EP3931185A1 - Matériaux de polyisocyanurate comme masses de scellement électriques - Google Patents

Matériaux de polyisocyanurate comme masses de scellement électriques

Info

Publication number
EP3931185A1
EP3931185A1 EP20706286.0A EP20706286A EP3931185A1 EP 3931185 A1 EP3931185 A1 EP 3931185A1 EP 20706286 A EP20706286 A EP 20706286A EP 3931185 A1 EP3931185 A1 EP 3931185A1
Authority
EP
European Patent Office
Prior art keywords
weight
casting resin
polyisocyanate
alkyl
isocyanate
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.)
Pending
Application number
EP20706286.0A
Other languages
German (de)
English (en)
Inventor
Mathias Matner
Michael Ehlers
Dirk Achten
Ralf Rott
Bengt ARHEDEN
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Covestro Deutschland AG
Original Assignee
Covestro Deutschland AG
Covestro Intellectual Property GmbH and Co KG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Covestro Deutschland AG, Covestro Intellectual Property GmbH and Co KG filed Critical Covestro Deutschland AG
Publication of EP3931185A1 publication Critical patent/EP3931185A1/fr
Pending legal-status Critical Current

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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
    • C08G18/08—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
    • C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
    • C08G18/022—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only the polymeric products containing isocyanurate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
    • C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
    • C07D273/04—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/161—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/161—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22
    • C08G18/163—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/166—Catalysts not provided for in the groups C08G18/18 - C08G18/26
    • C08G18/168—Organic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/1825—Catalysts containing secondary or tertiary amines or salts thereof having hydroxy or primary amino groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/225—Catalysts containing metal compounds of alkali or alkaline earth metals
    • 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
    • C08G18/2815—Monohydroxy compounds
    • C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
    • C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
    • 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
    • C08G18/4825—Polyethers containing two hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—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
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/24—Acids; Salts thereof
    • C08K3/26—Carbonates; Bicarbonates
    • 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
    • C08K3/34—Silicon-containing compounds
    • 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
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • 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
    • C08K9/00—Use of pretreated ingredients
    • C08K9/04—Ingredients treated with organic substances
    • C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C39/00—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor
    • B29C39/02—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor for making articles of definite length, i.e. discrete articles
    • B29C39/10—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor for making articles of definite length, i.e. discrete articles incorporating preformed parts or layers, e.g. casting around inserts or for coating articles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2075/00—Use of PU, i.e. polyureas or polyurethanes or derivatives thereof, as moulding material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
    • B29L2031/00—Other particular articles
    • B29L2031/34—Electrical apparatus, e.g. sparking plugs or parts thereof
    • B29L2031/3406—Components, e.g. resistors
    • 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
    • C08G2115/00—Oligomerisation
    • C08G2115/02—Oligomerisation to isocyanurate groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/24—Acids; Salts thereof
    • C08K3/26—Carbonates; Bicarbonates
    • C08K2003/265—Calcium, strontium or barium carbonate
    • 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
    • C08K2201/00—Specific properties of additives
    • C08K2201/002—Physical properties
    • C08K2201/006—Additives being defined by their surface area

Definitions

  • the present invention relates to potting compounds which cure to form polyisocyanurate plastics, the production of said potting compounds and the use of the potting compounds for the production of electrical components.
  • plastics are often used to embed electrical components, for example to protect them from dirt, moisture or contact.
  • the prior art describes the use of epoxy resins, polyurethanes and silicones for this purpose.
  • plastics mentioned above are often made up of two components.
  • the mixing ratio of the two components must be carefully observed in order to obtain optimum properties.
  • Polyurethane casting compounds are often based on polymeric methylene di (phenyl diisocyanate) (MDI) and castor oil.
  • MDI polymeric methylene di (phenyl diisocyanate)
  • castor oil polymeric methylene di (phenyl diisocyanate)
  • MDI has an intrinsically low viscosity in the range of 200 mPas, which allows high filler contents to be incorporated. These are desirable for reasons of flame protection and because of the high cost of the starting materials.
  • the two-component reaction mixtures also often have a short pot life. There is therefore a need for casting resins which do not have the disadvantages mentioned above.
  • Plastics that can be obtained by crosslinking isocyanate groups with one another are known in principle in the prior art (WO 2015/166983; WO 2016/170059; European Polymer Journal (1980) 16: 147-148).
  • Composite materials which contain such plastics as a matrix are disclosed in WO 2017/191175.
  • WO 2014/147072 describes reaction mixtures with a high filler content, which are based on bisphenol A diglycidyl ether and diphenylmethane diisocyanate, ie an aromatic polyisocyanate.
  • the crosslinking of the reaction mixture does not take place through the formation of isocyanurate groups, but rather through the reaction of epoxy groups with isocyanate groups to form oxazolidinones.
  • the electrical properties of polyisocyanurate plastics in particular permissivity and loss factor, are advantageous for use in electrical potting compounds.
  • the reaction mixture had a sufficiently low viscosity to enable the production of electro-casting compounds.
  • the present invention therefore relates to a casting resin having a molar ratio of isocyanate groups to isocyanate-reactive groups of at least 3: 1 and a solvent content of at most 10% by weight, the casting resin
  • At least one inorganic filler B which contains silicon oxide units, with an oil number of at most 25 g / 100 g, determined according to DIN EN ISO 787-5 (October 1995) and a Mohs ' hardness of at least 4;
  • a “casting resin” is a reactive resin which contains the components defined above and cures to form a polyisocyanurate composite material.
  • a polyisocyanurate plastic obtained from polyisocyanate A forms a polymer matrix in which the inorganic filler B is embedded.
  • the term "casting resin” denotes thus a reaction mixture in which the components defined above are present in reactive form and mixed, so that the polyisocyanate A can be crosslinked by the trimerization catalyst C.
  • the casting resin according to the invention is advantageously used for embedding electrical components, i.e. as an electrical potting compound.
  • the complete or partial embedding of electrical components in the cast resin according to the invention serves to protect against environmental influences, protection against contact, electrical insulation or mechanical stabilization.
  • a polyisocyanurate material is obtained by curing the casting resin.
  • This is a composite material made up of a polyisocyanurate plastic as the matrix material and an inorganic filler B. It also contains residues of the trimerization catalyst C and optional additives such as UV stabilizers, flow agents or pigments.
  • the electrical component is preferably selected from the group consisting of transformers, insulators, capacitors, semiconductors, sleeves for protecting cable connections and underground cable branches.
  • Polyisocyanurate art fabric is preferably selected from the group consisting of transformers, insulators, capacitors, semiconductors, sleeves for protecting cable connections and underground cable branches.
  • polyisocyanurate plastic denotes a plastic which is obtained by crosslinking isocyanate groups with one another. This is achieved in that the casting resin contains a catalyst C suitable for this crosslinking and at the same time has a high molar ratio of isocyanate groups to groups reactive with isocyanate groups. As a result, only other isocyanate groups are predominantly available as reactants for the isocyanate groups.
  • groups reactive with isocyanate groups is understood to mean epoxy, hydroxyl, amino and thiol groups.
  • the molar ratio of isocyanate groups to groups reactive with isocyanate groups in the casting resin is at least 3: 1, preferably at least 5: 1, even more preferably at least 10: 1 and most preferably at least 20: 1.
  • the casting resin according to the invention therefore contains a maximum of 10% by weight, preferably a maximum of 5% by weight and more preferably a maximum of 2% by weight of solvent.
  • solvents are all organic solvents that are liquid at room temperature and water. Chemical compounds with at least a group reactive with isocyanate groups as defined above or at least one isocyanate group are not solvents for the purposes of the present patent application, since they can be crosslinked with the polyisocyanate A via the relevant functional groups.
  • At least 50 mol%, preferably at least 60 mol%, particularly preferably at least 70 mol%, in particular at least 80 mol% and very particularly preferably 90 mol% of the free isocyanate groups present in polyisocyanate A are used converted to isocyanurate structural units.
  • Corresponding proportions of the nitrogen originally contained in polyisocyanate A are thus bound in isocyanurate structures in the finished polyisocyanurate plastic.
  • Side reactions in particular those to uretdione, allophanate and / or iminooxadiazinedione structures, however, usually occur and can even be used in a targeted manner, e.g. to influence the glass transition temperature (Tg) of the polyisocyanurate plastic obtained advantageously.
  • the term "polyisocyanate A” stands for all of them Compounds containing reaction mixture with an average of at least two isocyanate groups per molecule.
  • the polyisocyanate A can thus consist of a single polyisocyanate. But it can also be a mixture of several different polyisocyanates. In the context of the embodiments defined below, the polyisocyanate A can also contain admixtures of isocyanates with an average functionality of less than two.
  • polyisocyanates can be used to produce a large number of polymers (e.g. polyurethanes, polyureas and polyisocyanurates) and low molecular weight compounds (e.g. those with uretdione, isocyanurate, allophanate, biuret, iminooxadiazinedione and / or Oxadiazintrione structure).
  • polymers e.g. polyurethanes, polyureas and polyisocyanurates
  • low molecular weight compounds e.g. those with uretdione, isocyanurate, allophanate, biuret, iminooxadiazinedione and / or Oxadiazintrione structure.
  • polyisocyanates refers to monomeric and / or oligomeric polyisocyanates. In order to understand many aspects of the invention, however, it is important to distinguish between monomeric diisocyanates and oligomeric polyisocyanates.
  • oligomeric polyisocyanates are used in this application, then polyisocyanates are meant which are composed of at least two monomeric diisocyanate molecules, ie they are compounds which represent or contain a reaction product of at least two monomeric diisocyanate molecules.
  • oligomeric polyisocyanates from monomeric diisocyanates is also referred to here as modification of monomeric diisocyanates.
  • modification means the reaction of monomeric diisocyanates to form oligomeric polyisocyanates with a uretdione, isocyanurate, allophanate, biuret, iminooxadiazinedione and / or oxadiazinetrione structure.
  • hexamethylene 1,6-diisocyanate is a "monomeric diisocyanate” because it contains two isocyanate groups and is not a reaction product of at least two polyisocyanate molecules:
  • reaction products of at least two HDI molecules which still have at least two isocyanate groups are "oligomeric polyisocyanates" within the meaning of the invention.
  • oligomeric polyisocyanates are, based on the monomeric HDI, e.g. the HDI isocyanurate and the HDI biuret, which are each made up of three monomeric HDI molecules:
  • the proportion by weight of isocyanate groups based on the total amount of polyisocyanate A is at least 15% by weight.
  • polyisocyanate A can consist essentially of monomeric polyisocyanates or essentially of oligomeric polyisocyanates. However, it can also contain oligomeric and monomeric polyisocyanates in any mixing ratio.
  • the polyisocyanate A used as starting material is low in monomers (i.e. low in monomeric diisocyanates) and already contains oligomeric polyisocyanates.
  • the terms “low in monomer” and “low in monomeric diisocyanates” are used synonymously in relation to polyisocyanate A.
  • polyisocyanate A has a proportion of monomeric diisocyanates of not more than 20% by weight, in particular not more than 15% by weight or not more than 10% by weight, based in each case on the weight of polyisocyanate A.
  • polyisocyanate A has a monomeric diisocyanate content of at most 5% by weight, preferably at most 2.0% by weight, particularly preferably at most 1.0% by weight, based in each case on the weight of polyisocyanate A.
  • Particularly good results are obtained when the polyisocyanate A is essentially free from monomeric diisocyanates. Essentially free here means that the monomeric diisocyanate content is at most 0.5% by weight, based on the weight of the polyisocyanate A.
  • the polyisocyanate A consists entirely or at least 80, 85, 90, 95, 98, 99 or 99.5% by weight, based in each case on the weight of the polyisocyanate A, of oligomeric polyisocyanates.
  • a content of oligomeric polyisocyanates of at least 99% by weight is preferred here.
  • This oligomeric polyisocyanate content relates to polyisocyanate A as provided. I.e. the oligomeric polyisocyanates are not formed as an intermediate product during the process according to the invention, but are already present in the polyisocyanate A used as starting material at the beginning of the reaction.
  • Polyisocyanate compositions which are low in monomer or essentially free from monomeric isocyanates can be obtained by carrying out at least one further process step in each case to separate off the unreacted excess monomeric diisocyanates after the actual modification reaction.
  • This separation of monomers can be carried out in a particularly practical manner by processes known per se, preferably by thin-film distillation in a high vacuum or by extraction with suitable solvents which are inert towards isocyanate groups, for example aliphatic or cycloaliphatic hydrocarbons such as pentane, hexane, heptane, cyclopentane or cyclohexane.
  • polyisocyanate A is obtained by modifying monomeric diisocyanates with subsequent removal of unreacted monomers.
  • a low-monomer polyisocyanate A contains a monomeric foreign diisocyanate.
  • “monomeric foreign diisocyanate” means that it differs from the monomeric diisocyanates which were used to prepare the oligomeric polyisocyanates contained in polyisocyanate A.
  • isocyanate A has a proportion of monomeric foreign diisocyanate of at most 20% by weight, in particular at most 15% by weight or at most 10% by weight, based in each case on the weight of polyisocyanate A.
  • the isocyanate A preferably has a monomeric content External diisocyanate of at most 5% by weight, preferably at most 2.0% by weight, particularly preferably at most 1.0% by weight, based in each case on the weight of the polyisocyanate A.
  • polyisocyanate A contains monomeric monoisocyanates or monomeric isocyanates with an isocyanate functionality greater than two, i.e. with more than two isocyanate groups per molecule.
  • the addition of monomeric monoisocyanates or monomeric isocyanates with an isocyanate functionality greater than two has proven to be advantageous in order to influence the network density of the coating. Particularly practical results are obtained if isocyanate A has a proportion of monomeric monoisocyanates or monomeric isocyanates with an isocyanate functionality greater than two in polyisocyanate A of at most 20% by weight, in particular at most 15% by weight or at most 10% by weight, each based on the weight of the
  • Polyisocyanate A has.
  • the polyisocyanate A preferably has a monomeric content
  • no monomeric monoisocyanate or monomeric isocyanate with an isocyanate functionality greater than two is used in the trimerization reaction according to the invention.
  • the oligomeric polyisocyanates can in particular have uretdione, isocyanurate, aliophanate, biuret, iminooxadiazinedione and / or oxadiazinetrione structure.
  • the oligomeric polyisocyanates have at least one of the following oligomeric structure types or mixtures thereof:
  • a polyisocyanate A is used whose isocyanurate structural fraction is at least 50 mol%, preferably at least 60 mol%, more preferably at least 70 mol%, even more preferably at least 80 mol%, even more preferably at least 90 mol -% and particularly preferably at least 95 mol% based on the sum of the oligomeric structures present from the group consisting of uretdione, isocyanurate, aliophanate, biuret, iminooxadiazinedione and oxadiazinetrione structure in polyisocyanate A is.
  • a polyisocyanate A is used in the process according to the invention which, in addition to the isocyanurate structure, contains at least one further oligomeric polyisocyanate with uretdione, biuret, allophanate, iminooxadiazinedione and oxadiazinetrione structure and mixtures thereof.
  • the proportions of uretdione, isocyanurate, allophanate, biuret, iminooxadiazinedione and / or oxadiazinetrione structure in polyisocyanate A can e.g. can be determined by NMR spectroscopy. 13C-NMR spectroscopy, preferably proton-decoupled, can preferably be used here, since the oligomeric structures mentioned provide characteristic signals.
  • an oligomeric polyisocyanate A to be used in the process according to the invention preferably has an (average) NCO functionality of 2.0 to 5 , 0, preferably from 2.3 to 4.5.
  • the polyisocyanate A to be used according to the invention has an isocyanate group content of 8.0 to 28.0% by weight, preferably from 14.0 to 25.0% by weight, based in each case on the weight of the Polyisocyanate A has.
  • the polyisocyanate A is defined in that it contains oligomeric polyisocyanates which are obtained from monomeric diisocyanates regardless of the type of modification reaction used while maintaining a degree of oligomerization of 5 to 45%, preferably 10 to 40%, particularly preferred 15 to 30%.
  • "Degree of oligomerization” is to be understood as the percentage of isocyanate groups originally present in the starting mixture that is consumed during the production process with the formation of urethane, uretdione, isocyanurate, allophanate, biuret, iminooxadiazinedione and / or oxadiazinetrione structures.
  • Suitable polyisocyanates for preparing the polyisocyanate A to be used in the process according to the invention and the monomeric and / or oligomeric polyisocyanates contained therein are any polyisocyanates accessible in various ways, for example by phosgenation in the liquid or gas phase or by phosgene-free route, such as for example by thermal urethane cleavage . Particularly good results are obtained when it comes to the polyisocyanates monomeric diisocyanates.
  • Preferred monomeric diisocyanates are those which have a molecular weight in the range from 140 to 400 g / mol, with aliphatically, cycloaliphatically, araliphatically and / or aromatically attached isocyanate groups, such as. B.
  • 1,4-diisocyanatobutane 1,5-diisocyanatopentane (PDI), 1,6-diisocyanatohexane (HDI), 2-methyl-1,5-diisocyanatopentane, 1,5-diisocyanato-2,2-dimethylpentane , 2,2,4- or 2,4,4-trimethyl-1,6-diisocyanatohexane, 1,10-diisocyanatodecane, 1,3- and 1,4-diisocyanatocyclohexane, 1,4-diisocyanato-3,3, 5- trimethylcyclohexane, l, 3-diisocyanato-2-methylcyclohexane, l, 3-diisocyanato-4-methylcyclohexane, 1- isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane (isophorone diisocyanate;
  • Suitable monomeric monoisocyanates which can optionally be used in isocyanate component A are, for example, n-butyl isocyanate, n-amyl isocyanate, n-hexyl isocyanate, n-heptyl isocyanate, n-octyl isocyanate, undecyl isocyanate, dodecyl isocyanate, tetradecyl isocyanate, cetyl isocyanate, stearyl isocyanate, cyclohexyl isocyanate, cyclohexyl isocyanate, 3- or 4-methylcyclohexyl isocyanate or any mixtures of such monoisocyanates.
  • An example of a monomeric isocyanate with an isocyanate functionality greater than two, which can optionally be added to isocyanate component A, is 4-isocyanatomethyl-1,8-octane diisocyanate (triisocyanatononane; TIN).
  • the polyisocyanate A contains at most 30% by weight, in particular at most 20% by weight, at most 15% by weight, at most 10% by weight, at most 5% by weight or at most 1% by weight %, based in each case on the weight of the polyisocyanate A, of aromatic polyisocyanates.
  • aromatic polyisocyanate means a polyisocyanate which has at least one aromatically bound isocyanate group.
  • Aromatically bound isocyanate groups are understood to mean isocyanate groups which are bound to an aromatic hydrocarbon radical. According to a preferred embodiment of the process according to the invention, a polyisocyanate A is used which has exclusively aliphatically and / or cycloaliphatically bound isocyanate groups.
  • Aliphatically or cycloaliphatically bound isocyanate groups are understood to mean isocyanate groups which are bound to an aliphatic or cycloaliphatic hydrocarbon radical.
  • a polyisocyanate A is used which consists of or contains one or more oligomeric polyisocyanates, the one or more oligomeric polyisocyanates exclusively having aliphatically and / or cycloaliphatically bound isocyanate groups.
  • polyisocyanate A consists of at least 70, 80, 85, 90, 95, 98 or 99% by weight, based in each case on the weight of polyisocyanate A, of polyisocyanates which are exclusively aliphatically and / or cycloaliphatically bound Have isocyanate groups. Practical tests have shown that particularly good results can be achieved with polyisocyanates A in which the oligomeric polyisocyanates contained therein exclusively have aliphatically and / or cycloaliphatically bound isocyanate groups.
  • a polyisocyanate A which consists of or contains one or more oligomeric polyisocyanates, the one or more oligomeric polyisocyanates based on 1,4-diisocyanatobutane (BDI), 1,5-diisocyanatopentane (PDI), 1,6-diisocyanatohexane (HDI), isophorone diisocyanate (I PDI) or 4,4'-diisocyanatodicyclohexylmethane (H 12 M Dl) or mixtures thereof.
  • BDI 1,4-diisocyanatobutane
  • PDI 1,5-diisocyanatopentane
  • HDI 1,6-diisocyanatohexane
  • I PDI isophorone diisocyanate
  • H 12 M Dl 4,4'-diisocyanatodicyclohexylmethane
  • the inorganic filler B has a Mohs ' hardness of at least 4.0, preferably of at least 5.0 and more preferably at least 5.5.
  • Those fillers which contain silicon oxide units are according to the invention. These are in particular silicates and quartz.
  • the filler B is particularly preferably quartz or feldspar.
  • high filler contents are desirable in order to keep material costs low and to achieve good fire resistance.
  • high filler contents have the disadvantage that they increase the viscosity of the casting resins. This is less of a problem when using polymeric MDI (pMDl) as a structural component of a polyurethane, since pMDl has a viscosity of approximately 90-200 mPas. If pMDI is to be replaced by aliphatic isocyanates, the viscosity of the casting resin reaches a critical limit for processing more quickly because oligomeric aliphatic isocyanates often have viscosities in the range of 1,500 mPas and higher. Therefore, the selection of special fillers is necessary, which lead to low viscosities of the casting resin even with high filler contents in combination with aliphatic isocyanates.
  • the critical parameter here is the oil number.
  • the exemplary embodiments show that after storage of the reaction mixture at 60 ° C. for one hour, a viscosity of 110 Pas was not exceeded if the oil number of the inorganic filler B was at most 25 g / 100.
  • Comparative examples C6 and C7 show that even the use of a filler according to the invention, the oil number of which is slightly above the value according to the invention, already achieved high viscosities or the production of a liquid reaction mixture was no longer possible.
  • V4 shows that fillers that do not contain any silicon oxide units, even with an extremely low oil number (15 g / 100 g in V4 compared to 21 g / 100 g in E10), have a 40% higher viscosity after storage have one hour at 60 ° C.
  • the inorganic filler B therefore has an oil number of at most 25 g / 100 g, determined according to DIN EN ISO 787-5 (October 1995), preferably at most 22 g / 100 g and more preferably at most 20 g
  • the filler can be provided with conventional coatings such as fatty acids, silanes or titanates.
  • the casting resin preferably consists of 30 to 90% by weight, preferably 40 to 80% by weight, more preferably 50 to 80% by weight and particularly preferably 50 to 65% by weight of the inorganic filler B.
  • a casting resin for a highly filled material in particular for a material with a filler content of up to 65% by weight, still has a viscosity that is sufficiently low for processing.
  • the casting resin according to the invention is therefore preferably characterized in that when using up to 65% by weight of an inorganic filler according to the invention with an oil number of up to 25 g / 100 g determined according to DIN EN ISO 787-5 (October 1995) at 60 ° C has a viscosity of at most 200 Pas, preferably at most 150 Pas and this pot life is not exceeded even after at least one hour of storage at this temperature.
  • the viscosity is determined with an MCR301 rheometer from AntonPaar.
  • the polyisocyanate A has a viscosity of at most 20,000 mPas, preferably at most 10,000 mPas and more preferably at most 5,000 mPas at 25 ° C.
  • the viscosity here is preferably at least 500 mPas.
  • the trimerization catalyst C can be mixed from one or different types of catalyst, but contains at least one catalyst which effects the trimerization of isocyanate groups to form isocyanurates or iminooxadiazinediones.
  • Suitable catalysts for the process according to the invention are, for example, simple tertiary amines, e.g. Triethylamine, tributylamine, N, N-dimethylaniline, N-ethylpiperidine or N, N'-dimethylpiperazine.
  • Suitable catalysts are also the tertiary hydroxyalkylamines described in GB 2 221 465, e.g. Triethanolamine, N-methyl-diethanolamine, dimethylethanolamine, N-isopropyldiethanolamine and 1- (2-hydroxyethyl) pyrrolidine, or those known from GB 2 222 161, from mixtures of tertiary bicyclic amines, e.g. DBU, with simple low molecular weight aliphatic alcohols existing catalyst systems.
  • simple tertiary amines e.g. Triethylamine, tributylamine, N, N-dimethylaniline, N-ethy
  • a large number of different metal compounds are also suitable as trimerization catalysts for the process according to the invention.
  • the alkali or alkaline earth metal salts known from EP-A 0 100 129 of aliphatic, cycloaliphatic or aromatic mono- and polycarboxylic acids having 2 to 20 carbon atoms, such as sodium or potassium benzoate,
  • trimerization catalysts suitable for the process according to the invention are, for example, the quaternary ammonium hydroxides known from DE-A 1 667 309, EP-A 0 013 880 and EP-A 0 047 452, e.g.
  • N-methyl-N, N, N-trialkylammonium fluoride with C8-C10-alkyl radicals N, N, N, N-tetra-n-butylammonium fluoride, N, N, N-trimethyl-N-benzylammonium fluoride, tetra methylphosphonium fluoride ,
  • Phosphonium polyfluorides such as, for example, benzyltrimethylammonium hydrogen polyfluoride, the tetraalkylammonium alkyl carbonates known from EP-A 0 668 271, which are obtainable by reacting tertiary amines with dialkyl carbonates, or betaine-structured quaternary ammonio alkyl carbonates, the quaternary ammonium carbonates known from WO 1999/023128, such as, for example, cholinium hydrogen carbonate bicarbonate, the quaternary ammonium salts known from EP 0 102 482 and obtainable from tertiary amines and alkylating esters of acids of phosphorus, such as reaction products of triethylamine, DABCO or N-methylmorpholine with dimethyl methanephosphonate, or the tetra-substituted ones known from WO 2013/167404 Ammonium salts of lactams, for example trioctylammonium cap
  • Carboxylates and phenates with metal or ammonium ions as counterions are particularly preferred.
  • Suitable carboxylates are the anions of all aliphatic or cycloaliphatic carboxylic acids, preferably those with mono- or polycarboxylic acids having 1 to 20 carbon atoms.
  • Suitable metal ions are derived from alkali or alkaline earth metals, manganese, iron, cobalt, nickel, copper, zinc, zirconium, cerium, tin, titanium, hafnium or lead.
  • Preferred alkali metals are lithium, sodium and potassium, particularly preferably sodium and potassium.
  • Preferred alkaline earth metals are magnesium, calcium, strontium and barium.
  • the octoates and naphthenates of manganese, iron, cobalt, nickel, copper, zinc, zirconium, cerium or lead or their mixtures with acetates of lithium, sodium, potassium, calcium, described as catalysts in DE-A 3 240 613 are very particularly preferred or barium.
  • sodium or potassium benzoate the alkali metal phenolates known from GB-PS 1,391,066 and GB-PS 1,386,399, such as. B. sodium or potassium phenolate, and also the alkali and alkaline earth oxides, hydroxides, carbonates, alcoholates and phenolates known from GB 809 809.
  • the trimerization catalyst C preferably contains a polyether. This is particularly preferred when the catalyst contains metal ions. Preferred polyethers are selected from the group consisting of crown ethers, diethylene glycol, polyethylene and polypropylene glycols. In the process according to the invention, it has proven to be particularly practical to use a trimerization catalyst B which contains a polyethylene glycol or a crown ether, particularly preferably 18-crown-6 or 15-crown-5, as polyether.
  • the trimerization catalyst B preferably contains a polyethylene glycol with a number average molecular weight of 100 to 1000 g / mol, preferably 300 g / mol to 500 g / mol and in particular 350 g / mol to 450 g / mol.
  • R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, branched C5-alkyl, unbranched C5-alkyl, branched C6-alkyl, unbranched C6-alkyl, branched C7-alkyl and unbranched C7-alkyl;
  • A is selected from the group consisting of O, S and NR 3 , where R 3 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl and isobutyl; and
  • B is selected independently of A from the group consisting of OH, SH NHR 4 and NH, where R 4 is selected from the group consisting of methyl, ethyl and propyl
  • A is NR 3 , where R 3 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl and isobutyl.
  • R 3 is preferably methyl or ethyl.
  • R 3 is particularly preferably methyl.
  • B is OH and R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, branched C5-alkyl, unbranched C5-alkyl, branched C6 - Alkyl, unbranched C6-alkyl, branched C7-alkyl and unbranched C7-alkyl.
  • R 1 and R 2 are preferably, independently of one another, methyl or ethyl.
  • R 1 and R 2 are particularly preferably methyl.
  • B is SH and R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, branched C5-alkyl, unbranched C5-alkyl, branched C6 - Alkyl, unbranched C6-alkyl, branched C7-alkyl and unbranched C7-alkyl.
  • R 1 and R 2 are preferably, independently of one another, methyl or ethyl.
  • R 1 and R 2 are particularly preferably methyl.
  • B is NHR 4 and R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, branched C5-alkyl, unbranched C5-alkyl, branched C6-alkyl, unbranched C6-alkyl, branched C7-alkyl and unbranched C7-alkyl.
  • R4 is selected from the group consisting of methyl, ethyl and propyl.
  • R 4 is preferably methyl or ethyl.
  • R 4 is particularly preferably methyl.
  • BNH and R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, branched C5-alkyl, unbranched C5-alkyl, branched C6- Alkyl, unbranched C6-alkyl, branched C7-alkyl and unbranched C7-alkyl.
  • R 1 and R 2 are preferably, independently of one another, methyl or ethyl.
  • R 1 and R 2 are particularly preferably methyl.
  • A is oxygen
  • B is OH and R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, branched C5-alkyl, unbranched C5-alkyl, branched C6 - Alkyl, unbranched C6-alkyl, branched C7-alkyl and unbranched C7-alkyl.
  • R 1 and R 2 are preferably, independently of one another, methyl or ethyl.
  • R 1 and R 2 are particularly preferably methyl.
  • B is SH and R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, branched C5-alkyl, unbranched C5-alkyl, branched C6 - Alkyl, unbranched C6-alkyl, branched C7-alkyl and unbranched C7-alkyl.
  • R 1 and R 2 are preferably, independently of one another, methyl or ethyl.
  • R 1 and R 2 are particularly preferably methyl.
  • B is NHR 4 and R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, branched C5-alkyl, unbranched C5-alkyl, branched C6-alkyl, unbranched C6-alkyl, branched C7-alkyl and unbranched C7-alkyl.
  • R 1 and R 2 are preferably, independently of one another, methyl or ethyl.
  • R 1 and R 2 are particularly preferably methyl.
  • R 4 is selected from the group consisting of methyl, ethyl and propyl.
  • R 4 is preferably methyl or ethyl.
  • R 4 is particularly preferably methyl.
  • BNH and R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, branched C5-alkyl, unbranched C5-alkyl, branched C6- Alkyl, unbranched C6-alkyl, branched C7-alkyl and unbranched C7-alkyl.
  • Prefers R 1 and R 2 are independently methyl or ethyl.
  • R 1 and R 2 are particularly preferably methyl.
  • A is sulfur
  • B is OH and R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, branched C5-alkyl, unbranched C5-alkyl, branched C6 - Alkyl, unbranched C6-alkyl, branched C7-alkyl and unbranched C7-alkyl.
  • R 1 and R 2 are preferably, independently of one another, methyl or ethyl.
  • R 1 and R 2 are particularly preferably methyl.
  • B is SH and R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, branched C5-alkyl, unbranched C5-alkyl, branched C6 - Alkyl, unbranched C6-alkyl, branched C7-alkyl and unbranched C7-alkyl.
  • R 1 and R 2 are preferably, independently of one another, methyl or ethyl.
  • R 1 and R 2 are particularly preferably methyl.
  • B is NHR 4 and R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, branched C5-alkyl, unbranched C5-alkyl, branched C6-alkyl, unbranched C6-alkyl, branched C7-alkyl and unbranched C7-alkyl.
  • R 1 and R 2 are preferably, independently of one another, methyl or ethyl.
  • R 1 and R 2 are particularly preferably methyl.
  • R 4 is selected from the group consisting of methyl, ethyl and propyl.
  • R 4 is preferably methyl or ethyl.
  • R 4 is particularly preferably methyl.
  • BNH and R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, branched C5-alkyl, unbranched C5-alkyl, branched C6- Alkyl, unbranched C6-alkyl, branched C7-alkyl and unbranched C7-alkyl.
  • R 1 and R 2 are preferably, independently of one another, methyl or ethyl.
  • R 1 and R 2 are particularly preferably methyl.
  • Adducts of a compound of the formula (I) and a compound having at least one isocyanate group are also suitable.
  • adduct includes urethane, thiourethane and urea adducts of a compound according to formula (I) with a compound having at least one isocyanate group Roger that.
  • a urethane adduct is particularly preferred.
  • the adducts according to the invention arise from the fact that an isocyanate reacts with the functional group B of the compound defined in formula (I). When B is a hydroxyl group, a urethane adduct is formed. When B is a thiol group, a thiourethane adduct is formed. And when BNH or N is HR 4 , a urea adduct is formed.
  • phosphines of the general formula (II) or mixtures of such phosphines are phosphines of the general formula (II) or mixtures of such phosphines
  • RI, R2 and R3 stand for identical or different radicals and each is an alkyl or
  • Cycloalkyl group with up to 10 carbon atoms preferably an alkyl group with 2 to 8 carbon atoms or a cycloalkyl group with 3 to 8 carbon atoms, an aralkyl group with 7 to 10, preferably with 7 carbon atoms or optionally with alkyl radicals with up to 10, preferably 1 to 6, Carbon atoms are substituted aryl groups with 6 to 10, preferably 6 carbon atoms, with the proviso that at most one of the radicals is an aryl group and at least one of the radicals is an alkyl or cycloalkyl group, or in which
  • RI and R2 are aliphatic in nature and, linked together, together with the
  • Phosphorus atom form a heterocyclic ring with 4 to 6 ring members, where R3 stands for an alkyl group with up to 4 carbon atoms,
  • Suitable tertiary organic phosphines are, for example, tertiary phosphines with linear aliphatic substituents, such as trimethylphosphine, triethylphosphine, tri-n-propylphosphine, tripropylphosphine, dibutylethylphosphine, tri-n-butylphosphine, triisobutylphosphine, tri-tert.-butyl-pentylphosphine, tri-tert.-butylphosphine, penthylphosphine, tri-tert.-butylphosphine, pentyl-di-propylphosphine, Pentyldibutylphosphin, Pentyldihexylphosphin, Dipentylmethylphosphin, Dipentylethylphosphin, Dipentylpropylphosphin, Dipentylbutylphos
  • tertiary organic phosphines which are suitable for the process according to the invention are, for example, those known from EP 1 422 223 A1.
  • -Phosphines which have at least one cycloaliphatic radical bonded directly to phosphorus, such as.
  • Cyclopentyldiisopropylphosphin Cyclopentyldibutyl-phosphine with any isomeric butyl radicals
  • Cyclopentyldihexylphosphine with any isomeric hexyl radicals
  • the isomeric Cyclopentyldioctylphosphin with any isomeric octyl radicals Dicyclopentylmethylphosphin, Dicyclopentylethylphosphin, cyclopentyl-n-propylphosphine, Dicyclopentylisopropylphosphin, Dicyclopentylbutylphosphin with any isomeric butyl, Dicyclopentylhexylphosphin with any isomeric hexyl, Dicyclopentyloctylphosphin with any Octyl radical, tricyclopentylphosphine, cyclohexyldimethylphosphine,
  • Cyclohexyl-di-isopropylphosphin Cyclohexyldibutylphosphine with any isomeric butyl radicals
  • Cyclohexyldihexylphosphin with any isomeric hexyl radicals the isomeric octyl radicals
  • tertiary organic phosphines for the process according to the invention are, for example, those known from EP 1 982 979 A1.
  • -Phosphines which have one or two tertiary alkyl radicals bonded directly to phosphorus, such as. B.
  • tert-butyldimethylphosphine tert-butyldiethylphosphine, tert-butyldi-n-propylphosphine, tert-butyldiisopropylphosphine, tert-butyldibutylphosphine with any isomeric butyl radicals for the non-tertiary butyl radicals
  • the catalyst preferably contains at least one compound from the group of the tertiary phosphines mentioned with linear aliphatic substituents.
  • Very particularly preferred phosphine catalysts are tri-n-butylphosphine and / or trioctylphosphine or mixtures thereof.
  • Components with a very high degree of hardness can be produced from the casting compounds according to the invention.
  • the potting compound according to the invention is a one-component system. In contrast to two-component systems, no stoichiometry has to be adhered to exactly between two reactants in order to obtain good results. Slight deviations in the catalyst concentration used in the potting compound according to the invention may lead to slight variations in pot life and curing time, but do not affect the properties of the finished material.
  • the potting compounds still have such low viscosities that processing is possible without major problems.
  • the casting compounds according to the invention have a pot life of at least one hour, so that their processing is also facilitated as a result.
  • the casting compounds according to the invention have a pot life of at least one hour, even at elevated temperatures.
  • the casting compounds according to the invention have a lower fire load compared to the known polyurethane casting compounds.
  • the present invention relates to the use of a potting compound as defined above in this application as an electrical potting compound, i. for the production of an electrical component.
  • the electrical component is preferably selected from the group consisting of transformers, insulators, capacitors, semiconductors, sleeves for protecting cable connections and underground cable branches.
  • the term "production of an electrical component” refers to a method in which at least part of an electrical component is embedded in the potting compound according to the invention According to this application, a finished electrical component thus contains the potting compound according to the invention.
  • the present invention relates to a method for producing an electrical component comprising the steps a) providing a casting resin with a molar ratio of isocyanate groups to isocyanate-reactive groups of at least 3: 1 and a solvent content of at most 10% by weight containing
  • At least one trimerization catalyst C At least one trimerization catalyst C; b) encapsulating an electrical component that is not yet embedded with the casting resin provided in method step a); c) Catalytic trimerization of the casting resin.
  • provision of the casting resin in the context of this application only means that the casting resin mentioned is available at the end of process step a) in such a way that it is suitable for casting and can be catalytically trimerized.
  • An electrical component that has not yet been embedded can be potted by all methods known in the prior art for the use of potting compounds, in particular electrical potting compounds.
  • the catalytic trimerization takes place under reaction conditions under which the selected trimerization catalyst C effects the crosslinking of isocyanate groups to form isocyanurate groups.
  • an upper limit for the temperature of the reaction mixture that is harmless to the component in question is preferably maintained.
  • the "catalytic trimerization” is a process in which the isocyanate groups contained in polyisocyanate A form at least one structure selected from the group consisting of uretdione, isocyanurate, allophanate, biuret, iminooxadiazinedione and oxadiazinetrione structures with one another or with urethane groups that are already present This uses up the isocyanate groups originally present in polyisocyanate A. As a result of the formation of the aforementioned groups, the monomeric and oligomeric polyisocyanates contained in polyisocyanate A are linked to form a polymer network.
  • the isocyanate groups contained in the reaction mixture are crosslinked predominantly by trimerization of at least 50 mol%, preferably at least 60 mol%, particularly preferably at least 70 mol%, in particular at least 80 mol% and very particularly preferably 90 mol% % of the free isocyanate groups present in polyisocyanate A to form isocyanurate structural units.
  • trimerization of at least 50 mol%, preferably at least 60 mol%, particularly preferably at least 70 mol%, in particular at least 80 mol% and very particularly preferably 90 mol% % of the free isocyanate groups present in polyisocyanate A to form isocyanurate structural units.
  • Corresponding proportions of the nitrogen originally contained in polyisocyanate A are thus bound in isocyanurate structures in the finished polyisocyanurate material.
  • the catalytic trimerization is preferably carried out at temperatures between 50 ° C and 200 ° C, more preferably between 80 ° C and 180 ° C and even more preferably between 100 ° C and 150 ° C.
  • the abovementioned temperatures are maintained during the crosslinking of the isocyanate groups until at least 50 mol%, preferably at least 75 mol% and even more preferably at least 90 mol% of the free isocyanate groups present at the beginning of the crosslinking of the isocyanate groups in the semifinished product according to the invention have been consumed.
  • the percentage of isocyanate groups still present can be determined by comparing the content of isocyanate groups in the isocyanate component A present at the beginning of the crosslinking of the isocyanate groups with the content of isocyanate groups in the reaction product, for example by comparing the intensity of the isocyanate band at approx. 2270 cm 1 using ATR IR spectroscopy.
  • the present invention relates to an electrical component which has been produced according to the method defined above.
  • the polymer matrix formed by the casting resin is preferably characterized in that the temperature at which 5% by weight loss of mass occurs is at least 370 ° C, preferably at least 400 ° C and most preferably at least 420 ° C.
  • the following exemplary embodiments only serve to illustrate the invention. They are not intended to limit the scope of protection of the claims in any way.
  • Isocyanate 1 HDI polyisocyanate containing isocyanurate groups, prepared on the basis of Example 11 of EP-A 330 966, with the change that the catalyst solvent used was 2-ethylhexanol instead of 2-ethyl-1,3-hexanediol. The reaction was stopped by adding dibutyl phosphate when the NCO content of the crude mixture was 42% by weight. Unreacted HDI was then separated off by thin-film distillation at a temperature of 130 ° C. and a pressure of 0.2 mbar.
  • OH number 515 mg KOH / g
  • Monomeric HDI ⁇ 0.5% by weight
  • Isocyanate 3 Is a low-viscosity mixture of diphenylmethane-4,4'-diisocyanate (MDI) with isomers and higher functional homologues. NCO content: 31.5% by weight
  • Polyol 1 Is a linear polypropylene ether polyol produced by the propoxylation of 1,2-propanediol.
  • Polyol 2 Glycerine (1,2,3-propanetriol) was obtained from Calbiochem with a purity of 99.0%.
  • Silbond 126 EST is a quartz filler coated with epoxysilane and was obtained from Quarzwerke GmbH. According to the technical data sheet, the filler absorbs 11 g of oil per 100 g of filler (DIN ISO 787-5); the Mohs' hardness is 7.
  • Microdol 1-KN is a dolomite filler and was obtained from Omya. According to the technical data sheet, the filler absorbs 15 g of oil per 100 g of filler (ISO 787/5). According to Wikipedia (accessed 02-2019), the Mohs' hardness of dolomite is 3.5 - 4.
  • Unispar PG W13 is a feldspar filler and was obtained from Sibelco. According to the technical data sheet, the filler absorbs 22 g of oil per 100 g of filler (ISO 787/5); the Mohs' hardness is 6.2.
  • Unispar PG W20 is a feldspar filler and was obtained from Sibelco. According to the technical data sheet, the filler absorbs 19 g of oil per 100 g of filler (ISO 787/5); the Mohs' hardness is 6.2.
  • Filler 5 Omycarb 2T-AV is a calcium carbonate filler and was obtained from Omya. According to the technical data sheet, the filler absorbs 16 g of oil per 100 g of filler (ISO 787/5). According to Wikipedia (accessed in February 2019), the Mohs hardness of calcium carbonate (limestone) is 3. Filler 6 Silbond 800 EST is a quartz filler coated with epoxysilane and was obtained from Quarzwerke GmbHFI. According to the technical data sheet, the filler absorbs 26 g of oil per 100 g of filler (ISO 787/5).
  • Filler 7 Silbond 6000 MST is a methacrylsilane-coated cristobalite filler and was obtained from Quarzwerke GmbHFI. According to the technical data sheet, the filler absorbs 27 g of oil per 100 g of filler (ISO 787/5).
  • Filler 8 Sikron SF 800 is a quartz filler and was obtained from Quarzwerke GmbHFI. According to the technical data sheet, the filler absorbs 28 g of oil per 100 g of filler (ISO 787/5)
  • Filler 9 Chinafill 200 is a kaolin filler and was made by Amberger Kaolinwerke
  • the filler absorbs 46 g of oil per 100 g of filler (ISO 787/5).
  • the Mohs' hardness of kaolin is 2.5.
  • Silitin Z 86 is a mixture of corpuscular silica and lamellar kaolinite and was obtained from Floffmann Mineral GmbHFI. According to the technical data sheet, the filler absorbs 55 g of oil per 100 g of filler (ISO 787/5); the Mohs hardness is 7 for the silica component and 2.5 for the kaolinite component.
  • Silbond 006 MST is a methacrylsilane-coated cristobalite filler and was obtained from Quarzwerke GmbHFI. According to the technical data sheet, the filler absorbs 21 g of oil per 100 g of filler (ISO 787/5); the Mohs' hardness is 6.5.
  • the fillers were dried for 12 hours at 80 ° C. with regular shaking.
  • Catalyst 1 Desmorapid AP 100 was obtained from Covestro AG.
  • Trioctylphosphine was obtained from but GmbHFI in a purity of 97%.
  • Catalyst 3 Is a mixture of potassium acetate, [18] crown-6 and diethylene glycol in a ratio of 1.0: 2.7: 17.6 (obtained from Sigma-Aldrich in PA qualities and used as supplied).
  • the electrical properties of the materials were determined using a Keithley Model 8009 device, which operates on the basis of ASTM D 257 (May 2007). The measurements were carried out at 25 ° C.
  • the glass transition temperature was determined by means of DSC (differential scanning calorimetry) with a Mettler DSC 12E (Mettler Toledo GmbH, Giessen, DE) in accordance with DIN EN 61006 (November 2004). A calibration was carried out by the temperature of the melting onset of indium and lead. 10 mg of substance were weighed into normal capsules. The measurement was carried out by two heatings from -50 ° C to +200 ° C at a heating rate of 20 K / min with subsequent cooling at a cooling rate of 20 K / min. Liquid nitrogen was used for cooling. Nitrogen was used as the purge gas. The stated values are based on the evaluation of the 2nd heating curve.
  • the mass loss was determined using TGA (thermogravimetric analysis) in accordance with DIN EN ISO 11358-1: 2014-10. For this purpose, approx. 5.5 mg of the product were heated from 25 ° C. to 600 ° C. in an open platinum crucible in a TGA-8000 micro-thermal balance (Perkin-Elmer) under a constant stream of nitrogen. The heating rate was 20 k / minute. The temperature at which the mass loss accumulated over the measurement time reached 5% by weight was evaluated.
  • TGA thermogravimetric analysis
  • the two components were mixed and measured in a rheometer at 60 ° C. for one hour.
  • the viscosity value stated was that which was determined exactly after one hour.
  • An MCR301 rheometer from AntonPaar was used.
  • the plate / plate PP25 with the Peltier heater C-PTD200 was used.
  • T 60 ° C, 60 min.
  • test samples were cured in an oven at 180 ° C within 30 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)
  • Polyurethanes Or Polyureas (AREA)
  • Casting Or Compression Moulding Of Plastics Or The Like (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne des masses de scellement, qui durcissent sous la forme de plastiques de polyisocyanurate, la production des dites masses de scellement ainsi que l'utilisation des masses de scellement pour la production de composants électriques.
EP20706286.0A 2019-02-27 2020-02-26 Matériaux de polyisocyanurate comme masses de scellement électriques Pending EP3931185A1 (fr)

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CN117396532A (zh) * 2021-07-23 2024-01-12 Sika技术股份公司 具有高透明度的聚异氰脲酸酯塑料

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JP2022521878A (ja) 2022-04-13
CN113631545A (zh) 2021-11-09

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