EP0000548B1 - Verfahren zur Herstellung von Dihydroxypolyurethane und ihre Verwendung als Klebstoff oder als Klebstoffrohstoff - Google Patents

Verfahren zur Herstellung von Dihydroxypolyurethane und ihre Verwendung als Klebstoff oder als Klebstoffrohstoff Download PDF

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Publication number
EP0000548B1
EP0000548B1 EP78100448A EP78100448A EP0000548B1 EP 0000548 B1 EP0000548 B1 EP 0000548B1 EP 78100448 A EP78100448 A EP 78100448A EP 78100448 A EP78100448 A EP 78100448A EP 0000548 B1 EP0000548 B1 EP 0000548B1
Authority
EP
European Patent Office
Prior art keywords
groups
adhesive
ionic
dihydroxypolyurethanes
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.)
Expired
Application number
EP78100448A
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German (de)
English (en)
French (fr)
Other versions
EP0000548A1 (de
Inventor
Walter Dr. Meckel
Horst Dr. Müller-Albrecht
Manfred Dr. Dollhausen
Eugen Dr. Velker
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 AG
Original Assignee
Bayer 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 AG filed Critical Bayer AG
Publication of EP0000548A1 publication Critical patent/EP0000548A1/de
Application granted granted Critical
Publication of EP0000548B1 publication Critical patent/EP0000548B1/de
Expired 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
    • C09J175/06—Polyurethanes from polyesters
    • 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
    • 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
    • C08G18/0833—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups together with anionic or anionogenic groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6633—Compounds of group C08G18/42
    • C08G18/6659—Compounds of group C08G18/42 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
    • C08G2170/00—Compositions for adhesives
    • C08G2170/20—Compositions for hot melt adhesives
    • 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
    • C08G2170/90—Compositions for adhesives used in footwear
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S528/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S528/905—Polymer prepared from isocyanate reactant has adhesive property

Definitions

  • a disadvantage of these adhesives is a lack of adhesion to special, in particular soft, transparent rubber qualities, which can only be improved by a complex, additional operation.
  • oxidizing acids such as e.g. Sulfuric acid (DT-PS 807 719), halogenation with chlorine- or bromine-releasing agents (DT-OS 550 823) or application of a primer made of polychloroprene or other halogen-containing polymers (US Pat. No. 3,917,742). All of these steps involve an additional work step and are therefore more expensive; in addition, as with sulfuric acid or halogen pretreatment, there are toxic products that require complex protective measures.
  • dihydroxypolyurethanes which contain both chemically built-in ionic groups and chemically built-in carboxyl groups and which are prepared by the process according to the invention described below are outstandingly suitable for the bonding of rubber, since on the one hand the achievable separating strengths of the bonds are well above the separation strengths that can be achieved with the polyurethanes according to the prior art, and since, on the other hand, the disadvantages mentioned, which had to be observed in the case of addition of carboxylic acids to polyurethane adhesive solutions, no longer occur.
  • the nine process products according to the invention are also suitable for bonding any other substrates.
  • the present invention thus relates to a process for the preparation of dihydroxypolyurethanes containing carbocyl groups and chemically fixed ionic groups by reacting dihydroxypolyesters in the molecular weight range 600-8000, and optionally diols in the molecular weight range 62-300 with organic diisocyanates in the melt or in the presence of organic solvents the one-component or by the prepolymer process, characterized in that the reaction is carried out in the presence of carboxyl groups and two hydroxyl groups and in the presence of ionic groups and two hydroxyl-containing compounds.
  • the present invention also relates to the use of the products produced as an adhesive or adhesive raw material for bonding any substrates and in particular for bonding rubber to itself and other materials.
  • Starting materials for the process according to the invention are organic diisocyanates, dihydroxy polyesters, optionally low-molecular chain extenders and compounds containing both carboxyl groups and compounds containing ionic groups, each with hydroxyl groups. Accordingly, the process products according to the invention are predominantly linear polyurethanes.
  • the use of small amounts of structural components higher than difunctional, for example small amounts of trimethylolpropane, in order to achieve a certain degree of branching in the process according to the invention should not be ruled out by this, however, since such small branching of the process products according to the invention can often be advantageous.
  • the aromatic diisocyanates mentioned are preferably used in the process according to the invention.
  • suitable diisocyanates are, for example, 1,4-butane diiso, 1,6-hexane diisocyanate, 1,4-cychlohexylene diisocyanate, 1-methyl-2,4-diisocyanato-cyclohexane, 1-methyl-2,6-diisocyanato-cyclohexane, 1-isocyanato - 3 - isocyanatomethyl - 3,5,5 - trimethy - cyclohexane, 2 or 2,6 6-diisocyanatotoluene, 4,4 '- diphenylmethane diisocyanate, 4,4 - - diphenylpropane diisocyanate or mixtures of such diisocyanates.
  • 4,4'-Diphenylmethane diisocyanate is particularly suitable.
  • Dihydroxy polyesters suitable for the process according to the invention are in particular those of a molecular weight above 600, preferably between 1200 and 6000, particularly preferably between 2000 and 4000, as are known in a known manner from alkanedicarboxylic acids with preferably at least 6 carbon atoms and alkanediols with preferably at least 4 carbon atoms .
  • Suitable dicarboxylic acids are, for example, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, etc.
  • Suitable alkanediols are, for example, 1,4-butanediol, 1,5-pentanediol or 1,6-hexanediol.
  • polyesters are also dihydroxyl polycarbonates, in particular based on 1,6-hexanediol and terminal hydroxyl-containing esterification products of straight-chain hydroxylalkane monocarboxylic acids with at least 5 carbon atoms, such as E- hydroxycaproic acid or the corresponding lactone polymers.
  • chain extenders known per se in polyurethane chemistry are often used, although the use of such chain extenders is not absolutely necessary.
  • These chain extenders are, in particular, diols or diol mixtures in the molecular weight range 62-300, preferably 62-150.
  • Suitable such diols are e.g. Ester diols of the mentioned molecular weight range, e.g. Terephthalic acid bis-2-hydroxyethyl ester, ether diols of the stated molecular weight range, such as e.g. Hydroquinone bis - 2 - hydroxyethyl ether.
  • simple alkane diols having 2-8, preferably 4-6, carbon atoms such as ethylene glycol, trimethylene glycol, tetramethylene glycol, pentamethylene glycol or 1,6-hexanediol are preferably used as chain extenders.
  • the chain extenders are generally used in the process according to the invention in amounts such that 0-1, preferably 0.3-0.7, mol of the chain extender are present in each mole of the dihydroxy polyester.
  • the stated amounts relate to each of the glycols present in the mixture, so that the total amount of the glycol mixture can be measured in such a way that up to 2 moles, preferably up to 1.4 moles, of glycol are present per mole of dihydroxy polyester.
  • the compounds mentioned under a) and b) are also used in amounts such that 0.01 to 1.0, preferably 0.02 to 0.4,% by weight of -COOH and 0.1 to 10% by weight of carboxyl groups in the process products , preferably 0.5 to 5 milliequivalents per 100 g of ionic groups.
  • ionic groups are understood to mean, in particular, homopolar ammonium groups, sulfonium groups, carboxylate groups, sulfonate groups or phosphonate groups.
  • Preferred ionic groups are the sulfonate groups -S0 3 o .
  • the structural components mentioned under a) are preferably dihydroxycarboxylic acids, such as, in particular, 2,2-dimethylolpropionic acid or also dihydroxycarboxylic acids such as tartaric acid or ester-containing dihydroxycarboxylic acids, as obtained, for example, by reacting dicarboxylic acid anhydrides, e.g. Tetrahydrophthalic anhydride with trimethylolpropane in a molar ratio of 1: 1 are easily accessible.
  • dicarboxylic acid anhydrides e.g. Tetrahydrophthalic anhydride with trimethylolpropane in a molar ratio of 1: 1 are easily accessible.
  • Suitable examples of the structural components mentioned under b) are, in accordance with the statements made above, preferably diols containing phosphonate groups, carboxylate groups, sulfonate groups, ammonium groups or sulfonium groups, where, in the case of the preparation of process products according to the invention having ammonium groups, in particular using solvents when carrying out the process according to the invention also one Embodiment is conceivable in which diols containing tertiary amine nitrogen atoms are incorporated into the polyurethane, the tertiary nitrogen atoms of which are converted into quaternary ammonium groups only after the polyurethane has been built up by quaternization, for example with dimethyl sulfate.
  • the ionic components are preferably those which have 2 aliphatic hydroxyl groups.
  • Suitable structural components containing carboxylate groups are, for example, the alkali and ammonium salts of the dihydroxycarboxylic acids already mentioned by way of example which are optionally substituted on the ammonium group.
  • any organic compounds which, in addition to 2 aliphatically bonded hydroxyl groups, have at least 1 ammonium, sulfonium, carboxylate, sulfonate or phosphonate group and are otherwise inert under the conditions of the method according to the invention can be used as ionic structural components in the process according to the invention.
  • Such ionic structural components for the production of ionically modified polyurethanes are, for example, the difunctional ionic structural components of US Pat. No. 3,479,310, OT-OS 2,446,440, DT-OS 2,426,401, DT-OS 2,417,664, DT-OS 2,410,862 or US Pat. No. 3,708,303 or the structural components with potential ionic groups corresponding to the functional components described in these references which are difunctional in the context of the isocyanate addition reaction and which can be obtained by quaternization or neutralization of the potential ionic groups.
  • the diols containing ionic groups or carboxyl groups are preferably used in the process according to the invention as separate structural components.
  • the low-molecular weight ionic groups having glycols as build-up components in the preparation of the dihydroxy polyesters to be used in the process according to the invention, ie the ionic ones 'Groups are to be incorporated into the process products according to the invention at the stage of the dihydroxy polyesters to be used in the process according to the invention.
  • the amount of the constituent components having carboxyl groups or ionic groups is such that the content of carboxyl groups and ionic groups in the process products according to the invention within the abovementioned. Range.
  • the process according to the invention is preferably carried out in a one-pot process, i.e. by reacting the diisocyanate component with a mixture of all compounds having hydrogen atoms which are reactive toward isocyanate groups, preferably in the melt at 50 to 200, preferably 80 to 150 ° C., in an NCO / OH molar ratio of 0.9: 1 to 0.999: 1 is worked so that process products always having terminal hydroxyl groups are formed.
  • the reaction can of course also in the presence of inert solvents. such as. Toluene, methyl ethyl ketone, ethyl acetate or dimethylformamide or in the presence of mixtures of such solvents.
  • the process according to the invention can also be carried out according to the prepolymer principle, in which case, for example, the polyester component with the diisocyanate component is reacted in an NCO / OH molar ratio above 50: 150 to an NCO prepolymer, which is subsequently with a mixture of glycol having carboxyl groups, glycol having ionic groups and optionally simple glycol chain extender at 80 to 200 ° C.
  • the polyester component with the diisocyanate component is reacted in an NCO / OH molar ratio above 50: 150 to an NCO prepolymer, which is subsequently with a mixture of glycol having carboxyl groups, glycol having ionic groups and optionally simple glycol chain extender at 80 to 200 ° C.
  • Variants are of course conceivable, for example in such a way that one or two of the glycol types mentioned are already
  • the process products according to the invention are valuable adhesives or adhesive raw materials for bonding any substrates, but especially for bonding rubber to themselves or other materials.
  • the process products according to the invention are used for the purposes of the invention in the form of solutions in suitable solvents, for example of the type already mentioned above as examples or processed as a melt.
  • the process products according to the invention are preferably used in the form of 10-40% by weight solutions in polar solvents, for example acetone or methyl ethyl ketone.
  • the viscosity of these adhesive solutions can be adapted to the special requirements of the adhesive process or of the materials to be bonded by varying the content of hydroxyl polyurethane.
  • solutions according to the invention of the hydroxyl polyurethanes according to the invention are advantageously prepared by simply dissolving the polyurethanes in the polar solvents used at room temperature or at a moderately elevated temperature. If the hydroxyl polyurethanes were prepared in solution, the non-polar solvent which may be used for the preparation can either be drawn off first, or an amount of polar solvent adapted to the particular intended use can also be added to the system without first removing the non-polar solvent. When using polar solvents during the production of the polyurethanes, directly usable solutions are created.
  • the described adhesives can be natural or synthetic resins, such as Phenolic resins, ketone resins, rosin derivatives, phthalate resins, acetyl or nitrocellulose or other substances such as e.g. Silicate fillers are added.
  • crosslinking agents for example higher functional polyisocyanates such as e.g. Phosphoric acid tris isocyanatophenyl ester or tris isocyanato toloyl isocyanurate, to the adhesive solutions is possible.
  • the process products according to the invention can also be processed from the melt.
  • the adhesives present as a solution or melt are applied to the material surfaces to be bonded, which may be roughened or otherwise pretreated, for processing. This can be done using a roller, brush, spatula, spray gun or other device.
  • the adhesive spreads are heated, for example, to approximately 50 to 150, preferably approximately 55 to 100 ° C., and then immediately joined together with pressing pressure, or according to a preferred variant of this invention a material surface provided with an already dried adhesive layer a liquid plastic heated to 120 to 200 ° C, e.g. a plasticized vinyl chloride polymer, applied by injection molding.
  • Numerous materials such as paper, cardboard, wood, metal and leather, can be bonded with high strength using the process products according to the invention. They are preferably suitable for gluing rubber materials and other plastics, such as Polyurethane foams with a compact surface and - insofar as they correspond in their other composition to DT-PS 1 256 822 - plasticized homopolymers or copolymers of vinyl chloride, especially for gluing soles made of these materials to leather or synthetic leather shoe uppers.
  • plastics such as Polyurethane foams with a compact surface and - insofar as they correspond in their other composition to DT-PS 1 256 822 - plasticized homopolymers or copolymers of vinyl chloride, especially for gluing soles made of these materials to leather or synthetic leather shoe uppers.
  • the process products according to the invention are also outstandingly suitable as Coating agent for a wide variety of substrates, especially for rubber.
  • the polyester is mixed with the number of moles of the chain extender (butanediol or hexanediol) given in Table 1, the number of moles of the ionic synthesis components given in Table 1 and the number of moles of dimethylolpropionic acid given in Table 1.
  • the mixture is then dewatered at 100 ° C in a water jet vacuum.
  • test specimens were coated on both sides with 250 g / m 2 of the adhesive solution, the solvent is evaporated at 80 ° C, and the heat treatment activates the adhesive layer at the same time.
  • the bonding was carried out by compressing the test specimens provided with the activated adhesive layer under gentle pressure. After nine days of storage, the separation strengths listed in Table 2 were determined in kp / cm:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Polyurethanes Or Polyureas (AREA)
EP78100448A 1977-07-28 1978-07-20 Verfahren zur Herstellung von Dihydroxypolyurethane und ihre Verwendung als Klebstoff oder als Klebstoffrohstoff Expired EP0000548B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2734102 1977-07-28
DE19772734102 DE2734102A1 (de) 1977-07-28 1977-07-28 Verfahren zur herstellung von dihydroxypolyurethanen und ihre verwendung als klebstoff oder als klebstoffrohstoff

Publications (2)

Publication Number Publication Date
EP0000548A1 EP0000548A1 (de) 1979-02-07
EP0000548B1 true EP0000548B1 (de) 1980-07-23

Family

ID=6015060

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100448A Expired EP0000548B1 (de) 1977-07-28 1978-07-20 Verfahren zur Herstellung von Dihydroxypolyurethane und ihre Verwendung als Klebstoff oder als Klebstoffrohstoff

Country Status (9)

Country Link
US (1) US4240861A (enrdf_load_stackoverflow)
EP (1) EP0000548B1 (enrdf_load_stackoverflow)
JP (1) JPS5425997A (enrdf_load_stackoverflow)
AT (1) AT371488B (enrdf_load_stackoverflow)
BR (1) BR7804831A (enrdf_load_stackoverflow)
DE (2) DE2734102A1 (enrdf_load_stackoverflow)
ES (1) ES472092A1 (enrdf_load_stackoverflow)
IT (1) IT1105943B (enrdf_load_stackoverflow)
MX (1) MX148906A (enrdf_load_stackoverflow)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS55110034U (enrdf_load_stackoverflow) * 1979-01-29 1980-08-01
JPS59157277A (ja) * 1983-02-25 1984-09-06 Seiko Kasei Kk 金属蒸着皮膜
JPS59157276A (ja) * 1983-02-25 1984-09-06 Seiko Kasei Kk 金属蒸着皮膜
JPS60279U (ja) * 1983-06-17 1985-01-05 日産ディーゼル工業株式会社 パワ−ステアリング装置
EP0158086B1 (de) * 1984-03-10 1987-12-23 Bayer Ag Schmelzklebstoff und seine Verwendung zur Herstellung von Verbundstrukturen
JPS6126683A (ja) * 1984-07-17 1986-02-05 Polyurethan Kasei Kk 充填・接着剤組成物
DE3524333A1 (de) * 1985-07-08 1987-01-08 Basf Ag Polyurethan-klebstoff-mischungen
DE3942681A1 (de) * 1989-12-22 1991-06-27 Henkel Kgaa Haushaltskleber auf polyurethanbasis
US5091239A (en) * 1990-03-07 1992-02-25 Cms Gilbreth Packaging Systems, Inc. Methods and adhesives for bonding polyolefin film
DE4024567A1 (de) * 1990-08-02 1992-02-06 Basf Ag Herstellung von waessrigen polyurethandispersionen
US5089364A (en) * 1990-10-26 1992-02-18 Xerox Corporation Electrophotographic imaging members containing a polyurethane adhesive layer
DE4308079A1 (de) * 1993-03-13 1994-09-15 Basf Ag Verwendung von wäßrigen Polyurethandispersionen als Verbundfolienklebstoff
FR2838143B1 (fr) * 2002-04-05 2005-05-13 Soprema Procede de fixation d'une couche d'isolation et enduit mis en oeuvre dans ce procede

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1495745C3 (de) * 1963-09-19 1978-06-01 Bayer Ag, 5090 Leverkusen Verfahren zur Herstellung wäßriger, emulgatorfreier Polyurethan-Latices
US3658939A (en) * 1968-12-11 1972-04-25 Usm Corp Polyurethane and adhesive solution of a polyurethane
JPS4928653B1 (enrdf_load_stackoverflow) * 1970-04-21 1974-07-29
US3759873A (en) * 1971-05-20 1973-09-18 Ashland Oil Inc Boxy polyols water dispersible polyurethanes based on polyesters prepared from car
FR2290460A1 (fr) * 1974-11-05 1976-06-04 Rhone Poulenc Ind Procede de fabrication de polyurethannes hydrosolubles
US3994764A (en) * 1975-06-13 1976-11-30 Pratt & Lambert, Inc. Adhesive compositions
DE2541339A1 (de) * 1975-09-17 1977-03-24 Basf Ag Verfahren zur herstellung von polyurethanklebstoffen

Also Published As

Publication number Publication date
AT371488B (de) 1983-06-27
JPS5425997A (en) 1979-02-27
DE2734102A1 (de) 1979-02-15
US4240861A (en) 1980-12-23
ATA544478A (de) 1982-11-15
BR7804831A (pt) 1979-04-10
JPS6134729B2 (enrdf_load_stackoverflow) 1986-08-09
MX148906A (es) 1983-06-30
ES472092A1 (es) 1979-03-16
EP0000548A1 (de) 1979-02-07
IT1105943B (it) 1985-11-11
DE2860063D1 (en) 1980-11-13
IT7850472A0 (it) 1978-07-26

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