RU2018125548A - BRANCHED POLYESTER-URETANE RESINS AND INCLUDING THEIR COATINGS - Google Patents

BRANCHED POLYESTER-URETANE RESINS AND INCLUDING THEIR COATINGS Download PDF

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RU2018125548A
RU2018125548A RU2018125548A RU2018125548A RU2018125548A RU 2018125548 A RU2018125548 A RU 2018125548A RU 2018125548 A RU2018125548 A RU 2018125548A RU 2018125548 A RU2018125548 A RU 2018125548A RU 2018125548 A RU2018125548 A RU 2018125548A
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polyester
urethane resin
segment
urethane
composition
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RU2018125548A
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Russian (ru)
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RU2018125548A3 (en
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Франческо ЧАЧЧО
Аннамария АНТОНАЧИ
Эдди БОНЕЛЛО
Стефане ШОХ
Вольфганг КЛЭГЕР
Беате ЗАЙЛЕР
Хосе КАМЕРАНО
Дебра Л. СИНГЕР
Джон Е. ШВЕНДЕМАН
Шанти СВАРУП
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Ппг Индастриз Огайо, Инк.
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Priority claimed from US14/967,763 external-priority patent/US10035872B2/en
Application filed by Ппг Индастриз Огайо, Инк. filed Critical Ппг Индастриз Огайо, Инк.
Publication of RU2018125548A publication Critical patent/RU2018125548A/en
Publication of RU2018125548A3 publication Critical patent/RU2018125548A3/ru

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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
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D1/00—Processes for applying liquids or other fluent materials
    • B05D1/02—Processes for applying liquids or other fluent materials performed by spraying
    • B05D1/04—Processes for applying liquids or other fluent materials performed by spraying involving the use of an electrostatic field
    • 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
    • C08G18/08—Processes
    • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
    • C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
    • 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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
    • C08G18/348—Hydroxycarboxylic acids
    • 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
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • 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
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
    • C09D5/4419—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications with polymers obtained otherwise than by polymerisation reactions only involving carbon-to-carbon unsaturated bonds
    • C09D5/4465—Polyurethanes

Claims (43)

1. Неотверждённая разветвлённая полиэфир-уретановая смола, полученная путём свободнорадикальной полимеризации двойных связей ненасыщенного полиэфир-уретанового форполимера, включающая:1. Uncured branched polyester-urethane resin obtained by free radical polymerization of double bonds of an unsaturated polyester-urethane prepolymer, including: b) сегмент полиола;b) a polyol segment; c) ненасыщенную поликарбоновую кислоту и/или её ангидрид и/или эфир; иc) unsaturated polycarboxylic acid and / or its anhydride and / or ether; and d) уретановый сегмент.d) urethane segment. 2. Полиэфир-уретановая смола по п. 1, в которой сегмент полиола включает неопентилгликоль и сегмент ненасыщенной поликарбоновой кислоты, ангидрида и/или эфира включает малеиновую кислоту, малеиновый ангидрид и/или эфир малеиновой кислоты.2. The polyester-urethane resin according to claim 1, wherein the segment of the polyol comprises neopentyl glycol and the segment of unsaturated polycarboxylic acid, anhydride and / or ether includes maleic acid, maleic anhydride and / or maleic ester. 3. Полиэфир-уретановая смола по п. 1, в которой полиэфир-уретановый форполимер подвергают взаимодействию с карбоновой кислотой, ангидридом или сложным эфиром и нейтрализуют амином до свободнорадикальной полимеризации.3. The polyester-urethane resin according to claim 1, wherein the polyester-urethane prepolymer is reacted with a carboxylic acid, anhydride or ester and neutralized with an amine until free radical polymerization. 4. Полиэфир-уретановая смола по п. 3, в которой карбоновая кислота включает 2,2-диметилолпропионовую кислоту и амин включает триэтиламин.4. The polyester-urethane resin according to claim 3, wherein the carboxylic acid comprises 2,2-dimethylolpropionic acid and the amine comprises triethylamine. 5. Полиэфир-уретан по п. 1, в котором уретановый сегмент сформирован реакцией изоцианата, по меньшей мере, с одной гидроксильной группой сегмента полиола.5. The polyester-urethane according to claim 1, wherein the urethane segment is formed by reacting an isocyanate with at least one hydroxyl group of the polyol segment. 6. Полиэфир-уретан по п. 1, в котором изоцианат включает изофорондиизоцианат.6. The polyether-urethane according to claim 1, wherein the isocyanate comprises isophorondiisocyanate. 7. Полиэфир-уретановая смола по п. 1, в которой свободнорадикальную полимеризацию проводят в водном растворе.7. The polyester-urethane resin according to claim 1, wherein the free radical polymerization is carried out in an aqueous solution. 8. Полиэфир-уретановая смола по п. 1, в которой Mw полиэфир-уретановой смолы составляет 15000-1000000 определенную гель-проникающей хроматографией с использованием полистирольного стандарта для калибровки.8. The polyester-urethane resin according to claim 1, wherein the M w of the polyester-urethane resin is 15,000-1000000 determined by gel permeation chromatography using a polystyrene standard for calibration. 9. Полиэфир-уретановая смола по п. 1, в которой MW полиэфир-уретановой смолы составляет 30000 или выше определенную гель-проникающей хроматографией с использованием полистирольного стандарта для калибровки.9. The polyester-urethane resin according to claim 1, wherein the M W polyester-urethane resin is 30,000 or higher determined by gel permeation chromatography using a polystyrene standard for calibration. 10. Полиэфир-уретановая смола по п. 1, в которой MW, полиэфир-уретанового форполимера составляет 2500 или выше определенную гель-проникающей хроматографией с использованием полистирольного стандарта для калибровкию.10. The polyester-urethane resin according to claim 1, wherein the M W , polyester-urethane prepolymer is 2500 or higher determined by gel permeation chromatography using a polystyrene standard for calibration. 11. Полиэфир-уретановая смола по п. 1, причём полиэфир-уретановая смола не содержит (мет)акрилата или его остатков.11. The polyester-urethane resin according to claim 1, wherein the polyester-urethane resin does not contain (meth) acrylate or its residues. 12. Полиэфир-уретановая смола по п. 1, в которой полиэфир-уретановая смола имеет гидроксильное число 75-120 мг КОН на грамм, измеренное по методу ASTM D4274.12. The polyester-urethane resin according to claim 1, in which the polyester-urethane resin has a hydroxyl number of 75-120 mg KOH per gram, measured according to ASTM D4274. 13. Композиция покрытия, включающая полиэфир-уретановую смолу по п. 1, и её сшивающий агент.13. A coating composition comprising a polyester-urethane resin according to claim 1, and a crosslinking agent thereof. 14. Композиция покрытия по п. 13, имеющая стойкость к расщеплению менее 2, измеренную с помощью модели 508 для ударных испытания по Эриксену, работающей при 2 бар и 25°C.14. The coating composition according to claim 13, having a splitting resistance of less than 2, measured using the Eriksen impact test model 508, operating at 2 bar and 25 ° C. 15. Композиция покрытия по п. 13, в которой сегмент полиола включает неопентилгликоль и сегмент ненасыщенной поликарбоновой кислоты, ангидрида и/или эфира включает малеиновую кислоту, малеиновый ангидрид и/или эфир малеиновой кислоты.15. The coating composition of claim 13, wherein the polyol segment comprises neopentyl glycol and the unsaturated polycarboxylic acid, anhydride and / or ester segment comprises maleic acid, maleic anhydride and / or maleic acid ester. 16. Композиция покрытия по п. 13, в котором покрытие представляет собой базовое покрытие.16. The coating composition of claim 13, wherein the coating is a base coating. 17. Подложка, покрытая, по меньшей мере, частично композицией покрытия по п. 13.17. A substrate coated at least partially with a coating composition according to claim 13. 18. Подложка по п. 17, причём подложка является частью транспортного средства.18. The substrate according to claim 17, wherein the substrate is part of a vehicle. 19. Способ формирования системы многослойного покрытия на подложке, включающий:19. A method of forming a multilayer coating system on a substrate, including: формирование первого слоя базового покрытия, по меньшей мере, на части подложки путём нанесения первой композиции базового покрытия, по меньшей мере, на часть подложки;forming a first basecoat layer on at least a portion of the substrate by applying a first basecoat composition to at least a portion of the substrate; необязательно, сушку или отверждение первого слоя базового покрытия;optionally drying or curing the first basecoat layer; формирование второго слоя базового покрытия, по меньшей мере, на части первого слоя базового покрытия путём нанесения второй композиции базового покрытия, которая является такой же или отличной от первой композиции базового покрытия, непосредственно, по меньшей мере, на часть первого слоя базового покрытия;forming a second base coat layer at least on a portion of the first base coat layer by applying a second base coat composition that is the same or different from the first base coat composition directly to at least a portion of the first base coat layer; необязательно, сушку или отверждение второго слоя базового покрытия; иoptionally drying or curing the second base coat layer; and отверждение любого слоя неотверждённого покрытия,curing any layer of uncured coating причём, по меньшей мере, одна из первой композиции базового покрытия и второй композиции базового покрытия включает композицию покрытия по п. 13.moreover, at least one of the first basecoat composition and the second basecoat composition includes a coating composition according to claim 13. 20. Способ по п. 19, дополнительно включающий формирование прозрачной композиции, по меньшей мере, на части второго слоя базового покрытия путём нанесения композиции прозрачного покрытия, по меньшей мере, на часть второго слоя базового покрытия.20. The method according to p. 19, further comprising forming a transparent composition at least on a part of the second base coat layer by applying a transparent coating composition to at least a portion of the second base coat layer. 21. Способ по п. 19, дополнительно включающий формирование электроосаждением слоя покрытия путём электроосаждения электроосаждаемой композиции покрытия, по меньшей мере, на часть подложки до стадии формирования первого слоя базового покрытия.21. The method according to p. 19, further comprising the formation of electrodeposition of the coating layer by electrodeposition of the electrodepositable coating composition, at least on a portion of the substrate to the stage of formation of the first layer of the base coating. 22. Способ по п. 19, в котором вторая композиция базового покрытия отличается от первой композиции базового покрытия.22. The method of claim 19, wherein the second basecoat composition is different from the first basecoat composition. 23. Способ по п. 19, в котором вторая композиция базового покрытия включает композицию покрытия по п. 13.23. The method according to p. 19, in which the second composition of the base coating includes a coating composition according to p. 13. 24. Неотверждённая разветвлённая полиэфир-уретановая смола, полученная:24. Uncured branched polyester-urethane resin obtained: а) свободнорадикальной полимеризацией двойной связи, по меньшей мере, одного ненасыщенного полиэфирного форполимера, имеющего гидроксильную функциональную группу для формирования полиэфирного полимера иa) free radical polymerization of a double bond of at least one unsaturated polyester prepolymer having a hydroxyl functional group to form a polyester polymer and b) взаимодействие полиэфирного полимера стадии а) с изоцианатом,b) reacting the polyester polymer of step a) with an isocyanate, причём полиэфирный форполимер включает:moreover, the polyester prepolymer includes: i) сегмент полиола; иi) a polyol segment; and ii) сегмент ненасыщенной поликарбоновой кислоты и/или ангидрида и/или эфира.ii) a segment of unsaturated polycarboxylic acid and / or anhydride and / or ether. 25. Полиэфир-уретановая смола по п. 24, в которой продукт реакции стадии b) подвергают взаимодействию с карбоновой кислотой и нейтрализуют амином и диспергируют в воде.25. The polyester-urethane resin according to claim 24, wherein the reaction product of step b) is reacted with a carboxylic acid and neutralized with an amine and dispersed in water. 26. Полиэфир-уретановая смола по п. 24, в которой изоцианат включает изофорондиизоцианат.26. The polyester-urethane resin according to claim 24, wherein the isocyanate comprises isophorondiisocyanate. 27. Неотверждённая разветвлённая полиэфир-уретановая смола, полученная путём свободнорадикальной полимеризации двойной связи первого ненасыщенного полиэфирного форполимера и двойной связи второго ненасыщенного полиэфирного форполимера, приём каждый форполимер независимо включает:27. An uncured branched polyester-urethane resin obtained by free-radical polymerization of a double bond of a first unsaturated polyester prepolymer and a double bond of a second unsaturated polyester prepolymer, each prepolymer independently includes: а) сегмент полиола; иa) a polyol segment; and b) сегмент ненасыщенной поликарбоновой кислоты и/или ангидрида и/или эфира; и в которой, по меньшей мере, один из ненасыщенных полиэфирных форполимеров включает уретановый сегмент и форполимеры являются одинаковыми или различными.b) a segment of unsaturated polycarboxylic acid and / or anhydride and / or ether; and in which at least one of the unsaturated polyester prepolymers includes a urethane segment and the prepolymers are the same or different.
RU2018125548A 2015-12-14 2016-12-13 BRANCHED POLYESTER-URETANE RESINS AND INCLUDING THEIR COATINGS RU2018125548A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US14/967,763 2015-12-14
US14/967,763 US10035872B2 (en) 2010-04-01 2015-12-14 Branched polyester-urethane resins and coatings comprising the same
PCT/US2016/066303 WO2017106152A2 (en) 2015-12-14 2016-12-13 Branched polyester-urethane resins and coatings comprising the same

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RU2018125548A true RU2018125548A (en) 2020-01-16
RU2018125548A3 RU2018125548A3 (en) 2020-01-16

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KR (1) KR102080423B1 (en)
CN (1) CN108473655B (en)
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WO (1) WO2017106152A2 (en)

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WO2017106152A3 (en) 2017-09-14
KR20180093032A (en) 2018-08-20

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