WO2022118930A1 - Composition, composition de coloration de résine, et polymère - Google Patents

Composition, composition de coloration de résine, et polymère Download PDF

Info

Publication number
WO2022118930A1
WO2022118930A1 PCT/JP2021/044341 JP2021044341W WO2022118930A1 WO 2022118930 A1 WO2022118930 A1 WO 2022118930A1 JP 2021044341 W JP2021044341 W JP 2021044341W WO 2022118930 A1 WO2022118930 A1 WO 2022118930A1
Authority
WO
WIPO (PCT)
Prior art keywords
general formula
group
repeating unit
substituent
polymer
Prior art date
Application number
PCT/JP2021/044341
Other languages
English (en)
Japanese (ja)
Inventor
由記 福田
Original Assignee
富士フイルム株式会社
富士フイルム和光純薬株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 富士フイルム株式会社, 富士フイルム和光純薬株式会社 filed Critical 富士フイルム株式会社
Priority to JP2022566985A priority Critical patent/JPWO2022118930A1/ja
Publication of WO2022118930A1 publication Critical patent/WO2022118930A1/fr

Links

Classifications

    • 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
    • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F12/02—Monomers containing only one unsaturated aliphatic radical
    • C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
    • C08F12/26—Nitrogen
    • 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
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C08L101/06—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
    • C08L25/18—Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
    • 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
    • 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 composition, a resin coloring composition, and a polymer.
  • the main coloring method of the resin include a method of directly mixing the dye and the resin so as to obtain a desired color, and a method of passing through a masterbatch for coloring the resin.
  • the method via a resin coloring masterbatch is specifically described above in which a composition (for example, pellets) in which a dye and a resin are mixed so as to have a high dye concentration is used as a resin coloring masterbatch.
  • This is a method of mixing a masterbatch for resin coloring and a diluted resin so as to obtain a desired color.
  • a compound having a coumarin skeleton (hereinafter, also referred to as “coumarin compound”) is mainly used as a dye exhibiting a fluorescent yellow color.
  • coumarin compound A compound having a coumarin skeleton (hereinafter, also referred to as “coumarin compound”) is mainly used as a dye exhibiting a fluorescent yellow color.
  • Patent Document 1 discloses a low molecular weight coumarin compound shown below. ing.
  • Patent Document 2 discloses the following low-molecular-weight coumarin compounds.
  • the colored resin molded product has a wide range of uses, for example, it may be used as a decorative item or the like to be worn on the skin. Therefore, there is also a demand for performance that does not easily fade due to sweat from the user (excellent in sweat resistance).
  • the present inventor prepared and examined a composition in which the coumarin compound described in Patent Documents 1 and 2 was mixed with a resin as a dye, and it was clarified that the sweat resistance may not meet the recent requirements. did.
  • Another object of the present invention is to provide a composition having excellent sweat resistance. Another object of the present invention is to provide a resin coloring composition and a polymer having excellent sweat resistance.
  • a composition comprising a thermoplastic resin.
  • R 2 represents a group represented by the general formula (R1A) described later
  • R 3 represents a hydrogen atom or a methyl group, in [1] or [2].
  • the repeating unit represented by the general formula (1) is the repeating unit represented by the general formula (5) described later
  • the repeating unit represented by the general formula (2) is the general unit described later.
  • R 3 represents a hydrogen atom or a methyl group
  • R 15 may have a substituent, an aryl group, a benzyl group, an alkyl group, or hydrogen.
  • the above polymer is The weight average molecular weight is 1,000 to 100,000, and The description according to any one of [1] to [6], wherein the content of the repeating unit represented by the general formula (1) is 0.1 to 50% by mass with respect to all the repeating units in the polymer.
  • Composition. [8] A resin coloring composition comprising the composition according to any one of [1] to [7]. [9] A polymer containing a repeating unit represented by the general formula (4) described later and a repeating unit represented by the general formula (2) described later. [10] The repeating unit represented by the general formula (4) is the repeating unit represented by the general formula (5) described later, and the repeating unit represented by the general formula (2) is the general unit described later.
  • R 3 represents a hydrogen atom or a methyl group
  • R 15 may have a substituent, an aryl group, a benzyl group, an alkyl group, or hydrogen.
  • the weight average molecular weight is 1,000 to 100,000, and the weight average molecular weight is 1,000 to 100,000.
  • the present invention it is possible to provide a composition having excellent sweat resistance. Further, according to the present invention, it is possible to provide a resin coloring composition and a polymer having excellent sweat resistance.
  • the present invention will be described in detail.
  • the description of the constituent elements described below may be based on the representative embodiments of the present invention, but the present invention is not limited to such embodiments.
  • the group is further substituted with a substituent (for example, a substituent W described later) as long as the desired effect is not impaired. May be.
  • a substituent for example, a substituent W described later
  • the notation "alkyl group” means an alkyl group that may be substituted with a substituent (eg, a substituent W described below).
  • the "organic group” in the present specification means a group containing at least one carbon atom.
  • the numerical range represented by using “-” means a range including the numerical values before and after "-" as the lower limit value and the upper limit value.
  • the bonding direction of the divalent group described in the present specification is not particularly limited, and for example, in the case of -CO-O-, it may be either -CO-O- or -O-CO-.
  • (meth) acrylate represents acrylate and methacrylate
  • (meth) acrylic represents acrylic and methacrylic.
  • the weight average molecular weight (Mw) and the degree of dispersion (also referred to as molecular weight distribution) (Mw / Mn) of the polymer are measured by GPC (solvent: tetrahydrofuran) by a GPC (Gel Permeation Chromatography) apparatus (HLC-8220GPC manufactured by Tosoh).
  • Flow rate (sample injection amount): 10 ⁇ L
  • Column TSK gel polymer HXL-M manufactured by Toso Co., Ltd., Column temperature: 40 ° C.
  • Flow velocity 1.0 mL / min
  • Detector Differential refractometer (Refractometer) Defined as a polystyrene equivalent value by.
  • composition of the present invention comprises a polymer (hereinafter, also referred to as “specific polymer”) containing a repeating unit represented by the general formula (1) described later and a repeating unit represented by the general formula (2) described later, and heat. Including, with a plastic resin.
  • a specific polymer containing a coumarin dye as a repeating unit is used.
  • the specific polymer containing the coumarin dye in the structure forms a network with the thermoplastic resin, so that the coumarin dye is less likely to be attached or detached by sweat, resulting in fading.
  • the above composition is capable of stably coloring a resin even when a specific polymer is blended in a relatively high concentration, and is a resin coloring composition (resin coloring masterbatch). ), It is also clarified that it can be suitably used. Further, it has been clarified that the light resistance is also excellent by appropriately selecting the repeating unit represented by the general formula (2) in the specific polymer.
  • the fact that the composition is more excellent in sweat resistance and / or light resistance is also referred to as "the effect of the present invention is more excellent".
  • composition of the present invention comprises a specific polymer and a thermoplastic resin.
  • the specific polymer is a polymer containing a repeating unit represented by the following general formula (1) and a repeating unit represented by the following general formula (2). In the following, first, the repeating unit represented by the general formula (1) will be described.
  • R 1 represents a hydrogen atom or a substituent.
  • the type of the substituent represented by R 1 is not particularly limited, and examples thereof include the groups exemplified by the substituent W described later.
  • R 1 preferably represents an alkyl group which may have a hydrogen atom or a substituent, and may have a hydrogen atom or a substituent, because the effect of the present invention is more excellent. It is more preferable to represent a good alkyl group having 1 to 6 carbon atoms, and even more preferably to represent a hydrogen atom or a methyl group.
  • examples of the substituent that the above-mentioned alkyl group may have include the groups exemplified by the substituent W described later.
  • L represents a divalent linking group.
  • the divalent linking group represented by L is not particularly limited, and is, for example, -CO-, -O-, -S-, -SO-, -SO2- , -NR A- , and an alkylene group (straight chain). It may be in the form of a branched chain, a branched chain, or a cyclic chain. It is preferably 1 to 15 carbon atoms, more preferably 1 to 6 carbon atoms), an alkenylene group (preferably 2 to 6 carbon atoms), and a divalent aliphatic.
  • a heterocyclic group preferably a 5- to 10-membered ring having at least one nitrogen atom, an oxygen atom, or a sulfur atom in the ring structure, more preferably a 5- to 7-membered ring, and even more preferably a 5- to 6-membered ring).
  • a divalent arylene group preferably a 6-10 membered ring, more preferably a 6 membered ring
  • a divalent heteroarylene group (5- to 5 having at least one nitrogen atom, oxygen atom, or sulfur atom in the ring structure).
  • a 10-membered ring is preferable, a 5- to 7-membered ring is more preferable, and a 5- to 6-membered ring is more preferable), and a divalent linking group in which a plurality of these are combined can be mentioned.
  • the RA include a hydrogen atom or a monovalent organic group.
  • the monovalent organic group is not particularly limited, but for example, an alkyl group (preferably 1 to 6 carbon atoms) is preferable.
  • the alkylene group, the alkenylene group, the divalent aliphatic heterocyclic group, the divalent arylene group, and the divalent heteroarylene group may have a substituent. Examples of the substituent include the groups exemplified by the substituent W described later.
  • the effect of the present invention is more excellent, and among them, -CO-O-, an alkylene group, a divalent arylene group, a divalent heteroarylene group, or these. It is preferable that it is a divalent linking group in which a plurality of the above is combined, and it is more preferable that it is a —CO—O—, an alkylene group, a divalent arylene group, or a divalent linking group in which a plurality of these is combined.
  • a divalent linking group in which an alkylene group and a divalent arylene group are combined for example, * -CH2 -Ph- * (Ph represents a phenylene group which may have a substituent, * represents a bonding position). It is more preferable.
  • X 1 represents a residue derived from the compound represented by the following general formula (3).
  • X 2 represents a coumarin ring group which may have a substituent.
  • the coumarin ring group which may have a substituent is intended to be a group formed by removing one hydrogen atom from the coumarin ring which may have a substituent.
  • the position where the hydrogen atom is excluded is not particularly limited, and may be a hydrogen atom bonded to a carbon atom constituting the coumarin ring (in other words, a carbon atom which is a ring member atom of the coumarin ring) or a coumarin ring. It may be a hydrogen atom contained in the substituent of.
  • Examples of the coumarin ring group which may have a substituent include residues derived from the compound represented by the following general formula (3A).
  • R 16 in the general formula (3A) represents a hydrogen atom, and the hydrogen atom of R 16 is removed to form a compound represented by the general formula (3A). It is preferable that the derived residue is formed.
  • the substituents represented by R 9 , R 10 , R 11 , R 12 , R 13 , and R 16 are not particularly limited, and examples thereof include the groups exemplified by the substituent W described later. In particular, it is preferable that at least one of R 9 , R 10 , R 11 and R 12 has a substituent, and it is more preferable that the substituent has a dialkylamine having a total carbon number of 2 to 8. Further, in R 9 , R 10 , R 11 , R 12 , R 13 and R 16 , adjacent substituents may be bonded to each other to form a ring.
  • Y represents an oxygen atom, a sulfur atom, or NR 8 .
  • Y it is preferable to represent NR 8 in that the effect of the present invention is more excellent.
  • R 4 , R 5 , R 6 , R 7 and R 8 each independently represent a hydrogen atom or a substituent. However, at least one of R 4 , R 5 , R 6 , R 7 and R 8 in the general formula (3) represents a hydrogen atom, and one of the above hydrogen atoms is removed, so that the general formula ( Residues derived from the compound represented by 3) are formed. That is, the position where one of the hydrogen atoms is removed is the bond position with L specified in the general formula (1).
  • Y in the above general formula (3) represents NR 8 .
  • Y in the general formula (3) is NR 8 and R 8 represents a hydrogen atom, and the hydrogen atom of this R 8 is removed, so that the general formula (3) can be used.
  • Residues derived from the represented compound are formed, or at least one of R 5 and R 6 represents a hydrogen atom and one of at least one hydrogen atom of R 5 and R 6 is removed. Therefore, it is preferable that a residue derived from the compound represented by the general formula (3) is formed, and Y in the general formula ( 3 ) is NR 8 and R 8 represents a hydrogen atom. It is more preferable that a residue derived from the compound represented by the general formula (3) is formed by removing the hydrogen atom of.
  • R 4 , R 5 , R 6 , R 7 and R 8 are not particularly limited, and examples thereof include the groups exemplified by the substituent W described later.
  • R4 , R5 , R6 , R7 , and R8 it is preferable to represent a hydrogen atom.
  • the repeating unit represented by the above-mentioned general formula (1) the repeating unit represented by the following general formula (4) is preferable, and the repeating unit represented by the following general formula (5) is preferable. It is more preferable to have it.
  • R 4 , R 5 , R 6 and R 7 are synonymous with R 4 , R 5 , R 6 and R 7 in the above-mentioned general formula (3), and preferred embodiments are also included. It is the same.
  • R 1 and L are synonymous with R 1 and L in the above-mentioned general formula (1), respectively, and the preferred embodiments are also the same.
  • R 9 , R 10 , R 11 , R 12 and R 13 are synonymous with R 9 , R 10 , R 11 , R 12 and R 13 in the general formula (3A) described above. And the preferred embodiment is the same.
  • the content of the repeating unit represented by the general formula (1) is preferably 0.1% by mass or more, more preferably 1% by mass or more, still more preferably 5% by mass or more, based on all the repeating units in the specific polymer. 10% by mass or more is particularly preferable.
  • the upper limit is preferably 70% by mass or less, more preferably 60% by mass or less, and further preferably 50% by mass or less.
  • the repeating unit represented by the general formula (1) may be one type alone or a plurality of them in combination.
  • R 2 and R 3 each independently represent a hydrogen atom or a substituent.
  • the substituent represented by R2 is not particularly limited, and examples thereof include a group exemplified by the substituent W described later.
  • the substituent represented by R2 is preferably a group represented by the following general formula (R1A).
  • L 1 represents a single bond or an ester bond (-CO-O-).
  • R 14 represents a hydrogen atom or a substituent.
  • an aryl group, an aralkyl group, an alkyl group, or a heteroaryl group which may have a substituent is preferable, and an aryl group which may have a substituent may be used.
  • a benzyl group or an alkyl group is more preferable, and an alkyl group which may have a substituent is further preferable.
  • the alkyl group preferably does not have an aryl group as a substituent.
  • the substituents that the aryl group, the aralkyl group, the alkyl group, and the heteroaryl group may have are not particularly limited, and examples thereof include the groups exemplified by the substituent W described later. * Represents the bond position.
  • L 1 preferably represents an ester bond.
  • R 14 it is preferable to represent an aryl group, a benzyl group, an alkyl group, or a hydrogen atom which may have a substituent, and is an alkyl group which may have a substituent. It is more preferable to have it.
  • the type of the substituent represented by R 3 is not particularly limited, and examples thereof include the groups exemplified by the substituent W described later.
  • R 3 preferably represents an alkyl group which may have a hydrogen atom or a substituent, and may have a hydrogen atom or a substituent, because the effect of the present invention is more excellent. It is more preferable to represent a good alkyl group having 1 to 6 carbon atoms, further preferably to represent a hydrogen atom or a methyl group, and particularly preferably to represent a methyl group.
  • R 2 represents a group represented by the above general formula (R1A), and R 14 represents an aryl group, a benzyl group, or a group.
  • R 14 represents an aryl group, a benzyl group, or a group.
  • An alkyl group, or a hydrogen atom preferably an alkyl group which may have a substituent
  • R 3 represents a hydrogen atom or a methyl group (preferably a methyl group).
  • the repeating unit is represented by the general formula (6).
  • R 3 and R 15 each independently represent a hydrogen atom or a substituent.
  • the R 3 in the general formula (6) has the same meaning as the R 3 in the general formula (2), and the preferred embodiment is also the same.
  • Examples of the substituent represented by R 15 include the groups exemplified by the substituent W described later.
  • an aryl group, an aralkyl group, an alkyl group, or a heteroaryl group which may have a substituent is preferable, and an aryl group which may have a substituent may be used.
  • a benzyl group, or an alkyl group is more preferable, and an alkyl group which may have a substituent is further preferable.
  • the alkyl group preferably does not have an aryl group as a substituent.
  • the substituents that the aryl group, the aralkyl group, the alkyl group, and the heteroaryl group may have are not particularly limited, and examples thereof include the groups exemplified by the substituent W described later.
  • the R 15 is preferably an aryl group, a benzyl group, an alkyl group, or an alkyl group which may have a substituent, and may have a substituent. It is more preferable to have it.
  • the content of the repeating unit represented by the general formula (2) is preferably 30% by mass or more, more preferably 50% by mass or more, based on all the repeating units in the specific polymer.
  • the upper limit thereof is preferably 99.9% by mass or less, more preferably 99% by mass or less, further preferably 95% by mass or less, and particularly preferably 90% by mass or less.
  • the repeating unit represented by the general formula (2) may be one type alone or a plurality of them in combination.
  • the specific polymer may contain a repeating unit represented by the above general formula (1) and other repeating units other than the repeating unit represented by the general formula (2). good.
  • the specific polymer can be synthesized according to a conventional method (for example, radical polymerization).
  • the weight average molecular weight of the specific polymer is preferably 1,000 to 100,000, more preferably 1,000 to 20,000, still more preferably 1,500 to 15,000, and 1 , 500-10,000 are particularly preferred.
  • the dispersity (molecular weight distribution) of the specific polymer is preferably 1 to 3, more preferably 1.2 to 3, and even more preferably 1.2 to 2.
  • the lower limit of the content of the specific polymer is preferably 0.001% by mass or more, more preferably 0.1% by mass or more, and further preferably 1% by mass or more, based on the total solid content of the composition.
  • the upper limit of the content of the specific polymer is preferably 40% by mass or less, more preferably 35% by mass or less, further preferably 25% by mass or less, and 20% by mass or less, based on the total solid content of the composition. Is particularly preferable, and 15% by mass or less is most preferable.
  • the "solid content" of a composition means all components except the solvent. In addition, if it is a component other than a solvent, a liquid component is also regarded as a solid content. Further, the specific polymer may be used alone or in combination of two or more.
  • substituent W in the present specification will be described.
  • substituent W include a halogen atom, an alkyl group (including a cycloalkyl group, a bicycloalkyl group, and a tricycloalkyl group), an alkenyl group (including a cycloalkenyl group and a bicycloalkenyl group), an alkynyl group, and an aryl.
  • heterocyclic group may be called heterocyclic group
  • cyano group hydroxy group, nitro group, alkoxy group, aryloxy group, silyloxy group, heterocyclic oxy group
  • acyloxy group carbamoyloxy group, alkoxycarbonyloxy Group, aryloxycarbonyloxy group, amino group (including anilino group), ammonio group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl or arylsulfonylamino Group, mercapto group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, alkyl or arylsulfinyl group, alkyl or arylsulfonyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, ary
  • substituent W may be further substituted with the substituent W.
  • the alkyl group may be substituted with a halogen atom.
  • the details of the substituent W are described in paragraph [0023] of JP-A-2007-234651.
  • Aryl group, alkyl group, heteroaryl group that a specific polymer can have Hereinafter, one embodiment of an aryl group, an alkyl group, an aralkyl group, and a heteroaryl group that the specific polymer may have is shown.
  • the number of carbon atoms in the aryl group of the specific polymer is preferably 6 to 30, more preferably 6 to 18, and even more preferably 6.
  • the aryl group may have a monocyclic structure or a condensed ring structure in which two or more rings are fused (condensed ring structure). Further, the aryl group may be substituted with a substituent (for example, the substituent W).
  • a substituent for example, the substituent W.
  • a phenyl group or a naphthyl group is preferable, and a phenyl group is more preferable.
  • the alkyl group of the specific polymer preferably has 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms, further preferably 1 to 6 carbon atoms, and particularly preferably 1 to 4 carbon atoms.
  • the alkyl group may be linear, branched, or cyclic. Further, the alkyl group may be substituted with a substituent (for example, substituent W).
  • alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, an n-hexyl group, a 2-ethylhexyl group, a cyclohexyl group and the like. Can be mentioned.
  • the aralkyl group of the specific polymer is a group in which one of the hydrogen atoms of the alkyl group is substituted with an aryl group.
  • the alkyl group portion of the aralkyl group of the specific polymer is the same as the preferred embodiment of the alkyl group of the specific polymer described above.
  • the aryl group portion of the aralkyl group of the specific polymer is the same as the preferred embodiment of the aryl group of the specific polymer described above.
  • Examples of the aralkyl group include a benzyl group and a phenethyl group.
  • the number of carbon atoms in the heteroaryl group (monovalent aromatic heterocyclic group) of the specific polymer is preferably 3 to 30, and more preferably 3 to 18.
  • the heteroaryl group may be substituted with a substituent (for example, substituent W).
  • the heteroaryl group has a hetero atom in addition to a carbon atom and a hydrogen atom.
  • the hetero atom include a sulfur atom, an oxygen atom, a nitrogen atom, a selenium atom, a tellurium atom, a phosphorus atom, a silicon atom, and a boron atom, and a sulfur atom, an oxygen atom, or a nitrogen atom is preferable.
  • the number of heteroatoms contained in the heteroaryl group is usually about 1 to 10, preferably 1 to 4, and more preferably 1 to 2.
  • the number of ring members of the heteroaryl group is preferably 3 to 8, more preferably 5 to 7, and even more preferably 5 to 6.
  • the heteroaryl group may have a monocyclic structure or a condensed ring structure in which two or more rings are fused. In the case of a condensed ring structure, an aromatic hydrocarbon ring (for example, a benzene ring) having no heteroatom may be contained.
  • the repeating unit (A), the repeating unit (B), and the repeating unit (C) are derived from the monomers shown in the columns of the repeating unit (A), the repeating unit (B), and the repeating unit (C). Intended to be a repeating unit.
  • "Me” in the polymer represents a methyl group
  • "Et” represents an ethyl group.
  • the composition comprises a thermoplastic resin.
  • the thermoplastic resin is a resin different from the above-mentioned specific polymer.
  • the thermoplastic resin is not particularly limited, and for example, polyamide resin, polyolefin resin, polyester resin, polyurethane resin, polyether ketone resin, polyether resin, polyimide resin, polyarylene sulfide resin, polyarylene ether resin, polycarbonate resin and the like. Can be mentioned.
  • the thermoplastic resin is preferably at least one selected from the group consisting of a polyamide resin and a polyolefin resin, and more preferably a polyamide resin.
  • the polyamide resin is a polymer having an acid amide bond (-CONH-) in the main chain.
  • Examples of such polyamide resin include nylon 6 (also known as poly (caprolactum)), nylon 11 (also known as poly (11-aminoundecanoic acid)), nylon 12 (also known as poly (lauryllactam)) or poly (12-amino).
  • Dodecanoic acid) Nylon 6.6 (also known as poly (hexamethylene / adipamide)), Nylon 6.9 (also known as poly (hexamethylene / azelamide) or poly (hexamethylene / nonandiamide)), nylon 6.10 (also known as hexamethylene / nonandiamide).
  • Polyethylene resins include crystalline or amorphous polypropylene, polybutene-1, poly-4-methylpentene, low density or high density polyethylene, ethylene-propylene random, block, or graft copolymers, ⁇ -olefins and ethylene. Or a propylene copolymer, an ethylene- (meth) alkyl acid copolymer, an ethylene- (meth) acrylic acid copolymer, a poly (meth) acrylate, a binary of an olefin and an ⁇ , ⁇ -unsaturated carboxylic acid.
  • It consists of a resin made of a metal ion neutralized product of a copolymer and a metal ion neutralized product of a ternary copolymer of olefin, ⁇ , ⁇ -unsaturated carboxylic acid and ⁇ , ⁇ -unsaturated carboxylic acid ester.
  • resin A resin composed of a metal ion neutralized product of a binary copolymer of an olefin and an ⁇ , ⁇ -unsaturated carboxylic acid, and an olefin and an ⁇ , ⁇ -unsaturated carboxylic acid and an ⁇ , ⁇ -unsaturated carboxylic acid.
  • the type and valence of the metal ion that neutralizes at least a part of the carboxy group are not particularly limited, and are, for example, sodium, potassium, and lithium.
  • Monovalent metal ions such as; divalent metal ions such as magnesium, calcium, zinc, barium, and cadmium; trivalent metal ions such as aluminum; other ions such as tin and zirconium.
  • the lower limit of the content of the thermoplastic resin is preferably 1% by mass or more, more preferably 10% by mass or more, still more preferably 30% by mass or more, more preferably 60% by mass, based on the total solid content of the composition. Mass% or more is particularly preferable.
  • the upper limit of the content of the thermoplastic resin is preferably 99.999% by mass or less, more preferably 99.9% by mass or less, still more preferably 99% by mass or less, based on the total solid content of the composition. ..
  • the thermoplastic resin may be used alone or in combination of two or more.
  • the combination of the specific polymer and the thermoplastic resin is preferably selected from the viewpoint of compatibility between the repeating unit represented by the general formula (2) contained in the specific polymer and the thermoplastic resin.
  • the compatibility between the two is excellent (in addition, a uniformly colored resin molded product can be obtained.
  • the repeating unit represented by the general formula (2) is a repeating unit derived from (meth) acrylate
  • a preferred embodiment of the thermoplastic resin includes a polyolefin resin, a polyamide resin, a polyurethane resin, a polyester resin and the like. Can be mentioned.
  • thermoplastic resin when the repeating unit represented by the general formula (2) is a repeating unit derived from (meth) acrylic acid, a preferred embodiment of the thermoplastic resin includes a polyolefin resin, a polyamide resin and the like. When the repeating unit represented by the general formula (2) is a repeating unit derived from styrene, a preferred embodiment of the thermoplastic resin includes a polyolefin resin and the like.
  • the composition may contain additives other than the specific polymer and the thermoplastic resin.
  • the additive can be appropriately selected depending on the intended use, and is not particularly limited, and examples thereof include flame retardants, antioxidants, weather resistant agents, mold release agents, lubricants, plasticizers, fillers, and reinforcing materials.
  • the method for producing the above composition is not particularly limited, and examples thereof include a production method in which a specific polymer as a raw material component, a thermoplastic resin, and an arbitrary additive are premixed as necessary and then melt-kneaded. .. It is desirable to heat the melt kneading above the melting point of the thermoplastic resin. After melt kneading, it is preferably extruded into strands and then cut into granules such as pellets and chips.
  • melt-kneader for example, a melt-kneader equipped with a heating mechanism such as a Banbury mixer, a mixing roll, a single-screw or twin-screw extruder, and a kneader can be used.
  • a heating mechanism such as a Banbury mixer, a mixing roll, a single-screw or twin-screw extruder, and a kneader
  • the composition can be processed into a resin molded product having a desired shape by various melt molding such as injection molding, compression molding, composite, sheet, and pipe extrusion molding, pultrusion molding, blow molding, and transfer molding.
  • the shape of the resin molded product is not particularly limited, and examples thereof include fibers, sheets, and films.
  • the obtained resin molded product also has excellent sweat resistance.
  • the above composition can also be used as a resin coloring composition (resin coloring masterbatch).
  • a resin coloring composition master batch for resin coloring
  • the above composition and a diluted resin which is a thermoplastic resin are mixed and used to obtain a resin molded product adjusted to a desired color. Can be formed.
  • the obtained resin molded product also has excellent sweat resistance.
  • the content of the specific polymer in the composition is set to a relatively high concentration from the viewpoint of widening the color selection region. Is preferable.
  • the content of the specific polymer in the composition is preferably 10 to 70% by mass with respect to the total solid content of the composition.
  • the blending ratio of the resin coloring composition (resin coloring master batch) and the diluted resin (thermoplastic resin) is not particularly limited.
  • the blending amount of the resin coloring composition is preferably 1 to 50 parts by mass with respect to 100 parts by mass of the diluted resin (thermoplastic resin), preferably 3 to 10 parts by mass. More preferred.
  • the diluted resin is a thermoplastic resin as described above, and examples thereof include resins similar to the thermoplastic resin contained in the above composition, and among them, a polyamide resin or a polyolefin resin is preferable, and a polyamide resin is used. It is more preferable to have it.
  • the diluted resin to which the resin coloring composition is applied is preferably selected from the viewpoint of compatibility between the thermoplastic resin contained in the resin coloring composition and the diluted resin.
  • the combination of the thermoplastic resin and the diluted resin contained in the resin coloring composition has excellent compatibility between the two (in addition, it is easy to obtain a uniformly colored resin molded product). Is preferable.
  • thermoplastic resin contained in the resin coloring composition is a polyamide resin
  • a preferred embodiment of the diluted resin is a polyamide resin, a polyurethane resin, a polyolefin resin (preferably poly (meth) acrylate), or the like. Can be mentioned. Of these, a polyamide resin is preferable.
  • thermoplastic resin contained in the resin coloring composition is a polyolefin resin
  • a preferred embodiment of the diluted resin is a polyolefin resin.
  • a resin coloring composition master batch for resin coloring
  • a thermoplastic resin which is a diluted resin and an arbitrary additive component are premixed as necessary.
  • a manufacturing method of melt-kneading can be mentioned.
  • the melt kneading is preferably heated to a temperature equal to or higher than the melting point of the thermoplastic resin in the resin coloring composition and the thermoplastic resin which is a diluted resin. After melt kneading, it is preferably extruded into strands and then cut into granules such as pellets and chips.
  • the melt kneader that can be used, the above-mentioned melt kneader can be used.
  • Colored resin compositions obtained by mixing a resin coloring composition and a diluted resin include various types such as injection molding, compression molding, extrusion molding of composites, sheets, and pipes, extraction molding, blow molding, and transfer molding. By melt molding, it can be processed into a resin molded product having a desired shape.
  • the shape of the obtained resin molded product is not particularly limited, and examples thereof include fibers, sheets, and films.
  • the present invention also relates to polymers.
  • the polymer of the present invention is a polymer containing the repeating unit represented by the above-mentioned general formula (4) and the repeating unit represented by the above-mentioned general formula (2).
  • the polymer of the present invention corresponds to one aspect of the above-mentioned specific polymer, and the preferred embodiment thereof is the same as the preferred embodiment of the above-mentioned specific polymer.
  • the polymer of the present invention can stably function as a colorant for a resin even when used at a high concentration.
  • nitrobenzene (0.3 mL, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), sodium iodide (13.5 g, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), and 4-chloromethylstyrene (11.9 g).
  • Tokyo Kasei Kogyo Co., Ltd. was added, and the mixture was stirred at 50 ° C. for 2 hours.
  • the stirred solution was returned to room temperature, diluted with ethyl acetate, and water was added to separate the solutions. After the liquid separation, the organic phase was concentrated to precipitate a yellow solid, which was filtered and dried to obtain the monomer M-1.
  • Example 1 The polymer P-1 and the polyamide resin (nylon 6, manufactured by Sigma-Aldrich) are mixed so that the content of the polymer P-1 is 1% by mass with respect to the content of the polyamide resin, and the cylinder temperature: 270 ° C. , Screw rotation speed: Kneaded with a twin-screw extruder set to 100 rpm to prepare colored pellets.
  • Example 2 Colored pellets of Example 2 were prepared by the same method as in Example 1 except that the polymer P-2 was used instead of the polymer P-1.
  • Example 3 The colored pellets of Example 3 were prepared by the same method as in Example 1 except that the polymer P-3 was used instead of the polymer P-1.
  • Example 4 The colored pellets of Example 4 were prepared by the same method as in Example 1 except that the polymer P-4 was used instead of the polymer P-1.
  • Example 5 The polymer P-5 and the polyamide resin (nylon 6, manufactured by Sigma-Aldrich) are mixed so that the content of the polymer P-5 is 0.5% by mass with respect to the total amount of the polyamide resin, and the cylinder temperature: Colored pellets were prepared by kneading with a twin-screw extruder set at 270 ° C. and screw rotation speed: 100 rpm.
  • Example 6 The polymer P-6 and the polyamide resin (nylon 6, manufactured by Sigma-Aldrich) are mixed so that the content of the polymer P-6 is 0.2% by mass with respect to the content of the polyamide resin, and the cylinder temperature: Colored pellets were prepared by kneading with a twin-screw extruder set at 270 ° C. and screw rotation speed: 100 rpm.
  • Example 7 The colored pellets of Example 7 were prepared by the same method as in Example 1 except that the polymer P-7 was used instead of the polymer P-1.
  • Example 8 The polymer P-6 and the polyamide resin (nylon 6, manufactured by Sigma-Aldrich) are mixed so that the content of the polymer P-6 is 50% by mass with respect to the content of the polyamide resin, and the cylinder temperature: 270 ° C. , Screw rotation speed: Kneaded with a twin-screw extruder set to 100 rpm to prepare colored pellets.
  • Example 9 Polymer P-1 and polyethylene resin (trade name "Sumikasen", manufactured by Sumitomo Chemical Co., Ltd.) are mixed so that the content of polymer P-1 is 1% by mass with respect to the content of polyethylene resin, and the cylinder temperature is adjusted. Colored pellets were prepared by kneading with a twin-screw extruder set at 200 ° C. and screw rotation speed: 100 rpm.
  • Example 10 The colored pellets of Example 10 were prepared by the same method as in Example 9 except that the polymer P-2 was used instead of the polymer P-1.
  • Example 11 The colored pellets of Example 11 were prepared by the same method as in Example 9 except that the polymer P-3 was used instead of the polymer P-1.
  • Example 12 The colored pellets of Example 12 were prepared by the same method as in Example 9 except that the polymer P-4 was used instead of the polymer P-1.
  • Example 13 Polymer P-5 and polyethylene resin (trade name "Sumikasen", manufactured by Sumitomo Chemical Co., Ltd.) are mixed so that the content of polymer P-5 is 0.5% by mass with respect to the content of polyethylene resin. Colored pellets were produced by kneading with a twin-screw extruder set at a cylinder temperature of 200 ° C. and a screw rotation speed of 100 rpm.
  • Example 14 Polymer P-6 and polyethylene resin (trade name "Sumikasen", manufactured by Sumitomo Chemical Co., Ltd.) are mixed so that the content of polymer P-6 is 0.2% by mass with respect to the content of polyethylene resin. Colored pellets were produced by kneading with a twin-screw extruder set at a cylinder temperature of 200 ° C. and a screw rotation speed of 100 rpm.
  • Example 15 The colored pellets of Example 15 were prepared by the same method as in Example 9 except that the polymer P-7 was used instead of the polymer P-1.
  • Example 16 Polymer P-6 and polyethylene resin (trade name "Sumikasen", manufactured by Sumitomo Chemical Co., Ltd.) are mixed so that the content of polymer P-6 is 50% by mass with respect to the content of polyethylene resin, and the cylinder temperature is adjusted. Colored pellets were prepared by kneading with a twin-screw extruder set at 200 ° C. and screw rotation speed: 100 rpm.
  • Example 17 Polymer P-1 and polyester resin (trade name "polyethylene terephthalate", manufactured by Unitika Ltd.) are mixed so that the content of polymer P-1 is 1% by mass with respect to the content of polyester resin, and a cylinder is used. Colored pellets were prepared by kneading with a twin-screw extruder set at a temperature of 280 ° C. and a screw rotation speed of 100 rpm.
  • Example 18 The colored pellets of Example 18 were prepared by the same method as in Example 17 except that the polymer P-2 was used instead of the polymer P-1.
  • Example 19 The colored pellets of Example 19 were prepared by the same method as in Example 17 except that the polymer P-3 was used instead of the polymer P-1.
  • Example 20 The colored pellets of Example 20 were prepared by the same method as in Example 17 except that the polymer P-4 was used instead of the polymer P-1.
  • Example 21 Polymer P-5 and polyester resin (trade name "polyethylene terephthalate", manufactured by Unitika Ltd.) are mixed so that the content of polymer P-5 is 0.5% by mass with respect to the content of polyester resin. Colored pellets were produced by kneading with a twin-screw extruder set at a cylinder temperature of 280 ° C. and a screw rotation speed of 100 rpm.
  • Example 22 The polymer P-6 and the polyester resin (trade name "polyethylene terephthalate", manufactured by Unitika Ltd.) are mixed so that the content of the polymer P-6 is 0.2% by mass with respect to the content of the polyester resin. Colored pellets were produced by kneading with a twin-screw extruder set at a cylinder temperature of 280 ° C. and a screw rotation speed of 100 rpm.
  • Example 23 The colored pellets of Example 23 were prepared by the same method as in Example 17 except that the polymer P-7 was used instead of the polymer P-1.
  • ⁇ Comparative Example 1> The comparative compound C-1 described later and the polyamide resin (nylon 6, manufactured by Sigma-Aldrich) are mixed so that the content of the comparative compound C-1 is 0.1% by mass with respect to the content of the polyamide resin. , Cylon temperature: 270 ° C., screw rotation speed: 100 rpm, kneaded with a twin-screw extruder to prepare colored pellets.
  • ⁇ Comparative Example 2> The comparative compound C-2 described later and the polyamide resin (nylon 6, manufactured by Sigma-Aldrich) are mixed so that the content of the comparative compound C-2 is 0.1% by mass with respect to the content of the polyamide resin. , Cylon temperature: 270 ° C., screw rotation speed: 100 rpm, kneaded with a twin-screw extruder to prepare colored pellets.
  • Comparative Example 3 The comparative compound C-2 described later and the polyamide resin (nylon 6, manufactured by Sigma-Aldrich) are mixed so that the content of the comparative compound C-2 is 25% by mass with respect to the content of the polyamide resin, and the cylinder is used. Colored pellets were prepared by kneading with a twin-screw extruder set at a temperature of 270 ° C. and a screw rotation speed of 100 rpm.
  • ⁇ Comparative Example 4> The comparative compound C-1 described later and the polyethylene resin (trade name “Sumicasen”, manufactured by Sumitomo Chemical Co., Ltd.) are mixed so that the content of the comparative compound C-1 is 0.1% by mass with respect to the content of the polyethylene resin. And kneaded with a twin-screw extruder set at a cylinder temperature of 200 ° C. and a screw rotation speed of 100 rpm to prepare colored pellets.
  • Comparative Example 6 The comparative compound C-2, which will be described later, and a polyethylene resin (trade name “Sumikasen”, manufactured by Sumitomo Chemical Co., Ltd.) are mixed so that the content of the comparative compound C-2 is 25% by mass with respect to the content of the polyethylene resin. Then, the mixture was kneaded with a twin-screw extruder set at a cylinder temperature of 200 ° C. and a screw rotation speed of 100 rpm to prepare colored pellets.
  • a polyethylene resin trade name “Sumikasen”, manufactured by Sumitomo Chemical Co., Ltd.
  • Condition 1 In the repeating unit represented by the general formula (2) in the specific polymer, R 2 represents a group represented by the above general formula (R1A), and R 14 has a substituent. Represents a optionally alkyl group, where R 3 represents a hydrogen atom or a methyl group.
  • Condition 2 The content of the repeating unit satisfying the condition 1 satisfies 50% by mass or more with respect to all the repeating units in the specific polymer. On the other hand, the compositions of Comparative Examples did not meet the desired requirements.
  • Example 24 Performance evaluation as a resin coloring composition
  • the colored pellets prepared in Example 8 and the polyamide resin (nylon 6, manufactured by Sigma-Aldrich) were prepared so that the content of the colored pellets prepared in Example 8 was 4% by mass with respect to the content of the polyamide resin.
  • the mixture was mixed and kneaded by a twin-screw extruder set at a cylinder temperature of 270 ° C. and a screw rotation speed of 100 rpm to prepare colored pellets.
  • the obtained colored pellets were heated and formed to prepare a resin film having a thickness of 2 mm.
  • the prepared resin film was visually observed, it was confirmed that the polyamide resin was uniformly colored.
  • the degree of fading was small (“A” evaluation).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Un premier problème de la présente invention est de fournir une composition ayant une excellente résistance à la transpiration. Un second problème de la présente invention est de fournir une composition de coloration de résine et un polymère qui ont une excellente résistance à la transpiration. Ces compositions selon la présente invention comprennent chacune un polymère comprenant des motifs répétitifs représentés par la formule générale (1) et des motifs répétitifs représentés par la formule générale (2) et une résine thermoplastique.
PCT/JP2021/044341 2020-12-03 2021-12-02 Composition, composition de coloration de résine, et polymère WO2022118930A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2022566985A JPWO2022118930A1 (fr) 2020-12-03 2021-12-02

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2020201264 2020-12-03
JP2020-201264 2020-12-03

Publications (1)

Publication Number Publication Date
WO2022118930A1 true WO2022118930A1 (fr) 2022-06-09

Family

ID=81853359

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2021/044341 WO2022118930A1 (fr) 2020-12-03 2021-12-02 Composition, composition de coloration de résine, et polymère

Country Status (2)

Country Link
JP (1) JPWO2022118930A1 (fr)
WO (1) WO2022118930A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0673191A (ja) * 1992-04-23 1994-03-15 Bayer Ag プラスチツクの改良された同定法
JPH11130817A (ja) * 1997-08-28 1999-05-18 Junji Kido ビニル系重合体及びそれを用いたエレクトロルミネッセンス素子
JP2000087027A (ja) * 1998-09-11 2000-03-28 Fuji Photo Film Co Ltd 有機エレクトロルミネツセンス素子材料およびそれを使用した有機エレクトロルミネツセンス素子

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0673191A (ja) * 1992-04-23 1994-03-15 Bayer Ag プラスチツクの改良された同定法
JPH11130817A (ja) * 1997-08-28 1999-05-18 Junji Kido ビニル系重合体及びそれを用いたエレクトロルミネッセンス素子
JP2000087027A (ja) * 1998-09-11 2000-03-28 Fuji Photo Film Co Ltd 有機エレクトロルミネツセンス素子材料およびそれを使用した有機エレクトロルミネツセンス素子

Also Published As

Publication number Publication date
JPWO2022118930A1 (fr) 2022-06-09

Similar Documents

Publication Publication Date Title
KR100338904B1 (ko) 광확산체조성물
JPH0428748B2 (fr)
JPS6160746A (ja) 熱可塑性樹脂組成物
TW201005024A (en) Flameproof PMMA moulding material
JP2013522442A (ja) 耐衝撃性ポリスチレン難燃性組成物
CN104487512B (zh) 非卤化阻燃聚碳酸酯复合物
JPH09235320A (ja) オキサジン基を有するポリマーの製造法、成形材料の製造法、および成形材料から製造された成形体、フィルムおよび繊維
JP2019536851A (ja) ポリエステル組成物およびその調製方法
JP6911921B2 (ja) 熱可塑性樹脂組成物、成形体、及び車両用部品
WO2022118930A1 (fr) Composition, composition de coloration de résine, et polymère
KR20100072806A (ko) 열가소성 수지 조성물
JPH05170907A (ja) カルボキシル基含有ポリフェニレンスルフィドの製造方法
WO1991013937A1 (fr) Composition de resine ignifuge
JPS6326775B2 (fr)
BR112014031893B1 (pt) Artigo resistente a riscos feito a partir de misturas de policarbonato com polímero de metacrilato de metila modificado
EP0179175B1 (fr) Mélange de polymères contenant un copolymère méthacrylate de méthyle/N-phénylmaléimide
JP4954700B2 (ja) 熱可塑性樹脂組成物、および、押出しフィルムまたはシート
JPS5941355A (ja) 熱可塑性樹脂組成物
EP0568994A1 (fr) Mélanges miscibles de polyamides et de polymères contenant des groupes vinyl-phénol
JP2977261B2 (ja) 樹脂組成物
JP2018070874A (ja) 樹脂材料、表面硬度向上剤、ポリカーボネート樹脂組成物、成形体及びポリカーボネート樹脂組成物の製造方法
JPS601340B2 (ja) 樹脂組成物
JPH0517935B2 (fr)
JP2019104944A (ja) 樹脂材料、表面硬度向上剤、ポリカーボネート樹脂組成物、成形体
JPH02175743A (ja) Ｎ―置換マレイミド重合体組成物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 21900680

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2022566985

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 21900680

Country of ref document: EP

Kind code of ref document: A1