Scratch-resistant anti-fog coating composition incorporating isocyanate-reactive surfactants

• US 5,877,254 A
• Filed: 07/22/1996
• Issued: 03/02/1999
• Est. Priority Date: 07/22/1996
• Status: Expired due to Term

• Current Assignee: FSI Coating Technologies, Inc.
• Original Assignee: Film Specialties, Inc.
• Inventors: Creasy, Walter S., La Casse, Robert G.
• Primary Examiner(s): NILAND, PATRICK DENNIS
• Application Number:
  US08/681,154
• Time in Patent Office: 953 Days
• Field of Search: 524/589, 524/590, 427/162, 427/372.2, 427/385.5, 523/169
• US Class Current: 524/590
• CPC Class Codes: C08G 18/0828 containing sulfonate groups or groups forming them
• CPC Class Codes: C08G 18/0833 containing cationic or cationogenic groups together with anionic or anionogenic groups
• CPC Class Codes: C08J 2375/04 Polyurethanes
• CPC Class Codes: C08J 3/09 in organic liquids
• CPC Class Codes: C09D 175/04 Polyurethanes
• CPC Class Codes: C09K 3/18 for application to surfaces to minimize adherence of ice, mist or water thereto rendering particulate materials free flowing, in general, e.g. making them hydrophobic B01J2/30; Thawing or antifreeze materials for application to surfaces used in liquids for heat-transfer, heat-exchange or heat-storage or for the production of heat or cold other than by combustion, e.g. radiator liquids, C09K5/00

Abstract

Anti-fog and scratch resistant polyurethane compositions are disclosed which include an isocyanate prepolymer, a hydrophilic polyol and an isocyanate-reactive surfactant. The reaction product of the component produces enhanced properties having permanent anti-fog and scratch-resistant characteristics. These compositions may be used as coatings, films and self-supporting articles. Plastic substrates coated with these compositions may be subsequently subjected to thermoforming, such as molding and shaping, without loss of their properties.

Claims

1. A polymer composition which, when cured, provides a scratch-resistant, permanent anti-fog surface comprising:

i) an isocyanate prepolymer having unreacted isocyanate groups; and

ii) an organic solvent solution comprising a hydrophilic polyol compound and a surfactant comprising a non-ethoxylated hydrocarbon chain with greater than 16 carbon atoms containing an isocyanate-reactive group, said surfactant being selected from the group consisting of anionic surfactants, cationic surfactants and mixtures thereof, said surfactant having distinct hydrophobic and hydrophilic segments.

2. A composition as in claim 1, wherein said isocyanate-reactive group is selected from the group consisting of hydroxyl, amino, carboxyl and thiol functional groups.

6. A composition as in claim 1, wherein said hydrophilic polyol is selected from the group consisting of polyethylene glycol and ethylene glycol/propylene glycol copolymers.

7. A composition as in claim 1, wherein said isocyanate prepolymer is selected from the group consisting of biurets of diisocyanates and isocyanurates of diisocyanates.

8. A composition as in claim 7, wherein said diisocyanate is hexamethylene diisocyanate biuret.

9. A composition as in claim 1, further including a catalyst.

3. A polymer composition which, when cured, provides a scratch-resistant, permanent anti-fog surface comprising:

i) an isocyanate prepolymer having unreacted isocyanate groups; and

ii) an organic solvent solution comprising a hydrophilic polyol compound and a surfactant containing an isocyanate-reactive group, said surfactant being selected from the group consisting of anionic surfactants, cationic surfactants and mixtures thereof, said surfactants having distinct hydrophobic and hydrophilic segments, wherein said isocyanate-reactive groups of said surfactant are positioned in a cation portion of said surfactant.

4. A composition as in claim 3, wherein said surfactant is selected from the group consisting of monoethanolamine salts of sulfonic acids, diethanolamine salts of sulfonic acids and triethanolamine salts of sulfonic acids and mixtures thereof.

5. A composition as in claim 4, wherein said sulfonic acids are selected from the group consisting of dodecylbenzene sulfonic acid, napthalene sulfonic acid, lignin sulfonic acids, petroleum sulfonic acids and paraffin sulfonic acids.

10. A polyurethane composition comprising the reaction product of an isocyanate prepolymer, a hydrophilic polyol and a surfactant comprising a non-ethoxylated hydrocarbon chain with greater than 16 carbon atoms bearing an isocyanate reactive group selected from the group consisting of anionic surfactants, cationic surfactants and mixtures thereof, wherein said hydrophilic polyol and said surfactant react with isocyanate groups in said isocyanate prepolymer to form said polyurethane coating to provide a scratch-resistant and permanent anti-fog surface.

11. A method of providing an article with an anti-fog and anti-scratch surface comprising:

a) providing an isocyanate prepolymer having reactive isocyanate groups;

b) providing a reactive organic solvent solution comprising;

i) a hydrophilic polyol, and

ii) a surfactant bearing an isocyanate-reactive group and having a distinct hydrophobic portion and a distinct hydrophilic portion, said surfactant being selected from the group consisting of anionic surfactants, cationic surfactants and mixtures thereof, said hydrophilic polyol and said surfactant being distinct components;

c) reacting said isocyanate prepolymer with said reactive organic solvent solution, wherein said hydrophilic polyol and said surfactant bearing said isocyanate reactive-group react with said isocyanate groups in said isocyanate prepolymer, thereby forming a polyurethane composition having pendent hydrophilic and surfactant groups chemically reacted therein; and

d) applying said polyurethane to the surface of said article and heat curing.

12. A method as in claim 11, further including the step of thermoforming said article after said coating step d).

13. A polyurethane composition comprising the reaction product of an isocyanate prepolymer, a hydrophilic polyol and a surfactant bearing an isocyanate reactive group positioned in a cation portion of said surfactant, said surfactant being selected from the group consisting of anionic surfactants, cationic surfactants and mixtures thereof, wherein said hydrophilic polyol and said surfactant react with isocyanate groups in said isocyanate prepolymer to form said polyurethane coating to provide a scratch-resistant and permanent anti-fog surface.