EP0820480A1 - Prepolymere de polyurethanne a faible viscosite - Google Patents

Prepolymere de polyurethanne a faible viscosite

Info

Publication number
EP0820480A1
EP0820480A1 EP96913501A EP96913501A EP0820480A1 EP 0820480 A1 EP0820480 A1 EP 0820480A1 EP 96913501 A EP96913501 A EP 96913501A EP 96913501 A EP96913501 A EP 96913501A EP 0820480 A1 EP0820480 A1 EP 0820480A1
Authority
EP
European Patent Office
Prior art keywords
polyurethane prepolymer
prepolymer according
viscosity
polyols
group
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Withdrawn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
EP96913501A
Other languages
German (de)
English (en)
Inventor
Marc Rolf Billeter
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of EP0820480A1 publication Critical patent/EP0820480A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • 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
    • C08G18/088—Removal of water or carbon dioxide from the reaction mixture or reaction components
    • C08G18/0885—Removal of water or carbon dioxide from the reaction mixture or reaction components using additives, e.g. absorbing agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
    • C08G18/6461—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having phosphorus
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/01—Hydrocarbons
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
    • C08L2666/26—Natural polymers, natural resins or derivatives thereof according to C08L1/00 - C08L5/00, C08L89/00, C08L93/00, C08L97/00 or C08L99/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/28—Non-macromolecular organic substances

Definitions

  • the invention relates to low-viscosity polyurethane prepolymers.
  • Polyurethane prepolymers are used, for example, as edge and surface treatment agents for materials, in particular those which have a certain intrinsic moisture content or absorb moisture from the environment.
  • Shaped bodies, plates or the like made of wood, wood-based materials or other natural fiber materials may be mentioned as a typical example.
  • Low-solvent or even solvent-free polymer systems are increasingly being used to avoid solvent waste and emissions.
  • Such polymers are generally known and described in the literature.
  • Polyurethane adhesives are used, which are diluted down to the desired viscosity with predominantly less polar to non-polar solvents such as ethyl acetate, toluene or the like.
  • Such one-component polyurethane adhesives contain terminal NCO groups and are generally referred to as isocyanate polyurethanes.
  • isocyanatopolyurethanes also called prepolymers or pre-adducts, can be prepared with a stoichiometric polyisocyanate excess, both from low and from higher molecular weight hydroxyl polyester polyols and from corresponding hydroxyl polyether polyols.
  • the excess polyisocyanate and the functionality of the starting materials must be such that the compression or coating of the material edges or surfaces leads to satisfactory strength, durability and elasticity and, above all, sufficient storage stability of at least 6 months at, for example, 20 ° C is guaranteed with rapid curing of the isocyanatopolyurethane after application.
  • Such solvent-diluted isocyanate polyurethane prepolymers are disadvantageous in terms of the unpleasant odor, the toxicological concern, the solvent emissions, the hardening reaction delayed by the solvents (known and problematic, for example in the edge compaction of particle boards by retaining the solvents in the wood material) and the relatively high energy which is expended must be to to bring such tempered chipboard to drying and then to further processing within an economic time.
  • the curing reaction always takes place in two steps, namely on the one hand by evaporation of the solvents and on the other hand by the action of
  • the curing speed is essentially dependent on the moisture content of the material and the ambient air.
  • a by-product is C0 2 and the end product is cross-linked polyurethane biure.
  • the surfaces thus tempered must be machinable, for example by grinding, polishing or the like.
  • the object of the invention is to formulate a solvent-free, low-viscosity (50 to 120 mPas / 20 ° C.), moisture-curing isocyanatopolyurethane prepolymer which has an optimal wetting and penetration behavior compared to wood and other porous materials with a relatively short curing time and improved storage stability - did. It is also an object of the invention to improve the mechanical properties of the materials treated with it, such as shrinkage and swelling properties when exposed to moisture, transverse tensile, compressive, bending and tensile strength, and an adhesive base for adhesives, coating materials or the like on such treated
  • the surface coated with the prepolymer should be water-diffusion-tight or water-diffusion-capable.
  • organic polyisocyanates b) polyols from the group of the hydroxyl polyester polyols, hydroxyl polyether polyols or their mixed polyols, such as hydroxyl polyester polyether polyol,
  • accelerator catalysts for curing the prepolymer from the group of organic and organometallic amines are f) accelerator catalysts for curing the prepolymer from the group of organic and organometallic amines.
  • Suitable polyisocyanates according to feature a) are in particular aliphatic, cycloaliphatic and aromatic diisocyanates.
  • Those of the general formula X (NCO) 2 are preferably used, X being an aliphatic hydrocarbon radical having 4 to 12 C atoms, a cycloaliphatic hydrocarbon radical having 6 to 15 C atoms or an aromatic hydrocarbon having 6 to 15 C atoms stands.
  • Preferred aromatic, aliphatic or cycloaliphati ⁇ specific diisocyanates are nat 2,4- and 2, 6-toluene diisocyanates or isomeric mixtures thereof, 4, 4 • -Diphenylmethandiisocya- and 2, 4 'diphenylmethane diisocyanate, tetramethylene diisocyanate ethylxyly-, isophorone diisocyanate, 1, 6 -Hexane diisocyanate, 2,2,4- and 2,4,4-trimethylhexamethylene diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, preferably 4,4'-diphenylmethane diisocyanate with up to 80% 2,4'-diphenylmethane diisocyanate.
  • the mixture can have a density of 1.08 to 1.20 g / cm.
  • polyester and / or polyether polyols with a molecular weight of 200 to 10,000 are suitable as polyols according to feature b).
  • polyether ester or polyester ether polyols have also proven to a limited extent, which are obtained by alkoxylation of carboxylic acids or polyesters or can be obtained by condensation of polyethers with highly functional carboxylic acids.
  • these formulations only retain their low-viscosity state for a relatively short time (48 to 144 hours) and therefore require short-term processing.
  • Such polyols with a molecular weight between 700 and 3000 are preferred. They are prepared by reacting epoxides with alcohols. As alcohols e.g.
  • Ethylene glycol diethylene glycol, propylene glycol, glycerin, trimethylpropane, pentaeretrite can be used.
  • suitable epoxides are ethylene oxide, propylene oxide, butyl oxide, styrene oxide, cyclohexane oxide or epichlorohydrin.
  • tetrahydrofuran can also be used.
  • natural substances can also be used as polyol components, such as, for example, rosins and castor oil. Rosin resins with at least one methyl ester group with one to five conjugatable double bonds, which can be used in the addition reaction, are preferred.
  • the acid number of such compounds is ideally between 0.5 and 50 mg KOH / g, preferably between 2 and 20 mg KOH / g
  • esters of phosphoric acid preferably with a refractive index of 1,400 to 1,420 and a boiling temperature of 75 to 85 ° C at 5 mbar.
  • Triethyl phosphate has proven to be particularly effective. These additives do not hinder the polyaddition reaction and are also distinguished by their flame-retardant properties.
  • bifunctional aromatic diisocyanates preferably 2,4- and 2,6-tolylene diisocyanates, but also their isomer mixture are suitable.
  • additions of organic compounds such as 4-methyldioxolanone (2) or n-alkylbenzene can also contribute to the viscosity stabilization for several months.
  • catalysts such as dibutyltin dilaurate, tin-II-octoate or also amines of the general empirical formula c 12 H 2 4 N 2 ° 3 oc *, can be used to accelerate the reaction of the diisocyanant (feature f), such as those of the general empirical formula C 5H 14 N 2 or C g H 10 N 2 .
  • the non-metallic amine hardeners are preferably used, specifically in a mixture of 60 to 90% of the higher and 40 to 10% of the lower amine. Mixtures of the aforementioned organometallic compounds with the organic amines have also shown good results. With the composition described above, a
  • Flame retardants are also advantageously added to the prepolymer.
  • phosphoric acid polyols with a phosphorus content of 5 to 30 (m / m), preferably 10 to 20 (m / m), have proven successful.
  • moisture traps are preferably added.
  • Monocycliscl.es bifunctional oxazolidine has proven to be particularly suitable.
  • oxazolidine also serves as an antifoam and, as such, is of outstanding importance in the context of the invention. It prevents the foaming that can otherwise be observed when applying PUR prepolymers, which forces the application to be scraped off several times, which is done with the corresponding
  • the oxazolidine By suppressing the formation of foam and thus the formation of bubbles, the oxazolidine also has a flame-retardant effect.
  • Salts are added, namely those of carboxylic acids of the empirical formula c ⁇ o ⁇ 2 0 ° 2 k ⁇ - 3 c 22 ⁇ 44 ° 2 ', preferably 9 ⁇ we i ⁇ e
  • low-viscosity polyurethane formulations according to the invention are not only suitable for coating or densifying porous surfaces, but also as adhesives, as reactive thinners for a wide variety of polyurethane compounds or formulations and as primers for paints and varnishes, plastics or other materials.
  • PED polyether polyol with molecular mass from 700 to 3000
  • Example 1 low-viscosity PUR prepolymer with a
  • the MDI is placed in a double-walled (coolable) reactor, whereby the raw material temperature must not be below 18 and not above 22 ° C.
  • the dewatered PED water content max. 500 ppm
  • the polyol mass which should be in the same temperature range as the MDI, is then slowly added to the isocyanate with constant stirring and temperature control.
  • the mixing reactor is advantageously set to approx. 150 mbar evacuated.
  • the accelerator is mixed in. As soon as an exothermic temperature of max. 35 ° C is reached, the marker is added to the mixture and the mixture is cooled to below 28 ° C in any case. Then - to -
  • Stabilizer 1 (TDI) is added immediately with the exclusion of atmospheric moisture, mixed in without streaks and immediately mixed with stabilizer 2 and stirred well for at least 5 to 10 minutes.
  • the viscosity control must show 35 to 38 mPas / 20 ° C and a light yellowish, streak and flake-free, transparent solution testifies to a successful reaction.
  • the PUR prepolymer obtained in this way is left to stand for 24 hours with the exclusion of air humidity and at a storage temperature of approx. 20 ° C.
  • the viscosity measurement afterwards must be about 50 mPa ⁇ / 20 ° C.
  • Example 2 In addition to Example 1, an isocyanate emulsion polymer (SEM) is added to increase the final viscosity.
  • SEM isocyanate emulsion polymer
  • the MDI is placed in a double-walled (coolable) reactor, the raw material temperature not being below 18 ° C. or above 22 ° C.
  • the dewatered PED water content max. 500 ppm
  • the dewatered PED water content max. 500 ppm
  • the NH likewise dewatered to the same water content
  • the mixing reactor is advantageously evacuated to approximately 150 mbar.
  • the accelerator is added, but only if a max. Exothermic temperature of 35 ° C is not reached within 20 minutes. Otherwise, the specified amount of accelerator can be supplied. If the exothermic temperature of approx. 35 ° C is reached by the accelerator supply, the marking agent is mixed immediately and the mixture is cooled to below 28 ° C in any case.
  • the semiprepolymer with a viscosity of 7000 to 12000 mPas / 20 ° C., preferably one of 10000 mPas +/- 500 mPas, is stirred in with slow stirring.
  • masking agent 2 is masked immediately.
  • the TDI can be added with the exclusion of atmospheric moisture.
  • a viscosity constant of around 120 mPas / 20 ° C is reached.
  • Viscosity corrections are made after 24 hours; if the viscosity is too low, the semiprepolymer can be thickened; if the viscosity is too high, the mixture is diluted as described in Example 1. The corrections should not exceed 5% by mass on the
  • Viscosity as a function of time at a test temperature of 20 ° C Test time example 1 example 2
  • Example 1 after 12 to 24 hours, 80% of the final strength, after 72 hours 100% of the final strength are obtained.
  • the product can, however, already after 12 to 24 hours (depending on the respective air and material humidity and on the
  • Processing temperature can be mechanically processed, e.g. by grinding, calibrating, trimming the compressed chipboard or painting over the tempered material surface.
  • LM-PUR only reaches 80% of the final strength after 18 d, 100% of the final strength after 28 d.
  • the storage temperature is> 20 to 35 to 4 0 ° C
  • a material such as chipboard with a density between 400 and 800 kg / m, shows neither a swelling nor a shrinkage effect on the chipboard immediately after the curing of the polyurethane prepolymer according to Example 1. Such a particle board no longer has to be calibrated.
  • an LM-PUR system (as described above) has a shrinkage effect of 2% on average
  • Example 2 The procedure is as in Example 1, but the FS is slowly added with stirring at a low number of revolutions of the polyol composition (consisting of PED and NH) so that no streaks occur. If the FS is added too quickly, an undesirable incompatibility with the other polyols must be expected. In this case the polyol mixture has to be prepared again.
  • the STAB3 is premixed externally in the STAB2 and mixed together after the addition of STABl and after the corresponding stirring time. After a stirring time of 5 to 10 minutes, the FF is fed in with the exclusion of atmospheric moisture and stirring is again carried out for at least 10 minutes at a low number of turns. It is important to ensure that bubbles are not hammered in due to vigorous stirring.
  • Example 2 The same process technology with the parameters of Example 2 leads to a higher final viscosity.
  • the prepolymer obtained can be outstandingly post-processed mechanically, e.g. Grinding, polishing.
  • Examples 2 and 4 lead to a prepolymer with increased final viscosity.

Landscapes

  • 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)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention concerne un prépolymère de polyuréthanne à faible viscosité, constitué par: a) des polyisocyanates organiques; b) des polyols appartenant au groupe comprenant les hydroxypolyesterpolyols, les hydroxylpolyétherpolyols et leurs polyols mixtes; c) des matières naturelles organiques, comprenant au moins un groupe hydroxyle, un groupe carboxyle, un groupe ester ou une liaison double pouvant être conjuguée; d) un ester d'acide phosphorique comme marqueur; e) des stabilisateurs de viscosité; et f) des catalyseurs d'accélération, pour le durcissement du prépolymère, appartenant au groupe des amines organiques et organométalliques.
EP96913501A 1995-04-13 1996-04-14 Prepolymere de polyurethanne a faible viscosite Withdrawn EP0820480A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19513442 1995-04-13
DE19513442 1995-04-13
PCT/EP1996/001571 WO1996032431A1 (fr) 1995-04-13 1996-04-14 Prepolymere de polyurethanne a faible viscosite

Publications (1)

Publication Number Publication Date
EP0820480A1 true EP0820480A1 (fr) 1998-01-28

Family

ID=7759302

Family Applications (1)

Application Number Title Priority Date Filing Date
EP96913501A Withdrawn EP0820480A1 (fr) 1995-04-13 1996-04-14 Prepolymere de polyurethanne a faible viscosite

Country Status (3)

Country Link
EP (1) EP0820480A1 (fr)
CA (1) CA2218104A1 (fr)
WO (1) WO1996032431A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6908621B2 (ja) * 2016-03-28 2021-07-28 ダウ グローバル テクノロジーズ エルエルシー ２成分無溶剤接着剤組成物及びその作製方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1120638A (fr) * 1978-07-12 1982-03-23 Edward L. Hagen Composition de pulverisation a base de polyurethane, contenant un modificateur de viscosite a base de lactone
DE3139967A1 (de) * 1981-10-08 1983-04-28 Bayer Ag, 5090 Leverkusen Neue gemische von tertiaeren stickstoff aufweisenden nco-prepolymeren mit hilfs- und zusatzmitteln, sowie ihre verwendung als klebe- bzw. beschichtungsmittel
DE3339683A1 (de) * 1983-11-02 1985-05-15 BGB-Gesellschaft Reinmar John, Rainer-Leo Meyer & Olga Meyer geb. Klöpfer, 7580 Bühl Beschichtungsmasse fuer flexible substrate, deren verwendung, und verfahren zur erzeugung eines schutzueberzuges
DE4006248A1 (de) * 1990-02-28 1991-08-29 Bayer Ag Gemische aus urethangruppen enthaltenden praepolymeren und diisocyanatotoluolen sowie ihre verwendung
US5126421A (en) * 1990-04-27 1992-06-30 501 Tremco Ltd. Curing system for isocyanate prepolymers

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9632431A1 *

Also Published As

Publication number Publication date
CA2218104A1 (fr) 1996-10-17
WO1996032431A1 (fr) 1996-10-17

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