EP2356164A1 - Dispersions de polyuréthane modifiées anioniquement - Google Patents

Dispersions de polyuréthane modifiées anioniquement

Info

Publication number
EP2356164A1
EP2356164A1 EP09744350A EP09744350A EP2356164A1 EP 2356164 A1 EP2356164 A1 EP 2356164A1 EP 09744350 A EP09744350 A EP 09744350A EP 09744350 A EP09744350 A EP 09744350A EP 2356164 A1 EP2356164 A1 EP 2356164A1
Authority
EP
European Patent Office
Prior art keywords
mmol
polyurethane
polyurethaneurea
dispersions according
urea
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Withdrawn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
EP09744350A
Other languages
German (de)
English (en)
Inventor
Harald Kraus
Wolfgang Arndt
Wolfgang Henning
Alice Münzmay
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.)
Bayer Intellectual Property GmbH
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
Priority to EP09744350A priority Critical patent/EP2356164A1/fr
Publication of EP2356164A1 publication Critical patent/EP2356164A1/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Withdrawn legal-status Critical Current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
    • C08G18/08—Processes
    • 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
    • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
    • C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
    • 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
    • C08G18/65—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
    • C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
    • 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
    • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/08—Polyurethanes from polyethers
    • 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
    • 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
    • C09J175/08—Polyurethanes from polyethers
    • 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
    • C08G2170/00—Compositions for adhesives
    • C08G2170/80—Compositions for aqueous adhesives
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/21—Circular sheet or circular blank
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/249921—Web or sheet containing structurally defined element or component
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
    • Y10T428/2852—Adhesive compositions
    • Y10T428/2896—Adhesive compositions including nitrogen containing condensation polymer [e.g., polyurethane, polyisocyanate, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y10T428/31591—Next to cellulosic

Definitions

  • the invention relates to anionically modified polyurethaneureas based on aromatic polyisocyanates, a process for their preparation and their use for the production of laminations of laminar structures or for the production of adhesives.
  • polyurethane adhesives are becoming increasingly important in the field of wood bonding, since they have considerable advantages in terms of thermal and water resistance compared with the polyvinyl acetate dispersions which are also frequently used.
  • These polyurethane adhesives are generally NCO-terminated polyurethane prepolymers having significant NCO contents of between 5 and 20%. After application to wood, these react with their substrate moisture or the moisture of the ambient air to form a polyurethane polyurea.
  • Polyether-based polyurethane systems are generally preferred to polyester-based ones because they are more resistant to moisture and microbes.
  • Corresponding polyurethane adhesives are described, for example, in WO-A 03/066700.
  • a disadvantage of the use of polyurethane prepolymers as one-component polyurethane adhesives is the high content of NCO groups which require moisture-exclusion work in the formulation, processing and application of the adhesives. In addition, appropriate skin protection must be avoided by appropriate protective measures.
  • EP-A 0 615 988 describes the use of aqueous polyurethane dispersions containing a polyurethane with a very low urea group content as an adhesive.
  • the object of the present invention was therefore to provide polyurethane or polyurethane urea dispersions based on polyethers which, when used as one-component adhesives for wood bonding, lead to improved tensile shear strengths.
  • the present invention relates to aqueous polyurethaneurea dispersions comprising a polyurethaneurea polymer having structural units of the general formula (I)
  • aromatic phenylene, tolylene, xylylene, tetramethylxylylene or diphenylenemethane, preferably tolylene or diphenylenemethane and which is composed of
  • At least one polyether polyol having a number average molecular weight of from 300 to 1500 Da, preferably from 500 to 1250 Da,
  • the average total functionality of the isocyanate-reactive compounds B) to D) is from 1.85 to 2.2, preferably from 1.9 to 2.1, and in the polyurethane-urea polymer the sum of the content of aromatic urea groups and the content of urethane groups is 2700 to 5000 mmol per kg, preferably 2800 to 4000 mmol per kg and more preferably 2850 to 3500 mmol per kg polyurethaneurea polymer.
  • diisocyanate component A examples include: 1,4-diisocyanatobenzene, 2,4-diisocyanatotoluene, 2,6-diisocyanatotoluene, 4,4'-diisocyanatodiphenylmethane, 2,2'- and 2,4'-diisocyanatotoluene.
  • Diisocyanatodiphenylmethane tetramethylxylylene diisocyanate, p-xylylene diisocyanate and mixtures of these compounds. Preference is given to 2,4-diisocyanatotoluene, 2,6-
  • Polyether polyols B) are the polyaddition products of ethylene oxide, propylene oxide, butylene oxide and their mixed and graft polyaddition products, as well as by condensation of polyhydric alcohols or mixtures thereof and the polyethers obtained by alkoxylation of water, polyhydric alcohols, amines or aminoalcohols. Preference is given to homo- and / or MischpolyadditionsENSen of ethylene oxide and / or propylene oxide of molecular weight less than 1500 Da, preferably from 500 to 1250 Da.
  • the average functionality of the polyether polyols is greater than 1.85, preferably from 1.92 to 3. Particular preference is given to difunctional polyethers having a functionality of from 1.95 to 2.05.
  • the proportion of ethylene oxide in the Mischpolyadditionsberichten of ethylene oxide and propylene oxide is 1 to 50%, preferably 1 to 30%, particularly preferably 5 to 20%.
  • the polyether polyol B) is a homopoly addition product of the propylene oxide having a molecular weight of from 750 to 1250 Da and a functionality of from 1.95 to 2.05.
  • polyurethane chemistry e.g. from the classes of polyester, polylactone or polycarbonate polyols find use.
  • ionogenic compounds C) having one to two isocyanate-reactive groups and at least one ionogenic group compounds such as e.g. Hydroxy- and mercaptocarboxylic acids, aminocarboxylic acids such as glycine, alanine or 4-aminobutyric acid, di- and polyhydroxycarboxylic acids such as dimethylolpropionic acid or dimethylolbutanoic or sulfonate aliphatic diols according to DE-A 2 446 440 (page 4 - page 6) and 2 437 218 (p.3 - 4).
  • Preferred ionogenic components C) include dimethylol butyric or dimethylol propionic acid.
  • the neutralizing agents used are preferably tertiary amines such as triethylamine, tripropylamine, tributylamine, triisopropanolamine, triethanolamine, N, N-dimethylethanolamine or ammonia or alkali metal hydroxides such as Sodium or potassium hydroxide or alkali carbonates or bicarbonates in question.
  • Suitable polyols D) are compounds whose molecular weight is greater than 60 Da, preferably between 90 and 220 Da, and containing primary or secondary alcohol groups.
  • Suitable compounds D) are, for example, diols, such as ethanediol, di-, tri-, tetraethylene glycol, 1,2-propanediol, di-, tri-, tetrapropylene glycol, 1,3-propanediol, 1,4-butanediol, butanediol -1,3, butanediol-2,3, pentanediol-1,5, 1,6-hexanediol, 2,2-dimethyl-1,3-propanediol, 1,4-dihydroxycyclohexane, 1,4-dimethylolcyclohexane, octanediol-1 , 8, decanediol-1,10, dodecanediol 1,12
  • component D) compounds are polyol compounds having a hydroxyl functionality greater than 2, such as trimethylolpropane or glycerol.
  • Butane-1,4-diol, 1,3-butanediol, 2,3-butanediol, 1,5-pentanediol or 1,6-hexanediol are particularly preferred as component D).
  • the preparation of the aqueous polyurethane or urea polyurethanes according to the invention can be carried out in one or more stages in homogeneous or in multistage reaction, in some cases in disperse phase. After complete or partial polyaddition carried out a dispersing, emulsifying or dissolving step. This is followed, if appropriate, by a further polyaddition or modification in disperse phase. Any of the methods known in the art, such as emulsifier shear force, acetone, prepolymer blending, melt emulsifying, ketimine and solid spontaneous dispersing methods or derivatives thereof, may be used in the preparation.
  • the present invention also provides a process for the preparation of the aqueous polyurethane-polyurea dispersions according to the invention, characterized in that the components A), B), C) and D) for the preparation of a polyurethane prepolymer in the reactor are completely or partially presented and optionally with a water-miscible but isocyanate-inert solvent, but preferably without solvent, and heated to temperatures in the range of 50 to 120 0 C, preferably in the range of 70 to 100 0 C and then optionally not yet added at the beginning of the reaction Ingredients A), B), C) or D) is metered in and before or during the dispersion is neutralized with a suitable neutralizing agent and then the optionally used organic solvent is distilled off.
  • Suitable solvents are, for example, acetone, butanone, tetrahydrofuran, dioxane, acetonitrile, dipropylene glycol dimethyl ether or 1-methyl-2-pyrrolidone, which may be added not only at the beginning of the preparation but, if appropriate, also in portions later. Preferred are acetone and butanone. It is possible to carry out the reaction under normal pressure or elevated pressure.
  • the amounts used of the individual components A) to D) are such that an isocyanate index of 1.05 to 3.0, preferably from 1.1 to 1.8 results.
  • the isocyanate content of the prepolymers is between 1.0 and 9.0%, preferably between 1.3 and 7.0%, particularly preferably between 1, 5 and 6.0%.
  • the reaction of components A) with B), C) and D) is based on the total amount of isocyanate-reactive groups, partially or completely, but preferably completely.
  • the degree of conversion is usually monitored by monitoring the NCO content of the reaction mixture.
  • Spectroscopic measurements eg infrared or near-infrared spectra, determinations of the refractive index as well as chemical analyzes, such as titrations of samples taken, can be made for this purpose.
  • the prepolymer is treated directly or after dissolving in a suitable solvent, preferably acetone, optionally with high shear, such as e.g. vigorous stirring, either added to the dispersing water or, conversely, the dispersing water is stirred into the prepolymer.
  • a suitable solvent preferably acetone
  • high shear such as e.g. vigorous stirring
  • neutralization with a suitable neutralizing agent takes place before or during the dispersion; tertiary amines such as triethylamine, tripropylamine, tributylamine, triethanolamine, triisopropanolamine, ethyldiisopropylamine are preferred , N, N-dimethylethanolamine and alkali hydroxides, alkali carbonates and / or bicarbonates.
  • the amount is such that the degree of neutralization is preferably between 40 and 200%, more preferably between 50 and 100%.
  • the remaining isocyanate groups react with water to form urea groups.
  • the optionally used organic solvent for example acetone
  • the dispersions have a solids content of 10 to 70 wt .-%, preferably 25 to 50% by weight and particularly preferably 30 to 40 wt .-%.
  • the amounts of starting components A) to D) in the process according to the invention are such that anionically modified polyurethane ureas having 50 to 750 mmol, preferably 200 to 600 mmol and more preferably from 250 to 550 mmol anionic groups / kg polymer result.
  • the invention relates to the use of the polyurethaneurea dispersions according to the invention for the production of coatings of sheetlike structures or as an adhesive.
  • adhesives comprising the polyurethaneurea dispersions according to the invention.
  • the adhesives containing the polyurethaneurea dispersions of the invention are useful for bonding any substrates such as e.g. Paper, cardboard, wood, cork, textiles, metal, leather, polymeric or mineral materials.
  • the adhesives according to the invention are particularly suitable for bonding wood or cork.
  • the adhesives containing the polyurethaneurea dispersions according to the invention are preferably applied to the substrates to be bonded by the wet bonding method. This means carrying out the sieving without drying immediately after the application of the adhesive. Until the adhesive sets, a mechanical fixation of the parts to be joined is required. But it is also possible to work after the thermal activation process. In this case, the dispersion is applied to the substrate, and after complete evaporation of the water, the adhesive layer by heating, for. B. with an infrared radiator, activated and transferred into a sticky state.
  • the result is an adhesive composite comprising at least one substrate and an adhesive layer containing the polyurethaneurea dispersions according to the invention.
  • the adhesive composites produced in this way lead after application of the method of wet bonding of wood to tensile shear strength greater than 4.4 N / mm, preferably> 4.8 N / mm, more preferably> 5.0 N / mm.
  • the present invention is an adhesive composite, composed of one or more substrate (s), which may be the same or different and an adhesive layer, containing the polyurethane urea dispersions according to the invention.
  • the adhesives containing the polyurethaneurea dispersions according to the invention are suitable for bonding substrates such as glass fiber fabric, carbon fiber fabric or mineral fiber fabric or mineral substrates.
  • substrates such as glass fiber fabric, carbon fiber fabric or mineral fiber fabric or mineral substrates.
  • the glass fiber fabrics, carbon fiber fabrics or mineral fiber fabric composites are glued to a mineral substrate.
  • adhesive composites composed of one or more substrates selected from the group of glass fiber, carbon fiber or mineral fiber fabrics and a gluing agent are also preferred.
  • adhesive composites composed of two wood substrates and an adhesive layer containing the polyurethaneurea dispersions according to the invention.
  • adhesive composites composed of a cork granules bound with polymeric material, a cork disc and an adhesive layer containing the polyurethaneurea dispersions according to the invention.
  • the tensile shear strengths after application of the wet bonding method can be determined by the following method:
  • the determination is carried out in one component (without crosslinker).
  • the adhesive dispersion is applied to both beech wood test specimens by means of a brush.
  • the adhesive surface is 10 x 20 mm.
  • the two specimens are superimposed and added 72 h at room temperature and 5 bar pressure.
  • test specimens are loaded at room temperature at 180 0 C to the joint, and withdrawn at a rate of 100 mm per minute.
  • a quintuple determination is made and the average value is given.
  • Luphen ® D259U BASF AG, Ludwigshafen / D
  • Dispercoll® ® U XP 2643 (Bayer MaterialScience AG, Leverkusen / D):
  • the solids content is about 40%.
  • Example 1 (according to the invention):
  • Luphen D259U is used instead of the polyurethane dispersion of Example 1.
  • the determination of the tensile shear strength after application of the method of wet bonding gives a value of 2.6 N / mm 2 .
  • Example 1 Dispercoll U XP 2643 is used.
  • the determination of the tensile shear strength after application of the wet bonding method gives a value of 2.6 N / mm 2 .
  • the polyether-based polyurethane or polyurethane urea dispersions according to the invention when used as one-component adhesives for wood bonding, lead to significantly improved tensile shear strengths.
  • These are in Examples 1) to 5) between 5.3 and 6.7 N / mm 2 .
  • the values found in the comparative examples 6) to 9) found in the prior art are only between 2.6 and 4.0 N / mm 2 .

Landscapes

  • 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)
  • Manufacturing & Machinery (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne des polyuréthane-urées modifiées anioniquement à base de polyisocyanates aromatiques, leur procédé de fabrication et leur utilisation pour la fabrication de revêtements de structures plates ou pour la fabrication d'adhésifs.
EP09744350A 2008-11-14 2009-10-31 Dispersions de polyuréthane modifiées anioniquement Withdrawn EP2356164A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP09744350A EP2356164A1 (fr) 2008-11-14 2009-10-31 Dispersions de polyuréthane modifiées anioniquement

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP20080019883 EP2186840A1 (fr) 2008-11-14 2008-11-14 Dispersions de polyuréthane modifiées par anions
PCT/EP2009/007804 WO2010054761A1 (fr) 2008-11-14 2009-10-31 Dispersions de polyuréthane modifiées anioniquement
EP09744350A EP2356164A1 (fr) 2008-11-14 2009-10-31 Dispersions de polyuréthane modifiées anioniquement

Publications (1)

Publication Number Publication Date
EP2356164A1 true EP2356164A1 (fr) 2011-08-17

Family

ID=40545956

Family Applications (2)

Application Number Title Priority Date Filing Date
EP20080019883 Withdrawn EP2186840A1 (fr) 2008-11-14 2008-11-14 Dispersions de polyuréthane modifiées par anions
EP09744350A Withdrawn EP2356164A1 (fr) 2008-11-14 2009-10-31 Dispersions de polyuréthane modifiées anioniquement

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP20080019883 Withdrawn EP2186840A1 (fr) 2008-11-14 2008-11-14 Dispersions de polyuréthane modifiées par anions

Country Status (14)

Country Link
US (1) US20110217502A1 (fr)
EP (2) EP2186840A1 (fr)
JP (1) JP2012508799A (fr)
KR (1) KR20110101132A (fr)
CN (1) CN102216360B (fr)
AR (1) AR074006A1 (fr)
AU (1) AU2009316017A1 (fr)
BR (1) BRPI0921114A2 (fr)
CA (1) CA2745658A1 (fr)
HK (1) HK1159142A1 (fr)
MX (1) MX2011004619A (fr)
RU (1) RU2011123675A (fr)
TW (1) TW201035143A (fr)
WO (1) WO2010054761A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2014119115A (ru) 2011-10-14 2015-11-20 Байер Интеллектуэль Проперти Гмбх Контактные адгезивы холодного отверждения
CN106884332B (zh) * 2017-03-27 2019-01-22 浙江鸿辰新材料科技有限公司 一种聚氨酯弹性丝纤维及其制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001042327A1 (fr) * 1999-12-08 2001-06-14 Skw Bauchemie Gmbh Procede de production de resines de polyurethanne aqueuses auto-emulsifiantes, presentant des proprietes ameliorees

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA931688A (en) * 1968-08-02 1973-08-07 C. Carlson Robert Sulfonated aromatic polyisocyanates and preparation of stable anionic polyurethane or polyurea latices therefrom
US3835081A (en) * 1972-07-26 1974-09-10 American Cyanamid Co Textile adhesive from polyurethane
DE2437218C3 (de) * 1974-08-02 1980-12-04 Bayer Ag, 5090 Leverkusen Ätherstrukturen enthaltende Dihydroxysulfonate und Verfahren zu deren Herstellung
DE2446440C3 (de) 1974-09-28 1981-04-30 Bayer Ag, 5090 Leverkusen Verfahren zur Herstellung von wäßrigen Dispersionen von Sulfonatgruppen aufweisenden Polyurethanen
DE4011455A1 (de) * 1990-04-09 1991-10-10 Henkel Kgaa Haushaltsalleskleber auf polyurethanbasis
DE4308079A1 (de) * 1993-03-13 1994-09-15 Basf Ag Verwendung von wäßrigen Polyurethandispersionen als Verbundfolienklebstoff
JP3465980B2 (ja) * 1995-03-02 2003-11-10 第一工業製薬株式会社 合成繊維経糸用糊剤およびその製法
JP3047098B2 (ja) * 1995-12-28 2000-05-29 三洋化成工業株式会社 ポリウレタン樹脂水性分散体およびコーティング剤
DE19908561A1 (de) * 1998-03-26 1999-09-30 Henkel Kgaa Klebestift auf der Basis eines Seifengels
JP2000017034A (ja) * 1998-06-29 2000-01-18 Sanyo Chem Ind Ltd 水性樹脂分散体組成物および多孔性シート材料の製造方法
JP2000198962A (ja) * 1998-12-28 2000-07-18 Sanyo Chem Ind Ltd 化粧板もしくは壁紙用水性コ―ティング剤
EP1490418B2 (fr) * 2002-02-08 2011-06-29 Henkel AG & Co. KGaA Adhesif Polyurethane a une composante de couleur neutre
JP4246054B2 (ja) * 2003-02-05 2009-04-02 東邦化学工業株式会社 シクロヘキサンジメタノールを用いた防錆用水系ポリウレタン樹脂
JP5073470B2 (ja) * 2007-12-25 2012-11-14 三洋電機株式会社 ポリウレタンエマルジョンとその硬化物

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001042327A1 (fr) * 1999-12-08 2001-06-14 Skw Bauchemie Gmbh Procede de production de resines de polyurethanne aqueuses auto-emulsifiantes, presentant des proprietes ameliorees

Also Published As

Publication number Publication date
HK1159142A1 (en) 2012-07-27
AR074006A1 (es) 2010-12-15
CN102216360B (zh) 2013-08-14
JP2012508799A (ja) 2012-04-12
EP2186840A1 (fr) 2010-05-19
KR20110101132A (ko) 2011-09-15
MX2011004619A (es) 2011-08-15
WO2010054761A1 (fr) 2010-05-20
US20110217502A1 (en) 2011-09-08
AU2009316017A1 (en) 2010-05-20
BRPI0921114A2 (pt) 2016-02-16
CN102216360A (zh) 2011-10-12
CA2745658A1 (fr) 2010-05-20
RU2011123675A (ru) 2012-12-20
TW201035143A (en) 2010-10-01

Similar Documents

Publication Publication Date Title
EP0304718B1 (fr) Solutions et dispersions aqueuses de polymères d'addition de polyisocyanates, procédé pour la préparation de telles solutions et dispersions et leur utilisation comme adhésifs
EP1979390B1 (fr) Adhésif à polyuréthane comprenant des groupes silane et carbo-diimide
EP0526472B1 (fr) Colle universelle a usage menager a base de polyurethane
EP0259679B1 (fr) Adhésif et l'utilisation de l'adhésif pour l'élaboration d'adhésions
DE69606033T2 (de) Wässrige nichtgelierende, anionische polyurethan-dispersionen und verfahren zu ihrer herstellung
EP3150646B1 (fr) Dispersions aqueuses de prepolymeres phosphores a terminaison d'isocyanate et revetements ainsi produits et leurs utilisation
EP2356163A1 (fr) Dispersions de polyuréthane réticulables
DE3521618A1 (de) In wasser dispergierbare polyisocyanat-zubereitung und ihre verwendung als zusatzmittel fuer waessrige klebstoffe
EP2316866A1 (fr) Préparation aqueuse à base de polymères de polyuréthane cristallins ou semi-cristallins
EP3280775B1 (fr) Procédé de collage de substrats à l'aide de colles
DE4236569A1 (de) Wäßrige Beschichtungsmittel und ihre Verwendung zur Erzeugung wasserdampfdurchlässiger Beschichtungen
WO1995025138A1 (fr) Produit aqueux a base de polyurethane pour couche de fond
EP0709414B1 (fr) Utilisation d'huiles de ricin partiellement déshydratées pour la préparation de dispersions aqueuses de plyuréthane et revêtements préparés en utilisant ces dispersions aqueuses de polyuréthane
EP3227372B1 (fr) Dispersion aqueuse de matières adhésives contenant du polyuréthane et des alcools gras éthoxylés
EP0884336B1 (fr) Dispersions aqueuses de polyuréthane à base de polypropylène glycol à contenu faible d'urée
WO2003068703A1 (fr) Dispersions aqueuses constituees de polycarbodiimides
EP1687353A1 (fr) Adhesifs de contre-collage contenant un polyurethane et une resine epoxyde
WO2010054761A1 (fr) Dispersions de polyuréthane modifiées anioniquement
DE10360368A1 (de) Dispersionen
DE4013546A1 (de) Verwendung von essigsaeureestern bei der herstellung von polyurethandispersionen
DE4137556A1 (de) Waessrige polyurethandispersionen
DE3942681A1 (de) Haushaltskleber auf polyurethanbasis
EP1491563A2 (fr) Compositions aqueuses de polyuréthanes hydrophiliques
DE102007052966A1 (de) Dispersionsklebstoffe
EP1123335A2 (fr) Dispersions aqueuses a reticulation latente, contenant un polyurethanne

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20110614

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO SE SI SK SM TR

DAX Request for extension of the european patent (deleted)
17Q First examination report despatched

Effective date: 20130115

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: BAYER INTELLECTUAL PROPERTY GMBH

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN

18W Application withdrawn

Effective date: 20130612