JP5135808B2 - Resin composition for temperature-sensitive material and temperature-sensitive light transmission control material - Google Patents

Description

  The present invention relates to a temperature-sensitive material resin composition and a temperature-sensitive light transmission control material. In the present invention, the temperature-sensitive material resin composition refers to a resin composition that can provide a cured product whose light transmittance changes autonomously and reversibly in response to a change in temperature. The temperature-sensitive light transmission control material refers to a temperature-sensitive material that can control light transmittance autonomously and reversibly in accordance with a change in temperature. This material can be used as a material for a light control window or a light control sheet.

In recent years, in the field of optoelectronics, a need has arisen for a technique for effectively controlling light transmission. In addition, in recent years, while specific measures to reduce carbon dioxide emissions in the global warming problem have been demanded, a dimming window that can control the growth of animals and plants and the comfortable human environment by using solar rays and artificial rays effectively and energy-saving. And a light control sheet is needed.

As materials that satisfy these requirements, liquid crystal (see Patent Document 1), electrochromic, photochromic (see Patent Document 2), thermochromic, and thermotropic materials have been proposed. Generally, however, liquid crystals are expensive and electrochromic. The photochromic material has a problem of poor light resistance. On the other hand, thermochromic and thermotropic materials are excellent in practical use because they are easier to control and energy saving, and their manufacturing and maintenance costs are low.

As thermochromic and thermotropic materials, conventionally, a mixed solution of an amphiphile and a nonionic water-soluble polymer (see Patent Document 3), a polyalkylene glycol copolymer solution (see Patent Document 4), poly {N An alkyl-substituted (meth) acrylamide} aqueous solution (see Patent Document 5) has been proposed.

However, these thermochromic and thermotropic materials exhibit their functions for the first time in a system in which water is present. Therefore, in order to practically handle such materials as sheets and molded products, it is necessary to use a highly transparent resin made of barrier. There has been a problem that it is necessary to devise such as hermetically holding (Patent Document 6) and the handling property is poor.

Japanese Patent Laid-Open No. 01-62615 Japanese Patent Laid-Open No. 02-85274 JP 11-26500 A JP 2001-215456 A JP 2006-2104 A JP 09-140268 A

An object of the present invention is to provide a resin composition for a temperature-sensitive material and a temperature-sensitive light transmission control material that are inexpensive and easy to handle.

  As a result of intensive studies, the present inventors have found that a cured product obtained by curing a resin composition containing a polyurethane resin and a specific monomer component becomes a temperature-sensitive light transmission control material, and has completed the present invention. It was.

  That is, the present invention contains a polyurethane resin (A) (hereinafter referred to as component (A)) and a vinyl monomer (B) having an alicyclic structure in the molecule, and a resin composition for a temperature-sensitive material. A polyurethane resin (A), a vinyl monomer (B) having an alicyclic structure in the molecule (hereinafter referred to as component (B)), and a vinyl monomer (C) having an aromatic group and a hydroxyl group in the molecule (hereinafter referred to as (C A resin composition for a temperature-sensitive material, comprising a component)); and relates to a temperature-sensitive light transmission control material obtained by curing the resin composition for a temperature-sensitive material.

  If the resin composition for temperature sensitive materials of this invention is used, the temperature sensitive light transmission control material which becomes turbid or transparent according to a temperature change can be provided. Specifically, it is possible to provide a temperature-sensitive light transmission control material that becomes turbid when the temperature rises and becomes transparent when the temperature falls. Moreover, since the temperature-sensitive light transmission control material of the present invention does not require any volatile components such as water and organic solvents for the expression of temperature sensitivity, it can be practically handled as a sheet or a molded product. Further, the temperature at which light is transmitted and blocked can be arbitrarily controlled by selecting the components (A) and (B) and changing the blending ratio, and further by selecting the component (C) and changing the blending ratio. .

The resin composition of the present invention is characterized by containing a component (A) and a component (B).

Although the details of the thermosensitive expression mechanism of the thermosensitive light transmission control material of the present invention are unclear, the interaction between the polymer formed by curing the component (B) and the component (A) is probably the temperature sensitivity. This is considered to change dramatically at the onset temperature, that is, the cloud point temperature.

The component (A) used in the present invention is not particularly limited, and a known non-reactive polyurethane resin can be used. The polyol component (a) (hereinafter referred to as component (a)) and the polyisocyanate component (b) ) (Hereinafter referred to as the component (b)) is preferably used from the viewpoint of temperature sensitivity expression and temperature sensitivity expression temperature. In addition, nonreactive means here that it does not react with (B) component, (C) component, etc. by radical polymerization.

The component (a) is not particularly limited as long as it is a compound containing at least two hydroxyl groups in the molecule, and known compounds can be used. Specifically, for example, ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, neopentyl glycol, pentanediol Various known saturated or unsaturated compounds such as 3-methyl-1,5-pentanediol, 1,6-hexanediol, octanediol, 1,4-butynediol, dipropylene glycol, 1,4-cyclohexanedimethanol Low molecular glycols, diols obtained by hydrogenating dimer acid, ethylene oxide adducts of bisphenol A, polyether polyols such as polyethylene glycol, polypropylene glycol, polybutylene glycol, etc., obtained by reacting polyols with polybasic acids Polyester polyols that, polycarbonate polyols, polybutadiene polyols, and the like. These are used singly or in combination of two or more. In the present invention, other alcohols (monoalcohol, trihydric alcohol, etc.) can be used in addition to the diols within a range not impairing the effects of the present invention. These may be used alone or in combination of two or more. Among these, it is preferable to use a polyol having a weight average molecular weight of 5000 to 20000 from the viewpoint of temperature sensitivity expression and temperature sensitivity expression temperature. In particular, it is preferable to use polypropylene glycol having a weight average molecular weight of 5000 to 20000. The temperature sensitivity expression temperature can be controlled, for example, by changing the weight average molecular weight of the component (a). Specifically, the temperature-sensitive expression temperature increases as the weight average molecular weight decreases, and the temperature-sensitive expression temperature decreases as the weight average molecular weight increases.

The component (b) is not particularly limited as long as it is a compound having at least two isocyanate groups in the molecule, and known compounds can be used. Specifically, for example, methylene diisocyanate, isopropylene diisocyanate, butane-1,4-diisocyanate, hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, dimer acid A chain aliphatic diisocyanate such as dimerisocyanate in which the carboxyl group is substituted with an isocyanate group; cyclohexane-1,4-diisocyanate, isophorone diisocyanate, dicyclohexylmethane-4,4′-diisocyanate, 1,3-di (isocyanate methyl) Cycloaliphatic diisocyanates such as cyclohexane and methylcyclohexane diisocyanate; 4,4′-diphenyldimethylmethane diisocyanate Dialkyldiphenylmethane diisocyanate, tetraalkyldiphenylmethane diisocyanate such as 4,4′-diphenyltetramethylmethane diisocyanate, 1,5-naphthylene diisocyanate, 4,4′-diphenylmethane diisocyanate, 4,4′-diphenyldimethylmethane diisocyanate, 4, Aromatic diisocyanates such as 4'-dibenzyl isocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, tolylene diisocyanate, xylylene diisocyanate, m-tetramethylxylylene diisocyanate; amino acid diisocyanates such as lysine diisocyanate, etc. Is mentioned. These may be used alone or in combination of two or more. Among these, it is preferable to use cycloaliphatic diisocyanate. In addition to the diisocyanates, other isocyanates (monoisocyanate, trivalent isocyanate, etc.) may be used as long as the effects of the present invention are not impaired.

The component (A) can be obtained by reacting the component (a) and the component (b) with a known polyurethane production method. Specifically, it is obtained by reacting about 0.5 to 0.99 mol of component (b) with respect to 1 mol of component (a). The molar ratio of component (b) / component (a) is not particularly limited, but it is usually preferably about 0.5 to 0.95.

The temperature sensitivity expression temperature can be controlled, for example, by changing the molar ratio of component (b) / component (a). Specifically, the temperature-sensitive expression temperature increases as the (b) component / (a) component ratio decreases, and the temperature-sensitive expression temperature decreases as the ratio increases.

(B) component used for this invention is a compound which has an alicyclic structure and a vinyl group in a molecule | numerator, and is a thing except said (A) component, It will not specifically limit, A well-known thing can be used. . Specifically, for example, cyclohexyl (meth) acrylate, tricyclodecane (meth) acrylate, isobornyl (meth) acrylate, (meth) acrylic acid and ethylene oxide and / or propylene oxide modified alicyclic alcohol are reacted. Acrylate obtained by reacting (meth) acrylic acid with caprolactone-modified alicyclic alcohol, oligoacrylate obtained by reacting (meth) acrylic acid oligomer with alicyclic alcohol, and the like. These may be used alone or in combination of two or more. Among these, the general formula (1):

It is preferable to use a compound represented by the formula (wherein R ¹ is a hydrogen atom or a methyl group, and n is 0 to 5) because the temperature sensitive temperature can be easily controlled. The temperature-sensitive expression temperature can be controlled, for example, by changing n in the general formula (1). Specifically, the smaller the value of n, the higher the temperature-sensitive expression temperature, and the larger the value, the lower the temperature-sensitive expression temperature.

  The component (C) used in the present invention is a compound having an aromatic group, a hydroxyl group and a vinyl group in the molecule and is not particularly limited as long as it is other than the component (A) and the component (B). Things can be used. Specific examples include 2-hydroxy-3-phenoxypropyl acrylate and 2-hydroxy-3-trioxypropyl acrylate. These may be used alone or in combination of two or more. Among these, it is preferable to use 2-hydroxy-3-phenoxypropyl acrylate in terms of temperature sensitivity expression and temperature sensitivity expression temperature.

  In the temperature-sensitive resin composition of the present invention, the effect of the present invention is further impaired by using a radically polymerizable monomer (D) (hereinafter referred to as (D) component) other than the components (B) and (C). It can be used in a range that does not exist. Specific examples of component (D) include methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and polyethylene glycol. Mono (meth) acrylate, cyclohexyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, isobornyl (meth) acrylate, benzyl (meth) acrylate, phenoxy (Meth) acrylic esters such as ethyl (meth) acrylate, (meth) acrylamides such as (meth) acrylamide, N-butoxy (meth) acrylamide, styrene, α-methylstyrene, vinyl 1,4-butanediol di (1), a compound having one vinyl group in one molecule such as vinyl compounds such as toluene and vinyl acetate, and allyl ether alcohol compounds such as glycerin monoallyl ether, allyl alcohol and ethylene glycol monoallyl ether, (Meth) acrylate, 1,6-hexanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, ethylene glycol di (meth) acrylate, polyethylene glycol (n = 2-15) Di (meth) acrylate, polypropylene glycol (n = 2-15) di (meth) acrylate, polybutylene glycol (n = 2-15) di (meth) acrylate, 2,2-bis (4- ( (Meta) acryloyloxyethoxy Cyphenyl) propane, 2,2-bis (4- (meth) acryloyloxydiethoxyphenyl) propane, trimethylolpropane di (meth) acrylate, tricyclodecane dimethanol diacrylate, bis (2- (meth) acryloyloxyethyl) ) Di (meth) acrylate compounds such as hydroxyethyl-isocyanurate; trimethylolpropane tri (meth) acrylate, tris (2- (meth) acryloyloxyethyl) isocyanurate, tris (2- (meth) acryloyloxypropyl) isocyanate Nurate, bis (2- (meth) acryloyloxyethyl) hydroxyethyl isocyanurate, bis (2- (meth) acryloyloxypropyl) -2-ethoxypropyl isocyanurate, pentaerythritol tri ( Polyfunctional (meth) acrylate compounds such as acrylate), pentaerythritol tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate; bisphenol A Epoxy poly (meth) acrylate such as epoxy di (meth) acrylate obtained by reacting type diepoxy and (meth) acrylic acid; 1,6-hexamethylene diisocyanate trimer is reacted with 2-hydroxyethyl (meth) acrylate Urethane tri (meth) acrylate, urethane di (meth) acrylate, isophorone diisocyanate and pen reacted with isophorone diisocyanate and 2-hydroxypropyl (meth) acrylate Urethane hexa (meth) acrylate reacted with erythritol tri (meth) acrylate, urethane di (meth) acrylate reacted with dicyclomethane diisocyanate and 2-hydroxyethyl (meth) acrylate, dicyclomethane diisocyanate and poly (n = 6 to 15) Urethane poly (meth) acrylate such as urethane di (meth) acrylate obtained by reacting urethanation reaction product with tetramethylene glycol with 2-hydroxyethyl (meth) acrylate; trimethylolethane and succinic acid, ( Polyester polymers such as polyester (meth) acrylate reacted with (meth) acrylic acid, polyester (meth) acrylate reacted with trimethylolpropane and succinic acid, ethylene glycol, and (meth) acrylic acid. Examples thereof include ethylenically unsaturated compounds having at least two (meth) acryloyloxy groups in one molecule such as li (meth) acrylate. These may be used alone or in combination of two or more.

  Although the usage-amount of said (A)-(D) component is not specifically limited, In the resin composition for temperature sensitive materials containing (A) component which does not contain (C) component, and (B) component, a resin composition In 100 parts by weight of the total amount of components (A) to (B), component (A) is about 20 to 50 parts by weight, preferably 30 to 50 parts by weight, and component (B) is about 50 to 80 parts by weight, preferably 50 to 70 parts by weight. Moreover, in the resin composition for temperature sensitive materials containing (A)-(C) component, (A) component is 20-20 in 100 weight part of resin composition component (A)-(C) total amount normally. About 50 parts by weight, preferably 30 to 50 parts by weight, component (B) about 15 to 60 parts by weight, preferably 20 to 50 parts by weight, and component (C) about 15 to 60 parts by weight, preferably 20 to 50 parts by weight. Parts by weight. When the component (D) is used, the total amount of the resin composition components (A) to (D) (when the component (C) is not included, the components (A), (B) and (D) (Total amount) In 100 parts by weight, component (D) is about 0.1 to 20 parts by weight, preferably 0.5 to 10 parts by weight.

In the temperature-sensitive resin composition of the present invention, a polymerization initiator may be used in order to easily polymerize the component (B), the component (C), and the component (D). The polymerization initiator is not particularly limited, and a known radical polymerization initiator may be used. Specifically, for example, inorganic peroxides such as hydrogen peroxide, ammonium persulfate, and potassium persulfate, organic peroxides such as benzoyl peroxide, dicumyl peroxide, and lauryl peroxide, 2,2′-azobis Examples thereof include azo compounds such as isobutyronitrile and dimethyl-2,2′-azobisisobutyrate.

It is preferable to use a polymerization initiator for an ultraviolet curable resin because energy savings can be achieved. Examples of the polymerization initiator for the ultraviolet curable resin include 1-hydroxy-cyclohexyl-phenyl ketone, 2,2-dimethoxy-1,2-diphenylethane-1-one, 1-cyclohexyl phenyl ketone, 2-hydroxy-2-phenyl Methyl-1-phenyl-propan-1-one, 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propan-1-one, 2-methyl-1- [ 4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1, bis (2,4,6-trimethyl) Benzoyl) -phenylphosphine oxide, 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide, 4-methylbenzo Zofenon, etc. and the like. Although the usage-amount of a polymerization initiator is not specifically limited, Usually, it is about 0.1-20 weight part with respect to 100 weight part of total amounts of (A)-(D).

  Moreover, you may use the resin composition of this invention, making it melt | dissolve in a solvent as needed. The solvent that can be used is not particularly limited as long as it can dissolve the components (A) to (D), and known solvents can be used. Specifically, for example, alcohols such as methanol, ethanol, isopropanol, butanol, ethylene glycol monoethyl ether, propylene glycol monomethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone; methyl acetate, ethyl acetate, Esters such as butyl acetate, γ-butyrolactone and propylene glycol monomethyl ether acetate; Aromatic hydrocarbons such as toluene and xylene; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone Etc. Although the usage-amount of a solvent is not specifically limited, Usually, it is about 1-10000 weight part with respect to 100 weight part of total amounts of (A)-(D).

  Further, the temperature-sensitive resin composition of the present invention includes a chain transfer agent, a surfactant, a surface conditioner, an antifoaming agent, an antioxidant, a photosensitizer, a light stabilizer, a surface conditioner, a pigment, a filling Various known additives such as an agent and an antistatic agent can be used.

In the resin composition of the present invention, the components (B) to (D) are polymerized and cured by making the conditions capable of radical polymerization. The cured product thus obtained becomes a temperature-sensitive light transmission control material capable of autonomously and reversibly controlling a transparent (light transmission) state and a white turbidity (light shielding) state in response to a temperature stimulus.
In addition, since the temperature-sensitive light transmission control material of the present invention does not require any volatile components such as water and organic solvents for the expression of the temperature sensitivity, it can be practically handled as a sheet or a molded product. Furthermore, the temperature at which light is transmitted and blocked can be arbitrarily controlled by selecting the components (A) to (C) and changing the blending ratio.

Therefore, the temperature-sensitive light control material of the present invention can be used as a material for a light control window or a light control sheet. For example, if a light control sheet is installed inside the window of a building or house, a transparent open feeling is secured on the low temperature side below the cloudy temperature, but it becomes cloudy when the temperature rises above the cloudy temperature due to radiant heat of direct sunlight, Exhibits light-shielding effects like curtains and blinds. This dimming function can be controlled in an energy-saving manner without requiring electric power, and in particular, since the cooling efficiency in summer can be promoted, a carbon dioxide emission reduction effect can be expected. Light control windows and light control sheets are used in a wide range of fields, including buildings and houses, transportation related to automobiles, railway vehicles, ships, aircraft, etc., agriculture, industrial products such as greenhouses, chemical laboratories, and radioisotope laboratories. it can. The temperature-sensitive light transmission control material of the present invention can also be used as a temperature sensor for toys, interiors, displays, mechanochemical element materials, and the like.

EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to the following Example.

Example 1
A reaction vessel equipped with a stirrer and a temperature controller was charged with 295.6 parts by weight of polypropylene glycol having a weight average molecular weight of 10,000 and 4.4 parts by weight of isophorone diisocyanate, and the temperature was adjusted to 80 ° C. Here, 0.1 part by weight of tin octylate (manufactured by API Corporation, Stanoct) was charged, and stirring was continued for 2 hours. After confirming that the residual NCO was 0.1 parts by weight or less, the reaction was terminated, and a polyurethane resin was obtained. This was mixed with 700 parts by weight of isobornyl oligoacrylate (n = 1 in the general formula (1)) and 5 parts by weight of 2-hydroxy-2-methylpropiophenone to obtain a resin composition for a temperature sensitive material.

Example 2
A reaction vessel equipped with a stirrer and a temperature controller was charged with 295.6 parts by weight of polypropylene glycol having a weight average molecular weight of 10,000 and 4.4 parts by weight of isophorone diisocyanate, and the temperature was adjusted to 80 ° C. Here, 0.1 part by weight of tin octylate (manufactured by API Corporation, Stanoct) was charged, and stirring was continued for 2 hours. After confirming that the residual NCO was 0.1 parts by weight or less, the reaction was terminated, and a polyurethane resin was obtained. 550 parts by weight of this and 2-hydroxy-3-phenoxypropyl acrylate, 150 parts by weight of isobornyl acrylate (general formula (1) n = 0), 5 parts by weight of 2-hydroxy-2-methylpropiophenone A resin composition for a temperature sensitive material was obtained.

Example 3
A reaction vessel equipped with a stirrer and a temperature controller was charged with 295.6 parts by weight of polypropylene glycol having a weight average molecular weight of 10,000 and 4.4 parts by weight of isophorone diisocyanate, and the temperature was adjusted to 80 ° C. Here, 0.1 part by weight of tin octylate (manufactured by API Corporation, Stanoct) was charged, and stirring was continued for 2 hours. After confirming that the residual NCO was 0.1 parts by weight or less, the reaction was terminated, and a polyurethane resin was obtained. 150 parts by weight of this and 2-hydroxy-3-phenoxypropyl acrylate, 250 parts by weight of n = 1 of the general formula (1), and 5 parts by weight of 2-hydroxy-2-methylpropiophenone are blended to produce a temperature sensitive material. A resin composition was obtained.

Example 4
A reaction vessel equipped with a stirrer and a temperature controller was charged with 389.5 parts by weight of polypropylene glycol having a weight average molecular weight of 5500 and 10.5 parts by weight of isophorone diisocyanate, and the temperature was adjusted to 80 ° C. Here, 0.2 part by weight of tin octylate (manufactured by API Corporation, Stanocto) was charged, and stirring was continued for 2 hours. After confirming that the residual NCO was 0.1 parts by weight or less, the reaction was terminated, and a polyurethane resin was obtained. 250 parts by weight of this and 2-hydroxy-3-phenoxypropyl acrylate, 350 parts by weight of isobornyl acrylate, and 5 parts by weight of 2-hydroxy-2-methylpropiophenone are blended to obtain a resin composition for temperature sensitive materials. It was.

Example 5
A reaction vessel equipped with a stirrer and a temperature controller was charged with 396.1 parts by weight of polypropylene glycol having a weight average molecular weight of 15000 and 3.9 parts by weight of isophorone diisocyanate, and the temperature was set to 80 ° C. Here, 0.2 part by weight of tin octylate (manufactured by API Corporation, Stanocto) was charged, and stirring was continued for 2 hours. After confirming that the residual NCO was 0.1 parts by weight or less, the reaction was terminated, and a polyurethane resin was obtained. 250 parts by weight of this and 2-hydroxy-3-phenoxypropyl acrylate, 350 parts by weight of isobornyl acrylate, and 5 parts by weight of 2-hydroxy-2-methylpropiophenone are blended to obtain a resin composition for temperature sensitive materials. It was.

Comparative Example 1
A reaction vessel equipped with a stirrer and a temperature controller was charged with 394.2 parts by weight of polypropylene glycol having a weight average molecular weight of 10,000 and 5.8 parts by weight of isophorone diisocyanate, and the temperature was set to 80 ° C. Here, 0.2 part by weight of tin octylate (manufactured by API Corporation, Stanocto) was charged, and stirring was continued for 2 hours. After confirming that the residual NCO was 0.1 parts by weight or less, the reaction was terminated, and a polyurethane resin was obtained. 600 parts by weight of this and 2-hydroxy-3-phenoxypropyl acrylate and 5 parts by weight of 2-hydroxy-2-methylpropiophenone were blended to obtain a resin composition.

Comparative Example 2
A reaction vessel equipped with a stirrer and a temperature controller was charged with 394.2 parts by weight of polypropylene glycol having a weight average molecular weight of 10,000 and 5.8 parts by weight of isophorone diisocyanate, and the temperature was set to 80 ° C. Here, 0.2 part by weight of tin octylate (manufactured by API Corporation, Stanocto) was charged, and stirring was continued for 2 hours. After confirming that the residual NCO was 0.1 parts by weight or less, the reaction was terminated, and a polyurethane resin was obtained. This was mixed with 600 parts by weight of phenoxyethyl acrylate and 5 parts by weight of 2-hydroxy-2-methylpropiophenone to obtain a resin composition.

Comparative Example 3
A reaction vessel equipped with a stirrer and a temperature controller was charged with 281 parts by weight of polypropylene glycol having a weight average molecular weight of 10,000 and 12.5 parts by weight of isophorone diisocyanate, and the temperature was adjusted to 80 ° C. Here, 0.2 part by weight of tin octylate (manufactured by API Corporation, Stanocto) was charged, and stirring was continued for 2 hours. Thereafter, 6.5 parts by weight of hydroxyethyl acrylate (manufactured by Osaka Organic Chemical Industry Co., Ltd., HEA) was added, and stirring was continued at a temperature of 80 ° C. for 2 hours. After confirming that the residual NCO was 0.1 parts by weight or less, the reaction was terminated, and a reactive polyurethane resin was obtained. This was mixed with 550 parts by weight of 2-hydroxy-3-phenoxypropyl acrylate, 150 parts by weight of isobornyl acrylate, and 5 parts by weight of 2-hydroxy-2-methylpropiophenone to obtain a resin composition.

The resin compositions obtained in the examples and comparative examples were coated on a glass plate at a thickness of 500 μm and cured at 120 W, a high-pressure mercury lamp, a lamp height of 10 cm, a belt speed of 10 m / min, and one pass. The light transmittance was visually examined when this cured product was raised from 20 ° C. to 80 ° C. in a thermostatic bath. The results are shown in Tables 1 and 2.

As is clear from Tables 1 and 2, Example 1, Example 2, Example 3, Example 4, and Comparative Example 3 were transparent at 20 ° C. and transmitted light. When the temperature is increased, Example 1 is between 45 ° C. and 50 ° C., Example 2 is between 35 ° C. and 40 ° C., Example 3 is between 25 ° C. and 30 ° C., and Example 4 is While Example 5 became cloudy between 45 ° C. and 50 ° C. between 75 ° C. and 80 ° C., Comparative Example 3 was transparent even when the temperature was raised. Comparative Example 1 and Comparative Example 2 always remained cloudy between 20 and 80 ° C. As a result, at 80 ° C., Example 1, Example 2, Example 3, and Example 4 were cloudy and stopped transmitting light, whereas Comparative Example 3 was transparent and transmitted light.

Claims (4)

Non- reactive polyurethane resin (A) obtained by reacting polypropylene glycol having a weight average molecular weight of 5000 to 20000 and isophorone diisocyanate and general formula (1):
(Wherein R ¹ is a hydrogen atom or a methyl group, and n is 0 to 5) The vinyl monomer (B) having an alicyclic structure is contained in the molecule represented by Resin composition. Non- reactive polyurethane resin (A) obtained by reacting polypropylene glycol having a weight average molecular weight of 5000 to 20000 and isophorone diisocyanate, general formula (1):
(Wherein R ¹ is a hydrogen atom or a methyl group, n is 0 to 5) a vinyl monomer (B) having an alicyclic structure in the molecule represented by and a vinyl monomer having an aromatic group and a hydroxyl group in the molecule A resin composition for a temperature-sensitive material, comprising (C). The resin composition for a temperature-sensitive material according to claim 1 or 2, wherein the vinyl monomer (C) having an aromatic group and a hydroxyl group in the molecule is 2-hydroxy-3-phenoxypropyl acrylate. A temperature-sensitive light transmission control material obtained by curing the resin composition according to claim 1.