JP2012517497A - テトラメチルシクロブタンジオールを含有する脂肪族ポリエステルコーティング組成物 - Google Patents
テトラメチルシクロブタンジオールを含有する脂肪族ポリエステルコーティング組成物 Download PDFInfo
- Publication number
- JP2012517497A JP2012517497A JP2011549145A JP2011549145A JP2012517497A JP 2012517497 A JP2012517497 A JP 2012517497A JP 2011549145 A JP2011549145 A JP 2011549145A JP 2011549145 A JP2011549145 A JP 2011549145A JP 2012517497 A JP2012517497 A JP 2012517497A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- residue
- glycol
- mol
- residues
- 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.)
- Granted
Links
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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/123—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/137—Acids or hydroxy compounds containing cycloaliphatic rings
-
- 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
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
-
- 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
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- 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
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy 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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/199—Acids or hydroxy compounds containing cycloaliphatic rings
-
- 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
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/06—Unsaturated polyesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/06—Polyurethanes from polyesters
-
- 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
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/06—Polyurethanes from polyesters
-
- 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
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/423—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing cycloaliphatic groups
-
- 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
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
- C08G18/4241—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols from dicarboxylic acids and dialcohols in combination with polycarboxylic acids and/or polyhydroxy compounds which are at least trifunctional
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34922—Melamine; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
- C08L2666/18—Polyesters or polycarbonates according to C08L67/00 - C08L69/00; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/062—Copolymers with monomers not covered by C08L33/06
-
- 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
Abstract
Description
高い硬度を示す溶媒系のポリエステル熱硬化性コーティングは望ましい。高い硬度を有するコーティングは、典型的には高い光沢、良好な像の明瞭さ(DOI)、速い乾燥時間、耐スクラッチ性、耐ステイン性、耐化学物質性、および耐湿性、ならびに屋外耐久性を示す。
本発明は、2,2,4,4−テトラメチル−1,3−シクロブタンジオールから製造される硬化性脂肪族ポリエステルを提供する。よって、我々の発明の一態様は:
i.二塩基酸残基の総モル基準で少なくとも90モル%の、50〜100モル%の脂環式ジカルボン酸を含む少なくとも1種の脂肪族ジカルボン酸の残基、を含む二塩基酸残基;
ii.ジオール残基の総モル基準で50〜100モル%の2,2,4,4−テトラメチル−1,3−シクロブタンジオール残基を含むジオール残基;および
iii.ジオール残基とポリオール残基との総モル基準で2〜40モル%の、少なくとも1種のポリオール残基;
を含み、数平均分子量300〜10,000ダルトン、ガラス転移温度−35℃〜35℃、ヒドロキシル価20〜450mgKOH/ポリエステルg、および酸価0〜80mgKOH/ポリエステルgを有する、硬化性脂肪族ポリエステルである。
(A).(A)および(B)の総質量基準で50〜90質量%の、少なくとも1種の硬化性脂肪族ポリエステルであって、
i.二塩基酸残基の総モル基準で少なくとも90モル%の、少なくとも1種の脂肪族ジカルボン酸の残基を含む二塩基酸残基であって、該脂肪族ジカルボン酸が50〜100モル%の脂環式ジカルボン酸を含む、二塩基酸残基;
ii.ジオール残基の総モル基準50〜100モル%の2,2,4,4−テトラメチル−1,3−シクロブタンジオール残基を含むジオール残基;および
iii.ジオール残基とポリオール残基との総モル基準で2〜40モル%の少なくとも1種のポリオール残基;
を含み、数平均分子量300〜10,000ダルトン、ガラス転移温度−35℃〜35℃、ヒドロキシル価20〜450mgKOH/ポリエステルg、および酸価0〜80mgKOH/ポリエステルgを有する、硬化性脂肪族ポリエステル;
(B).(A)および(B)の総質量基準で10〜50質量%の、カルボン酸または水酸基との反応性を有する少なくとも1種の化合物を含む架橋剤;および
(C).(A)、(B)および(C)の総質量基準で10〜60質量%の少なくとも1種の非水性溶媒;
を含む、熱硬化性コーティング組成物である。
我々は、2,2,4,4−テトラメチル−1,3−シクロブタンジオール(本明細書で「TMCD」と略す)を含有する硬化性脂肪族ポリエステルを用いて、高い光沢、良好な硬度および可撓性;ならびに溶媒および化学物質に対する耐性を示す、溶媒系で高固形分の熱硬化性コーティングを製造できることを見出した。これらの脂肪族ポリエステルはまた、熱硬化性アクリルレジン(「TSA」)とブレンドして、低粘度、良好な親和性、可撓性およびTg保持を有するブレンド物を製造できる。よって、一般的な態様において、我々の発明は:
i.二塩基酸残基の総モル基準で少なくとも90モル%の、少なくとも1種の脂肪族ジカルボン酸の残基を含む二塩基酸残基であって、該脂肪族ジカルボン酸が50〜100モル%の脂環式ジカルボン酸を含む、二塩基酸残基;
ii.ジオール残基の総モル基準で50〜100モル%の2,2,4,4−テトラメチル−1,3−シクロブタンジオール残基を含むジオール残基;および
iii.ジオール残基とポリオール残基との総モル基準で2〜40モル%の少なくとも1種のポリオール残基;
を含み、数平均分子量300〜10,000ダルトン、ガラス転移温度−35℃〜35℃、ヒドロキシル価20〜450mgKOH/ポリエステルg、および酸価0〜80mgKOH/ポリエステルgを有する、硬化性脂肪族ポリエステルを提供する。本発明の別の側面は、上記脂肪族ポリエステルレジンを含む溶媒系熱硬化性コーティング配合物である。コーティング配合物は、任意に、架橋剤、種々の添加剤および顔料を含むことができる。
i.二塩基酸残基の総モル基準で50〜100モル%の、1,4−シクロヘキサンジカルボン酸、ヘキサヒドロフタル酸無水物、またはこれらの混合物の残基から選択される脂環式ジカルボン酸、を含む少なくとも1種の脂肪族ジカルボン酸の残基から本質的になる二塩基酸残基;
ii.ジオール残基の総モル基準で75〜100モル%の2,2,4,4−テトラメチル−1,3−シクロブタンジオール残基、から本質的になるジオール残基;および
iii.ジオール残基とポリオール残基との総モル基準で2〜40モル%の、少なくとも1種のポリオールの残基;
から本質的になり、数平均分子量300〜10,000ダルトン、ガラス転移温度−35℃〜35℃、ヒドロキシル価20〜450mgKOH/ポリエステルg、および酸価0〜80mgKOH/ポリエステルgを有する、硬化性脂肪族ポリエステルである。
(A).(A)および(B)の総質量基準で50〜90質量%の、少なくとも1種の硬化性脂肪族ポリエステルであって、
i.二塩基酸残基の総モル基準で少なくとも90モル%の、少なくとも1種の脂肪族ジカルボン酸の残基を含む二塩基酸残基であって、該脂肪族ジカルボン酸が50〜100モル%の脂環式ジカルボン酸を含む、二塩基酸残基;
ii.ジオール残基の総モル基準で50〜100モル%の2,2,4,4−テトラメチル−1,3−シクロブタンジオール残基を含むジオール残基;および
iii.ジオール残基とポリオール残基との総モル基準で2〜40モル%の少なくとも1種のポリオール残基;
を含み、数平均分子量300〜10,000ダルトン、ガラス転移温度−35℃〜35℃、ヒドロキシル価20〜450mgKOH/ポリエステルg、および酸価0〜80mgKOH/ポリエステルgを有する、硬化性脂肪族ポリエステル;
(B).(A)および(B)の総質量基準で10〜50質量%の、カルボン酸または水酸基との反応性を有する少なくとも1種の化合物を含む架橋剤;および
(C).(A)、(B)および(C)の総質量基準で10〜60質量%の少なくとも1種の非水性溶媒;
を含む、熱硬化性コーティング組成物である。
硬化性脂肪族ポリエステルの調製−比較例P1、例P2、例P3および例P4−例および比較の脂肪族ポリエステルレジン(表1)は、以下の手順に従い、目的の数平均分子量=1250、ヒドロキシル質量当量=500、ヒドロキシ官能性=2.5、および最終酸価=8、で調製した。
価は、ASTM法 D1639を用いて評価した。ヒドロキシル価は、レジンを過剰の無水酢酸とピリジン中で反応させることによってエステル化し、次いで未反応無水物を水で分解することにより評価した。次いで、得られる酢酸を、KOHの標準溶液で滴定する。1グラムのレジンサンプルに対する当量のKOHのミリグラム数を、ヒドロキシル価として報告する。数平均分子量は、ゲルパーミエーションクロマトグラフィによって、屈折率検出器を用いてポリスチレン標準で評価した。
(b)2,2−ジメチル−1,3−プロパンジオール(Eastman)
(c)2,2,4,4−テトラメチル−1,3−シクロブタンジオール(Eastman)
(d)トリメチロールプロパン(Perstorp)
(e)アジピン酸(DuPont)
(f)ブチルスタノイック酸(Arkema)
(g)1,4−シクロヘキサンジカルボン酸
(h)ヘキサヒドロフタル酸無水物
(b)全てのレジンは、n−BuOAC中の固形分70質量%
(b)BYK−Chemie
(c)Arkema (ジブチルスズジラウレート)
(d)Bayer MaterialScience (脂肪族ポリイソシアネートHDIトリマー)
Claims (12)
- i.二塩基酸残基の総モル基準で少なくとも90モル%の、少なくとも1種の脂肪族ジカルボン酸の残基を含む二塩基酸残基であって、該脂肪族ジカルボン酸が約50〜100モル%の脂環式ジカルボン酸を含む、二塩基酸残基;
ii.ジオール残基の総モル基準で約50〜100モル%の2,2,4,4−テトラメチル−1,3−シクロブタンジオール残基を含むジオール残基;および
iii.ジオール残基とポリオール残基との総モル基準で約2〜約40モル%の少なくとも1種のポリオール残基;
を含み、数平均分子量約300〜約10,000ダルトン、ガラス転移温度約−35℃〜約35℃、ヒドロキシル価約20〜約450mgKOH/ポリエステルg、および酸価0〜約80mgKOH/ポリエステルgを有する、硬化性脂肪族ポリエステル。 - 該二塩基酸残基が、約50〜約85モル%の、1,4−シクロヘキサンジカルボン酸、1,3−シクロヘキサンジカルボン酸、ヘキサヒドロフタル酸無水物から選択される少なくとも1種の脂環式ジカルボン酸の残基、および約50〜約15モル%の、アジピン酸、ドデカン二酸、セバシン酸、アゼライン酸、マレイン酸、フマル酸、コハク酸およびグルタル酸から選択される少なくとも1種の非環式脂肪族ジカルボン酸の残基を含み;そして該ジオール残基が、約50〜0モル%の、ネオペンチルグリコール、エチレングリコール、プロピレングリコール、ジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、ペンタエチレングリコール、ヘキサエチレングリコール、ヘプタエチレングリコール、オクタエチレングリコール、ノナエチレングリコール、デカエチレングリコール、1,3−プロパンジオール、2,4−ジメチル−2−エチル−ヘキサン−1,3−ジオール、2,2−ジメチル−1,2−プロパンジオール、2−エチル−2−ブチル−1,3−プロパンジオール、2−エチル−2−イソブチル−1,3−プロパンジオール、1,3−ブタンジオール、1,4−ブタンジオール、1,5−ペンタンジオール、1,6−ヘキサンジオール、2,2,4−トリメチル−1,6−ヘキサンジオール、チオジエタノール、1,2−シクロヘキサンジメタノール、1,3−シクロヘキサンジメタノール、1,4−シクロヘキサンジメタノール、2,2,4−トリメチル−1,3−ペンタンジオール、p−キシレンジオール、ヒドロキシピバリルヒドロキシピバレート、1,10−デカンジオール、および水素化ビスフェノールAから選択される少なくとも1種のジオールの残基を含む、請求項1に記載の硬化性脂肪族ポリエステル。
- 該二塩基酸残基が、約50〜約85モル%の1,4−シクロヘキサンジカルボン酸、ヘキサヒドロフタル酸無水物またはこれらの混合物の残基、および約15〜約50モル%のアジピン酸残基を含み;そして該ジオール残基が、約50〜0モル%のネオペンチルグリコール残基を含む、請求項2に記載の硬化性脂肪族ポリエステル。
- 該二塩基酸残基が、約50モル%のヘキサヒドロフタル酸無水物残基および約50モル%のアジピン酸残基を含み;そして該ジオール残基が、約75〜100モル%の2,2,4,4−テトラメチル−1,3−シクロブタンジオール残基および約25〜0モル%のネオペンチルグリコール残基を含む、請求項3に記載の硬化性脂肪族ポリエステル。
- 約3〜約30モル%の、トリメチロールプロパン、ペンタエリスリトール、トリメチロールエタン、エリスリトール、スレイトール、ジペンタエリスリトール、ソルビトールおよびグリセリンから選択される少なくとも1種のポリオールの残基を含む、請求項1に記載の硬化性脂肪族ポリエステル。
- ポリエステル1グラム当たりのヒドロキシル価約30〜約250mg水酸化カリウム、ポリエステル1グラムあたりの酸価約2〜約15mg水酸化カリウム、および数平均分子量約700〜約7000ダルトン、およびTg約−20℃〜約20℃を有する、請求項1に記載の硬化性脂肪族ポリエステル。
- (A).(A)および(B)の総質量基準で約50〜約90質量%の、請求項1〜6のいずれか1項に記載の少なくとも1種の硬化性脂肪族ポリエステル;
(B).(A)および(B)の総質量基準で約10〜約50質量%の、カルボン酸または水酸基との反応性を有する少なくとも1種の化合物を含む架橋剤;および
(C).(A)、(B)および(C)の総質量基準で約10〜約60質量%の少なくとも1種の非水性溶媒;
を含む、熱硬化性コーティング組成物。 - 該架橋剤が、メラミン、イソシアネートおよびイソシアヌレートから選択される少なくとも1種の化合物を含む、請求項7に記載のコーティング組成物。
- 該架橋剤が、ヘキサメトキシメチルメラミン、テトラメトキシメチルベンゾグアナミン、テトラメトキシメチルウレア、および混合ブトキシ/メトキシ置換メラミンから選択される少なくとも1種のメラミン化合物を含む、請求項8に記載のコーティング組成物。
- 該架橋剤が、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、1,6−ヘキサメチレンジイソシアネートのビウレット、1,6−ヘキサメチレンジイソシアネートのトリマー、またはこれらの組合せを含む、請求項8に記載のコーティング組成物。
- 該非水性溶媒が、ベンゼン、キシレン、ミネラルスピリット、ナフサ、トルエン、アセトン、メチルエチルケトン、メチルn−アミルケトン、メチルイソアミルケトン、n−ブチルアセテート、イソブチルアセテート、t−ブチルアセテート、n−プロピルアセテート、イソプロピルアセテート、エチルアセテート、メチルアセテート、エタノール、n−プロパノール、イソプロパノール、n−ブタノール、sec−ブタノール、イソブタノール、エチレングリコールモノブチルエーテル、プロピレングリコールn−ブチルエーテル、プロピレングリコールメチルエーテル、プロピレングリコールモノプロピルエーテル、ジプロピレングリコールメチルエーテル、ジエチレングリコールモノブチルエーテル、トリメチルペンタンジオールモノ−イソブチレート、エチレングリコールモノオクチルエーテル、ジアセトンアルコール、2,2,4−トリメチル−1,3−ペンタンジオールモノイソブチレート、またはこれらの組合せを含む、請求項7に記載のコーティング組成物。
- 請求項7に記載のコーティング組成物でコートされている、成形品。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/367,190 US9029461B2 (en) | 2009-02-06 | 2009-02-06 | Aliphatic polyester coating compositions containing tetramethyl cyclobutanediol |
US12/367,190 | 2009-02-06 | ||
PCT/US2010/000213 WO2010090712A1 (en) | 2009-02-06 | 2010-01-27 | Aliphatic polyester coating compositions containing tetramethyl cyclobutanediol |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2012517497A true JP2012517497A (ja) | 2012-08-02 |
JP5462285B2 JP5462285B2 (ja) | 2014-04-02 |
Family
ID=42034500
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011549145A Expired - Fee Related JP5462285B2 (ja) | 2009-02-06 | 2010-01-27 | テトラメチルシクロブタンジオールを含有する脂肪族ポリエステルコーティング組成物 |
Country Status (9)
Country | Link |
---|---|
US (2) | US9029461B2 (ja) |
EP (1) | EP2393865A1 (ja) |
JP (1) | JP5462285B2 (ja) |
KR (1) | KR20110127171A (ja) |
CN (1) | CN102307928B (ja) |
BR (1) | BRPI1007304A2 (ja) |
CA (1) | CA2750516A1 (ja) |
MX (1) | MX2011007470A (ja) |
WO (1) | WO2010090712A1 (ja) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012517500A (ja) * | 2009-02-06 | 2012-08-02 | イーストマン ケミカル カンパニー | テトラメチルシクロブタンジオールを含む熱硬化性ポリエステルコーティング組成物 |
JP2012517498A (ja) * | 2009-02-06 | 2012-08-02 | イーストマン ケミカル カンパニー | アクリルおよび脂肪族ポリエステルのブレンド物を含有するコーティング組成物 |
JP2012517499A (ja) * | 2009-02-06 | 2012-08-02 | イーストマン ケミカル カンパニー | テトラメチルシクロブタンジオールを含有するコーティング組成物 |
KR20150074136A (ko) * | 2012-10-23 | 2015-07-01 | 이스트만 케미칼 컴파니 | 네오펜틸 글리콜 및 2,2,4,4-테트라알킬-1,3-사이클로부탄다이올을 포함하는 코폴리에스터 |
JP2016148008A (ja) * | 2015-02-14 | 2016-08-18 | 三菱樹脂株式会社 | 積層ポリエステルフィルム |
Families Citing this family (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9029461B2 (en) * | 2009-02-06 | 2015-05-12 | Eastman Chemical Company | Aliphatic polyester coating compositions containing tetramethyl cyclobutanediol |
KR102135072B1 (ko) | 2011-02-07 | 2020-07-20 | 에스더블유아이엠씨 엘엘씨 | 용기 및 기타 물품을 위한 코팅 조성물 및 코팅 방법 |
CN104540907B (zh) | 2012-08-09 | 2018-04-10 | Swimc有限公司 | 用于容器和其它物品的组合物以及使用相同组合物的方法 |
CA2935134C (en) * | 2014-01-02 | 2019-12-03 | Emerald Kalama Chemical, Llc | Polyester plasticizers with benzoic acid end-caps |
WO2015160788A1 (en) | 2014-04-14 | 2015-10-22 | Valspar Sourcing, Inc. | Methods of preparing compositions for containers and other articles and methods of using same |
US9487619B2 (en) | 2014-10-27 | 2016-11-08 | Eastman Chemical Company | Carboxyl functional curable polyesters containing tetra-alkyl cyclobutanediol |
US9598602B2 (en) | 2014-11-13 | 2017-03-21 | Eastman Chemical Company | Thermosetting compositions based on phenolic resins and curable poleyester resins made with diketene or beta-ketoacetate containing compounds |
US20160115345A1 (en) * | 2014-10-27 | 2016-04-28 | Eastman Chemical Company | Curable polyesters and thermosetting compostions containing resole phenolic resins |
US9650539B2 (en) | 2014-10-27 | 2017-05-16 | Eastman Chemical Company | Thermosetting compositions based on unsaturated polyesters and phenolic resins |
CN107001772A (zh) * | 2014-10-27 | 2017-08-01 | 伊士曼化工公司 | 可固化聚酯和含有甲阶酚醛树脂的热固性组合物 |
US20160340471A1 (en) * | 2015-05-19 | 2016-11-24 | Eastman Chemical Company | Aliphatic polyester coating compositions containing tetramethyl cyclobutanediol |
BR112017026517A2 (pt) * | 2015-06-09 | 2018-08-14 | Ppg Ind Ohio Inc | composição de revestimento, substrato e dispositivo eletrônico ou componente eletrônico |
MX2017016073A (es) * | 2015-06-09 | 2018-02-21 | Ppg Ind Ohio Inc | Composiciones de revestimiento de tacto suave, resistentes a las manchas y revestimientos formados a partir de las mismas. |
US20170088665A1 (en) | 2015-09-25 | 2017-03-30 | Eastman Chemical Company | POLYMERS CONTAINING CYCLOBUTANEDIOL AND 2,2 BIS(HYDROXYMETHYL) AlKYLCARBOXYLIC ACID |
KR101811515B1 (ko) * | 2016-01-22 | 2017-12-22 | 주식회사 케이씨씨 | 내장부품용 하이그로시 도료 조성물 |
US9988553B2 (en) | 2016-02-22 | 2018-06-05 | Eastman Chemical Company | Thermosetting coating compositions |
US11208520B2 (en) | 2016-02-23 | 2021-12-28 | Eastman Chemical Company | Isocyanate-modified rigid thermoplastic polymer compositions |
EP3420011A4 (en) | 2016-02-23 | 2019-10-23 | Eastman Chemical Company | MODIFIED RIGID THERMOPLASTIC POLYMER COMPOSITIONS USING ISOCYANATE |
US10011737B2 (en) * | 2016-03-23 | 2018-07-03 | Eastman Chemical Company | Curable polyester polyols and their use in thermosetting soft feel coating formulations |
US11732165B2 (en) | 2017-06-13 | 2023-08-22 | Eastman Chemical Company | Low-temperature curable compositions |
EP3743475A1 (en) * | 2018-01-23 | 2020-12-02 | Eastman Chemical Company | Novel polyesteramides, processes for the preparation thereof, and polyesteramide compositions |
US20210348017A1 (en) * | 2018-10-11 | 2021-11-11 | Eastman Chemical Company | Coatings with improved scratch resistance |
CN112789324B (zh) * | 2018-10-11 | 2023-05-05 | 伊士曼化工公司 | 耐刮擦热固性涂层组合物 |
US20210348016A1 (en) * | 2018-10-11 | 2021-11-11 | Eastman Chemical Company | Thermosetting coating composition with improved scratch resistance |
EP3891240A4 (en) * | 2018-12-06 | 2022-07-13 | Eastman Chemical (China) Co., Ltd. | ADHESIVE COMPOSITIONS COMPRISING 1,4-CYCLOHEXANEDIMETHANOL AND METHODS OF PREPARING THEM |
WO2020123279A1 (en) * | 2018-12-11 | 2020-06-18 | Eastman Chemical Company | Self-curable and low temperature curable coating compositions |
US11261359B2 (en) | 2018-12-11 | 2022-03-01 | Eastman Chemical Company | Flexible substrates comprising curable compositions containing acetoacetylated resins |
CN113993977A (zh) | 2019-05-24 | 2022-01-28 | 伊士曼化工公司 | 进入气体裂化器中加工的液体流中混入少量热解油 |
EP3760658A1 (de) | 2019-07-03 | 2021-01-06 | Covestro Deutschland AG | Beständige 2k-pur-beschichtungen |
US20220363862A1 (en) * | 2019-07-29 | 2022-11-17 | Eastman Chemical Company | Recycle content cyclobutane diol polyester |
US11319262B2 (en) | 2019-10-31 | 2022-05-03 | Eastman Chemical Company | Processes and systems for making recycle content hydrocarbons |
US11945998B2 (en) | 2019-10-31 | 2024-04-02 | Eastman Chemical Company | Processes and systems for making recycle content hydrocarbons |
US20230374341A1 (en) * | 2020-10-27 | 2023-11-23 | Eastman Chemical Company | Coating composition containing tmcd polyester and a modifying polyester |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5097006A (en) * | 1990-11-21 | 1992-03-17 | U C B S.A. | Weatherable powder coating compositions |
JPH08503984A (ja) * | 1992-11-27 | 1996-04-30 | イーストマン ケミカル カンパニー | 熱硬化性塗料組成物 |
JPH08333442A (ja) * | 1995-05-31 | 1996-12-17 | Shell Internatl Res Maatschappij Bv | コポリエステル組成物 |
JPH08512078A (ja) * | 1993-07-01 | 1996-12-17 | イーストマン ケミカル カンパニー | 粉体塗料組成物 |
US5596037A (en) * | 1992-03-16 | 1997-01-21 | U C B S.A. | Carboxyl-terminated polyesters for the preparation of powder coating compositions |
JPH09111183A (ja) * | 1995-10-20 | 1997-04-28 | Kansai Paint Co Ltd | 塗料組成物及びワンコート塗装鋼板 |
Family Cites Families (97)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2891930A (en) | 1957-03-25 | 1959-06-23 | Eastman Kodak Co | Fiber-forming polyesters from trans-1, 4-cyclohexanedicarboxylic compounds and 1, 1-cyclohexane dimethanol |
FR83790E (fr) | 1959-12-18 | 1964-10-09 | Kodak Pathe | Nouveaux polymères dérivés des 2, 2, 4, 4-tétraalcoyl-1, 3-cyclobutanediols et leurs applications industrielles |
US3313777A (en) | 1959-12-18 | 1967-04-11 | Eastman Kodak Co | Linear polyesters and polyester-amides from 2, 2, 4, 4-tetraalkyl-1, 3-cyclobutanediols |
BE615850Q (fr) | 1960-12-16 | 1962-07-16 | Eastman Kodak Co | Nouveaux polymères dérivés des 2,2,4,4-tétraalcoyl-1,3-cyclobutanediols et leurs applications industrielles |
US3227764A (en) | 1960-12-30 | 1966-01-04 | Eastman Kodak Co | Separation of cis and trans isomers of tetraalkyl - 1,3 - cyclobutanediols and novel compound obtained thereby |
US3345313A (en) | 1963-02-20 | 1967-10-03 | Trojan Powder Co | Alkyd resins and their preparation from reaction mixtures comprising a polymethylolalkanoic acid |
FR1456345A (fr) | 1964-12-07 | 1966-10-21 | Eastman Kodak Co | Nouveau procédé de préparation de polyesters et nouveaux produits obtenus |
US3484339A (en) | 1966-05-02 | 1969-12-16 | Eastman Kodak Co | Blends of polyesters containing free carboxyl groups and laminate thereof |
US3502620A (en) | 1967-05-11 | 1970-03-24 | Eastman Kodak Co | Branched polyesters containing terminal carboxyl groups |
US3538187A (en) | 1969-03-04 | 1970-11-03 | Atlas Chem Ind | Polyester resin from a mixture of dihydric alcohols |
US3789044A (en) | 1971-01-26 | 1974-01-29 | Ashland Oil Inc | Novel cured compositions prepared from the reaction of a polyisocyanate and a hydroxybenzoic acid capped epoxide-containing material |
US3856830A (en) | 1971-12-23 | 1974-12-24 | Atlas Chem Ind | Polymerizable urethane compounds |
US4076766A (en) | 1975-03-27 | 1978-02-28 | E. I. Du Pont De Nemours And Company | Flexible thermosetting acrylic enamels |
US4074061A (en) | 1976-10-26 | 1978-02-14 | Eastman Kodak Company | Unsaturated polyester containing formal linkages |
US4322508A (en) | 1978-03-20 | 1982-03-30 | Ford Motor Company | High solids paint composition comprising hydroxy functional oligoesters and hydroxy functional copolymers |
US4267279A (en) * | 1979-07-27 | 1981-05-12 | Koppers Company, Inc. | Polyester composition stabilized against gel-time drift with amine salt and method for making same |
US4299933A (en) | 1980-06-02 | 1981-11-10 | Eastman Kodak Company | Polyester adhesives |
US4581093A (en) | 1980-12-15 | 1986-04-08 | Whittaker Corporation | Branched polyester adhesive compositions and method employing same |
US4350807A (en) | 1981-02-09 | 1982-09-21 | Eastman Kodak Company | Copolyester compositions |
US4338379A (en) | 1981-02-13 | 1982-07-06 | E. I. Du Pont De Nemours And Company | High-solids thermosetting enamel coating composition |
US4363908A (en) | 1981-08-31 | 1982-12-14 | Eastman Kodak Company | Polyester modified with alkyl- or alkenylsuccinic anhydrides |
US4397989A (en) | 1982-02-08 | 1983-08-09 | E. I. Du Pont De Nemours & Co. | High solids coating composition of an acrylic polymer a polyester polyol and an alkylated melamine crosslinking agent |
US4525544A (en) | 1982-04-12 | 1985-06-25 | The Dow Chemical Company | Vinyl ester resin composition |
US4480077A (en) | 1982-10-12 | 1984-10-30 | Dow Chemical Co | Heat resistant vinyl ester resin composition |
US5023367A (en) | 1982-12-27 | 1991-06-11 | King Industries, Inc. | Linear, low-molecular-weight polyester-based polyol |
US4525504A (en) | 1983-10-24 | 1985-06-25 | Eastman Kodak Company | Stabilized polyester compositions suitable for outdoor applications |
US4585854A (en) | 1984-04-16 | 1986-04-29 | The Goodyear Tire & Rubber Company | Polyester composition |
US4724173A (en) | 1986-01-29 | 1988-02-09 | The Board Of Governors For Higher Education, State Of Rhode Island | Method of preventing gel coat blistering in fiber glass reinforced polymers |
US4751267A (en) | 1986-03-06 | 1988-06-14 | The Glidden Company | Acrylic polyester high solids coatings |
US4716200A (en) | 1986-03-06 | 1987-12-29 | The Glidden Company | Acrylic polyester high solids coatings |
US4737551A (en) | 1986-06-23 | 1988-04-12 | E. I. Dupont De Nemours And Company | Coating composition of a hydroxy group-containing modified polyester with polymerized lactone monomers |
US4698391A (en) | 1986-07-30 | 1987-10-06 | Eastman Kodak Company | Crosslinked polymers with lowered resistivity and materials and methods for their preparation |
US4859760A (en) | 1987-12-07 | 1989-08-22 | Eastman Kodak Company | Polyurethane powder coating compositions |
FR2635716B1 (fr) | 1988-08-24 | 1990-11-02 | Beneteau Sa Chantiers | Procede de protection contre l'eau d'une paroi en resine stratifiee et paroi en resine stratifiee protegee ainsi obtenue |
US4910292A (en) | 1988-10-14 | 1990-03-20 | Eastman Kodak Company | Water-dissipatable polyester resins and coatings prepared therefrom |
US4939233A (en) | 1988-12-05 | 1990-07-03 | Eastman Kodak Company | Aqueous polymer compositions and methods for their preparation |
JPH0338281A (ja) | 1989-07-04 | 1991-02-19 | Nippon Steel Metal Prod Co Ltd | プレコート金属板製造法 |
US5017679A (en) | 1989-08-30 | 1991-05-21 | Eastman Kodak Company | Polyesters terminated with carboxycyclohexanecarboxylate groups |
US6184311B1 (en) * | 1990-03-26 | 2001-02-06 | Courtaulds Coatings (Holdings) Limited | Powder coating composition of semi-crystalline polyester and curing agent |
US5124388A (en) | 1990-05-07 | 1992-06-23 | Eastman Kodak Company | Films and containers of heat resistant copolyesters |
DE4024204A1 (de) | 1990-07-31 | 1992-02-06 | Basf Lacke & Farben | Ueberzugsmittel auf der basis hydroxylgruppen enthaltender polykondensations- und polyadditionsprodukte sowie deren verwendung |
US5025086A (en) | 1990-11-13 | 1991-06-18 | Eastman Kodak Company | Trifunctional monomer compounds, polyesters derived therefrom and thermosetting coating compositions containing the polyesters |
US5160792A (en) | 1991-02-04 | 1992-11-03 | Eastman Kodak Company | Thermosetting powder coating compositions |
US5254637A (en) | 1991-06-03 | 1993-10-19 | Eastman Kodak Company | Thermosetting coating compositions |
US5256759A (en) | 1991-06-10 | 1993-10-26 | Eastman Kodak Company | Thermosetting coating compositions |
US5245002A (en) | 1991-06-10 | 1993-09-14 | Eastman Kodak Company | Thermosetting coating compositions |
US5256761A (en) | 1991-09-23 | 1993-10-26 | Eastman Kodak Company | Polyester coatings containing covalently-bound mesogenic monomers |
ATE154380T1 (de) | 1992-07-06 | 1997-06-15 | Eastman Chem Co | Wärmehärtende pulverlackzusammensetzungen |
CZ138993A3 (en) * | 1992-07-15 | 1994-02-16 | Herberts & Co Gmbh | Aqueous, thermosetting coating composition, process of its preparation and use |
US5349026A (en) | 1992-11-20 | 1994-09-20 | Rohm And Haas Company | Reactive coalescents |
US5344872A (en) | 1993-02-19 | 1994-09-06 | Eastman Chemical Company | Ink compositions containing certain methacrylates |
GB9304940D0 (en) | 1993-03-11 | 1993-04-28 | Ucb Sa | Thermosetting powder compositions based on polyesters and acrylic copolymers |
US5371148A (en) | 1993-06-23 | 1994-12-06 | Union Carbide Chemicals & Plastics Technology Corporation | Reactive polymers having pendant flexible side chains prepared from ethylenically unsaturated carbodiimides |
US5393840A (en) * | 1993-11-01 | 1995-02-28 | Eastman Chemical Company | Thermosetting coating compositions |
US5416187A (en) | 1994-04-04 | 1995-05-16 | Eastman Chemical Company | Process for the preparation of phenol-functional polyester resins |
ES2163457T3 (es) | 1994-04-06 | 2002-02-01 | Ppg Ind Ohio Inc | Composiciones de revestimiento que comprenden 1,4-ciclohexano dimetanol. |
US5393609A (en) | 1994-06-13 | 1995-02-28 | Eastman Chemical Company | Weatherable powder coatings |
JPH0873781A (ja) | 1994-09-12 | 1996-03-19 | Sumitomo Metal Ind Ltd | 耐汚染性に優れた柚肌調意匠性金属板の製造方法 |
US5498668A (en) | 1994-10-31 | 1996-03-12 | Eastman Chemical Company | Blends of certain polyesters with acrylics |
DE19500358A1 (de) | 1995-01-09 | 1996-07-11 | Bayer Ag | Polyesterpolyole und ihre Verwendung in Zweikomponenten-Polyurethanlacken |
US5464909A (en) | 1995-03-24 | 1995-11-07 | Eastman Chemical Company | Powder coating having good UV resistance |
US5554701A (en) | 1995-03-24 | 1996-09-10 | Eastman Chemical Company | Crosslinked polyesters made from decahydronaphthalene dimethanol |
EP0769030A4 (en) | 1995-04-19 | 1997-10-22 | Exxon Chemical Patents Inc | COMPOSITIONS CONTAINING POLYOLS, PHENOLESTERS AND ISOCYANATES |
US5681906A (en) | 1995-04-19 | 1997-10-28 | Exxon Chemical Patents Inc. | Thermoset coating compositions having improved hardness |
JPH093341A (ja) | 1995-06-15 | 1997-01-07 | Nippon Oil & Fats Co Ltd | 熱硬化性組成物、塗装仕上げ方法及び塗装物品、並びに成形方法及び成形品 |
US5646237A (en) | 1995-08-15 | 1997-07-08 | Eastman Chemical Company | Water-dispersible copolyester-ether compositions |
JP2914297B2 (ja) * | 1996-05-29 | 1999-06-28 | 日本電気株式会社 | Pll周波数シンセサイザ |
DE19629823A1 (de) | 1996-07-24 | 1998-01-29 | Basf Lacke & Farben | Beschichtungsmittel auf Basis einer verzweigten hydroxylgruppenhaltigen, polyestermodifizierten Polyacrylatharzes und seine Verwendung in Verfahren zur Herstellung einer Mehrschichtlackierung |
US5955565A (en) | 1996-12-28 | 1999-09-21 | Eastman Chemical Company | Polyesters from terephthalic acid, 2,2,4,4-tetramethyl-1,3-cyclobutanediol and ethylene glycol |
NL1005809C2 (nl) | 1997-04-14 | 1998-10-19 | Dsm Nv | Poederverfbindmiddelsamenstelling. |
US6887937B1 (en) | 1997-05-21 | 2005-05-03 | Akzo Nobel Nv | Coating composition based on a hydroxy group-containing film forming polymer, a polyisocyanate compound, and a diol |
US6248843B1 (en) | 1998-09-18 | 2001-06-19 | Mcwhorter Technologies, Inc. | Powder coatings based on branched oligoesters and triazole blocked polyisocyanates |
US20010051706A1 (en) | 1998-12-03 | 2001-12-13 | Scott E. George | Terephthalate-based sulfopolyesters |
US6265072B1 (en) | 1999-04-27 | 2001-07-24 | Eastman Chemical Company | UV-stabilized polymeric structures |
EP1268691A1 (en) | 2000-02-08 | 2003-01-02 | The C.P. Hall Company | Low voc, nonlinear polyester polyol resin-based compositions |
WO2002020633A1 (en) | 2000-09-05 | 2002-03-14 | Dainippon Ink And Chemicals, Inc. | Unsaturated polyester resin composition |
JP2002235038A (ja) | 2001-02-08 | 2002-08-23 | Mitsubishi Electric Corp | 非水分散粉体塗料組成物 |
TWI237052B (en) | 2001-07-26 | 2005-08-01 | Surface Specialties Sa | Radiation curable powder coating compositions |
TW591341B (en) | 2001-09-26 | 2004-06-11 | Shipley Co Llc | Coating compositions for use with an overcoated photoresist |
US7087672B2 (en) | 2002-05-08 | 2006-08-08 | E. I. Du Pont De Nemours And Company | Non-yellowing polyester coating composition |
KR100905063B1 (ko) | 2002-06-13 | 2009-06-30 | 니폰 페인트 가부시키가이샤 | 수성 수지 조성물 |
US20040087736A1 (en) | 2002-11-04 | 2004-05-06 | Bin Wu | Powder coating compositions containing anhydride end-capped crystalline polyesters |
US20060079650A1 (en) | 2004-10-12 | 2006-04-13 | Stevenson Thomas A | Flexible, super durable powder coating composition |
WO2006083343A1 (en) | 2005-02-01 | 2006-08-10 | Henkel Corporation | Vinyl ether/acrylate block resins, compositions and methods of making same |
JP2006233068A (ja) | 2005-02-25 | 2006-09-07 | Nippon Ester Co Ltd | 共重合ポリエステル |
US20060287485A1 (en) | 2005-06-17 | 2006-12-21 | Crawford Emmett D | Sound barriers comprising polyester compositions formed from 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 1,4-cyclohexanedimethanol |
US7375144B2 (en) | 2005-06-16 | 2008-05-20 | Eastman Chemical Company | Abrasion resistant coatings |
US7470500B2 (en) | 2005-07-19 | 2008-12-30 | Az Electronic Materials Usa Corp. | Organic bottom antireflective polymer compositions |
US8586701B2 (en) | 2005-10-28 | 2013-11-19 | Eastman Chemical Company | Process for the preparation of copolyesters based on 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 1,4-cyclohexanedimethanol |
US20080139687A1 (en) | 2005-11-10 | 2008-06-12 | Henkel Corporation | Vinyl Ether/Acrylate Block Resins, Compositions and Methods of Making Same |
US7915319B2 (en) | 2005-12-19 | 2011-03-29 | Henkel Corporation | Visible light curing systems, methods for reducing health risks to individuals exposed to systems designed to cure curable compositions by exposure to radiation, methods for bonding substrates and visible light curing compositions |
US20070232778A1 (en) | 2006-03-28 | 2007-10-04 | Leslie Shane Moody | Certain polyester compositions which comprise cyclobutanediol, cyclohexanedimethanol, and high trans-cyclohexanedicarboxylic acid |
US9029460B2 (en) * | 2009-02-06 | 2015-05-12 | Stacey James Marsh | Coating compositions containing acrylic and aliphatic polyester blends |
US8324316B2 (en) | 2009-02-06 | 2012-12-04 | Eastman Chemical Company | Unsaturated polyester resin compositions containing 2,2,2,4-tetramethyl-1,3-cyclobutanediol and articles made therefrom |
US8163850B2 (en) | 2009-02-06 | 2012-04-24 | Eastman Chemical Company | Thermosetting polyester coating compositions containing tetramethyl cyclobutanediol |
US8168721B2 (en) | 2009-02-06 | 2012-05-01 | Eastman Chemical Company | Coating compositions containing tetramethyl cyclobutanediol |
US9029461B2 (en) * | 2009-02-06 | 2015-05-12 | Eastman Chemical Company | Aliphatic polyester coating compositions containing tetramethyl cyclobutanediol |
-
2009
- 2009-02-06 US US12/367,190 patent/US9029461B2/en active Active
-
2010
- 2010-01-27 MX MX2011007470A patent/MX2011007470A/es active IP Right Grant
- 2010-01-27 WO PCT/US2010/000213 patent/WO2010090712A1/en active Application Filing
- 2010-01-27 KR KR1020117020262A patent/KR20110127171A/ko not_active Application Discontinuation
- 2010-01-27 CN CN201080006610.2A patent/CN102307928B/zh active Active
- 2010-01-27 BR BRPI1007304A patent/BRPI1007304A2/pt not_active IP Right Cessation
- 2010-01-27 JP JP2011549145A patent/JP5462285B2/ja not_active Expired - Fee Related
- 2010-01-27 CA CA2750516A patent/CA2750516A1/en not_active Abandoned
- 2010-01-27 EP EP10703372A patent/EP2393865A1/en not_active Withdrawn
-
2014
- 2014-06-16 US US14/305,411 patent/US20140296407A1/en not_active Abandoned
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5097006A (en) * | 1990-11-21 | 1992-03-17 | U C B S.A. | Weatherable powder coating compositions |
US5596037A (en) * | 1992-03-16 | 1997-01-21 | U C B S.A. | Carboxyl-terminated polyesters for the preparation of powder coating compositions |
JPH08503984A (ja) * | 1992-11-27 | 1996-04-30 | イーストマン ケミカル カンパニー | 熱硬化性塗料組成物 |
JPH08512078A (ja) * | 1993-07-01 | 1996-12-17 | イーストマン ケミカル カンパニー | 粉体塗料組成物 |
JPH08333442A (ja) * | 1995-05-31 | 1996-12-17 | Shell Internatl Res Maatschappij Bv | コポリエステル組成物 |
JPH09111183A (ja) * | 1995-10-20 | 1997-04-28 | Kansai Paint Co Ltd | 塗料組成物及びワンコート塗装鋼板 |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012517500A (ja) * | 2009-02-06 | 2012-08-02 | イーストマン ケミカル カンパニー | テトラメチルシクロブタンジオールを含む熱硬化性ポリエステルコーティング組成物 |
JP2012517498A (ja) * | 2009-02-06 | 2012-08-02 | イーストマン ケミカル カンパニー | アクリルおよび脂肪族ポリエステルのブレンド物を含有するコーティング組成物 |
JP2012517499A (ja) * | 2009-02-06 | 2012-08-02 | イーストマン ケミカル カンパニー | テトラメチルシクロブタンジオールを含有するコーティング組成物 |
JP2016047915A (ja) * | 2009-02-06 | 2016-04-07 | イーストマン ケミカル カンパニー | テトラメチルシクロブタンジオールを含有するコーティング組成物 |
KR20150074136A (ko) * | 2012-10-23 | 2015-07-01 | 이스트만 케미칼 컴파니 | 네오펜틸 글리콜 및 2,2,4,4-테트라알킬-1,3-사이클로부탄다이올을 포함하는 코폴리에스터 |
JP2016500740A (ja) * | 2012-10-23 | 2016-01-14 | イーストマン ケミカル カンパニー | ネオペンチルグリコール及び2,2,4,4−テトラアルキル−1,3−シクロブタンジオールを含むコポリエステル |
KR102144143B1 (ko) | 2012-10-23 | 2020-08-12 | 이스트만 케미칼 컴파니 | 네오펜틸 글리콜 및 2,2,4,4-테트라알킬-1,3-사이클로부탄다이올을 포함하는 코폴리에스터 |
JP2016148008A (ja) * | 2015-02-14 | 2016-08-18 | 三菱樹脂株式会社 | 積層ポリエステルフィルム |
Also Published As
Publication number | Publication date |
---|---|
US20140296407A1 (en) | 2014-10-02 |
BRPI1007304A2 (pt) | 2016-02-10 |
US9029461B2 (en) | 2015-05-12 |
JP5462285B2 (ja) | 2014-04-02 |
CA2750516A1 (en) | 2010-08-12 |
CN102307928A (zh) | 2012-01-04 |
KR20110127171A (ko) | 2011-11-24 |
CN102307928B (zh) | 2014-05-07 |
MX2011007470A (es) | 2011-08-03 |
EP2393865A1 (en) | 2011-12-14 |
WO2010090712A1 (en) | 2010-08-12 |
US20100204401A1 (en) | 2010-08-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5462285B2 (ja) | テトラメチルシクロブタンジオールを含有する脂肪族ポリエステルコーティング組成物 | |
JP5855945B2 (ja) | テトラメチルシクロブタンジオールを含む熱硬化性ポリエステルコーティング組成物 | |
EP2393891B1 (en) | Coating compositions containing acrylic and aliphatic polyester blends | |
US10676565B2 (en) | Aliphatic polyester coating compositions containing tetramethyl cyclobutanediol | |
JP5855944B2 (ja) | テトラメチルシクロブタンジオールを含有するコーティング組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20130117 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130716 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130723 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20131021 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20131217 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140116 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
LAPS | Cancellation because of no payment of annual fees | ||
S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
R360 | Written notification for declining of transfer of rights |
Free format text: JAPANESE INTERMEDIATE CODE: R360 |
|
R360 | Written notification for declining of transfer of rights |
Free format text: JAPANESE INTERMEDIATE CODE: R360 |
|
R371 | Transfer withdrawn |
Free format text: JAPANESE INTERMEDIATE CODE: R371 |