US20230399772A1

US20230399772A1 - Filament, material, and method for producing the material

Info

Publication number: US20230399772A1
Application number: US18/030,472
Authority: US
Inventors: Masaki Yamanaka; Nobuhiko Matsumoto
Original assignee: Mitsubishi Gas Chemical Co Inc
Current assignee: Mitsubishi Gas Chemical Co Inc
Priority date: 2020-10-08
Filing date: 2021-09-01
Publication date: 2023-12-14
Also published as: TW202223182A; WO2022074965A1; KR20230082641A; EP4227452A1; CN116324059A; JPWO2022074965A1

Abstract

Provided are a filament that does not impair the strength that is intrinsic to the filament and contains a disperse dye, and has excellent color fastness, a material using the filament, and a method for producing the material. The filament containing a polyamide resin having an aromatic ring and/or a hetero ring, and a disperse dye having an aromatic ring and/or a hetero ring.

Description

TECHNICAL FIELD

The present invention relates to a filament, a material, and a method for producing the material. In particular, the present invention relates to a filament containing a polyamide resin and a dye.

BACKGROUND ART

Filaments containing polyamide resins as main raw materials have been used in various purposes. Since a filament containing a polyamide resin as a main raw material has high strength, it is highly useful.
Meanwhile, use of an acidic dye has been known for dying a filament containing a polyamide resin as a main raw material (Patent Document 1).

CITATION LIST

Patent Documents

Patent Document 1: JP 48-063050 A

SUMMARY OF INVENTION

Technical Problem

In dyeing a filament containing a polyamide resin as a main raw material, it was found that good color fastness would be achieved when an acidic dye is used as described in Patent Document 1. However, in a case of, for example, making a commingled fiber with a filament that can only be dyed with a disperse dyes, such as when dyeing a filament containing a polyamide resin as a main raw material, use of a disperse dye may be required.
Meanwhile, it was found that a filament with a polyamide resin as a main raw material often exhibits low color fastness when a disperse dye is used. For this reason, when a disperse dye is used in a case of dyeing a commingled weave fabric with another thermoplastic filament such as polyester, an issue of color transfer occurs on an end product such as clothing or a bag.
The present invention is to solve the issues described above, and an object of the present invention is to provide a filament that does not impair the strength that is intrinsic to the filament and contains a disperse dye, and has excellent color fastness, a material using the filament, and a method for producing the material.

Solution to Problem

As a result of studies conducted by the present inventor to solve the above issue, the issue has been solved by the following means.
<1> A filament including a polyamide resin having an aromatic ring and/or a hetero ring, and a disperse dye having an aromatic ring and/or a hetero ring.
<2> The filament according to <1>, in which the disperse dye includes at least one selected from an aromatic azo compound, a heterocyclic azo compound, and an anthraquinone compound.
<3> The filament according to <1>, in which the disperse dye has a skeleton represented by Formula (C1) below or a skeleton represented by Formula (C2):
Ar¹—N═N—Ar² Formula (C1)

- where in Formula (C1), Ar¹and Ar²each independently represent an aryl group having from 6 to 40 carbons or a heteroaryl group having from 5 to 40 carbons;

<4> The filament according to any one of <1> to <3>, in which a single fiber fineness is from 2.0×10⁻⁵to 50 dtex.
<5> The filament according to any one of <1> to <4>, in which an elongation percentage as measured in accordance with JIS L 1013:2010 is 30% or more.
<6> The filament according to any one of <1> to <5>, in which the filament includes the polyamide resin containing diamine-derived structural units and dicarboxylic acid-derived structural units, 70 mol % or more of the diamine-derived structural units are derived from xylylenediamine, and 70 mol % or more of the dicarboxylic acid-derived structural units are derived from α,ω-linear aliphatic dicarboxylic acid having from 4 to 20 carbons.
<7> The filament according to <6>, in which the xylylenediamine contains from 30 to 100 mol % of m-xylylenediamine and from 0 to 70 mol % of p-xylylenediamine.
<8> The filament according to <6> or <7>, in which the dicarboxylic acid contains α,ω-linear aliphatic dicarboxylic acid having from 11 to 14 carbons.
<9> The filament according to <6> or <7>, in which the dicarboxylic acid contains 1,12-dodecanedioic acid.
<10> The filament according to any one of <1> to <9>, in which a filament length is 5 mm or more.
<11> The filament according to any one of <1> to <10>, in which the polyamide resin is a crystalline polyamide resin.
<12> The filament according to any one of <1> to <11>, in which the filament is a multifilament.
<13> The filament according to any one of <1> to <12>, in which, among all structural units constituting the polyamide resin, from 20 to 80 mol % of structural units have aromatic rings and/or hetero rings.
<14> A material containing a filament, the filament contained in the material including a polyamide resin having an aromatic ring and/or a hetero ring, and a disperse dye having an aromatic ring and/or a hetero ring.
<15> The material according to <14>, in which the filament is a filament according to any one of <1> to <13>.
<16> The material according to <14> to <15>, in which the material is a knitted fabric or a woven fabric.
<17> The material according to any one of <14> to <16>, having color fastness of 3 or more, in which the color fastness is a grade corresponding to a degree of coloration on a white cotton fabric that is evaluated based on a gray scale for contamination in accordance with JIS L 0805:2011 when the material is fixed on a desk, and a 1 kg cylindrical weight is fully covered by cotton No. 3-1 specified in JIS L 0803:2011 is placed on the material and moved back and forth for 100 times.
<18> A method for producing a filament according to any one of <1> to <13>, the method including applying a polyamide filament containing a polyamide resin having an aromatic ring and/or a hetero ring to a liquid containing a disperse dye having an aromatic ring and/or a hetero ring and water.
<19> A method for producing a material, the method including applying a woven fabric or a knitted fabric, the woven fabric formed from a polyamide filament containing a polyamide resin having an aromatic ring and/or a hetero ring, the knitted fabric formed from a polyamide filament containing a polyamide resin having an aromatic ring and/or a hetero ring, to a liquid containing a disperse dye having an aromatic ring and/or a hetero ring and water.

Advantageous Effects of Invention

The present invention unable to provide a filament that does not impair the strength that is intrinsic to the filament and contains a disperse dye, and has excellent color fastness, a material using the filament, and a method for producing the material.

DESCRIPTION OF EMBODIMENTS

Hereinafter, embodiments for carrying out the present invention (referred to simply as “the present embodiment” below) will be described in detail. Note that the following present embodiments are examples for describing the present invention, and the present invention is not limited to the present embodiments.
In the present description, “from . . . to . . . ” or “of . . . to . . . ” is used to mean that the numerical values described before and after “to” are included as the lower limit and the upper limit, respectively.
In a description of a group (atomic group) in the present specification, a description not specifying whether the group is a substituted group or an unsubstituted group is meant to include a group (atomic group) having a substituent as well as a group (atomic group) having no substituent. For example, an “alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group). In the present specification, a description not specifying whether the group is a substituted group or an unsubstituted group means that the group is preferably an unsubstituted group.
In the present description, various physical property values and characteristic values are at 23° C. unless otherwise noted.
The filament according to the present embodiment contains a polyamide resin having an aromatic ring and/or a hetero ring, and a disperse dye having an aromatic ring and/or a hetero ring. Such a filament does not impair its strength that is intrinsic to the filament and contains a disperse dye, yet has excellent color fastness Although this reasoning is an assumption, it is assumed that the aromatic ring and/or the hetero ring that the polyamide resin has may interact with the aromatic ring and/or the hetero ring that the disperse dye has, thereby effectively taking the disperse dye into the polyamide filament. On the other hand, an acidic dye such as the one disclosed in Patent Document 1 is ionically bonded to an amino group at a terminal of the polyamide resin and is taken into the polyamide filament.
Note that, in the present description, a filament of the present embodiment before dyeing may be referred to as “polyamide filament”. That is, the polyamide filament does not generally contain a disperse dye having an aromatic ring and/or a hetero ring.
Polyamide Resin Having Aromatic Ring and/or Hetero Ring
The filament according to the present embodiment contains a polyamide resin having an aromatic ring and/or a hetero ring. By using such a polyamide resin, a polyamide filament can be dyed using a disperse dye having an aromatic ring and/or a hetero ring.
Although the type and the like of the polyamide resin having an aromatic ring and/or a hetero ring are not particularly specified, among all structural units constituting the polyamide resin having an aromatic ring and/or a hetero ring, from 20 to 80 mol % are preferably structural units having aromatic rings and/or hetero rings, from 30 to 70 mol % are more preferably structural units having aromatic rings and/or hetero rings, and from 40 to 60 mol % are even more preferably structural units having aromatic rings and/or hetero rings. With such a configuration, a melt spinning method or the like can also be employed in addition to a solution spinning method as a spinning method. Furthermore, even when a solution spinning method is employed, use of a strong acid, such as concentrated sulfuric acid, as a solvent is not required, and the productivity tends to improve.
The polyamide resin having an aromatic ring and/or a hetero ring used in the present embodiment preferably has an aromatic ring.
Furthermore, the structural unit having an aromatic ring and/or a hetero ring is preferably a diamine-derived structural unit having an aromatic ring and/or a hetero ring.
Examples of such a polyamide resin having an aromatic ring and/or a hetero ring used in the present embodiment include nylon 6T, nylon 6/6T, nylon 66/6T, nylon 6I, nylon 66/6I/6, nylon 66/6I, nylon 6T/6I, nylon 6T/12, nylon 66/6T/6I, nylon 9T, nylon 91, nylon 9T, 91, nylon 10T, 1,3-BAC10I (polyamide resin made of 1,3-bis(aminomethyl)cyclohexane, sebacic acid, and isophthalic acid), 1,4-BAC10I (polyamide resin made of 1,4-bis(aminomethyl)cyclohexane, sebacic acid, and isophthalic acid), and xylylenediamine-based polyamide resins described in detail below, and a xylylenediamine-based polyamide resin is preferred.
In the present embodiment, the polyamide resin (hereinafter, in the present description, also referred to as “xylylenediamine-based polyamide resin”) preferably contains diamine-derived structural units and dicarboxylic acid-derived structural units, 70 mol % or more of the diamine-derived structural units being preferably derived from xylylenediamine, and 70 mol % or more of the dicarboxylic acid-derived structural units being preferably derived from α,ω-linear aliphatic dicarboxylic acids having from 4 to 20 carbons. By using the xylylenediamine-based polyamide resin, a filament having a high Young's modulus in addition to excellent color fastness when the disperse dye described above is contained can be obtained. Furthermore, due to low water absorption, changes in mechanical properties, such as Young's modulus and strength, over time is small, and a textile product having tension and stiffness can be obtained.
In the xylylenediamine-based polyamide resin, 70 mol % or more of the diamine-derived structural units are derived from xylylenediamine; preferably 80 mol % or more, more preferably 90 mol % or more, even more preferably 95 mol % or more, and yet even more preferably 99 mol % or more of the diamine-derived structural units are derived from xylylenediamine. The upper limit may be 100 mol %.
The xylylenediamine preferably contains from 30 to 100 mol % of m-xylylenediamine and 0 to 70 mol % of p-xylylenediamine, and more preferably contain from 50 to 100 mol % of m-xylylenediamine and from 0 to 50 mol % of p-xylylenediamine. Furthermore, in the xylylenediamine, the total amount of m-xylylenediamine and p-xylylenediamine is preferably 95 mol % or more, more preferably 99 mol % or more, and even more preferably 100 mol %.
Examples of the diamine component besides xylylenediamine include aliphatic diamines, such as tetramethylenediamine, pentamethylenediamine, 2-methylpentanediamine, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine, decamethylenediamine, dodecamethylenediamine, 2,2,4-trimethyl-hexamethylenediamine, and 2,4,4-trimethylhexamethylenediamine; alicyclic diamines, such as 1,3-bis(aminomethyl)cyclohexane, 1,4-bis(aminomethyl)cyclohexane, 1,3-diaminocyclohexane, 1,4-diaminocyclohexane, bis(4-aminocyclohexyl)methane, 2,2-bis(4-aminocyclohexyl)propane, bis(aminomethyl)decalin, and bis(aminomethyl)tricyclodecane; and diamines having an aromatic ring, such as bis(4-aminophenyl)ether, p-phenylenediamine, and bis(aminomethyl)naphthalene. One type of these can be used, or two or more types can be mixed and used.
In the xylylenediamine-based polyamide resin, 70 mol % or more of the dicarboxylic acid-derived structural units are derived from α,ω-linear aliphatic dicarboxylic acids having from 4 to 20 carbons; however, preferably 80 mol % or more, more preferably 90 mol % or more, even more preferably 95 mol % or more, and yet even more preferably 99 mol % or more of the dicarboxylic acid-derived structural units are derived from α,ω-linear aliphatic dicarboxylic acids having from 4 to 20 carbons. The upper limit may be 100 mol %.
The number of carbons in the α,ω-linear aliphatic dicarboxylic acid having from 4 to 20 carbons is preferably 6 or more, more preferably 9 or more, and even more preferably 11 or more. Furthermore, the number of carbons in the α,ω-linear aliphatic dicarboxylic acid having from 4 to 20 carbons is preferably 16 or less, and more preferably 14 or less. The number of carbons in the α,ω-linear aliphatic dicarboxylic acid having from 4 to 20 carbons is even more preferably 12 or less, and yet even more preferably 12.
Setting the number of carbons to 4 or more allows the water absorption of the xylylenediamine-based polyamide resin to become low and physical properties to be less likely to deteriorate during dyeing of the polyamide filament by application of a liquid containing a disperse dye and water to the polyamide filament. Furthermore, by setting the number of carbons to 20 or less, practically adequate melting point as the polyamide filament can be achieved, and the polyamide filament will be easily usable by various processing as a textile product. In particular, due to high melting point, resistance to heating in dyeing process, drying after dyeing, and heating using an iron or the like becomes high. Furthermore, the Young's modulus can be set adequate, and a filament having tension and stiffness can be obtained.
Specific examples of the α,ω-linear aliphatic dicarboxylic acid having from 4 to 20 carbons include malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, 1,11-undecanedioic acid, and 1,12-dodecanedioic acid. Adipic acid, sebacic acid, and 1,12-dodecanedioic acid are preferred, sebacic acid and 1,12-dodecanedioic acid are more preferred, and 1,12-dodecanedioic acid is even more preferred. When the α,ω-linear aliphatic dicarboxylic acid having from 4 to 20 carbons is 1,12-dodecanedioic acid, the effects described above are particularly remarkably achieved.
Examples of dicarboxylic acid components other than the α,ω-linear aliphatic dicarboxylic acid having from 4 to 20 carbons include phthalic acid compounds, such as isophthalic acid, terephthalic acid, and ortho-phthalic acid; and naphthalenedicarboxylic acid, such as 1,2-naphthalenedicarboxylic acid, 1,3-naphthalenedicarboxylic acid, 1,4-naphthalenedicarboxylic acid, 1,5-naphthalenedicarboxylic acid, 1,6-naphthalenedicarboxylic acid, 1,7-naphthalenedicarboxylic acid, 1,8-naphthalenedicarboxylic acid, 2,3-naphthalenedicarboxylic acid, 2,6-naphthalenedicarboxylic acid, and 2,7-naphthalenedicarboxylic acid. One of these can be used alone, or two or more types can be mixed and used.
Here, “containing diamine-derived structural units and dicarboxylic acid-derived structural units” means that the amide bond constituting the xylylenediamine-based polyamide resin is formed by a bond between a dicarboxylic acid and a diamine. In addition, the xylylenediamine-based polyamide resin contains any other moiety, such as a terminal group, in addition to the dicarboxylic acid-derived structural units and the diamine-derived structural units. Furthermore, the XD-based polyamide may contain a repeating unit having an amide bond not derived from the bond between a dicarboxylic acid and a diamine, a trace amount of an impurity, or the like. Specifically, for the xylylenediamine-based polyamide resin, in addition to the diamine component and the dicarboxylic acid component, a lactam, such as s-caprolactam or laurolactam; or an aliphatic aminocarboxylic acid, such as aminocaproic acid or aminoundecanoic acid; can also be used as a copolymer component constituting the xylylenediamine-based polyamide resin within a range that does not impair the effects of the present invention. In an embodiment of the present invention, preferably 90 mass % or more, more preferably 95 mass % or more, and even more preferably 98 mass % or more, of the xylylenediamine-based polyamide resin is the diamine-derived structural unit or the dicarboxylic acid-derived structural unit.
Furthermore, also for the nylon 6T and the like described above, it is obvious that another structural unit derived from another monomer may be contained within a range that does not impair the effects of the present invention in addition to those containing only hexamethylenediamine and terephthalic acid.
The number average molecular weight (Mn) of the polyamide resin having an aromatic ring and/or a hetero ring used in the present embodiment is preferably from 6000 to 50000, more preferably from 8000 to 48000, and even more preferably from 9000 to 46000. The polyamide resin with a number average molecular weight in such a range provides better molding processability.
Note that the number average molecular weight (Mn) can be determined by gel permeation chromatography (GPC) analysis based on calibration with standard polymethylmethacrylate (PMMA).
The polyamide resin having an aromatic ring and/or a hetero ring may be a crystalline polyamide resin having a clear melting point or an amorphous polyamide resin having no clear melting point but is preferably a crystalline polyamide resin. Using a crystalline polyamide resin allows a disperse dye of the filament of the present embodiment to be less likely to fall off. In particular, when a commingled fiber yarn is formed with a dye that is easily dyed with a disperse dye, such as a polyester filament, if the disperse dye easily fall off from the filament of the present embodiment, color transfer tends to occur; however, the present embodiment can avoid this effectively.
Note that, in the present description, amorphous resin refers to a resin having a crystalline melting enthalpy ΔHm of less than 5 J/g, and crystalline resin refers a resin having a crystal melting enthalpy ΔHm of 5 J/g or more.
When the polyamide resin having an aromatic ring and/or a hetero ring has a melting point, the melting point is preferably from 170 to 250° C. Such a range can provide superior molding processability and can provide a molded product having superior thermal resistance.
Note that, in an embodiment of the present invention, the melting point means a temperature at which an endothermic peak reaches its maximum during a temperature increase when observed by a differential scanning calorimetry (DSC) method. Specifically, using a DSC instrument and a sample amount of 1 mg, a polyamide resin is melted by heating to a temperature that is equal to or higher than a predicted melting point from room temperature (25° C.) at a temperature increase rate of 10° C./min while nitrogen is streamed at 30 mL/min as an atmosphere gas, and then the melted polyamide resin is rapidly cooled using dry ice, and the temperature is increased again to a temperature that is equal to or higher than the melting point at a rate of 10° C./min. The temperature at which an endothermic peak reaches its maximum at this time is referred to as the melting point.
Furthermore, in the filament of the present embodiment, preferably 70 mass % or more, more preferably 80 mass % or more, and even more preferably 90 mass % or more, and may be 95 mass % or more, of the mass of the filament is the polyamide resin having an aromatic ring and/or a hetero ring. The upper limit is, for example, 99.9 mass % or less.
The filament of the present embodiment may contain only one type of the polyamide resin having an aromatic ring and/or a hetero ring or may contain two or more types thereof. When two or more types of mold release agents are contained, the total amount thereof is preferably in the above range.
Disperse Dye Having Aromatic Ring and/or Hetero Ring
The filament of the present embodiment contains a disperse dye having an aromatic ring and/or a hetero ring. Using a dye having an aromatic ring and/or a hetero ring allows the dye to be easily included in the polyamide filament due to the interaction with an aromatic ring and/or a hetero ring of the polyamide resin having the aromatic ring and/or the hetero ring. Furthermore, the disperse dye is preferably used in a case of making a commingled fiber yarn with a filament that can only be dyed with a disperse dye.
The disperse dye used in the present embodiment is not particularly limited as long as the disperse dye has an aromatic ring and/or a hetero ring, and a known disperse dye can be widely used. Examples of the disperse dye include disperse dyes of an aromatic azo compound, a heterocyclic azo compound, an anthraquinone compound, a quinoline compound, a quinophthalone compound, a benzodifuranone compound, and a coumarin compound. The disperse dye preferably contains at least one selected from the group consisting of an aromatic azo compound, a heterocyclic azo compound, and an anthraquinone compound, and more preferably contains at least one selected from the group consisting of an aromatic azo compound and an anthraquinone compound. By using such a compound, the color fastness tends to further improve. Note that the aromatic azo compound refers to a compound having an aromatic ring (preferably, a benzene ring) and an azo structure (—N═N—). The heterocyclic azo compound refers to a compound having a hetero ring and an azo structure (—N═N—). The anthraquinone compound refers to a compound having an anthraquinone ring. The quinoline compound refers to a compound having a quinoline ring. The quinophthalone compound refers to a compound having a quinophthalone ring. The benzodifuranone compound refers to a compound having a benzodifuranone ring. The coumarin compound refers to a compound having a coumarin ring. These compounds preferably have molecular weights of 300 to 1000. By using a compound having such a molecular weight, the polyamide filament tends to effectively incorporate the disperse dye.
The disperse dye used in the present embodiment is preferably a disperse dye having a skeleton represented by Formula (C1) below or a skeleton represented by Formula (C2) below. By using such a compound, the color fastness tends to further improve. Note that a compound having a skeleton means a compound including structures represented by Formula (C1) and Formula (C2) or structures in which hydrogen atom(s) contained in the structures represented by Formula (C1) and Formula (C2) are replaced with substituent(s) (e.g., substituent T described below):
Ar¹—N═N—Ar² Formula (C1)
In Formula (C1), Ar¹and Ar²each independently represent an aryl group having from 6 to 40 carbons or a heteroaryl group having from 5 to 40 carbons.
In Formula (C1), the aryl group having from 6 to 40 carbons (preferably from 6 to 20 carbons) include a phenyl group and a naphthyl group, and a phenyl group is preferred. Examples of the heteroaryl group having from 5 to 40 carbons (preferably from 5 to 20 carbons) include a pyrrolyl group, a pyrazolyl group, a pyridalyl group, a benzimidazolyl group, an oxadiazolyl group, a thiadiazolyl group, a tetrahydroquinolyl group, a dihydrobenzoxazinyl group, a tetrahydroisoquinolyl group, a thienyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, and a benzisothiazolyl group.
Hydrogen atom(s) contained in Formula (C1) (including hydrogen atoms contained in Ar¹and Ar²) may be replaced with substituent(s), and examples of the substituent include a substituent T described below. The substituent may be further replaced with another substituent.
Examples of the substituent T include alkyl groups (having preferably from 1 to 24 carbons, more preferably from 1 to 12 carbons, and even more preferably from 1 to 6 carbons), cycloalkyl groups (having preferably from 3 to 24 carbons, more preferably from 3 to 12 carbons, and even more preferably from 3 to 6 carbons), aralkyl groups (having preferably from 7 to 21 carbons, more preferably from 7 to 15 carbons, and even more preferably from 7 to 11 carbons), alkenyl groups (having preferably from 2 to 24 carbons, more preferably from 2 to 12 carbons, and even more preferably from 2 to 6 carbons), cycloalkenyl groups (having preferably from 3 to 24 carbons, more preferably from 3 to 12 carbons, and even more preferably from 3 to 6 carbons), a hydroxyl group, amino groups (having preferably from 0 to 24 carbons, more preferably from 0 to 12 carbons, and even more preferably from 0 to 6 carbons), a thiol group, a carboxyl group, aryl groups (having preferably from 6 to 22 carbons, more preferably from 6 to 18 carbons, and even more preferably from 6 to 10 carbons), acyl groups (having preferably from 2 to 12 carbons, more preferably from 2 to 6 carbons, and even more preferably from 2 to 3 carbons), acyloxy groups (having preferably from 2 to 12 carbons, more preferably from 2 to 6 carbons, and even more preferably from 2 to 3 carbons), aryloyl groups (having preferably from 7 to 23 carbons, more preferably from 7 to 19 carbons, and even more preferably from 7 to 11 carbons), aryloyloxy groups (having preferably from 7 to 23 carbons, more preferably from 7 to 19 carbons, even more preferably from 7 to 11 carbons), carbamoyl groups (having preferably from 1 to 12, more preferably from 1 to 6 carbons, and even more preferably from 1 to 3 carbons), sulfamoyl groups (having preferably from 0 to 12 carbons, more preferably from 0 to 6 carbons, and even more preferably from 0 to 3 carbons), a sulfo group, alkylsulfonyl groups (having preferably from 1 to 12 carbons, more preferably from 1 to 6 carbons, and even more preferably from 1 to 3 carbons), arylsulfonyl groups (having preferably from 6 to 22 carbons, more preferably from 6 to 18 carbons, and even more preferably from 6 to 10 carbons), hetero ring groups (having preferably from 1 to 12 carbons, more preferably from 1 to 8 carbons, and even more preferably 2 to 5 carbons, and preferably contains a five-membered ring or a six-membered ring), (meth)acryloyl groups, (meth)acryloyloxy groups, halogen atoms (e.g., fluorine atom, chlorine atom, bromine atom, and iodine atom), an oxo group (═O), imino groups (═NR^N), and alkylidene groups (═C(R^N)₂). R^Nis preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom. The alkyl moiety and alkenyl moiety contained in each substituent may be linear or branched and may be in a chain form or a cyclic form. In a case where the substituent T is a group that may accept a substituent, the substituent T may further contain another substituent T. For example, an alkyl group may be a halogenated alkyl group, or may be a (meth)acryloyloxyalkyl group, an aminoalkyl group, or a carboxyalkyl group. In a case where the substituent is a group that may form a salt of a carboxyl group or an amino group, the group may form a salt.
Hydrogen atom(s) contained in Formula (C2) may be replaced with substituent(s), and examples of the substituent include a substituent T described below. The substituent may be further replaced with another substituent.
An example of the disperse dye having a skeleton represented by Formula (C1) is the following compound:
An example of the disperse dye having a skeleton represented by Formula (C2) is the following compound:
In addition to these, as the disperse dye having an aromatic ring and/or a hetero ring, for example, those described in paragraphs [0040] to [0043] of JP 2019-182780 A and those described in paragraphs [0027] to [0045] of JP 2018-168486 A can be used, the contents of which are incorporated herein by reference.
The content of the disperse dye having an aromatic ring and/or a hetero ring in the filament of the present embodiment is preferably 0.1 mass % or more, more preferably 0.4 mass % or more, and even more preferably 0.5 mass % or more. Setting the content to not less than the lower limit value allows a target tone of color to be effectively exhibited. Furthermore, the content of the disperse dye having an aromatic ring and/or a hetero ring in the filament of the present embodiment is preferably 5 mass % or less, more preferably 3.5 mass % or less, and even more preferably 3 mass % or less. By setting the content to not greater than the upper limit value, differing from a target tone of color is prevented, and color transfer can be effectively suppressed at the time of use as a textile product.
The filament of the present embodiment may contain only one type of the disperse dye having an aromatic ring and/or a hetero ring or may contain two or more types thereof. When two or more types of mold release agents are contained, the total amount thereof is preferably in the above range.

Other Components

The filament of the present embodiment may contain another component besides the polyamide resin having an aromatic ring and/or a hetero ring and the disperse dye having an aromatic ring and/or a hetero ring.
The filament of the present embodiment may contain a polyamide resin besides the polyamide resin having an aromatic ring and/or a hetero ring, and/or a thermoplastic resin besides the polyamide resin.
Examples of the polyamide resin other than the polyamide resin having an aromatic ring and/or a hetero ring include aliphatic polyamide resins such as polyamide 4, polyamide 6, polyamide 11, polyamide 12, polyamide 46, polyamide 66, polyamide 6/66, polyamide 610, and polyamide 612.
Furthermore, examples of the thermoplastic resin other than the polyamide resin include polyolefin resins such as polyethylene and polypropylene; polyester resins such as polyethylene terephthalate and polybutylene terephthalate; polycarbonate resins; polyoxymethylene resins; polyether ketones, polyether sulfones, and thermoplastic polyether imides.
The content of the polyamide resin other than the polyamide resin having an aromatic ring and/or a hetero ring and the thermoplastic resin other than the polyamide resin is, in a case where these resins are contained, preferably from 1 to 10 mass % in the filament of the present embodiment.
The filament of the present embodiment may further contain additives such as antioxidants, thermal stabilizers, hydrolysis-resistance improving agents, weather resistant stabilizers, matting agents, UV absorbers, nucleating agents, plasticizers, flame retardants, antistatic agents, anti-gelling agents, release agents, and surfactants within a scope that does not impair the object and effect of the present invention. For details of these additives, reference can be made to the descriptions in paragraphs [0130] to [0155] of JP 4894982 B, paragraph [0021] of JP 2010-281027 A, and paragraph [0036] of JP 2016-223037 A, the contents of which are incorporated in the present specification. In a case where these components are contained, the content of these components is preferably from 0.001 to 5 mass % in the filament of the present embodiment.
In the filament of the present embodiment, a total of the polyamide resin having an aromatic ring and/or a hetero ring, the disperse dye having an aromatic ring and/or a hetero ring, and optionally blended other component(s) (e.g., resins and additives) is adjusted to 100 mass %.

Form and Physical Property of Filament

The filament of the present embodiment may be a monofilament or a multifilament and is preferably a multifilament. By forming a multifilament, processing into various textile forms, such as woven fabric, knitted fabric, braids, and non-woven fabric, becomes easy.
In a case where the filament of the present embodiment is a multifilament, the number of filaments constituting one multifilament is preferably 10 or more, more preferably 20 or more, and even more preferably 30 or more. Furthermore, the upper limit of the number of the filaments constituting one multifilament is preferably 100 or less, more preferably 60 or less, and even more preferably 55 or less. Setting the number in such a range allows fusion of single yarns during spinning to be prevented while patches of single fiber fineness during spinning is suppressed.
The cross section of the filament of the present embodiment is typically circular. Note that the circular includes those roughly circular in the technical field of the present embodiment in addition to circular in a geometrical sense. Furthermore, the cross section of the filament in the present embodiment may be a shape other than circular, and examples thereof include flat shapes such as an ellipse and an oval.
The filament of the present embodiment preferably has a single fiber fineness from 2.0×10⁻⁵to 50 dtex. By setting the single fiber fineness to not lower than the lower limit value, stable spinning can be performed, and adequate strength can be imparted to a textile product when processing into various textile product forms is performed. By setting the single fiber fineness to not higher than the upper limit value, the dye readily infiltrates into an inner part of a fiber, and more vivid dyeing can be performed. The lower limit of the single fiber fineness is preferably 8.0×10⁻⁵dtex or more, more preferably 9.0×10⁻³dtex or more, even more preferably 1.0×10⁻²dtex or more, yet even more preferably 0.5 dtex or more, and yet even more preferably 1 dtex or more. Furthermore, the upper limit of the single fiber fineness is preferably 40 dtex or less, more preferably 30 dtex or less, even more preferably 25 dtex or less, yet even more preferably 20 dtex or less, yet even more preferably 18 dtex or less, and yet even more preferably 10 dex or less.
Furthermore, the filament of the present embodiment is preferably from 10 to 1000 dtex in a case where the filament is a multifilament. By setting the single fiber fineness to not lower than the lower limit value, stable molding can be performed, and adequate strength can be imparted to a textile product when processing into various textile products is performed. By setting the single fiber fineness to not higher than the upper limit value, the dye readily infiltrates into an inner part of a fiber, and more vivid dyeing can be performed. The lower limit of the fineness of the multifilament is preferably 40 dtex or more, more preferably 60 dtex or more, and even more preferably 100 dtex or more. Furthermore, the upper limit of the fineness of the multifilament is preferably 800 dtex or less, more preferably 600 dtex or less, and even more preferably 500 dtex or less.
The fineness is measured in accordance with the method described in Examples below.
The filament length (mass average length) of the present embodiment is not particularly specified but is preferably 5 mm or more, more preferably 0.1 m or more, even more preferably 1 m or more, and yet even more preferably 100 m or more. Furthermore, the upper limit value of the length of the filament (mass average length) is preferably 20000 m or less, more preferably 1000 m or less, and even more preferably 100 m or less.
For the filament of the present embodiment, the elongation percentage measured in accordance with the JIS L 1013:2010 is preferably 30% or more. By setting the elongation percentage to 30% or more, breakage of yarn during processing can be effectively suppressed. The elongation percentage is preferably 35% or more, and more preferably 40% or more. The upper limit of the elongation percentage is preferably 70% or less, and more preferably 60% or less. By setting the elongation percentage to not higher than the upper limit value, processability upon processing into various textile forms, such as woven fabric, knitted fabric, braids, and non-woven fabric, tends to further improve.
The filament of the present embodiment preferably has high color fastness. Specifically, when a material containing the filament described in detail below is formed, the color fastness is preferably 3 or more. The upper limit is preferably 5 or less. The color fastness is a grade corresponding to a degree of coloration on a white cotton fabric that is evaluated based on a gray scale for contamination in accordance with JIS L 0805:2011 when the material is fixed on a desk, and a 1 kg cylindrical weight fully covered by cotton No. 3-1 specified in JIS L 0803:2011 is placed on the material and moved back and forth for 100 times.

Material

The material of the present embodiment contains a filament, and the filament contained in the material contains a polyamide resin having an aromatic ring and/or a hetero ring, and a disperse dye having an aromatic ring and/or a hetero ring. The material containing such a filament is suitably used for various purposes because of excellent design. The filament is preferably the filament of the present embodiment.
The filament of the present embodiment may be used as is or may be processed into a material such as commingled fiber yarn, braids, twisted string, yarn, or string having a core-in-sheath structure. In a case where a commingled fiber yarn is formed, the filament is preferably combined with another thermoplastic resin filament, reinforcement fiber (filament) such as a carbon fiber or glass fiber, or the like.
The material of the present embodiment may be, for example, a woven fabric, knitted fabric, or non-woven fabric made of the filament of the present embodiment. The material of the present embodiment may include the filament contained in the material contains a polyamide resin having an aromatic ring and/or a hetero ring and a disperse dye having an aromatic ring and/or a hetero ring by, for example, dyeing woven fabric, knitted fabric, or non-woven fabric constituting the polyamide filament. The woven fabric, knitted fabric, non-woven fabric, and the like in the present embodiment include woven fabric, knitted fabric, non-woven fabric, and the like made of commingled fiber yarn, braids, twisted string, and the like using the filament of the present embodiment. The material of the present embodiment is preferably knitted fabric or woven fabric.
The woven fabric may be any of a plain weave, a twill weave, a satin weave, a leno weave, and the like. An example of the knitted fabric is plain knitting.
The material of the present embodiment preferably has a density of 1.10 to 1.25 g/cm³.
The material of the present embodiment preferably has high color fastness. Specifically, the color fastness is preferably 3 or more. The upper limit is preferably 5 or less. Note that the color fastness is a grade corresponding to a case where the material is fixed on a desk, a 1 kg cylindrical weight fully covered by cotton No. 3-1 specified in JIS L 0803:2011 is placed on the material and moved back and forth for 100 times, and a degree of coloration of the white cotton fabric is evaluated based on a gray scale for contamination in accordance with JIS L 0805:2011.
The material of the present embodiment refers to a material in which the filament of the present embodiment keeps a filament form. Note that keep means that a filament form is substantially maintained, and includes a case where a part (e.g., 10 vol. % or less) of a filament is melted and bonded with, for example, another filament or reinforcement fiber.

Production Method

The filament of the present embodiment is obtained by shaping a composition containing a polyamide resin having an aromatic ring and/or a hetero ring. The shaping method can be freely chosen, and shaping into a desired shape may be performed by a freely chosen known shaping method such as melt spinning. For example, reference can be made to the disclosure of paragraphs [0051] to [0058] of WO 2017/010389, the contents of which are incorporated herein by reference.
In the present embodiment, in particular, the polyamide filament is preferably produced by a melt spinning method or an electrospinning method. The melt spinning method is a method in which a composition containing a polyamide resin having an aromatic ring and/or a hetero ring is extruded through a multi-hole die by an extruder and stretched by passing through a roll. Furthermore, the electrospinning method is a method in which a composition containing a polyamide resin having an aromatic ring and/or a hetero ring is dissolved in a solvent, and when the dissolved resin solution is discharged from a thin nozzle, an electric field is applied during discharging of the resin solution to electrify the resin solution itself, thus stretching is performed by the potential difference, and the solvent is removed.
Furthermore, for the filament of the present embodiment, preferably, a composition containing a polyamide resin having an aromatic ring and/or a hetero ring is typically formed into a polyamide filament first, and then a disperse dye is allowed to infiltrate into an inner part. Specifically, in the present embodiment, a polyamide filament is preferably dyed by applying (preferably infiltration) a liquid containing a disperse dye having an aromatic ring and/or a hetero ring and water to a polyamide filament containing a polyamide resin having an aromatic ring and/or a hetero ring.
In the present embodiment, when the liquid containing the disperse dye having an aromatic ring and/or a hetero ring and water is applied to the polyamide filament, the liquid containing the disperse dye having an aromatic ring and/or a hetero ring and water is preferably heated. The heating temperature is preferably 60° C. or higher, more preferably 100° C. or higher, even more preferably 120° C. or higher, and yet even more preferably 125° C. or higher. The upper limit value of the heating temperature is preferably 180° C. or lower, more preferably 160° C. or lower, even more preferably 155° C. or lower, and yet even more preferably 150° C. or lower. By setting the heating temperature to not lower than the lower limit value, color fastness of the polyamide filament after dyeing can be enhanced in addition to improved dye affinity. By setting the heating temperature to not higher than the upper limit value, hydrolysis during dyeing can be suppressed, and reduction in tensile strength can be more effectively suppressed.
Furthermore, the filament of the present embodiment is preferably stretched. The stretching may be performed before or after application of the liquid containing the disperse dye having an aromatic ring and/or a hetero ring and water to the polyamide filament, and is preferably performed before the application. The stretching ratio is preferably from 1.5 to 6.0-fold, and more preferably from 2.0 to 5.5-fold. By the stretching, molecular chains are oriented in one direction, and tensile strength of the filament can be further enhanced.
The application time of the liquid containing the disperse dye and water is preferably from 10 to 100 minutes.
Furthermore, in a case where the filament of the present embodiment is formed into a material such as knitted fabric or woven fabric, processing into a material such as knitted fabric or woven fabric may be performed after the polyamide filament is dyed. However, dyeing may be performed after the polyamide filament is processed into a material such as knitted fabric or woven fabric. By dyeing the polyamide filament after the polyamide filament is processed into a material such as knitted fabric or woven fabric, processing cost can be reduced, and it becomes easy to produce a wide variety of types in a small amount.
As a method for dyeing, application of a liquid containing a disperse dye having an aromatic ring and/or a hetero ring and water to the polyamide filament or to the knitted fabric or woven fabric made of the polyamide filament is preferred.
The disperse dye having an aromatic ring and/or a hetero ring in the liquid containing the disperse dye having an aromatic ring and/or a hetero ring and water is synonymous with the disperse dye having an aromatic ring and/or a hetero ring described above. In the liquid containing the disperse dye and water, from 0.01 to 1 mass % of the liquid is preferably the disperse dye and from 0.05 to 0.7 mass % of the liquid is preferably water. Furthermore, the liquid containing the disperse dye and water may contain another component besides the disperse dye and the water or may contain no such component. Examples of the component other than the disperse dye and water include anionic or nonionic-anionic surfactants, acetic acid, biphenyl, trichlorobenzene, methylnaphthalene, o-benzylphenol, p-benzylphenol, o-phenylphenol, propyl benzoate, butyl benzoate, 2-hydroxy-4-methoxybenzophenone, butyl paraben, methyl salicylate, and vanillin. The liquid containing the disperse dye and water may contain only one type of the disperse dye or may contain two or more types thereof. When two or more types of mold release agents are contained, the total amount thereof is preferably in the above range.

Applications

The filament of the present embodiment is suitably used in bags, socks, clothing, carpets, fishing line, fishnet, industrial materials, gut for rackets, and the like.
The filament and the material of the present embodiment are widely used in applications including components for transportation devices, such as automobiles; general mechanical components; precision mechanical components; electronic and electrical equipment components; OA equipment components; building materials and housing-related components; medical devices; leisure sporting goods (e.g., fishing line); amusement goods; medical products; food packaging films; daily necessities, such as clothing; and defense and aerospace products.
The filament of the present embodiment may be wound around a core material. That is, the filament of the present embodiment may be a wound body including a core material and a filament wound around the core material.

EXAMPLES

The present invention will be described more specifically with reference to examples below. Materials, amounts used, proportions, processing details, processing procedures, and the like described in the following examples can be appropriately changed as long as they do not depart from the spirit of the present invention. Thus, the scope of the present invention is not limited to the specific examples described below.
If a measuring device used in the examples is not readily available due to discontinuation or the like, another device with equivalent performance can be used for measurement.

1. Raw Material

Synthesis of Polyamide MP12

In a jacketed reactor equipped with an agitator, a partial condenser, a cooler, a thermometer, a dripping tank, and a nitrogen gas introduction tube, precisely weighed 60.00 mol of 1,12-dodecanedioic acid was placed, then the reactor was sufficiently purged with nitrogen and the temperature was increased to 180° C. under a small amount of nitrogen gas stream, and thus the 1,12-dodecanedioic acid was dissolved to form a uniformly fluidized state. To this, 60 mol of p/m-xylylenediamine containing a diamine component in which 30 mol % was p-xylylenediamine and 70 mol % was m-xylylenediamine was added dropwise over 160 minutes while agitation was performed. At this time, the inner pressure of the reaction system was at normal pressure, and the internal temperature was continuously increased to 250° C. The water that distilled out along with the dropwise addition of the p/m-xylylenediamine was removed from the system through the partial condenser and the cooler. After completion of the dropwise addition of the p/m-xylylenediamine, the liquid temperature of 250° C. was maintained to continue the reaction for 10 minutes. Thereafter, the internal pressure of the reaction system was continuously reduced to 600 Torr over 10 minutes, and then the reaction was continued for 20 minutes. At this time, the reaction temperature was continuously increased to 260° C. After completion of the reaction, by application of a pressure of 0.3 MPa using a nitrogen gas in the reactor, the polymer was taken out as a strand from a nozzle at a bottom part of the polymerization tank and cooled with water. Then, the strand was cut into a pallet shape, and thus pellets of a melt polymerization product were obtained. At room temperature, the obtained pellets were charged in a tumbler (rotational vacuum chamber) equipped with a jacket of heat medium heating. Inside of the chamber was set to a reduced pressure condition (0.5 to 10 Torr) while the tumbler was rotated, the circulating heat medium was heated to 150° C., and the pellet temperature was increased to 130° C. and this temperature was maintained for 3 hours. Thereafter, nitrogen was introduced again to set the pressure to normal pressure, and cooling was started. When the temperature of the pellets became 70° C. or lower, the pellets were taken out from the chamber, and thus a solid phase polymerization product was obtained.
The melting point of the obtained polyamide resin (MP12) was 206° C.

Synthesis of Polyamide MXD12

In a jacketed reactor equipped with an agitator, a partial condenser, a cooler, a thermometer, a dripping tank, and a nitrogen gas introduction tube, precisely weighed 60.00 mol of 1,12-dodecanedioic acid was placed, then the reactor was sufficiently purged with nitrogen and the temperature was increased to 180° C. under a small amount of nitrogen gas stream, and thus the 1,12-dodecanedioic acid was dissolved to form a uniformly fluidized state. To this, 60 mol of m-xylylenediamine was added dropwise over 160 minutes while agitation was performed. At this time, the inner pressure of the reaction system was at normal pressure, and the internal temperature was continuously increased to 250° C. The water that distilled out along with the dropwise addition of the m-xylylenediamine was removed from the system through the partial condenser and the cooler. After completion of the dropwise addition of the m-xylylenediamine, the liquid temperature of 250° C. was maintained to continue the reaction for 10 minutes. Thereafter, the internal pressure of the reaction system was continuously reduced to 600 Torr over 10 minutes, and then the reaction was continued for 20 minutes. At this time, the reaction temperature was continuously increased to 260° C. After completion of the reaction, by application of a pressure of 0.3 MPa using a nitrogen gas in the reactor, the polymer was taken out as a strand from a nozzle at a bottom part of the polymerization tank and cooled with water. Then, the strand was cut into a pallet shape, and thus pellets of a melt polymerization product were obtained. At room temperature, the obtained pellets were charged in a tumbler (rotational vacuum chamber) equipped with a jacket of heat medium heating. Inside of the chamber was set to a reduced pressure condition (0.5 to 10 Torr) while the tumbler was rotated, the circulating heat medium was heated to 150° C., and the pellet temperature was increased to 130° C. and this temperature was maintained for 3 hours. Thereafter, nitrogen was introduced again to set the pressure to normal pressure, and cooling was started. When the temperature of the pellets became 70° C. or lower, the pellets were taken out from the chamber, and thus a solid phase polymerization product was obtained.
The melting point of the obtained polyamide resin (MXD12) was 190° C.

Synthesis Example of Polyamide MP10 (M/P Ratio=7:3)

In a jacketed reactor equipped with an agitator, a partial condenser, a cooler, a thermometer, a dripping tank, and a nitrogen gas introduction tube, sebacic acid was placed, heated and dissolved in a nitrogen atmosphere, then, while the contents were agitated and while a diamine mixture (available from Mitsubishi Gas Chemical Company, Inc.) having a molar ratio of m-xylylenediamine to p-xylylenediamine of 7:3 was gradually added dropwise under increased pressure (0.35 MPa) to give a molar ratio of the diamines to sebacic acid of approximately 1:1, the temperature was increased to 235° C. After completion of the dropwise addition, the reaction was continued for 60 minutes, and the amount of components with a molecular weight of 1000 or less was adjusted. After completion of the reaction, the contents were taken out in the form of strands and pelletized with a pelletizer, and a polyamide resin (MP10, M/P=7:3) was obtained.
The melting point of the obtained polyamide resin (MP10) was 215° C.

Synthesis of Polyamide 1,3-BAC10I

In a pressure-resistant reaction vessel having an internal volume of 50 L equipped with an agitator, a partial condenser, a total condenser, a pressure regulator, a thermometer, a drop tank and a pump, an aspirator, a nitrogen-introducing tube, a bottom drain valve, and a strand die, precisely weighed 7000 g (34.61 mol) of sebacic acid (available from Itoh Oil Chemicals Co., Ltd.), 5750 g (34.61 mol) of isophthalic acid (available from A.G. International Chemical Co., Inc.), 3.3 g (0.019 mol) of calcium hypophosphite (available from Kanto Chemical Co., Inc.), and 1.4 g (0.018 mol) of sodium acetate (available from Kanto Chemical Co., Inc.) were placed. Then, the inside of the reaction vessel was adequately purged with nitrogen and then sealed, and the temperature was increased to 200° C. while agitation was performed and the inside of the vessel was maintained at 0.4 MPa. After the temperature reached 200° C., drop-wise addition of 9847 g (69.22 mol) of 1,3-bis(aminomethyl)cyclohexane (1,3-BAC; isomer molar ratio: cis/trans=75/25) (available from Mitsubishi Gas Chemical Company, Inc.) stored in the drop tank to the raw materials in the reaction vessel was started, and the temperature in the reaction vessel was raised to 295° C. while keeping the pressure in the vessel at 0.4 MPa and removing the generated condensed water out of the system. After the completion of dropwise addition of 1,3-BAC, the pressure in the reaction vessel was gradually returned to normal pressure, and then the aspirator was used to reduce the pressure inside the reaction tank to 80 kPa to remove the condensed water. Agitation torque of the agitator was observed under a reduced pressure, and agitation was terminated when a predetermined torque was reached. Then, the inside of the reaction tank was pressurized with nitrogen, the bottom drain valve was opened, the polymer was extruded from the strand die to form a strand and then cooled and pelletized by using a pelletizer, and thus a polyamide resin (1,3-BAC10I) was obtained. When the crystal melting enthalpy ΔHm (X) of the polyamide resin in the temperature increasing process was measured in accordance with JIS K 7121, the crystal melting enthalpy was 0 J/g, and the polyamide resin was an amorphous polyamide resin.
PA6: AMILAN CM1017, available from Toray Industries, Inc.; melting point: 225° C.
PA66: AMILAN CM3001, available from Toray Industries, Inc.; melting point: 265° C.
Aromatic azo compound: Disperse Blue 14, available from Tokyo Chemical Industry Co., Ltd.
Anthraquinone compound: Disperse Diazo Black 3BF, available from Tokyo Chemical Industry Co., Ltd.

Examples 1 to 6 and Comparative Examples 1 and 2

Production of Polyamide Filament

The polyamide resin listed in Table 1 was melted by using a single screw extruder and spun through a spinneret (the hole count is listed in Table 1) at the spinning temperature of 290° C. After the spun polyamide filament was passed through a hot zone and a cooling zone, the polyamide filament that was approximately at room temperature (hereinafter, also referred to as “filament before stretching”) was immersed in a sizing agent (DELION PP-807, available from Takemoto Oil & Fat Co., Ltd.), formed into a bundle form, and drawn by a roll 1 which was not heated and thus stretched continuously without being wound temporarily. The filament before stretching drawn by the roll 1 was heated by passing through a roller 2 heated at 80° C., subsequently passed through a roller 2, a roller 3, and a roller 4, which were heated at 170° C., and then wound by a winder. At this time, stretching was performed by providing a speed ratio for the roller 2 and the roller 3, and the speed ratio was adjusted to achieve a stretching ratio to 2 to 4. Furthermore, relaxation was performed by providing a speed ratio of the roller 3 and the roller 4, and the number of rotation of the roller 4 was slower than that of the roller 3 by 4%.

Fineness

In accordance with JIS L 1013:2010, the fineness of the filament (fineness based on corrected mass of multifilament, single fiber fineness) was measured. The fineness was expressed in units of dtex.

Tensile Strength

In accordance with JIS L 1013:2010, after the filament was subjected to humidity control in an environment at 23° C. and 50% RH, measurement was performed under conditions of a distance between chucks of 50 cm and a tensile speed of 50 cm/min. Calculation was performed by dividing the load at the time when the filament was broken by the fineness (fineness based on corrected mass) of the filament.
Units are shown in cN/dtex.

Elongation Percentage

In accordance with JIS L 1013:2010, after the filament was subjected to humidity control in an environment at 23° C. and 50% RH, measurement was performed under conditions of a distance between chucks of 50 cm and a tensile speed of 50 cm/min. The elongation percentage was determined by the following equation based on a distance between chucks at the time when the filament was broken.
Elongation percentage={[(distance between chucks at breakage)−(distance between chucks before test)]/(distance between chucks before test)}×100

- Units are shown in %.

Adsorptivity

Using the filament obtained above, evaluation of adsorptivity of dye was performed in accordance with the following method.
By using the polyamide filament, a tubular knitted fabric having a number of wales of 30/2.54 cm and a number of courses of 30/2.54 cm was produced and immersed in an aqueous solution in which an azo compound was dispersed (dye concentration: 0.5 mass %) or an aqueous solution in which an anthraquinone compound was dispersed (dye concentration: 0.5 mass %), and while being immersed, heated at 130° C. for 30 minutes and then cooled to room temperature (25° C.). The tubular knitted fabric was taken out from the solution, and subsequently immersed in an aqueous solution containing 1 g/L of sodium hydroxide (available from Tokyo Chemical Industry Co., Ltd.), 1 g/L of hydrosulfite (available from Tokyo Chemical Industry Co., Ltd.), and 1 g/L of Bisnol SK (available from Lion Specialty Chemicals Co., Ltd.), and while being immersed, heated at 80° C. for 10 minutes and then cooled to room temperature (25° C.). The tubular knitted fabric was taken out from the solution and rinsed with water, and then water was wiped.
After the tubular knitted fabric is naturally dried, the tubular knitted fabric was fixed on a desk, a cylindrical weight covered by white cotton fabric (cotton No. 3-1 specified in JIS L 0803:2011) was placed on the tubular knitted fabric and moved back and forth for 100 times. Based on occurrence of color transfer to the white cotton fabric, adsorptivity was evaluated. Five experts conducted the evaluation, and the adsorptivity was decided by a majority vote.
A: Color transfer to the white cotton fabric was not observed at all, or almost no color transfer to the white cotton fabric was observed.
B: Except those evaluated as A. For example, clear color transfer to the white cotton fabric was observed.

Color Fastness

The material was fixed on a desk, and a 1 kg cylindrical weight fully covered by cotton No. 3-1 specified in JIS L 0803:2011 was placed on the material and moved back and forth for 100 times. The degree of coloration on the white cotton fabric was evaluated to which grade it falls based on a corresponding gray scale for contamination in accordance with JIS L 0805:2011.

Tendency of Falling Out of Dye

A tubular knitted fabric produced and dyed in the same manner as for the adsorptivity evaluation described above was fixed on a desk, and white cotton fabric cut into 5 cm square (cotton No. 3-1 specified in JIS L 0803:2011) was placed on the tubular knitted fabric. An electric iron heated at 120 to 130° C. was placed on the white cotton fabric in a manner that the substantially center part of the bottom of the electric iron is in contact, and left for 3 minutes, and then the tubular knitted fabric and the white cotton fabric were taken out. Based on occurrence of color transfer to the white cotton fabric, tendency of falling out of the dye was evaluated. Five experts conducted the evaluation, and the tendency of falling out of the dye was decided by a majority vote.
A: Color transfer to the white cotton fabric was not observed at all, or almost no color transfer was observed.
B: Except those evaluated as A. For example, clear color transfer to the white cotton fabric was observed.

TABLE 1

	Example	Example	Example	Example	Example	Example	Comparative	Comparative
	1	2	3	4	5	6	Example 1	Example 2

Resin type	MP12	MXD12	MP12	MP12	MP10	1,3-	PA6	PA66
						BAC10I
Multifilament fineness (dtex)	233	236	459	78	233	166	235	235
Single fiber fineness (dtex)	4.85	4.92	9.56	3.25	6.47	3.46	6.53	9.79
Number of filaments (Hole count	48	48	48	24	36	48	36	24
of spinneret)
Tensile strength (cN/dtex)	5.1	5.2	5.1	5.3	5.8	3.4	4.0	5.8
Elongation percentage (%)	59	57	50	47	30	32	50	39

Adsorptivity	Aromatic azo compound	A	A	A	A	A	B	B	B
	Anthraquinone compound	A	A	A	A	A	B	B	B
	Color fastness	4	3 to 4	4	4	4	3	2	2
	Tendency of falling out	A	A	A	A	A	B	B	B
	of dye

As is clear from the results above, each of the filaments of embodiments of the present invention had excellent strength and high color fastness (Examples 1 to 6). On the other hand, each of the filaments of Comparative Examples had low color fastness (Comparative Examples 1 and 2).

Claims

1. A filament comprising: a polyamide resin having an aromatic ring and/or a hetero ring; and a disperse dye having an aromatic ring and/or a hetero ring.

2. The filament according to claim 1, wherein the disperse dye comprises at least one selected from an aromatic azo compound, a heterocyclic azo compound, and an anthraquinone compound.

3. The filament according to claim 1, wherein the disperse dye has a skeleton represented by Formula (C1) or a skeleton represented by Formula (C2):

Ar¹—N═N—Ar² Formula (C1)

where in Formula (C1) Ar¹and Ar²each independently represent an aryl group having from 6 to 40 carbons or a heteroaryl group having from 5 to 40 carbons,

4. The filament according to claim 1, wherein a single fiber fineness is from 2.0×10⁻⁵to 50 dtex.

5. The filament according to claim 1, wherein an elongation percentage as measured in accordance with JIS L 1013:2010 is 30% or more.

6. The filament according to claim 1, wherein the filament comprises a polyamide resin containing diamine-derived structural units and dicarboxylic acid-derived structural units, 70 mol % or more of the diamine-derived structural units are derived from xylylenediamine, and 70 mol % or more of the dicarboxylic acid-derived structural units are derived from α,ω-linear aliphatic dicarboxylic acid having from 4 to 20 carbons.

7. The filament according to claim 6, wherein the xylylenediamine contains from 30 to 100 mol % of m-xylylenediamine and from 0 to 70 mol % of p-xylylenediamine.

8. The filament according to claim 6, wherein the dicarboxylic acid contains α,ω-linear aliphatic dicarboxylic acid having from 11 to 14 carbons.

9. The filament according to claim 6, wherein the dicarboxylic acid contains 1,12-dodecanedioic acid.

10. The filament according to claim 1, wherein a filament length is 5 mm or more.

11. The filament according to claim 1, wherein the polyamide resin is a crystalline polyamide resin.

12. The filament according to claim 1, wherein the filament is a multifilament.

13. The filament according to claim 1, wherein, among all structural units constituting the polyamide resin, from 20 to 80 mol % of structural units have aromatic rings and/or hetero rings.

14. A material comprising a filament, the filament contained in the material comprising: a polyamide resin having an aromatic ring and/or a hetero ring; and a disperse dye having an aromatic ring and/or a hetero ring.

15. The material according to claim 14, wherein the filament a filament comprising: a polyamide resin having an aromatic ring and/or a hetero ring; and a disperse dye having an aromatic ring and/or a hetero ring.

16. The material according to claim 14, wherein the material is a knitted fabric or a woven fabric.

17. The material according to claim 14, having color fastness of 3 or more, wherein the color fastness is a grade corresponding to a degree of coloration on a white cotton fabric that is evaluated based on a gray scale for contamination in accordance with JIS L 0805:2011 when the material is fixed on a desk, and a 1 kg cylindrical weight fully covered by cotton No. 3-1 specified in JIS L 0803:2011 is placed on the material and moved back and forth for 100 times.

18. A method for producing a filament according to claim 1, the method comprising applying a polyamide filament containing a polyamide resin having an aromatic ring and/or a hetero ring to a liquid containing a disperse dye and water, the disperse eye having an aromatic ring and/or a hetero ring.

19. A method for producing a material, the method comprising applying a woven fabric or a knitted fabric, the woven fabric formed from a polyamide filament containing a polyamide resin having an aromatic ring and/or a hetero ring, the knitted fabric formed from a polyamide filament containing a polyamide resin having an aromatic ring and/or a hetero ring, to a liquid containing a disperse dye having an aromatic ring and/or a hetero ring and water.

20. The filament according to claim 1, wherein the disperse dye has a skeleton represented by Formula (C1) or a skeleton represented by Formula (C2); and

the filament comprises a polyamide resin containing diamine-derived structural units and dicarboxylic acid-derived structural units, 70 mol % or more of the diamine-derived structural units are derived from xylylenediamine, and 70 mol % or more of the dicarboxylic acid-derived structural units are derived from α,ω-linear aliphatic dicarboxylic acid having from 4 to 20 carbons;

Ar¹—N═N—Ar² Formula (C1)

where in Formula (C1) Ar¹and Ar²each independently represent an aryl group having from 6 to 40 carbons or a heteroaryl group having from 5 to 40 carbons, Formula (C2)