Silane coupling agents to improve resin adhesion

Patent metadata

Field	Value
Publication number	US-12031013-B2
Application number	US-202217865880-A
Country	US
Kind code	B2
Filing date	Jul 15, 2022
Priority date	Jul 19, 2021
Publication date	Jul 9, 2024
Grant date	Jul 9, 2024

Abstract

There is provided herein a resin composition comprising:
(i) a silane coupling agent of the general formula (I):

as described herein, and

(ii) at least one resin which is interactive with one or more of the R 1 , R 2 and X groups of silane coupling agent (i)
wherein: R 1 and R 2 each represent a hydrogen atom or a monovalent organic group having 1 to 40 carbon atoms; R 3 is independently a monovalent group selected from the group consisting of a straight chain alkyl containing from 1 to 12 carbon atoms, a branched chain alkyl containing from 3 to 12 carbon atoms, a cycloalkyl containing from 5 or 6 carbon atoms, an alkenyl containing from 2 to 12 carbon atoms, an aryl group containing 6 carbon atoms, or aralkyl containing from 7 to 12 carbon atoms, a straight chain alkyl containing 2 to 12 carbon atoms and a hydroxyl group, a branched chain alkyl containing 3 to 6 carbon atoms and a hydroxyl group, an alkyl group containing at least one oxygen atom having the structure:

—R 5 —(OCH 2 CH 2 ) m (OCH 2 CH(CH 3 )) n OR 6 ,

and a divalent group formed from two R 3 groups being bonded together through a covalent bond,
with the provisos that (i) if two R 3 groups are bonded together, then a is 2 or 3 and (ii) the sum of m+n is from 1 to 20; each R 4 is independently a monovalent group selected from the group consisting of a straight chain alkyl containing from 1 to 12 carbon atoms, a branched chain alkyl containing from 3 to 12 carbon atoms, a cycloalkyl containing from 5 or 6 carbon atoms, an alkenyl group containing from 2 to 12 carbon atoms, an aryl group containing 6 carbon atoms or aralkyl group containing from 7 to 12 carbon atoms; R 5 is divalent group selected from the group consisting of a straight chain alkylene containing from 1 to 10 carbon atoms, a branched chain alkylene containing from 3 to 10 carbon atoms, and a cycloalkylene containing from 5 to 10 carbon atoms; R 6 is a monovalent group selected from the group consisting of a straight chain alkyl containing from 1 to 18 carbon atoms, a branched chain alkyl containing from 3 to 18 carbon atoms, a cycloalkyl containing from 5 to 18 carbon atoms, an alkenyl containing from 2 to 18 carbon atoms, an aryl group containing from 6 to 18 carbon atoms, an aralkyl containing from 7 to 18 carbon atoms and hydrogen, or R 6 is a divalent group selected from the group consisting of an alkyl containing from 1 to 10 carbon atoms, a cycloalkyl containing from 5 to 10 carbon atoms and phenyl.

First claim

The invention claimed is:

1. A resin composition comprising:
(i) a silane coupling agent of the general formula (I):

where X is a heterocyclic group containing 1 or 2 N atoms, and wherein R 1 and R 2 are each H, Y is O, Z is a divalent straight chain alkylene group containing from 2 to 6 carbon atoms, the subscript a is 3, and each R 3 is a straight chain alkyl group containing from 1 to 3 carbon atoms;
Y is oxygen or sulfur;
Z is a divalent straight chain alkylene group containing from 1 to 20 carbon atoms, or a divalent branched chain alkylene group containing from 3 to 20 carbon atoms, each optionally containing a heteroatom;
the subscript a is 1, 2 or 3;
R 1 and R 2 each represent a hydrogen atom or a monovalent organic group having 1 to 40 carbon atoms;
R 3 is independently a monovalent group selected from the group consisting of a straight chain alkyl containing from 1 to 12 carbon atoms, a branched chain alkyl containing from 3 to 12 carbon atoms, a cycloalkyl containing from 5 or 6 carbon atoms, an alkenyl containing from 2 to 12 carbon atoms, an aryl group containing 6 carbon atoms, or aralkyl containing from 7 to 12 carbon atoms, a straight chain alkyl containing 2 to 12 carbon atoms and a hydroxyl group, a branched chain alkyl containing 3 to 6 carbon atoms and a hydroxyl group, an alkyl group containing at least one oxygen atom having the structure:
—R 5 —(OCH 2 CH 2 ) m (OCH 2 CH(CH 3 )) n OR 6 ,

and a divalent group formed from two R 3 groups being bonded together through a covalent bond,
with the provisos that (i) if two R 3 groups are bonded together, then a is 2 or 3 and (ii) the sum of m+n is from 1 to 20;
each R 4 is independently a monovalent group selected from the group consisting of a straight chain alkyl containing from 1 to 12 carbon atoms, a branched chain alkyl containing from 3 to 12 carbon atoms, a cycloalkyl containing from 5 or 6 carbon atoms, an alkenyl group containing from 2 to 12 carbon atoms, an aryl group containing 6 carbon atoms or aralkyl group containing from 7 to 12 carbon atoms;
R 5 is divalent group selected from the group consisting of a straight chain alkyl containing from 1 to 10 carbon atoms, a branched chain alkyl containing from 3 to 10 carbon atoms, and a cycloalkyl containing from 5 to 10 carbon atoms;
R 6 is a monovalent group selected from the group consisting of a straight chain alkyl containing from 1 to 18 carbon atoms, a branched chain alkyl containing from 3 to 18 carbon atoms, a cycloalkyl containing from 5 to 18 carbon atoms, an alkenyl containing from 2 to 18 carbon atoms, an aryl group containing from 6 to 18 carbon atoms, an aralkyl containing from 7 to 18 carbon atoms and hydrogen, or R 6 is a divalent group selected from the group consisting of an alkyl containing from 1 to 10 carbon atoms, a cycloalkyl containing from 5 to 10 carbon atoms and phenyl; and,
(ii) at least one resin which is interactive with one or more of the R 1 , R 2 , Y and X groups of silane coupling agent (i), and which is present in an amount of from about 10 weight percent to about 99.99 weight percent of the total weight of the resin composition.

2. The resin composition of claim 1 , wherein X is a heterocyclic group containing 2 N atoms and which is substituted with an O heteroatom.

3. The resin composition of claim 1 , wherein X is a heterocyclic group containing 2 N atoms and which is substituted with an O heteroatom and an alkyl group containing 1 or 2 carbon atoms.

4. The resin composition of claim 1 , wherein the resin (ii) is selected from the group consisting of polyimide, polyetherimide, polyurethane, silylated polyurethane, polyether, silylated polyether, polyphenylene ether, bismaleimide, polyisocyanurate, polyethylene terephthalate, glycol-modified polyethylene terephthalate, polybutylene terephthalate, low density polyethylene, very low density polyethylene, linear low density polyethylene, high density polyethylene, polypropylene, polyisobutylene, polyvinyl acetate, polyvinyl alcohol, polystyrene, polycarbonate, polyethylene napthalate, polyvinylchloride, polyvinylidene chloride, polyvinylidene fluoride, acrylonitrile butadiene styrene, polymethylmethacrylate, polyvinyl fluoride, polyamides, polymethylpentene, polyether ether ketone, polysulfone, polyether sulfone, ethylene chlorotrifluoroethylene, polytetrafluoroethylene, cellulose acetate, cellulose acetate butyrate, plasticized polyvinyl chloride, polyphenylene sulfide, styrene-maleic anhydride, modified polyphenylene oxide, ethylene-propylene rubber, polybutadiene, polychloroprene, polyisoprene, styrene-butadiene-styrene, styrene-ethylene-butadiene-styrene, and mixtures thereof.

5. The resin composition of claim 1 , wherein the resin (ii) is selected from the group consisting of polyimide, polyetherimide, polyurethane, polyphenylene ether, bismaleimide, polyisocyanurate, polyethylene terephthalate, polyethylene, polypropylene, polyisobutylene and combinations thereof.

6. The resin composition of claim 1 , wherein the resin (ii) is polyimide.

7. The resin composition of claim 1 , wherein X is a heterocyclic group containing 2 N atoms and which is substituted with an O heteroatom and an alkyl group containing 1 or 2 carbon atoms, and, wherein the resin (ii) is selected from the group consisting of polyimide, polyetherimide, polyurethane, polyphenylene ether, bismaleimide, polyethylene terephthalate, polyethylene, polypropylene, polyisobutylene and combinations thereof.

8. The resin composition of claim 7 , wherein the resin (ii) is polyimide.

9. A process of making the resin composition of claim 1 comprising contacting the silane coupling agent (i) and resin (ii).

10. An article made from the resin composition of claim 1 , wherein the article is selected from the group consisting of a resin film, a resin film with copper foil, a laminate prepreg, a printed circuit board, and a flexible electronic device.

11. The article of claim 10 , wherein article is a laminate prepreg comprising a substrate selected from the group consisting of plastic film, silicon wafer, ceramic, organic material, metal and glass.

12. The article of claim 11 wherein the substrate is a copper foil.

13. The article of claim 11 , which is a flexible copper clad laminate.

14. The article of claim 10 , which is a flexible electronic display device.

15. A foldable smartphone or a rollable smartphone comprising the flexible electronic display device of claim 14 .

16. A process for manufacturing a copper clad laminate comprising the steps of:
(a) coating the resin composition of claim 1 onto a copper foil; and,
(b) heating the coated copper foil to obtain the copper clad laminate.

17. A process for manufacturing a flexible display comprising the steps of:
(a) coating the resin composition of claim 1 onto a glass substrate; and,
(b) curing the resin composition to form a resin layer on the glass substrate.

Assignees

• Momentive Performance Mat Inc

Inventors

• Diao Cheng
• Phukan Monjit
• Patel Neal

Classifications

• C09D133/24

  Homopolymers or copolymers of amides or imides · CPC title

• C08G73/10

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• C09D7/63

  organic · CPC title

• C03C17/002

  for flat glass, e.g. float glass · CPC title

• C03C17/32

  with synthetic or natural resins (C03C17/30 takes precedence) · CPC title