IP Library Granted Patent US 11,161,976
Granted Patent B2
US 11,161,976 · App. 16/445,043 · Granted Nov 2, 2021

Phenolic epoxy system

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Quick Facts
Patent No.
US 11,161,976
App. No.
16/445,043
Granted
Nov 2, 2021
Kind
B2
Abstract

The embodiments described herein generally relate to methods and chemical compositions of phenolic epoxy systems. In one embodiment, a composition comprising a phenolic epoxy resin system includes an epoxy resin component and an alkoxylated phenol-aldehyde novolac resin.

Claims (40)

1. A composition consisting essentially of:

an epoxy resin component; and

a partially alkoxylated phenol-aldehyde novolac resin, and

an optional curing agent, wherein the composition is a powder.

2. The composition of claim 1 , wherein the epoxy resin component comprises an epoxy group functionality equal or greater than 2.

3. The composition of claim 1 , wherein the composition consists essentially of:

from 20 wt. % to 70 wt. % of the epoxy resin component; and

from 30 wt. % to 80 wt. % of the partially alkoxylated phenol-aldehyde novolac resin; and

from 0 wt. % to 5 wt. % of the optional curing agent, wherein the total weight percent is 100 weight percent.

4. The composition of claim 1 , wherein the optional curing agent is selected from the group consisting of hexamethylenetetramine, oxazolidine, paraformaldehyde, trioxane, 2-methyl imidazole, imidazole, melamine, triethanol amine, tributyl amine, and combinations thereof.

5. The composition of claim 1 , wherein the optional curing agent is present in the composition and comprises from 0.1 wt. % to 5 wt. % of the composition.

6. A composition consisting essentially of:

an epoxy resin component; and

a partially alkoxylated phenol-aldehyde novolac resin, and

an optional curing agent, wherein the partially alkoxylated phenol-aldehyde novolac resin comprises a reaction product from components comprising:

a phenol-aldehyde novolac resin; and

an alkoxylation agent selected from the group consisting of an alkylene oxide, an alkylene carbonate, and a combination thereof; and

an optional alkoxylation catalyst, wherein a molar ratio of the alkoxylation agent to phenolic hydroxyl group reactive sites of the phenol-aldehyde novolac resin is from 0.1:1 to 0.9:1 to form the partially alkoxylated phenol-aldehyde novolac resin.

7. The composition of claim 6 , wherein the composition is a powder.

8. The composition of claim 6 , wherein 10% to 50% of the phenolic hydroxyl group reactive sites of the phenol-aldehyde novolac resin are alkoxylated, the reaction product comprises a hydroxyl group functionality equal or greater than 2, or a combination thereof.

9. The composition of claim 6 , wherein the reaction product comprises a reaction product from components comprising:

from 59 wt. % to 90 wt. % of the phenol-aldehyde novolac resin; and

from 10 wt. % to 41 wt. % of the alkoxylation agent; and

from 0 wt. % to 5 wt. % of the optional catalyst, wherein the total weight percent is 100 weight percent.

10. The composition of claim 9 , wherein the optional catalyst is present in the amount from 0.05 wt. % to 5 wt. %.

11. The composition of claim 6 , wherein the alkylene oxide comprises a compound selected from the group consisting of ethylene oxide, propylene oxide, butylene oxide, and combinations thereof and wherein the alkylene carbonate comprises a compound selected from the group consisting of ethylene carbonate, propylene carbonate, butylene carbonate, and combinations thereof.

12. The composition of claim 6 , wherein the composition is a liquid.

13. A process comprising:

reacting a phenol-aldehyde novolac resin and an alkoxylation agent selected from the group consisting of an alkylene oxide, an alkylene carbonate, and a combination thereof, and an optional alkoxylation catalyst to form a partially alkoxylated phenol-aldehyde novolac resin; and

mixing the partially alkoxylated phenol-aldehyde novolac resin and an epoxy resin component and an optional curing agent to form a composition consisting essentially of: the epoxy resin component and the partially alkoxylated phenol-aldehyde novolac resin, and optionally the curing agent, wherein:

the composition is a powder,

a molar ratio of the alkoxylation agent to phenolic hydroxyl group reactive sites of the phenol-aldehyde novolac resin is from 0.1:1 to 0.9:1 to form the partially alkoxylated phenol-aldehyde novolac resin, or

the composition is a powder and a molar ratio of the alkoxylation agent to phenolic hydroxyl group reactive sites of the phenol-aldehyde novolac resin is from 0.1:1 to 0.9:1 to form the partially alkoxylated phenol-aldehyde novolac resin.

14. The process of claim 13 , wherein the partially alkoxylated phenol-aldehyde novolac resin and the epoxy resin component are mixed at room temperature to form the composition.

15. The process of claim 13 , wherein the partially alkoxylated phenol-aldehyde novolac resin and the epoxy resin component are mixed by grinding, blending, or a combination thereof to form the composition.

16. The process of claim 13 , wherein mixing the partially alkoxylated phenol-aldehyde novolac resin and the epoxy resin component is performed in the presence of the curing agent.

17. The process of claim 13 , wherein 10% to 50% of the phenolic hydroxyl group reactive sites of the phenol-aldehyde novolac resin are alkoxylated and the partially alkoxylated phenol-aldehyde novolac resin comprises a hydroxyl group functionality equal or greater than 2.

18. The process of claim 13 , wherein reacting the phenol-aldehyde novolac resin and the alkoxylation agent is performed in the presence of the alkoxylation catalyst.

19. The process of claim 13 , wherein the composition is in liquid or solid form.

20. The process of claim 13 , further comprising applying the composition as a composite, a liquid coating, a hot melt adhesive, a molding powder, a powder coating, or combinations thereof.

Assignments (16)
SECURITY INTEREST Recorded May 12, 2025
From: BAKELITE CHEMICALS LLC; BAKELITE UK HOLDING LTD.; BAKELITE GMBH; BAKELITE SYNTHETICS UK
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 071090/0740 →
ASSIGNMENT OF PATENT AND TRADEMARK SECURITY INTEREST Recorded May 12, 2025
From: MACQUARIE CAPITAL FUNDING LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 071276/0379 →
SECURITY INTEREST Recorded Jan 23, 2025
From: BAKELITE CHEMICALS LLC; BAKELITE UK HOLDING LTD.; BAKELITE GMBH; BAKELITE SYNTHETICS UK LIMITED
To: GOLDMAN SACHS BANK USA
Reel/Frame 069981/0468 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 15, 2023
From: BAKELITE LLC
To: BAKELITE UK HOLDING LTD.
Reel/Frame 062986/0879 →
CHANGE OF NAME Recorded Mar 15, 2023
From: HEXION VAD LLC
To: BAKELITE LLC
Reel/Frame 063100/0586 →
CHANGE OF NAME Recorded Mar 10, 2023
From: HEXION VAD LLC
To: BAKELITE LLC
Reel/Frame 063040/0875 →
RELEASE OF SECURITY INTEREST Recorded Jun 15, 2022
From: GOLDMAN SACHS SPECIALTY LENDING GROUP, L.P.
To: HEXION VAD LLC
Reel/Frame 060209/0558 →
SECURITY INTEREST Recorded Jun 9, 2022
From: GEORGIA-PACIFIC CHEMICALS LLC; GEORGIA-PACIFIC CONSUMER PRODUCTS LP; ENERG2 TECHNOLOGIES, INC.; KOCH AGRONOMIC SERVICES LLC; BAKELITE UK HOLDING LTD.
To: MACQUARIE CAPITAL FUNDING LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 060328/0327 →
SECURITY INTEREST Recorded Jun 9, 2022
From: GEORGIA-PACIFIC CHEMICALS LLC; GEORGIA-PACIFIC CONSUMER PRODUCTS LP; ENERG2 TECHNOLOGIES, INC.; KOCH AGRONOMIC SERVICES LLC; BAKELITE UK HOLDING LTD.; SURFACE TECH LLC
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 060328/0250 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 30, 2021
From: HEXION INC.
To: HEXION VAD LLC
Reel/Frame 057323/0086 →
RELEASE OF SECURITY INTEREST Recorded May 12, 2021
From: JPMORGAN CHASE BANK, N.A.
To: HEXION INC.
Reel/Frame 056219/0582 →
RELEASE OF SECURITY INTEREST Recorded May 12, 2021
From: JPMORGAN CHASE BANK, N.A.
To: HEXION INC.
Reel/Frame 056219/0677 →
SECURITY INTEREST Recorded May 5, 2021
From: HEXION VAD LLC
To: GOLDMAN SACHS SPECIALTY LENDING GROUP, L.P., AS COLLATERAL AGENT
Reel/Frame 056145/0957 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 2, 2019
From: GOODWIN, KIMBERLY; VISWANATHAN, GANAPATHY S.; PEACE, SCOTT; MAIORANA, ANTHONY; PATIL, VISHAL
To: HEXION INC.
Reel/Frame 049942/0475 →
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 →