JP7408602B2 - 優れた耐熱性および溶媒への溶解性を有するポリエステル樹脂、ならびにこれを含有するコーティング組成物 - Google Patents
優れた耐熱性および溶媒への溶解性を有するポリエステル樹脂、ならびにこれを含有するコーティング組成物 Download PDFInfo
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- JP7408602B2 JP7408602B2 JP2021129718A JP2021129718A JP7408602B2 JP 7408602 B2 JP7408602 B2 JP 7408602B2 JP 2021129718 A JP2021129718 A JP 2021129718A JP 2021129718 A JP2021129718 A JP 2021129718A JP 7408602 B2 JP7408602 B2 JP 7408602B2
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- KATXJJSCAPBIOB-UHFFFAOYSA-N cyclotetradecane Chemical compound C1CCCCCCCCCCCCC1 KATXJJSCAPBIOB-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000008397 galvanized steel Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 150000002291 germanium compounds Chemical class 0.000 description 1
- 229940119177 germanium dioxide Drugs 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- MOUPNEIJQCETIW-UHFFFAOYSA-N lead chromate Chemical compound [Pb+2].[O-][Cr]([O-])(=O)=O MOUPNEIJQCETIW-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- OBYVIBDTOCAXSN-UHFFFAOYSA-N n-butan-2-ylbutan-2-amine Chemical compound CCC(C)NC(C)CC OBYVIBDTOCAXSN-UHFFFAOYSA-N 0.000 description 1
- FQBQBRBAJDVVOH-UHFFFAOYSA-N n-ethyl-3-methylbutan-2-amine Chemical compound CCNC(C)C(C)C FQBQBRBAJDVVOH-UHFFFAOYSA-N 0.000 description 1
- XJINZNWPEQMMBV-UHFFFAOYSA-N n-methylhexan-1-amine Chemical compound CCCCCCNC XJINZNWPEQMMBV-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- RLUCXJBHKHIDSP-UHFFFAOYSA-N propane-1,2-diol;propanoic acid Chemical compound CCC(O)=O.CC(O)CO RLUCXJBHKHIDSP-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
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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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
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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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
- C09D167/025—Polyesters derived from dicarboxylic acids and dihydroxy compounds containing polyether sequences
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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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
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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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
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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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
[課題の解決手段]
(a)二価酸成分;ならびに
(b)イソソルビドおよび脂環式ジオールを含むジオール成分
を共重合させることによって得られる繰り返し単位を含むポリエステル樹脂であって、
ポリエステル樹脂が、80℃以上のガラス転移温度を有する、ポリエステル樹脂が提供される。
本発明の態様
以下において、本発明を、例および比較例によって、詳細に説明する。以下の例は、本発明の範囲を限定することなく、本発明をさらに説明することを目的とする。
二価酸成分として、157gのTPAおよび157gのIPA、ならびにジオール成分として、59gのNPG、9gのEG、82gのTCDDMおよび194gのISBを、1Lの三ツ口フラスコに添加し、0.10gの酢酸亜鉛をそこに添加し、続いて、1kgf/cm2の加圧条件下、260℃で、240分間、エステル化反応を行った。110gの水が、エステル化反応中に、系から流出した時に、0.2gの二酸化ゲルマニウム触媒および0.05gのトリエチルホスホノアセテート安定剤を、大気圧下、添加し、重縮合反応を行った。重縮合反応を、1.0mmHgの減圧条件下、270℃で行い、重合反応を、粘度が一定値(固有粘度の0.36dl/g)に達したときに、終了し、目的のポリエステル樹脂を得た。
以下の表1に列挙する成分および量を使用する以外は、例1の記載と同様の手順を行うことによって、ポリエステル樹脂を調製した。
上記の例および比較例で調製したポリエステル樹脂の性能の評価方法は以下の通りである。
(1)成分((TCDDM+ISB)/NPGの成分比)
核磁気共鳴(NMR、600MHz)分析を利用した。ポリエステル樹脂を、クロロホルム-Dに溶解し、プロトンNMRを測定して、(TCDDM+ISB)モル%/NPGモル%の成分比(モル比)を確認した。
(2)固有粘度(IV)
ポリエステル樹脂を、o-クロロフェノールに、150℃で、1.2g/dlの濃度で溶解し、固有粘度(dl/g)を、35℃の恒温槽中、ウベローデ粘度計を使用して測定した。
(3)耐熱性:ガラス転移温度(Tg)
ガラス-ゴムの転移温度(Tg)として、二次スキャニング中の昇温速度10℃/分で、Tg温度(℃)を測定した。
(4)数平均分子量(Mn)
数平均分子量を、ポリエステル樹脂をテトラヒドロフランに溶解後、ポリスチレン標準を使用して、ゲル浸透クロマトグラフィーによって測定した。
(5)溶媒溶解性
ポリエステル樹脂を、沸点により工業的に広く使用されている溶媒の中から、Kocosol-100(K-100)、シクロヘキサノン、トルエンおよびメチルエチルケトン(MEK)の典型的な4つの溶媒を選択することによって、以下の表2に列挙する溶媒成分中に、40重量%の濃度で溶解すること、および樹脂が完全に溶解したか否かを観察することによって、溶媒溶解性を得た。樹脂が完全に溶解して、透明な状態になった場合、〇で示し、不溶の樹脂が残っているか、または不透明な状態/層分離が経時的に観察された場合、×で示した。
シクロヘキサノン/ソルベントナフサ100(ソルベントナフサ100の製造者:SK Energy、製品名:Kocosol-100)の混合溶媒(重量比で50/50)中に、例1~5および比較例1~3のポリエステル樹脂のそれぞれを、40重量%の濃度で溶解し、樹脂溶液を調製した。208gの樹脂溶液、100gのTiO2(ルチル型)、および1.5gの湿潤剤(製造者:BYK、製品名:BYK-110)を混合して、分散混合物(ミルベース)を調製した。
例6~10および比較例4~6で調製したコーティング組成物の性能の評価方法は以下の通りである。
(6)光沢
0.5mmの厚さの亜鉛めっき鋼板を、コーティング組成物でコーティングし、熱風乾燥機を使用して、230℃で5分間、乾燥して、コーティング膜の厚さが20μmのコーティング鋼板を製造した。コーティング鋼板の60°の表面の光沢を、BYK製の光沢計を使用して、測定した。
(7)MEKラビング
上記(6)において使用されたものと同じコーティング鋼板を、MEKを十分に浸したガーゼを使用して擦り、耐薬品性を測定し、ラビング数を測定した。
(8)振り子硬度
上記(6)において使用されたものと同じコーティング鋼板に関して、振り子硬度を、ケーニッヒ測定法およびISO 1522 (2005)による、T.Q.Cの振り子硬度試験機を使用して、測定した。特に、振り子(重量:200g)を、コーティング鋼板の表面上に置き、振り子が停止した状態を、0°にセットした。次いで、振り子を、6°の角度に引っ張り、振り子運動を開始し、角度が3°になるまでの時間間隔を、3回測定した。
(9)鉛筆硬度
上記(6)において使用されたものと同じコーティング鋼板に関して、コーティング膜のひっかき硬度を、三菱鉛筆を使用して、測定した。様々な硬度の鉛筆を、45度の角度で、試験試料に立てかけた。次いで、表面を、750gの加重でひっかき、コーティング膜の硬度を、表面の損傷度に従って、測定した。上記に記載の条件下、表面を、特定の硬度を有する鉛筆を使用してひっかき、表面上にひっかき傷が発生しない最大硬度値を記録した。
Claims (10)
- (a)二価酸成分;ならびに
(b)イソソルビド、脂環式ジオールおよびネオペンチルグリコールを含むジオール成分、
を共重合させることによって得られる繰り返し単位を含むポリエステル樹脂であって、
前記ポリエステル樹脂が、80℃以上のガラス転移温度を有し、前記脂環式ジオールが、トリシクロC7~14アルカンの1つ以上のジオール誘導体であり、前記ジオール成分中の前記イソソルビドおよび前記脂環式ジオールの合計と前記ネオペンチルグリコールのモル比が、0.5~2.5:1であり、前記ジオール成分が、前記ジオール成分の総モル数に基づいて、20~45モル%の前記イソソルビドを含み、前記二価酸成分が、テレフタル酸、イソフタル酸、これらの誘導体およびこれらの混合物からなる群から選択される化合物を含む、ポリエステル樹脂。 - 前記ジオール成分が、前記ジオール成分の総モル数に基づいて20~30モル%の前記脂環式ジオールを含む、請求項1に記載のポリエステル樹脂。
- 前記脂環式ジオールが、トリシクロ[3.2.1.02,6]オクタン、トリシクロ[4.2.1.02,6]ノナン、トリシクロ[5.2.1.02,6]デカン、トリシクロ[6.2.1.02,6]ウンデカン、トリシクロ[7.2.1.02,6]ドデカン、トリシクロ[4.2.1.12,5]デカン、トリシクロ[4.3.1.12,5]デカン、トリシクロ[4.4.1.12,5]デカン、トリシクロ[2.2.1.02,6]ヘプタン、トリシクロ[2.2.2.02,6]オクタン、トリシクロ[3.2.2.02,6]ノナン、トリシクロ[3.3.1.13,6]デカン、トリシクロ[3.2.1.13,7]ノナン、トリシクロ[4.2.2.22,5]ドデカン、トリシクロ[4.3.2.22,5]トリデカン、トリシクロ[4.4.2.22,5]テトラデカン、トリシクロ[4.2.1.03,7]ノナン、トリシクロ[4.4.1.11,5]ドデカン、トリシクロ[6.2.1.02,7]ウンデカン、トリシクロ[5.2.2.02,6]ウンデカン、トリシクロ[6.2.2.02,7]ドデカン、トリシクロ[4.3.2.02,5]ウンデカン、トリシクロ[4.2.2.02,5]デカンおよびトリシクロ[5.5.1.03,11]トリデカンからなる群から選択される化合物のジオール誘導体、またはこれらの混合物である、請求項1に記載のポリエステル樹脂。
- 前記二価酸成分が、前記テレフタル酸、前記イソフタル酸またはこれらの混合物を、前記二価酸成分の総モル数に基づいて、1~100モル%の量で含む、請求項1に記載のポリエステル樹脂。
- 前記ポリエステル樹脂が、2,000~20,000の数平均分子量、2~60mgKOH/gのヒドロキシル価、および0.1~20mgKOH/gの酸価を有する、請求項1に記載のポリエステル樹脂。
- 前記ポリエステル樹脂が、80~150℃のガラス転移温度を有する、請求項1に記載のポリエステル樹脂。
- 請求項1~6のいずれか一項に記載のポリエステル樹脂;および
有機溶媒
を含む、コーティング組成物。 - 前記有機溶媒が、芳香族炭化水素溶媒、グリコールエステル溶媒、グリコールエーテル溶媒、ケトン溶媒、アルコール溶媒、およびこれらの混合物からなる群から選択される、請求項7に記載のコーティング組成物。
- 前記コーティング組成物が、10~40重量%の前記ポリエステル樹脂、および60~90重量%の前記有機溶媒を含む、請求項7に記載のコーティング組成物。
- 前記コーティング組成物が、架橋剤、硬化触媒、スリップ性のための添加剤、平滑剤、消泡剤、顔料、レベリング剤、およびこれらの混合物からなる群から選択される成分をさらに含む、請求項7に記載のコーティング組成物。
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KR102595616B1 (ko) * | 2018-02-07 | 2023-10-31 | 에스케이케미칼 주식회사 | 공중합 포화 폴리에스테르 수지 및 이를 함유하는 코팅 조성물 |
US11912862B2 (en) * | 2019-02-05 | 2024-02-27 | Eastman Chemical Company | Reduced haze compositions for coatings |
KR102318120B1 (ko) * | 2020-04-03 | 2021-10-26 | 도레이첨단소재 주식회사 | 유기용매 가용성 공중합 폴리에스테르 및 이를 포함하는 수처리막의 지지층 형성용 코팅액 |
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Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003119259A (ja) | 2001-10-12 | 2003-04-23 | Nippon Ester Co Ltd | ポリエステル樹脂 |
US20040092703A1 (en) | 2002-11-13 | 2004-05-13 | Germroth Ted Calvin | Method for making isosorbide containing polyesters |
WO2011031112A2 (en) | 2009-09-14 | 2011-03-17 | Sk Chemicals Co., Ltd. | Polyester resin and method for preparing the same |
JP2011190349A (ja) | 2010-03-15 | 2011-09-29 | Unitika Ltd | 可溶性共重合ポリエステル樹脂 |
US20120226014A1 (en) | 2009-11-13 | 2012-09-06 | Roy Lee | Copolymerized polyester heat shrinkable film |
JP2013189507A (ja) | 2012-03-13 | 2013-09-26 | Unitika Ltd | コーティング剤、塗膜および積層体 |
JP2013228697A (ja) | 2012-03-29 | 2013-11-07 | Mitsubishi Chemicals Corp | 眼鏡レンズ |
US20130295306A1 (en) | 2011-01-31 | 2013-11-07 | Sk Chemicals Co., Ltd. | Polyester resin composition and a production method therefor |
WO2015093453A1 (ja) | 2013-12-17 | 2015-06-25 | ユニチカ株式会社 | ポリエステル樹脂組成物およびそれを用いて得られる成形体 |
WO2015163400A1 (ja) | 2014-04-25 | 2015-10-29 | 三菱レイヨン株式会社 | ポリエステル樹脂、ポリエステル樹脂の製造方法及びポリエステル樹脂を含む塗料組成物 |
JP2018536073A (ja) | 2015-12-02 | 2018-12-06 | ロケット フレールRoquette Freres | 1,4:3,6−ジアンヒドロヘキシトールと種々の環状ジオールを含む、芳香族熱可塑性コポリエステル |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20100024304A (ko) | 2008-08-25 | 2010-03-05 | 에스케이씨 주식회사 | 편광판용 폴리에스터 보호필름 및 이를 포함하는 적층체 |
JP5370994B2 (ja) | 2008-09-17 | 2013-12-18 | ユニチカ株式会社 | 可溶性共重合ポリエステル樹脂 |
JP5717520B2 (ja) * | 2011-04-15 | 2015-05-13 | 三菱樹脂株式会社 | ポリエステル系樹脂組成物及び樹脂成形体 |
CN105237755B (zh) * | 2012-04-18 | 2017-09-29 | 帝人株式会社 | 共聚碳酸酯 |
EP2915849B1 (en) * | 2012-11-05 | 2018-03-28 | Idemitsu Kosan Co., Ltd. | Polycarbonate resin composition and molded article |
JP2014205335A (ja) * | 2013-04-16 | 2014-10-30 | 帝人株式会社 | 三次元構造を有するポリカーボネート樹脂成形品の製造方法およびその成形品 |
-
2016
- 2016-02-04 KR KR1020160014425A patent/KR102670942B1/ko active IP Right Grant
-
2017
- 2017-01-05 CN CN202310978066.7A patent/CN116987254A/zh active Pending
- 2017-01-05 US US16/063,387 patent/US11401372B2/en active Active
- 2017-01-05 CN CN201780006392.4A patent/CN108463480A/zh active Pending
- 2017-01-05 WO PCT/KR2017/000135 patent/WO2017135582A2/ko active Application Filing
- 2017-01-05 JP JP2018538105A patent/JP6957480B2/ja active Active
- 2017-01-05 EP EP17747627.2A patent/EP3412697B1/en active Active
- 2017-01-05 SG SG11201804740YA patent/SG11201804740YA/en unknown
- 2017-01-12 TW TW106100969A patent/TWI654220B/zh active
-
2021
- 2021-08-06 JP JP2021129718A patent/JP7408602B2/ja active Active
Patent Citations (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003119259A (ja) | 2001-10-12 | 2003-04-23 | Nippon Ester Co Ltd | ポリエステル樹脂 |
US20040092703A1 (en) | 2002-11-13 | 2004-05-13 | Germroth Ted Calvin | Method for making isosorbide containing polyesters |
JP2006506485A (ja) | 2002-11-13 | 2006-02-23 | イーストマン ケミカル カンパニー | イソソルビド含有ポリエステルの製造方法 |
WO2011031112A2 (en) | 2009-09-14 | 2011-03-17 | Sk Chemicals Co., Ltd. | Polyester resin and method for preparing the same |
JP2013504650A (ja) | 2009-09-14 | 2013-02-07 | エスケー ケミカルズ カンパニー リミテッド | ポリエステル樹脂およびその製造方法 |
US20120226014A1 (en) | 2009-11-13 | 2012-09-06 | Roy Lee | Copolymerized polyester heat shrinkable film |
JP2013510919A (ja) | 2009-11-13 | 2013-03-28 | エスケー ケミカルズ カンパニー リミテッド | 共重合ポリエステル熱収縮フィルム |
JP2011190349A (ja) | 2010-03-15 | 2011-09-29 | Unitika Ltd | 可溶性共重合ポリエステル樹脂 |
US20130295306A1 (en) | 2011-01-31 | 2013-11-07 | Sk Chemicals Co., Ltd. | Polyester resin composition and a production method therefor |
JP2014507531A (ja) | 2011-01-31 | 2014-03-27 | エスケー ケミカルズ カンパニー リミテッド | ポリエステル樹脂組成物およびその製造方法 |
JP2013189507A (ja) | 2012-03-13 | 2013-09-26 | Unitika Ltd | コーティング剤、塗膜および積層体 |
JP2013228697A (ja) | 2012-03-29 | 2013-11-07 | Mitsubishi Chemicals Corp | 眼鏡レンズ |
WO2015093453A1 (ja) | 2013-12-17 | 2015-06-25 | ユニチカ株式会社 | ポリエステル樹脂組成物およびそれを用いて得られる成形体 |
WO2015163400A1 (ja) | 2014-04-25 | 2015-10-29 | 三菱レイヨン株式会社 | ポリエステル樹脂、ポリエステル樹脂の製造方法及びポリエステル樹脂を含む塗料組成物 |
US20170037182A1 (en) | 2014-04-25 | 2017-02-09 | Mitsubishi Rayon Co., Ltd. | Polyester resin, method for manufacturing polyester resin, and coating composition containing polyester resin |
JP2018536073A (ja) | 2015-12-02 | 2018-12-06 | ロケット フレールRoquette Freres | 1,4:3,6−ジアンヒドロヘキシトールと種々の環状ジオールを含む、芳香族熱可塑性コポリエステル |
US20180362707A1 (en) | 2015-12-02 | 2018-12-20 | Roquette Freres | Aromatic thermoplastic copolyesters comprising 1,4:3,6-dianhydrohexitol and various cyclic diols |
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WO2017135582A3 (ko) | 2018-08-02 |
US20190077908A1 (en) | 2019-03-14 |
EP3412697A2 (en) | 2018-12-12 |
TWI654220B (zh) | 2019-03-21 |
SG11201804740YA (en) | 2018-07-30 |
JP2021185229A (ja) | 2021-12-09 |
JP2019510093A (ja) | 2019-04-11 |
KR102670942B1 (ko) | 2024-05-31 |
US11401372B2 (en) | 2022-08-02 |
KR20170093011A (ko) | 2017-08-14 |
EP3412697B1 (en) | 2022-09-07 |
CN108463480A (zh) | 2018-08-28 |
WO2017135582A2 (ko) | 2017-08-10 |
CN116987254A (zh) | 2023-11-03 |
EP3412697A4 (en) | 2019-07-03 |
TW201728611A (zh) | 2017-08-16 |
JP6957480B2 (ja) | 2021-11-02 |
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