HK1794A - Use of aqueous polyurethane dispersions as domestic universal adhesive and their preparation - Google Patents
Use of aqueous polyurethane dispersions as domestic universal adhesive and their preparation Download PDFInfo
- Publication number
- HK1794A HK1794A HK17/94A HK1794A HK1794A HK 1794 A HK1794 A HK 1794A HK 17/94 A HK17/94 A HK 17/94A HK 1794 A HK1794 A HK 1794A HK 1794 A HK1794 A HK 1794A
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- HK
- Hong Kong
- Prior art keywords
- polyol
- polyurethane dispersions
- weight
- difunctional
- propionic acid
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- C—CHEMISTRY; METALLURGY
- 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
- 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
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)
- Polyethers (AREA)
- Paints Or Removers (AREA)
- General Preparation And Processing Of Foods (AREA)
- Hydrogenated Pyridines (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Materials For Medical Uses (AREA)
- Adhesive Tapes (AREA)
Abstract
A general purpose household adhesive comprises an essentially clear and at least largely solvent-free polyurethane aqueous dispersion based on: a mixture of polyols composed wholly or partly of polytetrahydrofurane; a bi- or multi-functional isocyanate component having an OH:NCO ratio with respect to the mixture of polyols between 1:0.5 and 1:2.0, preferably between 1:1.0 and 1:1.7 and in particular between 1:1.05 and 1:1.6; a functional component capable of forming salts in an aqueous solution; and, if desired, a chain-lengthening agent.
Description
The invention relates to the use of special polyurethane dispersions, which are essentially clearer, more aqueous and at least largely solvent-free, as household adhesive.
The purpose of all-purpose adhesives is to adhere to a wide range of household substrates (paper, cardboard, photographs, textiles, leather, felt, felt, cork, film, metals such as aluminium and iron, porcelain, ceramics, glass, wood, various plastics, as well as polystyrene foams).
Compared to the great variety of adhesives used in industry and crafts, few materials can meet the high requirements for the universality of a household adhesive, and only polyvinyl acetate and its copolymers, usually in solution or as a dispersion for wood gluing, have been widely used.
The requirement of universality is a particularly difficult selection criterion for an adhesive, which ultimately means that the adhesive molecules must have an equal affinity for polar and nonpolar surfaces.
In addition to the demand for universality, the recent desire for household adhesives is to achieve odor-neutral, solvent-free, physiologically safe, clear, aqueous formulations, which should at the same time lead to adhesives whose dried films have a certain water resistance, and which should also be able to bind difficult-to-stick substrates such as plastics.
This requirement could not be met either by the polyvinyl acetate and vinyl acetate copolymers, the binders hitherto preferred for all adhesives, or by alternatives such as nitrocellulose in all respects. Although polyvinyl acetate can be produced solvent-free in the form of aqueous dispersions, these dispersions are not transparent but milky white. They exhibit good performance, for example, when used as wood glues.
Surprisingly, it has now been found that specially selected embodiments of the aqueous polyurethane dispersions known for decades are suitable as multi-purpose adhesives.
The German notice 15 95 602 of 1966 describes in detail a process for the production of cationically modified polyurethane dispersions containing quartz ammonium groups in a quantity of at least 0,21% as dispersive components. The notice mentions numerous polyoles, numerous isocyanate compounds and numerous cationic salt-forming components as modifying agents. The following are also the common chain-extenders. The procedure described therein makes it possible to produce optically clear, almost colloidal solutions of associates which are non-adhesive or sticky.
The broad disclosure of DE 15 95 602 covers both polyurethane dispersions using polyester as OH functional component and polyether or polyacetals; however, polyurethane dispersions based on polyurethanes made from OH functional polyesters are not suitable as household adhesives because they undergo hydrolysis when stored and therefore do not have the required storage stability; polyurethane dispersions based on polyurethylene oxide and/or polypropylene oxide as OH functional components are also not suitable as multi-purpose adhesives because they exhibit poor aeration on the plastic surface and thus do not meet the requirement of universality.
DE 15 95 602 lists polytetrahydrofuran as a possible polyol, but there is no evidence that this particular polyol is a suitable basis for polyurethane dispersions for household adhesives.
The Japanese patent application No 62 (1987)-112676, published on 23 May 1987, is known to contain an aqueous polyurethane adhesive containing an aqueous polyurethane dispersion obtained by conversion of a polytetrahydrofurandiol with a multifunctional isocyanate. In particular, the Japanese disclosure instructs that polytetrahydrofurandiol (molecular weights 400 to 2000) is to be converted with organic diisocyanates and a dimethyl sulphuric acid, to undergo a chain extension step with hydrazine and, after neutralization, to be converted with a tertiary amine with an aqueous epoxy or an aqueous azidine.
The purpose of the invention is therefore to demonstrate that special aqueous transparent polyurethane dispersions satisfy the complex and sometimes contradictory requirements previously described for household adhesives.
The invention is intended to use a substantially clear and at least largely solvent-free aqueous polyurethane dispersion based on the reaction products
A polyol mixture consisting wholly or partly of polytetrahydrofuran, with an OH:NCO ratio of 1: 0.5 to 1: 2,0 is preferred to 1: 1.0 to 1: 1,7 and in particular to 1: 1.05 to 1: 1.6, using a two- or multifunctional isocyanate component and dimethylolpropionic acid as a functional component capable of salting in aqueous solution as a household glue.
The polyurethanes used in the polyurethane dispersions of the invention are based on a polymeric mixture of polytetrahydrofuran, whether or not in whole or in part, with a polytetrahydrofuran content of not less than 30% and preferably not less than 70% by weight in relation to polymeric mixtures.
In addition to the polytetrahydrofuranediols, analogue compounds may be used, in which up to 50% of the tetrahydrofuran units involved in the construction of the polyoles are replaced by ethylene oxide or propylene oxide. Among these compounds, those composed of 25 to 30% mol of ethylene oxide units and 75 to 70% mol of tetrahydrofuranedioxide units are preferred.
The polytetrahydrofuran polyoles which are the basis of the polyurethane dispersions used in accordance with the invention can still be replaced up to 70% by weight by other polyoles commonly used in such preparations.
Polyethers are, for example, the polymerization products of ethylene oxide, propylene oxide, butylene oxide and their mixed or grafted polymerization products, as well as polyethers obtained by condensation of or mixtures of polyethylene alcohols and by alkoxylation of polyethylene alcohols, amines, polyamines and aminoalcohols.
For example, compounds which can be produced from glycols such as diethylene glycol, triethylene glycol, hexandiol and formaldehyde can be considered polyacetals.
The polythioethers are in particular the condensation products of thiodiglycol on its own and/or with other glycols, dicarboxylic acids, formaldehyde, aminocarboxylic acids or aminoalcohols. Depending on the co-components, the products are polythioether, polythiomischether, polythioeether ester, polythioeether esteramide. Such polyhydroxyl compounds can also be used in alkylated form or in combination with alkylating agents.
Polyesters, polyesters and polyamides include those derived from polyvalent saturated and unsaturated carbon acids or their anhydrides and polyvalent saturated and unsaturated alcohols, amino alcohols, diamines, polyamines and their mixtures, mainly linear condensates, as well as, for example, polyterephthalates or polycarbonates.
Polyhydroxyl compounds already containing urethane or urea groups and, where appropriate, modified natural polyoles such as castor oil are also suitable. In general, polyhydroxyl compounds with basic nitrogen atoms are also suitable, e.g. polyalkoxylated primary amines or polyester or polythioether containing alkyl diethanolamine in condensation. Polyoles which can be produced by complete or partial ring opening of epoxy triglycerides with primary or secondary hydroxyl compounds, such as the conversion product of epoxy soybean oil with methanol, may also be used.
All aromatic and aliphatic diisocyanates are suitable as polyisocyanates in the polyurethane dispersions of the invention, such as 1,5-naphthylenediisocyanate, 4,4-methylmethylmethylmethylisocyanate, 4,4-methylmethylmethylmethylmethylisocyanate, di- and tetraalkylmethylmethylisocyanate, 4,4-methylmethylisocyanate, 1,3-phenylenediisocyanate, 1,4-phenylenediisocyanate, which are isomers of toluene diisocyanate, given alone or in mixture, 1,4-methylmethylmethylmethylisocyanate, 1,4-methylmethylmethylmethylisocyanate, 1,4-methylmethylmethylmethylisocyanate, 1,4-methylmethylisocyanate, 1,4-methylisocyanate, 1,4-methylisocyanate, 1,4-methylisocyanate, 1,4-methylisocyanate, 1-methylisocyanate, 1-methylisocyanate, 1-methylisocyanate, 1-methylisocyanate, 1-methylisocyanate, 1-methylisocyanate, 1-methylisocyanate, 1-methylisocyanate, 1-methylisocyanate, 1-methylisocyanate, 1-methylisocyanate, 1-methylisocyanate, 1-methylisocyanate, 1-methylisocyanate, 1-methylisocyan, 1-methylisocyan, 1-methylisocyan, 1-methylisocyan, 1-methylisocyan, 1-methylisocyan, 1-methylisocyan, 1-methylisocyan, 1-methylisocyan, 1-methylisocyan, 1-methylisocyan, 1-methylisocyan, 1-methyl, 1-methylisocyl, 1-methylisocyl, 1-methyl, 1-methyl, 1-methyl, 2-methyl, 1-methyl, 2-methyl, 1-methyl, 2-methyl, 1-methyl, 2-methyl, 1-methyl, 2-methyl, 1-methyl, 2-meth
Partially capped polyisocyanates, which allow the formation of self-assembling polyurethanes, e.g. dimeric toluene isocyanate, or polyisocyanates partially converted with e.g. phenolics, tertiary butanol, phthalimide, caprolactam, are of interest.
The polyurethanes used in the polyurethane dispersions of the invention continue to have dimethyl propionic acid as an important functional component capable of salt formation in aqueous solution.
According to the invention, it is preferable to set the polyurethane prepolymers to be used to be soluble in water by the amount of dimethylolpropionic acid reacted, since such modified polyurethane dispersions can be replaced under alkaline conditions, i.e. such adhesives can be removed from certain substrates, e.g. textiles, under washing conditions.
The polymers in the dispersions of polyurethane used in accordance with the invention are in the form of salts. The polymers modified with dimethylolpropionic acid contain alkali metal salts, ammonia or amines, i.e. primary, secondary or tertiary amines, as antigenic agents. The groups capable of forming salts can be partially or completely neutralized by the antigenic agents. An excess of neutralizing agents is also possible.
The present invention is a universal all-purpose adhesive which is likely to be used by persons at greater risk to health, such as children, the elderly, the sick, pregnant women, etc. Therefore, in a particularly preferred embodiment, physiologically dangerous substances must be avoided and all components of the adhesive must be considered to be largely physiologically harmless. This includes, for example, the partial, if possible, complete exclusion of organic agents. The solutions often discussed in connection with polyurethane gases are known to be dangerously isolated from water by free polyurethane cyanide or by not dispersing or dispersing polyurethane cyanide in water, as is the case with the present invention, and it is not possible to ensure that the solution is immediately reactive to water, since the solution is known to be inert and the polyurethane cyanide is not dispersed in water.
In order to produce polyurethanes particularly suitable for the purposes of the invention, the polyoles and an excess of diisocyanate are converted into a polymer with finite isocyanate groups, with suitable reaction conditions and reaction times and temperatures being variable according to the isocyanate in question. The expert knows that the reactivity of the components to be converted requires a suitable balance between reaction rate and undesirable side reactions leading to discoloration and reduction in molecular weight within about 1 to 6 hours.
The manufacturing process is the so-called acetone process (D. Dietrich, Application of the Macromol Chem. 98, 133 (1981)). Furthermore, the polyurethane dispersions of the invention can also be manufactured by the DE 15 95 602 process. A newer process for the manufacture of polyurethane dispersions is described in DE 36 03 996 and in the state of the art specified therein, namely: DE-PS 8 80 485, DE-AS 10 44 404, US-PS 30 36 998, DE-PS 11 78 586, DE-PS 11 84 946, DE-AS 12 37 306, DE-AS 14 95 745, DE-OS 15 95 602, DE-OS 17 70 068, DE-OS 20 19 324, DE-OS 20 73 352, DE-OS 24 460, DE-OS 25 456, DE-OS 27 244, DE-OS 27 310 and 27 272, and in the Chemical and Chemical Appendices (1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972, 1972,
Err1:Expecting ',' delimiter: line 1 column 92 (char 91)
Further processes for the production of polyurethane prepolymers, in particular for the continuous production of polyurethane prepolymers, are described in German disclosures 22 60 870, 23 11 635 and 23 44 135.
In order to obtain essentially clear, i.e. opaque to water-clear polyurethane dispersions, the professional must pay attention to a certain ratio between the salt-forming component and the other substances which constitute the polyurethane. It is therefore advisable to use the salt-forming component - in this case dimethylpropionic acid - in quantities of 1 to 70, preferably 2 to 30, and in particular 10 to 18% by weight in relation to polyol.
Err1:Expecting ',' delimiter: line 1 column 355 (char 354)
The solids content of the adhesive solutions of the invention can vary widely; in practice, solids content has been shown to be between 20 and 70% by weight, in particular between 30 and 50% by weight.
The polyoles are diluted or dissolved or dispersed in acetone. Dimethylolpropionic acid is then added during stirring. Diisocyanate is then added at temperatures between 50 and 70°C until the NCO content no longer decreases. At 60°C it is then neutralized, e.g. with N-methylmorpholine. After a duration of about 30 minutes, water is then added. After 30 minutes of dispersing, the acetone is then distilled, later under a higher vacuum at temperatures of 55 to 60°C.
Apply a 60 μm adhesive film with a spiral rake to chrome paper, immediately glue with identical paper, slowly rub until the material tears in one unit of time:
Other
Polyurethane dispersions to be used in accordance with the invention, as described in the example and in comparison examples 1 to 4, were subjected to a storage test at 50 °C. The following viscosity changes were observed:
Other
Claims (8)
1. The use of a substantially clear and at least largely solventless, aqueous, one-component polyurethane dispersion based on the reaction products of
- a polyol mixture consisting completely or partly of polytetrahydrofuran,
- a difunctional or more than difunctional isocyanate component used in an OH:NCO ratio of 1:0.5 to 1:2.0, preferably 1:1.0 to 1:1.7 and more preferably 1:1.05 to 1:1.6 thereto and
- dimethylol propionic acid as a functional component capable of salt formation in aqueous solution as a universal household adhesive.
2. The use claimed in claim 1, characterized in that 30 to 100% by weight of the polyol mixtures on which the polyurethane dispersions are based consist of polytetrahydrofuran and 0 to 70% by weight of a polyether polyol, polyacetal polyol and/or polyester polyol containing on average 2 to at most 4 OH groups.
3. The use claimed in claim 1 or 2, characterized in that 70 to 100% by weight of the polyol mixtures on which the polyurethane dispersions are based consist of polytetrahydrofuran.
4. The use claimed in any of the preceding claims, characterized in that the polyurethanes on which the polyurethane dispersions are based are synthesized from difunctional or more than difunctional aliphatic and/or aromatic polyisocyanates, preferably from branched or cyclic aliphatic diisocyanates.
5. The use claimed in any of the preceding claims, characterized in that the polyurethanes on which the polyurethane dispersions are based contain co-condensed dimethylol propionic acid which may be present as an alkali metal salt, ammonium salt or as a salt of primary, secondary or tertiary amines.
6. The use claimed in any of the preceding claims, characterized in that the quantity of dimethylol propionic acid used is from 1 to 70% by weight, preferably from 2 to 30% by weight and more preferably from 10 to 18% by weight, based on polyol.
7. A process for the production of the universal household adhesive claimed in any of the preceding claims, characterized in that
- an NCO-terminated prepolymer is initially prepared from
- a polyol mixture consisting completely or partly of polytetrahydrofuran,
- a difunctional or more than difunctional isocyanate component used in an OH:NCO ratio of 1:0.5 to 1:2.0, preferably 1:1.0 to 1:1.7 and more preferably 1:1.05 to 1:1.6 thereto and
- dimethylol propionic acid as a functional component capable of salt formation in aqueous solution
- and is then dissolved in an inert solvent,
- dispersion is then carried out discontinuously in stirred tanks comprising stirrers and, optionally baffles and
- the solvent used is distilled off from the stirred tank, if desired immediately after dispersion in water.
8. A process for the production of the universal household adhesive claimed in any of the preceding claims, characterized in that
- the polyol component is diluted with acetone or is dissolved or dispersed therein,
- the dimethylol propionic acid is added with stirring,
- diisocyanate is added at temperatures of 50 to 70°C until there is no further reduction in the NCO content,
- the product is neutralized at 60°C,
- water is added after about 30 minutes and
- after dispersion for 30 minutes, the acetone is distilled off, subsequently in a relatively high vacuum at temperatures of 55 to 60°C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3827378A DE3827378A1 (en) | 1988-08-12 | 1988-08-12 | HOUSEHOLD ALL-PURPOSE GLUE BASED ON POLYURETHANE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HK1794A true HK1794A (en) | 1994-01-14 |
Family
ID=6360706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HK17/94A HK1794A (en) | 1988-08-12 | 1994-01-06 | Use of aqueous polyurethane dispersions as domestic universal adhesive and their preparation |
Country Status (19)
| Country | Link |
|---|---|
| EP (2) | EP0354471B1 (en) |
| JP (1) | JP2892409B2 (en) |
| KR (1) | KR900701883A (en) |
| CN (1) | CN1040386A (en) |
| AT (1) | ATE76415T1 (en) |
| AU (1) | AU4045589A (en) |
| BR (1) | BR8907594A (en) |
| CA (1) | CA1339656C (en) |
| DE (2) | DE3827378A1 (en) |
| DK (1) | DK305190A (en) |
| ES (1) | ES2037352T3 (en) |
| GR (1) | GR3005265T3 (en) |
| HK (1) | HK1794A (en) |
| IE (1) | IE63014B1 (en) |
| NO (1) | NO173703C (en) |
| PT (1) | PT91404B (en) |
| TR (1) | TR25089A (en) |
| WO (1) | WO1990001508A1 (en) |
| ZA (1) | ZA896159B (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3942681A1 (en) * | 1989-12-22 | 1991-06-27 | Henkel Kgaa | HOUSEHOLD GLUE BASED ON POLYURETHANE |
| DE4011455A1 (en) * | 1990-04-09 | 1991-10-10 | Henkel Kgaa | HOUSEHOLD ALL-PURPOSE GLUE BASED ON POLYURETHANE |
| DE4023005A1 (en) * | 1990-07-19 | 1992-01-23 | Henkel Kgaa | THIXOTROPE POLYURETHANE SYSTEMS |
| DE4109477A1 (en) * | 1991-03-22 | 1992-09-24 | Henkel Kgaa | POLYMER DISPERSIONS SUITABLE FOR REACTIVE SYSTEMS |
| DE4120432A1 (en) * | 1991-06-20 | 1992-12-24 | Henkel Kgaa | DIHYDROXY FATTY ACIDS AS POLYURETHANE BUILDING BLOCKS |
| JP3584480B2 (en) * | 1993-09-28 | 2004-11-04 | 大日本インキ化学工業株式会社 | Solvent-free composite laminate adhesive composition and bonding method using the same |
| DE4408487A1 (en) * | 1994-03-14 | 1995-09-21 | Henkel Kgaa | Aqueous polyurethane primer |
| GB0207205D0 (en) * | 2002-03-27 | 2002-05-08 | Avecia Ltd | Polyurethane dispersion, manufacture and uses |
| CN101585927B (en) * | 2008-05-20 | 2011-05-25 | 聚和国际股份有限公司 | Flow additive for water-based PU |
| WO2011124517A1 (en) | 2010-04-08 | 2011-10-13 | Construction Research & Technology Gmbh | Conductive adhesive for a floor covering |
| US10155891B2 (en) * | 2014-07-25 | 2018-12-18 | Dow Global Technologies Llc | One-component structural adhesive containing isocyanate-terminated prepolymer |
| CN110330627A (en) * | 2019-07-10 | 2019-10-15 | 福建元发树脂有限公司 | Non-solvent single-component polyurethane casting resin |
| CN111704883B (en) * | 2020-07-09 | 2021-09-17 | 旭川化学（苏州）有限公司 | Solvent-free single-component moisture curing polyurethane adhesive suitable for wood and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE880485C (en) | 1944-07-02 | 1953-06-22 | Bayer Ag | Process for the production of high polymers |
| DE1044404B (en) | 1957-02-23 | 1958-11-20 | Hoechst Ag | Process for the production of polyfunctional anion-active high molecular weight polyurethanes |
| US3036998A (en) | 1959-05-25 | 1962-05-29 | Grace W R & Co | Polymeric hydrazinium salts |
| NL299775A (en) | 1962-10-26 | |||
| BE640789A (en) | 1962-12-05 | |||
| DE1495745C3 (en) | 1963-09-19 | 1978-06-01 | Bayer Ag, 5090 Leverkusen | Process for the production of aqueous, emulsifier-free polyurethane latices |
| US3336376A (en) | 1964-09-03 | 1967-08-15 | Allied Chem | Perfluorocyclohexane-1, 4-diacyl fluoride and process for preparing perfluorocyclohexane mono-and diacyl fluorides |
| DE1237306B (en) | 1964-09-26 | 1967-03-23 | Bayer Ag | Process for the production of polyurethane plastics |
| FR1499121A (en) | 1964-12-08 | 1968-01-12 | ||
| DE1595602A1 (en) | 1966-03-12 | 1969-09-18 | Bayer Ag | Process for the production of polyurethane plastics |
| DE1770068C3 (en) | 1968-03-27 | 1981-01-15 | Bayer Ag, 5090 Leverkusen | Process for the production of polyurethanes Bayer AG, 5090 Leverkusen |
| DE1769387A1 (en) * | 1968-05-17 | 1971-10-28 | Bayer Ag | Use of aqueous polyurethane dispersions for bonding plasticized polyvinyl chloride plastics |
| DE2019324C3 (en) | 1970-04-22 | 1979-02-22 | Bayer Ag, 5090 Leverkusen | Process for the production of lightfast polyurethane ionomers |
| DE2035732A1 (en) | 1970-07-18 | 1972-01-27 | Farbenfabriken Bayer AG, 5090 Le verkusen | N (omega ammo a / kan) omega ammo a / kan sulfonic acid salts and their use as anionic structural components in the production of emulsifier-free polyurethane dispersions |
| DE2260870A1 (en) | 1972-12-13 | 1974-06-27 | Bayer Ag | PROCESS FOR THE CONTINUOUS PREPARATION OF Aqueous SOLID DISPERSIONS |
| DE2344135C2 (en) | 1973-09-01 | 1983-11-17 | Bayer Ag, 5090 Leverkusen | Process for the continuous production of aqueous polyurethane dispersions |
| DE2345256A1 (en) | 1973-09-07 | 1975-03-20 | Bayer Ag | PROCESS FOR THE PRODUCTION OF MICROPOROUS FLATS |
| DE2427274A1 (en) | 1974-06-06 | 1976-01-08 | Bayer Ag | Microporous polyurethane coatings - prepd by coagulating polyurethane contg anionic and or cationic polyurethanes |
| DE2446440C3 (en) | 1974-09-28 | 1981-04-30 | Bayer Ag, 5090 Leverkusen | Process for the preparation of aqueous dispersions of polyurethanes containing sulfonate groups |
| GB1575637A (en) * | 1976-10-04 | 1980-09-24 | Textron Inc | Aqueous colloidal polyurea-urethane ionomer dispersions |
| US4160065A (en) * | 1976-12-14 | 1979-07-03 | Witco Chemical Corporation | Polyurethane latexes from NCO prepolymers chain extended with polyepoxides, polyanhydrides or polyaldehydes, and layered products |
| DE3603996A1 (en) | 1986-02-08 | 1987-08-13 | Bayer Ag | METHOD FOR THE CONTINUOUS PRODUCTION OF AQUEOUS POLYURETHANE DISPERSIONS AND THEIR USE AS A COATING AGENT OR AS AN ADHESIVE |
-
1988
- 1988-08-12 DE DE3827378A patent/DE3827378A1/en not_active Withdrawn
-
1989
- 1989-07-05 TR TR89/0626A patent/TR25089A/en unknown
- 1989-08-03 EP EP89114337A patent/EP0354471B1/en not_active Expired - Lifetime
- 1989-08-03 BR BR898907594A patent/BR8907594A/en not_active Application Discontinuation
- 1989-08-03 DE DE8989114337T patent/DE58901469D1/en not_active Expired - Lifetime
- 1989-08-03 WO PCT/EP1989/000915 patent/WO1990001508A1/en not_active Ceased
- 1989-08-03 KR KR1019900700738A patent/KR900701883A/en not_active Withdrawn
- 1989-08-03 JP JP1508460A patent/JP2892409B2/en not_active Expired - Fee Related
- 1989-08-03 ES ES198989114337T patent/ES2037352T3/en not_active Expired - Lifetime
- 1989-08-03 AT AT89114337T patent/ATE76415T1/en not_active IP Right Cessation
- 1989-08-03 AU AU40455/89A patent/AU4045589A/en not_active Abandoned
- 1989-08-03 EP EP89908989A patent/EP0428578A1/en active Pending
- 1989-08-08 PT PT91404A patent/PT91404B/en not_active IP Right Cessation
- 1989-08-10 CN CN89105528A patent/CN1040386A/en active Pending
- 1989-08-10 CA CA000607989A patent/CA1339656C/en not_active Expired - Fee Related
- 1989-08-11 ZA ZA896159A patent/ZA896159B/en unknown
- 1989-08-11 IE IE258889A patent/IE63014B1/en not_active IP Right Cessation
-
1990
- 1990-12-21 DK DK305190A patent/DK305190A/en not_active Application Discontinuation
-
1991
- 1991-02-06 NO NO910460A patent/NO173703C/en unknown
-
1992
- 1992-07-24 GR GR920401594T patent/GR3005265T3/el unknown
-
1994
- 1994-01-06 HK HK17/94A patent/HK1794A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ZA896159B (en) | 1990-07-25 |
| CN1040386A (en) | 1990-03-14 |
| BR8907594A (en) | 1991-07-30 |
| IE63014B1 (en) | 1995-03-22 |
| JPH04500083A (en) | 1992-01-09 |
| PT91404A (en) | 1990-03-08 |
| WO1990001508A1 (en) | 1990-02-22 |
| KR900701883A (en) | 1990-12-04 |
| EP0428578A1 (en) | 1991-05-29 |
| JP2892409B2 (en) | 1999-05-17 |
| ATE76415T1 (en) | 1992-06-15 |
| IE892588L (en) | 1990-02-12 |
| DE58901469D1 (en) | 1992-06-25 |
| DK305190D0 (en) | 1990-12-21 |
| PT91404B (en) | 1995-05-04 |
| NO173703C (en) | 1994-01-19 |
| ES2037352T3 (en) | 1993-06-16 |
| NO910460L (en) | 1991-02-06 |
| AU4045589A (en) | 1990-03-05 |
| TR25089A (en) | 1992-09-23 |
| EP0354471B1 (en) | 1992-05-20 |
| CA1339656C (en) | 1998-02-03 |
| DE3827378A1 (en) | 1990-02-22 |
| NO173703B (en) | 1993-10-11 |
| NO910460D0 (en) | 1991-02-06 |
| DK305190A (en) | 1990-12-21 |
| EP0354471A1 (en) | 1990-02-14 |
| GR3005265T3 (en) | 1993-05-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PF | Patent in force | ||
| PC | Patent ceased (i.e. patent has lapsed due to the failure to pay the renewal fee) |
Effective date: 20070803 |