WO2018104003A1 - Matériau de revêtement polyuréthane à deux composants, procédé de revêtement et pièces revêtues - Google Patents

Matériau de revêtement polyuréthane à deux composants, procédé de revêtement et pièces revêtues Download PDF

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Publication number
WO2018104003A1
WO2018104003A1 PCT/EP2017/079006 EP2017079006W WO2018104003A1 WO 2018104003 A1 WO2018104003 A1 WO 2018104003A1 EP 2017079006 W EP2017079006 W EP 2017079006W WO 2018104003 A1 WO2018104003 A1 WO 2018104003A1
Authority
WO
WIPO (PCT)
Prior art keywords
component
beschichtungsmatenal
polyether
coating
coating material
Prior art date
Application number
PCT/EP2017/079006
Other languages
German (de)
English (en)
Inventor
Christian Bruchertseifer
Klaus Buck
Eugen HÖGELE
Jens KLAUER
Original Assignee
Basf Coatings Gmbh
Basf Se
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 Basf Coatings Gmbh, Basf Se filed Critical Basf Coatings Gmbh
Publication of WO2018104003A1 publication Critical patent/WO2018104003A1/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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/08—Polyurethanes from polyethers
    • 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
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/20—Heterocyclic amines; Salts thereof
    • C08G18/2081—Heterocyclic amines; Salts thereof containing at least two non-condensed heterocyclic 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/227—Catalysts containing metal compounds of antimony, bismuth or arsenic
    • 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
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225—Polyamines
    • C08G18/3237—Polyamines aromatic
    • C08G18/324—Polyamines aromatic containing only one aromatic ring
    • 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
    • C08G18/48—Polyethers
    • C08G18/4829—Polyethers containing at least three hydroxy 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
    • C08G18/6685—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
    • 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
    • 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
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0066—Flame-proofing or flame-retarding 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
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
    • 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
    • C08K5/34928—Salts
    • 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
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/524—Esters of phosphorous acids, e.g. of H3PO3

Definitions

  • the present invention relates to a two-component polyurethane coating material comprising a first component A and a second component B.
  • Wheel sets of rail vehicles must be protected against corrosion.
  • Wheel sets are wheels, axles including bogies and underframe of rail vehicles.
  • the coatings must therefore be very resistant and tough-elastic, in order to avoid damage to the wheelsets by said flying ballast stones.
  • Another important feature of such coatings is to ensure a high level of noise protection during operation, that is, when rail-mounted vehicles slide over the rail system.
  • Patent application WO 2012/152870 A1 discloses wheel sets for rail-bound vehicles or parts thereof with a hardened coating produced from a two-component polyurethane coating material.
  • the previously known coatings show satisfactory results, it is an object of the present invention to further improve the corrosion protection and the impact protection of such coatings.
  • the impact resistance should be improved at low temperatures.
  • It is a further object of the invention not only to obtain the described properties in terms of corrosion protection and impact protection, but in addition to these properties to ensure excellent flame retardance of the coatings. So it is particularly about the compatibility of flame retardants on the one hand, and still obtaining a coating that is conditioned so that it has excellent corrosion protection and impact protection. Furthermore, a good noise protection should be achieved.
  • component A contains,
  • the polyether and / or polyester polyol has a number average molecular weight of 2000 to 9000 g / mol, in particular 5000 to 7000 g / mol.
  • the determination of the number average molecular weight in the context of the present invention by means of GPC analysis with THF (+0.1% acetic acid) as eluent (1 ml / min) on a styrene-divinylbenzene column combination. The calibration is performed with polystyrene standards.
  • the hydroxyl number of the polyether and / or polyester polyol is preferably from 22 to 56, more preferably from 24 to 30.
  • the OH number (hydroxyl number) is measured in the context of the present invention according to DIN 53240.
  • polyether polyols in particular trifunctional (that is, on average three OH groups exhibiting) polyether polyols.
  • the coating material advantageously contains, as flame retardant, diphenyl cresyl phosphate, melamine phosphate and / or melamine cyanurate, more preferably a mixture of diphenyl cresyl phosphate on the one hand and melamine phosphate or melamine cyanurate on the other hand, the weight ratio of diphenyl cresyl phosphate: melamine phosphate or melamine cyanurate being from 1: 0.75 to 1: 3.
  • the coating material may of course contain conventional additives, for example wetting and dispersing additives and / or defoamers. Typical proportions range, for example, 0.05 to 2.0 wt .-% wetting and dispersing and 0.1 to 3.0 wt .-% defoamer, each based on the total amount of component A.
  • the wetting and dispersing additive used is advantageously a salt of unsaturated polyaminamides and acidic polyesters.
  • the defoamer is advantageously a silicone oil.
  • the aromatic diamine is preferably an isomeric mixture of 3,5-diethyltoluene-2,4-diamine and 3,5-diethyltoluene-2,6-diamine.
  • the amine catalyst is preferably the components known to the person skilled in the art in this connection, that is to say in particular aminic or diaminic organic compounds having exclusively tertiary and thus aprotic and non-reactive amino groups.
  • aminic or diaminic organic compounds having exclusively tertiary and thus aprotic and non-reactive amino groups.
  • DABCO diazabicyclooctane
  • metal-containing catalyst (s) for the polyurethane formation are basically known in the art components. Examples include zinc, zirconium, titanium, tin or bismuth-containing catalysts, in particular organometallic compounds or metal carboxylates.
  • the coating material may of course contain conventional pigments, for example in the form of pigment pastes.
  • the isocyanate prepolymers contained in component B preferably have an isocyanate content of 8 to 16%.
  • the isocyanate content is determined in the context of the present invention according to DIN EN ISO 1 1909 by reaction of the respective sample with excess dibutylamine and back-titration of the excess with hydrochloric acid against bromophenol blue.
  • such prepolymers can be prepared by reacting 35 to 65% by weight of aromatic diisocyanate and 65 to 35% by weight of hydroxyl-containing polyether and / or polyester, the sum of diisocyanate and polyether and / or polyester being 100% by weight, produced.
  • polyethers in particular polyoxyalkylene-based polyethers such as polyethylene and / or polypropylene-based polyethers.
  • the polyisocyanates contained in component B preferably consist of at least 90% by weight of the abovementioned prepolymers.
  • the use of further polyisocyanates is of course possible, but ultimately preferably increased or even exclusively the said prepolymers are used.
  • component B contains exclusively the said prepolymers as polyisocyanates.
  • the isocyanate-reactive groups of component A react with the isocyanate groups of component B.
  • the mixing ratio of component A: component B is advantageously adjusted so that the molar ratio of the isocyanate-reactive groups Component A to the isocyanate groups of component B 1, 1: 1 to 1: 1, 2, more preferably 1: 1 to 1: 1, 1.
  • the present invention also relates to a method for coating wheelsets, bogies and underframes for rail vehicles, railroad tracks and parts of said objects by applying and curing the coating material according to the invention.
  • the invention further relates to wheelsets, bogies and bases for rail vehicles, railroad tracks and parts of said objects, which are at least partially coated with a cured coating material according to the invention.
  • the coating material according to the invention can advantageously be applied with a 2K hot spray system.
  • the layer thickness of the cured coating is advantageously in the range of 2 to 6 mm.
  • the coating material according to the invention has very advantageous properties. It is highly reactive and fast curing. An application on vertical surfaces without drainage is possible.
  • the cured coating has excellent mechanical properties. It is heat resistant and shows no softening at elevated temperatures. Their elasticity is also at low temperatures up to -45 ° C.
  • it has a very good Flannnntik despite its clearly organic matrix, since it surprisingly succeeded, despite the high proportion of Flamnntiknnitteln on the other ingredients to produce a coating agent, which knows to fulfill the described properties in terms of corrosion protection and impact protection after application and curing.
  • the coating has very good noise protection properties.
  • the objects to be coated consisting of iron or steel can be cleaned by sandblasting or another suitable cleaning method.
  • an adhesion primer is applied to improve the adhesion prior to the application of the coating material according to the invention.
  • Suitable adhesion primers are epoxy resin coating compositions.
  • the coating which is produced from the coating material according to the invention is preferably a topcoat, that is to say in any case the topmost coating layer, even in the case of an optionally present multilayer coating structure.
  • Toluene diamine-based aromatic diamine crosslinking agent (BAYTEC VP PU 30EL14) was added to 1, 000 kg and stirred for 20 minutes. Thereafter, 13.650 kg of diphenyl cresyl phosphate, 2.500 kg of a 25 percent solution of diazabicyclooctane in 1, 4-butanediol, 0.100 kg of bismuth carboxylate, 1, 300 kg of white pigment paste (white pigment in castor oil) and 0.700 kg of black pigment paste (black pigment in castor oil) were added. Finally, it was stirred under vacuum at 700 rpm for 30 minutes.
  • the components A and B were mixed with each other in a volume ratio of 1: 1 and applied immediately afterwards with a 2K hot spray unit on a wheelset for rail vehicles.
  • the wheelset had previously been primed with an epoxy resin based zinc dust primer.
  • the applied coating material according to the invention was cured. This resulted in a layer thickness of 4 mm.
  • the qualification of protective coatings can be carried out according to the standard DIN EN 13261: 201 1 -01.
  • DIN EN 13261: 201 1 -01 This standard specifies four protection classes with regard to corrosion and impact protection.
  • the wheel sets coated with the material according to the invention were tested according to the said standard.
  • the coating meets all the requirements of protection class 2.
  • the thickness of the coating, the adhesion of the coating, the impact resistance, the resistance to blasting agents, the salt water resistance, the resistance tested against corrosive media and resistance to cyclic mechanical stress According to the standard, the thickness of the coating, the adhesion of the coating, the impact resistance, the resistance to blasting agents, the salt water resistance, the resistance tested against corrosive media and resistance to cyclic mechanical stress.
  • the coating of the invention has a very good adhesion and a low glass transition temperature.
  • the test to determine the flammability of materials and their flame propagation properties in accordance with ISO 5658-2: 2006 / Am1: 201 1 provided the required fire protection proof.
  • the impact resistance of the coating was also given at -45 ° C.

Landscapes

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

Abstract

La présente invention concerne un matériau de revêtement polyuréthane à deux composants, ainsi qu'un procédé de revêtement d'essieux, de bogies et de châssis pour des véhicules ferroviaires, de rails de chemin de fer et de parties desdits objets par application et durcissement dudit matériau de revêtement.
PCT/EP2017/079006 2016-12-05 2017-11-13 Matériau de revêtement polyuréthane à deux composants, procédé de revêtement et pièces revêtues WO2018104003A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP16202149 2016-12-05
EP16202149.7 2016-12-05

Publications (1)

Publication Number Publication Date
WO2018104003A1 true WO2018104003A1 (fr) 2018-06-14

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PCT/EP2017/079006 WO2018104003A1 (fr) 2016-12-05 2017-11-13 Matériau de revêtement polyuréthane à deux composants, procédé de revêtement et pièces revêtues

Country Status (1)

Country Link
WO (1) WO2018104003A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110563909A (zh) * 2019-09-03 2019-12-13 四川睿铁科技有限责任公司 一种导轨电车导向轨约束性浇注改性聚氨酯树脂及其制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012152870A1 (fr) 2011-05-10 2012-11-15 Basf Coatings Gmbh Essieux montés pour véhicules ferroviaires ou leurs pièces et procédé de revêtement

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012152870A1 (fr) 2011-05-10 2012-11-15 Basf Coatings Gmbh Essieux montés pour véhicules ferroviaires ou leurs pièces et procédé de revêtement

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110563909A (zh) * 2019-09-03 2019-12-13 四川睿铁科技有限责任公司 一种导轨电车导向轨约束性浇注改性聚氨酯树脂及其制备方法

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