EP3762438A1 - Matériau de revêtement biocide et procédé de production associé - Google Patents

Matériau de revêtement biocide et procédé de production associé

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Publication number
EP3762438A1
EP3762438A1 EP19708111.0A EP19708111A EP3762438A1 EP 3762438 A1 EP3762438 A1 EP 3762438A1 EP 19708111 A EP19708111 A EP 19708111A EP 3762438 A1 EP3762438 A1 EP 3762438A1
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EP
European Patent Office
Prior art keywords
amine
ether
component
mixture
urea
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP19708111.0A
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German (de)
English (en)
Inventor
Karim El Kudsi
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Individual
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Individual
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Publication date
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Publication of EP3762438A1 publication Critical patent/EP3762438A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225—Polyamines
    • C08G18/3234—Polyamines cycloaliphatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/285—Nitrogen containing compounds
    • C08G18/2865—Compounds having only one primary or secondary amino group; Ammonia
    • 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
    • C08G18/3228—Polyamines acyclic
    • 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
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • 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
    • C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
    • C08G18/722—Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
    • 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
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • C—CHEMISTRY; METALLURGY
    • 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
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
    • C08G18/8012—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with diols
    • C08G18/8016—Masked aliphatic or cycloaliphatic polyisocyanates
    • 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
    • C08G59/14—Polycondensates modified by chemical after-treatment
    • C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
    • C08G59/1477—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing nitrogen
    • 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

Definitions

  • the invention relates to a biocidal coating material and an associated production method.
  • Coatings based on epoxides are widely used. These are based essentially on bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol diglycidyl ether, novolak epoxy systems and various amines as Hartem, z. Diethylenetriamine, dipropylenetriamine, isophoronediamine, 2,2,4- / 2,4,4-trimethylhexanediamine, etc.
  • a biocidal effect, i. H. the prevention of the formation of biofilms on the surface of the coating and the subsequent growth of bacteria, algae, microfungi or marine organisms is usually achieved by additives.
  • Such additives may include metals such as copper, tin or silver in various forms, organic chloro and sulfur compounds such as carbendazim or 2-methylthio-4-ferf-butylamino-6-cyclopropylamino-s-triazine, propioconazole, 3- (3,4 Dichlorophenyl) -1, 1-dimethylurea (diuron), 2-octylisothiazol-3 (2H) on (octhilinone), or metal compounds such as bis (tributyltin) oxide, triphenyltin hydroxide, and triphenyltin chloride.
  • the active principle of all these compounds is based on the fact that small amounts are continuously released into the environment, but there can not be degraded due to their properties and accumulate.
  • WO 2014/008264 A1 describes antimicrobial compositions based on polyhaloolefin polymers and cationic antimicrobial reagents as well as a carrier with plasticizer and heat stabilizer, wherein the antimicrobial compound is incorporated into the polymer structure.
  • oligourea compounds are dispersed in glycols and / or polyether alcohols.
  • Polyurethane urea coatings based on this have inherently biocidal activity. These oligourea compounds are due to the content of diols / polyols as hardener components for epoxy resins less or not suitable, especially in coatings in which the leaching of ingredients of the coating is to be avoided in contact with water.
  • the method comprises the steps:
  • a ratio of the sum of the primary and secondary amine groups to the isocyanate groups is 10: 1 to 2: 1;
  • a ratio of the epoxy groups of the epoxy component to the amine groups of the urea amine component is 0.25: 1 to 1: 0.25, preferably 0.5: 1 to 1: 0.5.
  • the oligoureaamines obtainable by the process according to the invention based on mixtures of monoamines and di- and / or polyamines which have been partially reacted with one or more di- or triisocyanates can form layers or films in their further reaction with epoxide compounds which have inherent biocidal activity. These layers or films also have high water, oxygen and / or carbon dioxide blocking capability.
  • step (i) of the process an oligourea composite is first formed by an addition reaction of isocyanates and various amines. The latter is then reacted in step (iii) with polyfunctional glycidyl ethers to form a novel, crosslinked coating material.
  • step (i) used by amines, which differ by the number of existing primary or secondary amine groups.
  • a first amine has only a single primary or secondary amine group, while the second amine has 2 or more of these functionalities and may optionally include a tertiary amino group.
  • Subsequent reaction with polyfunctional isocyanates produces a complex mixture of oligoureas still having free amine groups and one or more amines.
  • the first amine is preferably a C 3 -C 15 -cycloamine or a compound of the formula (1)
  • R 1 selected from the group consisting of C 1 -C 15 alkyl, C 3 -C 10 cycloalkyl and C 3 -C 10 heterocycloalkyl and
  • R 2 selected from the group comprising hydrogen, C 1 -C 15 alkyl, C 3 -C 10 cycloalkyl and C 3 -C 10 heterocycloalkyl.
  • the second amine is preferably a C 3 -C 15 -cycloamine or a compound of the formula (2)
  • R 1 selected from the group consisting of C 1 -C 15 alkyl, C 3 -C 10 cycloalkyl and C 3 -C 10 heterocycloalkyl and
  • R 2 and R 3 are independently selected from the group comprising hydrogen, C1 - C15 alkyl, C3-C10 cycloalkyl, and C 3 -C 0 heterocycloalkyl.
  • the two amine groups (-NH 2 ) a and (-NH 2 ) b are bonded to the radical R 1 directly or via alkylene, in particular methylene bridges.
  • the alkyl groups of the diamines may also be linked by an optionally substituted amino group, such as in bis-N, N- (3-aminopropyl) -N-methylamine.
  • an aliphatic di- or triisocyanate is meant an acyclic or cyclic, saturated or unsaturated carbon compound having two or three isocyanate groups. Preference is given to diisocyanates of the formula (3)
  • R 1 selected from the group consisting of C 1 -C 15 alkyl, C 3 -C 10 cycloalkyl and C 3 -C 10 heterocycloalkyl.
  • the two isocyanate groups (-NCO) a and (-NCO) b are bonded directly to the radical R 1 .
  • araliphatic di- or triisocyanate is understood as meaning a carbon compound in which the two or three isocyanate groups are bonded directly to one or more aliphatic side chains of an aryl group. Preference is given to araliphatic diisocyanates of the formula (4)
  • the isocyanate components may be prepolymers (prepolymers or quasi-prepolymers) of di- and / or triols and diisocyanates, diamines and diisocyanates, or triisocyanates obtained by symmetrical or asymmetric trimerization of aliphatic and / or cycloaliphatic diisocyanates.
  • short-chain diols such as butane-1, 4-diol, dipropylene glycol, tripropylene glycol, diethylene glycol, polytetrahydrofurans of molecular weight 200 to 2000, ethylene oxide-propylene oxide copolymers of molecular weight 1000 to 4000 or polycarbonate diols of molecular weight 500 to 2000 used.
  • the ratio of the isocyanate groups to the hydroxyl groups is preferably between 2.1: 1 and 5: 1, in particular between 2.1: 1 and 2.8: 1.
  • prepolymers are formed from a diol and a diisocyanate in a ratio of 2.1: 1 to 3.5: 1 and added immediately after their preparation in a mixture of mono- and diamines and split therein again with urea formation and release of the diol
  • Suitable diols for this variant of the method according to the invention are, for.
  • ethylene glycol diethylene glycol, propane-1, 3-diol, butane-1, 4-diol, Dipropylene glycol, hexane-1, 6-diol, and 2-ethyl-1,3-hexanediol.
  • C 1 -C 5 alkyl includes, for example, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3 Methylbutyl, 1, 1-dimethylpropyl,
  • alkyl radicals with n> 6 include n-hexane, n-heptane, n-octane, n-nonane, n-decane, 1-methylpentyl, 1-methylhexyl, 1-methylheptyl, 1-methyloctyl, 1-methylnonyl, 1 Methyldecanyl, 1-ethylbutyl, 1-ethylpentyl, 1-ethylhexyl, 1-ethylheptyl, 1-ethyl octyl, 1-ethylnonyl, 1-ethyldecanyl, 2-methylpentyl, 2-methylhexyl, 2-methylheptyl, 2-methyloctyl, 2-methylnonyl, 2-methyldecanyl, 2-ethylpropyl, 2-ethylbut
  • 1,2-Dimethyldecanyl 2-ethyl-1-methylbutyl, 2-ethyl-1-methylpentyl, 2-ethyl-1-methylhexyl, 2-ethyl-1-methylheptyl, 2-ethyl-1-methyloctyl, 2-ethyl-1 methylnonyl, 2-ethyl-1-methyldecanyl, 1-ethyl-2-methylpropyl, 1-ethyl-2-methylbutyl, 1-ethyl-2-methylpentyl, 1-ethyl-2-methylhexyl,
  • C 3 -C 10 cycloalkyl is meant a monocyclic or bicyclic cycloalkyl radical having 3 to 15 carbon atoms. Examples include cycloalkyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.
  • the cycloalkyl radicals may in turn be monosubstituted or polysubstituted by C 1 -C 5 -alkyl radicals of the meaning given above.
  • substituted cycloalkyl radicals include 1-methyl-1-cyclopropyl, 1-methyl-1-cyclobutyl, 1-methyl-1-cyclopentyl, 1-methyl-1-cyclohexyl, 1-methyl-1-cycloheptyl,
  • C -C heterocycloalkyl is meant a monocyclic or bicyclic cycloalkyl radical having 3 to 15 carbon atoms, in which at least one carbon atom of the ring is replaced by a heteroatom selected from the group consisting of N, O, P and S.
  • the cycloalkyl radicals may in turn be monosubstituted or polysubstituted by C 1 -C 5 -alkyl radicals of the meaning given above.
  • C -C cycloamine is meant a monocyclic or bicyclic cycloalkyl compound of 3 to 15 carbon atoms in which at least one carbon atom of the ring is replaced by an NH group. Further carbon atoms of the ring can be replaced by a heteroatom selected from the group N, O, P and S. Examples include aziridine, azetidine, pyrrolidine, and piperidine.
  • the cycloamines can be monosubstituted or polysubstituted by C 1 -C 5 -alkyl radicals of the meaning given above.
  • first amine refers to both individual compounds and mixtures thereof.
  • first amine may comprise two or more individual compounds (amines having a primary or secondary amine group).
  • second amine refers analogously to the term "second amine”.
  • the first amine has a secondary amine group.
  • the first amine is particularly preferably a compound or a mixture of compounds which are selected from the group comprising di-n-butylamine, butylamine, piperidine, cyclohexylamine, N-ethyl-N-cyclohexylamine, 2-aminoethanol, dimethylamine, N-methyl N-cyclohexylamine, N-propyl-N-cyclohexylamine, N-butyl-N-cyclohexylamine, N, N-dicyclohexylamine and aziridine.
  • the second amine has two amine groups.
  • the second amine is preferably a compound or mixture of compounds selected from the group consisting of 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane (isophoronediamine), 1, 3-benzenedimethaneamine, bis (4- aminocyclohexyl) methane, 1, 4-diaminobutane, 1, 6-diaminohexane, 2-methyl-1,5-diaminopentane, 1,6-diamino-2,2,4-trimethylhexane, 1,6-diamino-2,4, 4-trimethylhexane, cyclohexane-1,4-diamine, 2-ethylimidazolidine, 1,5-pentanediamine, piperazine, ethylenediamine, N, N-bis (3-aminopropyl) -N-methylamine, 4,4'-methylenebis (cyclohexylamine), 1, 3-phenyl
  • polyamines such as N, N-dipropylenetriamine, N 2 -methyl-dipropylenetriamine, N, N-diethylenetriamine, tripropylenetetramine, triethylenetetramine, dicyandiamide, 2,4,6-triamino-1, 3,5-triamine, and hexamethylenetetramine used become.
  • heterocyclic di- and / or polyamines can be used alone or mixed or as a solution in one or more of the abovementioned amines, for example 2,4-diamino-6-phenyl-1,3,5-triazine, 2 , 4-diamino-6-capryl-1, 3,5-triazine and 2,4-diamino-6-undecyl-1,3,5-triazine.
  • 2,4-diamino-6-phenyl-1,3,5-triazine, 2 4-diamino-6-capryl-1, 3,5-triazine and 2,4-diamino-6-undecyl-1,3,5-triazine.
  • These compounds can be used as well as those mentioned above in combination with dycandiamide.
  • a molar ratio of the first amine to the second amine is in the range of 1.5: 1 to 1: 5.
  • one or more guanamines selected from the group consisting of adipoguanamine, isoadipoguanamine, 2-methylglutaroguanamine and caprinoguanamine are added to the urea-amine component provided in step (i).
  • the weight fraction of guanamines in the total weight of the provided urea amine component and the guanamines is 5 to 35 wt.%.
  • the di- or triisocyanate is a compound or a mixture of compounds which are selected from the group comprising isophorone diisocyanate (IPDI), 1,4-cyclohexane diisocyanate, 1, 3
  • 1, 3-tetramethylxylylene diisocyanate is particularly preferred.
  • Step (i) is preferably carried out at temperatures in the range of 10 to 180 ° C.
  • the reaction may preferably be carried out in such a way that a solution or a dispersion of the urea amine component is present in the excess amine.
  • reaction of the amines with the isocyanate or the prepolymer is carried out either in bulk or in the presence of solvents.
  • the amines are preferably initially charged and the isocyanate or prepolymer slowly added dropwise at a temperature below or equal to 45 ° C, if the amines are still liquid.
  • the reaction temperature should not exceed 120 ° C.
  • the amount of solvent between 1% and 90%, each based on the total mixture adjusted. Preference is given to the lowest possible amounts of solvent, for example 5 to 25% based on the total mixture.
  • the solvents used are preferably N-methylpyrrolidone, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, hexamethylphosphonamide, and tetrahydrofuran.
  • the prepolymer is added to the amine mixture at a temperature between 30 and 150 ° C. After completion of the addition, the mixture is reacted for a further 10 minutes to 8 hours, preferably 1 to 4 hours, at temperatures between 150 and 250 ° C, preferably 180 to 200 ° C, whereby the urethane groups of the prepolymer are split and converted to urea groups.
  • the term 'glycidyl ether' means both individual compounds and mixtures thereof.
  • the glycidyl ether may include two or more individual compounds (aliphatic polyfunctional glycidyl ethers).
  • polyfunctional glycidyl ethers are preferably mono-, di-, tri- or Tetraglycidether used.
  • the polyfunctional glycidyl ether is a compound or a mixture of compounds which are selected from the group consisting of ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, butanediol-1,4 diglycidyl ether, hexanediol 1,6-diglycidyl ether, octanediol -1, 8-diglycidyl ether, dodecane-1, 12-diglycidether, isosorbide diglycidyl ether, glycerol monoglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether, trimethylolpropane triglycidyl ether, pentaerythritol monog
  • the polyfunctional glycidyl ether is particularly preferably a mixture of trimethylolpropane monoglycidyl ether, trimethylolpropane diglycidyl ether and trimethylolpropane triglycidyl ether.
  • glycidol esters of dicarboxylic acids can be used, for example cyclohexane-1,2-dicarboxylic acid diglycidyl ester or terephthalic acid diglycidyl ester.
  • Trimethylolpropane monoglycidyl ether, trimethylolpropane diglycidyl ether and trimethylolpropane triglycidyl ether as epoxide component may be added to the urea amine component and / or the epoxy component.
  • Nanosized metal oxides, metal hydroxides, metal oxide hydroxides, semimetal oxides, silicates, layer silicates, surface-modified layer silicates, graphene, surface-modified graphenes, carbon hollow fibers and modified carbon hollow fibers can be used in particular as additives.
  • silicates such as albite, also calcite (calcium carbonate) or dolomite (calcium magnesium carbonate).
  • additives may include dyes, pigments, solid or liquid flame retardants, dispersing aids, compatibilizers, leveling agents and thixotropic agents.
  • solid pigments iron oxides, carbon black, titanium dioxide, hematite, etc.
  • silica fumed silica having a specific surface area of 90 to 380 m 2 / g.
  • the solid and / or liquid additives can be incorporated.
  • solid additives z.
  • a thixotropic agent such as fumed silica
  • pigments such as iron oxides
  • a nanoscale sheet silicate such as a montmorillonite surface-modified with onium ions.
  • the respective proportions can vary within a wide range, for example:
  • Pyrogenic silica 1 to 10 wt .-% based on the total mixture, in particular 1 to 5 wt .-%;
  • Iron black pigment 0.1 to 10% by weight, based on the total mixture, in particular 0.5 to 2.5%;
  • Nanoscale sheet silicate 0.001 to 20 wt .-% based on the total mixture, in particular 0.01 to 5 wt .-%.
  • Another aspect of the invention relates to a biocidal coating material prepared by the above-described method.
  • the biocidal coating material is preferably used to prepare a coating for Ship walls, ship interior, ship deck, ramps, propellers, wind power blades, wind turbine housings, floors (for example, in hypermarkets or cold stores) and pipes, in particular for the production of an inner pipe coating of hot water, hot water or drinking water pipes used.
  • the epoxy component and the urea amine component can be intimately mixed at a temperature of 5 to 45 ° C with each other.
  • the reaction time of the systems and their curing behavior can be controlled so that, for example, reaction times of 3 minutes to 90 minutes are possible.
  • the reacting mixture is processed after a time of 1 minute to 1 hour by means of a doctor blade, draw knife, patting or by entering into a pipe system with subsequent smoothing by a pig to the coatings according to the invention.
  • the application of a primer is possible before the coating according to the invention.
  • the mixture of the two components can be done manually or mechanically with 2-component mixing machines.
  • the components mixed by means of 2-component mixing machines can be entered into tubes through which tubes a compressed air is pressed by means of compressed air, so that tube inner coatings of 20 to 500 ⁇ m are produced on the inner wall.
  • Amine number means the amount of KOH in mg, which is equated to the amine content of 1 g of substance. According to DIN 53176, the amine number is determined by potentiometric titration. The viscosity of liquids is measured with a viscometer z. B. measured according to EN ISO 3219.
  • the epoxide component is prepared from 52.5 g of trimethylolpropane triglycidyl ether, 5.5 g of butane-1, 4-diol diglycidyl ether, 3.5 g of fumed silica (trade name Aerosil 380 from Evonik AG), 0.5 g of iron oxide black (Particle size 12 - 56 pm) and 0.5 g of a modified montmorillonite (trade name Nanocor I.30E).
  • 12.5 g of the epoxy component is mixed intensively at 30.degree. C. with 7.55 g of the urea amine and spread on a laboratory streak table with integrated dryer (LabCater from Mathis) to a 200 .mu.m film by means of a knife blade.
  • the pot life is 12 minutes.
  • the film is cured at 55 ° C for 30 minutes.
  • the epoxide component is prepared from 52.5 g of trimethylolpropane triglycidyl ether, 5.5 g of hexane-1, 6-diol diglycidyl ether, 3.5 g of fumed silica (trade name Aerosil R208 from Evonik AG), 0.5 g of iron oxide black (Particle size 12-56 pm) and 0.8 g of a modified montmorillonite (trade name Nanocor I.30E).
  • 12.5 g of the epoxy component is mixed intensively at 30.degree. C. with 7.75 g of the urea amine and spread on a laboratory streak table with integrated dryer (LabCater from Mathis) to a 200 .mu.m film by means of a knife blade.
  • the pot life is 6 minutes.
  • the film is cured at 55 ° C for 30 minutes.
  • the epoxide component is prepared from 49.7 g of pentaerythritol tetraglycidyl ether and triglycidyl ether (mixture about 1: 1), 7.5 g of butane-1, 4-diol diglycidyl ether, 3.5 g of fumed silica (trade name Aerosil 380 from Evonik AG), 0.5 g of iron oxide black (particle size 12-56 ⁇ m) and 0.25 g of a modified montmorillonite (trade name Nanocor I.30E).
  • 12.5 g of the epoxy component is at 30 ° C with 6.35 g of urea amine intensive mixed and spread on a laboratory blending table with integrated dryer (LabCoater Mathis) to a 200 pm film using knife blade.
  • the pot life is 9 minutes.
  • the film is cured at 55 ° C for 30 minutes.
  • the epoxide component is prepared from 52.5 g of trimethylolpropane triglycidyl ether, 5.5 g of butane-1, 4-diol diglycidyl ether, 3.5 g of fumed silica (trade name Aerosil 380 from Evonik AG), 0.5 g of iron oxide black (Particle size 12 - 56 pm) and 0.5 g of a modified montmorillonite (trade name Nanocor I.30E).
  • 12.5 g of the epoxy component is mixed intensively at 30.degree. C. with 7.75 g of the urea amine and spread on a laboratory streak table with integrated dryer (LabCater from Mathis) to a 200 .mu.m film by means of a knife blade.
  • the pot life is 16 minutes.
  • the film is cured at 55 ° C for 30 minutes.
  • the epoxide component is prepared from 52.5 g of trimethylolpropane triglycidyl ether, 5.5 g of butane-1, 4-diol diglycidyl ether, 3.5 g of fumed silica (trade name Aerosil 380 from Evonik AG), 0.5 g of iron oxide black (Particle size 12 - 56 pm) and 0.5 g of a modified montmorillonite (trade name Nanocor I.30E).
  • 12.5 g of the epoxy component is mixed intensively at 30.degree. C. with 7.75 g of the urea amine and spread on a laboratory streak table with integrated dryer (LabCater from Mathis) to a 200 .mu.m film by means of a knife blade.
  • the pot life is 16 minutes.
  • the film is cured at 55 ° C for 30 minutes.
  • the epoxide component is prepared from 52.5 g of trimethylolpropane triglycidyl ether, 5.5 g of butane-1, 4-diol diglycidyl ether, 3.5 g of fumed silica (trade name Aerosil 380 from Evonik AG), 0.5 g of iron oxide black (Particle size 12 - 56 pm) and 0.5 g of a modified montmorillonite (trade name Nanocor I.30E).
  • 12.5 g of the epoxy component is mixed intensively at 30.degree. C. with 7.4 g of the urea amine and spread on a laboratory streak table with integrated dryer (LabCater from Mathis) to a 200 .mu.m film by means of a knife blade.
  • the pot life is 10 minutes.
  • the film is cured at 55 ° C for 30 minutes.
  • the epoxide component is prepared from 500 g pentaerythritol tetraglycidyl ether, 125 g dipentaerythritol pentaglycidyl ether, 12.5 g micronized titanium dioxide, 12.5 g iron oxide black (particle size 12-56 pm) and 1.5 g of a modified montmorillonite (trade name Nanocor I. 30E).
  • the epoxy component is mixed by means of a static mixer at 30 ° C. by means of a mixing machine from Hilger & Kern in a ratio of 1.33: 1 and spread onto the screed of a concrete floor by means of a doctor, so that a coating of on average 400 ⁇ m was formed.
  • the pot life was 20 minutes, the tack-free time 56 minutes, the curing time 12 hours. This gives a black film with the glass transition temperature (DSC) 176 ° C, a tear strength of 22 N / mm 2 , a Shore D hardness of 62 and an elongation at break of 5.8%.
  • DSC glass transition temperature
  • this coating was also applied and overcoated with a water sample from a nearby body of water. After 30 days, the supernatant water was removed and the layer checked. After rinsing with 0.5 at water, the layer was completely clean.
  • the temperature is slowly increased to 125 ° C and stirred for 30 minutes at this temperature.
  • a clear solution of the urea amine in the amine mixture is obtained, the amine number is 205 mg KOH / g, the viscosity 1086 mPas (25 ° C).
  • the epoxide component is prepared from 525 g of trimethylolpropane triglycidyl ether, 75 g of pentaerythritol triglycidyl ether, 35 g of fumed silica (trade name Aerosil R208 from Evonik AG), 7 g of iron oxide black (particle size 12-56 ⁇ m) and 4 g of a modified montmorillonite ( Trade name Nanocor I.30E).
  • the epoxy component is mixed with the urea amine component by means of a static mixer at 30 ° C by means of a mixing machine from Hilger & Kern in the ratio 1, 48: 1 and placed in a HDPE pipe of 14 mm internal diameter. Thereafter, a 13 mm pig is guided through the tube by means of compressed air, so that a coating of an average of 300 pm was formed on the tube inner wall.
  • the pot life was 20 minutes, the tack-free time 56 minutes, the curing time 12 hours. This gives a black film with the glass transition temperature (DSC) 81 ° C, a Shore A hardness of 85, an elongation at break of 8.4% and a tear strength of 18 N / mm 2 .
  • a sample of the internally coated tube of 30 cm in length was treated with a drinking water sample which additionally contained 1000 germs per ml of Listeria. After 7 days at 25 ° C, the water was rechecked for its germ count. A value of 678 germs per ml was determined.
  • a heatable 750 ml glass reactor is charged with 341 g of isophoronediamine, 25 g of N-ethyl-N-cyclohexylamine and 145 g of N, N-bis (3-aminopropyl) -N-methylamine and 56 g of the prepolymer are added slowly under nitrogen blanketing gas Add 50 ° C, whereby the temperature rises to 75 ° C; after the addition is heated to 100 ° C and stirred for 1 h at this temperature. Thereafter, it is heated to 185 ° C for three hours with stirring and cooled.
  • the urea amine has the following properties:
  • the epoxide component is prepared from 525 g of trimethylolpropane triglycidyl ether, 75 g of pentaerythritol triglycidyl ether, 35 g of fumed silica (trade name Aerosil R208 from Evonik AG), 7 g of iron oxide black (particle size 12-56 ⁇ m) and 4 g of a modified montmorillonite ( Trade name Nanocor I.30E).
  • the epoxy component is mixed by means of a static mixer at 30 ° C. by means of a mixing machine from Hilger & Kern in a ratio of 1.75: 1 and introduced into an HDPE pipe of 14 mm internal diameter. Thereafter, a 13 mm pig was passed through the tube by means of compressed air, so that a coating of on average 300 pm was formed on the tube inner wall.
  • the pot life was 40 minutes, the tack-free time 250 minutes, the curing time 18 hours. This gives a black film with the glass transition temperature (DSC) 72 ° C, a Shore A hardness of 82, an elongation at break of 16.5% and a tensile strength of 33 N / mm 2 .
  • a sample of the internally coated tube of 30 cm in length was treated with a drinking water sample which additionally contained 1000 germs per ml of Listeria. After 7 days at 25 ° C, the water was rechecked for its germ count. A value of 82 germs per ml was determined.
  • the epoxide component is prepared from 525 g of trimethylolpropane triglycidyl ether, 75 g of pentaerythritol triglycidyl ether, 35 g of fumed silica (trade name Aerosil R208 from Evonik AG), 7 g of iron oxide black (particle size 12-56 ⁇ m) and 4 g of a modified montmorillonite ( Trade name Nanocor I.30E).
  • the epoxy component is mixed by means of a static mixer at 30 ° C. by means of a mixing machine from Hilger & Kern in a ratio of 1.75: 1 and introduced into an HDPE pipe of 14 mm internal diameter. Thereafter, a 13 mm pig was passed through the tube by means of compressed air, so that a coating of on average 300 pm was formed on the tube inner wall.
  • the pot life was 27 minutes, the tack-free time 130 minutes, the curing time 1 1 hours. This gives a black film with the glass transition temperature (DSC) 78 ° C, a Shore A hardness of 76, an elongation at break of 12% and a tensile strength of 21 N / mm 2 .
  • a sample of the internally coated tube of 30 cm in length was treated with a drinking water sample which additionally contained 1000 germs per ml of Listeria. After 7 days at 25 ° C, the water was rechecked for its germ count. A value of 255 germs per ml was determined.
  • the epoxy component is a mixture of 29% by weight of trimethylolpropane monoglycidyl ether, 30% by weight of trimethylolpropane diglycidyl ether and 41% by weight of trimethylolpropane triglycidyl ether.
  • glycidyl ether mixture 143 g are mixed at ambient temperature with 38.9 g of the hardener component for 5 minutes and then spread on silkoninstrumentem release paper on a laboratory Streichisch with integrated dryer (LabCoater® Mathis) to a 200 pm film using knife blade.
  • the pot life is 18 minutes.
  • the film is cured at 60 ° C for 300 minutes.
  • the epoxy component is a mixture of 29% by weight of trimethylolpropane monoglycidyl ether, 30% by weight of trimethylolpropane diglycidyl ether and 41% by weight of trimethylolpropane triglycidyl ether.
  • 143 g of the glycidyl ether mixture are mixed at ambient temperature with 40.3 g of the hardener component for 5 minutes and then spread on silkoninstrumentem release paper on a laboratory Streichisch with integrated dryer (LabCoater® Mathis) to a 200 pm film by knife blade.
  • the pot life is 18 minutes.
  • the film is cured at 60 ° C for 300 minutes.
  • the epoxy component is a mixture of 29% by weight of trimethylolpropane monoglycidyl ether, 30% by weight of trimethylolpropane diglycidyl ether and 41% by weight of trimethylolpropane triglycidyl ether.
  • 143 g of the Glycidethergemisches be at ambient temperature with 43.2 g of Hardener component mixed for 5 minutes and then spread on a siliconized release paper on a laboratory table with integrated dryers (LabCoater® Mathis) to a 200 pm film by knife blade.
  • the pot life is 18 minutes.
  • the film is cured at 60 ° C for 300 minutes.
  • the epoxy component is a mixture of 29% by weight of trimethylolpropane monoglycidyl ether, 30% by weight of trimethylolpropane diglycidyl ether and 41% by weight of trimethylolpropane triglycidyl ether.
  • Glycidethergemisches are mixed at ambient temperature with 1 18 g of the curing agent component for 5 minutes and then on silkoninstrumentem release paper on a laboratory Streichisch with integrated dryer (LabCoater® Mathis) to a 200 pm Film passed by knife blade.
  • the pot life is 18 minutes.
  • the film is cured at 60 ° C for 300 minutes.
  • Viscosity 25 ° C: 2310 mPas Laser light scattering: peaks at 0.85 and 13.2 nm
  • the epoxy component is a mixture of 29% by weight of trimethylolpropane monoglycidyl ether, 30% by weight of trimethylolpropane diglycidyl ether and 41% by weight of trimethylolpropane triglycidyl ether.
  • 143 g of Glycidethergemisches be at ambient temperature with 130.5 g of
  • Hardener component mixed for 5 minutes and then spread on a siliconized release paper on a laboratory table with integrated dryers (LabCoater® Mathis) to a 200 pm film by knife blade.
  • the pot life is 18 minutes.
  • the film is cured at 60 ° C for 300 minutes.

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  • 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)
  • General Chemical & Material Sciences (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne un matériau de revêtement biocide et un procédé de production associé. Le procédé comprend les étapes suivantes consistant à : (i) préparer un composant amine-urée, pouvant être obtenu en faisant réagir a) un diisocyanate ou un triisocyanate aliphatique ou araliphatique avec b) un mélange constitué d'une première amine comprenant un groupe amine primaire ou secondaire et une ou plusieurs secondes amines comprenant 2 groupes amine primaires ou secondaires ou plus, le rapport de la somme des groupes amine primaires et secondaires aux groupes isocyanate étant de 10/1 à 2/1 ; (ii) préparer un composant époxyde comprenant un ou plusieurs éthers glycidiques polyfonctionnels aliphatiques ; et (iii) faire réagir le composant amine-urée avec le composant époxyde, le rapport des groupes époxyde du composant époxyde aux groupes amines du composant amine-urée étant de 0,25/1 à 1/0,25.
EP19708111.0A 2018-03-06 2019-03-05 Matériau de revêtement biocide et procédé de production associé Withdrawn EP3762438A1 (fr)

Applications Claiming Priority (2)

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EP18160234.3A EP3536725A1 (fr) 2018-03-06 2018-03-06 Matériau de revêtement biocide et procédé de fabrication associé
PCT/EP2019/055413 WO2019170653A1 (fr) 2018-03-06 2019-03-05 Matériau de revêtement biocide et procédé de production associé

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DE102020127468A1 (de) 2020-10-19 2022-04-21 Werner H. Salewski Multifunktionale Epoxyd-Systeme
DE102022106745A1 (de) 2022-03-23 2023-09-28 Werner H. Salewski Thermoplast-Blends mit inhärent bioziden Eigenschaften

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US7201790B1 (en) 2005-12-02 2007-04-10 Savin Ronald R Zinc flake coating composition
EP1842882A1 (fr) 2006-04-07 2007-10-10 Ceram AG Méthode pour revêtir des surfaces et un système de revêtement des surfaces
DE102009031724A1 (de) 2009-07-01 2011-01-20 E.T.I. Gmbh Zusammensetzung zur Verhinderung / Verringerung der Mikroben-induzierten Biokorrosion durch Sulfatreduzierende Bakterien (SRB) und andere Mikroorganismen
DE102009042118A1 (de) 2009-09-18 2011-03-24 Teijin Monofilament Germany Gmbh Algenresistente Fäden
DE102011008535A1 (de) 2011-01-13 2012-07-19 Werner Klockemann Oligoharnstoff-Verbindungen und Verfahren zu ihrer Herstellung und ihre Verwendung
US9320834B2 (en) 2012-07-05 2016-04-26 3M Innovative Properties Company Hardenable antimicrobial composition
EP3101063A1 (fr) * 2015-05-31 2016-12-07 Karim El Kudsi Revêtements internes de tuyaux d'eau potable à base d'époxyde et leur procédé de fabrication

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