CA2072956A1 - Interior can coating compositions containing cyclodextrins - Google Patents
Interior can coating compositions containing cyclodextrinsInfo
- Publication number
- CA2072956A1 CA2072956A1 CA002072956A CA2072956A CA2072956A1 CA 2072956 A1 CA2072956 A1 CA 2072956A1 CA 002072956 A CA002072956 A CA 002072956A CA 2072956 A CA2072956 A CA 2072956A CA 2072956 A1 CA2072956 A1 CA 2072956A1
- Authority
- CA
- Canada
- Prior art keywords
- cyclodextrin
- composition
- interior
- resin
- coating
- 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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/10—Applications used for bottles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/16—Cyclodextrin; Derivatives thereof
Abstract
Abstract The flavor protecting properties of interior container coating compositions are improved by the inclusion of cyclodextrins in the composition.
Description
-DOCKET NO.: P-539 Interior Can Coat_ng Compositions Containing Cyclodextrins Backqround of the Invention The field of art to which this invention pertains is metal container coating compositions.
In the manufacture of metal containers, a thin protective synthetic resin coating is applied to the interior of the container to prevent contact of the metal surface of the can with its contents. Such coatings ideally should have good adhesion to the interior metal surface, low extractables to prevent contamination of the container contents, and a rapid cure or drying rate for economy of container manufacture. Coating compositions which have been used for a number of years include organic qolvent solut,ons and aqueous dispersions of synthetic thermoplastic and thermosetting resin which include such compos tions as vinyl res-ns, polybutadiene resins, epoxy resins, aminoplast resins, phenoplast resins, and oleoresinous materials.
It is particularly important that containers which are used for foods and beverages contain no contaminants which not only can affect the preservation of the foods or beverage but also can affect the taste of the stored material. Taste quality is particularly important in the storage of beverages, especially beer, wherein very small amounts, in the order of parts per million or even parts per billion, of extranious material can have a detrimental effect on taste.
20729~6 In an article published in nInclusion Compounds," Volume 3, Chapter 11, pp. 331-390, Academic Press, London, 1984, J. Szejtli discusses cyclodextrins, their chemistry, and present and potential uses..
As discussed in Food Engineering, July 1987, pp. 36-38, cyclodextrins have the ability to capture or encapsulate other molecules within their ring structures. Because of this property, cyclodextrins offer a wide range of applications across the food industry for modifying taste, texture, color and aroma of processed foods and for shielding ingredients from the degrading effect of heat, light and oxygen. One use for cyclodextrins has been the debittering of citrus fruit juices.
In "St;rch/Starke 27 (1975) pp 368-376, Szejtli and Banky-Eloa, discuss inclusion complexes of unsaturated fatty acids and cyclodextrins.
The stabilizat_on of autoxidizable fatty acids with cyclodextr-ns is described in U.S. Patent ~o. 2,827,452.
In U.S. Patent ~os. 4,722,815 and 4,725,657, synthetic resin compositions are disclosed which are made from a synthetic resin, cyclodextrin, glycitol, and a molecular inclusion compound included in the cyclode~trin. Molecular inclusion compounds are listed as being perfumes, insecticides, mold or mildew proofing agents, anti-fungi agents and bactericides.
~ here is a continuing need for interior container coating compositions which prevent contaminants from mixing with the container contents and affecting the quality of said contents.
In the manufacture of metal containers, a thin protective synthetic resin coating is applied to the interior of the container to prevent contact of the metal surface of the can with its contents. Such coatings ideally should have good adhesion to the interior metal surface, low extractables to prevent contamination of the container contents, and a rapid cure or drying rate for economy of container manufacture. Coating compositions which have been used for a number of years include organic qolvent solut,ons and aqueous dispersions of synthetic thermoplastic and thermosetting resin which include such compos tions as vinyl res-ns, polybutadiene resins, epoxy resins, aminoplast resins, phenoplast resins, and oleoresinous materials.
It is particularly important that containers which are used for foods and beverages contain no contaminants which not only can affect the preservation of the foods or beverage but also can affect the taste of the stored material. Taste quality is particularly important in the storage of beverages, especially beer, wherein very small amounts, in the order of parts per million or even parts per billion, of extranious material can have a detrimental effect on taste.
20729~6 In an article published in nInclusion Compounds," Volume 3, Chapter 11, pp. 331-390, Academic Press, London, 1984, J. Szejtli discusses cyclodextrins, their chemistry, and present and potential uses..
As discussed in Food Engineering, July 1987, pp. 36-38, cyclodextrins have the ability to capture or encapsulate other molecules within their ring structures. Because of this property, cyclodextrins offer a wide range of applications across the food industry for modifying taste, texture, color and aroma of processed foods and for shielding ingredients from the degrading effect of heat, light and oxygen. One use for cyclodextrins has been the debittering of citrus fruit juices.
In "St;rch/Starke 27 (1975) pp 368-376, Szejtli and Banky-Eloa, discuss inclusion complexes of unsaturated fatty acids and cyclodextrins.
The stabilizat_on of autoxidizable fatty acids with cyclodextr-ns is described in U.S. Patent ~o. 2,827,452.
In U.S. Patent ~os. 4,722,815 and 4,725,657, synthetic resin compositions are disclosed which are made from a synthetic resin, cyclodextrin, glycitol, and a molecular inclusion compound included in the cyclode~trin. Molecular inclusion compounds are listed as being perfumes, insecticides, mold or mildew proofing agents, anti-fungi agents and bactericides.
~ here is a continuing need for interior container coating compositions which prevent contaminants from mixing with the container contents and affecting the quality of said contents.
2~729~ 6 Summary of the Invention This invention is directed to coating compositions for use on the interior surfaces of containers wherein said coatings protect foods or beverages stored in the containers from contaminants which adversely affect taste.
The interi~r container coating composition of this invention is made from a solution or dispersion of a synthetic thermoplastic or thermosetting film forming resin having blended therein about 0.5 to about S weight~of a cyclodextrin wherein said weight percents are based on the total coating composition weight.
The coating composition of this invention is particularly useful for coating the nterior of beer containers to prevent the development of an "off-taste" similar to stale beer, which off-taste ls believed to be caused by trace amounts of certain aldehydes and ketones, e.g., aldehydes and ketones which contain about 6 to about 18 carbon atoms.
Detailed DescriPtion of the Invention Cyclodextrins are cyclic carbohydrate molecules composed of several glucose monomers bound together in a doughnut-shaped truncated cone. This configuration creates hydrophilic rims at top and bottom and a hydrophobic cavity in the middle, resulting in a structure capable of binding and encapsulating molecules of the proper size within the cavity. This phenomenon is known as "molecular inclusion. n Cyclodextrins have been made enzymatically from corn starch using a glucose transverse enzyme. ~hree cyclodextrins which have been produced in commercial quantities are the alpha, beta, and gamma forms. Alpha-cyclodextrin conta-ns 6 glucose units and has a molecular weight of 973. Its cavity diameter is 5-6 angstroms and it cavity depth is 7-8 angstroms.
Beta-cyclodextrin contains 7 glucose units and has a molecular weight of 1135. Its cavity diameter and its cavity depth are 7-8 angstroms. Gamma-cyclodextrin contains 8 glucose units and has a molecular weight of 1297. Its cavity diameter is 9-10 angstroms and its cavity deptl s 7-8 angstroms. The solubility in grams per 100 mls of water at 25C for alpha-cyclodextrin is 14.5, for beta-cyclodextrin - 1.85, and for gamma-cyclodextrin-23.2.
~ he coating compositions useful in this invention are all of the interior conta-ner coat'ng compositions which are well known to those skilled in the art. The polymer systems used to make the interior container coating compositions include oleoresinous compositions based on drying oils, alkyd resins, phenolic resins, polyamides, polyurethanes, epoxy resins, silicones, butadiene polymers, acrylic or methacrylic ester polymers, vinyl chloride polymers, vinyl acetal or vinyl butyral polymers, and fluorocarbon polymers. Comb_nations of useful polymer systems include acrylic and amino resins, acrylic and epoxy resins, alkyd and aminoresins, alkyd and acrylic resins, polyester and epoxy resins, polyester and aminores ns, phenolic and epoxy resins, epoxy and aminoresins, and phenolic and aminoresins.
The coating compositions can be used as organic solvent solutions of the polymer systems, as non-aqueous dispersion of 20729~
the polymers, as aqueous emulsions or latices, and as aqueous dispersions of the resins.
The polymer systems can be thermoplast c, e.g., the vinyl chloride polymers, or thermosetting, e.g., the epoxy-aminoresin compositions.
Coating compos-tions useful in this invention are well known in the art and are described in detail in the literature and the patent art. Examples of such compositions include organic solvent solutions of polyglycidyl ether~of polyhydric phenols which are cured with urea-for~aldehyde, melamine-formaldehyde, and phenol-formaldehyde resins.
Particularly preferred coating compositions for use in this invention are the aqueous dispersions of polyhydroxy polyether resins and acrylic resins, cured with aminoplast and phenolplast resins. Such compositions are described in detail in U.~. Patent Nos. 4,442,246; 4,212,731; and 4,751,256, wh,ch are hereby incorporated by reference.
In preparing the coating compositions of this invention, the cyclodextrin, in the amount of about 0.5 to about 5 weight percent and preerably about 1 to about 3 weight percent, based on the weight of the coating composition, is added to and blended into the coating compositions. $he compos tion is then applied to the interior surface of a container which is then heated to dry and/or cure the coating. Extraction ~tudies conducted on the coatings of this invention when compared to such studies conducted on identical coatings which do not contain _5_ ~72~
cyclodextrins show a dramatic decrease or absence of aldehydes and ketones which are considered to he the source of flavor problems in beer.
The following examples describe the invention in detail.
Parts and percentages unless otherwise designated are parts and percentages by weight.
ExamPle 1 An aqueous film-forming resin dispersion was made to which was added 1 percent beta-cyclodextrin based on the total dispersion weight. The dispersion contained the following components:
ComPOnentR Parts Epoxy Re~in * 13.27 Acrylic Copolymer ~* 4.38 Hexamethoxymethyl ~elamine 0.92 Dodecylbenzene Sulfonic Acid 0.75 Carnaba Wax 0.05 Dimethylethanol Amine 0.54 Triethanol Amine 0,55 N-Butyl Alcohol 8.38 2-Butyoxyethanol 5.58 N-Hexyl Alcohol 0.64 Deionized Water 64.72 Beta~Cyclodextrin 0.99 * Polyglycidyl ether of Bisphenol A - epoxide equivalent weight - 2246.
20729~6 ** Copolymer of 35.6 percent acrylic acid, 32.2 percent ethyl acrylate and 32.2 percent methyl acrylate.
The Acrylic Copolymer and the Hexamethoxy-methyl Melamine were incorporated in the dispersion composition using the procedure described in U.S. Patent No. 4,289,811, which is hereby incorporated by reference.
The interior surfaces of glass beakers were coated with the aqueou~ dispersion. One set of beakers was baked for 1 minute at 360F (Ex. lA), and another set was baked at 380F (Ex. lB~.
~ he interior surfaces of another set of glass beakers were coated with .the aqueous dispersion which contained no beta-cyclodextrin. The beakers baked at 360F were labelled Ex.
lC, the ones at 380F were labelled Ex. lD.
Each set in the examples contained 12 beakers.
Extraction studies were conducted on the coated beakers as follows:
One beaker in each set was filled with methylene chloride.
After S minutes at room temperature, the methylene chloride was transferred to another beaker n the set. After 5 minutes, the methylene chloride was again trar.~ferred to the next beaker. The transfers were continued using all twelve beakers in the set, thusly concentrating any extracted material. The methylene chloride was then analyzed for aldehydes and ketones using high performance chromatographic analysis. The results are listed in the Table.
20729~
Table Example 2-heptenal 2-heptanone 2-octenal octanal 2-nonenal PE~ ppb _ p~b pE?b_ ppb lA 0.2 - 0.4 lB
lC 0.2 0~95 0.65 0.3 lD - 0.45 0.3 0.3 0.3 2,4-decadienal n-nonanal 2-decenal n-decanal lA - 0.8 - 0.3 lB
lC 1.2 - 0.8 0.47 lD 0.35 0.2 - 0.3 Example 2 Simllar results were obtained uslng a coating composition which contained 2 weight percent beta-cyclodextrin.
~ aste tests conducted on beer ~Jhich had been stor0d n cans coated with the coatings of Example 1 and Example 2 were satisfactory.
The principles, preferred embodiments and modes of operation of the present invention have been described in the foregoing speclfication. The invention which is intended to protecteZ
herein, however, is not to be constructed as limited to the particular forms d.isclosed, since these are to be regarded as illustrative rather than restrictive. Variations and changes may be made by those skilled in the art without departing from the spirit of the invention.
The interi~r container coating composition of this invention is made from a solution or dispersion of a synthetic thermoplastic or thermosetting film forming resin having blended therein about 0.5 to about S weight~of a cyclodextrin wherein said weight percents are based on the total coating composition weight.
The coating composition of this invention is particularly useful for coating the nterior of beer containers to prevent the development of an "off-taste" similar to stale beer, which off-taste ls believed to be caused by trace amounts of certain aldehydes and ketones, e.g., aldehydes and ketones which contain about 6 to about 18 carbon atoms.
Detailed DescriPtion of the Invention Cyclodextrins are cyclic carbohydrate molecules composed of several glucose monomers bound together in a doughnut-shaped truncated cone. This configuration creates hydrophilic rims at top and bottom and a hydrophobic cavity in the middle, resulting in a structure capable of binding and encapsulating molecules of the proper size within the cavity. This phenomenon is known as "molecular inclusion. n Cyclodextrins have been made enzymatically from corn starch using a glucose transverse enzyme. ~hree cyclodextrins which have been produced in commercial quantities are the alpha, beta, and gamma forms. Alpha-cyclodextrin conta-ns 6 glucose units and has a molecular weight of 973. Its cavity diameter is 5-6 angstroms and it cavity depth is 7-8 angstroms.
Beta-cyclodextrin contains 7 glucose units and has a molecular weight of 1135. Its cavity diameter and its cavity depth are 7-8 angstroms. Gamma-cyclodextrin contains 8 glucose units and has a molecular weight of 1297. Its cavity diameter is 9-10 angstroms and its cavity deptl s 7-8 angstroms. The solubility in grams per 100 mls of water at 25C for alpha-cyclodextrin is 14.5, for beta-cyclodextrin - 1.85, and for gamma-cyclodextrin-23.2.
~ he coating compositions useful in this invention are all of the interior conta-ner coat'ng compositions which are well known to those skilled in the art. The polymer systems used to make the interior container coating compositions include oleoresinous compositions based on drying oils, alkyd resins, phenolic resins, polyamides, polyurethanes, epoxy resins, silicones, butadiene polymers, acrylic or methacrylic ester polymers, vinyl chloride polymers, vinyl acetal or vinyl butyral polymers, and fluorocarbon polymers. Comb_nations of useful polymer systems include acrylic and amino resins, acrylic and epoxy resins, alkyd and aminoresins, alkyd and acrylic resins, polyester and epoxy resins, polyester and aminores ns, phenolic and epoxy resins, epoxy and aminoresins, and phenolic and aminoresins.
The coating compositions can be used as organic solvent solutions of the polymer systems, as non-aqueous dispersion of 20729~
the polymers, as aqueous emulsions or latices, and as aqueous dispersions of the resins.
The polymer systems can be thermoplast c, e.g., the vinyl chloride polymers, or thermosetting, e.g., the epoxy-aminoresin compositions.
Coating compos-tions useful in this invention are well known in the art and are described in detail in the literature and the patent art. Examples of such compositions include organic solvent solutions of polyglycidyl ether~of polyhydric phenols which are cured with urea-for~aldehyde, melamine-formaldehyde, and phenol-formaldehyde resins.
Particularly preferred coating compositions for use in this invention are the aqueous dispersions of polyhydroxy polyether resins and acrylic resins, cured with aminoplast and phenolplast resins. Such compositions are described in detail in U.~. Patent Nos. 4,442,246; 4,212,731; and 4,751,256, wh,ch are hereby incorporated by reference.
In preparing the coating compositions of this invention, the cyclodextrin, in the amount of about 0.5 to about 5 weight percent and preerably about 1 to about 3 weight percent, based on the weight of the coating composition, is added to and blended into the coating compositions. $he compos tion is then applied to the interior surface of a container which is then heated to dry and/or cure the coating. Extraction ~tudies conducted on the coatings of this invention when compared to such studies conducted on identical coatings which do not contain _5_ ~72~
cyclodextrins show a dramatic decrease or absence of aldehydes and ketones which are considered to he the source of flavor problems in beer.
The following examples describe the invention in detail.
Parts and percentages unless otherwise designated are parts and percentages by weight.
ExamPle 1 An aqueous film-forming resin dispersion was made to which was added 1 percent beta-cyclodextrin based on the total dispersion weight. The dispersion contained the following components:
ComPOnentR Parts Epoxy Re~in * 13.27 Acrylic Copolymer ~* 4.38 Hexamethoxymethyl ~elamine 0.92 Dodecylbenzene Sulfonic Acid 0.75 Carnaba Wax 0.05 Dimethylethanol Amine 0.54 Triethanol Amine 0,55 N-Butyl Alcohol 8.38 2-Butyoxyethanol 5.58 N-Hexyl Alcohol 0.64 Deionized Water 64.72 Beta~Cyclodextrin 0.99 * Polyglycidyl ether of Bisphenol A - epoxide equivalent weight - 2246.
20729~6 ** Copolymer of 35.6 percent acrylic acid, 32.2 percent ethyl acrylate and 32.2 percent methyl acrylate.
The Acrylic Copolymer and the Hexamethoxy-methyl Melamine were incorporated in the dispersion composition using the procedure described in U.S. Patent No. 4,289,811, which is hereby incorporated by reference.
The interior surfaces of glass beakers were coated with the aqueou~ dispersion. One set of beakers was baked for 1 minute at 360F (Ex. lA), and another set was baked at 380F (Ex. lB~.
~ he interior surfaces of another set of glass beakers were coated with .the aqueous dispersion which contained no beta-cyclodextrin. The beakers baked at 360F were labelled Ex.
lC, the ones at 380F were labelled Ex. lD.
Each set in the examples contained 12 beakers.
Extraction studies were conducted on the coated beakers as follows:
One beaker in each set was filled with methylene chloride.
After S minutes at room temperature, the methylene chloride was transferred to another beaker n the set. After 5 minutes, the methylene chloride was again trar.~ferred to the next beaker. The transfers were continued using all twelve beakers in the set, thusly concentrating any extracted material. The methylene chloride was then analyzed for aldehydes and ketones using high performance chromatographic analysis. The results are listed in the Table.
20729~
Table Example 2-heptenal 2-heptanone 2-octenal octanal 2-nonenal PE~ ppb _ p~b pE?b_ ppb lA 0.2 - 0.4 lB
lC 0.2 0~95 0.65 0.3 lD - 0.45 0.3 0.3 0.3 2,4-decadienal n-nonanal 2-decenal n-decanal lA - 0.8 - 0.3 lB
lC 1.2 - 0.8 0.47 lD 0.35 0.2 - 0.3 Example 2 Simllar results were obtained uslng a coating composition which contained 2 weight percent beta-cyclodextrin.
~ aste tests conducted on beer ~Jhich had been stor0d n cans coated with the coatings of Example 1 and Example 2 were satisfactory.
The principles, preferred embodiments and modes of operation of the present invention have been described in the foregoing speclfication. The invention which is intended to protecteZ
herein, however, is not to be constructed as limited to the particular forms d.isclosed, since these are to be regarded as illustrative rather than restrictive. Variations and changes may be made by those skilled in the art without departing from the spirit of the invention.
Claims (12)
1. An interior container coating composition comprising a solution, emulsion, or dispersion of a synthetic thermoplastic or thermosetting film forming resin having blended therein about 0.5 to about 5 weight percent, based on the weight of the coating composition, of a cyclodextrin.
2. The composition of Claim 1 wherein the cyclodextrin is beta-cyclodextrin.
3. The composition of Claim 2 which contains about 1 to about 3 weight percent beta-cyclodextrin.
4. The composition of Claim 1 wherein the composition is an aqueous dispersion of a synthetic film forming resin.
5. The composition of Claim 4 wherein the synthetic film forming resin is a thermosetting resin.
6. The composition of Claim 5 wherein the thermosetting resin is an epoxy resin and an aminoresin.
7. A process for protecting the flavor of food or beverages stored in containers which comprises: (a) coating the interior of the containers with a coating compositions which is a solution, emulsion, or dispersion of a synthetic thermoplastic or thermosetting film forming resin having blended therein about 0.5 to about 5 weight percent, based on the weight of the coating composition, of a cyclodextrin, and (b) drying the coating composition.
8. The process of Claim 7 wherein the cyclodextrin is beta-cyclodextrin.
9. The process of Claim 8 wherein the amount of beta-cyclodextrin is about 1 to about 3 weight percent.
10. The process of Claim 7 wherein the coating composition is an aqueous dispersion o a synthetic film forming resin.
11. The process of Claim 10 wherein the synthetic film forming resin is a thermosetting resin.
12. The process of Claim 11 wherein the thermosetting resin is an epoxy resin and an aminoresin.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/688,842 US5177129A (en) | 1991-04-22 | 1991-04-22 | Interior can coating compositions containing cyclodextrins |
| JP4174286A JPH0632344A (en) | 1991-04-22 | 1992-07-01 | Composition for coating inside of cyclodextrin containing can |
| CA002072956A CA2072956A1 (en) | 1991-04-22 | 1992-07-02 | Interior can coating compositions containing cyclodextrins |
| ES92306164T ES2094298T3 (en) | 1991-04-22 | 1992-07-03 | COATING COMPOSITIONS FOR THE INSIDE OF JARS, CONTAINING CYCLODEXTRINES. |
| EP92306164A EP0576756B1 (en) | 1991-04-22 | 1992-07-03 | Interior can coating compositions containing cyclodextrins |
| DE69215507T DE69215507T2 (en) | 1991-04-22 | 1992-07-03 | Cyclodextrin-containing composition for coatings on inner surfaces of tins |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/688,842 US5177129A (en) | 1991-04-22 | 1991-04-22 | Interior can coating compositions containing cyclodextrins |
| JP4174286A JPH0632344A (en) | 1991-04-22 | 1992-07-01 | Composition for coating inside of cyclodextrin containing can |
| CA002072956A CA2072956A1 (en) | 1991-04-22 | 1992-07-02 | Interior can coating compositions containing cyclodextrins |
| EP92306164A EP0576756B1 (en) | 1991-04-22 | 1992-07-03 | Interior can coating compositions containing cyclodextrins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2072956A1 true CA2072956A1 (en) | 1994-01-03 |
Family
ID=27426925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002072956A Abandoned CA2072956A1 (en) | 1991-04-22 | 1992-07-02 | Interior can coating compositions containing cyclodextrins |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5177129A (en) |
| EP (1) | EP0576756B1 (en) |
| JP (1) | JPH0632344A (en) |
| CA (1) | CA2072956A1 (en) |
| DE (1) | DE69215507T2 (en) |
| ES (1) | ES2094298T3 (en) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4009621A1 (en) * | 1990-03-26 | 1991-10-02 | Henkel Kgaa | (ALPHA) -CYANACRYLATE ADHESIVE COMPOSITIONS |
| US5352717A (en) * | 1990-05-04 | 1994-10-04 | American Maize Technology Inc. | Adhesives and sealants |
| JPH06340793A (en) * | 1992-12-22 | 1994-12-13 | Du Pont Kk | Polyacetal resin composition excellent in moldability and reduced in formaldehyde odor from molded product thereof |
| US5928745A (en) * | 1994-06-23 | 1999-07-27 | Cellresin Technologies, Llc | Thermoplastic fuel tank having reduced fuel vapor emissions |
| US5492947A (en) * | 1994-06-23 | 1996-02-20 | Aspen Research Corporation | Barrier material comprising a thermoplastic and a compatible cyclodextrin derivative |
| US5776842A (en) | 1994-06-23 | 1998-07-07 | Cellresin Technologies, Llc | Cellulosic web with a contaminant barrier or trap |
| US5985772A (en) | 1994-06-23 | 1999-11-16 | Cellresin Technologies, Llc | Packaging system comprising cellulosic web with a permeant barrier or contaminant trap |
| US5837339A (en) * | 1994-06-23 | 1998-11-17 | Cellresin Technologies, Llc | Rigid polymeric beverage bottles with improved resistance to permeant elution |
| US5701090A (en) * | 1994-11-15 | 1997-12-23 | Mitsubishi Denki Kabushiki Kaisha | Data output circuit with reduced output noise |
| US5567747A (en) * | 1995-07-18 | 1996-10-22 | Sun Chemical Corporation | Water-based printing ink |
| US5882565A (en) | 1995-12-11 | 1999-03-16 | Cellresin Technologies, Llc | Barrier material comprising a thermoplastic and a compatible cyclodextrin derivative |
| WO1997030122A1 (en) * | 1996-02-20 | 1997-08-21 | Cellresin Technologies, L.L.C. | Rigid polymer beverage bottles with improved resistance to permeant elution |
| DE19615494A1 (en) * | 1996-04-19 | 1997-10-23 | Basf Lacke & Farben | Process for improving the gloss and leveling of paints |
| US20020132861A1 (en) * | 2000-08-18 | 2002-09-19 | Hirotaka Uchiyama | Reduction of odors from coating material |
| US7638179B2 (en) * | 2001-05-05 | 2009-12-29 | Cellresin Technologies, Llc | Sealing element for vessel or container closures having improved barrier properties |
| US6924328B2 (en) | 2001-09-06 | 2005-08-02 | Valspar Sourcing, Inc. | Stabilized coating compositions |
| EP1434831B1 (en) * | 2001-09-06 | 2005-03-16 | Valspar Sourcing, Inc. | Stabilized coating compositions |
| US6916874B2 (en) | 2001-09-06 | 2005-07-12 | Valspar Sourcing, Inc. | Coating compositions having epoxy functional stabilizer |
| US6851462B2 (en) * | 2001-10-30 | 2005-02-08 | The Goodyear Tire & Rubber Company | Rubber compositions containing a cyclodextrin compound |
| US20030207056A1 (en) * | 2002-05-03 | 2003-11-06 | Will Wood | Sealing element for vessel or container closures having improved barrier properties |
| WO2004090020A1 (en) | 2003-04-02 | 2004-10-21 | Valspar Sourcing, Inc. | Aqueous dispersions and coatings |
| ATE513025T1 (en) * | 2004-10-20 | 2011-07-15 | Valspar Sourcing Inc | COATING COMPOSITIONS FOR CANS AND COATING PROCESSES |
| CN101076261B (en) * | 2004-12-16 | 2011-10-05 | 道康宁公司 | Method of preventing or reducing off-flavor in a beverage using silane-treated silica filter media |
| PL2416962T3 (en) | 2009-04-09 | 2017-07-31 | Valspar Sourcing, Inc. | Polymer having unsaturated cycloaliphatic functionality and coating compositions formed therefrom |
| US8486574B2 (en) * | 2009-07-14 | 2013-07-16 | Ford Global Technologies, Llc | Method and system for power control in an automotive vehicle |
| US8754614B2 (en) * | 2009-07-17 | 2014-06-17 | Tesla Motors, Inc. | Fast charging of battery using adjustable voltage control |
| US8747979B2 (en) | 2009-07-17 | 2014-06-10 | Valspar Sourcing, Inc. | Coating compositions and articles coated therewith |
| US9011999B2 (en) | 2009-09-18 | 2015-04-21 | Valspar Sourcing, Inc. | Coating composition including an unsaturated polymer |
| WO2012039708A1 (en) * | 2010-09-22 | 2012-03-29 | Empire Technology Development Llc | Can with bisphenol a capture system |
| WO2014058438A1 (en) * | 2012-10-12 | 2014-04-17 | Empire Technology Development Llc | Paints and coatings containing cyclodextrin additives |
| EP2943530A1 (en) * | 2013-01-08 | 2015-11-18 | Sika Technology AG | Reduction of benzyl alcohol emissions from epoxy amine formulations by adding cyclodextrin |
| US9263397B2 (en) | 2013-03-12 | 2016-02-16 | Microchip Technology Incorporated | Wafer mapping process control with indicator line |
| JP6308256B2 (en) * | 2016-08-09 | 2018-04-11 | 住友化学株式会社 | Composition, film, electronic device, and organic thin film transistor |
| DE102019109425B4 (en) | 2019-04-10 | 2022-01-05 | Uvex Safety Gloves Gmbh & Co. Kg | Process for the production of an impregnated polymer substrate, Process for the production of chemical protective gloves and Use of an impregnated polymer substrate for protective clothing |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4289674A (en) * | 1978-11-29 | 1981-09-15 | Ppg Industries, Inc. | Base-solubilized acrylic polymers and aqueous resinous dispersions of acrylic polymers and epoxy resins |
| JPS60252658A (en) * | 1984-05-28 | 1985-12-13 | Ichiro Shibauchi | Rust-proofing material |
| JPS61152765A (en) * | 1984-12-27 | 1986-07-11 | Nippon Ekishiyou Kk | Synthetic resin product including compound clathrated with cyclodextrin |
| US4917956A (en) * | 1988-07-11 | 1990-04-17 | Uop | Method of preparing cyclodextrin-coated surfaces |
| US5098793A (en) * | 1988-09-29 | 1992-03-24 | Uop | Cyclodextrin films on solid substrates |
| US5063251A (en) * | 1990-05-04 | 1991-11-05 | American Maize-Products Company | Blowing and curing of resins and plastics materials with cyclodextrin complexes |
| US5137571A (en) * | 1990-06-05 | 1992-08-11 | Rohm And Haas Company | Method for improving thickeners for aqueous systems |
-
1991
- 1991-04-22 US US07/688,842 patent/US5177129A/en not_active Expired - Fee Related
-
1992
- 1992-07-01 JP JP4174286A patent/JPH0632344A/en active Pending
- 1992-07-02 CA CA002072956A patent/CA2072956A1/en not_active Abandoned
- 1992-07-03 ES ES92306164T patent/ES2094298T3/en not_active Expired - Lifetime
- 1992-07-03 EP EP92306164A patent/EP0576756B1/en not_active Expired - Lifetime
- 1992-07-03 DE DE69215507T patent/DE69215507T2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0576756A1 (en) | 1994-01-05 |
| EP0576756B1 (en) | 1996-11-27 |
| ES2094298T3 (en) | 1997-01-16 |
| DE69215507T2 (en) | 1997-03-27 |
| US5177129A (en) | 1993-01-05 |
| JPH0632344A (en) | 1994-02-08 |
| DE69215507D1 (en) | 1997-01-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5177129A (en) | Interior can coating compositions containing cyclodextrins | |
| US5840825A (en) | Gas barrier coating compositions containing platelet-type fillers | |
| CN1031615C (en) | Spray-dried fixed flavorants in a carbohydrate substrate and process | |
| US5728439A (en) | Multilayer packaging material for oxygen sensitive food and beverage | |
| EP3017942B1 (en) | Resin molded article provided with surface having exceptional water-sheeting properties | |
| US5523338A (en) | Synthetic hectorite coated flexible film | |
| EP1674522A1 (en) | Enhanced lubrication in polyolefin closure with polyolefin grafted cyclodextrin | |
| CN101316892A (en) | Paint for pot not containing BADGE and BPA | |
| JP2005500205A (en) | Packaging material with improved barrier properties | |
| EP0665263B1 (en) | Gas barrier laminate and production process thereof | |
| KR102344166B1 (en) | Polyolefin Silicon Coating Composition | |
| JP3096318B2 (en) | Composite film and method for producing the same | |
| US5709951A (en) | Composite deposited film and production process thereof | |
| KR20040050062A (en) | Container having improved organoleptic barrier properties | |
| EP3947182A1 (en) | Biodegradable and compostable vessels, such as coffee pods, coated with pecvd coatings or layers | |
| JP2000005019A (en) | Food and drink container for infant | |
| JP5391454B2 (en) | Modified cyclodextrin particle dispersion and process for producing the same | |
| TWI294907B (en) | Anti-fog resin sheet and process for producing molded article | |
| US20210206891A1 (en) | Tube and method for making same | |
| FR2755972A1 (en) | PROCESS FOR THE PREPARATION OF MICROPARTICLES OF MINERAL PIGMENTS COATED WITH A CHAIN LAYER, MICROPARTICLES OBTAINED AND USE OF SUCH MICROPARTICLES | |
| Liu et al. | Application of surface‐modified functional packaging in food storage: A comprehensive review | |
| KR100507792B1 (en) | Lithium and potassium copolysilicate barrier coatings | |
| JPH02173072A (en) | Composition for forming ultraviolet-absorbing thin film | |
| EP0180360A2 (en) | Polymeric composite sheet | |
| JPS60161463A (en) | Synthetic resin emulsion composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |