Low VOC, fluorocompound-containing one-component and two-component coating compositions for slippery coatings

• US 5,496,642 A
• Filed: 05/09/1994
• Issued: 03/05/1996
• Est. Priority Date: 05/09/1994
• Status: Expired due to Term

• Current Assignee: Bayer Corporation (Bayer AG)
• Original Assignee: OLIN Corporation
• Inventors: Martinez, Michael M., Chandalia, Kiran B., Malofsky, Adam G., Stuber, Fred A.
• Primary Examiner(s): Seidleck, James J.
• Assistant Examiner(s): Truong, Duc
• Application Number:
  US08/239,883
• Time in Patent Office: 666 Days
• Field of Search: 521/49, 521/49.5, 428/423.1, 428/422.8, 520/45, 520/67, 520/73, 427/385.5, 528/45, 528/67, 528/73
• US Class Current: 428/423.1
• CPC Class Codes: C08G 18/165 covered by C08G18/18 and C08G18/24
• CPC Class Codes: C08G 18/283 Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
• CPC Class Codes: C08G 18/2885 containing halogen atoms
• CPC Class Codes: Y10T 428/3154 Of fluorinated addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31547 Of polyisocyanurate
• CPC Class Codes: Y10T 428/31551 Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]

Abstract

This invention relates to one-component and two-component heat-curable or moisture-curable coating compositions, and processes for their use in providing a slippery coating on a substrate utilizing a polyisocyanate-based low VOC coating composition, employing a fluoro-containing active hydrogen-containing compound, and which is suitably rapidly hardened under the influence of heat or moisture.

Claims

1. A process for providing a slippery coating on a substrate which comprises:

(a) contacting said substrate with a low volatile-organics, one-component, heat curable coating composition to form a coating on said substrate, said coating composition having a viscosity as measured by ZAHN cup 2 of less than about 200 seconds and consisting essentially of at least one blocked polyisocyanate, a fluorine-containing monoahl alone or in combination with a fluorine-free active hydrogen-containing compound, a solvent in an amount of between 0% and 45% by weight based upon the amount of said polyisocyanate in said composition, and a trimerization catalyst, said composition being essentially free of any mono- and di-isocyanate monomers, and

(b) heating said coating to a curing temperature of between 120°

F. and 350°

F. for a curing time of between about ten minutes and about six hours in order to cure said coating by trimerizing at least some isocyanate groups of said polyisocyanate to provide a heat-cured coating on said substrate,

said heat-cured coating being characterized by a contact angle of greater than 63 degrees.

5. The process of any of claims 1 through 4 wherein said fluorine-containing monoahl is selected from the group consisting of monoahls, polyols, imines and combinations thereof.

6. The process of any of claims 1 through 4 wherein said solvent is selected from the group consisting of toluene, xylene, butyl acetate, methyl ethyl ketone, methyl isobutyl ketone, methylamyl ketone, ethoxyethylacetate, ethylethoxy propionate an aromatic hydrocarbon mixture having a boiling point of 152-174°

C., and combinations thereof.

7. The process of any of claims 1 through 4 wherein said polyisocyanate has an average functionality of least 2.

8. The process of any of claims 1 through 4 wherein said fluorine-free active hydrogen-containing compound is selected from the group consisting of monoahls, polyols, imines and combinations thereof.

9. The process of any of claims 1 through 4 wherein said polyisocyanate contains a moiety selected from the group consisting of biuret, uretidione, isocyanurate, urethane, allophanate, and combinations thereof.

10. The process of any of claims 1 through 4 wherein said polyisocyanate is selected from the group consisting of tris-(isocyanatohexyl)-biuret, tris-(isocyanatohexyl)-isocyanurate, cyclodimerized hexamethylene diisocyanate, and combinations thereof.

11. A coated substrate produced by the process of any of claims 1 through 4 and characterized by a fluoro-containing coating on said coated substrate.

2. A process for providing a slippery coating on a substrate which comprises:

(a) contacting said substrate with a low volatile-organics, two-component, heat curable coating composition to form a coating on said substrate, said coating composition having a viscosity as measured by ZAHN cup 2 of less than about 200 seconds and consisting essentially of at least one polyisocyanate, a fluorine-containing monoahl alone or in combination with a fluorine-free active hydrogen-containing compound, a solvent in an amount of between 0% and 45% by weight based upon the amount of said polyisocyanate in said composition, and a trimerization catalyst, said composition being essentially free of any mono- and di-isocyanate monomers, and

(b) heating said coating to a curing temperature of between 120°

F. and 350°

F. for a curing time of between about ten minutes and about six hours in order to cure said coating by trimerizing at least some isocyanate groups of said polyisocyanate to provide a heat-cured coating on said substrate,

said heat-cured coating being characterized by a contact angle of greater than 63 degrees.

3. A process for providing a slippery coating on a substrate which comprises:

(a) contacting said substrate with a low volatile organics-containing, one-component, moisture curable coating composition to form a coating on said substrate, said coating composition having a viscosity as measured by ZAHN cup 2 of less than about 200 seconds and consisting essentially of at least one polyisocyanate prepolymer which is the reaction product of a polyisocyanate with a fluorine-containing, monoahl alone or in combination with a fluorine-free active hydrogen-containing compound, a solvent in an amount of between 0% and 45% by weight based upon the amount of said composition, and a tertiary amine catalyst, said composition being essentially free of any mono- and di-isocyanate monomers, and said composition being moisture curable upon exposure to atmospheric or added moisture, and

(b) exposing said coating to atmospheric or added moisture to provide a moisture-cured coating on said substrate,

said moisture-cured coating being characterized by a contact angle for deionized water on the coating of greater than 63 degrees.

4. A process for providing a slippery coating on a substrate which comprises:

(a) contacting said substrate with a low volatile organics-containing, two-component, moisture curable coating composition to form a coating on said substrate, said coating composition having a viscosity as measured by ZAHN cup 2 of less than about 200 seconds and consisting essentially of at least one polyisocyanate, a fluorine-containing, monoahl alone or in combination with a fluorine-free active hydrogen-containing compound, a solvent in an amount of between 0% and 45% by weight based upon the amount of said polyisocyanate in said composition, and a tertiary amine catalyst, said composition being essentially free of any volatile mono- and di-isocyanates, and said composition being moisture curable upon exposure to atmospheric or added moisture, and

(b) exposing said coating to atmospheric or added moisture to provide a moisture-cured coating on said substrate,

said moisture-cured coating being characterized by a contact angle of greater than 63 degrees.