WO2018025673A1 - Nitrogenous-compound-containing polyketone composition, polyketone cured product, optical element, and image display device - Google Patents

Abstract

A polyketone composition contains a polyketone and a nitrogenous compound. The polyketone comprises a structural unit represented by general formula (I) in a main chain thereof. The nitrogenous compound contains a nitrogen atom and at least one group selected from the group consisting of a hydroxymethyl group and a alkoxymethyl group that will bind to the nitrogen atom. In formula (I), each X independently represents an optionally substituted divalent group comprising 1–50 carbon atoms, each Y independently represents an optionally substituted divalent hydrocarbon group comprising 1–30 carbon atoms, and n represents an integer from 3 to 1000.

Description

Polyketone composition, polyketone cured product, optical element and image display device containing nitrogen-containing compound

The present invention relates to a polyketone composition containing a nitrogen-containing compound, a polyketone cured product, an optical element, and an image display device.

An aromatic polyketone having an aromatic ring and a carbonyl group in the main chain has excellent heat resistance and mechanical properties and is used as an engineering plastic. Most of the polymers belonging to the aromatic polyketone are aromatic polyether ketones polymerized using a nucleophilic aromatic substitution reaction, and have an ether bond in the main chain. On the other hand, it is known that an aromatic polyketone having no ether bond in the main chain is superior in heat resistance and chemical resistance to aromatic polyether ketone (for example, Patent Document 1 and Patent Document 2).

Recently, it has been reported that an aromatic polyketone having both high transparency and heat resistance can be obtained by directly polymerizing alicyclic dicarboxylic acid and 2,2′-dialkoxybiphenyl compound by Friedel-Crafts acylation. (For example, refer to Patent Document 3), application to optical components is expected.

When applying a resin material such as an aromatic polyketone to an optical component, lightness and flexibility are expected as characteristics that cannot be obtained with an inorganic material, for example, as compared with an inorganic material. Examples of the application destination of the resin material include a coating material that utilizes light weight, a glass substitute material, and a flexible display that utilizes flexibility. In particular, realization of application to flexible displays has attracted particular attention in recent years.

JP-A-62-273030 JP 2005-272728 A JP 2013-53194 A

Furthermore, when an aromatic polyketone is used as a film, it may be desired to have a high elongation in addition to transparency, heat resistance and chemical resistance.

The present invention has been made in view of the above-mentioned present situation. When a cured film is used, the polyketone composition, the polyketone cured product, and the polyketone cured product that are excellent in heat resistance, transparency, and chemical resistance and exhibit a high elongation rate. It is an object to provide an optical element and an image display apparatus having the above.

The means for solving the above problems include the following embodiments.

<1> a polyketone containing a structural unit represented by the following general formula (I) in the main chain, and
A nitrogen-containing compound having a nitrogen atom and at least one group selected from the group consisting of a hydroxymethyl group and an alkoxymethyl group bonded to the nitrogen atom,
Containing a polyketone composition.

In the general formula (I), each X independently represents a divalent group having 1 to 50 carbon atoms that may have a substituent, and each Y independently has a substituent. Represents a divalent hydrocarbon group having 1 to 30 carbon atoms, and n represents an integer of 3 to 1000.

<2> The polyketone composition according to <1>, wherein, in the general formula (I), each X independently includes a bivalent group having 6 to 50 carbon atoms including an aromatic ring.

<3> In the general formula (I), each X is independently a divalent group represented by at least one selected from the group consisting of the following general formulas (II-1) to (II-3) The polyketone composition according to <1> or <2>.

In general formula (II-1), each R ¹ independently represents a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 30 carbon atoms, and each R ² independently represents a substituted group. A hydrocarbon group having 1 to 30 carbon atoms which may have a group, and each m independently represents an integer of 0 to 3.

In general formula (II-2), each R ¹ independently represents a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 30 carbon atoms, and each R ² independently represents a substituted group. A hydrocarbon group having 1 to 30 carbon atoms which may have a group, m independently represents an integer of 0 to 3, and Z represents an oxygen atom or the following general formula (III-1) ) To (III-7).

In general formulas (III-1) to (III-7), each R ¹ independently represents a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 30 carbon atoms, and R ² represents Each independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ³ and R ⁴ each independently represents a carbon atom which may have a hydrogen atom or a substituent. Represents a hydrocarbon group of 1 to 30. m independently represents an integer of 0 to 3, n independently represents an integer of 0 to 4, and p independently represents an integer of 0 to 2, respectively.

In general formula (II-3), each R ⁵ independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and n is each independently an integer of 0 to 4 Indicates.

<4> The polyketone composition according to any one of <1> to <3>, wherein Y in the general formula (I) includes a divalent saturated hydrocarbon group.

<5> The polyketone composition according to <4>, wherein, in the general formula (I), Y includes a divalent saturated alicyclic hydrocarbon group.

<6> The polyketone composition according to any one of <1> to <5>, wherein in the general formula (I), Y has 6 to 30 carbon atoms.

<7> The polyketone composition according to any one of <1> to <6>, wherein the nitrogen-containing compound has a total number of hydroxymethyl groups and alkoxymethyl groups bonded to nitrogen atoms of 2 to 6. object.

<8> The polyketone composition according to any one of <1> to <7>, further containing a thermal latent acid generator.

<9> The polyketone composition according to any one of <1> to <8>, further containing a solvent.

<10> A cured polyketone, which is a cured product of the polyketone composition according to any one of <1> to <9>.

<11> An optical element having the polyketone cured product according to <10>.

<12> An image display device having the polyketone cured product according to <10>.

ADVANTAGE OF THE INVENTION According to this invention, when it is set as a cured film, it is excellent in heat resistance, transparency, and chemical resistance, and shows the high elongation rate, the polyketone composition and polyketone hardened | cured material, and the optical element and image display apparatus which have polyketone hardened | cured material Can be provided.

Hereinafter, the present invention will be described in detail. However, the present invention is not limited to the following embodiments. In the following embodiments, the components (including element steps and the like) are not essential unless otherwise specified. The same applies to numerical values and ranges thereof, and the present invention is not limited thereto.

In the present disclosure, numerical ranges indicated using “to” indicate ranges including numerical values described before and after “to” as the minimum value and the maximum value, respectively.
In the numerical ranges described stepwise in the present disclosure, the upper limit value or the lower limit value described in one numerical range may be replaced with the upper limit value or the lower limit value of another numerical description. . Further, in the numerical ranges described in the present disclosure, the upper limit value or the lower limit value of the numerical range may be replaced with the values shown in the examples.
In the present disclosure, the content of each component in the composition is the total of the plurality of substances present in the composition unless there is a specific indication when there are a plurality of substances corresponding to each component in the composition. Mean content.
In the present disclosure, the term “layer” or “film” includes only a part of the region in addition to the case where the layer or film is formed over the entire region. The case where it is formed is also included.

In the present disclosure, “a plurality of aromatic rings are non-conjugated to each other or weakly conjugated to each other” means that two aromatic rings are via an ether bond or a methylene bond, or 2,2′-substituted It means that conjugation between aromatic rings is suppressed by being twisted moderately like biphenyl.

In the present disclosure, “excellent transparency” means that the transmittance of visible light (transmittance of visible light having a wavelength of 400 nm) is 80% or more (in terms of a film thickness of 1 μm).

In the present disclosure, “heat resistance” means that the thermal decomposition temperature of the member containing polyketone is 400 ° C. or higher.

In the present disclosure, “high elongation” means that the elongation at break of the formed film is 5% or more.

In the present disclosure, “chemical resistance of the cured film” means that the polyketone film does not peel from the base material even when the film-like polyketone cured product (polyketone film) formed on the silicon substrate is exposed to a chemical solution. Does not dissolve.

<Polyketone composition>
The polyketone composition of the present embodiment binds to a polyketone (hereinafter, also referred to as “specific polyketone”) containing a structural unit represented by the following general formula (I) in the main chain, a nitrogen atom, and the nitrogen atom. A nitrogen-containing compound having a hydroxymethyl group or an alkoxymethyl group (hereinafter also referred to as “specific nitrogen-containing compound”).

In general formula (I), each X independently represents an optionally substituted divalent group having 1 to 50 carbon atoms, and each Y independently represents a substituent. Represents a divalent hydrocarbon group having 1 to 30 carbon atoms, and n represents an integer of 3 to 1000.

The polyketone composition of this embodiment is excellent in heat resistance, transparency, and chemical resistance when it is used as a cured film by having the above-described configuration, and exhibits a high elongation rate. The reason is not clear, but is presumed as follows.
Since the specific polyketone contains a carbonyl group in the main chain, it is excellent in heat resistance and transparency. In addition, since the main chain of the specific polyketone is formed with almost C—C bonds, the molecular chain itself is stable against a chemical solution. And it is thought that the nitrogen atom in a specific nitrogen-containing compound acts, the cohesion force of specific polyketone becomes strong, and elongation rate when a polyketone composition is used as a cured film becomes large. In the case where the specific nitrogen-containing compound functions as a crosslinking agent, the polyketone main chains are cross-linked, and as a result, the specific polyketone is entangled with each other. Conceivable.
Therefore, by using a polyketone composition in which a specific nitrogen-containing compound is combined with a specific polyketone, when it is a cured film, it is excellent in heat resistance, transparency and chemical resistance, and can exhibit a higher elongation. Conceivable.
Hereinafter, each component will be described.

(A) Polyketone The polyketone composition contains a specific polyketone. The specific polyketone contains a structural unit represented by the following general formula (I) in the main chain.

In the general formula (I), each X independently represents a divalent group having 1 to 50 carbon atoms which may have a substituent. Y independently represents a divalent hydrocarbon group having 1 to 30 carbon atoms which may have a substituent. n represents an integer of 3 to 1000. When the divalent group or the divalent hydrocarbon group has a substituent, the carbon number of the divalent group does not include the carbon number of the substituent. The same applies thereafter.

The number of carbon atoms of the divalent group represented by X is 1 to 50, preferably 1 to 30, and more preferably 1 to 24.

The substituent that X may have is not particularly limited, and specific examples include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, an acyl group having 2 to 5 carbon atoms, and the like.

The divalent group represented by X is preferably a hydrocarbon group, and more preferably contains an aromatic ring. When X has an aromatic ring, higher heat resistance tends to be realized.

X preferably contains a divalent group having 6 to 50 carbon atoms including an aromatic ring from the viewpoint of achieving high heat resistance. Examples of the aromatic ring include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a naphthacene ring, a chrysene ring, a pyrene ring, a triphenylene ring, a pentacene ring, and a benzopyrene ring.

Furthermore, X preferably contains a plurality of aromatic rings, and the plurality of aromatic rings are non-conjugated with each other or are divalent groups having a weak conjugated relationship (hereinafter also referred to as “specific aromatic ring groups”). ) Is more preferable. Thereby, good diacylation can be realized at a low reaction temperature during the synthesis of the polyketone, and the polyketone has a high molecular weight and excellent heat resistance. The specific aromatic ring group preferably has 12 to 50 carbon atoms.

Here, “a plurality of aromatic rings are non-conjugated with each other or have a weak conjugated relationship” means that a plurality of aromatic rings are bonded via an ether bond or a methylene bond; It means that conjugation between aromatic rings is suppressed by steric hindrance by a substituent such as 2′-substituted biphenyl.

X includes divalent groups represented by the following general formulas (II-1) to (II-3).

In general formula (II-1), each R ¹ independently represents a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 30 carbon atoms, and each R ² independently represents a substituted group. A hydrocarbon group having 1 to 30 carbon atoms which may have a group, and each m independently represents an integer of 0 to 3. The part with a wavy line means a bond. The same applies thereafter.

From the viewpoint of heat resistance, the hydrocarbon group represented by R ¹ has 1 to 30 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms. When the hydrocarbon group has a substituent, the carbon number of the hydrocarbon group does not include the carbon number of the substituent. The same applies thereafter.

Examples of the hydrocarbon group represented by R ¹ include a saturated aliphatic hydrocarbon group, an unsaturated aliphatic hydrocarbon group, and an alicyclic hydrocarbon group.

Examples of the saturated aliphatic hydrocarbon group represented by R ¹ include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, and n-pentyl. Group, isopentyl group, sec-pentyl group, neo-pentyl group, t-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-icosanyl group, Examples include an n-triacontanyl group. In addition, the saturated aliphatic hydrocarbon group may have an alicyclic hydrocarbon group described below at the terminal portion.

Examples of the unsaturated aliphatic hydrocarbon group represented by R ¹ include an alkenyl group such as a vinyl group and an allyl group, and an alkynyl group such as an ethynyl group. Further, the unsaturated aliphatic hydrocarbon group may have an alicyclic hydrocarbon group to be described later at its terminal portion.

Examples of the alicyclic hydrocarbon group represented by R ¹ include cycloalkyl groups such as cyclohexyl group, cycloheptyl group, cyclooctyl group and norbornyl group, and cycloalkenyl groups such as cyclohexenyl group. The alicyclic hydrocarbon group may have at least one selected from the group consisting of a saturated aliphatic hydrocarbon group and an unsaturated aliphatic hydrocarbon group in the alicyclic ring.

The substituent that the hydrocarbon group represented by R ¹ may have is not particularly limited, and examples thereof include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and an acyl group having 2 to 5 carbon atoms.

In general formula (II-1), each R ² independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent. From the viewpoint of heat resistance, the hydrocarbon group represented by R ² preferably has 1 to 10 carbon atoms, and more preferably 1 to 5 carbon atoms.

Examples of the hydrocarbon group having 1 to 30 carbon atoms represented by R ² include those similar to the hydrocarbon group having 1 to 30 carbon atoms exemplified for R ¹ . In addition, examples of the substituent that the hydrocarbon group represented by R ² may have include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and an acyl group having 2 to 5 carbon atoms.

In general formula (II-1), each m independently represents an integer of 0 to 3, preferably an integer of 0 to 2, and more preferably 0 or 1.

In general formula (II-2), each R ¹ independently represents a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 30 carbon atoms, and each R ² independently represents a substituted group. A hydrocarbon group having 1 to 30 carbon atoms which may have a group; m independently represents an integer of 0 to 3; Z is an oxygen atom or the following general formula (III-1): And a divalent group represented by (III-7).

In general formulas (III-1) to (III-7), each R ¹ independently represents a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 30 carbon atoms, and R ² represents Each independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ³ and R ⁴ each independently represents a carbon atom which may have a hydrogen atom or a substituent. Represents a hydrocarbon group of 1 to 30. m independently represents an integer of 0 to 3, n independently represents an integer of 0 to 4, and p independently represents an integer of 0 to 2, respectively.

R ³ and R ⁴ in the general formula (III-1) are preferably a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent from the viewpoint of heat resistance. Examples of the hydrocarbon group having 1 to 30 carbon atoms represented by R ³ and R ⁴ include the same hydrocarbon groups having 1 to 30 carbon atoms as exemplified for R ¹ in the general formula (II-1). It is done. Examples of the substituent that R ³ and R ⁴ may have include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and an acyl group having 2 to 5 carbon atoms.

N in the general formulas (III-2) and (III-3) each independently represents an integer of 0 to 4, preferably an integer of 0 to 2, and more preferably 0 or 1.
P in the general formulas (III-4), (III-5) and (III-7) each independently represents an integer of 0 to 2, and is preferably 0 or 1.

Each of the details of the ^R 1, ^{R 2,} and m in formula (II-2), is the same as ^R 1, ^{R 2,} and m in Formula (II-1).

In general formula (II-3), each R ⁵ independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and n is each independently an integer of 0 to 4 Indicates.
From the viewpoint of heat resistance, the hydrocarbon group represented by R ⁵ preferably has 1 to 10 carbon atoms, and more preferably 1 to 5 carbon atoms.
Examples of the hydrocarbon group having 1 to 30 carbon atoms represented by R ⁵ include the same hydrocarbon groups having 1 to 30 carbon atoms as exemplified for R ¹ in formula (II-1). Examples of the substituent that R ⁵ may have include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and an acyl group having 2 to 5 carbon atoms.

In general formula (II-3), each n independently represents an integer of 0 to 4, preferably an integer of 1 to 4, more preferably an integer of 1 to 3, or 1 or 2. More preferably.

In the general formula (I), each Y independently represents a divalent hydrocarbon group having 1 to 30 carbon atoms which may have a substituent. The hydrocarbon group represented by Y has 1 to 30 carbon atoms, preferably 4 to 30 carbon atoms, and more preferably 6 to 30 carbon atoms from the viewpoint of heat resistance.

The hydrocarbon group represented by Y preferably contains a saturated hydrocarbon group from the viewpoint of transparency. The saturated hydrocarbon group may be a saturated aliphatic hydrocarbon group or a saturated alicyclic hydrocarbon group. From the viewpoint of achieving both higher heat resistance and transparency, the hydrocarbon group represented by Y preferably includes a saturated alicyclic hydrocarbon group. Since the alicyclic hydrocarbon group is bulky as compared with the aliphatic hydrocarbon group having the same carbon number, it tends to be excellent in solubility in a nitrogen-containing compound and a solvent while maintaining high heat resistance and transparency.
Moreover, the hydrocarbon group represented by Y may include a plurality of types of saturated aliphatic hydrocarbon groups or a plurality of types of saturated alicyclic hydrocarbon groups. Y may contain a combination of a saturated aliphatic hydrocarbon group and a saturated alicyclic hydrocarbon group.

The saturated aliphatic hydrocarbon group represented by Y has 1 to 30 carbon atoms, and preferably 3 to 30 carbon atoms.
Saturated aliphatic hydrocarbon groups include methylene, ethylene, trimethylene, methylethylene, tetramethylene, 1-methyltrimethylene, 2-methyltrimethylene, ethylethylene, 1,1-dimethylethylene Group, 1,2-dimethylethylene group, pentylene group, 1-methyltetramethylene group, 2-methyltetramethylene group, 1-ethyltrimethylene group, 2-ethyltrimethylene group, 1,1-dimethyltrimethylene group, 2,2-dimethyltrimethylene group, 1,2-dimethyltrimethylene group, propylethylene group, ethylmethylethylene group, hexylene group, 1-methylpentylene group, 2-methylpentylene group, 3-methylpentylene group 1-ethyltetramethylene group, 2-ethyltetramethylene group, 1-propyltrimethylene group, 2 Propyl trimethylene group, butyl ethylene group, 1,1-dimethyltetramethylene group, 2,2-dimethyltetramethylene group, 1,2-dimethyltetramethylene group, 1,3-dimethyltetramethylene group, 1,4-dimethyl Tetramethylene group, 1,2,3-trimethyltrimethylene group, 1,1,2-trimethyltrimethylene group, 1,1,3-trimethyltrimethylene group, 1,2,2-trimethyltrimethylene group, 1- Ethyl-1-methyltrimethylene group, 2-ethyl-2-methyltrimethylene group, 1-ethyl-2-methyltrimethylene group, 2-ethyl-1-methyltrimethylene group, 2,2-ethylmethyltrimethylene group Group, heptylene group, octylene group, nonylene group, decylene group, icosanylene group, triacontanilene group and the like.

From the viewpoint of heat resistance, the saturated aliphatic hydrocarbon group is preferably a hexylene group, a methylpentylene group, an ethyltetramethylene group, a propyltrimethylene group, a butylethylene group, a dimethyltetramethylene group, a trimethyltrimethylene group, Examples thereof include an ethylmethyltrimethylene group, a heptylene group, an octylene group, a nonylene group, a decylene group, an icosanylene group, and a triacontanilene group.

The saturated alicyclic hydrocarbon group represented by Y has 3 to 30 carbon atoms, preferably 4 to 30 carbon atoms, more preferably 6 to 30 carbon atoms.
The saturated alicyclic hydrocarbon group includes a cyclopropane skeleton, a cyclobutane skeleton, a cyclopentane skeleton, a cyclohexane skeleton, a cycloheptane skeleton, a cyclooctane skeleton, a cubane skeleton, a norbornane skeleton, and a tricyclo [5.2.1.0] decane skeleton. , A divalent group having an adamantane skeleton, a diadamantane skeleton, a bicyclo [2.2.2] octane skeleton, a decahydronaphthalene skeleton, or the like.

From the viewpoint of heat resistance, the saturated alicyclic hydrocarbon group is preferably a cyclohexane skeleton, a cycloheptane skeleton, a cyclooctane skeleton, a cubane skeleton, a norbornane skeleton, a tricyclo [5.2.1.0] decane skeleton, or an adamantane skeleton. And divalent groups such as a diadamantane skeleton, a bicyclo [2.2.2] octane skeleton, and a decahydronaphthalene skeleton.

Examples of the substituent that the hydrocarbon group represented by Y may have include an amino group, an oxo group, a hydroxyl group, and a halogen atom.

Y preferably contains at least a divalent group represented by at least one selected from the group consisting of the following general formula (IV) and the following general formulas (V-1) to (V-3). More preferably, it contains at least a divalent hydrocarbon group represented by the general formula (IV).

 

Hydrogen atom of adamantane skeleton in general formula (IV), hydrogen atom of cyclohexane skeleton in general formula (V-1), hydrogen atom of decalin skeleton in general formula (V-2), and norbornane in general formula (V-3) The hydrogen atom of the skeleton may be substituted with a hydrocarbon group, an amino group, an oxo group, a hydroxyl group or a halogen atom, respectively. In general formula (IV), each Z independently represents a single bond or a divalent saturated hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.
From the viewpoint of obtaining a flexible cured film, each Z is preferably independently a divalent saturated hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, from the viewpoint of heat resistance. Therefore, Z is preferably a divalent saturated hydrocarbon group having 1 to 5 carbon atoms.

Examples of the divalent saturated hydrocarbon group represented by Z include a methylene group, an ethylene group, a trimethylene group, a methylethylene group, a tetramethylene group, a 1-methyltrimethylene group, a 2-methyltrimethylene group, an ethylethylene group, 1,1-dimethylethylene group, 1,2-dimethylethylene group, pentylene group, 1-methyltetramethylene group, 2-methyltetramethylene group, 1-ethyltrimethylene group, 2-ethyltrimethylene group, 1,1 -Dimethyltrimethylene group, 2,2-dimethyltrimethylene group, 1,2-dimethyltrimethylene group, propylethylene group, ethylmethylethylene group, hexylene group, 1-methylpentylene group, 2-methylpentylene group, 3-methylpentylene group, 1-ethyltetramethylene group, 2-ethyltetramethylene group, 1-propyltrimethyl group Tylene group, 2-propyltrimethylene group, butylethylene group, 1,1-dimethyltetramethylene group, 2,2-dimethyltetramethylene group, 1,2-dimethyltetramethylene group, 1,3-dimethyltetramethylene group, 1,4-dimethyltetramethylene group, 1,2,3-trimethyltrimethylene group, 1,1,2-trimethyltrimethylene group, 1,1,3-trimethyltrimethylene group, 1,2,2-trimethyltrimethyl group Methylene group, 1-ethyl-1-methyltrimethylene group, 2-ethyl-2-methyltrimethylene group, 1-ethyl-2-methyltrimethylene group, 2-ethyl-1-methyltrimethylene group, heptylene group, Examples include octylene group, nonylene group, decylene group and the like.

Examples of the substituent that Z may have include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and an acyl group having 2 to 5 carbon atoms. When Z has a substituent, the carbon number of the divalent saturated hydrocarbon group of Z does not include the carbon number of the substituent.

The divalent group represented by the general formula (V-3) may be the following general formula (VI-1).

Y may include both the general formula (IV) and at least one divalent group selected from the group consisting of the general formulas (V-1) to (V-3). When Y includes both the general formula (IV) and at least one group selected from the group consisting of the general formulas (V-1) to (V-3), the general formula (IV) And the mass ratio ((IV) :( V-1) to (V-3)) of the total content of general formulas (V-1) to (V-3) is not particularly limited. From the viewpoints of heat resistance and elongation, the mass ratio is preferably 5:95 to 95: 5, and more preferably 5:95 to 90:10 from the viewpoint of heat resistance and solubility.

The specific polyketone may be a commercially available product or may be synthesized by a known method.

The weight average molecular weight (Mw) of the specific polyketone is preferably 500 or more in terms of polystyrene standard GPC (gel permeation chromatograph) from the viewpoint of maintaining heat resistance. From the viewpoint of solubility in a nitrogen compound and a solvent, it is more preferably 10,000 to 1,000,000. When higher heat resistance is required, the weight average molecular weight (Mw) is more preferably 20,000 to 1,000,000. The weight average molecular weight (Mw) of the specific polyketone refers to a value measured by the method described in Examples.

Specific polyketone may be used individually by 1 type, and may be used in combination of 2 or more type.
Moreover, the polyketone composition may contain other polyketones other than the specific polyketone. Hereinafter, the specific polyketone and other polyketones may be collectively referred to as “polyketone”. From the viewpoint of heat resistance, transparency, and chemical resistance when a cured film is used, the content of the specific polyketone relative to the total amount of polyketone is preferably 50% by mass or more, and preferably 60% by mass or more. More preferably, it is more preferably 70% by mass or more.

From the viewpoint of heat resistance, transparency and chemical resistance when used as a cured film, the total content of polyketone is 50 to 99 parts by mass with respect to 100 parts by mass of the total amount of polyketone and nitrogen-containing compound. It is preferably 50 parts by mass to 95 parts by mass.

<Specific nitrogen-containing compounds>
The polyketone composition of the present embodiment contains a nitrogen-containing compound (specific nitrogen-containing compound) having a nitrogen atom and a hydroxymethyl group or an alkoxymethyl group bonded to the nitrogen atom.
The specific nitrogen-containing compound is preferably a compound having both a hydroxymethyl group and an alkoxymethyl group, or a compound having no hydroxymethyl group and having an alkoxymethyl group, more preferably a compound having no hydroxymethyl group and having an alkoxymethyl group. preferable.

The total number of hydroxymethyl groups and alkoxymethyl groups contained in the molecule of the specific nitrogen-containing compound is not particularly limited as long as it is 1 or more. The total number of hydroxymethyl groups and alkoxymethyl groups contained in the molecule is preferably 2 to 6, and 4 to 6 from the viewpoint of elongation and chemical resistance when used as a cured film. It is more preferable.

The number of carbon atoms of the alkoxy group in the alkoxymethyl group is preferably 1-30, more preferably 1-15, still more preferably 1-10, and particularly preferably 1-3. 1 is very particularly preferred.

Specific nitrogen-containing compounds include compounds represented by the following general formulas (VII-1) and (VII-2).

 

In general formula (VII-1), A represents an n-valent organic group, and W ¹ and W ² are each independently a hydrogen atom or the following general formula (VIII-1) or (VIII-2) N represents 2 or 3. However, among the plurality of ^{W 1} and ^{W 2,} at least one is a group represented by the following general formula (VIII-1) or (VIII-2), 2 of the plurality of ^{W 1} and ^{W 2} The above is preferably a group represented by the following general formula (VIII-1) or (VIII-2).

In general formula (VIII-2), R ¹ represents an alkyl group having 1 to 30 carbon atoms which may have a substituent. The alkyl group represented by R ¹ preferably has 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms, still more preferably 1 to 10 carbon atoms, and particularly preferably 1 to 3 carbon atoms. 1 is very preferable.

In the general formula (VII-1), examples of the organic group represented by A include groups represented by the following general formulas (IX-1) and (IX-2).

 

In general formula (VII-2), W ³ to W ⁶ are each independently a hydrogen atom or a group represented by general formula (VIII-1) or (VIII-2). ^However, among the W 3 ~ ^{W 6,} at least one is a group represented by the following general formula (VIII-1) or ^(VIII-2), 2 or more of W 3 ~ ^{W 6} is the following A group represented by the general formula (VIII-1) or (VIII-2) is preferable.

Examples of the specific nitrogen-containing compound include compounds represented by the following general formulas (X-1) to (X-3).

In the general formulas (X-1) to (X-3), each R ¹ independently represents an alkyl group having 1 to 30 carbon atoms which may have a substituent. Details of R ^1, is the same as ^{R 1} in the general formula (VIII-2).

The specific nitrogen-containing compound may be a monomer or an oligomer, or a mixture of a monomer and an oligomer. Examples of oligomers include those formed by self-reaction of monomers.

The specific nitrogen-containing compound may be used alone or in combination of two or more. The content of the specific nitrogen-containing compound is from 1 part by mass to 50 parts per 100 parts by mass of the total amount of the polyketone and the specific nitrogen-containing compound from the viewpoint of heat resistance, transparency, and chemical resistance when used as a cured film. The mass is preferably 5 parts by mass, more preferably 5 parts by mass to 50 parts by mass, and still more preferably 5 parts by mass to 20 parts by mass.

<Heat latent acid generator>
The polyketone composition may further contain a thermal latent acid generator. The thermal latent acid generator is a compound that generates an acid by heating. When the polyketone composition contains a thermal latent acid generator, the crosslinking reaction by the specific nitrogen-containing compound is promoted, and a stronger cured product can be obtained, so that the chemical resistance of the cured film tends to be improved. .

Examples of the acid generated from the thermal latent acid generator include aryl sulfonic acids such as p-toluenesulfonic acid and benzenesulfonic acid, and paroxyls such as (±) -10-camphorsulfonic acid, trifluoromethanesulfonic acid, and nonafluorobutanesulfonic acid. Examples thereof include alkyl sulfonic acids such as fluoroalkyl sulfonic acid, methane sulfonic acid, ethane sulfonic acid, and butane sulfonic acid.

The thermal latent acid generator may be used alone or in combination of two or more. The content of the thermal latent acid generator is preferably 0.05 to 30 parts by mass with respect to 100 parts by mass of the total amount of the polyketone, the nitrogen-containing compound, and the thermal latent acid generator. More preferably, it is from 20 parts by weight to 20 parts by weight, and even more preferably from 0.2 to 10 parts by weight.

<Solvent>
The polyketone composition may further contain a solvent. The solvent is not particularly limited as long as it dissolves or disperses each component. Solvents include γ-butyrolactone, ethyl lactate, propylene glycol monomethyl ether acetate, butyl acetate, benzyl acetate, n-butyl acetate, ethoxyethyl propionate, 3-methylmethoxypropionate, N-methyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, hexamethylphosphorylamide, tetramethylene sulfone, diethyl ketone, diisobutyl ketone, methyl amyl ketone, cyclopentanone, cyclohexanone, propylene glycol monomethyl Ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, xylene, mesitylene, ether Rubenzen, propylbenzene, cumene, diisopropylbenzene, hexyl benzene, anisole, diglyme, dimethyl sulfoxide, chloroform, dichloromethane, dichloroethane, chlorobenzene and the like. These solvents may be used alone or in combination of two or more.

When the polyketone composition contains a solvent, the content of the solvent is 5 mass with respect to 100 mass parts of the total amount of the polyketone, the nitrogen-containing compound, and the latent thermal acid generator contained as necessary, and the solvent. Part to 95 parts by weight, preferably 10 parts to 90 parts by weight.

<Other additives>
The polyketone composition may further contain other additives. Examples of other additives include adhesion assistants, surfactants, leveling agents, antioxidants, and UV degradation inhibitors.

<Polyketone cured product>
The polyketone cured product of the present embodiment is a cured product of the polyketone composition of the present embodiment.
The polyketone cured product can be produced, for example, by the following method. First, the polyketone composition is applied to at least a part of the surface of the substrate to form a composition layer. The method for applying the polyketone composition to the substrate is not particularly limited as long as the composition layer can be formed in an arbitrary shape at an arbitrary location on the substrate. Examples of the method for applying the polyketone composition to the substrate include an immersion method, a spray method, a screen printing method, a spin coating method, a spin coating method, and a bar coating method.

The base material to which the polyketone composition is applied is not particularly limited, and glass, semiconductor, metal oxide insulator (titanium oxide, silicon oxide, etc.), inorganic materials such as silicon nitride, triacetyl cellulose, transparent polyimide, polycarbonate, Examples thereof include a transparent substrate composed of a transparent resin such as an acrylic polymer and a cycloolefin resin. The shape of the substrate is not particularly limited, and may be a plate shape or a film shape. Since the polyketone composition of the present embodiment exhibits a high elongation when it is used as a cured film and is excellent in chemical resistance, it can be suitably used as a coating material for a substrate, a molded product, and the like.

When the polyketone composition contains a solvent, it may be dried before and after curing. The drying method is not particularly limited, and examples thereof include a heat treatment method using an apparatus such as a hot plate or an oven. The drying conditions are not particularly limited as long as the solvent in the polyketone composition is sufficiently volatilized, and is usually about 50 to 150 ° C. for about 1 to 90 minutes.

After forming the composition layer, it is cured to obtain a polyketone cured product. The curing method is not particularly limited and can be cured by heat treatment or the like. For curing by heat treatment, ovens such as box dryers, hot air conveyor dryers, quartz tube furnaces, hot plates, rapid thermal annealing, vertical diffusion furnaces, infrared curing furnaces, electron beam curing furnaces, microwave curing furnaces, etc. Can be used.

The atmosphere for curing may be selected from the air or an inert atmosphere such as nitrogen, and is preferably performed in a nitrogen atmosphere from the viewpoint of preventing oxidation of the polyketone composition.
The temperature and time of the heat treatment for curing can be arbitrarily set in consideration of the composition conditions, work efficiency, etc., and are usually about 60 minutes to 200 ° C. for about 30 minutes to 2 hours.

The obtained polyketone cured product can be used as a substrate with a polyketone cured product with the substrate attached, and can be used after being peeled off from the substrate, if necessary.
In the base material with a polyketone cured product, the polyketone cured product may be provided on at least a part of the surface of the base material, and may be provided on only one surface of the base material or on both surfaces. The polyketone cured product may have a single-layer structure or a multi-layer structure in which two or more layers are laminated.

<Optical element and image display device>
The optical element and the image display device of the present embodiment each have the polyketone cured product of the present embodiment. The polyketone cured product applied to the optical element and the image display device may be the above-described base material with a polyketone cured product. Moreover, if a base material is a transparent base material, it can use suitably for an optical element. Examples of the transparent substrate include those exemplified in the production of the polyketone cured product.

Optical element and image display device, for example, paste the base material side of the base material with polyketone cured product to the application location such as LCD (Liquid Crystal Display), ELD (Electro Luminescence Display) etc. via adhesive, adhesive, etc. Can be obtained.

The polyketone cured product and various optical elements such as a polarizing plate using the polyketone can be preferably used for various image display devices such as a liquid crystal display device. The image display device may have the same configuration as the conventional image display device except that the polyketone cured product of the present embodiment is used. When the image display device is a liquid crystal display device, by appropriately assembling each component such as a liquid crystal cell, an optical element such as a polarizing plate, and an illumination system (backlight, etc.) as necessary, and incorporating a drive circuit, etc. Can be manufactured. The liquid crystal cell is not particularly limited, and various types such as a TN type, an STN type, and a π type can be used.

Applications of image display devices include OA equipment such as desktop personal computers, notebook personal computers, and copiers, mobile phones, watches, digital cameras, personal digital assistants (PDAs), portable devices such as portable game machines, video cameras, televisions, and electronic devices. Household electrical equipment such as a range, back monitor, car navigation system monitor, in-vehicle equipment such as car audio, display equipment such as information monitors for commercial stores, security equipment such as monitoring monitors, nursing care such as nursing monitors Examples thereof include medical devices and medical devices such as medical monitors.

The disclosure of Japanese Patent Application No. 2016-153622 is incorporated herein by reference in its entirety.
All references, patent applications, and technical standards in this disclosure are included in this disclosure to the same extent as if individual references, patent applications, and technical standards were specifically and individually stated to be incorporated by reference. Incorporated by reference.

Hereinafter, the present embodiment will be specifically described by way of examples, but the present embodiment is not limited to these examples.

<Polyketone composition>
Components (A) to (D) were blended in the proportions shown in Tables 1 to 4 and filtered through a PTFE (polytetrafluoroethylene) filter to obtain polyketone compositions of Examples and Comparative Examples. The numerical value in the parenthesis represents the blending ratio (part by mass, solid content ratio). “-” Indicates that the component is not contained. Each component in Tables 1 to 4 is as follows.

Component (A) (Synthesis Example 1) Synthesis of Polyketone PK-1 As a monomer, a flask containing 10 mmol of 2,2′-dimethoxybiphenyl and 10 mmol of cis-1,4-cyclohexanedicarboxylic acid was charged with diphosphorus pentoxide and methanesulfone. 30 ml of an acid mixture (mass ratio 1:10) was added and stirred at 60 ° C. After the reaction, the content was poured into 500 ml of methanol, and the produced precipitate was collected by filtration. The obtained solid was washed with distilled water and methanol and then dried to obtain polyketone PK-1.
The resulting polyketone PK-1 had a weight average molecular weight of 20,000 and a number average molecular weight of 8,000. In addition, a weight average molecular weight and a number average molecular weight are measured and calculated by the method described later. The weight average molecular weight (Mw) and number average molecular weight (Mn) of polyketone PK-2 to polyketone PK-15 described later were also measured in the same manner.

Synthesis Example 2 Synthesis of Polyketone PK-2 Polyketone PK-2 was obtained in the same manner as in Example 1, except that 10 mmol of 2,2′-dimethoxybiphenyl and 13 mmol of 1,3-adamantanedicarboxylic acid were used as monomers. It was. The resulting polyketone PK-2 had a weight average molecular weight of 280,000 and a number average molecular weight of 44,000.

Synthesis Example 3 Synthesis of Polyketone PK-3 Polyketone PK-3 was obtained in the same manner as in Example 1 except that 10 mmol of 2,2′-dimethoxybiphenyl and 10 mmol of 1,3-adamantanediacetic acid were used as monomers. It was. The resulting polyketone PK-3 had a weight average molecular weight of 42,000 and a number average molecular weight of 12,000.

Synthesis Example 4 Synthesis of Polyketone PK-4 Example 1 except that 10 mmol of 2,2′-dimethoxybiphenyl, 5 mmol of 1,3-adamantane dicarboxylic acid and 5 mmol of cis-1,4-cyclohexanedicarboxylic acid were used as monomers. In the same manner as above, polyketone PK-4 was obtained. The resulting polyketone PK-4 had a weight average molecular weight of 36,000 and a number average molecular weight of 12,000.

(Synthesis Example 5) Synthesis of Polyketone PK-5 A polyketone was obtained in the same manner as in Example 1 except that 10 mmol of 2,2′-dimethoxybiphenyl, 5 mmol of 1,3-adamantanedicarboxylic acid and 5 mmol of dodecanedioic acid were used as monomers. PK-5 was obtained. The resulting polyketone PK-5 had a weight average molecular weight of 36,000 and a number average molecular weight of 13,000.

Synthesis Example 6 Synthesis of Polyketone PK-6 The polyketone was obtained in the same manner as in Example 1 except that 10 mmol of 2,2′-dimethoxybiphenyl, 5 mmol of 1,3-adamantanediacetic acid, and 5 mmol of dodecanedioic acid were used as monomers. PK-6 was obtained. The resulting polyketone PK-6 had a weight average molecular weight of 39,000 and a number average molecular weight of 12,000.

Synthesis Example 7 Synthesis of Polyketone PK-7 A polyketone was obtained in the same manner as in Example 1 except that 10 mmol of 2,2′-dimethoxybiphenyl, 5 mmol of 1,3-adamantanediacetic acid, and 5 mmol of hexanedioic acid were used as monomers. PK-7 was obtained. The resulting polyketone PK-7 had a weight average molecular weight of 39,000 and a number average molecular weight of 12,000.

Synthesis Example 8 Synthesis of Polyketone PK-8 Except that 10 mmol of 2,2′-dimethoxybiphenyl, 5 mmol of 1,3-adamantanediacetic acid and 5 mmol of cis-1,4-cyclohexanedicarboxylic acid were used, the same procedure as in Example 1 was performed. Polyketone PK-8 was obtained. The resulting polyketone PK-8 had a weight average molecular weight of 45,000 and a number average molecular weight of 11,000.

(Synthesis Example 9) Synthesis of Polyketone PK-9 Example 1 except that 10 mmol of 2,2′-dimethoxybiphenyl, 5 mmol of 1,3-adamantanediacetic acid, and 5 mmol of trans-1,4-cyclohexanedicarboxylic acid were used as monomers. In the same manner as above, polyketone PK-9 was obtained. The resulting polyketone PK-9 had a weight average molecular weight of 37,000 and a number average molecular weight of 10,000.

Synthesis Example 10 Synthesis of Polyketone PK-10 As monomers, 2,2′-dimethoxybiphenyl 10 mmol, 1,3-adamantanediacetic acid 5 mmol and 1,4-cyclohexanedicarboxylic acid (mixture of cis and trans, cis: trans (Molar ratio) = 7: 3) Polyketone PK-10 was obtained in the same manner as in Example 1 except that 5 mmol was used. The resulting polyketone PK-10 had a weight average molecular weight of 33,000 and a number average molecular weight of 11,000.

Synthesis Example 11 Synthesis of Polyketone PK-11 Example 1 was used except that 10 mmol of 2,2′-dimethoxybiphenyl, 5 mmol of 1,3-adamantanediacetic acid, and 5 mmol of decalin-2,6-dicarboxylic acid were used as monomers. Similarly, polyketone PK-11 was obtained. The resulting polyketone PK-11 had a weight average molecular weight of 33,000 and a number average molecular weight of 10,000.

Synthesis Example 12 Synthesis of Polyketone PK-12 As a monomer, 10 mmol of 2,2′-dimethoxybiphenyl, 5 mmol of 1,3-adamantanediacetic acid, and 5 mmol of norbornane dicarboxylic acid (2,4-, 2,5-mixture) A polyketone PK-12 was obtained in the same manner as in Example 1 except that it was used. The resulting polyketone PK-12 had a weight average molecular weight of 27,000 and a number average molecular weight of 9,200.

Synthesis Example 13 Synthesis of Polyketone PK-13 Example 1 except that 10 mmol of 2,2′-dimethoxybiphenyl, 5 mmol of 1,3-adamantanediacetic acid, and 5 mmol of trans-2,3-norbornane dicarboxylic acid were used as monomers. In the same manner as above, polyketone PK-13 was obtained. The resulting polyketone PK-13 had a weight average molecular weight of 26,000 and a number average molecular weight of 8,100.

Synthesis Example 14 Synthesis of Polyketone PK-14 As monomers, 2,2′-bis (2-methoxyphenyl) propane 10 mmol, 1,3-adamantanediacetic acid 5 mmol and 1,4-cyclohexanedicarboxylic acid (of cis and trans Polyketone PK-14 was obtained in the same manner as in Example 1 except that 5 mmol of the mixture, cis: trans (molar ratio) = 7: 3) was used. The resulting polyketone PK-14 had a weight average molecular weight of 28,000 and a number average molecular weight of 8,300.

Synthesis Example 15 Synthesis of Polyketone PK-15 As monomers, 10 mmol of diphenyl ether, 5 mmol of 1,3-adamantanediacetic acid and 1,4-cyclohexanedicarboxylic acid (mixture of cis and trans, cis: trans (molar ratio) = 7) : 3) A polyketone PK-15 was obtained in the same manner as in Example 1 except that 5 mmol was used. The resulting polyketone PK-15 had a weight average molecular weight of 27,000 and a number average molecular weight of 8,000.

(B) Component B1: Compound represented by the following formula (XII)

B2: Compound represented by the following formula (XIII)

B3: Compound represented by the following formula (XIV)

B4: Compound represented by the following formula (XV)

B5: Compound represented by the following formula (XVI) (epoxy equivalent 188)

B6: Compound represented by the following formula (XVII)

B7: Triglycidyl-p-aminophenol

(B ′) Component B′1: Compound represented by the following formula (XVIII)

(C) Component C1: Compound represented by the following formula (XVIV)

C2: Compound represented by the following formula (XX)

(D) Component D1: N-methyl-2-pyrrolidone

 

<Preparation of sample for evaluation>
Using the obtained polyketone composition, a polyketone cured product was prepared by the following method, and a sample for evaluation described later was prepared.

(1) Sample for chemical resistance test A polyketone composition was applied to a silicon substrate by a spin coating method. The obtained silicon substrate was dried for 3 minutes on a hot plate heated to 120 ° C. Furthermore, the silicon substrate after drying is heat-treated at 200 ° C. for 1 hour in a nitrogen stream using an inert gas oven (Koyo Thermo System Co., Ltd.) to obtain a silicon substrate with a cured polyketone, which is chemically resistant. It was set as the sample for a test.

(2) Sample for transmittance measurement A polyketone composition was applied to a glass substrate by a spin coating method. The obtained glass substrate was dried in the same manner as (1) and heat-treated to obtain a glass substrate with a polyketone cured product, which was used as a transmittance measurement sample.

(3) Sample for measuring pyrolysis temperature A polyketone composition was dropped into an aluminum cup, dried in the same manner as in (1), and heat-treated to obtain a cured polyketone (polyketone molded product) molded in the aluminum cup. . The polyketone molded body was peeled off from the aluminum cup, and this was used as a sample for measuring the thermal decomposition temperature.

(4) Sample for measuring elongation rate The polyketone composition was applied onto a polyimide film by a bar coating method, dried in the same manner as (1), and heat-treated to obtain a polyimide film with a cured polyketone. This polyketone cured product was peeled from the polyimide film to obtain a polyketone cured product (polyketone film), which was used as a sample for measuring elongation.

<Measurement of molecular weight of polyketone>
The molecular weight (weight average molecular weight and number average molecular weight) of the polyketone was measured by GPC method using tetrahydrofuran (THF) as an eluent, and was determined in terms of standard polystyrene. Details are as follows.

-Device name: Ecosec HLC-8320GPC (Tosoh Corporation)
Column: TSKgel Supermultipore HZ-M (Tosoh Corporation)
・ Detector: UV detector and RI detector combined ・ Flow rate: 0.4 ml / min

<Chemical resistance test>
The silicon substrate with a polyketone cured product was separated into individual test pieces. Each test piece was immersed in the chemical solution under the following conditions (a) and (b). It was observed whether the polyketone film, which is a polyketone cured product, was dissolved during the immersion, or whether the polyketone film was peeled off from the silicon substrate. The observation results are shown in Tables 5 and 6. In this test, when dissolution and peeling were not observed, it was set as “no change”.

Condition (a): A mixed solution of dimethyl sulfoxide (DMSO), 2-ethanolamine (2AE) and (DMSO: 2AE is 7: 3 by volume) was heated to 60 ° C., and the test piece was immersed for 30 minutes.
Condition (b): The test piece was immersed in a 0.5% by mass hydrofluoric acid (HF) aqueous solution at 23 ° C. for 30 minutes.

<Transmittance measurement>
The visible light transmittance at 400 nm of the glass substrate with a cured polyketone was measured by an ultraviolet-visible absorption spectrum method using a spectrophotometer (V-570, JASCO Corporation). Tables 5 and 6 show the transmittance of the film converted to a film thickness of 1 μm using a glass substrate having no polyketone cured product as a reference.

<Pyrolysis temperature measurement>
The weight loss of the cured polyketone was measured using a thermogravimetric balance TG-DTA6300 (Hitachi High-Tech Science Co., Ltd. (Hitachi High-Technologies Corporation)). The intersection of the tangents of the curves where the weight is greatly reduced by heating is defined as the pyrolysis temperature. The results are shown in Tables 5 and 6.

<Elongation measurement>
Using a tensile tester (AUTOGRAPH EZ-TEST EZ-S, manufactured by Shimadzu Corporation), the polyketone cured product (polyketone film) was subjected to a tensile test at a speed of 5 mm / min, and the elongation was measured. The results are shown in Tables 5 and 6.

It turned out that the polyketone hardened | cured material obtained from the polyketone composition of an Example is excellent in chemical resistance, transparency, and heat resistance, and also has a high elongation rate.
On the other hand, Comparative Examples 1 to 3 not containing a specific nitrogen-containing compound were inferior in chemical resistance and had a low elongation. In Comparative Examples 4 to 13 containing an epoxy compound instead of the specific nitrogen-containing compound, the chemical resistance, transparency and heat resistance were the same as those in the example, but it was found that the elongation was low.

Claims (12)

1. A polyketone containing a structural unit represented by the following general formula (I) in the main chain, and
   A nitrogen-containing compound having a nitrogen atom and at least one group selected from the group consisting of a hydroxymethyl group and an alkoxymethyl group bonded to the nitrogen atom,
   Containing a polyketone composition.
   

   

   
   
   [In general formula (I), each X independently represents a divalent group having 1 to 50 carbon atoms which may have a substituent, and Y each independently has a substituent. Represents a divalent hydrocarbon group having 1 to 30 carbon atoms, and n represents an integer of 3 to 1000. ]
2. The polyketone composition according to claim 1, wherein, in the general formula (I), each X independently contains a bivalent group having 6 to 50 carbon atoms including an aromatic ring.
3. In the general formula (I), each X independently contains a divalent group represented by at least one selected from the group consisting of the following general formulas (II-1) to (II-3): The polyketone composition according to claim 1 or 2.
   

   

   
   
   [In General Formula (II-1), each R ¹ independently represents a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 30 carbon atoms, and each R ² independently represents A hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and each m independently represents an integer of 0 to 3. ]
   

   

   
   [In General Formula (II-2), each R ¹ independently represents a hydrogen atom or an optionally substituted hydrocarbon group having 1 to 30 carbon atoms, and each R ² independently represents A hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, m independently represents an integer of 0 to 3, and Z represents an oxygen atom or a compound represented by the following general formula (III- 1) to divalent groups represented by (III-7). ]
   

   

   
   [In the general formulas (III-1) to (III-7), each R ¹ independently represents a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ² Each independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and R ³ and R ⁴ may each independently have a hydrogen atom or a substituent. This represents a hydrocarbon group having 1 to 30 carbon atoms. m independently represents an integer of 0 to 3, n independently represents an integer of 0 to 4, and p independently represents an integer of 0 to 2, respectively. ]
   

   

   
   [In General Formula (II-3), each R ⁵ independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and n represents each independently 0 to 4 Indicates an integer. ]
4. The polyketone composition according to any one of claims 1 to 3, wherein, in the general formula (I), Y contains a divalent saturated hydrocarbon group.
5. The polyketone composition according to claim 4, wherein, in the general formula (I), Y contains a divalent saturated alicyclic hydrocarbon group.
6. The polyketone composition according to any one of claims 1 to 5, wherein in the general formula (I), Y has 6 to 30 carbon atoms.
7. The polyketone composition according to any one of claims 1 to 6, wherein the nitrogen-containing compound has a total number of hydroxymethyl groups and alkoxymethyl groups bonded to nitrogen atoms of 2 to 6.
8. The polyketone composition according to any one of claims 1 to 7, further comprising a thermal latent acid generator.
9. The polyketone composition according to any one of claims 1 to 8, further comprising a solvent.
10. A cured product of a polyketone, which is a cured product of the polyketone composition according to any one of claims 1 to 9.
11. An optical element having the polyketone cured product according to claim 10.
12. An image display device comprising the polyketone cured product according to claim 10.