JP2017517591A - 分枝状ポリエステルポリマーおよびそれを含むソフトタッチコーティング - Google Patents
分枝状ポリエステルポリマーおよびそれを含むソフトタッチコーティング Download PDFInfo
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- JP2017517591A JP2017517591A JP2016560731A JP2016560731A JP2017517591A JP 2017517591 A JP2017517591 A JP 2017517591A JP 2016560731 A JP2016560731 A JP 2016560731A JP 2016560731 A JP2016560731 A JP 2016560731A JP 2017517591 A JP2017517591 A JP 2017517591A
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- Prior art keywords
- polyester
- coating
- prepolymer
- acid
- anhydride
- Prior art date
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- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims description 8
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 4
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- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
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- 239000001384 succinic acid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000010435 syenite Substances 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
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- 125000005627 triarylcarbonium group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- MTPVUVINMAGMJL-UHFFFAOYSA-N trimethyl(1,1,2,2,2-pentafluoroethyl)silane Chemical compound C[Si](C)(C)C(F)(F)C(F)(F)F MTPVUVINMAGMJL-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/04—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters
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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
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
- B32B27/365—Layered products comprising a layer of synthetic resin comprising polyesters comprising polycarbonates
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/02—Physical, chemical or physicochemical properties
- B32B7/025—Electric or magnetic properties
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/02—Physical, chemical or physicochemical properties
- B32B7/027—Thermal properties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/04—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters
- C08F299/0407—Processes of polymerisation
- C08F299/0421—Polymerisation initiated by wave energy or particle radiation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/044—Forming conductive coatings; Forming coatings having anti-static properties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/052—Forming heat-sealable coatings
-
- 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
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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
- C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
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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
- C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
- C09D167/07—Unsaturated polyesters having carbon-to-carbon unsaturation having terminal carbon-to-carbon unsaturated bonds
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Paints Or Removers (AREA)
- Polyesters Or Polycarbonates (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Laminated Bodies (AREA)
Abstract
Description
本願は、“BRANCHED POLYESTER POLYMERS AND COATINGS COMPRISING THE SAME”と題する、2010年4月1日に出願された米国特許出願第12/752,570号の一部継続出願である。
本発明は、第1の不飽和ポリエステルプレポリマーと第2の不飽和ポリエステルプレポリマーの二重結合のフリーラジカル重合によって調製される架橋性分枝状ポリエステルポリマーに関する。このポリエステルポリマーは25℃のTgまたはそれより低いTgを有する。本発明は、さらに、そうしたポリエステルを含むコーティング、およびそうしたコーティングが塗布されている基材に関し、硬化した場合、このコーティングはソフトなタッチを基材に付与する。
ポリオールとポリ酸の様々な組合せの重縮合によって製造される従来の直鎖状および分枝状ポリエステル樹脂は、コーティング産業において広範に使用されている。これらは、多くの様々な産業において使用される広範な金属性および非金属性基材をコーティングするために使用されている。これらの産業は、可撓性コーティングが所望されるものを特に含む。特に適切な例には、包装産業、コイルコーティングならびに特定の産業用および自動車用コーティングにおいて使用される基材が含まれる。コーティングは特定の「タッチ感触」を有することが所望されることが多い。例えば、消費者用電子機器産業では、「ソフトな感触」または「ソフトなタッチ」を有するコーティングが所望されることが多い。ソフトタッチコーティングは、ある範囲のタッチ感触、例えばビロードのような感触、絹のような感触またはゴムのような感触を基材に付与することができる。コーティングの感触にかかわらず、コーティングが摩耗、損傷(marring)、引っかきおよび/または汚染に対して少なくともある程度の耐性を有することも所望される。したがって、許容できる性能特性を有するソフトタッチコーティングが所望される。
本発明は、第1の不飽和ポリエステルプレポリマーの二重結合と第2の不飽和ポリエステルプレポリマーの二重結合のフリーラジカル重合によって調製される架橋性分枝状ポリエステルポリマーであって、各プレポリマーが独立に、a)ポリオールセグメントと;b)不飽和ポリカルボン酸ならびに/またはその無水物および/もしくはエステルとを含み、該分枝状ポリエステルポリマーが25℃のTgまたはそれより低いTgを有する、ポリエステルポリマーを対象とする。そうしたポリエステルを含むコーティングも、そのようなコーティングで少なくとも一部分がコーティングされた基材と同様に、やはり本発明の範囲内である。
本発明は、一般にプレポリマーの反応生成物を含む架橋性分枝状ポリエステルポリマーを対象とし、このプレポリマーは、ポリオールセグメントと不飽和ポリカルボン酸ならびに/またはその無水物および/もしくはエステルとを含む成分の反応生成物である。このプレポリマーは、不飽和ポリエステルであり、本明細書では「不飽和ポリエステルプレポリマー」、「プレポリマー」または同様の用語で称されることがある。フリーラジカル開始剤は、不飽和ポリエステルプレポリマーの不飽和を介して重合を開始させ、それによって分枝状ポリエステルをもたらすために使用される。この分枝状ポリエステルは架橋性であり、これは、別の化合物と架橋を施され得ることを意味する。すなわち、このポリエステルは、クロスリンカーなどの別の化合物上の官能基と反応する官能基を有する。プレポリマーの不飽和の反応は、架橋性分枝状ポリエステルをもたらす。このポリエステルはポリマーである。それは硬化したコーティングではない。したがって、本発明は、モノマーおよび/またはポリマー上の不飽和点の架橋が硬化したコーティングをもたらす従来技術とは異なる。
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(実施例6)
Claims (21)
- 第1の不飽和ポリエステルプレポリマーの二重結合と第2の不飽和ポリエステルプレポリマーの二重結合のフリーラジカル重合によって調製される架橋性分枝状ポリエステルポリマーであって、各プレポリマーが独立に、
a)ポリオールセグメントと、
b)不飽和ポリカルボン酸ならびに/またはその無水物および/もしくはエステルと
を含み、
前記分枝状ポリエステルポリマーが25℃のTgまたはそれより低いTgを有するポリエステルポリマー。 - 前記プレポリマーがソフトセグメントをさらに含む、請求項1に記載のポリエステル。
- 前記ソフトセグメントがアジピン酸を含む、請求項2に記載のポリエステル。
- 前記プレポリマーがイソフタル酸をさらに含む、請求項1に記載のポリエステル。
- 前記ポリオールセグメントが2−メチル−1,3−プロパンジオールを含む、請求項1に記載のポリエステル。
- 前記不飽和ポリカルボン酸/無水物/エステルが、マレイン酸/無水物/エステルおよび/またはイタコン酸/無水物/エステルを含む、請求項1に記載のポリエステル。
- 少なくとも1つのプレポリマーが、アジピン酸、2−メチル−1,3−プロパンジオールおよびマレイン酸/無水物/エステルを含む、請求項2に記載のポリエステル。
- 前記プレポリマーのMWが5,000〜10,000である、請求項1に記載のポリエステル。
- 前記ポリエステルのMWが4,000〜10,000である、請求項1に記載のポリエステル。
- 前記ポリエステルのマーク・ホーウィンクパラメータが0.48またはそれ未満である、請求項1に記載のポリエステル。
- コーティングであって、請求項1に記載のポリエステルおよびそのためのクロスリンカーを含む、コーティング。
- フィッシャー微小硬度試験で測定した場合に2〜10N/mm2の硬度、ASTM法D1894で測定した場合に0.05〜0.2の摩擦係数、ASTM法F2357で測定した場合に250〜500サイクルの耐摩耗性および/またはテーラー・ホブソン精密サートロニックデュオ粗さ測定機で測定した場合に20μm〜50μmの表面粗さを有する、請求項11に記載のコーティング。
- 前記プレポリマーの少なくとも1つが、アジピン酸、2−メチル−1,3−プロパンジオールおよびマレイン酸/無水物/エステルを含む、請求項11に記載のコーティング。
- 着色剤をさらに含む、請求項11に記載のコーティング。
- 前記クロスリンカーがイソシアネートを含む、請求項11に記載のコーティング。
- 少なくとも一部において請求項11に記載のコーティングでコーティングされている基材。
- 消費者用電子機器部品を含む、請求項16に記載の基材。
- PC/ABSを含む、請求項16に記載の基材。
- 金属缶を含む、請求項16に記載の基材。
- 前記ポリエステルが(メタ)アクリレートまたはその残基を含まない、請求項1に記載のポリエステル。
- 前記プレポリマー中の唯一の不飽和が成分b)からのものである、請求項1に記載のポリエステル。
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US14/245,399 US9115241B2 (en) | 2010-04-01 | 2014-04-04 | Branched polyester polymers and soft touch coatings comprising the same |
US14/245,399 | 2014-04-04 | ||
PCT/US2015/024012 WO2015153844A1 (en) | 2014-04-04 | 2015-04-02 | Branched polyester polymers and soft touch coatings comprising the same |
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US10035872B2 (en) | 2010-04-01 | 2018-07-31 | Ppg Industries Ohio, Inc. | Branched polyester-urethane resins and coatings comprising the same |
CA3008414C (en) * | 2015-12-14 | 2021-05-18 | Ppg Industries Ohio, Inc. | Branched polyester-urethane resins and coatings comprising the same |
EP3667662B1 (en) | 2018-12-12 | 2022-08-10 | Panasonic Intellectual Property Corporation of America | Acoustic echo cancellation device, acoustic echo cancellation method and acoustic echo cancellation program |
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JPH09501712A (ja) * | 1993-08-12 | 1997-02-18 | イーストマン ケミカル カンパニー | 被覆に使用する水分散性アクリル変性ポリエステル樹脂及びその製造方法 |
JP2013523962A (ja) * | 2010-04-01 | 2013-06-17 | ピーピージー・インダストリーズ・オハイオ・インコーポレイテッド | 分枝ポリエステルポリマーおよびそれを含むコーティング |
JP2013527268A (ja) * | 2010-04-01 | 2013-06-27 | ピーピージー・インダストリーズ・オハイオ・インコーポレイテッド | 高官能性ポリエステルおよびそれを含むコーティング |
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CA2944749C (en) | 2019-03-26 |
WO2015153844A1 (en) | 2015-10-08 |
JP2019073738A (ja) | 2019-05-16 |
CN106414530A (zh) | 2017-02-15 |
RU2643808C1 (ru) | 2018-02-06 |
KR101811170B1 (ko) | 2018-01-25 |
MX2016013008A (es) | 2017-04-27 |
TW201546111A (zh) | 2015-12-16 |
CA2944749A1 (en) | 2015-10-08 |
TWI577712B (zh) | 2017-04-11 |
SG11201608263PA (en) | 2016-10-28 |
EP3126427A1 (en) | 2017-02-08 |
CN106414530B (zh) | 2020-04-24 |
KR20160141820A (ko) | 2016-12-09 |
JP6526048B2 (ja) | 2019-06-05 |
MY176199A (en) | 2020-07-24 |
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