US2022119588A1PendingUtilityA1
Recyclable and reworkable epoxy resins
Assignee: ADITYA BIRLA CHEMICALS THAILAND LTD EPOXY DIVPriority: Feb 4, 2019Filed: Dec 11, 2019Published: Apr 21, 2022
Est. expiryFeb 4, 2039(~12.5 yrs left)· nominal 20-yr term from priority
C08G 59/3254C08G 59/3281C08G 59/5026C08G 59/063C08G 59/306C08G 59/24C08J 11/26C08L 63/00C08G 59/3218C08G 59/3227C08G 59/226C08G 59/30C08G 59/687C08G 59/245C08J 2363/00C08J 11/28Y02W30/62
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Claims
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
exact text as granted — not AI-modified1 . An epoxy resin component for a recyclable epoxy resin system, the epoxy resin component having a structural Formula I or a structural Formula II:
wherein
m=0 then n=4,
m=1 then n=3,
m=2 then n=2,
A is carbon or silicon,
D is oxygen or nitrogen or carboxylic group,
X is oxygen or sulfur,
s and t is independently from 1 to 20,
R 1 and R 2 is independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heterocyclic, heterocycloalkyl, cycloalkenyl, heteroaryl, alkoxyaryl, alkoxy alkyl,
B is independently arylene, arylene ethers, alkylene—arylene, alkylene—arylene alkylene, alkenylene—arylene, alkenylene—arylene alkenylene, alkylene—arylene—alkenylene, alkynylene arylene, alkynylene—arylene—alkynylene, heteroarylene, alkylene—heteroarylene, alkylene—heteroarylene—alkylene, alkenylene—heteroarylene, alkenylene—heteroarylene—alkenylene, alkylene—heteroarylene—alkenylene, alkynylene heteroarylene, alkynylene—heteroarylene—alkynylene, alkylene, alkylene—hetero—alkylene, alkenylene, alkenylene—hetero—alkenylene, alkylene—hetero—alkenylene, alkynylene, cycloalkylene, alkylene—cycloalkylene, alkylene—cycloalkylene alkylene, alkenylene—cycloalkylene, alkenylene cycloalkylene—alkenylene, alkylene—cycloalkylene alkenylene, alkynylene—cycloalkylene, alkynylene cycloalkylene—alkynylene, heterocycloalkylene, alkylene heterocycloalkylene, alkylene—heterocycloalkylene alkylene, alkenylene—heterocycloalkylene, alkenylene heterocycloalkylene—alkenylene, alkylene heterocycloalkylene—alkenylene, alkynylene heterocycloalkylene, alkynylene—heterocycloalkylene alkynylene, cycloalkenylene, alkylene—cycloalkenylene, alkylene—cycloalkenylene—alkylene, alkenylene—cycloalkenylene, alkenylene—cycloalkenylene—alkenylene, alkylene cycloalkenylene—alkenylene, alkynylene—cycloalkenylene, alkynylene—cycloalkenylene—alkynylene, heterocycloalkenylene, alkylene—heterocycloalkenylene, alkylene—hetero cycloalkenylene—alkylene, alkenylene—heterocycloalkenylene, alkenylene—heterocycloalkenylene—alkenylene, alkylene—heterocycloalkenylene—alkenylene, alkynylene heterocycloalkenylene, alkynylene—heterocycloalkenylene, alkynylene.
2 . The epoxy resin component as claimed in claim 1 , wherein the epoxy resin component having the structural Formula I is:
S.No.
Compounds of structural Formula I
ERC-1
ERC-2
ERC-3
ERC-4
ERC-5
ERC-6
ERC-7
ERC- 8
ERC-9
ERC-10
ERC-11
ERC-12
ERC-13
ERC-14
ERC-15
ERC-16
ERC-17
ERC-18
ERC-19
ERC-20
ERC-21
ERC-22
ERC-23
ERC-24
ERC-25
ERC-26
ERC-27
ERC-28
ERC-29
ERC-30
ERC-31
ERC-32
ERC-33
ERC-34
ERC-35
ERC-36
ERC-37
ERC-38
ERC-39
ERC-40
ERC-41
ERC-42
ERC-43
ERC-44
ERC-45
ERC-46
ERC-47
ERC-48
ERC-49
ERC-50
ERC-51
ERC-52
ERC-53
ERC-54
ERC-55
ERC-56
ERC-57
ERC-58
ERC-59
ERC-60
ERC-61
ERC-62
ERC-63
ERC-64
ERC-65
ERC-66
ERC-67
3 . The epoxy resin component as claimed in claim 1 , wherein the epoxy resin component having the structural Formula II is:
S.No.
Compounds of Structural Formula II
ERC-1
ERC-2
ERC-3
ERC-4
ERC-5
ERC-6
4 . A process for preparing an epoxy resin component having a structural Formula I and an epoxy resin component having a structural Formula II for an epoxy resin system, the process comprising:
partially epoxidizing a polyhydric alcohol having one or more hydroxyl group with an epihalohydrin in the presence of a base to obtain a partially epoxidized alcohol; and reacting the partially epoxidized alcohol with a compound having a structural Formula III, a compound having a structural Formula IV or a compound having a structural Formula V in the presence of an acidic catalyst to obtain the epoxy resin component having the structural Formula I and the epoxy resin component having the structural Formula II, wherein the compound having the structural Formula III is represented by:
wherein R 1 and R 2 are independently hydrogen, alkyl, alkenyl, alkynyl, methylene, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heterocyclic, heterocycloalkyl, cycloalkenyl, heteroaryl, alkoxy, alkoxyaryl, alkoxy alkyl, aryloxy,
the compound having the structural Formula IV is represented by:
wherein R 1 is independently hydrogen, alkyl, aryl, aralkyl, alkenyl, alkynyl;
R 2 , R 3 , R 4 are independently hydrogen, alkyl, alkenyl, alkynyl, methylene, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heterocyclic, heterocycloalkyl, cycloalkenyl, heteroaryl, alkoxy, alkoxyaryl, alkoxy alkyl, aryloxy;
the compound having the structural Formula V is represented by:
wherein
R 1 R 2 , R 3 , R 4 are independently hydrogen, alkyl, alkenyl, alkynyl, methylene, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heterocyclic, heterocycloalkyl, cycloalkenyl, heteroaryl, alkoxy, alkoxyaryl, alkoxy alkyl, aryloxy,
wherein the epoxy resin component having the structural Formula I and the structural Formula II is:
wherein
m=0 then n=4,
m=1 then n=3,
m=2 then n=2,
A is carbon or silicon,
D is oxygen or nitrogen or carboxylic group,
X is oxygen or sulfur,
s and t is independently from 1 to 20,
R 1 and R 2 is independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heterocyclic, heterocycloalkyl, cycloalkenyl, heteroaryl, alkoxyaryl, alkoxy alkyl,
B is independently arylene, arylene ethers, alkylene—arylene, alkylene—arylene alkylene, alkenylene—arylene, alkenylene—arylene alkenylene, alkylene—arylene—alkenylene, alkynylene arylene, alkynylene—arylene—alkynylene, heteroarylene, alkylene—heteroarylene, alkylene—heteroarylene—alkylene, alkenylene—heteroarylene, alkenylene—heteroarylene—alkenylene, alkylene—heteroarylene—alkenylene, alkynylene heteroarylene, alkynylene—heteroarylene—alkynylene, alkylene, alkylene—hetero—alkylene, alkenylene, alkenylene—hetero—alkenylene, alkylene—hetero—alkenylene, alkynylene, cycloalkylene, alkylene—cycloalkylene, alkylene—cycloalkylene alkylene, alkenylene—cycloalkylene, alkenylene cycloalkylene—alkenylene, alkylene—cycloalkylene alkenylene, alkynylene—cycloalkylene, alkynylene cycloalkylene—alkynylene, heterocycloalkylene, alkylene heterocycloalkylene, alkylene—heterocycloalkylene alkylene, alkenylene—heterocycloalkylene, alkenylene heterocycloalkylene—alkenylene, alkylene heterocycloalkylene—alkenylene, alkynylene heterocycloalkylene, alkynylene—heterocycloalkylene alkynylene, cycloalkenylene, alkylene—cycloalkenylene, alkylene—cycloalkenylene—alkylene, alkenylene—cycloalkenylene, alkenylene—cycloalkenylene—alkenylene, alkylene cycloalkenylene—alkenylene, alkynylene—cycloalkenylene, alkynylene—cycloalkenylene—alkynylene, heterocycloalkenylene, alkylene—heterocycloalkenylene, alkylene—hetero cycloalkenylene—alkylene, alkenylene—heterocycloalkenylene, alkenylene—heterocycloalkenylene—alkenylene, alkylene—heterocycloalkenylene—alkenylene, alkynylene heterocycloalkenylene, alkynylene—heterocycloalkenylene, alkynylene.
5 . The process as claimed in claim 4 , wherein the polyhydric alcohol having one or more hydroxyl group is selected from a group comprising of hydroxy phenyl alkanol, hydroxy cycloalkyl alkanol, and hydroxy diphenyl alkanol.
6 . The process as claimed in claim 4 , wherein the polyhydric alcohol having one or more hydroxyl group to the epihalohydrin are added in a molar ratio in a range of 0.01 to 5.
7 . The process as claimed in claim 4 , wherein the partially epoxidized alcohol to the compound having the structural Formula III, the compound having the structural Formula IV or the compound having the structural Formula V are added in a molar ratio in a range of 0.01 to 10.
8 .- 13 . (canceled)
14 . The process as claimed in claim 4 , wherein the acidic catalyst is selected from a group comprising of a proton donor, a homogeneous acid catalyst and a heterogeneous acid catalyst.
15 .- 20 . (canceled)
21 . The process as claimed in claim 4 , wherein the base is selected from a group comprising of hydroxides of alkali metals and carbonates of alkali metals.
22 . (canceled)
23 . The process as claimed in claim 4 , wherein the compound having the structural Formula III is selected from a group comprising of formaldehyde, paraformaldehyde, acetaldehyde, benzaldehyde, acetone, and methyl ethyl ketone.
24 . The process as claimed in claim 4 , wherein the compound having the structural Formula IV is selected from a group comprising of 2-methoxy propene, 2-2 di methoxy propane, 2 ethoxy propene, 2-2 di ethoxy propane, and 2-2 di propoxy propane.
25 . The process as claimed in claim 4 , wherein the compound having the structural Formula V is selected from a group comprising of tetra alkoxy silane, tri alkoxy silanes and di alkoxy silanes.
26 . A recyclable epoxy resin system comprising:
a curing agent; and an epoxy resin component having a structural Formula I or an epoxy resin component having a structural Formula II; wherein the epoxy resin component having the structural Formula I and the structural Formula II is:
wherein
m=0 then n=4,
m=1 then n=3,
m=2 then n=2,
A is carbon or silicon,
D is oxygen or nitrogen or carboxylic group;
X is oxygen or sulfur,
s and t is independently from 1 to 20
R 1 and R 2 is independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heterocyclic, heterocycloalkyl, cycloalkenyl, heteroaryl, alkoxyaryl, alkoxy alkyl;
B is independently arylene, arylene ethers, alkylene—arylene, alkylene—arylene alkylene, alkenylene—arylene, alkenylene—arylene alkenylene, alkylene—arylene—alkenylene, alkynylene arylene, alkynylene—arylene—alkynylene, heteroarylene, alkylene—heteroarylene, alkylene—heteroarylene—alkylene, alkenylene—heteroarylene, alkenylene—heteroarylene—alkenylene, alkylene—heteroarylene—alkenylene, alkynylene heteroarylene, alkynylene—heteroarylene—alkynylene, alkylene, alkylene—hetero—alkylene, alkenylene, alkenylene—hetero—alkenylene, alkylene—hetero—alkenylene, alkynylene, cycloalkylene, alkylene—cycloalkylene, alkylene—cycloalkylene alkylene, alkenylene—cycloalkylene, alkenylene cycloalkylene—alkenylene, alkylene—cycloalkylene alkenylene, alkynylene—cycloalkylene, alkynylene cycloalkylene—alkynylene, heterocycloalkylene, alkylene heterocycloalkylene, alkylene—heterocycloalkylene alkylene, alkenylene—heterocycloalkylene, alkenylene heterocycloalkylene—alkenylene, alkylene heterocycloalkylene—alkenylene, alkynylene heterocycloalkylene, alkynylene—heterocycloalkylene alkynylene, cycloalkenylene, alkylene—cycloalkenylene, alkylene—cycloalkenylene—alkylene, alkenylene—cycloalkenylene, alkenylene—cycloalkenylene—alkenylene, alkylene cycloalkenylene—alkenylene, alkynylene—cycloalkenylene, alkynylene—cycloalkenylene—alkynylene, heterocycloalkenylene, alkylene—heterocycloalkenylene, alkylene—hetero cycloalkenylene—alkylene, alkenylene—heterocycloalkenylene, alkenylene—heterocycloalkenylene—alkenylene, alkylene—heterocycloalkenylene—alkenylene, alkynylene heterocycloalkenylene, alkynylene—heterocycloalkenylene, alkynylene.
27 . The recyclable epoxy resin system as claimed in claim 26 , wherein the curing agent is selected from a group comprising of aliphatic amines, alicyclic polyamines, aromatic amines, polyether amine, ketoimines, anhydrides, polyamides, imidazoles, polythiols, polyphenols, polycorboxylic acid, carboxylic based polyesters, carboxylic based polyacrylates, UV curing agents and a combination thereof.
28 . The recyclable epoxy resin system as claimed in claim 26 , for use as a matrix in manufacturing of a high-performance composites reinforced with glass, carbon, polyaramid and natural fibres in wind turbine rotor blades, automotive composites, sports and recreational goods, infrastructure, aerospace and defense and marine applications, consumer adhesives, industrial adhesives, structural adhesives, decorative coatings, industrial coatings, electrical, electronics, civil engineering and construction applications.
29 . A process for recycling an epoxy resin system, the process comprising:
heating the epoxy resin system; and immersing the heated epoxy resin system in an acid and a solvent at a temperature in a range of 50 to 150° C.; the recyclable epoxy resin system being a reaction product of an epoxy resin component having a structural Formula I or an epoxy resin component having a structural Formula II and a curing agent.
30 . The process as claimed in claim 29 , wherein the acid is selected from a group comprising of strong proton donor acid compounds and weak proton acid compounds.
31 . The process as claimed in claim 29 , wherein the solvent is selected from a group comprising of aliphatic hydrocarbons, aromatic hydrocarbons, ethers, ketones, acetates, aldehydes, furans, and water.Join the waitlist — get patent alerts
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