JPH07207020A - Photosensitive elastomer and method for producing the same - Google Patents

Abstract

(57) [Summary] [Structure] An aromatic dicarboxylic acid having a phenolic hydroxyl group (for example, 2,5-dihydroxyisophthalic acid, 2,
5-dihydroxy-1,4-benzenediacetic acid, etc.) and an aromatic diamine (eg 3,4′-oxydianiline, phenylenedianiline, etc.) are polycondensed to produce an end-reactive aromatic polyamide oligomer, The resulting oligomer and a polybutadiene-acrylonitrile-based copolymer having a carboxyl group at the terminal are polymerized to produce an aromatic polyamide-polybutadiene-based block copolymer having a phenolic hydroxyl group, and this block copolymer is cinnamoyl chloride-containing. A photosensitive elastomer obtained by reacting with. [Effect] This photosensitive elastomer is excellent in thermal stability and mechanical properties as compared with conventional photosensitive resins.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel heat-resistant photosensitive elastomer, more specifically, a heat-resistant photosensitive elastomer having excellent mechanical properties and good solubility in an organic solvent. And the manufacturing method thereof.

[0002]

2. Description of the Related Art Photosensitive resins are highly useful materials used in various fields such as resist materials, printing inks, paints, plate-making materials and adhesives. Generally, rubber type, acrylic type, acrylate type, thiol type, epoxy type,
A wide range of silicone materials, either alone or mixed,
in use. In particular, a photosensitive resin material using a sulfonyl azide compound and a rubber material having a double bond in the polymer molecular chain such as polyisoprene and polybutadiene is
A detailed study was reported in "Photoresist (1975)" by William S. Deforest, and it is known that it is a negative photoresist which is insolubilized by ultraviolet irradiation. In the case of 1,2-polybutadienes having a double bond at the terminal or in the side chain, in the presence of oxygen, or,
In the presence of 4,4'-diazidophenyl, it exhibits UV photosensitivity and becomes insoluble. Kakuta et al.
It is reported by the Proceedings of the Annual Meeting of the Spring Meeting 906 (1975).

An elastomeric block copolymer obtained by anionic polymerization is also known as a photosensitive elastomer composition having another unsaturated double bond in the polymer structure. For example, a solvent-soluble thermoplastic elastomer comprising a block of a non-elastomeric polymer block having a glass transition temperature of 25 ° C. or higher and an elastomer having a glass transition temperature of 10 ° C. or lower disclosed in JP-B-51-43374 is disclosed. Are known. In addition, the Japanese Examined Sho 63-
70242 discloses a solvent-soluble thermoplastic multi-branched block copolymer in which a non-elastomer portion composed of a polyfunctional vinyl derivative and an elastomer portion composed of butadiene and an isoprene derivative are formed. As another polymer material, polyvinyl cinnamate, which is a polyvinyl type having no unsaturated double bond in the main chain (US Pat.
2725372, Japanese Patent Publication No. 38-1492, Japanese Patent Publication No. 40-
20188), cinnamic acid ester of ethylene-vinyl alcohol copolymer ((US Pat. 325766).
4), cinnamic acid ester of glyptal resin (engineering, 6
8,387 (1965)), cinnamic acid ester of epoxy resin (Brit. Pat. 3257664), cinnamic acid ester of polyether (Japanese Patent Publication No. 48-17,000,
JP-B-51-17465), cinnamoyl type polymer having a polystyrene skeleton (JP-B-49-46396),
Acrylic type cinnamoyl type polymer (JP-A-48-74)
594) is well known, and in the above-mentioned fields,
Various applications have been studied.

[0004]

However, the above-mentioned photosensitive resin compositions that have been proposed hitherto have room temperature to 10%.
The temperature range around 0 ° C is intended for the operating environment. In the temperature range higher than that, it is easily deformed by heat, and it is thermoplastic and has a double bond portion at the end, so that it is used during molding. Consideration at the time of processing was necessary, such as the addition of a thermal polymerization inhibitor. The present invention has been made in view of the above-mentioned problems in the conventional technique. Therefore,
An object of the present invention is to provide a photocurable elastomer that can be used in a high temperature range (150 ° C or higher).

[0005]

The inventors of the present invention have conducted research to solve the above-mentioned problems in the conventionally proposed techniques, and as a result, in order to impart heat resistance to the photosensitive resin, Instead of polyvinyl alcohol that can easily introduce a functional group, focusing on an aromatic polyamide having a reactive group that can introduce a photosensitive group, found that the above problems can be solved, and to complete the present invention I arrived. That is, the photosensitive elastomer of the present invention has a block copolymer composed of a heat-resistant aromatic polyamide and a polybutadiene-based rubber as a polymer main chain, and a phenolic hydroxyl group which is a reactive group present in an aromatic polyamide moiety is interposed. Is a side chain and is represented by the following general formula (I) having photosensitivity.

[0006]

[Chemical 6] (In the formula, X and Y are 0.7 ≦ X ≦ 1.0 and 0 ≦ Y ≦ 0.3.
Where Z represents the average degree of polymerization, and 10 ≦ Z ≦ 20.
Represents an integer of 0, R is an organic group having a phenolic hydroxyl group, Ar is a divalent aromatic group, and W is the following formula (II).
Is a photosensitive group represented by, p represents an integer of 2 ≦ p ≦ 100, m and n are the introduction ratios of the photosensitive group W, and 0.0
1 ≦ m ≦ 1, 0 ≦ n ≦ 0.99, 0.01 ≦ m / (m
+ N) ≦ 1, and Mw of the photosensitive elastomer of formula (I)
= 15,000 to 250,000. )

[0007]

Embedded image -CO-CH = CH-R 'or _{-CH 2 -CH = CH-R'} (II) ( wherein, R 'is an aliphatic group having not more than 10 carbon atoms, cyclic aliphatic group or benzene Means an aromatic group represented by a ring)

The photosensitive elastomer of the present invention comprises an aromatic polyamide butadiene block copolymer having a phenolic hydroxyl group represented by the following general formula (III) and a compound represented by the following general formulas (IV) and (V). Can be produced in the presence of a polar solvent.

[0009]

[Chemical 8] (In the formula, R, Ar, X, Y, Z, and P have the same meanings as described above.)

Embedded image Y—CO—CH═CH—R ′ (IV) (In the formula, Y represents a halogen atom, Cl, Br or I
And R ′ has the same meaning as described above. )

Embedded image Y—CH ₂ —CH═CH—R ′ (V) (wherein Y and R ′ have the same meanings as described above).

The aromatic polyamide-polybutadiene block copolymer having a phenolic hydroxyl group which is a reactive group represented by the above general formula (I) used in the present invention may be one synthesized by any method. After polycondensing an aromatic diamine compound and a phenol aromatic carboxylic acid in an amide-based organic solvent represented by N-methyl-2-pyrrolidone under heating in the presence of a phosphite ester catalyst, a carboxyl group is formed at both terminals. It is desirable to synthesize it by block copolymerizing with a polybutadiene-based copolymer having a group. Examples of the polybutadiene-based copolymer having a carboxyl group at both ends which can be used here include a carboxyl group-terminated polybutadiene, or a carboxyl group-terminated polybutadiene-acrylonitrile copolymer and the like, which are easily commercially available. It is available. It can also be easily synthesized by radical polymerization or anionic polymerization. Examples of the commercially available product include
Hycar CTB and Hycar CTBN (both are trade names) manufactured by Goodrich.

As the aromatic diamine, for example, metaphenylenediamine, paraphenylenediamine, 4,4'-
Ethylene dianiline, 4,4'-isopropylidene dianiline, 3,4'-oxydianiline, 4,4'-oxydianiline, 3,3'-sulfonyldianiline, 4,
4'-sulfonyldianiline, 1,4-naphthalenediamine, 1,5-naphthalenediamine, 2,6-naphthalenediamine, 1,3-bis (metaaminophenyl)-
1,1,3,3-tetramethyldisiloxane, 4,4 '
-Bis (4-aminophenoxy) diphenyl sulfone,
4,4'-bis (3-aminophenoxy) diphenyl sulfone, 4,4'-bis (4-aminophenoxy) benzophenone, 4,4'-bis (3-aminophenoxy)
Benzophenone, 4,4'-bis (4-aminophenylmercapto) benzophenone, 2,2-bis [4- (2
-Trifluoromethyl-4-aminophenoxy) phenyl] hexafluoropropane, 2,2-bis [4- (3
-Trifluoromethyl-5-aminophenoxy) phenyl] hexafluoropropane, 2,2-bis [4- (3
-Trifluoromethyl-4-aminophenoxy) phenyl] hexafluoropropane, 2,2-bis [4- (2
-Trifluoromethyl-5-aminophenoxy) phenyl] hexafluoropropane, 2,2-bis [4- (4
-Trifluoromethyl-5-aminophenoxy) phenyl] hexafluoropropane, 2,2-bis [4- (2
-Nonafluorobutyl-5-aminophenoxy) phenyl] hexafluoropropane, 2,2-bis [4- (4
-Nonafluorobutyl-5-aminophenoxy) phenyl] hexafluoropropane, 4,4'-diaminodiphenylmethane, o-tolidine, o-dianisidine and the like can be mentioned, but not limited thereto. Moreover, you may implement these aromatic diamines individually or in combination.

As the phenol aromatic carboxylic acid,
2,5-dihydroxy-1,4-benzenediacetic acid, 5-
Examples thereof include, but are not limited to, dicarboxylic acids such as hydroxyisophthalic acid, 4-hydroxyisophthalic acid, 4,6-dihydroxyisophthalic acid and derivatives thereof. Moreover, you may implement these individually or in combination of multiple. Examples of the phosphite used in this synthesis include triphenyl phosphite, diphenyl phosphite, tri-o-tolyl phosphite, di-o-tolyl phosphite, and tri-m-tolyl phosphite. , Di-m-tolyl phosphite, tri-p-tolyl phosphite, di-p-tolyl phosphite, tri-o-chlorophenyl phosphite, di-o-chlorophenyl phosphite, triphosphite −
Examples thereof include, but are not limited to, p-chlorophenyl and di-p-chlorophenyl phosphite. Further, as the pyridine derivative used together with the phosphite in the present invention, pyridine, 2-pyricon,
3-pyridone, 4-pyridone, 2,4-lutidine, 2,
Examples thereof include 6-lutidine and 3,5-lutidine.

The above reaction is carried out by polycondensation in the presence of a phosphite and a pyridine derivative. In this reaction, a solution polymerization method using a mixed solvent containing a pyridine derivative is usually employed. The organic solvent used here is limited in that it does not substantially react with both reaction components and the phosphite ester, but it is also a good solvent for the components and good for the reaction product polymer. It is preferably a solvent. A typical example of such an organic solvent is an amide solvent such as N-methyl-2-pyrrolidone or N, N-dimethylacetamide. Here, in order to obtain a polymer having a high degree of polymerization, an alkali metal salt represented by lithium chloride or an alkaline earth metal salt represented by calcium chloride can be added to this reaction system.

Further, the amount of the pyridine derivative used here needs to be an equimolar amount or more with respect to the carboxyl group, but in practice, it is often used in a large excess including the role as a reaction solvent. . Here, a mixed solvent comprising a pyridine derivative and an organic solvent represented by N-methyl-2-pyrrolidone is preferably used, and the amount of the mixed solvent used is usually 5 to 30% by weight of the reaction components. Only the amount used. Usually, the reaction temperature is preferably in the range of 60 to 140 ° C. The reaction time is largely influenced by the reaction temperature, but in any case it is advisable to stir the reaction system until the maximum viscosity which means the highest degree of polymerization is obtained, often between a few minutes and 20 hours.

Under the above reaction conditions, it is possible to produce a polymer having an average degree of polymerization of 2 to 100 using equimolar amounts of the reaction components. If the average degree of polymerization exceeds 100, it is not preferable in terms of processability, but for one purpose, one of them may be used in excess to reduce the average degree of polymerization. After completion of the reaction, the reaction mixture is thrown into a non-solvent such as methanol or hexane to separate the produced polymer, and further purified by a reprecipitation method to remove by-products and inorganic salts. You can get coalesced. In this manner, the aromatic polyamide-butadiene block copolymer thus obtained is used as a main raw material, and a compound represented by the general formula (IV) or (V), which is a photosensitive group, is generally known. By using the method described above, the photosensitive elastomer of the present invention can be synthesized.

As the reaction between the aromatic polyamide butadiene block copolymer and the compound represented by the general formula (IV), a condensation reaction with a base is preferably used. Examples of this base include pyridine, triethylamine, sodium hydroxide, dimethylaniline, tetramethylurea, metallic magnesium and the like. If necessary, a metal salt such as lithium chloride or calcium chloride may be added for the reaction. The acid halide (I
V) is cinnamoyl chloride, cinnamoyl bromide, 3- (2-nitrophenyl) propenoyl chloride, 3- (4-nitrophenyl) propenoyl chloride, 3- (2,4-dinitrophenyl) propenoylbromide. , 3- (2,6-dinitrophenyl) propenoyl chloride, 3- (2,6-dinitrophenyl) propenoyl bromide, 3- (2,4,6-trinitrophenyl) propenoyl chloride, 3- (2 , 4,6-Trinitrophenyl) propenoyl bromide, 3-o-tolylpropenoyl chloride, 3-m-tolylpropenoyl chloride, 3-p-tolylpropenoyl chloride, 3-
(2,6-dimethylphenyl) propenoyl chloride,
3- (2,4-dimethylphenyl) propenoyl chloride, 3- (3,5-dimethylphenyl) propenoyl chloride, 3- (2,4,6-trimethylphenyl) propenoyl chloride, acryloyl chloride, acryloyl bromide, Crotyl chloride, crotyl bromide, 2
-Pentenoyl chloride, 2-hexenoyl chloride,
4-methyl-2-pentenoyl chloride, 2-butenoyl chloride, 2-nonenoyl chloride, 2-undecenoyl chloride, 2-tridecenoyl chloride, 3-cyclohexylpropenoyl chloride, 3-cyclopentylpropenoyl chloride , 3- (1-naphthyl) propenoyl chloride, 3- (2-naphthyl) propenoyl chloride and the like, but the present invention is not limited thereto.

As the reaction between the aromatic polyamide butadiene block copolymer and the compound represented by the general formula (V), a condensation reaction with a base is preferably used. As this base, sodium hydroxide, potassium hydroxide, sodium hydride, potassium hydride, sodium amide,
Examples thereof include sodium carbonate and potassium carbonate. The acid halide (V) used in this reaction includes cinnamyl chloride, cinnamyl bromide, 3- (2-nitrophenyl) propenyl chloride, 3- (4-nitrophenyl) propenyl chloride and 3- (2,4). -Dinitrophenyl) propenyl chloride, 3- (2,4-dinitrophenyl) propenyl bromide, 3- (2,6-dinitrophenyl) propenyl chloride, 3- (2,6-dinitrophenyl) propenyl bromide, 3- (2 , 4, 6
-Trinitrophenyl) propenyl chloride, 3-
(2,4,6-Trinitrophenyl) propenyl bromide, 3-o-tolylpropenyl chloride, 3-m-tolylpropenyl chloride, 3-p-tolylpropenyl chloride, 3- (2,6-dimethylphenyl) propenyl chloride , 3- (2,4-dimethylphenyl) propenyl chloride, 3- (3,5-dimethylphenyl) propenyl chloride, 3- (2,4,6-trimethylphenyl)
Propenyl chloride, 2-propenyl chloride, 2-propenyl bromide, 2-butenyl chloride, 2-butenyl bromide, 2-pentenyl chloride, 2-hexenyl chloride, 4-methyl-2-pentenyl chloride, 2-
Heptenyl chloride, 2-nonenyl chloride, 2-undecenyl chloride, 2-tridecenyl chloride, 3-cyclohexyl-2-propenyl chloride, 3-cyclopentyl-2-propenyl chloride, 3- (1-naphthyl) propenyl chloride, Examples thereof include 3- (2-naphthyl) propenyl chloride, but the present invention is not limited thereto.

Further, in the photosensitive elastomer of the present invention,
A good photocurable resin cured product can also be obtained by mixing a photopolymerization initiator. Specific examples of the photopolymerization initiator include benzophenone, benzoin alkyl ethers such as benzoyl methyl, ethyl, isopropyl and isobutyl ether, α-methylbenzoyl, α-methoxybenzoin methyl ether, α-methylbenzoin methyl ether, benzoinphenyl. Ether, α-t-butylbenzoin, anthraquinone, 2-chloroanthraquinone, 2,2′-dimethoxyacetophenone, 2,2 ′
-Diethoxyacetophenone, benzyl, vivaloin,
2,4,6-trinitroaniline, 1-nitropyrene,
1,8-dinitropyrene, cyanoacridine, azobisisobutyronitrile, 2,2'-azobispropane,
m, m'-azoxystyrene, benzoyl peroxide, di-t-butyl peroxide, 1- or 2-
Naphthyl peroxide, diphenyl sulfide, diphenyl disulfide, dibenzyl sulfide, dibenzyl disulfide, dibenzothiazoyl disulfide, methyldiethyldithiocarbamate, S-acyldithiocarbamate, decylthiobenzoate, p, p'-tetramethyldiaminobenzophenone, N- Acetyl-4-
Examples thereof include, but are not limited to, nitro-1-naphthylamine and the like. The amount of the compound used is usually 0.01 to 5 parts by weight in the photosensitive composition,
They can be used alone or in combination of two or more. In addition to the above photopolymerization initiator, a photosensitization aid may be used for the purpose of widening the photosensitization wavelength range. As the auxiliary agent, 1,2-
Examples thereof include, but are not limited to, quinone-based compounds such as benzanthraquinone and anthraquinone, 5-nitrofluorene, aromatic nitro compounds such as 5-nitroacenaphthene, and ketone-based compounds other than the above.

Further, in order to obtain a film-shaped molded product, a solvent casting method in which the solution of the above-mentioned photocurable resin composition is cast on a suitable substrate is desirable. Usually, a film-shaped molded product is obtained by casting the solution-type photocurable resin composition of the present invention on a suitable substrate, drying it by a conventional method, and peeling it from the substrate. As the base material of the molded product, it is desirable that a film-shaped molded product can be easily formed on the surface of the base material and can be peeled off, and the material is not particularly limited. For example, a glass plate having a smooth surface, a PET film, a Kapton film, etc., a metal plate such as an aluminum plate, a copper plate, etc., a metal net-like molding, or the above-mentioned material surface-treated with a release agent may be used. Can be used without. As a light source that can be used in the photocuring method of the photocurable resin composition of the present invention, a light source such as an ultraviolet fluorescent lamp, a low pressure mercury lamp, a high pressure mercury lamp, an electron beam, or a laser can be used.
The irradiation time is several minutes to several hours, and is set by the distance to the light source, the light source illuminance, and the photosensitivity. Further, the photocurable resin composition of the present invention, if necessary, a thermal polymerization inhibitor, a colorant, a filler (inorganic powder, glass fiber, shirasu balloon,
Glass hollow bodies, etc.) and other chain transfer agents can be added and used.

[0020]

The present invention will be described in detail below with reference to examples, but the present invention is not limited thereto. Synthesis Example 1: Synthesis of aromatic polyamide having cinnamoyl group 5.018 g (27.56 mmol) of 5-hydroxyisophthalic acid, 3,4 'in a 500 ml three-neck round bottom flask.
-Oxydianiline 6.074 g (30.32 mmol), calcium chloride 2.08 g, lithium chloride 0.6
9 g, 55.5 g of N, N-dimethylacetamide, 8.6 g of pyridine, and 18.8 g of triphenyl phosphite were added, and polycondensation was performed at 90 ° C. for 2 hours in a dry nitrogen atmosphere to obtain an end-reactive aromatic polyamide oligomer. Prepared. Next, 10 g of liquid polybutadiene acrylonitrile rubber having a carboxyl group at the end dissolved in 50 ml of N, N-dimethylacetamide (Hycar CTBN10).
08-SP: BF-Goodrich) was added to the reactor, and the reaction was further continued for 2 hours. This was allowed to cool to room temperature, diluted with 40 ml of N, N-dimethylacetamide, and then poured into 800 ml of a methanol precipitation bath with stirring to obtain a polymer powder. This crude polymer was purified by a conventional method. Yield 19.91 g (yield 99
%), Intrinsic viscosity η inh = 0.51 dl / g (30 ° C.,
It was measured with an Oswald viscometer in N, N-dimethylacetamide). In order to introduce a cinnamoyl group, which is a photosensitive group, into this crude polymer, the crude polymer 1.
5 g was dissolved in 40 ml of pyridine, and then 2.5 g of lithium chloride was added and dissolved, and then cinnamoyl chloride 0.
72 g was added and the mixture was reacted with stirring at room temperature for 24 hours, and after the reaction was completed, it was poured into 800 ml of methanol to obtain a crude photosensitive resin. It was produced by a conventional method to give the desired product in a yield of 2.69.
g, cinnamoyl group introduction rate 75% (determined by ¹ H-NMR method), polystyrene conversion weight average molecular weight of about 42
000 (GPC method, solvent 0.1 wt% LiBr / N-methyl-2-pyrrolidone, column: Shodex KD-
80M).

Synthetic Example 2: Synthesis of aromatic polyamide-block copolymer having cinnamyl group An aromatic polyamide having a phenolic hydroxyl group as a main raw material was synthesized in the same manner as in Synthetic Example 1 [yield 19.80 g, yield 9
8%, intrinsic viscosity η inh = 0.45 dl / g (30 ° C,
In an N, N-dimethylacetamide, measured with an Oswald viscometer)] and then in a 100 ml three-necked round bottom flask, 6.0 g of the crude polymer was dissolved in 40 ml of N, N-dimethyl-imidazolidinone to give 0.2 g of After adding metallic Na and stirring, 1.52 g of cinnamilk chloride was added over 10 minutes, and the mixture was reacted at room temperature for 24 hours. After the reaction, the reaction solution was slowly dropped into 2 liters of methanol to precipitate the reaction product. After filtration, the product was purified by a conventional method to give a yield of 6.8 g and a polystyrene-equivalent weight average molecular weight of about 32000 (GPC
Method, solvent 0.1 wt% LiBr / N-methyl-2-pyrrolidone, column: Shodex KD-80M) to obtain a photosensitive polymer.

Example 1 2.0 g of the photosensitive resin obtained in Synthesis Example 1 was dissolved in 8 ml of N, N-dimethylacetamide and then 20 cm × 2.
It is drowned on a 0 cm glass substrate and a cast film is prepared by a conventional method. A conveyor type ultraviolet curing device (light source: low pressure mercury lamp (1500 w), 900 mJ /
cm ^2/1 pass) was evaluated using. Example 2 1 part by weight of Michler's ketone as a sensitizer was added to the coating material of Example 1 and evaluated in the same manner. Example 3 1, 2 parts of the sensitizer of Example 2 (1 part by weight of Michler's ketone) was added.
Benzanthraquinone was replaced with 1 part by weight and evaluated in the same manner.

Example 4 The photosensitive resin obtained in Synthesis Example 2 was treated and evaluated in the same manner as in Example 1. Example 5 The photosensitive resin obtained in Synthesis Example 2 was treated and evaluated in the same manner as in Example 2. Example 6 The photosensitive resin obtained in Synthesis Example 2 was treated and evaluated in the same manner as in Example 3. Evaluation Results Photosensitivity was evaluated by a solubility test of N, N-dimethylformamide of sample films having different numbers of light irradiations. The results are shown in Table 1.

[0024]

[Table 1] ×: dissolved Δ: partially dissolved ○: insoluble

[0025]

INDUSTRIAL APPLICABILITY The photosensitive resin of the present invention has an aromatic polyamide main chain and polybutadiene acrylonitrile as an elastomer portion and is excellent in thermal stability as compared with a normal photosensitive resin, and is amide-based or tetrahydrofuran. Excellent solvent solubility in ether organic solvents,
It has utility in fields requiring heat stability and strength. A wide range of physical properties can be controlled by controlling the molecular weight of the main raw material aromatic polyamide and the amount of the photosensitive group introduced, and wide application is expected.

Claims (2)

[Claims] 1. A photosensitive elastomer having a structure represented by the following general formula (I). [Chemical 1] (In the formula, X and Y are 0.7 ≦ X ≦ 1.0 and 0 ≦ Y ≦ 0.3.
Where Z represents the average degree of polymerization, and 10 ≦ Z ≦ 20.
Represents an integer of 0, R is an organic group having a phenolic hydroxyl group, Ar is a divalent aromatic group, W is a photosensitive group represented by the following formula (II), and p is 2 ≦ p ≦ 100. Represents the integer of m, n is the introduction ratio of the photosensitive group W, 0.01
≦ m ≦ 1, 0 ≦ n ≦ 0.99, 0.01 ≦ m / (m +
n) ≦ 1, and Mw of the photosensitive elastomer of formula (I) =
15,000 to 250,000) embedded image —CO—CH═CH—R ′ or —CH ₂ —CH═CH—R ′ (II) (wherein R ′ is an aliphatic group having 10 or less carbon atoms, a cyclic group). Means an aliphatic group or an aromatic group represented by a benzene ring) 2. A compound represented by the following general formula (IV) or general formula (V) is obtained by converting an aromatic polyamide butadiene block copolymer having a phenolic hydroxyl group, which is a precursor represented by the following general formula (III), into The method for producing a photosensitive elastomer according to claim 1, wherein the photosensitive elastomer is reacted with ## STR3 ## - {OC - _{[(CH 2 -CH = CH-CH} 2) X - (CH-CH 2) Y ] _{Z CO- * | CN * -NH-} Ar-NH- (CO-R -CO -NH-Ar-NH) _p }-(III) | OH (In the formula, R, Ar, X, Y, Z and p have the same meanings as described above.) Embedded image Y-CO-CH = CH -R '(IV) (In the formula, Y represents a halogen atom, Cl, Br or I
And R ′ has the same meaning as described above. ) Embedded image Y—CH ₂ —CH═CH—R ′ (V) (In the formula, Y and R ′ have the same meanings as described above.)