EP3207072A1 - Composition à base de polyurée - Google Patents

Composition à base de polyurée

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Publication number
EP3207072A1
EP3207072A1 EP15778978.5A EP15778978A EP3207072A1 EP 3207072 A1 EP3207072 A1 EP 3207072A1 EP 15778978 A EP15778978 A EP 15778978A EP 3207072 A1 EP3207072 A1 EP 3207072A1
Authority
EP
European Patent Office
Prior art keywords
mol
component
composition
composition according
mdi
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Withdrawn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
EP15778978.5A
Other languages
German (de)
English (en)
Inventor
Steffen Maier
Dominik Huber
Steffen Kelch
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.)
Sika Technology AG
Original Assignee
Sika Technology AG
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 Sika Technology AG filed Critical Sika Technology AG
Publication of EP3207072A1 publication Critical patent/EP3207072A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • 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
    • C08G18/28—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
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
    • C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
    • C08G18/5027—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups directly linked to carbocyclic groups
    • 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
    • B29C73/00—Repairing of articles made from plastics or substances in a plastic state, e.g. of articles shaped or produced by using techniques covered by this subclass or subclass B29D
    • B29C73/02—Repairing of articles made from plastics or substances in a plastic state, e.g. of articles shaped or produced by using techniques covered by this subclass or subclass B29D using liquid or paste-like material
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225—Polyamines
    • C08G18/3237—Polyamines aromatic
    • C08G18/324—Polyamines aromatic containing only one aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • C08G18/482—Mixtures of polyethers containing at least one polyether containing nitrogen
    • 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
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
    • C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
    • 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
    • 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
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine 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
    • C09D175/02—Polyureas
    • 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
    • C09J175/02—Polyureas
    • 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
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • 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
    • B29K2075/02—Polyureas
    • 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
    • C09J2400/00—Presence of inorganic and organic materials
    • C09J2400/20—Presence of organic materials
    • C09J2400/22—Presence of unspecified polymer
    • C09J2400/226—Presence of unspecified polymer in the substrate

Definitions

  • the invention relates to the field of polyurea compositions and their use, in particular as an adhesive, as a coating or filling compound on substrates of unsaturated units
  • the present invention relates to a method for
  • the conveyor belt is that element of such conveyor systems, which comes into direct contact with the material to be transported. It usually consists of a multi-layered element that can be reinforced with different materials.
  • the surface layer is usually made of elastomeric material having unsaturated units. In addition, depending on the particular application, other materials such as polymers or steel may be used.
  • conveyor belt types for wet and dry materials, large and small particle materials or solids of different hardness. Conveyors are subject to a high as a result of their use
  • EPDM ethylene propylene diene copolymer
  • NBR acrylonitrile butadiene rubber
  • SBR styrene butadiene rubber
  • Adhesives on such substrates have insufficient adhesion. Particularly high adhesion requirements are placed on substrates which are stressed dynamically, as in the case of a bypass roll in conveyor belts, or are subjected to shocks, sudden deformations or shocks.
  • materials having unsaturated double bonds such as EPDM, NBR or SBR
  • the composition has the following mechanical properties:
  • Elongation at break 100-800%, especially 200-800%
  • compositions which have a high tensile strength of the bond and nevertheless a high ductility over the largest possible temperature range combined with a little pronounced dependence of the strength on the temperature. Also desirable are compositions which exhibit good adhesion to substrates comprising elastomeric material having unsaturated moieties, especially when such substrates are dynamically stressed.
  • Object of the present invention is therefore, a
  • the present invention relates to a composition
  • a composition comprising at least a first and a second component; in which
  • G is a bivalent radical derived from poly (tetramethylene oxide) diol is derived, and - the second component K2
  • At least one aromatic polyisocyanate B1 having an average molecular weight of 160 g / mol to 1 100 g / mol, preferably 500 g / mol to 800 g / mol, wherein the molar ratio of the isocyanate groups of the second
  • molecular weight refers to the molar mass (in grams per mole) of a molecule.
  • Average molecular weight refers to the number average molecular weight M n of an oligomeric or polymeric mixture of molecules, usually by GPC versus polystyrene Standard is determined.
  • OH group an OH group is referred to, which is bonded to a carbon atom with two hydrogens.
  • open time in this document refers to the time within which the parts to be bonded must be joined after the components have been mixed.
  • the tensile strength and the modulus of elasticity (modulus of elasticity), in particular in the expansion range 0.05 to 0.25%, are meant.
  • room temperature is referred to in this document a temperature of 23 ° C.
  • polyurethane polymer encompasses all polymers which are prepared by the so-called diisocyanate-polyaddition process
  • polyurethane polymer also encompasses polyurethane polymers having isocyanate groups, as is known from the reaction of
  • Polyisocyanates and polyols are available and themselves represent polyisocyanates and are often called prepolymers.
  • glass transition temperature or “Tg” refers to the glass transition temperature determined by means of dynamic-mechanical thermal analysis (DMTA), which is obtained as the maximum in the curve for the loss angle "tan ⁇ ".
  • DMTA dynamic-mechanical thermal analysis
  • isocyanate-reactive groups refers in particular to hydroxyl, mercapto or primary or secondary amino groups, preferably hydroxyl or primary or secondary amino groups.
  • the “gel time” is determined in this document as follows: 30 g of a mixed composition are determined by placing the mixture in a thermally insulated vessel (styrofoam) immediately after mixing at room temperature and stirring well with a spatula every 60 seconds The duration of the gel time is determined until it is no longer possible to move the spatula by hand without great effort.
  • the first component K1 of the composition comprises at least one di (aminobenzoate) ester A1 of the formula (I)
  • G is a bivalent radical derived from poly (tetramethylene oxide ) Diol is derived.
  • G of the di (aminobenzoate) ester A1 is - (CH 2 -CH 2 -CH 2 -CH 2 -O) n-, where n is 9-14.
  • the di (aminobenzoate) ester A1 is a compound of the formula (II)
  • n is a value of 9-14.
  • the di (aminobenzoate) esters A1 can be prepared, for example, by the reaction of a nitro-substituted benzoyl halide or a
  • Poly (tetramethylene oxide) diol be provided followed by the reduction of the nitro groups of the resulting product to the corresponding amino groups.
  • An advantageous di (aminobenzoate) ester can thus be obtained, for example, by the reaction of two moles of p-nitrobenzoyl chloride with one mole of a
  • dihydric alcohol such as poly (tetramethylene oxide) diol with a middle Molecular weight in the range of about 230 to about 1730 g / mol and by
  • the poly (tetramethylene oxide) diol can for example by
  • a suitable poly (tetramethylene oxide) diol is preferably> 90% by weight, especially> 95% by weight, of a polymerization product of tetramethylene oxide or a polycondensation product of 1,4-butanediol.
  • Such poly (tetramethylene oxide) diols can be prepared, for example, by polycondensation, in particular acid-catalyzed polycondensation, of 1, 4-butanediol or by a
  • Suitable di (aminobenzoate) esters A1 are, for example, commercially available under the trade name VERSALINK and are available from Air
  • Di (aminobenzoate) ester A1 to a mixture of di (aminobenzoate) esters A1 - 1 with an average molecular weight of 700 - 1000 g / mol and
  • Di (aminobenzoate) esters A1 -2 having an average molecular weight of 1 100 - 1300 g / mol, wherein the molar ratio of A1 -1 / A1 -2 from 0.01 to 100, in particular from 0.5 to 2, is. This is advantageous in that it increases the gel time.
  • di (aminobenzoate) esters A1 -2 lead to a first Tg at low temperatures, in particular in the range of -40 ° C to -20 ° C. This is advantageous in that the advantageous mechanical properties found are already present at lower temperatures.
  • di (aminobenzoate) esters A1 -2 lead to a temperature range between two consecutive Tgs of -20 ° C to 40 ° C, preferably from -20 ° C to 50 ° C, this is with respect to constant mechanical
  • the first component K1 further comprises an aliphatic, preferably a non-branched, polyetherdiamine A2 having an average molecular weight of from 900 g / mol to 2100 g / mol, preferably from 1200 g / mol to 1500 g / mol, the polyether diamine A2 of 1-15
  • Component K1 has. This is advantageous in that it requires less di (aminobenzoate) ester A1, which typically has a higher price than aliphatic polyether diamine A2, and yet the composition retains similar mechanical properties, particularly with respect to tensile strength and elongation at break. A further advantage is an increase in stability, which may be advantageous in particular when using the composition during repairs, preferably as a filler compound during repairs.
  • the aliphatic polyether diamine A2 is typically one
  • Polyoxyalkylene diamine in particular selected from the group consisting of polyoxypropylene diamines, polyoxybutylene diamines and
  • Polytetramethylene oxide diamine more preferably polyoxypropylene diamines and polytetramethylene oxide diamine, most preferably polytetramethylene oxide diamine.
  • polyoxyalkylene polyamines having two amino groups for example, available under the name Jeffamine® (from
  • the first component K1 preferably has an aliphatic polyetherdiamine A2 mentioned above, if the
  • the first component K1 further comprises an aliphatic polyetherdiamine A2 in an amount such that the aliphatic polyetherdiamine A2 is from 0-5, preferably 0-3, in particular 0-1, most preferably 0-0.1, on most preferred 0
  • the first component K1 further comprises an aliphatic, preferably non-branched, polyether-diol A3, in particular poly (tetramethylene oxide) diol having an average molecular weight of 600 g / mol to 1200 g / mol, preferably 900 g / mol to 1100 g / mol, where the polyether diol A3 is from 1 to 40 mol%, preferably 2 to 10 mol%, more preferably 3-7 mole percent, over
  • Isocyanate-reactive groups of the first component K1 represents. This is advantageous in that the composition thereby obtains a higher elongation at break with a substantially constant tensile strength. Further, this is advantageous for increasing the energy of breakage and the gel time can be increased.
  • the first component K1 further comprises an aliphatic polyether diol A3 previously described, when the
  • Di (aminobenzoate) ester A1 is di (aminobenzoate) ester A1 -2.
  • the first component K1 further comprises an aliphatic polyether diol A3 previously described in an amount such that the polyether diol A3 has from 0 to 5, preferably 0 to 3,
  • the first component K1 comprises an aliphatic
  • Polyetherdiol A3 in an amount mentioned above, when the di (aminobenzoate) ester A1 is di (aminobenzoate) ester A1 -2. This is advantageous in that the composition thereby has higher modulus values and achieves a shorter gel time.
  • the molar ratio of the isocyanate groups of the second component K2 and the isocyanate-reactive groups of the first component K1 is in the range from 1 .3 to 1 .0, preferably 1 .15 to 1 .05. This is
  • composition thereby have a higher tensile strength, higher modulus of elasticity and a shorter gel time.
  • the composition may additionally contain further isocyanate-reactive substances as constituent of the first component K1.
  • the first component K1 has a proportion of less than 3 wt .-%, preferably from 0-2.5 wt .-%, in particular from 0-1.8 wt .-%, particularly preferably 0-1 wt .-%, on most preferably 0 wt .-%, based on the total amount of amine compounds in the first component K1, of a polyamine PA having a molecular weight in the range of 60 to 500 g / mol, in particular 60 to 400 g / mol. Most preferably, the first component K1 does not contain a polyamine PA.
  • the first component K1 has a content of less than 17 mol%, preferably 0-15 mol%, in particular 0-12 mol%, particularly preferably 0-10 mol%, most preferably 0 mol% , based on the total amount of amine compounds in the first
  • Component K1 of a polyamine PA having a molecular weight in the range of 60 to 500 g / mol, in particular 60 to 400 g / mol.
  • the polyamine PA is preferably aromatic
  • Polyamines in particular aromatic polyamines selected from the list consisting of m- and p-phenylenediamine, 4,4'-, 2,4 'and / or 2,2'-diaminodiphenylmethane, 3,3'-dichloro-4,4' diaminodiphenylmethane (MOCA), 2,4- and / or 2, 6-toluenediamine, mixtures of 3,5-dimethylthio-2,4- and - 2,6-toluene diamine (available as Ethacure 300 from Albermarle ®), mixtures of 3,5-diethyl-2,4- and -2,6-toluenediamine (DETDA), 3,3 ', 5,5'-tetraethyl-4,4'-diaminodiphenylmethane (M-DEA), 3,3', 5,5'-tetraethyl-2,2'-dichloro-4,4'-diaminodiphenylmethan
  • composition thereby has a higher open time. Furthermore, this is conducive to achieving a higher elongation at break and a higher modulus of elasticity (0.05-0.25%).
  • the first component contains K1
  • Fillers in particular Russian, chalks and phyllosilicates, pigments and
  • Rheology modifiers in particular amorphous silicic acids, and optionally further constituents.
  • a first component K1 contains 80 to 100% by weight, in particular 90 to 100% by weight, most preferably 98 to 100% by weight, of the total
  • the second component K2 of the composition comprises at least one aromatic polyisocyanate B1 having an average molecular weight of 160 g / mol to 1100 g / mol, preferably 300 g / mol to 800 g / mol, most preferably 500 g / mol to 800 g / mol.
  • Suitable aromatic polyisocyanates are in particular monomeric di- or triisocyanates, as well as oligomers, polymers and derivatives of the monomeric di- or triisocyanates, as well as any desired mixtures thereof.
  • Suitable aromatic monomeric di- or triisocyanates are in particular 2,4- and 2,6-toluene diisocyanate and any desired mixtures of these isomers (TDI), 4,4'-, 2,4'- and 2,2'-diphenylmethane diisocyanate and any mixtures of these Isomers (MDI), mixtures of MDI and MDI homologs (polymeric MDI or PMDI), 1, 3 and 1, 4-phenylene diisocyanate, 2,3,5,6-tetramethyl-1, 4-diisocyanatobenzene, Naphthalene-1,5-diisocyanate (NDI), 3,3'-dimethyl-4,4'-diisocyanatodiphenyl (TODI), dianisidine diisocyanate (DADI), 1,3,5-tris (isocyanatomethyl) benzene, tris (4-isocyanatophenyl) methane and tris (4-isocyanatophenyl)
  • the polyisocyanate B1 has an NCO functionality of
  • Polyisocyanate B1 to MDI and / or TDI, preferably MDI, is.
  • the aromatic polyisocyanate B1 is preferably carbodiimides or uretonimines or urethanes of these polyisocyanates, in particular MDI carbodiimides or MDI uretonimines or MDI urethanes, particularly preferably MDI carbodiimides.
  • the second component contains 60 to 100% by weight, preferably 80 to 100% by weight, more preferably 90 to 100% by weight, most preferably 98 to 100% by weight, of the aromatic polyisocyanate B1.
  • aromatic polyisocyanate B1 95-100 mol%, preferably 98-100 mol%, particularly preferably 99-100 mol%, most preferably 100 mol%, of all isocyanate groups of the second
  • Component K2 has. Suitable oligomers, polymers and derivatives of said monomeric di- and triisocyanates are in particular derived from MDI and TDI.
  • TDI oligomers as Desmodur ® IL (Bayer).
  • modified MDI geeak liquid forms of MDI
  • modified MDI mixtures of MDI with MDI derivatives, such as especially MDI-carbodiimides or MDI uretonimines or MDI urethanes are at room temperature showing, known under trade names such as Desmodur ® CD, Desmodur ® PF, Desmodur ® PC (all from Bayer) ® or Isonate M 143 (Dow), as well as mixtures of MDI and MDI homologues (polymeric MDI or PMDI), available under trade names such as Desmodur ® VL, Desmodur ® VL50, Desmodur ® VL R10, Desmodur ® VL R20, Desmodur ® VH 20 N and Desmodur ® VKS 20F (all from Bayer) ®, Isonate ® M 309, Voranate M 229 and Voranate ® M 580 (all from Dow) or Lupranat ® M 10 R ( The aforementioned oligo
  • Polyisocyanate B1 is a liquid at room temperature form.
  • aromatic polyisocyanate B1 are liquid MDI types at room temperature, in particular mixtures of MDI with MDI derivatives, in particular MDI carbodiimides or MDI uretonimines or MDI urethanes, in particular with an NCO functionality of 2.1-2.4. More preferably, the second component contains 60 to 100% by weight, preferably 80 to 100% by weight, particularly preferably 90 to 100
  • aromatic polyisocyanates is advantageous in that the composition is thereby higher Have tensile strength, higher modulus, higher elongation at break and shorter gel time.
  • the second component K2 further contains at least one polyurethane polymer B2 containing isocyanate groups.
  • the polyurethane polymer B2 preferably has 50-95% by mass, in particular 70-90% by mass, of polyoxyalkylene units, particularly preferably polyoxyethylene and / or polyoxypropylene units, in particular polyoxypropylene units.
  • polyoxyalkylene units particularly preferably polyoxyethylene and / or polyoxypropylene units, in particular polyoxypropylene units.
  • Such a polyurethane polymer has a low viscosity and enables good elongation to be achieved.
  • the polyurethane polymer B2 preferably has a middle one
  • the polyurethane polymer B2 preferably has an average NCO functionality in the range from 1.7 to 3, in particular from 1.8 to 2.5.
  • the polyurethane polymer B2 particularly preferably has an average NCO functionality of from 2.05 to 2.5.
  • the polyurethane polymer B2 preferably has a content of free isocyanate groups of from 1 to 10% by weight, more preferably from 1 to 5% by weight.
  • B2 is obtainable from the reaction of at least one polyisocyanate with at least one polyol.
  • This reaction can be carried out by using the polyol and the polyisocyanate by conventional methods, for example at room temperature. temperatures of 50 ° C to 100 ° C, optionally with the concomitant use of suitable catalysts are reacted, wherein the polyisocyanate is metered so that its isocyanate groups in proportion to the hydroxyl groups of the polyol in stoichiometric excess are present.
  • the polyisocyanate is metered so that an NCO / OH ratio of 1 .3 to 5, in particular one of 1 .5 to 3, is maintained.
  • NICO / OH ratio is understood to mean the ratio of the number of isocyanate groups used to the number of hydroxyl groups used.
  • the polyurethane polymer B2 has an average molecular weight of preferably 500 g / mol or more. In particular, this indicates
  • Polyurethane polymer B2 an average molecular weight of 1 ⁇ 00 to 20 ⁇ 00 g / mol, preferably from 2 ⁇ 00 to 10 ⁇ 00 g / mol, on.
  • Preferred as the polyol for producing a polyurethane polymer B2 are polyoxyalkylene polyols, polyester polyols, polycarbonate polyols and
  • Polyacrylate Particular preference is given to polyoxyalkylene polyols, in particular polyoxybutylene polyols, polyoxypropylene polyols and
  • the polyol for preparing a polyurethane polymer B2 preferably has an average molecular weight of 500-20 ⁇ 00 g / mol, in particular from 1 ⁇ 00 to 8 ⁇ 00 g / mol.
  • the polyol for preparing a polyurethane polymer B2 is preferably a diol or a mixture of at least one diol and at least one triol, in particular a mixture of at least one diol and at least one triol.
  • MDI, TDI, IPDI and HDI are preferable. Particularly preferred is MDI.
  • 4,4'- and 2,4'-MDI and any mixtures of these isomers are advantageous in that the composition thereby has higher elongation at break values, in particular when the di (aminobenzoate) ester A1 of the first component K1 is around
  • Di (aminobenzoate) esters A1 -1 having an average molecular weight of 700 - 1000 g / mol.
  • the polyurethane polymer B2 has 0.1-5 mol%, in particular 0.5-3 mol%, particularly preferably 2-3 mol%, of all the isocyanate groups of the second component K2.
  • Polyurethane polymer B2 0-2 mol%, in particular 0-1 mol%, particularly preferably 0-0.2 mol%, most preferably 0 mol%, of all isocyanate groups of the second component K2. Most preferably, the second component K2 thus contains no polyurethane polymer B2.
  • composition thereby has higher E-modulus and higher tensile strength values.
  • a preferred composition contains a second component K2 which contains 90 to 100% by weight, in particular 95 to 100% by weight, of aromatic polyisocyanate B1 and optionally polyurethane polymer B2.
  • the composition may contain catalysts which accelerate the reaction of hydroxyl groups with isocyanate groups, in particular tin, zinc, zirconium and bismuth organic metal catalysts, for example dibutyltin dilaurate, or tertiary amines, amidines or guanidines, for example 1, 4-diazabicyclo [2.2.2] octane (DABCO) or 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU).
  • DABCO 1, 4-diazabicyclo [2.2.2] octane
  • DBU 1,8-diazabicyclo [5.4.0] undec-7-ene
  • the tertiary amines amidines or guanidines may be blocked with phenol or carboxylic acids, in particular phenolic or other aromatic carboxylic acids. It forms reversibly a salt or a complex, which are decomposed with increasing temperature.
  • Component K1 together with the second component K2 a proportion of less than 1 .5 wt .-%, preferably from 0 to 1 wt .-%, in particular from 0 to 0.2 wt .-%, particularly preferably 0-0.05 wt .-% , most preferably 0% by weight, of a trimerization catalyst TK.
  • trimerization catalysts are used herein
  • tertiary amines and dibutyltin dilaurate which allow the catalysis of the reactions to form isocyanurates.
  • the trimerization catalyst TK is selected from the list consisting of DMEA (dimethylethanolamine), TMBDA
  • composition does not cure too rapidly in the curing reaction, respectively
  • Composition does not overheat during the curing reaction.
  • composition may contain, in addition to the other constituents already mentioned, as known to the person skilled in the art from the polyurea compositions. These can be in just one
  • solvents such as, in particular, Russian, chalks or phyllosilicates, furthermore pigments, rheology modifiers such as, in particular, amorphous silicic acids,
  • Desiccants such as, in particular, zeolites, adhesion promoters such as, in particular, trialkoxysilanes, stabilizers against oxidation, heat, light and UV radiation, flame-retardant substances, and also surface-active agents
  • the composition does not contain foaming agents or substances capable of foaming the reaction product.
  • the first and second components are advantageously formulated such that their mixing ratio in parts by weight ranges from 10: 1 to 1: 1, in particular 7.5: 1 to 2: 1.
  • the mixing ratio between the two components is preferably such that mixed in the
  • Composition the ratio between the number of isocyanate groups and the number of isocyanate-reactive groups before curing in the range of about 1 .2 to 1, preferably 1 .15 to 1 .05, lies.
  • the two components are produced separately from one another and, at least for the second component K2, preferably with the exclusion of moisture. Both components are typically each stored in a separate container.
  • the further constituents of the composition may be present as constituent of the first or the second component, with further constituents reactive toward isocyanate groups preferably being a constituent of the first component.
  • Container for storing the respective component is in particular a barrel, a hobbock, a bag, a bucket, a can, a cartridge or a tube.
  • the components are both shelf-stable, which means that they can be stored for several months to a year and longer before being used, without being in their respective
  • the two components are stored separately prior to mixing the composition and mixed together only at or just prior to use. They are advantageously present in a packaging which consists of two separate chambers.
  • the invention comprises a package consisting of a package with two separate chambers, which each contains the first component or the second component of the composition.
  • the mixing is typically done by static mixers or by means of dynamic mixers.
  • mixing make sure that the two components are mixed as homogeneously as possible. If the two components are mixed incompletely, local deviations from the favorable mixing ratio occur, which may result in deterioration of adhesion and mechanical properties.
  • curing begins by chemical reaction. In this case, the existing hydroxyl groups and optionally present further isocyanate-reactive substances with existing isocyanate groups. As a result of these reactions hardens the
  • Composition to a solid material This process is also referred to as networking.
  • Another object of the invention is therefore also a cured composition obtained from the curing of the composition as described in this document.
  • a further aspect of the present invention therefore relates to a process for bonding substrates, wherein at least one, in particular both, substrates are unsaturated units having elastomeric material comprising
  • composition coated and then with the substrate S1 in Be brought in contact It is also possible to coat both substrates S1 and S2 with the composition. After that they become
  • Open time is used to ensure that both parts are reliably glued together.
  • At least one of the two substrates S1 and S2 is unsaturated units having elastomeric material.
  • both substrates S1 and S2 are elastomeric material having unsaturated moieties.
  • the substrate S2 may be another material or the same material as S1.
  • S1 and S2 are made of the same material.
  • the unsaturated elastomeric material is nonpolar, rubbery material, especially selected from the group consisting of rubber, EPDM, NBR, SBR, SBS (styrene / butadiene / styrene triblock copolymer) and SIS
  • polystyrene / isoprene / styrene triblock copolymer more preferably NBR, SBR and EPMD, most preferably NBR.
  • Another aspect of the present invention relates to a method for repairing voids, particularly cracks or holes, in substrates, wherein the substrates are elastomeric material having unsaturated moieties
  • Defects means one or more defects.
  • the substrates are not pretreated prior to applying the composition.
  • Such pretreatments are preferably not physical and / or chemical cleaning processes, for example grinding, sandblasting, brushing or the like, or treatment with chemical cleaning agents, but physical or chemical methods for increasing the adhesion of the composition to the
  • Substrate especially in its purified form.
  • Such physical or chemical methods are in particular selected from the list consisting of chemical adhesion promoters, chemical oxidants, in particular chlorine-releasing oxidants and hydrogen peroxide-containing oxidants, corona treatment, plasma treatment and
  • Another aspect of the present invention relates to a
  • the composite structure is um
  • Conveyor belts, damping elements and tires most preferably to conveyor belts, in particular conveyor belts.
  • Another aspect of the present invention relates to the use of a composition as described above for repairing defects, in particular cracks or holes, for coating or bonding substrates, in particular of
  • Conveyor belts where the substrates are unsaturated units exhibiting elastomeric material is.
  • the substrate mentioned is the component of a conveyor belt, particularly preferably a conveyor belt in the mining industry.
  • the prepolymer-1 was prepared by adding 1300 g
  • Polyoxypropylene diol (Acclaim® 4200N, Bayer, OH number 28.5 mg KOH / g), 2600 g polyoxypropylene polyoxyethylene triol (Caradol® MD34-02, Shell, OH number 35.0 mg KOH / g), 600 g 4.4 '-Methylendiphenyldiisocyanat (Desmodur® 44 MC L, Bayer) and 500 g of diisodecyl phthalate after
  • Ethacure 100 mixture of mixtures of 3,5-diethyl-2,4- and -2,6-toluylenediamine, amine number 630 mg KOH / g, (PA)
  • compositions 1-64 those given in Table 1 and Table 3, respectively Table 5, respectively Table 9, were given.
  • the tensile strength and elongation at break of the specimens thus produced are measured according to ISO 527 on a Zwick Z020 tensile testing machine at the temperature given in the table and a test speed of 50 mm / min ,
  • the gel time was determined as follows. 30 g of a mixed composition were determined by placing the mixture in a thermally insulated vessel (made of styrofoam) immediately after mixing and thoroughly stirring it manually every 60 seconds with a spatula. As a gel time, the time was set until it was no longer possible to move the spatula by hand without much effort.
  • the Tg values were determined by DMTA measurements on strip-shaped samples (height 2-3 mm, width 2-3 mm, length 8.5 mm), which at 23 ° C and 24 h
  • the measurement conditions were: measurement in the tensile modulus, 10 Hz excitation frequency and heating rate of 5 K / min.
  • the samples were cooled to -60 ° C. and heated to 200 ° C. while determining the complex elastic modulus E * [MPa], a maximum in the curve for the loss angle "tan ⁇ " being read off as the Tg value.
  • the corresponding composition was applied.
  • the composition was poured into molds (1 .3 cm wide / 13 cm long / 0.6 cm deep) which were laterally taped to the sample body and left in the mold for 12 hours. Thereafter, the mold was removed and the samples (caterpillars) for 7 days at 23 ° C, 50% rel. Humidity, cured and then tested.
  • the adhesion of the adhesive was tested by means of a 'bead test'.
  • the bead is cut after curing at the end just above the adhesive surface.
  • the cut end of the caterpillar is with held a circular pliers and pulled from the ground. This is done by carefully rolling up the bead on the pliers tip, as well as placing a cut perpendicular to the track pulling direction down to the bare ground.
  • the caterpillar removal speed should be selected so that a cut must be made approx. Every 3 seconds.
  • the test track must be at least 8 cm. Is assessed after the removal of the caterpillar remaining on the substrate adhesive (cohesion failure).
  • the assessment of the adhesive properties is carried out by estimating the cohesive part of the adhesive surface:
  • compositions 1 to 29 and composition 57 are examples according to the invention. For the rest
  • Compositions are comparative examples.
  • MV 100 K1: means that the number of parts by weight of component K2 has been used per 100 parts by weight of component K.
  • Components K1 and K2, respectively, are composed of the amounts listed (indicated in For example, in the composition 9 is the
  • Component K1 of 96.7 parts by weight of Versalink 650 and 3.3 parts by weight of pTHFdiAmin1300.
  • NICO React
  • novel compositions show over a wide temperature range, a small change in the E-modulus.
  • compositions with Isonate M143 have two discrete Tgs versus Desmodur VKS20, respectively, rather than a mixed Tgs, respectively
  • Consistent mechanical properties, especially over a wider temperature range, is beneficial.
  • compositions showed only adhesion to rubber, but not to TPO or rigid PVC.
  • compositions show the best adhesion to NBR, the second best adhesion to SBR, the third best adhesion to EPDM.
  • Compositions containing Isonate M143 instead of Desmodur VKS20 show better adhesion on all rubber substrates.
  • Compositions containing only Versalink P1000 A1 -2 instead of just Versalink P650 A1 -2 show better adhesion to EPDM.

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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)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention concerne des compositions contenant au moins un premier et un second composant ; le premier composant K1 contient au moins un ester di(aminobenzoate) A1 de Formule (I) avec un poids moléculaire moyen de 500 g/mole à 2 000 g/mole, de préférence 600 g/mole à 1 500 g/mole, de manière particulièrement préférée 650 g/mole à 1 300 g/mole, dans laquelle G est un résidu divalent, qui est dérivé du poly(oxyde de tétraméthylène)diol, et le second composant K2 comporte au moins un polyisocyanate aromatique B1 avec un poids moléculaire moyen de 160 g/mole à 1 100 g/mole, de préférence 500 g/mole à 800g/mole.
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AU2020407855A1 (en) 2019-12-19 2022-05-19 Sika Technology Ag Polyurea coating systems for construction waterproofing
WO2021123109A1 (fr) 2019-12-19 2021-06-24 Chemetall Gmbh Systèmes de revêtement de polyurée utilisés en tant que produits d'étanchéité pour l'extérieur de réservoirs de carburant
CN112341916A (zh) * 2020-10-14 2021-02-09 西南科技大学 一种耐伽玛射线辐照聚脲材料及其制备方法

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CL2017000926A1 (es) 2018-01-12
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AU2015332733A1 (en) 2017-05-04
AU2015332733B2 (en) 2019-11-21
CA2964038A1 (fr) 2016-04-21
US10189938B2 (en) 2019-01-29

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