IP Library Granted Patent US 10,125,205
Granted Patent B2
US 10,125,205 · App. 14/652,361 · Granted Nov 13, 2018

Cross-linkable acid copolymer composition and its use in glass laminates

Inventors: Steven C. Pesek (Orange, TX); Charles Anthony Smith (Vienna, WV)
Assignee: E. I. DU PONT DE NEMOURS AND COMPANY
C08F222/02A63B37/0003B32B17/10018B32B17/10036B32B17/10697B32B17/10743C08J5/18C09D123/0869C09D123/0876H01L51/448B32B2307/558C08J2323/08C08J2333/02C08L2203/204C08L2312/00Y02E10/549Y10T428/31507Y10T428/31576Y10T428/31649Y10T428/31663Y10T428/31699Y10T428/31757Y10T428/31797Y10T428/31913Y10T428/31935
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Quick Facts
Patent No.
US 10,125,205
App. No.
14/652,361
Granted
Nov 13, 2018
Kind
B2
Abstract

Provided herein are glass laminates, preferably safety glass laminates, that comprise a polymeric interlayer sheet formed of an acid copolymer composition. The acid copolymer composition comprises an ethylene acid copolymer which, in turn, comprises copolymerized units of ethylene, about 5 to about 90 wt % of copolymerized units of a first α,β-unsaturated carboxylic acid having 3 to 10 carbon atoms; and optionally about 2 to about 40 wt % of copolymerized units of a derivative of a second α,β-unsaturated carboxylic acid having 3 to 10 carbon atoms. Optionally, a portion of the carboxylic acid groups of the copolymerized units of the ethylene acid copolymer are neutralized to form carboxylate salts. The acid copolymer composition also includes a hydroxyl-containing crosslinking agent and may also include an adjuvant. The glass laminates have superior resistance to creeping due to the properties of the acid copolymer composition, which may optionally be cross-linked.

Claims (19)

1. A safety laminate comprising at least one interlayer sheet that is laminated to one or more rigid sheets, one or more other polymeric interlayer sheets, or one or more film layers; said at least one interlayer sheet comprising a product of cross-linking an acid copolymer composition; said acid copolymer composition comprising an ethylene copolymer, and said ethylene copolymer comprising copolymerized units of ethylene, about 5 to about 90 wt % of copolymerized units of a first α,β-unsaturated carboxylic acid having 3 to 10 carbon atoms; and optionally about 2 to about 40 wt % of copolymerized units of a derivative of a second α,β-unsaturated carboxylic acid having 3 to 10 carbon atoms; wherein the weight percentages of the copolymerized units are based on the total weight of the ethylene copolymer and the sum of the weight percentages of the copolymerized units in the ethylene copolymer resin is 100 wt %; and wherein optionally at least a portion of the carboxylic acid groups of the copolymerized units of the α,β-unsaturated carboxylic acid units are neutralized to form carboxylate salts;

from 0.05 wt % to about 2 wt % of a hydroxyl-containing crosslinking agent, based on the total weight of the acid copolymer composition; and

a silane adjuvant;

wherein at least a portion of the carboxylic acid groups or carboxylate groups of two or more ethylene copolymers are reacted with at least two of the hydroxyl groups of the hydroxyl-containing crosslinking agent, so that the hydroxyl-containing crosslinking agent forms a cross-link between the two or more ethylene copolymer molecules.

2. The safety laminate of claim 1 , wherein the ethylene copolymer has a MFR of about 20 to about 400 g/10 min.

3. The safety laminate of claim 1 , wherein the ethylene copolymer comprises about 5 to about 30 wt % of copolymerized units of the first α,β ethylenically unsaturated carboxylic acid.

4. The safety laminate of claim 1 , wherein the derivative of the second α,β-unsaturated carboxylic acid is an alkyl (meth)acrylate.

5. The safety laminate of claim 1 , wherein the hydroxyl-containing crosslinking agent is a diol.

6. The safety laminate of claim 1 , wherein the silane adjuvant is selected from the group consisting of n-(2-aminoethyl-3-aminopropyl) trimethoxysilane; 3-glycidoxy propyl trimethoxysilane; and a combination of n-(2-aminoethyl-3-aminopropyl) trimethoxysilane and 3-glycidoxy propyl trimethoxysilane.

7. The safety laminate of claim 1 , wherein the rigid sheet comprises a material having a modulus of about 690 MPa or greater, as determined in accordance with ASTM D638, and wherein the material is selected from the group consisting of glass, metal, ceramic, and polymers.

8. The safety laminate of claim 1 , wherein the film layer is a metal film or a polymeric film comprising one or more materials selected from the group consisting of polyesters, polycarbonates, polyolefins, norbornene polymers, polystyrenes, styrene-acrylate copolymers, acrylonitrile-styrene copolymers, polysulfones, polyamides, polyurethanes, acrylic polymers, cellulose acetates, cellophanes, vinyl chloride polymers and fluoropolymers.

9. The safety laminate of claim 1 , further comprising one or more other polymeric interlayer sheets, wherein the one or more other polymeric interlayer sheets comprise one or more materials selected from the group consisting of poly(vinyl acetals), poly(vinyl chlorides), polyurethanes, ethylene/vinyl acetate copolymers, acid copolymers, and ionomers.

10. The safety laminate of claim 1 , wherein the at least one interlayer sheet comprising the acid copolymer composition is laminated between two glass sheets.

11. The safety laminate of claim 1 , wherein the at least one interlayer sheet comprising the acid copolymer composition is laminated between a glass sheet and a polyester film that is coated with an abrasion resistant hardcoat on the surface that is facing away from the interlayer sheet.

12. The safety laminate of claim 11 , which comprises n rigid sheet or film layers and (n−1) polymeric interlayer sheets, wherein (a) each of the adjacent pairs of the rigid sheet or film layers is interspaced by one of the polymeric interlayer sheets; (b) at least one of the (n−1) polymeric interlayer sheets comprises the acid copolymer composition, and (c) n is an integer and 2<n<10.

13. The safety laminate of claim 12 , which comprises an impact zone that faces to the impact force and an anti-spall zone that is firmly adhered to the impact zone and faces away from the impact force, wherein (A) the impact zone is formed by the n rigid sheets and the (n−1) polymeric interlayer sheets; and (B) the anti-spall zone is formed of an additional polymer sheet and an additional film layer with a first surface of the additional polymer sheet adhered firmly to the impact zone and a second surface of the polymer sheet adhered firmly to the additional polymer film.

14. The safety laminate of claim 13 , wherein (A) each of the n rigid sheets are glass sheets; (B) each of the (n−1) polymeric interlayer sheets comprises the acid copolymer composition; (C) the additional polymeric interlayer sheet comprises a poly(vinyl butyral); and (D) the additional polymer film is a poly(ethylene terephthalate) film having a surface that is opposite from the impact zone and a hardcoat adhered to the surface.

15. The safety laminate of claim 5 , wherein the diol is selected from the group consisting of 1,4-butanediol, 1,3-propanediol and 1,6-hexanediol.

16. The safety laminate of claim 15 , wherein the diol comprises 1,4-butanediol.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 14, 2021
From: PERFORMANCE MATERIALS NA, INC.
To: THE DOW CHEMICAL COMPANY
Reel/Frame 057813/0792 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 14, 2021
From: THE DOW CHEMICAL COMPANY
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 057813/0928 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2019
From: E.I. DU PONT DE NEMOURS AND COMPANY
To: PERFORMANCE MATERIALS NA, INC.
Reel/Frame 050149/0728 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 22, 2015
From: PESEK, STEVEN C.; SMITH, CHARLES ANTHONY
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 036857/0016 →
Continuity (4)
Provisional Application 61739562 · Dec 19, 2012
Provisional Application 61739572 · Dec 19, 2012
Provisional Application 61739557 · Dec 19, 2012
Related Publication 20150343745A1 · Dec 3, 2015
Cited By (1)
US 12,337,575