WO2022128839A1 - Peinture intumescente - Google Patents

Peinture intumescente Download PDF

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Publication number
WO2022128839A1
WO2022128839A1 PCT/EP2021/085354 EP2021085354W WO2022128839A1 WO 2022128839 A1 WO2022128839 A1 WO 2022128839A1 EP 2021085354 W EP2021085354 W EP 2021085354W WO 2022128839 A1 WO2022128839 A1 WO 2022128839A1
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WO
WIPO (PCT)
Prior art keywords
intumescent coating
amine
bis
coating according
formula
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PCT/EP2021/085354
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German (de)
English (en)
Inventor
Johannes VIERTEL
Andreas ROTHENGASS
Edis Kasemi
Jochen Grötzinger
Original Assignee
Sika Technology Ag
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Publication of WO2022128839A1 publication Critical patent/WO2022128839A1/fr

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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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C08G59/5033—Amines aromatic
    • 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
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • 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
    • C09D5/18—Fireproof paints including high temperature resistant paints
    • C09D5/185—Intumescent paints
    • 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
    • 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
    • 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
    • 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
    • C08K3/32—Phosphorus-containing compounds
    • C08K2003/321—Phosphates
    • C08K2003/322—Ammonium phosphate
    • C08K2003/323—Ammonium polyphosphate
    • 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
    • C08K5/34922—Melamine; Derivatives thereof

Definitions

  • the invention relates to epoxy resin coatings with intumescent properties and their use for passive fire protection of components.
  • Intumescent coatings are coatings that foam up considerably under the influence of heat and form a charred, solid material with high thermal insulation with a high increase in volume.
  • a component coated with it for example a steel girder, is protected from high heat for a certain period of time by the foamed material in the event of a fire.
  • the insulation formed delays the component from heating up to a temperature that is critical for its stability, which allows a longer period of time for people to be evacuated before the component could fail.
  • Intumescent coatings based on epoxy resins are particularly suitable. They each comprise a liquid resin and hardener component, which are mixed before application, applied in a layer thickness of about 1 to 8 mm and harden at ambient temperatures in the range of about 5 to 40 °C to form a solid coating.
  • the coating should have a low viscosity with as little or no content as possible of thinners such as organic solvents or benzyl alcohol, should cure quickly and without problems, and at the same time form a tack-free surface without clouding, stains or deposits caused by blushing, so that good intermediate adhesion can be achieved in the case of a multi-layer application is guaranteed.
  • the coating For the service life of the component, the coating remains on its surface, where it can protect it from corrosion and, in the event of a fire, insulates the component against heat through intumescence as described.
  • the requirements for coatings in the event of a fire are regulated in various standards and guidelines, for example DIN EN 13381-8, and are divided into fire resistance classes such as R30, R90 or R120, which differ in the length of time up to which the temperature of the coated component below e.g. 500 °C must.
  • An advantageous intumescent coating achieves long-lasting heat protection with the lowest possible layer thickness, with the requirements for the duration of the heat protection being dependent on the specific application.
  • Intumescent coatings based on epoxy resin from the prior art typically contain significant amounts of thinners such as benzyl alcohol or are too highly viscous to be able to be applied by spraying without prior heating. They typically contain ammonium polyphosphate, melamine and mostly polyamidoamines or polyetheramines as hardeners for the epoxy resin, with polyalkyleneamines such as diethylenetriamine (DETA) or triethylenetetramine (TETA) and aliphatic primary diamines such as isophoronediamine or 1,3-bis(aminomethyl)benzene also being mentioned , for example in US 10,442,937 or US 10,131,800.
  • DETA diethylenetriamine
  • TETA triethylenetetramine
  • aliphatic primary diamines such as isophoronediamine or 1,3-bis(aminomethyl)benzene also being mentioned , for example in US 10,442,937 or US 10,131,800.
  • Epoxy resin coatings without intumescence properties with N-benzyl-1,2-ethanediamine in the hardener are described, for example, in EP 3,344,677. This amine enables low-viscosity coatings with trouble-free curing even at cold ambient temperatures.
  • an intumescent coating according to claim 1 solves this problem.
  • the amine of the formula (I) enables particularly low-viscosity coatings with rapid and trouble-free curing with moderate hazard identification. Particularly surprising is the fact that the heat protection with the intumescent coating according to the invention in the event of a fire is higher than with a comparable system according to the prior art.
  • the intumescent coating according to the invention can be applied in one or more layers without heating and without the addition of solvents using a commercially available single-feed airless spray apparatus. She has good adhesion properties, high inter-adhesion in multi-layer application, high mechanical resistance with good shock, impact and abrasion resistance and good anti-corrosion properties.
  • the preferred combination of amine of the formula (I), 1,3-bis(aminomethyl)cyclohexane and polyetheramine is particularly advantageous.
  • the intumescent coating according to the invention is preferably used to protect components against the effects of heat in the event of a fire. It is used to particular advantage to protect steel girders, load-bearing concrete elements, plastic components such as insulation boards, or in vehicle construction, for example to coat battery boxes in electric vehicles.
  • the intumescent coating is particularly suitable for factory coating of steel beams.
  • the steel girders are already coated at the place of manufacture and delivered in this form, with simple, emission-free processing, rapid curing and high mechanical strength being advantageous so that the coated steel girders can be efficiently manufactured, stacked and transported without the coating being damaged is damaged.
  • the subject matter of the invention is an intumescent coating
  • A is a divalent alkylene, cycloalkylene or arylalkylene radical having 2 to 15 carbon atoms, and
  • Y is H or an alkyl, cycloalkyl, aralkyl or aryl radical with 1 to 11 carbon atoms which may have an oxygen or nitrogen atom, where the two nitrogen atoms to which the radical A is attached are separated from one another by at least two carbon atoms and the amine of the formula (I) contains a total of at least 8 carbon atoms,
  • epoxy liquid resin A technical polyepoxide with a glass transition temperature below 25°C is referred to as "epoxy liquid resin”.
  • a “primary amino group” means an amino group attached to a single organic residue and bearing two hydrogen atoms; a “secondary amino group” denotes an amino group which is bonded to two organic radicals, which can also jointly be part of a ring, and which carries a hydrogen atom; and a “tertiary amino group” denotes an amino group which is bonded to three organic radicals, which can also be two or three parts of one or more rings, and does not carry a hydrogen atom.
  • amine hydrogen The hydrogen atoms of primary and secondary amino groups are referred to as “amine hydrogen”.
  • amine hydrogen equivalent weight refers to the mass of an amine or amine-containing composition that contains one molar equivalent of amine hydrogen. It is given in the unit of measurement "g/eq”.
  • Epoxy equivalent weight is the mass of an epoxide group-containing compound or composition that contains one molar equivalent of epoxide groups. It is given in the unit of measurement "g/eq”.
  • a “thinner” is a liquid that is able to reduce the viscosity of a curable composition and is not chemically bound into the polymer during curing.
  • a composition is referred to as “storable” if it can be stored at room temperature in a suitable container for a longer period of time, typically for at least 3 months up to 6 months or more, without its application or usage properties deteriorating due to storage modified to an extent relevant to their use.
  • Molecular weight is the molar mass (in grams per mole) of a molecule.
  • the number average Mn of a polydisperse mixture of oligomeric or polymeric molecules is referred to as the "average molecular weight”. It is determined using gel permeation chromatography (GPC) against polystyrene as a standard.
  • the “pot life” refers to the period of time from the mixing of the components of a multi-component curable composition within which the composition can be processed without losses.
  • room temperature A temperature of 23 °C is referred to as "room temperature”.
  • Percentages by weight refer to mass fractions of a component of a composition or molecule based on the total composition or molecule, unless otherwise indicated.
  • the terms “mass” and “weight” are used synonymously in this document.
  • the intumescent coating preferably comprises a resin component and a hardener component, the liquid epoxy resin being part of the resin component, the amine of the formula (I) being part of the hardener component and the salt S1 and the substance S2 are each independently a part of the resin and/or the hardener component.
  • liquid epoxy resin is aromatic epoxy resins, in particular the glycidyl ethers of: - Bisphenol A, bisphenol F or bisphenol A/F, where A stands for acetone and F for formaldehyde, which serve as starting materials for the production of these bisphenols.
  • aromatic epoxy resins in particular the glycidyl ethers of: - Bisphenol A, bisphenol F or bisphenol A/F, where A stands for acetone and F for formaldehyde, which serve as starting materials for the production of these bisphenols.
  • positional isomers may also be present, in particular derived from 2,4'- or 2,2'-hydroxyphenylmethane.
  • Dihydroxybenzene derivatives such as resorcinol, hydroquinone or catechol;
  • bisphenols or polyphenols such as bis (4-hydroxy-3-methylphenyl) - methane, 2,2-bis (4-hydroxy-3-methylphenyl) propane (bisphenol C), bis (3,5-dimethyl-4 -hydroxyphenyl)methane, 2,2-bis(3,5-dimethyl-4-hydroxyphenyl)propane, 2,2-bis(3,5-dibromo-4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy -3-tert-butylphenyl)propane, 2,2-bis(4-hydroxyphenyl)butane (bisphenol B), 3,3-bis(4-hydroxyphenyl)pentane, 3,4-bis(4-hydroxyphenyl )hexane, 4,4-bis(4-hydroxyphenyl)heptane, 2,4-bis(4-hydroxyphenyl)-2-methylbutane, 2,4-bis(3,5-dimethyl-4-hydroxyphenyl)- 2-methylbutane, 1,1-bisbisphenol
  • 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane bisphenol TMC
  • 1,1-bis(4-hydroxyphenyl)-1-phenylethane 1,4-bis[2-(4-hydroxyphenyl )-2-propyl]benzene
  • bisphenol P 1,3-bis[2-(4-hydroxyphenyl)-2-propyl]benzene
  • bisphenol M 1,4'-dihydroxydiphenyl (DOD), 4,4 '-Dihydroxybenzophenone, bis(2-hydroxy-naphth-1-yl)methane, bis(4-hydroxynaphth-1-yl)methane, 1,5-dihydroxynaphthalene, tris(4-hydroxyphenyl)methane, 1,1, 2,2-tetrakis(4-hydroxyphenyl)ethane, bis(4-hydroxyphenyl)ether or bis(4-hydroxyphenyl)sulfone;
  • Aromatic amines such as aniline, toluidine, 4-aminophenol, 4,4'-methylenediphenyldiamine, 4,4'-methylenediphenyldi-(N-methyl)amine, 4,4'-[1,4-phenylenebis( 1-methylethylidene)]bisaniline (bisaniline P) or 4,4'-[1,3-phenylenebis(1-methylethylidene)]bisaniline (bisaniline M).
  • epoxy resins are aliphatic or cycloaliphatic polyepoxides, in particular
  • Glycidyl ethers of saturated or unsaturated, branched or unbranched, cyclic or open-chain di-, tri- or tetrafunctional C2 to C50 alcohols in particular ethylene glycol, propylene glycol, butylene glycol, hexanediol, octanediol, polypropylene glycols, dimethylolcyclohexane, neopentyl glycol, dibromoneopentyl glycol, castor oil, trimethylolpropane, trimethylolethane, pentaerythrol, sorbitol or glycerol, or alkoxylated glycerol or alkoxylated trimethylolpropane;
  • N-glycidyl derivative of amides or heterocyclic nitrogen bases such as triglycidyl cyanurate or triglycidyl isocyanurate, or reaction products of epichlorohydrin with hydantoin.
  • aromatic diepoxides which are liquid at room temperature and have an epoxide equivalent weight in the range from 110 to 200 g/mol, preferably 150 to 200 g/mol, in particular bisphenol A diglycidyl ether and/or bisphenol F diglycidyl ether, such as those commercially available, for example from Olin, Huntsman or Momentive are available.
  • bisphenol A diglycidyl ether and/or bisphenol F diglycidyl ether such as those commercially available, for example from Olin, Huntsman or Momentive are available.
  • the intumescent coating can contain proportions of bisphenol A solid resin or novolak glycidyl ethers or reactive diluents.
  • Suitable reactive diluents are in particular butanediol diglycidyl ether, hexanediol diglycidyl ether, trimethylolpropane di- or triglycidyl ether, phenyl glycidyl ether, cresyl glycidyl ether, guaiacol glycidyl ether, 4-methoxyphenyl glycidyl ether, p-n-butylphenyl glycidyl ether, p-tert.
  • A is preferably selected from the group consisting of 1,2-ethylene, 1,2-propylene, 1,3-propylene, 1,4-butylene, 1,3-butylene, 2-methyl- 1,2-propylene, 1,3-pentylene, 1,5-pentylene, 2,2-dimethyl-1,3-propylene, 1,6-hexylene, 2- Methyl-1,5-pentylene, 1,7-heptylene, 1,8-octylene, 2,5-dimethyl-1,6-hexylene, 1,9-nonylene, 2,2(4), 4-trimethyl-1 ,6-hexylene, 1,10-decylene, 1,11-undecylene, 2-butyl-2-ethyl-1,5-pentylene, 1,12-dodecylene, 1,2-cyclohexylene, 1,3-cyclohexylene, 1 ,4-cyclohexylene, (1,5,5-trimethylcyclohe
  • These amines of the formula (I) enable particularly trouble-free curing.
  • A is particularly preferably 1,2-ethylene.
  • Y is preferably selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, pentyl, heptyl, hept-2-yl, benzyl, cyclohexyl, phenyl, 4-methylphenyl, 4-isopropylphenyl, 4-tert. butylphenyl, 4-methoxyphenyl, 4-dimethylaminophenyl and 1-naphthyl.
  • Y is particularly preferably phenyl or cyclohexyl, in particular phenyl.
  • Such an amine of the formula (I) enables particularly rapid curing and particularly trouble-free curing.
  • the amine of the formula (I) is preferably selected from the group consisting of N-benzyl-1,2-ethanediamine, N-(4-methylbenzyl)-1,2-ethanediamine, N-(4-isopropylbenzyl)-1 ,2-ethanediamine, N-(4-tert.butylbenzyl)-1,2-ethanediamine, N-(4-methoxybenzyl)-1,2-ethanediamine, N-(4-dimethylaminobenzyl)-1,2-ethanediamine , N-(1-Naphthylmethyl)-1,2-ethanediamine, N-cyclohexylmethyl-1,2-ethanediamine, N-benzyl-1,2- propanediamine, N-benzyl-1,3-bis(aminomethyl)cyclohexane, N-benzyl-1,4-bis(aminomethyl)cyclohexane, N-benzyl-1,3-bis(aminomethyl)
  • A is 1,2-ethylene and Y is phenyl.
  • This amine of formula (I) is N-benzyl-1,2-ethanediamine. It enables intumescent coatings with a particularly low viscosity, particularly fast curing and particularly high heat protection in the event of a fire.
  • the amine of formula (I) may contain moieties of dialkylated amine of formula Af-NH—CH 2 -Y] 2 . It preferably contains only a small amount of dialkylated amine, in particular a content of at most 35% by weight, preferably at most 30% by weight, based on the sum of the amine of the formula (I) and the corresponding dialkylated amine.
  • Preferably it contains less than 5% by weight of the corresponding dialkylated amine. This enables particularly fast curing.
  • the amine of formula (I) is preferably prepared by partial alkylation of at least one amine of formula H2N-A-NH2 with at least one alkylating agent.
  • the alkylation is preferably a reductive alkylation, the alkylating agent used being an aldehyde of the formula Y—CH ⁇ O and hydrogen.
  • the amine of the formula (I) can then be freed from the corresponding dialkylated amine by means of distillation.
  • the intumescent coating additionally contains adducts of the amine of the formula (I) with at least one epoxy resin.
  • the epoxy resin has in particular an average epoxy equivalent weight in the range from 155 to 250 g/eq.
  • it is an aromatic diepoxide, in particular bisphenol A or F diglycidyl ether, in particular a liquid resin.
  • Suitable adducts of the amine of the formula (I) with at least one epoxy resin are prepared in particular with such an excess of amine that 1.3 to 3 mol, preferably 1.4 to 2 mol, of amine of the formula (I) were used per molar equivalent of epoxide groups .
  • Such an adduct enables particularly fast curing with moderate viscosity.
  • the intumescent coating preferably contains at least one further amine together with the amine of the formula (I) and, if appropriate, its adducts.
  • Preferred further amines are polyamines with at least four aliphatic amine hydrogens, in particular 2,2-dimethyl-1,3-propanediamine, 1,3-pentanediamine (DAMP), 1,5-pentanediamine, 1,5-diamino-2-methylpentane (MPMD ), 2-butyl-2-ethyl-1,5-pentanediamine (C11-neodiamine), 1,6-hexanediamine, 2,5-dimethyl-1,6-hexanediamine, 2,2(4),4- Trimethyl-1,6-hexanediamine (TMD), 1,7-heptanediamine, 1,8-octanediamine, 1,9-nonanediamine, 1,10-decanediamine, 1,11-undecanediamine, 1,12-dodecanediamine , 1-amino-3
  • dipropylenetriamine DPTA
  • N-(2-aminoethyl)-1,3-propanediamine N3-amine
  • N,N'-bis(3-aminopropyl)-ethylenediamine N4-amine
  • N,N'- Bis(3-aminopropyl)-1,4-diaminobutane N5-(3-aminopropyl)-2-methyl-1,5-pentanediamine, N3-(3-aminopentyl)-1,3-pentanediamine, N5-( 3-amino-1-ethylpropyl)-2-methyl-1,5-pentanediamine, N,N'-bis(3-amino-1-ethylpropyl)-2-methyl-1,5-pentanediamine, 3-(2- Aminoethyl)aminopropylamine or bis(hexamethylene)triamine (BHMT), or alkylated polyalkyleneamines such as,
  • primary diamines without secondary amino groups are preferred. These amines enable fast, trouble-free curing with good inter-layer adhesion in multi-layer applications.
  • the further amine is optionally present in the form of an adduct with an epoxide, in particular a diepoxide such as in particular bisphenol A or F diglycidyl ether or a monoepoxide such as in particular cresyl glycidyl ether.
  • an epoxide in particular a diepoxide such as in particular bisphenol A or F diglycidyl ether or a monoepoxide such as in particular cresyl glycidyl ether.
  • the further amine is preferably selected from the group consisting of TMD, IPDA, 1,2-diaminocyclohexane, 1,3-diaminocyclohexane, 1,4-diaminocyclohexane, 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl).
  • the intumescent coating particularly preferably contains 1,3-bis(aminomethyl)cyclohexane, at least one polyoxypropylene di- or triamine with an average molecular weight Mn in the range from 200 to 500 g/mol and optionally Adducts of the amine of formula (I) with at least one epoxy resin.
  • a preferred polyoxypropylene di- or triamine is a polyoxypropylene diamine with an average molecular weight M n in the range from 200 to 300 g/mol.
  • the intumescent coating most preferably contains at least one amine of the formula (I), at least one adduct of the amine of the formula (I) with at least one epoxy resin, in particular an aromatic diepoxide, 1,3-bis(aminomethyl)cyclohexane and at least a polyoxypropylene diamine with an average molecular weight Mn ranging from 200 to 300 g/mol.
  • the amine of the formula (I) and adducts thereof with at least one epoxy resin are preferably present in an amount such that 5 to 80%, preferably 10 to 60%, in particular 10 to 30% of all amine hydrogens of amines present in the intumescent coating of the formula (I) or its adducts originate.
  • amine hydrogens present in the intumescent coating 10 to 60%, preferably 10 to 30%, particularly preferably derive from amines of the formula (I) or its adducts, 30 to 80%, preferably 50 to 80%, from 1,3- bis(aminomethyl)cyclohexane and 10 to 30% of polyoxypropylene di- or tri-amines.
  • the intumescent coating also contains at least one salt S1, which releases phosphoric acid when heated.
  • phosphoric acid is produced in the coating, which together with the organic component of the coating forms a charred, solid mass consisting mainly of carbon and phosphorus oxides.
  • Phosphorus-containing salts are suitable as salt S1, in particular phosphates, polyphosphates, phosphonates or phosphites, in particular sodium phosphate, potassium phosphate, calcium phosphate, magnesium phosphate, ammonium phosphate or the corresponding pyrophosphates or polyphosphates.
  • Ammonium phosphate, ammonium pyrophosphate or ammonium polyphosphate is preferred as salt S1.
  • ammonium polyphosphate APP
  • the intumescent coating preferably contains a content of salt S1, in particular ammonium polyphosphate, in the range from 10 to 70% by weight, preferably 20 to 60% by weight, in particular 30 to 50% by weight, based on the entire intumescent coating.
  • salt S1 in particular ammonium polyphosphate
  • the salt S1 can be present as part of the resin and/or hardener component.
  • the salt S1 is preferably part of the resin component.
  • the intumescent coating also contains at least one substance S2, which releases a non-combustible gas when heated.
  • Nitrogen is preferred as the non-combustible gas.
  • the substance S2 leads to foaming of the melting and ultimately charring coating, with the salt S1 and the organic component of the coating together with the phosphoric acid forming a large-volume, highly foamed, solid mass with good thermal insulation, which the coating is particularly good at protecting the component from the heat of the fire.
  • Melamine or a derivative of melamine such as in particular melamine cyanurate, melamine phosphate, melamine polyphosphate or melamine borate, is preferred as substance S2.
  • the intumescent coating preferably contains a content of substance S2, in particular melamine, in the range from 1 to 25% by weight, preferably 2 to 20% by weight, in particular 5 to 15% by weight, based on the entire intumescent coating.
  • Substance S2 can be present as part of the resin and/or hardener component. Substance S2 is preferably part of the resin component.
  • the intumescent coating preferably contains at least one further substance selected from acrylates, organophosphates, fibers, inorganic fillers, pigments, diluents and accelerators.
  • Suitable acrylates are in particular acrylates or methacrylates having one, two or more (meth)acrylate groups, in particular difunctional or polyfunctional (meth)acrylates of low viscosity at room temperature. In particular, they are present as part of the resin component.
  • the intumescent coating preferably contains at least one difunctional or polyfunctional (meth)acrylate.
  • diethylene glycol di(meth)acrylate triethylene glycol di(meth)acrylate or higher polyethylene glycol di(meth)acrylates, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate or higher polypropylene glycol di(meth)acrylates, butanediol di(meth) acrylate, hexanediol di(meth)acrylate, dodecanediol di(meth)acrylate, glycerol di(meth)acrylate or trimethylolpropane tri(meth)acrylate. Trimethylolpropane triacrylate is preferred.
  • Such an acrylate enables a particularly low viscosity and particularly fast curing.
  • the content of acrylates is preferably such that 1 to 50, preferably 2 to 35, in particular 5 to 20, parts by weight of acrylates are present per 100 parts by weight of liquid epoxy resin.
  • Suitable organophosphates are in particular alkyl or aryl phosphates of low viscosity at room temperature, in particular diphenyl cresyl phosphate, triethyl phosphate, tripropyl phosphate, triisopropyl phosphate, tributyl phosphate, triisobutyl phosphate, tri(2-ethylhexyl) phosphate or tris(2-butoxyethyl) phosphate, in particular triisobutyl phosphate.
  • Such an organophosphate enables a particularly low viscosity and also promotes the formation of a well-insulating, foamed, hard layer in the event of a fire.
  • a content of organophosphates such as in particular triisobutyl phosphate, in the range from 1 to 30% by weight, preferably 2 to 20% by weight, in particular 3 to 15% by weight, based on the entire intumescent coating, is preferred.
  • Suitable fibers are, in particular, mineral fibers, glass fibers, ceramic fibers, basalt fibers or carbon fibers. Mineral fibers and/or carbon fibers are particularly suitable. Mineral fibers or a combination of mineral fibers and carbon fibers are most suitable.
  • Fibers with a length in the range from 0.1 to 10 mm are preferred.
  • Carbon fibers preferably have a length in the range from 1 to 4 mm.
  • a certain fiber content is preferred for particularly long-lasting heat protection.
  • Suitable inorganic fillers are, in particular, ground or precipitated calcium carbonate, baryte (heavy spar), talc, quartz powder, quartz sand, silicon carbide, iron mica, dolomite, wollastonite, kaolin, mica (potassium aluminum silicate), molecular sieve, aluminum oxide, zinc oxide, aluminum hydroxide, Magnesium hydroxide, silicic acid, cement, gypsum, fly ash, soot, graphite or hollow spheres. Of these, talc, ground quartz, kaolin, aluminum hydroxide or a combination thereof are preferred.
  • Suitable pigments are, in particular, titanium dioxide, iron oxide, chromium(III) oxide or carbon black.
  • the intumescent coating preferably contains at least one titanium dioxide, in particular in an amount in the range from 1 to 10% by weight, preferably 2 to 8% by weight, based on the entire intumescent coating.
  • Organophosphates, fibers, fillers or pigments can be present as part of the resin and/or hardener component. They are preferably present as part of the resin component.
  • Suitable diluents are in particular ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tert. Butanol, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl-1-butanol, 3-methyl-1-butanol, 3-methyl-2-butanol, n-hexanol, 2-ethylhexanol, xylene, 2-methoxyethanol , dimethoxyethanol, 2-ethoxyethanol, 2-propoxyethanol, 2-iso-propoxyethanol, 2-butoxyethanol, 2-phenoxyethanol, 2-benzyloxyethanol, benzyl alcohol, ethylene glycol, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol diphenyl ether, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether,
  • the intumescent coating preferably contains a low content of diluents, in particular less than 10% by weight, preferably less than 5% by weight, particularly preferably less than 3% by weight, based on the entire intumescent coating.
  • Thinners can be present as part of the resin and/or the hardener component.
  • Suitable accelerators are, in particular, acids or compounds which can be hydrolyzed to form acids, water, nitrates, tertiary amines or Mannich bases.
  • Salicylic acid calcium nitrate, water, 2,4,6-tris(dimethylaminomethyl)phenol or a combination of these accelerators are preferred.
  • 2,4,6-Tris(dimethylaminomethyl)phenol is particularly preferred, in particular in an amount in the range from 0.1 to 2% by weight, preferably 0.2 to 1.5% by weight, particularly preferably 0.3 to 1% by weight, based on the total Intumescent coating.
  • Accelerators can be present as part of the resin and/or the hardener component. They are preferably present as part of the hardener component.
  • the intumescent coating contains other substances, in particular
  • amines in particular adducts of small volatile amines such as 1,2-ethanediamine or 1,2-propanediamine with epoxy resins or monoepoxides, N-aminoethylpiperazine, 3-dimethylaminopropylamine (DMAPA), 3-(3-(dimethylamino)propylamino) propylamine (DMAPAPA), monoamines, polyamidoamines, in particular reaction products of a monobasic or polybasic carboxylic acid or its ester or anhydride, in particular a dimeric fatty acid, with a polyamine used in a stoichiometric excess, in particular DETA or TETA, Mannich bases, in particular phenalkamines, i.e.
  • small volatile amines such as 1,2-ethanediamine or 1,2-propanediamine with epoxy resins or monoepoxides, N-aminoethylpiperazine, 3-dimethylaminopropylamine (DMAPA), 3-(
  • Polymers in particular polyamides, polysulfides, polyvinyl formal (PVF), polyvinyl butyral (PVB), polyurethanes (PUR), polymers with carboxyl groups, polyamides, butadiene-acrylonitrile copolymers, styrene-acrylonitrile copolymers, butadiene-styrene copolymers, homo - or copolymers of unsaturated monomers such as in particular ethylene, propylene, butylene, isobutylene, isoprene, vinyl acetate or alkyl (meth)acrylates, or chlorosulfonated polyethylenes, fluorine-containing polymers or sulfonamide-modified melamines,
  • microspheres made of plastic, in particular hollow spheres
  • Adhesion improvers in particular organoalkoxysilanes such as 3-glycidoxypropyltrimethoxysilane or 3-glycidoxypropyltriethoxysilane,
  • phosphates such as in particular diphenyl cresyl phosphate, resorcinol bis(diphenyl phosphate) , resorcinol diphosphate oligomer, tetraphenylresorcinol diphosphite, ethylenediamine diphosphate or bisphenol A bis(diphenyl phosphate), tris(chloroethyl) phosphate, tris(chloropropyl) phosphate or tris(dichloroisopropyl) phosphate, tris[3-bromo-2,2- bis(bromomethyl)propyl] phosphate, tetrabromo-bisphenol A, bis(
  • additives in particular defoamers, deaerators, wetting agents, dispersants, leveling agents, dispersed paraffin wax, film-forming aids or biocides.
  • the intumescent coating is preferably not water-based. It preferably has a water content of less than 2% by weight, in particular less than 1% by weight, based on the coating as a whole.
  • the resin component and the hardener component of the intumescent coating are stored in separate containers and only mixed shortly before application.
  • the resin component contains all compounds containing epoxy groups and the hardener component contains all compounds reactive with epoxy groups.
  • a hardener component comprising at least one amine of the formula (I), optionally adducts of the amine of the formula (I) with at least one epoxy resin, optionally other amines, optionally at least one accelerator and optionally other components.
  • the intumescent coating particularly preferably contains at least one adduct of the amine of formula (I) with at least one epoxy resin, in particular an aromatic diepoxide, 1,3-bis(aminomethyl)cyclohexane, at least one polyoxypropylenediamine with an average molecular weight Mn in the range from 200 to 300 g/mol and at least a two- or polyfunctional (meth)acrylate.
  • epoxy resin in particular an aromatic diepoxide, 1,3-bis(aminomethyl)cyclohexane, at least one polyoxypropylenediamine with an average molecular weight Mn in the range from 200 to 300 g/mol and at least a two- or polyfunctional (meth)acrylate.
  • the components of the intumescent coating are mixed shortly before or during application.
  • the mixing ratio is preferably chosen so that the molar ratio of the groups reactive toward epoxide groups to the epoxide groups plus acrylate groups is in the range from 0.5 to 1.5, in particular 0.7 to 1.2.
  • the mixing ratio between the resin component and the hardener component is typically in the range from 1:1 to 20:1, preferably 2:1 to 20:1.
  • the components are mixed continuously or in batches by means of a suitable method, it being important to ensure that not too much time elapses between the mixing of the components and the application and that the application takes place within the pot life.
  • Mixing and application take place in particular at ambient temperature, which is typically in the range from about 5 to 40°C, preferably from about 10 to 35°C.
  • the hardening of the intumescent coating begins through a chemical reaction.
  • Primary and secondary amino groups and, if present, further groups which are reactive toward epoxide groups react with epoxide groups and, if appropriate, acrylate groups.
  • the intumescent coating polymerizes and thereby hardens.
  • Curing typically takes a few hours to days. The duration depends, among other things, on the temperature, the reactivity of the components, their stoichiometry and the presence or amount of accelerators.
  • the intumescent coating When freshly mixed, the intumescent coating has a low viscosity.
  • the viscosity at 20° C. 5 minutes after the components have been mixed is preferably in the range from 1 to 20 Pa s, particularly preferably 2 to 15 Pa s, in particular 3 to 10 Pa s, measured using a plate-plate viscometer at a shear rate of 100s -1 .
  • the freshly mixed intumescent coating is applied to at least one substrate within the pot life, preferably by means of a spray apparatus or with the aid of a brush or a roller, in particular in an airless spraying process using a commercially available single-feed apparatus. In particular, it is not necessary to dilute the coating with added solvent or to heat it in order to achieve a viscosity suitable for spray application.
  • Suitable substrates to which the intumescent coating is applied are, in particular
  • Metals or alloys such as iron, steel, aluminum, copper, other non-ferrous metals, including surface-treated metals or alloys such as galvanized or chrome-plated metals,
  • Plastics such as hard and soft PVC, polycarbonate, polystyrene, polyester, polyamide, PMMA, ABS, SAN, epoxy resins, phenolic resins, PUR, POM, TPO, PE, PP, EPM or EPDM, each untreated or surface-treated, for example using plasma , corona or flames,
  • CFRP carbon fiber reinforced plastics
  • GFRP glass fiber reinforced plastics
  • SMC sheet molding compounds
  • PCC polymer-modified cement mortar
  • ECC epoxy resin-modified cement mortar
  • the substrates can be pretreated before application, in particular by physical and/or chemical cleaning methods or by applying a primer.
  • the intumescent coating is preferably applied overall in a layer thickness in the range from 0.5 to 10 mm, preferably 1 to 8 mm, in particular 2 to 6 mm, with the dry layer thickness largely corresponding to the wet layer thickness.
  • the intumescent coating is applied in a layer thickness in the range from 0.5 to 2 mm per operation.
  • the desired layer thickness depends on the desired heat protection properties of the respective application. A higher layer thickness enables higher and thus longer-lasting heat protection.
  • the intumescent coating is preferably applied in more than one operation. With a desired layer thickness of 5 mm, for example, almost 1.7 mm are preferably applied three times.
  • the application of the subsequent layer is preferably delayed until the previous layer has hardened to such an extent that it has a dry, non-tacky surface. It is important that the intumescent coating has good intermediate adhesion, i.e. that the further layer adheres well to the previous layer after curing. For good intermediate adhesion, it is advantageous if the cured coating has a non-tacky surface without cloudiness, stains or other disturbances, such as are typically caused by blushing effects.
  • the cured intumescent coating has excellent adhesion to different substrates, excellent inter-adhesion, high mechanical resistance with good shock, impact and abrasion resistance and good anti-corrosion properties.
  • the strong heating of the component should be delayed by around 30, 90 or 120 minutes, for example, with a long delay resulting in a mechanically very stable foamed intumescent material.
  • a coating preferably contains fibers, in particular a combination of mineral fibers and carbon fibers.
  • Another object of the invention is the use of the intumescent coating described for protecting components against heat in the event of a fire.
  • Components that are protected in this way are, in particular, steel girders, supports, load-bearing concrete elements, components made of plastic or fiber composite materials such as insulating panels made of expanded polystyrene, components made of wood and wood hybrids, containers and tanks for fuel and combustible (liquid) Gases such as hydrogen cylinders, components for aerospace and components in vehicle construction, in particular battery boxes of electric vehicles, the vehicle and the occupants being protected from the heat in the event of a battery fire.
  • the intumescent coating preferably contains fibers.
  • the intumescent coating is intended to increase the length of time before the steel beam or column reaches a temperature of more than 500 °C and begins to lose stability. Due to the excellent heat-insulating properties of the intumescent coating according to the invention, this period of time can be extended by up to 30, 90 or 120 minutes, for example, depending on the layer thickness and composition of the coating. This extended period of time allows a much longer window of time in which the Fire brigade can stay in a building or a steel structure and/or this can be safely evacuated.
  • Steel beams are preferably already coated at their place of manufacture and stacked and transported in this form.
  • the ease of application, the rapid and trouble-free curing and the high mechanical strength of the cured coating are particularly advantageous.
  • the use for the protection of battery boxes, in particular of electric vehicles, is also preferred.
  • the intumescent coating is preferably free of fibers. In battery fires, very high temperatures quickly develop, which are extremely dangerous for the stability of the vehicle and for the occupants. In the event of a battery fire, a battery box coated with the intumescent coating made of aluminum, for example, can keep the high heat away from the rest of the vehicle for a certain time thanks to the foamed, highly heat-insulating mass, which means that the stability of the vehicle is maintained for longer and it is easier to leave the vehicle safely .
  • the coating causes practically no emissions when the vehicle paint is baked at temperatures of up to 200° C. and its intumescent properties are not impaired.
  • an electric car with an integrated, intumescent-coated battery box can be painted with the final top coat and baked.
  • Another subject of the invention is a method for protecting components, comprising the steps
  • step (v) optionally repeating step (iv), and
  • the component is protected in particular from heat in the event of a fire and, if necessary, also from corrosion, particularly in the case of components made of steel or aluminum.
  • a suitable component is in particular a steel girder, a support made of steel or concrete, a load-bearing concrete element such as in particular an intermediate floor or a ceiling, a component made of plastic such as in particular an insulating board, a support in vehicle construction or a battery box for electric vehicles, in particular an aluminum battery box .
  • the surface of the component is preferably cleaned, in particular by brushing, blasting, vacuum cleaning or blowing off, and free of oil, grease, cement skin, oxide layers, rust and dust.
  • the surface is preferably prepared in such a way that the old coating is at least partially removed from the surface became.
  • a primer is applied to the surface of the component, in particular by spraying or using a brush.
  • Particularly suitable as a primer for steel are SikaCor® Zinc R, SikaCor® Zinc W, Sika® Permacor®-1705 or Sika® Permacor®-2706 EG (all from Sika).
  • SikaCor® Zinc R SikaCor® Zinc R
  • Such a primer enables particularly good anti-corrosion properties and excellent adhesion of the subsequent intumescent coating.
  • Particularly suitable as a primer for concrete is Sikafloor®-150, Sikafloor®-151, Sikafloor®-160 or Sikafloor®-161 (all from Sika).
  • Sikafloor®-150, Sikafloor®-151, Sikafloor®-160 or Sikafloor®-161 all from Sika.
  • Such a primer binds existing dust, closes the pores and enables excellent adhesion of the subsequent intumescent coating.
  • the mixed intumescent coating is applied to the optionally primed surface of the component within the pot life in step (iii).
  • the application is preferably carried out by means of a spray apparatus or with the aid of a brush, a roller, a roller or a doctor blade, preferably in an airless spraying process, in particular with a single-feed airless spraying apparatus.
  • a layer thickness in the range from 0.5 to 2 mm is preferably applied in one operation.
  • step (iv) is carried out one or more times, waiting in between in each case until the previous layer has hardened to such an extent that a dry, non-tacky surface has formed.
  • the intumescent coating is preferably applied in a layer thickness in the range from 0.5 to 10 mm, preferably 1 to 8 mm, in particular 2 to 6 mm.
  • the intumescent coating is preferably applied in more than one operation. With a desired layer thickness of 5 mm, for example, almost 1.7 mm are preferably applied three times. If necessary, a top coat is applied to the cured intumescent coating. This is particularly preferred when the cured intumescent coating remains clearly visible and should have a particularly decorative, color-stable appearance.
  • SikaCor® EG-4, SikaCor® EG-5, Sika® Permacor®-2230 VHS, Sika® Permacor®-2330, Sika® Unitherm® Top S or Sika® Unitherm® Top W are particularly suitable as a top coat. .
  • Another object of the invention is a coated component obtained from the method for protecting components as previously described.
  • the coated component is in particular a steel girder, a support made of steel or concrete, a load-bearing concrete element such as in particular an intermediate floor or a ceiling, a component made of plastic such as in particular an insulating board, a support in vehicle construction or a battery box for electric vehicles, in particular an aluminum battery box .
  • the coating preferably has a layer thickness in the range from 0.5 to 10 mm, preferably 1 to 8 mm, in particular 2 to 6 mm.
  • the coating When exposed to high heat in the event of a fire, the coating forms a hard, stable, multiplied in volume, porous material with surprisingly high thermal insulation, as previously described.
  • AHEW 1 stands for the amine hydrogen equivalent weight.
  • NK standard climate
  • HDDGE hexanediol diglycidyl ether (Araldite® DY-H with EEW approx.
  • the viscosity was measured using a cone-plate viscometer (cone diameter 25 mm, cone angle 1°, cone-plate distance 0.05 mm) at a shear rate of 10 s -1 .
  • a resin component with an EEW of 740 g/eq was prepared by using 17 parts by weight (pbw) BADGE, 6.6 pbw HDDGE, 1.8 pbw trimethylolpropane triacrylate, 43.5 pbw ammonium polyphosphate, 12.5 pbw melamine, 6.6 pbw triisobutyl phosphate, 3 pbw methylstyrenated phenol, 4 GT titanium dioxide, 4 GT fillers and 1 GT other additives were mixed and stored with exclusion of moisture.
  • a separate hardener component was then produced for each example by mixing the ingredients of the hardener component specified in Table 1 in the specified amounts (in parts by weight) and storing them with the exclusion of moisture.
  • the viscosity was measured 5 minutes after the resin and hardener components had been mixed, using a plate-plate viscometer (plate diameter 50 mm, plate distance 0.05 mm) at the specified shear rate.
  • the pot life was determined as the time taken for the viscosity to double.
  • the time to degree of dryness 1 (dust-dry) and degree of dryness 6 (touch-dry, walkable) in standard climate as described in DIN 53150 and the Shore D hardness according to DIN 53505 were determined according to 1d and 2d in standard climate.
  • This was primed with Sika® Permacor®-2706 EG (two-component epoxy resin micaceous iron oxide coating, from Sika) (dry layer thickness 40 mm) and stored in a standard climate for 24 hours. Then a temperature sensor was attached to the center of the primed inside of the H-shaped profile, a total of 6 Piece.
  • the respective intumescent coating was then applied to the entire component by applying three layers of just under 1.7 mm each with a waiting time of 24 hours between the layers with a brush in such a way that the component was finally completely covered with a layer thickness of 5 mm of the respective Intumescent coating was coated, which covered the attached thermocouples. After a storage time of 3 days in standard climate, the coated component showed a slightly rough, non-tacky, defect-free surface due to the mineral fibers it contained.
  • FIG. 1 shows the temperature of the component as a function of time
  • Table 1 shows the temperature of the component after 5, 10, 20, 30, 40, 50 and 60 minutes.
  • a slow increase in temperature shows a high insulating effect of the intumescent coating, which corresponds to a longer period of time before the component becomes thermally unstable.
  • the cooled test specimen was removed from the furnace, with the component (H-profile) embedded in a hard, large-volume, foamed mass.
  • FIG. 1 shows the temperature of the component during the fire test for example 1 and for example 2 (reference) versus time.
  • Table 1 Composition and properties of Examples 1 to 2.

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Abstract

L'invention concerne une peinture intumescente comprenant – au moins une résine époxyde liquide, - au moins une amine de formule (I), dans laquelle A représente un résidu alkylène, cycloalkylène ou arylalkylène divalent ayant 2 à 15 atomes de carbone et Y représente H ou un résidu alkyle, cycloalkyle, aralkyle ou aryle ayant 1 à 11 atomes de carbone, qui éventuellement porte un atome d'oxygène ou d'azote, les deux atomes d'azote auxquels le radical A est lié étant séparés l'un de l'autre d'au moins deux atomes de carbone, et l'amine de formule (I) contenant au moins 8 atomes de carbone en tout, - au moins un sel S1, qui dégage de l'acide phosphorique après chauffage, - et au moins une substance S2, qui dégage un gaz non combustible après chauffage. La peinture intumescente est de préférence utilisée pour la protection de composants vis-à-vis des effets du chauffage au cours d'un incendie. L'amine de formule (I) permet d'obtenir des peintures intumescentes ayant une protection exceptionnellement bonne vis-à-vis de la chaleur.
PCT/EP2021/085354 2020-12-18 2021-12-13 Peinture intumescente WO2022128839A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116574429A (zh) * 2023-05-16 2023-08-11 北京慕成防火绝热特种材料有限公司 一种桥梁斜拉索抗特种火防火涂料、制备工艺及施工方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3138863A1 (fr) * 2015-09-01 2017-03-08 Sika Technology AG Composition de resine hepoxyde pauvre en emissions
US10131800B2 (en) 2013-07-16 2018-11-20 Akzo Nobel Coatings International B.V. Intumescent coating composition
US10442937B2 (en) 2015-04-24 2019-10-15 PPG Coating Europe B.V. Intumescent coating composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10131800B2 (en) 2013-07-16 2018-11-20 Akzo Nobel Coatings International B.V. Intumescent coating composition
US10442937B2 (en) 2015-04-24 2019-10-15 PPG Coating Europe B.V. Intumescent coating composition
EP3138863A1 (fr) * 2015-09-01 2017-03-08 Sika Technology AG Composition de resine hepoxyde pauvre en emissions
EP3344677A1 (fr) 2015-09-01 2018-07-11 Sika Technology AG Composition de résine époxyde à faible émission

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116574429A (zh) * 2023-05-16 2023-08-11 北京慕成防火绝热特种材料有限公司 一种桥梁斜拉索抗特种火防火涂料、制备工艺及施工方法

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