Non-fogging material

• US 3,867,175 A
• Filed: 09/28/1972
• Issued: 02/18/1975
• Est. Priority Date: 11/04/1970
• Status: Expired due to Term

• Current Assignee: C & D Acquisition Corporation
• Original Assignee: Ralph William Dornte
• Inventors: Dornte, Ralph William
• Primary Examiner(s): Willis, Jr., P. E.
• Application Number:
  US05/292,939
• Time in Patent Office: 873 Days
• Field of Search: 117/124E,47A,138.8A,138.8F,138.8UA,161UN,161UT,161P 106/13 260/874,836
• US Class Current: 428/412
• CPC Class Codes: C08G 73/0213 Preparatory process
• CPC Class Codes: C08J 2479/00 Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2461/00 - C08J2477/00
• CPC Class Codes: C08J 7/0427 with only one layer of a composition containing a polymer binder with more layers C08J7/042
• CPC Class Codes: C08J 7/043 Improving the adhesiveness of the coatings per se, e.g. forming primers adhesives in the form of films or foils characterised by the primer layers between the polymer carriers and the adhesives C09J7/50
• CPC Class Codes: C08J 7/046 Forming abrasion-resistant coatings; Forming surface-hardening coatings
• CPC Class Codes: C08J 7/054 Forming anti-misting or drip-proofing coatings
• CPC Class Codes: C08J 7/056 Forming hydrophilic coatings
• CPC Class Codes: C09D 179/02 Polyamines
• 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
• CPC Class Codes: Y10T 428/31507 Of polycarbonate

Abstract

A non-fogging, abrasion resistant material is provided by applying a transparent, non-fogging coating to a normally fogging, transparent or reflecting substrate. The non-fogging, abrasion resistant coating comprises a highly cross-linked alkylene imine polymer. The polyalkylene imine may be further modified by an adhesion promoter through reaction with the amine hydrogens of the polyimine. The non-fogging articles include goggles - safety and ski, bathroom mirrors, windows, boat windshields, packages, eyeglasses and gas masks.

Claims

1. A NON-FOGGING MATERIAL COMPRISING A NORMALLY FOGGING SUBSTRATE HAVING ON AT LEAST ONE SURFACE THEREOF A NON-FOGGING, WATER INSOLUBLE, HYDROPHILIC POLYMERIC COATING COMPRISING A POLYALKYLENE IMINE HAING SUBSTANTIALLY ALL OF ITS NITROGEN ATOMS ATTACHED TO A PLURALITY OF REACTIVE COMPOUNDS, AT LEAST ONE OF SAID REACTIVE COMPOUNDS BEING A CROSS-LINLING COMPOUND HAVING AT LEAST TWO FUNCTIONAL GROUPS CAPABLE OF REACTING WITH THE POLYALKYLENE IMINE SELECTED FROM A NONAROMATIC ETHYLENIC UNSAURATED GROUP, AN EPOXY GROUP, A HALO GROUP, A CARBOXYLIC ACID OR ANHYDRIDE GROUP, AN ALDEHYDE GROUP, A KETONIC GROUP, AN ISOCYANATO OR ISOTHIOCYANATO GROUP AND A PHENOLIC HYDRXY GROUP AND ANOTHER POLYFUNCTIONAL REACTIVE COMPOUND CONTAINING A POLAR FUNCTIONAL GROUP TO PROMOTE ADHESION TO THE SUBSTRATE SELECTED FROM A CYANO GROUP, AN AMIDO GROUP, AN ACETYL GROUP AND ARYL GROUP AND HAVING AT LEAST TWO FUNCTIONAL GROUPS SELECTED FROM A NONAROMATIC ETHYLENIC UNSATURATED GROUP, AN EPOXY GROUP, A HALO GROUP, A CARBOXYLIC ACID OR ANHYDRIDE GROUP, AN ALDEHYDE GROUP, A KETONIC GROUP, AN ISOCYANATO GROUP OR ISOTHIOCYANATO GROUP AND A PHENOLIC HYDROXY GROUP, SAID REACTIVE COMPOUNDS BEING REACTED WITH THE POLYALKYLENE IMINE IN AN AMOUNT OF AT LEAST ONE REACTIVE EQUIVALENT PER EQUIVALENT WEIGHT OF THE POLYALKYLENE IMINE.

2. adding at least two polyfunctional reactive compounds containing a polar functional group selected from a cyano group, an amido group, an acetyl group and an aryl group to said polyalkylene imine solution and reacting said polyfunctional compounds having at least two functional groups selected from a nonaromatic ethylenic unsaturated group, an epoxy group, a halo group, a carboxylic acid or anhydride group, an aldehyde group, a ketonic group, an isocyanato or isothiocyanato group and a phenolic hydroxy group with the amine hydrogen of the polyalkylene imine, said reaction being exothermic;

3. A material in accordance with claim 1 in which the cross-linking compound is epichlorohydrin, and the polyfunctional reactive compounds containing a polar functional group are glycidyl methacrylate and methylene bisacrylamide.

4. after thermally staBilizing the reaction of step (2), adding at least one cross-linking compound to the solution which has at least two functional groups selected from a nonaromatic ethylenic unsaturated group, an epoxy group, a halo group, a carboxylic acid or anhydride group, an aldehyde group, a ketonic group, an isocyanato or isothiocyanato group and a phenolic hydroxy group and is capable of reacting with and cross-linking the polyalkylene imine to a water insoluble coating upon complete reaction;

5. heating the solution containing the cross-linking compound to partially react it with the polyalkylene imine without cross-linking the imine polymer to a degree that the polymer will gel or come out of solution;

6. A material in accordance with claim 1 in which the cross-linking compound is present in an amount of about 0.3 to 2.5 moles per equivalent weight of the alkylene imine repeating unit and the polyfunctional reactive compound containing a polar functional group is present in an amount up to about 0.8 mole per equivalent weight of the alkylene imine repeating unit.

7. applying the partially cross-linked polyalkylene imine solution to at least one surface of the substrate;

and

8. A material in accordance with claim 3 in which the substrate is polycarbonate.

9. A method of applying a non-fogging polymeric coating to a substrate comprising:

10. The method of claim 9 in which the polyalkylene imine is polyethylene imine and a solvent for the partially cross-linked polyethylene imine is added to the solution in step (4) after the cross-linking compound is added to the solution.

11. The method of claim 9 in which the substrate is polycarbonate whose surface is treated with the solution of chromic acid and sulfuric acid prior to applying the coating thereto in step (7).

12. The method of claim 9 in which the polyfunctional reactive compounds containing a polar functional group are methylene bisacrylamide and glycidyl methacrylate.

13. The method of claim 9 in which the cross-linking compound is epichlorohydrin.