Novel compositions with improved characteristics

Abstract

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

Description

[Technical Field]

[0001] The present invention relates to novel compositions comprising cyanate ester resins and substituted bisimides (citraconimides, bisitaconimides, citraconic-itaconimides, bisnadicimides, bistetrahydroimides and mixtures thereof), and to thermoset composites based on these compositions. [Background technology]

[0002] Thermoset composite matrices are typically based on polyesters, vinyl esters, epoxies, bismaleimides, cyanate esters, polyimides, and phenolics.

[0003] CA2464339A1, US3553244, US3755402, US3740348 and US4578439, as well as EP1190184, EP1195764, US9263360, EP327926, EP1566377, EP2722363 disclose cyanate ester composites that can be used in compression molding, printed wiring boards, prepreg resins, composite sheets, and metal fol-clad laminate plates.

[0004] US20120049106, US7271227B1, US5198515 and US4568733, RSC Adv., 2017, 7, 23149 disclose bismaleimide composites that can be used to make laminates and prepregs by curing the compositions into polymers.

[0005] US2009 / 0110938A1 discloses a cyanate ester resin composition for printed wiring board materials, which contains a cyanate ester resin component A and / or its oligomer and at least one component B selected from the group consisting of epoxy resins and unsubstituted bismaleimide compounds. These bismaleimides are not well suited for high temperature applications due to their high mass loss at high temperatures in long-term stability tests (see Table 2).

[0006] US2014199549A1 discloses a thermosetting resin composition for electronic packaging devices, comprising a hydrophobic solid bismaleimide, a benzoxazine monomer, and an epoxy anhydride or epoxy phenol novolac or epoxy cresol novolac anhydride adduct. As noted in the examples, bismaleimide is not particularly suitable for high-temperature applications due to its high mass loss at high temperatures. Furthermore, benzoxazine and cyanate esters are known to have different curing mechanisms, leading to different network structures and performance.

[0007] However, many of the current thermoset composites based on bismaleimide compounds have limitations or disadvantages that limit their use as thermosets in high temperature applications and easy processing. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] CA2464339A1 [Patent Document 2] US3553244 [Patent Document 3] US3755402 [Patent Document 4] US3740348 [Patent Document 5] US4578439 [Patent Document 6] EP1190184 [Patent Document 7] EP1195764 [Patent Document 8] US9263360 [Patent Document 9] EP327926 [Patent Document 10] EP1566377 [Patent Document 11] EP2722363 [Patent Document 12] US20120049106 [Patent Document 13] US7271227B1 [Patent Document 14] US5198515 [Patent Document 15] US4568733 [Patent Document 16] US2009 / 0110938A1 [Patent Document 17] US2014199549A1 [Non-patent literature]

[0009] [Non-Patent Document 1] RSC Adv., 2017, 7, 23149 Summary of the Invention [Problem to be solved by the invention]

[0010] Therefore, there remains a need for new thermoset composite materials with improved properties. [Means for solving the problem]

[0011] Therefore, the present invention provides: providing a composition comprising components (a) and (b); Component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0012] [ka]

[0013] (In the formula, R 1 ~R 8 are independently hydrogen, straight chain C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl, and phenoxy; R 1 ~R 8 At least one of the following is a straight chain C2 to C 10 Alkenyl and branched C3-C 10 alkenyl; Z 1 indicates a direct bond or -O-, -S-, -S(=O)-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, CH(CF3)-, -C(CF3)2-, -C(=O)-, -C(=CH2)-, -C(=CCl2)-, -Si(CH3)2-, straight chain C 1~10 Alkanediyl, branched chain C 4~10 Alkanediyl, C 3~8 Cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, -N(R 13 )-(wherein, R 13 is hydrogen, linear C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, phenyl and phenoxy, and moieties of formula

[0014] [ka]

[0015] wherein X represents a divalent moiety selected from the group consisting of: (a) is a mixture of (i) and (ii), (ii) is a polyfunctional cyanate ester of formula (II)

[0016] [ka]

[0017] (wherein n is an integer of 1 to 20; R 10 and R 11 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-1)

[0018] [ka]

[0019] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0020] [ka]

[0021] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0022] [ka]

[0023] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0024] [ka]

[0025] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers, or mixtures thereof; or Any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4) and Component (b) is a compound of formula (X)

[0026] [ka]

[0027] (wherein * and ** respectively indicate a covalent bond to the respective C atom of the residue indicated by * and **, The residues may be the same or different,

[0028] [ka]

[0029] are independently selected from R is independently selected from alkyl, cycloalkyl, alkyne, aryl, aralkyl, and alkaryl; Ra, Rb, and Rc are independently hydrogen, straight chain C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl and phenoxy; or Ra and Rb, Ra and Rc, or Rb and Rc may together form a 3- to 8-membered cycloalkyl or 3- to 8-membered cycloalkenyl), and an oligomer, prepolymer, polymer, or mixture of these compounds. and one or more substituted bisimide compounds independently selected from:

[0030] The term "halogen" refers to fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine.

[0031] The term "substituted bisimide" refers to compounds having substituents on the CC double bond (3 and / or 4 positions) of the maleimide group.

[0032] Alkyl substituents (either alone or as part of a larger group such as an alkoxy group) may be straight-chained or branched. Alkyl, either alone or as part of another substituent, is, depending on the number of carbon atoms referred to, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, and their isomers, such as isopropyl, isobutyl, sec-butyl, tert-butyl, or isoamyl.

[0033] Alkenyl substituents (either alone or as part of a larger group such as alkenyloxy) may be in the form of straight or branched chains, and the alkenyl moiety, as appropriate, may be in either the (E)- or (Z)-configuration.

[0034] Alkynyl substituents (either alone or as part of a larger group such as alkynyloxy) may be in the form of straight or branched chains.

[0035] An aryl group (either alone or as part of a larger group, e.g., aryloxy, aryl-alkyl, etc.) is an aromatic ring system, which may be in the form of mono-, bi-, or tricyclic rings. Examples of such rings include phenyl, naphthyl, anthracenyl, indenyl, or phenanthrenyl. Preferred aryl groups are phenyl and naphthyl, with phenyl being most preferred.

[0036] The term "linear C 1~10"Alkyl" refers to a straight chain saturated hydrocarbon group having from 1 to 10 carbon atoms, examples of which include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl.

[0037] The term "branched chain C 4~10 "Alkyl" refers to a branched chain saturated hydrocarbon group having 4 to 10 carbon atoms, examples of which include butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl.

[0038] The term "straight chain C2-C 10 "Alkenyl" refers to a straight-chain group having one or more double bonds, where the alkenyl moiety may, as appropriate, be in either the (E)- or (Z)-configuration. 10 Examples of "alkenyl" groups include vinyl, allyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, and octenyl.

[0039] The term "branched chain C3-C 10 "Alkenyl" refers to a branched group having one or more double bonds, where the alkenyl moiety may be in either the (E)- or (Z)-configuration, as appropriate. The branching site may be at either an unsaturated or saturated carbon atom. "Branched chain C3-C 10Examples of "alkenyl" groups include isopropenyl, sec-butenyl, tert-butenyl, isopentenyl, and isohexenyl.

[0040] The term "3- to 8-membered cycloalkyl" or "C 3~8 "Cycloalkyl" refers to a saturated carbocyclic compound which may contain one or more rings. "3-8 membered cycloalkyl" or "C 3~8 Examples of "cycloalkyl" groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, norbornyl, and bicyclo[2.2.2]octyl.

[0041] The term "3- to 8-membered cycloalkenyl" refers to an unsaturated carbocyclic compound that may contain one or more rings. Examples of "3- to 8-membered cycloalkenyl" groups include cyclopropenyl, cyclopropyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, norbornenyl, bicyclo[2.2.2]octenyl, and phenyl.

[0042] Alkyl, cycloalkyl, alkyne, aryl, aralkyl, alkaryl, linear C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 It will be understood that the alkoxy, phenyl, phenoxy, 3- to 8-membered cycloalkyl, and 3- to 8-membered cycloalkenyl can be optionally further substituted. Exemplary substituents include hydroxy, carboxy, amino, sulfonyl, halogen, and phenyl groups.

[0043] As used herein, the term "comprising" is to be interpreted as encompassing both "including" and "consisting of," both meanings being specifically intended for embodiments according to the present invention and, therefore, individually disclosed.

[0044] As used herein, the articles "a" and "an" preceding an element or component are intended to be open-ended regarding the number of instances (i.e., occurrences) of the element or component. Thus, "a" or "an" shall be understood to include one, or at least one, and singular forms of elements or components also include the plural, unless the number is clearly meant to be singular.

[0045] As used herein, the term "about" modifies the amount of a substance, component, ingredient, or parameter employed, and refers to the variation in quantity that may occur, for example, through typical measurement and handling procedures, such as the handling procedures of the liquid used to make concentrates or solutions.Furthermore, variation may occur due to unintentional errors in measurement procedures, differences in the manufacture, source, or purity of the components employed to carry out the method, etc.In one embodiment, the term "about" means within 10% of the reported numerical value.In a more specific embodiment, the term "about" means within 5% of the reported numerical value.

[0046] Surprisingly, it has been found that thermoset composite compositions according to the present invention may have numerous benefits, including, inter alia, improved processability, improved toughness, improved thermo-oxidative stability, increased safety profile, and / or improved physicochemical properties compared to the individual components of the resulting thermoset composite.

[0047] In particular, compositions according to the present invention have been found to have improved thermo-oxidative stability, which can be measured in terms of mass loss and surface damage of the resulting composite material.

[0048] Furthermore, the compositions according to the present invention also exhibit improved glass transition temperatures (Tg) of the resulting composite materials.

[0049] Furthermore, the compositions according to the present invention exhibit improvements in terms of material processability, such as reduced viscosity, reduced void formation, and reduced shrinkage and distortion in the resulting composite material, thereby reducing the need for lengthy degassing steps and resulting reduced pressure during polymerization.

[0050] Substituted bisimides have been found to improve the properties and / or processability of thermoset composites.

[0051] In particular, it has been found that thermoset composites based on substituted bisimides exhibit improved thermo-oxidative stability, improved fracture toughness, and reduced brittleness. Thermoset composites containing cyanate ester resins and substituted bisimides have superior handling, processing, and thermal stability.

[0052] Biscitraconimide is the 3-methyl analog of bismaleimide. Biscitraconimide resins can be prepared by the general reaction of two equivalents of citraconic anhydride with a bisamine, with the elimination of water. In "The Synthesis of Bisitaconamic Acids and Isomeric Bisimide Monomers," Galanti, AV et al., Journ. Poly. Sci.: Polymer Chemistry Edition, Vol. 20, pp. 233-239 (1982), a method for preparing biscitraconimide in the form of an isomeric mixture of citraconic and itaconimide is disclosed.

[0053] Methyl nadic imide can be prepared by the general reaction of two equivalents of methyl nadic anhydride with a bisamine by removing water. US4110294 "POLYMER, 1989, Vol. 30, June (Conference Issue) 1039" and JP20130551725 disclose a method for preparing an isomeric mixture of methyl nadic imide.

[0054] A wide variety of cyanate esters are known to those skilled in the art, examples of which include, but are not limited to, novolac cyanate esters (Primaset® PT resins from Arxada), naphthol-aralkyl cyanate esters, naphtholphenol novolac-type cyanate esters, 2,2-bis(4-cyanatophenyl)propane (known as bisphenol-A dicyanate and available under the trade names Primaset® BADCy, AroCy® B-10), bis( 4-cyanato-3,5-dimethylphenyl)methane (known as bisphenol-F dicyanate and available under the trade names Primaset® METHYLCy, AroCy® M-10), 1,1'-bis(4-cyanatophenyl)ethane (known as bisphenol-E dicyanate and available under the trade names Primaset® LeCy, AroCy® L-10), bis(4-cyanatophenyl)thioether (available under the trade name AroCy® T-10), 3-bis(4-cyanatophenyl-1-(1-methylethylidene))benzene (known as bisphenol-M dicyanate and available under the trade names Primaset® LM-500, AroCy® XU366, RTX366), cyanated phenol-dicyclopentadiene adduct (available under the trade names Primaset® DT-4000, AroCy® XU-71787.02L, XU71787), 1,3-phenylene-dicyanate (known as resorcinol dicyanate and available under the trade name REX-370), fused ring cyanate monomers such as naphthalene and anthraquinone, fluoroaliphatic dicyanates, propane-2,2-diylbis-2-(prop-2-en-1-yl)benzene-4,1-diyl dicyanate (known as diallyl bisphenol A dicyanate), available as Primaset® ULL-950S, Primaset® HTL-300, Primaset® CL-100, and mixtures / prepolymers thereof.Preferably, the difunctional cyanate compound of formula (I) according to the present invention is propane-2,2-diylbis-2-(prop-2-en-1-yl)benzene-4,1-diyl dicyanate (known as diallyl bisphenol A dicyanate).

[0055] Further cyanate esters which can be used in combination with the cyanate esters according to the invention are:

[0056] a. Reaction products of 2,2-bis(4-cyanatophenyl)propane (known as bisphenol-A dicyanate and available under the trade names Primaset® BADCy, AroCy® B-10) with hydroxyl-terminated polybutadiene (HTPB), which is an oligomer of butadiene terminated at each end with a hydroxyl group; b. Rubber-modified cyanate esters by incorporating crosslinked styrene-butadiene rubber copolymers and styrene-acrylonitrile copolymers into cyanated phenol-dicyclopentadiene adducts (Primaset® DT-4000, AroCy® XU-71787.02L, XU71787); c. Cyanate ester prepolymer obtained by prepolymerization reaction of bisphenol-A dicyanate.

[0057] According to the present invention, in the bifunctional cyanate ester compound of formula (I), R 1 ~R 8 At least one of the following is a straight chain C2 to C 10 Alkenyl and branched C3-C 10 In one embodiment, R is selected from the group consisting of alkenyl. 1 ~R 8 At least two of them are straight chain C2-C 10 Alkenyl and branched C3-C 10 In one embodiment, R is selected from the group consisting of alkenyl. 1 ~R 8 One or two of these are straight chain C2 to C 10 Alkenyl and branched C3-C10 In one embodiment, R is selected from the group consisting of alkenyl. 1 ~R 8 At least two of R are selected from vinyl and allyl. 1 and R 5 is a straight chain C2~C 10 Alkenyl and branched C3-C 10 More preferably, R is selected from the group consisting of alkenyl. 1 and R 5 are each independently a straight chain C2 to C 10 Even more preferably, R is alkenyl. 1 and R 5 are each independently selected from vinyl and allyl. Most preferably, R 1 and R 5 is an allyl.

[0058] According to the present invention, component (a) may comprise a mixture of a difunctional cyanate ester compound of formula (I) and a polyfunctional cyanate ester of formula (II).

[0059] In one embodiment, the polyfunctional cyanate ester is a polyfunctional cyanate ester of formula (II)

[0060] [ka]

[0061] (wherein n is an integer of 1 to 20; R 10 and R 11 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof.

[0062] In one embodiment, the polyfunctional cyanate ester is a polyfunctional cyanate ester of formula (IX-1)

[0063] [ka]

[0064] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof.

[0065] In one embodiment, in the polyfunctional cyanate ester of formula (IX-1), R 30 , R 31 , R 32 , and R 33 is hydrogen.

[0066] In one embodiment, the polyfunctional cyanate ester is a polyfunctional cyanate ester of formula (IX-2)

[0067] [ka]

[0068] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10alkenyl) and oligomers, prepolymers, polymers or mixtures thereof.

[0069] In one embodiment, in the polyfunctional cyanate ester of formula (IX-2), R 34 , R 35 , and R 36 is hydrogen.

[0070] In one embodiment, the polyfunctional cyanate ester is a polyfunctional cyanate ester of formula (IX-3)

[0071] [ka]

[0072] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof.

[0073] In one embodiment, in the polyfunctional cyanate ester of formula (IX-3), R 37 is hydrogen or methyl.

[0074] In one embodiment, the polyfunctional cyanate ester is a polyfunctional cyanate ester of formula (IX-4)

[0075] [ka]

[0076] (wherein n is an integer from 1 to 20), or an oligomer, prepolymer, polymer or mixture thereof.

[0077] In one embodiment, the polyfunctional cyanate ester is any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4).

[0078] In one embodiment, the polyfunctional cyanate ester is selected from polyfunctional cyanate esters of formula (IX-1), (IX-2), (IX-3), and any combination thereof.

[0079] In one embodiment, the polyfunctional cyanate ester is a polyfunctional cyanate ester of formula (II)

[0080] [ka]

[0081] (wherein n is an integer of 1 to 15; R 10 and R 11 are the same or different and independently represent hydrogen, linear C 1~8 Alkyl, branched chain C 4~8 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof.

[0082] In one embodiment, the polyfunctional cyanate ester is a polyfunctional cyanate ester of formula (II)

[0083] [ka]

[0084] (wherein n is an integer of 1 to 10; R 10 and R 11 are the same or different and independently represent hydrogen, linear C 1~5 Alkyl, branched chain C 4~6 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof.

[0085] In one embodiment, a polyfunctional cyanate ester of formula (II)

[0086] [ka]

[0087] are independently selected from the group consisting of Compound III, Compound IV, Compound V, Compound VI, and oligomers, prepolymers, polymers, or mixtures thereof.

[0088] [ka]

[0089] In one embodiment, component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0090] [ka]

[0091] (In the formula, R 1 ~R 8 are independently hydrogen, straight chain C 1~10 Alkyl, C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl; R 1 ~R 8 At least one of the following is a straight chain C2 to C 10 Alkenyl and branched C3-C 10 alkenyl; Z 1indicates a direct bond or -O-, -S-, -S(=O)-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, CH(CF3)-, -C(CF3)2-, -C(=O)-, -C(=CH2)-, -C(=CCl2)-, -Si(CH3)2-, straight chain C 1~10 Alkanediyl, branched chain C 4~10 Alkanediyl, C 3~8 Cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, -N(R 13 )-(wherein, R 13 is hydrogen, linear C 1~10 Alkyl, C 3~8 Cycloalkyl, phenyl, and phenoxy, and moieties of formula

[0092] [ka]

[0093] wherein X represents a divalent moiety selected from the group consisting of: (a) is a mixture of (i) and (ii), (ii) is a polyfunctional cyanate ester of formula (II)

[0094] [ka]

[0095] (wherein n is an integer of 1 to 20; R 10 and R 11 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-1)

[0096] [ka]

[0097] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0098] [ka]

[0099] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0100] [ka]

[0101] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0102] [ka]

[0103] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers or mixtures thereof; or any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4). is.

[0104] In another embodiment, component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0105] [ka]

[0106] (In the formula, R 1 ~R 8 are independently hydrogen, straight chain C 1~3 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl; R 1 ~R 8 At least one of the following is a straight chain C2 to C 10 Alkenyl and branched C3-C 10alkenyl; Z 1 indicates a direct bond or -O-, -S-, -S(=O)-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, CH(CF3)-, -C(CF3)2-, -C(=CCl2)-, -Si(CH3)2-, branched chain C 4~8 Alkanediyl, C 3~8 one or more cyanate esters independently selected from the group consisting of cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, and oligomers, prepolymers, polymers, or mixtures thereof; or (a) is a mixture of (i) and (ii), (ii) is a polyfunctional cyanate ester of formula (II)

[0107] [ka]

[0108] (wherein n is an integer of 1 to 15; R 10 and R 11 are the same or different and independently represent hydrogen, linear C 1~8 Alkyl, branched chain C 4~8 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-1)

[0109] [ka]

[0110] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0111] [ka]

[0112] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0113] [ka]

[0114] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0115] [ka]

[0116] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers or mixtures thereof; or any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4). is.

[0117] In another embodiment, component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0118] [ka]

[0119] (In the formula, R 1 ~R 8 are independently hydrogen, straight chain C 1~3 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl; R 1 ~R 8 At least one of the following is a straight chain C2 to C 10 Alkenyl and branched C3-C 10 alkenyl; Z 1 indicates a direct bond or -O-, -S-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, -C(CF3)2-, -C(=CCl2)-, branched chain C 4~6 Alkanediyl, C 3~8 one or more cyanate esters independently selected from the group consisting of cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, and oligomers, prepolymers, polymers, or mixtures thereof; or (a) is a mixture of (i) and (ii), (ii) is a polyfunctional cyanate ester of formula (II)

[0120] [ka]

[0121] (wherein n is an integer of 1 to 10; R 10 and R 11 are the same or different and independently represent hydrogen, linear C 1~5 Alkyl, branched chain C 4~6 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-1)

[0122] [ka]

[0123] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0124] [ka]

[0125] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0126] [ka]

[0127] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0128] [ka]

[0129] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers or mixtures thereof; or any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4).

[0130] In another embodiment, component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0131] [ka]

[0132] and The difunctional cyanate ester of formula I is i)R 1 and R 5 is an allylic and R 2 and R 6 is methyl, and R 3 , R 4 , R 7 and R 8 is hydrogen, and Z 1 is -CH2- (methylene); ii)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen and Z1 is -CH2- (methylene); iii)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen and Z1 is -C(CH3)2-; iv) R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -C(=O)-; v)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7and R 8 is hydrogen, and Z 1 is -S(=O)-; vi)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 but -S-; vii)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -C(CF3)2-; viii)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -C(=CCl2)-; ix)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 but,

[0133] [ka]

[0134] independently selected from the group consisting of: x)R 1 and R 5 is an allylic and R 2, R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 but,

[0135] [ka]

[0136] that which is; or xi)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -CH(CH3)-; and oligomers, prepolymers, polymers or mixtures thereof are independently selected from the group consisting of: (a) is a mixture of (i) and (ii), (ii) is a polyfunctional cyanate ester of formula (II)

[0137] [ka]

[0138] and the polyfunctional cyanate ester is independently selected from Compound III, Compound IV, Compound V, Compound VI, and oligomers, prepolymers, polymers, or mixtures thereof.

[0139] [ka]

[0140] or Polyfunctional cyanate ester of formula (IX-1)

[0141] [ka]

[0142] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0143] [ka]

[0144] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0145] [ka]

[0146] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0147] [ka]

[0148] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers or mixtures thereof; or Any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4) is.

[0149] In one embodiment, the polyfunctional cyanate ester is (i) Polyfunctional cyanate ester of formula (IX-1)

[0150] [ka]

[0151] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; (ii) Polyfunctional cyanate ester of formula (IX-2)

[0152] [ka]

[0153] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; (iii) Polyfunctional cyanate ester of formula (IX-3)

[0154] [ka]

[0155] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or (iv) Polyfunctional cyanate ester of formula (IX-4)

[0156] [ka]

[0157] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers, or mixtures thereof; and any combination thereof.

[0158] In one embodiment, in the difunctional cyanate ester compound of formula (I): (i)R 1 ~R8 At least two of the above are independently straight chain C2 to C 10 Alkenyl and branched C3-C 10 alkenyl; Preferably, R 1 ~R 8 Two of them are independently straight chain C2 to C 10 Alkenyl and branched C3-C 10 alkenyl; More preferably, R 1 and R 5 are independently linear C2 to C 10 Alkenyl and branched C3-C 10 alkenyl; R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen; (ii)R 1 ~R 8 at least two of are independently selected from the group consisting of allyl and vinyl; Preferably, R 1 ~R 8 two of which are independently selected from the group consisting of allyl and vinyl; More preferably, R 1 and R 5 is independently selected from the group consisting of allyl and vinyl, and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen; or (iii)R 1 and R 5 is an aryl and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen.

[0159] In another embodiment, component (a) (i) a difunctional cyanate ester compound of the formula:

[0160] [ka]

[0161] (In the formula, Z 1 indicates a direct bond or -O-, -S-, -S(=O)-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, CH(CF3)-, -C(CF3)2-, -C(=O)-, -C(=CH2)-, -C(=CCl2)-, -Si(CH3)2-, straight chain C 1~10 Alkanediyl, branched chain C 4~10 Alkanediyl, C 3~8 Cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, -N(R 13 )-(wherein, R 13 is hydrogen, linear C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, phenyl and phenoxy, and moieties of formula

[0162] [ka]

[0163] wherein X is independently selected from hydrogen and halogen; and one or more cyanate esters independently selected from the group consisting of: (a) is a mixture of (i) and (ii), (ii) is a polyfunctional cyanate ester of formula (II)

[0164] [ka]

[0165] (In the formula, n is an integer from 1 to 20; R 10 and R 11 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-1)

[0166] [ka]

[0167] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0168] [ka]

[0169] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0170] [ka]

[0171] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0172] [ka]

[0173] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers, or mixtures thereof; or Any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4) is.

[0174] In a particularly preferred embodiment, component (a) is (i) a difunctional cyanate ester compound of the formula:

[0175] [ka]

[0176] or one or more cyanate esters independently selected from (a) is a mixture of (i) and (ii), (ii) is a polyfunctional cyanate ester of formula (II)

[0177] [ka]

[0178] (wherein n is an integer of 1 to 20; R 10 and R 11 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof.

[0179] In a particularly preferred embodiment, component (a) is (i) a difunctional cyanate ester compound of the formula:

[0180] [ka]

[0181] or one or more cyanate esters independently selected from (a) is a mixture of (i) and (ii), (ii) is a polyfunctional cyanate ester of formula (II)

[0182] [ka]

[0183] (wherein n is an integer of 1 to 20; R 10 and R 11are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-1)

[0184] [ka]

[0185] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0186] [ka]

[0187] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0188] [ka]

[0189] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0190] [ka]

[0191] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers, or mixtures thereof; or Any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4) is.

[0192] In one embodiment, component (b) is a compound of formula (X)

[0193] [ka]

[0194] (wherein * and ** respectively indicate a covalent bond to the respective C atom of the residue indicated by * and **, The residues may be the same or different,

[0195] [ka]

[0196] are independently selected from R is independently selected from alkyl, cycloalkyl, alkyne, aryl, aralkyl, and alkaryl; Ra, Rb, and Rc are independently hydrogen, straight chain C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl, and phenoxy; Alternatively, Ra and Rb, Ra and Rc, or Rb and Rc may join together to form a 3- to 8-membered cycloalkyl or a 3- to 8-membered cycloalkenyl. and one or more substituted bisimide compounds independently selected from oligomers, prepolymers, polymers or mixtures of these compounds.

[0197] In another embodiment, R in the components of formula (X) is independently aryl, straight or branched chain C 1~10 Alkyl, C3-C8 cycloalkyl, C 2~10 an alkyne or moiety <<"N"-R-"N">>, wherein <<"N"-R-"N">> is selected from

[0198] [ka]

[0199] During the ceremony, R1, R2, R3 and R4 are each independently hydrogen, C2 to C 20 Alkyl, C2-C 20 Alkenes, C2-C 20selected from alkynes, halogens (preferably Cl, Br, F, or I), NO, and sulfones; X is independently C1 to C 20 Alkyl, C2-C 20 Alkenes, C2-C 20 alkynes and sulfones; and oligomers, prepolymers, polymers or mixtures thereof ("N" denotes a point of attachment).

[0200] Suitable substituted bisimide compounds as component (b) include:

[0201] [ka]

[0202] Examples include:

[0203] In another embodiment, component (b) is b1) at least one selected from the group consisting of biscitraconimide compounds of formula (X1), bisitaconimide compounds of formula (X2), and citraconic acid-itaconimide compounds of formula (X3), and oligomers, prepolymers, polymers, or mixtures thereof;

[0204] [ka]

[0205] or b2) Visnadic imide compounds of formula (X4), and oligomers, prepolymers, polymers or mixtures thereof

[0206] [ka]

[0207] (In the formula, Ra, Rb, and Rc are independently hydrogen, straight chain C 1~10Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl and phenoxy; or Ra and Rb, Ra and Rc, or Rb and Rc may join together to form a 3- to 8-membered cycloalkyl or a 3- to 8-membered cycloalkenyl; or b3) Bistetrahydroimide compounds of formula (X5), and oligomers, prepolymers, polymers or mixtures thereof

[0208] [ka]

[0209] wherein R is independently aryl, straight or branched chain C1-C 10 Alkyl, C3-C8 cycloalkyl, C2-C 10 an alkyne, or the moiety "N"-R-"N"; wherein "N"-R-"N" is

[0210] [ka]

[0211] During the ceremony, R1, R2, R3 and R4 are each independently hydrogen, C1 to C 20 Alkyl, C2-C 20 Alkenes, C2-C 20 selected from alkynes, halogens (preferably Cl, Br, F, or I), NO, and sulfones; X is independently C1 to C 20 Alkyl, C2-C 20Alkenes, C2-C 20 an aromatic amine moiety independently selected from alkynes and sulfones (where "N" denotes a point of attachment); and their oligomers, prepolymers, polymers or mixtures and one or more substituted bisimide compounds independently selected from:

[0212] In another embodiment, component (b) is b1) at least one selected from the group consisting of biscitraconimide compounds of formula (X1), bisitaconimide compounds of formula (X2), and citraconic-itaconimide compounds of formula (X3), and oligomers, prepolymers, polymers, or mixtures thereof;

[0213] [ka]

[0214] or b2) Visnadic imide compounds of formula (X4), and oligomers, prepolymers, polymers or mixtures thereof

[0215] [ka]

[0216] (In the formula, Ra, Rb, and Rc are independently hydrogen, straight chain C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl and phenoxy; or Ra and Rb, Ra and Rc, or Rb and Rc may join together to form a 3- to 8-membered cycloalkyl or a 3- to 8-membered cycloalkenyl; or b3) Bistetrahydroimide compounds of formula (X5), and oligomers, prepolymers, polymers or mixtures thereof

[0217] [ka]

[0218] wherein R is <<"N"-R-"N">>, where <<"N"-R-"N">> is an aromatic amine moiety independently selected from the following (where "N" denotes a point of attachment):

[0219] [ka]

[0220] where: R1, R2, R3 and R4 are each independently selected from hydrogen, C1-C5 alkyl, halogen (preferably Cl, Br, or F), NO2, and sulfone; X is independently C1 to C 20 Alkyl, C2-C 20 Alkenes, C2-C 20 selected from alkynes and sulfones); and oligomers, prepolymers, polymers or mixtures thereof and one or more substituted bisimide compounds independently selected from:

[0221] In another embodiment, component (b) is b1) at least one selected from the group consisting of biscitraconimide compounds of formula (X1), bisitaconimide compounds of formula (X2), and citraconic-itaconimide compounds of formula (X3), and oligomers, prepolymers, polymers, or mixtures thereof;

[0222] [ka]

[0223] or b2) Visnadic imide compounds of formula (X4), and oligomers, prepolymers, polymers or mixtures thereof

[0224] [ka]

[0225] (In the formula, Ra, Rb, and Rc are independently hydrogen, straight chain C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl and phenoxy; or Ra and Rb, Ra and Rc, or Rb and Rc may join together to form a 3- to 8-membered cycloalkyl or a 3- to 8-membered cycloalkenyl; or b3) Bistetrahydroimide compounds of formula (X5), and oligomers, prepolymers, polymers or mixtures thereof

[0226] [ka]

[0227] wherein R is independently selected from 4,4'-methylenediphenylene, o-phenylene, and m-xylylene; and oligomers, prepolymers, polymers or mixtures thereof and one or more substituted bisimide compounds independently selected from:

[0228] It will be understood that in the context of the present invention, component (b) may be any mixture of compounds of formula X, for example any mixture containing two or more of X1, X2, X3, X4, and X5, or any mixture containing X1, X2, and X3.

[0229] In a further preferred embodiment, component (b) is selected from the group consisting of biscitraconimide compounds of formula (X1), bisitaconimide compounds of formula (X2) and citraconic-itaconimide compounds of formula (X3)

[0230] [ka]

[0231] wherein R is independently selected from 4,4'-methylenediphenylene, o-phenylene, and m-xylylene; and oligomers, prepolymers, polymers or mixtures thereof and one or more substituted bisimide compounds selected from the group consisting of:

[0232] In another embodiment, component (b) is a biscitraconimide compound of formula (X1), a bisitaconimide compound of formula (X2), and a citraconic-itaconimide compound of formula (X3)

[0233] [ka]

[0234] (wherein R is m-xylylene); and oligomers, prepolymers, polymers or mixtures thereof and one or more substituted bisimide compounds selected from the group consisting of:

[0235] In another embodiment, component (b) is a biscitraconimide compound of formula (X1)

[0236] [ka]

[0237] (wherein R is m-xylylene); and oligomers, prepolymers, polymers or mixtures thereof is.

[0238] In compositions according to the present invention, the ratio of component (a) to component (b) may vary depending on the thermoset composite material to be formed and its desired properties, such as thermo-oxidative stability, glass transition temperature (Tg), and reduced void formation.

[0239] In one embodiment, the ratio of component (a) to component (b) is, based on the total amount of the resin composition, 80 wt.% component (a) to 20 wt.% component (b), 75 wt.% component (a) to 25 wt.% component (b), 70 wt.% component (a) to 30 wt.% component (b), 65 wt.% component (a) to 35 wt.% component (b), 60 wt.% component (a) to 40 wt.% component (b), 55 wt.% component (a) to 60 wt.% component (b), 60 wt.% component (a) to 60 wt.% component (b), 5 ...). (a) vs. 45 wt.% of component (b), 50 wt.% of component (a) vs. 50 wt.% of component (b), 45 wt.% of component (a) vs. 55 wt.% of component (b), 40 wt.% of component (a) vs. 60 wt.% of component (b), 35 wt.% of component (a) vs. 65 wt.% of component (b), 30 wt.% of component (a) vs. 70 wt.% of component (b), or 25 wt.% of component (a) vs. 75 wt.% of component (b).

[0240] In one embodiment, the ratio of component (a) to (b) is in the range of 10 to 70 wt.% component (a) to 90 to 30 wt.% component (b), based on the total amount of the resin composition.

[0241] In one embodiment, the ratio of component (a) to (b) is in the range of 20-70 wt.% component (a) to 80-30 wt.% component (b), based on the total weight of the resin composition.

[0242] In one embodiment, the ratio of component (a) to (b) is in the range of 30 to 70 wt.% component (a) to 70 to 30 wt.% component (b), based on the total weight of the resin composition.

[0243] In one embodiment, the ratio of component (a) to (b) is in the range of 40 to 60 wt.% component (a) to 60 to 40 wt.% component (b), based on the total weight of the resin composition.

[0244] In one embodiment, the ratio of component (a) to (b) is in the range of 25 to 75 wt.% component (a) to 75 to 25 wt.% component (b), based on the total weight of the resin composition.

[0245] In one embodiment, the ratio of component (a) to component (b) is 80 parts by weight of component (a) to 20 parts by weight of component (b), based on the total amount of the resin composition, to allow for excellent processability of the mixture.

[0246] In one embodiment, the ratio of component (a) to component (b) is 70 parts by weight of component (a) to 30 parts by weight of component (b), based on the total amount of the resin composition, to allow for excellent processability of the mixture.

[0247] In one embodiment, the ratio of component (a) to component (b) is 60 parts by weight of component (a) to 40 parts by weight of component (b), based on the total amount of the resin composition, to allow for excellent processability of the mixture.

[0248] In one embodiment, the ratio of component (a) to component (b) is 50 parts by weight of component (a) to 50 parts by weight of component (b), based on the total amount of the resin composition, to allow for excellent processability of the mixture.

[0249] In one embodiment, the ratio of component (a) to component (b) is 40 parts by weight of component (a) to 60 parts by weight of component (b), based on the total amount of the resin composition, to allow for excellent processability of the mixture.

[0250] In one embodiment, the ratio of component (a) to component (b) is 30 parts by weight of component (a) to 70 parts by weight of component (b), based on the total amount of the resin composition, to allow for excellent processability of the mixture.

[0251] In one embodiment, the ratio of component (a) to component (b) is 20 parts by weight of component (a) to 80 parts by weight of component (b), based on the total amount of the resin composition, to allow for excellent processability of the mixture.

[0252] In one embodiment, 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 5- or 6-membered nitrogen-containing heterocycle, hydroxyamines, phosphines, phenols, bisphenols, and mixtures thereof.

[0253] The catalyst may be included in the composition in an amount of 0 to 20 wt.% based on the total amount of the resin composition. The catalyst may be included in the composition in an amount of 0.01 to 20 wt.% based on the total amount of the resin composition. An amount of 0 to 20 wt.% includes about 1 wt.%, about 2 wt.%, about 3 wt.%, about 4 wt.%, about 5 wt.%, about 6 wt.%, about 7 wt.%, about 8 wt.%, about 9 wt.%, about 10 wt.%, about 11 wt.%, about 12 wt.%, about 13 wt.%, about 14 wt.%, about 15 wt.%, about 16 wt.%, about 17 wt.%, about 18 wt.%, about 19 wt.%, or about 20 wt.% based on the total amount of the resin composition. In one embodiment, the catalyst may be included in the composition in an amount of 0 to 20 wt.%, 0 to 15 wt.%, or 0 to 10 wt.%, based on the total amount of the resin composition. In one embodiment, the catalyst may be included in the composition in an amount of 0.01 to 20 wt.%, 0.1 to 15 wt.%, or 1 to 10 wt.%, based on the total amount of the resin composition.

[0254] In one embodiment, the catalyst comprises a bisphenol, such as bisphenol A or a substituted bisphenol A.

[0255] In one embodiment, the catalyst is a compound of formula (VII)

[0256] [ka]

[0257] (In the formula, R 1 ~R 8 are independently hydrogen, straight chain C 1~10 Alkyl, straight chain C2-C 10 Alkenyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, branched chain C3-C 10 Alkenyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, C 1~10is selected from the group consisting of alkoxy, halogen, phenyl and phenoxy, preferably R 1 ~R 8 are independently hydrogen, straight chain C 1~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl, R 1 ~R 8 At least one of the following is a straight chain C2 to C 10 Alkenyl (e.g., allyl or vinyl) and branched C-C 10 alkenyl, preferably R 1 and R 5 is a straight chain C2~C 10 Alkenyl (e.g., allyl or vinyl) and branched C-C 10 alkenyl, and optionally R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen; Z represents a direct bond or -O-, -S-, -S(=O)-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, -CH(CF3)-, -C(CF3)2-, -C(=O)-, -C(=CH2)-, -C(=CCl2)-, -Si(CH3)2-, linear C 1~10 Alkanediyl, branched chain C 4~10 Alkanediyl, C 3~8 Cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, -N(R 13 )-(wherein, R 13 is hydrogen, linear C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 cycloalkyl, phenyl, and phenoxy), and a moiety of formula

[0258] [ka]

[0259] wherein X is independently selected from hydrogen and halogen. represents a divalent moiety selected from the group consisting of and oligomers, prepolymers, polymers or mixtures thereof.

[0260] Preferably, the catalyst is a compound according to the formula:

[0261] [ka]

[0262] (In the formula, Z represents a direct bond or -O-, -S-, -S(=O)-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, CH(CF3)-, -C(CF3)2-, -C(=O)-, -C(=CH2)-, -C(=CCl2)-, -Si(CH3)2-, linear C 1~10 Alkanediyl, branched chain C 4~10 Alkanediyl, C 3~8 Cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, -N(R 13 )-(wherein, R 13 is hydrogen, linear C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 cycloalkyl, phenyl, and phenoxy), and a moiety of formula

[0263] [ka]

[0264] wherein X represents a divalent moiety selected from the group consisting of: hydrogen and halogen; and oligomers, polymers or mixtures thereof.

[0265] More preferably, the catalyst is a compound according to the formula

[0266] [ka]

[0267] where: Z represents a direct bond or a divalent moiety selected from the group consisting of -CH2-, -CH(CH3)-, and -C(CH3)2-, preferably Z is -C(CH3)2-.

[0268] Even more preferably, the catalyst is 4,4'-propane-2,2-diylbis[2-(prop-2-en-1-yl)phenol].

[0269] [ka]

[0270] Embodiments according to the present invention are provided as follows: Embodiment 1 provides a composition comprising components (a) and (b) as defined above.

[0271] Embodiment 2 is a method for preparing a compound according to the present invention, wherein component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0272] [ka]

[0273] (In the formula, R 1 ~R 8 are independently hydrogen, straight chain C 1~10Alkyl, C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl; R 1 ~R 8 At least one of the following is a straight chain C2 to C 10 Alkenyl and branched C3-C 10 alkenyl; Z 1 indicates a direct bond or -O-, -S-, -S(=O)-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, CH(CF3)-, -C(CF3)2-, -C(=O)-, -C(=CH2)-, -C(=CCl2)-, -Si(CH3)2-, straight chain C 1~10 Alkanediyl, branched chain C 4~10 Alkanediyl, C 3~8 Cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, -N(R 13 )-(wherein, R 13 is hydrogen, linear C 1~10 Alkyl, C 3~8 cycloalkyl, phenyl, and phenoxy), and a moiety of formula

[0274] [ka]

[0275] wherein X represents a divalent moiety selected from the group consisting of: hydrogen and halogen. and one or more cyanate esters independently selected from: and oligomers, prepolymers, polymers, or mixtures thereof; or (a) is a mixture of (i) and (ii), (ii) is a polyfunctional cyanate ester of formula (II)

[0276] [ka]

[0277] (wherein n is an integer of 1 to 20; R 10 and R 11 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-1)

[0278] [ka]

[0279] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0280] [ka]

[0281] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0282] [ka]

[0283] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0284] [ka]

[0285] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers, or mixtures thereof; or Any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4) The composition of embodiment 1 is provided, wherein

[0286] Embodiment 3 is directed to a compound in which component (b) is a biscitraconimide compound of formula (X1)

[0287] [ka]

[0288] wherein R is m-xylylene, and oligomers, prepolymers, polymers or mixtures thereof; or b1) at least one selected from the group consisting of biscitraconimide compounds of formula (X1), bisitaconimide compounds of formula (X2), and citraconic-itaconimide compounds of formula (X3), and oligomers, prepolymers, polymers, or mixtures thereof;

[0289] [ka]

[0290] or b2) Visnadic imide compounds of formula (X4), and oligomers, prepolymers, polymers or mixtures thereof

[0291] [ka]

[0292] (In the formula, Ra, Rb, and Rc are independently hydrogen, straight chain C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl and phenoxy; or Ra and Rb, Ra and Rc, or Rb and Rc may join together to form a 3- to 8-membered cycloalkyl or a 3- to 8-membered cycloalkenyl; or b3) Bistetrahydroimide compounds of formula (X5), and oligomers, prepolymers, polymers or mixtures thereof

[0293] [ka]

[0294] wherein R is independently aryl, straight or branched chain C1-C 10 Alkyl, C3-C8 cycloalkyl, C2-C 10 an alkyne or moiety <<"N"-R-"N">>, where <<"N"-R-"N">> is an aromatic amine moiety independently selected from the following (where "N" denotes a point of attachment):

[0295] [ka]

[0296] where: R1, R2, R3 and R4 are each independently hydrogen, C1 to C 20 Alkyl, C2-C 20 Alkenes, C2-C 20 selected from alkynes, halogens (preferably Cl, Br, F, or I), NO, and sulfones; X is independently C1 to C 20 Alkyl, C2-C 20 Alkenes, C2-C 20 alkynes and sulfones) and oligomers, prepolymers, polymers or mixtures thereof; The composition of any one of the preceding claims is provided, wherein the bisimide is one or more substituted bisimides independently selected from:

[0297] Embodiment 4 is a method for preparing a compound according to the present invention, wherein component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0298] [ka]

[0299] (In the formula, R1 ~R 8 are independently hydrogen, straight chain C 1~3 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl, R 1 ~R 8 At least one of the following is a straight chain C2 to C 10 Alkenyl and branched C3-C 10 alkenyl; Z 1 indicates a direct bond or -O-, -S-, -S(=O)-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, CH(CF3)-, -C(CF3)2-, -C(=CCl2)-, -Si(CH3)2-, branched chain C 4~8 Alkanediyl, C 3~8 one or more cyanate esters independently selected from the group consisting of cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, and oligomers, prepolymers, polymers, or mixtures thereof; or (a) is a mixture of (i) and (ii), (ii) is a polyfunctional cyanate ester of formula (II)

[0300] [ka]

[0301] (wherein n is an integer of 1 to 15; R 10 and R 11 are the same or different and independently represent hydrogen, linear C 1~8 Alkyl, branched chain C 4~8 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-1)

[0302] [ka]

[0303] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0304] [ka]

[0305] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0306] [ka]

[0307] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0308] [ka]

[0309] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers, or mixtures thereof; or Any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4) 4. The composition of any one of embodiments 1, 2, or 3, wherein

[0310] Embodiment 5 is directed to a compound in which component (b) is a biscitraconimide compound of formula (X1)

[0311] [ka]

[0312] wherein R is m-xylylene, and oligomers, prepolymers, polymers or mixtures thereof; or b1) at least one selected from the group consisting of biscitraconimide compounds of formula (X1), bisitaconimide compounds of formula (X2), and citraconic acid-itaconimide compounds of formula (X3), and oligomers, prepolymers, polymers, or mixtures thereof;

[0313] [ka]

[0314] or b2) Visnadic imide compounds of formula (X4), and oligomers, prepolymers, polymers or mixtures thereof

[0315] [ka]

[0316] (In the formula, Ra, Rb, and Rc are independently hydrogen, straight chain C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl and phenoxy; or Ra and Rb, Ra and Rc, or Rb and Rc may join together to form a 3- to 8-membered cycloalkyl or a 3- to 8-membered cycloalkenyl; or b3) Bistetrahydroimide compounds of formula (X5), and oligomers, prepolymers, polymers or mixtures thereof

[0317] [ka]

[0318] wherein R is the moiety "N"-R-"N"; and the moiety "N"-R-"N" is an aromatic amine moiety independently selected from the following (where "N" denotes a point of attachment):

[0319] [ka]

[0320] where: R1, R2, R3 and R4 are each independently selected from hydrogen, C1-C5 alkyl, halogen (preferably Cl, Br, or F), NO2, and sulfone; X is independently C1 to C 20 Alkyl, C2-C 20 Alkenes, C2-C 20 alkynes and sulfones) and oligomers, prepolymers, polymers or mixtures thereof

[0023] Embodiment 5 provides the composition of any one of embodiments 1, 2, 3, or 4, wherein the bisimide is one or more substituted bisimides independently selected from:

[0321] Embodiment 6 is directed to a compound wherein component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0322] [ka]

[0323] (In the formula, R 1 ~R 8 are independently hydrogen, straight chain C 1~3 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl, R 1 ~R 8 At least one of the following is a straight chain C2 to C 10 Alkenyl and branched C3-C 10 alkenyl; Z 1 indicates a direct bond or -O-, -S-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, -C(CF3)2-, -C(=CCl2)-, branched chain C 2~6 Alkanediyl, C 3~8one or more cyanate esters independently selected from the group consisting of cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, and oligomers, prepolymers, polymers, or mixtures thereof; or (a) is a mixture of (i) and (ii), (ii) is a polyfunctional cyanate ester of formula (II)

[0324] [ka]

[0325] (wherein n is an integer of 1 to 10; R 10 and R 11 are the same or different and independently represent hydrogen, linear C 1~5 Alkyl, branched chain C 4~6 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-1)

[0326] [ka]

[0327] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0328] [ka]

[0329] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0330] [ka]

[0331] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0332] [ka]

[0333] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers, or mixtures thereof; or Any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4) 6. The composition of any one of embodiments 1, 2, 3, 4, or 5, wherein

[0334] Embodiment 7 is directed to a compound in which component (b) is a biscitraconimide compound of formula (X1)

[0335] [ka]

[0336] wherein R is m-xylylene, and oligomers, prepolymers, polymers or mixtures thereof; or b1) at least one selected from the group consisting of biscitraconimide compounds of formula (X1), bisitaconimide compounds of formula (X2), and citraconic acid-itaconimide compounds of formula (X3), and oligomers, prepolymers, polymers, or mixtures thereof;

[0337] [ka]

[0338] ,or b2) Visnadic imide compounds of formula (X4), and oligomers, prepolymers, polymers or mixtures thereof

[0339] [ka]

[0340] (In the formula, Ra, Rb, and Rc are independently hydrogen, straight chain C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl and phenoxy; or Ra and Rb, Ra and Rc, or Rb and Rc may join together to form a 3- to 8-membered cycloalkyl or 3- to 8-membered cycloalkenyl; or b3) Bistetrahydroimide compounds of formula (X5), and oligomers, prepolymers, polymers or mixtures thereof

[0341] [ka]

[0342] wherein R is independently selected from 4,4'-methylenediphenylene, o-phenylene, and m-xylylene; preferably, R is m-xylylene. and oligomers, prepolymers, polymers or mixtures thereof

[0023] Embodiment 7. The composition of any one of embodiments 1, 2, 3, 4, 5, or 6, wherein the bisimide is one or more substituted bisimides independently selected from:

[0343] Embodiment 8 is an embodiment wherein component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0344] [ka]

[0345] and one or more cyanate esters independently selected from The difunctional cyanate ester of formula I is i)R 1 and R 5 is an allylic and R 2 and R 6 is methyl, and R 3 , R4 , R 7 and R 8 is hydrogen, and Z 1 is -CH2- (methylene); ii)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen and Z1 is -CH2- (methylene); iii)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen and Z1 is -C(CH3)2-; iv) R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -C(=O)-; v)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -S(=O)-; vi)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 but -S-; vii)R1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -C(CF3)2-; viii)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -C(=CCl2)-; ix)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 but,

[0346] [ka]

[0347] independently selected from the group consisting of: x)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 but,

[0348] [ka]

[0349] that which is; or xi)R 1 and R 5 is an aryl and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -CH(CH3)-, and oligomers, prepolymers, polymers or mixtures thereof; or (a) is a mixture of (i) and (ii), (ii) is a polyfunctional cyanate ester of formula (II)

[0350] [ka]

[0351] and the polyfunctional cyanate ester is independently selected from Compound III, Compound IV, Compound V, and Compound VI, and oligomers, prepolymers, polymers, or mixtures thereof.

[0352] [ka]

[0353] or Polyfunctional cyanate ester of formula (IX-1)

[0354] [ka]

[0355] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0356] [ka]

[0357] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0358] [ka]

[0359] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0360] [ka]

[0361] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers, or mixtures thereof; or Embodiment 8. The composition of any one of embodiments 1, 2, 3, 4, 5, 6, or 7, wherein the polyfunctional cyanate esters of formulas (II), (IX-1), (IX-2), (IX-3), and (IX-4) are any combinations thereof.

[0362] Embodiment 9 is directed to a compound in which component (b) is a biscitraconimide compound of formula (X1)

[0363] [ka]

[0364] wherein R is m-xylylene, and oligomers, prepolymers, polymers or mixtures thereof; or b1) at least one selected from the group consisting of biscitraconimide compounds of formula (X1), bisitaconimide compounds of formula (X2), and citraconic acid-itaconimide compounds of formula (X3), and oligomers, prepolymers, polymers, or mixtures thereof;

[0365] [ka]

[0366] or b2) Visnadic imide compounds of formula (X4), and oligomers, prepolymers, polymers or mixtures thereof

[0367] [ka]

[0368] (In the formula, Ra, Rb, and Rc are independently hydrogen, straight chain C 1~10 Alkyl, halogenated linear C1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl and phenoxy; or Ra and Rb, Ra and Rc, or Rb and Rc may join together to form a 3- to 8-membered cycloalkyl or a 3- to 8-membered cycloalkenyl; or b3) Bistetrahydroimide compounds of formula (X5), and oligomers, prepolymers, polymers or mixtures thereof

[0369] [ka]

[0370] wherein R is independently selected from 4,4'-methylenediphenylene, o-phenylene, and m-xylylene; and oligomers, prepolymers, polymers or mixtures thereof

[0023] Embodiment 9. The composition of any one of embodiments 1, 2, 3, 4, 5, 6, 7, or 8, wherein the bisimide is one or more substituted bisimides independently selected from:

[0371] Embodiment 10 is directed to a compound in which component (b) is a biscitraconimide compound of formula (X1), and oligomers, prepolymers, polymers, or mixtures thereof:

[0372] [ka]

[0373] or b1) at least one selected from the group consisting of biscitraconimide compounds of formula (X1), bisitaconimide compounds of formula (X2), and citraconic acid-itaconimide compounds of formula (X3), and oligomers, prepolymers, polymers, or mixtures thereof;

[0374] [ka]

[0375] or b2) visnadic imide compounds of formula (X4), and oligomers, prepolymers, polymers or mixtures thereof;

[0376] [ka]

[0377] (In the formula, Ra, Rb, and Rc are independently hydrogen, straight chain C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl and phenoxy; or Ra and Rb, Ra and Rc, or Rb and Rc may join together to form a 3- to 8-membered cycloalkyl or a 3- to 8-membered cycloalkenyl; or b3) Bistetrahydroimide compounds of formula (X5), and oligomers, prepolymers, polymers or mixtures thereof

[0378] [ka]

[0379] (wherein R is m-xylylene); and oligomers, prepolymers, polymers or mixtures thereof

[0023] Embodiment 10 is one or more substituted bisimide compounds independently selected from:

[0380] Embodiment 11 provides the composition of any one of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, wherein the ratio of component (a) to component (b) is 80 wt. % component (a) to 20 wt. % component (b), based on the total weight of the resin composition.

[0381] Embodiment 12 provides the composition of any one of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, wherein the ratio of component (a) to component (b) is 75 wt. % component (a) to 25 wt. % component (b), based on the total weight of the resin composition.

[0382] Embodiment 13 provides the composition of any one of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12, wherein the ratio of component (a) to component (b) is 70 wt. % component (a) to 30 wt. % component (b), based on the total weight of the resin composition.

[0383] Embodiment 14 provides the composition of any one of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13, wherein the ratio of component (a) to component (b) is 60 wt. % component (a) to 40 wt. % component (b), based on the total weight of the resin composition.

[0384] Embodiment 15 provides the composition of any one of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14, wherein the ratio of component (a) to component (b) is 55 wt. % component (a) to 45 wt. % component (b), based on the total weight of the resin composition.

[0385] Embodiment 16 provides the composition of any one of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15, wherein the ratio of component (a) to component (b) is 50 wt. % component (a) to 50 wt. % component (b), based on the total weight of the resin composition.

[0386] Embodiment 17 provides the composition of any one of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, or 16, 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 5- or 6-membered nitrogen-containing heterocycle, hydroxyamines, phosphines, phenols, bisphenols, and mixtures thereof.

[0387] Embodiment 18 is a method for preparing a composition comprising the steps of:

[0388] [ka]

[0389] (In the formula, R 1 ~R 8 are independently hydrogen, straight chain C 1~10 Alkyl, straight chain C2-C 10 Alkenyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, branched chain C3-C 10 Alkenyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, C 1~10 R is selected from the group consisting of alkoxy, halogen, phenyl, and phenoxy; 1 ~R 8 At least one of the following is a straight chain C2 to C 10Alkenyl and branched C3-C 10 alkenyl; Z represents a direct bond or -O-, -S-, -S(=O)-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, -CH(CF3)-, -C(CF3)2-, -C(=O)-, -C(=CH2)-, -C(=CCl2)-, -Si(CH3)2-, linear C 1~10 Alkanediyl, branched chain C 4~10 Alkanediyl, C 3~8 Cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, -N(R 13 )-(wherein, R 13 is hydrogen, linear C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 cycloalkyl, phenyl, and phenoxy), and a moiety of formula

[0390] [ka]

[0391] wherein X is independently selected from hydrogen and halogen, and further comprising a divalent moiety selected from the group consisting of: and oligomers, prepolymers, polymers, or mixtures thereof.

[0392] Embodiment 19 is an embodiment of the present invention, wherein the catalyst is 4,4′-propane-2,2-diylbis[2-(prop-2-en-1-yl)phenol]:

[0393] [ka]

[0394] 19. The composition of claim 18, wherein

[0395] Embodiment 20 provides the composition of any one of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, or 19, wherein the composition further comprises reinforcing fibers selected from the group consisting of carbon fibers, glass fibers (e.g., E-glass fibers, S-glass fibers), aramid fibers (e.g., KEVLAR®), basalt fibers (geotextile fibers), natural fibers (e.g., flax, hemp, jute, or sisal), fleece and woven fabrics (multi-layer or single layer), and mixtures thereof.

[0396] Embodiment 21 provides the composition of any one of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, wherein the composition further comprises a filler selected from the group consisting of organic fillers such as thermoplastics and elastomers, inorganic fillers such as glass microspheres, graphite, or silica, CaCO, coated CaCO, kaolin clay, SiO, talc, graphite, corundum (α-AlO), wollastonite, SiC, glass microspheres, mica, calcium silicate (CaOSi), MgO, anhydrous calcium sulfate (CaSO or anhydrite), ceramic hollow microspheres, fused mullite (AlO—SiO), boron nitride (BN), vermiculite, or basalt, and mixtures thereof.

[0397] Embodiment 22 is an embodiment wherein component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0398] [ka]

[0399] (In the formula, R 1 and R 5is an aryl and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is —C(CH3)2—) and one or more cyanate esters independently selected from oligomers, prepolymers, polymers, or mixtures thereof; or (a) is a mixture of (i) and (ii), (ii) is a polyfunctional cyanate ester of formula (II)

[0400] [ka]

[0401] wherein the polyfunctional cyanate ester is independently selected from the group consisting of Compound III, Compound IV, and Compound V, and oligomers, prepolymers, polymers, or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-1)

[0402] [ka]

[0403] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0404] [ka]

[0405] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0406] [ka]

[0407] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0408] [ka]

[0409] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers, or mixtures thereof; or Any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4) 22. The composition of any one of embodiments 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, or 21, wherein

[0410] Embodiment 23 is directed to a compound in which component (b) is a biscitraconimide compound of formula (X1)

[0411] [ka]

[0412] wherein R is m-xylylene, and a substituted bisimide compound selected from:

[0413] One group of compositions according to the present invention comprises components (a) and (b), wherein component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0414] [ka]

[0415] (In the formula, R 1 ~R 8 are independently hydrogen, straight chain C 1~10 Alkyl, C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl, R 1 ~R 8 At least one of the following is a straight chain C2 to C 10 Alkenyl and branched C3-C 10 alkenyl; Z 1indicates a direct bond or -O-, -S-, -S(=O)-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, -CH(CF3)-, -C(CF3)2-, -C(=O)-, -C(=CH2)-, -C(=CCl2)-, -Si(CH3)2-, straight chain C 1~10 Alkanediyl, branched chain C 4~10 Alkanediyl, C 3~8 Cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, -N(R 13 )-(wherein, R 13 is hydrogen, linear C 1~10 Alkyl, C 3~8 cycloalkyl, phenyl, and phenoxy), and a moiety of formula

[0416] [ka]

[0417] wherein X is independently selected from hydrogen and halogen; and one or more cyanate esters independently selected from the group consisting of: (a) is a mixture of (i) and (ii), (ii) is a polyfunctional cyanate ester of formula (II)

[0418] [ka]

[0419] (wherein n is an integer of 1 to 20; R 10 and R 11 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-1)

[0420] [ka]

[0421] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0422] [ka]

[0423] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0424] [ka]

[0425] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0426] [ka]

[0427] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers, or mixtures thereof; or Any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4) and; Component (b) is a biscitraconimide compound of formula (X1)

[0428] [ka]

[0429] wherein R is m-xylylene, and oligomers, prepolymers, polymers or mixtures thereof; or b1) at least one selected from the group consisting of biscitraconimide compounds of formula (X1), bisitaconimide compounds of formula (X2), and citraconic acid-itaconimide compounds of formula (X3), and oligomers, prepolymers, polymers, or mixtures thereof;

[0430] [ka]

[0431] or b2) visnadic imide compounds of formula (X4), and oligomers, prepolymers, polymers or mixtures thereof;

[0432] [ka]

[0433] (In the formula, Ra, Rb, and Rc are independently hydrogen, straight chain C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl and phenoxy; or Ra and Rb, Ra and Rc, or Rb and Rc may join together to form a 3- to 8-membered cycloalkyl or a 3- to 8-membered cycloalkenyl; or b3) Bistetrahydroimide compounds of formula (X5), and oligomers, prepolymers, polymers or mixtures thereof

[0434] [ka]

[0435] wherein R is independently aryl, straight or branched chain C1-C 10 Alkyl, C3-C8 cycloalkyl, C2-C 10 an alkyne or moiety <<"N"-R-"N">>, where <<"N"-R-"N">> is an aromatic amine moiety independently selected from the following (where "N" denotes a point of attachment):

[0436] [ka]

[0437] where: R1, R2, R3 and R4 are each independently hydrogen, C1 to C 20 Alkyl, C2-C 20 Alkenes, C2-C 20 selected from alkynes, halogens (preferably Cl, Br, F, or I), NO, and sulfones; X is independently C1 to C 20 Alkyl, C2-C 20 Alkenes, C2-C 20 alkynes and sulfones and oligomers, prepolymers, polymers or mixtures thereof and one or more substituted bisimides independently selected from:

[0438] Another group of compositions according to the present invention are those comprising components (a) and (b): Component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0439] [ka]

[0440] (In the formula, R 1 ~R 8 are independently hydrogen, straight chain C 1~3 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl, R 1 ~R 8 At least one of the following is a straight chain C2 to C 10 Alkenyl and branched C3-C 10 alkenyl; Z 1indicates a direct bond or -O-, -S-, -S(=O)-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, -CH(CF3)-, -C(CF3)2-, -C(=CCl2)-, -Si(CH3)2-, branched chain C 2~8 Alkanediyl, C 3~8 one or more cyanate esters independently selected from the group consisting of cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, and oligomers, prepolymers, polymers, or mixtures thereof; or (a) is a mixture of (i) and (ii), (ii) is a polyfunctional cyanate ester of formula (II)

[0441] [ka]

[0442] (wherein n is an integer of 1 to 15; R 10 and R 11 are the same or different and independently represent hydrogen, linear C 1~8 Alkyl, branched chain C 4~8 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-1)

[0443] [ka]

[0444] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0445] [ka]

[0446] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0447] [ka]

[0448] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0449] [ka]

[0450] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers, or mixtures thereof; or Any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4) and; Component (b) is a biscitraconimide compound of formula (X1)

[0451] [ka]

[0452] wherein R is m-xylylene, and oligomers, prepolymers, polymers or mixtures thereof; or b1) at least one selected from the group consisting of biscitraconimide compounds of formula (X1), bisitaconimide compounds of formula (X2), and citraconic acid-itaconimide compounds of formula (X3), and oligomers, prepolymers, polymers, or mixtures thereof;

[0453] [ka]

[0454] or b2) Visnadic imide compounds of formula (X4), and oligomers, prepolymers, polymers or mixtures thereof

[0455] [ka]

[0456] (In the formula, Ra, Rb, and Rc are independently hydrogen, straight chain C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl and phenoxy; or Ra and Rb, Ra and Rc, or Rb and Rc may join together to form a 3- to 8-membered cycloalkyl or 3- to 8-membered cycloalkenyl; or b3) Bistetrahydroimide compounds of formula (X5), and oligomers, prepolymers, polymers or mixtures thereof

[0457] [ka]

[0458] wherein R is the moiety "N"-R-"N"; and the moiety "N"-R-"N" is an aromatic amine moiety independently selected from the following (where "N" denotes a point of attachment):

[0459] [ka]

[0460] where: R1, R2, R3 and R4 are each independently selected from hydrogen, C1-C5 alkyl, halogen (preferably Cl, Br, or F), NO2, and sulfone; X is independently C1 to C 20 Alkyl, C2-C 20 Alkenes, C2-C 20 selected from alkynes and sulfones); and oligomers, prepolymers, polymers or mixtures thereof and one or more substituted bisimides independently selected from:

[0461] Another group of compositions according to the present invention are those comprising components (a) and (b), wherein component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0462] [ka]

[0463] (In the formula, R 1 ~R 8 are independently hydrogen, straight chain C 1~3 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl, R 1 ~R 8 At least one of the following is a straight chain C2 to C 10 Alkenyl and branched C3-C 10 alkenyl; Z 1 indicates a direct bond or -O-, -S-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, -C(CF3)2-, -C(=CCl2)-, branched chain C 4~6 Alkanediyl, C 3~8 one or more cyanate esters independently selected from the group consisting of cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, and oligomers, prepolymers, polymers, or mixtures thereof; or (a) is a mixture of (i) and (ii), (ii) is a polyfunctional cyanate ester of formula (II)

[0464] [ka]

[0465] (wherein n is an integer of 1 to 10; R 10 and R 11are the same or different and independently represent hydrogen, linear C 1~5 Alkyl, branched chain C 4~6 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-1)

[0466] [ka]

[0467] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0468] [ka]

[0469] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0470] [ka]

[0471] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0472] [ka]

[0473] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers, or mixtures thereof; or Any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4) and; Component (b) is a biscitraconimide compound of formula (X1)

[0474] [ka]

[0475] wherein R is m-xylylene, and oligomers, prepolymers, polymers or mixtures thereof; or b1) at least one selected from the group consisting of biscitraconimide compounds of formula (X1), bisitaconimide compounds of formula (X2), and citraconic acid-itaconimide compounds of formula (X3), and oligomers, prepolymers, polymers, or mixtures thereof;

[0476] [ka]

[0477] or b2) Visnadic imide compounds of formula (X4), and oligomers, prepolymers, polymers or mixtures thereof

[0478] [ka]

[0479] (In the formula, Ra, Rb, and Rc are independently hydrogen, straight chain C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl and phenoxy; or Ra and Rb, Ra and Rc, or Rb and Rc may join together to form a 3- to 8-membered cycloalkyl or a 3- to 8-membered cycloalkenyl; or b3) Bistetrahydroimide compounds of formula (X5), and oligomers, prepolymers, polymers or mixtures thereof

[0480] [ka]

[0481] wherein R is independently selected from 4,4'-methylenediphenylene, o-phenylene, and m-xylylene; and oligomers, prepolymers, polymers or mixtures thereof and one or more substituted bisimides independently selected from:

[0482] Another group of compositions according to the present invention are those comprising components (a) and (b), wherein component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0483] [ka]

[0484] and one or more cyanate esters independently selected from The difunctional cyanate ester of formula I is i)R 1 and R 5 is an allylic and R 2 and R 6 is methyl, and R 3 , R 4 , R 7 and R 8 is hydrogen, and Z 1 is -CH2- (methylene); ii)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen and Z1 is -CH2- (methylene); iii)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen and Z1 is -C(CH3)2-; iv) R 1 and R 5 is an allylic and R2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -C(=O)-; v)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -S(=O)-; vi)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 but -S-; vii)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -C(CF3)2-; viii)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -C(=CCl2)-; ix)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R8 is hydrogen, and Z 1 but,

[0485] [ka]

[0486] independently selected from the group consisting of: x)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 but,

[0487] [ka]

[0488] that which is; or xi)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -CH(CH3)-; and oligomers, prepolymers, polymers or mixtures thereof or (a) is a mixture of (i) and (ii), (ii) is a polyfunctional cyanate ester of formula (II)

[0489] [ka]

[0490] and the polyfunctional cyanate ester is independently selected from Compound III, Compound IV, Compound V, Compound VI, and oligomers, prepolymers, polymers, or mixtures thereof.

[0491] [ka]

[0492] or is selected from the group consisting of Polyfunctional cyanate ester of formula (IX-1)

[0493] [ka]

[0494] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0495] [ka]

[0496] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0497] [ka]

[0498] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0499] [ka]

[0500] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers or mixtures thereof; or any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4). and; Component (b) is a biscitraconimide compound of formula (X1)

[0501] [ka]

[0502] wherein R is m-xylylene, and oligomers, prepolymers, polymers or mixtures thereof; or b1) at least one selected from the group consisting of biscitraconimide compounds of formula (X1), bisitaconimide compounds of formula (X2), and citraconic acid-itaconimide compounds of formula (X3), and oligomers, prepolymers, polymers, or mixtures thereof;

[0503] [ka]

[0504] or b2) Visnadic imide compounds of formula (X4), and oligomers, prepolymers, polymers or mixtures thereof

[0505] [ka]

[0506] (In the formula, Ra, Rb, and Rc are independently hydrogen, straight chain C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl and phenoxy; or Ra and Rb, Ra and Rc, or Rb and Rc may join together to form a 3- to 8-membered cycloalkyl or a 3- to 8-membered cycloalkenyl; or b3) Bistetrahydroimide compounds of formula (X5), and oligomers, prepolymers, polymers or mixtures thereof

[0507] [ka]

[0508] wherein R is the moiety "N"-R-"N"; and the moiety "N"-R-"N" is an aromatic amine moiety independently selected from the following (where "N" denotes a point of attachment):

[0509] [ka]

[0510] where: R1, R2, R3 and R4 are each independently selected from hydrogen, C1-C5 alkyl, halogen (preferably Cl, Br, or F), NO2, and sulfone; X is independently C1 to C 20 Alkyl, C2-C 20 Alkenes, C2-C 20 selected from alkynes and sulfones); and oligomers, prepolymers, polymers or mixtures thereof and one or more substituted bisimides independently selected from:

[0511] Another group of compositions according to the present invention are those comprising components (a) and (b), wherein component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0512] [ka]

[0513] and one or more cyanate esters independently selected from The difunctional cyanate ester of formula I is i)R 1 and R 5 is an allylic and R 2 and R 6 is methyl, and R 3 , R 4 , R 7 and R8 is hydrogen, and Z 1 is -CH2- (methylene); ii)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -CH2- (methylene); iii)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -C(CH3)2-; iv) R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -C(=O)-; v)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -S(=O)-; vi)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 but -S-; vii)R1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -C(CF3)2-; viii)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -C(=CCl2)-; ix)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 but,

[0514] [ka]

[0515] Independently selected from the group consisting of: x)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 but,

[0516] [ka]

[0517] Something that is; or xi)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -CH(CH3)-; and oligomers, prepolymers, polymers or mixtures thereof or a difunctional cyanate ester independently selected from the group consisting of: (a) is a mixture of (i) and (ii), (ii) is a polyfunctional cyanate ester of formula (II),

[0518] [ka]

[0519] 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;

[0520] [ka]

[0521] Component (b) is a biscitraconimide compound of formula (X1)

[0522] [ka]

[0523] wherein R is m-xylylene, and oligomers, prepolymers, polymers or mixtures thereof; or b1) at least one selected from the group consisting of biscitraconimide compounds of formula (X1), bisitaconimide compounds of formula (X2), and citraconic acid-itaconimide compounds of formula (X3), and oligomers, prepolymers, polymers, or mixtures thereof;

[0524] [ka]

[0525] or b2) Visnadic imide compounds of formula (X4), and oligomers, prepolymers, polymers or mixtures thereof

[0526] [ka]

[0527] (In the formula, Ra, Rb, and Rc are independently hydrogen, straight chain C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl and phenoxy; or Ra and Rb, Ra and Rc, or Rb and Rc may join together to form a 3- to 8-membered cycloalkyl or a 3- to 8-membered cycloalkenyl; or b3) Bistetrahydroimide compounds of formula (X5), and oligomers, prepolymers, polymers or mixtures thereof

[0528] [ka]

[0529] wherein R is independently selected from 4,4'-methylenediphenylene, o-phenylene, and m-xylylene; and oligomers, prepolymers, polymers or mixtures thereof and one or more substituted bisimide compounds independently selected from:

[0530] Another group of compositions according to the present invention are those comprising components (a) and (b), wherein component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0531] [ka]

[0532] (In the formula, R 1 ~R 8 are independently hydrogen, straight chain C2 to C 10 Alkenyl and branched C3-C 10 alkenyl, R 1 ~R 8 At least one of the following is a straight chain C2 to C 10 Alkenyl and branched C3-C 10 alkenyl; Z 1 is —C(CH3)2—) and one or more cyanate esters independently selected from oligomers, prepolymers, polymers, or mixtures thereof; or (a) is a mixture of (i) and (ii), (ii) is a polyfunctional cyanate ester of formula (II)

[0533] [ka]

[0534] wherein the polyfunctional cyanate ester is independently selected from Compound III, Compound IV, Compound V, and oligomers, prepolymers, polymers, or mixtures thereof;

[0535] [ka]

[0536] is selected from the group consisting of Component (b) is a biscitraconimide compound of formula (X1)

[0537] [ka]

[0538] wherein R is m-xylylene, and a substituted bisimide compound selected from oligomers, prepolymers, polymers, or mixtures thereof; or At least one selected from the group consisting of biscitraconimide compounds of formula (X1), bisitaconimide compounds of formula (X2), and citraconic acid-itaconimide compounds of formula (X3); and oligomers, prepolymers, polymers, or mixtures thereof.

[0539] [ka]

[0540] (wherein R is m-xylylene).

[0541] In one embodiment, after curing a composition comprising components (a) and (b) according to the present invention, the cured composition exhibits a weight loss of less than about 2.5 wt.%, preferably a weight loss of less than about 2.0 wt.%, and more preferably a weight loss of less than about 1.75 wt.% after 1000 hours at 250°C.

[0542] Preparation of the composition according to the invention The present invention relates to novel compositions comprising cyanate ester resins and substituted bisimides (citraconimide, bisitaconimide, citraconic-itaconimide, bisnadicimide, bismethylnadicimide, bistetrahydroimide and mixtures thereof), and to thermoset composites based on these compositions.

[0543] The preparation of the viscous liquid mixture of component (a) the cyanate ester and component (b) the substituted bisimide compound can be accomplished, inter alia, by intimately mixing the components together in their liquid state (i.e., at the required temperature) until homogenization is achieved. It is also possible to produce the mixture of components at lower temperatures by the use of a solvent.

[0544] The preparation of the cyanate esters of component (a) is described, inter alia, in JP1990251518A, EP1566377, EP2722363, and JP2018062568A, or can be prepared by analogous procedures described therein, or by standard synthetic techniques known to those skilled in the art. In addition, many of the cyanate esters of component (a) are also commercially available (e.g., under the brand name Primaset from Arcade, Switzerland).

[0545] The preparation of the compounds of component (b) is described, inter alia, in US20120049106, US7271227B1, US5198515, US4110294, JP20130551725, EP2799497B1, and US4568733, RSC Adv., 2017, 7, 23149, or can be prepared by analogous procedures described therein, or by standard synthetic techniques known to those skilled in the art. In addition, many of the compounds of component (b) are also commercially available (e.g., from HOS Technik and Lanxess, among others). Homide 400 is commercially available from HOS, among others, and 1,3-bis(citraconimidomethyl)benzene (CAS-RN119462-56-5, also referred to as 1,3-bis((3-methyl-2,5-dioxopyrrol-1-yl)methyl)benzene) is commercially available from Lanxess, among others (available as Perkalink® 900).

[0546] The viscous liquid mixture can be used as a stand-alone thermoset resin for casting processes, adhesives, insulating films, or alternatively, in combination with fibers or fabrics for the production of fiber-reinforced parts. For the production of fiber-reinforced parts, there are a number of established and well-known methods that can be used, such as traditional prepreg (hot melt and solvated), resin infusion, resin injection, filament winding, pultrusion, hand lamination, and compression molding.

[0547] Preparation of thermosetting composite materials according to the present invention Preparation of thermoset composite materials according to the present invention can be accomplished as follows: providing a viscous liquid mixture of the cyanate ester of component (a) and the substituted bisimide compound of component (b) described above; casting the mixture into a desired form; and then initiating polymerization of the mixture (e.g., by, among other things, increasing the temperature, using a catalyst as described above and below, or other methods generally known in the art).

[0548] Additionally, as described above and below, the mixture may further comprise additional components selected from catalysts and / or fibers, fillers, pigments and / or additives that may be desirable or useful in the resin casting process and / or in the preparation of adhesives and insulating films. The inclusion of these optional components is achieved by adding them to the mixture in the processes described above.

[0549] In one embodiment, a thermosetting composite according to the present invention exhibits less than about 2.5 wt.% weight loss, preferably less than about 2.0 wt.% weight loss, and more preferably less than about 1.75 wt.% weight loss after 1000 hours at 250°C.

[0550] In one embodiment, a method for the preparation of a thermoset composite part produced according to the present invention comprises: (i) mixing component (a) a cyanate ester and component (b) a substituted bisimide compound to obtain a homogeneous mixture; a. optionally, a catalyst and a solvent may be added to the mixture composition; (ii) providing a fiber structure; (iii) placing the fibrous structure in a mold or on a substrate; (iv) impregnating the fibrous structure with the mixture (from step (i)), optionally by applying elevated pressure and / or removing air and solvent from the mold and fibrous structure, preferably at a temperature of 50-150°C; and The liquid mixture is cured into a cured laminate by a heating step, preferably by applying a temperature of 50-200°C, for a time sufficient to achieve a degree of conversion that allows removal of the part from the mold. A post-cure step may be performed directly following the cure cycle and / or independently after removal of the part from the mold. Preferably, the post-cure is applied independently by applying a temperature of 200-300°C to achieve a very high degree of conversion and optimal heat resistance, respectively.

[0551] In another embodiment, the impregnation in step (iv) is achieved using a method selected from the group consisting of prepreg (hot melt and solvent methods), resin transfer molding, vacuum assisted resin transfer molding, vacuum resin infusion, Seemann composite resin infusion molding process, injection molding, compression molding, spray molding, pultrusion, hand laminating, filament winding, the Quickstep process, or the Roctool process.

[0552] In another embodiment, the impregnation in step (iv) is accomplished using a hybrid molding process method selected from the group consisting of prepreg (hot melt and solvent methods), resin transfer molding, liquid resin infusion, Seaman composite resin infusion molding process, vacuum assisted resin infusion, injection molding, BMC / SMC bulk and sheet molding compounds, and EADS vacuum assisted process (VAP®).

[0553] The mixture of cyanate ester of component (a) and substituted bisimide compound of component (b) can optionally be formulated with at least one di- or multi-functional epoxy resin selected from the group consisting of bisphenol A diglycidyl ether resin, bisphenol F diglycidyl ether resin, N,N,O-triglycidyl-3-aminophenol, N,N,O-triglycidyl-4-aminophenol, N,N,N',N'-tetraglycidyl-4,4'-methylenebisbenzenamine, 4,4',4"-methylidene trisphenol triglycidyl ether resin, naphthalenediol diglycidyl ether, and mixtures thereof.

[0554] The mixture of cyanate ester of component (a) and substituted bisimide of compound of component (b) can optionally be formulated with at least one bismaleimide compound known to those skilled in the art, such as, for example, selected from the group consisting of 2,2′-bis(4-(4-maleimidophenoxy)-phenyl)propane, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, and mixtures thereof, as disclosed in WO 2018 / 139368.

[0555] The mixture of cyanate esters of component (a) and substituted bisimides of compounds of component (b) can optionally be formulated with at least one benzoxazine compound known to those skilled in the art, such as, for example, selected from the group consisting of bisphenol-A benzoxazine, bisphenol-F benzoxazine, phenolphthalein (PhPTH) benzoxazine, dicyclopentadiene (DCPD) benzoxazine, thiodiphenol benzoxazine, and mixtures thereof.

[0556] The mixture of cyanate esters of component (a) and substituted bisimides of compounds of component (b) can optionally be formulated with at least one unsaturated polyester compound known to those skilled in the art, such as, for example, isophthalic acid polyesters, acrylic acid-based unsaturated polyesters, methyl methacrylate (MMA)-based unsaturated polyesters, butyl methacrylate (BMA)-based unsaturated polyesters, acrylonitrile (AN)-based unsaturated polyesters, and mixtures thereof.

[0557] The mixture of cyanate ester of component (a) and substituted bisimide of compound of component (b) can optionally be formulated with at least one vinyl ester compound known to those skilled in the art, such as, for example, a compound selected from the group consisting of methacrylic acid vinyl ester, acrylic acid vinyl ester, bisphenol-A epoxy-based vinyl ester, phenolic novolac-based vinyl ester, tetrabromobisphenol-A epoxy-based vinyl ester, and mixtures thereof.

[0558] Additionally, the mixture of cyanate esters of component (a) and substituted bisimides of compounds of component (b) can optionally be formulated with at least one reactivity modifier, such as, but not limited to, thermoplastics, small organic molecules, rubbers, and inorganic / organometallic polymers. Reactive groups on the additive include, but are not limited to, hydroxyl, acrylate, methacrylate, phenol, bisphenol, thiol, epoxy, bismaleimide, benzoxazine, amine, thiol, thiophenol, and phosphorus-containing groups.

[0559] Compositions according to the present invention may optionally further comprise a catalyst to aid in the curing process.

[0560] Suitable catalysts are 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 5- or 6-membered nitrogen-containing heterocycle, hydroxyamines, phosphines, phenols, bisphenols, and mixtures thereof.

[0561] Preferably, the catalyst comprises a bisphenol, such as bisphenol A or a substituted bisphenol A, e.g., a linear C2-C6 bisphenol, such as vinyl or allyl. 10 Includes alkenyl-substituted bisphenol A.

[0562] The catalyst may be included in the composition in an amount of 0 to 20 wt.%, based on the total amount of the resin composition. An amount of 0 to 20 wt.% includes about 1 wt.%, about 2 wt.%, about 3 wt.%, about 4 wt.%, about 5 wt.%, about 6 wt.%, about 7 wt.%, about 8 wt.%, about 9 wt.%, about 10 wt.%, about 11 wt.%, about 12 wt.%, about 13 wt.%, about 14 wt.%, about 15 wt.%, about 16 wt.%, about 17 wt.%, about 18 wt.%, about 19 wt.%, or about 20 wt.%, based on the total amount of the resin composition. In one embodiment, the catalyst may be included in the composition in an amount of 0 to 20 wt.%, 0 to 15 wt.%, or 0 to 10 wt.%, based on the total amount of the resin composition.

[0563] Particularly suitable catalysts are compounds of formula (VII) and oligomers, prepolymers, polymers or mixtures thereof,

[0564] [ka]

[0565] During the ceremony, R 1 ~R 8 are independently hydrogen, straight chain C 1~10 Alkyl, straight chain C2-C 10 Alkenyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10Alkyl, branched chain C3-C 10 Alkenyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl, and phenoxy; R 1 ~R 8 At least one of the following is a straight chain C2 to C 10 Alkenyl and branched C3-C 10 alkenyl; Z represents a direct bond or -O-, -S-, -S(=O)-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, -CH(CF3)-, -C(CF3)2-, -C(=O)-, -C(=CH2)-, -C(=CCl2)-, -Si(CH3)2-, linear C 1~10 Alkanediyl, branched chain C 4~10 Alkanediyl, C 3~8 Cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, -N(R 13 )-(wherein, R 13 is hydrogen, linear C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 cycloalkyl, phenyl, and phenoxy), and a moiety of formula

[0566] [ka]

[0567] wherein X is independently selected from hydrogen and halogen.

[0568] Preferably, the catalyst is a compound according to the following formula and oligomers, polymers or mixtures thereof:

[0569] [ka]

[0570] where: Z represents a direct bond or -O-, -S-, -S(=O)-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, CH(CF3)-, -C(CF3)2-, -C(=O)-, -C(=CH2)-, -C(=CCl2)-, -Si(CH3)2-, linear C 1~10 Alkanediyl, branched chain C 4~10 Alkanediyl, C 3~8 Cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, -N(R 13 )-(wherein, R 13 is hydrogen, linear C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 cycloalkyl, phenyl, and phenoxy), and a moiety of formula

[0571] [ka]

[0572] wherein X is independently selected from hydrogen and halogen.

[0573] More preferably, the catalyst is a compound according to the formula

[0574] [ka]

[0575] wherein Z represents a direct bond or a divalent moiety selected from the group consisting of -CH2-, -CH(CH3)-, and -C(CH3)2-. is.

[0576] Even more preferably, the catalyst is

[0577] [ka]

[0578] is.

[0579] Furthermore, the resin composition of the present invention may optionally contain a curing accelerator to appropriately control the curing rate as needed. Any of those commonly used as curing accelerator catalysts for cyanate and bismaleimide ester compounds, epoxy resins, etc. can be suitably used as the curing accelerator, and the type is not particularly limited. Specific examples of the curing accelerator include organic metal salts such as aluminum acetylacetonate, zinc octylate, zinc naphthenate, cobalt naphthenate, copper naphthenate, iron acetylacetonate, nickel octylate, and manganese octylate; phenol or phenolic compounds such as 2,2'-bis(3-allyl-4-hydroxyphenyl)propane, xylenol, cresol, resorcinol, catechol, octylphenol, and nonylphenol; alcohols such as 1-butanol and 2-ethylhexanol; 2-phenylimidazole, 4-phenylimidazole, 1-phenylimidazole, 2-methylimidazole, 2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, and 2-phenyl-4-methyl-5-hydroxyimidazole. imidazoles such as methylimidazole, and derivatives of these imidazoles, such as their carboxylic acid or anhydride adducts; amines such as dicyandiamide, benzyldimethylamine, and 4-methyl-N,N-dimethylbenzylamine; phosphorus compounds such as phosphine-based compounds, phosphine oxide-based compounds, phosphonium salt-based compounds, and diphosphine compounds; epoxy-imidazole adduct-based compounds; peroxides such as benzoyl peroxide, p-chlorobenzoyl peroxide, di-t-butyl peroxide, diisopropyl peroxycarbonate, and di-2-ethylhexyl peroxycarbonate 2,5-dimethyl-2,5-di(tert-butylperoxy)hexyne-3 (Trigonox 145-E85 manufactured by Nouryon); and azo compounds such as azobisisobutyronitrile.Many curing accelerators (polymerization catalysts) are commercially available, such as Amicure PN-23 (a product name manufactured by and available from Ajinomoto Fine-Techno Co., Ltd.), Novacure HX-3721 (a product name manufactured by and available from Asahi Kasei Advance Co., Ltd.), and Fujicure FX-1000 (a product name manufactured by and available from Fuji Kasei Co., Ltd.).

[0580] In one embodiment, the catalyst is selected from the group consisting of an aromatic diamine catalyst, a transition metal salt catalyst, a peroxide catalyst, an imidazole catalyst, or 1,4-diazabicyclo[2.2.2]octane (DABCO), as defined directly below, and mixtures thereof.

[0581] The aromatic diamine catalyst is represented by the formula VIIa and VIIb

[0582] [ka]

[0583] and wherein the aromatic diamine is selected from the group consisting of: R 12 , R 13 , R 14 , R 17 , R 16 , R 18 , R 19 , R 21 , R 22 and R 23 are independently hydrogen, C 1~4 Alkyl, C 1~4 Alkoxy, C 1~4 selected from alkylthio and chlorine; R 15 , R 16 , R 20 and R 24 are independently hydrogen and C 1~8 alkyl; Z 2indicates a direct bond or -O-, -S-, -S(=O)-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, -CH(CF3)-, -C(CF3)2-, -C(=O)-, -C(=CH2)-, -C(=CCl2)-, -Si(CH3)2-, straight chain C 1~10 Alkanediyl, branched chain C 4~10 Alkanediyl, C 3~8 Cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, -N(R 25 )-(wherein, R 25 is hydrogen, linear C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 represents a divalent moiety selected from the group consisting of cycloalkyl, phenyl, and phenoxy.

[0584] Expression “C 1~4 "Alkyl" is meant herein to include methyl, ethyl, 1-propyl, 2-propyl (isopropyl), 1-butyl, 2-butyl (sec-butyl), 2-methyl-1-propyl (isobutyl) and 2-methyl-2-propyl (tert-butyl), while the expression "C 1~8 "Alkyl" is a straight chain C 1~10 Alkyl and Branched Chain C 4~10 In accordance with the definition given above for alkyl, it is meant to include the hitherto mentioned and all straight and branched chain alkyl groups having from 5 to 8 carbon atoms.

[0585] Preferably, R 12 , R 13 , R 14 , R 17 , R 16 , R 18 , R 19 , R 21 , R 22 and R 23 are independently hydrogen, C 1~4 Alkyl, and C 1~4selected from alkoxy; R 15 , R 16 , R 20 and R 24 are independently hydrogen and C 1~4 alkyl; Z 2 is a methylene (-CH2-) group.

[0586] The transition metal salt catalyst is preferably selected from the group consisting of aluminum(III) acetylacetonate, manganese(II) acetylacetonate, zinc(II) acetylacetonate, cobalt(II) acetylacetonate, cobalt(III) acetylacetonate, copper(II) acetylacetonate, iron(III) acetylacetonate, and mixtures thereof.

[0587] The peroxide catalyst is preferably benzoyl peroxide, p-chlorobenzoyl peroxide, di-t-butyl peroxide, diisopropyl peroxycarbonate and di-2-ethylhexyl peroxycarbonate, or 2,5-dimethyl-2,5-di(tert-butylperoxy)hexyne-3 (Trigonox 145-E85 manufactured by Nouryon).

[0588] The imidazole catalyst is preferably 2-phenylimidazole, 4-phenylimidazole, 1-phenylimidazole, 2-methylimidazole, 2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, and 2-phenyl-4-methyl-5-hydroxymethylimidazole.

[0589] Alternatively, the catalyst is preferably 1,4-diazabicyclo[2.2.2]octane (DABCO).

[0590] Preferably, the catalyst is selected from the group consisting of an aromatic diamine catalyst, a transition metal salt catalyst, a peroxide catalyst, an imidazole catalyst, or 1,4-diazabicyclo[2.2.2]octane (DABCO), as defined directly below, and mixtures thereof.

[0591] Preferably, the aromatic diamine catalyst is selected from the group consisting of 3,5-diethyltoluene-2,4-diamine, 3,5-diethyltoluene-2,6-diamine, 4,4'-methylene-bis(2,6-diisopropylaniline), 4,4'-methylene-bis(2-isopropyl-6-methylaniline), 4,4'-methylene-bis(2,6-diethylaniline) (M-DEA), 4,4'-methylene-bis(3-chloro-2,6-diethylaniline) (M-CDEA), 4,4'-methylene-bis(2-ethyl-6-methylaniline), 4,4'-methylene-bis(N-sec-butylaniline), dimethylthiotoluenediamine (DMTDA), and mixtures thereof.

[0592] Preferably, the transition metal salt catalyst is selected from the group consisting of aluminum(III) acetylacetonate, manganese(II) acetylacetonate, zinc(II) acetylacetonate, cobalt(II) acetylacetonate, cobalt(III) acetylacetonate, copper(II) acetylacetonate, iron(III) acetylacetonate, and mixtures thereof.

[0593] Preferably, the peroxide catalyst is more preferably benzoyl peroxide, p-chlorobenzoyl peroxide, di-t-butyl peroxide, diisopropyl peroxycarbonate and di-2-ethylhexyl peroxycarbonate or 2,5-dimethyl-2,5-di(tert-butylperoxy)hexyne-3 (Trigonox 145-E85 manufactured by Nouryon).

[0594] Preferably, the imidazole catalyst is 2-phenylimidazole, 4-phenylimidazole, 1-phenylimidazole, 2-methylimidazole, 2-ethyl-4-methylimidazole, more preferably.

[0595] Alternatively, the catalyst is more preferably 1,4-diazabicyclo[2.2.2]octane (DABCO).

[0596] In one embodiment, the catalyst is selected from the group consisting of an aromatic diamine catalyst, a transition metal salt catalyst, a peroxide catalyst, an imidazole catalyst, or 1,4-diazabicyclo[2.2.2]octane (DABCO), as defined directly below, and mixtures thereof.

[0597] In one embodiment, the aromatic diamine catalyst is selected from the group consisting of 3,5-diethyltoluene-2,4-diamine, 3,5-diethyltoluene-2,6-diamine, 4,4'-methylene-bis(2,6-diisopropylaniline), 4,4'-methylene-bis(2-isopropyl-6-methylaniline), 4,4'-methylene-bis(2,6-diethylaniline) (M-DEA), 4,4'-methylene-bis(3-chloro-2,6-diethylaniline) (M-CDEA), 4,4'-methylene-bis(2-ethyl-6-methylaniline), 4,4'-methylene-bis(N-sec-butylaniline), and mixtures thereof.

[0598] The transition metal salt catalyst is most preferably selected from the group consisting of aluminum(III) acetylacetonate, manganese(II) acetylacetonate, zinc(II) acetylacetonate, cobalt(II) acetylacetonate, cobalt(III) acetylacetonate, copper(II) acetylacetonate, iron(III) acetylacetonate, and mixtures thereof. The transition metal salt catalyst is most particularly preferably aluminum(III) acetylacetonate.

[0599] The peroxide catalyst is more preferably benzoyl peroxide, di-t-butyl peroxide, diisopropyl peroxycarbonate and di-2-ethylhexyl peroxycarbonate, or 2,5-dimethyl-2,5-di(tert-butylperoxy)hexyne-3 (Trigonox 145-E85 manufactured by Nouryon).

[0600] The imidazole catalyst is more preferably 2-phenylimidazole, 4-phenylimidazole, or 1-phenylimidazole.

[0601] Alternatively, the catalyst is more preferably 1,4-diazabicyclo[2.2.2]octane (DABCO).

[0602] The above catalysts have been found to act as curing catalysts when used in compositions according to the present invention.

[0603] The amount of catalyst can be varied to suit various applications and needs, and typically ranges from 0.05 to 20.0 wt.%, more preferably from 0.1 to 15 wt.%, and even more preferably from 0.15 to 10 wt.%, based on the total weight of the cyanate ester bisimide mixture.

[0604] The composition according to the present invention may optionally further comprise reinforcing fibers to improve the mechanical performance of the final composite material.

[0605] Suitable reinforcing fibers are known in the art and can be selected from materials such as carbon fiber, glass fiber (e.g., E-glass fiber, S-glass fiber), aramid fiber (e.g., KEVLAR®, etc.), basalt fiber (geotextile fiber), natural fibers (e.g., flax, hemp, jute, or sisal), fleece, and woven fabrics (multi-layer or single layer).

[0606] A mixture of two or more types of reinforcing fibers may also be applied.

[0607] In one embodiment, the reinforcing fibers are carbon fibers, such as polyacrylonitrile PAN-based carbon fibers, glass fibers, basalt fibers, aramid fibers, or natural fibers, or mixtures thereof.

[0608] In another embodiment, the reinforcing fibers are glass fibers, carbon fibers, or aramid fibers, or mixtures thereof.

[0609] The reinforcing fibers may be preformed fibers, chopped or continuous, random or oriented, woven or nonwoven, knitted or non-knitted, or braided fibers according to the requirements of any of the various different parts of the desired structure of the molded composite or fiber-reinforced part.

[0610] The preformed form of the reinforcing fibers can be selected taking into consideration the desired form of the composite material (also referred to as the reinforced part) to be formed, and the fibers may have the form of sheets, mats, beads, strands, threads, bands, webs, rovings, bands of rovings, bundles, etc.

[0611] The amount of reinforcing fiber can vary depending on the desired thermoset composite material.

[0612] The composition according to the present invention may optionally further comprise a filler.

[0613] Suitable fillers known to those skilled in the art are, for example, organic fillers such as thermoplastics and elastomers, or inorganic fillers such as glass microspheres, graphite, or silica.

[0614] Further suitable fillers known in the art are mineral powder fillers such as, for example, CaCO, coated CaCO, kaolin clay, SiO, talc, graphite, corundum (α-AlO), SiC, glass microspheres, mica, calcium silicate (CaOSi), wollastonite, MgO, anhydrous calcium sulfate (CaSO or anhydrite), ceramic hollow microspheres, fused mullite (AlO-SiO), boron nitride (BN), vermiculite, or basalt. Mixtures of the above fillers can also be used.

[0615] In one embodiment, the fillers that may be used in the present invention are independently selected from the group consisting of CaCO, coated CaCO, kaolin clay, SiO, talc, graphite, graphene / nanographene, carbon nanotubes (SWCNT and / or MWCNT), corundum (α-AlO), SiC, glass microspheres, mica, calcium silicate (CaOSi), wollastonite, MgO, anhydrous calcium sulfate (CaSO or anhydrite), ceramic hollow microspheres, fused mullite (AlO—SiO), boron nitride (BN), vermiculite, basalt, and mixtures thereof.

[0616] In another embodiment, the fillers are independently selected from the group consisting of CaC0, coated CaC0, kaolin clay, SiO, wollastonite, talc, graphene / nanographene, carbon nanotubes (SWCNT and / or MWCNT), and mixtures thereof.

[0617] In another embodiment, the fillers are independently selected from the group consisting of coated CaCO3, talc, and mixtures thereof.

[0618] The filler may be in the form of particles, powder, spheres, chips and / or strands and may have an average particle size ranging from nanoscale to millimeter level, preferably the filler has an average particle size of 0.01 to 1000 μm, more preferably the filler has an average particle size of 0.5 to 500 μm.

[0619] The amount of filler can vary and is preferably 5 to 60 wt.%, preferably 15 to 50 wt.%, more preferably 15 to 45 wt.%, based on the total weight of the thermosetting composite material.

[0620] The present invention is further defined by the following numbered items: 1. A composition comprising components (a) and (b), wherein component (a) is: (i) a difunctional cyanate ester compound of formula (I)

[0621] [ka]

[0622] (In the formula, R 1 ~R 8 are independently hydrogen, straight chain C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl, and phenoxy; R 1 ~R 8 At least one of the following is a straight chain C2 to C 10 Alkenyl and branched C3-C 10 alkenyl; Z1 indicates a direct bond or -O-, -S-, -S(=O)-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, -CH(CF3)-, -C(CF3)2-, -C(=O)-, -C(=CH2)-, -C(=CCl2)-, -Si(CH3)2-, straight chain C 1~10 Alkanediyl, branched chain C 4~10 Alkanediyl, C 3~8 Cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, -N(R 13 )-(wherein, R 13 is hydrogen, linear C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 cycloalkyl, phenyl, and phenoxy), and a moiety of formula

[0623] [ka]

[0624] wherein X represents a divalent moiety selected from the group consisting of: and oligomers, prepolymers, polymers, or mixtures thereof; Optionally, (a) is a mixture of (i) and (ii) polyfunctional cyanate esters of formula (II), (ii) is a polyfunctional cyanate ester of formula (II)

[0625] [ka]

[0626] (wherein n is an integer of 1 to 20; R 10 and R 11 are the same or different and independently represent hydrogen, linear C 1~10Alkyl, branched chain C 4~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-1)

[0627] [ka]

[0628] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0629] [ka]

[0630] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0631] [ka]

[0632] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0633] [ka]

[0634] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers, or mixtures thereof; or Any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4) and; Component (b) is a compound of formula (X)

[0635] [ka]

[0636] (wherein * and ** respectively indicate a covalent bond to the respective C atom of the residue indicated by * and **, The residues may be the same or different,

[0637] [ka]

[0638] are independently selected from R is independently selected from alkyl, cycloalkyl, alkyne, aryl, aralkyl, and alkaryl; Ra, Rb, and Rc are independently hydrogen, straight chain C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl and phenoxy; Alternatively, Ra and Rb, Ra and Rc, or Rb and Rc may join together to form a 3- to 8-membered cycloalkyl or a 3- to 8-membered cycloalkenyl. and one or more substituted bisimide compounds independently selected from an oligomer, a prepolymer, a polymer, or a mixture of these compounds.

[0639] 2. Component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0640] [ka]

[0641] (In the formula, R 1 ~R 8 are independently hydrogen, straight chain C 1~10 Alkyl, C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl, R 1 ~R 8 At least one of the following is a straight chain C2 to C 10 Alkenyl and branched C3-C 10alkenyl; Z 1 indicates a direct bond or -O-, -S-, -S(=O)-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, -CH(CF3)-, -C(CF3)2-, -C(=O)-, -C(=CH2)-, -C(=CCl2)-, -Si(CH3)2-, straight chain C 1~10 Alkanediyl, branched chain C 4~10 Alkanediyl, C 3~8 Cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, -N(R 13 )-(wherein, R 13 is hydrogen, linear C 1~10 Alkyl, C 3~8 cycloalkyl, phenyl, and phenoxy), and a moiety of formula

[0642] [ka]

[0643] wherein X represents a divalent moiety selected from the group consisting of: and oligomers, prepolymers, polymers, or mixtures thereof; Optionally, (a) is a mixture of (i) and (ii) polyfunctional cyanate esters of formula (II); (ii) is a polyfunctional cyanate ester of formula (II)

[0644] [ka]

[0645] (wherein n is an integer of 1 to 20; R 10 and R 11 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, straight chain C2-C 10Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-1)

[0646] [ka]

[0647] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0648] [ka]

[0649] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0650] [ka]

[0651] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0652] [ka]

[0653] 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).

[0654] 3. Component (b) is a compound of formula (X)

[0655] [ka]

[0656] (wherein * and ** respectively indicate a covalent bond to the respective C atom of the residue indicated by * and **, The residues may be the same or different,

[0657] [ka]

[0658] are independently selected from Ra, Rb, and Rc are independently hydrogen, straight chain C1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl and phenoxy; or Ra and Rb, Ra and Rc, or Rb and Rc may join together to form a 3- to 8-membered cycloalkyl or a 3- to 8-membered cycloalkenyl; R is independently an aryl, straight or branched chain C 1~10 Alkyl, C3-C8 cycloalkyl, C 2~10 an alkyne, or a moiety <<"N"-R-"N">>, wherein <<"N"-R-"N">> is an aromatic amine moiety independently selected from the following (where "N" denotes a point of attachment):

[0659] [ka]

[0660] where: R1, R2, R3 and R4 are each independently hydrogen, C2 to C 20 Alkyl, C2-C 20 Alkenes, C2-C 20 selected from alkynes, halogens (preferably Cl, Br, F, or I), NO, and sulfones; X is independently C1 to C 20 Alkyl, C2-C 20 Alkenes, C2-C 20 3. The composition of claim 1 or 2, wherein the bisimide compound is one or more substituted bisimide compounds independently selected from alkyl, alkoxy, methyl ...

[0661] 4. Component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0662] [ka]

[0663] (In the formula, R 1 ~R 8 are independently hydrogen, straight chain C 1~3 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl, R 1 ~R 8 At least one of the following is a straight chain C2 to C 10 Alkenyl and branched C3-C 10 alkenyl; Z 1 indicates a direct bond or -O-, -S-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, -C(CF3)2-, -C(=CCl2)-, branched chain C 4~6 Alkanediyl, C 3~8 one or more cyanate esters independently selected from the group consisting of cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, and oligomers, prepolymers, polymers, or mixtures thereof; Optionally, (a) is a mixture of (i) and (ii) polyfunctional cyanate esters of formula (II), (ii) is a polyfunctional cyanate ester of formula (II)

[0664] [ka]

[0665] (wherein n is an integer of 1 to 10; R 10 and R 11are the same or different and independently represent hydrogen, linear C 1~5 Alkyl, branched chain C 4~6 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-1)

[0666] [ka]

[0667] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0668] [ka]

[0669] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0670] [ka]

[0671] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0672] [ka]

[0673] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers, or mixtures thereof; or Any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4) 4. The composition of any one of items 1, 2 or 3, wherein

[0674] 5. The component (b) is a biscitraconimide compound of the formula (X1)

[0675] [ka]

[0676] wherein R is m-xylylene, and oligomers, prepolymers, polymers or mixtures thereof; or b1) at least one selected from the group consisting of biscitraconimide compounds of formula (X1), bisitaconimide compounds of formula (X2), and citraconic acid-itaconimide compounds of formula (X3), and oligomers, prepolymers, polymers, or mixtures thereof;

[0677] [ka]

[0678] or b2) Visnadic imide compounds of formula (X4), and oligomers, prepolymers, polymers or mixtures thereof

[0679] [ka]

[0680] (In the formula, Ra, Rb, and Rc are independently hydrogen, straight chain C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl and phenoxy; or Ra and Rb, Ra and Rc, or Rb and Rc may join together to form a 3- to 8-membered cycloalkyl or a 3- to 8-membered cycloalkenyl; or b3) Bistetrahydroimide compounds of formula (X5), and oligomers, prepolymers, polymers or mixtures thereof

[0681] [ka]

[0682] wherein R is independently aryl, straight or branched chain C1-C 10 Alkyl, C3-C8 cycloalkyl, C2-C 10 an alkyne or moiety <<"N"-R-"N">>, where <<"N"-R-"N">> is an aromatic amine moiety independently selected from the following (where "N" denotes a point of attachment):

[0683] [ka]

[0684] where: R1, R2, R3 and R4 are each independently hydrogen, C1 to C 20 Alkyl, C2-C 20 Alkenes, C2-C 20 selected from alkynes, halogens (preferably Cl, Br, F, or I), NO, and sulfones; X is independently C1 to C 20 Alkyl, C2-C 20 Alkenes, C2-C 20 alkynes and sulfones and oligomers, prepolymers, polymers or mixtures thereof 5. The composition of any one of items 1, 2, 3 or 4, wherein the bisimide is a substituted bisimide independently selected from

[0685] 6. Component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0686] [ka]

[0687] and one or more cyanate esters independently selected from The difunctional cyanate ester of formula I is i)R 1and R 5 is an allylic and R 2 and R 6 is methyl, and R 3 , R 4 , R 7 and R 8 is hydrogen, and Z 1 is -CH2- (methylene); ii)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -CH2- (methylene); iii)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -C(CH3)2-; iv) R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -C(=O)-; v)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -S(=O)-; vi)R 1 and R 5 is an allylic and R 2 , R 3 , R4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 but -S-; vii)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -C(CF3)2-; viii)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -C(=CCl2)-; ix)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 but,

[0688] [ka]

[0689] independently selected from the group consisting of: x)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 but,

[0690] [ka]

[0691] Something that is; or xi)R 1 and R 5 is an allylic and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, and Z 1 is -CH(CH3)-; and oligomers, prepolymers, polymers or mixtures thereof are independently selected from the group consisting of Optionally, (a) is a mixture of (i) and (ii) polyfunctional cyanate esters of formula (II), (ii) is a polyfunctional cyanate ester of formula (II)

[0692] [ka]

[0693] and the polyfunctional cyanate ester is independently selected from Compound III, Compound IV, Compound V, Compound VI, and oligomers, prepolymers, polymers, or mixtures thereof.

[0694] [ka]

[0695] or selected from the group consisting of Polyfunctional cyanate ester of formula (IX-1)

[0696] [ka]

[0697] (wherein n is an integer of 1 to 20; R30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0698] [ka]

[0699] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0700] [ka]

[0701] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0702] [ka]

[0703] wherein n is an integer from 1 to 20; and oligomers, prepolymers, polymers or mixtures thereof; or Any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4) 6. The composition of any one of items 1, 2, 3, 4 or 5, wherein

[0704] 7. Component (b) is a biscitraconimide compound of formula (X1)

[0705] [ka]

[0706] wherein R is m-xylylene, and oligomers, prepolymers, polymers or mixtures thereof; or b1) at least one selected from the group consisting of biscitraconimide compounds of formula (X1), bisitaconimide compounds of formula (X2), and citraconic acid-itaconimide compounds of formula (X3), and oligomers, prepolymers, polymers, or mixtures thereof;

[0707] [ka]

[0708] or b2) Visnadic imide compounds of formula (X4), and oligomers, prepolymers, polymers or mixtures thereof

[0709] [ka]

[0710] (In the formula, Ra, Rb, and Rc are independently hydrogen, straight chain C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, straight chain C2-C 10 Alkenyl, branched C3-C 10 Alkenyl, C 1~10 selected from the group consisting of alkoxy, halogen, phenyl and phenoxy; or Ra and Rb, Ra and Rc, or Rb and Rc may join together to form a 3- to 8-membered cycloalkyl or a 3- to 8-membered cycloalkenyl; or b3) Bistetrahydroimide compounds of formula (X5), and oligomers, prepolymers, polymers or mixtures thereof

[0711] [ka]

[0712] wherein R is the moiety "N"-R-"N"; and the moiety "N"-R-"N" is an aromatic amine moiety independently selected from the following (where "N" denotes a point of attachment):

[0713] [ka]

[0714] where: R1, R2, R3 and R4 are each independently selected from hydrogen, C1-C5 alkyl, halogen (preferably Cl, Br, or F), NO2, and sulfone; X is independently C1 to C 20 Alkyl, C2-C 20Alkenes, C2-C 20 selected from alkynes and sulfones); and oligomers, prepolymers, polymers or mixtures thereof 7. The composition of any one of items 1, 2, 3, 4, 5 or 6, wherein the bisimide is one or more substituted bisimides independently selected from:

[0715] 8. The composition of any one of items 1, 2, 3, 4, 5, 6 or 7, wherein the ratio of component (a) to (b) is 80 wt.% component (a) to 20 wt.% component (b), based on the total amount of the resin composition.

[0716] 9. The composition of any one of items 1, 2, 3, 4, 5, 6, 7 or 8, 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 5- or 6-membered nitrogen-containing heterocycle, hydroxyamines, phosphines, phenols, bisphenols, and mixtures thereof.

[0717] 10. The catalyst is a compound of formula (VII)

[0718] [ka]

[0719] (In the formula, R 1 ~R 8 are independently hydrogen, straight chain C 1~10 Alkyl, straight chain C2-C 10 Alkenyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, branched chain C3-C 10 Alkenyl, halogenated branched chain C 4~10 Alkyl, C 3~8 Cycloalkyl, halogenated C 3~8 Cycloalkyl, C 1~10selected from the group consisting of alkoxy, halogen, phenyl, and phenoxy; R 1 ~R 8 At least one of the following is a straight chain C2 to C 10 Alkenyl and branched C3-C 10 alkenyl; Z represents a direct bond or -O-, -S-, -S(=O)-, -S(=O)2-, -CH2-, -CH(CH3)-, -C(CH3)2-, -CH(CF3)-, -C(CF3)2-, -C(=O)-, -C(=CH2)-, -C(=CCl2)-, -Si(CH3)2-, linear C 1~10 Alkanediyl, branched chain C 4~10 Alkanediyl, C 3~8 Cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, -N(R 13 )-(wherein, R 13 is hydrogen, linear C 1~10 Alkyl, halogenated linear C 1~10 Alkyl, branched chain C 4~10 Alkyl, halogenated branched chain C 4~10 Alkyl, C 3~8 cycloalkyl, phenyl, and phenoxy), and a moiety of formula

[0720] [ka]

[0721] wherein X is independently selected from hydrogen and halogen, and a divalent moiety selected from the group consisting of: and oligomers, prepolymers, polymers, or mixtures thereof.

[0722] 11. The composition according to item 9 or 10, wherein the catalyst is present in an amount of about 0 to 20 wt.%, based on the total amount of the resin composition.

[0723] 12. The composition of any one of items 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, wherein the composition further comprises reinforcing fibers selected from the group consisting of carbon fibers, glass fibers (e.g., E-glass fibers, S-glass fibers), aramid fibers (e.g., KEVLAR®, etc.), basalt fibers (geotextile fibers), natural fibers (e.g., flax, hemp, jute, or sisal), fleece and woven fabrics (multi-layer or single layer), and mixtures thereof.

[0724] 13. The composition of any one of items 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12, wherein the composition further comprises a filler selected from the group consisting of organic fillers such as thermoplastics and elastomers, inorganic fillers such as glass microspheres, graphite, graphene / nanographene, carbon nanotubes (SWCNT and / or MWCNT) or silica, and mineral powder fillers such as CaCO, coated CaCO, kaolin clay, SiO, talc, graphite, corundum (α-AlO), wollastonite, SiC, glass microspheres, mica, calcium silicate (CaOSi), MgO, anhydrous calcium sulfate (CaSO or anhydrite), ceramic hollow microspheres, fused mullite (AlO—SiO), boron nitride (BN), vermiculite, or basalt, and mixtures thereof.

[0725] 14. Component (a) is (i) a difunctional cyanate ester compound of formula (I)

[0726] [ka]

[0727] (In the formula, R 1 ~R 8 are independently hydrogen, straight chain C2 to C 10 Alkenyl and branched C3-C 10 alkenyl, R1 ~R 8 At least one of the following is a straight chain C2 to C 10 Alkenyl and branched C3-C 10 alkenyl, Preferably, R 1 and R 5 are each independently a straight chain C2 to C 10 Alkenyl or branched C3-C 10 alkenyl, and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen, Even more preferably, R 1 and R 5 is an aryl and R 2 , R 3 , R 4 , R 6 , R 7 and R 8 is hydrogen; Z 1 is -C(CH3)2-) and one or more cyanate esters independently selected from: and oligomers, prepolymers, polymers, or mixtures thereof; Optionally, (a) is a mixture of (i) and (ii); (ii) is a polyfunctional cyanate ester of formula (II)

[0728] [ka]

[0729] wherein the polyfunctional cyanate ester is independently selected from the group consisting of Compound III, Compound IV, and Compound V, and oligomers, prepolymers, polymers, or mixtures thereof;

[0730] [ka]

[0731] or Polyfunctional cyanate ester of formula (IX-1)

[0732] [ka]

[0733] (wherein n is an integer of 1 to 20; R 30 , R 31 , R 32 and R 33 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2)

[0734] [ka]

[0735] (wherein n is an integer of 1 to 20; R 34 , R 35 and R 36 are the same or different and independently represent hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3)

[0736] [ka]

[0737] (wherein n is an integer of 1 to 20; R 37 is hydrogen, linear C 1~10 Alkyl, branched chain C 3~10 Alkyl, straight chain C2-C 10 Alkenyl and branched C3-C 10 alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4)

[0738] [ka]

[0739] wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers, or mixtures thereof; or Any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4) and; Component (b) is a biscitraconimide compound of formula (X1)

[0740] [ka]

[0741] 14. The composition according to any one of items 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13, wherein R is m-xylylene and oligomers, prepolymers, polymers or mixtures thereof.

[0742] 15. A method for preparing a composition according to any one of items 1 to 14, comprising: i) providing the components of the mixture according to any one of items 1 to 14; and ii) intimately mixing the ingredients together The above method, comprising:

[0743] 16. A method for the preparation of a thermosetting composite material, comprising: i) providing the components of the mixture according to any one of items 1 to 14; ii) intimately mixing the ingredients together; iii) casting the mixture into a desired form; and iv) initiating polymerization of the mixture. The above method, comprising:

[0744] 17. Use of a composition as defined in any one of items 1 to 14 for producing a thermosetting composite material.

[0745] 18. The thermosetting composite material of any one of items 16 or 17, exhibiting a mass loss of less than about 2.5 wt.%, preferably a mass loss of less than about 2.0 wt.%, and more preferably a mass loss of less than about 1.75 wt.% after 1000 hours at 250°C. [Example]

[0746] [Table 1]

[0747] Experimental Procedure for Comparative Example 1 6 g of DABA-CN was poured into an aluminum pan with a diameter of 5 cm at room temperature and subsequently cured according to the following curing cycle: Cure cycle: 1K / min from 25°C to 175°C, hold at 175°C for 3 hours Heat from 175°C to 220°C at 1K / min, hold at 220°C for 2 hours Heat from 220 to 260°C at 1 K / min and hold at 260°C for 16 hours.

[0748] The cured DABA-CN material was cooled to room temperature and removed from the aluminum pan (de-mold). The cured material was evaluated in terms of mass loss (thermo-oxidative stability) and glass transition temperature.

[0749] The hardened material had the following dimensions: diameter = 5 cm, thickness = 2 cm.

[0750] Experimental Procedures for Examples 2, 3 and 4 DABA-CN and Perkalink were mixed at 90-100°C until homogenization was complete, and 6 g of the mixture was poured into an aluminum pan with a diameter of 5 cm, followed by curing according to the following curing cycle: Cure cycle: 1K / min from 25°C to 175°C, hold at 175°C for 3 hours Heat from 175°C to 220°C at 1K / min, hold at 220°C for 2 hours Heat from 220 to 260°C at 1 K / min and hold at 260°C for 16 hours.

[0751] The cured material was cooled to room temperature and removed from the aluminum pan (de-mold). The cured material was evaluated in terms of mass loss (thermo-oxidative stability) and glass transition temperature.

[0752] The hardened material had the following dimensions: diameter = 5 cm, thickness = 2 cm.

[0753] The ingredients used in Comparative Example 1 and Examples 2, 3 and 4 and their amounts in grams (g) and wt.% (% based on the total weight of the mixture) are shown in Table 1 (g) and Table 2 (wt.%).

[0754] [Table 2]

[0755] Experimental Procedures for Testing Cured Samples of Comparative Example 1 and Examples 2, 3, and 4 Thermal oxidative stability: The thermo-oxidative stability of the above cured samples was evaluated based on weight loss during isothermal aging at 250°C. The cured samples (5 cm diameter and 2 cm thickness) were placed in an oven at 250°C for long-term aging tests. Before starting the aging test, the initial weight (w0) of the cured sample was measured with an analytical balance with a resolution of at least 0.1 mg. The sample was then reweighted (w) after different thermal aging periods at 250°C. xhours The corresponding mass loss in % was calculated using the following formula: Mass loss [%]=((w0-w xhours ) / w0)×100 The samples were then placed back in the oven at 250° C. to continue the aging test. The weight loss results are shown in Table 3.

[0756] Glass transition temperature: In addition to the thermo-oxidative stability testing, samples of the cured compositions obtained after the cure cycles defined above for Comparative Example 1 and Examples 2, 3, and 4 were cut into specimens and analyzed for glass transition temperature (Tg) by thermomechanical analysis (TMA).

[0757] The glass transition temperature is the temperature at which the physical properties of a polymeric material change from an amorphous, hard, glassy or crystalline state to a flexible, rubber-like state. The instrument used was a Mettler Toledo TMA SDTA840 instrument. The sample dimensions were 6 x 6 mm. 2 (length × width) and a thickness of 2.0 mm. In this test method, two heating gradients were applied (first heating: 25 to 250°C at 10 K / min, second heating: 25 to 400°C at 10 K / min). Tg was evaluated with the second gradient. The results are shown in Table 3.

[0758] [Table 3]

Claims

1. A composition comprising components (a) and (b), Component (a) is (i) a difunctional cyanate ester compound of formula (I) 【Chemistry 1】 (In the formula, R １ ~R ８ are independently hydrogen, linear C １～１０ Alkyl, halogenated linear C １～１０ Alkyl, branched chain C ４～１０ Alkyl, halogenated branched chain C ４～１０ Alkyl, C ３～８ Cycloalkyl, halogenated C ３～８ Cycloalkyl, linear C ２ ~C １０ Alkenyl, branched chain C ３ ~C １０ Alkenyl, C １～１０ selected from the group consisting of alkoxy, halogen, phenyl, and phenoxy; R １ ~R ８ At least one of the ２ ~C １０ Alkenyl and Branched Chain C ３ ~C １０ alkenyl, Z １ represents a direct bond or -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 chain C ４～１０ Alkanediyl, C ３～８ Cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, -N(R １３ )-(wherein, R １３ is hydrogen, linear C １～１０ Alkyl, halogenated linear C １～１０ Alkyl, branched chain C ４～１０ Alkyl, halogenated branched chain C ４～１０ Alkyl, C ３～８ cycloalkyl, phenyl, and phenoxy), and a moiety of formula 【Chemistry 2】 wherein X is independently selected from hydrogen and halogen; and one or more cyanate esters independently selected from the group consisting of: (a) is a mixture of (i) and (ii), (ii) is Polyfunctional cyanate ester of formula (II) 【Transformation 3】 (wherein n is an integer from 1 to 20; R １０ and R １１ are the same or different and independently represent hydrogen, linear C １～１０ Alkyl, branched chain C ４～１０ Alkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-1) 【Chemistry 4】 (wherein n is an integer from 1 to 20; R ３０ , R ３１ , R ３２ and R ３３ are the same or different and independently represent hydrogen, linear C １～１０ Alkyl, branched chain C ３～１０ Alkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2) 【Transformation 5】 (wherein n is an integer from 1 to 20; R ３４ , R ３５ and R ３６ are the same or different and independently represent hydrogen, linear C １～１０ Alkyl, branched chain C ３～１０ Alkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3) 【Transformation 6】 (wherein n is an integer from 1 to 20; R ３７ is hydrogen, linear C １～１０ Alkyl, branched chain C ３～１０ Alkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4) 【Transformation 7】 wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers or mixtures thereof; or Any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4). and Component (b) is Biscitraconimide compounds of formula (X1), bisitaconimide compounds of formula (X2), and citraconic acid-itaconimide compounds of formula (X3) 【Transformation 8】 wherein R is m-xylylene, and oligomers, prepolymers, polymers or mixtures thereof and one or more substituted bisimide compounds selected from the group consisting of: The above composition, wherein the ratio of component (a) to component (b) is within the range of 10 to 70 wt. % of component (a) to 90 to 30 wt. % of component (b), based on the total amount of the resin composition.

2. Component (a) is (i) a difunctional cyanate ester compound of formula (I) 【Chemistry 9】 (In the formula, R １ ~R ８ are independently hydrogen, linear C １～１０ Alkyl, C ３～８ Cycloalkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl, R １ ~R ８ At least one of the ２ ~C １０ Alkenyl and Branched Chain C ３ ~C １０ alkenyl, Z １ represents a direct bond or -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 chain C ４～１０ Alkanediyl, C ３～８ Cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, -N(R １３ )-(wherein, R １３ is hydrogen, linear C １～１０ Alkyl, C ３～８ cycloalkyl, phenyl, and phenoxy), and a moiety of formula 【Chemistry 10】 wherein X is independently selected from hydrogen and halogen; and one or more cyanate esters independently selected from the group consisting of: (a) is a mixture of (i) and (ii), (ii) is Polyfunctional cyanate ester of formula (II) 【Chemistry 11】 (wherein n is an integer from 1 to 20; R １０ and R １１ are the same or different and independently represent hydrogen, linear C １～１０ Alkyl, branched chain C ４～１０ Alkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-1) 【Chemistry 12】 (wherein n is an integer from 1 to 20; R ３０ , R ３１ , R ３２ and R ３３ are the same or different and independently represent hydrogen, linear C １～１０ Alkyl, branched chain C ３～１０ Alkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2) 【Chemistry 13】 (wherein n is an integer from 1 to 20; R ３４ , R ３５ and R ３６ are the same or different and independently represent hydrogen, linear C １～１０ Alkyl, branched chain C ３～１０ Alkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3) 【Chemistry 14】 (wherein n is an integer from 1 to 20; R ３７ is hydrogen, linear C １～１０ Alkyl, branched Chain C ３～１０ Alkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4) 【Chemistry 15】 wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers or mixtures thereof; or Any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4).

2. The composition of claim 1, wherein:

3. Component (a) is (i) a difunctional cyanate ester compound of formula (I) 【Chemistry 16】 (In the formula, R １ ~R ８ are independently hydrogen, linear C １～３ Alkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl, R １ ~R ８ At least one of the ２ ~C １０ Alkenyl and Branched Chain C ３ ~C １０ alkenyl, Z １ represents a direct bond or -O-, -S-, -S(=O) ２ -, -CH ２ -, -CH(CH ３ ) -, -C(CH ３ ) ２ -, -C(CF ３ ) ２ -, -C(=CCl ２ ) -, branched chain C ４～６ Alkanediyl, C ３～８ or one or more cyanate esters independently selected from the group consisting of cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, and oligomers, prepolymers, polymers, or mixtures thereof; (a) is a mixture of (i) and (ii), (ii) is Polyfunctional cyanate ester of formula (II) 【Chemistry 17】 (wherein n is an integer from 1 to 10; R １０ and R １１ are the same or different and independently represent hydrogen, linear C １～５ Alkyl, branched chain C ４～６ Alkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-1) [Chemistry 18] (wherein n is an integer from 1 to 20; R ３０ , R ３１ , R ３２ and R ３３ are the same or different and independently represent hydrogen, linear C １～１０ Alkyl, branched chain C ３～１０ Alkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2) 【Chemistry 19】 (wherein n is an integer from 1 to 20; R ３４ , R ３５ and R ３６ are the same or different and independently represent hydrogen, linear C １～１０ Alkyl, branched chain C ３～１０ Alkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3) 【Chemistry 20】 (wherein n is an integer from 1 to 20; R ３７ is hydrogen, linear C １～１０ Alkyl, branched chain C ３～１０ Alkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4) 【Chemistry 21】 wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers or mixtures thereof; or Any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4). The composition according to claim 1 or 2,

4. Component (a) is (i) a difunctional cyanate ester compound of formula (I) 【Chemistry 22】 and one or more cyanate esters selected from The difunctional cyanate ester of formula I is i) R １ and R ５ is allyl and R ２ and R ６ is methyl, and R ３ , R ４ , R ７ and R ８ is hydrogen, and Z １ But -CH ２ -(methylene); ii) R １ and R ５ is allyl and R ２ , R ３ , R ４ , R ６ , R ７ and R ８ is hydrogen, and Z １ But -CH ２ -(methylene); iii) R １ and R ５ is allyl and R ２ , R ３ , R ４ , R ６ , R ７ and R ８ is hydrogen, and Z １ But -C(CH ３ ) ２ - that which is; iv) R １ and R ５ is allyl and R ２ , R ３ , R ４ , R ６ , R ７ and R ８ is hydrogen, and Z １ is —C(═O)—; v) R １ and R ５ is allyl and R ２ , R ３ , R ４ , R ６ , R ７ and R ８ is hydrogen, and Z １ is —S(═O)—; vi) R １ and R ５ is allyl and R ２ , R ３ , R ４ , R ６ , R ７ and R ８ is hydrogen, and Z １ is -S-; vii) R １ and R ５ is allyl and R ２ , R ３ , R ４ , R ６ , R ７ and R ８ is hydrogen, and Z １ But -C(CF ３ ) ２ - that which is; viii) R １ and R ５ is allyl and R ２ , R ３ , R ４ , R ６ , R ７ and R ８ is hydrogen, and Z １ But -C(=CCl ２ )-; ix) R １ and R ５ is allyl and R ２ , R ３ , R ４ , R ６ , R ７ and R ８ but , hydrogen, and Z １ but, 【Chemistry 23】 Independently selected from the group consisting of: x) R １ and R ５ is allyl and R ２ , R ３ , R ４ , R ６ , R ７ and R ８ is hydrogen, and Z １ but, 【Chemistry 24】 or xi) R １ and R ５ is allyl and R ２ , R ３ , R ４ , R ６ , R ７ and R ８ is hydrogen, and Z １ But -CH(CH ３ )-; and oligomers, prepolymers, polymers or mixtures thereof or independently selected from the group consisting of (a) is a mixture of (i) and (ii); (ii) is Polyfunctional cyanate ester of formula (II) 【Chemistry 25】 and the polyfunctional cyanate ester is Compound III, Compound IV, Compound V, Compound VI, and oligomers, prepolymers, polymers, or mixtures thereof. 【Chemistry 26】 or independently selected from the group consisting of: or Polyfunctional cyanate ester of formula (IX-1) 【Chemistry 27】 (wherein n is an integer from 1 to 20; R ３０ , R ３１ , R ３２ and R ３３ are the same or different and independently represent hydrogen, linear C １～１０ Alkyl, branched chain C ３～１０ Alkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2) 【Chemistry 28】 (wherein n is an integer from 1 to 20; R ３４ , R ３５ and R ３６ are the same or different and independently represent hydrogen, linear C １～１０ Alkyl, branched chain C ３～１０ Alkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3) 【Chemistry 29】 (wherein n is an integer from 1 to 20; R ３７ is hydrogen, linear C １～１０ Alkyl, branched chain C ３～１０ Alkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4) 【Transformation 30】 wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers or mixtures thereof; or 3. The composition of claim 1 or 2, which is any combination of polyfunctional cyanate esters of formulas (II), (IX-1), (IX-2), (IX-3), and (IX-4).

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

6. 3. The composition of claim 1 or 2, further comprising 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 5- or 6-membered nitrogen-containing heterocycle, hydroxyamines, phosphines, phenols, bisphenols, and mixtures thereof.

7. the catalyst is a compound of formula (VII) and its oligomers, prepolymers, polymers or mixtures 【Chemistry 31】 (In the formula, R １ ~R ８ are independently hydrogen, linear C １～１０ Alkyl, linear C ２ ~C １０ Alkenyl, halogenated linear C １～１０ Alkyl, branched chain C ４～１０ Alkyl, branched chain C ３ ~C １０ Alkenyl, halogenated branched chain C ４～１０ Alkyl, C ３～８ Cycloalkyl, halogenated C ３～８ Cycloalkyl, C １～１０ selected from the group consisting of alkoxy, halogen, phenyl, and phenoxy; R １ ~R ８ At least one of the ２ ~C １０ Alkenyl and Branched Chain C ３ ~C １０ alkenyl, Z represents a direct bond, or -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 chain C ４～１０ Alkanediyl, C ３～８ Cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, -N(R １３ )-(wherein, R １３ is hydrogen, linear C １～１０ Alkyl, halogenated linear C １～１０ Alkyl, branched chain C ４～１０ Alkyl, halogenated branched chain C ４～１０ Alkyl, C ３～８ cycloalkyl, phenyl, and phenoxy), and a moiety of formula 【Chemistry 32】 wherein X represents a divalent moiety selected from the group consisting of: The composition of claim 6, wherein

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

9. 3. The composition of claim 1 or 2, further comprising reinforcing fibers selected from the group consisting of carbon fibers, glass fibers, aramid fibers, basalt fibers, natural fibers, fleece, and woven fabrics, and mixtures thereof.

10. Organic fillers; selected from glass microspheres, graphite, graphene / nanographene, carbon nanotubes (SWCNT and / or MWCNT) or silica 3. The composition of claim 1, further comprising a filler selected from: inorganic fillers containing hydroxypropyl methylcellulose; and mineral powder fillers; and mixtures thereof.

11. Component (a) is (i) a difunctional cyanate ester compound of formula (I) 【Transformation 33】 (In the formula, R １ ~R ８ are independently hydrogen, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl, R １ ~R ８ At least one of the ２ ~C １０ Alkenyl and Branched Chain C ３ ~C １０ alkenyl; Z １ is -C(CH ３ ) ２ -) and one or more cyanate esters independently selected from oligomers, prepolymers, polymers or mixtures thereof; or (a) is a mixture of (i) and (ii); (ii) is Polyfunctional cyanate ester of formula (II) 【Transformation 34】 and the polyfunctional cyanate ester is independently selected from Compound III, Compound IV, Compound V, and oligomers, prepolymers, polymers, or mixtures thereof. 【Chemistry 35】 or selected from the group consisting of: or Polyfunctional cyanate ester of formula (IX-1) 【Transformation 36】 (wherein n is an integer from 1 to 20; R ３０ , R ３１ , R ３２ and R ３３ are the same or different and independently represent hydrogen, linear C １～１０ Alkyl, branched chain C ３～１０ Alkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-2) 【Chemistry 37】 (wherein n is an integer from 1 to 20; R ３４ , R ３５ and R ３６ are the same or different and independently represent hydrogen, linear C １～１０ Alkyl, branched chain C ３～１０ Alkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-3) 【Transformation 38】 (wherein n is an integer from 1 to 20; R ３７ is hydrogen, linear C １～１０ Alkyl, branched chain C ３～１０ Alkyl, linear C ２ ~C １０ Alkenyl, and branched chain C ３ ~C １０ alkenyl) and oligomers, prepolymers, polymers or mixtures thereof; or Polyfunctional cyanate ester of formula (IX-4) 【Chemistry 39】 wherein n is an integer from 1 to 20, and oligomers, prepolymers, polymers or mixtures thereof; or Any combination of polyfunctional cyanate esters of formula (II), (IX-1), (IX-2), (IX-3), and (IX-4); Component (b) is Biscitraconimide compounds of formula (X1) 【Chemistry 40】 3. The composition of claim 1 or 2, wherein R is m-xylylene, and oligomers, prepolymers, polymers or mixtures thereof.

12. R １ and R ５ are each independently a linear C ２ ~C １０ Alkenyl or branched chain C ３ ~C １０ alkenyl, and R ２ , R ３ , R ４ , R ６ , R ７ and R ８ 3. The composition of claim 1 or 2, wherein is hydrogen.

13. R １ and R ５ is allyl, and R ２ , R ３ , R ４ , R ６ , R ７ and R ８ 3. The composition of claim 1 or 2, wherein is hydrogen.

14. 3. A method for the preparation of a composition according to claim 1 or 2, comprising: i) providing components (a) and (b) according to claim 1 or 2; and ii) mixing components (a) and (b) together A method comprising:

15. 1. A method for the preparation of a thermosetting composite material, comprising: i) providing components (a) and (b) according to claim 1 or 2; ii) mixing components (a) and (b) together; iii) providing fibers, fillers, pigments, and / or additives; iv) contacting the mixture obtained in step ii) with fibers, fillers, pigments, and / or additives; and v) initiating polymerization of the mixture obtained in step iv). The above method, comprising:

16. 10. Use of a composition as defined in claim 1 or 2 for producing a thermosetting composite material.

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