WO2017082058A1 - 爪または人工爪用光硬化性組成物およびこれを用いた被覆方法 - Google Patents
爪または人工爪用光硬化性組成物およびこれを用いた被覆方法 Download PDFInfo
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- WO2017082058A1 WO2017082058A1 PCT/JP2016/081780 JP2016081780W WO2017082058A1 WO 2017082058 A1 WO2017082058 A1 WO 2017082058A1 JP 2016081780 W JP2016081780 W JP 2016081780W WO 2017082058 A1 WO2017082058 A1 WO 2017082058A1
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- WIPO (PCT)
- Prior art keywords
- meth
- component
- nail
- photocurable composition
- nails
- Prior art date
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- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
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- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
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- C09D193/00—Coating compositions based on natural resins; Coating compositions based on derivatives thereof
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- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
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- B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
- B05D3/061—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation using U.V.
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Abstract
Description
(A)成分:ウレタン変性(メタ)アクリルオリゴマー
(B)成分:(メタ)アクリルアミドモノマー
(C)成分:酸性基を有する(メタ)アクリルモノマー
(D)成分:光開始剤。
[(A)成分]
本発明の組成物に係る(A)成分は、ウレタン変性(メタ)アクリルオリゴマーである。取扱の容易さの観点から、(A)成分は、25℃で液状である(すなわち流動性を有する)ことが好ましい。また、(A)成分は、組成物の硬化速度および形成される硬化物の靱性を高める観点から、1分子内に2個以上10個以下の(メタ)アクリル基を有することが好ましい。中でも、硬化物が脆くなりすぎることなく剪断接着力が向上することから、1分子内に(メタ)アクリル基を2つ有することがより好ましい。(A)成分は本発明の(B)成分~(D)成分との相溶性が良好なものを使用することが好ましい。
本発明に係る組成物の(B)成分は、(メタ)アクリルアミドモノマーである。組成物が(B)成分を含まない場合、形成される硬化物の耐久性(爪に対する接着維持性)が著しく低下する(比較例1~7参照)。この理由としては、特にこれに制限されないが、(B)成分を含まない組成物は、硬質な硬化物を形成しにくいため、形成される硬化物が湿度の影響を受けやすいことが考えられる。作業性の観点から、(B)成分は、25℃で液状である(すなわち流動性を有する)ことが好ましく、具体的には、25℃での粘度が約500mPa・s以下であることが好ましい。
本発明に係る組成物の(C)成分は、酸性基を有する(メタ)アクリルモノマーである。組成物が(C)成分を含まない場合、形成される硬化物の耐久性および剪断接着力が顕著に低下する(比較例8参照)。この理由としては、特に制限されないが、(C)成分を含まない組成物から形成される硬化物は、被着体との界面の密着性が乏しいこと、およびこれにより水分が当該界面に多く存在しやすいことが考えられる。酸性基としては、特に制限されず、カルボキシル基、リン酸基、スルホン酸基、およびこれらの塩の基などが挙げられる。中でも、密着性のさらなる向上の観点から、酸性基はカルボキシル基またはその塩の基であることが好ましい。
本発明に係る組成物の(D)成分は、光開始剤であり、可視光線、紫外線、X線、電子線等のエネルギー線の照射によりラジカル種を発生するラジカル系光開始剤であれば限定されない。
密着性のさらなる向上の観点から、本発明に係る組成物は、シラン系カップリング剤をさらに含むことが好ましい。シラン系カップリング剤は、エポキシ基、ビニル基、アクリル基またはメタクリル基および加水分解性シリル基(例えば、メトキシシリル基、エトキシシリル基などのアルコキシシリル基)を有するシラン系カップリング剤、フェニル基および加水分解性シリル基を有するポリオルガノシロキサン、エポキシ基および加水分解性シリル基を有するポリオルガノシロキサンなどが挙げられるが、これらに限定されるものではない。シラン系カップリング剤の具体例としては、アリルトリメトキシシラン、ビニルトリメトキシシラン、3-グリシドキシプロピルトリメトキシシラン、3-メタクリロキシプロピルトリメトキシシラン、3-アクリロキシプロピルトリメトキシシラン、3-クロロプロピルトリメトキシシランなどが挙げられるがこれらに限定されない。これらは1種単独で使用してもよいし、2種以上を併用してもよい。
本発明に係る組成物は、無機充填剤や有機充填剤などの充填剤をさらに含むことが好ましい。充填剤を添加することで、粘性やチクソ性だけでなく硬化性や靱性を調整することができる。無機充填剤としては、アルミナ、シリカ、アモルファスシリカなどが挙げられるが、これらに限定されるものではない。中でも、ヒュームドシリカが好ましく、未処理のヒュームドシリカがより好ましい。一方、有機充填剤としては、スチレンフィラー、ゴムフィラー、コアシェルアクリルフィラーなどが挙げられるが、これらに限定されるものではない。
本発明に係る組成物は、上記(B)成分および(C)成分以外の(メタ)アクリルモノマー(その他の(メタ)アクリルモノマー)を含んでもよく、1官能および/または2官能(メタ)アクリルモノマーを含んでもよい。
本発明では、本発明の特性を損なわない範囲において可塑剤を添加することができる。可塑剤の具体例としては、ポリカルボン酸エステル系可塑剤として、芳香族ポリカルボン酸エステル、フタル酸エステルとしてジオクチルフタレート(DOP)、ジブチルフタレート(DBP)、ジヘプチルフタレート(DHP)、ジイソノニルフタレート(DINP)、ジイソデシルフタレート(DIDP)、ブチルベンジルフタレート(BBP)など、トリメリット酸エステルとしてトリメリット酸トリオクチル(TOTM)、トリメリット酸トリイソデシル(TITM)など、ピロメリット酸エステルとしてピロメリット酸テトラオクチルなど、脂肪族ポリカルボン酸エステルとしてアジピン酸ジ2-エチルヘキシル(DOA)、アジピン酸イソデシル(DIDA)、セバシン酸ジ2-エチルヘキシル(DOS)、セバシン酸ジブチル(DBS)、マレイン酸ジ2-エチルヘキシル(DOM)、フマル酸ジブチル(DBF)、アゼライン酸ジ2-エチルヘキシル(DOZ)、エポキシヘキサヒドロフタル酸ジ2-エチルヘキシル、クエン酸トリオクチル、グリセロールトリアセテートなどが挙げられるが、これらに限定されるものではない。また、リン酸エステル系可塑剤として、トリメチルホスフェート、トリブチルホスフェート、トリ-(2-エチルヘキシル)ホスフェート、トリブトキシエチルホスフェート、トリフェニルホスフェート、トリクレジルホスフェート、アルキルアリルホスフェート、トリエチルホスフェート、トリ(クロロエチル)ホスフェート、トリスジクロロプロピルホスフェート、トリス(β-クロロプロピル)ホスフェート、オクチルジフェニルホスフェート、トリス(イソプロピルフェニル)ホスフェート、クレジルフェニルホスフェートなどが挙げられるがこれらに限定されるものではない。また、複数の可塑剤を組み合わせて使用することもできる。
本発明は、本発明に係る組成物を人間の爪または人工爪上に塗布して塗膜を形成後、エネルギー線を照射して塗膜を硬化する、人間の爪または人工爪の被覆方法についても提供する。当該方法における好ましい塗布および照射条件は、以下のとおりである。ここで、「人間の爪または人工爪上に塗布する」とは、人間の爪または人工爪の表面に直接塗布してもよいし、人間の爪または人工爪の表面に形成された1以上の層の最表面に塗布してもよいことを表す。中でも、本発明に係る組成物は、光を照射して硬化する際の発熱が少ないため、爪または人工爪(特に人間の爪)に直接塗布するベースコート剤として好適に使用することができる。すなわち、本発明の好ましい一実施形態は、ベースコート剤である上記の爪または人工爪用光硬化性組成物である。なお、本発明に係る組成物は、ベースコート剤以外の爪または人工爪用被覆剤(例えば、トップコート剤)として使用してもよい。
爪または人工爪用光硬化性組成物を調製するために下記成分を準備した:
[(A)成分:ウレタン変性(メタ)アクリルオリゴマー]
・ウレタンアクリルオリゴマー(2官能、重量平均分子量:4500)(UF-8001G 共栄社化学株式会社製)
[(B)成分:(メタ)アクリルアミドモノマー]
・4-アクリロイルモルホリン(ACMO(登録商標) KJケミカルズ株式会社製)
・N,N-ジメチルアクリルアミド(DMAA(登録商標) KJケミカルズ株式会社製)
[(B’)成分:(B)成分以外のモノマー]
・4-ヒドロキシブチルアクリレート(4HBA 日本化成株式会社製)
・2-ヒドロキシプロピルメタクリレート(HPMA 株式会社日本触媒製)
・イソボルニルアクリレート(ライトアクリレート(登録商標)IB-XA 共栄社化学株式会社製)(下記表1において「IB-XA」と称する)
・ネオペンチルグリコールジアクリレート(サートマーSR247 サートマー社製)(下記表1において「SR247」と称する)
・トリメチロールプロパントリメタクリレート(NKエステルTMPT 新中村化学工業株式会社製)(下記表1において「TMPT」と称する)
・エトキシ化(9)トリメチロールプロパントリアクリレート(サートマーSR502 サートマー社製)(下記表1において「SR502」と称する)
・テトラエチレングリコールジアクリレート(サートマーSR268 サートマー社製)(下記表1において「SR268」と称する)
[(C)成分:酸性基を有する(メタ)アクリルモノマー]
・メタクリル酸(三菱レイヨン株式会社製)
[(D)成分:光開始剤]
・2,4,6-トリメチルベンゾイル-ジフェニル-フォスフィンオキサイド(可視光型光開始剤)(LUCIRIN(登録商標)TPO BASF社製)(下記表1において「TPO」と称する)
・1-ヒドロキシシクロヘキシルフェニルケトン(非可視光型光開始剤)(Suncure84 Chemark社製)(下記表1において「84」と称する)
[シラン系カップリング剤]
・3-アクリロキシプロピルトリメトキシシラン(KBM-5103 信越化学工業株式会社製)(下記表1において「5103」と称する)
[充填剤]
・未処理のヒュームドシリカ(BET比表面積200m2/g)(アエロジル200 日本アエロジル株式会社製)(下記表1において「200」と称する)。
人間の手の指の爪に対してサンディングを実施した後、エタノールを主成分とする爪専用溶剤で埃や油分を取り除いた。爪の表面に、実施例1~2および比較例1~8の組成物を、ウェット状態でおよそ300μmの厚さとなるよう刷毛で塗布した。その後、ネイル用LEDランプ(定格電圧:240V 50~60Hz、消費電力:30W、波長:400~410nm)を10秒照射して組成物を硬化させて、ベースコート(硬化物)を形成した。同様の方法で、ベースコートの上に、カラーコートおよびトップコートを順に塗布し、硬化させた。カラーコートはPREGEL社製のスーパーカラーEX(色:パステルピーチ)を、トップコートはVETRO社製のVL-00を使用した。一人の人間の手の指の爪の総数(10本)について、施術して3週間後に剥離していない爪の数を「耐久性(本/10本)」とする。ここで剥離とは、全面が剥がれることおよび端部のみ剥がれることの両方を含む。実用性(ベースコート剤としての適用可能性)を考慮すると、「耐久性」は5以上であることが好ましく、6以上であることがより好ましい。
厚さ2.0mm×幅25mm×長さ100mmのアクリル板の上に、実施例1~2および比較例1~8の組成物を、ウェットの状態で厚さがおよそ300μmとなるよう刷毛で塗布した。ネイル用UVランプ(定格電圧:AC100V 50~60Hz、消費電力:36W、波長:350~400nm)を60秒照射して組成物を硬化させた。その際の硬化状態を下記の評価基準に従い判断して、「表面硬化性(UVランプ)」とした。
≪評価基準≫
○:表面に成分の滲みが生じない
×:表面に成分の滲みが生じる。
人体の手の爪に、実施例1~2および比較例1~8の組成物をドライ状態で厚さがおよそ100μmになる様に塗布した後、上記ネイル用LEDランプにて10秒照射して組成物を硬化させた。硬化時の手の感覚により以下の評価基準に従って「硬化時発熱」を確認した。作業性および被施術者の安全性を確保する観点から、「○」であることが好ましい:
≪評価基準≫
○:爪に熱さを感じない
×:爪に熱さを感じる。
実施例1~2および比較例1~8の組成物を入れた容器の端部から10cm離れたところに人間の鼻を固定し、人間の感覚で臭気を確認する。下記の評価基準に従い、「臭気」を確認した。取扱者への影響を考慮すると、「臭気」は「○」であることが好ましい:
≪評価基準≫
○:臭気に刺激が無い
×:臭気に刺激が有る。
厚さ2.0mm×幅25mm×長さ100mmのアクリル板2枚の間に、25mm×10mmで実施例1~2および比較例1~8の組成物を塗布して貼り合わせた。はみ出した組成物を除去した後、貼り合わせ部分の両端を治具で固定した。これをベルトコンベアー式UV照射器に通して積算光量30kJ/m2のUVを照射した後、治具を外して再度同条件で照射し、組成物を硬化した。この方法により、組成物の硬化物を含むテストピースをn=5で作成した。万能試験機を用いて、テストピースを剪断方向に引張速度50mm/分で引っ張り、最大荷重時の強度を「剪断接着力(MPa)」とし、被着体に対する硬化物の接着力の指標とした。詳細は、JIS K 6850(1999)に従う。表2の剪断接着力は、各テストピースの剪断接着力の平均値(n=5)を表し、初期の接着力を維持するためには、剪断接着力は2.5MPa以上であることが好ましい。
Claims (8)
- 下記の(A)~(D)成分を含む、爪または人工爪用光硬化性組成物:
(A)成分:ウレタン変性(メタ)アクリルオリゴマー
(B)成分:(メタ)アクリルアミドモノマー
(C)成分:酸性基を有する(メタ)アクリルモノマー
(D)成分:光開始剤。 - 前記(A)成分が、1分子中に(メタ)アクリル基を2つ有するウレタン変性(メタ)アクリルオリゴマーである、請求項1に記載の爪または人工爪用光硬化性組成物。
- 前記(A)成分100質量部に対して、前記(B)成分を15~50質量部含み、かつ、前記(C)成分を1~10質量部含む、請求項1または2に記載の爪または人工爪用光硬化性組成物。
- 前記(B)成分が、4-アクリロイルモルホリンおよびジアルキルアクリルアミドの少なくとも一方である、請求項1~3のいずれか1項に記載の爪または人工爪用光硬化性組成物。
- 前記(C)成分が(メタ)アクリル酸である、請求項1~4のいずれか1項に記載の爪または人工爪用光硬化性組成物。
- シラン系カップリング剤をさらに含む、請求項1~5のいずれか1項に記載の爪または人工爪用光硬化性組成物。
- 請求項1~6のいずれか1項に記載の爪または人工爪用光硬化性組成物を、人間の爪または人工爪上に塗布して塗膜を形成後、エネルギー線を照射して前記塗膜を硬化する、人間の爪または人工爪の被覆方法。
- ベースコート剤である、請求項1~6のいずれか1項に記載の爪または人工爪用光硬化性組成物。
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CN201680064589.9A CN108348446B (zh) | 2015-11-09 | 2016-10-26 | 指甲或人工指甲用光固化性组合物以及使用其的涂覆方法 |
US15/774,415 US10500144B2 (en) | 2015-11-09 | 2016-10-26 | Photocurable composition to be used on fingernails or artificial nails, and method for coating by using same |
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JP6912726B2 (ja) | 2021-08-04 |
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CN108348446A (zh) | 2018-07-31 |
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