WO2020197512A1 - Composition de polyuréthane durcissant à l'humidité en une partie pour revêtement protecteur haute performance - Google Patents

Composition de polyuréthane durcissant à l'humidité en une partie pour revêtement protecteur haute performance Download PDF

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Publication number
WO2020197512A1
WO2020197512A1 PCT/TH2019/000005 TH2019000005W WO2020197512A1 WO 2020197512 A1 WO2020197512 A1 WO 2020197512A1 TH 2019000005 W TH2019000005 W TH 2019000005W WO 2020197512 A1 WO2020197512 A1 WO 2020197512A1
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WO
WIPO (PCT)
Prior art keywords
weight
moisture curing
part moisture
protective coating
curing polyurethane
Prior art date
Application number
PCT/TH2019/000005
Other languages
English (en)
Inventor
Pinai Mungsantisuk
Original Assignee
Thai Marine Protection Co., Ltd.
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
Application filed by Thai Marine Protection Co., Ltd. filed Critical Thai Marine Protection Co., Ltd.
Priority to PCT/TH2019/000005 priority Critical patent/WO2020197512A1/fr
Publication of WO2020197512A1 publication Critical patent/WO2020197512A1/fr

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Classifications

    • 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
    • C09D5/08—Anti-corrosive paints
    • C09D5/10—Anti-corrosive paints containing metal dust
    • C09D5/103—Anti-corrosive paints containing metal dust containing Al
    • 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
    • C08G18/70—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
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/62—Metallic pigments or fillers
    • C09C1/64—Aluminium
    • C09C1/644—Aluminium treated with organic compounds, e.g. 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
    • 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
    • C09D7/20—Diluents or solvents
    • 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
    • C09D7/61—Additives non-macromolecular inorganic
    • C09D7/62—Additives non-macromolecular inorganic modified by treatment with other compounds
    • 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
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/20—Particle morphology extending in two dimensions, e.g. plate-like
    • C01P2004/24—Nanoplates, i.e. plate-like particles with a thickness from 1-100 nanometer
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/60—Particles characterised by their size
    • C01P2004/61—Micrometer sized, i.e. from 1-100 micrometer
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/60—Particles characterised by their size
    • C01P2004/62—Submicrometer sized, i.e. from 0.1-1 micrometer
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/60—Particles characterised by their size
    • C01P2004/64—Nanometer sized, i.e. from 1-100 nanometer
    • 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
    • C08G2150/00—Compositions for coatings
    • C08G2150/90—Compositions for anticorrosive coatings
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • 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
    • C08K3/02—Elements
    • C08K3/08—Metals
    • C08K2003/0812—Aluminium
    • 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
    • C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
    • C08K5/353—Five-membered rings

Definitions

  • This invention is related to one-part moisture curing polyurethane composition for high performance protective coating.
  • Protective coatings have been used to protect significant works or structures, such as seagoing ships, power plants, offshore platforms, petrochemical plants, many marine and industrial structures.
  • the old traditional coating systems are based upon sandblasting for surface preparation, multiple coats, short lifetime endurance and required continual repair. Thus, die better performance and easy to use coatings are of great interest.
  • Polyurethane coatings are widely used as protective coating and topcoat for both new and old structures because they possess recoat ability, chemical resistance, UV resistance, abrasion resistance, low curing temperature, etc.
  • MCP moisture curing polyurethane coatings
  • the moisture curable polyurethane composition comprises a urethane prepolymer, and a morpholine catalyst comprising a dimorpholinodiethylether (i) and a N,N-dimethylaminoethylmorpholine (ii).
  • content of the dimorpholinodiethylether (i) in the polyurethane composition is preferably less than 0.15% by weight
  • content of the N,N- dimethylaminoethylmorpholine (ii) in the polyurethane composition is preferably in the range of 0.04 to 2% by weight.
  • one-part moisture curable urethane composition comprises an isocyanate-terminated urethane prepolymer as a main component
  • the additional components comprise of (A), an aliphatic hydrocarbon compound having a solubility parameter value of 7.0 to 8.0 cal/cm 3 and (B), a compound having in the molecule at least one basic structure represented by the following formula:
  • n 0 to 3.
  • the content of the compound (A) is 0.5 to 2.0% by weight in the whole composition.
  • the content of the compound (B) is 0.5 to 2.0% by weight in the whole composition.
  • the moisture curing polyisocyanate mixtures for coating comprise of a solvent-containing polyisocyanate mixture having a solvent content of less than 50 weight %, an NCO content of from 7 to 15 weight %, a content of monomeric TDI of less than 0.2 weight %, and a content of monomeric aliphatic and/or cycloaliphatic isocyanate of less than 0.2 weight %.
  • a TDI component contains TDI isocyanurate poly isocyanates.
  • the present invention relates to one-part moisture curing polyurethane composition for high performance protective coating.
  • the composition of high performance protective coating comprises aromatic polyisocyanate prepolymer based on diphenylmethane diisocyanate (MDI) (i), resin coated non-leafing aluminium flakes (ii), unsaturated polycarboxylic acid polymer (iii), polysiloxane copolymer (iv) and mono-oxazolidine (v)
  • the polyisocyanates cure through the reaction of free isocyanates, active NCO group, with atmospheric moisture or residual moisture in the surface rust.
  • the primary amino group and carbon dioxide are produced from this reaction.
  • the amino groups react with isocyanate to form urea as shown below
  • One-component coating based on aromatic isocyanates generally requires shorter drying time than that based on aliphatic isocyanates.
  • Coatings based on MDI have a tendency to yellow in the light and show loss of gloss on weathering.
  • Non-leafing aluminium flakes in the coating are uniformly dispersed in the coating film which will provide great barrier effects for moisture corrosive substances.
  • the aluminium flakes also reflect light and heat through the coating film which make the coating films UV and heat resistance with bright surface finish.
  • the aluminium flakes can be coated with some resin such as acrylic resin.
  • the resin coated aluminium flakes have excellent chemical resistance, adhesiveness and arc resistance.
  • Unsaturated polycarboxylic acid polymer and polysiloxane copolymer are additives having medium to high polarity which will act as bridges between the individual pigment particles, thereby creating three-dimensional networks. This mechanism helps to control flocculation of the pigments.
  • Mono-oxazolidine is an additive that acts as moisture scavenger in polyurethane coating. It is used to eliminate moisture from the raw materials, the atmosphere and substrate. It prevents bubbling and downglossing caused by high moisture levels.
  • the one-part moisture curing polyurethane for high performance protective coating can be prepared by mixing the following raw materials together:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne la composition d'un polyuréthane durcissant à l'humidité en une partie pour un revêtement protecteur haute performance. Les plaques d'acier revêtues du polyuréthane durcissant à l'humidité en une partie ont été alternées dans une solution neutre de chlorure de sodium à 3,5 % telle que mentionnée dans la norme ASTM G 44-99 pendant 6500 heures. Seule une légère rouille a été trouvée au niveau du bord des plaques d'acier, mais il n'y a pas de cloques de peinture ou de rouille détectée sur les plaques. Le polyuréthane durcissant à l'humidité en une partie selon la présente invention peut être utilisé comme revêtement protecteur dans un environnement difficile comme une zone de marée ou une zone d'éclaboussement en eau de mer.
PCT/TH2019/000005 2019-03-28 2019-03-28 Composition de polyuréthane durcissant à l'humidité en une partie pour revêtement protecteur haute performance WO2020197512A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/TH2019/000005 WO2020197512A1 (fr) 2019-03-28 2019-03-28 Composition de polyuréthane durcissant à l'humidité en une partie pour revêtement protecteur haute performance

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/TH2019/000005 WO2020197512A1 (fr) 2019-03-28 2019-03-28 Composition de polyuréthane durcissant à l'humidité en une partie pour revêtement protecteur haute performance

Publications (1)

Publication Number Publication Date
WO2020197512A1 true WO2020197512A1 (fr) 2020-10-01

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PCT/TH2019/000005 WO2020197512A1 (fr) 2019-03-28 2019-03-28 Composition de polyuréthane durcissant à l'humidité en une partie pour revêtement protecteur haute performance

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5473043A (en) * 1993-04-09 1995-12-05 Dai-Ichi Kogyo Seiyaku Co., Ltd. Moisture-curable urethane resin compositions
US5747627A (en) * 1994-12-27 1998-05-05 The Yokohama Rubber Co., Ltd. Room temperature curing polyurethane compositions
JP2003128743A (ja) * 2001-10-18 2003-05-08 Dainippon Ink & Chem Inc 湿気硬化型ウレタン組成物
US20090069482A1 (en) * 2006-07-18 2009-03-12 Takeaki Mizutari Aqueous Coating Composition
JP2010189541A (ja) * 2009-02-18 2010-09-02 Auto Kagaku Kogyo Kk この上に更に上塗り塗装を行うための一液型熱硬化性組成物及びそれを用いた鋼板接合構造体の被覆、塗装方法
US20160024318A1 (en) * 2013-01-22 2016-01-28 Sika Technology Ag Liquid-applied waterproofing membrane comprising oxazolidine and aldimine

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5473043A (en) * 1993-04-09 1995-12-05 Dai-Ichi Kogyo Seiyaku Co., Ltd. Moisture-curable urethane resin compositions
US5747627A (en) * 1994-12-27 1998-05-05 The Yokohama Rubber Co., Ltd. Room temperature curing polyurethane compositions
JP2003128743A (ja) * 2001-10-18 2003-05-08 Dainippon Ink & Chem Inc 湿気硬化型ウレタン組成物
US20090069482A1 (en) * 2006-07-18 2009-03-12 Takeaki Mizutari Aqueous Coating Composition
JP2010189541A (ja) * 2009-02-18 2010-09-02 Auto Kagaku Kogyo Kk この上に更に上塗り塗装を行うための一液型熱硬化性組成物及びそれを用いた鋼板接合構造体の被覆、塗装方法
US20160024318A1 (en) * 2013-01-22 2016-01-28 Sika Technology Ag Liquid-applied waterproofing membrane comprising oxazolidine and aldimine

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