HIGH HEAT COMPOSITE COMPOSITIONS, ARTICLES, AND USES THEREOF

1 . A high heat epoxy composite comprising:

a substrate;

a matrix composition comprising:

a high heat epoxy compound having formula:

wherein

R 1 and R 2 at each occurrence are each independently an epoxide-containing functional group;

R a and R b at each occurrence are each independently halogen, C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 3 -C 8 cycloalkyl, or C 1 -C 12 alkoxy;

p and q at each occurrence are each independently 0 to 4; R 13 at each occurrence is independently a halogen or a C 1 -C 6 alkyl group;

c at each occurrence is independently 0 to 4; R H at each occurrence is independently a C 1 -C 6 alkyl, phenyl, or phenyl substituted with up to five halogens or C 1 -C 6 alkyl groups;

R g at each occurrence is independently C 1 -C 12 alkyl or halogen, or two R g groups together with the carbon atoms to which they are attached form a four-, five, or six-membered cycloalkyl group; and

t is 0 to 10; and

a hardener;

wherein the matrix composition comprises 20 to 60 total weight percent of the composite-; and

wherein

a cured sample of the matrix composition has a glass transition temperature of greater than or equal to 200° C., and

a cured, laminated sample of the composite has a flexural strength of greater than 850 MPa measured as per ASTM D7264; and a flexural modulus of greater than 65 GPa measured as per ASTM D7264.

2 . The composite of claim 1 , wherein R 1 and R 2 at each occurrence are each independently:

wherein R 3a and R 3b are each independently hydrogen or C 1 -C 12 alkyl.

3 . The composite of claim 1 , wherein the high heat epoxy compound has the formula (1-a), (2-a), or (4-b)

4 . The composite of claim 1 , wherein the substrate comprises a woven fabric, non-woven fabric, plain weave cloth, satin weave cloth, non-crimp fabric, unidirectional fibers, braid, tow, end, rope, or a combination comprising at least one of the foregoing.

5 . The composite of claim 1 , wherein the substrate comprises a high modulus carbon-fiber, intermediate modulus carbon-fiber, high strength carbon-fiber, E-glass, S-glass, aramid fiber, or a combination comprising at least one of the foregoing.

6 . The composite of claim 1 , wherein the hardener is an aromatic diamine compound, preferably wherein the aromatic diamine amine compound comprises 4-aminophenyl sulfone (DDS), 4,4′-methylenedianiline, diethyltoluenediamine, 4,4′-methylenebis(2,6-diethyl)-aniline, m-phenylenediamine, p-phenylenediamine, 2,4-bis(p-aminobenzyl)aniline, 3,5-diethyltoluene-2,4-diamine, 3,5-diethyltoluene-2,6-diamine, m-xylylenediamine and p-xylylenediamine, diethyl toluene diamines, or a combination comprising at least one of the foregoing.

7 . The composite of claim 1 , wherein the composite is cured or laminated.

8 . The composite of claim 1 , wherein the matrix composition comprises 50 to 85 weight percent of the high heat epoxy compound and 15 to 50 weight percent of the hardener.

9 . A method of manufacturing a high heat epoxy prepreg, comprising

coating a substrate with a matrix composition comprising

a compound having formula:

wherein

R 1 and R 2 at each occurrence are each independently an epoxide-containing functional group;

R a and R b at each occurrence are each independently halogen, C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 3 -C 8 cycloalkyl, or C 1 -C 12 alkoxy;

p and q at each occurrence are each independently 0 to 4;

R 13 at each occurrence is independently a halogen or a C 1 -C 6 alkyl group;

c at each occurrence is independently 0 to 4;

R 14 at each occurrence is independently a C 1 -C 6 alkyl, phenyl, or phenyl substituted with up to five halogens or C 1 -C 6 alkyl groups;

R g at each occurrence is independently C 1 -C 12 alkyl or halogen, or two R g groups together with the carbon atoms to which they are attached form a four-, five, or six-membered cycloalkyl group; and

t is 0 to 10;

a hardener; and

optionally a solvent, to form the high heat epoxy prepreg,

wherein

the prepreg comprises

40 to 80 wt %, substrate,

20 to 60 wt % matrix composition, wherein the prepreg comprises 15 to 50 wt % of the compound having formula (I) to (IX), and

wherein

a cured, laminated sample of the prepreg has a flexural strength of greater than 850 MPa measured as per ASTM D7264 and a flexural modulus of greater than 65 GPa measured as per ASTM D7264, and

a cured sample of the matrix composition has a glass transition temperature of greater than or equal to 200° C.

10 . The method of claim 9 , wherein the matrix composition comprises 10 to 26 wt % of the solvent.

11 . The method of claim 9 , wherein coating comprises immersing the substrate into the matrix composition minutes; spraying the matrix composition onto the substrate; curtain coating the substrate with the polymer solution; pouring the matrix composition onto the substrate; or a combination comprising at least one of the foregoing.

12 . The method of claim 9 , wherein heating comprises a temperature of 25 to 100° C. for 1 to 10 hours.

13 . The method of claim 9 , wherein the substrate comprises a woven fabric, non-woven fabric, plain weave cloth, satin weave cloth, non-crimp fabric, unidirectional fibers, braid, tow, end, rope, a high modulus carbon-fiber, intermediate modulus carbon-fiber, high strength carbon-fiber, E-glass, S-glass, aramid fiber, or a combination comprising at least one of the foregoing.

14 . A prepreg formed by the method of claim 9 .

15 . A high heat epoxy composite produced by consolidating a prepreg formed by the method of claim 9 .

16 . The composite of claim 15 , in the form of a laminate produced by consolidating at least two of the prepreg under heat and pressure.

17 . The composite of claim 16 , wherein the prepreg layers are in the form of continuous unidirectional fiber-reinforced tapes.

18 . The composite of claim 15 , wherein the composite is thermoformed to form a shape.

19 . The composite of claim 15 , wherein

a cured sample of the matrix composition has a glass transition temperature of greater than or equal to 200° C.; and

a cured, laminated sample of the composite has

a flexural strength of greater than 850 MPa measured as per ASTM D7264; and

a flexural modulus of greater than 65 GPa measured as per ASTM D7264.

20 . An article comprising the composite of claim 15 .