# US 12,215,185 B2 · Recyclable and reworkable epoxy resins

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- Number: US 12,215,185 B2
- Document ID: US12215185B2
- Status: Granted
- Kind: B2
- Application number: 17/392,907
- Filed: 2021-08-03
- Published: 2021-11-25
- Granted: 2025-02-04
- Earliest claimed: 2019-02-04
- Assignees: Aditya Birla Chemicals (Thailand) Ltd. (Epoxy Division)
- Applicants: Aditya Birla Chemicals (Thailand) Ltd. (Epoxy Division)
- Inventors: Chandan Kumar Singh; Pradip Kumar Dubey; Weerawat Sripet; Kanyarat Sittipummongkol
- Web page: https://patentgrep.com/patent/US12215185B2

## CPC

- C08G 59/245: {aromatic}
- C08G 59/063: {with epihalohydrins}
- C08G 59/24: carbocyclic
- C08G 59/306: {containing silicon}
- C08G 59/3218: {Carbocyclic compounds}
- C08G 59/3227: {Compounds containing acyclic nitrogen atoms}
- C08G 59/3281: {containing silicon}
- C08G 59/5026: {cycloaliphatic}
- C08G 59/687: {containing sulfur}
- C08J 11/26: containing carboxylic acid groups, their anhydrides or esters
- C08J 11/28: by treatment with organic compounds containing nitrogen, sulfur or phosphorus
- C08J 2363/00: Characterised by the use of epoxy resins; Derivatives of epoxy resins
- C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- Y02W 30/62: Plastics recycling; Rubber recycling
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- Y02W: CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT

## Abstract

An epoxy resin component(s) for a recyclable epoxy resin system is disclosed. The recyclable epoxy resin system comprises an epoxy resin component having a structural Formula I or an epoxy resin component having a structural Formula II and a curing agent. A process(es) for preparing the epoxy resin component having the structural Formula I and the epoxy resin system having the structural Formula II is also disclosed.

## Claims

### Claim 1

A process for preparing an epoxy resin component having a structural Formula I for an epoxy resin system, the process comprising:
epoxidizing a compound having a structural Formula VI with a percarboxylic acid compound or hydrogen peroxide to obtain an epoxidized alcohol; and
reacting the epoxidized alcohol with a compound having a structural Formula III or a compound selected from a group consisting of 2-methoxy propene, 2-2 di methoxy propane, 2 ethoxy propene, 2-2 di ethoxy propane, and 2-2 di propoxy propane in the presence of an acidic catalyst to obtain the epoxy resin component having the structural Formula I,
wherein
the compound having the structural Formula VI is represented by:
wherein R1, R2, and R3, are hydrogen,
R4 is any one of:
the compound having the structural Formula III is represented by:
wherein
R1 and R2 are independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heterocyclic, heterocycloalkyl, cycloalkenyl, heteroaryl, alkoxy, alkoxyaryl, alkoxy alkyl, or aryloxy, and
the epoxy resin component having the structural Formula I is:
wherein
m=0, 1 or 2 such that
if m=0 then n=4,
if m=1 then n=3, or
if m=2 then n=2,
A is carbon,
D is oxygen,
X is oxygen, and
B is independently alkylene-arylene, arylene-alkylene-arylene, alkylene, or alkylene-cycloalkylene.

### Claim 2 (depends on 1)

The process as claimed in claim 1, wherein the percarboxylic acid compound is selected from a group consisting of peracetic acid, m-chloro perbenzoic acid, and per trifluoro acetic acid.

### Claim 3 (depends on 1)

The process as claimed in claim 1, wherein the compound having the structural Formula VI and the percarboxylic acid compound or hydrogen peroxide are provided in a molar ratio in a range of 0.5 to 2.

### Claim 4 (depends on 1)

The process as claimed in claim 1, wherein the acidic catalyst is selected from a group consisting of a proton donor, a homogeneous acid catalyst and a heterogeneous acid catalyst.

### Claim 5 (depends on 1)

The process as claimed in claim 1, wherein the epoxidized alcohol and the compound having the structural Formula III or the compound selected from a group consisting of 2-methoxy propene, 2-2 di methoxy propane, 2 ethoxy propene, 2-2 di ethoxy propane, and 2-2 di propoxy propane are provided in a molar ratio in a range of 0.01 to 10.

### Claim 6 (depends on 1)

The process as claimed in claim 1, wherein the compound having the structural Formula III is selected from a group consisting of formaldehyde, paraformaldehyde, acetaldehyde, benzaldehyde, acetone, and methyl ethyl ketone.

### Claim 7

A process for preparing an epoxy resin component of Formula I, said process comprising the steps of:
a. epoxidizing 4-(2-propen-1-yloxy)-benzenemethanol with a percarboxylic acid compound or hydrogen peroxide to obtain 4-(2-Oxiranylmethoxyl)-benzenemethanol; and
b. reacting the obtained 4-(2-Oxiranylmethoxyl)-benzenemethanol with 2-methoxy propene in the presence of an acid catalyst to obtain the epoxy resin component of Formula I,
wherein the epoxy resin component of formula I is represented by:

### Claim 8 (depends on 7)

The process as claimed in claim 7, wherein 4-(2-propen-1-yloxy)-benzenemethanol and the percarboxylic acid compound or hydrogen peroxide are provided in a molar ratio in the range of 0.5 to 2.

### Claim 9 (depends on 7)

The process as claimed in claim 7, wherein 4-(2-Oxiranylmethoxyl)-Benzenemethanol and 2-methoxy propene are provided in a molar ratio in the range of 0.01 to 10.

### Claim 10 (depends on 7)

The process as claimed in claim 7, wherein the epoxidation of 4-(2-propen-1-yloxy)-benzenemethanol is carried out with hydrogen peroxide to obtain 4-(2-Oxiranylmethoxyl)-benzenemethanol.

### Claim 11 (depends on 7)

The process as claimed in claim 7, wherein the acidic catalyst is p-toluene sulphonic acid.