CAGNARD ALAIN MICHEL (US)
US3799380A | 1974-03-26 | |||
US20110290696A1 | 2011-12-01 | |||
US10450449B2 | 2019-10-22 | |||
US10189610B2 | 2019-01-29 | |||
EP2509883B1 | 2017-03-22 |
What is claimed is: 1. A method for manufacturing a vessel cap for use with a vessel adapted to store foods or beverages, the method comprising: providing a cap body configured for attachment to a neck of a vessel; reacting an isocyanate component and a curative component at a temperature of from 60 ºC to 140 ºC along a cap body to form a polyurethane elastomer gasket, wherein the polyurethane elastomer gasket is positioned on the cap body such that it may be deformed and compressed when the cap body is attached to a vessel, wherein the polyurethane elastomer gasket and the cap body together form a vessel cap. 2. The method of claim 1, wherein the vessel cap is a lug screw cap, a Press-on Twist-Off® cap, a hooded lid, a crimp-on or single-use cap, or a metal cap that can be rolled on to the vessel. 3. The method of claims 1 and 2, polyurethane elastomer gasket is substantially free of components that are liquid at room temperature. 4. The method of claims 1-3, polyurethane elastomer gasket is substantially free of polyvinyl chloride. 5. The method of claims 1-4, wherein the polyurethane elastomer gasket has a Shore A hardness of from 50 to 95. 6. The method of claims 1-5, wherein the isocyanate component comprises: i. a polyisocyanate that is an aliphatic isocyanate or a cycloaliphatic isocyanate; and ii. an isocyanate reactive component. 7. The method of claim 6, wherein the polyisocyanate is selected from the group consisting of hexamethylene diisocyanate (“HDI”) and isomers thereof, isophorone diisocyanate (“IPDI”) and isomers thereof, norbornane diisocyanate (“NBDI”) and isomers thereof, tetramethylxylylene diisocyanate (“TMXDI”) and isomers thereof, and xylylene diisocyanate (“XDI”) and isomers thereof, and mixtures thereof. 8. The method of claims 6 or 7, wherein the isocyanate reactive component is selected from the group consisting of polyether polyols, polyester polyols, polycaprolactone polyols, polycarbonate polyols, hydroxyl-terminated polybutadiene polyols, natural oil-based polyols, and short chain glycols, or combinations thereof. 9. The method of claims 6-8, wherein the isocyanate reactive component is a polyester polyol comprising: i. an acid component comprising residues of at least one dicarboxyl monomer; and ii. a diol component comprising residues of (a) a 2,2,4,4-tetraalkyl-1,3-cyclobutanediol (TACD); and (b) at least one diol or polyol other than TACD, wherein the polyester polyol has a hydroxyl functionality of from 2 to 3. 10. The method of claims 1-9, wherein the curative component comprises: i. one or more isocyanate reactive compounds; and ii. a catalyst. 11. The method of claim 10, wherein the one or more isocyanate reactive compounds are hydroxyl-terminated isocyanate reactive compounds or amine- terminated isocyanate reactive compounds. 12. The method of claim 11, wherein the hydroxyl-terminated isocyanate reactive compounds are selected from the group consisting of polyether polyols, polyester polyols, polycaprolactone polyols, polycarbonate polyols, hydroxyl-terminated polybutadiene polyols, natural oil-based polyols, short chain glycols, and mixtures thereof. 13. The method of claim 10-12, wherein the one or more isocyanate reactive compound is 2,2,4,4-tetraalkyl-1,3-cyclobutanediol. 14. The method of claim 8, wherein the catalyst is selected from the group consisting of amine-based catalysts, tin-based catalysts, zinc-based catalyst, zirconium-based catalysts, bismuth-based catalysts, and mixtures thereof. |
Table 1 – Raw Materials [0036] Polyester Polyol A is prepared as follows: in a four-neck 5-liter glass reactor equipped with a mechanical stirrer, a thermocouple, a heated partial condenser (100°C), a Dean-Stark trap, a chilled condenser (15°C), and a nitrogen inlet, 1753.2 grams of adipic acid, 1040.6 grams of 1,5-pentanediol, 411.8 grams of 1,4-cyclohexanedimethanol, 205.9 grams of 2,2,4,4- tetramethyl-1,3-cyclobutanediol, 3.41 grams of IRGAFOS™ 168, and 3.41 grams of WESTON™ 618F are charged. The reactor is placed in a heating mantle connected to a temperature controller. With nitrogen on, the mixture in the reactor is slowly heated up to 110°C. Once the mixture is melted, agitation is applied at 200 rpm. With agitation on under nitrogen sweep, the mixture is heated to 230°C at a ramp speed of 0.2°C/minute. The mixture is allowed to react further under a nitrogen blanket at 230°C. A sample is taken after 6 hours at 230°C for acid number analysis. If the acid number is more than 1.0 mg KOH/g, the reaction will be allowed to continue until the acid number of the reaction mixture reaches less than or equal to 1.0 mg KOH/g. The resultant material is a clear liquid at room temperature. [0037] Comparative Example A is prepared by adding into a dry 200 Max FlackTek cup, 100 grams of VESTOLIT G 178 and 73 grams of DRAPEX™ 6.8. The cup is then placed in a FlackTek DAC 1200-500 VAC and mixed at 2000 rpm for 5 minutes followed by mixing at 2000 rpm for an additional 5 minutes under vacuum. A homogenous, viscous, off-white dispersion is obtained. The mixture is then poured into an aluminum mold preconditioned at 190°C to form a sample sheet at about 1.9 mm thickness and the gel point is determined. After curing at 190°C for 1 hour, the specimen is removed from the mold and conditioned at an ambient environment for two weeks before it is subjected to testing of physical properties. Shore A hardness, tensile strength, and elongation at break are measured and the results are provided in Table 3. [0038] The exemplary formulations are prepared as follows: Inventive Example 1 [0039] Isocyanate Component: A 500 ml lab glass reactor consisting of a 4- neck flask equipped with a mechanical stir and a temperature controller is used to produce the isocyanate component. Under nitrogen blanket, into the lab glass reactor, 81.8 grams of DESMODUR™ H is first loaded. The temperature of the reactor is set to 50°C. With agitation on, 100.0 grams of POLYOL™ P- 510 polyol preheated to 60°C is added to the reactor. Cooling is applied if the reaction temperature exceeds 95°C. Reset the temperature of the reactor to 95°C after exotherm of the reaction is leveled off. The reaction is held at 95°C for 5 hours followed by addition of 32.1 grams of DESMODUR™ N3300. After mixing for additional 45 minutes at 95°C, a clear, low viscosity prepolymer is obtained. The prepolymer is found to have an NCO content of 14.3%. [0040] Curative Component: A 500 ml lab glass reactor consisting of a 4- neck flask equipped with a mechanical stir and a temperature controller is used to produce the isocyanate reactive component. The temperature of the reactor is set at 65°C. Under N2 purge and with agitation on, 170.0 grams of POLYOL™ P-510 polyol preheated to 60°C is charged to the reactor, followed by the addition of 30.0 grams of 1,4 butanediol, and 2.0 grams of K-KAT XK- 672. After mixing at 60°C for 45 minutes, a clear, low viscosity liquid is obtained. The mixture has an OH number of 377.5. [0041] Polyurethane Elastomer: Into a dry 200 Max FlackTek cup, 50.0 grams of the curative component preheated at 65°C and 101.7 grams of the isocyanate component preheated at 65°C are added. Mixing is done on a FlackTek DAC 1200-500 VAC at 2000 rpm under vacuum for 1 minutes. The mixture is then poured into an aluminum mold preconditioned at 120°C to form a sample sheet at about 1.9 mm thickness and determine the gel point. After cured at 120°C for 1 hour, the specimen is removed from the mold and conditioned at an ambient environment for two weeks before it is subjected to physical property testing. Results are listed in Table 2. Inventive Example 2 [0042] Isocyanate Component: Example 1 is repeated except that 60.4 grams of DESMODUR™ H, 100.0 grams of PTMEG 650, and 40.1 grams of DESMODUR™ N3300 are used. The prepolymer is a clear, low viscosity liquid at room temperature and has an NCO content of 12.8%. [0043] Curative component: Example 1 is repeated except that 180.0 grams of PH-50, 20.0 grams of 1,4 butanediol, and 2.0 grams of K-KAT XK-672 are used. The mixture is a clear, low viscosity liquid at room temperature and has an OH number of 319.5. [0044] Polyurethane Elastomer: Example 1 is repeated except that 96.7 grams of the isocyanate component and 50.0 grams of the curative component are used. Results are listed in Table 2. Inventive Example 3 [0045] Isocyanate Component: Example 1 is repeated except that 73.7 grams of DESMODUR™ H, 100.0 grams of PC-1011P-210, and 43.4 grams of DESMODUR™ N3300 are used. The prepolymer is a clear, low viscosity liquid at room temperature and has an NCO content of 13.9%. [0046] Curative component: Example 1 is repeated except that 147.2 grams of PC-1011-55, 12.8 grams of 1,4 butanediol, and 1.6 grams of K-KAT XK-672 are used. The mixture is a clear, viscous liquid at room temperature and has an OH number of 150.3. [0047] Polyurethane Elastomer: Example 1 is repeated except that 68.7 grams of the isocyanate component and 80.0 grams of the curative component are used. Results are listed in Table 2. Inventive Example 4 [0048] Isocyanate Component: Example 1 is repeated except that 77.9 grams of DESMODUR™ H, 100.0 grams of PH-50, and 31.4 grams of DESMODUR™ N3300 are used. The prepolymer is a clear, low viscosity liquid at room temperature and has an NCO content of 13.9%. [0049] Curative Component: Example 1 is repeated except that 170.0 grams of PH-50, 30.0 grams of 1,4 butanediol, and 2.0 grams of K-KAT XK-672 are used. The mixture is a clear, viscous liquid at room temperature and has an OH number of 371.5. [0050] Polyurethane Elastomer: Example 1 is repeated except that 103.8 grams of the isocyanate component and 50.0 grams of the curative component are used. Results are listed in Table 2. Inventive Example 5 [0051] Isocyanate Component: Example 1 is repeated except that 77.9 grams of DESMODUR™ H, 100.0 grams of PH-50, and 31.4 grams of DESMODUR™ N3300 are used. The prepolymer is a clear, low viscosity liquid at room temperature and has an NCO content of 13.9%. [0052] Curative Component: Example 1 is repeated except that 170.0 grams of PH-100, 30.0 grams of 1,4 butanediol, and 2.0 grams of K-KAT XK-672 are used. The mixture is a clear, viscous liquid at room temperature and has an OH number of 284.8. [0053] Polyurethane Elastomer: Example 1 is repeated except that 79.6 grams of the isocyanate component and 50.0 grams of the curative component are used. Results are listed in Table 2. Inventive Example 6 [0054] Isocyanate Component: Example 1 is repeated except that 77.9 grams of DESMODUR™ H, 100.0 grams of PH-50, and 31.4 grams of DESMODUR™ N3300 are used. The prepolymer is a clear, low viscosity liquid at room temperature and has an NCO content of 13.9%. [0055] Curative Component: Example 1 is repeated except that 102.0 grams of DESMOPHEN™ C2202, 18.0 grams of 1,4 butanediol, and 1.2 grams of K- KAT XK-672 are used. The mixture is a clear, viscous liquid at room temperature and has an OH number of 234.6. [0056] Polyurethane Elastomer: Example 1 is repeated except that 78.6 grams of the isocyanate component and 60.0 grams of the curative component are used. Results are listed in Table 2. Inventive Example 7 [0057] Isocyanate Component: Example 1 is repeated except that 126.4 grams of TAKENATE™ 500, 75.0 grams of POLYOL™ P-510, 25.0 grams of 3-methyl 1,5 pentanediol, and 25.2 grams of DESMODUR™ N3300 are used. The prepolymer is a clear, low viscosity liquid at room temperature and has an NCO content of 12.5%. [0058] Curative Component: Example 1 is repeated except that 85.0 grams of POLYOL™ P-510, 15.0 grams of 1,4 butanediol, and 1.0 grams of K-KAT XK-672 are used. The mixture is a clear, viscous liquid at room temperature and has an OH number of 377.4. [0059] Polyurethane Elastomer: Example 1 is repeated except that 116.7 grams of the isocyanate component and 50.0 grams of the curative component are used. Results are listed in Table 2. Inventive Example 8 [0060] Isocyanate Component: Example 1 is repeated except that 111.1 grams of TAKENATE™ 500, 75.0 grams of PTMEG 650, 25.0 grams of 3- methyl 1,5 pentanediol, and 37.3 grams of DESMODUR™ N3300 are used. The prepolymer is a clear, low viscosity liquid at room temperature and has an NCO content of 12.1%. [0061] Curative Component: Example 1 is repeated except that 80.0 grams of PTMEG 650, 20.0 grams of 1,4 butanediol, and 1.0 grams of K-KAT XK-672 are used. The mixture is a clear, viscous liquid at room temperature and has an OH number of 387.8. [0062] Polyurethane Elastomer: Example 1 is repeated except that 123.5 grams of the isocyanate component and 50.0 grams of the curative component are used. Results are listed in Table 2. Inventive Example 9 [0063] Isocyanate Component: Example 1 is repeated except that 88.7 grams of DESMODUR™ H, 80.0 grams of POLYOL™ P2010, 20.0 grams of 1,3 butanediol, and 21.0 grams of DESMODUR™ N3300 are used. The prepolymer is a clear, low viscosity liquid at room temperature and has an NCO content of 12.6%. [0064] Curative Component: Example 1 is repeated except that 69.0 grams of POLYOL™ P-510, 11.0 grams of 1,4 butanediol, and 0.8 grams of K-KAT XK-672 are used. The mixture is a clear, viscous liquid at room temperature and has an OH number of 364.6. [0065] Polyurethane Elastomer: Example 1 is repeated except that 91.0 grams of the isocyanate component and 40.0 grams of the curative component are used. Results are listed in Table 2. Inventive Example 10 [0066] Isocyanate Component: Example 1 is repeated except that 182.8 grams of DESMODUR™ H, 160.0 grams of Polyester Polyol A, 40.0 grams of 1,3 butanediol, and 42.6 grams of DESMODUR™ N3300 are used. The prepolymer is a clear, low viscosity liquid at room temperature and has an NCO content of 12.8%. [0067] Curative Component: Example 1 is repeated except that 60.0 grams of Polyester Polyol A, 20.0 grams of 1,4 butanediol, and 0.8 grams of K-KAT XK-672 are used. The mixture is a clear, viscous liquid at room temperature and has an OH number of 361.2. [0068] Polyurethane Elastomer: Example 1 is repeated except that 97.7 grams of the isocyanate component and 40.0 grams of the curative component are used. Results are listed in Table 2. Inventive Example 11 [0069] Isocyanate Component: is the same as in Inventive Example 10. [0070] Curative Component: Example 1 is repeated except that 88.4 grams of Polyester Polyol A, 15.6 grams of 1,4 butanediol, and 1.0 grams of K-KAT XK-672 are used. The mixture is a clear, viscous liquid at room temperature and has an OH number of 243.1. [0071] Polyurethane Elastomer: Example 1 is repeated except that 77.7 grams of the isocyanate component and 52.0 grams of the curative component are used. Results are listed in Table 2. Inventive Example 12 [0072] Isocyanate Component: is the same as in Inventive Example 10. [0073] Curative Component: Example 1 is repeated except that 108.0 grams of Polyester Polyol A, 12.0 grams of 1,4 butanediol, and 1.2 grams of K-KAT XK-672 are used. The mixture is a clear, viscous liquid at room temperature and has an OH number of 184.1. [0074] Polyurethane Elastomer: Example 1 is repeated except that 67.9 grams of the isocyanate component and 60.0 grams of the curative component are used. Results are listed in Table 2.
Table 2 - Results [0075] As shown in the Tables above, the formulations of the present invention exhibit lower processing temperatures and, at the same time, the mechanical properties of the formulations are either not compromised or significantly improved. [0076] The dimensions and values disclosed herein are not to be understood as being strictly limited to the exact numerical values recited. Instead, unless otherwise specified, each such dimension is intended to mean both the recited value and a functionally equivalent range surrounding that value. For example, a dimension disclosed as “40 mm” is intended to mean “about 40 mm.” [0077] Every document cited herein, if any, including any cross- referenced or related patent or application and any patent application or patent to which this application claims priority or benefit thereof, is hereby incorporated herein by reference in its entirety unless expressly excluded or otherwise limited. The citation of any document is not an admission that it is prior art with respect to any invention disclosed or claimed herein or that it alone, or in any combination with any other reference or references, teaches, suggests or discloses any such invention. Further, to the extent that any meaning or definition of a term in this document conflicts with any meaning or definition of the same term in a document incorporated by reference, the meaning or definition assigned to that term in this document shall govern. [0078] While particular embodiments of the present invention have been illustrated and described, it would be obvious to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the invention. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this invention.
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