Compositions with improved characteristics

1. A composition comprising components (a) and (b) wherein component (a) is one or more cyanate esters independently selected from

(i) a difunctional cyanate ester compound of formula (I)

wherein

R 1 through R 8 are independently selected from the group consisting of hydrogen, linear C 1-10 alkyl, halogenated linear C 1-10 alkyl, branched C 4-10 alkyl, halogenated branched C 4-10 alkyl, C 3-8 cycloalkyl, halogenated C 3-8 cycloalkyl, C 1-10 alkoxy, halogen, phenyl and phenoxy;

Z 1 indicates a direct bond or a divalent moiety selected from the group consisting of —O—, —S—, —S(═O)—, —S(═O) 2 —, —CH 2 —, —CH(CH 3 )—, —C(CH 3 ) 2 —, —CH(CF 3 )—, —C(CF 3 ) 2 —, —C(═O)—, —C(═CH 2 )—, —C(═CCl 2 )—, —Si(CH 3 ) 2 —, linear C 1-10 alkanediyl, branched C 4-10 alkanediyl, C 3-8 cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, —N(R 13 )— wherein R 13 is selected from the group consisting of hydrogen, linear C 1-10 alkyl, halogenated linear C 1-10 alkyl, branched C 4-10 alkyl, halogenated branched C 4-10 alkyl, C 3-8 cycloalkyl, phenyl and phenoxy, and moieties of formulas

wherein X is independently selected from hydrogen and halogen;

and oligomers, prepolymers, polymers or mixtures thereof;

and

(ii) a polyfunctional cyanate ester of formula (II)

wherein

n is an integer from 1 to 20; and R 10 and R 11 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C 1-10 alkyl and branched C 4-10 alkyl;

and oligomers, prepolymers, polymers or mixtures thereof;

and wherein

component (b) is one or more substituted bisimide compound independently selected from a compound of formula (X)

wherein * and ** each denotes a covalent bond to the respective C atom denoted with * and of a residue,

wherein the residues are identical or different and independently selected from

and wherein R is independently selected from C 7-8 cycloalkyl, C 2-10 alkyne or the moiety <<“N”—R—“N”>>, wherein “N” denotes the point of connectivity and <<“N”—R—“N”>> is an aromatic amine moiety independently selected from

wherein

“N” corresponds to N in formula (X), and

R 1 , R 2 , and R 3 are each independently selected from hydrogen, C 2 -C 20 alkyl, C 2 -C 20 alkene, C 2 -C 20 alkyne, halogen, NO 2 , and sulfone, wherein the halogen is selected from Cl, Br, F, or I;

and oligomers, prepolymers, polymers or mixtures of these compounds.

2. A composition according to claim 1 wherein component (a) is one or more cyanate esters independently selected from

(i) a difunctional cyanate ester compound of formula (I)

wherein

R 1 through R 8 are independently selected from the group consisting of hydrogen, linear C 1-10 alkyl, C 3-8 cycloalkyl;

Z 1 indicates a direct bond or a divalent moiety selected from the group consisting of —O—, —S—, —S(═O)—, —S(═O) 2 —, —CH 2 —, —CH(CH 3 )—, —C(CH 3 ) 2 —, —CH(CF 3 )—, —C(CF 3 ) 2 —, —C(═O)—, —C(═CH 2 )—, —C(═CCl 2 )—, —Si(CH 3 ) 2 —, linear C 1-10 alkanediyl, branched C 4-10 alkanediyl, C 3-8 cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, —N(R 13 )— wherein R 13 is selected from the group consisting of hydrogen, linear C 1-10 alkyl, C 3-8 cycloalkyl, phenyl and phenoxy, and moieties of formulas

wherein X is independently selected from hydrogen and halogen; and oligomers, prepolymers, polymers or mixtures thereof;

and

(ii) a polyfunctional cyanate ester of formula (II)

wherein

n is an integer from 1 to 20; and R 10 and R 11 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C 1-10 alkyl and branched C 4-10 alkyl; and oligomers, prepolymers, polymers or mixtures thereof.

3. A composition according to claim 1 wherein component (a) is one or more cyanate esters independently selected from

(i) a difunctional cyanate ester compound of formula (I)

wherein

R 1 through R 8 are independently selected from the group consisting of hydrogen, linear C 1-3 alkyl;

Z 1 indicates a direct bond or a divalent moiety selected from the group consisting of —O—, —S—, —S(═O) 2 —, —CH 2 —, —CH(CH 3 )—, —C(CH 3 ) 2 —, —C(CF 3 ) 2 —, —C(═CCl 2 )—, branched C 4-6 alkanediyl, C 3-8 cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene; and oligomers, prepolymers, polymers or mixtures thereof;

and

(ii) a polyfunctional cyanate ester of formula (II)

wherein

n is an integer from 1 to 10; and R 10 and R 11 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C 1-5 alkyl and branched C 4-6 alkyl, and oligomers, prepolymers, polymers or mixtures thereof.

4. A composition according to claim 1 wherein component (b) is one or more substituted bisimide independently selected from

b1) at least one selected from the group of biscitraconimide compound of formula (X1), bisitaconimide compound of formula (X2) and citraconimido-itaconimide compound of formula (X3),

or

b2) a bisnadicimide compound of formula (X4) and oligomers, prepolymers, polymers or mixtures thereof,

or

b3) a bistetrahydroimide compound of formula (X5) and oligomers, prepolymers, polymers or mixtures thereof

5. A composition according to claim 1 wherein component (a) is one or more cyanate esters independently selected from

(i) a difunctional cyanate ester compound of formula (I)

wherein the difunctional cyanate ester of formula I is independently selected from the group consisting of

(a) R 1 , R 2 , R 5 and R 6 are methyl, R 3 , R 4 , R 7 and R 8 are hydrogen and wherein Z 1 is —CH 2 —(methylene) and oligomers, prepolymers, polymers or mixtures thereof, or

(b) R 1 through R 8 are hydrogen and Z 1 is —C(CH 3 ) 2 — and oligomers, prepolymers, polymers or mixtures thereof, or

(c) R 1 through R 8 are hydrogen and Z 1 is —S— and oligomers, prepolymers, polymers or mixtures thereof, or

(d) R 1 through R 8 are hydrogen and Z 1 is —C(CF 3 ) 2 — and oligomers, prepolymers, polymers or mixtures thereof, or

(e) R 1 through R 8 are hydrogen and Z 1 is —C(═CCl 2 )— and oligomers, prepolymers, polymers or mixtures thereof, or

(f) R 1 through R 8 are hydrogen and Z 1 is independently selected from the group consisting of

and oligomers, prepolymers, polymers or mixtures thereof, or

(g) R 1 through R 8 are hydrogen and Z 1 is

and oligomers, prepolymers, polymers or mixtures thereof, or

(h) R 1 through R 8 are hydrogen and Z 1 is —CH(CH 3 )— and oligomers, prepolymers, polymers or mixtures thereof,

and oligomers, prepolymers, polymers or mixtures thereof;

and/or

ii) a polyfunctional cyanate ester of formula (II)

wherein the polyfunctional cyanate ester is independently selected from the group consisting of compound III of formula

compound IV of formula

compound V of formula

compound VI of formula

and

oligomers, prepolymers, polymers or mixtures thereof.

6. A composition according to claim 1 wherein the ratio of component (a) to (b) is 80 wt % component (a) to 20 wt % component (b) based on total amount of the resin composition.

7. A composition according to claim 1 wherein component (a) is one or more cyanate esters independently selected from

(i) a difunctional cyanate ester compound of formula (I)

wherein R 1 through R 8 are hydrogen and Z 1 is —CH(CH 3 )— and oligomers, prepolymers, polymers or mixtures thereof;

and

(ii) a polyfunctional cyanate ester of formula (II)

wherein the polyfunctional cyanate ester is independently selected from the group consisting of compound III, compound IV, compound V, and oligomers, prepolymers, polymers or mixtures thereof;

and wherein component (b) is a biscitraconimide compound of formula (X1),

wherein R is

 and “N” corresponds to N in formula (X1),

and oligomers, prepolymers, polymers or mixtures thereof.

8. A method for the preparation of a composition according to claim 1 comprising the steps of:

i) providing a mixture components according to claim 1 ; and

ii) intimately mixing the components together.

9. A composition according to claim 1 wherein the composition further comprises a catalyst selected from the group consisting of aliphatic mono-, di- and polyamines, aromatic mono-, di- and polyamines, carbocyclic mono-, di and polyamines, heterocyclic mono-, di- and polyamines, compounds containing a five- or six-membered nitrogen-containing heterocyclic ring, hydroxyamines, phosphines, phenols, and mixtures thereof.

10. A composition according to claim 1 wherein the composition further comprises reinforcement fibres selected from the group consisting of carbon fibres, glass fibres, aramid fibres, basalt fibres, natural fibres, fleeces and woven fabrics, and mixtures thereof.

11. A composition according to claim 1 wherein the composition further comprise a filler selected from the group consisting of organic fillers, inorganic fillers, mineral powder fillers, and mixtures thereof.

12. A composition according to claim 1 wherein the composition further comprise a filler selected from the group consisting of thermoplastics, elastomers, silica, CaCO 3 , coated CaCO 3 , kaolin clay, talc, graphite, corundum, wollastonite, SiC, glass microspheres, mica, calcium silicate, MgO, anhydrous calcium sulfate, ceramic hollow microspheres, fused mullite, boron nitride, vermiculite, basalt, and mixtures thereof.

13. A method for the preparation of a thermoset composite material comprising the steps of:

i) providing a mixture components according to claim 1 ;

ii) intimately mixing the components together;

iii) casting the mixture into the desired form; and

iv) initiating polymerization of the mixture.

14. A method for producing a thermoset composite material comprising a composition as defined in claim 1 .

15. A composition comprising components (a) and (b) wherein component (a) is one or more cyanate esters independently selected from

(i) a difunctional cyanate ester compound of formula (I)

wherein

R 1 through R 8 are independently selected from the group consisting of hydrogen, linear C 1-10 alkyl, halogenated linear C 1-10 alkyl, branched C 4-10 alkyl, halogenated branched C 4-10 alkyl, C 3-8 cycloalkyl, halogenated C 3-8 cycloalkyl, C 1-10 alkoxy, halogen, phenyl and phenoxy;

Z 1 indicates a direct bond or a divalent moiety selected from the group consisting of —O—, —S—, —S(═O)—, —S(═O) 2 —, —CH 2 —, —CH(CH 3 )—, —C(CH 3 ) 2 —, —CH(CF 3 )—, —C(CF 3 ) 2 —, —C(═O)—, —C(═CH 2 )—, —C(═CCl 2 )—, —Si(CH 3 ) 2 —, linear C 1-10 alkanediyl, branched C 4-10 alkanediyl, C 3-8 cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, —N(R 13 )— wherein R 13 is selected from the group consisting of hydrogen, linear C 1-10 alkyl, halogenated linear C 1-10 alkyl, branched C 4-10 alkyl, halogenated branched C 4-10 alkyl, C 3-8 cycloalkyl, phenyl and phenoxy, and moieties of formulas

wherein X is independently selected from hydrogen and halogen;

and oligomers, prepolymers, polymers or mixtures thereof;

and

(ii) a polyfunctional cyanate ester of formula (II)

wherein

n is an integer from 1 to 20; and R 10 and R 11 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C 1-10 alkyl and branched C 4-10 alkyl;

and oligomers, prepolymers, polymers or mixtures thereof;

wherein component (b) is one or more substituted bisimide independently selected from

b1) at least one selected from the group of biscitraconimide compound of formula (X1), bisitaconimide compound of formula (X2) and citraconimido-itaconimide compound of formula (X3),

or

b2) a bisnadicimide compound of formula (X4) and oligomers, prepolymers, polymers or mixtures thereof,

or

b3) a bistetrahydroimide compound of formula (X5) and oligomers, prepolymers, polymers or mixtures thereof

wherein R is the moiety << “N”—R—“N”>>, wherein “N” denotes the point of connectivity and R is an aromatic amine moiety independently selected from

wherein

R 1 , R 2 , and R 3 are each independently selected from hydrogen, C 1 -C 5 alkyl, halogen, NO 2 , and sulfone, wherein the halogen is selected from Cl, Br or F;

and oligomers, prepolymers, polymers or mixtures thereof.

16. A composition comprising components (a) and (b) wherein component (a) is one or more cyanate esters independently selected from

(i) a difunctional cyanate ester compound of formula (I)

wherein

R 1 through R 8 are independently selected from the group consisting of hydrogen, linear C 1-10 alkyl, halogenated linear C 1-10 alkyl, branched C 4-10 alkyl, halogenated branched C 4-10 alkyl, C 3-8 cycloalkyl, halogenated C 3-8 cycloalkyl, C 1-10 alkoxy, halogen, phenyl and phenoxy;

Z 1 indicates a direct bond or a divalent moiety selected from the group consisting of —O—, —S—, —S(═O)—, —S(═O) 2 —, —CH 2 —, —CH(CH 3 )—, —C(CH 3 ) 2 —, —CH(CF 3 )—, —C(CF 3 ) 2 —, —C(═O)—, —C(═CH 2 )—, —C(═CCl 2 )—, —Si(CH 3 ) 2 —, linear C 1-10 alkanediyl, branched C 4-10 alkanediyl, C 3-8 cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, —N(R 13 )— wherein R 13 is selected from the group consisting of hydrogen, linear C 1-10 alkyl, halogenated linear C 1-10 alkyl, branched C 4-10 alkyl, halogenated branched C 4-10 alkyl, C 3-8 cycloalkyl, phenyl and phenoxy, and moieties of formulas

wherein X is independently selected from hydrogen and halogen; and oligomers, prepolymers, polymers or mixtures thereof;

and

(ii) a polyfunctional cyanate ester of formula (II)

wherein

n is an integer from 1 to 20; and R 10 and R 11 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C 1-10 alkyl and branched C 4-10 alkyl; and oligomers, prepolymers, polymers or mixtures thereof;

and wherein

component (b) is one or more substituted bisimide independently selected from

b1) at least one selected from the group of biscitraconimide compound of formula (X1), bisitaconimide compound of formula (X2) and citraconimido-itaconimide compound of formula (X3), and oligomers, prepolymers, polymers or mixtures thereof,

or

b2) a bisnadicimide compound of formula (X4) and oligomers, prepolymers, polymers or mixtures thereof,

or

b3) a bistetrahydroimide compound of formula (X5) and oligomers, prepolymers, polymers or mixtures thereof,

wherein R is o-xylylene; and oligomers, prepolymers, polymers or mixtures thereof.