JP6637437B2 - 透明フィルムをラミネートするためのuv反応性ホットメルト接着剤 - Google Patents
透明フィルムをラミネートするためのuv反応性ホットメルト接着剤 Download PDFInfo
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- JP6637437B2 JP6637437B2 JP2016556779A JP2016556779A JP6637437B2 JP 6637437 B2 JP6637437 B2 JP 6637437B2 JP 2016556779 A JP2016556779 A JP 2016556779A JP 2016556779 A JP2016556779 A JP 2016556779A JP 6637437 B2 JP6637437 B2 JP 6637437B2
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- Prior art keywords
- acrylate
- meth
- hot melt
- melt adhesive
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- TVIDDXQYHWJXFK-UHFFFAOYSA-N n-Dodecanedioic acid Natural products OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 claims 1
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- 239000003999 initiator Substances 0.000 description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 7
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 239000004926 polymethyl methacrylate Substances 0.000 description 6
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 5
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Classifications
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives 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; Adhesives based on derivatives of such polymers
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- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
- B32B37/1207—Heat-activated adhesive
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
- C08G18/673—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen containing two or more acrylate or alkylacrylate ester groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/675—Low-molecular-weight compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
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- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
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Description
a) 少なくとも1つのUV硬化性ウレタン(メタ)アクリレート、ここで、該ウレタン(メタ)アクリレートは、モル過剰のヒドロキシおよび/またはアミン変性(メタ)アクリレート)によりNCO官能性ポリウレタンプレポリマーを修飾することにより得ることができ;
b) 少なくとも1つの(メタ)アクリレートモノマー又はオリゴマー、ここで、少なくとも1つの(メタ)アクリレートモノマーおよび/またはオリゴマーは、50〜400mgKOH/g、好ましくは100〜200mgKOH/gの酸価を有する酸修飾された(メタ)アクリレートを含んでなり;および
c) 少なくとも1つの光開始剤
を含有するUV硬化性ホットメルト接着剤組成物に関する。
a) 50〜85重量%、特に、55〜75重量%の少なくとも1つのUV硬化性ウレタン(メタ)アクリレート;
b) 15〜45重量%、特に、25〜35重量%の少なくとも1つの(メタ)アクリレートモノマー又はオリゴマー;および
c) 0.02〜5重量%、特に、0.1〜3重量%の少なくとも1つの光開始剤
を含有する。
20gのVoranol 2000L(ポリプロピレングリコール)、5gのDynacoll 7360 (ポリエステルポリオール)、13gのElvacite 2013(メチルメタクリレート/ブチルメタクリレートコポリマー)、及び1gのIrganox 1010(抗酸化剤)を、ガラス反応器中に秤量し、メタクリレートコポリマーがポリプロピレングリコール中に溶解するまで、攪拌下に真空中で130℃〜140℃までゆっくり加熱した。その後、0.1gのリン酸および5.5gのIPDI(Bayer社製のDesmodur I)を添加し、混入させた。生成物を100℃〜110℃へ調節し、その後、0.5gの触媒BDTLを計量した。保護ガス雰囲気下の反応時間は60〜120分であり、その後、プレポリマーは、2.4%のNCO含有量および110℃で10,000mPasの粘度を有していた。
90gのVoranol 2000L(ポリプロピレングリコール)、15gのDynacoll 7360(ポリエステルポリオール)、45gのElvacite 2013(メチルメタクリレート/ブチルメタクリレートコポリマー)、及び4gのIrganox 1010(抗酸化剤)を、ガラス反応器中に秤量し、メタクリレートコポリマーがポリプロピレングリコール中に溶解するまで、攪拌下に真空中で130℃〜140℃までゆっくり加熱した。その後、10gのAC540および10gのAC578(変性PEワックス; Honeywell社製)を添加し均質化した。次に、0.5gのリン酸および19gのIPDI(Bayer社製のDesmodur I)を添加し、混入させた。生成物を100℃〜110℃へ調節し、その後、2gの触媒BDTLを計量した。保護ガス大気の下の反応時間は60〜120分だった、その後、プレポリマーは、1.4%のNCO含有量および110℃で16,000mPasの粘度を有していた。
実施例1での本発明によるホットメルト接着剤を、100℃でノズルによって透明フィルム(Senosan社製 ABS/PMMA高光沢アクリルAM 1800 TopX)上に塗布した。塗布量は30g/m2であった。同じ温度で、次いで、フィルムをメラミン被覆プレートに対し、50N/mmのライン圧でプレスした。このとき、プレッシャーローラーとメラミンプレートは同一温度を有していた。供給速度は8m/分であった。コーティングに引き続き直ちに、UVラジエーター(Gaドープした水銀灯)により、約100W/cmのキャパシティーで照射を行い、その時間の間、供給速度を維持した。
Claims (11)
- (a) 全組成物に対して50〜85重量%の、少なくとも1つのUV硬化性ウレタン(メタ)アクリレート、ここで、該ウレタン(メタ)アクリレートは、モル過剰のヒドロキシおよび/またはアミン変性(メタ)アクリレートとNCO官能性ポリウレタンプレポリマーの反応生成物であり;
(b) 全組成物に対して15〜45重量%の、少なくとも1つの(メタ)アクリレートモノマー又はオリゴマー、ここで、少なくとも1つの(メタ)アクリレートモノマー又はオリゴマーは、50〜400mgKOH/gの酸価を有する酸修飾された(メタ)アクリレートを含んでなり;および
(c) 全組成物に対して0.02〜5重量%の、少なくとも1つの光開始剤
を含有する、フィルムをメラミン又はPVCでコーティングされた成型体上へラミネートするためのUV硬化性ホットメルト接着剤組成物。 - 少なくとも1つの(メタ)アクリレートモノマー又はオリゴマーは、モノマーのおよび/またはオリゴマーの(メタ)アクリレートの混合物である、酸価が50〜400mgKOH/gの少なくとも1つの酸修飾された(メタ)アクリレートを、それぞれモノマーのおよび/またはオリゴマーの(メタ)アクリレートの全質量に対して5〜40重量%の量で含有することを特徴とする請求項1に記載のUV硬化性ホットメルト接着剤組成物。
- モノマーのおよび/またはオリゴマーの(メタ)アクリレートの混合物は、ポリエステルアクリレート、プロポキシル化ネオペンチルグリコールジアクリレート、2-(2-エトキシ
エトキシ)エチルアクリレートおよびテトラヒドロフルフリルアクリレートから選択された一以上の(メタ)アクリレートをさらに含有することを特徴とする、請求項2に記載のUV硬化性ホットメルト接着剤組成物。 - NCO官能性ポリウレタンプレポリマーは、
(a) 少なくとも1つのポリエーテルポリオール、少なくとも1つのポリエステルポリオール、又はそれらの混合物、及び任意に、ヒドロキシ基および/またはカルボキシル基含有(メタ)アクリレート、無水マレイン酸又はアクリル酸とポリエチレンのコポリマー、および/または酸化ポリエチレンワックスと、
(b) 化学量論過剰の少なくとも1つのポリイソシアネート
との反応生成物であることを特徴とする、請求項1〜3のいずれかに記載のUV硬化性ホットメルト接着剤組成物。 - (d) ポリエーテルポリオールは、1800〜2200g/molの分子量Mw、および50〜60mgKOH/gのヒドロキシル価を有する、ポリプロピレングリコールであり;
(e) ポリエステルポリオールは、1,6-ヘキサンジオールとアジピン酸又は1,12-ドデカンジオン酸に基づく、コポリエステルであり;
(f) ヒドロキシ基-あるいはカルボキシル基含有(メタ)アクリレートは、ヒドロキシ修飾されたメチルメタクリレート/ブチルメタクリレートコポリマーであり;
(g) エチレンと無水マレイン酸またはアクリル酸とのコポリマーは、コポリマーに対して、1〜5重量%の無水マレイン酸単位および/または5〜20重量%のアクリル酸ユニットを有するポリエチレンワックスであり;
(h) 前記少なくとも1つのポリイソシアネートは、ジイソシアネート、ポリマーイソシアネート、およびポリエステルとジイソシアネートの2官能性プレポリマーから選択され;
および/または
(i) 化学量論過剰のポリイソシアネートは、NCO基:OH基のモル比に関して、1.25:1〜2.5:1である
ことを特徴とする請求項4に記載のUV硬化性ホットメルト接着剤組成物。 - 前記少なくとも1つのUV硬化性ウレタンアクリレートを製造するために用いられるヒドロキシ基および/またはアミン修飾された(メタ)アクリレートは、アクリレート官能価が1〜6、およびヒドロキシおよび/またはアミン官能価が1〜4であるモノマーのおよび/またはオリゴマーの(メタ)アクリレートであることを特徴とする、請求項1〜5のいずれかに記載のUV硬化性ホットメルト接着剤組成物。
- 少なくとも1つのUV硬化性ウレタンアクリレートは、
(j) 2000g/molを超える分子量Mwを有する、および/または
(k) 1〜50mgKOH/gのヒドロキシル価を有する
ことを特徴とする請求項1〜6のいずれかに記載のUV硬化性ホットメルト接着剤組成物。 - 該組成物は、ワックス、樹脂、接着促進剤、安定剤、抗酸化剤、流れ促進剤、充填剤、湿潤剤、脱気剤、染料、顔料および可塑剤からなる群から選択された一以上の化合物をさらに含有することを特徴とする、請求項1〜7のいずれかに記載のUV硬化性ホットメルト接着剤組成物。
- フィルムをメラミン又はPVCでコーティングされた成型体上へラミネートする方法であって、該方法は、請求項1〜8のいずれかに記載のUV硬化性ホットメルト接着剤組成物を、成型体の表面、フィルムの表面、又は両者の上に塗布し、次いで、成型体とフィルムを一緒に付着させることを特徴とする方法。
- メラミンあるいは塩化ビニルコーティングを含んでなる成型体と、それに付着しかつ請求項9に記載の方法により製造されたフィルムとから構成される複合材料。
- 請求項1〜8のいずれかに記載のUV硬化性ホットメルト接着剤組成物の、フィルムを成型体へ接着させるための使用。
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DE102014204465.0A DE102014204465A1 (de) | 2014-03-11 | 2014-03-11 | UV-reaktiver Schmelzklebstoff für die Laminierung transparenter Folien |
DE102014204465.0 | 2014-03-11 | ||
PCT/EP2015/054423 WO2015135800A1 (de) | 2014-03-11 | 2015-03-03 | Uv-reaktiver schmelzklebstoff für die laminierung transparenter folien |
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WO2016040483A1 (en) * | 2014-09-09 | 2016-03-17 | H.B. Fuller Company | A disposable article including at least one elastic bonded region |
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CN106939069A (zh) * | 2016-11-28 | 2017-07-11 | 江南大学 | 一种可uv固化水性含氟有机硅和环氧复合改性聚氨酯树脂的制备方法 |
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EP3116925A1 (de) | 2017-01-18 |
DE102014204465A1 (de) | 2015-09-17 |
RU2016139570A3 (ja) | 2018-10-23 |
JP2017512242A (ja) | 2017-05-18 |
CN106103524B (zh) | 2020-01-17 |
CL2016002280A1 (es) | 2016-12-16 |
PL3116925T3 (pl) | 2019-06-28 |
AU2015230204A1 (en) | 2016-10-27 |
ES2708828T3 (es) | 2019-04-11 |
WO2015135800A1 (de) | 2015-09-17 |
CN106103524A (zh) | 2016-11-09 |
RU2016139570A (ru) | 2018-04-11 |
RU2687096C2 (ru) | 2019-05-07 |
US20160376482A1 (en) | 2016-12-29 |
AU2015230204B2 (en) | 2018-06-28 |
EP3116925B1 (de) | 2019-01-02 |
US10407596B2 (en) | 2019-09-10 |
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