JP6400849B2 - 電磁線硬化型被覆組成物 - Google Patents
電磁線硬化型被覆組成物 Download PDFInfo
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- JP6400849B2 JP6400849B2 JP2017529993A JP2017529993A JP6400849B2 JP 6400849 B2 JP6400849 B2 JP 6400849B2 JP 2017529993 A JP2017529993 A JP 2017529993A JP 2017529993 A JP2017529993 A JP 2017529993A JP 6400849 B2 JP6400849 B2 JP 6400849B2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- 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
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
-
- C—CHEMISTRY; METALLURGY
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Description
従って、本発明の目的は、硬度、耐性および他の基本的な特性を劣化させることなく、改善された屈曲特性を有する保護用および/または装飾用の膜(フィルム)、特に触覚膜(haptic films)を生成する被覆組成物(coating composition)を実現することである。
本発明による被覆組成物は、(a)少なくとも1種のウレタン(メタ)アクリラートを40〜70重量%、例えば50〜60重量%または40〜50重量%、(b)少なくとも1つのオレフィン性炭素−炭素二重結合を有する少なくとも1種の反応性希釈剤を20〜50重量%、例えば30〜40重量%または40〜50重量%、および(c)少なくとも1種の光開始剤を0.5〜10重量%、例えば1〜10重量%、2〜8重量%または3〜6重量%、含む紫外線硬化型被覆組成物である。好ましい実施形態において、そのウレタン(メタ)アクリラート(a)は、(a1)少なくとも1種のポリカプロラクトンポリオールと、(a3)少なくとも1種のポリイソシアナートと(a4)少なくとも1種のヒドロキシアルキル(メタ)アクリラートの間の(a2)少なくとも1種の付加物と、の間の反応において得られる生成物である。同様の好ましい実施形態において、そのポリカプロラクトンポリオール(a1)は、(a5)少なくとも1種のポリアルコキシル化ポリオールと、(a6)少なくとも1種のカプロラクトン単量体(モノマー)、例えばα−、β−、γ−、δ−または最も好ましくはε−ポリカプロラクトンとの間の反応において得られる生成物である。
ポリカプロラクトンポリオールの生成が、ε−カプロラクトンを、次の特性(表1)を有する、アルコキシル化トリメチロールプロパンポリオール3165TM、ポリオール3380TM(スウェーデン、ペルストルプ アーベー(Perstorp AB))またはプロポキシル化ネオペンチルグリコールポリオールR2490TM(スウェーデン、ペルストルプ アーベー(Perstorp AB))のいずれか一方と、次(表2)の特性を有するポリカプロラクトンポリオールを生成するモル比で、反応(開環および縮合)させることによって、行われた。
イソホロンジイソシアナートと2−ヒドロキシエチルアクリラートの間の付加物は、65〜70℃で、抑制剤として4−メトキシフェノールを用い、触媒としてラウリン酸ジブチルスズを用いて、上述のジイソシアナート 対 上述のアクリラートのモル比1.0:0.95で生成された。
例1で得られたポリカプロラクトンポリオールと、例2で得られた付加物とを、ヒドロキシル基対イソシアナート基のモル比1.0:0.9で反応させて、ウレタンアクリラートが生成された。その反応は、60℃で、抑制剤としてブチル化ヒドロキシトルエン、触媒としてラウリン酸ジブチルスズ、および溶媒としてトルエンを用いて行われた。その反応は、NCO含有量を分析することによってモニターされ、NCO値がゼロに近くなったときに反応を停止させた。次(表3)の特性を有する生成物が生成された。
− SCDによるTg(ガラス転移温度):メトラー社(Mettler)のDSCで測定。10mgの試料が40μLのアルミニウム・パン(pan)で分析された。温度範囲は−100〜+120℃。傾斜(ramp)10℃/分。
例3で得られたウレタンアクリラートA、B、CまたはDを44.8重量部と、反応性希釈剤としてのトリプロピレングリコールジアクリラートを49.7重量部と、光開始剤としてのイルガキュア(Irgacure(登録商標))1173(バスフ社(BASF AG))を5.5重量部とを混合することによって、紫外線硬化型被覆が、調整されまたは生成された。得られた被覆は、Kバーを用いてガラス・パネルおよびアルミニウム・パネル上に被覆されて、厚さ30〜40μmの湿潤膜が得られた。硬化は、5〜6J/cm2の紫外線照射線量で、H蒸気ランプ(Fusion F600最高240W/cm)下で行われた。硬化した膜は次(表4)の特性を示した。
− アセトン・スポット試験:SS 83 91 18による評価。
− DMAによるTg(℃、最高E”):メトラー社(Mettler)のDMAを用いて測定。テンション・モード。温度範囲−100乃至150℃(傾斜3℃/分)。振幅および周波数は、それぞれ15μmおよび1Hzに等しい。各試料の3つの標本が試験され、平均値が報告された。
例3で得られたウレタンアクリラートCを44.8重量部、またはウレタンアクリラートを44.8重量部(ここで、ポリカプロラクトンポリオールにおいて使用されたポリアルコキシル化トリメチロールプロパン(Polyol 3380TM)が非アルコキシル化トリメチロールプロパンで置換された)と、反応性希釈剤としてのジプロピレングリコールジアクリラートを49.7重量部と、光開始剤としてのイルガキュア(Irgacure(登録商標))1173(バスフ社(BASF AG))を5.5重量部とを混合することによって、紫外線硬化型被覆が、調整されまたは生成された。得られた被覆は、ガラス・パネルおよびアルミニウム・パネル上に被覆され、例4におけるように硬化された。硬化された膜(フィルム)は次(表5)の特性を示した。
− アセトン・スポット試験:SS 83 91 18による評価。
− DMAによるTg(℃、最高E”)およびE’:メトラー社(Mettler)のDMAを用いて測定。テンション・モード。温度範囲−100乃至150℃(傾斜3℃/分)。振幅および周波数は、それぞれ15μmおよび1Hzに等しい。各試料の3つの標本が試験され、平均値が報告された。
− Mc∝(3ρRT)/E’。ここで、E’はゴム状プラトー(rubbery plateau:ゴム状平坦領域)上の貯蔵弾性率(storage modulus)(J・m−3)であり、ρはTにおける材料密度(kg・m3)であり、Rは気体定数(8,314J・mol−1・K−1)であり、Tはゴム状プラトーにおける温度(K)である。
ウレタンアクリラートAまたはCを44.8重量部、または例3で得られたウレタンアクリラートCおよびEの60/40(重量)混合物を44.8重量部と、反応性希釈剤としてのジプロピレングリコールジアクリラートを49.7重量部と、光開始剤としてのイルガキュア(Irgacure(登録商標))1173(バスフ社(BASF AG))を5.5重量部とを混合することによって、紫外線硬化型被覆が、調製されまたは生成された。デュテロン(Deuteron(登録商標))UV RS20(無機変性ポリエチレンワックス分散液、デュテロン社(Deuteron GmbH))またはオルガソル(Orgasol(登録商標))2001 UD NAT1(ポリアミド12、仏国、アルケマ社(Arkema))が、艶消剤として用いられて、得られた組成物に対してその組成物で(を基準にして)計算された10重量%の量が添加された。得られた被覆が、例4におけるようにガラス・パネルおよびアルミニウム・パネル上に被覆された。硬化した膜は次(表6)の特性を示した。
Claims (19)
- (a)少なくとも1種のポリカプロラクトンポリオール(a1)と少なくとも1種の付加物(a2)の間の反応の生成物である少なくとも1種のウレタン(メタ)アクリラートを40〜70重量%を含み、
前記付加物(a2)は、少なくとも1種のポリイソシアナート(a3)と少なくとも1種のヒドロキシアルキル(メタ)アクリラート(a4)の間の反応の生成物であり、
前記ポリカプロラクトンポリオール(a1)は、少なくとも1種のポリアルコキシル化ポリオール(a5)と少なくとも1種のカプロラクトン単量体(a6)の間の反応の生成物であり、
さらに、
(b)少なくとも1つのオレフィン性炭素−炭素二重結合を有する少なくとも1種の反応性希釈剤を20〜50重量%と、
(c)少なくとも1種の光開始剤を0.5〜10重量%と、
(d)少なくとも1種の艶消剤を、前記の成分(a)乃至(c)の合計に基づいて計算して1〜15重量%と、
を含む紫外線硬化型被覆組成物であることを特徴とする、被覆組成物。 - 前記艶消剤(d)が、ポリアミド、微粉化バイオポリマー、合成アモルファスシリカ、表面処理された合成アモルファスシリカ、微粒子穏微晶質アモルファスシリカ、層状カオリンおよび/または無機変性ポリエチレンワックス分散液である、請求項1に記載の被覆組成物。
- 前記ポリカプロラクトンポリオール(a1)が、2〜10個のカプロラクトン単位/分子を有する、請求項1または2に記載の被覆組成物。
- 前記ポリカプロラクトンポリオール(a1)が、−40℃未満のガラス転移温度(Tg)を有する、請求項1乃至3のいずれかに記載の被覆組成物。
- 前記ポリカプロラクトンポリオール(a1)が、1000〜6000g/molの分子量(Mw)を有する、請求項1乃至4のいずれかに記載の被覆組成物。
- 前記付加物(a2)は、ポリイソシアナート(a3)対ヒドロキシアルキル(メタ)アクリラート(a4)のモル比1:0.8乃至1:1で得られるものである、請求項1乃至5のいずれかに記載の被覆組成物。
- 前記ポリイソシアナート(a3)が、脂肪族または脂環式ジまたはトリイソシアナート、および/またはそのまたはそれを有するNCO官能性二量体、三量体またはポリマーである、請求項1乃至6のいずれかに記載の被覆組成物。
- 前記ポリイソシアナート(a3)が、ヘキサメチレンジイソシアナート、イソホロンジイソシアナート、ジシクロヘキシルメタンジイソシアナート、テトラヒドロフランジイソシアナート、シクロヘキシレンジイソシアナートおよび/またはノナントリイソシアナート、および/またはそのまたはそれを有するNCO官能性二量体、三量体またはポリマーであることを特徴とする、請求項1乃至7のいずれかに記載の被覆組成物。
- 前記ヒドロキシアルキル(メタ)アクリラート(a4)が、ヒドロキシエチル(メタ)アクリラート、ヒドロキシプロピル(メタ)アクリラート、トリメチロールエタンジ(メタ)アクリラート、トリメチロールプロパンジ(メタ)アクリラート、トリメチロールブタンジ(メタ)アクリラートおよび/またはペンタエリスリトールトリ(メタ)アクリラートであることを特徴とする、請求項1乃至8のいずれかに記載の被覆組成物。
- 前記ポリアルコキシル化ポリオール(a5)が、1〜30個のエトキシ、プロポキシおよび/またはブトキシ単位/分子を有するポリエトキシル化、ポリプロポキシル化および/またはポリブトキシル化ジオールまたはトリオールである、請求項1乃至9のいずれかに記載の被覆組成物。
- 前記ポリアルコキシル化ポリオール(a5)が、ポリエトキシル化および/またはポリプロポキシル化ネオペンチルグリコール、グリセロール、トリメチロールエタン、トリメチロールプロパンまたはトリメチロールブタンである、請求項1乃至10のいずれかに記載の被覆組成物。
- 前記カプロラクトン単量体(a6)がε−カプロラクトンである、請求項1乃至11のいずれかに記載の被覆組成物。
- 前記反応性希釈剤(b)が、少なくとも1種の、アルキル(メタ)アクリラート、ビニル(メタ)アクリラート、(メタ)アリル(メタ)アクリラート、ポリエステル(メタ)アクリラート、エポキシ(メタ)アクリラート、ウレタン(メタ)アクリラートおよび/またはメラミン(メタ)アクリラートである、請求項1乃至12のいずれかに記載の被覆組成物。
- 前記反応性希釈剤(b)が、イソボルニル(メタ)アクリラート、ジプロピレングリコールジ(メタ)アクリラート、トリプロピレングリコールジ(メタ)アクリラート、ヘキサンジオールジ(メタ)アクリラートおよび/またはトリメチロールプロパントリ(メタ)アクリラートである、請求項1乃至13のいずれかに記載の被覆組成物。
- 前記光開始剤(c)が、ベンゾインエーテル、アシルホスフィン、アセトフェノン、アミノアルキルフェノン、ベンゾフェノンおよび/またはアントラキノンである、請求項1乃至14のいずれかに記載の被覆組成物。
- さらに、少なくとも1種の顔料、充填剤および/または染料を含む、請求項1乃至15のいずれかに記載の被覆組成物。
- さらに、少なくとも1種の紫外線安定剤、流動/レベリング剤、レオロジー剤、抑制剤および/または紫外線吸収剤を含む、請求項1乃至16のいずれかに記載の被覆組成物。
- 装飾用および/または保護用トップコートを得るための、請求項1乃至17のいずれかに記載の被覆組成物の使用。
- 触覚装飾用および/または保護用トップコートを得るための、請求項2乃至17のいずれかに記載の被覆組成物の使用。
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SE1400571A SE537921C2 (sv) | 2014-12-04 | 2014-12-04 | Radiation curing coating composition |
PCT/SE2015/000072 WO2016089271A1 (en) | 2014-12-04 | 2015-11-26 | Radiation curing coating composition |
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KR (2) | KR102492657B1 (ja) |
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SE540989C2 (en) * | 2017-08-31 | 2019-02-19 | Perstorp Ab | Novel oligomer or polymer and composition comprising the same |
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CN113227165A (zh) * | 2018-12-26 | 2021-08-06 | 株式会社可乐丽 | 涂覆性优异的组合物 |
EP3990513A1 (en) * | 2019-06-27 | 2022-05-04 | Allnex Belgium, S.A. | Curable compositions with outdoor performances |
EP3838592A1 (en) * | 2019-12-17 | 2021-06-23 | Evonik Operations GmbH | Composition comprising polyesters for additive manufacturing |
CN113528000B (zh) * | 2021-07-09 | 2022-06-21 | 广东华润涂料有限公司 | 可辐射固化的双组分水性涂料组合物以及由其制成的涂布制品 |
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EP3227396A1 (en) | 2017-10-11 |
KR20170092600A (ko) | 2017-08-11 |
TW201627436A (zh) | 2016-08-01 |
US20170355807A1 (en) | 2017-12-14 |
KR102429909B1 (ko) | 2022-08-04 |
TWI564353B (zh) | 2017-01-01 |
EP3227396B1 (en) | 2019-06-26 |
SE1400571A1 (sv) | 2015-11-24 |
KR20220112308A (ko) | 2022-08-10 |
SE537921C2 (sv) | 2015-11-24 |
CN111040620A (zh) | 2020-04-21 |
CN107001856A (zh) | 2017-08-01 |
US10167359B2 (en) | 2019-01-01 |
CN107001856B (zh) | 2019-12-17 |
EP3227396A4 (en) | 2018-08-08 |
KR102492657B1 (ko) | 2023-01-26 |
WO2016089271A1 (en) | 2016-06-09 |
JP2018501348A (ja) | 2018-01-18 |
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