JP2019509362A - 放射線硬化性コーティング組成物、耐引掻性コーティングを製造する方法、コーティング組成物を使用する方法、およびコーティング組成物でコーティングされた基材 - Google Patents
放射線硬化性コーティング組成物、耐引掻性コーティングを製造する方法、コーティング組成物を使用する方法、およびコーティング組成物でコーティングされた基材 Download PDFInfo
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- JP2019509362A JP2019509362A JP2018538588A JP2018538588A JP2019509362A JP 2019509362 A JP2019509362 A JP 2019509362A JP 2018538588 A JP2018538588 A JP 2018538588A JP 2018538588 A JP2018538588 A JP 2018538588A JP 2019509362 A JP2019509362 A JP 2019509362A
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- 239000013638 trimer Substances 0.000 claims abstract description 14
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 claims abstract description 13
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 claims abstract description 7
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims abstract description 7
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- SITYOOWCYAYOKL-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(3-dodecoxy-2-hydroxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COCCCCCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 SITYOOWCYAYOKL-UHFFFAOYSA-N 0.000 description 1
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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
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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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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- 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
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- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups 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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Abstract
Description
ii) 25.0〜37.0質量% の少なくとも1種の四官能性ポリエステルアクリレートモノマー、
iii) 8.0〜12.0質量% の少なくとも1種のジオールジアクリレートエステルおよび/または少なくとも1種のモノアクリレートエステル、
iv) 2.3〜3.5質量% の少なくとも1種の光開始剤、
v) 2.1〜3.1質量% の少なくとも1種の反応性アクリロイルトリアゾールUV吸収剤、
vi) 1.5〜2.0質量% の少なくとも1種の非反応性UV吸収剤、
vii) 0.7〜1.0質量% の少なくとも1種の立体障害アミン、および
viii) 0.4〜0.9質量% の少なくとも1種の流れ調整剤、
を含み、
質量パーセントの範囲は、記載された成分i)〜viii)の固形分の合計に対してであり、それらの合計は100質量%である。
ウレタンアクリレートは、一般にヒドロキシアルキルアクリレート、ジイソシアネートおよびポリオールの付加反応によって、またはヒドロキシアルキルアクリレートのポリイソシアネートへの直接付加反応によって製造することができる。これにより、光重合の硬化速度および効率と相まって、ポリウレタンコーティングの性能レベルを高め、多様な用途を実現することが可能になる。ウレタンアクリレートは、工業用途用の放射線硬化性コーティングに使用される。
本発明のコーティング組成物は、成分i)〜viii)の固形分の合計に対して、25.0〜37.0質量%の少なくとも1種の四官能性ポリエステルアクリレートモノマーを含む。コーティング組成物は、成分i)〜viii)の固形分の合計に対して、好ましくは、27.0〜37.0質量%の少なくとも1種の四官能性ポリエステルアクリレートモノマーを含む。
本発明によれば、放射線硬化性コーティング組成物は、成分iii)として、8.0〜12.0質量%の少なくとも1種のジオールジアクリレートエステルおよび/または少なくとも1種のモノアクリレートエステルを含む。より好ましくは、コーティング組成物は、成分i)〜viii)の固形分の合計に対して、9.0〜10.0質量%の少なくとも1種のジオールジアクリレートエステルおよび/または少なくとも1種のモノアクリレートエステルを含む。したがって、上記の質量パーセント範囲内で、コーティング組成物は、少なくとも1種のジオールジアクリレートエステルもしくは少なくとも1種のモノアクリレートエステルのどちらか、または少なくとも1種のジオールジアクリレートエステルと少なくとも1種のモノアクリレートエステルとの混合物を含み、ジオールジアクリレートエステルの使用が好ましい。
本発明のコーティング組成物は、成分i)〜viii)の固形分の合計に対して、2.3〜3.5質量%の少なくとも1種の光開始剤を含む。光開始剤は、放射線に曝露させるときに架橋反応を開始させるために使用する。
本発明のコーティング組成物は、ラジカルスカベンジャーとして少なくとも2つのUV吸収剤と少なくとも1種の立体障害アミンとの組み合わせを含む種々の光安定剤を含む。光安定剤の機能は、架橋されたコーティング膜の分解をもたらし得る化学的に反応性の中間成分の形成を防止することである。周囲からの有害なUV照射によってもたらされる化学結合の切断の結果として形成される、コーティング内のフリーラジカルは、このようにして捕捉され、不活性化される。化学結合の切断の結果として形成されるラジカルは、コーティング内で連鎖反応をもたらし、さらなる結合の切断が生じる。したがって、光安定剤の使用は、本発明のコーティング組成物から製造されたコーティングの長期的に有効な耐候安定性を保証するために、本発明にとって必須である。
本発明のコーティング組成物は、反応性アクリロイルトリアゾールUV吸収剤と非反応性UV吸収剤の組み合わせを含む。ここで、「反応性」とは、放射線硬化におけるUV吸収剤が、他の放射線硬化性成分と反応し、共重合により組み込まれることを意味する。対照的に、非反応性UV吸収剤は、コーティング組成物の他の成分と反応しない。
本発明のコーティング組成物は、成分i)〜viii)の固形分の合計に対して、ラジカルスカベンジャーとして作用する、0.7〜1.0質量%の少なくとも1種の立体障害アミンを含む。
本発明のコーティング組成物は、成分i)〜viii)の固形分の合計に対して、0.4〜0.9質量%の少なくとも1種の流れ調整剤を含む。
本発明のコーティング組成物は、好ましくは有機溶剤の使用により所望の塗布粘度に調整する。コーティング組成物は、有利には、コーティング組成物の総質量に対して、27.0〜70.0質量%の有機溶剤を含む。
ベース樹脂は、以下の成分を、記載した割合(グラムで表示)で一緒に混合することにより製造する。
1000mlの三つ口フラスコに、170.70gのイソシアネート三量体(Desmodur N3300、Bayer製)を仕込む。装置には、KPG羽根付き撹拌棒、滴下ロート、および希薄空気を導入するためのガス供給部を取り付けている。
1.5mmのノズルを介して3バールの圧縮空気をスプレーする重力供給カップガン(例えば、DeVilbissGTI重力スプレーガン)を用いて、スプレー塗布を行った。2回のスプレーパスで、必要な膜厚を塗布した。
膜/層の厚さの測定は、白色光干渉計(例えばFuchs製「FTM−Lite UVNIR膜厚測定器」という名称の)を用いて行った。試料の塗布後に測定された曇価は<1%であるべきである。
耐引掻性試験は、Taber Industries製5155 Abraser装置を使用して行った。引掻試験は、ASTM規格ASTM D1044−13(Standard Test Method for Resistance of Transparent Plastics to Surface Abrasion, Standard by ASTM International, 09/01/2013)に従って実施し、試験を行った。評価は、ASTM規格ASTM D1003−13(Standard Test Method for Haze and Luminous Transmittance of Transparent Plastics)に従って行った。
ポリカーボネートランプハウジング上のコーティングの耐引掻性は、Taber Abraser試験の実施時に、≦15のΔ曇価を示す(Taber Abraser試験で300回転後)場合に良好である。
Claims (15)
- 1,6−ヘキサメチレンジイソシアネートのイソシアヌレート三量体およびブタンジオールモノアクリレートから製造される少なくとも1種のウレタンアクリレートを含む、特にポリカーボネート表面上に耐引掻性コーティングを製造するための、放射線硬化性コーティング組成物であって、前記イソシアヌレート三量体は、19.6〜24.0質量%のNCO含量および175〜214当量を有し、
前記ウレタンアクリレートは、イソシアヌレート三量体とブタンジオールモノアクリレートとの質量比1.0:0.65〜1.0:0.9を有し、前記コーティング組成物は、
i) 45.0〜59.0質量% の少なくとも1種のウレタンアクリレート、
ii) 25.0〜37.0質量% の少なくとも1種の四官能性ポリエステルアクリレートモノマー、
iii) 8.0〜12.0質量% の少なくとも1種のジオールジアクリレートエステルおよび/または少なくとも1種のモノアクリレートエステル、
iv) 2.3〜3.5質量% の少なくとも1種の光開始剤、
v) 2.1〜3.1質量% の少なくとも1種の反応性アクリロイルトリアゾールUV吸収剤、
vi) 1.5〜2.0質量% の少なくとも1種の非反応性UV吸収剤、
vii) 0.7〜1.0質量% の少なくとも1種の立体障害アミン、および
viii) 0.4〜0.9質量% の少なくとも1種の流れ調整剤、
を含み、
質量パーセントの範囲が、記載された成分i)〜viii)の固形分の合計に対してであり、それらの合計が100質量%である、放射線硬化性コーティング組成物。 - 成分i)〜viii)の固形分の合計に対して、45.0〜55.0質量%の前記ウレタンアクリレートを含む、請求項1に記載のコーティング組成物。
- 前記四官能性ポリエステルアクリレートモノマーがエーテル結合を有する、請求項1または2に記載のコーティング組成物。
- 成分iii)がジオールジアクリレートエステルである、請求項1から3のいずれか一項に記載のコーティング組成物。
- 前記ジオールジアクリレートエステルが、最も長い炭素鎖に2〜12個の炭素原子を含む、請求項4に記載のコーティング組成物。
- 前記光開始剤が、少なくとも1種のリン含有化合物を含む、請求項1から5のいずれか一項に記載のコーティング組成物。
- 前記光開始剤が、少なくとも1種のリン含有化合物と少なくとも1種の芳香族α−ヒドロキシケトンとの混合物を含む、請求項6に記載のコーティング組成物。
- 前記反応性アクリロイルトリアゾールUV吸収剤が、アクリロイルフェノールベンゾトリアゾールである、請求項1から7のいずれか一項に記載のコーティング組成物。
- 前記立体障害アミンが、セバシン酸のジエステルである、請求項1から8のいずれか一項に記載のコーティング組成物。
- UV照射で硬化可能である、請求項1から9のいずれか一項に記載のコーティング組成物。
- クリアコート材料である、請求項1から10のいずれか一項に記載のコーティング組成物。
- i)ポリカーボネート表面上に、請求項1から11のいずれか一項に記載のコーティング組成物を塗布し、
ii)コーティング組成物をUV照射で硬化させる
ことにより、ポリカーボネート表面上に耐引掻性コーティングを製造する方法。 - 前記耐引掻性コーティングの乾燥膜厚が8〜25μmである、請求項12に記載の方法。
- 引掻傷および風化の影響から車両用ヘッドランプの表面を保護するためのコーティングを製造するための、請求項1から11のいずれか一項に記載のコーティング組成物を使用する方法。
- 請求項1から11のいずれか一項に記載の硬化コーティング組成物でコーティングされた基材。
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US20190016919A1 (en) | 2019-01-17 |
EP3405528B1 (de) | 2020-01-01 |
MX2018008944A (es) | 2018-11-09 |
KR20180095052A (ko) | 2018-08-24 |
JP6594558B6 (ja) | 2020-01-15 |
KR102190088B1 (ko) | 2020-12-11 |
BR112018014761A2 (pt) | 2018-12-11 |
BR112018014761B1 (pt) | 2022-08-30 |
EP3405528A1 (de) | 2018-11-28 |
WO2017125339A1 (de) | 2017-07-27 |
JP6594558B2 (ja) | 2019-10-23 |
RU2689747C1 (ru) | 2019-05-28 |
CN108473793B (zh) | 2020-05-12 |
ES2779007T3 (es) | 2020-08-13 |
CN108473793A (zh) | 2018-08-31 |
US10465092B2 (en) | 2019-11-05 |
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