CA2343392A1 - Curing of resins - Google Patents
Curing of resins Download PDFInfo
- Publication number
- CA2343392A1 CA2343392A1 CA002343392A CA2343392A CA2343392A1 CA 2343392 A1 CA2343392 A1 CA 2343392A1 CA 002343392 A CA002343392 A CA 002343392A CA 2343392 A CA2343392 A CA 2343392A CA 2343392 A1 CA2343392 A1 CA 2343392A1
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- CA
- Canada
- Prior art keywords
- resin
- catalyst
- curing
- trapped
- tert
- 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.)
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Classifications
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- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
- C08J3/241—Preventing premature crosslinking by physical separation of components, e.g. encapsulation
-
- 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
- C08K9/00—Use of pretreated ingredients
- C08K9/10—Encapsulated ingredients
-
- 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
- C08K9/00—Use of pretreated ingredients
- C08K9/12—Adsorbed ingredients, e.g. ingredients on carriers
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
Abstract
A method of manufacturing a product comprising at least two parts includes the steps of coating one of the parts at least partially with a resin having a trapped catalyst distributed therein, placing the parts together with the resin therebetween and releasing the catalyst into the resin to initiate curing at the desired time. The catalyst may be trapped either by encapsulation or by absorption/adsorption into the structure of a suitable substrate such as almond shell. The catalyst may be an organic peroxide, formic acid or toluene sulphonic acid. An accelerator may be used to accelerate curing.
Description
CURING OF RESINS
The present invention relates to a method of controlling the curing of a resin and to a resin modified to provide such control. The invention also includes the application of the method and the use of the resin in the production of articles.
In the production of plywood, for example, individual layers of wood are coated with resin, pressed together and subjected to heat in order to cure the resin. The time for which the heat is supplied to obtain a cure can be considerable slowing down the production process. Curing times can be reduced by mixing a catalyst with the resin, but this may interfere with the production process itself as curing may start either before or during the application of the resin.
According to one aspect of the present invention, there is provided a method of curing a resin including the steps of trapping a catalyst which when released into the resin initiates curing, mixing the trapped catalyst with the resin and releasing the catalyst into the resin to initiate curing at the desired time.
According to another aspect of the present invention, there is provided a method of manufacturing a product comprising at least two parts including the steps of coating one of the parts at least partially with a resin having a trapped catalyst distributed therein, placing the parts together with the resin therebetween and releasing the catalyst into the resin to initiate curing at the desired time.
The invent'ron also includes products made by the above method and resins with distributed catalysts for use in the above methods.
The catalyst may be trapped either by encapsulation or by adsorption/absorption into the structure of a suitable substrate such as almond shell.
The resin may be any of the following Polyester resin, Vinyl esterresin, Phenol formaldehyde resin, Epoxy resin, Acrylic resin, melaminelurea formaldehyde resin, Phenolic resin.
The catalyst may be any appropriate catalyst such as:-Organic peroxides for example Di benzoyl peroxide, Methyl ethyl keto-peroxide, Cumene hydroperoxide, Acetylacetone peroxide Isold under trade name Triganox 44B), tert-Butyl peroxybenzoate (sold under trade name Triganox C), tert-Butyl-2-ethyl hexanoate (sold under trade name Triganox 21 ), tert-Butylperoxy-3,5,5, trimethyl hexanoate (sold under trade name Triganox 42s), Cumene hydroperoxide Isoid under trade name Triganox K-80), Biz (4-tert-butylcyclohexyl-peroxdicarbonate) (sold under trade name Perkadox 16). Amine Catalysts for example: Diethyltetra amine, Triethylamine Isocyanates, Boron tri fluoride, UV Curing Catalysts, Alkyl Carbonates for example: Propylene and Ethylene carbonate, and mineral and organic acids such as Formic acid, toluene sulphonic acid, or sulphuric acid.
The encapsulating material may be any one of the following; gelatine, thermoset resins, fats, waxes, thermoplastics, polymeric compounds, or silane compounds or any of the encapsulation materials disclosed in the applicants copending international application published under publication No. WO 98/26865.
Accelerators may also be used such as Colbalt octoate (sold under trade name NL-49-P), Diethylaniline fsold under trade name NL-64-10P).
Ammonium Sulphate or Ammonium Chloride.
The size of the encapsulated or coated particles may lie in the range 0.5 to 1000 microns.
Embodiments of the invention will now be described, by way of 16 example.
In a first embodiment, which relates to the manufacture of plywood, layers of plies of wood are coated with resin, placed together with the resin sandwiched between adjacent plies and subject to pressure urging them together and/or heat to cure the resin so that the plies adhere strongly together. In the conventional methods of production pressure and heat may _q,...
have to be applied for a considerable period of time, for example, several minutes, adding to the production time and to the expense of production.
In accordance with the invention, a catalyst is distributed through the resin.
The catalyst is distributed through the resin. The catalyst which may be propylene carbonate, ethylene carbonate or any other suitable catalyst initiates curing of the resin to produce a bond between adjacent plies of wood. However, if curing is initiated too early or progresses too quickly, it may be difficult or impossible to carry out the manufacturing process satisfactorily and/or efficiently. For example, if curing is already proceeding when the pees are coated with res~ 'rt may not be possible to coat the plies readily and, even if it is, the strength of the bond between plies may be adversely affected.
In order to overcome this possible disadvantage, the release of the catalyst into the resin to initiate curing is controlled by encapsulating the catalyst. Encapsulation is achieved by irradiating the catalyst with ultrasound in the presence of an encapsulating material to produce microcapsules of catalyst coated with encapsulating material. The coating isolates the catalyst from the resin even though the encapsulated resin capsules are distributed through the resin. In this state, the resin may be applied to the plies of wood as described previously, but curing will not begin and will therefore not affect this process until the granules are ruptured to release the catalyst into the resin. Rupturing may be effected by irradiating the capsules with ultrasound or by heat or any other suitable method.
In an alternative method of encapsulation, catalyst is adsorbed into the surface of granules of an inert substance which are coated with an encapsulating material again by irradiating with ultrasound. In both cases the size of the coated particles would generally lie in the range 0.5 to 1000 microns.
The catalyst may be any of the following materials, or any mixture thereof:-Organic peroxides for example Di benzoyl peroxide, Methyl ethyl keto-peroxide, Cumene hydroperoxide, Acetylacetone peroxide (sole under trade name Triganox 44B), tert-Butyl peroxybenzoate (sold under trade name Triganox C, tart-Butyl-2-ethyl hexanoate (sold under trade name Triganox 211, tert-Butylperoxy-3,5,5, trimethyl hexanoate (sold under trade name Triganox 42s), Cumene hydroperoxide (sold under trade name Triganox K-80), Biz (4-tert-butylcyclohexyl-peroxdicarbonate) (sold under trade name Perkadox 16). Amine Catalysts for example: Diethyltetra amine, Triethylamine Isocyanates, Boron tri fluoride, UV Curing Catalysts, A
The present invention relates to a method of controlling the curing of a resin and to a resin modified to provide such control. The invention also includes the application of the method and the use of the resin in the production of articles.
In the production of plywood, for example, individual layers of wood are coated with resin, pressed together and subjected to heat in order to cure the resin. The time for which the heat is supplied to obtain a cure can be considerable slowing down the production process. Curing times can be reduced by mixing a catalyst with the resin, but this may interfere with the production process itself as curing may start either before or during the application of the resin.
According to one aspect of the present invention, there is provided a method of curing a resin including the steps of trapping a catalyst which when released into the resin initiates curing, mixing the trapped catalyst with the resin and releasing the catalyst into the resin to initiate curing at the desired time.
According to another aspect of the present invention, there is provided a method of manufacturing a product comprising at least two parts including the steps of coating one of the parts at least partially with a resin having a trapped catalyst distributed therein, placing the parts together with the resin therebetween and releasing the catalyst into the resin to initiate curing at the desired time.
The invent'ron also includes products made by the above method and resins with distributed catalysts for use in the above methods.
The catalyst may be trapped either by encapsulation or by adsorption/absorption into the structure of a suitable substrate such as almond shell.
The resin may be any of the following Polyester resin, Vinyl esterresin, Phenol formaldehyde resin, Epoxy resin, Acrylic resin, melaminelurea formaldehyde resin, Phenolic resin.
The catalyst may be any appropriate catalyst such as:-Organic peroxides for example Di benzoyl peroxide, Methyl ethyl keto-peroxide, Cumene hydroperoxide, Acetylacetone peroxide Isold under trade name Triganox 44B), tert-Butyl peroxybenzoate (sold under trade name Triganox C), tert-Butyl-2-ethyl hexanoate (sold under trade name Triganox 21 ), tert-Butylperoxy-3,5,5, trimethyl hexanoate (sold under trade name Triganox 42s), Cumene hydroperoxide Isoid under trade name Triganox K-80), Biz (4-tert-butylcyclohexyl-peroxdicarbonate) (sold under trade name Perkadox 16). Amine Catalysts for example: Diethyltetra amine, Triethylamine Isocyanates, Boron tri fluoride, UV Curing Catalysts, Alkyl Carbonates for example: Propylene and Ethylene carbonate, and mineral and organic acids such as Formic acid, toluene sulphonic acid, or sulphuric acid.
The encapsulating material may be any one of the following; gelatine, thermoset resins, fats, waxes, thermoplastics, polymeric compounds, or silane compounds or any of the encapsulation materials disclosed in the applicants copending international application published under publication No. WO 98/26865.
Accelerators may also be used such as Colbalt octoate (sold under trade name NL-49-P), Diethylaniline fsold under trade name NL-64-10P).
Ammonium Sulphate or Ammonium Chloride.
The size of the encapsulated or coated particles may lie in the range 0.5 to 1000 microns.
Embodiments of the invention will now be described, by way of 16 example.
In a first embodiment, which relates to the manufacture of plywood, layers of plies of wood are coated with resin, placed together with the resin sandwiched between adjacent plies and subject to pressure urging them together and/or heat to cure the resin so that the plies adhere strongly together. In the conventional methods of production pressure and heat may _q,...
have to be applied for a considerable period of time, for example, several minutes, adding to the production time and to the expense of production.
In accordance with the invention, a catalyst is distributed through the resin.
The catalyst is distributed through the resin. The catalyst which may be propylene carbonate, ethylene carbonate or any other suitable catalyst initiates curing of the resin to produce a bond between adjacent plies of wood. However, if curing is initiated too early or progresses too quickly, it may be difficult or impossible to carry out the manufacturing process satisfactorily and/or efficiently. For example, if curing is already proceeding when the pees are coated with res~ 'rt may not be possible to coat the plies readily and, even if it is, the strength of the bond between plies may be adversely affected.
In order to overcome this possible disadvantage, the release of the catalyst into the resin to initiate curing is controlled by encapsulating the catalyst. Encapsulation is achieved by irradiating the catalyst with ultrasound in the presence of an encapsulating material to produce microcapsules of catalyst coated with encapsulating material. The coating isolates the catalyst from the resin even though the encapsulated resin capsules are distributed through the resin. In this state, the resin may be applied to the plies of wood as described previously, but curing will not begin and will therefore not affect this process until the granules are ruptured to release the catalyst into the resin. Rupturing may be effected by irradiating the capsules with ultrasound or by heat or any other suitable method.
In an alternative method of encapsulation, catalyst is adsorbed into the surface of granules of an inert substance which are coated with an encapsulating material again by irradiating with ultrasound. In both cases the size of the coated particles would generally lie in the range 0.5 to 1000 microns.
The catalyst may be any of the following materials, or any mixture thereof:-Organic peroxides for example Di benzoyl peroxide, Methyl ethyl keto-peroxide, Cumene hydroperoxide, Acetylacetone peroxide (sole under trade name Triganox 44B), tert-Butyl peroxybenzoate (sold under trade name Triganox C, tart-Butyl-2-ethyl hexanoate (sold under trade name Triganox 211, tert-Butylperoxy-3,5,5, trimethyl hexanoate (sold under trade name Triganox 42s), Cumene hydroperoxide (sold under trade name Triganox K-80), Biz (4-tert-butylcyclohexyl-peroxdicarbonate) (sold under trade name Perkadox 16). Amine Catalysts for example: Diethyltetra amine, Triethylamine Isocyanates, Boron tri fluoride, UV Curing Catalysts, A
Carbonates for example: Propylene and Ethylene carbonate and mineral and organic acids such as Formic acid, toluene sulphonic acid, or sulphuric acid.
Accelerators may also be used such as Colbalt octoate 4sold under trade name , NL-49-P1, Diethyianiline (sold under trade name NL-64-10P).
The encapsulating material may be any one of the following or any mixture thereof:- gelatine, thermoset resins, fats, waxes, thermoplastics, polymeric compounds, or silane compounds or any of the encapsulation materials disclosed in the applicants copending international application published under publication No. WO 98/26865.
The resin may be any one of the following or any mixture thereof:-Polyester resin, Vinyl esterresin, Phenol formaldehyde resin, Epoxy resin, Acrylic resin, melamine/urea formaldehyde resin, Phenolic resin.
In a second embodiment, a catalyst is trapped by absorption into a suitable substrate rather than by adsorption as previously described. A
suitable substrate is almond shell which has a surface which facilitates absorption/adsorption of catalyst into 'rts porous structure. The catalyst is formic acid and the resin is a melamine/urea formaldehyde resin although other catalysts and resins, for example, as detailed above may be used.
The process for making the almond shell formic acidltoluene sulphonic acid catalyst material is as follows.
i) The formic acid/toluene sulphonic acid is first dissoived/dispersed inrnto acetone. Acetone acts as a carrier solvent for the acid catalyst into the porous structure of the almond shell.
ii) almond shell is then added to the acid/acetone mixture.
iii) The acid/acetone/almond shell mixture is sonicated using a 20kHz, 400 Watt ultrasonic probe for 3-5 minutes until the acetonelacid has absorbed/adsorbed into the almond shell structure.
This process can be easily observed by a significant thickening appearance of the mixture. One of the reasons a solvent is used is in order for ultrasound to work effectively with a high solid almond shell content present. Excess liquid is required li.e. acetone) in which cavitation can develop. When the cavitation bubbles collapse, a large energy source/shock wave is created and 'rt is this energy which drives the liquid mixture into the almond shell structure.
iv) The acetone solvent is removed from the slurry mixture using drying methods leaving just the acid catalyst embedded in the almond shell. The acetone may be removed and re-cycled using condensers.
The almond shell/acid catalyst product is a fairly free flowing powder which can be easily dispersed in resin.
Acetone is used as a solvent because;
_g_ a) It has very good dissolving properties. For example, para toluene sulphonic acid catalyst (PTSA) which is a solid powder, needs to be dissolved in the acetone before 'rt can be driven into the almond shell.
b) It has a very low boiling point which facilitates its removal during the drying process at low temperature. This is a very important characteristic when formic acid is used because this catalyst has a relatively low boiling point and therefore if high drying temperatures were used, the formic acid would be removed as well.
c) The presence of acetone in the svnication process keeps the temperature very low (specific heat capacity characteristic) reducing or eliminating vaporisation problems.
When the almond shell/acid catalyst is dispersed with the resin, the molecules of the resin are so large that they cannot access the almond shell structure very easily or quickly and therefore cannot come into contact with the acid catalyst which is embedded in the structure. Curing of the resin will therefore not begin. The acid catalyst can be activated by heat. This will cause the structure to expand and open up allowing the resin to get at the catalyst. It needs to be noted that this is not an encapsulation technology and no coating has been used. However a coating could be applied if the end user/application required much greater pot-life stability.
It will be appreciated that the above embodiments have been described by way of example only and that many variations are possible without departing from the scope of the invention. For example, the method of the invention may be applied to any product manufacture where one or more parts are coated and/or impregnated with a curable resin either to enable the parts to be secured together or as part of the production process.
Felts or glass fibre may be impregnated with a curable resin of the invention formed into a desired shape and the resin then cured. Material may be supplied pre-impregnated with resin for use in a downstream production process. These material composites could be employed in the following general areas:-il Bvat construction, ii) Automotive industry - for example interior/exterior components and body panels, iii) Train/Aeorplane construction - for example interior/exter'ror components and body panels, iv) Off shore marine/oil drilling applications, v) Building construction - wall panels (interior/exterior), roofing vi) House-hold goods, vii) Surface coatings viii) Fire retardent foams/coatings/compos'rtes, ix) Binders for the paint and paper industry, x) Binders for use in the foundry industry, xi) Filament windings, xii) Plastic extrusions, xiii) Adhesives, xiv) MDF/Particle Board, xvl Dough Moulding compounds, xvi) Pre-impregnated products, xvii) Binders for concrete applications used in the building/construction industry.
Accelerators may also be used such as Colbalt octoate 4sold under trade name , NL-49-P1, Diethyianiline (sold under trade name NL-64-10P).
The encapsulating material may be any one of the following or any mixture thereof:- gelatine, thermoset resins, fats, waxes, thermoplastics, polymeric compounds, or silane compounds or any of the encapsulation materials disclosed in the applicants copending international application published under publication No. WO 98/26865.
The resin may be any one of the following or any mixture thereof:-Polyester resin, Vinyl esterresin, Phenol formaldehyde resin, Epoxy resin, Acrylic resin, melamine/urea formaldehyde resin, Phenolic resin.
In a second embodiment, a catalyst is trapped by absorption into a suitable substrate rather than by adsorption as previously described. A
suitable substrate is almond shell which has a surface which facilitates absorption/adsorption of catalyst into 'rts porous structure. The catalyst is formic acid and the resin is a melamine/urea formaldehyde resin although other catalysts and resins, for example, as detailed above may be used.
The process for making the almond shell formic acidltoluene sulphonic acid catalyst material is as follows.
i) The formic acid/toluene sulphonic acid is first dissoived/dispersed inrnto acetone. Acetone acts as a carrier solvent for the acid catalyst into the porous structure of the almond shell.
ii) almond shell is then added to the acid/acetone mixture.
iii) The acid/acetone/almond shell mixture is sonicated using a 20kHz, 400 Watt ultrasonic probe for 3-5 minutes until the acetonelacid has absorbed/adsorbed into the almond shell structure.
This process can be easily observed by a significant thickening appearance of the mixture. One of the reasons a solvent is used is in order for ultrasound to work effectively with a high solid almond shell content present. Excess liquid is required li.e. acetone) in which cavitation can develop. When the cavitation bubbles collapse, a large energy source/shock wave is created and 'rt is this energy which drives the liquid mixture into the almond shell structure.
iv) The acetone solvent is removed from the slurry mixture using drying methods leaving just the acid catalyst embedded in the almond shell. The acetone may be removed and re-cycled using condensers.
The almond shell/acid catalyst product is a fairly free flowing powder which can be easily dispersed in resin.
Acetone is used as a solvent because;
_g_ a) It has very good dissolving properties. For example, para toluene sulphonic acid catalyst (PTSA) which is a solid powder, needs to be dissolved in the acetone before 'rt can be driven into the almond shell.
b) It has a very low boiling point which facilitates its removal during the drying process at low temperature. This is a very important characteristic when formic acid is used because this catalyst has a relatively low boiling point and therefore if high drying temperatures were used, the formic acid would be removed as well.
c) The presence of acetone in the svnication process keeps the temperature very low (specific heat capacity characteristic) reducing or eliminating vaporisation problems.
When the almond shell/acid catalyst is dispersed with the resin, the molecules of the resin are so large that they cannot access the almond shell structure very easily or quickly and therefore cannot come into contact with the acid catalyst which is embedded in the structure. Curing of the resin will therefore not begin. The acid catalyst can be activated by heat. This will cause the structure to expand and open up allowing the resin to get at the catalyst. It needs to be noted that this is not an encapsulation technology and no coating has been used. However a coating could be applied if the end user/application required much greater pot-life stability.
It will be appreciated that the above embodiments have been described by way of example only and that many variations are possible without departing from the scope of the invention. For example, the method of the invention may be applied to any product manufacture where one or more parts are coated and/or impregnated with a curable resin either to enable the parts to be secured together or as part of the production process.
Felts or glass fibre may be impregnated with a curable resin of the invention formed into a desired shape and the resin then cured. Material may be supplied pre-impregnated with resin for use in a downstream production process. These material composites could be employed in the following general areas:-il Bvat construction, ii) Automotive industry - for example interior/exterior components and body panels, iii) Train/Aeorplane construction - for example interior/exter'ror components and body panels, iv) Off shore marine/oil drilling applications, v) Building construction - wall panels (interior/exterior), roofing vi) House-hold goods, vii) Surface coatings viii) Fire retardent foams/coatings/compos'rtes, ix) Binders for the paint and paper industry, x) Binders for use in the foundry industry, xi) Filament windings, xii) Plastic extrusions, xiii) Adhesives, xiv) MDF/Particle Board, xvl Dough Moulding compounds, xvi) Pre-impregnated products, xvii) Binders for concrete applications used in the building/construction industry.
Claims (10)
1. A method of curing a resin including the steps of trapping a catalyst which when released into tho resin initiator curing, mixing the trapped catalyst with the resin and releasing the catalyst into the resin to initiate curing at the desired time, in which the catalyst is trapped by absorption into the surface of almond shell.
2. A method of manufacturing a product comprising at least two parts including the steps of coating one of the parts at least partially with a resin having a trapped catalyst distributed therein, placing the parts together with the resin therebetween and releasing the catalyst into the resin to initiate curing at the desired time, in which the catalyst is trapped by absorption into the surface of almond shell.
3. A method as claimed in claim 1 or 2, in which the catalyst is trapped by encapsulation.
4. A method as claimed in claim 3, in which the encapsulation material comprises one or more of the following:-gelatine, thermoset resins, fats, waxes. thermoplastics. polymeric compounds, or silane compounds.
5. A method as claimed in any of claims 1 to 4, in which the rosin comprises one or more of the following Polyester rosin, Vinyl esterresin, Phenol formaldehyde rosin, Epoxy resin, Acrylic resin, melamine/urea formaldehyde resin, Phenolic resin.
6. A method as claimed in any preceding claim, in which the catalyst is an organic peroxide.
7. A method as claimed in any of claims 1 to 5, in which the catalyst comprise one or more of the following:-Organic peroxides for example Di benzoyl peroxide, Methyl ethyl keto-peroxide, Cumene hydroperoxide, Acetylacetone peroxide, tart-Butyl peroxybenzoate, tert-Butyl-2-ethyl hexanoate, tert-Butylperoxy-3,5,5, trimethyl hexanoate, Cumene hydroperoxide, Biz (4-tert-butylcyclohexyl-peroxdicarbonate). Amine Catalysts for example: Diethyltetra amine, Triethylamine isocyanate, Boron tri fluoride, UV Curing Catalysts, Alkyl Carbonates for example; Propylene and Ethylene carbonate, and mineral and organic adds such as Formic acid, toluene sulphonic acid, or sulphuric acid.
8. A method as claimed in any of claims 1 to 7, in which an accelerator is used to accelerate curing.
9. A method as claimed in claim 8, in which the accelerator is Cobalt octoate, Diethylaniline. Ammonium Sulphate or Ammonium Chloride.
10. A product made by the method as claimed in any preceding claim.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9819815.3A GB9819815D0 (en) | 1998-09-12 | 1998-09-12 | Curing of resins |
| GB9819815.3 | 1998-09-12 | ||
| GBGB9909763.6A GB9909763D0 (en) | 1998-09-12 | 1999-04-29 | Cluring of resins |
| GB9909763.6 | 1999-04-29 | ||
| PCT/GB1999/002830 WO2000015694A2 (en) | 1998-09-12 | 1999-09-10 | Curing of resins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2343392A1 true CA2343392A1 (en) | 2000-03-23 |
Family
ID=26314359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002343392A Abandoned CA2343392A1 (en) | 1998-09-12 | 1999-09-10 | Curing of resins |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1112303A2 (en) |
| JP (1) | JP2002524634A (en) |
| CN (1) | CN1325418A (en) |
| AU (1) | AU5870799A (en) |
| CA (1) | CA2343392A1 (en) |
| GB (1) | GB9909763D0 (en) |
| NO (1) | NO20011212L (en) |
| WO (1) | WO2000015694A2 (en) |
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|---|---|---|---|---|
| DE102009046251A1 (en) | 2009-10-30 | 2011-05-19 | Evonik Röhm Gmbh | Reactive 1-component road markings |
| FR2953524B1 (en) * | 2009-12-03 | 2012-12-14 | Arkema France | HIGH SPEED CROSSLINKING SYSTEM |
| EP2691433A1 (en) | 2011-03-31 | 2014-02-05 | OCV Intellectual Capital, LLC | Microencapsulated curing agent |
| JP5677922B2 (en) * | 2011-09-27 | 2015-02-25 | 積水化学工業株式会社 | Curing agent and / or curing accelerator encapsulating capsule, and thermosetting resin composition |
| EP2788406A1 (en) | 2011-12-08 | 2014-10-15 | OCV Intellectual Capital, LLC | Fiber reinforced resin molding compound and manufacturing method for fiber reinforced resin molded article therefrom |
| JP5964085B2 (en) * | 2012-02-13 | 2016-08-03 | 株式会社松風 | Organic peroxide-containing composite fine particles |
| US20150132592A1 (en) | 2013-11-08 | 2015-05-14 | Ppg Industries Ohio, Inc. | Curable film-forming compositions comprising catalyst associated with a carrier and methods for coating a substrate |
| EP3115348A1 (en) * | 2015-07-07 | 2017-01-11 | BAE Systems PLC | Cast explosive composition |
| CA2991169C (en) | 2015-07-07 | 2023-03-28 | Bae Systems Plc | Pbx composition |
| US11001540B2 (en) | 2015-07-07 | 2021-05-11 | Bae Systems Plc | Cast explosive composition |
| CN111019554B (en) * | 2019-12-23 | 2021-09-10 | 天津渤海化学股份有限公司 | Curing resin regulator, bi-component epoxy system adhesive and preparation method thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3036980A (en) * | 1956-12-31 | 1962-05-29 | Union Carbide Corp | Rubber composition containing zeolitic molecular sieve and process for curing |
| GB1029732A (en) * | 1961-09-29 | 1966-05-18 | Union Carbide Corp | Improved release of agents from adsorbate-containing molecular sieves |
| JPS60168642A (en) * | 1984-02-14 | 1985-09-02 | 呉羽化学工業株式会社 | Manufacture of laminated film |
| US4808639A (en) * | 1986-07-16 | 1989-02-28 | Production Previews, Inc. | Liquid curable adhesive composition comprising a polyester resin and a microencapsulated peroxide curing agent |
| GB9623878D0 (en) * | 1996-11-15 | 1997-01-08 | Marlit Ltd | Bonding materials |
| GB9626152D0 (en) * | 1996-12-17 | 1997-02-05 | Cehmcolloids Ltd | Encapsulation |
-
1999
- 1999-04-29 GB GBGB9909763.6A patent/GB9909763D0/en not_active Ceased
- 1999-09-10 CA CA002343392A patent/CA2343392A1/en not_active Abandoned
- 1999-09-10 WO PCT/GB1999/002830 patent/WO2000015694A2/en not_active Application Discontinuation
- 1999-09-10 EP EP99946287A patent/EP1112303A2/en not_active Withdrawn
- 1999-09-10 AU AU58707/99A patent/AU5870799A/en not_active Abandoned
- 1999-09-10 JP JP2000570228A patent/JP2002524634A/en active Pending
- 1999-09-10 CN CN 99813045 patent/CN1325418A/en active Pending
-
2001
- 2001-03-09 NO NO20011212A patent/NO20011212L/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1112303A2 (en) | 2001-07-04 |
| AU5870799A (en) | 2000-04-03 |
| NO20011212D0 (en) | 2001-03-09 |
| WO2000015694A3 (en) | 2000-07-13 |
| JP2002524634A (en) | 2002-08-06 |
| CN1325418A (en) | 2001-12-05 |
| GB9909763D0 (en) | 1999-06-23 |
| NO20011212L (en) | 2001-03-09 |
| WO2000015694A2 (en) | 2000-03-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20030612 |