WO2017078478A1 - Polyglutarimide réticulé contenant de l'isosorbide, et son procédé de production - Google Patents

Polyglutarimide réticulé contenant de l'isosorbide, et son procédé de production Download PDF

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WO2017078478A1
WO2017078478A1 PCT/KR2016/012690 KR2016012690W WO2017078478A1 WO 2017078478 A1 WO2017078478 A1 WO 2017078478A1 KR 2016012690 W KR2016012690 W KR 2016012690W WO 2017078478 A1 WO2017078478 A1 WO 2017078478A1
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group
substituted
unsubstituted
branched
polyglutarimide
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정민경
임병탁
김인범
조대희
김승환
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에스케이이노베이션 주식회사
에스케이종합화학 주식회사
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Publication of WO2017078478A1 publication Critical patent/WO2017078478A1/fr

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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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors

Definitions

  • the present invention relates to a crosslinked polyglutarimide comprising isosorbide and a process for preparing the same.
  • Polymethyl methacrylate is one of the polymers of methyl methacrylate. It is not only excellent in transparency and weather resistance, but also excellent in hardness, chemical resistance, surface gloss and adhesion, and is widely used as a substitute for glass. It is used to replace tempered glass, which is used as a window material applied to the housing of a home appliance and a touch surface of a mobile phone.
  • methacrylate-based resins have a problem that heat distortion temperature (HDT) is 80 to 97 ° C. and continuous use temperature is low to 60 to 80 ° C., compared with other plastic materials, and thus has low heat resistance. .
  • HDT heat distortion temperature
  • continuous use temperature is low to 60 to 80 ° C.
  • Polyglutalimide which is applied as a substitute for polymethyl methacrylate, contains imide bonds, has excellent mechanical properties and optical properties with high modulus, viscosity, and refractive index, and has a glass transition temperature of 130 ° C. or higher. It has a better heat resistance than polymethyl methacrylate.
  • polyglutarimide has a glass transition temperature of up to 180 ° C., and when a high temperature is applied thereto, mechanical properties and optical properties change. Accordingly, there is a demand for a method for imparting heat resistance and mechanical properties to the polyglutarimide chemical structure to solve the above problem.
  • the present invention has been made to solve the problems described above, as a cross-linking agent to polyglutarimide, two tetrahydrofuran ring has a structure bonded at an angle of 120 °, giving heat resistance, transparency and surface hardness improvement effect
  • isosorbide which is capable of crosslinking polyglutarimide
  • the present invention provides a crosslinked polyglutarimide and a method for preparing the same, which have better mechanical, optical and thermal properties than general polyglutarimide. .
  • the present invention provides a polyglutarimide comprising a glutarimide repeating unit represented by the following formula (1),
  • 0.001 to 1.2 mole% of the glutarimide repeating unit relates to a polyglutarimide which forms a crosslinked structure represented by Chemical Formula 2.
  • R 1 And R 3 are independently of each other hydrogen or CH 3 ;
  • R 2 Is a substituted or unsubstituted linear or branched C1-C20 alkyl group, a substituted or unsubstituted straight or branched C3-C20 alkenyl group, a substituted or unsubstituted C3-C20 alkynyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C18 aryl group, straight or branched C1-C20 hydroxyalkyl group, straight or branched C1-C18 epoxyalkyl group, acryloyl group, methacryloyl group And acrylooxy group is any one selected from the group consisting of;
  • R z Is a substituted or unsubstituted linear or branched C1-C20 alkyl group, a substituted or unsubstituted straight or branched C3-C20 alkenyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted Any one selected from the group consisting of a C6-C18 aryl group, a straight or branched C1-C18 epoxyalkyl group, an acryloyl group, a methacryloyl group, and an acrylooxy group;
  • a and b are each independently an integer of 1 to 1,000, and may be 0.001a ⁇ b ⁇ 0.33a.
  • the crosslinked polyglutarimide including isosorbide according to the present invention includes isosorbide, which exhibits transparency and surface hardness enhancement effect, as a crosslinking agent in the polyglutarimide, thereby significantly improving heat resistance and mechanical properties. It is possible to enable the production of molded articles such as improved display optical members and electrical and electronic circuit members.
  • Example 1 is prepared according to the method of Example 1 (top right), Example 2 (center top), Example 3 (top left), Example 6 (bottom left) and Example 8 (bottom right) of the present invention. It is the result of visual observation whether the film of the formed XLPGI was formed.
  • Comparative Example 2 is prepared according to the method of Comparative Example 1 (top right), Comparative Example 2 (top left), Comparative Example 3 (bottom left), Comparative Example 4 (center bottom) and Comparative Example 5 (bottom right) of the present invention. It is the result of visual observation whether the film of the formed XLPGI was formed.
  • substituted silver 'in the compound or structure constituting the compound, a hydrogen element bonded to a carbon element is halogen, nitro, hydroxy, C1-C7 alkyl, C1-C7 alkoxy, C1-C7 alkylcarbonyl, Substituted with one or more substituents selected from C1-C7 alkoxycarbonyl, formyl (-CHO) and the like.
  • polyglutarimide means 'crosslinked polyglutarimide comprising isosorbide structure'.
  • the present invention relates to a polyglutarimide having excellent optical properties and remarkably improved heat resistance and mechanical properties, and in the polyglutarimide comprising a glutarimide repeating unit represented by Formula 1 below,
  • 0.001 to 1.2 mole% of the glutarimide repeating unit relates to a polyglutarimide which forms a crosslinked structure represented by Chemical Formula 2.
  • R 1 in Formula 1 And R 3 can independently be hydrogen or CH 3 ;
  • R 2 Is a substituted or unsubstituted linear or branched C1-C20 alkyl group, a substituted or unsubstituted straight or branched C3-C20 alkenyl group, a substituted or unsubstituted C3-C20 alkynyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C18 aryl group, straight or branched C1-C20 hydroxyalkyl group, straight or branched C1-C18 epoxyalkyl group, acryloyl group, methacryloyl group And it may be any one selected from the group consisting of acrylooxy group and the like, preferably any one selected from C1-C20 alkyl group, C3-C20 alkenyl group, C3-C20 alkynyl group and C6
  • the alkyl group and alkenyl group which may be included in the R 2 may be a linear or branched C1 to C20 alkyl group and a linear or branched C3 to C20 alkenyl group, preferably C1 to C10 alkyl group , C3 to C10 alkenyl group and C3 to C10 alkynyl group
  • the cycloalkyl group may be a C3 to C10 cycloalkyl group, preferably C3 to C6 cycloalkyl group, but is not limited thereto.
  • R z Is a substituted or unsubstituted linear or branched C1-C20 alkyl group, a substituted or unsubstituted straight or branched C3-C20 alkenyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C18 aryl group, linear or branched C1-C18 epoxyalkyl group, acryloyl group, methacryloyl group and acrylooxy group and the like can be any one selected from the group consisting of, preferably C1-C20 It may be any one selected from an alkyl group, a C3-C20 alkenyl group, a C3-C20 alkynyl group, and a C6-C18 aryl group, but is not particularly limited thereto.
  • a and B may be any one selected from a single bond and 'R'-X-' form independently of each other, and when A and B are in the 'R'-X-' form, R ′ is bonded to an imide group, and substituted or unsubstituted linear or branched C1-C20 alkylene, substituted or unsubstituted linear or branched C3-C20 alkenylene, substituted or unsubstituted C3-C20 alkynylene, substituted or unsubstituted C3-C10 cycloalkylene and substituted or unsubstituted C6-C18 arylene and the like, and the like, wherein X- is combined with isosorbide May be a single bond, O—, —S—, C ( ⁇ O) —, —C ( ⁇ O) O— or SO 2 —, wherein a and b are integers of 1 to 1,000 independently of each other, 0.001a ⁇ b
  • the polyglutarimide polymer chain bonded with the crosslinked structure represented by Chemical Formula 2 may be a crosslink between different glutarimide repeat units in the same polymer molecule or a bond between glutarimide repeat units between different polymer molecules. Can be.
  • a and B are preferably a single bond
  • It may be any one selected from the group consisting of, but is not particularly limited thereto.
  • Polyglutalimide including the repeating unit of Formula 1 according to the present invention may have a weight average molecular weight of 50,000 to 500,000 g / mol.
  • the weight average molecular weight was measured by using Agilent Technologies' 1260 Infinity (standard sample: Polystyrene), column was used PL gel Olexis, sample was 100ml LiCl (concentration) using DMAc as a solvent : 0.5wt%) contained 4mg.
  • the present invention relates to a method for producing a polyglutarimide crosslinked with an isosorbide structure
  • the method for producing a polyglutarimide is a diamine represented by the formula (3) comprising an acrylate-based polymer, isosorbide It may include the step of reacting the compound and the amine compound represented by the formula (4), wherein the poly glutarimide comprising a repeating unit of the formula (1) prepared through the above step is from 0.001 to the total glutarimide repeating unit 1.2 mol% may include a crosslinked structure represented by Formula 2 below.
  • R 1 of Chemical Formula 1 and Chemical Formula 2 And R 3 Can independently be hydrogen or CH 3 ;
  • R 2 Is a substituted or unsubstituted linear or branched C1-C20 alkyl group, a substituted or unsubstituted straight or branched C3-C20 alkenyl group, a substituted or unsubstituted C3-C20 alkynyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C18 aryl group, straight or branched C1-C20 hydroxyalkyl group, straight or branched C1-C18 epoxyalkyl group, acryloyl group, methacryloyl group And it may be any one selected from the group consisting of acrylooxy group and the like;
  • R z Is a substituted or unsubstituted linear or branched C1-C
  • a and B of Formula 2 may be any one selected from a single bond and 'R'-X-' form independently of each other, when A and B is a 'R'-X-' form, the R ' Is bonded to an imide group and is substituted or unsubstituted straight or branched C1-C20 alkylene, substituted or unsubstituted straight or branched C3-C20 alkenylene, substituted or unsubstituted C3-C20 It may be one or more selected from the group consisting of alkynylene, substituted or unsubstituted C3-C10 cycloalkylene, substituted or unsubstituted C6-C18 arylene, and the like, wherein X- is combined with isosorbide, May be a bond, O—, —S—, C ( ⁇ O) —, —C ( ⁇ O) O—, or SO 2 —, wherein a and b in Formula 1 are each independently an integer of 1
  • a and B are the same as A and B defined in Chemical Formula 2, and may be any one selected from a single bond and a 'R'-X-' form independently of each other, and A and B Is a 'R'-X-' form, R 'is bonded to an amine group, and substituted or unsubstituted linear or branched C1-C20 alkylene, substituted or unsubstituted linear or branched One or more selected from the group consisting of C3-C20 alkenylene, substituted or unsubstituted C3-C20 alkynylene, substituted or unsubstituted C3-C10 cycloalkylene, substituted or unsubstituted C6-C18 arylene, and the like.
  • a and B are preferably a single bond,
  • It may be any one selected from the group consisting of, but is not particularly limited thereto.
  • R 4 z R z is as defined in formula (I)
  • a substituted or unsubstituted linear or branched C1-C20 alkyl group a substituted or unsubstituted straight or branched C3-C20 alkenyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or It may be any one selected from the group consisting of an unsubstituted C6-C18 aryl group, linear or branched C1-C18 epoxyalkyl group, acryloyl group, methacryloyl group and acrylooxy group, and the like.
  • It may be any one selected from the group consisting of linear or branched C1-C20 alkyl group, linear or branched C3-C20 alkenyl group, C3-C10 cycloalkyl and C6-C18 aryl group, but is not particularly limited thereto. .
  • the said acrylate-type monomer used by the manufacturing method of the polyglutarimide of this invention is a monofunctional or polyfunctional alkyl (meth) acrylate and alkenyl (meth) acrylate containing one or more acrylate functional groups.
  • the acrylate polymer may be prepared through polymerization of an acrylate monomer, wherein the polymerization further includes one or more other additives such as radical initiators, suspending agents, buffer salts and chain transfer transfer agents. It can be carried out by conventional polymerization reactions such as suspension polymerization, emulsion polymerization, dispersion polymerization and precipitation polymerization. In this case, any radical initiator, suspending agent, buffer salt, and chain transfer transfer agent used in the polymerization may be used without particular limitation as long as they are commonly used in the polymerization of the acrylate polymer.
  • the acrylate polymer used in the present invention may have a weight average molecular weight of 5,000 to 300,000 g / mol, preferably 10,000 to 200,000 g / mol, more preferably 15,000 to 120,000 g / mol.
  • the weight average molecular weight of the acrylate-based polymer is not particularly limited thereto, but when satisfying the above range, it is possible to dissolve the acrylate-based polymer in a polar organic solvent, so that the acrylate-based polymer and The condensation crosslinking reaction of the diamine of the present invention can be evenly generated, and the XLPGI can be produced as a film having high heat resistance and high elasticity through a solution process.
  • the diamine compound used in the present invention includes an isosorbide structure in the mother nucleus, any diamine compound having an amine group at both ends can be used without limitation, the amine compound also has a compound having one amine group at the end of the chemical structure If it is not limited, all can be used.
  • the addition content of the diamine compound used in the present invention is not particularly limited thereto, but when the content range is satisfied, the cross-linked polyglutarimide (XLPGI) prepared by the reaction with the acrylate polymer of the present invention ) Does not exhibit a gel form, and the efficiency of improving the heat resistance and surface strength of the acrylate-based polymer may be maximized, and thus, polyglutarimide having excellent mechanical strength and heat resistance may be effectively produced.
  • the excessive crosslinking reaction does not occur in the molecular structure of the crosslinked polyglutalimide (XLPGI) to be produced, so that the XLPGI has a thermal crosslinking property, and thus secondary processing is performed. As it becomes possible, it is desirable to be widely used in various forms in various fields.
  • the acrylate-based polymer, the diamine compound and the amine compound may be dissolved in a solvent, and may be prepared as polyglutarimide through a polymerization reaction in a solution.
  • a solvent used for the reaction a polar organic solvent capable of dissolving the acrylate-based polymer and the diamine compound may be used.
  • NMP N-methyl-2-pyrrolidone
  • DMF Dimethylformamide
  • DMAc dimethylacetamide
  • DMSO dimethyl sulfoxide
  • acetone and diethyl acetate and the like, but may include one or more selected from the above.
  • one or more selected from a low boiling point solvent such as tetrahydrofuran (THF) and chloroform and a low absorbing solvent such as ⁇ -butyrolactone may be used as the reaction solvent.
  • the content of the solvent used in the reaction is not particularly limited, but the content of the solvent is 20 to 100 wt%, preferably 30 to 75 wt% based on the total weight of the acrylate-based polymer, diamine compound and amine compound.
  • the condensation polymerization reaction of the acrylate-based polymer and the diamine compound can proceed smoothly and at the same time can prevent excessive use of the solvent, it is preferable in terms of environmental and economic.
  • the reaction may be carried out through a conventional method of stirring or heat treating a solution, and stirring or heat treatment for 6 to 10 hours at a temperature condition of 200 to 250 ° C. and a pressure condition of 10 to 30 kPa. It may be carried out by, but is not particularly limited thereto.
  • the weight average molecular weight of the crosslinked polyglutarimide including the isosorbide structure synthesized from the method for preparing polyglutarimide of the present invention may be 50,000 to 500,000 g / mol.
  • the weight average molecular weight of the polyglutarimide produced through the present invention is not particularly limited thereto, but if the above range is satisfied, not only excellent optical properties but also mechanical properties suitable for use as members in the field of optical members and electrical and electronic materials And it has a high heat resistance, does not cause deformation at a high temperature of 200 to 500 °C, and at the same time can exhibit mechanical properties such as strength, elasticity and surface hardness is preferred.
  • the polyglutarimide prepared from the method for producing polyglutarimide of the present invention is excellent in optical, mechanical and thermal properties through secondary processing such as solution process, extrusion or injection process in a dissolved state in a solution. It can be produced in various forms such as injection molded articles, such as electronic components, automotive parts, and extrusion molded articles such as films, monofilaments, and fibers.
  • the present invention comprises the steps of (1) preparing a mixture by adding a diamine compound comprising a poly glutimide and isosorbide structure to the solvent; And (2) preparing the molded article by secondary processing the mixture.
  • the polyglutarimide used in step (1) of the present invention comprises a polyglutarimide comprising a glutarimide repeat unit represented by the following formula (1); And a polyglutarimide comprising a glutarimide repeating unit represented by Formula 1 below, wherein 0.001 to 1.2 mol% of the glutarimide repeating unit forms a crosslinked structure represented by the following Formula 2; It may be one or more polyglutarimides.
  • R 1 And R 3 are independently of each other hydrogen or CH 3 ;
  • R 2 Is a substituted or unsubstituted linear or branched C1-C20 alkyl group, a substituted or unsubstituted straight or branched C3-C20 alkenyl group, a substituted or unsubstituted C3-C20 alkynyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C18 aryl group, straight or branched C1-C20 hydroxyalkyl group, straight or branched C1-C18 epoxyalkyl group, acryloyl group, methacryloyl group And it is any one selected from the group consisting of acrylooxy group, etc .;
  • R z Is a substituted or unsubstituted linear or branched C1-C20 alkyl group, a substituted or unsubstituted
  • a polar organic solvent capable of dissolving the polyglutarimide and the diamine compound may be used, and the diamine compound including the isosorbide structure may be used as the polyglue. 2 to 100 mol% may be used based on the content of the acrylate repeating unit in the acrylate polymer used to synthesize the tarimide, but is not limited thereto.
  • the mixture prepared through step (1) of the present invention may be manufactured into a molded article through the processing step of step (2), and the processing of step (2) is a molding method generally used for thermoplastic resins, specifically As an injection molding, it may be carried out by a method such as extrusion molding and press molding, but is not particularly limited thereto.
  • the molded article prepared through step (2) of the present invention is crosslinked by a diamine compound containing the isosorbide structure in which the acrylate repeating unit present in the polyglutarimide of the present invention is added during the secondary process.
  • a fully-crosslinked polyglutarimide hereinafter referred to as cross-linked polyglutarimide
  • cross-linked polyglutarimide molded article including the cross-linked glutarimide repeat unit of Formula 2, wherein the optical, mechanical and thermal properties Injection molded articles such as excellent electrical, electronic components, automotive parts, and extrusion molded articles such as films, monofilaments, fibers, and the like, and preferably, may include display optical members, electronic circuit members, and the like.
  • the polyglutarimide molded article produced through the present invention includes the cross-linked polyglutarimide, in addition to the light stabilizer, impact modifier, catalyst, plasticizer, dye, colorant, organic pigment, inorganic pigment, flame retardant, antistatic agent, It may further comprise one or more other components such as bio-stabilizers, compatibilizers, curing agents, lubricants, heat stabilizers, antioxidants, UV stabilizers.
  • the display optical member and the electronic circuit member can be adjusted by controlling the degree of crosslinking of the cross-linked polyglutarimide, optical properties, mechanical properties and thermal properties can be adjusted It can be characterized.
  • the display optical member typically includes a window applied to a touch surface of a refrigerator, an air conditioner, a mobile phone, and the like, a resin for a large backlight unit light guide plate, and the electronic circuit member includes electrical wiring for a radio, a television, and a computer. Electrical wiring coatings, printed wiring boards, dielectrics of semiconductors and electrical networks, and the like, but is not limited thereto.
  • the gel synthesis phenomenon was observed by visually observing a solution synthesized with each of the polyglutarimides (XLPGI) prepared in Example 2 and Comparative Example, step 2). At this time, when gelation occurs, it is indicated by ⁇ , when partially generated by ⁇ , and when not generated, by x.
  • the XLPGI film samples prepared through Examples and Comparative Examples were visually observed to observe the formation of the XLPGI film and the yellowness of the formed XLPGI film.
  • the glass transition temperature of the XLPGI film samples prepared in Examples and Comparative Examples was measured.
  • the sample was vacuum dried at 60 ° C. for 24 hours at a heating rate of 10 ° C./min, and the glass transition temperature was measured under nitrogen atmosphere.
  • the coating was cast on a glass substrate at a coating gap of 200 ⁇ m and a coating rate of 4 mm / min, followed by drying at 50 ° C. for 24 hours.
  • a partially crosslinked XLPGI film sample having an isosorbide structure having a thickness of 30 ⁇ m was prepared.
  • the physical properties of the prepared samples were measured and listed in Table 1.
  • step 1) of Example 1 polymethyl methacrylate having a weight average molecular weight of 120,000 g / mol (PMMA; Sigma Aldrich, USA) is used in place of polymethyl methacrylate having a weight average molecular weight of 15,000 g / mol. Except for the rest, XLPGI film samples partially crosslinked with an isosorbide structure having a thickness of 30 ⁇ m were prepared in the same process.
  • Example 1 of Example 1 Except for using butylamine (hereinafter, BA; Sigma Aldrich, USA) in place of isopropylamine (IPA) in Example 1 of Example 1, a polyglutalimide film sample was prepared in the same process. .
  • BA butylamine
  • IPA isopropylamine
  • the second mixed solution was prepared by further adding 0.115 g (0.0008 mol) of isosorbide diamine to the mixed solution including partially crosslinked XLPGI prepared in Step 1) of Example 1 to Example 8, respectively.
  • a polyglutalimide (XLPGI) film sample was prepared by crosslinking the second mixed solution with an isosorbide structure having a thickness of 30 ⁇ m through an injection machine at 330 ° C.
  • Example 1 Except for using the polymethyl methacrylate having a weight average molecular weight of 10,000g / mol in place of the polymethyl methacrylate having a weight average molecular weight of 15,000g / mol in step 1) of Example 1 the rest are the same Polyglutalimide film samples were prepared by the procedure.
  • Example 1 Except for using a polymethyl methacrylate having a weight average molecular weight of 400,000 g / mol in place of the polymethyl methacrylate having a weight average molecular weight of 15,000 g / mol in step 1) of Example 1 A polyglutarimide film was prepared by the procedure.
  • Example 1 PMMA Diamine Compound (Content) Amine compound (content) Solvent (usage) Mw content
  • Example 1 15,000 4 g ISBDA 0.028 g IPA 9.45 g 10 g of toluene
  • Example 2 120,000
  • Example 3 15,000 BA 9.45 g
  • Example 4 120,000
  • Example 5 15,000 ISBDA 0.0575 g IPA 9.45 g
  • Example 6 120,000
  • Example 7 15,000 BA 9.45 g
  • Example 8 120,000
  • Example 9 15,000 4 g ISBDA 0.143 g (0.028 + 0.115) IPA 9.45 g
  • Example 10 120,000
  • Example 11 15,000 BA 9.45 g
  • Example 12 120,000
  • Example 13 15,000 ISBDA 0.1725 g (0.0575 + 0.115) IPA 9.45 g
  • Example 14 120,000
  • Example 15 15,000 BA 9.45 g
  • Example 16 120,000 Comparative Example 1 1,000 4 g ISBDA 0.028 g IPA 9.45 g Comparative Example 2 400,000
  • Examples 1 to 16 of the present invention shows that the gelled polyglutarimide (XLPGI) is not produced on the crosslinked solution, and according to the embodiment of the present invention through the above results.
  • the crosslinked polyglutarimide (XLPGI) produced is partially crosslinked without excessive crosslinking reaction and uniformly crosslinked, so that crosslinked polyglutalimide (XLPGI) is prepared by dissolving in a solvent to enable secondary processing. It can be confirmed.
  • the comparative example of the present invention the result of the formation of the partially or fully gelled XLPGI in the solution, it can be seen that the cross-linking reaction in the resulting XLPGI occurs unevenly.
  • the polyglutalimide film samples of Examples 1 to 16 of the present invention have a glass transition temperature of 138.32 to 153.72 °C, it can be seen that the glass transition temperature is up to 47 °C compared to the film sample of the comparative example, through this general Compared with the case of using a diamine compound, it turns out that the heat resistance of the polyglutarimide manufactured by using the diamine compound which has the isosorbide mother nucleus of this invention can be improved effectively.
  • the existing polymethyl methacrylate through the polyglutarimide prepared according to Examples 1 to 16 of the present invention It can be seen that the low heat resistance of the acrylate can be effectively improved, and thus it can maintain a stable state even at high temperatures.
  • the polyglutarimide of the comparative example is dried after casting. Due to the cracking phenomenon in the process, it is impossible to produce a film, and also the polyglutarimide of the comparative example may be colored and thus, it may be confirmed that the production of a transparent film is impossible.
  • the low-molecular-weight PMMA is included through a contrast between the polyglutalimide film sample of Example 1 present in the upper right side of FIG. 1 and the polyglutarimide film sample of Comparative Example 1 present in the upper right side of FIG. 2.

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  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

La présente invention concerne un polyglutarimide réticulé contenant de l'isosorbide et son procédé de production. Le polyglutarimide réticulé contenant de l'isosorbide selon la présente invention comprend de l'isosorbide comme agent de réticulation qui affiche des effets améliorés de transparence et de dureté de surface par rapport au polyglutarimide, et présente non seulement d'excellentes propriétés optiques, mais également des propriétés de résistance à la chaleur et des propriétés physiques et mécaniques améliorées de façon significative, de telle sorte que le polyglutarimide réticulé contenant de l'isosorbide peut être produit en tant que matériau de formage, par exemple pour un élément optique d'affichage et un élément de circuit électrique/électronique.
PCT/KR2016/012690 2015-11-05 2016-11-04 Polyglutarimide réticulé contenant de l'isosorbide, et son procédé de production WO2017078478A1 (fr)

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KR1020150154971A KR102323832B1 (ko) 2015-11-05 2015-11-05 이소소르비드를 포함하는 가교된 폴리글루타르이미드 및 이의 제조방법
KR10-2015-0154971 2015-11-05

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WO2017078478A1 true WO2017078478A1 (fr) 2017-05-11

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR870002178A (ko) * 1985-08-27 1987-03-30 윌리엄 이. 램버트 3세 이미드 중합체
US20020021883A1 (en) * 1999-08-26 2002-02-21 Takeshi Koyano Optical waveguide made of polymer material and a method of fabricating the same
US20040127057A1 (en) * 2002-12-25 2004-07-01 Tdk Corporation Method for fabricating a patterned thin film and a micro device
CN1616462A (zh) * 2004-09-29 2005-05-18 清华大学 含有二脱水已糖醇单元的二胺单体及其制备方法
KR20130140771A (ko) * 2011-02-21 2013-12-24 가부시키가이샤 가네카 아크릴계 수지 필름

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR870002178A (ko) * 1985-08-27 1987-03-30 윌리엄 이. 램버트 3세 이미드 중합체
US20020021883A1 (en) * 1999-08-26 2002-02-21 Takeshi Koyano Optical waveguide made of polymer material and a method of fabricating the same
US20040127057A1 (en) * 2002-12-25 2004-07-01 Tdk Corporation Method for fabricating a patterned thin film and a micro device
CN1616462A (zh) * 2004-09-29 2005-05-18 清华大学 含有二脱水已糖醇单元的二胺单体及其制备方法
KR20130140771A (ko) * 2011-02-21 2013-12-24 가부시키가이샤 가네카 아크릴계 수지 필름

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KR102323832B1 (ko) 2021-11-09

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