WO2021205806A1 - 硬化性樹脂、硬化性樹脂組成物、及び、硬化物 - Google Patents

硬化性樹脂、硬化性樹脂組成物、及び、硬化物 Download PDF

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WO2021205806A1
WO2021205806A1 PCT/JP2021/009703 JP2021009703W WO2021205806A1 WO 2021205806 A1 WO2021205806 A1 WO 2021205806A1 JP 2021009703 W JP2021009703 W JP 2021009703W WO 2021205806 A1 WO2021205806 A1 WO 2021205806A1
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curable resin
cured product
group
groups
integer
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English (en)
French (fr)
Japanese (ja)
Inventor
立宸 楊
龍一 松岡
広義 神成
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DIC Corp
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DIC Corp
Dainippon Ink and Chemicals Co Ltd
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Priority to JP2021529432A priority Critical patent/JP6962507B1/ja
Priority to KR1020227032188A priority patent/KR102880664B1/ko
Priority to CN202180023844.6A priority patent/CN115348977B/zh
Priority to US17/917,232 priority patent/US12359020B2/en
Publication of WO2021205806A1 publication Critical patent/WO2021205806A1/ja
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/10—Esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/54—Acrylic acid esters; Methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F12/34—Monomers containing two or more unsaturated aliphatic radicals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/10—Esters
    • C08F22/1006—Esters of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/127—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from carbon dioxide, carbonyl halide, carboxylic acids or their derivatives

Definitions

  • the present invention relates to a curable resin having an indan skeleton, a curable resin composition containing the curable resin, and a cured product obtained from the curable resin composition.
  • vinyl group-containing curable resins having various chemical structures have been conventionally proposed.
  • a curable resin for example, a curable resin such as bisphenol divinylbenzyl ether or novolac polyvinylbenzyl ether has been proposed (see, for example, Patent Documents 1 and 2).
  • these vinylbenzyl ethers cannot give a cured product having sufficiently small dielectric properties, and the obtained cured product has a problem in stable use in a high frequency band, and further, bisphenol divinylbenzyl ether. Was not sufficiently high in heat resistance.
  • the conventional curable resin containing a vinyl group containing polyvinylbenzyl ether can withstand the low dielectric loss tangent required for electrical insulating material applications, especially for high frequency electrical insulating materials, and lead-free soldering. It did not give a cured product having both heat resistance.
  • Japanese Unexamined Patent Publication No. 63-68537 Japanese Unexamined Patent Publication No. 64-65110 Special Table 1-503238 Gazette Japanese Unexamined Patent Publication No. 9-31006 Japanese Unexamined Patent Publication No. 2005-314556
  • the problem to be solved by the present invention is to provide a cured product having excellent heat resistance and dielectric properties (low dielectric properties) by using a curable resin having an indane skeleton.
  • the present inventors have conducted a curable resin having an indan skeleton capable of contributing to heat resistance and low dielectric properties, and a curable resin containing the curable resin. We have found that the cured product obtained from the resin composition is excellent in heat resistance and low dielectric properties, and have completed the present invention.
  • the present invention relates to a curable resin having an indane skeleton represented by the following general formula (1).
  • X represents a (meth) acryloyl group.
  • Ra and Rb are independently alkyl groups, aryl groups, aralkyl groups, or cycloalkyl groups having 1 to 12 carbon atoms, respectively, and j.
  • k and l independently indicate an integer of 0 to 4.
  • n is an average number of repeating units, indicates a numerical value of 0.5 to 20, and m is an integer of 0 to 2.
  • the straight line from Ra, X and the carbon atom to the aromatic ring indicates that it may be bonded to any position on the aromatic ring.
  • the curable resin of the present invention is preferably a resin having an indane skeleton represented by the following general formula (2).
  • R 1 and R 2 are independently hydrogen atoms, alkyl groups having 1 to 12 carbon atoms, aryl groups, aralkyl groups, or cycloalkyl groups, respectively, and R 1 and R 2 and never both R 2 are hydrogen atoms at the same time, n is the average number of repeating units, indicating the numerical value of 0.5 to 20.
  • the curable resin composition of the present invention preferably contains the curable resin.
  • the cured product of the present invention is preferably obtained by subjecting the curable resin composition to a curing reaction.
  • the curable resin of the present invention can contribute to heat resistance and low dielectric properties
  • the cured product obtained from the curable resin composition containing the curable resin has heat resistance and dielectric properties (low dielectric properties). Excellent in characteristics) and useful.
  • the present invention relates to a curable resin having an indane skeleton represented by the following general formula (1).
  • X represents a (meth) acryloyl group.
  • Ra and Rb are independently alkyl groups, aryl groups, aralkyl groups, or cycloalkyl groups having 1 to 12 carbon atoms, respectively, and j.
  • k and l independently indicate an integer of 0 to 4.
  • n is an average number of repeating units, indicates a numerical value of 0.5 to 20, and m is an integer of 0 to 2.
  • the straight line from Ra, X and the carbon atom to the aromatic ring indicates that it may be bonded to any position on the aromatic ring.
  • the curable resin having the indan skeleton has a low-polarity indan skeleton, the proportion of polar functional groups in the structure of the curable resin is reduced, and the curable resin produced by using the curable resin is cured.
  • the material is preferable because it has excellent dielectric properties. Further, since the curable resin has an indane skeleton, it is excellent in flexibility and flexibility, and improvement in brittleness is expected, which is preferable.
  • X is a (meth) acryloyl group serving as a cross-linking group, that is, an acryloyl group or a methacryloyl group, and a methacryloyl group is particularly preferable.
  • a (meth) acryloyl group in the curable resin a cured product having a lower dielectric adjacency than other cross-linking groups (for example, vinylbenzyl ether group (styryl group), dihydroxybenzene group, etc.) can be obtained. It is obtained and becomes a preferable embodiment.
  • the vinylbenzyl ether group (styryl) contained in the conventionally used curable resin is not clear.
  • (group) or the like it has an ether group which is a polar group, and when it has a dihydroxybenzene group, it has a plurality of hydroxyl groups which are polar groups.
  • ester group based on the meta) acryloyl group contributes to the lower molecular motility (when it has a highly polar polar group such as an ether group or a hydroxyl group, the dielectric constant and the dielectric tangent are Tends to be higher).
  • the cross-linking group is a methacryloyl group
  • the structure contains a methyl group, it is presumed that steric hindrance becomes large and the molecular motility is further lowered, and a cured product having a lower dielectric loss tangent can be obtained, which is preferable. ..
  • the cross-linking density is increased and the heat resistance is improved.
  • Ra independently represents an alkyl group having 1 to 12 carbon atoms, an aryl group, an aralkyl group, or a cycloalkyl group, and preferably an alkyl group having 1 to 4 carbon atoms. It is an aryl group or a cycloalkyl group.
  • Rb independently represents an alkyl group having 1 to 12 carbon atoms, an aryl group, an aralkyl group, or a cycloalkyl group, and preferably an alkyl group having 1 to 4 carbon atoms. It is an aryl group or a cycloalkyl group.
  • j represents an integer of 1 to 3, preferably an integer of 1 to 2.
  • k and l each independently represent an integer of 0 to 4, preferably an integer of 0 to 2. When it is within the above range, the reactivity is excellent, which is a preferable embodiment.
  • m represents an integer of 0 to 2, that is, when m is 0, it is a benzene ring, when m is 1, it is a naphthalene ring, and when m is 2, it is an anthracene ring. Yes, preferably a benzene ring with 0 m.
  • the solvent solubility is excellent, which is a preferable embodiment.
  • n is the average number of repeating units, showing a numerical value of 0.5 to 20, preferably 0.5 to 5, and more preferably 0.95 to 2.5. .. Having an indane skeleton within the above range is excellent in solvent solubility, which is a preferable embodiment.
  • n is less than 0.5, the content ratio of the refractory substance in the structure of the curable resin having the indane skeleton becomes high, the solvent solubility is inferior, and the high degree contributing to brittleness. Since the proportion of the molecular weight component is low, the brittleness of the obtained cured product is lowered, and the flexibility and flexibility may be lowered, which is not preferable.
  • n exceeds 20
  • the viscosity becomes high when dissolved in a solvent, and there is a concern that the heat resistance of the obtained cured product is inferior.
  • the high molecular weight component becomes too large, and the cured product is molded. When doing so, there is a concern that the fluidity will decrease and the handleability will be inferior, which is not preferable.
  • the value of n is particularly preferably 0.95 to 2.5 from the viewpoint of the high thermal deformation temperature of the cured product, the high glass transition temperature, and the like.
  • the curable resin Since the curable resin has an indan skeleton, an alicyclic structure having an excellent balance between heat resistance and dielectric properties is introduced into the structure of the curable resin, and a cured product produced using the curable resin. Is preferable because it has an excellent balance between heat resistance and dielectric properties (particularly low dielectric tangent), and further low dielectric properties can be exhibited by having a (meth) acryloyl group as a cross-linking group in the molecular structure. ..
  • the curable resin of the present invention preferably has an indane skeleton represented by the following general formula (2).
  • R 1 and R 2 are independently hydrogen atoms, alkyl groups having 1 to 12 carbon atoms, aryl groups, aralkyl groups, or cycloalkyl groups, respectively, and R 1 and R 2 and Both of R 2 are not hydrogen atoms at the same time, n is the average number of repeating units, and indicates a numerical value of 0.5 to 20.
  • R 1 and R 2 are independently hydrogen atoms, alkyl groups having 1 to 12 carbon atoms, aryl groups, aralkyl groups, or cycloalkyl groups, and both are hydrogen atoms at the same time. It is not present, and is preferably an alkyl group having 1 to 4 carbon atoms, an aryl group, or a cycloalkyl group.
  • the alkyl group having 1 to 12 carbon atoms or the like the flatness in the vicinity of the benzene ring is lowered, and the crystallinity is lowered, so that the solvent solubility is improved and the melting point is lowered, which is a preferable embodiment.
  • n is the average number of repeating units, showing a numerical value of 0.5 to 20, preferably 0.5 to 5, and more preferably 0.95 to 2.5. .. Having an indane skeleton within the above range is excellent in solvent solubility, which is a preferable embodiment. If n is less than 0.5, the content ratio of the refractory substance in the structure of the curable resin having an indane skeleton becomes high, the solvent solubility is inferior, and the high degree contributing to brittleness. Since the proportion of the molecular weight component is low, the brittleness of the obtained cured product is lowered, and the flexibility and flexibility may be lowered, which is not preferable.
  • n exceeds 20
  • the viscosity becomes high when dissolved in a solvent, and there is a concern that the heat resistance of the obtained cured product is inferior.
  • the high molecular weight component becomes too large, and the cured product is molded. When doing so, there is a concern that the fluidity will decrease and the handleability will be inferior, which is not preferable.
  • the value of n is particularly preferably 0.95 to 2.5 from the viewpoint of the high thermal deformation temperature of the cured product, the high glass transition temperature, and the like.
  • the curable resin Since the curable resin has an indan skeleton, an alicyclic structure having an excellent balance between heat resistance and dielectric properties is introduced into the structure of the curable resin, and a cured product produced using the curable resin. Has an excellent balance between heat resistance and dielectric properties (particularly low dielectric loss tangent), and by having a methacryloyl group at the end of the molecular structure, steric damage becomes larger than in the case of an acryloyl group, and further. It is preferable because it can exhibit low dielectric properties.
  • the following general formula (3) represents a monovalent functional group in which Rc is independently selected from the group consisting of the following general formulas (4) and (5), and the ortho of at least one of the two Rc is Rc.
  • the position is a hydrogen atom, and Rb and l are compounds showing the same as above.
  • the following general formula (6-1) is when m in the above general formula (1) is 0, that is, when the curable resin having an indane skeleton is a benzene ring, and i is 1 or 2. Is preferable, and i is more preferably 1.
  • the following general formula (6-2) is a case where m in the above general formula (1) is 1, that is, a naphthalene ring, i is preferably 1 or 2, and i is 1. More preferably.
  • the following general formula (6-3) is a case where m in the above general formula (1) is 2, that is, an anthracene ring, i is preferably 1 or 2, and i is 1. More preferably.
  • Ra and k are phenols or derivatives thereof, respectively, which are similar to the above, and are compounds of the above general formula (3) and any of the following general formulas (6-1) to (6-3).
  • an intermediate phenol compound represented by the following general formula (7) can be obtained.
  • Ra, Rb, k, l, i and n in the following general formula (7) indicate the same as above.
  • the following general formula (7) exemplifies the case where m in the above general formula (1) is 0, that is, the case of a benzene ring.
  • the average number of repeating units n is a low melting point (low softening point), a low melt viscosity, and excellent handleability. Therefore, the average number of repeating units n indicates a numerical value of 0.5 to 20, preferably 0.5 to 5, and more preferably 0.95 to 2.5. Having an indane skeleton in the structure of the intermediate phenol compound is excellent in solvent solubility, which is a preferable embodiment. If n is less than 0.5, the content ratio of the refractory substance in the structure of the intermediate phenol compound becomes high, the solvent solubility is inferior, and the high molecular weight component contributing to brittleness.
  • the ratio is low, the brittleness of the cured product obtained by using the curable resin having an indan skeleton using the intermediate phenol compound as a raw material (precursor) is lowered, and further, the flexibility and flexibility are also lowered. It is not preferable because there is a risk of doing so.
  • n exceeds 20, the viscosity becomes high when dissolved in a solvent, and there is a concern that the heat resistance of the obtained cured product is inferior. Further, the high molecular weight component becomes too large, and the cured product is molded. At that time, there is a concern that the fluidity will decrease and the handleability will be inferior, which is not preferable.
  • compound (a) is not particularly limited, but is typically p- and m-diisopropenylbenzene, p- and. m-bis ( ⁇ -hydroxyisopropyl) benzene ( ⁇ , ⁇ '-dihydroxy-1,3-diisopropylbenzene), p- and m-bis ( ⁇ -chloroisopropyl) benzene, 1- ( ⁇ -hydroxyisopropyl) -3 -Isopropenylbenzene, 1- ( ⁇ -hydroxyisopropyl) -4-isopropenylbenzene or a mixture thereof is used.
  • nuclear alkyl group substituents of these compounds such as diisopropenyltoluene and bis ( ⁇ -hydroxyisopropyl) toluene can also be used, and further nuclear halogen substituents such as chlorodiisopropenylbenzene and chlorobis ( ⁇ ). -Hydroxyisopropyl) benzene and the like can also be used.
  • examples of the compound (a) include 2-chloro-1,4-diisopropenylbenzene, 2-chloro-1,4-bis ( ⁇ -hydroxyisopropyl) benzene, and 2-bromo-1,4-di.
  • the substituent contained in the compound (a) is not particularly limited, and the above-exemplified compounds can be used. However, in the case of a substituent having a large steric disorder, a substituent having a small steric disorder is used. Stacking of the obtained intermediate phenol compounds is unlikely to occur, and crystallization of the intermediate phenol compounds is unlikely to occur, that is, the solvent solubility of the intermediate phenol compounds is improved, which is a preferable embodiment.
  • the compound represented by any of the above general formulas (6-1) to (6-3) is phenol or a derivative thereof, and is not particularly limited, but is typical.
  • cresols such as o-cresol, m-cresol, p-cresol; phenol; 2,3-xylenol, 2,4-xylenol, 2,5-xylenol, 2,6-xylenol (2,6-dimethyl) Phenol
  • xylenol such as 3,4-xylenol, 3,5-xylenol
  • ethylphenol such as o-ethylphenol, m-ethylphenol, p-ethylphenol
  • butylphenol such as isopropylphenol, butylphenol, pt-butylphenol
  • Alkylphenol such as p-pentylphenol, p-octylphenol, p-nonylphenol, p
  • phenols or derivatives thereof may be used alone or in combination of two or more.
  • the compound (b) having an alkyl group having 1 to 4 carbon atoms should be used. Is preferable.
  • the compound (a) and the compound (b) are converted into moles of the compound (b) with respect to the compound (a).
  • An intermediate phenol compound having an indan skeleton by reacting the ratio (compound (b) / compound (a)) at a ratio of preferably 0.1 to 10, more preferably 0.2 to 8 in the presence of a charged acid catalyst. Can be obtained.
  • Examples of the acid catalyst used in the reaction include inorganic acids such as phosphoric acid, hydrochloric acid and sulfuric acid, oxalic acid, benzenesulfonic acid, toluenesulfonic acid, methanesulfonic acid, fluoromethanesulfonic acid and other organic acids, and active white clay.
  • Acidic white clay, silica alumina, zeolite, solid acids such as strongly acidic ion exchange resin, heteropolyhydrochloride, etc. can be mentioned, but it is a homogeneous catalyst that can be easily removed by neutralization with a base and washing with water after the reaction. It is preferable to use oxalic acid, benzenesulfonic acid, toluenesulfonic acid, methanesulfonic acid, fluoromethanesulfonic acid.
  • the blending amount of the acid catalyst is such that the acid catalyst is blended in the range of 0.001 to 40 parts by mass with respect to 100 parts by mass of the compound (a) and the compound (b), which are the raw materials to be charged first.
  • 0.001 to 25 parts by mass is preferable from the viewpoint of handleability and economy.
  • the reaction temperature is usually in the range of 50 to 300 ° C., but in order to suppress the formation of isomer structures, avoid side reactions such as thermal decomposition, and obtain a high-purity intermediate phenol compound, 80 ⁇ 200 ° C. is preferable.
  • the reaction time the reaction does not proceed completely in a short time, and side reactions such as a thermal decomposition reaction of the product occur when the reaction time is long. Therefore, under the reaction temperature conditions, the total reaction time is usually 0. It is in the range of .5 to 24 hours, but preferably in the range of 0.5 to 12 hours in total.
  • phenol or a derivative thereof also serves as a solvent
  • a solvent capable of co-boiling dehydration such as toluene, xylene, or chlorobenzene is used. After completing the dehydration reaction, the solvent may be distilled off, and then the reaction may be carried out within the above reaction temperature range.
  • Examples of the organic solvent used for synthesizing the intermediate phenol compound include ketones such as acetone, methyl ethyl ketone (MEK), methyl isobutyl ketone, cyclohexanone and acetophenone, N, N-dimethylformamide and N, N-dimethylacetamide. , Dimethylsulfoxide, N-methyl-2-pyrrolidone, aprotonic solvents such as acetonitrile and sulfolane, cyclic ethers such as dioxane and tetrahydrofuran, esters such as ethyl acetate and butyl acetate, aromatics such as benzene, toluene and xylene. Examples thereof include system solvents, and these may be used alone or in combination.
  • ketones such as acetone, methyl ethyl ketone (MEK), methyl isobutyl ketone, cyclohexanone and aceto
  • the hydroxyl group equivalent (phenol equivalent) of the intermediate phenol compound is preferably 200 to 2000 g / eq, and more preferably 220 to 500 g / eq, from the viewpoint of heat resistance.
  • the hydroxyl group equivalent (phenol equivalent) of the intermediate phenol compound is calculated by a titration method and refers to a neutralization titration method based on JIS K0070.
  • the curable resin having an indane skeleton is a known method such as reaction of the intermediate phenol compound with anhydrous (meth) acrylic acid or (meth) acrylic acid chloride in the presence of a basic or acidic catalyst. Can be obtained by
  • anhydrous (meth) acrylic acid examples include methacrylic anhydride and methacrylic anhydride.
  • examples of the (meth) acrylic acid chloride include methacrylic acid chloride and acrylic acid chloride. These may be used alone or in combination. Above all, it is preferable to use methacrylic anhydride, which can obtain a cured product having a lower dielectric loss tangent.
  • the basic catalyst include dimethylaminopyridine, alkaline earth metal hydroxide, alkali metal carbonate, and alkali metal hydroxide.
  • the acidic catalyst include sulfuric acid and methanesulfonic acid.
  • dimethylaminopyridine is excellent in terms of catalytic activity.
  • anhydrous (meth) acrylic acid or the like The reaction between the intermediate phenol compound and the anhydrous (meth) acrylic acid or the (meth) acrylic acid chloride (hereinafter, may be referred to as “anhydrous (meth) acrylic acid or the like”) is the intermediate.
  • anhydrous (meth) acrylic acid or the like To 1 mol of the hydroxyl group contained in the phenol compound, 1 to 5 mol of the above-mentioned anhydrous (meth) acrylic acid or the like is added, and 0.03 to 1 basic catalyst is added all at once or gradually while adding 30. Examples thereof include a method of reacting at a temperature of about 150 ° C. for 1 to 40 hours.
  • an organic solvent in combination during the reaction with anhydrous (meth) acrylic acid or the like (introduction of (meth) acryloyl group), the reaction rate in the synthesis of a curable resin having an indane skeleton can be increased.
  • an organic solvent is not particularly limited, and for example, ketones such as acetone and methyl ethyl ketone, alcohols such as methanol, ethanol, 1-propyl alcohol, isopropyl alcohol, 1-butanol, secondary butanol and tertiary butanol, and methyl.
  • Examples include cellosolves such as cellosolve and ethyl cellosolve, ethers such as tetrahydrofuran, 1,4-dioxane, 1,3-dioxane and diethoxyethane, aprotic polar solvents such as acetonitrile, dimethylsulfoxide and dimethylformamide, and toluene. Be done. Each of these organic solvents may be used alone, or two or more kinds may be used in combination as appropriate to adjust the polarity.
  • the reaction product is washed with water and then unreacted anhydrous (meth) acrylic acid or the like under heating and reduced pressure conditions.
  • the combined organic solvent is distilled off.
  • the curable resin having an indan skeleton is again dissolved in an organic solvent such as toluene, methylisobutylketone or methylethylketone, and hydroxideed. Further reaction can be carried out by adding an aqueous solution of an alkali metal hydroxide such as sodium or potassium hydroxide.
  • phase transfer catalyst such as a quaternary ammonium salt or a crown ether may be present for the purpose of improving the reaction rate.
  • the amount used is preferably in the range of 0.1 to 10% by mass with respect to the curable resin having an indane skeleton to be used.
  • the produced salt is removed by filtration or washing with water, and the organic solvent is distilled off under heating and reduced pressure conditions to obtain a curable resin having a target indane skeleton having a low content of hydrolyzable chlorine. be able to.
  • the softening point of the curable resin having an indane skeleton is preferably 150 ° C. or lower, more preferably 30 to 100 ° C. It is preferable that the softening point of the curable resin having the indane skeleton is within the above range because the processability is excellent.
  • the curable resin composition of the present invention preferably contains the curable resin having the indane skeleton. Since the curable resin having an indane skeleton has an indane skeleton, it has excellent solvent solubility, easy preparation of a curable resin composition, excellent handleability, and in the structure of the curable resin having the indane skeleton. Since the proportion of polar functional groups is small, a cured product having excellent dielectric properties can be obtained.
  • the curable resin composition of the present invention can be used without particular limitation as long as the purpose is not impaired, and alkenyl group-containing compounds such as vinylids, allyl ether compounds, allylamine compounds, triallyl cyanurate, and alkenyl phenols can be used.
  • alkenyl group-containing compounds such as vinylids, allyl ether compounds, allylamine compounds, triallyl cyanurate, and alkenyl phenols can be used.
  • a system compound, a vinyl group-containing polyolefin compound, or the like can also be added.
  • other thermosetting resins such as a thermosetting polyimide resin, an epoxy resin, a phenol resin, an active ester resin, a benzoxazine resin, and a cyanate resin can also be appropriately blended depending on the intended purpose.
  • the curable resin composition of the present invention may contain a curing agent.
  • the curing agent include amine compounds, amide compounds, acid anhydride compounds, phenolic compounds, cyanate ester compounds and the like. These curing agents may be used alone or in combination of two or more.
  • a curing accelerator may be appropriately used in combination with the curable resin composition of the present invention, if necessary.
  • Various types of curing accelerators can be used, and examples thereof include phosphorus compounds, tertiary amines, imidazoles, organic acid metal salts, Lewis acids, and amine complex salts.
  • phosphorus compounds such as triphenylphosphine or imidazoles are preferable from the viewpoint of excellent curability, heat resistance, electrical properties, moisture resistance reliability and the like.
  • These curing accelerators can be used alone or in combination of two or more.
  • the amount of the curing accelerator added is preferably in the range of 0.01 to 10 parts by mass with respect to 100 parts by mass of the epoxy resin, for example.
  • the curable resin composition of the present invention can be blended with a non-halogen flame retardant that does not substantially contain a halogen atom in order to exhibit flame retardancy.
  • a non-halogen flame retardant include phosphorus flame retardants, nitrogen flame retardants, silicone flame retardants, inorganic flame retardants, organic metal salt flame retardants, and the like, and these are used alone or in combination. be able to.
  • An inorganic filler can be added to the curable resin composition of the present invention, if necessary.
  • the inorganic filler include fused silica, crystalline silica, alumina, silicon nitride, aluminum hydroxide and the like.
  • fused silica When the blending amount of the inorganic filler is particularly large, it is preferable to use fused silica.
  • the molten silica can be used in either a crushed form or a spherical shape, but in order to increase the blending amount of the molten silica and suppress an increase in the melt viscosity of the molding material, it is better to mainly use a spherical one. preferable.
  • a conductive filler such as silver powder or copper powder can be used.
  • Various compounding agents such as a silane coupling agent, a mold release agent, a pigment, and an emulsifier can be added to the curable resin composition of the present invention, if necessary.
  • the cured product of the present invention is preferably obtained by subjecting the curable resin composition to a curing reaction.
  • the curable resin composition can be obtained by uniformly mixing each component such as the above-mentioned curing agent in addition to the curable resin having the indane skeleton alone or the curable resin having the indane skeleton.
  • a cured product can be easily obtained by the same method as a conventionally known method. Examples of the cured product include molded products such as laminates, cast products, adhesive layers, coating films, and films.
  • thermosetting and ultraviolet curing reactions examples include thermosetting and ultraviolet curing reactions.
  • the thermosetting reaction is easily carried out even without a catalyst, but if a faster reaction is desired, an organic peroxide or an azo compound is used. It is effective to add a polymerization initiator such as, a phosphine compound, or a basic catalyst such as a tertiary amine. Examples thereof include benzoyl peroxide, dicumyl peroxide, azobisisobutyronitrile, triphenylphosphine, triethylamine, imidazoles and the like.
  • the cured product obtained by the curable resin composition of the present invention is excellent in heat resistance and dielectric properties, it can be suitably used for heat-resistant members and electronic members.
  • it can be suitably used for prepregs, circuit boards, semiconductor encapsulants, semiconductor devices, build-up films, build-up boards, adhesives, resist materials and the like.
  • it can be suitably used for a matrix resin of a fiber reinforced resin, and is particularly suitable as a prepreg having high heat resistance.
  • the curable resin having the indane skeleton contained in the curable resin composition can be made into a paint because it exhibits excellent solubility in various solvents.
  • the heat-resistant members and electronic members thus obtained can be suitably used for various purposes.
  • industrial mechanical parts For example, industrial mechanical parts, general mechanical parts, automobile / railway / vehicle parts, space / aviation-related parts, electronic / electrical parts, etc.
  • Examples include, but are not limited to, building materials, container / packaging materials, daily necessities, sports / leisure products, and housing materials for wind power generation.
  • ⁇ GPC measurement evaluation of number average molecular weight and average number of repeating units
  • the measurement was carried out using the following measuring device and measuring conditions, and a GPC chart of a curable resin having an indane skeleton obtained by the synthesis method shown below was obtained. From the results of the GPC chart, the average number of repeating units n that contributes to the indane skeleton in the curable resin having an indane skeleton was calculated based on the number average molecular weight (Mn) of the curable resin having an indane skeleton.
  • Mn number average molecular weight
  • Measuring device "HLC-8320 GPC” manufactured by Tosoh Corporation Column: Guard column “HXL-L” manufactured by Tosoh Corporation + “TSK-GEL G2000HXL” manufactured by Tosoh Corporation + “TSK-GEL G2000HXL” manufactured by Tosoh Corporation + “TSK-GEL G3000HXL” manufactured by Tosoh Corporation + Tosoh Corporation Made by “TSK-GEL G4000HXL” Detector: RI (Differential Refractometer) Data processing: "GPC Workstation EcoSEC-WorkStation” manufactured by Tosoh Corporation Measurement conditions: Column temperature 40 ° C Developing solvent Tetrahydrofuran Flow velocity 1.0 ml / min Standard: The following monodisperse polystyrene with a known molecular weight was used in accordance with the measurement manual of the above-mentioned "GPC workstation EcoSEC-WorkStation".
  • Example 1 48.9 g (0.4 mol) of 2,6-dimethylphenol and 272.0 g (1) of ⁇ , ⁇ '-dihydroxy-1,3-diisopropylbenzene in a 1 L flask equipped with a thermometer, a cooling tube, a Dean Stark trap, and a stirrer. .4 mol), 280 g of xylene, and 70 g of active white clay were charged and heated to 120 ° C. with stirring. Further, the distillate was removed with a Dean-Stark tube, the temperature was raised to 210 ° C., and the reaction was carried out for 3 hours.
  • the average number of repeating units n was calculated by GPC measurement, the GPC chart of which is shown in FIG. 1, and the number average molecular weight (Mn).
  • Mn number average molecular weight
  • Tg glass transition point temperature
  • the dielectric constant and dielectric loss tangent at a frequency of 10 GHz by the split post dielectric resonator method using a network analyzer N5247A manufactured by Keysight Technology Co., Ltd. was measured. If the dielectric loss tangent is 10 ⁇ 10 -3 or less, there is no practical problem, preferably 7.5 ⁇ 10 -3 or less, and if the dielectric constant is 3 or less, there is no practical problem. There is no problem, preferably 2.7 or less, and more preferably 2.5 or less.
  • Comparative Example 1 since the curable resin having an indane skeleton does not have a (meth) acryloyl group, the dielectric loss tangent is higher than that of the example, and both heat resistance and dielectric properties are achieved. It was confirmed that there was no such thing.
  • the cured product obtained by using the curable resin of the present invention is excellent in heat resistance and dielectric properties, and therefore can be suitably used for heat-resistant members and electronic members.
  • prepregs, semiconductor encapsulants, and circuits It can be suitably used for substrates, build-up films, build-up substrates, etc., adhesives and resist materials. Further, it can be suitably used for a matrix resin of a fiber reinforced resin, and is suitable as a prepreg having high heat resistance.

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  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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JP2023057680A (ja) * 2021-10-12 2023-04-24 Dic株式会社 硬化性樹脂組成物、硬化物、絶縁材料及びレジスト部材
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JP2023127139A (ja) * 2022-03-01 2023-09-13 Dic株式会社 重合性不飽和基を有する樹脂、硬化性樹脂組成物、硬化物及び物品
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KR20250061625A (ko) 2023-10-27 2025-05-08 디아이씨 가부시끼가이샤 경화성 수지 조성물, 경화물, 바니시, 프리프레그 및 회로 기판
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