JPS6332091B2 - - Google Patents
Info
- Publication number
- JPS6332091B2 JPS6332091B2 JP56118176A JP11817681A JPS6332091B2 JP S6332091 B2 JPS6332091 B2 JP S6332091B2 JP 56118176 A JP56118176 A JP 56118176A JP 11817681 A JP11817681 A JP 11817681A JP S6332091 B2 JPS6332091 B2 JP S6332091B2
- Authority
- JP
- Japan
- Prior art keywords
- curing
- acrylic
- paint
- ultraviolet
- adhering
- 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
- 238000000034 method Methods 0.000 claims description 18
- 239000003973 paint Substances 0.000 claims description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 13
- 230000001678 irradiating effect Effects 0.000 claims description 4
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims description 3
- -1 acrylic ester Chemical class 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 2
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000004925 Acrylic resin Substances 0.000 description 5
- 229920000178 Acrylic resin Polymers 0.000 description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- FCSHDIVRCWTZOX-DVTGEIKXSA-N clobetasol Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CCl)(O)[C@@]1(C)C[C@@H]2O FCSHDIVRCWTZOX-DVTGEIKXSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Application Of Or Painting With Fluid Materials (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
Description
本発明は紫外線硬化塗料を紫外線の照射によつ
てアクリルシートへ強固に接着させるアクリルシ
ートへの紫外線硬化塗料の硬化接着方法に関す
る。
従来、アクリル樹脂のシートなどに化学的手法
によつて被接着物を接着する方法としては大別し
て溶剤法と重合法とが知られている。前者はアク
リル樹脂をよく溶解する揮発度の高い溶剤によつ
て接着すべきアクリル樹脂面を膨潤,溶解させ、
のち圧着して接着させる方法である。一方、後者
はメタクリル酸メチルモノマーとポリメタクリル
酸メチルのシラツプ状混合物を使用して、これに
熱重合開始剤または光重合開始剤を加えてシート
と被接着物との接着面間に流し込み、のち加熱あ
るいは紫外線を照射して接着させる方法である。
しかし、前者の溶剤法による接着法では、圧着
後溶剤が揮散することによつて接着が生じること
になるので、溶剤が系外に揮散しやすい比較的接
着面積の小さいまたは細長い形状の接着面をもつ
場合には適しているが、接着面が正方形に近くか
つ接着面積の大きい場合には内部の溶剤が揮散し
にくゝ残存溶剤による弊害を生じる場合が多い。
また後者の重合法による接着法では使用する接
着液に熱重合開始剤または光重合開始剤がすでに
添加されているため、使用前の環境下での熱ある
いは光によるポツトライフに問題が生じてくる。
また一方、硬質プララスチツクシートへ紫外線
照射によつて紫外線硬化塗料を硬化接着させる方
法については、紫外線硬化塗料中の成分等に反応
性稀釈剤の性質を検討することによりその接着性
を上げる試みも行なわれている。しかし紫外線硬
化塗料に要求される他の種々の特性、たとえば光
硬化性、ポツトライフ、表面硬度、耐熱性あるい
は硬化収縮率などを総合的に満足させるためには
使用すべき反応性稀釈剤は制約を受け、必ずしも
満足すべき結果が出ていないのが現状である。
このため如何なる種類の紫外線硬化塗料に対し
ても共通して利用でき、また接着後溶剤の揮散す
る心配がなく、かつ如何なる環境下でもポツトラ
イフに制約を受けない処理液でもつてアクリルシ
ートを処理し、それによつて接着性を増大させる
方法が強く要望されている。
本発明は従来の欠点を除去するため、紫外線の
照射によつてアクリルシートへ紫外線硬化塗料を
硬化、接着させる方法において、前記アクリルシ
ートの接着面にアクリルシートを溶解、膨潤させ
るN―ビニル―2―ピロリドン、またはアクリル
酸エステルもしくはメタクリル酸エステルのうち
少くとも一つを薄く塗布し、ついでその処理面に
紫外線硬化塗料を所望の厚みに塗布し、次に紫外
線を照射することを特徴とし、その目的は光硬化
性、ポツトライフ、表面硬度、耐熱性あるいは硬
化収縮率を満足すると共に接着性を向上するにあ
る。
本発明は紫外線硬化塗料を塗布する前にアクリ
ルシート面に塗布する処理液としてはアクリル樹
脂を溶解、膨潤させるものが好ましく、N―ビニ
ル―2―2ピロリドン、アクリル酸エステルのヒ
ドロキシエチルアクリレートまたはテトラヒドロ
フルフリールアクリレート、メタクリル酸エステ
ルのベンジルメタクリレート、グリシジルメタク
リレートまたはエチレングリコールジメタクリレ
ートなどが挙げられ、これら処理液はそのままで
あるいはシートに害を及ぼさない、たとえばアル
コール溶液として用いられる。
以下、本発明のメタクリシートへの紫外線硬化
塗料の硬化接着方法およびその作用効果について
説明する。
〔実施例 1〕
アクリルシート上に第1表に示した処理液の10
%エチルアルコール溶液を回転塗布機を用いて
300回転で回転塗布し1分間回転を続ける。のち
その処理面上に、2,2―ビス(4―アクリロイ
ルオキシジエチレンオキシフエニル)プロパン
(商品名、NKエステル、A―BPE―4)100重量
部、ベンゾインイソプロピルエーテル2重量部か
らなる紫外線硬化塗料を100μmの厚みとなるよう
に塗布し、1KW高圧水銀灯15cmの距離より30秒
間照射する。得られたそれぞれの試料についてク
ロスカツトによる密着性試験を行ない第2表の結
果を得た。
The present invention relates to a method for curing and adhering an ultraviolet curable paint to an acrylic sheet, in which the ultraviolet curable paint is firmly adhered to the acrylic sheet by irradiation with ultraviolet rays. BACKGROUND ART Conventionally, methods for bonding objects to acrylic resin sheets or the like by chemical methods are broadly classified into solvent methods and polymerization methods. The former uses a highly volatile solvent that dissolves acrylic resin well to swell and dissolve the acrylic resin surface to be bonded.
This method is followed by pressure bonding and adhesion. On the other hand, the latter uses a syrup-like mixture of methyl methacrylate monomer and polymethyl methacrylate, adds a thermal polymerization initiator or a photopolymerization initiator, and pours the mixture between the bonding surfaces of the sheet and the object to be bonded. This is a method of bonding by heating or irradiating with ultraviolet rays. However, in the former solvent-based bonding method, adhesion occurs when the solvent evaporates after pressure bonding, so the bonding surface is relatively small or has a long and narrow shape where the solvent easily evaporates outside the system. However, if the bonding surface is close to a square and the bonding area is large, the solvent inside is difficult to volatilize and residual solvent often causes problems. Furthermore, in the latter adhesive method using the polymerization method, a thermal polymerization initiator or a photopolymerization initiator is already added to the adhesive liquid used, so there is a problem with pot life due to heat or light in the environment before use. On the other hand, regarding a method of curing and adhering an ultraviolet curable paint to a hard plastic sheet by irradiating it with ultraviolet rays, an attempt was made to improve the adhesion by examining the properties of a reactive diluent in the components of the ultraviolet curable paint. is also being carried out. However, in order to comprehensively satisfy the various other properties required for UV-curable paints, such as photocurability, pot life, surface hardness, heat resistance, and curing shrinkage rate, there are restrictions on the reactive diluents that should be used. Currently, the results are not necessarily satisfactory. Therefore, the acrylic sheet can be treated with a treatment liquid that can be commonly used for any type of ultraviolet curing paint, and there is no need to worry about solvent volatilization after adhesion, and there are no restrictions on pot life under any environment. There is a strong need for a method of increasing adhesion thereby. In order to eliminate the conventional drawbacks, the present invention provides a method for curing and adhering an ultraviolet curing paint to an acrylic sheet by irradiation with ultraviolet rays. - It is characterized by applying a thin layer of at least one of pyrrolidone, acrylic ester, or methacrylic ester, then applying an ultraviolet curing paint to the desired thickness on the treated surface, and then irradiating it with ultraviolet rays. The purpose is to satisfy photocurability, pot life, surface hardness, heat resistance, or curing shrinkage rate, and to improve adhesiveness. In the present invention, the treatment liquid applied to the acrylic sheet surface before applying the ultraviolet curable paint is preferably one that dissolves and swells the acrylic resin, such as N-vinyl-2-2-pyrrolidone, hydroxyethyl acrylate of acrylic acid ester, or tetrahydrochloride. Examples include furfuryl acrylate, benzyl methacrylate of methacrylic acid esters, glycidyl methacrylate, and ethylene glycol dimethacrylate, and these treatment liquids can be used as they are or as solutions that do not harm the sheet, such as alcohol. Hereinafter, the method of curing and adhering an ultraviolet curable paint to a methacrylate sheet of the present invention and its effects will be explained. [Example 1] 100% of the treatment solution shown in Table 1 was placed on an acrylic sheet.
% ethyl alcohol solution using a spin coater
Apply by spinning at 300 rpm and continue spinning for 1 minute. Afterwards, on the treated surface, an ultraviolet curing solution consisting of 100 parts by weight of 2,2-bis(4-acryloyloxydiethyleneoxyphenyl)propane (trade name, NK ester, A-BPE-4) and 2 parts by weight of benzoin isopropyl ether was applied. Apply the paint to a thickness of 100μm and irradiate it for 30 seconds with a 1KW high-pressure mercury lamp from a distance of 15cm. An adhesion test using a cross cut was conducted on each of the obtained samples, and the results shown in Table 2 were obtained.
【表】
なお比較例として、処理液を用いない場合と、
処理液としてアクリル樹脂を殆んど溶解、膨潤さ
せないヒドロキシプロピルアクリレートおよびカ
ルビトールアクリレートを用いた場合にいても行[Table] As a comparative example, when no treatment liquid is used and
Even when using hydroxypropyl acrylate and carbitol acrylate, which hardly dissolve or swell the acrylic resin, as the treatment liquid,
【表】
なつたのでその結果をも示した。
また同じく比較例として、処理液を用いない
で、かつ主成分としての2,2―ビス(4―アク
リロオキシジエチレンオキシフエニル)プロパン
に、試料No.1〜No.6の反応性稀釈剤を20、40、60
重量部、ベンゾインイソプロピルエーテルを2重
量%の割合になるように添加した試料について
も、同じ条件で硬化した時の硬化性(表面のべと
つきがなくなる時間)、密着性を評価したのでそ
の結果を第3表に示した。[Table] The results are also shown. Similarly, as a comparative example, the reactive diluent of Samples No. 1 to No. 6 was added to 2,2-bis(4-acrylooxydiethyleneoxyphenyl)propane as the main component without using a treatment liquid. 20, 40, 60
We also evaluated the curing properties (time for the surface to become sticky) and adhesion when cured under the same conditions for samples to which benzoin isopropyl ether was added at a ratio of 2% by weight. It is shown in Table 3.
【表】
ただしクロスカツトによる密着性試験とは、得
られた紫外線硬化塗膜に、素地に達するように1
mm角の碁盤目を100個カミソリの刃で入れ、その
塗膜表面に粘着テープを張りつけ、ついでテープ
を急激に剥離させて塗膜が付着している碁盤目の
数を測定した。
第2表中、密着性が100/100とあるのは上記密
着性試験の結果、100個の碁盤目中100個の碁盤目
が基材に付着していることを示している。
以上のように、紫外線硬化塗料のベース樹脂に
反応性稀釈剤の種類、添加量を調整することによ
つてアクリルシートへの密着性は改良できるが、
反面、硬化性の低下をもたらし、また表面硬度の
低下、硬化収縮の増大に伴なう表面平滑性の減少
が見られた。
一方、本発明の方法によれば、紫外線の照射に
よつて紫外線硬化塗料をアクリルシートへ強固な
密着性でもつて接着できる作用効果を生じること
がわかる。[Table] However, the cross-cut adhesion test means that the obtained ultraviolet-cured coating film is
100 mm square grids were made with a razor blade, adhesive tape was pasted on the surface of the coating film, and the tape was then rapidly peeled off to measure the number of grids to which the coating film was attached. In Table 2, the adhesion of 100/100 indicates that as a result of the adhesion test, 100 out of 100 grids adhered to the base material. As mentioned above, the adhesion to the acrylic sheet can be improved by adjusting the type and amount of reactive diluent added to the base resin of the UV-curable paint.
On the other hand, a decrease in curability was observed, and a decrease in surface smoothness was observed due to a decrease in surface hardness and an increase in curing shrinkage. On the other hand, it can be seen that the method of the present invention has the effect of adhering the ultraviolet curable paint to the acrylic sheet with strong adhesion by irradiation with ultraviolet rays.
Claims (1)
線硬化塗料を硬化、接着させる方法において、前
記アクリルシートの接着面にアクリルシートを溶
解、膨潤させるN―ビニル―2―ピロリドン、ま
たはアクリル酸エステルもしくはメタクリル酸エ
ステルのうち少なくともいずれか一つを薄く塗布
し、次にその処理面に紫外線硬化塗料を所望の厚
みに塗布し、ついで紫外線を照射することによつ
て紫外線硬化塗料を硬化させるアクリルシートへ
の紫外線硬化塗料の硬化接着方法。 2 アクリル酸エステルもしくはメタクリル酸エ
ステルが少なくとも前者がヒドロキシエチルアク
リレートまたはテトラヒドロフルフリールアクリ
レート、後者がベンジルメタクリレート、グリシ
ジルメタクリレートまたはエチレングリコールジ
メタクリレートの一つからなることを特徴とする
特許請求の範囲第1項記載のアクリルシートへの
紫外線硬化塗料の硬化接着方法。[Claims] 1. In a method of curing and adhering an ultraviolet curing paint to an acrylic sheet by irradiation with ultraviolet rays, N-vinyl-2-pyrrolidone, which dissolves and swells the acrylic sheet on the adhesive surface of the acrylic sheet, or Apply a thin layer of at least one of acrylic ester or methacrylic ester, then apply UV-curable paint to the desired thickness on the treated surface, and then cure the UV-curable paint by irradiating it with ultraviolet light. A method for curing and adhering UV-curable paint to acrylic sheets. 2. Claim 1, wherein the acrylic ester or methacrylic ester is at least one of hydroxyethyl acrylate or tetrahydrofurfuryl acrylate, and the latter one of benzyl methacrylate, glycidyl methacrylate, or ethylene glycol dimethacrylate. Method for curing and adhering an ultraviolet curing paint to an acrylic sheet as described in Section 1.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP56118176A JPS5819333A (en) | 1981-07-28 | 1981-07-28 | Method for bonding ultraviolet-curing paint to acrylic sheet and curing it |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP56118176A JPS5819333A (en) | 1981-07-28 | 1981-07-28 | Method for bonding ultraviolet-curing paint to acrylic sheet and curing it |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5819333A JPS5819333A (en) | 1983-02-04 |
JPS6332091B2 true JPS6332091B2 (en) | 1988-06-28 |
Family
ID=14730005
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP56118176A Granted JPS5819333A (en) | 1981-07-28 | 1981-07-28 | Method for bonding ultraviolet-curing paint to acrylic sheet and curing it |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5819333A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6217365B2 (en) * | 2012-12-25 | 2017-10-25 | 大日本印刷株式会社 | OPTICAL LAMINATE, MANUFACTURING METHOD THEREOF, AND POLARIZING PLATE AND IMAGE DISPLAY DEVICE USING THE SAME |
JP2017094231A (en) * | 2015-11-18 | 2017-06-01 | オリンパス株式会社 | Printing method, resin molding, and medical device |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5497633A (en) * | 1978-01-18 | 1979-08-01 | Mitsubishi Rayon Co Ltd | Coating composition and preparation of synthetic resin molding articles coated with said composition and having improved wear resistance and smoothness |
JPS5659878A (en) * | 1979-10-01 | 1981-05-23 | Gen Aniline & Film Corp | Abrasionnresistant radiationnhardenable coating |
-
1981
- 1981-07-28 JP JP56118176A patent/JPS5819333A/en active Granted
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5497633A (en) * | 1978-01-18 | 1979-08-01 | Mitsubishi Rayon Co Ltd | Coating composition and preparation of synthetic resin molding articles coated with said composition and having improved wear resistance and smoothness |
JPS5659878A (en) * | 1979-10-01 | 1981-05-23 | Gen Aniline & Film Corp | Abrasionnresistant radiationnhardenable coating |
Also Published As
Publication number | Publication date |
---|---|
JPS5819333A (en) | 1983-02-04 |
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