Novel Compositions with Improved Characteristics

Abstract

The present invention relates to novel compositions comprising cyanate ester resins and substituted bisimides (citracon-imides, bisitaconimide, citraconimido-itaconimide, bisnadicimide, bistetrahydroimide and mixtures thereof) as defined in claim 1, and thermoset composite materials based on these compositions.

Claims

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) ##STR00278## wherein R.sup.1 through R.sup.8 are independently selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, halogenated linear C.sub.1-10 alkyl, branched C.sub.4-10 alkyl, halogenated branched C.sub.4-10 alkyl, C.sub.3-8 cycloalkyl, halogenated C.sub.3-8 cycloalkyl, linear C.sub.2-C.sub.10 alkenyl, branched C.sub.3-C.sub.10 alkenyl, C.sub.1-10 alkoxy, halogen, phenyl and phenoxy, wherein at least one of R.sup.1 to R.sup.8 is selected from the group consisting of linear C.sub.2-C.sub.10 alkenyl and branched C.sub.3-C.sub.10 alkenyl; Z.sup.1 indicates a direct bond or a divalent moiety selected from the group consisting of O, S, S(O), S(O).sub.2, CH.sub.2, CH(CH.sub.3), C(CH.sub.3).sub.2, CH(CF.sub.3), C(CF.sub.3).sub.2, C(O), C(CH.sub.2), C(CCl.sub.2), Si(CH.sub.3).sub.2, linear C.sub.1-10 alkanediyl, branched C.sub.4-10 alkanediyl, C.sub.3-8 cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, N(R.sup.13) wherein R.sup.13 is selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, halogenated linear C.sub.1-10 alkyl, branched C.sub.4-10 alkyl, halogenated branched C.sub.4-10 alkyl, C.sub.3-8 cycloalkyl, phenyl and phenoxy, and moieties of formulas ##STR00279## wherein X is independently selected from hydrogen and halogen; and oligomers, prepolymers, polymers or mixtures thereof; or wherein (a) is a mixture of (i) and (ii), wherein (ii) is a polyfunctional cyanate ester of formula (II) ##STR00280## wherein n is an integer from 1 to 20; and R.sup.10 and R.sup.11 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, branched C.sub.4-10 alkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl; and oligomers, prepolymers, polymers or mixtures thereof; or a polyfunctional cyanate ester of formula (IX-1) ##STR00281## wherein n is an integer from 1 to 20; and R.sup.30, R.sup.31, R.sup.32 and R.sup.33 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, branched C.sub.3-10 alkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl; and oligomers, prepolymers, polymers or mixtures thereof; or a polyfunctional cyanate ester of formula (IX-2) ##STR00282## wherein n is an integer from 1 to 20; and R.sup.34, R.sup.35 and R.sup.36 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, branched C.sub.3-10 alkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl; and oligomers, prepolymers, polymers or mixtures thereof; or a polyfunctional cyanate ester of formula (IX-3) ##STR00283## wherein n is an integer from 1 to 20; and R.sup.37 is selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, branched C.sub.3-10 alkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl; and oligomers, prepolymers, polymers or mixtures thereof; or a polyfunctional cyanate ester of formula (IX-4) ##STR00284## wherein n is an integer from 1 to 20; and oligomers, prepolymers, polymers or mixtures thereof; or any combination of polyfunctional cyanate esters of formulas (II), (IX-1), (IX-2), (IX-3), and (IX-4); and wherein component (b) is one or more substituted bisimide compound selected from the group consisting of biscitraconimide compound of formula (X1), bisitaconimide compound of formula (X2), and citraconimido-itaconimide compound of formula (X3) ##STR00285## wherein R is m-xylylene; and oligomers, prepolymers, polymers or mixtures thereof; wherein the ratio of component (a) to (b) is in the range of from 10-70 wt.-% component (a) to 90-30 wt.-% component (b) based on total amount of the resin composition.

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) ##STR00286## wherein R.sup.1 through R.sup.8 are independently selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, C.sub.3-8 cycloalkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl, wherein at least one of R.sup.1 to R.sup.8 is selected from the group consisting of linear C.sub.2-C.sub.10 alkenyl and branched C.sub.3-C.sub.10 alkenyl; Z.sup.1 indicates a direct bond or a divalent moiety selected from the group consisting of O, S, S(O), S(O).sub.2, CH.sub.2, CH(CH.sub.3), C(CH.sub.3).sub.2, CH(CF.sub.3), C(CF.sub.3).sub.2, C(O), C(CH.sub.2), C(CCl.sub.2), Si(CH.sub.3).sub.2, linear C.sub.1-10 alkanediyl, branched C.sub.10 alkanediyl, C.sub.3-8 cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, N(R.sup.13) wherein R.sup.13 is selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, C.sub.3-8 cycloalkyl, phenyl and phenoxy, and moieties of formulas ##STR00287## wherein X is independently selected from hydrogen and halogen; and oligomers, prepolymers, polymers or mixtures thereof; or wherein (a) is a mixture of (i) and (ii), wherein (ii) is a polyfunctional cyanate ester of formula (II) ##STR00288## wherein n is an integer from 1 to 20; and R.sup.10 and R.sup.11 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, branched C.sub.4-10 alkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl; and oligomers, prepolymers, polymers or mixtures thereof; or a polyfunctional cyanate ester of formula (IX-1) ##STR00289## wherein n is an integer from 1 to 20; and R.sup.30, R.sup.31, R.sup.32 and R.sup.33 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, branched C.sub.3-10 alkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl; and oligomers, prepolymers, polymers or mixtures thereof; or a polyfunctional cyanate ester of formula (IX-2) ##STR00290## wherein n is an integer from 1 to 20; and R.sup.34, R.sup.35 and R.sup.36 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, branched C.sub.3-10 alkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl; and oligomers, prepolymers, polymers or mixtures thereof; or a polyfunctional cyanate ester of formula (IX-3) ##STR00291## wherein n is an integer from 1 to 20; and R.sup.37 is selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, branched C.sub.3-10 alkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl; and oligomers, prepolymers, polymers or mixtures thereof; or a polyfunctional cyanate ester of formula (IX-4) ##STR00292## wherein n is an integer from 1 to 20; and oligomers, prepolymers, polymers or mixtures thereof; or any combination of polyfunctional cyanate esters of formulas (II), (IX-1), (IX-2), (IX-3), and (IX-4).

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) ##STR00293## wherein R.sup.1 through R.sup.8 are independently selected from the group consisting of hydrogen, linear C.sub.1-3 alkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl, wherein at least one of R.sup.1 to R.sup.8 is selected from the group consisting of linear C.sub.2-C.sub.10 alkenyl and branched C.sub.3-C.sub.10 alkenyl; Z.sup.1 indicates a direct bond or a divalent moiety selected from the group consisting of O, S, S(O).sub.2, CH.sub.2, CH(CH.sub.3), C(CH.sub.3).sub.2, C(CF.sub.3).sub.2, C(CCl.sub.2), branched C.sub.4-6 alkanediyl, C.sub.3-8 cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene; and oligomers, prepolymers, polymers or mixtures thereof; or wherein (a) is a mixture of (i) and (ii) wherein (ii) is a polyfunctional cyanate ester of formula (II) ##STR00294## wherein n is an integer from 1 to 10; and R.sup.10 and R.sup.11 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C.sub.1-5 alkyl, branched C.sub.4-6 alkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl; and oligomers, prepolymers, polymers or mixtures thereof; or a polyfunctional cyanate ester of formula (IX-1) ##STR00295## wherein n is an integer from 1 to 20; and R.sup.30, R.sup.31, R.sup.32 and R.sup.33 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, branched C.sub.3-10 alkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl; and oligomers, prepolymers, polymers or mixtures thereof; or a polyfunctional cyanate ester of formula (IX-2) ##STR00296## wherein n is an integer from 1 to 20; and R.sup.34, R.sup.35 and R.sup.36 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, branched C.sub.3-10 alkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl; and oligomers, prepolymers, polymers or mixtures thereof; or a polyfunctional cyanate ester of formula (IX-3) ##STR00297## wherein n is an integer from 1 to 20; and R.sup.37 is selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, branched C.sub.3-10 alkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl; and oligomers, prepolymers, polymers or mixtures thereof; or a polyfunctional cyanate ester of formula (IX-4) ##STR00298## wherein n is an integer from 1 to 20; and oligomers, prepolymers, polymers or mixtures thereof; or any combination of polyfunctional cyanate esters of formulas (II), (IX-1), (IX-2), (IX-3), and (IX-4).

4. 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) ##STR00299## wherein the difunctional cyanate ester of formula I is independently selected from the group consisting of i) R.sup.1 and R.sup.5 are allyl, R.sup.2 and R.sup.6 are methyl, R.sup.3, R.sup.4, R.sup.7 and R.sup.8 are hydrogen and wherein Z.sup.1 is CH.sub.2 (methylene); ii) R.sup.1 and R.sup.5 are allyl and R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7 and R.sup.8 are hydrogen and wherein Z.sup.1 is CH.sub.2 (methylene); iii) R.sup.1 and R.sup.5 are allyl and R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7 and R.sup.8 are hydrogen and wherein Z.sup.1 is C(CH.sub.3).sub.2; iv) R.sup.1 and R.sup.5 are allyl and R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7 and R.sup.8 are hydrogen and Z.sup.1 is C(O); v) R.sup.1 and R.sup.5 are allyl and R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7 and R.sup.8 are hydrogen and Z.sup.1 is S(O); vi) R.sup.1 and R.sup.5 are allyl and R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7 and R.sup.8 are hydrogen and Z.sup.1 is S; vii) R.sup.1 and R.sup.5 are allyl and R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7 and R.sup.8 are hydrogen and Z.sup.1 is C(CF.sub.3).sub.2; viii) R.sup.1 and R.sup.5 are allyl and R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7 and R.sup.8 are hydrogen and Z.sup.1 is C(CCl.sub.2); ix) R.sup.1 and R.sup.5 are allyl and R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7 and R.sup.8 are hydrogen and Z.sup.1 is independently selected from the group consisting of ##STR00300## x) R.sup.1 and R.sup.5 are allyl and R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7 and R.sup.8 are hydrogen and Z.sup.1 is ##STR00301## or xi) R.sup.1 and R.sup.5 are allyl and R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7 and R.sup.8 are hydrogen and Z.sup.1 is CH(CH.sub.3); and oligomers, prepolymers, polymers or mixtures thereof, or wherein (a) is a mixture of (i) and (ii), wherein (ii) is a polyfunctional cyanate ester of formula (II) ##STR00302## wherein the polyfunctional cyanate ester is independently selected from the group consisting of compound III, compound IV, compound V, compound VI, and oligomers, prepolymers, polymers or mixtures thereof ##STR00303## a polyfunctional cyanate ester of formula (IX-1) ##STR00304## wherein n is an integer from 1 to 20; and R.sup.30, R.sup.31, R.sup.32 and R.sup.33 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, branched C.sub.3-10 alkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl; and oligomers, prepolymers, polymers or mixtures thereof; or a polyfunctional cyanate ester of formula (IX-2) ##STR00305## wherein n is an integer from 1 to 20; and R.sup.34, R.sup.35 and R.sup.36 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, branched C.sub.3-10 alkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl; and oligomers, prepolymers, polymers or mixtures thereof; or a polyfunctional cyanate ester of formula (IX-3) ##STR00306## wherein n is an integer from 1 to 20; and R.sup.37 is selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, branched C.sub.3-10 alkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl; and oligomers, prepolymers, polymers or mixtures thereof; or a polyfunctional cyanate ester of formula (IX-4) ##STR00307## wherein n is an integer from 1 to 20; and oligomers, prepolymers, polymers or mixtures thereof; or any combination of polyfunctional cyanate esters of formulas (II), (IX-1), (IX-2), (IX-3), and (IX-4).

5. A composition according to claim 1, wherein the ratio of component (a) to (b) is in the range of from 20-70 wt.-% component (a) to 80-30 wt.-% component (b) based on total amount of the resin composition.

6. 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, bisphenols, and mixtures thereof.

7. A composition according to claim 6, wherein the catalyst is a compound of formula (VII) ##STR00308## wherein R.sup.1 through R.sup.8 are independently selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, linear C.sub.2-C.sub.10 alkenyl, halogenated linear C.sub.1-10 alkyl, branched C.sub.4-10 alkyl, branched C.sub.3-C.sub.10 alkenyl, halogenated branched C.sub.4-10 alkyl, C.sub.3-8 cycloalkyl, halogenated C.sub.3-8 cycloalkyl, C.sub.1-10 alkoxy, halogen, phenyl and phenoxy, wherein at least one of R.sup.1 to R.sup.8 is selected from the group consisting of linear C.sub.2-C.sub.10 alkenyl and branched C.sub.3-C.sub.10 alkenyl; Z indicates a direct bond or a divalent moiety selected from the group consisting of O, S, S(O), S(O).sub.2, CH.sub.2, CH(CH.sub.3), C(CH.sub.3).sub.2, CH(CF.sub.3), C(CF.sub.3).sub.2, C(O), C(CH.sub.2), C(CCl.sub.2), Si(CH.sub.3).sub.2, linear C.sub.1-10 alkanediyl, branched C.sub.4-10 alkanediyl, C.sub.3-8 cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, N(R.sup.13) wherein R.sup.13 is selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, halogenated linear C.sub.1-10 alkyl, branched C.sub.4-10 alkyl, halogenated branched C.sub.4-10 alkyl, C.sub.3-8 cycloalkyl, phenyl and phenoxy, and moieties of formulas ##STR00309## wherein X is independently selected from hydrogen and halogen; and oligomers, prepolymers, polymers or mixtures thereof.

8. A composition according to claim 6, wherein the catalyst is present in an amount of about 0.01 to 20 wt.-% based on the total amount of the resin composition.

9. A composition according to claim 1, wherein the composition further comprises reinforcement fibres selected from the group consisting of carbon fibres, glass fibres (such as E glass fibres, S glass fibres), aramid fibres (including KEVLAR), basalt fibres (geotextile fibers), natural fibres (such as flax, hemp, jute or sisal), fleeces and woven fabrics (multi-layered or single layered), and mixtures thereof.

10. A composition according to claim 1, wherein the composition further comprises a filler selected from the group consisting of organic fillers, such as thermoplastics and elastomers, inorganic fillers, wherein the inorganic filler is selected from glass microspheres, graphite, graphene/nano-graphen, carbon nanotubes (SWCNT and/or MWCNT) or silica, and mineral powder fillers, such as CaCO.sub.3, coated CaCO.sub.3, kaolin clay, SiO.sub.2, talc, graphite, corundum (-Al.sub.2O.sub.3), wollastonite, SiC, glass microspheres, mica, calcium silicate (Ca.sub.2O.sub.4Si), MgO, anhydrous calcium sulfate (CaSO.sub.4 or anhydrite), ceramic hollow microspheres, fused mullite (Al.sub.2O.sub.3SiO.sub.2), boron nitride (BN), vermiculite, or basalt, and mixtures thereof.

11. 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) ##STR00310## wherein R.sup.1 through R.sup.8 are independently selected from the group consisting of hydrogen, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl, wherein at least one of R.sup.1 to R.sup.8 is selected from the group of consisting of linear C.sub.2-C.sub.10 alkenyl and branched C.sub.3-C.sub.10 alkenyl, preferably wherein R.sup.1 and R.sup.5 are each independently linear C.sub.2-C.sub.10 alkenyl or branched C.sub.3-C.sub.10 alkenyl and R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7 and R.sup.8 are hydrogen, even more preferably wherein R.sup.1 and R.sup.5 are allyl and R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7 and R.sup.8 are hydrogen; and Z.sup.1 is C(CH.sub.3).sub.2 and oligomers, prepolymers, polymers or mixtures thereof; or wherein (a) is a mixture of (i) and (ii), wherein (ii) is a polyfunctional cyanate ester of formula (II) ##STR00311## 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; ##STR00312## or a polyfunctional cyanate ester of formula (IX-1) ##STR00313## wherein n is an integer from 1 to 20; and R.sup.30, R.sup.31, R.sup.32 and R.sup.33 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, branched C.sub.3-10 alkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl; and oligomers, prepolymers, polymers or mixtures thereof; or a polyfunctional cyanate ester of formula (IX-2) ##STR00314## wherein n is an integer from 1 to 20; and R.sup.34, R.sup.35 and R.sup.36 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, branched C.sub.3-10 alkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl; and oligomers, prepolymers, polymers or mixtures thereof; or a polyfunctional cyanate ester of formula (IX-3) ##STR00315## wherein n is an integer from 1 to 20; and R.sup.37 is selected from the group consisting of hydrogen, linear C.sub.1-10 alkyl, branched C.sub.3-10 alkyl, linear C.sub.2-C.sub.10 alkenyl, and branched C.sub.3-C.sub.10 alkenyl; and oligomers, prepolymers, polymers or mixtures thereof; or a polyfunctional cyanate ester of formula (IX-4) ##STR00316## wherein n is an integer from 1 to 20; and oligomers, prepolymers, polymers or mixtures thereof; or any combination of polyfunctional cyanate esters of formulas (II), (IX-1), (IX-2), (IX-3), and (IX-4); and wherein component (b) is a biscitraconimide compound of formula (X1) ##STR00317## wherein R is m-xylylene; and oligomers, prepolymers, polymers or mixtures thereof.

12. A method for the preparation of a composition according to claim 1, comprising: i) providing a mixture components according to any one of claims 1-11; and ii) intimately mixing the components together.

13. A method for the preparation of a thermoset composite material, comprising: i) providing a mixture components according to claim 1; ii) intimately mixing the components together; iii) providing fibres, fillers, pigments and/or additives; iv) contacting the mixture obtained in step ii) with the fibres, fillers, pigments and/or additives; v) optionally casting the mixture into the desired form; and vi) initiating polymerization of the mixture.

14. Use of a composition as defined in claim 1 for producing a thermoset composite material.

15. A thermoset composite material obtained by the method according to claim 13, wherein the thermoset composite material exhibits a mass loss after 1000 h at 250 C. of less than about 2.5 wt.-%, preferably of less than about 2.0 wt.-%, more preferably of less than about 1.75 wt.-%.

Description

EXAMPLES

Abbreviations

TABLE-US-00001 TMA Thermal mechanical analysis RT Room temperature Tg Glass transition temperature

Materials

TABLE-US-00002 Perkalink 1,3-bis(citraconimidomethyl)benzene, CAS 119462-56-5 DABA-CN Primaset CL-100/DABA-CN Propane-2,2- diylbis-2-(prop-2-en-1-yl)benzene-4,1-diyl dicyanate -from Arxada AG, Switzerland. CAS: 126791-29-5.

Experimental Procedure for Comparative Example 1

[1061] 6 g of DABA-CN was poured at RT into an aluminum pan with a diameter of 5 cm and subsequently cured according to the following cure cycle: [1062] Cure cycle: heat-up from 25 C. to 175 C. at 1K/min, hold 3 h at 175 C. [1063] heat-up from 175 C. to 220 C. at 1K/min, hold 2 h at 220 C. [1064] heat-up from 220 C. to 260 C. at 1K/min, hold 16 h at 260 C.

[1065] The cured DABA-CN material was cooled to RT and was removed from the aluminum pan (de-molded). The cured material was evaluated in term of mass loss (thermal-oxidative stability) and glass transition temperature.

[1066] The cured material had the following dimensions: diameter=5 cm, thickness=2 cm.

Experimental Procedure for Examples 2, 3 and 4

[1067] DABA-CN and Perkalink were mixed at 90-100 C. until complete homogenization and 6 g of said mixture was poured into an aluminum pan with a diameter of 5 cm and subsequently cured according to the following cure cycle: [1068] Cure cycle: heat-up from 25 C. to 175 C. at 1K/min, hold 3 h at 175 C. [1069] heat-up from 175 C. to 220 C. at 1K/min, hold 2 h at 220 C. [1070] heat-up from 220 C. to 260 C. at 1K/min, hold 16 h at 260 C.

[1071] The cured material was cooled to RT and was removed from the aluminum pan (de-molded). The cured material was evaluated in term of mass loss (thermal-oxidative stability) and glass transition temperature.

[1072] The cured material had the following dimensions: diameter=5 cm, thickness=2 cm.

[1073] The components and their amounts in gram (g) and wt.-% (% based on the total weight of the mixture) used in Comparative Example 1 and Examples 2, 3 and 4 are given in Table 1 (g) and Table 2 (wt.-%).

TABLE-US-00003 TABLE 1 Components and their amounts in gram (g) for Comparative Example 1 and Examples 2 to 4. Comp. Ex. 1 Example 2 Example 3 Example 4 Perkalink 7.5 5.0 2.5 DABA-CN 10 2.5 5.0 7.5 Total gram 10 10 10 20

TABLE-US-00004 TABLE 2 Components and their amounts in wt.-% based on the total weight of the mixture for Comparative Example 1 and Examples 2 to 4. Example Comp. Ex. 1 Example 2 Example 3 Example 4 Perkalink 75 50 25 DABA-CN 100 25 50 75 Total wt.-% 100 100 100 100

Experimental Procedure for Testing the Cured Samples of Comparative Example 1 and Examples 2, 3, and 4

Thermal Oxidative Stability:

[1074] The thermal oxidative stability of above cured samples was evaluated based upon weight loss during isothermal aging at 250 C. The cured samples (diameter 5 cm and thickness of 2 cm) were placed in an oven at 250 C. for a long term aging test. The initial weight (w.sub.0) of the cured samples was measured with an analytical balance having a resolution of at least 0.1 mg before starting aging test. Then the weight of the samples was re-measured (w.sub.xhours) after different thermal aging periods at 250 C. The correspondent mass loss in % was calculated using the following formula:

[00001]$\mathrm{Mass}\mathrm{Loss}\left[\%\right]=\left(\left(w_0-w_{\mathrm{xhours}}\right)/w_0\right)100$

[1075] The samples were then re-placed in the oven at 250 C. for continuing the aging test. The weight loss results are given in Table 3.

Glass Transition Temperature:

[1076] In addition to thermal oxidative stability testing, samples of the cured composition obtained after the curing cycle defined above for Comparative Example 1 and Examples 2, 3, and 4 were cut to specimens and the glass transition temperature (Tg) was analysed by Thermal Mechanical Analysis (TMA).

[1077] Glass transition temperature is the temperature at which the physical properties of a polymeric materials change from amorphous rigid, glassy or crystalline state to a flexible rubbery state. The machine used was a Mettler Toledo instrument TMA SDTA840. The sample dimensions were 66 mm.sup.2 (lengthwidth) and 2.0 mm thickness. The test method applied two heating ramps (1.sup.st heat-up: 25-250 C. at 10 K/min, 2.sup.nd heat-up: 25-400 C. at 10 K/min). The Tg was evaluated on the second ramp. The result are given in Table 3.

TABLE-US-00005 TABLE 3 Mass loss and Tg onset for Comparative Example 1 and Examples 2, 3, and 4 mass loss mass loss mass loss 500 h 1000 h 3000 h T.sub.g at 250 C. at 250 C. at 250 C. onset by [%] [%] [%] TMA [ C.] Comp. Ex. 1 **NR 2.19 **NR >240 Example 2 **NR 1.54 **NR >240 Example 3 **NR 1.95 **NR >240 Example 4 **NR **NR **NR >240 **NR = not recorded