JP2019026668A - ウレタン塗料組成物、硬化塗膜、および樹脂部材 - Google Patents
ウレタン塗料組成物、硬化塗膜、および樹脂部材 Download PDFInfo
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- JP2019026668A JP2019026668A JP2017144206A JP2017144206A JP2019026668A JP 2019026668 A JP2019026668 A JP 2019026668A JP 2017144206 A JP2017144206 A JP 2017144206A JP 2017144206 A JP2017144206 A JP 2017144206A JP 2019026668 A JP2019026668 A JP 2019026668A
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- 238000000576 coating method Methods 0.000 title claims abstract description 80
- 239000011248 coating agent Substances 0.000 title claims abstract description 79
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 239000008199 coating composition Substances 0.000 title claims abstract description 37
- 229920005989 resin Polymers 0.000 title claims abstract description 19
- 239000011347 resin Substances 0.000 title claims abstract description 19
- 150000003077 polyols Chemical class 0.000 claims abstract description 80
- 229920005862 polyol Polymers 0.000 claims abstract description 58
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 40
- 229920000570 polyether Polymers 0.000 claims abstract description 40
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 40
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 40
- 239000004094 surface-active agent Substances 0.000 claims abstract description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 35
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000003945 anionic surfactant Substances 0.000 claims abstract description 16
- 239000002563 ionic surfactant Substances 0.000 claims abstract description 15
- 239000002280 amphoteric surfactant Substances 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 30
- 229920001610 polycaprolactone Polymers 0.000 claims description 17
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- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 5
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
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- 239000002253 acid Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
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- 125000000217 alkyl group Chemical group 0.000 description 4
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- 150000002513 isocyanates Chemical class 0.000 description 4
- 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 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
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- 125000002091 cationic group Chemical group 0.000 description 3
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- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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
- C09D175/08—Polyurethanes from polyethers
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
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Abstract
Description
本発明のポリイソシアネート(a)は、ジイソシアネートおよびその誘導体からなる群から選ばれる少なくとも1種のポリイソシアネート化合物と熱解離性ブロック剤を反応して得られるブロックポリイソシアネート化合物である。前記ポリイソシアネート(a)は、それぞれ単独で用いてもよく、2種以上を混合して用いてもよい。
本発明のポリエーテルポリオール(b)は、少なくとも、数平均分子量が300以上600未満であるポリエーテルポリオール(b−1)と、数平均分子量が600以上900未満であるポリエーテルポリオール(b−2)と、数平均分子量が900以上1800以下であるポリエーテルポリオール(b−3)である。なお、当該数平均分子量は、ポリエーテルポリオール(b)の水酸基価を測定して次式により求めることができる。後述するポリカプロラクトンポリオール(e)の数平均分子量についても同様である。
数平均分子量=水酸基価×N×1,000/56.11
水酸基価:JIS K−1577の6.4に準じて測定した値
N:ポリオールの平均官能基数(ポリオール1分子中の水酸基の数平均数)
本発明の界面活性剤(c)は、分子内に水酸基を有するイオン性界面活性剤と、イソシアネート基との反応性基を有さない、アニオン性界面活性剤および/または両性界面活性剤である。
R1−NH−(CH2)n−N+R2R3R4 X−
(一般式(1)中、R1は炭素数8〜24の直鎖または分岐鎖を有する飽和または不飽和のアシル基を表し、かつ1つ以上の水酸基を有し、nは1〜10を表し、R2〜R4は、独立して、水素原子、炭素数1〜6のアルキル基、炭素数1〜6のアルコキシ基を表し、Xはアニオンを表す。)で表される化合物が挙げられる。
本発明のウレタン塗料組成物は、通常の塗料において行われる塗装方法により基材に塗装し、加熱硬化することによって、基材の表面に硬化塗膜を形成することができる。
<原料>
<ポリイソシアネート(a)>
a−1:1,6−ヘキサメチレンジイソシアネートの誘導体とマロン酸ジメチル/3,5−ジメチルピラゾールのブロックポリイソシアネート化合物(固形分70重量%、プロピレングリコールモノメチルエーテル30重量%、対溶液イソシアネート基含有率9.2%、BAXENDEN社製、TRIXENE BI7992)
a−2:イソホロンジイソシアネートの誘導体と3,5−ジメチルピラゾールのブロックポリイソシアネート化合物(固形分65重量%、酢酸ブチル12.5重量%、C9Aromatic12.5重量%、対溶液イソシアネート基含有率7.8%、BAXENDEN社製、TRIXENE BI7951)
<ポリエーテルポリオール(b)>
b−1:ポリオキシエチレングリセリルエーテル(固形分100%、1分子あたりの水酸基数3、数平均分子量450、日油株式会社製、ユニオックスG450)
b−2:ポリオキシエチレングリセリルエーテル(固形分100%、1分子あたりの水酸基数3、数平均分子量750、日油株式会社製、ユニオックスG750)
b−3:ポリオキシプロピレングリセリルエーテル(固形分100%、1分子あたりの水酸基数3、数平均分子量1500、三洋化成工業株式会社製、サンニックスGP1500)
<界面活性剤(c)>
c−1:リシノールアミドプロピルエチルジモニウムエトサルフェート(固形分100%、VANTAGE Specialty Ingredient,Inc製、Lipoquat R)
c−2:ジ−2−エチルヘキシルスルホコハク酸ナトリウム
c−3:アニオン性フッ素系界面活性剤(固形分100%、スルホン酸ナトリウム塩、株式会社ネオス製、フタージェント100)
c−4:両性フッ素系界面活性剤(固形分50%、株式会社ネオス製、フタージェント400SW)
<シリコーンオイル(d)>
d−1:ポリエーテル変性オルガノポリシロキサン(HLB値=12、信越化学工業株式会社製KF−642)
d−2:ポリエーテル変性オルガノポリシロキサン(HLB値=14、信越化学工業株式会社製KF−640)
<ポリカプロラクトンポリオール(e)>
e−1:ポリカプロラクトントリオール(固形分100%、1分子あたりの水酸基数3、数平均分子量800、株式会社ダイセル製、プラクセル308)
<その他成分>
b´−1:ポリエチレングリコール(固形分100%、1分子あたりの水酸基数2、数平均分子量200、東京化成工業株式会社製、PEG200)
b´−2:ポリエチレングリコール(固形分100%、1分子あたりの水酸基数2、数平均分子量2000、東京化成工業株式会社製、PEG2000)
c´−1:ノニオン性フッ素系界面活性剤(固形分100%、株式会社ネオス製、フタージェント215M)
c´−2:カチオン性フッ素系界面活性剤(固形分100%、4級アンモニウム塩(I塩またはBr塩)、株式会社ネオス製、フタージェント300)
<有機溶剤>
ダイアセトンアルコール(DAA)
<実施例1〜10、比較例1〜13>
上記原料を表1および表2に示す割合で配合し、さらに、それぞれ、触媒として、ポリイソシアネート100重量部に対し、0.5重量部のジラウリル酸ジ−n−ブチルスズを加え、実施例および比較例のウレタン塗料組成物を得た。
硬化塗膜の表面を目視によって判断し、下記の評価基準で評価した。
○:正常
×:不透明、白化などの異常がある、あるいは平滑でない
荷重500gを載せたスチールウール(#0000)を硬化塗膜の表面上に置き、ラビングテスターで11往復させる試験条件で試験した後、ヘイズメーター(日本電色工業株式会社製NDH5000)によって、試験後の硬化塗膜を有する樹脂部材のヘイズ(%)を測定し、下記の評価基準で評価した。
○:試験後のヘイズの値が10未満
×:試験後のヘイズの値が10以上
硬化塗膜を10×10マス(1mm間隔)にクロスカットした後、セロハンテープ剥離試験を行い、目視により残っているマスを確認した。
○:剥離なし
×:剥離あり
25℃の恒温室内で、硬化塗膜の表面を50℃の温水蒸気に1分間さらし、目視にて曇りの有無を下記の評価基準で評価した。
◎:速やかに水膜を形成する
○:一瞬曇った後に水膜を形成する
×:曇りが発生する
常温の蒸留水に、硬化塗膜を有する樹脂基材を1時間浸積させた後、取り出して室温で1時間静置させた。その後、上記の初期防曇性の評価の試験を行い、曇りの有無を確認した。
◎:速やかに水膜を形成する
○:一瞬曇った後に水膜を形成する
×:曇りが発生する
蒸留水を5ml程度染み込ませたウェス(BEMCOT M−3II、250mm×250mm、小津産業株式会社製)を硬化塗膜の表面に置き、3往復させる。さらに、この硬化塗膜を有する樹脂基材(部材)を25℃50%RHの室内で1時間静置した後、25℃の恒温室内で、硬化塗膜の表面を50℃温水蒸気に5分間さらした。当該操作を5回繰り返した後、目視にて曇りの有無を下記の評価基準で評価した。硬化塗膜の表面にのみ界面活性剤が存在する場合、界面活性剤がウェスに拭き取られ、曇りが発生しやすい傾向にある。
◎:5回目の評価で速やかに水膜を形成する
○:5回目の評価で一瞬曇った後に水膜を形成する
×:5回目の評価で曇りが発生する
Claims (5)
- ポリイソシアネート(a)、ポリエーテルポリオール(b)、および界面活性剤(c)を含むウレタン塗料組成物であって、
前記ポリイソシアネート(a)は、ジイソシアネートおよびその誘導体からなる群より選ばれる少なくとも1種のポリイソシアネート化合物と熱解離性ブロック剤を反応して得られるブロックポリイソシアネート化合物であり、
前記ポリエーテルポリオール(b)は、数平均分子量が300以上600未満であるポリエーテルポリオール(b−1)と、数平均分子量が600以上900未満であるポリエーテルポリオール(b−2)と、数平均分子量が900以上1800以下であるポリエーテルポリオール(b−3)であり、
前記界面活性剤(c)は、分子内に水酸基を有するイオン性界面活性剤と、イソシアネート基との反応性基を有さない、アニオン性界面活性剤および/または両性界面活性剤であり、
前記(a)〜(c)成分の合計重量において、前記(a)成分が35重量%以上85重量%以下であり、前記(b−1)成分が3重量%以上18重量%以下であり、前記(b−2)成分が8重量%以上38重量%以下であり、前記(b−3)成分が0.5重量%以上8重量%以下であり、前記(c)成分が1重量%以上10重量%以下であることを特徴とするウレタン塗料組成物。 - HLBが10〜18であるシリコーンオイル(d)を含み、
前記(a)〜(d)成分の合計重量において、前記(d)成分が3重量%以下であることを特徴とする請求項1記載のウレタン塗料組成物。 - ポリカプロラクトンポリオール(e)を含み、
前記ポリカプロラクトンポリオール(e)は、数平均分子量が300以上1800以下であって、
前記(a)〜(e)成分の合計重量において、前記(e)成分が10重量%以下であることを特徴とする請求項2記載のウレタン塗料組成物。 - 請求項1〜3のいずれかに記載のウレタン塗料組成物から形成されることを特徴とする硬化塗膜。
- 請求項4記載の硬化塗膜を有することを特徴とする樹脂部材。
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