IP Library Granted Patent US 11,492,522
Granted Patent B2
US 11,492,522 · App. 15/629,130 · Granted Nov 8, 2022

Chemical products for adhesive applications

Inventors: Charles Zha (Katy, TX); Jan Beetge (Pearland, TX); Leo Elder (Tomball, TX); John W. Green (Cypress, TX)
Assignee: HEXION INC.
C09J133/02C04B26/14C04B26/20C08G73/028C08K3/06C09J133/068C09J133/24C09J177/08C09J179/02C09K8/805C04B2103/0075C04B2111/00698C04B2111/00732C04B2201/50C09K8/575C09K8/5756Y02W30/91
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Quick Facts
Patent No.
US 11,492,522
App. No.
15/629,130
Granted
Nov 8, 2022
Kind
B2
Abstract

The embodiments described herein generally relate to methods and chemical compositions for coating substrates with a composition. In one embodiment, an adhesive composition is provided comprising a reaction product of a polyacid selected from the group consisting of an aromatic polyacid, an aliphatic polyacid, an aliphatic polyacid with an aromatic group, and combinations thereof, or a diglycidyl ether; and a polyamine; and one or more compounds selected from the group consisting of a branched aliphatic acid, a cyclic aliphatic acid with a cyclic aliphatic group, a linear aliphatic, and combinations thereof.

Claims (57)

1. An adhesive composition, comprising:

a reaction product comprising:

an adduct or product comprising from about 25 wt. % to about 96 wt. % of the adhesive composition, the adduct or product comprising:

a diacid comprising from about 40 wt. % to about 90 wt. % of the adduct or product, and the diacid is selected from the group consisting of an aromatic diacid, an aliphatic diacid with an aromatic group, and combinations thereof, wherein an aromatic ring of the aromatic diacid and the aromatic group of the aliphatic diacid are, independently, substituted with a functional group selected from the group consisting of amine, hydroxyl (—OH), C1-C12 alkyl, alkylamino, alkyloxy, alkenyloxy, alkylcarboxy, alkylnitro, and alkylsulfonyl; and

a polyamine comprising from about 10 wt. % to about 60 wt % of the adduct or product, and the polyamine is selected from the group consisting of triamines, tetramines, and combinations thereof; and

one or more compounds comprising from about 4 wt. % to about 75 wt. % of the adhesive composition, the one or more compounds selected from the group consisting of a branched aliphatic acid having C2-C26 alkyl group, a cyclic aliphatic acid with C7-C30 cyclic aliphatic group, a linear aliphatic acid having C2-C26 alkyl group, and combinations thereof, the reaction product comprising

R 1 -dAm dAc-dAm n R 2 ,

 wherein:

n is 1 to 10,

R1 and R2 are each independently selected from the group consisting of a branched aliphatic acid having C2-C26 alkyl group, cyclic aliphatic acid with C7-C30 cyclic aliphatic group, a linear aliphatic acid having C2-C26 alkyl group, and combinations thereof,

dAm comprises a polyamine, and

dAc comprises a diacid; and

wherein a total wt. % of the adhesive composition is 100 wt. %.

2. The adhesive composition of claim 1 , wherein:

the polyamine comprises diethylenetriamine,

the branched aliphatic acid having C2-C26 alkyl group comprises versatic acid,

the cyclic aliphatic acid with C7-C30 cyclic aliphatic group comprises rosin, and

the linear aliphatic acid having C2-C26 alkyl group comprises tall oil fatty acid.

3. The adhesive composition of claim 2 , wherein the one or more compounds is the cyclic aliphatic acid with C7-C30 cyclic aliphatic group.

4. The adhesive composition of claim 1 , wherein:

the branched aliphatic acid having C2-C26 alkyl group comprises versatic acid,

the cyclic aliphatic acid with C7-C30 cyclic aliphatic group comprises rosin, and

the linear aliphatic acid having C2-C26 alkyl group comprises tall oil fatty acid (TOFA).

5. The adhesive composition of claim 1 , wherein n of the reaction product is 1 to 5.

6. The adhesive composition of claim 1 , wherein the polyamine comprises a polyethertriamine.

7. The adhesive composition of claim 1 , wherein the polyamine is selected from the group consisting of diethylenetriamine, triethylenetetraamine, polyethertriamine, and combinations thereof.

8. The adhesive composition of claim 1 , wherein the aliphatic diacid with an aromatic group is

or combinations thereof, wherein:

each of R1 and R2 of the aliphatic diacid with an aromatic group are independent functional groups selected from the group consisting of C1-C12 alkyl, alkyloxy, alkylamino, and alkylcarboxy, and

each of R3, R4, R5, and R6 of the aliphatic diacid with an aromatic group are independent functional groups selected from the group consisting of hydroxyl (—OH), amino, nitro, sulfonyl, C1-C12 alkyl, alkyloxy, alkylamino, and alkylcarboxy.

9. The adhesive composition of claim 1 , wherein the adhesive composition further comprises a solvent selected from the group consisting of aromatic solvents, ethers, alcohols, and water.

10. The adhesive composition of claim 9 , wherein the solvent is selected from the group consisting of toluene, xylene, naphtha, diglyme, triglyme, polyglyme, proglyme, ethylene glycol butyl ether methanol, isopropanol, ethanol, propanol, butanol, ethoxytriglycol, methoxytriglycol, tripropyleneglycol methyl ether, ethyleneglycol butyl ether, dipropylene glycol ethyl ether, tripropylene glycol ethyl ether, diethylene glycol ethyl ether, diethyleneglycol butyl ether, water, and combinations thereof.

11. The adhesive composition of claim 1 , further comprising a cross-linking agent.

12. The adhesive composition of claim 11 , wherein the cross-linking agent is selected from the group consisting of diglycidyl ether of bisphenol A, diglycidyl ether of bisphenol F, diglycidyl ether of bisphenol B, diglycidyl ether of bisphenol C, diglycidyl ether of bisphenol E, diglycidyl ether of bisphenol AP, diglycidyl ether of bisphenol AF, diglycidyl ether of bisphenol BP, diglycidyl ether of bisphenol G, diglycidyl ether of bisphenol M, diglycidyl ether of bisphenol S, diglycidyl ether of bisphenol P, diglycidyl ether of bisphenol PH, diglycidyl ether of bisphenol TMC, diglycidyl ether of bisphenol Z, and combinations thereof.

13. The adhesive composition of claim 1 , wherein the linear aliphatic acid having C2-C26 alkyl group comprises any plant and animal fatty acid selected from the group consisting of tall oil fatty acid, and fatty acids made from chicken fat, lard, beef tallow, canola oil, flaxseed oil, sunflower oil, corn oil, olive oil, sesame oil, peanut oil, cottonseed oil, palm oil, butter, and cocoa butter, palm kernel oil, coconut oil, and combinations thereof.

14. The adhesive composition of claim 1 , wherein the cyclic aliphatic acid with C7-C30 cyclic aliphatic group is selected from the group consisting of rosin, naphthenic acid, and combinations thereof.

15. An adhesive composition, comprising:

a reaction product comprising:

an adduct or product comprising from about 25 wt. % to about 96 wt. % of the adhesive composition, the adduct or product comprising:

a diacid comprising from about 40 wt. % to about 90 wt. % of the adduct or product, and the diacid is selected from the group consisting of an aromatic diacid, an aliphatic diacid with an aromatic group, and combinations thereof; and

a polyamine comprising from about 10 wt. % to about 60 wt. % of the adduct or product, and the polyamine is selected from the group consisting of triamines, tetramines, and combinations thereof; and

one or more compounds comprising from about 4 wt. % to about 75 wt. % of the adhesive composition, the one or more compounds are selected from the group consisting of a branched aliphatic acid having C2-C26 alkyl group, a cyclic aliphatic acid with C7-C30 cyclic aliphatic group, a linear aliphatic acid having C2-C26 alkyl group, and combinations thereof,

wherein the reaction product comprises

R 1 -dAm dAc-dAm n R 2 ,

wherein:

n is 1 to 10,

R1 is a branched aliphatic acid having C2-C26 alkyl group,

R2 is a branched aliphatic acid having C2-C26 alkyl group, a cyclic aliphatic acid with C7-C30 cyclic aliphatic group, or a linear aliphatic acid having C2-C26 alkyl group,

dAm comprises a polyamine, and

dAc comprises a diacid; and

wherein a total wt. % of the adhesive composition is 100 wt. %.

16. The adhesive composition of claim 15 , wherein the aliphatic diacid with an aromatic group is represented by

or combinations thereof, wherein:

each of R1 and R2 of the aliphatic diacid with an aromatic group are independent functional groups selected from the group consisting of C1-C12 alkyl, alkyloxy, alkylamino, and alkylcarboxy, and

each of R3, R4, R5, and R6 of the aliphatic diacid with an aromatic group are independent functional groups selected from the group consisting of hydroxyl (—OH), amino, nitro, sulfonyl, C1-C12 alkyl, alkyloxy, alkylamino, and alkylcarboxy.

17. The adhesive composition of claim 15 , wherein the linear aliphatic acid having C2-C26 alkyl group comprises any plant and animal fatty acid selected from the group consisting of tall oil fatty acid, and fatty acids made from chicken fat, lard, beef tallow, canola oil, flaxseed oil, sunflower oil, corn oil, olive oil, sesame oil, peanut oil, cottonseed oil, palm oil, butter, and cocoa butter, palm kernel oil, coconut oil, and combinations thereof.

18. The adhesive composition of claim 15 , wherein the cyclic aliphatic acid with C7-C30 cyclic aliphatic group is selected from the group consisting of rosin, naphthenic acid, and combinations thereof.

Assignments (16)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 8, 2024
From: HEXION INC.
To: CANADIAN ENERGY SERVICES L.P.
Reel/Frame 068227/0121 →
PARTIAL RELEASE OF US ABL IP SECURITY AGREEMENT RECORDED AT R/F 059436/0748 Recorded May 28, 2024
From: GOLDMAN SACHS BANK USA
To: HEXION INC.
Reel/Frame 067553/0894 →
PARTIAL RELEASE OF SECOND LIEN IP SECURITY AGREEMENT RECORDED AT R/F 059436/0842 Recorded May 28, 2024
From: ROYAL BANK OF CANADA
To: HEXION INC.
Reel/Frame 067553/0787 →
PARTIAL RELEASE OF FIRST LIEN IP SECURITY AGREEMENT RECORDED AT R/F 059436/0823 Recorded May 28, 2024
From: GOLDMAN SACHS BANK USA
To: HEXION INC.
Reel/Frame 067553/0061 →
SECURITY INTEREST Recorded Mar 18, 2022
From: HEXION INC.; HEXION INVESTMENTS INC.
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0823 →
SECURITY INTEREST Recorded Mar 18, 2022
From: HEXION INC.; HEXION INVESTMENTS INC.
To: ROYAL BANK OF CANADA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0842 →
RELEASE OF SECURITY INTEREST IN PATENTS (TERM LOAN) RECORDED AT REEL/FRAME 049741/0425 Recorded Mar 18, 2022
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: HEXION INC.
Reel/Frame 059435/0473 →
RELEASE OF SECURITY INTEREST IN PATENTS (ABL) RECORDED AT REEL/FRAME 049740/0770 Recorded Mar 18, 2022
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: HEXION INC.
Reel/Frame 059435/0490 →
SECURITY INTEREST Recorded Mar 18, 2022
From: HEXION INC.; HEXION INVESTMENTS INC.
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0748 →
PATENT SECURITY INTEREST (ABL) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049740/0770 →
PATENT SECURITY INTEREST (TERM LOAN) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049741/0425 →
SECURITY INTEREST Recorded Feb 2, 2018
From: HEXION INC.
To: WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT
Reel/Frame 044814/0971 →
SECURITY INTEREST Recorded Feb 2, 2018
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 044814/0920 →
SECURITY INTEREST Recorded Feb 2, 2018
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 044814/0825 →
SECURITY INTEREST Recorded Jul 26, 2017
From: HEXION INC.
To: WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT
Reel/Frame 043097/0626 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 10, 2017
From: ZHA, CHARLES; BEETGE, JAN; ELDER, LEO; GREEN, JOHN W.
To: HEXION INC.
Reel/Frame 042955/0124 →