# US 10,308,769 B2 · [(2-ethoxy-5-trans-1-propen-1-yl)-phenoxyl]-terminated compounds

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- Number: US 10,308,769 B2
- Document ID: US10308769B2
- Status: Granted
- Kind: B2
- Application number: 15/551,923
- Filed: 2016-09-02
- Published: 2018-02-01
- Granted: 2019-06-04
- Earliest claimed: 2015-09-16
- Assignees: Evonik Technochemie GmbH
- Applicants: Evonik Technochemie GmbH
- Inventors: Sergey Evsyukov; Tim Pohlmann; Horst Stenzenberger; Matthijs Ter Wiel
- Web page: https://patentgrep.com/patent/US10308769B2

## CPC

- C07C 43/21: containing rings other than six-membered aromatic rings
- C07C 43/23: containing hydroxy or O-metal groups
- C07C 49/84: containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups
- C07C 317/22: with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07D 239/52: Two oxygen atoms
- C08F 222/404: {substituted imides comprising oxygen other than the carboxy oxygen}
- C08G 63/13: containing two or more aromatic rings
- C08G 65/34: from hydroxy compounds or their metallic derivatives {(C08G65/26 takes precedence)}
- C08G 65/4012: {Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones}
- C08G 65/48: Polymers modified by chemical after-treatment
- C08G 75/23: Polyethersulfones
- C08L 71/00: Compositions of polyethers obtained by reactions forming an ether link in the main chain (of polyacetals C08L59/00; of epoxy resins C08L63/00; of polythioether-ethers C08L81/02; of polyether-sulfones C08L81/06); Compositions of derivatives of such polymers
- C09J 4/00: Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)

## Abstract

A compound according to formula (I) can be part of a heat-curable resin composition based on polymaleimide resin systems comprising such compound as co-monomer: wherein D is an x-functional group; and x is an integer ≥2; with the proviso that the x-functional group D is not a polycarbonate with an average molar mass in the range of 15000 g/mol to 150000 g/mol. A crosslinked resin is obtainable by curing such composition. The compounds can be used in structural adhesives, matrix resins for fiber prepregs, moulding compounds, and structural and/or electrical composites.

## Claims

### Claim 1

A [(2-ethoxy-5-trans-1-propen-1-yl)-phenoxy]-terminated compound according to formula (I)
wherein
D is a difunctional group; and
x is 2;
with the proviso that
the difunctional group D is not a polycarbonate with an average molar mass in the range of 15000 g/mol to 150000 g/mol, and
wherein difunctional group D is selected from the group consisting of:
(a) alkylene or alkenylene group with 2 to 12 carbon atoms:
(b) cycloalkylene group with 5 or 6 carbon atoms;
(c) heterocyclic group with 3 to 5 carbon atoms and at least one nitrogen sulfur or oxygen atom in the heterocyclic ring;
(d) mono- or dicarbocyclic group;
(e) bridged multicyclic group consisting of at least two groups selected from the following: monocarbocyclic aromatic groups, dicarbocyclic aromatic groups, cycloalkylene groups; wherein these groups are linked to each other by direct carbon-carbon bonds or by divalent groups; and
(f) one of the groups of the following structures
wherein AR1, AR2, AR3, AR4, AR5 and AR6 are independently difunctional aliphatic or aromatic residues;
and wherein n is an integer selected in the range from 2 to 100 and represents the number of repeating structural units in the polymer backbone:
(g) group of the following structure
wherein R26 is a monofunctional group selected from the group consisting of:
(1) alkyl or alkenyl group with 2 to 12 carbon atoms,
(2) cycloalkyl group with 5 or 6 carbon atoms,
(3) aryl group with 6 to 12 carbon atoms, and
(4) [(2-ethoxy-5-trans-1-propen-1-yl)-phenoxy]-group.

### Claim 2 (depends on 1)

The [(2-ethoxy-5-trans-1-propen-1-yl)-phenoxy]-terminated compound according to claim 1,
wherein D is a difunctional group selected from the group consisting of:
wherein n is an integer selected in the range from 2 to 100 and represents the number of repeating structural units in the polymer backbone.

### Claim 3 (depends on 1)

A curable composition, comprising:
i. at least one [(2-ethoxy-5-trans-1-propen-1-yl)-phenoxy]-terminated compound according to claim 1;
ii. at least one polyimide of formula (II)
wherein
B is a difunctional group containing a carbon-carbon double bond, and
A is a y-functional group; and
y is an integer ≥2.

### Claim 4 (depends on 3)

The curable composition according to claim 3,
wherein
the y-functional group A in the polyimide according to formula (II) is selected from the following difunctional groups:
a) alkylene group with 2 to 12 carbon atoms;
b) cycloalkylene group with 5 to 6 carbon atoms;
c) heterocyclic group with 4 to 5 carbon atoms and at least one nitrogen, oxygen, or sulphur atom in the ring;
d) mono- or dicarbocyclic group;
e) bridged multicyclic group consisting of at least two groups selected from the following: monocarbocyclic aromatic groups, dicarbocyclic aromatic groups, cycloalkylene groups; wherein these groups are linked to each other by direct carbon-carbon bonds or by divalent groups;
and
f) a group defined by formula (III)
wherein R9 is one of the following groups

### Claim 5 (depends on 3)

A curable composition according to claim 3,
wherein
B in the polyimide according to formula (II), is selected from the following difunctional groups:

### Claim 6 (depends on 3)

A curable composition according to claim 3, wherein the polyimide according to formula (II) is at least one polyimide selected from the group consisting of:
4,4′-bismaleimidodiphenylmethane, bis(3-methyl-5-ethyl-4-maleimidophenyl)methane, bis(3,5-dimethyl-4-maleimidophenyl)methane, 4,4′-bismaleimidodiphenylether, 4,4′-bismaleimidodiphenylsulfone, 3,3′-bismaleimidodiphenylsulfone, bismaleimidodiphenylindane, 2,4-bismaleimidotoluene, 2,6-bismaleimidotoluene, 1,3-bismaleimidobenzene, 1,2-bismaleimidobenzene, 1,4-bismaleimidobenzene, 1,2-bismaleimidoethane, 1,6-bismaleimidohexane, 1,6-bismaleimido-(2,2,4-trimethyl)hexane, 1,6-bismaleimido-(2,4,4-trimethyl)hexane, 1,4-bis(maleimidomethyl)cyclohexane, 1,3-bis(maleimidomethyl)cyclohexane, 1,4-bismaleimidodicyclohexylmethane, 1,3-bis(maleimidomethyl)benzene, and 1,4-bis(maleimidomethyl)benzene.

### Claim 7 (depends on 3)

A curable composition according to claim 3, wherein D is selected from the group consisting of:
wherein n is an integer selected in the range from 2 to 100 and represents the number of repeating structural units in the polymer backbone,
and wherein the polyimide according to formula (II) is selected from the group consisting of:
4,4′-bismaleimidodiphenylmethane, bis(3-methyl-5-ethyl-4-maleimidophenyl)methane, bis(3,5-dimethyl-4-maleimidophenyl)methane, 4,4′-bismaleimidodiphenylether, 4,4′-bismaleimidodiphenylsulfone, 3,3′-bismaleimidodiphenylsulfone, bismaleimidodiphenylindane, 2,4-bismaleimidotoluene, 2,6-bismaleimidotoluene, 1,3-bismaleimidobenzene, 1,2-bismaleimidobenzene, 1,4-bismaleimidobenzene, 1,2-bismaleimidoethane, 1,6-bismaleimidohexane, 1,6-bismaleimido-(2,2,4-trimethyl)hexane, 1,6-bismaleimido-(2,4,4-trimethyl)hexane, 1,4-bis(maleimidomethyl)cyclohexane, 1,3-bis(maleimidomethyl)cyclohexane, 1,4-bismaleimidodicyclohexylmethane, 1,3-bis(maleimidomethyl)benzene, and 1,4-bis(maleimidomethyl)benzene.

### Claim 8 (depends on 3)

A curable composition according to claim 3, further comprising a cure accelerator or a cure inhibitor.

### Claim 9 (depends on 3)

A process for the manufacture of a curable composition according to claim 3, comprising blending the components of the composition using a powder-, melt-, or solvent-assisted blending process resulting in a solid, low-melting, or tacky curable composition.

### Claim 10 (depends on 3)

A curable pre-polymer obtainable from a curable composition according to claim 3, by a process comprising heating the curable composition to a temperature in the range of 50° C. to 250° C., for a time sufficient to obtain the pre-polymer which is still formable upon the application of heat and/or pressure.

### Claim 11 (depends on 3)

A crosslinked polymer obtainable from the curable composition according to claim 3 by a process comprising the heating the curable composition to a temperature in the range of 70° C. to 280° C. for a time sufficient to obtain a polymer.

### Claim 12 (depends on 3)

A process for the manufacture of a composite material, comprising: combining a curable composition according to claim 3 with a fibrous or particulate reinforcement, and curing a resultant product.

### Claim 13 (depends on 12)

A composite material obtainable by a process according to claim 12.

### Claim 14 (depends on 10)

A process for the manufacture of a composite material, comprising: combining a curable pre-polymer according to claim 10 with a fibrous or particulate reinforcement, and curing a resultant product.