TW201821524A - Polyketone composition including nitrogen-containing compound, cured polyketone, optical element, and image display device - Google Patents

Abstract

A polyketone composition includes a polyketone and a nitrogen-containing compound. The polyketone has a structural unit represented by the following Formula (I) in a main chain. The nitrogen-containing compound has a nitrogen atom and at least one group selected from the group consisting of a hydroxymethyl group and an alkoxymethyl group, the hydroxymethyl group and the alkoxymethyl group being linked to the nitrogen atom. In Formula (I), X represents a bivalent group which has from 1 to 50 carbon atoms and may have a substituent group, Y represents a bivalent hydrocarbon group which has from 1 to 30 carbon atoms and may have a substituent group, and n represents an integer from 3 to 1000.

Description

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

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, which has excellent heat resistance and mechanical properties, and can be utilized as an engineering plastic. The polymer belonging to the aromatic polyketone is almost always an aromatic polyether ketone polymerized by an aromatic nucleophilic aromatic substitution reaction, and has an ether bond in the main chain. On the other hand, an aromatic polyketone having no ether bond in the main chain is known to have further excellent heat resistance and chemical resistance compared to the aromatic polyether ketone (for example, refer to Patent Document 1 and Patent). Literature 2).

In recent years, there has been reported a technique capable of obtaining an aromatic polyketone having both high transparency and heat resistance (for example, refer to Patent Document 3), and is expected to be applied to an optical member by utilizing a husband- Friedel-Crafts Acylation is used to directly polymerize an alicyclic dicarboxylic acid with a 2,2'-dialkoxybiphenyl compound.

When a resin material such as an aromatic polyketone is applied to an optical component, it is desired to exhibit properties that cannot be obtained from an inorganic material, and such properties are, for example, lightness and flexibility. Examples of the application of the resin material include a lightweight coating material, a glass substitute material, and the like, and a flexible display that exhibits flexibility. Among them, in recent years, applications in flexible displays have received particular attention. [Previous Technical Literature] (Patent Literature)

Patent Document 1: Japanese Laid-Open Patent Publication No. 62-7730. Patent Document 2: Japanese Laid-Open Patent Publication No. 2005-272728. Patent Document 3: Japanese Laid-Open Patent Publication No. 2013-53194.

[Problems to be Solved by the Invention] Further, when an aromatic polyketone is formed into a film, in addition to transparency, heat resistance, and chemical resistance, it is also desirable to have a high elongation.

The present invention has been made in view of the above circumstances, and an object thereof is to provide a polyketone composition and a polyketone cured product, and an optical element and an image display device having the polyketone cured product, wherein the polyketone composition is formed into a cured film, It is excellent in heat resistance, transparency, and chemical resistance, and exhibits high elongation. [Technical means to solve the problem]

The technical means for solving the above-mentioned problems to be solved includes the following embodiments.

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

In the formula (I), X each independently represents a divalent group having 1 to 50 carbon atoms which may have a substituent, and Y each independently represents a divalent hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and n represents An integer from 3 to 1000.

<2> The polyketone composition according to <1>, wherein, in the above formula (I), X each independently contains a divalent group having 6 to 50 carbon atoms, and the divalent group contains an aromatic ring .

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

In the formula (II-1), R ¹ each 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. m each independently represents an integer of 0 to 3.

In the formula (II-2), R ¹ each 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. m each independently represents an integer of 0 to 3, and Z represents an oxygen atom or a divalent group represented by the following general formulae (III-1) to (III-7).

In the general formulae (III-1) to (III-7), R ¹ each 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 carbon number which may have a substituent The hydrocarbon group of 1 to 30, R ³ and R ⁴ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and m each independently represents an integer of 0 to 3, and n each independently represents 0 to 4 The integers, p each independently represent an integer from 0 to 2.

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

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

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

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

The polyketone composition according to any one of the above-mentioned nitrogen-containing compounds, wherein the total number of the methylol group and the alkoxymethyl group bonded to the nitrogen atom is two. ~6.

The polyketone composition according to any one of <1> to <7> which further contains a latent heat acid generator.

The polyketone composition according to any one of <1> to <8> which further contains a solvent.

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

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

<12> An image display device comprising the polyketone cured product according to <10>. [Effects of the Invention]

According to the present invention, it is possible to provide a polyketone composition and a polyketone cured product, and an optical element and an image display device having the polyketone cured product, which are heat-resistant, transparent, and resistant when formed into a cured film. Excellent chemical properties and high elongation.

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 constituent elements (including the element steps and the like) are not necessarily required unless otherwise specified. The same values and ranges are not intended to limit the invention.

In the present specification, the numerical range indicated by "~" is a range including the numerical values before and after the "~" as the minimum value and the maximum value, respectively. In the numerical range stated in the specification, the upper or lower limit of the numerical range stated in a certain stage may be replaced with the upper or lower limit of the numerical range stated in other stages. . Further, in the numerical ranges described in the present specification, the upper limit or the lower limit of the numerical range may be replaced with the values shown in the examples. In the present specification, when the content of each component in the composition is a plurality of substances corresponding to the respective components in the composition, unless otherwise specified, it means the total of the plurality of substances present in the composition. The content rate. In the present specification, the term "layer" or "film" means that when a region in which the layer or film is present is observed, a part of the region is formed in addition to the entire region.

In the present specification, the phrase "a plurality of aromatic rings are non-conjugated with each other or a weak conjugate relationship with each other" means that two aromatic rings are separated by an ether bond or a methylene linkage, or Conjugation of the aromatic rings to each other is suppressed by appropriate twisting such as 2,2'-substituted biphenyl.

In the present specification, the term "excellent transparency" means that the transmittance of visible light (the permeability 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 specification, the term "heat resistance" means that the thermal decomposition temperature is 400 ° C or higher in a member containing a polyketone.

In the present specification, the term "high elongation" means that the film formed has an elongation at break of 5% or more.

In the present specification, the term "chemical resistance of a cured film" means that even if a film-like polyketone cured product (polyketone film) formed on a substrate is exposed to a liquid medicine, the polyketone film does not. The substrate was peeled off and the polyketone film did not dissolve.

<Polyketone composition> The polyketone composition of the present embodiment contains a polyketone containing a structural unit represented by the following formula (I) (hereinafter also referred to as "specific polyketone") in the main chain; And a nitrogen-containing compound (hereinafter also referred to as "specific nitrogen-containing compound") having a nitrogen atom and a methylol group or an alkoxymethyl group bonded to the nitrogen atom.

In the formula (I), X each independently represents a divalent group having 1 to 50 carbon atoms which may have a substituent, and Y each independently represents a divalent hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and n represents An integer from 3 to 1000.

In the polyketone composition of the present embodiment, when the cured film is formed, it is excellent in heat resistance, transparency, and chemical resistance, and can exhibit high elongation. Although this reason is not clear, it can be estimated as follows. Since a specific polyketone contains a carbonyl group in a main chain, it is excellent in heat resistance and transparency. Further, since the specific polyketone is formed almost by a C-C bond, the molecular chain itself is stable to a liquid drug. Further, it is considered that the nitrogen atom in the specific nitrogen-containing compound acts to increase the cohesive force of the specific polyketone, so that the elongation at the time of forming the polyketone composition as a cured film becomes large. Further, it is considered that when a specific nitrogen-containing compound acts as a crosslinking agent, the polyketone main chains crosslink with each other, and as a result, since the specific polyketones are interlocked with each other, when the cured film is formed The elongation will become larger. Therefore, it is considered that by using a polyketone composition in which a specific nitrogen-containing compound is combined in a specific polyketone, when a cured film is formed, it is excellent in heat resistance, transparency, and chemical resistance, and can exhibit high performance. Elongation. Hereinafter, each component is demonstrated.

(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 formula (I), X each independently represents a divalent group having 1 to 50 carbon atoms which may have a substituent. Y each 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. Further, when the divalent group or the divalent hydrocarbon group has a substituent, the carbon number of the divalent group is set to a carbon number which does not include a substituent. The same is true below.

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

The substituent which the X can have is not particularly limited, and specific examples thereof include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and a fluorenyl group having 2 to 5 carbon atoms.

The divalent group represented by X is preferably a hydrocarbon group, and more preferably contains an aromatic ring. If X has an aromatic ring, there is a tendency to exhibit higher heat resistance.

X, from the viewpoint of exhibiting high heat resistance, preferably contains a divalent group having 6 to 50 carbon atoms, and the divalent group contains an aromatic ring. Examples of the aromatic ring include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a condensed tetraphenyl ring, a 1,2-benzopyrene ring, an anthracene ring, a terphenylbenzene ring, a condensed pentabenzene ring, and a benzene group. And benzopyrene ring.

Further, X preferably contains a plurality of aromatic rings, more preferably a plurality of aromatic rings which are non-conjugated with each other or a weakly conjugated group (hereinafter, also referred to as "specific aromatic ring group" ). Thereby, in the case of synthesizing a polyketone, a good deuteration can be achieved at a low reaction temperature, and a polyketone having a high molecular weight and excellent heat resistance can be obtained. The specific aromatic ring group preferably has a carbon number of 12 to 50.

Here, the phrase "a plurality of aromatic rings are non-conjugated with each other or a weak conjugate relationship with each other" means that a plurality of aromatic rings are bonded or borrowed via an ether bond or a methylene linkage. The conjugate of the aromatic rings is inhibited by steric hindrance caused by the substituent such as 2,2'-substituted biphenyl.

Examples of X include a divalent group represented by the following general formulae (II-1) to (II-3).

In the formula (II-1), R ¹ each 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. m each independently represents an integer of 0 to 3. The portion marked with a wavy line means an atomic bond. The same is true below.

The hydrocarbon group represented by R ¹ has a carbon number of from 1 to 30, preferably from 1 to 10, more preferably from 1 to 6, from the viewpoint of heat resistance. Further, when the hydrocarbon group has a substituent, the carbon number of the hydrocarbon group is set to a carbon number which does not include a substituent. The same is true below.

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 a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a secondary butyl group, a tertiary butyl group, and a n-pentyl group. Isoamyl, secondary pentyl, neopentyl, tertiary pentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, n-decyl, n-icosyl, n-tridecyl and the like. Further, the saturated aliphatic hydrocarbon group may be one having an alicyclic hydrocarbon group to be described later at the terminal portion.

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

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

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

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

Examples of the hydrocarbon group having 1 to 30 carbon atoms represented by R ² include the same hydrocarbon groups as those of the hydrocarbon group having 1 to 30 carbon atoms which are exemplified in R ¹ . In addition, examples of the substituent which the hydrocarbon group represented by R ² may have include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and a fluorenyl group having 2 to 5 carbon atoms.

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

In the formula (II-2), R ¹ each 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. m each independently represents an integer of 0 to 3, and Z represents an oxygen atom or a divalent group represented by the following general formulae (III-1) to (III-7).

In the general formulae (III-1) to (III-7), R ¹ each 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 carbon number which may have a substituent The hydrocarbon group of 1 to 30, R ³ and R ⁴ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and m each independently represents an integer of 0 to 3, and n each independently represents 0 to 4 The integers, p each independently represent an integer from 0 to 2.

R ³ and R ⁴ in the 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. As the hydrocarbon group having 1 to 30 carbon atoms in R ³ and R ⁴ include been illustrated with the general formula R (II-1) carbon atoms in ^a hydrocarbon group of the same hydrocarbon group having 1 to 30. In addition, examples of the substituent which R ³ and R ⁴ may have include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and an anthracene group having 2 to 5 carbon atoms. n in the general formulae (III-2) to (III-3) each independently represents an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 0 or 1. p in the general formulae (III-4), (III-5) and (III-7) each independently represents an integer of 0 to 2, preferably 0 or 1. The details of each of R ¹ , R ² and m in the formula (II-2) are the same as those of R ¹ , R ² and m in the formula (II-1).

In the formula (II-3), R ⁵ each independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and n each independently represents an integer of 0 to 4. The carbon number of the hydrocarbon group represented by R ⁵ is preferably from 1 to 10, more preferably from 1 to 5, from the viewpoint of heat resistance. The hydrocarbon group having 1 to 30 carbon atoms represented by R ⁵ may be the same hydrocarbon group as the hydrocarbon group having 1 to 30 carbon atoms of R ¹ exemplified in the general formula (II-1). In addition, examples of the substituent which R ⁵ can have include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and a fluorenyl group having 2 to 5 carbon atoms.

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

In the general formula (I), Y each independently represents a divalent hydrocarbon group having 1 to 30 carbon atoms which may have a substituent. The hydrocarbon group represented by Y has a carbon number of 1 to 30, preferably 4 to 30, and more preferably 6 to 30 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 having higher heat resistance and transparency, the hydrocarbon group represented by Y preferably contains a saturated alicyclic hydrocarbon group. Since the alicyclic hydrocarbon group has a larger volume than the aliphatic hydrocarbon group having the same carbon number, it can maintain high heat resistance and transparency, and has a tendency to be excellent in solubility in a nitrogen-containing compound and a solvent. Further, the hydrocarbon group represented by Y may contain a plurality of saturated aliphatic hydrocarbon groups or a plurality of saturated alicyclic hydrocarbon groups. Further, Y may be contained by combining a saturated aliphatic hydrocarbon group and a saturated alicyclic hydrocarbon group.

The saturated aliphatic hydrocarbon group represented by Y has a carbon number of from 1 to 30, preferably from 3 to 30. Examples of the saturated aliphatic hydrocarbon group include a methylene group, an ethyl group, a propyl group, a methyl group, a methyl group, a butyl group, a 1-methyl propyl group, a 2-methyl propyl group, and an ethyl group. 1,1,1-dimethylexylethyl, 1,2-dimethylexylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl , 2-ethyl-propyl, 1,1-dimethyl-propyl, 2,2-dimethyl-propyl, 1,2-dimethyl-propyl, propyl-ethyl, ethylmethyl Ethyl, hexyl, 1-methyl-amyl, 2-methyl-amyl, 3-methyl-amyl, 1-ethylbutyl, 2-ethylbutyl, 1-propyl Base, 2-propylpropyl, butylethyl, 1,1-dimethylbutylene, 2,2-dimethylbutylene, 1,2-dimethylbutylene, 1,3 - dimethyl-tert-butyl, 1,4-dimethyl-butylene, 1,2,3-trimethyl-propyl, 1,1,2-trimethyl-propyl, 1,1,3 - Trimethyl propyl, 1,2,2-trimethyl propyl, 1-ethyl-1-methyl propyl, 2-ethyl-2-methyl propyl, 1-B Benzyl-2-methylpropanyl, 2-ethyl-1-methylpropyl, 2,2-ethylmethylpropyl, heptyl, octyl, extens Base, stretching decyl, eicosyl stretch, stretch triacontyl.

From the viewpoint of heat resistance, preferred examples of the saturated aliphatic hydrocarbon group include an exohexyl group, a methyl pentyl group, an ethyl butyl group, a propyl propyl group, a butyl group ethyl group, and a dimethyl butyl group. Trimethyl propyl, ethyl methyl propyl, heptyl, octyl, decyl, decyl, eicosyl, tridecyl and the like.

The saturated alicyclic hydrocarbon group represented by Y has a carbon number of from 3 to 30, preferably from 4 to 30, more preferably from 6 to 30. Examples of the saturated alicyclic hydrocarbon group include a divalent group having a skeleton of a cyclopropane skeleton, a cyclobutane skeleton, a cyclopentane skeleton, a cyclohexane skeleton, a cycloheptane skeleton, and cyclooctane. Skeleton, cubic alkane skeleton, norbornane skeleton, tricyclo [5.2.1.0] decane, adamantane skeleton, bisadamantane skeleton, bicyclo [2.2.2] octane skeleton, decalin skeleton, and the like.

From the viewpoint of heat resistance, examples of the saturated alicyclic hydrocarbon group include a cyclohexane skeleton, a cycloheptane skeleton, a cyclooctane skeleton, a cubane skeleton, a norbornane skeleton, and a tricyclic ring [5.2.1.0]. A divalent group such as a decane, an adamantane skeleton, a bisadamantane skeleton, a bicyclo[2.2.2]octane skeleton, or a decalin skeleton.

Examples of the substituent which the hydrocarbon group represented by Y may have are an amine group, an oxy group, a hydroxyl group, a halogen atom or the like.

Y preferably contains at least one divalent group represented by at least one selected from the group consisting of the following general formula (IV) and the following general formulae (V-1) to (V-3), It is preferred to contain at least a divalent group represented by the following formula (IV).

a hydrogen atom of an adamantane skeleton in the formula (IV), a hydrogen atom of a cyclohexane skeleton in the formula (V-1), a hydrogen atom of a decalin skeleton in the formula (V-2) And the hydrogen atom of the norbornane skeleton in the formula (V-3) may be each substituted with a hydrocarbon group, an amine group, an oxy group, a hydroxyl group or a halogen atom. Further, in the formula (IV), Z each 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 soft cured film, Z is preferably a divalent saturated hydrocarbon group each having 1 to 10 carbon atoms which may have a substituent, and Z is preferably a carbon number from the viewpoint of heat resistance. a divalent saturated hydrocarbon group of 1 to 5.

Examples of the divalent saturated hydrocarbon group represented by Z include a methylene group, an exoethyl group, a propyl group, a methyl group ethyl group, a butyl group, a 1-methyl propyl group, and a 2-methyl propyl group. , ethyl ethyl, 1,1-dimethylexylethyl, 1,2-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 1- Ethyl propyl, 2-ethyl-propyl, 1,1-dimethyl-propyl, 2,2-dimethyl-propyl, 1,2-dimethyl-propyl, propyl-ethyl Ethylmethylethyl, exohexyl, 1-methyl-amyl, 2-methyl-amyl, 3-methyl-amyl, 1-ethylbutyl, 2-ethylbutyl, 1 -propylpropyl, 2-propylpropyl, butylethyl, 1,1-dimethylbutylene, 2,2-dimethylbutylene, 1,2-dimethylbutylene , 1,3-dimethylexylbutyl, 1,4-dimethylexylbutyl, 1,2,3-trimethylpropyl, 1,1,2-trimethylpropyl, 1 , 1,3-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 2-ethyl-2-methylpropyl , 1-ethyl-2-methylpropyl, 2-ethyl-1-methylpropyl, heptyl, octyl, thiol, hydrazine .

Examples of the substituent which Z can have include a halogen atom, an alkoxy group having 1 to 5 carbon atoms, and a fluorenyl group having 2 to 5 carbon atoms. Further, when Z has a substituent, the carbon number of the divalent saturated hydrocarbon group of Z is set to the carbon number which does not contain a substituent.

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

Y may contain both the above formula (IV) and a divalent group represented by at least one selected from the group consisting of the above formulas (V-1) to (V-3). When Y contains both the above formula (IV) and at least one group selected from the group consisting of the above formulas (V-1) to (V-3), the formula (IV) The mass ratio of the content to the total content of the general formulae (V-1) to (V-3) ((IV): (V-1) to (V-3)) is not particularly limited. From the viewpoint of heat resistance and elongation, the above-mentioned mass is preferably from 5:95 to 95:5, and more preferably from 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-converted standard GPC (gel permeation chromatography) from the viewpoint of maintaining heat resistance. The heat resistance and the solubility to a nitrogen-containing compound and a solvent are more preferably 10,000 to 1,000,000. When higher heat resistance is required, the weight average molecular weight (Mw) is further preferably from 20,000 to 1,000,000. The weight average molecular weight (Mw) of a particular polyketone means the value determined by the method described in the examples.

The specific polyketone may be used singly or in combination of two or more. Further, the polyketone composition may contain a polyketone other than the specific polyketone. Hereinafter, a specific polyketone and other polyketones may be collectively referred to as "polyketones". The content of the specific polyketone relative to the total amount of the polyketone is preferably 50% by mass or more, and more preferably 60% by mass or more from the viewpoint of heat resistance, transparency, and chemical resistance at the time of forming the cured film. Further, it is more preferably 70% by mass or more.

The total content of the polyketone is preferably from 50 parts by mass to 99% by mass based on 100 parts by mass of the total amount of the polyketone and the nitrogen-containing compound from the viewpoint of heat resistance, transparency, and chemical resistance at the time of forming the cured film. More preferably, it is 50 mass parts - 95 mass parts.

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

The total number of the methylol group and the alkoxymethyl group contained in the molecule of the specific nitrogen-containing compound is not particularly limited as long as it is one or more. The total number of the methylol group and the alkoxymethyl group contained in the molecule is preferably from 2 to 6, and from the viewpoint of the elongation at the time of forming the cured film and the chemical resistance, it is more preferably four. Six.

The carbon number of the alkoxy group in the alkoxymethyl group is preferably from 1 to 30, more preferably from 1 to 15, still more preferably from 1 to 10, particularly preferably from 1 to 3, and most preferably 1.

The specific nitrogen-containing compound may, for example, be a compound represented by the following general formulae (VII-1) and (VII-2).

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

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

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

In the general formula (VII-2), W ³ to W ⁶ are each independently a hydrogen atom or a group represented by the above formula (VIII-1) or (VIII-2). However, at least one of W ³ to W ⁶ is a group represented by the following formula (VIII-1) or (VIII-2), and preferably two or more of W ³ to W ⁶ are A group represented by the following formula (VIII-1) or (VIII-2).

The specific nitrogen-containing compound can be exemplified by the compounds represented by the following general formulae (X-1) to (X-3).

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

The specific nitrogen-containing compound may be a monomer or an oligomer, or may be a mixture of a monomer and an oligomer. Examples of the oligomer include those in which a monomer is formed by a reaction.

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 preferably 1 part by mass based on 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 at the time of forming the cured film. ～50 parts by mass, more preferably 5 parts by mass to 50 parts by mass, still more preferably 5 parts by mass to 20 parts by mass.

<Hot latent acid generator> The polyketone composition may further contain a latent heat acid generator. The latent heat acid generator is a compound which generates an acid by heating. When the polyketone composition contains a latent heat acid generator, since a cross-linking reaction by a specific nitrogen-containing compound can be promoted to obtain a stronger cured product, the chemical resistance of the cured film tends to be improved.

Examples of the acid produced by the latent heat acid generator include arylsulfonic acid such as p-toluenesulfonic acid and benzenesulfonic acid; (±)-10-camphorsulfonic acid, trifluoromethanesulfonic acid, and nonafluorobutanesulfonic acid; Perfluoroalkanesulfonic acid; methanesulfonic acid, sulfonic acid, butanesulfonic acid and the like.

The latent heat acid generator may be used singly or in combination of two or more. The content of the latent heat acid generator is preferably from 0.05 part by mass to 30 parts by mass, more preferably from 0.1 part by mass to 20 parts by mass, per 100 parts by mass of the total of the polyketone, the nitrogen-containing compound, and the latent heat acid generator. Further preferably, it is 0.2 part by mass to 10 parts by mass.

<Solvent> The polyketone composition may further contain a solvent. The solvent is not particularly limited as long as it can dissolve or disperse each component, and examples of the solvent include γ-butyrolactone, ethyl lactate, propylene glycol monomethyl ether acetate, butyl acetate, and benzyl acetate. N-butyl acetate, ethoxyethyl propionate, 3-methylmethoxypropionate, N-methyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, N,N-di Methylformamide, N,N-dimethylacetamide, hexamethylphosphoniumamine, butyl hydrazine, 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, ethylbenzene, propylbenzene, cumene, dicumyl , hexylbenzene, anisole, diethylene glycol dimethyl ether (diglyme), dimethyl hydrazine, 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 preferably 5 parts by mass to 95 parts by mass based on 100 parts by mass of the total amount of the polyketone, the nitrogen-containing compound, and the latent heat acid generator and the solvent contained as necessary. More preferably, it is 10 mass parts - 90 mass parts.

<Other Additives> The polyketone composition may further contain other additives. As other additives, an adhesion aid, a surfactant, a leveling agent, an antioxidant, an ultraviolet-ray agent, etc. are mentioned.

<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, a polyketone composition is coated on at least a portion of the surface of the substrate to form a composition layer. The method of applying the polyketone composition to the substrate is not particularly limited as long as the composition layer can be formed in any shape on the substrate in an arbitrary shape. Examples of the method of applying the polyketone composition onto the substrate include a dipping method, a spray coating method, a screen printing method, a spin coating method, a spin coating method, and a bar coating method.

The substrate on which the polyketone composition is applied is not particularly limited, and examples thereof include inorganic materials such as glass, semiconductor, metal oxide insulator (titanium oxide, cerium oxide, etc.) and cerium nitride; and cellulose triacetate and transparent polyfluorene. A transparent substrate composed of a transparent resin such as an imine, a polycarbonate, an acrylic polymer or a cycloolefin resin. The shape of the substrate is not particularly limited, and may be a plate shape or a film shape. The polyketone composition of the present embodiment is excellent in chemical resistance when it is formed into a cured film, and is excellent in chemical resistance. Therefore, it can be suitably used as a coating material or a molded article of a substrate.

When the polyketone composition contains a solvent, it can be dried before and after hardening. The drying method is not particularly limited, and examples thereof include a method of heat treatment using a device such as a hot plate or a drying furnace. The drying conditions are not particularly limited as long as the solvent in the polyketone composition is sufficiently volatilized, and it is usually carried out at 50 to 150 ° C for about 1 minute to 90 minutes.

After the composition layer is formed, it is hardened to obtain a polyketone cured product. The hardening method is not particularly limited, and it can be cured by heat treatment or the like. By hardening by heat treatment, a box dryer, a hot air conveyor type dryer, a quartz tube furnace, a heating plate, a rapid thermal annealing furnace, a vertical diffusion furnace, an infrared curing furnace, an electron beam curing furnace, and a microwave hardening can be used. It is carried out by a drying furnace such as a furnace.

The atmosphere at the time of hardening may be selected from any of an inert atmosphere such as the atmosphere or nitrogen, and is preferably carried out in a nitrogen atmosphere from the viewpoint of preventing oxidation of the polyketone composition. The temperature and time of the heat treatment for hardening can be arbitrarily set with reference to the composition conditions, work efficiency, and the like, and is usually carried out at 60 ° C to 200 ° C for about 30 minutes to 2 hours.

The obtained polyketone cured product can be used as a substrate having a polyketone cured product in a state of adhering to a substrate, and can be used by being peeled off from the substrate as needed. In the substrate to which the polyketone hardened material is attached, the polyketone hardened material may be provided on at least a part of the surface of the substrate, or may be provided only on one side of the substrate, or may be provided on both sides. Further, the polyketone cured product may have a single layer structure of one layer, or may have a plurality of layers having a laminate of two or more layers.

<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 which can be used for the optical element and the image display device may be the above-mentioned substrate with a polyketone hardened material. Further, the substrate can be applied to an optical element as long as it is a transparent substrate. Examples of the transparent substrate include a transparent substrate which has been exemplified in the production of a polyketone cured product.

The optical element and the image display device can be attached to an LCD (Liquid-Crystal Display) by, for example, a substrate on the substrate to which the polyketone cured product is attached, via a binder, an adhesive, or the like. The use of an ELD (Electroluminescence Display) or the like is obtained.

Various optical elements such as a polyketone cured product and a polarizing plate using a polyketone cured product can be preferably used in various image display devices such as liquid crystal display devices. 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, it can be manufactured by appropriately assembling optical elements such as a liquid crystal cell and a polarizing plate, and various constituent members such as an illumination system (such as a backlight), and mounting a driving circuit. The liquid crystal cell is not particularly limited, and various types such as a TN (Twisted Nematic) type, an STN (Super Twisted Nematic) type, and a π type can be used.

Examples of the use of the image display device include an OA (Office Automation) machine such as a desktop computer, a notebook computer, and a printer; a mobile phone, a clock, a digital camera, and a mobile information terminal (PDA (Personal Digital) Assistant)), personal digital assistants, mobile games and other mobile devices; home electric appliances such as cameras, televisions, microwave ovens; rearview mirrors, car navigation system screens, car audio and other in-vehicle devices; commercial shop information screens Such as display machines; maintenance screens such as monitor screens; care machines such as care screens; and medical devices such as medical screens. The entire disclosure of Japanese Patent Application No. 2016-153622 is incorporated herein by reference. All of the documents, patent applications, and technical specifications described in the specification are incorporated by reference to the individual documents, patent applications, and technical specifications. To be incorporated into this specification. [Examples]

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

<Polyketone Composition> The components (A) to (D) were blended in the ratios shown in Tables 1 to 4, and then filtered through a membrane filter made of PTFE (polytetrafluoroethylene) to obtain Examples and Comparative Examples. Polyketone composition. The values in parentheses indicate the blending ratio (parts by mass, solids ratio). "-" means that it does not contain this ingredient. The components in Tables 1 to 4 are as follows.

(A) component (Synthesis Example 1) Synthesis of polyketone PK-1 as a monomer containing 10 mmol of 2,2'-dimethoxybiphenyl and 10 mmol of cis-1,4-cyclohexanedicarboxylic acid Into the flask, 30 mL of a mixture of phosphorus pentoxide and methanesulfonic acid (mass ratio 1:10) was added, and stirred at 60 °C. After the reaction, the contents were poured into 500 mL of methanol, and the resulting precipitate was taken out by filtration. The obtained solid was washed with distilled water and methanol, and then dried to obtain a polyketone PK-1. The polyketone PK-1 obtained had a weight average molecular weight of 20,000 and a number average molecular weight of 8,000. In addition, the weight average molecular weight and the number average molecular weight are values calculated and calculated by the method described later. The weight average molecular weight (Mw) and the number average molecular weight (Mn) of the polyketone PK-2 to polyketone PK-15 described later were also measured by the same method.

(Synthesis Example 2) Synthesis of Polyketone PK-2 The same procedure as in Example 1 was carried out except that 10 mmol of 2,2'-dimethoxybiphenyl and 13 mmol of 1,3-adamantane dicarboxylic acid were used as a monomer. To obtain polyketone PK-2. The polyketone PK-2 obtained 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 The same procedure as in Example 1 was carried out except that 10 mmol of 2,2'-dimethoxybiphenyl and 10 mmol of 1,3-adamantane diacetic acid were used as a monomer. To obtain polyketone PK-3. The polyketone PK-3 obtained 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 except that 10 mmol of 2,2'-dimethoxybiphenyl, 5 mmol of 1,3-adamantane dicarboxylic acid, and 5 mmol of cis-1,4-cyclohexane were used. Polyketone PK-4 was obtained in the same manner as in Example 1 except that dicarboxylic acid was used as a monomer. The polyketone PK-4 obtained 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 except that 10 mmol of 2,2'-dimethoxybiphenyl, 5 mmol of 1,3-adamantane dicarboxylic acid, and 5 mmol of dodecanedioic acid were used as a monomer The polyketone PK-5 was obtained in the same manner as in Example 1. The polyketone PK-5 obtained 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 except that 10 mmol of 2,2'-dimethoxybiphenyl, 5 mmol of 1,3-adamantane diacetic acid, and 5 mmol of dodecanedioic acid were used as a monomer The polyketone PK-6 was obtained in the same manner as in Example 1. The polyketone PK-6 obtained 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, except that 10 mmol of 2,2'-dimethoxybiphenyl, 5 mmol of 1,3-adamantane diacetic acid, and 5 mmol of adipic acid were used as a monomer, Example 1 was operated in the same manner to obtain polyketone PK-7. The polyketone PK-7 obtained 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 for using 10 mmol of 2,2'-dimethoxybiphenyl, 5 mmol of 1,3-adamantane diacetic acid, and 5 mmol of cis-1,4-cyclohexane Polyketone PK-8 was obtained in the same manner as in Example 1 except that dicarboxylic acid was used as a monomer. The polyketone PK-8 obtained 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 except for using 10 mmol of 2,2'-dimethoxybiphenyl, 5 mmol of 1,3-adamantane diacetic acid, and 5 mmol of trans-1,4-cyclohexane Polyketone PK-9 was obtained in the same manner as in Example 1 except that dicarboxylic acid was used as a monomer. The polyketone PK-9 obtained 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 except that 10 mmol of 2,2'-dimethoxybiphenyl, 5 mmol of 1,3-adamantane diacetic acid, and 5 mmol of 1,4-cyclohexanedicarboxylic acid were used. (Polymer PK-10 was obtained in the same manner as in Example 1 except that the mixture of cis and trans, cis: reverse (mole ratio) = 7:3). The polyketone PK-10 obtained 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 except using 10 mmol of 2,2'-dimethoxybiphenyl, 5 mmol of 1,3-adamantane diacetic acid, and 5 mmol of decalin-2,6-di Polyketone PK-11 was obtained in the same manner as in Example 1 except that formic acid was used as a monomer. The polyketone PK-11 obtained 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 except for using 10 mmol of 2,2'-dimethoxybiphenyl, 5 mmol of 1,3-adamantane diacetic acid, and 5 mmol of norbornane dicarboxylic acid (2,4) Polyketone PK-12 was obtained in the same manner as in Example 1 except that a mixture of norbornanedicarboxylic acid and 2,5-norbornanedicarboxylic acid was used as a monomer. The polyketone PK-12 obtained 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 except for using 10 mmol of 2,2'-dimethoxybiphenyl, 5 mmol of 1,3-adamantane diacetic acid, and 5 mmol of trans-2,3-norbornane Polyketone PK-13 was obtained in the same manner as in Example 1 except that dicarboxylic acid was used as a monomer. The obtained 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 except that 10 mmol of 2,2'-bis(2-methoxyphenyl)propane, 5 mmol of 1,3-adamantane diacetic acid, and 5 mmol of 1,4-ring were used. Polyketone PK-14 was obtained in the same manner as in Example 1 except that hexanedicarboxylic acid (mixture of cis and trans, cis:trans (mole ratio) = 7:3) was used. The polyketone PK-14 obtained 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 except using 10 mmol of diphenyl ether, 5 mmol of 1,3-adamantane diacetic acid, and 5 mmol of 1,4-cyclohexanedicarboxylic acid (mixture of cis and trans) , cis: reverse (mole ratio) = 7: 3) The polyketone PK-15 was obtained in the same manner as in Example 1 except that the monomer was used. The polyketone PK-15 obtained had a weight average molecular weight of 27,000 and a number average molecular weight of 8,000.

(B) Component B1: a compound represented by the following formula (XII).

B2: a compound represented by the following formula (XIII).

B3: a compound represented by the following formula (XIV).

B4: a compound represented by the following formula (XV).

B5: a compound represented by the following formula (XVI) (epoxy equivalent: 188).

B6: a compound represented by the following formula (XVII).

B7: triepoxypropyl-p-aminophenol.

(B') component B'1: a compound represented by the following formula (XVIII).

(C) Component C1: A compound represented by the following formula (XVIV).

C2: a compound represented by the following formula (XX).

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

[Table 1]

[Table 2]

[table 3]

[Table 4]

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

(1) Sample for chemical resistance test The polyketone composition was applied onto a ruthenium substrate by a spin coating method. The obtained tantalum substrate was dried on a hot plate heated to 120 ° C for 3 minutes. Further, an inert gas drying oven (manufactured by Kokon Thermal Systems Co., Ltd.) was used, and the dried ruthenium substrate was subjected to heat treatment at 200 ° C for 1 hour under a nitrogen gas stream to obtain a cured polyketone. The substrate was rubbed and made into a sample for chemical resistance test.

(2) Sample for transmittance measurement The polyketone composition was applied onto 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 having a polyketone cured product, which was used as a sample for transmittance measurement.

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

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

<Molecular weight determination of polyketone> The molecular weight (weight average molecular weight and number average molecular weight) of polyketone is determined by gel permeation chromatography (GPC) using tetrahydrofuran (THF) as a washing liquid, and is used in standard polystyrene. Calculated in the conversion. The details are as follows.

‧ Device name: Ecosec HLC-8320GPC (manufactured by Tosoh Corporation). ‧ Pipe column: TSK gel Supermultipore HZ-M (manufactured by Tosoh Corporation). ‧Detector: Use UV detector and RI detector. ‧ Flow rate: 0.4 mL / min.

<Chemical Resistance Test> A test piece was prepared by cutting a ruthenium substrate with a polyketone hardened material. The test piece was immersed in the liquid medicine by the following conditions (a) or (b), respectively. It is observed whether the polyketone hardened material in the impregnation is whether the polyketone film is dissolved or whether the polyketone film is peeled off from the tantalum substrate. The observation results are shown in Tables 5 and 6. In this test, the case where no dissolution or peeling was found was regarded as "no change".

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

<Determination of Transmittance> The visible light penetration of a glass substrate with a polyketone hardened material at 400 nm was measured by a spectrophotometer (V-570, manufactured by JASCO Corporation) and by ultraviolet visible light absorption spectroscopy. rate. A glass substrate having no polyketone cured product was used as a reference value, and the film penetration ratio converted to a film thickness of 1 μm was shown in Tables 5 and 6.

<Measurement of Thermal Decomposition Temperature> The weight reduction of the polyketone cured product was measured using a thermogravimetric scale TG-DTA6300 (manufactured by Hitachi Advanced Science Co., Ltd. (Hitachi Advanced Technology Co., Ltd.)). The intersection of the tangent of the curve in which the weight is largely reduced by heating is defined as the thermal decomposition temperature. The results are shown in Tables 5 and 6.

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

[table 5]

[Table 6]

It is understood that the polyketone cured product obtained from the polyketone composition of the example is excellent in chemical resistance, transparency, and heat resistance, and further has high elongation. On the other hand, Comparative Examples 1 to 3 which did not contain a specific nitrogen-containing compound were inferior in chemical resistance and elongation. Further, in Comparative Examples 4 to 13 in which an epoxy compound was used instead of the specific nitrogen-containing compound, the chemical resistance, transparency, and heat resistance were similar to those of the examples, but the elongation was low.

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Claims (12)

A polyketone composition comprising: a polyketone comprising a structural unit represented by the following general formula (I) in a main chain; and a nitrogen-containing compound having a nitrogen atom and bonded to the nitrogen atom a group selected from at least one of the group consisting of a methylol group and an alkoxymethyl group; In the formula (I), X each independently represents a divalent group having 1 to 50 carbon atoms which may have a substituent, and Y each independently represents a divalent hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and n represents An integer from 3 to 1000. The polyketone composition according to claim 1, wherein, in the above formula (I), X each independently contains a divalent group having 6 to 50 carbon atoms, and the divalent group contains an aromatic ring. The polyketone composition according to claim 1 or 2, wherein, in the above formula (I), X each independently comprises a compound selected from the group consisting of the following general formulae (II-1) to (II-3) At least one of the groups represents a divalent group: In the formula (II-1), R ¹ each 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. m each independently represents an integer of 0 to 3; In the formula (II-2), R ¹ each 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. m each independently represents an integer of 0 to 3, and Z represents an oxygen atom or a divalent group represented by the following general formulae (III-1) to (III-7). In the general formulae (III-1) to (III-7), R ¹ each 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 carbon number which may have a substituent The hydrocarbon group of 1 to 30, R ³ and R ⁴ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and m each independently represents an integer of 0 to 3, and n each independently represents 0 to 4 Integer, p each independently represents an integer from 0 to 2; In the formula (II-3), R ⁵ each independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and n each independently represents an integer of 0 to 4. The polyketone composition according to any one of claims 1 to 3, wherein, in the above formula (I), Y contains a divalent saturated hydrocarbon group. The polyketone composition according to claim 4, wherein, in the above formula (I), Y contains a divalent saturated alicyclic hydrocarbon group. The polyketone composition according to any one of claims 1 to 5, wherein, in the above formula (I), the carbon number of Y is from 6 to 30. The polyketone composition according to any one of claims 1 to 6, wherein the total number of the methylol-bonded hydroxymethyl group and the alkoxymethyl group in the nitrogen-containing compound is from 2 to 6. The polyketone composition according to any one of claims 1 to 7, further comprising a latent heat acid generator. The polyketone composition according to any one of claims 1 to 8, which further contains a solvent. A cured polyketone which is a cured product of the polyketone composition according to any one of claims 1 to 9. An optical element having the polyketone hardened material of claim 10. An image display device having the polyketone hardened material of claim 10.