EP1824941A1 - Adhesifs de polyurethanne a deux constituants, additifs pour des adhesifs de polyurethanne a deux constituants et utilisation desdits additifs - Google Patents

Adhesifs de polyurethanne a deux constituants, additifs pour des adhesifs de polyurethanne a deux constituants et utilisation desdits additifs

Info

Publication number
EP1824941A1
EP1824941A1 EP05812167A EP05812167A EP1824941A1 EP 1824941 A1 EP1824941 A1 EP 1824941A1 EP 05812167 A EP05812167 A EP 05812167A EP 05812167 A EP05812167 A EP 05812167A EP 1824941 A1 EP1824941 A1 EP 1824941A1
Authority
EP
European Patent Office
Prior art keywords
adhesive
additive
diisocyanate
adhesives
terminal hydroxyl
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Withdrawn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
EP05812167A
Other languages
German (de)
English (en)
Inventor
Petra Padurschel
Rolf Tenhaef
Olaf Lammerschop
Thomas Huver
Hubert Schenkel
Andreas Ferencz
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP1824941A1 publication Critical patent/EP1824941A1/fr
Withdrawn legal-status Critical Current

Links

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
    • 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
    • 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
    • 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
    • C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
    • C08L2666/18—Polyesters or polycarbonates according to C08L67/00 - C08L69/00; Derivatives thereof
    • 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
    • C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
    • C08L2666/20—Macromolecular compounds having nitrogen in the main chain according to C08L75/00 - C08L79/00; Derivatives thereof

Definitions

  • the invention relates to a two-component polyurethane adhesive based on a polyol component and a polyisocyanate component.
  • the invention also relates to an additive for such an adhesive and the use of the additive.
  • Polyurethane adhesives are described, for example, in the following patent applications or patents: EP 0 504 436 B1, EP 0 411 432 B1, EP 0 442 084 B1, DE 40 33 221 A1, EP 0 597 636 B1 and EP 0 740 675 B1.
  • Polyurethane adhesives have long been known and widely used. Particularly important, especially in technical applications, are the two-component adhesives, which are stirred by the user before use to a reaction mixture, which then hardens after application to the substrates to be bonded.
  • Such two-component adhesives consist of a polyol component and an isocyanate component of functionality 2 or higher. These adhesives are preferred over other adhesives for many applications because the adhesive bonds made with them have outstanding tack, flexibility, and resistance to shock and fatigue.
  • epoxy adhesives have hitherto been used extensively, in particular as hot-curing one-component adhesives, which are frequently also formulated as reactive hot-melt adhesives.
  • Reactive hot melt adhesives are solid at high temperatures. They soften at temperatures up to about 80 - 90 0 C and behave like a thermoplastic material. Only at higher temperatures from about 100 0 C present in these hot melt adhesives latent curing agent are thermally activated, so that irreversible curing takes place to a thermoset.
  • the adhesive is first applied warm to at least one substrate surface, the components to be joined are then joined. Upon cooling, the adhesive solidifies and, by this physical solidification, provides sufficient handling strength, ie a preliminary bond. The so interconnected components are further treated in various washing, phosphating and dip coating. Only then is the adhesive cured in an oven at higher temperatures.
  • the present invention therefore has for its object to provide two-component polyurethane adhesives, which in the temperature range from - have a high strength 40 0 C to +80 0 C, without becoming brittle in the range of low temperatures.
  • the impact peel strength according to ISO 11343 apply.
  • the present invention is therefore a two-component polyurethane adhesive based on a polyol component and a polyisocyanate component, which is characterized in that an adhesive bond produced by the adhesive of two coated with cathodic electrodeposition paint steel sheets at a temperature of -40 0 C. has a peel strength to ISO 11343 of at least 11 N / mm. Two-component polyurethane adhesives with such impact peel strength are not yet known.
  • Suitable polyol components are both low molecular weight polyols and relatively high molecular weight polyols, for example hydroxyl-bearing polyesters, which have at least 2 hydroxyl groups per molecule.
  • a polyisocyanate component the usual Isocyanathmaschineter are suitable for polyurethane adhesives having at least 2 isocyanate groups per molecule.
  • suitable polyol components are liquid polyhydroxy compounds having two or three hydroxyl groups per molecule, such as. B. di- and / or trifunctional polypropylene glycols in the molecular weight range from 200 to 6000, preferably in the range of 400 to 3000.
  • polyether polyols are the polytetramethylene glycols, z.
  • Example be prepared by the acidic polymerization of tetrahydrofuran, wherein the molecular weight range of the polytetramethylene glycols preferably between 200 and 6000, more preferably in the range of 400 to 4000.
  • the liquid polyesters are suitable, which by condensation of di- or tricarboxylic acids, such as. B. adipic acid, sebacic acid, glutaric acid with low molecular weight diols or triols such.
  • ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, dipropylene glycol, 1, 4-butanediol, 1, 6-hexanediol, glycerol or trimethylolpropane can be produced.
  • the polyols which can be used are the polyesters based on lactones, such as caprolactone or valerolactone. However, it is also possible to use polyester polyols of oleochemical origin.
  • polyester polyols can be prepared, for example, by complete ring opening of epoxidized triglycerides of a fat mixture containing at least partially olefinically unsaturated fatty acid with one or more alcohols having 1 to 12 carbon atoms and subsequent partial transesterification of the triglyceride derivatives to alkyl ester polyols having 1 to 12 carbon atoms in the alkyl radical.
  • suitable polyols are polycarbonate polyols and dimer diols, and in particular castor oil and its derivatives.
  • the hydroxy-functional polybutadienes, as z. B. under the trade name "poly-BD" are available, can be used for the inventive compositions as polyols.
  • Suitable polyisocyanates are, for example, aromatic isocyanates, eg.
  • diphenylmethane diisocyanate either in the form of the pure isomers, as a mixture of isomers of 2,4 '- / 4,4'-isomers or the liquefied with carbodiimide diphenylmethane diisocyanate (MDI), the z. B. under the trade name Isonate 143 L is known.
  • MDI carbodiimide diphenylmethane diisocyanate
  • the so-called "crude MDI” that is to say the isomer / oligomer mixture of the MDI, can be used as described, for example, in US Pat. B. under the trade name PAPI or Desmodur VK are commercially available.
  • d. H Reaction products of MDI or toluene diisocyanate (TDI) with low molecular weight diols such.
  • MDI toluene diisocyanate
  • ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol or triethylene glycol can be used.
  • isocyanates are the most preferred isocyanates, aliphatic or cycloaliphatic di- or polyisocyanates can be used such.
  • H12MDI Hydrogenated MDI
  • TXDI tetramethylxylylene diisocyanate
  • IPDI 1-isocyanatomethyl-3-isocyanato-1,5,5-trimethyl-cyclohexane
  • HDI hexane-1,6-diisocyanate
  • biuretization product of HDI Isocyanuration product of HDI or dimer fatty acid diisocyanate.
  • Suitable polyols are compounds having at least two hydroxyl groups. Suitable polyols are preferably the liquid Polyhydroxy compounds having two or three hydroxyl groups per molecule, such as. B. di- and / or trifunctional polypropylene glycols in the molecular weight range from 200 to 6000, preferably in the range of 400 to 3000. It can also be used random and / or block copolymers of ethylene oxide and propylene oxide. Another group of preferably used polyether polyols are the polytetramethylene glycols, z.
  • Example be prepared by the acidic polymerization of tetrahydrofuran, wherein the molecular weight range of the polytetramethylene glycols preferably between 200 and 6000, more preferably in the range of 400 to 4000.
  • the liquid polyesters are suitable, which by condensation of di- or tricarboxylic acids, such as. B. adipic acid, sebacic acid, glutaric acid with low molecular weight diols or triols such.
  • ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, dipropylene glycol, 1, 4-butanediol, 1, 6-hexanediol, glycerol or trimethylolpropane can be produced.
  • Another group of usable polyols are the lactones-based polyesters, such as caprolactone or valerolactone.
  • polyester polyols of oleochemical origin is also possible to use.
  • polyester polyols can be prepared, for example, by complete ring opening of epoxidized triglycerides of a fat mixture containing at least partially olefinically unsaturated fatty acid with one or more alcohols having 1 to 12 carbon atoms and subsequent partial transesterification of the triglyceride derivatives to alkyl ester polyols having 1 to 12 carbon atoms in the alkyl radical.
  • suitable polyols are polycarbonate polyols and dimer diols, and in particular castor oil and its derivatives.
  • the hydroxy-functional polybutadienes, as z. B. under the trade name "poly-BD" are available, can be used for the inventive compositions as polyols.
  • test specimens consist of steel coated with cathodic electrodeposition paint (KTL) and have a size of 20 ⁇ 90 mm 2 .
  • the size of the adhesive surface was 20 ⁇ 30 mm 2 , and the thickness of the adhesive layer was 0.2 mm.
  • the wedge had a length of 14 mm and a height of 4 mm.
  • the angle between the faces of the wedge was 8 ° 46 '18 ". It was moved at a speed of 2 ms " 1 .
  • an adhesive bond produced with the adhesive at a temperature of -40 ° C a impact peel strength according to ISO 11343 of at least 15 N / mm.
  • a two-component polyurethane adhesive which leads to the said high impact peel strength, can be achieved in that, in addition to at least one polyol component and at least one polyisocyanate component as an additive, at least one hydroxyl- or amine-terminated reaction product of a hydroxyl-terminated compound Amino groups of the general formula (I)
  • R H or a straight-chain or branched alkyl radical having 1 to 20
  • the additives are reactive prepolymers which when cured react with the resin component of the adhesive so that the additives are firmly incorporated into the polymer structure.
  • soft phases are introduced into the adhesive bond, which cause the adhesive bond is retained even in a strong shock or impact.
  • the soft phases absorb the energy of a shock, and the bond is impact resistant.
  • the compound of the formula (I) used for the preparation of the additive is advantageously polytetrahydrofuran or polytetramethylene oxide-di-p-aminobenzene.
  • the dicarboxylic acid to be used is advantageously a dimerized fatty acid, and a preferred diisocyanate is the diphenyl diisocyanate.
  • the adhesive according to the invention advantageously contains the additive in an amount of 5 to 30% by weight, based on the total weight of the adhesive, preferably 10 to 20% by weight, very particularly preferably 13 to 17% by weight.
  • the invention also relates to the additive for two-component polyurethane adhesives, which consists of a hydroxyl- or an amine-terminated reaction product of a compound having terminal hydroxyl or amino groups of the general formula (I)
  • R H or a straight-chain or branched alkyl radical having 1 to 20
  • Is carbon atoms m is 3 or 4 and n is 5 to 50, with a di- or tricarboxylic acid or a di- or triisocyanate.
  • the additive has a number average molecular weight of from 1000 to 20 000 g / mol, preferably from 1000 to 12000 g / mol, very particularly preferably from 2000 to 8000 g / mol.
  • the invention further relates to the use of a hydroxyl- or amine-terminated reaction product of a compound having terminal hydroxyl or amino groups of the general formula (I)
  • Component A (resin):
  • Baycoll VP 8576 (Bayer AG, resin component polyol base)
  • Component B (hardener):
  • the additives were incorporated in the basic formulation and bonded to cathodically dip-coated test specimens.
  • the adhesive bonds were subjected to various destructive test methods, such as pull shear, peel and impact peel tests.
  • Polytetramethylene oxide di-p-aminobenzene and diphenyl-4,4'-diisocyanate are converted by a polyaddition to a prepolymer.
  • reaction mixture is reacted for 1 hour at 100 0 C and is then cooled to room temperature.
  • the no longer meltable substance is cooled with liquid nitrogen and ground.
  • the product is in the form of a light yellow, fine and acetone-soluble powder and has an amine value of 41.2 (additive 1).
  • Polytetramethylene oxide di-p-aminobenzene and diphenyl-4,4'-diisocyanate are converted by a polyaddition to a prepolymer.
  • reaction mixture is reacted for 1 hour at 100 0 C and then on
  • the no longer meltable substance is cooled with liquid nitrogen and ground.
  • the product is a light yellow, fine and acetone-soluble powder and has an amine value of 26.8 (additive 2).
  • This mixture is stirred intimately and quickly and glued to KTL test specimens.
  • Dimer fatty acid (SZ 190) and polytetrahydrofuran 650 are replaced by a
  • thermometer and condenser In a round bottom flask with gas transfer, thermometer and condenser with
  • Water separators are 0.05 mol (29.5 g) of dimer fatty acid, 0.1 mol (63 g)
  • the product is deep yellow and honey-like at room temperature and has a
  • Cooled 0 C and bottled the product It is at room temperature as a colorless, non-flowable resin and has an OH number of 48 (additive 4).
  • Polytetrahydrofuran 2000 and diphenyl-4,4'-diisocyanate are converted by a polyaddition to a prepolymer.
  • reaction mixture is stirred for a further 3 hours at 80.degree. Finally, it is cooled to 40 ° C. and the product is bottled. It is present at room temperature as a white, slightly waxy or rubbery resin and has an OH number of 44 (additive 5).
  • This mixture is stirred intimately and quickly and glued to KTL test specimens.
  • Polytetrahydrofuran 650 and diphenyl-4,4'-diisocyanate are converted by a polyaddition to a prepolymer.
  • Polytetrahydrofuran 650 and diphenyl-4,4'-diisocyanate are converted by a polyaddition to a prepolymer.
  • This mixture is stirred intimately and quickly and glued to KTL test specimens.
  • This mixture is stirred intimately and quickly and glued to KTL test specimens.
  • Polytetrahydrofuran 1000 and diphenyl-4,4'-diisocyanate are converted by a polyaddition to a prepolymer.
  • reaction mixture is stirred for a further 3 hours at 80 0 C. Finally, it is cooled to 40 ° C. and the product is bottled. It is at room temperature as a white, rubbery resin and is still fluid in the heat. It has an OH number of 17.5 (additive 10).
  • Polytetrahydrofuran 1000 and diphenyl-4,4'-diisocyanate are converted by a polyaddition to a prepolymer.
  • reaction mixture is stirred for a further 3 hours at 80 0 C. Finally, it is cooled to 40 ° C. and the product is bottled. It is present as a white, gelatinous resin at room temperature and is heat-curable. It has an OH number of 12.4 (additive 11).
  • This mixture is stirred intimately and quickly and glued to KTL test specimens.
  • Polytetrahydrofuran 2000 and diphenyl-4,4'-diisocyanate are converted by a polyaddition to a prepolymer.
  • reaction mixture is stirred for a further 3 hours at 80 0 C. Finally, it is cooled to 40 ° C. and the product is bottled. It is at room temperature as a white, gelatinous resin and is just flowable in the heat. It has an OH number of 17.1 (additive 12).
  • Polytetrahydrofuran 2000 and diphenyl-4,4'-diisocyanate are converted by a polyaddition to a prepolymer.
  • reaction mixture is stirred for a further 3 hours at 80 0 C. Finally, it is cooled to 40 ° C. and the product is bottled. It is present at room temperature as a white, rigid, hardly flowable resin and can be melted again. It has an OH number of 12.7 (additive 13).
  • Polytetrahydrofuran 650 and diphenyl-4,4'-diisocyanate are converted by a polyaddition to a prepolymer.
  • reaction mixture for an additional 3 hours at 80 0 C is annealed without stirring. Finally, it is cooled to 40 ° C. and the product is bottled. It is at room temperature as a white, solid, rubbery resin and has an OH number of 10.7 (Additive 14).
  • Polytetrahydrofuran 2000 and diphenyl-4,4'-diisocyanate are converted by a polyaddition to a prepolymer.
  • reaction mixture for an additional 3 hours at 80 0 C is annealed without stirring. Finally, it is cooled to 40 ° C. and the product is bottled. It is at room temperature as a slightly cloudy, rubbery, non-flowable resin and has an OH number of 10.3 (Additive 15).

Landscapes

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

Abstract

Adhésif de polyuréthanne à deux constituants, à base d'un constituant polyol et d'un constituant polyisocyanate. Une liaison par collage à l'aide dudit adhésif de deux tôles d'acier couvertes d'une couche de peinture appliquée par électrodéposition cathodique possède à une température de -40 °C une résistance au pelage dû aux chocs selon la norme ISO 11343 d'au moins 11 N/mm. La présente invention concerne en outre un additif pour des adhésifs de polyuréthanne, ainsi que l'utilisation de cet additif.
EP05812167A 2004-11-30 2005-11-21 Adhesifs de polyurethanne a deux constituants, additifs pour des adhesifs de polyurethanne a deux constituants et utilisation desdits additifs Withdrawn EP1824941A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004057699A DE102004057699A1 (de) 2004-11-30 2004-11-30 Zwei-Komponenten-Polyurethanklebstoffe, Additive für Zwei-Komponenten-Polyurethanklebstoffe und Verwendung der Additive
PCT/EP2005/012422 WO2006058624A1 (fr) 2004-11-30 2005-11-21 Adhesifs de polyurethanne a deux constituants, additifs pour des adhesifs de polyurethanne a deux constituants et utilisation desdits additifs

Publications (1)

Publication Number Publication Date
EP1824941A1 true EP1824941A1 (fr) 2007-08-29

Family

ID=35781267

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05812167A Withdrawn EP1824941A1 (fr) 2004-11-30 2005-11-21 Adhesifs de polyurethanne a deux constituants, additifs pour des adhesifs de polyurethanne a deux constituants et utilisation desdits additifs

Country Status (6)

Country Link
US (1) US20070282090A1 (fr)
EP (1) EP1824941A1 (fr)
JP (1) JP2008521979A (fr)
KR (1) KR20070085585A (fr)
DE (1) DE102004057699A1 (fr)
WO (1) WO2006058624A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8410213B2 (en) * 2009-01-26 2013-04-02 Michael James Barker Primerless two-part polyurethane adhesive
EP3310825B1 (fr) * 2015-06-18 2022-06-22 DDP Specialty Electronic Materials US, LLC Adhésifs contenant du polyuréthane en deux parties fabriqués à l'aide de quasi-prépolymeres comportant un isocyanate en position terminale à base de poly(oxyde de butylène)
CN116836670A (zh) * 2022-12-13 2023-10-03 江苏长能节能新材料科技有限公司 深冷绝缘用双组分胶水、制备方法及其应用

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US6359100B1 (en) * 1998-01-28 2002-03-19 Bristol-Myers Squibb Company Methods of preparing polyurethane adhesives, adhesives produced thereby and medical devices employing the same
DE19961941A1 (de) * 1999-12-22 2001-07-05 Henkel Kgaa Polyurethan-Zusammensetzungen auf der Basis von Polyether-Copolymeren
DE10009407A1 (de) * 2000-02-28 2001-08-30 Bayer Ag Polyurethan-Beschichtungen
DE50309990D1 (de) * 2002-02-22 2008-07-31 Jowat Ag Polyurethan-Zusammensetzungen mit geringem Anteil an Diisocyanatmonomer(en)
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Also Published As

Publication number Publication date
US20070282090A1 (en) 2007-12-06
WO2006058624A1 (fr) 2006-06-08
DE102004057699A1 (de) 2006-06-01
KR20070085585A (ko) 2007-08-27
JP2008521979A (ja) 2008-06-26

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