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US 12,163,024 B2Granted
Compositions with improved characteristics
AssigneeArxada AG
InventorsGaetano La Delfa, Stefan Ellinger, Roger Mazotti, Magnus Abgottspon, Viktor Dick
Life of this patent
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Abstract
The present invention relates to novel compositions comprising cyanate ester resins and substituted bisimides (citraconimides, bisitaconimide, citraconimido-itaconimide, bisnadicimide, bistetrahydroimide and mixtures thereof) as defined in claim 1, and thermoset composite materials based on these compositions.
Claims16
A composition comprising components (a) and (b) wherein component (a) is one or more cyanate esters independently selected from
- (i) a difunctional cyanate ester compound of formula (I)
- wherein
- R1 through R8 are independently selected from the group consisting of hydrogen, linear C1-10 alkyl, halogenated linear C1-10 alkyl, branched C4-10 alkyl, halogenated branched C4-10 alkyl, C3-8 cycloalkyl, halogenated C3-8 cycloalkyl, C1-10 alkoxy, halogen, phenyl and phenoxy;
- Z1 indicates a direct bond or a divalent moiety selected from the group consisting of —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 C1-10 alkanediyl, branched C4-10 alkanediyl, C3-8 cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, —N(R13)— wherein R13 is selected from the group consisting of hydrogen, linear C1-10 alkyl, halogenated linear C1-10 alkyl, branched C4-10 alkyl, halogenated branched C4-10 alkyl, C3-8 cycloalkyl, phenyl and phenoxy, and moieties of formulas
- wherein X is independently selected from hydrogen and halogen;
- and oligomers, prepolymers, polymers or mixtures thereof;
- and
- (ii) a polyfunctional cyanate ester of formula (II)
- wherein
- n is an integer from 1 to 20;
- and R10 and R11 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C1-10 alkyl and branched C4-10 alkyl;
- and oligomers, prepolymers, polymers or mixtures thereof;
- and wherein
- component (b) is one or more substituted bisimide compound independently selected from a compound of formula (X)
- wherein * and ** each denotes a covalent bond to the respective C atom denoted with * and of a residue,
- wherein the residues are identical or different and independently selected from
- and wherein R is independently selected from C7-8 cycloalkyl, C2-10 alkyne or the moiety <<“N”—R—“N”>>, wherein “N” denotes the point of connectivity and <<“N”—R—“N”>> is an aromatic amine moiety independently selected from
- wherein
- “N” corresponds to N in formula (X), and
- R1, R2, and R3 are each independently selected from hydrogen, C2-C20 alkyl, C2-C20 alkene, C2-C20 alkyne, halogen, NO2, and sulfone, wherein the halogen is selected from Cl, Br, F, or I;
- and oligomers, prepolymers, polymers or mixtures of these compounds.
18 more elements
A composition comprising components (a) and (b) wherein component (a) is one or more cyanate esters independently selected from
- (i) a difunctional cyanate ester compound of formula (I)
- wherein
- R1 through R8 are independently selected from the group consisting of hydrogen, linear C1-10 alkyl, halogenated linear C1-10 alkyl, branched C4-10 alkyl, halogenated branched C4-10 alkyl, C3-8 cycloalkyl, halogenated C3-8 cycloalkyl, C1-10 alkoxy, halogen, phenyl and phenoxy;
- Z1 indicates a direct bond or a divalent moiety selected from the group consisting of —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 C1-10 alkanediyl, branched C4-10 alkanediyl, C3-8 cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, —N(R13)— wherein R13 is selected from the group consisting of hydrogen, linear C1-10 alkyl, halogenated linear C1-10 alkyl, branched C4-10 alkyl, halogenated branched C4-10 alkyl, C3-8 cycloalkyl, phenyl and phenoxy, and moieties of formulas
- wherein X is independently selected from hydrogen and halogen;
- and oligomers, prepolymers, polymers or mixtures thereof;
- and
- (ii) a polyfunctional cyanate ester of formula (II)
- wherein
- n is an integer from 1 to 20;
- and R10 and R11 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C1-10 alkyl and branched C4-10 alkyl;
- and oligomers, prepolymers, polymers or mixtures thereof;
- wherein component (b) is one or more substituted bisimide independently selected from
- b1) at least one selected from the group of biscitraconimide compound of formula (X1), bisitaconimide compound of formula (X2) and citraconimido-itaconimide compound of formula (X3),
- or
- b2) a bisnadicimide compound of formula (X4) and oligomers, prepolymers, polymers or mixtures thereof,
- or
- b3) a bistetrahydroimide compound of formula (X5) and oligomers, prepolymers, polymers or mixtures thereof
- wherein R is the moiety << “N”—R—“N”>>, wherein “N” denotes the point of connectivity and R is an aromatic amine moiety independently selected from
- wherein
- R1, R2, and R3 are each independently selected from hydrogen, C1-C5 alkyl, halogen, NO2, and sulfone, wherein the halogen is selected from Cl, Br or F;
- and oligomers, prepolymers, polymers or mixtures thereof.
19 more elements
A composition comprising components (a) and (b) wherein component (a) is one or more cyanate esters independently selected from
- (i) a difunctional cyanate ester compound of formula (I)
- wherein
- R1 through R8 are independently selected from the group consisting of hydrogen, linear C1-10 alkyl, halogenated linear C1-10 alkyl, branched C4-10 alkyl, halogenated branched C4-10 alkyl, C3-8 cycloalkyl, halogenated C3-8 cycloalkyl, C1-10 alkoxy, halogen, phenyl and phenoxy;
- Z1 indicates a direct bond or a divalent moiety selected from the group consisting of —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 C1-10 alkanediyl, branched C4-10 alkanediyl, C3-8 cycloalkanediyl, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, —N(R13)— wherein R13 is selected from the group consisting of hydrogen, linear C1-10 alkyl, halogenated linear C1-10 alkyl, branched C4-10 alkyl, halogenated branched C4-10 alkyl, C3-8 cycloalkyl, phenyl and phenoxy, and moieties of formulas
- wherein X is independently selected from hydrogen and halogen;
- and oligomers, prepolymers, polymers or mixtures thereof;
- and
- (ii) a polyfunctional cyanate ester of formula (II)
- wherein
- n is an integer from 1 to 20;
- and R10 and R11 are identical or different and independently from each other selected from the group consisting of hydrogen, linear C1-10 alkyl and branched C4-10 alkyl;
- and oligomers, prepolymers, polymers or mixtures thereof;
- and wherein
- component (b) is one or more substituted bisimide independently selected from
- b1) at least one selected from the group of biscitraconimide compound of formula (X1), bisitaconimide compound of formula (X2) and citraconimido-itaconimide compound of formula (X3), and oligomers, prepolymers, polymers or mixtures thereof,
- or
- b2) a bisnadicimide compound of formula (X4) and oligomers, prepolymers, polymers or mixtures thereof,
- or
- b3) a bistetrahydroimide compound of formula (X5) and oligomers, prepolymers, polymers or mixtures thereof,
- wherein R is o-xylylene;
- and oligomers, prepolymers, polymers or mixtures thereof.
18 more elements
Dependencies are inferred from the claim text.