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WO2009141080A1 - Éléments composites en matière plastique et leur procédé de production - Google Patents

Éléments composites en matière plastique et leur procédé de production Download PDF

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Publication number
WO2009141080A1
WO2009141080A1 PCT/EP2009/003385 EP2009003385W WO2009141080A1 WO 2009141080 A1 WO2009141080 A1 WO 2009141080A1 EP 2009003385 W EP2009003385 W EP 2009003385W WO 2009141080 A1 WO2009141080 A1 WO 2009141080A1
Authority
WO
WIPO (PCT)
Prior art keywords
optionally
isocyanate
composite elements
production
mixture
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.)
Ceased
Application number
PCT/EP2009/003385
Other languages
German (de)
English (en)
Inventor
Catherine LÖVENICH
Eva Emmrich
Manfred Schmidt
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
Bayer MaterialScience 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 Bayer MaterialScience AG filed Critical Bayer MaterialScience AG
Publication of WO2009141080A1 publication Critical patent/WO2009141080A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B27/065—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of foam
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
    • B32B27/20—Layered products comprising a layer of synthetic resin characterised by the use of special additives using fillers, pigments, thixotroping agents
    • B32B27/205—Layered products comprising a layer of synthetic resin characterised by the use of special additives using fillers, pigments, thixotroping agents the fillers creating voids or cavities, e.g. by stretching
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/28—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42
    • B32B27/285—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42 comprising polyethers
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • B32B27/302—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising aromatic vinyl (co)polymers, e.g. styrenic (co)polymers
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    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
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    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4072—Mixtures of compounds of group C08G18/63 with other macromolecular compounds
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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    • C08G18/40—High-molecular-weight compounds
    • C08G18/63—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers
    • C08G18/632—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers onto polyethers
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    • 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
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    • 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
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    • 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
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    • 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
    • C08G18/6685—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 with compounds of group C08G18/3225 or polyamines of C08G18/38
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    • 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
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Definitions

  • the invention relates to composite elements of a plastic layer and a polyurethane layer, a process for their preparation and their use.
  • Polyisocyanate polyaddition products obtainable by reacting isocyanates with isocyanate-reactive compounds, for example, polyols, i. Compounds having at least two hydroxyl groups as well as composite elements of these products with other plastics are well known. Exposing these composite elements to high temperatures and humidities often leads to undesired detachment of the plastics from the polyisocyanate polyaddition products. In particular, when using such composite elements in the automotive industry, for which such a burden can not be excluded, a replacement of the polyisocyanate polyaddition of the other plastics and thus destruction of the composite element is not acceptable.
  • the problem may arise that they do not give stable mixtures at low temperatures. Especially at very low temperatures, for example below 0 ° C., these polyisocyanates may tend to crystallize out. Especially for the reproducible production of high quality products, however, it is important to avoid this problem.
  • DE-A 10 022 280 describes a process for producing composite elements of thermoplastics and polyurethanes with improved adhesion and moisture aging properties.
  • the composite is used, for example, for the manufacture of instrument panels, which panels are usually made of a thermoplastic substrate [such as a thermoplastic).
  • a thermoplastic substrate such as a thermoplastic.
  • PUR polyurethane foam
  • another decorative layer of polyvinyl chloride (PVC), thermoplastic Polyolefins (TPO), thermoplastic polyurethanes (TPU), polyurethane spray skins, etc.
  • Polyester prepolymers for the production of polyurethane foams according to DE-A 10 022 280 have improved properties, in particular a good adhesion between the thermoplastic and such polyurethane foams. In a moist storage of such a composite up to 80 hours at 80 0 C and 80% relative humidity is also an intact composite of thermoplastic and polyurethane foam before.
  • EP-A 1 531 173 Another possibility for the production of composite components is shown in EP-A 1 531 173, in which isocyanate-polycarbonate prepolymers for the production of polyurethane foams with improved adhesion to other thermoplastics in wet aging are described. - -
  • No. 5,300,531 describes the use of fatty acid amides for improving the adhesion to or avoiding blisters with a PVC decorative layer. It is preferred to use polymeric diphenylmethane diisocyanate (MDI) mixtures as the polyisocyanate component.
  • MDI polymeric diphenylmethane diisocyanate
  • the currently available systems provide adhesion values measured according to the
  • Measuring method PV 2034 of Volkswagen AG before aging of> 10 N / 5 cm. After heat storage (500 h storage at 120 0 C circulating air), climate change test (storage 12 cycles ( 144 h) according to the measuring method PV 1200 of Volkswagen AG) or solar simulation (test after 360 h drying cycle and then 240 h wet cycle or another 240 h according to DIN 75 220), values of> 4N / 5cm and ⁇ 15 N / 5 cm are achieved.
  • the object of the invention was to provide composite elements which can be used, for example, in automobile construction because of their excellent mechanical properties and in which the adhesion between the plastic and the polyisocyanate polyaddition products adhering thereto is very good, so that in the roller peel test or in the separation test values> 20N / 5cm can be achieved.
  • the composite elements with starting components should be produced, which give crystallization-stable mixtures even at temperatures ⁇ 0 0 C and thus can be used easily and reproducibly even at low temperatures.
  • the invention relates to composite elements containing as a layer
  • the modified isocyanate prepolymer is obtainable from at least one isocyanate containing carbodiimide (CD) uretonimine (UI) groups and a polyol and / or a chain extender.
  • This prepolymer may preferably be blended with polymeric diphenylmethane diisocyanate (MDI).
  • MDI polymeric diphenylmethane diisocyanate
  • Carbodiimide-modified isocyanates are known per se and e.g. in WO 2007/006622 and in GB 2 268 180.
  • Prepolymers based on carbodiimide-modified isocyanates are also known and e.g. in WO 2002/048231 and WO 2006/069624.
  • the composite elements according to the invention may comprise as plastic (A) Polyurethanansprühfeldute or conventional thermoplastics, such as polyphenylene oxide (PPO), polyvinyl chloride (PVC), acrylonitrile-butadiene-styrene acrylic ester (ASA), polycarbonate (PC), thermoplastic polyurethane (TPU), polyethylene (PE), polypropylene (PP), styrene-maleic anhydride (SMA), polycarbonate / styrene-acrylonitrile / acrylonitrile-butadiene blend (PC / ABS) and blends thereof.
  • PPO polyphenylene oxide
  • PVC polyvinyl chloride
  • ASA acrylonitrile-butadiene-styrene acrylic ester
  • PC thermoplastic polyurethane
  • TPU thermoplastic polyurethane
  • PE polyethylene
  • PP polypropylene
  • SMA styrene-maleic anhydride
  • PC / ABS polycarbon
  • the plastics (A) can be used for example in the form of films for the production of the composite elements.
  • the films Preferably, the films have a thickness of 0.2 to 2 mm.
  • the composite elements can preferably be used as a stiffening part for instrument panels or door side parts.
  • Preferred as product (B) are polyurethanes which may be present in a compact or preferably cellular form, for example as flexible foam, semi-rigid foam or rigid foam, particularly preferably as semi-rigid foam.
  • the products (B) are preferably obtainable from the following starting compounds: - - a) a mixture having an isocyanate content of 20 to 30 wt .-% of carbodiimide / uretonimine having Isocyanatprepolymeren and optionally polymeric MDI
  • the prepolymers under (a) are preferably from
  • aromatic isocyanates such as.
  • isocyanate-reactive compounds for example polyetherpolyalcohols, polyesterpolyalcohols and / or polycarboxylate diols having molecular weights of between 500 and 12,000 and functionalities of 2 to 6 and / or
  • Chain extenders and / or crosslinking agents having molecular weights of 60 to 499 and functionalities of 2 to 6, preferably 2, obtained.
  • the mixture a) may optionally contain polymeric MDI.
  • the polymeric MDI used are preferably crude polymer-MDI mixtures, as obtained in the phosgenation of crude diphenylmethanediamine. Crude polymer-MDI mixtures, as obtained in the phosgenation of crude Diphenylrnethanediamine, preferably still have a proportion of monomeric MDI from 20 to 60 wt .-% and have a viscosity of 1200 mPas / 20 ° C to 100 mPas / 20 ° C (the monomeric MDI is present as a mixture of 4,4'-, 2,4'- and 2,2'-di-phenylmethane diisocyanate).
  • component (b) it is possible to use generally known isocyanate-reactive compounds, for example polyetherpolyalcohols, polyesterpolyalcohols and / or polycarbonatediols, preferably polyetherpolyols and / or polyesterpolyalcohols, preferably having a molecular weight of from 500 to 10,000, in particular from 1,000 to 6,000, and having one Functionality of 2 to 6.
  • filled polyether polyols such as styrene-acrylonitrile (SAN) - - or polyurea (PHD) - or polyisocyanate polyaddition (PIPA) -Polyethe ⁇ lyole be used.
  • SAN styrene-acrylonitrile
  • PPD polyurea
  • PIPA polyisocyanate polyaddition
  • the compounds (b) can also be used in admixture with chain extenders and / or crosslinking agents.
  • the chain extenders are preferably bifunctional alcohols having molecular weights of from 60 to 499, for example ethylene glycol, propylene glycol, 1,4-butanediol, 1,5-pentanediol.
  • the crosslinking agents are preferably compounds having molecular weights of from 60 to 499 and functionalities of from 3 to 6, preferably amines and more preferably alcohols, for example glycerol, trimethylolpropane and pentaerythritol.
  • the chain extenders and / or crosslinkers may also be used alone as component (b).
  • catalysts (c) conventional compounds can be used, for example, the
  • component (a) Rapidly accelerate the reaction of component (a) with component (b).
  • component (b) for example, tertiary amines generally known for this purpose and / or organic metal compounds, in particular tin compounds, are suitable.
  • the catalysts used are preferably those which have the lowest possible emission (for example VOC and FOG values in VDA278 test and fogging values according to DIN 75201), ie. to the lowest possible release of volatile
  • Suitable blowing agents (d) for the production of foamed products (B), for example polyurea soft, semi-hard or rigid foams, which may optionally have urea and / or isocyanurate structures, are generally known chemically or physically active compounds .
  • a chemically acting blowing agent it is also possible with preference to use water which forms carbon dioxide by reaction with the isocyanate groups.
  • physical blowing agents, i. inert compounds which evaporate under the conditions of polyurethane formation are (cyclo) aliphatic hydrocarbons, preferably those having 4 to 8, more preferably 4 to 6 and in particular 5 carbon atoms, partially halogenated hydrocarbons or ethers, ketones or acetates.
  • the amount of blowing agent used depends on the desired density of the foams.
  • the different blowing agents can be used individually or in any mixtures with each other.
  • the reaction may optionally be carried out in the presence of (e) auxiliaries and / or additives, such as adhesion promoters, fillers, fibers (eg in the form of fabrics and / or mats), cell regulators, surface-active compounds, stabilizers against oxidation, thermal or microbial degradation or aging and chain breakers.
  • auxiliaries and / or additives such as adhesion promoters, fillers, fibers (eg in the form of fabrics and / or mats), cell regulators, surface-active compounds, stabilizers against oxidation, thermal or microbial degradation or aging and chain breakers.
  • the mixture (a) and the isocyanate-reactive compounds (b) are preferably reacted in amounts such that the equivalence ratio of NCO groups from (a) to the sum of the reactive hydrogen atoms from (b ) and optionally from (d) 0.3: 1 to 1.8: 1, more preferably 0.4: 1 to 1.0: 1 and in particular 0.4: 1 to 0.6: 1, is.
  • the product (B) at least partially contains isocyanurate groups is preferably a ratio of NCO groups to the sum of the reactive
  • the conversion to the product (B) can be carried out, for example, by hand casting, by high-pressure or low-pressure machines or by the RIM process (reaction injection molding) usually in open or preferably closed molds. Suitable processing machines are commercially available.
  • the starting components a) to e) are usually mixed at a temperature of 0 to 100 0 C, preferably from 20 to 80 0 C, and introduced, for example, in a mold.
  • the mixing can be carried out mechanically by means of a stirrer or carried out in a conventional high-pressure mixing head.
  • reaction of the reaction mixture can be carried out, for example, in customary, preferably heatable and sealable forms.
  • the molds - - To be able to be tempered in order to set the preferred temperatures, and be closed.
  • the starting components are preferably used at a temperature of 20 to 50 0 C.
  • the reaction to the products is usually carried out at a mold temperature of 20 to 120 0 C, preferably 25 to 100 0 C, particularly preferably 30 to 80 0 C, for a period of usually 0.5 to 30 minutes, preferably 1 to 5 min.
  • the reaction in the mold takes place in accordance with Erftndungs in direct contact with (A). This can be achieved, for example, by placing a plastic (A) as a decorative skin and optionally additionally a support before reacting the reaction mixture in the mold and then adding the reaction mixture to the mold.
  • the production of composite elements can be either open or closed
  • any fibers used as component (e) may be used both in the reaction mixture and in the form of mats or fabrics. If mats or fabrics are used as component (e), they may, for example, be applied to the film (A) present in the mold before the reaction mixture is introduced, and then the reaction mixture, which in this case preferably contains no additional fibers, can be applied the mold will be filled.
  • the composite elements of the invention have a significantly improved adhesion between (A) and (B) by the use of the mixture (a), which also has a high low-temperature stability.
  • the composite elements according to the invention have values above aging of more than 20 N / 5 cm.
  • Another object of the invention are isocyanate mixtures having an isocyanate content of 20 to 30 wt .-% of carbodiimide / uretonimine-modified Isocyanatprepolymeren and optionally polymeric MDI.
  • the composite elements according to the invention are preferably used as components in vehicle, aircraft or real estate construction, for example as dashboards, door panels, hat racks, consoles, armrests or door mirrors.
  • Polyol I Polyether polyol having an average molecular weight of 6000 g / mol prepared by addition of propylene oxide / ethylene oxide (83/17) to glycerol as a starter and having a polyurea filler content of 20 wt .-%.
  • Polyol 2 Polyether polyol having an average molecular weight of 4800 g / mol prepared by addition of propylene oxide / ethylene oxide (83/17) to glycerol as a starter.
  • Polyol 3 Polyether polyol having an average molecular weight of 6235 g / mol prepared by addition of propylene oxide / ethylene oxide (78/22) to glycerol as a starter.
  • Polyol 4 Polyether polyol having an average molecular weight of 6000 g / mol and at least 80% of primary OH groups, prepared by addition of propylene / ethylene oxide (82/18) to glycerol as starter and having a grafted filler content of 20% by weight. of styrene / acrylonitrile (40% / 60%).
  • Chain extender 1 Polyether polyol having a molecular weight of 356 g / mol and a functionality of 4 prepared by propylenoxylation with ethylenediamine.
  • Chain extender 2 diethanolamine
  • Catalyst 1 Dabco ® NE 1070 from Air Products (dimethylaminopropyl about 60% strength (in diethylene glycol gel catalyst))
  • Catalyst 3 Desmorapid 59EF05 ® from Bayer MaterialScience AG (poly (oxyalkylene) - amine catalyst
  • Additive 1 black paste N from Fa. ISL Chemie (black paste based on carbon black)
  • Additive 2 Ethacure 100 ® LC Fa of Albemarle (diethyltoluylenediamine-80).
  • polyurethane molded foams were prepared.
  • the polyols, water, activators and other additives were mixed into a polyol formulation.
  • the polyol formulation with the isocyanate component was homogenized in a high-pressure mixing head and poured into a mold with a temperature of 40 0 C.
  • the mold already contained a PVC decorative film (type DSY 260/02 from Resinoplast) and a support made of polypropylene.
  • additional plates with a size of 200 * 200 * 40 mm were produced.
  • the composite properties to the decorative layer were also plates with a size of

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne des éléments composites constitués d'une couche de matière plastique thermoplastique et d'une couche de polyuréthane, ainsi qu'un procédé de production et qu'un procédé d'utilisation de tels éléments.
PCT/EP2009/003385 2008-05-23 2009-05-13 Éléments composites en matière plastique et leur procédé de production Ceased WO2009141080A1 (fr)

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EP2399946A1 (fr) * 2010-06-24 2011-12-28 Bayer MaterialScience AG Pièces revêtues et leur utilisation

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DE10056309A1 (de) 2000-11-14 2002-05-16 Bayer Ag Aktivatoren für die Herstellung von Polyurethanschaumstoffen
DE10062410A1 (de) 2000-12-14 2002-06-20 Bayer Ag Verfahren zur Herstellung von Polyurethanelastomeren mit hohem Wärmestandverhalten
DE10352951A1 (de) 2003-11-13 2005-06-16 Bayer Materialscience Ag Kunststoffverbundelemente und ein Verfahren zu ihrer Herstellung
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US5338820A (en) * 1993-04-15 1994-08-16 Basf Corporation Water-blown polyurethane integral skin foam
US5510053A (en) * 1994-12-29 1996-04-23 Basf Corporation Water-blown polyurethane sealing devices and compositions for producing same
DE10160375A1 (de) * 2001-12-10 2003-06-18 Basf Ag Polyurethane und deren Verwendung als Karosserieaußenteile

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WO2011003529A1 (fr) * 2009-07-07 2011-01-13 Bayer Materialscience Ag Polyuréthanne et son utilisation
EP2399946A1 (fr) * 2010-06-24 2011-12-28 Bayer MaterialScience AG Pièces revêtues et leur utilisation
WO2011161047A1 (fr) * 2010-06-24 2011-12-29 Bayer Materialscience Ag Éléments dotés d'un revêtement et leur utilisation
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