JP6903832B2 - ポリウレタン水分散体およびコーティング剤 - Google Patents
ポリウレタン水分散体およびコーティング剤 Download PDFInfo
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- JP6903832B2 JP6903832B2 JP2021509053A JP2021509053A JP6903832B2 JP 6903832 B2 JP6903832 B2 JP 6903832B2 JP 2021509053 A JP2021509053 A JP 2021509053A JP 2021509053 A JP2021509053 A JP 2021509053A JP 6903832 B2 JP6903832 B2 JP 6903832B2
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- aqueous dispersion
- mass
- polyurethane
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- 229920002635 polyurethane Polymers 0.000 title claims description 84
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- 150000003077 polyols Chemical class 0.000 claims description 70
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 57
- 239000005056 polyisocyanate Substances 0.000 claims description 32
- 229920001228 polyisocyanate Polymers 0.000 claims description 32
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- 125000000129 anionic group Chemical group 0.000 claims description 6
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- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
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- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
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- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 3
- SDQROPCSKIYYAV-UHFFFAOYSA-N 2-methyloctane-1,8-diol Chemical compound OCC(C)CCCCCCO SDQROPCSKIYYAV-UHFFFAOYSA-N 0.000 description 3
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 3
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- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- 238000011156 evaluation Methods 0.000 description 3
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- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 3
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 3
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- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
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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
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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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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C—CHEMISTRY; METALLURGY
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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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- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3212—Polyhydroxy compounds containing cycloaliphatic groups
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- 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
- C08G18/30—Low-molecular-weight compounds
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- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
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- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6659—Compounds of group C08G18/42 with compounds of group C08G18/34
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
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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
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- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
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- C—CHEMISTRY; METALLURGY
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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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
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Description
装置:東ソー(株)製 HLC−8120
カラム:東ソー(株)製 TSK GEL GMH6 2本
測定温度:40℃
試料溶液:0.25重量%のテトラヒドロフラン溶液
溶液注入量:100μL
検出装置:屈折率検出器
基準物質:東ソー(株)製 標準ポリスチレン(TSKstandard POLYSTYREN E)12点(分子量 500、1050、2800、5970、9100、18100、37900、96400、190000、355000、1090000、2890000)
ウレア結合量(mol/kg)={(WA1/MWA1×FA1+WA2/MWA2×FA2+…+WAj/MWBj×FAj)−(WB1/MWB1×FB1+WB2/MWB2×FB2+…+WBk/MWBk×FBk+WC1/MWC1×FC1+WCm/MWCm×FCm)}×10
[実施例1]
攪拌機、還流冷却管、温度計および窒素吹き込み管を備えた4つ口フラスコに、ポリエステルポリオール(旭化成ケミカルズ株式会社製、商品名「PCDL T−4671」、原料として1,4−ブタンジオールと1,6−ヘキサンジオールを含む。繰り返し単位:1,4−ブタンジオール/1,6−ヘキサンジオール=7/3(モル比)、水酸基価=112.2mgKOH/g、数平均分子量=1000)を65.00質量部、ジメチロールプロピオン酸(DMPA)を5.00質量部、メチルエチルケトン100質量部を加え十分攪拌溶解し、次いでジシクロヘキシルメタンジイソシアネート(H12MDI)30.00質量部を加えNCO含量が0.84%になるまで75℃で反応させた。なお、「NCO含量」とは、イソシアネート基の含量を意味している。その後、このプレポリマー溶液を45℃まで冷却し、中和剤としてトリエチルアミン(TEA)3.77質量部を加えてホモミキサーを用いて乳化した後、ジエチレントリアミン(DETA)0.65質量部を添加し、鎖伸長反応を30℃で30分行った。この樹脂溶液を加熱減圧下、メチルエチルケトンを留去し、固形分25%のポリウレタン水分散体を得た。下記表1に、ウレタンプレポリマー(A)の重量平均分子量(PP分子量)(Mw)と、ポリウレタン(C)の架橋度(mol/kg)と、ポリウレタン(C)のウレア結合量(mol/kg)とを示した。
各原料の種類と仕込み量を下記表1に示すとおりに変更した以外は、実施例1と同様に製造を行い各ポリウレタン水分散体を得た。なお、表1において、1,4−CHDMは1,4−シクロヘキサンジメタノールを意味し、EGはエチレングリコールを意味し、TMPはトリメチロールプロパンを意味し、EDAはエチレンジアミンを意味している。また、1,4−CHDMとEGとTMPとは、いずれも上述の数平均分子量が400以下のポリオールに相当する。
上記ポリウレタン水分散体をポリエチレンテレフタレート基材(東レ株式会社製PET、型番:#100 T60)上に膜厚が約20μmになるように塗布し、80℃で6時間乾燥することによりコーティング層を作成した。
上記コーティング層同士を500g荷重で張り付け剥離する際のコーティング面の状態を目視にて観察した。コーティング面同士が接着しない場合を〇とし、貼り付けた面積の50%以上が接着している場合は△とし、すべて接着している場合は×とした。
コーティング層に酢酸エチル/トルエンの混合溶剤をしみ込ませたフェルトで500g荷重でラビング試験を10回行い、コーティング面の状態を目視で観察した。コーティング面が変化しない場合は〇とし、浸食されている場合は△、コーティング層が剥離した場合は×とした。
コーティング面を500g荷重の真鍮ワイヤーブラシ(藤原産業株式会社製No.9)にて5往復こすり、硬化フィルム上の傷のつき具合を目視にて観察した。評価は、室温23℃で行い、10秒以内で傷が復元しているものを○とし、10秒〜10分程度かかるものを△とし、1時間たっても復元しない場合は×とした。
Claims (14)
- ポリイソシアネート(a)、ポリオール(b)、および親水性基を有するポリオール(c)を反応させて得られるウレタンプレポリマー(A)と鎖伸長剤(B)とを反応させて得られるポリウレタン(C)が水に分散されてなるポリウレタン水分散体であって、上記ウレタンプレポリマー(A)の重量平均分子量が2,000以上30,000以下であり、上記ポリウレタン(C)の架橋度が、0.03mol/kg以上0.15mol/kg以下であり、上記ポリウレタン(C)のウレア結合量が0.5mol/kg以下であり、
上記ポリイソシアネート(a)は、脂環族ポリイソシアネートを含む、ポリウレタン水分散体。 - 請求項1に記載のポリウレタン水分散体において、上記ウレタンプレポリマー(A)の重量平均分子量は、5,000以上15,000以下であることを特徴とする、ポリウレタン水分散体。
- 請求項1または請求項2に記載のポリウレタン水分散体において、上記ポリウレタン(C)の架橋度は、0.05mol/kg以上0.10mol/kg以下であることを特徴とする、ポリウレタン水分散体。
- 請求項1から請求項3までのいずれか一項に記載のポリウレタン水分散体において、上記ポリウレタン(C)のウレア結合量は、0.1mol/kg以上0.25mol/kg以下であることを特徴とする、ポリウレタン水分散体。
- 請求項1から請求項4までのいずれか一項に記載のポリウレタン水分散体において、上記ポリオール(b)は、ポリエステルポリオールと、ポリカーボネートジオールと、ポリエーテルポリオールとからなる群より選ばれる少なくとも1種を含むことを特徴とする、ポリウレタン水分散体。
- 請求項1から請求項5までのいずれか一項に記載のポリウレタン水分散体において、上記ポリオール(b)の数平均分子量は、400以上3,000以下であることを特徴とする、ポリウレタン水分散体。
- 請求項1から請求項6までのいずれか一項に記載のポリウレタン水分散体において、上記親水性基を有するポリオール(c)の親水性基は、アニオン性親水基であることを特徴とする、ポリウレタン水分散体。
- 請求項7に記載のポリウレタン水分散体において、上記ポリウレタン(C)の酸価は、10mgKOH/g以上45mgKOH/g以下であることを特徴とする、ポリウレタン水分散体。
- 請求項1から請求項8までのいずれか一項に記載のポリウレタン水分散体において、上記ウレタンプレポリマー(A)は、上記ウレタンプレポリマー(A)100質量部のうち、上記ポリイソシアネート(a)を15質量部以上45質量部以下含むことを特徴とする、ポリウレタン水分散体。
- 請求項1から請求項9までのいずれか一項に記載のポリウレタン水分散体において、上記ウレタンプレポリマー(A)は、上記ウレタンプレポリマー(A)100質量部のうち、上記ポリオール(b)を50質量部以上80質量部以下含むことを特徴とする、ポリウレタン水分散体。
- 請求項1から請求項10までのいずれか一項に記載のポリウレタン水分散体において、上記ウレタンプレポリマー(A)は、上記ウレタンプレポリマー(A)100質量部のうち、上記親水性基を有するポリオール(c)を1質量部以上10質量部以下含むことを特徴とする、ポリウレタン水分散体。
- 請求項1から請求項11までのいずれか一項に記載のポリウレタン水分散体において、上記鎖伸長剤(B)は、ポリアミンを含むことを特徴とする、ポリウレタン水分散体。
- 請求項1から請求項12までのいずれか一項に記載のポリウレタン水分散体において、上記ポリウレタン(C)は、上記ウレタンプレポリマー(A)100質量部に対し、上記鎖伸長剤(B)を、0.4質量部以上1.0質量部以下含むことを特徴とする、ポリウレタン水分散体。
- 請求項1から請求項13までのいずれか一項に記載のポリウレタン水分散体を含有することを特徴とするコーティング剤。
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US20230398770A1 (en) * | 2022-06-09 | 2023-12-14 | Stek Co., Ltd. | Exterior film of building for protecting glass |
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EP0552420A3 (en) * | 1992-01-24 | 1993-09-15 | H.B. Fuller Licensing & Financing, Inc. | Water dispersed polyurethane polymer for improved coatings and adhesives |
US5763526A (en) * | 1995-07-31 | 1998-06-09 | Nippon Paint Co., Ltd. | Urethane prepolymer, process for producing urethane prepolymer, isocyanate compound, and polyurethane dispersion |
US5798409A (en) * | 1995-10-03 | 1998-08-25 | Minnesota Mining & Manufacturing Company | Reactive two-part polyurethane compositions and optionally self-healable and scratch-resistant coatings prepared therefrom |
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