WO2016170850A1 - Organosiloxane cyclique contenant un groupe époxy - Google Patents

Organosiloxane cyclique contenant un groupe époxy Download PDF

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WO2016170850A1
WO2016170850A1 PCT/JP2016/056363 JP2016056363W WO2016170850A1 WO 2016170850 A1 WO2016170850 A1 WO 2016170850A1 JP 2016056363 W JP2016056363 W JP 2016056363W WO 2016170850 A1 WO2016170850 A1 WO 2016170850A1
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group
epoxy
substituent
integer
carbon atoms
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PCT/JP2016/056363
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Japanese (ja)
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哲郎 山田
裕司 吉川
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信越化学工業株式会社
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule

Definitions

  • the present invention relates to a cyclic organosiloxane containing one or more hydrolyzable silyl groups and two or more epoxy groups in one molecule having a cyclic siloxane as a main skeleton.
  • a silane coupling agent having an epoxy group and a hydrolyzable silyl group includes an adhesion improver (Patent Document 1: Japanese Patent Laid-Open No. 06-287456) and a silica surface treatment (Patent Document 2: Japanese Patent Laid-Open No. 08-146435).
  • an adhesion improver Patent Document 1: Japanese Patent Laid-Open No. 06-287456
  • a silica surface treatment Patent Document 2: Japanese Patent Laid-Open No. 08-146435.
  • paints, coating agents, electronic parts, etc. In this case, one hydrolyzable silyl group and one epoxy group per molecule. It is only a silane coupling agent having one by one, and a binder effect cannot be expected.
  • an organooligosiloxane obtained by partially hydrolytic condensation of a silane coupling agent (hereinafter referred to as a siloxane oligomer) is a material having a plurality of organic groups and hydrolyzable silyl groups in the structure.
  • a hydrolyzable organic group such as an epoxy group
  • the epoxy group also reacts simultaneously with the hydrolytic condensation of the silyl group portion, so the same technology cannot be applied, and stability over time was required.
  • Patent Document 3 Patent No. 2816082
  • Patent Document 4 Patent No. 3067312).
  • the siloxane compounds synthesized by these methods have a problem that the molecular weight distribution is wide and compatibility with other compounds deteriorates due to the influence of polymer components.
  • the present invention has been made in view of the above circumstances, and provides a cyclic organosiloxane having one or more hydrolyzable silyl groups and two or more epoxy groups in one molecule having a cyclic siloxane as a main skeleton. Objective.
  • the crosslink density of the resin can be dramatically increased by using a trifunctional or higher functional epoxy group-containing compound, the mechanical strength of the obtained resin molded product is expected to be improved.
  • a compound having, for example, a hydrolyzable silyl group as another organic group functions as a binder in the resin and is expected to be effective as a silane coupling agent. .
  • the present invention provides the following epoxy group-containing cyclic organosiloxane.
  • An epoxy group-containing cyclic organosiloxane represented by the following general formula (1).
  • R 1 is each independently an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms
  • R 2 is each independently having 1 to 14 carbon atoms which may have a hydrogen atom or a substituent
  • the substituent is a halogen atom, vinyl group, epoxy group, thiirane group, (meth) acryl group, mercapto group, iso (thio) cyanate group, hydrolyzable silyl group, succinic anhydride group, perfluoroalkyl group, those selected from polyether groups and perfluoropolyether group
  • R 2 is one or more of the inner hydrolyzable silyl group and a substituted group, R 2 to the epoxy group with a substituent 2 or more, and n is an integer of 3
  • R 1 is as defined above, R 3 is each independently a substituent containing an epoxy group, R 4 is each independently an alkyl group having 1 to 4 carbon atoms, and R 5 is each independently a halogen atom. , An alkoxy group having 1 to 20 carbon atoms, or an aryloxy group having 6 to 10 carbon atoms, which may have an oxygen atom between them, and each R 6 may independently have a hydrogen atom or a substituent.
  • the substituent is a halogen atom, vinyl group, thiirane group, (meth) acryl group, mercapto group, iso (thio) cyanate group, succinic anhydride group, perfluoroalkyl group, polyether Group and a perfluoropolyether group, k is an integer of 2 to 8, m is an integer of 2 to 14, and x is an integer of 1 to 3.
  • p ⁇ 2, q ⁇ 1, r ⁇ 0 and p + q + r are integers of 3 to 6.
  • the cyclic organosiloxane of the present invention has two or more epoxy groups in one molecule
  • the compound contains an organic group (for example, amine, hydroxyl group, acid anhydride group) having reactivity with the functional group,
  • an organic group for example, amine, hydroxyl group, acid anhydride group
  • it since it does not contain a high molecular weight substance, it has excellent compatibility with other organic resins, and functions as a binder. Since it contains a decomposable silyl group, it is an unprecedented material that can be expected to be effective as a silane coupling agent.
  • Example 1 is a 1 H-NMR spectrum of 1,3,5-tris (2- (3,4-epoxycyclohexyl) ethyl) -7-trimethoxysilyloctyltetramethylcyclotetrasiloxane obtained in Example 1.
  • 4 is an IR spectrum of 1,3,5-tris (2- (3,4-epoxycyclohexyl) ethyl) -7-trimethoxysilyloctyltetramethylcyclotetrasiloxane obtained in Example 1.
  • FIG. 2 is a 1 H-NMR spectrum of 1,3,5-tris (3-glycidoxypropyl) -7-trimethoxysilyloctyltetramethylcyclotetrasiloxane obtained in Example 2.
  • FIG. 3 is an IR spectrum of 1,3,5-tris (3-glycidoxypropyl) -7-trimethoxysilyloctyltetramethylcyclotetrasiloxane obtained in Example 2.
  • FIG. 2 is a 1 H-NMR spectrum of 1,3,5-tris (3-glycidoxypropyl) -7-trimethoxysilylethyltetramethylcyclotetrasiloxane obtained in Example 3.
  • 3 is an IR spectrum of 1,3,5-tris (3-glycidoxypropyl) -7-trimethoxysilylethyltetramethylcyclotetrasiloxane obtained in Example 3.
  • FIG. 3 is an IR spectrum of 1,3,5-tris (3-glycid
  • the cyclic organosiloxane of the present invention has only to have a cyclic siloxane structure as a main skeleton and one molecule containing one or more hydrolyzable silyl groups and two or more epoxy groups, and more preferably an epoxy. It contains 3 or more groups.
  • the detailed structure of the organosiloxane is a cyclic siloxane represented by the following general formula (1), and may have the organic functional groups listed below in addition to the hydrolyzable silyl group and the epoxy group.
  • R 1 is each independently an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms
  • R 2 is each independently having 1 to 14 carbon atoms which may have a hydrogen atom or a substituent
  • the substituent is a halogen atom, vinyl group, epoxy group, thiirane group, (meth) acryl group, mercapto group, iso (thio) cyanate group, hydrolyzable silyl group, succinic anhydride group, perfluoroalkyl group, those selected from polyether groups and perfluoropolyether group
  • R 2 is one or more of the inner hydrolyzable silyl group and a substituted group, R 2 to the epoxy group with a substituent 2 or more
  • n is an integer of 3 to 6. Arrangement of each repeating unit is arbitrary.
  • R 1 is a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms, typically a methyl group.
  • Ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, pentyl group, isopentyl group, cyclopentyl group, hexyl group, cyclohexyl group, octyl group, decyl group, etc. are mentioned as alkyl groups, phenyl group, naphthyl group, etc. Are mentioned as an aryl group.
  • R 2 is a hydrogen atom or an optionally substituted alkyl group having 1 to 14 carbon atoms, particularly 1 to 8 carbon atoms, and the alkyl group of the main structure is the same as the alkyl group for R 1 described above.
  • substituents halogen atoms such as chlorine and fluorine atoms, vinyl groups, epoxy groups, thiirane groups, (meth) acryl groups, mercapto groups, iso (thio) cyanate groups, hydrolyzable silyl groups, succinic anhydride Group, trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, nonafluorobutyl group, tridecafluorohexyl group, heptadecafluorooctyl group and other perfluoroalkyl groups, poly (ethylene oxide) group, poly (propylene oxide) ) Groups such as polyether groups and poly (hexafluoroethylene oxide) groups
  • the organosiloxane of the present invention must contain a hydrolyzable silyl group in addition to the epoxy group.
  • a hydrolyzable silyl group By containing a hydrolyzable silyl group, the organosiloxane functions as a silane coupling agent.
  • the hydrolyzable silyl group is composed of a monovalent hydrolyzable atom directly bonded to a silicon atom (an atom that generates a silanol group by reacting with water) and a monovalent hydrolyzable group directly bonded to a silicon atom (reacted with water).
  • the group is not particularly limited as long as it is a silyl group having at least one of groups capable of producing a silanol group.
  • One or two or more hydrolyzable silyl groups may be present in the organosiloxane, and when two or more hydrolyzable silyl groups are present, they may be the same or different.
  • the specific structure of the organosiloxane having a hydrolyzable silyl group and an epoxy group can be represented by the following general formula (2).
  • R 1 is as defined above, R 3 is each independently a substituent containing an epoxy group, R 4 is each independently an alkyl group having 1 to 4 carbon atoms, and R 5 is each independently a halogen atom.
  • R 4 is each independently an alkyl group having 1 to 4 carbon atoms, and R 5 is each independently a halogen atom.
  • p ⁇ 2, q ⁇ 1, r ⁇ 0, p + Q + r is an integer of 3 to 6.
  • the arrangement of each repeating unit is arbitrary.)
  • Examples of the substituent containing the epoxy group of R 3 include substituents represented by the following general formulas (A) to (C).
  • R 4 may be linear or branched, and specific examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, and an isobutyl group.
  • a methyl group is preferred because of the ease of production of the raw material.
  • R 5 is a group that generates silanol by reacting with water, specifically, a halogen atom such as a chlorine atom or a bromine atom, or an alkoxy group such as a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, or a butoxy group.
  • alkoxy groups in which some carbon atoms are substituted with oxygen atoms such as aryloxy groups such as phenoxy groups, ethylene glycol monoalkyl ether groups (for example, ethylene glycol monobutyl ether groups), and the like. Not limited to things. Among these, a methoxy group and an ethoxy group are preferable from the standpoint of ease of raw material production and hydrolyzability.
  • halogen atom, perfluoroalkyl group, polyether group, and perfluoropolyether group of the substituent of R 6 include the same as those described for R 2 in the general formula (1).
  • organosiloxane represented by the general formula (2) include, for example, those represented by the following general formula (3) or (4).
  • organosiloxane of the present invention for example, a compound represented by the following general formula (5), (6) or (7), that is, 1,3,5-tris (2- (3,4-) Epoxycyclohexyl) ethyl) -7-trimethoxysilyloctyltetramethylcyclotetrasiloxane, 1,3-bis (2- (3,4-epoxycyclohexyl) ethyl) -5,7-bis (trimethoxysilyloctyl) tetramethyl Cyclotetrasiloxane, 1,5-bis (2- (3,4-epoxycyclohexyl) ethyl) -3,7-bis (trimethoxysilyloctyl) tetramethylcyclotetrasiloxane, 1,3-bis (2- (3 , 4-Epoxycyclohexyl) ethyl) -5,7-bis (trimethoxysilylethy
  • the organosiloxane of the present invention comprises a cyclic organohydrogensiloxane having at least two Si—H groups and at least one hydrolyzable silyl group in one molecule, and an epoxy group-containing compound having a carbon-carbon unsaturated bond Are hydrosilylated in the presence of platinum and / or platinum complexes.
  • an epoxy group-containing compound having a carbon-carbon unsaturated bond are hydrosilylated in the presence of platinum and / or platinum complexes.
  • the desired compound can be obtained by hydrosilylating the Si—H group remaining in the cyclic organohydrogensiloxane with an epoxy group-containing compound having a carbon-carbon unsaturated bond.
  • the order of hydrosilylation is not particularly limited, but it is preferable that the epoxy group-containing compound containing a carbon-carbon unsaturated bond is hydrosilylated later from the viewpoint of reaction efficiency.
  • Si—H groups contained in a cyclic organohydrogensiloxane having at least two Si—H groups and at least one hydrolyzable silyl group in one molecule and if necessary, as substituents At least one selected from a halogen atom, vinyl group, thiirane group, (meth) acryl group, mercapto group, iso (thio) cyanate group, succinic anhydride group, perfluoroalkyl group, polyether group and perfluoropolyether group
  • the hydrosilylation reaction of a substituted or unsubstituted unsaturated hydrocarbon compound with a seed in the presence of platinum and / or a platinum complex the remaining Si—H group in the resulting cyclic organohydrogensiloxane and carbon-carbon It is preferable to carry out a hydrosilylation reaction with an epoxy group-containing compound having an unsaturated bond.
  • the reaction temperature is room temperature (25 ° C.) to 150 ° C., preferably 40 to 130 ° C., more preferably 70 to 120 ° C. If the temperature is lower than room temperature, the reaction does not proceed, or the reaction rate is extremely low, so that productivity may be lacking. On the other hand, when it exceeds 150 ° C., there is a possibility that thermal decomposition or unintended side reaction may occur.
  • the reaction time is 10 minutes to 24 hours.
  • the time may be a time at which the raw material is sufficiently consumed by the progress of the reaction, but it is preferably 1 to 10 hours, more preferably 2 to 7 hours. If it is less than 10 minutes, the consumption of the raw material may be insufficient, and if it exceeds 24 hours, the raw material has already been completely consumed, which may be an unnecessary process and may reduce the production efficiency.
  • a reaction solvent may be appropriately used in the method for producing an organosiloxane of the present invention.
  • an aliphatic hydrocarbon solvent such as hexane or heptane, or an aromatic such as toluene or xylene.
  • hydrocarbon solvents include hydrocarbon solvents, alcohol solvents such as methanol, ethanol, propanol and isopropanol, and ketone solvents such as acetone, methyl ethyl ketone and methyl isobutyl ketone.
  • the organohydrogensiloxane in the present invention is not particularly limited as long as it has a cyclic siloxane as a main skeleton and contains at least two Si—H groups and at least one hydrolyzable silyl group in one molecule.
  • the structure may have a linear structure or a branched structure.
  • an unnecessary increase in crosslink density can be avoided if the molecular weight distribution is narrow to some extent, so that it is essential to be a cyclic siloxane in order to achieve a low molecular weight.
  • cyclic organohydrogensiloxane examples include 1,3,5-trimethyl-1-trimethoxysilyloctylcyclotrisiloxane, 1,3,5-trimethyl-1-trimethoxysilylhexylcyclotrisiloxane, , 3,5-trimethyl-1-trimethoxysilylethylcyclotrisiloxane, 1,3,5-trimethyl-1-triethoxysilyloctylcyclotrisiloxane, 1,3,5-trimethyl-1-triethoxysilylhexylcyclo Trisiloxane, 1,3,5-trimethyl-1-triethoxysilylethylcyclotrisiloxane, 1,3,5,7-tetramethyl-1-trimethoxysilyloctylcyclotetrasiloxane, 1,3,5,7- Tetramethyl-1-trimethoxysilyloctyl-3-pro Rucyclotetrasiloxane, 1,3,5,7-tetramethyl
  • 1,3,5,7-tetramethyl-1-trimethoxysilyloctylcyclotetrasiloxane, 1,3,5,7-tetramethyl-1-trimethoxy are explained above and the raw materials are easily available.
  • Most preferred is silylethylcyclotetrasiloxane.
  • the unsaturated hydrocarbon compound added if necessary is represented by the following formula CH 2 ⁇ CH—R 6a.
  • R 6a is a hydrogen atom or an alkyl group having 1 to 14, particularly 1 to 8 carbon atoms which may have a substituent, and the substituent is a halogen atom, a vinyl group, a thiirane group, (meta )
  • An epoxy group-containing compound having a carbon-carbon unsaturated bond is represented by the following formula:
  • R 3 is a substituent containing an epoxy group, and k1 is an integer of 0 to 6)
  • R 1 is as defined above, R 3 is each independently a substituent containing an epoxy group, R 4 is each independently an alkyl group having 1 to 4 carbon atoms, and R 5 is each independently a halogen atom.
  • R 4 is each independently an alkyl group having 1 to 4 carbon atoms, and R 5 is each independently a halogen atom.
  • p ⁇ 2, q ⁇ 1, r ⁇ 0, p + Q + r is an integer of 3 to 6.
  • the arrangement of each repeating unit is arbitrary.)
  • the epoxy group-containing compound having a carbon-carbon unsaturated bond in the present invention is not particularly limited as long as it is an olefin-containing epoxy group-containing compound having hydrosilylation reactivity, and specifically, 1,2-epoxy-4- Examples include, but are not limited to, vinylcyclohexane, allyl glycidyl ether, 1,2-epoxy-5-hexene, and 1,2-epoxy-7-octene.
  • an olefin compound having the substituent (described above, CH 2 ⁇ CH—R 6a ) may be used.
  • the ratio of the reaction raw materials used in the present invention is preferably 0.7 to 1.5 moles, more preferably a total of compounds having a carbon-carbon unsaturated bond per mole of Si—H groups in the organohydrogensiloxane. 0.9 to 1.1 mol.
  • the hydrosilylation reaction catalyst in the present invention is a complex compound having platinum (Pt) and / or platinum (Pt) as a central metal, which is known as a known technique.
  • a complex compound having platinum (Pt) and / or platinum (Pt) as a central metal which is known as a known technique.
  • an alcohol solution of chloroplatinic acid, a 1,3-divinyltetramethyldisiloxane complex of chloroplatinic acid, a compound obtained by neutralizing the complex, and the oxidation number of the central metal is Pt (II) or Pt ( 0) 1,3-divinyltetramethyldisiloxane complex.
  • the oxidation number of the central metal is a complex other than Pt (IV) from the viewpoint of addition site selectivity, and Pt (0) and Pt (II) are particularly preferable.
  • the amount of the hydrosilylation reaction catalyst used in the present invention is not particularly limited as long as the catalytic effect of the hydrosilylation reaction is manifested, but is preferably 0.000001 to 0.000001 to in terms of platinum metal with respect to 1 mol of the total amount of olefin compounds. 1 mol, more preferably 0.000003 to 0.01 mol.
  • the amount is less than 0.000001 mol, there is a possibility that a sufficient catalytic effect may not be exhibited.
  • the amount is more than 1 mol, the effect is saturated, and the production cost may be increased, which may be uneconomical.
  • a viscosity shows the value in 25 degreeC measured with the Ostwald viscometer.
  • the title siloxane was obtained as a colorless transparent liquid having a viscosity of 74 mm 2 / s and a refractive index of 1.4559 (25 ° C.) by removing toluene and excess allyl glycidyl ether by distillation under reduced pressure (80 ° C., 2 mmHg).
  • the obtained title siloxane was subjected to 1 H-NMR and IR measurement. The results are shown in FIGS. 3 and 4, respectively.
  • the title siloxane was obtained as a colorless transparent liquid having a viscosity of 64 mm 2 / s and a refractive index of 1.4552 (25 ° C.) by removing toluene and excess allyl glycidyl ether by distillation under reduced pressure (80 ° C., 2 mmHg).
  • the obtained title siloxane was subjected to 1 H-NMR and IR measurement. The results are shown in FIGS. 5 and 6, respectively.

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  • Organic Chemistry (AREA)
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Abstract

La présente invention concerne un organosiloxane cyclique contenant un groupe époxy représenté par la formule (1), comprenant au moins deux groupes époxy dans une seule molécule, et présentant ainsi une excellente compatibilité avec d'autres résines organiques lorsqu'il est préparé en une composition avec un composé comprenant un groupe organique qui est réactif avec lesdits groupes fonctionnels, et présente également une fonction en tant que liant. L'organosiloxane cyclique contenant un groupe époxy comprend également un groupe silyle hydrolysable, et l'on peut ainsi s'attendre également à ce qu'il soit un agent de couplage silane efficace. (R1 est un groupe alkyle ou un groupe aryle ; R2 est un atome d'hydrogène ou un groupe alkyle qui peut avoir un substituant choisi parmi un atome d'halogène, un groupe vinyle, un groupe époxy, un groupe thiiranne, un groupe (méth)acrylique, un groupe mercapto, un groupe iso(thio)cyanate, un groupe silyle hydrolysable, un groupe anhydride succinique, un groupe perfluoroalkyle, un groupe polyéther, et un groupe perfluoropolyéther ; il y a au moins un R2 comprenant un groupe silyle hydrolysable en tant que substituant et au moins deux R2 comprenant un groupe époxy en tant que substituant ; et n est un nombre entier allant de 3 à 6.)
PCT/JP2016/056363 2015-04-20 2016-03-02 Organosiloxane cyclique contenant un groupe époxy WO2016170850A1 (fr)

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CN112752778A (zh) * 2018-12-26 2021-05-04 宝理塑料株式会社 聚缩醛共聚物和其制造方法
CN112752779A (zh) * 2018-12-26 2021-05-04 宝理塑料株式会社 聚缩醛树脂组合物和聚缩醛树脂组合物的制造方法

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JP2018118940A (ja) * 2017-01-27 2018-08-02 モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 熱伝導性ポリシロキサン組成物用表面処理剤
JP2024147227A (ja) * 2023-04-03 2024-10-16 信越化学工業株式会社 有機ケイ素化合物及びその製造方法並びに添加剤

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CN112752779B (zh) * 2018-12-26 2023-08-29 宝理塑料株式会社 聚缩醛树脂组合物和聚缩醛树脂组合物的制造方法
CN112752778B (zh) * 2018-12-26 2023-12-29 宝理塑料株式会社 聚缩醛共聚物和其制造方法

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