US3867175A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Non-fogging material
Assignee: C & D ACQUISITION CORP A CORP OF DE
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Filing: 1972-09-28
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Granted: 1975-02-18
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Expires: 1992-09-28
Abstract
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.
Inventors
- 👤 Ralph William Dornte
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 05:13
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/02; C08G73/0206; C08G73/0213; C08J; C08J7/00; C08J7/04; C08J7/0427; C08J7/043; C08J7/046; C08J7/054; C08J7/056; C09; C09D; C09D179/00; C09D179/02; C09K; C09K3/00; C09K3/18; C08J2479/00; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31507
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
197 words
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.
Claim 2
Dependent Claim
197 words
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.
Claim 3
Dependent Claim
50 words
A material in accordance with claim 1 in which the functional groups capable of reacting with the polyalkylene imine contained by both the cross-linking compound and the polyfunctional reactive compound containing a polar functional group are selected from a nonaromatic ethylenic unsaturated group, an epoxy group and a halo group.
Claim 4
Dependent Claim
90 words
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;
Claim 5
Dependent Claim
90 words
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;
Claim 6
Dependent Claim
14 words
cooling the reaction of step (2) if necessary to prevent an exothermic runaway reaction;
Claim 7
Dependent Claim
14 words
cooling the reaction of step (2) if necessary to prevent an exothermic runaway reaction;
Claim 8
Dependent Claim
30 words
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.
Claim 9
Dependent Claim
15 words
A material in accordance with claim 1 in which the polyalkylene imine is polyethylene imine.
Claim 10
Dependent Claim
78 words
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;
Claim 11
Dependent Claim
78 words
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;
Claim 12
Dependent Claim
15 words
A material in accordance with claim 3 in which the polyalkylene imine is polyethylene imine.
Claim 13
Dependent Claim
33 words
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;
Claim 14
Dependent Claim
33 words
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;
Claim 15
Dependent Claim
10 words
cooling the partially cross-linked polyalkylene imine solution to stabilize it;
Claim 16
Dependent Claim
10 words
cooling the partially cross-linked polyalkylene imine solution to stabilize it;
Claim 17
Dependent Claim
61 words
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.
Claim 18
Dependent Claim
13 words
A material in accordance with claim 1 in which the substrate is polycarbonate.
Claim 19
Dependent Claim
16 words
applying the partially cross-linked polyalkylene imine solution to at least one surface of the substrate; and
Claim 20
Dependent Claim
16 words
applying the partially cross-linked polyalkylene imine solution to at least one surface of the substrate; and
Claim 21
Dependent Claim
38 words
heating the coated substrate to cause the cross-linking reaction to be completed whereby substantially all of the nitrogen atoms of the polyalkylene imine are attached to reactive compound so as to provide a non-fogging, abrasion resistant coated substrate.
Claim 22
Dependent Claim
38 words
heating the coated substrate to cause the cross-linking reaction to be completed whereby substantially all of the nitrogen atoms of the polyalkylene imine are attached to reactive compound so as to provide a non-fogging, abrasion resistant coated substrate.
Claim 23
Dependent Claim
13 words
A material in accordance with claim 3 in which the substrate is polycarbonate.
Claim 24
Independent Claim
12 words
A method of applying a non-fogging polymeric coating to a substrate comprising:
Claim 25
Independent Claim
12 words
A method of applying a non-fogging polymeric coating to a substrate comprising:
Claim 26
Dependent Claim
39 words
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.
Claim 27
Dependent Claim
33 words
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).
Claim 28
Dependent Claim
22 words
The method of claim 9 in which the polyfunctional reactive compounds containing a polar functional group are methylene bisacrylamide and glycidyl methacrylate.
Claim 29
Dependent Claim
12 words
The method of claim 9 in which the cross-linking compound is epichlorohydrin.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-02-17 | 1978-08-19 | 1979-02-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-02-17 | 1982-08-19 | 1983-02-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-02-17 | 1986-08-19 | 1987-02-18 | $7700.00 | Window Closed / Lapsed |