WO2024029515A1 - Composition de résine, film, feuille polarisante, procédé de production de composition de résine et procédé de fabrication de film - Google Patents
Composition de résine, film, feuille polarisante, procédé de production de composition de résine et procédé de fabrication de film Download PDFInfo
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- WO2024029515A1 WO2024029515A1 PCT/JP2023/028063 JP2023028063W WO2024029515A1 WO 2024029515 A1 WO2024029515 A1 WO 2024029515A1 JP 2023028063 W JP2023028063 W JP 2023028063W WO 2024029515 A1 WO2024029515 A1 WO 2024029515A1
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- film
- resin composition
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- cyclic ether
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- 239000011342 resin composition Substances 0.000 title claims abstract description 79
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 24
- 229920006122 polyamide resin Polymers 0.000 claims abstract description 65
- 150000004292 cyclic ethers Chemical group 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 229920005989 resin Polymers 0.000 claims description 20
- 239000011347 resin Substances 0.000 claims description 20
- 230000001681 protective effect Effects 0.000 claims description 16
- 239000004953 Aliphatic polyamide Substances 0.000 claims description 9
- 229920003231 aliphatic polyamide Polymers 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 238000004898 kneading Methods 0.000 claims description 7
- 125000003566 oxetanyl group Chemical group 0.000 claims description 7
- 239000004593 Epoxy Substances 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 6
- 238000000465 moulding Methods 0.000 abstract description 4
- -1 cyclic ether compound Chemical class 0.000 description 46
- 125000004432 carbon atom Chemical group C* 0.000 description 29
- 239000000178 monomer Substances 0.000 description 15
- 239000002994 raw material Substances 0.000 description 13
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 12
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 10
- 150000004985 diamines Chemical class 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 238000010186 staining Methods 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 239000004372 Polyvinyl alcohol Substances 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 229920002451 polyvinyl alcohol Polymers 0.000 description 8
- 125000002723 alicyclic group Chemical group 0.000 description 6
- 239000004959 Rilsan Substances 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 229920006020 amorphous polyamide Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 235000011037 adipic acid Nutrition 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 3
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 3
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 3
- OXIKYYJDTWKERT-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCC(CN)CC1 OXIKYYJDTWKERT-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000005022 packaging material Substances 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- BIDWUUDRRVHZLQ-UHFFFAOYSA-N 3-ethyl-3-(2-ethylhexoxymethyl)oxetane Chemical compound CCCCC(CC)COCC1(CC)COC1 BIDWUUDRRVHZLQ-UHFFFAOYSA-N 0.000 description 1
- FNYWFRSQRHGKJT-UHFFFAOYSA-N 3-ethyl-3-[(3-ethyloxetan-3-yl)methoxymethyl]oxetane Chemical compound C1OCC1(CC)COCC1(CC)COC1 FNYWFRSQRHGKJT-UHFFFAOYSA-N 0.000 description 1
- LMIOYAVXLAOXJI-UHFFFAOYSA-N 3-ethyl-3-[[4-[(3-ethyloxetan-3-yl)methoxymethyl]phenyl]methoxymethyl]oxetane Chemical compound C=1C=C(COCC2(CC)COC2)C=CC=1COCC1(CC)COC1 LMIOYAVXLAOXJI-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 1
- 125000004427 diamine group Chemical group 0.000 description 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 239000005003 food packaging material Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229920006012 semi-aromatic polyamide Polymers 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
Classifications
-
- 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
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1515—Three-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1525—Four-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
Definitions
- the present invention relates to a resin composition, a film, a polarizing sheet, a method for producing a resin composition, and a method for producing a film.
- the present invention relates to a resin composition containing a polyamide resin as a main component.
- Polyamide resins have excellent mechanical properties such as rigidity and strength, and heat resistance, so they are used in a wide variety of applications, including electrical and electronic equipment, automobiles, machinery, and building materials (Patent Documents 1 to 3).
- polyamide resins are used in a wide variety of fields, but they generally have poor transparency and have not been used for applications that require transparency. Under such circumstances, the present inventors have investigated the use of polyamide resins in transparent applications such as protective films for polarizing films. However, it has been found that when polyamide resin is molded into a film, the molding roll becomes stained and foreign matter is formed. Such roll dirt and foreign matter have not been a problem in the past for transparent materials and transparent films such as food packaging materials that used polyamide resin, but in applications that require extremely high transparency such as sunglasses. It turned out to be a problem.
- the present invention aims to solve such problems, and provides a resin composition that can suppress the formation of dirt on the forming roll even when molded into a film, and that is less likely to cause foreign matter to form on the film.
- Another object of the present invention is to provide a method for producing a film, a polarizing sheet, a resin composition, and a method for producing a film.
- ⁇ 3> The resin composition according to ⁇ 1> or ⁇ 2>, wherein the polyamide resin includes an aliphatic polyamide resin.
- the polyamide resin includes an aliphatic polyamide resin.
- ⁇ 4> The resin composition according to any one of ⁇ 1> to ⁇ 3>, wherein the compound having 1 to 3 cyclic ether structures in one molecule contains an epoxy ring and/or an oxetane ring.
- ⁇ 5> A compound in which the filler content in the resin composition is 0 to 10% by mass, the polyamide resin contains an aliphatic polyamide resin, and has 1 to 3 cyclic ether structures in one molecule, The resin composition according to ⁇ 1>, containing an epoxy ring and/or an oxetane ring.
- ⁇ 6> The resin composition according to any one of ⁇ 1> to ⁇ 5>, which is used as a protective film for a polarizing sheet.
- ⁇ 7> A film formed from the resin composition according to any one of ⁇ 1> to ⁇ 6>.
- ⁇ 8> The film according to ⁇ 7>, having a thickness of 100 to 1000 ⁇ m.
- ⁇ 9> The film according to ⁇ 7> or ⁇ 8>, which is a protective film for a polarizing sheet.
- ⁇ 10> Comprising a polarizing film and a protective film on at least one surface of the polarizing film, A polarizing sheet, wherein the protective film is the film according to any one of ⁇ 7> to ⁇ 9>.
- ⁇ 11> A method for producing a resin composition, comprising adding 0.05 to 10 parts by mass of a compound having 1 to 3 cyclic ether structures in one molecule to 100 parts by mass of polyamide resin, and melt-kneading the mixture. .
- ⁇ 12> The method for producing a resin composition according to ⁇ 11>, wherein the resin composition has a haze of 10% or less when formed into a 200 ⁇ m thick film.
- ⁇ 13> A method for producing a film, which comprises adding 0.05 to 10 parts by mass of a compound having 1 to 3 cyclic ether structures in one molecule to 100 parts by mass of polyamide resin, and melt-kneading the mixture.
- ⁇ 14> The method for producing a film according to ⁇ 13>, wherein the film has a haze of 10% or less.
- a resin composition that can suppress the formation of stains on a forming roll even when molded into a film, and that prevents foreign matter from forming on the film, as well as a method for manufacturing the film, a polarizing sheet, and a resin composition, and a method for manufacturing the film. method is now available.
- this embodiment a mode for carrying out the present invention (hereinafter simply referred to as “this embodiment”) will be described in detail.
- the present embodiment below is an illustration for explaining the present invention, and the present invention is not limited only to this embodiment.
- " ⁇ " is used to include the numerical values described before and after it as a lower limit value and an upper limit value.
- various physical property values and characteristic values are assumed to be at 23° C. unless otherwise stated.
- the weight average molecular weight and number average molecular weight can be measured according to the description in paragraph 0047 of JP 2018-165298A, the contents of which are incorporated herein.
- film and sheet refer to a generally flat molded body that is thin relative to its length and width, respectively. Further, the “film” and “sheet” in this specification may be a single layer or a multilayer. If the measurement methods, etc. explained in the standards shown in this specification differ from year to year, unless otherwise stated, they shall be based on the standards as of January 1, 2022.
- the resin composition of this embodiment is a resin composition containing 0.05 to 10 parts by mass of a compound having 1 to 3 cyclic ether structures in one molecule based on 100 parts by mass of polyamide resin, and has a thickness of 200 ⁇ m.
- the film is characterized by a haze of 10% or less.
- cyclic ether compound a compound having 1 to 3 cyclic ether structures in one molecule (hereinafter sometimes referred to as a "cyclic ether compound") into the polyamide resin.
- a cyclic ether compound reacts with diamines and aminocarboxylic acids that are raw material monomers, dimers and trimers of raw material monomers, or decomposition products that may be generated when extruding the resin composition into a film.
- diamines and aminocarboxylic acids that are raw material monomers, dimers and trimers of raw material monomers, or decomposition products that may be generated when extruding the resin composition into a film.
- the cyclic ether compound contains a large number of cyclic ether structures, foreign substances will be formed in the film when the cyclic ether compound and the diamine react with each other.
- the generation of foreign substances could be suppressed by setting the number of cyclic ether structures in the cyclic ether compound to three or less. This embodiment will be described below.
- the resin composition of this embodiment includes a polyamide resin.
- the polyamide resin used in this embodiment is not particularly specified as long as it does not depart from the spirit of the present invention, but from the viewpoint of transparency, it is preferably an amorphous polyamide resin.
- the amorphous polyamide resin is a polyamide resin that does not have a clear melting point, and specifically refers to a crystal melting enthalpy ⁇ Hm of less than 5 J/g, preferably 3 J/g or less, and 1 J /g or less is more preferable.
- the crystal melting enthalpy ⁇ Hm is determined by measuring the value during the temperature rising process according to JIS K7121 and K7122, and more specifically, according to the description in paragraph 0101 of Patent No.
- the polyamide resin used in this embodiment may be a semi-aromatic polyamide resin or an aliphatic polyamide resin, but it is preferably an aliphatic polyamide resin, and more preferably an alicyclic polyamide resin. preferable.
- the aliphatic polyamide resin means that preferably 90% by mass or more, more preferably 95% by mass or more, still more preferably 98% by mass or more of the monomers that are raw materials thereof are aliphatic monomers.
- Alicyclic polyamide refers to a polyamide resin containing an alicyclic monomer unit among aliphatic polyamide resins, preferably 10% by mass or more (more preferably 30% by mass or more) of all monomer units constituting the polyamide resin.
- the polyamide resin includes a polyamide resin in which the main component of the raw material monomer (for example, 50% by mass or more, preferably 90% by mass or more) is synthesized from diamine and dicarboxylic acid, and a polyamide resin in which the main component of the raw material monomer is synthesized from aminocarboxylic acid.
- examples include polyamide resins and polyamide resins whose main components as raw material monomers are diamines, dicarboxylic acids, and aminocarboxylic acids.
- the polyamide resin used in this embodiment 90% by mass or more (preferably 95% by mass or more, and 100% by mass or less) of the raw material monomers are preferably synthesized from diamine and dicarboxylic acid.
- roll staining can be particularly effectively suppressed for a resin composition using such a polyamide resin.
- Examples of the diamine unit include linear or branched aliphatic diamines having 4 to 20 carbon atoms and alicyclic diamines having 6 to 25 carbon atoms, with alicyclic diamines having 6 to 25 carbon atoms being preferred.
- the straight chain or branched aliphatic diamine having 4 to 20 carbon atoms is preferably a straight chain aliphatic diamine having 4 to 20 carbon atoms.
- the number of carbon atoms constituting the linear or branched aliphatic diamine having 4 to 20 carbon atoms is preferably 6 or more, preferably 18 or less, more preferably 16 or less, even more preferably 14 or less, and even more preferably 12 or less. Preferably, 10 or less is even more preferable.
- aliphatic diamines having 4 to 20 carbon atoms include 1,6-hexamethylene diamine, 1,7-heptamethylene diamine, 1,8-octamethylene diamine, 1,9-nonamethylene diamine, and 1,10-hexamethylene diamine.
- - Decamethylene diamine is exemplified.
- the number of carbon atoms constituting the alicyclic diamine having 6 to 25 carbon atoms is preferably 6 or more, more preferably 8 or more, and preferably 22 or less, more preferably 20 or less, and even more preferably 18 or less.
- alicyclic diamines having 6 to 25 carbon atoms include 1,3-bisaminomethylcyclohexane, 1,4-bisaminomethylcyclohexane, 4,4'-methylenebis(2-methylcyclohexylamine), and isophoronediamine. is exemplified.
- dicarboxylic acid unit examples include straight chain or branched aliphatic dicarboxylic acids having 4 to 20 carbon atoms, alicyclic dicarboxylic acids having 6 to 25 carbon atoms, and linear or branched aliphatic dicarboxylic acids having 4 to 20 carbon atoms.
- Group dicarboxylic acids are preferred.
- the straight chain or branched aliphatic dicarboxylic acid having 4 to 20 carbon atoms is preferably a straight chain aliphatic dicarboxylic acid having 4 to 20 carbon atoms.
- the number of carbon atoms constituting the linear or branched aliphatic dicarboxylic acid having 4 to 20 carbon atoms is preferably 6 or more, preferably 22 or less, more preferably 20 or less, and even more preferably 18 or less.
- Specific examples of linear or branched aliphatic dicarboxylic acids having 4 to 20 carbon atoms include adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, decanedioic acid, dodecanedioic acid, etc. and sebacic acid are preferred, and sebacic acid is more preferred.
- the number of carbon atoms constituting the alicyclic dicarboxylic acid having 6 to 25 carbon atoms is preferably 6 or more, preferably 18 or less, more preferably 16 or less, even more preferably 14 or less, even more preferably 12 or less, and 10 or less. is even more preferable.
- Specific examples of the alicyclic dicarboxylic acid having 6 to 25 carbon atoms include 1,3-cyclohexanedicarboxylic acid and 1,4-cyclohexanedicarboxylic acid.
- aminocarboxylic acid unit examples include aminocarboxylic acid units having 4 to 20 carbon atoms.
- the aminocarboxylic acid preferably consists of an amino group, a carboxyl group, and an aliphatic group (preferably an alkylene group, more preferably a straight-chain alkylene group).
- the number of carbon atoms constituting the aminocarboxylic acid unit having 4 to 20 carbon atoms is preferably 6 or more, more preferably 8 or more, and is preferably 18 or less, more preferably 16 or less, even more preferably 14 or less, and 13 or less. More preferred.
- a specific example of the aminocarboxylic acid is 11-aminoundecanoic acid.
- Polyamide 11 is exemplified as an example of the polyamide resin used in this embodiment.
- alicyclic diamine units having 6 to 25 carbon atoms and linear aliphatic dicarboxylic acid units having 4 to 20 carbon atoms account for 90% by mass of all monomer units. It is preferable that it accounts for 95% by mass or more, more preferably 95% by mass or more, and may account for 100% by mass.
- a specific example of the polyamide resin used in this embodiment is a polyamide resin obtained from 4,4'-methylenebis(2-methylcyclohexylamine) and sebacic acid.
- polyamide resin used in this embodiment examples include polyamide resins obtained from 1,3-bisaminomethylcyclohexane and/or 1,4-bisaminomethylcyclohexane and adipic acid. Further, other examples of the polyamide resin used in this embodiment include 1,3-bisaminomethylcyclohexane and/or 1,4-bisaminomethylcyclohexane, adipic acid and 1,4-cyclohexanedicarboxylic acid (adipic acid and 1,4-cyclohexanedicarboxylic acid in a molar ratio of preferably 85 to 95:15 to 5).
- a portion of the polyamide resin may be substituted with other monomers (diamine, dicarboxylic acid, aminocarboxylic acid, lactam, etc.).
- the polyamide resin used in this embodiment may be a commercially available product.
- Commercially available products include, for example, "Trogamid CX7323” manufactured by Daicel Evonik Co., Ltd., “Grylamid TR90” manufactured by M Chemie Co., Ltd., and "Rilsan (registered trademark) Clear G350", “Rilsan Clear G850", and “Rilsan Clear” manufactured by Arkema Corporation. G820'' and the like, with “Rilsan Clear G850” being particularly preferred.
- the content of the polyamide resin (preferably amorphous polyamide resin) in the resin composition of the present embodiment is preferably 95% by mass or more, more preferably 96% by mass or more, It is more preferably 97% by mass or more, even more preferably 98% by mass or more, even more preferably 99% by mass or more.
- the upper limit of the content of the polyamide resin (preferably amorphous polyamide resin) in the resin composition of the present embodiment is such that the total amount of the polyamide resin and the cyclic ether compound is 100% by mass.
- the resin composition of this embodiment may contain only one type of polyamide resin (preferably amorphous polyamide resin), or may contain two or more types. When two or more types are included, it is preferable that the total amount falls within the above range.
- the resin composition of the present embodiment contains 0.05 to 10 parts by mass of a compound having 1 to 3 cyclic ether structures in one molecule (cyclic ether compound) per 100 parts by mass of the polyamide resin.
- a cyclic ether compound By including a cyclic ether compound, it reacts with diamines, dimers and trimers of raw material monomers, decomposition products, etc. that remain in the polyamide resin, and forms the resin composition into a film. At the same time, it is possible to effectively prevent diamine and the like from adhering to the roll and contaminating the roll.
- the number of cyclic ether structures in the cyclic ether compound is preferably one or two.
- the cyclic ether compound contains an epoxy ring and/or an oxetane ring.
- the molecular weight of the cyclic ether compound is preferably 180 or more, more preferably 1000 or less, and more preferably 800 or less.
- volatilization of the cyclic ether compound itself can be more effectively suppressed.
- the amount to be equal to or less than the above upper limit the mass per cyclic ether structure can be reduced, and the amount of the cyclic ether compound to be blended for suppressing roll staining can be reduced.
- the heat resistance (glass transition temperature) of the resulting film can be improved.
- the molecular weight of the cyclic ether compounds is the sum of the molecular weights of each cyclic ether compound multiplied by mass fraction.
- the cyclic ether compound used in this embodiment preferably consists of only carbon atoms, hydrogen atoms, and oxygen atoms as constituent elements. With such a configuration, it is possible to more effectively suppress staining of the roll and suppress the generation of foreign matter.
- the cyclic ether compound used in this embodiment preferably has three or less aromatic rings in one molecule, and more preferably does not contain any aromatic rings. By having fewer aromatic rings, compatibility with polyamide resins (especially aliphatic polyamide resins) tends to improve, and the effects of the present invention tend to be more effectively exhibited.
- the cyclic ether compound used in this embodiment contains an epoxy ring and/or an oxetane ring, consists of only carbon atoms, hydrogen atoms, and oxygen atoms, has a molecular weight of 180 to 1000, and has an aromatic aroma in one molecule. It is preferable that the number of rings is 3 or less (preferably 1 or 2). With such a configuration, it is possible to more effectively suppress staining of the roll and suppress the generation of foreign matter.
- the cyclic ether compound used in the present embodiment preferably has a formula (molecular weight of compound having 1 to 3 cyclic ether structures in one molecule/number of cyclic ether structures) ⁇ 250.
- the cyclic ether compound used in this embodiment may or may not have a group that reacts with an amino group other than the cyclic ether structure.
- An example of the cyclic ether compound used in this embodiment is a compound that does not have a group that reacts with an amino group other than the cyclic ether structure.
- Another example of the cyclic ether compound used in this embodiment is a compound that does not have an allyl group.
- the cyclic ether compound used in this embodiment is also a compound having 1 to 2 functional groups that can react with an amino group, and at least one of the functional groups that can react with an amino group is an epoxy group or an oxetanyl group. It is also preferable that it is a compound. With the above configuration, the effects of the present invention tend to be more effectively exhibited.
- the content of the cyclic ether compound in the resin composition of the present embodiment is 0.05 parts by mass or more, preferably 0.08 parts by mass or more, and 0.1 parts by mass based on 100 parts by mass of the polyamide resin.
- the amount is more preferably 0.2 parts by mass or more, even more preferably 0.3 parts by mass or more, and even more preferably 0.4 parts by mass or more.
- the upper limit of the content of the cyclic ether compound is 10 parts by mass or less, preferably 8 parts by mass or less, and more preferably 5 parts by mass or less, based on 100 parts by mass of the polyamide resin.
- the resin composition of this embodiment may contain only one type of cyclic ether compound, or may contain two or more types of cyclic ether compounds. When two or more types are included, it is preferable that the total amount falls within the above range.
- the resin composition of the present embodiment also preferably does not substantially contain a compound having four or more cyclic ether structures in one molecule.
- substantially free means that the content of a compound having 4 or more cyclic ether structures in one molecule is less than 10% by mass of the content of a compound having 1 to 3 cyclic ether structures in one molecule. In other words, it is preferably 5% by mass or less, more preferably 3% by mass or less, and may be 1% by mass or less.
- the resin composition of this embodiment includes a light stabilizer, a heat stabilizer, an antioxidant, an infrared absorber, a hydrolysis resistance improver, an ultraviolet absorber, an antistatic agent, an anticoloring agent, and a gel. Antioxidants, photochromic dyes, etc. may also be added.
- the resin composition of the present embodiment contains components other than the polyamide resin and the cyclic ether compound, the total content thereof is preferably 0.001% by mass or more of the resin composition, and 20% by mass. It is preferably at most 10% by mass, more preferably at most 5% by mass, even more preferably at most 3% by mass, even more preferably at most 1% by mass.
- the filler content in the resin composition is preferably 0 to 10% by mass, more preferably 0 to 5% by mass, even more preferably 0 to 3% by mass, and even more preferably 0 to 1% by mass. It is more preferably 0 to 0.1% by mass, even more preferably 0 to 0.01% by mass, and even more preferably substantially free.
- Substantially free means, for example, that the content of the cyclic ether compound contained in the resin composition is 10% by mass or less, preferably 5% by mass or less, and preferably 3% by mass or less. More preferably, it is 1% by mass or less. Moreover, in the resin composition of this embodiment, it is preferable that the total of the polyamide resin and the cyclic ether compound accounts for 99% by mass or more of the resin composition.
- the resin composition of this embodiment is preferably a thermoplastic resin composition. It is preferable that the resin composition of this embodiment does not substantially contain a solvent.
- Substantially free means that the content of the solvent is, for example, 10% by mass or less of the content of the cyclic ether compound contained in the resin composition, preferably 5% by mass or less, It is more preferably 3% by mass or less, and even more preferably 1% by mass or less.
- the resin composition of this embodiment has high transparency. Specifically, when the resin composition is made into a film with a thickness of 200 ⁇ m, the haze is 10% or less. Such a haze is achieved by using a polyamide resin that is inherently highly transparent, by controlling the filler content in the resin composition to 10% by mass or less, and the like.
- the haze when the resin composition is made into a film with a thickness of 200 ⁇ m is preferably 5% or less, more preferably 3% or less, even more preferably 1.1% or less, and 0.8% or less. % or less, and even more preferably 0.6% or less. While the haze of polyamide resin films used as packaging materials is usually more than 10%, the haze of the resin composition of this embodiment is much lower.
- Any method can be employed as a method for manufacturing the resin composition of this embodiment. For example, it can be obtained by adding 0.05 to 10 parts by mass of a compound having 1 to 3 cyclic ether structures per molecule to 100 parts by mass of polyamide resin and melt-kneading the mixture. More specifically, a polyamide resin, a compound having 1 to 3 cyclic ether structures in one molecule, and other components blended as necessary are mixed using a mixing means such as a V-type blender. , a method of preparing a batch blend product and then melt-kneading it in a vented extruder to pelletize it.
- the film of this embodiment is formed from the resin composition of this embodiment.
- the thickness of the film of this embodiment is preferably 100 ⁇ m or more, more preferably 120 ⁇ m or more, even more preferably 140 ⁇ m or more, even more preferably 160 ⁇ m or more, and preferably 180 ⁇ m or more. Even more preferred. Further, the thickness of the film of this embodiment is preferably 1000 ⁇ m or less, more preferably 900 ⁇ m or less, even more preferably 800 ⁇ m or less, even more preferably 600 ⁇ m or less, and even more preferably 500 ⁇ m or less. is even more preferable, and may be 300 ⁇ m or less. It is preferable that the film of this embodiment has excellent transparency.
- the haze is preferably 10% or less, more preferably 5% or less, even more preferably 3% or less, even more preferably 1.1% or less, and 0. The content is even more preferably 0.8% or less, and even more preferably 0.6% or less. While the haze of polyamide resin films used as packaging materials is usually more than 10%, the haze of the film of this embodiment is much lower.
- the film of this embodiment is usually manufactured by extrusion molding, that is, it is an extrusion molded product. Further, the film of this embodiment is usually formed using a roll. It is preferable that the film of this embodiment is, for example, a continuous film.
- the continuous film is, for example, a film with a length of 10 m or more (preferably 10,000 m or less). The continuous film can be wound into a roll to form a wound body.
- the film of this embodiment is used for applications requiring high transparency. Specifically, it is preferably used as a protective film for a polarizing sheet, and more preferably used as a protective film for a polarizing sheet. In particular, it is preferably used for sunglasses and goggles. That is, in this embodiment, a polarizing sheet is exemplified, which has a polarizing film and a protective film on at least one surface of the polarizing film, and the protective film is the film of this embodiment.
- FIG. 1 is a schematic diagram showing the layer structure of the polarizing sheet of this embodiment, where 1 is a polarizing film, 2 is a protective film (film of this embodiment), and 3 is a polarizing film and a protective film bonded together. The adhesive layer is shown.
- a polyvinyl alcohol resin film is preferably used as the polarizing film.
- the polyvinyl alcohol resin include polyvinyl alcohol (PVA) and derivatives or analogs thereof such as polyvinyl formal, polyvinyl acetal, and saponified poly(ethylene-vinyl acetate) copolymers, with PVA being preferred.
- the weight average molecular weight of the PVA film is preferably 50,000 or more, more preferably 150,000 or more, and preferably 350,000 or less, more preferably 300,000 or less.
- the polarizing film is preferably formed by stretching and dyeing a polyvinyl alcohol resin film or the like.
- the stretching ratio is preferably 2 times or more, more preferably 3 times or more, preferably 8 times or less, and more preferably 6.5 times or less.
- the thickness of the polarizing film is preferably 10 ⁇ m or more, more preferably 20 ⁇ m or more, preferably 50 ⁇ m or less, and more preferably 40 ⁇ m or less.
- An adhesive can be used when attaching the film of this embodiment to both sides of the polarizing film.
- adhesives polyvinyl alcohol resin materials, acrylic resin materials, urethane resin materials, polyester resin materials, melamine resin materials, epoxy resin materials, silicone materials, etc. can be used. It is preferable that there be.
- the polarizing sheet of this embodiment is not limited to the above-mentioned range, and for example, a light stabilizer, a heat Using stabilizers, antioxidants, infrared absorbers, hydrolysis resistance improvers, ultraviolet absorbers, antistatic agents, coloring inhibitors, gelling inhibitors, light control dyes, etc., dissolved as appropriate. Good too.
- the method for producing a film of the present embodiment includes adding 0.05 to 10 parts by mass of a compound having 1 to 3 cyclic ether structures in one molecule to 100 parts by mass of polyamide resin, and melt-kneading the mixture. .
- the obtained film preferably satisfies the above-mentioned film of this embodiment. More specifically, the film can be produced by extruding a molten resin composition into a sheet while conveying it using rolls.
- the resin composition preferably satisfies the resin composition of the present embodiment described above.
- Raw materials The following raw materials were used.
- A1 Rilsan Clear G850, manufactured by Arkema, polyamide resin obtained from 4,4'-methylenebis(2-methylcyclohexylamine) and sebacic acid
- B1 OXT-221, manufactured by Toagosei B2: 2021P, manufactured by Daicel Corporation
- B3 OXT-121, manufactured by Daicel Corporation
- B4 OXT-212, manufactured by Toagosei Co., Ltd.
- n is a mixture of 1 to 3
- B5 Epogose PT, manufactured by Yokkaichi Gosei Co., Ltd.
- n is a mixture of 1 to 25.
- B6 TETRAD-X, manufactured by Mitsubishi Gas Chemical Co., Ltd.
- a polyamide resin film was produced by extruding it in a molten state under the conditions of a discharge rate of 8 kg/h and a screw rotation speed of 100 rpm, and cooling and solidifying only with the first roll of a film/sheet take-off device (manufactured by Toyo Seiki Co., Ltd., "FT3W20"). did.
- the cylinder/die head temperature was 290°C, and the roll temperature was 130°C.
- the final film thickness was adjusted to 200 ⁇ m by changing the roll speed of the first roll.
- Roll stains> Regarding roll stains, the presence or absence of roll stains was visually confirmed on the first roll 20 minutes after the resin was first taken up by a film/sheet take-up device. It was evaluated as follows. A: No stains were observed on the roll B: Dirt was observed on the roll
- ⁇ Haze> The haze (unit: %) of the film obtained above was measured using a haze meter under the conditions of a D65 light source and a 10° field of view.
- the haze meter used was "HM-150" manufactured by Murakami Color Research Institute.
- the unit of each component is parts by mass.
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- Organic Chemistry (AREA)
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Abstract
L'invention concerne : une composition de résine qui peut supprimer l'apparition de taches sur un rouleau de moulage et grâce à laquelle une matière étrangère est peu susceptible d'être formée dans un film ; un film ; une feuille polarisante ; un procédé de production de composition de résine ; et un procédé de fabrication de film. Cette composition de résine contient, par rapport à 100 parties en masse d'une résine de polyamide, 0,05-10 parties en masse d'un composé comprenant 1-3 structures d'éther cyclique par molécule et présente un voile de 10 % ou moins lorsqu'elle est façonnée en un film de 200 µm d'épaisseur.
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JP2022124978A JP2024021847A (ja) | 2022-08-04 | 2022-08-04 | 樹脂組成物、フィルム、偏光シート、樹脂組成物の製造方法、および、フィルムの製造方法 |
JP2022-124978 | 2022-08-04 |
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WO2024029515A1 true WO2024029515A1 (fr) | 2024-02-08 |
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PCT/JP2023/028063 WO2024029515A1 (fr) | 2022-08-04 | 2023-08-01 | Composition de résine, film, feuille polarisante, procédé de production de composition de résine et procédé de fabrication de film |
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WO (1) | WO2024029515A1 (fr) |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH03237161A (ja) * | 1990-02-15 | 1991-10-23 | Mitsui Petrochem Ind Ltd | 成型用ポリアミド組成物 |
JPH03237159A (ja) * | 1990-02-15 | 1991-10-23 | Mitsui Petrochem Ind Ltd | ポリアミド組成物 |
US5605945A (en) * | 1994-06-03 | 1997-02-25 | Bayer Aktiengesellschaft | Polyamide compounds containing diepoxide and having high viscosity |
JPH09511267A (ja) * | 1994-03-11 | 1997-11-11 | ヘンケル・コマンディットゲゼルシャフト・アウフ・アクチエン | 二量体脂肪酸からのポリアミド |
JP2003226818A (ja) * | 2001-11-30 | 2003-08-15 | Polyplastics Co | 難燃性樹脂組成物 |
JP2011180266A (ja) * | 2010-02-26 | 2011-09-15 | Yamamoto Kogaku Co Ltd | 偏光積層体および偏光レンズ、および偏光眼鏡 |
JP2013109116A (ja) * | 2011-11-21 | 2013-06-06 | Konica Minolta Advanced Layers Inc | 偏光膜保護フィルムの製造方法、偏光膜保護フィルム、偏光板及びそれを用いた液晶表示装置 |
JP2019045813A (ja) * | 2017-09-07 | 2019-03-22 | ダイセル・エボニック株式会社 | 偏光性シート、及びこれを備えた偏光レンズ |
JP2021507979A (ja) * | 2017-12-20 | 2021-02-25 | パフォーマンス ポリアミドス,エスエーエス | 高耐熱性のポリアミド成形化合物 |
-
2022
- 2022-08-04 JP JP2022124978A patent/JP2024021847A/ja active Pending
-
2023
- 2023-08-01 WO PCT/JP2023/028063 patent/WO2024029515A1/fr unknown
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH03237161A (ja) * | 1990-02-15 | 1991-10-23 | Mitsui Petrochem Ind Ltd | 成型用ポリアミド組成物 |
JPH03237159A (ja) * | 1990-02-15 | 1991-10-23 | Mitsui Petrochem Ind Ltd | ポリアミド組成物 |
JPH09511267A (ja) * | 1994-03-11 | 1997-11-11 | ヘンケル・コマンディットゲゼルシャフト・アウフ・アクチエン | 二量体脂肪酸からのポリアミド |
US5605945A (en) * | 1994-06-03 | 1997-02-25 | Bayer Aktiengesellschaft | Polyamide compounds containing diepoxide and having high viscosity |
JP2003226818A (ja) * | 2001-11-30 | 2003-08-15 | Polyplastics Co | 難燃性樹脂組成物 |
JP2011180266A (ja) * | 2010-02-26 | 2011-09-15 | Yamamoto Kogaku Co Ltd | 偏光積層体および偏光レンズ、および偏光眼鏡 |
JP2013109116A (ja) * | 2011-11-21 | 2013-06-06 | Konica Minolta Advanced Layers Inc | 偏光膜保護フィルムの製造方法、偏光膜保護フィルム、偏光板及びそれを用いた液晶表示装置 |
JP2019045813A (ja) * | 2017-09-07 | 2019-03-22 | ダイセル・エボニック株式会社 | 偏光性シート、及びこれを備えた偏光レンズ |
JP2021507979A (ja) * | 2017-12-20 | 2021-02-25 | パフォーマンス ポリアミドス,エスエーエス | 高耐熱性のポリアミド成形化合物 |
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