Alkenylphenoxy-substituted 1,1-diphenylethylenes, processes for their preparation, and their use

1. An alkenylphenoxy-1,1-diphenylethylene of formula (I):

wherein:

R 1 is hydrogen or an alkenylphenoxy group,

R 2 is an alkenylphenoxy group, and

R 3 is hydrogen or an alkyl group with 1 to 4 carbon atoms.

2. The alkenylphenoxy-1,1-diphenylethylene of claim 1 , wherein alkenylphenoxy groups R 1 and R 2 are independently selected from the group consisting of the following structures:

in which the ALKENYL residue is a 1-alkenyl group with 2 to 6 carbon atoms or a 2-alkenyl group with 3 to 6 carbon atoms.

3. A curable composition, comprising:

(a) at least one alkenylphenoxy-diphenylethylene according to claim 1 ; and

(b) at least one polyimide of formula (II):

wherein:

B is a difunctional group containing a carbon-carbon double bond, and

A is an x-functional group, and

x is an integer ≥2.

4. The curable composition according to claim 3 , wherein B in the polyimide according to formula (II) is selected from the group consisting of the following difunctional groups:

5. The curable composition according to claim 3 , wherein the x-functional group A in the polyimide of formula (II), is selected from the group consisting of:

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 R 12 is one of the following groups:

6. The curable composition according to claim 3 , wherein the polyimide of 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-bis maleimido-(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.

7. A process for manufacturing the curable composition of claim 3 , the process comprising blending components (a) and (b) with a powder-, melt-, or solvent assisted blending process resulting in a solid, low-melting, or tacky curable composition.

8. A curable prepolymer obtained from the curable composition according to claim 3 , by a process comprising heating the curable composition to a temperature ranging from 50° C. to 250° C. for a time sufficient to obtain a prepolymer, which is still formable upon the application of heat, pressure, or both.

9. A crosslinked polymer obtained from the curable composition according to claim 3 by a process comprising heating the curable composition to a temperature ranging from 70° C. to 280° C. for a time sufficient to obtain a polymer.

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

11. A composite material obtained by the process according to claim 10 .

12. The curable composition according to claim 5 , wherein the x-functional group A in the polyimide of formula (II) is

e) bridged multicyclic group consisting of at least two groups selected from the following: monocarbocyclic aromatic groups, dicarbocyclic aromatic groups, cycloalkylene groups;

these groups are linked to each other by direct carbon-carbon bonds or by divalent groups, and

the divalent groups are selected from the following: oxy-group, thio-group, alkylene-group with 1 to 3 carbon atoms, sulfone-group, methanone-group, or one of the following groups:

wherein

R 4 , R 5 , R 6 , R 7 , R 8 , R 9 are independently alkyl groups with 1 to 6 carbon atoms; and

R 10 and R 11 are independently alkylene groups with 1 to 6 carbon atoms.