CA3008414C - Branched polyester-urethane resins and coatings comprising the same - Google Patents

Branched polyester-urethane resins and coatings comprising the same Download PDF

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Publication number
CA3008414C
CA3008414C CA3008414A CA3008414A CA3008414C CA 3008414 C CA3008414 C CA 3008414C CA 3008414 A CA3008414 A CA 3008414A CA 3008414 A CA3008414 A CA 3008414A CA 3008414 C CA3008414 C CA 3008414C
Authority
CA
Canada
Prior art keywords
coatings
same
branched polyester
urethane resins
disclosed
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.)
Active
Application number
CA3008414A
Other languages
French (fr)
Other versions
CA3008414A1 (en
Inventor
Francesco Ciaccio
Annamaria Antonaci
Eddy Bonello
Stephane Schoch
Wolfgang Klaeger
Beate Seiler
Jose CAMERANO
Debra L. Singer
Shanti Swarup
John E. Schwendeman
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
PPG Industries Ohio Inc
Original Assignee
PPG Industries Ohio Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US14/967,763 external-priority patent/US10035872B2/en
Application filed by PPG Industries Ohio Inc filed Critical PPG Industries Ohio Inc
Publication of CA3008414A1 publication Critical patent/CA3008414A1/en
Application granted granted Critical
Publication of CA3008414C publication Critical patent/CA3008414C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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
    • 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
    • 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
    • C08G18/28—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
    • C08G18/28—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
    • C08G18/74—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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Manufacturing & Machinery (AREA)
  • Molecular Biology (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Paints Or Removers (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

An uncured branched polyester-urethane resin prepared by free radical polymerization of an unsaturated polyester prepolymer having a polyol segment, an unsaturated polycarboxylic acid and/or an anhydride and/or ester thereof, and a urethane segment, wherein the polymerization occurs primarily by reaction of the unsaturation is disclosed. Coatings comprising the same are also disclosed, as are substrates coated at least in part with such coatings.
CA3008414A 2015-12-14 2016-12-13 Branched polyester-urethane resins and coatings comprising the same Active CA3008414C (en)

Applications Claiming Priority (3)

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

Publications (2)

Publication Number Publication Date
CA3008414A1 CA3008414A1 (en) 2017-06-22
CA3008414C true CA3008414C (en) 2021-05-18

Family

ID=58745340

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3008414A Active CA3008414C (en) 2015-12-14 2016-12-13 Branched polyester-urethane resins and coatings comprising the same

Country Status (7)

Country Link
EP (1) EP3390484A2 (en)
KR (1) KR102080423B1 (en)
CN (1) CN108473655B (en)
CA (1) CA3008414C (en)
MX (1) MX2018007177A (en)
RU (1) RU2018125548A (en)
WO (1) WO2017106152A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115717018B (en) * 2022-12-05 2024-07-16 德清县金秋塑粉有限公司 Special anti-corrosion powder coating for suspension spring of automobile shock absorber

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4650718A (en) 1985-08-19 1987-03-17 Ppg Industries, Inc. Color plus clear coatings employing polyepoxides and polyacid curing agents
US4933056A (en) 1988-09-26 1990-06-12 Ppg Industries, Inc. Cationic electrodepositable compositions through the use of sulfamic acid and derivatives thereof
TW242644B (en) 1992-10-30 1995-03-11 Ppg Industries Inc
DE4317981A1 (en) 1993-05-28 1994-12-01 Ranco Inc Gas-air ratio control device for a temperature control loop for gas appliances
US5530043A (en) 1994-05-25 1996-06-25 Ppg Industries, Inc. Low volatile organic content pigment grind composition
US5582704A (en) 1994-11-04 1996-12-10 Ppg Industries, Inc. Cationic resin and capped polyisocyanate curing agent suitable for use in electrodeposition
ES2191751T3 (en) 1995-05-01 2003-09-16 Ppg Ind Ohio Inc COMPOSITE COATINGS AND ENDURECIBLE COMPOSITIONS AND PROCEDURE FOR INCREASING STRIPPING AND ABRASION RESISTANCE.
US5820987A (en) 1996-08-21 1998-10-13 Ppg Industries, Inc. Cationic electrocoating compositions, method of making, and use
AU2681399A (en) 1998-02-18 1999-09-06 Ppg Industries Ohio, Inc. Low temperature cure waterborne coating compositions having improved appearance and humidity resistance and methods for coating substrates
ATE282652T1 (en) * 1998-08-17 2004-12-15 Bayer Materialscience Ag AQUEOUS COATING AGENT, ITS PRODUCTION AND USE FOR STORING PAINTS
US6875800B2 (en) 2001-06-18 2005-04-05 Ppg Industries Ohio, Inc. Use of nanoparticulate organic pigments in paints and coatings
US6894086B2 (en) 2001-12-27 2005-05-17 Ppg Industries Ohio, Inc. Color effect compositions
JP4775929B2 (en) 2002-02-13 2011-09-21 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 Coating line and process for forming a multilayer composite coating on a substrate
US7438972B2 (en) 2004-06-24 2008-10-21 Ppg Industries Ohio, Inc. Nanoparticle coatings for flexible and/or drawable substrates
FR2903412B1 (en) * 2006-07-07 2012-10-05 Cray Valley Sa URETHANE PRE-POLYMER - UNSATURATED POLYESTER AND APPLICATIONS THEREOF
US20110021694A1 (en) * 2009-07-23 2011-01-27 E.I. Du Pont De Nemours And Company Polyesterurethane for coating compositions
WO2013151050A1 (en) * 2012-04-03 2013-10-10 関西ペイント株式会社 Aqueous paint composition and method for forming coating
US8846156B2 (en) 2013-02-28 2014-09-30 Ppg Industries Ohio, Inc. Methods and compositions for coating substrates
SG11201608263PA (en) * 2014-04-04 2016-10-28 Ppg Ind Ohio Inc Branched polyester polymers and soft touch coatings comprising the same

Also Published As

Publication number Publication date
RU2018125548A3 (en) 2020-01-16
MX2018007177A (en) 2018-08-01
CN108473655B (en) 2021-08-03
KR20180093032A (en) 2018-08-20
WO2017106152A3 (en) 2017-09-14
CA3008414A1 (en) 2017-06-22
WO2017106152A2 (en) 2017-06-22
EP3390484A2 (en) 2018-10-24
CN108473655A (en) 2018-08-31
KR102080423B1 (en) 2020-02-21
RU2018125548A (en) 2020-01-16

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Effective date: 20180613