Curable organosiloxane-modified reaction resins
A curable composition of cyanate ester resin and poly(diorgano)siloxane with phenolic hydroxy groups addresses brittleness and hydrolysis issues, enhancing crack strength and water resistance in composite materials.
Patent Information
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2024-08-28
- Publication Date
- 2026-03-05
AI Technical Summary
Existing cyanate ester resin systems used in composite materials suffer from brittleness and susceptibility to hydrolysis due to high cross-linking density, leading to low crack strength and increased water absorption, which limits their use in high-temperature applications.
A curable composition of organic cyanate ester resin and linear poly(diorgano)siloxane with phenolic hydroxy groups, which are miscible without pre-crosslinking, resulting in modified polycyanurate networks with reduced water absorption and improved crack strength.
The modified networks exhibit reduced water absorption, higher fracture toughness, and high glass transition temperature, maintaining mechanical strength and thermal resistance without segregation or sticky surfaces.
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Abstract
Description
[0001]WA12420S / Mk Curable Organosiloxane-Modified Reaction Resins The invention relates to curable compositions of reaction resins with polymerizable functional cyanate ester groups and poly(diorgano)siloxanes with phenolic hydroxy groups, processes for their production, and cured materials and composites obtainable therefrom, which exhibit low water absorption, high fracture toughness, and a high glass transition temperature. Epoxy (EP) resins or epoxy resin systems are used in a wide variety of applications and have become established today in composite materials, for example in combination with glass, carbon (CFRP), or aramid fibers, as one of the most widely used thermoset classes. In addition, high-performance organic reaction resins, such as cyanate ester (CE), bismaleimide (BMI), polyimide (PI), benzoxazine, or phthalonitrile resins, orReactive resin mixtures, such as bis(benzocyclobutenimide) / bismaleimide, cyanate ester / epoxide, or bismaleimide / cyanate ester (BT resins), have gained increasing importance as matrix resins in fiber-reinforced composites in industry, automotive engineering, and aerospace in recent years. Compared to epoxy resins, for example, matrix resins based on CE, BMI, or PI polymers combine high mechanical strength with high glass transition temperatures, high thermal resistance, and long-term stability, which greatly expands the application possibilities of these thermosets, especially in high-temperature applications. However, thermoset systems based on CE resins also have disadvantages. During thermal curing, the reactive cyanate ester groups (= "N^CO-") trimerize to form cyclic triazine rings, resulting in so-called polycyanurate networks with high crosslinking density (WA12420S / Mk 2).As a consequence of their highly cross-linked state, cured cyanate ester resins exhibit high mechanical stability; however, this also makes the networks brittle, meaning they possess low crack and impact strength. Another significant disadvantage of cyanate ester resin systems is their susceptibility to hydrolysis: water penetrating the cured thermoset network causes network degradation (hydrolytic degradation), which impairs the material properties. It would therefore be desirable to provide suitable high-temperature stable modifiers for these already commercially available CE reactive resins that contribute to both a reduction in water absorption and increased crack strength of the cured thermoset networks, enabling their commercial use as matrix resins in demanding high-temperature composite applications, preferably for the aerospace industry.It is crucial that the modifiers are compatible with the cyanate ester resins, i.e., processable to form macroscopically homogeneous compositions, and that the cured thermoset compositions show no signs of segregation, such as oiling or seepage of the siloxane component from the polycyanurate network or sticky surfaces, which is undesirable because segregation alters the material properties and impairs the matrix-fiber bond. Several approaches have been developed for modifying polycyanurate networks with poly(diorgano)siloxanes ("silicones") that possess reactive functional groups copolymerizable with cyanate ester resins. WA12420S / Mk 3US5539041 (equivalent to EP0518654B1) claims compositions of cyanate ester resins and silicones with reactive, copolymerizable functional groups.In the exemplary embodiments, only amine-functionalized linear siloxanes are disclosed as modifiers for cyanatester resins. The main disadvantage of using amine-functionalized modifiers is their strong accelerating effect on the curing reaction of the cyanatester groups, making the curing of cyanatester resin compositions with higher proportions of amino group-containing modifiers uncontrollable. On the other hand, amino groups contribute to higher water uptake, which leads to increased polycyanurate network degradation through aminolysis and is thus noticeable in a higher hydrolysis rate. In JP2014012759A, JP2002309084A, JP2011202175A and US2022289965A (=equivalent to EP4056371A) the production of compositions from cyanate ester resins with at least two cyanate ester groups and longer-chain poly(dimethyl)siloxanes with terminal phenolpropyl groups is described in the exemplary embodiments.To prevent phase separation of the two incompatible components, the compositions are thermally pre-crosslinked to a prepolymer in the presence of a curing accelerator that accelerates the reaction of the cyanate esters with the phenol OH groups; the pre-crosslinking is carried out either in an organic solvent (JP2014012759A, JP2002309084A, JP2011202175A) or without solvent, but in a multi-stage mixing process (EP4056371A). In this context, "pre-crosslinked prepolymers" refer to the oligomers obtainable by partial trimerization of the cyanate ester groups involving the functional phenol groups of the siloxanes. This means that both a reaction of cyanate ester groups with each other and a reaction of phenol groups with cyanate ester groups take place, also resulting in cyanurate units, i.e., substituted triazine rings. The main disadvantages of these approaches include, among others...The disadvantages lie in the fact that the pre-crosslinking reactions are time-consuming and require additional process steps, and that the use of organic solvents is generally problematic for reasons of economy, toxicology, and disposal. Furthermore, the further processing of prepolymers that may have been pre-crosslinked in a solvent is not suitable for all processing methods and conditions, e.g., in infusion processes. In addition, the described pre-crosslinked prepolymers exhibit lower storage stability. These disadvantages are even more apparent in the publication by Mayra Y. Rivera Lopez et al., "Development of cyanate ester-oligosiloxane copolymers for deployable satellite applications," Polymer 209, (2024), 126573, than in the corresponding patent specification US2022289965A. Pre-crosslinking is always mandatory.This process is quite complex, as the conditions for correctly setting the temperature, time, energy input through mixing, and selecting a suitable catalyst must always be tailored to the specific starting materials and apparatus used. Furthermore, the aforementioned publications provide no information or guidance on whether, or how, the modification of cyanate ester resins with phenolpropyl-terminated poly(diorgano)siloxanes affects properties such as water absorption, glass transition temperature, or fracture toughness of the cured compounds. They also fail to mention that phenol-terminated siloxanes with shorter chain lengths might be compatible with cyanate ester resins even without pre-crosslinking.WA12420S / Mk 5 The present invention is based on the objective of providing a particularly easy-to-handle, curable composition consisting of an organic cyanate ester resin and a linear poly(diorgano)siloxane with phenolic hydroxy groups, such that modified polycyanurate networks are obtained after the shaping and curing process. These networks exhibit reduced water absorption and thus improved hydrolysis resistance as well as higher crack strength (KIc). The advantageous properties inherent in cyanate ester resins, such as good processability, high thermo-oxidative resistance, high glass transition temperature, and high mechanical strength, are largely retained in the thermosets modified in this way. Surprisingly, it was found that the short-chain, linear poly(diorgano)siloxanes with phenolic hydroxy groups according to the invention are completely miscible with cyanate resins.Therefore, pre-crosslinking in the presence of a curing accelerator and / or in an organic solvent can be omitted. Furthermore, the cured compositions according to the invention show no signs of segregation, such as oiling or seepage of the siloxane component from the polycyanurate network, or sticky surfaces. The cured compositions according to the invention advantageously combine properties such as reduced water absorption (and consequently reduced hydrolytic network degradation), higher fracture toughness, high thermo-oxidative stability, and a high glass transition temperature, which was previously unknown in the art.WA12420S / Mk 6 The subject of the invention is curable compositions containing (A) at least one organic compound free of siloxy (≡Si-O-) units with at least two reactive cyanate ester (-OC≡N) groups (also referred to in the present document as “cyanate ester resin”), (B) at least one poly(diorgano)siloxane of the general formula (i) R. k (R 2 -Z-) (3-k) SiO (R p (R 2 -Z-) (2-p) SiO-) q SiR o (R 2 -Z-) (3-o) wherein R is the same or different and -monovalent, SiC-bonded, optionally ether (COC) and / or epoxide (COC) groups, saturated hydrocarbon residues, -monovalent, SiC-bonded, optionally halogen-substituted, aromatic hydrocarbon residues free of phenolic OH groups or aliphatic C=C multiple bonds, which may be interrupted by heteroatoms, means, R2 is the same or different and is described by formula (IV), (IV), wherein WA12420S / Mk 7 -R6 and R8 each independently represent a hydrogen atom, a hydroxyl (HO) group, or a hydrocarbon residue with 1 to 12 carbon atoms, optionally linked via an ether (COC) unit; -R7, R9, and R10 each independently represent a hydrogen atom or a hydrocarbon residue with 1 to 12 carbon atoms, optionally linked via an ether (COC) unit; k is 2 or 3, preferably 2; o is 2 or 3, preferably 2; p is 0, 1, or 2, preferably 1 or 2, particularly preferably 2; q is an integer from 0 to 11, preferably from 0 to 7, particularly preferably from 0 to 3; Z is the same or different; and divalent saturated hydrocarbon residues with 2 to 5 carbon atoms, consisting of 1 to 3 units of F ormel (III) bedeutet -(CH(2-g)R3g)h- (III), wherein R 3is the same or different and represents a monovalent methyl, ethyl, or isopropyl group, g0, 1, or 2, h1, 2, or 3, with the proviso that one or two groups (R2-Z-), preferably two groups (R2-Z-), are present per poly(diorgano)siloxane molecule (B) of general formula (i), and that NO WA12420S / Mk 8 pre-crosslinking of components (A) with (B) is required in the presence of a curing accelerator. The composition according to the invention is preferably curable without the addition of a curing accelerator, in particular without the addition of a curing accelerator for pre-crosslinking components (A) and (B).In a particular embodiment, the following also applies: - no pre-crosslinking of components (A) with (B) takes place in the presence of a curing accelerator, and / or - without the addition of solvents and in the absence of a curing accelerator, components (A) and (B) can be processed in liquid form, preferably at a temperature of 100 °C, to form a stable, homogeneous composition, wherein this stable, homogeneous composition is characterized in particular by the fact that, after storage of the composition at 100 °C for at least 15 minutes, no macroscopic demixing occurs through the formation of a phase interface visible to the naked eye, i.e., recognizable two-phase structure.Furthermore, another characteristic of the stability of the composition according to the invention is that the hardened composition according to the invention also exhibits no macroscopic segregation in the form of seepage or oiling of the siloxane component (B) from the polycyanurate network visible to the naked eye, nor any sticky surfaces. The lack of stickiness or seepage after hardening of the obtained compositions according to the invention can preferably be demonstrated by applying and removing an LDPE film WA12420S / Mk 9 (CAS: 9002-88-4) or a filter paper (Whatman™ Filter Paper Grade 589 / 2) from the air-side surface. This property of the invention is also demonstrated later in the examples during the compatibility testing. In the present invention disclosure, the designation “1-propenyl” refers to the residue “−CH=CH−CH3”, “2-propenyl” or “allyl” to the residue “−CH2-CH=CH2” and the designation “propenyl” to the 1- or 2-propenyl residue.In this invention disclosure, "phenolic hydroxy group" means an aromatic hydroxy compound in which the hydroxy group is directly bonded to aromatic carbon atoms. In the present invention, the designation "component (A)" refers to the entirety of the at least one compound (A), and the designation "component (B)" refers to the entirety of the at least one compound (B). To avoid making the description of the present invention too lengthy, only the preferred embodiments for each feature are listed. However, the reader skilled in the art should understand this type of disclosure to explicitly disclose and explicitly desire any combination of different preferred states—that is, any combination both within a single compound / feature and between different compounds / features.Cyanate ester resin (A) WA12420S / Mk 10. This is an organic compound free of siloxy (≡Si-O-) units, containing at least two reactive cyanate ester groups (= “N^CO-”) per molecule. Compound (A) may be substituted and may also contain heteroatoms. Preferably, compound (A) is an aromatic hydrocarbon compound, optionally substituted and optionally containing heteroatoms, with at least two cyanate ester groups bonded to aromatic carbon atoms per molecule.Particularly preferred are at least two aromatic hydrocarbon residues per molecule in compound (A), optionally substituted and optionally containing heteroatoms, each with a cyanate ester group bonded to an aromatic carbon atom; In particular, compound (A) comprises the aromatic hydrocarbon residues, optionally substituted and containing heteroatoms, each with a cyanate ester group bonded to an aromatic carbon atom via a covalent bond or at least one bridging unit, selected from the group consisting of –(CR42)1-10-, -CR4=CR4-, -C(=CR42)-, -O-, -S-, -N=N-, -CR4=N-, -C(=O)-, -C(=O)O-, -OC(=O)O-, -S(=O)-, -S(=O)2-,O=P(O-)3, -SiR42-, a divalent aromatic hydrocarbon residue, such as phenylene, toluene, biphenylene and naphthylene; or a divalent cycloalkanediyl or polycycloalkanediyl residue, such as 1,4-cyclohexanediyl-, tricyclo[5.2.1.0. 2,6[decanediyl] and bicyclo[2.2.1]heptanediyl are linked together. At residue R 4 Each of these is independently a hydrogen atom, a halogen atom, or a monovalent, possibly substituted, hydrocarbon residue with 1 to 18 carbon atoms, which may be substituents either WA12420S / Mk 11 or the other residue R. 4 can be connected to form a cyclic unit. Examples of remainder R 4are monovalent residues, such as the methyl, ethyl, trifluoromethyl, phenyl, chlorine and fluorenyl residues; ring structures consisting of two residues R4, such as the 1,1-cyclohexanediyl-, cyclohexene-1,2-diyl-, 9H-fluoro-9,9-diyl-, N-phenyl-1-isoindolinone-3,3-diyl-, 1(3H)-isobenzofuranone-3,3-diyl-, anthracene-9(10H)-one-10,10-diyl, 9,10-dihydroanthracene-9,9-diyl- and the 3,3,5-trimethylcyclohexane-1,1-diyl residue. Examples of the component (A) used according to the invention are di- and poly-cyanate esters of monoaromatic hydrocarbons, such as phenylene 1,2-dicyanoate, phenylene 1,3-dicyanoate (CAS 1129-88-0, trade name: REX-370), phenylene 1,4-dicyanoate (CAS 1129-80-2), 2,4,5-trifluorophenylene 1,3-dicyanoate, 1,3,5-tricyanatobenzene, methyl (2,4-dicyanophenyl)ketone and 2,7-dicyanophthalene; cyanate esters of bisphenols, such as 2,2-bis(4-cyanatophenyl)butane, 2,2-bis(4-cyanatophenyl)propane (CAS 1156-51-0, bisphenol A cyanate ester;Handelsbezeichnungen: AroCy® B10, PRIMASET® BADCy bzw. CYTESTER®TA), 2,2-Bis(4-cyanatophenyl)-1,1,1,3,3,3-hexafluoropropane (CAS 32728-27-1, Bisphenol AF-Cyanate ester), 2,2-Bis(3-methyl-4-cyanatophenyl)propane (Bisphenol C-Cyanate ester), 1,1Bis(4-cyanatophenyl)ethane (CAS 47073-92-7, Bisphenol E—Cyanate ester; Trade names: AroCy® L-10, PRIMASET® LECy, CYTESTER®P201), 1,1-Bis(4-cyanatophenyl)-1-phenylethane (Bisphenol AP-Cyanate ester), Bis(4-cyanatophenyl)methane (Bisphenol F-Cyanate ester), Bis(4-cyanato-3,5-dimethylphenyl)methane (CAS 101657-77-6, Tetramethyl-Bisphenol F-Cyanate ester), 1,3-Bis(2-(4-cyanatophenyl)propan-2-yl)benzene (CAS 127667-44-1, Bisphenol M-cyanate ester;Trade names: PRIMASET® LM-500, AroCy® XU366, RTX-366), Bis(4-cyanatophenyl)thioether WA12420S / Mk 12 (trade name: AroCy® T-10), Bis(4-cyanatophenyl)ether, 1,1-Bis(4-cyanatophenyl)-3,3,5-trimethyl-cyclohexane, 1,1-Bis(4-cyanatophenyl)cyclohexane, 9,9-Bis(4-cyanatophenyl)fluorene (Bisphenol FL cyanate ester), Bis(4-cyanatophenyl)sulfone (CAS2918-28-7;Bisphenol S-cyanate ester), Bis(4-cyanatophenyl)ketone, Bis(4-(4-cyanatophenoxy)phenyl)ketone, Bis(4-(4-cyanatophenoxy)phenyl)sulfone, Bis(4-cyanatophenoxy)sulfoxide, Bis(4-(4-cyanatophenoxy)phenyl)(phenyl)phosphine oxide, Bis(4-cyanatophenyl)(methyl)phosphine oxide, 1,1-Dibromo-2,2-bis(4-cyanatophenyl)ethylene, 1,1-Dichloro-2,2-bis(4-cyanatophenyl)ethylene, 3,3-Bis(4-cyanatophenyl)-N-phenylphthalimide, 3,3-Bis(4-cyanatophenyl)-1(3H)-isobenzofuranone (CAS 32728-31-7), 3,3-Bis(4-cyanatophenyl)-2-benzofuran-1-one,10,10-bis(4-cyanatophenyl)anthracen-9(10H)-one, 1-Ethyl-2-methyl-3-(4-cyanatophenyl)-5-cyanatoindan, 1,1-Dimethyl-3-methyl-3-(4-cyanatophenyl)cyanatoindan, bis(2-cyanato-3-methoxy-5-methylphenyl)methane and 1,1-bis(3-methyl-4-cyanatophenyl)cyclohexane (bisphenol Z cyanate ester);Cyana esters of propenyl-substituted bisphenols, such as 2,2-bis(3-(2-propenyl)-4-cyanatophenyl)propane, bis{[4-[(3-allyl-4-cyanatophenyl)isopropylidene]phenoxy]phenyl}sulfone and bis{4-[4-cyanato-3-(2-propenyl)phenoxy]phenyl}sulfone; cyanate esters of biphenyls, such as 4,4'-dicyanobiphenyl (CAS 1219-14-3), 2,4'-dicyanobiphenyl and 2,2'-dicyanobiphenyl; Cyanate esters of phenol-dicyclopentadiene adducts (CAS 135507-71-0, CAS 119505-06-5; trade name: AroCy® XU-71787.02L, XU-71787; Primaset® DT-4000); Cyana esters of phenol-formaldehyde resins, which are produced, for example, by acid- or alkali-catalyzed condensation of phenols, naphthols, naphthalenediols, xylenols or cresols with formaldehyde, such as resol cyanate esters or novolac cyanate esters (e.g., BCAS 87397-54-4, CAS 153191-90-3, CAS 268734-03-8, CAS 30944-92-4 and CAS 173452-35-2; examples of trade names: WA12420S / Mk 13 Primaset® PT-15, PT-30, PT-60, PT-90 and CT-90, as well as AroCy® XU-371);Cyana esters of fluoroalkanediols, such as 1,8-dicyanotoperfluorooctane; cyanate esters of naturally occurring polyphenols, such as trans-3,5,4'-tricyanatostilbene; cyanate esters of bisphenol silanes, such as dimethylbis(4-cyanatophenyl)silane; 1,1,1-tris(4-cyanatophenyl)ethane (CAS 113151-22-7), 1,2,3-tris(4-cyanatophenyl)propane;as well as terminally terminated cyanatester polymer resins, which are composed of at least two identical or different repeating units, wherein the backbone of each repeating unit contains at least one divalent aromatic hydrocarbon residue, such as phenylene, biphenyls and naphthylene, or 9H-fluoro-9,9-diyl, and at least one bridging unit selected from the group consisting of -CR52-, -CR5=CR5-, -C(=CR52)-, -O-, -S-, -N=N-, -CR5=N-, -C(=O)-, -C(=O)O-, -OC(=O)O-, -S(=O)-, -S(=O)2-, O=P(O-)3, -SiR52- or a divalent cycloalkanediyl residue, such as tricyclo[5.2.1.02,6]decanediyl and Bicyclo[2.2.1]heptanediyl. Examples of repeating units in cyanatester polymer resins are arylene ethers, arylene ether sulfones, or arylene ether ketones. For residue R; 5 These are each, independently of each other, the ones for R 4The aforementioned residues. Preferably, component (A) is 2,2-bis(4-cyanatophenyl)propane, 1,1-bis(4-cyanatophenyl)ethane, bis(4-cyanatophenyl)methane, 1,3-bis(2-(4-cyanatophenyl)propan-2-yl)benzene, 2,2-bis(3-(2-propenyl)-4-cyanatophenyl)propane, bis(4-cyanatophenyl)thioether, bis(4-cyanatophenyl)sulfone, phenol-dicyclopentadiene cyanate ester resins, and cyanate esters of phenol-formaldehyde resins. Component (A) is particularly preferably 2,2-bis(4-cyanatophenyl)propane, bis(4-cyanatophenyl)methane, 1,1-bis(4-cyanatophenyl)ethane, 1,3-bis(2-WA12420S / Mk 14(4-cyanatophenyl)propan-2-yl)benzene, bis(4-cyanatophenyl)thioether, bis(4-cyanatophenyl)sulfone, phenol-dicyclopentadiene cyanate ester resins, and cyanate esters of phenol-formaldehyde resins. In particular, component (A) is 1,1-bis(4-cyanatophenyl)ethane, 1,3-bis(2-(4-cyanatophenyl)propan-2-yl)benzene, and cresol or phenol-novolac cyanate esters.Only one cyanate ester resin (A) or a mixture of different cyanate ester resins (A) can be used, or prepolymers made from one cyanate ester resin (A) (i.e., prepolymerized cyanate ester resins (A)) or prepolymers made from different cyanate ester resins (A), as well as mixtures of prepolymerized cyanate ester resins or mixtures of prepolymerized cyanate ester resins with one or more cyanate ester resins (A) can be used. An example of a prepolymer made from a cyanate ester resin (A) is bisphenol A dicyanate homopolymer (CAS 25722-66-1, trade name: Primaset® BA-200). Compound (B)The compounds (B) used according to the invention are linear poly(diorgano)siloxanes of the general formulas (i) as described above.Poly(diorgano)siloxanes (B) can be solid or liquid at 23°C and 1013 hPa, wherein the poly(diorgano)siloxanes (B) are preferably liquid at 23°C and 1013 hPa.If the poly(diorgano)siloxanes(B) used according to the invention are liquid, they have a dynamic viscosity preferably of 5 mPa·s to 10000 mPa·s, particularly preferably 5 mPa·s WA12420S / Mk 15 to 1000 mPa. .s, in particular 10 mPa·s to 500 mPa·s, each at 23°C. Method for determining dynamic viscosity. Within the scope of the present invention, the dynamic viscosity according to DIN 53019 is determined at a temperature of 23°C and an atmospheric pressure of 1013 hPa, unless otherwise specified. The measurement is carried out with a rotational rheometer “Physica MCR 300” from Anton Paar. For viscosities from 1 to 200 mPa·s, a coaxial cylinder measuring system (CC 27) with a ring measuring gap of 1.13 mm is used; for viscosities greater than 200 mPa·s, a cone-plate measuring system (Searle system with measuring cone CP 50-1) is used.The shear rate is adjusted to the polymer viscosity (1 to 99 mPa·s at 100 s⁻¹; 100 to 999 mPa·s at 200 s⁻¹; 1000 to 2999 mPa·s at 120 s⁻¹; 3000 to 4999 mPa·s at 80 s⁻¹; 5000 to 9999 mPa·s at 62 s⁻¹; 10000 to 12499 mPa·s at 50 s⁻¹; 12500 to 15999 mPa·s at 38.5 s⁻¹; 16000 to 19999 mPa·s at 33 s⁻¹; 20000 to 24999 mPa·s at 25 s⁻¹; 25000 to 29999 mPa·s at 20 s⁻¹; 30,000 to 39,999 mPa·s at 17 s⁻¹; 40,000 to 59,999 mPa·s at 10 s⁻¹; 60,000 to 149,999 mPa·s at 5 s⁻¹; 150,000 to 199,999 mPa·s at 3.3 s⁻¹; 200,000 to 299,999 mPa·s at 2.5 s⁻¹; 300,000 to 1,000,000 mPa·s at 1.5 s⁻¹. After the measuring system has been brought to the measurement temperature, a three-stage measurement program consisting of a run-in phase, a pre-shearing phase, and a viscosity measurement is applied.The initial phase involves gradually increasing the shear rate within one minute to the shear rate specified above, which depends on the expected viscosity and at which the measurement is to be taken. Once this rate is reached, a pre-shearing phase is performed for 30 seconds at a constant shear rate. Subsequently, to determine the viscosity of WA12420S / Mk 16, 25 individual measurements are carried out for 4.8 seconds each, from which the mean value is determined. The mean value corresponds to the dynamic viscosity, which is given in mPa·s. The poly(diorgano)siloxanes (B) used according to the invention have a weight-average molar mass Mw of preferably 200 to 4500 g / mol, particularly preferably 300 g / mol to 3500 g / mol, and in particular 500 g / mol to 3000 g / mol. The poly(diorgano)siloxanes (B) used according to the invention have a number-average molar mass Mn of preferably 200 to 3500 g / mol, particularly preferably 300 g / mol to 2500 g / mol, and in particular 400 g / mol to 1800 g / mol.Examples of monovalent, SiC-bonded, optionally ether (COC) and / or epoxide (COC) groups, saturated hydrocarbon residues R are alkyl residues, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, n-pentyl, iso-pentyl, neo-pentyl, and tert-pentyl residues; hexyl residues, such as n-hexyl; heptyl residues, such as n-heptyl; octyl residues, such as n-octyl and iso-octyl, such as 2,4,4-trimethylpentyl and 2,2,4-trimethylpentyl; and nonyl residues, such as n-nonyl. Decyl groups, such as the n-decyl group; dodecyl groups, such as the n-dodecyl group; hexadecyl groups, such as the n-hexadecyl group; octadecyl groups, such as the n-octadecyl group; as well as cycloalkyl groups, such as the cyclopentyl, cyclohexyl, cycloheptyl and methylcyclohexyl groups; as well as epoxy groups, such as the 3-glycidoxypropyl, oxiran-2-yl and 2-(3,4-epoxycyclohexyl)ethyl groups.Examples of monovalent, SiC-bonded, optionally halogen-substituted, aromatic hydrocarbon residues R free of phenolic OH groups or aliphatic C=C multiple bonds, which may be interrupted by heteroatoms, are aryl residues such as phenyl, biphenyl, cumylphenyl, benzylphenyl, naphthyl, anthryl, and phenanthryl; alkaryl residues such as tolyl, xylyl, and ethylphenyl; aralkyl residues such as benzyl, cumyl, α-, and β-phenylethyl; alkoxyaryl residues such as methoxyphenyl; aryloxyaryl residues such as phenoxyphenyl; and halogenaryl residues such as fluorophenyl, chlorophenyl, bromophenyl, and trifluoromethylphenyl. as well as heterocyclic aromatic hydrocarbon residues, such as pyridyl, pyrazinyl, quinolinyl, furyl residues and the (9,10-dihydro-9-oxa-10-phosphaphenanthren-10-oxide-10-yl)ethyl residue.Preferably, the R group consists of monovalent, SiC-bound alkyl groups with 1 to 8 carbon atoms and aryl groups, particularly preferably the methyl group and the phenyl group, especially the methyl group. The aromatic hydrocarbon groups R2 are described by formula (IV). (IV), wherein R6 and R8 each independently comprise a hydrogen atom, a hydroxyl (HO) group or a hydrocarbon residue with 1 to 12 carbon atoms, optionally bound via a WA12420S / Mk 18 ether (COC) unit; R 7 , R 9 and R 10 Each independently represents a hydrogen atom or a hydrocarbon residue with 1 to 12 carbon atoms, optionally bound via an ether (COC) unit. Although not explicitly expressed in formula (IV), as a further embodiment of the invention, two or more residues R 6 , R 7 , R 8 , R 9 and R 10the meaning of divalent hydrocarbon residues, optionally containing a hydroxyl group and optionally bound via an ether (COC) unit, which together form one or more ring structures. For example, R 7 and R 8 together form a ring, as in 5,6,7,8-tetrahydro-1-naphthol or 1-naphthol. In a preferred embodiment, residue R6 is a hydroxy group, and residues R7, R8, R9, and R10 are each, independently of one another, a hydrogen atom, a phenyl, phenoxy, methyl, isopropyl, tert-butyl, or cumyl (C6H5-C(CH3)2-) residue. In a further preferred embodiment, residue R8 is a hydroxy group, residue R7 is a methoxy group, and residue R 6 , R 9 and R 10around hydrogen atom. Examples of R2 are hydroxyphenyl [-C6H4(OH)]-, hydroxy(methyl)phenyl [-C6H3(OH)(CH3)]-, hydroxy(tert-butyl)phenyl [-C6H3(OH)(C(CH3)3)]-, hydroxy(dimethyl)phenyl[-C6H2(OH)(CH3)2]-, Hydroxy(di-tert-Butyl)phenyl[-C6H2(OH)(C(CH3)3)2]-, Hydroxy(methoxy)phenyl [-C6H3(OH)(OCH3)]-,Hydroxy(phenyl)phenyl [-C6H3(OH)(C6H5)]-, Hydroxy(tert- WA12420S / Mk 19Octyl)phenyl [-C6H3(OH)((C(CH3)2)(CH2)(C(CH3)3))]-,Hydroxy(nonyl)phenyl [-C6H3(OH)((CH2)8CH3)]-,Hydroxy(dodecyl)phenyl [-C6H3(OH)((CH2)11CH3)]-, Hydroxy(tert-Amyl)phenyl [-C6H3(OH)((C(CH3)2)CH2CH3)]-,Hydroxy(isopropyl)phenyl [-C6H3(OH)(CH(CH3)2)]-,Hydroxy(cumyl)phenyl [-C6H3(OH)((C(CH3)2)(C6H5))]-,Hydroxy(phenoxy)phenyl [-C6H3(OH)(OC6H5)]- and the hydroxynaphthyl [-C10H6(OH)] residue. Preferably, residue R 2around hydroxy(methoxy)phenyl, hydroxy(phenyl)phenyl, hydroxy(tert-butyl)phenyl, hydroxyphenyl, hydroxy(phenoxy)phenyl and hydroxy(cumyl)phenyl radical, preferably around the 3-methoxy-4-hydroxyphenyl, 2-hydroxyphenyl, 2-hydroxy-5-phenylphenyl, 2-hydroxy-3-phenylphenyl, 2-hydroxy-5-tert-butylphenyl, 2-hydroxy-5-tert-octylphenyl, 2-hydroxy-5-phenoxyphenyl and 2-hydroxy-5-cumylphenyl radical, particularly preferably around the 2-hydroxy-5-cumylphenyl, 2-hydroxyphenyl and 2-hydroxy-5-tert-butylphenyl radical, in particular around the 2-hydroxy-5-cumylphenyl, 2-hydroxyphenyl and 2-hydroxy-5-tert-butylphenyl radical. Examples of Z are Divalent saturated hydrocarbon residues with 2 to 5 carbon atoms such as -CH2-CH2-, -CHMe-, -CH2-CH2-CH2-, -CMe2-, -CH2-CHMe-, -CHEt-, - CH2-CH2-CHMe-, -CH2-CHEt-, -CH2-CHMe-CH2-, -CH2-CMe2-, -CHiPr-, -CH2-CH2-CMe2-, -CH2-CHiPr-, -CHMe-CHMe-CH2-, -CHMe-CMe2- and -CMe2-CHMe-, where Me represents the methyl, Et the ethyl and iPr the isopropyl residue.Preferably, the residue Z is -CH2-CH2-, -CHMe-, -CH2-CH2-CH2-, -CH2-CHMe-, -CH2-CHMe-CH2- and -CH2-CMe2-; particularly preferred is -CH2-CH2-, -CHMe-, -CH2-CH2-CH2-, -CH2-CHMe-CH2- and WA12420S / Mk 20-CH2-CHMe-; especially is -CH2-CH2-CH2- and -CH2-CHMe-CH2-; where Me means methyl residue. Examples of the component (B) used according to the invention are preferably those of formulas (V) to (XVIII). , WA12420S / Mk 21 5 WA12420S / Mk 22 (XVIII), wherein WA12420S / Mk 23n is 1 to 12, preferably 1 to 8, particularly preferably 1 to 4, and r, s, u and v are 1 to 11, with the proviso that the sum of r + s and u + v is each equal to 1 to 12, preferably 1 to 8, particularly preferably 1 to 4. Preferably, the component (B) used according to the invention is one of formulas (V), (VI), (VII), (VIII), (IX), (X), and (XVII) with n equal to 1 to 12. Particularly preferably, the component (B) used according to the invention is one of formulas (V), (VI), (VII), (VIII), (IX), (X) and (XVII) with n equal to 1 to 8. In particular, the component (B) used according to the invention is one of formulas (V), (VI),(VII) and (X) with n equal to 1 to 8. Components (B) used according to the invention are commercially available products or can be produced according to processes commonly used in chemistry.Preferably, poly(diorgano)siloxanes (B) are prepared by hydrosilylation reaction of linear poly(diorgano)siloxanes having terminal Si-bonded hydrogen atoms with aromatic compounds having at least one phenolic hydroxyl group and an unsaturated aliphatic hydrocarbon residue, preferably vinyl, allyl or 2-methyl-2-propen-1-yl (“Methallyl”) residue, in the presence of a catalyst accelerating the hydrosilylation reaction, e.g. platinum complexes such as the Karstedt catalyst, wherein aromatic compounds with a propenyl or methallyl residue ortho to the phenolic hydroxyl group are particularly preferred. WA12420S / Mk 24 For the preparation of compound (B) only a poly(diorgano)siloxane or a mixture of different poly(diorgano)siloxanes can be reacted with one or more different aromatic compounds having at least one phenolic hydroxy group and an unsaturated aliphatic residue.Only one poly(diorgano)siloxane (B) or a mixture of different poly(diorgano)siloxanes (B) may be used. The compositions according to the invention contain poly(diorgano)siloxane (B) preferably in amounts of 5 to 70 parts by weight, more preferably 5 to 50 parts by weight, and more preferably 5 to 30 parts by weight, each based on 100 parts by weight of component (A). In addition to components (A) and (B), the compositions according to the invention may contain further substances that are different from components (A) and (B), such as modifier (C), reactive resin (D), filler (E), curing accelerator (F), solvent (G), and additives (H).The composition according to the invention can comprise ^only one compound (C) or a mixture of different compounds (C), preferably only one compound (C); ^only one compound (D) or a mixture of different compounds (D), preferably only one compound (D); WA12420S / Mk 25 ^only one compound (E) or a mixture of different compounds (E), preferably only one compound (E); ^only one compound (F) or a mixture of different compounds (F), preferably only one compound (F); ^only one compound (G) or a mixture of different compounds (G), preferably only one compound (G); and / or ^only one compound (H) or a mixture of different compounds (H), preferably only one compound (H).In the present invention, the designation “component (C)” refers to the entirety of the at least one compound (C), the designation “component (D)” refers to the entirety of the at least one compound (D), the designation “component (E)” refers to the entirety of the at least one compound (E), the designation “component (F)” refers to the entirety of the at least one compound (F), the designation “component (G)” refers to the entirety of the at least one compound (G), and the designation “component (H)” refers to the entirety of the at least one compound (H). Compound (C) The optional at least one modifier (C) preferably comprises organosilicon compounds (C1) different from (B) containing units of formula (xiii) R. 11 i (OR 12 ) j SiO (4-i-j) / 2 (xiii), wherein WA12420S / Mk 26 R 11may be the same or different and means hydrogen atom or monovalent, SiC-bonded, optionally substituted, optionally heteroatom-interrupted, hydrocarbon residues, R12 may be the same or different and means hydrogen atom or monovalent, optionally heteroatom-interrupted hydrocarbon residues with 1 to 18 carbon atoms, i is 0, 1, 2 or 3, preferably 1, 2 or 3, j is 0, 1, 2 or 3, preferably 0, 1 or 2, particularly preferably 0 or 1, in particular 0, and provided that in formula (xiii) the sum i+j<3 is, that compound (C1) contains 2 to 20 units of formula (xiii) and that compound (C1) does not contain any phenolic hydroxy groups.Examples of monovalent, SiC-bonded, optionally substituted, optionally heteroatom-interrupted, hydrocarbon residues R11 are the residues mentioned for R; unsaturated hydrocarbon residues, such as vinyl-, propenyl-, 5-hexenyl-, cyclohexenyl-, 2-(3-cyclohexenyl)ethyl-, bicyclo[2.2.1]hepten-2-yl, dicyclopentenyl, 7-octenyl, 10-undecenyl, 4-vinylcyclohexyl, 3-norbornenyl, vinylphenyl, propenylphenyl, ethynyl, propynyl and butynyl, arylethynyl and ethynylphenyl residue; imido residues such as N-(5-ethynylphthalimido)phenyl, N-(5-(phenylethynyl)phthalimido)phenyl, nadimidophenyl, maleimidophenyl and 3-maleimidopropyl; Epoxide residues, again 3-glycidoxypropyl, 4-(oxiran-2-yl)phenyl, oxiran-2-yl and 2-(3,4-epoxycyclohexyl)ethyl residue; Acrylate residues, such as the 3-methacryloxypropyl, acryloxymethyl, and methacryloxymethyl residues; amine residues, such as aminophenyl residues, the 3-aminopropyl, N-(2-aminoethyl)-3-aminopropyl, and N-phenylaminomethyl residues; hydroxyalkyl residues, such as the hydroxypropyl residue; as well as bicyclo[4.2.0]octa-1,3,5-trienyl (= benzocyclobutenyl)-, WA12420S / Mk 27 polycaprolactone-, polycaprolactam-, cyanatophenyl-, 3-cyanatopropyl-, isocyanatophenyl-, and 3-isocyanatopropyl residues. The residue R is preferably... 11around a hydrogen atom, the phenyl, methyl, or maleimidophenyl group, and especially preferably the methyl and phenyl group. Preferably, the group R is... 12 around aliphatic hydrocarbon residues with 1 to 12 carbon atoms, particularly preferably around alkyl residues with 1 to 6 carbon atoms, in particular around the methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl or iso-butyl residue, especially around the methyl or ethyl residue. Examples of organosilicon compounds (C1) are 1,3,5,7-tetrakis(2-(3,4-epoxycyclohexyl)ethyl)-1,3,5,7-tetramethylcyclotetrasiloxane (CAS 121225-98-7), 2,4,6,8-tetramethyl-2,4,6,8-tetrakis[3-(glycidoxy)propyl]cyclotetrasiloxane (CAS 257284-60-9), Bis[2-(3,4-epoxycyclohex-1-yl)ethyl]-1,1,3,3-tetramethyldisiloxane (CAS 18724-32-8), 1,3-Bis(norbornenylethyl)-1,1,3,3,-tetramethyldisiloxane, organopolysiloxane of medium composition (PhSiO₂) 3 / 2 ) 20 (PhSi(OMe)O 2 / 2 ) 66 (PhSi(OMe)2O 1 / 2 ) 14and a weight-average molar mass Mw = 2190 g / mol, organopolysiloxane of the medium composition (PhSiO3 / 2)75(Me3SiO1 / 2)25 and a weight-average molar mass Mw = 1380 g / mol, octa(epoxycyclohexyl)-POSS (CAS 187333-74-0), octaphenyl-POSS (CAS 5256-79-1), octaphenylcyclotetrasiloxane (CAS 546-56-5), 2,4,6,8-tetramethyl-2,4,6,8-tetraphenylcyclotetrasiloxane (CAS 77-63-4), 1,1,3,3,5,7-hexamethyl-5,7-diphenylcyclotetrasiloxane, 1,1,3,3-tetramethyl-5,5,7,7-tetraphenylcyclotetrasiloxane (CAS WA12420S / Mk 28 1693-47-6), 1,3,5-trimethyl-1,1,3,5,5-pentaphenyltrisiloxane (3390-61-2), 1,3,3,5-tetramethyl-1,1,5,5-tetraphenyltrisiloxane (3982-82-9), 1,3,5,7-tetramethyl-1,1,3,5,7,7-hexaphenyltetrasiloxane (CAS 38421-40-8), and 1,9-dimethoxy-1,3,5,7,9-pentamethyl-1,3,5,7,9-pentaphenylpentasiloxane.The optional at least one modifier (C) is preferably a thermoplastic organic polymer (“thermoplastic”) (C2) free of siloxy (≡Si-O-) units and cyanate ester groups, with at least two repeating units, selected from the group consisting of polyarylenes, polyarylene ethers, polyarylene sulfides, polysulfones, polyethersulfones, polyetherketones, polyetheretherketones, polyetherketoneketones, polyetheretherketoneketones, polyimides, polybenzimidazoles, polyamides, poly(amide-imides), polyarylates, polyesterimides, polyetherimides, polyaramides, polyacrylates, polyhydantoins, liquid crystal polymers, polycarbonates, polyestercarbonates, and polyethylene terephthalates; as well as mixtures or copolymers thereof. The thermoplastics (C2) have either reactive or chemically inert end groups. Due to the manufacturing process, reactive end groups remain after the polymerization reaction from the corresponding reactive groups of the monomers.These are preferably hydroxy, amino, carboxy, and isocyanate groups. Examples of chemically inert end groups are methyl or phenyl groups. The thermoplastics (C2) have glass transition temperatures above 100°C, preferably from 130°C to 450°C, particularly preferably from 150°C to 400°C, and especially from 180°C to 350°C; the number-average molar mass Mn of (C2) is preferably 1,100 to 100,000 g / mol, preferably 2,000 to 50,000 g / mol, particularly preferably 2,000 to 30,000 g / mol, and especially 3,000 to 20,000 g / mol. WA12420S / Mk 29 The optional at least one modifier (C) is preferably an organic, monofunctional cyanate ester (C3) of the general formula (xiv)R13-OCN (xiv), free of siloxy (≡Si-O-) units and phenolic hydroxy groups, wherein R. 13a monovalent, possibly substituted, aromatic hydrocarbon residue, which may be interrupted by heteroatoms, means, with the proviso that the cyanate ester group is directly bonded to an aromatic carbon atom. Examples of suitable compounds (C3) are cyanatobenzene (CAS 1122-85-6), 1-cyanato-4-cumylbenzene (CAS 110215-65-1), 1-cyanato-4-tert-butylbenzene, 1-cyanato-2-tert-butylbenzene, 4-cyanatobiphenyl, 1-cyanatonaphthalene, 2-cyanatonaphthalene, 4-cyanatononylbenzene, 4-chlorocyanatobenzene, 4-cyanatodiphenylsulfone, 4-cyanatotoluene, 4-cyanatodiphenyl ether, 4-cyanatodiphenyl ketone, 4-(cyanato)methoxybenzene; as well as propenyl-substituted monofunctional cyanate esters, such as 2-(2-propenyl)cyanatobenzene or 2-(1-propenyl)cyanatobenzene. Preferably, the compounds (C3) have a boiling point at 1013 hPa of at least 150°C, particularly preferably at least 180°C.in particular at least 220°C. The optional at least one modifier (C) is preferably a monomonomeric hydrocarbon (C4) free of siloxy (≡Si-O-), epoxide, imide and cyanate groups, with at least one phenolic hydroxy group and optionally one or more aliphatic carbon-carbon multiple bonds. WA12420S / Mk 30 The optional aliphatic carbon-carbon multiple bonds in compound (C4) are preferably propenyl groups bonded to aromatic carbon atoms, wherein in compound (C4) a phenolic hydroxyl group and optionally a propenyl group are particularly preferably bonded to an aromatic residue. Examples of compounds (C4) without aliphatic carbon-carbon multiple bonds are monovalent, optionally substituted phenols, such as phenol, cresol, naphthol, 4-phenylphenol, thymol, guaiacol (2-methoxyphenol), 4-cumylphenol, 4-benzylphenol, 4-isopropylphenol, 4-tert-butylphenol,2-tert-Butylphenol, 2,4-Di-tert-butylphenol, 2,4-Bis(α,α-dimethylbenzyl)phenol, Nonylphenol, Xylenol or 2,6-Dinonylphenol; polyhydric phenols, such as catechol (benzene-1,2-diol), resorcinol (benzene-1,3-diol), hydroquinone (benzene-1,4-diol), pyrogallol (benzene-1,2,3-triol), phloroglucinol (benzene-1,3,5-triol), dihydroxynaphthalene; Aromatic compounds with two (bisphenol) or more hydroxyphenyl groups, such as bis-(2-hydroxyphenyl)methane, 2,2-bis(3-methyl-4-hydroxyphenyl)propane (bisphenol C), 1,1-bis(4-hydroxyphenyl)ethane (bisphenol E), 2,2-bis(4-hydroxyphenyl)propane (bisphenol A), 2,2-bis(4-hydroxyphenyl)butane (bisphenol B), 2,2-bis(4-hydroxyphenyl)hexafluoropropane (bisphenol AF), 9,9-bis(4-hydroxyphenyl)fluorene (bisphenol FL), bis(4-hydroxyphenyl)sulfone (bisphenol S), 1,3-bis(2-(4-hydroxyphenyl)-2-propyl)benzene (bisphenol M), 1,4-bis-[2-(4-hydroxyphenyl)-2-propyl]benzene (bisphenol P), bis(4-hydroxyphenyl)methane (Bisphenol F), bis(4-hydroxyphenyl) ether,Bis(4-hydroxyphenyl)thioether and 1,1,1-Tris(4-hydroxyphenyl)ethane. WA12420S / Mk 31 Examples of compounds (C4) with propenyl groups are 2,2-bis(3-(2-propenyl)-4-hydroxyphenyl)propane (CAS 1745-89-7), 2-methoxy-4-(2-propenyl)phenol (CAS 97-53-0), 4-(2-propenyl)-2,6-dimethoxyphenol (CAS 6627-88-9), 2-(2-propenyl)-6-methylphenol (CAS 3354-58-3), 2-(2-propenyl)phenol (CAS 1745-81-9), 5,5′-bis(2-propenyl)-2,2′-biphenyldiol (CAS 528-43-8), 3′,5-Bis(2-propenyl)-2,4'-biphenyldiol (CAS 35354-74-6), bis(3-(2-propenyl)-4-hydroxyphenyl)sulfone (CAS 41481-66-7), 4-cumyl-2-(2-propenyl)phenol, 4-cumyl-2-(2-methyl-2-propenyl)phenol, 4-tert-butyl-2-(2-propenyl)phenol, 4-tert-butyl-2-(2-methyl-2-propenyl)phenol, 2,2′-bis(3-propenyl-4-hydroxyphenyl)-p-diisopropylbenzene, 2,2′-bis(3-propenyl-4-hydroxyphenyl)perfluoropropane and 9,9′-bis(3-propenyl-4-hydroxyphenyl)fluorene and 4-(1-(4-Hydroxy-3-propenylphenyl)propyl)-2-propenylphenol. Compound (C4) is preferably 4-phenylphenol,2-methoxy-4-(2-propenyl)-phenol, 4-cumylphenol, 4-isopropylphenol, 4-tert-butylphenol, 2-tert-butylphenol, bisphenols, 2,2-bis(3-(2-propenyl)-4-hydroxyphenyl)propane, 4-(1-(4-hydroxy-3-propenylphenyl)propyl)-2-propenylphenol, 4-cumyl-2-(2-propenyl)phenol, 4-cumyl-2-(2-methyl-2-propenyl)phenol, 4-tert-butyl-2-(2-propenyl)phenol, 4-tert-butyl-2-(2-methyl-2-propenyl)phenol and 2-(2-propenyl)phenol; wherein 2-methoxy-4-(2-propenyl)phenol, 4-cumylphenol, 4-tert-butylphenol, 2,2-bis(3-(2-propenyl)-4-hydroxyphenyl)propane, bis(3-(2-propenyl)-4-hydroxyphenyl)sulfone, 4-cumyl-2-(2-propenyl)phenol, 4-tert-butyl-2-(2-propenyl)phenol, as well as bisphenol A, E, F, M and S are particularly preferred. If the compositions according to the invention contain at least one modifier (C),The composition may contain either only one modifier WA12420S / Mk 32(C1) to (C4) or several different modifiers (C1) to (C4) in a mixture. If the compositions according to the invention contain at least one modifier (C), the at least one modifier (C) is present in amounts preferably 1 to 30 parts by weight, particularly preferably 1 to 20 parts by weight, and in particular 1 to 10 parts by weight, in each case based on 100 parts by weight of the sum of components (A) and (B). In one of the preferred embodiments, the compositions according to the invention do not contain any component (C). Compound (D) The optional at least one reactive resin (D) is preferably an aromatic hydrocarbon compound free of siloxy (≡Si-O-) units and of cyanate ester and phenolic hydroxy groups, optionally substituted, optionally heteroatom-interrupted, selected from the group consisting of epoxides (D1) and imides (D2) with the stipulation thatthat epoxides (D1) have at least two, preferably at least two, polymerizable glycidyloxy, glycidyloxycarbonyl, glycidylamino, diglycidylamino or oxiran-2-yl groups per molecule bonded to aromatic carbon atoms; and that imides (D2) have at least two, preferably at least two, polymerizable 5-ethynylphthalimido, 5-(phenylethynyl)phthalimido, nadimido, benzocyclobutenphthalimido or maleimido groups per molecule, wherein the maleimido, glycidyloxy, glycidylamino and diglycidylamino groups are particularly preferred. WA12420S / Mk 33 Preferably, the optional reactive resin (D) contains at least two, optionally substituted, optionally heteroatom-interrupted, aromatic hydrocarbon residues, each with a maleimido-, glycidyloxy-, glycidyloxycarbonyl- bonded to an aromatic carbon atom.Glycidylamino or diglycidylamino group. Particularly preferably, (D) are compounds comprising at least two, optionally substituted, optionally heteroatom-interrupted, aromatic hydrocarbon residues, each with a maleimido, glycidyloxy, glycidylamino, or diglycidylamino group bonded to an aromatic carbon atom, which are connected via a covalent bond or a bridging unit selected from the group consisting of -CR142-, -CR14=CR14-, =C=CR142, -O-, -S-, -N=N-, -CR14=N-, -C(=O)-, -C(=O)O-, -OC(=O)O-, -S(=O)2-, O=P(O-)3, -SiR142-, phenylene, arylene, biphenylene, biarylene, naphthylene, or cycloalkandiyl groups, such as Tricyclo[5.2.1.02,6]decanediyl or bicyclo[2.2.1]heptanediyl are linked together. At residue R, 14 These are each, independently of each other, the ones for R 4The aforementioned residues. Preferably, reactive resins (D) contain heteroatom-free aromatic ring frameworks. Epoxy resins (D1) are preferably copolymerizable with cyanate ester resin (A). Preferably, imide resins (D2) are not copolymerizable with cyanate ester resin (A). WA12420S / Mk 34 Examples of polymerizable epoxy resins (D1) are glycidyl ethers of phenolic compounds, such as 2,2-bis(4-glycidyloxyphenyl)propane (CAS 1675-54-3), bis(4-glycidyloxyphenyl)methane (CAS 2095-03-6), 1,2-bis(glycidyloxy)benzene (CAS 2851-82-3), 1,3-bis(glycidyloxy)benzene (CAS 101-90-6), 1,4-bis(glycidyloxy)benzene (CAS 129375-41-3), 3,5,3',5'-tetramethyl-4,4'-diglycidyloxybiphenyl (CAS 85954-11-6), 2,2- Bis(3,5-dibromo-4-glycidyloxyphenyl)propane (CAS 3072-84-2), Tris(4-glycidyloxyphenyl)methane (CAS 66072-38-6), 1,1,2,2-Tetrakis(4-glycidyloxyphenyl)ethane (CAS 7328-97-4), 4,4'-Bis(glycidyloxyphenyl)sulfone (CAS 878-43-1), 9,9-Bis(4-glycidyloxyphenyl)fluorene (CAS 47758-37-2), 1,6-(Diglycidyloxy)naphthalene (CAS 27610-48-6); Glycidyl ethers of phenol, naphthol, naphthalenediol, bisphenol, or cresol-formaldehyde condensation products, such as cresol-novolac glycidyl ether (CAS 29690-82-2), phenol-novolac glycidyl ether (CAS 9003-36-5, CAS 28064-14-4, CAS 158163-01-0), and bisphenol A-epichlorohydrin-formaldehyde copolymer (CAS 28906-96-9); glycidyl ethers of phenol or cresol-dicyclopentadiene condensation products, such as CAS 68610-51-5 and CAS 119345-05-0; glycidyl esters of aromatic carboxylic acids, such as diglycidyl phthalate (CAS 7195-45-1), diglycidyl terephthalate (CAS 7195-44-0), diglycidyl isophthalate (CAS 7195-43-9), triglycidyl 1,2,3-benzene tricarboxylate, triglycidyl 1,2,4-benzene tricarboxylate (CAS 7237-83-4) and triglycidyl 1,3,5-benzene tricarboxylate (CAS 7176-19-4); glycidyl derivatives of aromatic amines and aminophenols, such as N,N-diglycidyl-4-glycidyloxyaniline (CAS 5026-74-4), 4,4'-methylenebis(N,N-diglycidylaniline) (CAS 28768-32-3), N,N,N',N'-tetraglycidyl-4,4'-diamino-3,3'-diethyldiphenylmethane (CAS 130728-76-6) and m-(Glycidyloxy)-N,N-diglycidylaniline (CAS 71604-74-5); Glycidyl-terminated thermoplastic polymers, which WA12420S / Mk 35 can be prepared, for example, by reacting amino- or hydroxy-terminated thermoplastics (C2) with epichlorohydrin, such as glycidyloxy- or digylcidylamino-terminated polysulfones; Homopolymers or copolymer epoxy resins, such as bisphenol A-epichlorohydrin copolymer (CAS25036-25-3), 2,2',6,6'-tetrabromobisphenol A-epichlorohydrin copolymer (CAS 40039-93-8) and reaction products of diglycidylbisphenol A with m-phenylenebis(methylamine) (CAS110839-13-9); as well as mixtures of various epoxy resins (D1). Examples of polymerizable maleimide resins (D2) are 4,4'-bis(maleimidophenyl)methane (CAS 13676-54-5), m-xylylenebismaleimide (CAS 13676-53-4), 1,1'-(2,2,4-trimethylhexane-1,6-diyl)bis-1H-pyrrole-2,5-dione (CAS 39979-46-9), bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (CAS 105391-33-1),Bis(4-maleimido-3-methylphenyl)methane, Bis(4-maleimido-3,5-dimethylphenyl)methane, 1,1-Bis(4-maleimidophenyl)cyclohexane, 2,4-Bismaleimidotoluene (CAS 6422-83-9), N,N'-1,2-Phenylenebismaleimide (CAS 13118-04-2), N,N'-1,3-Phenylenebismaleimide (CAS 3006-93-7), N,N'-1,3-Phenylenebismaleimide (CAS 3278-31-7), copolymers of bismaleimides and aromatic amines, such as 4,4'-Bis(maleimidophenyl)methane / 4,4'-Bis(aminophenyl)methane copolymer (CAS 26140-67-0); Reaction product of a condensation product of formaldehyde and aniline with maleic anhydride (CAS 28630-26-4, CAS 67784-74-1); Bis(4-maleimidophenyl) ether, 2,2-Bis[4-(maleimidophenoxy)phenyl]propane (CAS 79922-55-7), Bis(4-maleimidophenyl)sulfone (CAS 13102-25-5), Bis(4-maleimidophenyl)ketone, 1,1'-(benzene-1,3-diyldimethandiyl)bis(1H-pyrrole-2,5-dione) (CAS 13676-53-4), 4,4'-Bis(maleimido)-1,1'-biphenyl (CAS 3278-30-6), 4,4'-Bis(3-maleimidophenoxy)diphenylsulfone; or maleimide-terminated WA12420S / Mk 36 thermoplastic polymers (D2),which can be produced, for example, by reacting amino-terminated thermoplastics (C2) with maleic anhydride, such as maleimide-terminated polysulfone ethers; as well as mixtures of various maleimide resins (D2). Preferably, the at least one compound (D) is a monomeric compound without a thermoplastic, homo-, or copolymeric polymer component. If the compositions according to the invention contain at least one reactive resin (D1), the at least one reactive resin is used in amounts preferably 1 to 40 parts by weight, more preferably 1 to 30 parts by weight, and more preferably 1 to 20 parts by weight, in each case based on 100 parts by weight of component (A). If the compositions according to the invention contain at least one reactive resin (D2), the at least one reactive resin is used in amounts preferably 1 to 60 parts by weight, more preferably 1 to 50 parts by weight, and more preferably 1 to 40 parts by weight.in particular 1 to 30 parts by weight, each based on 100 parts by weight of component (A). In one of the preferred embodiments, the compositions according to the invention do not contain any reactive resins (D). In one of the further preferred embodiments, the compositions according to the invention contain reactive resin (D2). If the compositions according to the invention contain at least polymerizable imide (D2), this is preferably in combination with components which are copolymerizable with both cyanate ester groups and imide groups, preferably maleimido groups. These components are selected from such cyanate esters (A), modifiers (C3) or modifiers (C4) which have propenyl groups bonded to aromatic carbon atoms; or to aromatic hydrocarbon compounds,which have one or two hydroxy groups bonded to aromatic carbon atoms per molecule, as well as one or two polymerizable imido groups, preferably maleimido groups, bonded to aromatic carbon atoms, such as N-(4-hydroxyphenyl)maleimide (CAS 7300-91-6). If the compositions according to the invention contain at least one polymerizable imide resin (D2) in combination with the components mentioned in the preceding paragraph, the molar ratio of the sum of the imido groups to the sum of the propenyl groups is in a range of preferably 45:55 to 95:5, particularly preferably 55:45 to 90:10, and particularly 65:45 to 80:20. Compound (E) The at least one optional filler (E) in the compositions according to the invention can be any particle-shaped filler known to date. The optional at least one filler (E) according to the invention is preferably such aswhich dissolve in toluene at 23°C and 1000 hPa in less than 1 wt%. Examples of fillers are non-reinforcing particulate fillers, i.e., fillers with a BET surface area of preferably up to 50 m². 2 / g, for example, from quartz, glass, cristobalite, diatomaceous earth; water-insoluble silicates WA12420S / Mk 38, such as calcium silicate, calcium metasilicate, magnesium silicate, zirconium silicate, talc, mica, feldspar, kaolin, zeolites; metal oxides, such as aluminum, titanium, iron, boron, or zinc oxides or their mixed oxides; barium sulfate, calcium carbonate, marble flour, gypsum, silicon nitride, silicon carbide, boron nitride, plastic powders, such as polyacrylonitrile or polyetherimide powders; reinforcing fillers, i.e., fillers with a BET surface area of more than 50 m² 2 / g, such as pyrogenic silica, precipitated silica, precipitated chalk, carbon black, such as furnace and acetylene carbon black and silicon-aluminum mixed oxides of large BET surface area; aluminum trihydroxide, magnesium hydroxide, hollow spherical fillers, such as glass microballoons, glass spheres, phenolic thermal spheres or ceramic microspheres, such as those available under the trade name Zeeospheres™ from 3M Germany GmbH in Neuss, Germany; fibrous fillers, such as wollastonite, montmorrilonite, basalt, bentonite, as well as cut and / or ground fibers of glass (short glass fibers) or mineral wool; metallic fibers, fibers consisting of metal oxides, glass, ceramics, carbon or plastic; as well as natural fibers made of cellulose, flax, hemp, wood or sisal. The optional at least one filler (E) according to the invention can be a single filler or a mixture of at least two different fillers (E) in the composition according to the invention. In the case of component(E) These are selected particle-shaped fillers including fibers up to a length of 5 cm (E1) and fiber semi-finished products (E2) containing fibers with a length of over 5 cm, with fiber semi-finished products (E2) being preferred. WA12420S / Mk 39 The optional at least one filler (E2) is preferably all previously known fiber-forming materials made of polypropylene, polyethylene, polytetrafluoroethylene, polyester; metallic fibers made of steel; oxide and non-oxide ceramics, such as silicon carbide, aluminum oxide, silicon dioxide, boron oxide; glass, quartz, carbon, aramid, asbestos, graphite, acrylonitrile, poly(benzothiazole), poly(benzimidazole), poly(benzoxazole), titanium dioxide, boron; as well as aromatic polyamide fibers, such as poly(p-phenylene terephthalamide). The aforementioned at least one filler (E) may optionally be surface-treated to make the surface hydrophobic, to improve the bonding to the resin matrix or to facilitate processing;for example, by treatment with organosilanes or siloxanes, such as modifier (C1), stearic acid, or thermoplastics (C2). Furthermore, at least one filler (E) can be modified by oxidation or treatment with acids or bases. Preferably, at least one filler (E2) is surface-treated. The optional at least one filler (E) according to the invention can be a single filler or a mixture of at least two different fillers (E) in the composition according to the invention. If the composition according to the invention contains at least one (E1), the proportion of the at least one filler (E1) is preferably 5 to 900 parts by weight, particularly preferably 10 to 400 parts by weight, and in particular 15 to 150 parts by weight, each based on 100 parts by weight of the sum of components (A) and (B). WA12420S / Mk 40 If the composition according to the invention contains at least one filler (E2), the proportion of the at leastThe filler (E2) preferably comprises 20 to 900 parts by weight, particularly preferably 60 to 900 parts by weight, and especially 100 to 400 parts by weight, each based on 100 parts by weight of the sum of components (A) and (B). The at least one filler (E2) can be present in the composition according to the invention in various forms, e.g., as continuous ropes with 1,000 to 400,000 individual filaments each, woven fabrics, nonwovens, knitted fabrics, braids, mats, fleeces, whiskers, cut short fibers, or random fiber felt. The compositions according to the invention preferably contain at least one filler (E), wherein the at least one filler (E) particularly preferably consists predominantly, and especially entirely, of filler (E2). Preferably, the compositions according to the invention contain as filler (E2) ropes, woven fiber fabrics, nonwoven fiber fabrics, knitted fiber fabrics, or Fiber braids, particularly preferably consisting of carbon fibers, aromatic polyamide fibers,ceramic and / or glass fibers, wherein either the respective fibers and / or the ropes, fiber fabrics, fiber woven fabrics, fiber knitted fabrics or fiber braids produced therefrom are particularly surface-treated. The respective fibers are particularly preferably surface-treated. The fiber fabrics (E2) or fiber woven fabrics (E2) optional according to the invention are preferably used in multiple layers. WA12420S / Mk 41 In a preferred embodiment, component (E2) comprises at least 80 wt.%, particularly preferably at least 90 wt.%, fiber fabrics, fiber woven fabrics, fiber knitted fabrics or fiber braids, based on 100 wt.% component (E2). Compound (F) The composition according to the invention can be cured in the presence of at least one curing accelerator (F) as known from the prior art. Suitable hardening accelerators (F1) include, for example, acids and bases such as hydrochloric acid, phosphinic acid, phosphonic acid, phosphoric acid, sulfonic acid, aliphatic and aromatic acids.Amines, such as triethylamine, N,N-dimethylaniline and pyridine; amidines, guanidines, sodium hydroxide; halides, such as aluminum chloride, lithium chloride, boron fluoride, iron chloride, zinc chloride, zinc fluoride, tin chloride, cobalt chloride and titanium chloride; as well as organometallic compounds, such as metal alcoholates, metal carboxylates or metal chelate complexes of aluminum, copper, zinc, titanium, iron, manganese, cobalt, chromium or nickel. Examples of organometallic compounds are cobalt(II) naphthenate, nickel(II) naphthenate, iron(III) naphthenate, copper(II) naphthenate, manganese(II) naphthenate, aluminum(III) naphthenate, zinc(II) naphthenate, zinc(II) octoate, zinc(II) acetylacetonate, iron(III) acetylacetonate, cobalt(II) acetylacetonate, chromium(III) acetylacetonate, aluminum(III) acetylacetonate, and copper(II) acetylacetonate. If at least one accelerator (F1) is used for the hardening of the compositions according to the invention, it is preferably a combination oforganometallic compound and a co-accelerator having at least one active proton, particularly preferably a combination WA12420S / Mk 42 of an organometallic compound and a phenol (C4), such as Nonylphenol. If the compositions according to the invention contain at least one accelerator (F1), the amounts are preferably 0.00001 to 5 parts by weight based on 100 parts by weight of component (A), wherein organometallic compounds (F1) are particularly preferably used in amounts of 0.0001 to 0.02 parts by weight based on 100 parts by weight of component (A). If the compositions according to the invention contain radically polymerizable functional groups such as aliphatic carbon-carbon multiple bonds, radical-forming curing accelerators (F2), such as organic peroxides, e.g., dicumyl peroxide, di-tert-butyl peroxide, dibenzoyl peroxide, dilauroyl peroxide, 1,1-bis(tert-butylperoxy)cyclohexane, and tert-butyl perbenzoate, can be used.or azo compounds, such as azobis(isobutyronitrile); either alone or in addition to (F1). If the compositions according to the invention contain radical-forming curing accelerators (F2), these are amounts of preferably 0.1 to 2 parts by weight based on 100 parts by weight of the sum of imido-group-containing modifier (C1) and imide resin (D2). Preferably, no radical-forming curing accelerators (F2) are used. Compound (G) Examples of the optional at least one solvent (G) are aliphatic mono- and polyhydric alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, iso-butanol, sec-butanol, 1,2-ethanediol, 1,2-propanediol, 1,3-propanediol, polypropylene glycol, polyethylene glycol, 1,2-butanediol, 1,3-WA12420S / Mk 43 butanediol, polybutylene glycol and glycerol; ethers, such as methyl tert-butyl ether, di-tert-butyl ether and di-, tri- or tetraethylene glycol dimethyl ether; saturated hydrocarbons, such as n-hexane, cyclohexane, n-heptane, n-octaneand isomeric octanes, such as 2-ethylhexane, 2,4,4-trimethylpentane, 2,2,4-trimethylpentane, 2-methylheptane and trichloroethylene, as well as mixtures of saturated hydrocarbons with boiling ranges between 60-300°C, such as those available under the trade names Exxsol™, Hydroseal® or Shellsol®; aromatic solvents, such as benzene, toluene, styrene, o-, m- or p-xylene, solvent naphtha, dimethyl phthalate, diisobutyl phthalate, dicyclohexyl phthalate, mesitylene and chlorobenzene; aldehyde acetals, such as methylal, ethylhexylal, butylal, 1,3-dioxolane and glycerol formal; Carbonates, such as 1,3-dioxolan-2-one, diethyl carbonate, dimethyl carbonate, dipropyl carbonate, propylene glycol carbonate, ethylene carbonate; ketones, such as acetone, methyl isobutyl ketone, methyl ethyl ketone, methyl isoamyl ketone, diisobutyl ketone, acetone, and cyclohexanone; esters, such as ethyl acetate, n-butyl acetate, ethylene glycol diacetate, gamma-butyrolactone, 2-methoxypropyl acetate (MPA), dipropylene glycol dibenzoate, and ethyl ethoxypropionate; amides, such asN,N-Dimethylformamide, N,N-Dimethylacetamide, N-Methyl-2-pyrrolidone and N-Ethyl-2-pyrrolidone; acetonitrile; and dimethyl sulfoxide. The at least one solvent (G) is preferably an aromatic hydrocarbon or a ketone. If the compositions according to the invention contain at least one solvent (G), the amounts are preferably 1 to 300 parts by weight, particularly preferably 1 to 100 parts by weight, and in particular 5 to 50 parts by weight, each based on 100 parts by weight of the sum of components (A) and (B). The compositions according to the invention preferably contain no solvent (G). No solvent (G) in this context means that its presence in the scope of usual impurities is permissible in order to still be included in the scope of this preferred embodiment. Compound (H) The at least one auxiliary substance (H) according to the invention is preferably a pigment, dye,Fragrances, processing aids such as agents to influence stickiness, lubricants, demolding agents, antiblocking agents or dispersing agents; stabilizers against hydrolysis, light, oxidation, heat, discoloration; flame retardants or plasticizers. If the compositions according to the invention contain at least one excipient (H), the at least one excipient (H) is present in amounts preferably of 0.01 to 20 parts by weight, particularly preferably 0.1 to 10 parts by weight, and especially 0.1 to 5 parts by weight, each based on 100 parts by weight of the sum of components (A) and (B). The compositions according to the invention preferably do not contain any excipient (H). In a preferred embodiment, the compositions according to the invention are those containing (A) at least one cyanate ester resin, (B) at least one poly(diorgano)siloxane, optionally (C) at least one modifier, optionally (D) at least one reactive resin, (E2) at least onefiber-reinforcing filler, optionally (F) at least one curing accelerator, optionally (G) at least one solvent, and optionally (H) at least one excipient. In a further preferred embodiment, the compositions according to the invention are those containing (A) at least one cyanate ester resin, (B) at least one poly(diorgano)siloxane, optionally (C) at least one modifier selected from group (C1) to (C4), (D2) at least one maleimide resin, (E2) at least one fiber-reinforcing filler, optionally (F) at least one curing accelerator, optionally (G) at least one solvent, and optionally (H) at least one excipient, with the proviso that at least one component (A), (C3), or (C4) has propenyl groups directly bonded to aromatic carbon atoms, or at least one aromatic hydrocarbon compound, which has one or two per molecule bonded to aromatic carbon atomsThe compositions according to the invention contain bound hydroxy groups as well as one or two polymerizable imido groups, preferably maleimido groups, bonded to aromatic carbon atoms. The compositions according to the invention preferably contain, in addition to components (A) and (B), the optional components (C) to (H), and optionally raw material-specific impurities, for example, catalyst residues such as sodium chloride, potassium chloride, or platinum compounds, impurities in technical cyanate ester resin monomers, solvent residues, and optionally reaction products of the components used that arise during mixing or storage, no further components. WA12420S / Mk 46 In the compositions according to the invention, the components described above can each be used individually or in the form of a mixture of at least two of the respective components. The compositions according to the invention can be prepared according to known processes, such asFor example, by mixing the individual components in any order and in a previously known manner. A further object of the present invention is a method for producing the compositions according to the invention by mixing the individual components in any order. In the method according to the invention, the mixing can take place at temperatures in the range of preferably 20 to 150°C, particularly preferably in the range of 50 to 130°C, and especially at temperatures of 60 to 120°C. It is particularly preferred to mix at the temperature that results from mixing at ambient temperature, based on the temperature of the raw materials plus the temperature increase due to the energy input during mixing, whereby heating or cooling can be carried out as required. The mixing can take place at atmospheric pressure, i.e., approximately 900 to 1100 hPa. Furthermore, it is possible to mix temporarily or continuously under reduced pressure, such as at 30 to500 hPa absolute pressure to remove volatile compounds and / or air, or to operate under overpressure, such as at pressures between 1100 hPa and 3000 hPa absolute pressure, particularly in continuous operation, where, for example, these pressures result in closed systems due to WA12420S / Mk 47, the pressure during pumping, and the vapor pressure of the materials used at elevated temperatures. The process according to the invention can be carried out continuously, discontinuously, or semi-continuously; it is preferably carried out discontinuously. In a preferred embodiment of the process according to the invention for producing the compositions according to the invention, the individual components, except for component (E), are premixed in any order. Subsequently, filler (E2) is added to the premix using known processing techniques, such as prepregging (from the melt, solution, or suspension), sheet molding compound (SMC), or winding (filament) processes.Winding), compression molding, pultrusion, fiber spraying, and injection processes such as resin transfer molding or vacuum infusion are used to impregnate the components without bubbles and process them into molded parts. The compositions according to the invention can be used for all purposes for which organic reactive resin systems or their prepolymers have previously been used for subsequent curing in thermosets. In one variant of the process according to the invention, components (A) and (B), as well as the optional components (C), (D), (F), (G), and (H), are preferably first mixed in any sequence to form a premix, and then component (E2), preferably ropes, woven fabrics, non-woven fabrics, knitted fabrics, or braids, is impregnated with the premix, optionally under pressure, and optionally degassed. In the case of multilayer woven fabrics, non-woven fabrics, knitted fabrics, or braids (E2), each layer WA12420S / Mk 48 can be impregnated and degassed individually or all layers together. In a furtherIn a preferred embodiment of the process according to the invention, components (A) and (B) as well as the optional components (C), (D), (F), (G), and (H) are first mixed in any order to form a premix, and then injected into a mold cavity containing component (E2), preferably ropes, woven fabrics, non-woven fabrics, knitted fabrics, or braids, preferably degassing occurs simultaneously during the injection process. In a further preferred embodiment of the process according to the invention, components (A) and (B) as well as the optional components (C), (D), (F), (G), and (H) are first mixed in any order to form a premix, and then applied to a carrier (release paper or release film) which can subsequently be rolled up; subsequently, component (E2), preferably aligned ropes, woven fabrics, non-woven fabrics, knitted fabrics, or braids, is pressed between two coated carriers, preferably at a temperature above 50°C and / or under pressure.The component (E2) is guided by a series of heated rollers to ensure complete wetting. In a further preferred embodiment of the inventive method, components (A) and (B), as well as the optional components (C), (D), (F), (G), and (H), are first mixed in any order to form a premix and then applied to the top surface of component (E2), preferably woven fabric, non-woven fabric, knitted fabric, or braid. Subsequently, the wet blank is transferred to a lower tool of a series of adapted molds and pressed in a press, WA12420S / Mk 49, which presses the composition mainly in the Z-direction into the fabric. The inventive compositions can be formed into any desired shape by mechanical pressure at ambient temperature or, optionally, at elevated temperature. The inventive compositions are preferably malleable and are particularly preferably formed in a mold cavity or around a mold template.modeled and cured. Another object of the invention is therefore the use of the composition according to the invention for the production of molded parts or fiber-reinforced composites. Another object of the invention is therefore a method for producing molded parts by shaping the composition and subsequent curing. Another object of the invention is therefore molded parts obtainable from the compositions according to the invention by shaping and curing. The compositions according to the invention or produced according to the invention are preferably degassed before curing, particularly preferably after shaping and before curing. The curing according to the invention preferably takes place at temperatures in the range of 50 to 350°C, particularly preferably from 100 to 300°C, and especially from 120 to 270°C. Most preferably, the curing according to the invention takes place in stages at temperatures from 120 to 270°C. WA12420S / Mk 50 By increasing the temperature, theThe curing process can be accelerated so that shaping and curing can be carried out in a single step. The molded parts according to the invention are preferably fiber-reinforced composites (or fiber-reinforced plastics "FRP"). A further object of the invention is a method for producing fiber-reinforced composites, characterized in that the compositions according to the invention are shaped and cured. The compositions according to the invention can be solid or liquid at a temperature of 100°C and an atmospheric pressure of 1013 hPa, preferably being liquid at 100°C and 1013 hPa. If the compositions according to the invention are liquid at 100°C and 1013 hPa, they have a dynamic viscosity of preferably 1 to 5,000 mPa·s, more preferably 1 to 2,000 mPa·s, particularly preferably 1 to 1,000 mPa·s, and especially 1 to 500 mPa·s. at 100°C and 1013 hPa. The quotient of the critical voltage intensity factor KIc of theThe water absorption of the hardened compositions according to the invention, for example, consisting of 85 parts by weight of cyanate ester resin (A) and 15 parts by weight of poly(diorgano)siloxane (B), to the respective hardened, unmodified cyanate ester resin (A), is preferably greater than 1.1, particularly preferably greater than 1.2, and especially greater than 1.3, each measured at 23°C. WA12420S / Mk 51 The hardened compositions according to the invention, for example, consisting of 85 parts by weight of cyanate ester resin (A) and 15 parts by weight of poly(diorgano)siloxane (B), exhibit a reduction in water absorption of preferably at least 20%, preferably at least 30%, particularly preferably at least 40%, and especially at least 45% after 1600 hours of water storage at 70°C compared to the corresponding unmodified cyanate ester resin (A). The hardened compositions according to the invention, for example consisting of 85 parts by weight of cyanate ester resin (A) and 15 parts by weight of poly(diorgano)siloxane (B), exhibit a glass transition temperature of preferablygreater than 170°C, particularly preferably greater than 200°C, and especially greater than 230°C. The cured compositions according to the invention, for example, consisting of 85 parts by weight of cyanate ester resin (A) and 15 parts by weight of poly(diorgano)siloxane (B), exhibit a weight loss after 200 hours of storage at 240°C that is preferably a maximum of 150%, more preferably a maximum of 100%, more preferably a maximum of 90%, and particularly a maximum of 80%, higher compared to the corresponding unmodified cyanate ester resins (A). The compositions according to the invention have the advantage that cyanate ester resin (A) is homogeneously miscible with poly(diorgano)siloxane (B) without the addition of further solvent and without pre-crosslinking in the presence of a curing accelerator, and that poly(diorgano)siloxane (B) does not seep or oil out of the thermoset network during or after curing. The compositions according to the invention have the advantage that they exhibit a high glass transition temperature in the cured state, WA12420S / Mk 52a high fracture toughness (K Ic) and exhibit reduced water absorption and thus improved hydrolysis resistance compared to the corresponding unmodified cyanate ester resins. The compositions according to the invention also have the advantage of exhibiting high thermo-oxidative stability in the cured state. The molded bodies according to the invention have the advantage of being heat-stable and having a reduced fire load compared to composite materials made from purely organic cyanate ester resin systems. The compositions according to the invention have the advantage of being easily produced from readily available raw materials. The compositions according to the invention have the advantage that no harmful emissions are produced during processing, unlike those typically associated with organic cyanate ester resins used in the prior art.Exemplary embodiments The following examples were carried out at ambient atmospheric pressure, i.e., at approximately 1013 hPa, and at room temperature, i.e., approximately 23°C or a temperature that occurs when the reactants are combined at room temperature without additional heating or cooling, and describe the basic feasibility of the present invention, without, however, limiting it to the contents disclosed therein.WA12420S / Mk 53 Molar masses Within the scope of the present invention, the weight mean molar mass Mw and the number mean molar mass Mn, each in the unit g / mol, rounded to whole numbers of 10 according to DIN 1333:1992-02 Section 4, are determined by size exclusion chromatography (SEC / GPC) according to DIN 55672-1 / ISO 16014-1 and ISO 16014-3 with toluene as eluent, by calibrating a column set based on polystyrene-co-divinylbenzene as the stationary phase from three columns with different pore size distributions in the order 10000 Å, 500 Å and 100 Å with an exclusion size of greater than 450000 g / mol against polystyrene standards. The analyses are performed at a column temperature of 45±1°C using a refractive index detector. Preparation of the test specimens: First, 85 parts by weight, based on 100 parts by weight of the sum of components (A) and (B), of cyanate ester resin (A) were heated to 80°C while being thoroughly mixed to improve processability.Then, 15 parts by weight of poly(diorgano)siloxane (B), based on 100 parts by weight of the sum of components (A) and (B), were added. The composition was homogenized for 30 minutes at 100°C, then degassed for 15 minutes at 100°C and a pressure of 10 mbar. After breaking the vacuum with nitrogen, the compatibility of the test composition was visually assessed before hardening at 100°C, and the result was recorded in Table 1. The assessment was based on the criteria “+” = compatible, i.e., no macroscopic phase separation visible to the naked eye, and “-” = incompatible, i.e., macroscopic phase separation of components (A) and (B) visible to the naked eye.The test composition was then immediately hot-poured into a two-part, screw-on aluminum mold (WA12420S / Mk 54) preheated to 160°C. The mold cavity dimensions were 200 mm x 100 mm x 6.5 mm (length x width x height) for the production of test specimens for determining fracture toughness, water absorption, thermo-oxidative stability, and for performing dynamic mechanical analysis (DMA). To prevent sticking and leakage, the mold cavity surface on the inside of the mold was treated with a mold release agent (LOCTITEFREKOTE HMT-2; commercially available from Henkel AG & Co. KGaA, DE-Düsseldorf), and a 2 mm thick round cord of fluororubber with a hardness of 75 Shore A was placed around the mold cavity.To determine the compatibility of compound (B) with cyanate ester resin (A) after curing, the test composition was half-filled into an aluminum tray measuring 45 mm x 10 mm (diameter x height) and cured without covering the surface. For curing, the filled molds were stored in a convection oven according to the following temperature program: 1) 18 hours of curing at 180°C; 2) temperature increase to 200°C within 30 minutes; 3) 3 hours of curing at 200°C; 4) temperature increase to 240°C within 30 minutes; 5) 2 hours of curing at 240°C. The specimen was then allowed to cool to 23°C in the mold before being demolded. For further use, the upper 10 mm of the hardened specimen side, which was open and exposed to air during hardening in the mold, were cut off and discarded.The test specimens for measuring fracture toughness, water absorption, thermo-oxidative stability, and DMA were then cut from the large, hardened specimen plate (WA12420S / Mk 55, 6.5 mm high) using a diamond cutting saw to the corresponding length x width dimensions. The 2.00 mm thick test specimens for measuring water absorption were cut from the inner part of the pre-cut piece using an internal-hole diamond saw, ensuring that all six surfaces of these specimens were sawn. The composition hardened in the aluminum mold was not demolded after cooling; compatibility was assessed based on the air-side surface. Fracture Toughness KIc: The measurement of fracture toughness, or the critical stress intensity factor KIc, was performed as described in the publication "Reactive and Functional Polymers 142 (2019) 159-182" at 23°C and 50% relative humidity. The thickness of the test specimens was 6.5 mm.The value for fracture toughness KIc in MN× m-3 / 2 given in Table 1 was rounded to two decimal places according to DIN 1333:1992-02 Section 4. Dynamic mechanical analysis (DMA) Measurement conditions: ^Measuring instrument: ARES rheometer (TA instruments)^ Temperature range: -100°C – 300°C^ Heating rate: 4 K / min with nitrogen purge^ Frequency: 1 Hz^ Strain: Initial 0.03%, automatically increased when measurement signal falls below threshold. For the investigations, cuboid test specimens with dimensions length x width x height = 40 mm x 6 mm x 3 mm were used; The resulting clamping length was 25 mm. In the present invention, the glass transition temperature TG corresponds to the maximum value of the tangent delta curve (= tan deltamax), i.e., the measurement temperature at which the WA12420S / Mk 56 ratio of loss modulus G'' to storage modulus G' is greatest. The value for the glass transition temperature TG given in Table 1 has been rounded to whole numbers, in accordance with DIN 1333:1992-02 Section 4.Water Absorption: In the present invention, water absorption was determined gravimetrically after storage of the test specimens in tempered water. Cuboid test specimens with dimensions length x width x thickness = 30.00 mm x 17.00 mm x 2.00 mm were used; the accuracy of the weight determination was ±0.01 mg. The test specimens were first dried in a vacuum oven at 70°C and 30 mbar until a constant weight was achieved, with the weight being determined at 24-hour intervals. The test specimens were considered "dry" if no further weight loss was measured over a period of 48 hours. Each dry test specimen was then immersed in 45 ml of deionized water in a suitable sealable container; the sealed container was then placed in a convection oven preheated to 70°C and maintained at this temperature throughout the entire test period.After 1600 hours, the test specimens were removed, cooled to 23°C, and the surfaces were wiped dry with a cloth; the weight of the test specimens was then determined again. The water absorption (or weight gain) was calculated according to the values in Table 1. Water absorption value given in % and rounded to two decimal places according to DIN 1333:1992-02, Section 4. Thermo-oxidative stability WA12420S / Mk 57. In the present invention, the thermo-oxidative stability was determined gravimetrically after storage of the test specimens at 240°C. Cuboid test specimens with dimensions length x width x thickness = 12.00 mm x 6.50 mm x 6.50 mm were used; the accuracy of the weight determination was ±0.1 mg. The test specimens were first dried in a vacuum oven at 70°C and 30 mbar until a constant weight was achieved, with the weight being determined at 24-hour intervals. The test specimens were considered "dry" if no further weight loss was measured over a period of 48 hours. Subsequently, the test specimens were stored in a convection oven at 240°C. After 200 hours, the test specimens were removed and their weight was determined again. The weight loss was calculated according to the values in Table 1.Weight loss value given in % and rounded to two decimal places according to DIN 1333:1992-02, Section 4. Compatibility: The compatibility of compound (B) with cyanate ester resins (A) was visually assessed based on the criteria specified in Table 1: - Before curing and after storing the composition for 15 minutes at 100°C: "+" = composition is macroscopically homogeneous (single-phase), and "-" = composition is macroscopically inhomogeneous (two-phase); - After curing: "+" = good compatibility, i.e., no visible oiling or seepage of compound (B) from the cured composition, and "-" = poor compatibility, i.e., visible oiling or seepage of component (B) from the cured composition. Furthermore, the stickiness or oiliness of the air-side surface was tested using an LDPE film. (CAS: 9002-88-4) and a filter paper (Whatman™ Filter Paper Grade 589 / 2) determined by examining the film orthe filter paper was pressed onto the surface and then peeled off. As shown in Table 1, surface stickiness / oiliness was differentiated into “+” (test specimen surface dry, not sticky and not oily (filter paper dry)) and “-” (test specimen surface soft, sticky and / or oily (filter paper moist)). Preparation of 1-allyloxy-4-(1-methyl-1-phenyl-ethyl)benzene (“1-allyloxy-4-cumylbenzene”; CAS 68443-36-7): 200 g (942 mmol) of 4-cumylphenol (CAS 599-64-4; commercially available from Sigma-Aldrich Chemie GmbH, D-82024 Taufkirchen) and 38.0 g (950 mmol) of sodium hydroxide pellets (commercially available from abcr GmbH, D-76187 Karlsruhe) are dissolved in 300 g of solution at 23°C under a nitrogen atmosphere. Dimethyl sulfoxide anhydrous (available for purchase from Sigma-Aldrich Chemie GmbH, D-82024 Taufkirchen) is mixed, the mixture is stirred for 15 minutes.Then, 76.6 g (1001 mmol) of allyl chloride (CAS 107-05-1; commercially available from Sigma-Aldrich Chemie GmbH, D-82024 Taufkirchen) are added dropwise over a period of 1 hour. After the addition is complete, the mixture is stirred for 6 hours at 40°C and then overnight at room temperature. The composition is then modified with 400 ml of pentane; subsequently, deionized water is added until phase separation begins. The organic phase is separated from the aqueous phase and extracted successively twice with a composition of 90 g distilled water, 10 g absolute ethanol and 5 g potassium hydroxide (absolute ethanol and potassium hydroxide commercially available from Sigma-Aldrich Chemie GmbH, D-82024 Taufkirchen), WA12420S / Mk 59, once with a composition of 90 g distilled water and 10 g ethanol and finally once with distilled water.The organic phase is dried over anhydrous sodium sulfate (commercially available from Sigma-Aldrich Chemie GmbH, D-82024 Taufkirchen, Germany). Subsequently, the volatile components of the composition are removed using a rotary evaporator. 224 g of reaction product remain as an oily residue in the flask and are processed further without further purification. Preparation of 2-allyl-4-(1-methyl-1-phenyl-ethyl)phenol (“2-allyl-4-cumylphenol”): 200 g of the previously prepared 1-allyloxy-4-cumylbenzene are heated to 200°C for 5 hours under a nitrogen atmosphere with thorough mixing. The product is then obtained by fractional distillation under vacuum. Yield 192 g. Preparation of Si-H-terminated poly(dimethyl)siloxane (“SiH_1”) The mixture of 200.0 g (1489 mmol) 1,1,3,3-tetramethyldisiloxane, 222.5 g (1000 mmol)hexamethylcyclotrisiloxane and 30.0 g Purolite CT269 is stirred moderately under reflux for 4 h at 90°C oil bath temperature.The mixture is then filtered and separated by fractional distillation under vacuum. The fraction in the boiling range of 80°C to 85°C at a pressure of 0.3 mbar has an average composition (HMe2SiO1 / 2)2(Me2SiO2 / 2)6,5, a weight-average molar mass Mw of 870 g / mol and a number-average molar mass Mn of 770 g / mol. Hydrosilylation reaction for the preparation of compound (B) Under a nitrogen atmosphere, 25 g of a linear poly(dimethyl)siloxane with terminal Si-bonded hydrogen atoms (Si-H) WA12420S / Mk 60 are mixed with 30 g of anhydrous toluene (commercially available from Sigma-Aldrich Chemie GmbH, D-82024 Taufkirchen), then 0.01 g of platinum catalyst (commercially available under the name WACKER® CatalystOL from Wacker Chemie AG, D-Munich) are added.Then, while stirring, a mixture of an aromatic hydrocarbon compound, which has a phenolic hydroxyl group and an aliphatic unsaturated carbon-carbon (C=C) double bond, is added dropwise to 20 ml of toluene over 30 minutes; the amount of aromatic compound used is calculated so that the molar ratio (in mmol / mmol) of silicon-bonded hydrogen atoms (Si-H) to aliphatic unsaturated carbon-carbon double bonds is 1:1.05. After the addition is complete, the mixture is stirred for 5 hours at 90°C and, after cooling to 50°C, 1 g of Köstrosorb® 1020 (commercially available from Chemiewerk Bad Köstritz GmbH, D-07586 Bad Köstritz) is added and stirred for a further 30 minutes at 23°C. The mixture is filtered and the volatile components are removed from the filtrate using a rotary evaporator at 100°C and 5 mbar.The 1H and 29Si NMR controls indicate an almost complete conversion of the Si-H groups and the C=C double bonds; The conversion is more than 96 mol-%. Example B1 According to the manufacturing procedure “Hydrosilylation reaction for the preparation of compound (B)”, a (cumylphenol)propyl-terminated poly(dimethyl)siloxane is produced from the reaction of 2-allyl-4-cumylphenol with a linear poly(dimethyl)siloxane with terminal Si-bonded hydrogen atoms of the medium composition (HMe2SiO1 / 2)2(Me2SiO2 / 2)6,9, a weight-average molar mass Mw of 1060 g / mol and a number-average molar mass Mn of 690 g / mol WA12420S / Mk 61 (commercially available under the name WACKER® 1085 silicone oil from Wacker Chemie AG, D-Munich). The reaction product has a weight-average molar mass Mw of 1570 g / mol, a number-average molar mass Mn of 950 g / mol and a dynamic viscosity of 467 mPa·s.As described in the section "Preparation of the test specimens", 1,1-bis(4-cyanatophenyl)ethane (CAS 47073-92-7; commercially available under the trade name Primaset® LECy from Arxada Ltd., CH-4002 Basel) is mixed as component (A) with the previously prepared component (B) and then processed. The results are shown in Table 1a. Example B2 According to the manufacturing procedure “Hydrosilylation reaction for the preparation of compound (B)”, a (cumylphenol)propyl-terminated poly(dimethyl)siloxane is produced from the reaction of 2-allyl-4-cumylphenol (manufacturing procedure see above) with a linear poly(dimethyl)siloxane with terminal Si-bonded hydrogen atoms of the average composition (HMe2SiO1 / 2)2(Me2SiO2 / 2)10.5, a weight-average molar mass Mw of 1780 g / mol and a number-average molar mass Mn of 930 g / mol (commercially available under the name WACKER® H-Polymer 13 from Wacker Chemie AG, D-Munich).The reaction product has a weight-average molar mass Mw of 2660 g / mol, a number-average molar mass Mn of 1440 g / mol, and a dynamic viscosity of 405 mPa·s. As described in the section "Preparation of Test Specimens," 2,2-bis(4-cyanatophenyl)propane (CAS 1156-51-0; commercially available under the trade name Primaset® BADCy from Arxada WA12420S / Mk 62 Ltd., CH-4002 Basel) is mixed as component (A) with the previously prepared component (B) and then processed. The results are shown in Table 1a. Example B3: According to the manufacturing procedure “Hydrosilylation reaction for the preparation of compound (B)”, a phenolpropyl-terminated poly(dimethyl)siloxane is prepared from the reaction of 2-allylphenol (CAS 1745-81-9; commercially available from Sigma-Aldrich Chemie GmbH, D-82024 Taufkirchen) with “SiH_1”. The reaction product has an intermediate composition (HMe2SiO). 1 / 2 )2(Me2SiO 2 / 2 ) 6,7, a weight-average molar mass Mw of 640 g / mol, a number-average molar mass Mn of 530 g / mol, and a dynamic viscosity of 53 mPa·s. As described in the section "Preparation of the Test Specimens," a novolac cyanate ester resin (CAS 87397-54-4; commercially available under the trade name Primaset® PT-15 from Arxada Ltd., CH-4002 Basel) is mixed as component (A) with the previously prepared component (B) and then processed. The results are shown in Table 1a. Comparative Example V1: The procedure described in Example B1 is repeated with the modification that no component (B) is added to component (A). The results are shown in Table 1b. WA12420S / Mk 63 Comparison Example V2: The procedure described in Example B2 is repeated with the modification that no component (B) is added to component (A). The results can be found in Table 1b.Comparative Example V3: The procedure described in Example B3 is repeated with the modification that no component (B) is added to component (A). The results can be found in Table 1b. Comparative Example V4: As described in the section "Preparation of the Test Specimens," a novolac cyanate ester resin PRIMASET® PT-15 as component (A) is mixed with a phenolpropyl-terminated poly(dimethyl)siloxane of the average composition ((HOC6H4(CH2)3)Me2SiO1 / 2)2(Me2SiO2 / 2)36, a weight-mean molar mass Mw of 5930 g / mol, a number-mean molar mass Mn of 3400 g / mol, and a dynamic viscosity of 100 mPa·s (commercially available under the name WACKER® Fluid PF 37 from Wacker Chemie AG, Munich, Germany) as component (B) and then processed. The results can be found in Table 1b.Comparative Example V5: As described in the section "Preparation of Test Specimens," a novolac cyanate ester resin (CAS 87397-54-4; commercially available under the trade name Primaset® PT-15 from Arxada Ltd., CH-4002 Basel) as component (A) is mixed with a phenolpropyl WA12420S / Mk 64-terminated poly(dimethyl)siloxane of the medium composition ((HOC6H4(CH2)3)Me2SiO1 / 2)2(Me2SiO2 / 2)72, with a dynamic viscosity of 106 mPa·s (commercially available under the name silicone oil X-22-1822 from Shin-Etsu Chemical Co., Ltd., Tokyo 100-0005, Japan) as component (B) and subsequently processed. The results are shown in Table 1b. eispiel B1 B2 B3 Compatibility before hardening after + + + Storage for 15 minutes at 100°C, visual compatibility after curing, visual + + +compatibility after curing, + + + LDPE film & filter paper Glass transition temperature TG 236 264 274 Stress intensity factor KIc 0.82 0.71 0.55 at 23°C [MN × m -3 / 2Water absorption at 70°C: 1.5% 1.7% 2.4% after 1600 hours [%] Thermo-oxidative stability, weight loss at 240°C 1,4 2,1 0,9 after 200 hours [%] Table 1b Example V1 V2 V3 V4 V5 Compatibility before curing after 15 min storage at 100°C,*1 *1 *1 - -visual Compatibility after curing, * 1 * 1 * 1 * 2 * 2 visual compatibility after curing, * 1 * 1 * 1 * 2 * 2 LDPE film & filter paper glass transition temperature TG 302 318 339 *2 *2 [°C] Voltage intensity factor KIc 2 2 at 23°C [MN × m -3 / 2 0.55 0.51 0.48 * *] WA12420S / Mk 65 Water absorption at 70°C 2.3 3.1 3.9 *2 *2 after 1600 hours [%] Thermo-oxidative stability, weight loss at 240°C 0,9 1,3 0,7 *2 *2 after 200 hours [%] * 1 not judged. *2 No measurement possible, as (A) and (B) are not compatible / mixable.
Claims
1. WA12420S / Mk 66 Claims 1. Curable compositions comprising (A) at least one organic compound free of siloxy (≡Si-O-) units, with at least two reactive cyanate ester (-OC≡N) groups, (B) at least one poly(diorgano)siloxane of the general formula (i) R k (R 2 -Z-) (3-k) SiO (R p (R 2 -Z-) (2-p) SiO-) q SiR o (R 2 -Z-) (3-o) wherein R is the same or different and -monovalent, SiC-bonded, optionally ether (COC) and / or epoxide (COC) groups, saturated hydrocarbon residues, -monovalent, SiC-bonded, aromatic hydrocarbon residues free of phenolic OH groups or aliphatic C=C multiple bonds, which may be interrupted by heteroatoms, means R 2 is the same or different and is described by formula (IV), (IV) wherein WA12420S / Mk 67 --R6 and R8 each independently contain a hydrogen atom, a hydroxyl (HO) group or a hydrocarbon residue with 1 to 12 carbon atoms, possibly bound via an ether (COC) unit, -R 7 , R 9 and R 10 each independently of one another means a hydrogen atom or a hydrocarbon residue with 1 to 12 carbon atoms, optionally bound via an ether (COC) unit, k is 2 or 3, preferably 2, o is 2 or 3, preferably 2, p is 0, 1 or 2, preferably 1 or 2, particularly preferably 2, q is an integer from 0 to 11, Z is the same or different, and divalent saturated hydrocarbon residues with 2 to 5 carbon atoms consisting of 1 to 3 units of formula (III) means -(CH(2-g)R3g)h- (III), wherein R 3is the same or different and represents a monovalent methyl, ethyl or isopropyl residue, g is 0, 1 or 2, h is 1, 2 or 3, provided that - per poly(diorgano)siloxane molecule (B) of the general formula(i) there are one or two residues (R2-Z-), and WA12420S / Mk 68 - that NO pre-crosslinking of components (A) with (B) is required in the presence of a curing accelerator.
2. Curable compositions according to claim 1, characterized in that, without the addition of solvents and in the absence of a curing accelerator, components (A) and (B) can be processed in liquid form to form a stable, homogeneous composition, wherein this stable, homogeneous composition is particularly characterized in that, after storage of the composition at 100°C for at least 15 minutes, no macroscopic segregation occurs through the formation of a phase interface visible to the naked eye, i.e., recognizable two-phase structure.
3. Curable compositions according to claim 1, characterized in that no pre-crosslinking of components (A) with (B) takes place in the presence of a curing accelerator.
4. Curable compositions according to any one of claims 1 to 3, characterized in that R 2ausgewählt wird aus der Gruppe umfassend Hydroxyphenyl [-C6H4(OH)]-, Hydroxy(methyl)phenyl [-C6H3(OH)(CH3)]-, Hydroxy(tert-Butyl)phenyl [-C6H3(OH)(C(CH3)3)]-, Hydroxy(dimethyl)phenyl[-C6H2(OH)(CH3)2]-, Hydroxy(di-tert-Butyl)phenyl [-C6H2(OH)(C(CH3)3)2]-, Hydroxy(methoxy)phenyl [-C6H3(OH)(OCH3)]-, Hydroxy(phenyl)phenyl [-C6H3(OH)(C6H5)]-, Hydroxy(tert-Octyl)phenyl [-C6H3(OH)((C(CH3)2)(CH2)(C(CH3)3))]-, Hydroxy(nonyl)phenyl [-C6H3(OH)((CH2)8CH3)]-, Hydroxy(dodecyl)phenyl [-C6H3(OH)((CH2) 11 CH3)]-, Hydroxy(tert-Amyl)phenyl [-C6H3(OH)((C(CH3)2)CH2CH3)]-, Hydroxy(isopropyl)phenyl [-C6H3(OH)(CH(CH3)2)]-, Hydroxy(cumyl)phenyl WA12420S / Mk 69 [-C6H3(OH)((C(CH3)2)(C6H5))]-, Hydroxy(phenoxy)phenyl[-C6H3(OH)(OC6H5)]- and the Hydroxynaphthyl [-C10H6(OH)] residue.
5. Curable compositions according to any one of claims 1 to 4, characterized in that Z is selected from the group comprising -CH2-CH2-, -CHMe-, -CH2-CH2-CH2-, -CMe2-, -CH2-CHMe-, -CHEt-, -CH2-CH2-CHMe-, -CH2-CHEt-, -CH2-CHMe-CH2-, -CH2-CMe2-, -CHiPr-, -CH2-CH2-CMe2-, -CH2-CHiPr-, -CHMe-CHMe-CH2-, -CHMe-CMe2- and -CMe2-CHMe-, wherein Me represents the methyl, Et the ethyl and iPr the isopropyl group.6.Curable compositions according to any one of claims 1 to 5, characterized in that R is selected from the group comprising methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, n-pentyl, iso-pentyl, neo-pentyl, tert-pentyl residues, n-hexyl residues, n-heptyl residue, n-octyl residue, 2,4,4-trimethylpentyl residue, 2,2,4-trimethylpentyl residue, n-nonyl residue, n-decyl residue, n-dodecyl residue, n-hexadecyl residue, n-octadecyl residue, cyclopentyl, cyclohexyl, cycloheptyl residue, methylcyclohexyl residues, 3-glycidoxypropyl, Oxiran-2-yl and 2-(3,4-epoxycyclohexyl)ethyl radical, phenyl, biphenyl, cumylphenyl, naphthyl, anthryl and phenanthryl radical, tolyl, xylyl and ethylphenyl radicals, benzyl radical, ^- and the ^-phenylethyl radical, methoxyphenyl radical, phenoxyphenyl radical, Fluorophenyl, chlorophenyl, bromophenyl and trifluorometylphenyl residues, pyridyl, pyrazinyl, quinolinyl, furyl residues and the (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxid-10-yl)ethyl residue. WA12420S / Mk 707. Curable compositions according to any one of claims 1 to 6, characterized in that (B) is selected from the list , WA12420S / Mk 71 , WA12420S / Mk 72 (XVIII), where n means 1 to 12, r means 1 to 11, s means 1 to 11, u means 1 to 11, v means 1 to 11, and r + s means 1 to 12, u + v means 1 to 12, WA12420S / Mk 73.
8. Curable composition according to any one of claims 1 to 7, characterized in that it additionally contains (E2) at least one filler.
9. Method for producing the curable compositions according to any one of claims 1 to 8 by mixing the individual components in any order.
10. Method for producing molded parts by shaping the curable composition according to any one of claims 1 to 8 and subsequently curing.
11. Use of the curable compositions according to any one of claims 1 to 8 for producing molded parts or fiber-reinforced composites.
12. Molded parts obtainable from the method according to claim 10.
Citation Information
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