JP7060586B2 - 含フッ素共重合体 - Google Patents
含フッ素共重合体 Download PDFInfo
- Publication number
- JP7060586B2 JP7060586B2 JP2019513572A JP2019513572A JP7060586B2 JP 7060586 B2 JP7060586 B2 JP 7060586B2 JP 2019513572 A JP2019513572 A JP 2019513572A JP 2019513572 A JP2019513572 A JP 2019513572A JP 7060586 B2 JP7060586 B2 JP 7060586B2
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- JP
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- Prior art keywords
- fluorine
- monomer
- containing copolymer
- coating composition
- curing agent
- 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.)
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- 229920001577 copolymer Polymers 0.000 title claims description 166
- 239000011737 fluorine Substances 0.000 title claims description 144
- 229910052731 fluorine Inorganic materials 0.000 title claims description 144
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims description 140
- 239000000178 monomer Substances 0.000 claims description 195
- 239000003795 chemical substances by application Substances 0.000 claims description 88
- 239000008199 coating composition Substances 0.000 claims description 87
- 238000000576 coating method Methods 0.000 claims description 85
- 239000011248 coating agent Substances 0.000 claims description 82
- -1 isocyanate compound Chemical class 0.000 claims description 71
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 239000000470 constituent Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 37
- 239000012948 isocyanate Substances 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 29
- 229920001567 vinyl ester resin Polymers 0.000 claims description 29
- 238000004519 manufacturing process Methods 0.000 claims description 28
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 20
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 19
- 239000000758 substrate Substances 0.000 claims description 18
- 125000001931 aliphatic group Chemical group 0.000 claims description 15
- 230000009477 glass transition Effects 0.000 claims description 13
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- 125000002723 alicyclic group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 8
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 claims description 7
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 7
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 6
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- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 11
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- 239000003960 organic solvent Substances 0.000 description 10
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- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
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- 229910001369 Brass Inorganic materials 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
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- 229910003872 O—Si Inorganic materials 0.000 description 5
- 229920001807 Urea-formaldehyde Polymers 0.000 description 5
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 5
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- 150000002978 peroxides Chemical class 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
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- 238000007334 copolymerization reaction Methods 0.000 description 4
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- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920002799 BoPET Polymers 0.000 description 3
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- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 2
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Description
従来、屋外で長期間暴露され、直射日光を受け、酸性雨や鳥糞、洗剤、日焼け止めクリーム等の種々の薬害を受けることになる各種用途、例えば、自動車外装フィルムや自動車塗装保護フィルム、ウィンドウフィルム、マーキングフィルムなど、主として樹脂を基体としたフィルム類、更に屋内外で使用される各種建材や物品に対し、耐候性と耐薬品性などを付与するために、有機溶剤に溶解された含フッ素樹脂を主成分とする塗料又は塗料組成物が塗布されることが行われてきた。特にジメチルシロキサン構造を側鎖あるいは主鎖骨格に有する含フッ素共重合体は、耐候性や耐薬品性を与えるだけでなく、優れた耐汚染性と撥水撥油性、すべり性等を付与できることから、広範な分野で有効に用いられてきたが、耐キズ性の向上が求められていた。
従来の自己修復性を与える含フッ素共重合体は、耐候性や耐薬品性と耐キズ性には優れるものの、ジメチルシロキサン構造を側鎖あるいは主鎖骨格に有する含フッ素共重合体にみられる高い耐汚染性や撥水撥油性、すべり性を有さないことから、当該特性が要求される用途への適用が困難であった。また、ポリジメチルシロキサン構造を有し、含フッ素共重合体を含まない自己修復性塗料組成物は、高いすべり性を発現するが、含フッ素共重合体を含んだ塗料組成物に比べて耐候性、耐や薬品性に劣るといった課題があった。
(B)下記の一般式(1)で表される化合物及び下記一般式(2)で表される化合物から選ばれる1種以上の有機ケイ素化合物〔以下、単量体(B)という〕を構成単量体中0.001~10モル%、
(C)ビニルエーテル、ビニルエステル、メタクリル酸エステル及びアクリル酸エステルから選ばれる単量体であって、硬化反応性基を有さず、炭素数1~20の脂肪族飽和炭化水素基を有し、該単量体のホモポリマーのガラス転移温度が0℃未満である単量体から選ばれる1種以上の単量体〔以下、単量体(C)という〕を構成単量体中5~40モル%、並びに
(D)ビニルエーテル、ビニルエステル、アリルエーテル、メタクリル酸エステル及びアクリル酸エステルから選ばれる単量体であって、硬化反応性基を有する単量体から選ばれる1種以上の単量体〔以下、単量体(D)という〕を構成単量体中1~25モル%
含む含フッ素共重合体であって、
ガラス転移温度が-30℃~20℃であり、
数平均分子量が2.0×104~7.0×104であり、
重量平均分子量が1.0×105~3.0×105である、
含フッ素共重合体に関する。
以下に本発明の詳細を説明する。
〔含フッ素共重合体及びその製造方法〕
本発明の含フッ素共重合体は、重合単位として、単量体(A)である、フルオロオレフィンを構成単量体中15~85モル%含む。
一般式(1)あるいは(2)で示される有機ケイ素化合物の数平均分子量は、200~30,000が好ましい。
CH2=C(CH3)-COO-C3H6-Si(CH3)2-〔O-Si(CH3)2〕m-R3 (3)
(ここで、R3は炭素数1~6のアルキル基を示し、mは1~250、好ましくは5~200を示す。)
CH2=CH-COO-C3H6-Si(CH3)2-〔O-Si(CH3)2〕p-R4 (4)
(ここで、R4は炭素数1~6のアルキル基を示し、pは1~250、好ましくは5~200を示す。)
R5-C3H6-Si(CH3)2-〔O-Si(CH3)2〕q-C3H6-R5 (5)
(ここで、R5は-OOC(CH3)C=CH2を示し、qは1~250、好ましくは5~200を示す。)
CH2=C(CH3)COO-C3H6Si〔O-Si(CH3)3〕3 (6)
単量体(E)としては、シクロヘキシルビニルエーテル、2-(パーフルオロヘキシル)エチルビニルエーテルなどの、その他のビニルエーテル、
エチルアリルエーテル、ブチルアリルエーテル、シクロヘキシルアリルエーテル、イソブチルアリルエーテル、n-プロピルアリルエーテルなどの、その他のアリルエーテル、
メチルメタクリレート、エチルメタクリレート、n-ブチルメタクリレート、t-ブチルメタクリレート、シクロヘキシルメタクリレート、ジシクロペンタニルメタクリレート、2-(パーフルオロブチル)エチルメタクリレート、2-(パーフルオロヘキシル)エチルメタクリレートなどの、その他のメタクリル酸エステル、
メチルアクリレート、エチルアクリレート、t-ブチルアクリレート、2-(パーフルオロブチル)エチルアクリレート、2-(パーフルオロヘキシル)エチルアクリレートなどの、その他のアクリル酸エステル、
が挙げられる。
また、単量体(E)としては、例えば、エチレン、プロピレン等のオレフィン、塩化ビニル、塩化ビニリデン等のハロオレフィンが挙げられる。
本発明の含フッ素共重合体は、単量体(E)の割合が構成単量体中20モル%未満、更に15モル%以下、であることが好ましい。
換樹脂等のイオン交換樹脂、炭酸水素ナトリウム、炭酸ナトリウム、炭酸水素カリウム、炭酸カリウム、リン酸ナトリウム等のアルカリ金属塩類又はアルカリ土類金属塩類、アルミナ、ジルコニア、チタニア等の金属酸化物、モレキュラーシーブス等のゼオライト類等を添加し、フッ化水素等の酸性物質を中和してもよい。添加のタイミングは重合前、重合中、重合後のいずれの場合でもよく、2回以上に分けてもよい。
また、本発明の含フッ素共重合体は、重量平均分子量が1.0×105~3.0×105である。この重量均分子量は、好ましくは1.5×105~2.7×105、より好ましくは1.6×105~2.5×105である。
含フッ素共重合体の数平均分子量が2.0×104以上、且つ重量平均分子量が1.0×105以上であれば、該含フッ素共重合体を含む被膜用組成物のレベリングが良好で、平滑な塗膜を得ることができると同時に被膜の強度も高く、有効な自己修復性が得られる。また、含フッ素共重合体の数平均分子量が7.0×104以下、且つ重量平均分子量が3.0×105以下であれば、該含フッ素共重合体を含む被膜用組成物の粘度が適切となり、ハンドリング性も良好となる。
ここで、含フッ素共重合体の数平均分子量及び重量平均分子量は、それぞれ、以下の条件でゲル パーミエーション クロマトグラフィーにより測定されたものである。
測定装置:HLC-8320GPC(東ソー株式会社)
カラム:TDgel SuperHZM-M(東ソー株式会社)
検出器:RI(装置付属の示差屈折計)
標準物質:ポリスチレン
データ処理:EcoSEC-WS(東ソー株式会社)
測定条件:カラム温度(40℃)、溶剤(テトラヒドロフラン)、流速(0.35mL/min)、試料濃度(0.14wt%)、試料注入量(20μL)
本発明は、本発明の含フッ素共重合体と、該含フッ素共重合体の硬化剤とを含有し、該硬化剤が多価イソシアネート化合物のアダクト変性体又はアロファネート変性体である、被膜用組成物を提供する。例えば、本発明の含フッ素共重合体を用いて、ワニスや塗料組成物を調製し、それらを用いて被膜を形成させることにより、自己修復性に優れた被膜を得ることができる。本発明の被膜用組成物に用いる含フッ素共重合体は、水酸基、エポキシ基のような硬化反応性基を有するものが好ましい。
また、その他の硬化剤として、メラミン硬化剤、尿素樹脂硬化剤、多基塩基酸硬化剤などを用いることもできる。該メラミン硬化剤としては、例えばブチル化メラミン、メチル化メラミン、エポキシ変性メラミン等が挙げられ、用途に応じて各種変性度の硬化剤が適宜用いられ、また自己縮合度も適宜選ぶことができる。尿素樹脂硬化剤としては、例えばメチル化尿素樹脂やブチル化尿素樹脂等が挙げられる。多基塩基酸硬化剤としては、例えば長鎖脂肪族ジカルボン酸、芳香族多価カルボン酸類及びこれらの酸無水物等が挙げられる。
本発明は、基材と、該基材上に形成された本発明の被膜用組成物の硬化被膜と、を有する塗装物品を提供する。本発明の塗装物品には、本発明の含フッ素共重合体及び被膜用組成物で述べた事項を適宜適用することができる。
これら以外の用途として、例えば、携帯電話、スマートフォン、パソコン、テレビ、ポータブル端末(ゲーム機を含む)、プリンター等の電子機器、テレビ、エアコン、電子レンジ、冷蔵庫、洗濯機、空気清浄機、掃除機、換気扇等の家電類、玩具類、棚、書棚、ベッド、机、椅子、ソファー等のインテリア類、換気扇、レンジフード、キッチンパネル、ステンレスシンク、浴槽、トイレ等の用途、及びこれらの用途における塗料、保護フィルム、意匠性フィルム等が挙げられる。また、建築物等におけるウィンドウフィルム、ガラス表面コート、屋外マーキングフィルム、各種物品の保護フィルム、建材用塗装等が挙げられる。
本発明は、基材に前記本発明の被膜用組成物を塗布して塗膜を形成し、該塗膜を硬化させて硬化被膜を形成する、硬化被膜の形成方法を提供する。本発明の硬化被膜の形成方法には、本発明の含フッ素共重合体、被膜用組成物及び塗装物品で述べた事項を適宜適用することができる。
本明細書は、単量体(A)を構成単量体中15~85モル%、単量体(B)を構成単量体中0.001~10モル%、単量体(C)を構成単量体中5~40モル%、及び単量体(D)を構成単量体中1~25モル%含む含フッ素共重合体であって、ガラス転移温度が-30℃~20℃であり、数平均分子量が2.0×104~7.0×104であり、重量平均分子量が1.0×105~3.0×105である、含フッ素共重合体と、
該含フッ素共重合体の硬化剤とを含有し、
該硬化剤が多価イソシアネート化合物のアダクト変性体又はアロファネート変性体である、組成物の、被膜用組成物としての使用を開示する。
該含フッ素共重合体の硬化剤とを含有し、
該硬化剤が多価イソシアネート化合物のアダクト変性体又はアロファネート変性体である、被膜剤のための組成物を開示する。
(A)フルオロオレフィンを構成単量体中15~85モル%、
(B)下記の一般式(1)で表される化合物及び下記一般式(2)で表される化合物から選ばれる1種以上の有機ケイ素化合物を構成単量体中0.001~10モル%、
(C)ビニルエーテル、ビニルエステル、メタクリル酸エステル及びアクリル酸エステルから選ばれる単量体であって、硬化反応性基を有さず、炭素数1~20の脂肪族飽和炭化水素基を有し、該単量体のホモポリマーのガラス転移温度が0℃未満である単量体から選ばれる1種以上の単量体を構成単量体中5~40モル%、並びに
(D)ビニルエーテル、ビニルエステル、アリルエーテル、メタクリル酸エステル及びアクリル酸エステルから選ばれる単量体であって、硬化反応性基を有する単量体から選ばれる1種以上の単量体〔以下、単量体(D)という〕を構成単量体中1~25モル%
含む含フッ素共重合体であって、
ガラス転移温度が-30℃~20℃であり、
数平均分子量が2.0×104~7.0×104であり、
重量平均分子量が1.0×105~3.0×105である、
含フッ素共重合体。
前記いずれかの態様の含フッ素共重合体と、該含フッ素共重合体の硬化剤とを含有し、該硬化剤が多価イソシアネート化合物のアダクト変性体又はアロファネート変性体である、被膜用組成物。
前記いずれかの態様の含フッ素共重合体を、好ましくは0.5~90質量%、より好ましくは1~80質量%、
該含フッ素共重合体の硬化剤を、含フッ素共重合体100質量部に対して、好ましくは1~300質量部、より好ましくは2~250質量部、更に好ましくは3~200質量部、及び
溶剤、好ましくは有機溶剤を、好ましくは5~99質量%、より好ましくは10~98質量%、更に好ましくは20~95質量%
含有し、
前記含フッ素共重合体の単量体(D)が、硬化反応性基として、水酸基及びエポキシ基から選ばれる1種以上の基を有する単量体であり、
前記硬化剤が、ヘキサメチレンジイソシアネート、ペンタメチレンジイソシアネート、イソホロンジイソシアネートから選ばれる多価イソシアネート化合物のアダクト変性体であってNCO基を3つ以上、好ましくは5つ以下有する化合物又はアロファネート変性体であってNCO基を3つ以上、好ましくは5つ以下有する化合物である、
被膜用組成物。
基材と、該基材上に形成された前記いずれかの態様の被膜用組成物の硬化被膜と、を有する塗装物品。
基材に前記いずれかの態様の被膜用組成物を塗布して塗膜を形成し、該塗膜を硬化させて硬化被膜を形成する、硬化被膜の形成方法。
製造例及び比較製造例
硬化性含フッ素共重合体を、次のようにして調製した。表1~4に共重合体の単量体組成を示した。
(製造例1)
内容積1Lのステンレス製攪拌機付きオートクレーブ(耐圧10MPa)に、脱気したのち、フッ化ビニリデン(以下VDFと略す)96g、テトラフルオロエチレン(以下TFEと略す)84g、ノルマルブチルビニルエーテル(以下NBVEと略す、ホモポリマーのTg:-55℃)36g、ヒドロキシブチルビニルエーテル(以下HBVEと略す)36g、下記構造式で示されるメタクリル変性シリコーンオイルA(数平均分子量約3500)15g、酢酸ブチル450ml、及びt-ブチルパーオキシピバレート1.0gを入れ、攪拌しながら内温を60℃に昇温した。
メタクリル変性シリコーンオイルA:
CH2=C(CH3)-COO-C3H6-Si(CH3)2-〔O-Si(CH3)2〕44-OSi(CH3)3
内容積1Lのステンレス製攪拌機付きオートクレーブ(耐圧10MPa)に、脱気したのち、VDF96g、TFE84g、オクタデシルビニルエーテル(以下ODVEと略す、ホモポリマーのTg:-100℃未満)45g、HBVE36g、シクロヘキシルビニルエーテル(以下CHVEと略す)26g、実施例1と同様のメタクリル変性シリコーンオイルA(数平均分子量約3500)15g、酢酸ブチル450ml、及びt-ブチルパーオキシピバレート1.0gを入れ、攪拌しながら内温を60℃に昇温した。
内容積1Lのステンレス製攪拌機付きオートクレーブ(耐圧10MPa)に、脱気したのち、VDF80g、TFE70g、エチルビニルエーテル(以下EVEと略す、ホモポリマーのTg:-43℃)70g、HBVE39g、実施例1と同様のメタクリル変性シリコーンオイルA(数平均分子量約3500)15g、酢酸ブチル450ml、及びt-ブチルパーオキシピバレート1.0gを入れ、攪拌しながら内温を60℃に昇温した。
内容積1Lのステンレス製攪拌機付きオートクレーブ(耐圧10MPa)に、脱気したのち、VDF96g、TFE84g、NBVE36g、HBVE39g、下記構造式で示されるメタクリル変性シリコーンオイルB(数平均分子量約8000)16g、酢酸ブチル450ml、及びt-ブチルパーオキシピバレート1.0gを入れ、攪拌しながら内温を60℃に昇温した。
メタクリル変性シリコーンオイルB:
CH2=C(CH3)-COO-C3H6-Si(CH3)2-〔O-Si(CH3)2〕140-OSi(CH3)3
内容積1Lのステンレス製攪拌機付きオートクレーブ(耐圧10MPa)に、脱気したのち、VDF56g、TFE87g、NBVE49g、HBVE14g、CHVE13g、実施例1と同様のメタクリル変性シリコーンオイルA(数平均分子量約3500)15g、酢酸ブチル450ml、及びt-ブチルパーオキシピバレート1.0gを入れ、攪拌しながら内温を60℃に昇温した。
内容積1Lのステンレス製攪拌機付きオートクレーブ(耐圧10MPa)に、脱気したのち、VDF96g、TFE84g、NBVE60g、ヒドロキシエチルビニルエーテル(以下HEVEと略す)24g、実施例1と同様のメタクリル変性シリコーンオイルA(数平均分子量約3500)15g、酢酸ブチル450ml、及びt-ブチルパーオキシピバレート1.0gを入れ、攪拌しながら内温を60℃に昇温した。
内容積1Lのステンレス製攪拌機付きオートクレーブ(耐圧10MPa)に、脱気したのち、VDF56g、TFE87g、HBVE35g、CHVE53g、実施例1と同様のメタクリル変性シリコーンオイルA(数平均分子量約3500)15g、酢酸ブチル450ml、及びt-ブチルパーオキシピバレート1.0gを入れ、攪拌しながら内温を60℃に昇温した。
内容積1Lのステンレス製攪拌機付きオートクレーブ(耐圧10MPa)に、脱気したのち、VDF56g、TFE87g、NBVE28g、HBVE29g、CHVE25g、酢酸ブチル450ml、及びt-ブチルパーオキシピバレート1.0gを入れ、攪拌しながら内温を60℃に昇温した。
含フッ素共重合体の酢酸ブチル溶液(ワニス)を100℃-24時間の条件で乾燥させ、これを、入力補償型ダブルファーネス示差走査熱量測定装置DSC8000(PerkinElmer株式会社製)を用い、窒素雰囲気下、昇温速度10℃/min、測定範囲-50℃~+150℃にてTgを測定した。結果を表1~4に示した。
<被膜用組成物の調製>
[被膜用組成物の調製(1)]
製造例1~6及び比較製造例1~2の各含フッ素共重合体溶液に対し、硬化剤としてヘキサメチレンジイソシアネートのトリメチロールプロパンによるアダクト変性体(NCO含有量7%)(旭化成ケミカルズ株式会社製、デュラネートE402-80B)(3官能)をNCO/OH=1.1の割合で加え、酢酸ブチルにて溶液の固形分濃度が23%となるよう希釈し、被膜用組成物を調製した。ここで用いた硬化剤は、表中、「アダクト変性体」と示した。なお、含フッ素共重合体100質量部に対する硬化剤の量は12.8~34.0質量部の範囲であった。
製造例1~6及び比較製造例2の各含フッ素共重合体溶液に対し、硬化剤としてペンタメチレンジイソシアネートによるアロファネート変性体(NCO含有量16.2%)(東ソー株式会社製、コロネート2793)(5官能)をNCO/OH=1.1の割合で加え、酢酸ブチルにて溶液の固形分濃度が23%となるよう希釈し、被膜用組成物を調製した。ここで用いた硬化剤は、表中、「アロファネート変性体1」と示した。なお、含フッ素共重合体100質量部に対する硬化剤の量は5.6~14.8質量部の範囲であった。
製造例1の含フッ素共重合体溶液に対し、比較の硬化剤としてヘキサメチレンジイソシアネートのイソシアヌレート変性体(NCO含有量21%)(東ソー株式会社製、コロネートHX)(3官能)をNCO/OH=1.1の割合で加え、酢酸ブチルにて溶液の固形分濃度が23%となるよう希釈し、比較例5の被膜用組成物を調製した。ここで用いた硬化剤は、表中、「イソシアヌレート変性体」と示した。なお、含フッ素共重合体100質量部に対する硬化剤の量は10.8質量部であった。
製造例1の含フッ素共重合体溶液に対し、硬化剤としてヘキサメチレンジイソシアネートによるアロファネート変性体(NCO含有量19.5%)(旭化成ケミカルズ株式会社製、デュラネートD101)(2官能)をNCO/OH=1.1の割合で加え、酢酸ブチルにて溶液の固形分濃度が23%となるよう希釈し、実施例3の被膜用組成物を調製した。ここで用いた硬化剤は、表中、「アロファネート変性体2」と示した。なお、含フッ素共重合体100質量部に対する硬化剤の量は17.7質量部であった。
[基材:ガラス板]
被膜用組成物を、表面をアセトンで脱脂した厚さ2mmのガラス板に#20バーコーター(乾燥後膜厚の計算値:約10μm)を用いてハンド塗布し、100℃に加熱された乾燥機で4時間加熱硬化させ、実施例又は比較例の含フッ素共重合体とその硬化剤とからなる被膜が形成された塗装物品を得た。塗装物品の被膜について以下の評価を行った。結果を表1~4に示した。
被膜用組成物を、表面をイソプロピルアルコールで脱脂した厚さ1mmのポリエステル系ウレタンゴムフィルムに#10バーコーター(乾燥後膜厚の計算値:約5μm)を用いてハンド塗布し、120℃に加熱された乾燥機で3分加熱硬化させ、50℃で3日養生した。これにより、実施例又は比較例の含フッ素共重合体とその硬化剤とからなる被膜が形成された塗装物品を得た。この塗装物品の被膜について、後述の「耐擦傷試験(真鍮ブラシ)」を行った。結果を表1~4に示した。
剥離紙、粘着剤層、ウレタン層、並びに、含フッ素共重合体とその硬化剤とからなる被膜を有する塗膜保護フィルムを、以下の手順で作製した。
被膜用組成物を、基材である厚さ150μmの熱可塑性ポリエステル系ポリウレタン(TPU)フィルム(SHG2086-CR(6OPP)、シーダム株式会社製)に、#10バーコーター(乾燥後膜厚の計算値:約5μm)及び#20バーコーター(乾燥後膜厚の計算値:約10μm)を用いてハンド塗布し、120℃に加熱された乾燥機で1分加熱硬化させ、60℃で3日養生した。これにより、TPUフィルムの片面に、実施例又は比較例の含フッ素共重合体とその硬化剤とからなる被膜が形成された複合材(I)を得た。
還流器及び攪拌機を備えたフラスコに、アクリル酸ブチル95質量部、アクリル酸5質量部、過酸化物系開始剤及びトルエン(溶剤)を混合し、窒素雰囲気下で加温、撹拌し、重合反応によりアクリル系ポリマーを得た(重量平均分子量=500,000)。
前記アクリル系ポリマー100質量部(固形分換算)、及びエポキシ系架橋剤(商品名:TETRAD-X、三菱ガス化学株式会社製)0.01質量部を混合して粘着剤を得た。
前記粘着剤を剥離紙(厚さ170μm)にナイフコーターを用いて乾燥後膜厚が約20μmとなるように塗工し、乾燥して粘着剤層を剥離紙上に形成し、粘着剤と剥離紙の複合材(II)を得た。
前記複合材(I)の、TPU基材の含フッ素共重合体とその硬化剤とからなる被膜がコートされた面の逆側にあたるコートされていない面に対して、前記複合材(II)の粘着剤層を貼付して、塗膜保護フィルムを作製した。
基材として厚さ0.3mmの非フタル酸系塩化ビニルフィルム(セレブ 267(硬度#360)、石塚株式会社が販売)を用いた以外は、上記TPUを用いた塗膜保護フィルムと同条件、同処理として、塗膜保護フィルムを作製した。この塗膜保護フィルムにおける前記被膜の面を対象として、後述の「耐擦傷試験(真鍮ブラシ)」を行った。結果を表1~4に示した。
基材として厚さ125μmの易接着PETフィルム(コスモシャイン A4300、東洋紡株式会社製)を用いた以外は、上記TPUを用いた塗膜保護フィルムと同条件、同処理として、塗膜保護フィルムを作製した。この塗膜保護フィルムにおける前記被膜の面を対象として、後述の「耐擦傷試験(真鍮ブラシ)」を行った。結果を表1~4に示した。
JIS-K5400 8.5.2(1990)(碁盤目テープ試験)により以下の2通りの方法で測定した。
・被膜表面をそのまま測定に供する(表中、未処理と標記)。
・被膜表面を塗膜が剥離しない程度に軽くサンドペーパー(粒度1200)で処理して測定に供する(表中、サンドペーパー処理と標記)。
10%HCl溶液による24時間スポットテスト後の被膜外観を目視観察し、以下の基準で判定した。
◎:異状なし
○:ほとんど変化なし
△:やや侵される
×:侵される
10%NaOH溶液による24時間スポットテスト後の被膜外観を目視観察し、以下の基準で判定した。
◎:異状なし
○:ほとんど変化なし
△:やや侵される
×:侵される
キシレンによる30分スポットテスト後の被膜外観を目視観察し、以下の基準で判定した。
◎:異状なし
○:ほとんど変化なし
△:やや侵される
×:侵される
油性フェルトペン(黒色)により被膜表面を塗りつぶし、室温で1時間放置後、乾拭きによりインクを除去した。その際の被膜表面のインクの除去性を以下の基準で評価した。なお、黒色油性フェルトペンはマジックインキ(商品名)、寺西化学工業株式会社製を用いた。
◎:全く跡が付かない
○:ごくわずか跡が付く
△:かなり跡が付く
×:完全に跡が残る
被膜における純水及びオレイン酸の接触角(単位:度)を、Drop Master DM300(協和界面化学株式会社製)を用い、気温20℃、湿度40%RHの条件下にて、滴下量10μLにて測定した。
被膜の60°光沢値を、GLOSS CHECKER IG-330(株式会社堀場製作所)を用いてn=3の水準で測定した。その後、超促進耐候性試験機メタルウェザーKW-R7TP(ダイプラ・ウィンテス株式会社製)を用い、紫外線強度65mW/cm2、ブラックパネル温度53℃、相対湿度50%の条件で、被膜に対して紫外線を20時間照射後、ブラックパネル温度30℃、相対湿度98%の条件で4時間無照射状態にするサイクルを計8サイクル行うことにより、耐候性促進試験を行った。紫外線照射後の被膜の60°光沢値を照射前と同様の方法で測定し、光沢保持率を、以下の式で求めた。なお、促進耐候性試験を行わなかった例は、表中、「ND」と記載した。
光沢保持率(%)={60°光沢値(照射後)/60°光沢値(照射前)}×100
気温20℃環境下にて、180mm真鍮ブラシ(エスコ)に200g荷重を取り付け、被膜上をこれで20往復(移動幅40mm、移動速度80mm/秒)し、傷が修復するまでの時間を最大2分まで計測した。
Claims (9)
- 下記の含フッ素共重合体と、該含フッ素共重合体の硬化剤とを含有し、該硬化剤が多価イソシアネート化合物のアダクト変性体又はアロファネート変性体であって、官能基を3つ以上有する硬化剤である、被膜用組成物。
<含フッ素共重合体>
(A)フルオロオレフィンを構成単量体中15~85モル%、
(B)下記の一般式(1)で表される化合物及び下記一般式(2)で表される化合物から選ばれる1種以上の有機ケイ素化合物を構成単量体中0.001~10モル%、
(C)ビニルエーテル、ビニルエステル、メタクリル酸エステル及びアクリル酸エステルから選ばれる単量体であって、硬化反応性基である水酸基及びエポキシ基を有さず、炭素数1~20の脂肪族飽和炭化水素基を有し、該単量体のホモポリマーのガラス転移温度が0℃未満である単量体から選ばれる1種以上の単量体を構成単量体中5~40モル%、並びに
(D)ビニルエーテル、ビニルエステル、アリルエーテル、メタクリル酸エステル及びアクリル酸エステルから選ばれる単量体であって、水酸基及びエポキシ基から選ばれる1種以上の硬化反応性基を有する単量体から選ばれる1種以上の単量体〔以下、単量体(D)という〕を構成単量体中1~25モル%
含む含フッ素共重合体であって、
ガラス転移温度が-30℃~20℃であり、
数平均分子量が2.0×104~7.0×104であり、
重量平均分子量が1.0×105~3.0×105である、
含フッ素共重合体。
[ここで、R1は炭素数1~6のアルキル基、-(CH2)r-OOC(CH3)C=CH2、-(CH2)r-OOC-HC=CH2又は-CH=CH2を示し、R2は-(CH2)r-OOC(CH3)C=CH2、-(CH2)r-OOC-HC=CH2又は-CH=CH2を示し、nは1~420の数を示し、rは1~6の数を示す。] - 前記硬化剤が、ヘキサメチレンジイソシアネート、ペンタメチレンジイソシアネート、イソホロンジイソシアネートから選ばれる多価イソシアネート化合物のアダクト変性体又はアロファネート変性体である、請求項1記載の被膜用組成物。
- 硬化剤を、含フッ素共重合体100質量部に対して、1~300質量部含有する、請求項1又は2に記載の被膜用組成物。
- 単量体(D)が、炭素数1~20の脂肪族飽和炭化水素基、炭素数1~20の脂環式飽和炭化水素基、及びアルキレン基の炭素数が1~20で繰り返し単位数が1~10であるアルキレングリコール基から選ばれる基を有する、請求項1~3の何れか1項に記載の被膜用組成物。
- 請求項1~4の何れか1項に記載の被膜用組成物の製造方法であって、前記含フッ素共重合体と前記硬化剤とを混合する、被膜用組成物の製造方法。
- 基材と、該基材上に形成された請求項1~4の何れか1項に記載の被膜用組成物の硬化被膜と、を有する塗装物品。
- 硬化被膜の膜厚が0.5~1000μmである、請求項6に記載の塗装物品。
- 基材に請求項1~4の何れか1項に記載の被膜用組成物を塗布して塗膜を形成し、該塗膜を硬化させて硬化被膜を形成する、硬化被膜の形成方法。
- 前記塗膜を、30~250℃で硬化させる、請求項8に記載の硬化被膜の形成方法。
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KR102490295B1 (ko) | 2023-01-20 |
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