WO2006054410A1 - Procédé servant à produire une résine d'imide, résine d'imide obtenue par un tel procédé et corps moulé en résine d'imide - Google Patents
Procédé servant à produire une résine d'imide, résine d'imide obtenue par un tel procédé et corps moulé en résine d'imide Download PDFInfo
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- WO2006054410A1 WO2006054410A1 PCT/JP2005/019002 JP2005019002W WO2006054410A1 WO 2006054410 A1 WO2006054410 A1 WO 2006054410A1 JP 2005019002 W JP2005019002 W JP 2005019002W WO 2006054410 A1 WO2006054410 A1 WO 2006054410A1
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- imide resin
- carbon atoms
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- resin
- imide
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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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/48—Isomerisation; Cyclisation
Definitions
- the present invention relates to an imide resin, a imide resin, and an imide resin obtained by the method of manufacturing the imide resin.
- polymethyl methacrylate which is representative, has better moldability and caloric properties than glass, is difficult to break, is lightweight, and is inexpensive.
- the development to etc. is examined, and a part is put to practical use.
- the application range of acrylic resin may be limited in applications that require high heat resistance, which is generally poor in heat resistance.
- Patent Document 1 Japanese Patent Laid-Open No. 6-240017
- Patent Document 2 JP-A-6-256537
- An object of the present invention is to provide a method for producing an imide resin that reduces imidii-derived foreign matters, and further to provide an imide resin and an imide-resin-molded product in which foreign substances derived from imidi are reduced. .
- the present invention provides an imide resin and an imide resin molded body formed by using the above production method.
- an imide resin and an imide resin molded product in which foreign substances derived from imido resin are reduced. Further, these imide resin and imide resin molded bodies can be used for optical applications, for example, where the demand for reducing foreign matters is increasing.
- the present invention relates to a method for producing an imide resin characterized by treating an (meth) acrylate ester resin with an imidizing agent in the presence of a heat stabilizer.
- the total number of imidized foreign substances contained in a molded body of 210mm, width 300mm and thickness 3mm is 100.
- the present invention relates to a method for producing imide resin having less than one.
- foreign substances in the resin include those mixed from the environment, those generated during the molding process, those generated during the synthesis of the resin (for example, scale), and the like.
- imidization-derived foreign matters foreign matters generated in the imidation reaction
- the imido-derived foreign material here is a component that is different from the surrounding imide resin that occurs during the imidization reaction, and the shape is not particularly limited, but the foreign material has a long side of 10 m or more. To tell. These can be observed with an optical microscope, for example, many of them appear yellow or colorless and transparent.
- (meth) acrylic acid ester-based resins are obtained by copolymerization of acrylic acid esters such as methyl acrylate in order to suppress the dibbing reaction caused by high-temperature heating.
- acrylic acid esters such as methyl acrylate
- conditions such as the reaction temperature being high and the presence of amines affect the tertiary hydrogen of the main chain of (meth) acrylic acid esters and the carbon radical. Will occur.
- This carbon radical can be the starting point, and it can be considered that a heterogeneous resin is generated due to main chain cleavage or intermolecular coupling reaction. It is considered that a component different from the imide resin produced in this way becomes a foreign substance derived from imidization.
- the foreign material in the resin so that the foreign material does not become a fatal defect for example, the foreign material force derived from the imido resin, for example, longitudinal
- the number is 100 or less. 50 or less is more preferable, and 20 or less is preferable.
- the imide resin of the present invention can be produced by various methods as long as it is a method of treating an (meth) acrylate ester resin with an imidizing agent in the presence of a heat stabilizer. It can be obtained by adding an imidizing agent to a molten acrylic resin using an extruder.
- the imidizing agent used in the present invention is not particularly limited as long as it can imidize a (meth) acrylic ester-based resin.
- a (meth) acrylic ester-based resin For example, methylamine, ethylamine, n-propylamine, i-propylamine, n -Aliphatic hydrocarbon group-containing amines such as butyramine, i-butylamine, tert-butylamine, n-hexylamine, aniline, toluidine, trichloro
- aromatic hydrocarbon group-containing amines such as roamirin
- alicyclic hydrocarbon group-containing amines such as cyclohexylamine.
- urea compounds that generate these amines by heating such as urea, 1,3 dimethylurea, 1,3-jetylurea, and 1,3 dipropylurea can also be used.
- these imidizing agents methylamine is preferable from the viewpoint of cost and physical properties.
- the amount of the imidizing agent added in the production of the imide resin of the present invention can be determined as appropriate so as to reach the imidity ratio necessary for expressing the necessary physical properties.
- the reaction temperature is 180 to 320 ° C in order to promote imidization and to suppress decomposition and coloring of the resin due to excessive heat history. It is preferable to perform in the range. Further, 180-320 ° C force S is preferable, and 200-280 ° C is particularly preferable.
- the heat stabilizer used in the present invention is not particularly limited as long as it can suppress the occurrence of imidation-derived foreign matters, but it is not limited to a hindered phenol compound, a rataton compound, a phosphorus compound, a hindered amine compound, and A compound having at least one compound selected from thioether compounds is preferred.
- the hindered phenolic compound is not particularly limited as long as it is a compound containing a phenolic hydroxyl group.
- triethylene glycol bis [3- (3-tert-butyl 5-methyl 4-hydroxyphenol- Propionate], pentaerythrityl tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenol) propionate], octadecyl-3- (3,5 di-tert-butyl-4-hydroxyphenol) ) Propionate, 1, 3, 5 —trimethyl 2, 4,6 tris (3,5 di-t-butyl 4-hydroxybenzyl) benzene, 3, 9 bis [2- ⁇ 3 -— (3-t-butyl-4-hydroxy — 5—Methylphenol) pio-loxy ⁇ -1, 1-dimethylethyl] —2, 4, 8, 10—tetraoxaspiro [5.5] undecane, 2—t-butyl—6— (3'— t-But
- the ratatone compound is not particularly limited as long as it is a compound containing a rataton ring.
- 5, 7-di-tert-butyl 3- (3,4-dimethylphenol) 3H-benzofuran 2 — I can mention it.
- the phosphorous compound is not particularly limited as long as it is phosphoric acid and alkyl esters thereof, and examples thereof include tris (2,4-di-t-butylphenol) phosphite, tetrakis (2,4 dione t-Butylphenol) 1, 4, 4'-Bipherene phosphite, trisnolfalphosphite, bis (2,4 di-tert-butylphenol) pentaerythritol diphosphite, distearyl pentaerythritol di A phosphite etc. can be mentioned.
- the hindered amine compound is not particularly limited as long as it is a compound containing a 2, 2, 6, 6, -tetramethyl-4-piperidyl group.
- the thioether compound is not particularly limited as long as it is a compound containing a thioether group.
- the amount of the heat stabilizer added to the (meth) acrylate ester-based resin is preferably 0.01 to 5 parts by weight with respect to 100 parts by weight of the (meth) acrylate-based resin resin.
- the addition amount 0.01 parts by weight or more, the effect of suppressing the occurrence of imido soot-derived foreign matter is likely to occur.
- the addition amount is 5 parts by weight or less, the transparency of the imide resin can be easily obtained, and it is suitable for applications requiring transparency.
- a batch type reaction vessel pressure vessel or the like may be used.
- twin-screw extruder is preferable as an extruder that can promote mixing of an imidizing agent or a ring closure accelerator with a raw material polymer.
- twin-screw extruders non-matching type co-rotating type, mating type co-rotating type, non-matching type counter-rotating type, mating type counter-rotating type, etc.
- the counter-rotating co-rotating type is preferable because high-speed rotation is possible and mixing of an imidizing agent or a ring-closing accelerator to be used if necessary can be accelerated.
- These extruders may be used alone or connected in series.
- the extruder is equipped with a vent port that can be depressurized below atmospheric pressure in order to remove unreacted imidizing agent or ring closure accelerator and by-products.
- a high-viscosity reactor such as a horizontal biaxial reactor such as Bipolak manufactured by Sumitomo Heavy Industries, Ltd. or a vertical biaxial agitation tank such as Super Blend is also preferred. Can be used properly.
- the production method of the imide resin of the present invention is carried out in a batch type reaction vessel (pressure vessel), the raw material polymer can be melted by heating and stirred, and an imidizing agent or a ring closure accelerator can be added. If it is, there is no particular limitation, but the polymer viscosity may increase with the progress of the reaction, and those with good stirring efficiency are preferable.
- a stirring tank Max blend manufactured by Sumitomo Heavy Industries, Ltd. can be exemplified.
- the method for producing an imide resin according to the present invention includes the following general formulas (1) and (2) and, if necessary, the production of an imide resin containing a repeating unit represented by the following general formula (3). In particular, it can be used particularly preferably.
- R 1 and R 2 each independently represent hydrogen or an alkyl group having 1 to 8 carbon atoms;
- R 3 represents an alkyl group having 1 to 18 carbon atoms or 3 to 12 carbon atoms;
- a cycloalkyl group or a substituent containing an aromatic ring having 5 to 15 carbon atoms, hereinafter, this unit may be referred to as a dartalimide unit.
- R 4 and R 5 each independently represents hydrogen or an alkyl group having 1 to 8 carbon atoms;
- R 6 represents an alkyl group having 1 to 18 carbon atoms or an alkyl group having 3 to 12 carbon atoms;
- a cycloalkyl group or a substituent containing an aromatic ring having 5 to 15 carbon atoms, hereinafter, this unit may be referred to as an acrylate ester or methacrylate ester unit.
- R 7 represents hydrogen or an alkyl group having 1 to 8 carbon atoms
- R 8 represents an aryl group having 6 to 10 carbon atoms.
- the general formula (3) is represented by an aromatic butyl group. . sometimes referred to as a unit) in particular, the imide ⁇ orientation birefringence -. 0. 1 X 10- 3 ⁇ 0 1 X 10- 3 and it is preferred arbitrariness.
- the dartalimide unit can be easily formed by treating an (meth) acrylic ester-based resin with an imidizing agent.
- R 2 is hydrogen or a methyl group
- R 3 is hydrogen or a methyl group. It is particularly preferred if R 1 is a methyl group, R 2 is hydrogen and R 3 is a methyl group.
- the glutarimide unit may be of a single type. A plurality of different types of R 3 may be included.
- Examples of the raw material monomer that produces an acrylic ester or methacrylic ester unit as a residue include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meta ) Atarylate, t-butyl (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate and the like.
- acid anhydrides such as maleic anhydride or half esters of them with linear or branched alcohols having 1 to 20 carbon atoms; acrylic acid, methacrylic acid, maleic acid, maleic anhydride, itaconic acid, itaconic anhydride A, ⁇ -ethylenically unsaturated carboxylic acids such as crotonic acid, fumaric acid and citraconic acid can also be imidized and used in the present invention. Of these, methyl methacrylate is particularly preferred.
- These acrylic acid ester units or methacrylic acid ester units may be of a single type, or may include a plurality of types in which R 4 , R 5 , and R 6 are different.
- the third structural unit contained in the preferred imide resin according to the present invention as required is represented by the following general formula (3), and is generally called an aromatic bulule unit. Many. [0042] [Chemical 7]
- R 7 represents hydrogen or an alkyl group having 1 to 8 carbon atoms
- R 8 represents an aryl group having 6 to 10 carbon atoms.
- Preferred aromatic vinyl structural units include styrene, methyl styrene and the like. Of these, styrene is particularly preferred.
- the content of Darutaruimido unit represented by the general formula (1) is not particularly restricted in the imide ⁇ , and orientation birefringence -0. 1 X 10- 3 ⁇ 0. 1 X 10- 3 Therefore, the range of 1 to 30% by weight is particularly preferable, and 3 to 25% by weight is more preferable. If Darutaruimido units is less than 1 wt%, the orientation birefringence of the resulting imide ⁇ is - smaller than 0. 1 X 10- 3, the orientation birefringence of the imide ⁇ that if more than 30 wt% is obtained 0 > 1 X 10—greater than 3, limiting its use in applications that do not want to cause orientation birefringence.
- the imide resin of the present invention may further include a copolymer having a fourth structural unit different from the general formulas (1), (2), and (3). Don't hesitate.
- the fourth building block copolymerized -tolyl monomers such as acrylonitrile methacrylo-tolyl, maleimide monomers such as maleimide, N-methylmaleimide, N-phenylmaleimide, N-cyclohexylmaleimide These structural units can be used. These may be copolymerized in a specific form, such as graft copolymerization, which may be directly copolymerized in thermoplastic resin.
- the (meth) acrylate ester resin that can be used in the present invention is not particularly limited as long as an imidization reaction is possible, and may be a linear (linear) polymer or a block polymer. It may be a core-shell polymer, a branched polymer, a ladder polymer, or a crosslinked polymer. Block polymers are A-B, A-B-C, A-B-A, or other V, even a misaligned type block polymer! / There is no problem even if the core-shell polymer is composed of only one core and only one shell, or each layer is multi-layered.
- the imide resin of the present invention preferably has substantially no orientation birefringence, particularly considering use in optical applications.
- Oriented birefringence refers to birefringence that develops when stretched at a predetermined temperature and a predetermined draw ratio. In the present specification, unless otherwise specified, it means birefringence that develops when stretched 100% at a glass transition temperature of imide resin + 5 ° C.
- the orientation birefringence is the product of the intrinsic birefringence derived from the polymer structure and the orientation distribution function derived from the molecular orientation state, and the refractive index (nx) in the stretching axis direction and the axial bending perpendicular thereto. It is a value obtained by dividing the phase difference Re (nm), which is defined by the following formula 1 and measured by the phase difference meter, as shown in the following formula 2, by the thickness d ( ⁇ m).
- the orientation birefringence is the difference between the refractive index (nx) in the stretching axis direction and the refractive index (ny) in the axial direction perpendicular thereto, so if nx is greater than ny, a positive value is obtained. Conversely, if nx is less than ny, it indicates a negative value.
- orientation birefringence in 0. 1 X 10- 3 ⁇ 0. 1 X 10- 3 it is preferably an instrument 0. 0 1 X 10- 3 ⁇ 0. 01 X 10- 3 More preferably.
- orientation birefringence is out of the above range, it may cause birefringence during molding processing or a stable optical characteristic may not be obtained due to environmental changes.
- the glass transition temperature of the thermoplastic resin is preferably 110 ° C or higher, and can be suitably used in applications requiring heat resistance.
- the imide resin has a viscosity at the time of melting while ensuring the mechanical strength when the molded article preferably has a weight average molecular weight of 1 ⁇ 10 4 3 ⁇ 4V and 5 ⁇ 10 5. Easy to mold It can be an enclosure.
- the imide resin of the present invention can exhibit characteristics such as high tensile strength and bending strength, solvent resistance, thermal stability, good optical properties, and weather resistance by appropriately setting the composition and composition ratio. Can be made.
- thermoplastic resin of the present invention If necessary, other thermoplastic resin can be added to the thermoplastic resin of the present invention.
- Imido resin alone or blends with other thermoplastic polymers can be produced by various plastic calorific methods such as injection molding, melt extrusion film molding, blow molding, compression molding, and spinning molding. Can be processed. Further, the imide resin obtained in the present invention such as methylene chloride can be dissolved in a solvent that dissolves, and the casting method using the resulting polymer solution can be molded by spin coating.
- antioxidants In the molding process, generally used antioxidants, heat stabilizers, plasticizers, lubricants, ultraviolet absorbers, antistatic agents, colorants, antishrink agents, and the like are impaired. You may add it as long as it is not.
- Molded articles obtained from the imide resin of the present invention include, for example, video fields such as cameras, VTRs, projector lenses, viewfinders, filters, prisms, and Fresnel lenses, CD players, DVD players, and MD players.
- video fields such as cameras, VTRs, projector lenses, viewfinders, filters, prisms, and Fresnel lenses, CD players, DVD players, and MD players.
- Lens field such as pick-up lens for optical disk such as, optical recording field for optical disk such as CD player, DVD player, MD player, liquid crystal light guide plate, liquid crystal display film such as polarizer protective film and retardation film, surface Information equipment field such as protective film, optical communication field such as optical fiber, optical switch, optical connector, vehicle field such as automobile headlight, tail lamp lens, inner lens, instrument cover, sunroof, eyeglasses contact lens, internal vision Environmental lenses and medical supplies that require sterilization Medical equipment field, road translucent plate, pair glass lens, lighting window and carport, lighting lens and lighting cover, building material sizing, building materials field, microwave cooking container (tableware), home appliances It can be used for housing, toys, sunglasses, stationery, etc.
- the imidity ratio (Im%) is obtained by the following formula 3.
- the imido ratio refers to the ratio of imide carbo- yl groups in all carbonyl groups.
- I m% A bs imide / (A bs ester + A bs (S
- a test piece having a size of 210 mm in length and 300 mm in width was cut out from the obtained sheet-like molded product having a thickness of 3 mm. While this test piece was irradiated with light from a desk stand (National SQ948H, Fluorescent Lamp 27W) in a dark room, the periphery of the visually observed foreign matter was checked with an oil pen. Subsequently, the checked foreign matter was observed with a transmission optical microscope (digital microscope (VH-Z75), manufactured by Keyence Corporation) with a magnification of 50 times. The above observation was performed on both sides of the sheet-like molded body, and the total number and types of foreign matters were measured.
- the color was determined based on the color of the foreign substances when observed with a transmission optical microscope with a magnification of 50 times or more. It was judged that the imidation-derived foreign substances looked yellow and colorless and transparent, and the general foreign substances looked other colors.
- a differential scanning calorimeter (DSC, DSC-50 manufactured by Shimadzu Corporation) was used and measured under a nitrogen atmosphere at a heating rate of 20 ° C. Zmin and determined by the midpoint method.
- a test piece having a length of 50 mm and a width of 50 mm was cut out from the obtained sheet-like molded product having a thickness of 3 mm.
- the test piece was measured according to JIS K7105 at a temperature of 23 ° C ⁇ 2 ° C and a humidity of 50% ⁇ 5% using a turbidimeter 300A manufactured by Nippon Denshoku Industries Co., Ltd. [0067] (5) Turbidity
- the test piece obtained in (4) was adjusted to a temperature of 23 ° C ⁇ 2 ° C, a humidity of 50% and 5%! /, According to JIS K7136. It was measured.
- the product was dissolved in methylene chloride (resin concentration 25 wt%), coated on a PET film, and dried to produce a 80 m thick film.
- a sample having a width of 50 mm and a length of 150 mm was cut from this film, and a stretched film was prepared at a stretch ratio of 100% and at a temperature 5 ° C higher than the glass transition temperature.
- a 3.5 cm ⁇ 3.5 cm test piece was cut out from the center in the TD direction of this uniaxially double stretched film.
- phase difference of this test piece was measured using a KOBRA-21ADH manufactured by Oji Scientific Instruments at a temperature of 23 ⁇ 2 ° C and humidity of 50 ⁇ 5% at a wavelength of 590 nm and an incident angle of 0 °.
- the value obtained by dividing the phase difference by the thickness of the test piece measured using a Mitutoyo Digimatic Indicator was defined as orientation birefringence.
- the extruder used was a counter-rotating, co-rotating twin screw extruder with a diameter of 15 mm.
- the set temperature of each temperature control zone of the extruder was 230 ° C and the screw speed was 150 rpm.
- the heat stabilizer from 0.2 to 0.2 parts by weight of dry blended resin is supplied at lkgZhr, melted and filled with the kneading block, and then 5 parts by weight of monomethyla Min was injected.
- a seal ring and a reverse fly were put to fill the resin.
- By-products and excess methylamine after the reaction were removed by reducing the Ventro pressure to -0.08 MPa.
- the resin that came out as a strand from the die provided at the exit of the extruder was cooled in a water tank and then pelletized with a pelletizer.
- the imido resin ratio of the obtained imide resin was 22%, and the glass transition temperature was 123 ° C.
- the resulting imide resin had an imido ratio of 20% and a glass transition temperature of 121 ° C.
- the imide resin obtained had an imido ratio of 20% and a glass transition temperature of 123 ° C.
- the imido resin ratio of the obtained imide resin was 20%, and the glass transition temperature was 121 ° C.
- the imido resin ratio of the obtained imide resin was 18%, and the glass transition temperature was 116 ° C.
- the raw material of the resin is a commercially available methyl methacrylate-styrene copolymer (Sumipex HS manufactured by Sumitomo Chemical Co., Ltd.) and methylamine is 40 parts by weight with respect to the resin. 7 to go to.
- the imido ratio of the obtained imide resin was 70%, and the glass transition temperature was 154 ° C.
- the imido resin ratio of the obtained imide resin was 72%, and the glass transition temperature was 157 ° C.
- a sheet-like molded product having a thickness of 3 mm was obtained in the same manner as in Example 1 except that the imide resin obtained in Production Example 2 was used.
- Table 1 shows the foreign matter inspection, total light transmittance, turbidity, and orientation birefringence of the obtained molded body.
- a sheet-like molded product having a thickness of 3 mm was obtained in the same manner as in Example 1 except that the imide resin obtained in Production Example 3 was used.
- Table 1 shows the foreign matter inspection, total light transmittance, turbidity, and orientation birefringence of the obtained molded body.
- a sheet-like molded article having a thickness of 3 mm was obtained in the same manner as in Example 1 except that the imide resin obtained in Comparative Production Example 1 was used.
- Table 1 shows the foreign matter inspection, total light transmittance, turbidity, and orientation birefringence of the obtained molded body.
- Example 5 A sheet-like molded article having a thickness of 3 mm was obtained in the same manner as in Example 1 except that the imide resin obtained in Production Example 4 was used. Table 1 shows the foreign matter inspection, total light transmittance, turbidity, and orientation birefringence of the obtained molded body. [0092] (Example 5)
- a sheet-like molded product having a thickness of 3 mm was obtained in the same manner as in Example 1 except that the imide resin obtained in Production Example 5 was used.
- Table 1 shows the foreign matter inspection, total light transmittance, turbidity, and orientation birefringence of the obtained molded body.
- a sheet-like molded article having a thickness of 3 mm was obtained in the same manner as in Example 1 except that the imide resin obtained in Production Example 6 was used.
- Table 1 shows the foreign matter inspection, total light transmittance, turbidity, and orientation birefringence of the obtained molded body.
- a sheet-like molded product having a thickness of 3 mm was obtained in the same manner as in Example 1 except that the imide resin obtained in Production Example 7 was used.
- Table 1 shows the foreign matter inspection, total light transmittance, turbidity, and orientation birefringence of the obtained molded body.
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Priority Applications (1)
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JP2006544813A JPWO2006054410A1 (ja) | 2004-11-19 | 2005-10-17 | イミド樹脂の製造方法、およびこれにより得られるイミド樹脂、イミド樹脂成形体 |
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JP2004336781 | 2004-11-19 | ||
JP2004-336781 | 2004-11-19 |
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WO2006054410A1 true WO2006054410A1 (fr) | 2006-05-26 |
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PCT/JP2005/019002 WO2006054410A1 (fr) | 2004-11-19 | 2005-10-17 | Procédé servant à produire une résine d'imide, résine d'imide obtenue par un tel procédé et corps moulé en résine d'imide |
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JP (1) | JPWO2006054410A1 (fr) |
TW (1) | TW200631972A (fr) |
WO (1) | WO2006054410A1 (fr) |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60177034A (ja) * | 1984-02-21 | 1985-09-11 | Mitsubishi Rayon Co Ltd | 耐摩耗性に優れた耐熱性樹脂成形品およびその製造法 |
JPS60210606A (ja) * | 1984-04-03 | 1985-10-23 | Mitsubishi Rayon Co Ltd | 透明性および耐熱性に優れたメタクリルイミド含有重合体の製造方法 |
JPS624704A (ja) * | 1985-07-01 | 1987-01-10 | Asahi Chem Ind Co Ltd | 六員環イミド基含有重合体の製造方法 |
JPH02178309A (ja) * | 1988-12-29 | 1990-07-11 | Mitsubishi Rayon Co Ltd | メタクリルイミド含有重合体 |
JPH04149209A (ja) * | 1990-10-15 | 1992-05-22 | Monsant Kasei Kk | イミド化共重合体樹脂組成物の製造方法 |
JPH07138318A (ja) * | 1993-11-19 | 1995-05-30 | Tosoh Corp | 共重合体の製造方法 |
JPH0812722A (ja) * | 1994-06-28 | 1996-01-16 | Ube Ind Ltd | 耐熱性樹脂の製造法 |
-
2005
- 2005-10-17 JP JP2006544813A patent/JPWO2006054410A1/ja active Pending
- 2005-10-17 WO PCT/JP2005/019002 patent/WO2006054410A1/fr active Application Filing
- 2005-11-16 TW TW094140281A patent/TW200631972A/zh unknown
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60177034A (ja) * | 1984-02-21 | 1985-09-11 | Mitsubishi Rayon Co Ltd | 耐摩耗性に優れた耐熱性樹脂成形品およびその製造法 |
JPS60210606A (ja) * | 1984-04-03 | 1985-10-23 | Mitsubishi Rayon Co Ltd | 透明性および耐熱性に優れたメタクリルイミド含有重合体の製造方法 |
JPS624704A (ja) * | 1985-07-01 | 1987-01-10 | Asahi Chem Ind Co Ltd | 六員環イミド基含有重合体の製造方法 |
JPH02178309A (ja) * | 1988-12-29 | 1990-07-11 | Mitsubishi Rayon Co Ltd | メタクリルイミド含有重合体 |
JPH04149209A (ja) * | 1990-10-15 | 1992-05-22 | Monsant Kasei Kk | イミド化共重合体樹脂組成物の製造方法 |
JPH07138318A (ja) * | 1993-11-19 | 1995-05-30 | Tosoh Corp | 共重合体の製造方法 |
JPH0812722A (ja) * | 1994-06-28 | 1996-01-16 | Ube Ind Ltd | 耐熱性樹脂の製造法 |
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JPWO2006054410A1 (ja) | 2008-05-29 |
TW200631972A (en) | 2006-09-16 |
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