CA2003423A1 - Wet adhesion epoxy resin systems - Google Patents
Wet adhesion epoxy resin systemsInfo
- Publication number
- CA2003423A1 CA2003423A1 CA002003423A CA2003423A CA2003423A1 CA 2003423 A1 CA2003423 A1 CA 2003423A1 CA 002003423 A CA002003423 A CA 002003423A CA 2003423 A CA2003423 A CA 2003423A CA 2003423 A1 CA2003423 A1 CA 2003423A1
- Authority
- CA
- Canada
- Prior art keywords
- epoxy resin
- composition
- epoxy
- hardener
- weight
- 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.)
- Abandoned
Links
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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- 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
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
- C04B41/48—Macromolecular compounds
- C04B41/4853—Epoxides
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/56—Amines together with other curing agents
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/66—Mercaptans
-
- 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
- C04B2111/00—Mortars, concrete or artificial stone or mixtures to prepare them, characterised by specific function, property or use
- C04B2111/00474—Uses not provided for elsewhere in C04B2111/00
- C04B2111/00637—Uses not provided for elsewhere in C04B2111/00 as glue or binder for uniting building or structural materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Ceramic Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Epoxy Resins (AREA)
Abstract
WET ADHESION EPOXY RESIN SYSTEMS
Abstract of the Disclosure Epoxy resin systems with improved wet adhesion strength and bond durability comprising an epoxy resin and hardener in combination with an organo silane modified with mercapto groups.
Abstract of the Disclosure Epoxy resin systems with improved wet adhesion strength and bond durability comprising an epoxy resin and hardener in combination with an organo silane modified with mercapto groups.
Description
2~)3423 WET AD~IESION EPOXY RESIN SYSTE~MS
The present invention relates to epoxy adhesive composi~ions comprising an organosilane with a terrninal mercapto group for improved wet adhesion, to the products obtained by curing said compositions and to a process for improving the wet adhesion of an epoxy adhesive system.
Epoxy resins are extensively utilized as adhesives for the bonding and repair of concrete surfaces. lt has been determined, however, that epoxy adhesive strength and bond durabili-ty are poor under moist conditions. Such exposure is frequently encountered under adverse weather conditions of rain, snow or ice or during application in moist environments. The unacceptable adhesive characteristics come into play in the bonding of wet or damp concrete to wet or damp concrete, the bonding of old concrete to new concrete, the bond-ing of metal to moist concrete, and the like. Since currently utilized epoxy adhesives do not provide the desired performance, there is a current need for epoxy adhesive systems which are readily applicable to all surface configurations and which perform under all environmental conditions.
It has now been surprisingly discovered that by incorporating specified concentrations of organo silanes containing terminal functional groups into epoxy resin formulations, en-hanced adhesive perforrmance characteristics are obtained. Thus, the improved systems are applicable for use under a wide range of conditions. The systems are particularly useful under moist conditions when the adhesive bonding occurs in a damp environment.
Contrary to prior art systems, excellent adhesive strength and bond durability are obtained.
The instant invention relates to an adhesive composition comprising a) an epoxy resin having on average more than one epoxy group per molecule b) an amine hardener therefor; and c) from about 0.5-10 % by weight of a) and b) of an organo silane containing a terminal mercapto group.
20~3423 The instan~ compositions facilitate the bonding of moist concrete to other concrete compo-sitions, to metal, and the like.
The epoxy resins used according to the invention may be any polyepoxide so far as it has on average, more than one epoxy group per molecule. It may be any of saturated and unsaturated, aliphatic, alicyclic, aromatic and heterocyclic epoxides. If desired, it may have a non-hindering substituent such as halogen atom, hydroxyl group, ether group, ester group and the like. Examples of said polyepoxides inciude epoxy novolac resins; poly-glycidyl ethers of dihydric phenols such as 2,2-bis(4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)ethane, bis(4-hydroxyphenyl)methane, bis(4-hydroxyphenyl)sulfone, resorcinol and hydroquinone; polyglycidyl ethers of trihydric alcohols such as glycerin;
polyglycidyl esters such as diglycidyl phthalate and diglycidyl isophthalate; cycloaliphatic epoxy resins; epoxidized esters of polyethylenically unsaturated fatty acids such as epoxi-dized linseed oil; epoxidized esters of unsaturated alcohols and unsaturated carboxylic acids such as 3,4-epoxycyclohexylmethyl, 3,4-epoxycyclohexylcarboxylate; and epoxi-dized polyethylenically unsaturated hydrocarbons.
Diglycidyl ethers of dihydric phenols are preferred. Particularly preferred is the diglycidyl ether of 2,2-~is(4-hydroxyphenyl)propane.
Applicable resins also include epoxy resins with lowered viscosities resulting from the presence of reactive diluents such as glycidyl ethers, glycol ethers, aromatic hydrocarbons, and the like.
As suitable hardeners for use in the systems, there may be mentioned aliphatic or cycloali-phatic primar~ and secondary amines, including mixnlres. Typical amines include ethylenediamine, hexamethylenediamine, trimethylhexamethylenediamine, methylpenta-methylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, N,N-dimethylpropylenediamine,1,3, N,N-diethylpropylenediamine-1,3, bis(4-amino-3-methyl-cyclohexyl)methane, bis(p-aminocyclohexyl)methane, 2,2-bis(4-aminocyclo-hexyl)-propane, 3,5,5-trimethyl-s-(aminomethyl)-cyclohexylamine, 1,2-diaminocyclo-hexane, 1,4-diaminocyclohexane, 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(amino-methyl)-cyclohexane, N-aminoethylpiperazine, isophorone diamine, p-pllenylenediamine, m-phenylenediamine, bis(4-aminop'henyl)-methane, bis(4-aminophenyl)ether, bis(4-aminophenyl)ketone, aniline-formaldehyde resins, bis(4-aminophenyl)sulfone, bis(3-aminophenyl)sulfone and 2,4'-diaminodiphenyl sulfone.
2003a~23 The preferred hardeners include 2,2,4-trimethylhexamethylenediamine, 2,4,4-trimethyl-hexamethylenediamine, 2-methylpentamethylenediamine, diethylenetriamine, triethylene-tetramine, tetraethylenepentamine, 1,2-diaminocyclohexane, bis(p-aminocyclohexyl)-methane, isophorone diamine, 1,4-bis(aminomethyl)-cyclohexane, N-aminoethylpipera-zine and 1,3-bis(aminomethyl)cyclohexane.
Examples for the organo silanes containing a terminal mercapto group include gamma-mercapto-propyltrimethoxysilane, beta-mercaptoethyltrimethoxysilane, mercaptomethyl-trimethoxysilane, beta-mercaptoethyltripropoxysilane, gamma-mercaptopropylphenyldi-methoxysilalle and beta-mercaptoethylmethyldimethoxysilane.
Particularly preferred is gamma-mercaptopropyltrimethoxysilane.
The silane is present in concentrations varying from 0.5-10 ~o by weight based on the resin/hardener combination and preferably 0.5-5 % by weight. Concentrations which noticeably deviate from the prescribed range have an adverse effect on adhesive properties, particularly on the wet adhesive strength and durability.
The silane may be mixed either with the epoxy resin or with the hardener at room tempe-rature prior to combination of resin and hardener. In general, it is preferred to mix the epoxy and vinyl silanes with the epoxy resin and the amino and mercapto silanes with the amine hardener.
The subsequent curing of the epoxy resin compositions of this invention is within the knowledge of the art. Curing is generally effected at temperatures of between 5-40C for the appropriate period of time in the presence of a hardener. The hardener is utilized in stoichiometric amounts +50 % relative to the modified epoxy resin, with 1:1 stoichiometry being preferred. Upon curing, a network of high crosslink density occurs. Accordingly, the expression "cure" as used herein, denotes the conversion of the above epoxide material into insoluble and infusible crosslinked products. Said products are also an object of the present invention.
The epoxy resins prepared according to the invention can furthermore be mixed, at any stage before cure, with usual modifiers such as extenders, fillers and reinforcing agents, pigments, dyestuffs, organic solvents, plasticizers, tackifiers, rubbers, accelerators, 21D~3~23 diluents, and the like. As extenders, reinforcing agents, fillers and pigments which can be employed in the curable mixtllres according to the invention there may be mentioned, for example: coal tar, bitumen, glass fibers, boron fibers, carbon fibers, cellulose, poly-ethylene powder, polypropylene powder, mica, asbestos, quartz powder, gypsum, anti-mony trioxide, bentones, lithopone, barite, titanium dioxide, carbon black or g}aphite. It is also possible to add other usual additives, for example flameproofing agents, agents for conferring thixotropy, flow conlrol agents such as silicones, cellulose acetate butyr~te, polyvinyl butyrate, waxes, stearates and the like (which are in part also used as mold release agents) to the curable mixtures.
Although the curable epoxide resin mixtures are noted as being especially useful in the fields of adhesion and surface protection and repair, they are also applicable to the electrical industry, laminating processes and the building industry. They can be used in a formulation which is in each case suited to the particular end use such as compression molding compositions, casting resins, tooling resins, laminating resins, sealing and filling compositions and floor covering compositions.
The following examples will further illustrate the embodiments of the instant invention. In these examples, all parts are given by weight unless otherwise noted.
Example 1: This example illustrates the preparation of typical epoxy resin adhesive systems of the instant invention.
Resin: diglycidyl ether of bisphenol A with a functional diluent (ARALDITE EP-IS from CIBA-GEIGY Corp.).
Hardener: 2,2,4- and/or 2,4,4-trimethylhexamethylene diamine Wet Bondin~ System Preparation: The epoxy resin or hardener is blended with the indicated silane (epoxy silane with epoxy resin and amino or mercapto silane with hardener) at room temperature at the indicated weight ratio.
Evaluation of Bond Stren~th A. Damp Concrete to Steel - Concrete cubes 5 cm x 5 cm x 5 cm are soaked in water at room temperature for 24 hours, surface wiped, coated on opposite sides thereof with a 5 mil thick layer of epoxy adhesive and bonded to 5 cm x 5 cm steel adherends. The Z~(~34Z3 bonded specimens are cured at room temperature for seven days while the concrete block is maintained in a moist condition. The samples are then placed in an Instron Tensile Tester whereby the opposing steel adherends are subjected to a tensile pull of 0.127 cm/minute. The pressure load necessary to cause breakage and the type of failure, i.e. either in the concrete or in ihe adhesive interface, are noted for each system.
B. Damp Concrete to Damp Concrete - Concrete cubes 5 cm x 5 cm x 5 cm are soaked in water at room temperature for 24 hours, surface wiped and bonded to each other with a 5 mil layer of epoxy adhesive within a bonding area of 13 sq. cm. The bonded cubes are cured at room temperature for one week and then subjected to impact with a hammer at a distance of one cm above the bond line until fracture occurs. The failure mode is noted either as adhesive or concrete, with failure predominantly in the concrete being indicative of effective adhesive perforrnance.
The results are noted below.
Bond Strength Conc. Resin/Hardener Test A Test B
Silane (% by wt of R&H) Mix Ratio [N/cm2]
- --- 100:30 110.3 A A
1 0.65 100:35 399.9 C C
1 1.30 100:35 344.7 C C
1 2.60 100:35 320.6 C C
1 5.20 100:35 255.1 C C
A- break in adhesive bond C- break in concrete
The present invention relates to epoxy adhesive composi~ions comprising an organosilane with a terrninal mercapto group for improved wet adhesion, to the products obtained by curing said compositions and to a process for improving the wet adhesion of an epoxy adhesive system.
Epoxy resins are extensively utilized as adhesives for the bonding and repair of concrete surfaces. lt has been determined, however, that epoxy adhesive strength and bond durabili-ty are poor under moist conditions. Such exposure is frequently encountered under adverse weather conditions of rain, snow or ice or during application in moist environments. The unacceptable adhesive characteristics come into play in the bonding of wet or damp concrete to wet or damp concrete, the bonding of old concrete to new concrete, the bond-ing of metal to moist concrete, and the like. Since currently utilized epoxy adhesives do not provide the desired performance, there is a current need for epoxy adhesive systems which are readily applicable to all surface configurations and which perform under all environmental conditions.
It has now been surprisingly discovered that by incorporating specified concentrations of organo silanes containing terminal functional groups into epoxy resin formulations, en-hanced adhesive perforrmance characteristics are obtained. Thus, the improved systems are applicable for use under a wide range of conditions. The systems are particularly useful under moist conditions when the adhesive bonding occurs in a damp environment.
Contrary to prior art systems, excellent adhesive strength and bond durability are obtained.
The instant invention relates to an adhesive composition comprising a) an epoxy resin having on average more than one epoxy group per molecule b) an amine hardener therefor; and c) from about 0.5-10 % by weight of a) and b) of an organo silane containing a terminal mercapto group.
20~3423 The instan~ compositions facilitate the bonding of moist concrete to other concrete compo-sitions, to metal, and the like.
The epoxy resins used according to the invention may be any polyepoxide so far as it has on average, more than one epoxy group per molecule. It may be any of saturated and unsaturated, aliphatic, alicyclic, aromatic and heterocyclic epoxides. If desired, it may have a non-hindering substituent such as halogen atom, hydroxyl group, ether group, ester group and the like. Examples of said polyepoxides inciude epoxy novolac resins; poly-glycidyl ethers of dihydric phenols such as 2,2-bis(4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)ethane, bis(4-hydroxyphenyl)methane, bis(4-hydroxyphenyl)sulfone, resorcinol and hydroquinone; polyglycidyl ethers of trihydric alcohols such as glycerin;
polyglycidyl esters such as diglycidyl phthalate and diglycidyl isophthalate; cycloaliphatic epoxy resins; epoxidized esters of polyethylenically unsaturated fatty acids such as epoxi-dized linseed oil; epoxidized esters of unsaturated alcohols and unsaturated carboxylic acids such as 3,4-epoxycyclohexylmethyl, 3,4-epoxycyclohexylcarboxylate; and epoxi-dized polyethylenically unsaturated hydrocarbons.
Diglycidyl ethers of dihydric phenols are preferred. Particularly preferred is the diglycidyl ether of 2,2-~is(4-hydroxyphenyl)propane.
Applicable resins also include epoxy resins with lowered viscosities resulting from the presence of reactive diluents such as glycidyl ethers, glycol ethers, aromatic hydrocarbons, and the like.
As suitable hardeners for use in the systems, there may be mentioned aliphatic or cycloali-phatic primar~ and secondary amines, including mixnlres. Typical amines include ethylenediamine, hexamethylenediamine, trimethylhexamethylenediamine, methylpenta-methylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, N,N-dimethylpropylenediamine,1,3, N,N-diethylpropylenediamine-1,3, bis(4-amino-3-methyl-cyclohexyl)methane, bis(p-aminocyclohexyl)methane, 2,2-bis(4-aminocyclo-hexyl)-propane, 3,5,5-trimethyl-s-(aminomethyl)-cyclohexylamine, 1,2-diaminocyclo-hexane, 1,4-diaminocyclohexane, 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(amino-methyl)-cyclohexane, N-aminoethylpiperazine, isophorone diamine, p-pllenylenediamine, m-phenylenediamine, bis(4-aminop'henyl)-methane, bis(4-aminophenyl)ether, bis(4-aminophenyl)ketone, aniline-formaldehyde resins, bis(4-aminophenyl)sulfone, bis(3-aminophenyl)sulfone and 2,4'-diaminodiphenyl sulfone.
2003a~23 The preferred hardeners include 2,2,4-trimethylhexamethylenediamine, 2,4,4-trimethyl-hexamethylenediamine, 2-methylpentamethylenediamine, diethylenetriamine, triethylene-tetramine, tetraethylenepentamine, 1,2-diaminocyclohexane, bis(p-aminocyclohexyl)-methane, isophorone diamine, 1,4-bis(aminomethyl)-cyclohexane, N-aminoethylpipera-zine and 1,3-bis(aminomethyl)cyclohexane.
Examples for the organo silanes containing a terminal mercapto group include gamma-mercapto-propyltrimethoxysilane, beta-mercaptoethyltrimethoxysilane, mercaptomethyl-trimethoxysilane, beta-mercaptoethyltripropoxysilane, gamma-mercaptopropylphenyldi-methoxysilalle and beta-mercaptoethylmethyldimethoxysilane.
Particularly preferred is gamma-mercaptopropyltrimethoxysilane.
The silane is present in concentrations varying from 0.5-10 ~o by weight based on the resin/hardener combination and preferably 0.5-5 % by weight. Concentrations which noticeably deviate from the prescribed range have an adverse effect on adhesive properties, particularly on the wet adhesive strength and durability.
The silane may be mixed either with the epoxy resin or with the hardener at room tempe-rature prior to combination of resin and hardener. In general, it is preferred to mix the epoxy and vinyl silanes with the epoxy resin and the amino and mercapto silanes with the amine hardener.
The subsequent curing of the epoxy resin compositions of this invention is within the knowledge of the art. Curing is generally effected at temperatures of between 5-40C for the appropriate period of time in the presence of a hardener. The hardener is utilized in stoichiometric amounts +50 % relative to the modified epoxy resin, with 1:1 stoichiometry being preferred. Upon curing, a network of high crosslink density occurs. Accordingly, the expression "cure" as used herein, denotes the conversion of the above epoxide material into insoluble and infusible crosslinked products. Said products are also an object of the present invention.
The epoxy resins prepared according to the invention can furthermore be mixed, at any stage before cure, with usual modifiers such as extenders, fillers and reinforcing agents, pigments, dyestuffs, organic solvents, plasticizers, tackifiers, rubbers, accelerators, 21D~3~23 diluents, and the like. As extenders, reinforcing agents, fillers and pigments which can be employed in the curable mixtllres according to the invention there may be mentioned, for example: coal tar, bitumen, glass fibers, boron fibers, carbon fibers, cellulose, poly-ethylene powder, polypropylene powder, mica, asbestos, quartz powder, gypsum, anti-mony trioxide, bentones, lithopone, barite, titanium dioxide, carbon black or g}aphite. It is also possible to add other usual additives, for example flameproofing agents, agents for conferring thixotropy, flow conlrol agents such as silicones, cellulose acetate butyr~te, polyvinyl butyrate, waxes, stearates and the like (which are in part also used as mold release agents) to the curable mixtures.
Although the curable epoxide resin mixtures are noted as being especially useful in the fields of adhesion and surface protection and repair, they are also applicable to the electrical industry, laminating processes and the building industry. They can be used in a formulation which is in each case suited to the particular end use such as compression molding compositions, casting resins, tooling resins, laminating resins, sealing and filling compositions and floor covering compositions.
The following examples will further illustrate the embodiments of the instant invention. In these examples, all parts are given by weight unless otherwise noted.
Example 1: This example illustrates the preparation of typical epoxy resin adhesive systems of the instant invention.
Resin: diglycidyl ether of bisphenol A with a functional diluent (ARALDITE EP-IS from CIBA-GEIGY Corp.).
Hardener: 2,2,4- and/or 2,4,4-trimethylhexamethylene diamine Wet Bondin~ System Preparation: The epoxy resin or hardener is blended with the indicated silane (epoxy silane with epoxy resin and amino or mercapto silane with hardener) at room temperature at the indicated weight ratio.
Evaluation of Bond Stren~th A. Damp Concrete to Steel - Concrete cubes 5 cm x 5 cm x 5 cm are soaked in water at room temperature for 24 hours, surface wiped, coated on opposite sides thereof with a 5 mil thick layer of epoxy adhesive and bonded to 5 cm x 5 cm steel adherends. The Z~(~34Z3 bonded specimens are cured at room temperature for seven days while the concrete block is maintained in a moist condition. The samples are then placed in an Instron Tensile Tester whereby the opposing steel adherends are subjected to a tensile pull of 0.127 cm/minute. The pressure load necessary to cause breakage and the type of failure, i.e. either in the concrete or in ihe adhesive interface, are noted for each system.
B. Damp Concrete to Damp Concrete - Concrete cubes 5 cm x 5 cm x 5 cm are soaked in water at room temperature for 24 hours, surface wiped and bonded to each other with a 5 mil layer of epoxy adhesive within a bonding area of 13 sq. cm. The bonded cubes are cured at room temperature for one week and then subjected to impact with a hammer at a distance of one cm above the bond line until fracture occurs. The failure mode is noted either as adhesive or concrete, with failure predominantly in the concrete being indicative of effective adhesive perforrnance.
The results are noted below.
Bond Strength Conc. Resin/Hardener Test A Test B
Silane (% by wt of R&H) Mix Ratio [N/cm2]
- --- 100:30 110.3 A A
1 0.65 100:35 399.9 C C
1 1.30 100:35 344.7 C C
1 2.60 100:35 320.6 C C
1 5.20 100:35 255.1 C C
A- break in adhesive bond C- break in concrete
Claims (8)
1. An adhesive composition comprising (a) an epoxy resin having on average more than one epoxy group per molecule; (b) an amine hardener therefor; and (c) from about0.5-10 % by weight of (a) and (b) of an organo silane containing a terminal mercapto group.
2. The composition of claim 1, wherein said epoxy resin is an epoxy novolac resin, a poly-glycidyl ether of a dihydric phenol, a polyglycidyl ether of a trihydric alcohol, a cyclo-aliphatic epoxy resin, a polyglycidyl ester, an epoxidized ester of a polyethylenically unsaturated fatty acid, an epoxidized ester of an unsaturated alcohol and an unsaturated carboxylic acid or an epoxidized polyethylenically unsaturated hydrocarbon.
3. The composition of claim 1, wherein said epoxy resin is modified with a reactive diluent.
4. The composition of claim 2, wherein said epoxy resin is a diglycidyl ether of a dihydric phenol.
5. The composition of claim 1, wherein component (c) is gamma-mercaptopropyltri-methoxysilane.
6. The composition of claim 1, wherein component (c) is present in a concentration of 0.5-5.0 % by weight.
7. The product obtained by curing the composition of claim 1 at a temperature of 5-40°C.
8. A process for improving the wet adhesion properties of an epoxy resin/amine hardener adhesive system which comprises incorporating into either the epoxy resin or hardener component from about 0.5-10 % by weight of epoxy resin and hardener of an organosilane containing a terminal mercapto group.
FO 7.3/SEN/cc*
FO 7.3/SEN/cc*
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27525188A | 1988-11-23 | 1988-11-23 | |
| US275,251 | 1988-11-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2003423A1 true CA2003423A1 (en) | 1990-05-23 |
Family
ID=23051488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002003423A Abandoned CA2003423A1 (en) | 1988-11-23 | 1989-11-21 | Wet adhesion epoxy resin systems |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0370954A3 (en) |
| JP (1) | JPH02185584A (en) |
| KR (1) | KR900007987A (en) |
| CA (1) | CA2003423A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4203741C2 (en) * | 1992-02-09 | 1996-07-11 | Dyckerhoff & Widmann Ag | Process for the positive filling of cracks in structural parts made of concrete |
| AU3190895A (en) * | 1995-08-04 | 1997-03-05 | Asahi Denka Kogyo Kabushiki Kaisha | Curable epoxy resin composition which gives flexible cured aticle |
| NL1009134C2 (en) * | 1998-05-12 | 1999-08-24 | Vincent Alfred Joseph Woudsma | Method for repairing or filling or gluing or protecting organic or inorganic materials by means of mixing and / or dilution of elastic curable epoxy based products. |
| KR101210788B1 (en) * | 2012-08-24 | 2012-12-13 | 김승우 | Luminescence apparatus for wheel of bicycle |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58129072A (en) * | 1982-01-28 | 1983-08-01 | Sutaaraito Kogyo Kk | Electrically conductive primer composition |
| JPH0832850B2 (en) * | 1986-05-16 | 1996-03-29 | 日東電工株式会社 | Anticorrosion construction method for underwater steel structure |
-
1989
- 1989-11-08 KR KR1019890016154A patent/KR900007987A/en not_active Application Discontinuation
- 1989-11-14 EP EP19890810873 patent/EP0370954A3/en not_active Withdrawn
- 1989-11-21 CA CA002003423A patent/CA2003423A1/en not_active Abandoned
- 1989-11-22 JP JP1304575A patent/JPH02185584A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0370954A3 (en) | 1992-02-12 |
| KR900007987A (en) | 1990-06-02 |
| JPH02185584A (en) | 1990-07-19 |
| EP0370954A2 (en) | 1990-05-30 |
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