manner as in Example 1 except that the composition of the radiation curable coating agent was the following.
【００４１】 成分 （化１） １００重量部 計 １００重量部Component (Chemical Formula 1) 100 parts by weight Total 100 parts by weight
【００４２】＜比較例２＞実施例１において、放射線硬
化型塗工剤の組成が以下であること以外は、実施例１と
同様の方法で塗膜を硬化させた。<Comparative Example 2> A coating film was cured in the same manner as in Example 1 except that the composition of the radiation curable coating agent in Example 1 was as follows.
【００４３】 成分 （化２） １００重量部 計 １００重量部Ingredient (Chemical Formula 2) 100 parts by weight Total 100 parts by weight
【００４４】＜比較例３＞実施例１において、放射線硬
化型塗工剤の組成が以下であること以外は、実施例１と
同様の方法で塗膜を硬化させた。Comparative Example 3 A coating film was cured in the same manner as in Example 1 except that the composition of the radiation curable coating agent was the following.
【００４５】 成分 （化４）（ｎ＝３） １００重量部 計 １００重量部Component (Chemical Formula 4) (n = 3) 100 parts by weight Total 100 parts by weight
【００４６】＜比較例４＞実施例１において、放射線硬
化型塗工剤の組成が以下であること以外は、実施例１と
同様の方法で塗膜を硬化させた。<Comparative Example 4> A coating film was cured in the same manner as in Example 1 except that the composition of the radiation curable coating agent was the following.
【００４７】 成分 （化４）（ｎ＝６） １００重量部 計 １００重量部Component (Chemical Formula 4) (n = 6) 100 parts by weight Total 100 parts by weight
【００４８】＜比較例５＞実施例１において、放射線硬
化型塗工剤の組成が以下であること以外は、実施例１と
同様の方法で塗膜を硬化させた。<Comparative Example 5> A coating film was cured in the same manner as in Example 1 except that the composition of the radiation curable coating agent was the following.
【００４９】 成分 （化７）（ｎ＝９） １００重量部 計 １００重量部Component (Chemical formula 7) (n = 9) 100 parts by weight Total 100 parts by weight
【００５０】＜比較例６＞実施例１において、放射線硬
化型塗工剤の組成が以下であること以外は、実施例１と
同様の方法で塗膜を硬化させた。<Comparative Example 6> A coating film was cured in the same manner as in Example 1 except that the composition of the radiation curable coating agent was the following.
【００５１】 成分 （化８）（ｎ＝１８） １００重量部 計 １００重量部Ingredient (Chemical Formula 8) (n = 18) 100 parts by weight Total 100 parts by weight
【００５２】実施例１〜実施例１０、比較例１〜比較例
６にて得られた硬化塗膜の表面の硬度を鉛筆硬度試験で
評価した。また、表面の耐擦傷性を見るために、摩耗輪
ＣＳ−１０を用い１００回転でテーバー摩耗試験を行
い、曇り値（ヘイズ値）で評価した。The surface hardness of the cured coating films obtained in Examples 1 to 10 and Comparative Examples 1 to 6 was evaluated by a pencil hardness test. Further, in order to check the scratch resistance of the surface, a Taber abrasion test was performed at 100 rotations using an abrasion wheel CS-10, and the haze value (haze value) was evaluated.
【００５３】[0053]
【表１】 [Table 1]
【００５４】[0054]
【発明の効果】以上に示したように、本発明により、硬
化時の収縮が低く抑えられ、なおかつ硬化塗膜の架橋密
度は低下しない、表面保護性に優れ可撓性および強靱性
に優れた放射線硬化型塗工剤を得ることができる。ま
た、フレキシブルな柔軟性が要求される素材において、
表面保護のための印刷およびコーティングを施すことに
対する制限がなくなった。As described above, according to the present invention, the shrinkage upon curing is suppressed to a low level, the crosslink density of the cured coating film does not decrease, the surface protection is excellent, and the flexibility and toughness are excellent. A radiation curable coating agent can be obtained. Also, for materials that require flexible flexibility,
There are no restrictions on printing and coating for surface protection.
Claims (1)
上、さらに好ましくは３つ以上のアクリロイル基を有
し、主鎖構造として側鎖を持たない直鎖脂肪族よりなる
モノマーまたはオリゴマー、成分２として、両末端に１
つずつのアクリロイル基を有し、主鎖構造として側鎖を
持たない直鎖脂肪族よりなるモノマーまたはオリゴマ
ー、以上の２つの主成分の比が８：２〜２：８の範囲で
あることを特徴とする放射線硬化型塗工剤。1. A component 1 is a linear aliphatic monomer or oligomer having at least two, and more preferably three or more acryloyl groups at both ends and having no side chain as a main chain structure, and a component. 2 as 1 at both ends
A straight-chain aliphatic monomer or oligomer having each acryloyl group and having no side chain as the main chain structure, and the ratio of the above two main components is in the range of 8: 2 to 2: 8. A characteristic radiation-curable coating agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25149591A JPH0586307A (en) | 1991-09-30 | 1991-09-30 | Radiation-curable coating composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25149591A JPH0586307A (en) | 1991-09-30 | 1991-09-30 | Radiation-curable coating composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0586307A true JPH0586307A (en) | 1993-04-06 |
Family
ID=17223653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25149591A Pending JPH0586307A (en) | 1991-09-30 | 1991-09-30 | Radiation-curable coating composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0586307A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002327063A (en) * | 2001-05-01 | 2002-11-15 | Asahi Kasei Aimii Kk | Hydrophilic polysiloxane monomer, contact-lens material comprising copolymer thereof, and contact-lens |
| WO2005044777A1 (en) * | 2003-11-07 | 2005-05-19 | Taiyo Ink Manufacturing Co., Ltd. | Tetra(meth)acrylate compound, curing composition containing same, and cured products of those |
| WO2007080936A1 (en) * | 2006-01-13 | 2007-07-19 | Denki Kagaku Kogyo Kabushiki Kaisha | Curable resin composition, surface protection method, temporary fixation method, and separation method |
| US8519018B2 (en) * | 2009-10-21 | 2013-08-27 | Innovative Bottles, Llc | Biodegradable material and container for fluids |
| US11111057B2 (en) | 2016-03-04 | 2021-09-07 | Amisha Patel | Bioplastic collapsible dispensing tube |
-
1991
- 1991-09-30 JP JP25149591A patent/JPH0586307A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002327063A (en) * | 2001-05-01 | 2002-11-15 | Asahi Kasei Aimii Kk | Hydrophilic polysiloxane monomer, contact-lens material comprising copolymer thereof, and contact-lens |
| WO2005044777A1 (en) * | 2003-11-07 | 2005-05-19 | Taiyo Ink Manufacturing Co., Ltd. | Tetra(meth)acrylate compound, curing composition containing same, and cured products of those |
| JPWO2005044777A1 (en) * | 2003-11-07 | 2007-11-29 | 太陽インキ製造株式会社 | Tetra(meth)acrylate compound, curable composition containing the same, and cured products thereof |
| WO2007080936A1 (en) * | 2006-01-13 | 2007-07-19 | Denki Kagaku Kogyo Kabushiki Kaisha | Curable resin composition, surface protection method, temporary fixation method, and separation method |
| US8519018B2 (en) * | 2009-10-21 | 2013-08-27 | Innovative Bottles, Llc | Biodegradable material and container for fluids |
| US11111057B2 (en) | 2016-03-04 | 2021-09-07 | Amisha Patel | Bioplastic collapsible dispensing tube |
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