WO1996006897A2 - Physikalisch und/oder chemisch abbindende bindemittel - Google Patents
Physikalisch und/oder chemisch abbindende bindemittel Download PDFInfo
- Publication number
- WO1996006897A2 WO1996006897A2 PCT/EP1995/003331 EP9503331W WO9606897A2 WO 1996006897 A2 WO1996006897 A2 WO 1996006897A2 EP 9503331 W EP9503331 W EP 9503331W WO 9606897 A2 WO9606897 A2 WO 9606897A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- binder according
- fatty
- acid
- binder
- physically
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/02—Alcohols; Phenols; Ethers
- C04B24/026—Fatty alcohols
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/08—Fats; Fatty oils; Ester type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
- C08L91/005—Drying oils
-
- 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
- C09D125/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
- C09D125/02—Homopolymers or copolymers of hydrocarbons
- C09D125/04—Homopolymers or copolymers of styrene
- C09D125/06—Polystyrene
-
- 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
- C09D131/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid, or of a haloformic acid; Coating compositions based on derivatives of such polymers
- C09D131/02—Homopolymers or copolymers of esters of monocarboxylic acids
- C09D131/04—Homopolymers or copolymers of vinyl acetate
-
- 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
- C09J1/00—Adhesives based on inorganic constituents
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- 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
- C09J125/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Adhesives based on derivatives of such polymers
- C09J125/02—Homopolymers or copolymers of hydrocarbons
- C09J125/04—Homopolymers or copolymers of styrene
- C09J125/06—Polystyrene
-
- 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
- C09J127/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Adhesives based on derivatives of such polymers
- C09J127/02—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
- C09J127/04—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Adhesives based on derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C09J127/06—Homopolymers or copolymers of vinyl chloride
-
- 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
- C09J131/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid, or of a haloformic acid; Adhesives based on derivatives of such polymers
- C09J131/02—Homopolymers or copolymers of esters of monocarboxylic acids
- C09J131/04—Homopolymers or copolymers of vinyl acetate
-
- 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
- C09J191/00—Adhesives based on oils, fats or waxes; Adhesives based on derivatives thereof
- C09J191/005—Drying oils
-
- 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
- C08L2666/34—Oxygen-containing compounds, including ammonium and metal salts
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/04—Non-macromolecular organic compounds
- C09K2200/0441—Carboxylic acids, salts, anhydrides or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/04—Non-macromolecular organic compounds
- C09K2200/0447—Fats, fatty oils, higher fatty acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09K2200/0632—Polystyrenes
Definitions
- the invention relates to binders, their production and use for gluing, coating and sealing.
- Binder should be understood to mean those substances which connect the same or different types of substrates or can adhere to them themselves. They are usually based on substances, especially polymers, that chemically or physically set. The physical setting consists in solidification from the melt or in the drying of an aqueous or organic solution or dispersion.
- the substances or polymers are generally modified by additives so that they are more suitable for gluing, adhesive sealing and coating. Such additives are e.g. Resins, plasticizers, solvents, fillers, pigments, accelerators, stabilizers and dispersants.
- the adhesives, the sealing compounds and the coating agents are based on such modified binders.
- Plasticizers are added in order to improve the shape-changing capacity or reduce the hardness of adhesives, sealants and sealants. These are liquid or solid, generally indifferent organic substances with low vapor pressure. According to the general specialist knowledge (see habenicht, gerd: "gluing: basics, technology applications", 2nd edition, 1990, page 100), the disadvantage of plasticized adhesive layers lies in the deteriorated aging and Adhesion properties, furthermore in the reduced adhesive layer strengths, their tendency to creep and their tendency to emigrate. A well-balanced examination of the priorities between deformability on the one hand and strength on the other hand is therefore necessary.
- plasticizers In "Ullmann's Encyclopedia of Technical Chemistry” the use of plasticizers is also described under the keyword “plasticizers” (see pages 371 to 377, volume 24, 4th edition, 1983). Accordingly, dibutyl phthalate, possibly together with tricresyl phosphate, is the most popular plasticizer for adhesives based on polyvinyl acetate. The compatibility of the phthalic acid esters with polyvinyl acetate ceases with diayl phthalate. Dioctyl phthalate is unsuitable for the polymer. Dicyclohexyl phthalate is available for powdered hot melt adhesives. 25 to 30% plasticizer is added to the polyvinyl acetate.
- the so-called all-purpose glue contains a maximum of 10% plasticizer, calculated on the binder; many products of this type are even free of plasticizers.
- Adhesives produced from high molecular weight polyvinyl chloride are only added in small amounts to plasticizers, such as dioctyl phthalate, if they are intended for bonding soft films.
- plasticizers such as dioctyl phthalate
- dibutyl phthalate and tricresyl phosphate alone or in a mixture, are the most important plasticizers.
- Adipic acid esters, apart from the polymer plasticizers, are also suitable, while esters of higher fatty acids and castor oil cannot be used (see page 376, left column).
- the plasticizer can also be built into the polymer (inner plasticizer). Suitable comonomers are used for this purpose, in the case of vinyl acetate, for example vinyl laurate, vinyl stearate or dioctyl maleate. A migration of the plasticizer is excluded. However, the production process is very complex, since the co-monomers first have to be prepared and the type and concentration of the comonomer is different for each application. In the older German application DE 4324474 a polyvinyl acetate dispersion for sand or earth wall attachment is described.
- plasticizer As a plasticizer, it contains nature-based triesters of glycerol of aliphatic monocarboxylic acids with 2 to 6 carbon atoms in the molecule, citric acid triesters with aliphatic monoalcohols with 2 to 6 carbon atoms and epoxidized rapeseed oil or epoxidized soybean oil in an amount of about 1 to 15% by weight. -%, based on an approximately 50 wt .-% aqueous polyvinyl acetate dispersion. The content of this teaching is to be excluded from protection.
- the object of the invention is to soften or elasticize binders and still not get the usual disadvantages, in particular not to reduce the adhesion to unacceptable values.
- the solution according to the invention can be found in the patent claims. It consists essentially in the addition of fatty substances.
- the fact that the strength is hardly changed is surprising, given the constant demand (see adhesive tubes) to dry the substrate surfaces and make them grease-free in order to achieve good adhesion.
- the surprise is particularly great because the fat content is not just a few percent, but generally 0.5 to 60 and expediently 10 to 50% by weight, in particular 15 to 40% by weight, based on the binder can be.
- the tensile shear strength of adhesives is then still> 1, preferably> 2, in particular> 4 N / mm 2 for beech wood.
- Fatty substances are to be understood as meaning fatty acids, fatty alcohols and their derivatives. Fat substances with a molecular weight> 300 or oligomerized fat substances with a molecular weight> 1000 are preferably used. You are lipophilic. “Fatty acids” mean acids which contain one or more carboxyl groups (-C00H), preferably one. The carboxyl groups can be connected to saturated, unsaturated and / or branched alkyl radicals having more than 8 carbon atoms. They can contain further groups such as ether, ester, halogen, amide, amino, urethane, hydroxyl and urea groups. However, carboxylic acids such as native fatty acids or fatty acid mixtures, dimer fatty acids and tri-fatty acids are preferred.
- carboxylic acids according to the invention are: capronic, caprylic, capric, lauric, myristic, palmitic, stearic, isostearic, isopalmitic, arachinic, behenic, cerotinic and melissic acids and also one - or polyunsaturated acids palmitoleic, oleic, elaidic, petroselinic, eurca, linoleic, linolenic, gadoleic acid and fatty acids obtained by oligomerization, eg dimer fatty acids.
- polyhydroxy fatty acids can also be used.
- These can be prepared, for example, by epoxidizing unsaturated fatty acids and ring-opening them with H-active compounds, for example alcohols, carboxylic acids, amines.
- H-active compounds for example alcohols, carboxylic acids, amines.
- the carboxylic acids can also be produced by chemical modification of fats and oils.
- the fats or oils or derivatives produced therefrom can be both of vegetable and animal origin or, if appropriate, can be specifically synthesized by a petrochemical route.
- Suitable carboxylic acids are also derivatives of all oil- and fat-based raw materials which are accessible, for example, through ene reactions, transesterifications, condensation reactions, grafting (for example with maleic anhydride or acrylic acid, etc.) and, for example, epoxidations with subsequent ring opening.
- Such basic oleochemical reactions can preferably be carried out on fats and oils with double bonds and / or OH groups, for example on fats and oils of rapeseed (new), sunflowers, soybeans, linseed, coconuts, oil pales, oil palm kernels and oil trees.
- Preferred fats and oils are, for example, beef tallow with a chain distribution of 67% oleic acid, 2% stearic acid, 1% heptadecanoic acid, 10% saturated acids with chain length C12 to C15, 12% linoleic acid and 2% saturated acids with> Ci ⁇ carbon atoms or e.g. the oil of the new sunflower (NSb) with a composition of approx. 80% oleic acid, 5% stearic acid, 8% linoleic acid and approx. 7% palmitic acid.
- NBS new sunflower
- En reactions are carried out at elevated temperature with e.g. Acid anhydrides performed on unsaturated fats and oils.
- Epoxidation of double bonds and subsequent ring opening with e.g. Amines, amino alcohols, alcohols, diols, polyols, hydroxycarboxylic acids or polycarboxylic acids enable e.g. access to the necessary fat and oil-based raw materials with acid or acid anhydride groups.
- the fatty acids as cleavage products of fats and oils with unsaturated groups or 0H functions can also be used for such reactions.
- Other reactions such as simultaneous or subsequent condensation or transesterification reactions can lead to a molecular weight build-up of the C00H-terminated fat and oil-based building blocks.
- the degree of oligomerization or the molecular weight and the nature of the starting raw materials should be chosen according to aspects generally known to the person skilled in the art so that the resulting oligomer can be readily processed.
- Esters or partial esters with mono- or polyhydric alcohols can be prepared as derivatives of the above-mentioned fatty acids.
- “Alcohol” means hydroxyl derivatives of aliphatic and alicyclic saturated, unsaturated and / or branched hydrocarbons. Both 1- and 2- or higher alcohols can be used. In addition to monohydric alcohols, this also includes the low molecular weight chain extenders or crosslinkers with hydroxyl groups which are known per se from polyurethane chemistry.
- Monophenyl glycol Monophenyl glycol glycol,
- the esterification with alcohols can also be carried out with the addition of other polycarboxylic acids for oligomerization.
- dicarboxylic acids are oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, glutaric acid, adipic acid, suberic acid, sebacic acid, 1,11-undecanedioic acid, 1,12-dodecanedioic acid, phthalic acid, isophthalic acid, terephthalic acid, hexahydrophthalic acid, dimer fatty acid or Tetrahydrophtha1klare.
- Adipic acid is preferably used.
- Amides of the above-mentioned fatty acids can also be used as derivatives. These can be obtained by reaction with primary and secondary amines or polyamines, e.g. with monoethanolamine, diethanolamine, ethylene diamine, hexamethyl diamine, ammonia etc.
- “Fatty alcohols” are understood to mean compounds which contain one or more hydroxyl groups.
- the hydroxyl groups can be connected to saturated, unsaturated and / or branched alkyl radicals having more than 8 carbon atoms. They can contain further groups, for example ether, ester, halogen, amide, amino, urea and urethane groups.
- fatty alcohols are: ricinoleyl alcohol, eruca alcohol, 12-hydroxystearyl alcohol, capron alcohol, caprylic alcohol, pelargoan alcohol, capric alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, erucyl alcohol, Ricinol alcohol, linoleyl alcohol, linolenyl alcohol, arachidyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol.
- symmetrical and asymmetrical ethers and esters with various mono- and polycarboxylic acids can be used.
- Monocarboxylic acids are ant, vinegar, propion, butter, valerie, capron, oenanth, caprylic, pelargon, caprin, undecane, lauric, tridecane, myristic, pentadecane, palmitin -, margarin, stearic, nonadecanoic, arachic, behenic, lignoceric, cerotinic and melissic acid.
- Polycarboxylic acids are, for example, oxalic acid, adipic acid, maleic acid, tartaric acid and citric acid.
- the fatty acids described above can also be used as the carboxylic acid.
- Esters of glycerol with fatty acids and their derivatives accessible via epoxidation are preferably used.
- examples of such derivatives are: epoxystearic acid methyl ester, epoxystearic acid, -2-ethyl-hexyl ester.
- the triglycerides of the glycerides are preferred, for example soybean oil epoxide, linseed oil epoxide, rapeseed oil epoxide, epoxidized sunflower oil.
- epoxidized triglycerides of unsaturated fatty acids ring-opened with nucleophiles can be used.
- nucleophiles are alcohols such as e.g. Methanol, ethanol, ethylene glycol, glycerol or trimethylolpropane or carboxylic acids such as e.g. To understand acetic acid, dimer fatty acid, maleic acid, phthalic acid or a mixture of fatty acids with 6 to 36 carbon atoms.
- the fatty alcohols can also be etherified, in particular with the same or different fatty alcohols, but also with other polyhydric alcohols, e.g. Alkyl polyglycosides.
- fats and oils are expediently used in their native form. Under certain circumstances, they can also be used after thermal and / or oxidative treatment. It is also possible to use epoxidation or the addition of maleic anhydride use accessible derivatives. Specific examples are: palm oil, peanut oil, turnip oil, cottonseed oil, soybean oil, castor oil, sunflower oil, linseed oil, stand oils, blown oils, epoxidized soybean oil, epoxidized linseed oil, rapeseed oil, coconut oil, palm kernel oil and tallow if the fatty substance contains the fatty poly mer is added, and greater than 100 if it is present in a radical polymerization. These fatty substances are particularly suitable for polyvinyl esters.
- desiccants in amounts of 1 to 5% by weight, based on the fatty substance.
- binder are the usual inorganic or organic substances, in particular natural or synthetic polymers.
- inorganic binders are in question: water glass, cement, plaster, anhydrite, magnesia or lime. These binders are notable for particularly high hardness and often for insufficient water resistance. Here it can be particularly advantageous to add the fatty substances according to the invention before or during the hardening phase in order to improve the elasticity and the water resistance.
- the synthetic polymers have an average molecular weight of 8,000 to 2,000,000, preferably 10,000 to 800,000 and in particular from 30,000 to 300,000.
- the polymers can also contain monomers in minor amount contained, for example ⁇ 20, in particular ⁇ than 5 wt .-%, based on the polymer. They usually form the basis for hot melt, plastisol, dispersion and solvent adhesives.
- These are the following polymers: polyurethanes, poly (meth) acrylates, polyvinyl esters, polystyrene, polybutadiene, polyamides, polyesters and polyvinyl chloride. The following are preferably excluded: polystyrene and polycyanoacrylate.
- the corresponding copolymers can also be used, e.g. Made of polyvinyl ester / ethylene, polyacrylate / vinyl ester.
- the preferred polymers are polyurethanes, polyacrylates with 1 to 22, in particular 1 to 4, carbon atoms in the alcoholic component and polyvinyl esters with 1 to 22, in particular 1 to 10, carbon atoms in the acid residue, for example vinyl acetate, vinyl propionate, vinyl butyrate, vinyl versatate, Vinyl laurate, vinyl stearate or ethyl, butyl and 2-ethylhexyl acrylate.
- Polyvinyl acetate is particularly preferred.
- This also includes its copolymers, in particular with ethylene, acrylates, acrylic acid, methacrylic acid and maleinates, in particular with up to 8 carbon atoms in the alcohol component, vinyl chloride and crotonic acid.
- Specific comonomers of vinyl acetate are: dibutyl and diethyl maleate, ethyl, butyl and 2-ethylhexyl acrylate.
- Typical terpolymers are obtained from vinyl acetate and butyl acrylate / N-hydroxyethyl-acrylamide, ethylene / vinyl chloride, vinyl laurate / vinyl chloride and ethylene / acrylamide.
- the acetate groups can also be partially saponified.
- the amount of comonomers e.g. in the PVAC can make up 0 to 30% by weight, based on the copolymer.
- the above-mentioned physically setting polymers can also contain reactive groups which react in particular with the moisture, the light or the oxygen in the air.
- reactive groups which react in particular with the moisture, the light or the oxygen in the air.
- Specific examples are: isocyanate and silane groups. They are contained in a concentration of up to 10% by weight, based on the polymer.
- the chemically setting polymers are also suitable.
- These can be oxygen-induced post-polymerizations, for example in the case of strongly unsaturated oils and fats such as linseed oil and window putty.
- Another possibility is the moisture-induced reaction of, for example, NCO- or alkoxysilane-terminated polymers and polymer precursors.
- Examples of this are the light-induced polymerizations, in particular of acrylates, the self-crosslinking of dispersions via ionic reactions after evaporation of the water or the solvent, or the postcrosslinking due to the reaction of aldehyde or keto groups.
- crosslinking via polyvalent metal ions such as Zn2 + , Zr2 + , Fe3 + , Al3 + f Cr3 + and Mg2 + or postcrosslinking via diaziridines or aldehydes in the case of dispersions with keto, aldehyde or hydroxyl groups are known.
- the binder can be liquid, pasty or solid at room temperature (20 ° C). In particular, it is liquid, expediently an aqueous dispersion with a solids content of 20 to 85, preferably 35 to 80, in particular 45 to 75% by weight.
- the preparation of the binder according to the invention can be designed very flexibly. It is thus possible to add the fatty substance before, during or after the production of the physically setting polymer, if it does not interfere. This could be expected, for example, with cyanoacrylates.
- the preparation of the polymers can be carried out by various processes known in polymer chemistry, e.g. via bulk polymerization, polymerization in a suitable solvent, e.g. Toluene, or - preferably - in an aqueous emulsion or suspension according to the methods of emulsion or suspension polymerization known per se.
- a suitable solvent e.g. Toluene
- the monomers and the fatty substances are polymerized in water with the addition of an emulsifier or a protective colloid.
- the polymerization can preferably be carried out in the presence of a protective colloid.
- Protective colloids include hydrophilic polymers such as Carboxymethyl cellulose or gum arabic in question.
- Polyvinyl alcohol can particularly preferably be used. In this sense, polyvinyl alcohol is also understood to mean a partially saponified polyvinyl acetate.
- the amount of protective colloid can be in the range from 0.5 to 10% by weight, based on monomers, which is customary for suspension polymerizations. Amounts of 1 to 3% by weight, based on monomers, are preferred.
- the polymerization can be carried out in such a way that the vinyl esters and optionally other free-radically polymerizable olefinic monomers are mixed with the fatty substances and this mixture is added to an aqueous solution of the protective colloid. This addition can preferably be carried out continuously with simultaneous polymerization, but batchwise polymerization of the entire amount of monomer is also possible.
- the solids content of the emulsions or suspensions of the binder according to the invention is between 20 and 75% by weight, preferably between 40 and 60% by weight.
- Organosoluble initiators such as e.g. Benzoyl peroxide or water-soluble initiators such as e.g. Hydrogen peroxide or the alkali or ammonium salts of persulfates can be used. So-called redox initiators can also be used.
- the amount of initiator can be in the usual range from 0.01 to 1% by weight, based on monomers. Quantities of 0.1 to 0.5% by weight are preferably used.
- the reaction temperatures can be between 20 and 95 ° C, the reaction times can be between 1 and 8 hours.
- the fatty substance can be added during the polymerization, but it is expedient to add it after the polymerization. It is simplest to produce the binder according to the invention by intensive mixing of the fatty substance with a dispersion of the polymer. This can e.g. in stirring units, high-speed stirrers or in a ball mill. However, it is also possible to first disperse the fatty substance with the addition of dispersants and then to mix the two dispersions. The fatty substance can, however, also be admixed with the melted, physiologically setting polymer, if appropriate in the heat.
- additives can be added to the binder, for example waxes, fillers, pigments, dispersants, stabilizers, viscosity regulators, preservatives, solvents and resins. They are known, as is their admixture.
- the fatty substances according to the invention can also be mixed in together with these additives. A later addition is also possible.
- the addition of the fatty substances according to the invention to the physically binding polymers results in an increased shape-changing capacity and a reduced hardness. Surprisingly, the tendency to exudate is also very low, at least up to fat additions of 20% by weight.
- the water resistance of the bonds is also positively influenced.
- the wetting properties of the aqueous dispersion adhesives are also more favorable.
- the strength is hardly reduced: wood gluing still causes a wood break, at least in part. This also applies to long-term warm storage. The heat resistance is also remarkably high. The viscosity is reduced and thus the workability is improved.
- the binders according to the invention can be used as adhesives, adhesive sealants and coating compositions, in particular when peak strengths are less important than an inexpensive means.
- they are suitable for substrates with different elastic behavior or different coefficients of thermal expansion, which is usually the case with different substrates.
- Suitable substrates are: wood, cardboard, paper, wall coverings such as wallpaper, cork, leather, felt, textiles, plastics - in particular floor coverings made of PVC, linoleum and polyolefins, be it in the form of foils or textile fabrics -, mineral substrates such as glass , Quartz, slag, rock and ceramics and metals.
- the binders according to the invention are particularly suitable for the production of dispersion adhesives, glue sticks, plastisols and hot melt adhesives or of melt sealants or paste-like sealants such as joint sealants. Coating of hard surfaces such as textiles and paper is also possible.
- the compositions according to the invention are suitable as binders for the assembly of adhesives, sealants and coating compositions.
- adhesives hotmelt, solvent, dispersion, assembly, pressure-sensitive and contact adhesives as well as redispersible powder, all-purpose glue and glue sticks.
- adhesives hotmelt, solvent, dispersion, assembly, pressure-sensitive and contact adhesives as well as redispersible powder, all-purpose glue and glue sticks.
- the following are to be glued: paper, cardboard, wood, textiles, wall coverings, tiles, labels, leather, rubber, plastics, glass, ceramics and metal.
- coatings plastisol, emulsion paint and roof insulation.
- the sealing compounds can be used both in the construction and in the vehicle sector.
- the composition according to the invention can also be added to hydraulic binders, e.g. Cement or plaster.
- the adhesive obtained was applied on both sides to the narrow ends of the large wooden surfaces of six three-layer 50x80x4 mm beech plywood panels using a 1 mm notched trowel.
- two wooden plates were brought into contact overlapping 2 cm on the narrow side, fixed with four clothes pegs each and, after a storage time of 16 hours at room temperature, torn with a pull of 15 mm / minute on a Zwick tearing machine.
- the composition of the adhesives and the result of the bonds are shown in Table 1.
- perforated solid 25xl00x4mm beechwood plates were glued as described above with an overlap zone of 25x25mm. After a drying time of 16 hours at room temperature, the bonds under a load of 1350 g were heated from 50 to 200 ° C. in the course of 5 hours and left at this temperature for 20 minutes. All bonds withstood this strain.
- uncoated white writing paper was thinly coated on one side with adhesive and glued to a second layer of paper with manual smoothing.
- the penetration of the fats contained in the adhesive was assessed optically again and again in the backlight up to a total storage time of four weeks.
- Mix 5 and Ponal wood adhesive were drawn out using a stainless steel doctor with a gap width of 250 ⁇ m on glass plates to form a film of approximately 45 ⁇ m (determined using an Erichsen film thickness measuring device).
- the polymerization was started by draining 11.1 ml of the ammonium persulfate solution into the flask and starting the continuous metering of the vinyl acetate / fat mixture. The metering was controlled so that the total amount was metered in in about 4 hours. The remaining ammonium peroxodisulfate solution was also metered in continuously over the same period.
- the dispersion was cooled to room temperature and filled.
- the dispersion was stable for 6 months.
- the films from it were soft and elastic.
- Fatty substances also show excellent plasticizing effects with polyacrylates.
- Homo-polybutyl acrylate films are immersed in the test substances for 24 hours at room temperature (20 ° C) and at 60 ° C.
- the swelling of the homopolymer is given in percent, 100% representing the starting volume.
- oleochemical esters have a swelling capacity similar to that of plasticizers a), b) and c) recommended for acrylate dispersions:
- TG glass transition temperature
- the solids concentration (LC) was determined as follows: 5 to 10 g of the sample are heated in an aluminum dish at 120 to 130 ° C. for 2 hours. Then it is weighed back.
- the viscosity (Visk) was determined as follows: Brookfield RVT (20 ° C).
- the elongation at break was determined under the following conditions: Instron 4302, automatic material testing system Series IX, sample width 5 mm, sample thickness 1 mm, sample length 15 mm, tensile speed 200 mm / min ..
- the compatibility of the components was determined as follows: The films were stored at 60 ° C. between silicone paper and assessed after 3 weeks with regard to staining of the paper.
- the tackiness (RK) was determined as follows: A steel ball (diameter 20 mm, weight 32.25 g) rolled down a ramp (height 26 mm; running distance 115 mm) onto a film of the composition according to the invention). The distance covered on the polymer film was measured (in mm).
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Ceramic Engineering (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Structural Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Inorganic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Fats And Perfumes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Laminated Bodies (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK95931182T DK0778870T3 (da) | 1994-08-31 | 1995-08-22 | Fysisk og/eller kemisk afbindende bindemiddel |
MX9701585A MX9701585A (es) | 1994-08-31 | 1995-08-22 | Aglutinantes de fraguado fisico y/o quimico. |
DE59506114T DE59506114D1 (de) | 1994-08-31 | 1995-08-22 | Physikalisch und/oder chemisch abbindende bindemittel |
EP95931182A EP0778870B1 (de) | 1994-08-31 | 1995-08-22 | Physikalisch und/oder chemisch abbindende bindemittel |
JP8508465A JPH10505373A (ja) | 1994-08-31 | 1995-08-22 | 物理的および/または化学的に硬化するバインダー |
GR990401464T GR3030410T3 (en) | 1994-08-31 | 1999-06-03 | Physically and/or chemically setting binders |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4430875A DE4430875A1 (de) | 1993-10-20 | 1994-08-31 | Bindemittel |
DEP4430875.2 | 1994-08-31 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1996006897A2 true WO1996006897A2 (de) | 1996-03-07 |
WO1996006897A3 WO1996006897A3 (de) | 1996-05-30 |
Family
ID=6526994
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1995/003331 WO1996006897A2 (de) | 1994-08-31 | 1995-08-22 | Physikalisch und/oder chemisch abbindende bindemittel |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP0778870B1 (de) |
JP (1) | JPH10505373A (de) |
AT (1) | ATE180820T1 (de) |
CA (1) | CA2198773A1 (de) |
DE (1) | DE19531849A1 (de) |
DK (1) | DK0778870T3 (de) |
ES (1) | ES2135085T3 (de) |
GR (1) | GR3030410T3 (de) |
MX (1) | MX9701585A (de) |
WO (1) | WO1996006897A2 (de) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999024522A1 (de) * | 1997-11-07 | 1999-05-20 | Henkel Kommanditgesellschaft Auf Aktien | Polyacrylat-fugendichtungsmasse |
JPH11335629A (ja) * | 1998-05-26 | 1999-12-07 | Haseko Corp | 建築物用無機系水性接着剤及びそれを用いた建築物の施工法 |
EP1247464A2 (de) * | 2001-04-06 | 2002-10-09 | Hauni Maschinenbau AG | Transportmittel für die tabakverarbeitende Industrie |
WO2003040234A1 (de) * | 2001-11-07 | 2003-05-15 | Cognis Deutschland Gmbh & Co. Kg | Giessbare zusammensetzungen |
WO2005108571A1 (ja) * | 2004-05-07 | 2005-11-17 | Konica Minolta Medical & Graphic, Inc. | 検査用マイクロリアクタおよび遺伝子検査装置ならびに遺伝子検査方法 |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6559213B2 (en) | 1995-03-16 | 2003-05-06 | Henkel-Teroson Gmbh | Plastisol composition |
DE19509085B4 (de) * | 1995-03-16 | 2004-05-19 | Henkel Teroson Gmbh | Plastisol-Zusammensetzung, ihre Herstellung und Verwendung |
DE19624148A1 (de) | 1995-06-22 | 1997-01-02 | Henkel Kgaa | Masse zum Kleben, Dichten und Beschichten |
AU9303398A (en) * | 1997-09-08 | 1999-03-29 | National Starch And Chemical Investment Holding Corporation | The use of natural oils in hot melt adhesives |
DE19831000C1 (de) * | 1998-07-10 | 1999-10-21 | Henkel Kgaa | Mischung aus Kolophonium-Harz und Wachs |
US7160945B1 (en) | 1999-03-22 | 2007-01-09 | The Curators Of The University Of Missouri | Water borne film-forming compositions |
DE10034607A1 (de) | 2000-07-20 | 2002-02-07 | Gundram Jung | Multispezifisches Reagenz zur selektiven Stimulierung von Zelloberflächenrezeptoren |
EP1541625B1 (de) * | 2002-07-11 | 2008-05-07 | Mitsubishi Rayon Co., Ltd. | Viskositaetsmodifikator für eine plastisolzusammensetzung, plastisolzusammensetzung und produkt und formkoerper daraus |
DE102005031945A1 (de) * | 2005-07-08 | 2007-01-11 | Construction Research & Technology Gmbh | Verwendung von entfärbtem Biodiesel als Weichmacher |
RU2421560C2 (ru) | 2006-03-23 | 2011-06-20 | Геркулес Инкорпорейтед | Улучшенная бумага для гипсовых стеновых плит |
UA112960C2 (uk) | 2009-12-18 | 2016-11-25 | Акцо Нобель Кемікалз Інтернешнл Б.В. | Спосіб і добавка для поліпшення адгезії будівельних композицій до основ |
MX2013014200A (es) | 2011-06-10 | 2014-03-21 | Akzo Nobel Chemicals Int Bv | Proceso y aditivo para mejorar la adherencia de las composiciones a los sustratos. |
DE102012207801A1 (de) | 2012-05-10 | 2013-11-14 | Wacker Chemie Ag | Verwendung von Copolymerisaten als Klebrigmacher für Klebstoffe |
DE102013226505A1 (de) * | 2013-12-18 | 2015-06-18 | Henkel Ag & Co. Kgaa | Hitzehärtbare Kautschuk-Zusammensetzungen mit plastisol-artigem Fließverhalten |
KR101887638B1 (ko) * | 2017-09-27 | 2018-08-10 | 한화케미칼 주식회사 | 염화비닐계 수지 조성물 및 이의 제조 방법 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH257408A (de) * | 1947-08-01 | 1948-10-15 | Roempler George | Wasserlöslicher, elastischer Leim, z. B. für Etiketten und Tapeten. |
FR1011688A (fr) * | 1949-03-04 | 1952-06-25 | Dawant Et Kurt Elias A | Procédé pour rendre fluide les mélanges à base d'acétates polyvinyliques fortement polymérisés |
DE1054621B (de) * | 1957-08-19 | 1959-04-09 | Blanc Omya Sa Du | Verfahren zur Herstellung eines Grundstoffes fuer die Anfertigung von Kitten und Spachtelmassen |
FR2069573A5 (en) * | 1969-11-17 | 1971-09-03 | Ici Ltd | Water activated adhesives |
US3991025A (en) * | 1974-04-12 | 1976-11-09 | Novagard Corporation | Urethane containing hot melt sealants, adhesives and the like |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4124551A (en) * | 1977-09-26 | 1978-11-07 | The Sherwin-Williams Company | Aliphatic hydrocarbon solvent reducible acrylic enamel of improved quality |
DE3110967A1 (de) * | 1981-03-20 | 1982-09-30 | Henkel KGaA, 4000 Düsseldorf | Kleber und/oder beschichtungsmassen auf basis von alkalimetallsilikatloesungen und deren verwendung |
US4656213A (en) * | 1984-10-26 | 1987-04-07 | Atlantic Richfield Company | Acrylic hot melt pressure sensitive adhesive compounds |
DE3523319A1 (de) * | 1985-06-29 | 1987-01-08 | Basf Ag | Bindemittel fuer waessrige, physikalisch trocknende korrosionsschutzanstriche auf basis einer phosphorsaeuremonoalkylester enthaltenden polymer-dispersion |
CS259825B1 (cs) * | 1986-09-11 | 1988-11-15 | Lumir Mandik | Snimateiná akrylátová kontaktní lepidla |
DE3638224A1 (de) * | 1986-11-08 | 1988-05-19 | Baden Chemie Gmbh | Elastische dichtungsmasse |
US4869934A (en) * | 1988-09-16 | 1989-09-26 | Sterling Drug Inc. | Floor polishing and coating composition |
JPH0341465A (ja) * | 1989-07-10 | 1991-02-21 | Tomoegawa Paper Co Ltd | 静電荷像現像用トナー |
-
1995
- 1995-08-11 DE DE19531849A patent/DE19531849A1/de not_active Withdrawn
- 1995-08-22 JP JP8508465A patent/JPH10505373A/ja active Pending
- 1995-08-22 CA CA002198773A patent/CA2198773A1/en not_active Abandoned
- 1995-08-22 DK DK95931182T patent/DK0778870T3/da active
- 1995-08-22 WO PCT/EP1995/003331 patent/WO1996006897A2/de not_active Application Discontinuation
- 1995-08-22 AT AT95931182T patent/ATE180820T1/de not_active IP Right Cessation
- 1995-08-22 ES ES95931182T patent/ES2135085T3/es not_active Expired - Lifetime
- 1995-08-22 MX MX9701585A patent/MX9701585A/es unknown
- 1995-08-22 EP EP95931182A patent/EP0778870B1/de not_active Revoked
-
1999
- 1999-06-03 GR GR990401464T patent/GR3030410T3/el unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH257408A (de) * | 1947-08-01 | 1948-10-15 | Roempler George | Wasserlöslicher, elastischer Leim, z. B. für Etiketten und Tapeten. |
FR1011688A (fr) * | 1949-03-04 | 1952-06-25 | Dawant Et Kurt Elias A | Procédé pour rendre fluide les mélanges à base d'acétates polyvinyliques fortement polymérisés |
DE1054621B (de) * | 1957-08-19 | 1959-04-09 | Blanc Omya Sa Du | Verfahren zur Herstellung eines Grundstoffes fuer die Anfertigung von Kitten und Spachtelmassen |
FR2069573A5 (en) * | 1969-11-17 | 1971-09-03 | Ici Ltd | Water activated adhesives |
US3991025A (en) * | 1974-04-12 | 1976-11-09 | Novagard Corporation | Urethane containing hot melt sealants, adhesives and the like |
Non-Patent Citations (1)
Title |
---|
DATABASE KKF DKI/FIZ CHEMIE 81(47):5381, & PLASTE KAUTSCH., Bd. 27, Nr. 9, 1980 DE, Seiten 526-527, PAWLOWA M. ET AL. 'Wasserbeständige Polyurethandichtungskitte auf der Basis von umgeestertem Rizinusöl.' * |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999024522A1 (de) * | 1997-11-07 | 1999-05-20 | Henkel Kommanditgesellschaft Auf Aktien | Polyacrylat-fugendichtungsmasse |
AU735891B2 (en) * | 1997-11-07 | 2001-07-19 | Henkel Kommanditgesellschaft Auf Aktien | A Polyacrylate jointing compound |
CN1121467C (zh) * | 1997-11-07 | 2003-09-17 | 亨克尔两合股份公司 | 聚丙烯酸酯粘接配料 |
US6828382B1 (en) | 1997-11-07 | 2004-12-07 | Henkel Kommanditgesellschaft Auf Aktien | Polyacrylate joint sealants |
JPH11335629A (ja) * | 1998-05-26 | 1999-12-07 | Haseko Corp | 建築物用無機系水性接着剤及びそれを用いた建築物の施工法 |
EP1247464A2 (de) * | 2001-04-06 | 2002-10-09 | Hauni Maschinenbau AG | Transportmittel für die tabakverarbeitende Industrie |
EP1247464A3 (de) * | 2001-04-06 | 2004-05-26 | Hauni Maschinenbau AG | Transportmittel für die tabakverarbeitende Industrie |
WO2003040234A1 (de) * | 2001-11-07 | 2003-05-15 | Cognis Deutschland Gmbh & Co. Kg | Giessbare zusammensetzungen |
WO2005108571A1 (ja) * | 2004-05-07 | 2005-11-17 | Konica Minolta Medical & Graphic, Inc. | 検査用マイクロリアクタおよび遺伝子検査装置ならびに遺伝子検査方法 |
Also Published As
Publication number | Publication date |
---|---|
ATE180820T1 (de) | 1999-06-15 |
MX9701585A (es) | 1997-05-31 |
GR3030410T3 (en) | 1999-09-30 |
DE19531849A1 (de) | 1996-03-07 |
ES2135085T3 (es) | 1999-10-16 |
CA2198773A1 (en) | 1996-03-07 |
EP0778870A2 (de) | 1997-06-18 |
DK0778870T3 (da) | 1999-12-27 |
EP0778870B1 (de) | 1999-06-02 |
JPH10505373A (ja) | 1998-05-26 |
WO1996006897A3 (de) | 1996-05-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0778870B1 (de) | Physikalisch und/oder chemisch abbindende bindemittel | |
DE69424105T2 (de) | Verwendung von niedrig-toxischen Lösungsmitteln in Klebstoffen auf wässriger Basis | |
EP0370299B1 (de) | Wässriges Beschichtungsmittel, ein Verfahren zu seiner Herstellung und seine Verwendung | |
EP0843710B1 (de) | Polystyrol-bindemittel | |
DE2354362A1 (de) | Klebemasse | |
EP0833864B2 (de) | Masse zum kleben, dichten und beschichten | |
CH708031B1 (de) | Chloroprenkautschukbasierte Polymerlatexzusammensetzung. | |
EP0062906A2 (de) | Wässrige Polyvinylester-Dispersion, Verfahren zu ihrer Herstellung und ihre Verwendung | |
DE60004034T2 (de) | Wässrige filmbildende zusammensetzungen | |
WO1997040117A1 (de) | Harzhaltige dispersionsklebstoffe | |
EP1030897B1 (de) | Polyacrylat-fugendichtungsmasse | |
DE60210589T2 (de) | Verdickte wässrige Überzugszusammensetzungen, die filmbildende Polymerbindemittel enthalten | |
DE4430875A1 (de) | Bindemittel | |
DE19944159A1 (de) | Emissionsarmer, biologisch abbaubarer Klebstoff | |
DE1569910C3 (de) | Kitte und Dichtungsmassen auf der Basis von Polymerisaten äthylenisch ungesättigter Verbindungen | |
EP0897965A2 (de) | Physikalisch und/oder chemisch abbindende Bindemittel | |
DE2636863A1 (de) | Kaltvernetzende dispersionskleber | |
DE10338858A1 (de) | Montagekleber auf Basis einer wässrigen Polymer-Dispersion | |
EP0144808B1 (de) | Haftschmelzklebstoffe, ihre Herstellung und Verwendung | |
DE19725038B4 (de) | Emissionsarmer wäßriger Dispersions-Klebstoff und seine Verwendung | |
EP1474493B1 (de) | Emissionsarmer wässriger dispersions-klebstoff | |
DE1949497C (de) | Verfahren zur Herstellung von Dispersions-Anstrichstoffen | |
DE10252978A1 (de) | Chemisch inerter Haftkleber mit verbesserter Haftung, Verfahren zu seiner Herstellung und Verwendung | |
EP0521920B1 (de) | Tiefenwirksame grundierung | |
EP0633898B1 (de) | Ionische polymere |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 95194596.3 Country of ref document: CN |
|
AK | Designated states |
Kind code of ref document: A2 Designated state(s): CA CN JP MX RU US |
|
AL | Designated countries for regional patents |
Kind code of ref document: A2 Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE |
|
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
AK | Designated states |
Kind code of ref document: A3 Designated state(s): CA CN JP MX RU US |
|
AL | Designated countries for regional patents |
Kind code of ref document: A3 Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 1995931182 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: 2198773 Country of ref document: CA Ref document number: 2198773 Country of ref document: CA Kind code of ref document: A |
|
ENP | Entry into the national phase |
Ref document number: 1997 793589 Country of ref document: US Date of ref document: 19970228 Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: PA/a/1997/001585 Country of ref document: MX |
|
WWP | Wipo information: published in national office |
Ref document number: 1995931182 Country of ref document: EP |
|
WWG | Wipo information: grant in national office |
Ref document number: 1995931182 Country of ref document: EP |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: 1995931182 Country of ref document: EP |