WO2016080762A1 - Résine de phtalonitrile - Google Patents

Résine de phtalonitrile Download PDF

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Publication number
WO2016080762A1
WO2016080762A1 PCT/KR2015/012419 KR2015012419W WO2016080762A1 WO 2016080762 A1 WO2016080762 A1 WO 2016080762A1 KR 2015012419 W KR2015012419 W KR 2015012419W WO 2016080762 A1 WO2016080762 A1 WO 2016080762A1
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Prior art keywords
formula
group
compound
cyano
phthalonitrile
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PCT/KR2015/012419
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English (en)
Korean (ko)
Inventor
김상우
이승희
안기호
Original Assignee
주식회사 엘지화학
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Priority claimed from KR1020150161314A external-priority patent/KR101772287B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to US15/524,497 priority Critical patent/US10400065B2/en
Priority to CN201580061646.3A priority patent/CN107001616B/zh
Publication of WO2016080762A1 publication Critical patent/WO2016080762A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
    • C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/48—Polymers modified by chemical after-treatment

Definitions

  • the present application relates to phthalonitrile resins, polymerizable compositions, prepolymers, composites, methods of making and uses thereof.
  • the phthalonitrile resin can be used for various applications.
  • a composite formed by impregnating a phthalonitrile resin into a filler such as glass fiber or carbon fiber may be used as a material for automobiles, airplanes, ships, and the like.
  • the manufacturing process of the composite may include, for example, curing after mixing a filler and a prepolymer formed by a mixture of a phthalonitrile and a curing agent or a mixture thereof.
  • Such contents are disclosed in Korean Patent No. 0558158 and the like.
  • the monomer phthalonitrile or the polymerizable composition or prepolymer formed therefrom have appropriate meltability and fluidity, and a so-called process window is wide.
  • the present application provides a phthalonitrile resin, a polymerizable composition, a prepolymer, a composite, a precursor of the composite, and a method and use of the preparation.
  • the present application provides a phthalonitrile, a polymerizable composition and a prepolymer using the same, which exhibits excellent curability, exhibits a suitable processing temperature and a wide process window, and can form a composite of excellent physical properties.
  • the present application is directed to phthalonitrile resins.
  • the phthalonitrile resin may include a polymerized unit derived from the compound of formula (1).
  • the term “polymerized unit derived from a compound” may refer to a skeleton of a polymer formed by polymerization or curing of the compound.
  • R 1 to R 10 are each independently hydrogen, an alkyl group, an alkoxy group, an aryl group, or a cyano group, at least two of R 1 to R 5 are cyano groups, and at least two of R 6 to R 10 are Is a cyano group, X 1 and X 2 are each independently an alkylene group, an alkylidene group, an oxygen atom or a sulfur atom, Ar 1 , Ar 2 and Ar 3 are the same or different aromatic divalent radicals, n is one or more Wherein m is one or more numbers, L 1 is an alkylene group or an alkylidene group, and L 2 is an alkylene group or alkylidene group substituted with a monovalent radical of formula (2):
  • R 11 to R 15 are each independently hydrogen, an alkyl group, an alkoxy group, an aryl group, or a cyano group, at least two of R 11 to R 15 are cyano groups, X 3 is an alkylene group, an alkylidene group, Is an oxygen atom or a sulfur atom, and Ar 4 is an aromatic divalent radical.
  • alkyl group may be an alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms, unless otherwise specified.
  • the alkyl group may be linear, branched or cyclic and may be substituted by one or more substituents if necessary.
  • alkoxy group in the present application may be an alkoxy group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms, unless otherwise specified.
  • the alkoxy group may be linear, branched or cyclic and may be substituted by one or more substituents if necessary.
  • aryl group in the present application may mean a monovalent moiety derived from a benzene ring, a compound containing a benzene ring, or a derivative of any one of the above, unless otherwise specified.
  • the compound including the benzene ring it may mean a compound having a structure in which two or more benzene rings are condensed while sharing one or two carbon atoms, or are directly connected or connected by an appropriate linker.
  • biphenyl, naphthalene, etc. can be illustrated.
  • the aryl group may include, for example, 6 to 25, 6 to 20, or 6 to 12 carbon atoms.
  • aryl group may include, but are not limited to, a phenyl group, benzyl group, biphenyl group or naphthalenyl group.
  • the scope of the aryl group in the present application may include a functional group commonly referred to as an aryl group as well as a so-called aralkyl group or an arylalkyl group.
  • aromatic divalent radical means a benzene ring, a compound containing a benzene ring, or a divalent moiety derived from any one of the above-mentioned derivatives unless otherwise specified.
  • the aromatic divalent radical may include, for example, 6 to 25, 6 to 20, or 6 to 12 carbon atoms.
  • Representative types of aromatic divalent radicals include, but are not limited to, phenylene groups.
  • alkylene group or alkylidene group in the present application means an alkylene group or alkylidene group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms, unless otherwise specified. can do.
  • the alkylene group or alkylidene group may be linear, branched or cyclic.
  • the alkylene group or alkylidene group may be optionally substituted with one or more substituents.
  • the substituent which may be optionally substituted with the alkyl group, alkoxy group, aryl group, aromatic divalent radical, alkylene group or alkylidene group, halogen, glycidyl group, epoxyalkyl group, glyci such as chlorine or fluorine Epoxy groups, such as a doxyalkyl group or an alicyclic epoxy group, acryloyl group, methacryloyl group, an isocyanate group, a thiol group, an alkyl group, an alkoxy group, or an aryl group etc. can be illustrated, but it is not limited to these.
  • R 1 to R 10 are each independently hydrogen, an alkyl group, an alkoxy group, an aryl group, or a cyano group, at least two of R 1 to R 5 are cyano groups, and at least two of R 6 to R 10 It is a cyano group.
  • R 1 to R 10 which are not a cyano group are each independently hydrogen, an alkyl group, or an alkoxy group, or may be hydrogen or an alkyl group.
  • R 3 , R 4 , R 8 and R 9 are cyano groups
  • R 1 , R 2 , R 5 , R 6 , R 7 and R 10 are each independently hydrogen, an alkyl group, alkoxy It may be a group or an aryl group, hydrogen, an alkyl group, or an alkoxy group, or hydrogen or an alkyl group.
  • X 1 and X 2 in Formula 1 are each independently an alkylene group, an alkylidene group, an oxygen atom or a sulfur atom, and in another example, may be an alkylene group, an alkylidene group or an oxygen atom, or may be an oxygen atom.
  • Ar 1 , Ar 2, and Ar 3 in Formula 1 may be the same or different aromatic divalent radicals, and the aromatic divalent radical may be, for example, phenylene, but is not limited thereto.
  • the substitution position of L 1 based on X 1 in Ar 1 of Formula 1 may be an ortho, meta, or para position, for example, a para position. have.
  • the substitution position of L 2 based on L 1 in Ar 2 of Formula 1 may be an ortho, meta, or para position, for example, a para position.
  • the substitution position of X 2 based on L 2 may be an ortho, meta, or para position, for example, a para position. have.
  • N may be any number of one or more
  • m may be any number of one or more.
  • the fact that n and m are at least one at the same time allows the compound to exhibit excellent curing properties and to exhibit appropriate processing temperature and process window characteristics.
  • n and m in the formula (1) at the same time at least 1, while maintaining the number of phthalonitrile groups participating in the curing reaction is appropriate, the structure of the overall compound can be maintained advantageously to the processing temperature and process window properties.
  • m is 0, the number of phthalonitrile groups included in the compound of Formula 1 is limited, and at the same time, the structure of the core portion of the compound may exhibit symmetry. This results in an increase in processing temperature, such as melting temperature, and at the same time deteriorates process window characteristics.
  • the structure of the compound of Formula 1 may exhibit symmetry that facilitates intermolecular overlap, and this symmetry causes an increase in crystallinity, resulting in processing temperature (ex. ) And deterioration of the process window characteristics can be induced.
  • N in Formula 1 may be in the range of 1 to 10, 1 to 8, 1 to 6, 1 to 4, or 1 to 3, or 1 or 2 in another example.
  • M in formula 1 may be in the range of 1 to 10, 1 to 8, 1 to 6, 1 to 4 or 1 to 3, or 1 or 2.
  • L 1 may be an alkylene group or an alkylidene group
  • L 2 may be an alkylene group or an alkylidene group substituted with the monovalent radical of Formula 2 above.
  • R 11 to R 15 are each independently hydrogen, an alkyl group, an alkoxy group, an aryl group, or a cyano group, and at least two of R 11 to R 15 are cyano groups.
  • R 1 to R 5 which are not cyano groups are each independently hydrogen, an alkyl group or an alkoxy group, or may be hydrogen or an alkyl group.
  • R 13 and R 14 are cyano groups, and R 11 , R 12 and R 15 are each independently hydrogen, an alkyl group, an alkoxy group or an aryl group, a hydrogen, an alkyl group or an alkoxy group, or It may be hydrogen or an alkyl group.
  • X 3 in Formula 2 is an alkylene group, an alkylidene group, an oxygen atom or a sulfur atom, and in another example, may be an alkylene group, an alkylidene group or an oxygen atom, or may be an oxygen atom.
  • Ar 4 is an aromatic divalent radical
  • the aromatic divalent radical may be, for example, phenylene, but is not limited thereto.
  • the substitution position of X3 based on the site linked to L 2 of Formula 1 in Ar 4 of Formula 2 may be an ortho, meta, or para position, for example, para (para) location.
  • Sign in formula (2) May mean that the site is linked to L in the general formula (1).
  • Suitable compounds in one example are compounds in which X 1 and X 2 in formula 1 are oxygen atoms, Ar 1 , Ar 2 and Ar 3 are phenylene groups, n is 1 or 2 and m is 1 or 2 Can be.
  • Ar 4 in Formula 2 may be a phenylene group, and X 3 may be an oxygen atom.
  • the above descriptions may be applied to specific types of R1 to R15 and substitution positions of L 1 , L 2 , X 2 and X 3 in the phenylene group.
  • the compound may provide a polymerizable composition and a prepolymer excellent in curability, exhibiting an appropriate processing temperature and a wide process window, and capable of forming a complex of excellent physical properties.
  • the processing temperature of the compound may be, for example, in the range of 100 ° C. to 250 ° C. or 100 ° C. to 200 ° C.
  • the term processing temperature in the present application may mean a temperature at which the compound, the following polymerizable composition or prepolymer including the same, and the like exist in a processable state.
  • Such a processing temperature may be, for example, a softening point, a melting temperature (Tm) or a glass transition temperature (Tg). This range is advantageous for implementing a polymerizable composition or prepolymer that exhibits proper fluidity and processability, ensures a wide process window, and can form a composite of good physical properties.
  • the compound of formula 1 can be synthesized according to the synthesis method of known organic compounds.
  • the compound of Formula 1 may be reacted with a reaction known as a nitro displacement reaction, for example, a compound containing a hydroxy group and a compound containing a nitrile group in the presence of a basic catalyst or the like. Can be synthesized.
  • the phthalonitrile resin may further include a polymerization unit of another phthalonitrile compound in addition to the polymerization unit of the compound of the formula (1).
  • the kind of phthalonitrile compound that can be selected and used is not particularly limited, and known compounds known to be useful for the formation of phthalonitrile resins and the control of their physical properties can be applied. Examples of such compounds include U.S. Patent 4,408,035, U.S. Patent 5,003,039, U.S. Patent 5,003,078, U.S. Patent 5,004,801, U.S. Patent 5,132,396, U.S. Patent 5,139,054, U.S. Patent 5,208,318, U.S. Patent Compounds known from US Pat. No. 5,237,045, US Pat. No. 5,292,854, US Pat. No. 5,350,828, and the like can be exemplified, and various compounds known in the art other than those described above can be included in the examples.
  • the phthalonitrile resin may include a polymer unit of the compound of Formula 1 or a polymer unit of a phthalonitrile compound including the compound as a main component.
  • the inclusion of any component as a main component means that the component is 55% or more, 60% or more, 65% or more, 70% or more, 75% or more, 80% or more, 85% or more, 90% or more by weight. Or 95% or more.
  • the upper limit of the ratio is not particularly limited and may be, for example, 100% or less, less than 100%, 95% or less, or 90% or less by weight.
  • the polymer unit of the compound of Formula 1 may be a polymer unit formed by the reaction of the compound of Formula 1 and a curing agent.
  • the type of curing agent that can be used in this case is not particularly limited as long as it can react with the compound of Formula 1 to form a polymer.
  • any compound may be used as long as it is a compound known to be useful for forming a phthalonitrile resin. Can be.
  • Such hardeners are known in various documents, including the US patents described above.
  • an amine compound or a hydroxy compound such as an aromatic amine compound may be used as a curing agent.
  • a hydroxy compound may mean a compound including at least one or two hydroxy groups in a molecule.
  • Curing agents capable of curing the phthalonitrile compound to form a resin are variously known, and such curing agents can be applied to most of the present application.
  • the present application also relates to polymerizable compositions.
  • the polymerizable composition may include the compound of Formula 1 described above.
  • the polymerizable composition may further include a curing agent together with the compound of Formula 1.
  • the type of curing agent that can be used above is not particularly limited, and for example, a curing agent as described above can be used.
  • the proportion of the curing agent in the polymerizable composition is not particularly limited.
  • the ratio may be adjusted to ensure the desired curability in consideration of the ratio or type of the curable component such as the compound of Formula 1 included in the composition.
  • the curing agent may be included in an amount of about 0.02 mol to 1.5 mol per mol of the compound of Formula 1 included in the polymerizable composition.
  • the ratio is only an example of the present application.
  • the ratio of the curing agent in the polymerizable composition is high, but the process window is narrow, and when the ratio of the curing agent is low, the curing property tends to be insufficient, so in view of this point, an appropriate ratio of curing agent can be selected. have.
  • the polymerizable composition of the present application can exhibit an appropriate processing temperature and a wide process window while being excellent in curability.
  • the processing temperature of the polymerizable composition may be in the range of 100 ° C to 250 ° C or 100 ° C to 200 ° C.
  • the absolute value of the process window of the polymerizable composition i.e., the difference between the processing temperature (Tp) and the curing temperature (Tc) of the compound of Formula 1 and the curing agent (Tc) is 50 ° C or more, 70 ° It may be above C or above 100 ° C.
  • the curing temperature (Tc) may be higher than the processing temperature. This range may be advantageous to secure appropriate processability in the process of producing a composite, for example, which will be described later using the polymerizable composition.
  • the upper limit of the process window is not particularly limited, but for example, the absolute value of the difference (Tc-Tp) between the processing temperature (Tp) and the curing temperature (Tc) may be 300 ° C or less or 200 ° C or less. have.
  • the polymerizable composition may further include various additives including other phthalonitrile compounds in addition to the compound of Chemical Formula 1.
  • additives may include, but are not limited to, fillers or dispersants such as glass fibers, carbon fibers, graphene, or carbon nanotubes as described below.
  • the polymerizable composition may include a compound of Formula 1 or a phthalonitrile compound including the compound as a main component. Accordingly, the polymerizable composition may contain at least 55%, at least 60%, at least 65%, at least 70%, at least 75%, at least 80% of the compound of Formula 1 or the phthalonitrile compound including the compound by weight. 85% or more, 90% or more, or 95% or more.
  • the upper limit of the ratio is not particularly limited and may be, for example, 100% or less, less than 100%, 95% or less, or 90% or less by weight.
  • the present application also relates to a prepolymer formed by the reaction of the polymerizable composition, that is, the polymerizable composition comprising the compound of Formula 1 and a curing agent.
  • prepolymer state refers to a state in which the compound of Formula 1 and a curing agent occur to some extent in the polymerizable composition (for example, a state in which polymerization of the A or B stage stage occurs), It can mean the state which can process a composite_body
  • the prepolymer state may refer to a state in which polymerization of the polymerizable composition is performed to some extent.
  • the prepolymer may also exhibit good curability, suitable processing temperatures and a wide process window.
  • the prepolymer may exhibit stability over time even when stored at room temperature for a long time.
  • the processing temperature of the prepolymer for example, glass transition temperature or melting temperature
  • the absolute value of the process window of the prepolymer i.e. the difference (Tc-Tp) between the processing temperature (Tp) and the curing temperature (Tc) of the prepolymer
  • the curing temperature Tc may be higher than the processing temperature Tp. This range may be advantageous to ensure appropriate processability using a prepolymer, for example, in the preparation of the composite described below.
  • the upper limit of the process window is not particularly limited, but for example, the absolute value of the difference (Tc-Tp) between the processing temperature (Tp) and the curing temperature (Tc) may be 300 ° C or less or 200 ° C or less. have.
  • the prepolymer may further comprise any known additive in addition to the above components.
  • examples of such an additive may include, but are not limited to, the aforementioned fillers.
  • the present application also relates to composites.
  • the composite may include the phthalonitrile resin and filler described above.
  • the composite formed as described above may include the phthalonitrile resin and the filler, and may be applied to various applications including, for example, durable materials such as automobiles, airplanes, or ships.
  • filler is not particularly limited and may be appropriately selected in consideration of the intended use.
  • Fillers that can be used include fibrous materials such as carbon fibers, aramid fibers, glass fibers or ceramic fibers, or carbon nanomaterials such as woven fabrics, nonwovens, strings or strings or carbon nanotubes or graphemes formed by the materials. Etc. may be exemplified, but is not limited thereto.
  • the proportion of the filler is also not particularly limited and may be set in an appropriate range depending on the intended use.
  • the present application also relates to a precursor for preparing the composite, which precursor may comprise, for example, the polymerizable composition and the filler described above, or may comprise the prepolymer and the filler described above.
  • the composite can be prepared in a known manner using the precursor.
  • the composite may be formed by curing the precursor.
  • the precursor is a polymerizable composition comprising the compound of Formula 1 and a curing agent, or the filler, if necessary, in a state in which the prepolymer formed by temporarily curing the polymerizable composition is melted by heating or the like. It can mix and manufacture.
  • the precursor prepared as described above may be molded into a desired shape and then cured to prepare the above-described composite.
  • the polymerizable composition or prepolymer has an appropriate processing temperature and a wide process temperature, and excellent curing property, so that molding and curing can be efficiently performed in the process.
  • a method of forming a prepolymer or the like, a method of mixing the prepolymer or the like with filler, processing and curing to prepare a composite, and the like may be performed according to a known method.
  • DSC analysis was performed in a N2 flow atmosphere using a TA instrument Q20 system at a rate of temperature rise of 10 ° C / min from 35 ° C to 450 ° C.
  • TGA analysis was performed using a TGA e850 instrument from Mettler-Toledo.
  • the compound prepared in Preparation Example was analyzed in an N2 flow atmosphere while raising the temperature at a temperature increase rate of 10 ° C / min from 25 ° C to 800 ° C, in the case of the composition prepared in Examples or Comparative Examples of 375 ° C
  • After post-curing at the temperature was analyzed in the N2 flow atmosphere while raising the temperature at a temperature rising rate of 10 ° C / min from 25 ° C to 900 ° C.
  • results of NMR analysis for the compound of formula C are shown in FIG. 1.
  • DSC analysis of the compound of Formula C showed that the processing temperature (softening point) was about 104 ° C.
  • the residue at 800 ° C. was found to be as high as 42% by weight, indicating that it had excellent thermal stability.
  • the compound of formula J (CA1) was obtained from TCI (Tokyo Chemical Industry Co., Ltd.) and used without further purification.
  • the polymerizable composition may be melted at 150 ° C. and stirred for 5 minutes to prepare a prepolymer.
  • the polymerizable composition may be melted at 240 ° C. and stirred for 5 minutes to prepare a prepolymer.
  • the polymerizable composition may be melted at 240 ° C. and stirred for 5 minutes to prepare a prepolymer.
  • Example 1 using a compound having a structure of m and n in the formula (1) while having three phthalonitrile groups, much lower processing compared to the case of Comparative Examples 1 and 2 having two phthalonitrile groups It can be seen that it is possible to prepare the prepolymer at a low temperature with a temperature, to secure a wide process window of 100 ° C. or more, and to exhibit excellent heat resistance.
  • Comparative Example 3 it has three phthalonitrile groups as in the case of Example 1, but due to the symmetry of the core structure, the crystallinity is increased, thereby increasing the processing temperature, as a result the process window It was confirmed very narrowly.

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Abstract

La présente invention concerne une résine de phtalonitrile, une composition polymérisable, un prépolymère, un composite, un procédé de préparation de celle-ci, et son utilisation. La présente application permet d'obtenir du phtalonitrile présentant une excellente aptitude au durcissement, une température de traitement appropriée et une large fenêtre de traitement, et permet de former un composite ayant d'excellentes propriétés physiques; une composition polymérisable à l'aide de celui-ci; et un prépolymère.
PCT/KR2015/012419 2014-11-18 2015-11-18 Résine de phtalonitrile WO2016080762A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US15/524,497 US10400065B2 (en) 2014-11-18 2015-11-18 Phthalonitrile resin
CN201580061646.3A CN107001616B (zh) 2014-11-18 2015-11-18 邻苯二甲腈树脂

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2014-0160813 2014-11-18
KR20140160813 2014-11-18
KR1020150161314A KR101772287B1 (ko) 2014-11-18 2015-11-17 프탈로니트릴 수지
KR10-2015-0161314 2015-11-17

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018084465A1 (fr) * 2016-11-04 2018-05-11 주식회사 엘지화학 Composition polymérisable
EP3597957A4 (fr) * 2017-05-22 2020-04-29 LG Chem, Ltd. Composition de résine pour matériau de frottement de plaquette de frein et matériau de frottement de plaquette de frein fabriqué à l'aide de la composition de résine

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5389441A (en) * 1993-06-28 1995-02-14 The United States Of America As Represented By The Secretary Of The Navy Phthalonitrile prepolymer as high temperature sizing material for composite fibers
KR20010030872A (ko) * 1997-10-02 2001-04-16 더 거번먼트 오브 더 유나이티드 스테이츠 오브 아메리카, 애즈 레프리젠티드 바이 더 세크러테리 오브 더 네이비 네이벌 리서치 래보러토리 낮은 반응성을 지닌 방향족 아민 경화제로 경화시킨섬유-강화 프탈로니트릴 조성물
JP2005105193A (ja) * 2003-10-01 2005-04-21 Rikogaku Shinkokai デンドリティック多量体及び高誘電率高分子材料
KR100525304B1 (ko) * 1998-06-26 2005-11-02 미합중국 (관리부서 : 미합중국 해군성) 프탈로니트릴 수지로부터 유도된 탄소 베이스 복합물
CN103834008A (zh) * 2014-03-10 2014-06-04 中国科学院化学研究所 一种新型邻苯二甲腈树脂及其制备方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5389441A (en) * 1993-06-28 1995-02-14 The United States Of America As Represented By The Secretary Of The Navy Phthalonitrile prepolymer as high temperature sizing material for composite fibers
KR20010030872A (ko) * 1997-10-02 2001-04-16 더 거번먼트 오브 더 유나이티드 스테이츠 오브 아메리카, 애즈 레프리젠티드 바이 더 세크러테리 오브 더 네이비 네이벌 리서치 래보러토리 낮은 반응성을 지닌 방향족 아민 경화제로 경화시킨섬유-강화 프탈로니트릴 조성물
KR100525304B1 (ko) * 1998-06-26 2005-11-02 미합중국 (관리부서 : 미합중국 해군성) 프탈로니트릴 수지로부터 유도된 탄소 베이스 복합물
JP2005105193A (ja) * 2003-10-01 2005-04-21 Rikogaku Shinkokai デンドリティック多量体及び高誘電率高分子材料
CN103834008A (zh) * 2014-03-10 2014-06-04 中国科学院化学研究所 一种新型邻苯二甲腈树脂及其制备方法

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018084465A1 (fr) * 2016-11-04 2018-05-11 주식회사 엘지화학 Composition polymérisable
US11091592B2 (en) 2016-11-04 2021-08-17 Lg Chem, Ltd. Polymerizable composition
EP3597957A4 (fr) * 2017-05-22 2020-04-29 LG Chem, Ltd. Composition de résine pour matériau de frottement de plaquette de frein et matériau de frottement de plaquette de frein fabriqué à l'aide de la composition de résine
US11002329B2 (en) 2017-05-22 2021-05-11 Lg Chem, Ltd Resin composition for brake pad friction materials and brake pad friction materials made of the resin composition

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