Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/02—Silicon compounds
  • C07F7/08—Compounds having one or more C—Si linkages
  • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
  • C07F7/1804—Compounds having Si-O-C linkages
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
  • C07C271/62—Compounds containing any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylcarbamates
  • C07C271/66—Y being a hetero atom
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
• • 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
  • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
  • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
  • C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
  • C08G18/6225—Polymers of esters of acrylic or methacrylic acid
• • 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
  • C08G18/71—Monoisocyanates or monoisothiocyanates
  • C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
• • 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
  • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
  • C08G18/78—Nitrogen
  • C08G18/7806—Nitrogen containing -N-C=0 groups
  • C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
  • C08G18/7837—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing allophanate groups
• • 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
  • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
  • C09D133/04—Homopolymers or copolymers of esters
  • C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
  • C09D133/062—Copolymers with monomers not covered by C09D133/06
  • C09D133/066—Copolymers with monomers not covered by C09D133/06 containing -OH groups
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
  • C09D175/04—Polyurethanes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
  • C09J175/04—Polyurethanes

Definitions

• the invention relates to novel monoallophanates based on alkoxysilane alkyl isocyanates a process for the preparation and use.
• Polyurethanes have been proven for many decades as high-quality building blocks for paint, adhesive, sealant and plastic systems.
• additional alkoxysilane groups can play an important role here, e.g. in terms of network density, chemical resistance and scratch resistance, primarily through the formation of siloxane structures.
• Such systems are also known.
• Molecules which have both alkoxysilane groups and also isocyanate groups offer the possibility of incorporating both said functionalities, siloxanes and polyurethane groups by means of one component. Also such substances have been in use for a long time, e.g.
• Isocyanatoalkyltrialkoxysilane These substances can be converted by reaction with
• Polyalcohols are prepared isocyanate-free moisture-curing crosslinkers.
• SiPUR alkoxysilane-containing polyurethanes
• DE102005041953A1 describes a reaction of a polyol having an average molecular weight of 3000-20000 g / mol with an excess of
• EP2089444A1 claims allophanate-containing polyurethanes which, in addition to an unsaturated functionality, also contain silane-containing components.
• the object of this invention was to provide new compounds bearing alkoxysilane groups
• monoallophanates consisting of an isocyanate-modified alkoxysilane-containing monourethane has the desired properties.
• R, R-R 6 independently of one another denote identical or different hydrocarbon radicals having 1-8 C atoms, which may be branched or cyclic, or may also be cyclic in one another, and m and n independently of one another denote 0-2.
• m and n are 0.
• R and R 5 are independently of each other preferably methyl or ethyl.
• R 2 and R 4 are preferably independently of one another methyl or propyl.
• compounds with m and n are 0, R and R 5 are methyl or ethyl, and R 2 and R 4 are methyl or propyl.
• the subject matter is also a process for the preparation of the monoallophanates according to the invention by a reaction of
• Alkoxysilane-containing isocyanates A) have the formula 2: where R 6 , R 5 and R 4 independently of one another denote identical or different hydrocarbon radicals having 1-8 C atoms, which may be branched or cyclic, or may also merge cyclically into one another, and m is 0-2.
• m 0.
• R 4 is preferably methyl or propyl.
• R 5 is preferably methyl or ethyl.
• compounds with m equal to 0 and R 4 are methyl or propyl, and R 5 is methyl or ethyl.
• Alkoxysilane-containing monourethanes B) have the formula 3:
• R n (OR) 3 - n Si-R 2 -NH- (C O) -OR 3 where R, R, R 2 and R 3 are independently the same or different
• Hydrocarbon radicals having 1-8 C atoms which may be branched or cyclic, or may also merge into one another cyclically, and n is 0-2 means.
• n 0.
• R is preferably methyl or ethyl.
• R 2 is preferably methyl or propyl.
• R 3 R.
• N-trimethoxysilylpropylmethylcarbamate is N-trimethoxysilylpropylmethylcarbamate.
• the preparation of the monoallophanates according to the invention is generally carried out solvent-free or using non-protic solvents, wherein the reaction can be carried out batchwise or continuously.
• the reaction is carried out in suitable units, eg stirred tank, extruder, static mixers, kneading chambers.
• the reaction can be carried out at room temperature, that is to say at temperatures in the range from 20 to 22 ° C., but preference is given to using higher temperatures in the range from 80 to 220 ° C., in particular in the range from 80 to 120 ° C.
• catalysts known in urethane chemistry for example organometallic compounds, such as tin or zinc-containing compounds, salts, such as, for example, Zn (II) chloride and / or bases.
• organometallic compounds such as tin or zinc-containing compounds
• salts such as, for example, Zn (II) chloride and / or bases.
• Sn, Bi, Zn and other metal carboxylates such as z, B are suitable.
• Bismuth neodecanoate tertiary amines such as 1,4-diazabicyclo [2.2.2] octane (DABCO), triethylamine, amidines, and guanidines, as well as quaternary ammonium salts
• Tetralkylammonium salts and / or quaternary phosphonium salts.
• Suitable catalysts are metal acetylacetonates. Examples are
• Zinc acetylacetonate lithium acetylacetonate, iron acetylacetonate and tin acetylacetonate, alone or in mixtures.
• Zinc acetylacetonate is preferably used.
• Also suitable as catalysts are quaternary ammonium acetylacetonates or quaternary phosphonium acetylacetonates.
• the reaction is carried out in the absence of water. The reaction is preferably carried out solvent-free.
• the invention also relates to the use of the monoallophanates according to the invention in coating compositions for metal, plastic, glass, wood, MDF (Middle Density Fiber Boards) or leather substrates or other heat-resistant substrates.
• MDF Middle Density Fiber Boards
• the invention also provides for the use of the monoallophanates according to the invention in adhesive compositions for bonding metal, plastic, glass, wood, MDF or leather substrates or other heat-resistant substrates.
• Isocyanatopropyltrimethoxysilane (Evonik Industries AG) are mixed together and heated to 175 ° C for 2 h. Thereafter, the starting materials are separated at 100 ° C and 0.3 mbar via a short path distillation. This leaves 183 g (41.5%) of a pure, water-clear liquid.
• Viscosity is about 200 mPas and is therefore very low viscosity
• product according to the invention a) are mixed with 25 g of butyl acetate / xylene (1: 1) and admixed with 0.5 g of catalyst (VESTANAT EP-CAT 11, Evonik Industries AG). This mixture is knife-coated with a 120 ⁇ spiral blade on a steel sheet and baked at 140 ° C for 22 min.
• the coating (30 ⁇ layer thickness) has a pendulum hardness of 176 s and a
• the initial gloss level is 86 divisions (Skt.) (20 °). After the brush test is the
• the lacquer surface is damaged with a sieve cloth (nylon mesh No. 1 1, mesh size 25 ⁇ ), which is loaded with a mass (2 kg).
• the screen cloth and the paint surface are wetted abundantly with a detergent solution (0.25% Persil solution in water).
• the test panel is pushed back and forth by means of a motor drive in strokes under the screen fabric. Before and after the test, the gloss level is measured.
• the paint surface is damaged with a fabric (3M 281 Q WetOrying Polishing Paper), which is loaded with a mass (920 g).
• the test panel is pushed back and forth by means of a motor drive in strokes under the tissue.

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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)
• Paints Or Removers (AREA)
• Adhesives Or Adhesive Processes (AREA)
• Polyurethanes Or Polyureas (AREA)

Priority Applications (3)

Applications Claiming Priority (2)

Publications (1)

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Family Applications (1)

Country Status (8)

Cited By (2)

Families Citing this family (1)

Citations (8)

Family Cites Families (5)

• 2015
  • 2015-10-29 ES ES15192085.7T patent/ES2668777T3/es active Active
  • 2015-10-29 NO NO15192085A patent/NO3162807T3/no unknown
  • 2015-10-29 DK DK15192085.7T patent/DK3162807T3/en active
  • 2015-10-29 EP EP15192085.7A patent/EP3162807B1/de not_active Not-in-force
• 2016
  • 2016-10-11 JP JP2018521935A patent/JP2018538250A/ja active Pending
  • 2016-10-11 WO PCT/EP2016/074267 patent/WO2017071941A1/de not_active Ceased
  • 2016-10-11 US US15/771,227 patent/US10351579B2/en not_active Expired - Fee Related
  • 2016-10-11 CN CN201680062781.4A patent/CN108137623A/zh active Pending

Patent Citations (8)

Non-Patent Citations (2)

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