JP2008195808A - Reactive diluent and polyurethane composition by using the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a reactive diluent excellent in compatibility with a polyol for a urethane, and capable of improving workability and productivity in using a highly viscous polyol, and by using the same, to obtain a polyurethane resin excellent in heat resistance and stability over time, and especially the reactive diluent capable of being used for a non-solvent type acrylic urethane coating and a urethane resin-sealing agent for electric insulation. <P>SOLUTION: This polyurethane resin excellent in especially heat resistance and stability over time is found to be obtained by using the reactive diluent consisting of a polyglycerol polyoxyalkylene fatty acid ester obtained by reacting a polyglycerol (average-degree of polymerization is 2 to 10), an alkylene oxide (the alkylene oxide has 2 to 4 number of carbon atoms and the added number of moles is 4 to 80) and a saturated or unsaturated fatty acid having a linear or branched chain (the number of carbon atoms is 2 to 18), and having 20 to 80% esterification rate. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a reactive diluent for a polyol for polyurethane using polyglycerin, alkylene oxide and carboxylic acid as raw materials, and further relates to a polyurethane resin using the same. Specifically, it is excellent in compatibility with polyols and in reducing the viscosity of polyols, and since it becomes a cross-linked structural component when made into a urethane resin, it has excellent heat resistance and stability over time in that it does not cause bleeding. It is related with the reactive diluent which can obtain.

  Generally, in applications where high-viscosity polyols such as polybutadiene glycol, polyisoprene polyol, polycarbonate polyol, and acrylic polyol are used as urethane resin polyols, the viscosity of the polyol is reduced from the viewpoint of improving workability and improving productivity. It is hoped that The method generally includes the addition of a reactive diluent. This reduces the viscosity, similar to the solvent, but is incorporated into the resulting polyurethane because it participates in the reaction. As such a diluent, a low molecular weight compound containing a hydroxyl group that reacts with an isocyanate is generally used. It is known to use low molecular weight and low viscosity diols, triols such as ethylene glycol, propylene glycol, dipropylene glycol, butanediol, glycerin and the like. However, these alcohols have poor compatibility with the above-described high-viscosity polyol, and adversely affect the properties of the cured product. Furthermore, since the hydroxyl value is high, the amount of isocyanate used increases, which is uneconomical.

On the other hand, DOP (dioctyl phthalate), DOA (dioctyl adipate), ATBC (acetyl tributyl citrate), etc. are known as general plasticizers used for the purpose of reducing viscosity and imparting flexibility. . These are excellent in compatibility with polyol and viscosity reduction effect on polyol, but since they do not contain a hydroxyl group that reacts with isocyanate, they tend to cause bleeding when used as a polyurethane resin, thus causing problems in heat resistance. The blending amount was limited (Patent Document 1). Further, as a general reactive diluent, castor oil-modified polyol having a low viscosity such as methyl ricinoleate and methyl acetylricinoleate is known (Patent Document 2). These castor oil-modified polyols are excellent in reducing the viscosity of the polyol and do not bleed, but it is difficult to maintain the heat resistance of the polyurethane resin because the molecular weight is relatively small. In addition, polyoxypropylene derivatives such as polyoxypropylene triol obtained by adding propylene oxide to glycerin and polyoxypropylene tetraol obtained by adding propylene oxide to pentaerythritol are used (Patent Document 3). Was not sufficient in reducing the viscosity of the polyol. Polypropylene glycol having a molecular weight of about 1000 has good compatibility and relatively low viscosity, but has insufficient heat resistance, so that it is difficult to achieve both a viscosity reduction effect and heat resistance.
JP 07-292237 A JP 2006-096912 A Japanese Patent No. 3347763

  The problem to be solved by the present invention is to provide a reactive diluent that is excellent in compatibility with a polyol for urethane and can improve workability and productivity when using a highly viscous polyol. Furthermore, by using the reactive diluent, it is possible to obtain a polyurethane resin having excellent heat resistance and stability over time, and in particular, a reaction that can be used as a solvent-free acrylic urethane paint and a urethane resin sealing material for electrical insulation. Providing a functional diluent.

  As a result of intensive studies to solve the above problems, the present inventors have found that polyglycerin (average degree of polymerization 2 to 10) and alkylene oxide (alkylene oxide having 2 to 4 carbon atoms and an added mole number of 4 to 80). And a polyglycerol polyoxyalkylene fatty acid ester having an esterification rate of 20 to 80% obtained by reacting a saturated or unsaturated fatty acid (having 2 to 18 carbon atoms) having a linear or branched chain. As a result, the present inventors have found that the above-mentioned problems have been solved, and that a polyurethane resin having particularly excellent heat resistance and stability over time can be obtained.

  By using the reactive diluent of the present invention, it becomes possible to reduce the viscosity of the polyol for urethane, leading to improvement in workability and productivity, and a polyurethane resin excellent in heat resistance and stability over time is obtained. It is done.

  The present invention is described in detail below.

  The reactive diluent of the present invention comprises polyglycerin (average polymerization degree 2 to 10), alkylene oxide (alkylene oxide having 2 to 4 carbon atoms and 4 to 80 added moles), and straight chain or branched chain. It is a product having an esterification rate of 20 to 80% obtained by reacting a saturated or unsaturated fatty acid (having 2 to 18 carbon atoms). These compounds were synthesized according to a general production method. That is, it comprises a step of adding an alkylene oxide to polyglycerol in the presence of a catalytic amount of alkali and a step of esterifying the adduct with various fatty acids by a dehydration condensation reaction. However, this manufacturing method is an illustration, and when manufacturing the reactive diluent shown by this invention, it is not necessarily limited to this manufacturing method.

  The polyglycerin used in the reactive diluent of the present invention preferably has an average degree of polymerization of 2 to 10 obtained from a hydroxyl group equivalent, and more preferably has an average degree of polymerization of 2 to 6. If the average degree of polymerization is too low, the heat resistance of the resulting polyurethane resin tends to decrease, whereas if the average degree of polymerization is too high, the viscosity of the reactive diluent tends to increase, and workability when blended with a polyol is increased. This range is preferable because it is difficult to improve the productivity and productivity.

  Examples of the alkylene oxide used in the reactive diluent of the present invention include ethylene oxide, propylene oxide, and butylene oxide. Ethylene oxide or propylene oxide is preferable, and ethylene oxide and propylene oxide may be used alone or in combination. The number of addition units of alkylene oxide is preferably 4 to 80 mol, more preferably 4 to 60 mol, per 1 mol of polyglycerol. If the added mole number of the alkylene oxide is too low, the compatibility with the polyol for urethane tends to be deteriorated. On the other hand, if the added mole number of the alkylene oxide is too high, the water resistance is deteriorated.

  The fatty acid used in the reactive diluent of the present invention may be any linear or branched, saturated or unsaturated fatty acid having 2 to 18 carbon atoms, and can be used alone or in a mixture. Specifically, acetic acid, propionic acid, butyric acid, caproic acid, caprylic acid, 2-ethylhexanoic acid, isononanoic acid, capric acid, undecylenic acid, lauric acid, myristic acid, palmitic acid, stearic acid, isostearic acid, ricinoleic acid Oleic acid, linoleic acid, linolenic acid and the like, among which caprylic acid and oleic acid are preferable.

  The esterification rate of the reactive diluent of the present invention is preferably in the range of 20 to 80%, more preferably 30 to 70%. If the esterification rate is less than 20%, the compatibility with the main component polyol is deteriorated, or the flexibility of the obtained polyurethane resin is lowered, and the amount of polyisocyanate used is increased, which is uneconomical. On the other hand, when the esterification rate exceeds 80%, the heat resistance of the obtained polyurethane resin is lowered, or the physical properties are lowered such as bleeding.

  The viscosity at 25 ° C. of the reactive diluent of the present invention is preferably in the range of 10 to 1000 mPa · s, more preferably 50 to 400 mPa · s. Since the reaction diluent having a viscosity of less than 10 mPa · s has a high esterification rate, it causes a decrease in physical properties such as a decrease in the heat resistance of the resulting polyurethane resin or the occurrence of bleeding. On the other hand, when the viscosity exceeds 1000 mPa · s, the effect of reducing the viscosity of the polyol is small and the workability is not improved.

  The hydroxyl value of the reactive diluent of the present invention can be appropriately changed by adjusting the degree of polymerization of polyglycerol, the number of added moles of alkylene oxide, and the esterification rate, but is preferably in the range of 50 to 400 mgKOH / g. More preferably, it is 100-200 mgKOH / g. If the hydroxyl value is less than 50 mgKOH / g, the heat resistance of the resulting polyurethane resin may be reduced, or physical properties such as bleeding may be caused. On the other hand, if the hydroxyl value exceeds 400 mgKOH / g, This is a cause of deterioration in physical properties such as deterioration of the solubility or bleed in the obtained polyurethane resin, and is also uneconomical because the amount of polyisocyanate used is increased.

  Specific examples of the reactive diluent of the present invention include polyoxyethylene (4) diglyceryl ether caprylic acid ester (esterification rate 65%), polyoxyethylene (6) diglyceryl ether oleic acid ester (esterification). 33%), caprylic acid ester of polyoxyethylene (13) diglyceryl ether (esterification rate 50%), 2-ethylhexanoic acid ester of polyoxyethylene (13) diglyceryl ether (esterification rate 50%), etc. Is mentioned.

  The polyurethane composition of the present invention is prepared through a step of blending an isocyanate after previously mixing the reactive diluent of the present invention with polybutadiene glycol, polyisoprene glycol, polycarbonate diol, acrylic polyol, etc., which are the main polyols. The

  The addition amount of the reactive diluent of the present invention is usually 1 to 80% by weight, preferably 5 to 60% by weight, and more preferably 10 to 40% by weight based on the weight of the main component polyol. When the addition amount is 1% by weight or less, the effect of reducing the viscosity of the polyol is small and the workability is not improved. On the other hand, if it exceeds 80% by weight, the heat resistance and water resistance of the resulting polyurethane resin deteriorate, so this range is preferred.

  The kind of polyol used in the present invention is not particularly limited, and polyols generally available to those skilled in the art can be used. Specific examples of polyols used in the present invention include polycarbonate polyols such as trade names PCDL T-5562, T-5651, T-5650J (above, manufactured by Asahi Kasei Chemicals Corporation), trade names poly bd R-45HT, R -15HT (above, hydroxyl-terminated liquid polybutadiene made by Idemitsu Kosan Co., Ltd.), trade names G-1000, G-2000, G-3000 (above, α, ω-polybutadiene glycol made by Nippon Soda Co., Ltd.), trade names GI-1000 , GI-2000, GI-3000 (above, hydrogenated polybutadiene glycol manufactured by Nippon Soda Co., Ltd.), etc., trade name poly ip (hydroxyl-terminated liquid isoprene manufactured by Idemitsu Kosan Co., Ltd.), trade name Epol (Idemitsu Kosan) Hydrogenated polio manufactured by KK Acrylic polyols such as polyisoprene polyols such as (Refin polyol) and trade names ARUFON UH-2000, UH-2032, UH-2041 (manufactured by Toagosei Co., Ltd.). These descriptions are examples of polyols suitable for the present invention, and the present invention is not limited by these.

  Specific examples of the polyisocyanate component used in the polyurethane composition of the present invention include 4,4′- or 2,4-diphenylmethane diisocyanate, carbodiimide-modified diphenylmethane diisocyanate, polymerized diphenylmethane diisocyanate, hydrogenated diphenylmethane diisocyanate, tolylene diisocyanate. , Xylylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, isophorone diisocyanate, phenylene diisocyanate, naphthalene diisocyanate, triphenylmethane diisocyanate, diphenylsulfone diisocyanate, 3-isocyanate methyl-3,5,5-trimethylcyclohexyl isocyanate, 3- Isocyanatoethyl-3 Various polyisocyanates including 5,5, -trimethylcyclohexyl isocyanate, 3-isocyanatoethyl-3,5,5, -triethylcyclohexyl isocyanate, diphenylpropane diisocyanate, diphenyl ether-4,4'-diisocyanate, cyclohexylylene diisocyanate 3,3'-diisocyanate dipropyl ether, or urethane-modified products, dimers, trimers, carbodiimide products, allophanate-modified products, urea-modified products, biuret-modified products, pole polymers, and blocked products of these polyisocyanates. can give. When weather resistance is required, it is desirable to select a non-yellowing polyisocyanate such as hexamethylene diisocyanate or isophorone diisocyanate.

  The polyurethane composition of the present invention comprises the aforementioned polyol component and polyisocyanate component. The blending ratio of both components is usually 0.7 to 1.4, preferably 0.8 to 1.2 in terms of an equivalent ratio of NCO / OH. If it is outside these ranges, this range is preferable because sufficient curing cannot be achieved, such as bleeding of unreacted components in the polyurethane cured product.

  In preparing the polyurethane composition of the present invention, a chain extender, a crosslinking agent, a filler, a pigment, a filler, a plasticizer, a urethanization catalyst, an ultraviolet absorber, an antioxidant, an anti-aging agent, and moisture as necessary. It is manufactured by adding an absorbent, an antifoaming agent, an antifungal agent, a silane-based or titanium-based coupling agent, a release agent, a flame retardant, a surfactant, a pH adjuster, and the like.

  Curing of the polyurethane composition of the present invention can be carried out at a temperature of room temperature to about 110 ° C. When the temperature is raised, the curing reaction is accelerated accordingly. The curing time may be appropriately determined as about 1 to 7 days at room temperature and about 1 to 10 hours at 100 ° C. curing, and can be adjusted depending on the type of catalyst used. As an example, after casting, a method of heating at 60 ° C. for 1 hour and then allowing to stand at room temperature for about 4 days, or a method of leaving at 110 ° C. for 6 hours is employed.

  Hereinafter, although the reactive diluent and polyurethane composition of this invention are demonstrated in detail, this invention is not limited to these synthesis examples and Examples.

<Synthesis Example 1>
In a reactor equipped with a thermometer, a stirrer, a nitrogen blowing tube and an exhaust line, 393.5 g (1.150 mol) of ethylene oxide adduct of polyglycerin (average polymerization degree 2) (addition mole number 4), caprylic acid 464 .5 g (3.221 mol) and 0.1 g of sodium hydroxide were charged, a certain amount of nitrogen was blown in, and the temperature was raised to 180 ° C. with stirring and reacted for 1 hour, then the temperature was raised to 220 ° C. and reacted for 5 hours. went. After completion of the reaction, the reaction mixture was cooled to 60 ° C. to obtain 795.0 g of a caprylic acid ester (RD1) of polyglycerin (average polymerization degree 2) ethylene oxide adduct (addition mole number 4). The obtained product had an esterification rate of 65%, a viscosity of 94 mPa · s (25 ° C.), and a hydroxyl value of 110 mgKOH / g.

<Synthesis Example 2>
In a reactor equipped with a thermometer, stirrer, nitrogen blowing tube, and exhaust line, 393.5 g (1.150 mol) of ethylene oxide adduct of polyglycerin (average polymerization degree 2) (addition mole number 4), 2-ethyl Charge 464.5 g (3.221 mol) of hexanoic acid and 0.1 g of sodium hydroxide, blow in a certain amount of nitrogen, raise the temperature to 180 ° C. with stirring and react for 1 hour, then raise the temperature to 220 ° C. The reaction was performed for 5 hours. After completion of the reaction, the reaction mixture was cooled to 60 ° C. to obtain 788.0 g of 2-ethylhexanoic acid ester (RD2) of polyglycerin (average polymerization degree 2) ethylene oxide adduct (addition mole number 4). The obtained product had an esterification rate of 65%, a viscosity of 121 mPa · s (25 ° C.), and a hydroxyl value of 126 mgKOH / g.

<Synthesis Example 3>
In a reactor equipped with a thermometer, a stirrer, a nitrogen blowing pipe, and an exhaust line, 581.3 g (0.788 mol) of ethylene oxide adduct (addition mole number 13) of polyglycerin (average polymerization degree 2), caprylic acid 249 .9 g (1.733 mol) and 0.1 g of sodium hydroxide were charged, a certain amount of nitrogen was blown in, and the temperature was raised to 180 ° C. with stirring and reacted for 1 hour, then the temperature was raised to 220 ° C. and reacted for 5 hours. went. After completion of the reaction, the mixture was cooled to 60 ° C. to obtain 791.5 g of a caprylic acid ester (RD3) of polyglycerin (average polymerization degree 2) ethylene oxide adduct (addition mole number 13). The obtained product had an esterification rate of 50%, a viscosity of 171 mPa · s (25 ° C.), and a hydroxyl value of 115 mgKOH / g.

<Synthesis Example 4>
In a reactor equipped with a thermometer, a stirrer, a nitrogen blowing tube and an exhaust line, 545.7 g (0.739 mol) of ethylene oxide adduct of polyglycerin (average polymerization degree 2) (addition mole number 13), oleic acid 271 .6 g (0.961 mol) and 0.1 g of sodium hydroxide were charged, a certain amount of nitrogen was blown in, and the temperature was raised to 230 ° C. with stirring to carry out the reaction for 5 hours. After completion of the reaction, the reaction mixture was cooled to 60 ° C. to obtain 798.0 g of oleic acid ester (RD4) of polyglycerin (average polymerization degree 2) ethylene oxide adduct (added mole number 13). The obtained product had an esterification rate of 33%, a viscosity of 314 mPa · s (25 ° C.), and a hydroxyl value of 140 mgKOH / g.

<Comparative Synthesis Example 1>
In a reactor equipped with a thermometer, a stirrer, a nitrogen blowing tube and an exhaust line, 228.0 g (1.373 mol) of polyglycerin (average polymerization degree 2), 653.6 g (4.533 mol) of caprylic acid, sodium hydroxide 0.1 g was charged, a certain amount of nitrogen was blown, and the temperature was raised to 180 ° C. with stirring and reacted for 1 hour, and then the temperature was raised to 220 ° C. and reacted for 5 hours. After completion of the reaction, the mixture was cooled to 60 ° C. to obtain 790.5 g of polyglycerin (average polymerization degree 2) caprylic acid ester (RD5). The obtained product had an esterification rate of 75%, a viscosity of 70 mPa · s (25 ° C.), and a hydroxyl value of 103 mgKOH / g.

<Comparative Synthesis Example 2>
In a reactor equipped with a thermometer, stirrer, nitrogen blowing tube and exhaust line, polyglycerin (average polymerization degree 2) 160.5 g (0.967 mol), oleic acid 683.0 g (2.418 mol), sodium hydroxide 0.1 g was charged, a certain amount of nitrogen was blown, and the temperature was raised to 230 ° C. while stirring, and the reaction was carried out for 5 hours. After completion of the reaction, the reaction mixture was cooled to 60 ° C. to obtain 796.0 g of polyglycerol (average polymerization degree 2) oleate (RD6). The obtained product had an esterification rate of 63%, a viscosity of 220 mPa · s (25 ° C.), and a hydroxyl value of 105 mgKOH / g.

<Comparative Synthesis Example 3>
In a reactor equipped with a thermometer, a stirrer, a nitrogen blowing tube and an exhaust line, 259.5 g (1.022 mol) of ethylene oxide adduct of polyglycerin (average polymerization degree 2) (addition mole number 2), 577 oleic acid .3 g (2.043 mol) and 0.1 g of sodium hydroxide were charged, a certain amount of nitrogen was blown in, and the temperature was raised to 230 ° C. with stirring to carry out the reaction for 5 hours. After completion of the reaction, the reaction mixture was cooled to 60 ° C. to obtain 798.0 g of an oleic acid ester (RD7) of polyglycerin (average polymerization degree 2) ethylene oxide adduct (added mole number 2). The obtained product had an esterification rate of 50%, a viscosity of 250 mPa · s (25 ° C.), and a hydroxyl value of 143 mgKOH / g.

<Example 1>
80 parts by weight of polycarbonate polyol (PCDL T-5651 <manufactured by Asahi Kasei Chemicals>) and 20 parts by weight of the reactive diluent described in Synthesis Example 1 were mixed and stirred until uniform. The viscosity of this blend was 3770 mPa · s (25 ° C.). Next, with respect to this polyol component, NCO (wt%) = 23.1% of polyisocyanurate (Duranate TPA-100 <manufactured by Asahi Kasei Chemicals Co., Ltd.>) in NCO / OH equivalent ratio of 1.0 In addition, 2.0 parts of a hindered phenolic antioxidant and 0.05 part of a silicone-based antifoaming agent were blended, and after stirring until uniform again, defoamed for 10 minutes under a vacuum of 5 torr, 110 A polyurethane resin was obtained by heat-curing under the conditions of ° C and 6 hours.

<Examples 2 to 4, Comparative Examples 1 to 5>
A polyurethane resin was obtained in the same manner as in Example 1 except that the reactive diluent in Example 1 was changed.

The reactive diluents used in Examples 2 to 4 and Comparative Examples 1 to 5 are shown below.
Example 2: Reactive diluent described in Synthesis Example 2 Example 3: Reactive diluent described in Synthesis Example 3 Example 4: Reactive diluent described in Synthesis Example 4 Comparative Example 1: Comparison Reactive Diluent Comparative Example 2 described in Synthesis Example 1 Reactive Diluent Comparative Example 3 described in Comparative Synthesis Example 2 Reactive Diluent Comparative Example 4 described in Comparative Synthesis Example 3 Methyl ricinoleate (Viscosity = 24 mPa · s (25 ° C.), hydroxyl value = 165 mgKOH / g, molecular weight = 313)
Comparative Example 5: Polypropylene glycol (viscosity = 148 mPa · s (25 ° C.), hydroxyl value = 110 mgKOH / g, molecular weight = 1000)

<Evaluation>
The result of having evaluated the compatibility with polycarbonate polyol about said reactive diluent according to the following evaluation method (1) was shown to Tables 1-2. Moreover, about the thing with favorable compatibility, the result of having measured the viscosity of a polyol composition, the hardness (Shore A) of a polyurethane resin, and heat resistance according to the following evaluation methods (2)-(4) was shown to Tables 3-4. .
(1) Compatibility With 66.7 parts by weight of polycarbonate polyol, 33.3 parts by weight of various reactive diluents were mixed and allowed to stand at 25 ° C. for 1 day to observe compatibility.
○ ・ ・ ・ Transparent uniform Δ ・ ・ ・ White turbid × ・ ・ ・ Separated into two layers (2) Viscosity Measure the viscosity of a polyol composition containing 20 parts by weight of various reactive diluents with respect to 80 parts by weight of polycarbonate polyol. did. In addition, Tokyo Keiki Co., Ltd. B type rotational viscometer was used for the measurement.
(3) Hardness (Shore A)
The hardness of the polyurethane resin prepared by blending 20 parts by weight of various reactive diluents with respect to 80 parts by weight of the polycarbonate polyol was measured according to a plastic durometer hardness test method JIS K 7215.
The durometer hardness tester used was CL-150 manufactured by Kobunshi Keiki Co., Ltd.
(4) Heat resistance The initial weight of a polyurethane resin prepared by blending 20 parts by weight of various reactive diluents with respect to 80 parts by weight of a polycarbonate polyol, and the weight after being left in a 150 ° C. dryer for 4 weeks were measured. The weight loss by heating (%) was determined by the following formula.
Calculation formula: Heated weight decrease (%) = (initial weight−weight after heating) ÷ initial weight × 100
○: Less than 4.0% Δ: 4.0% or more, less than 8.0% × ... 8.0% or more

※１〜９は表１〜４参照
※１：合成例１に記載される反応性希釈剤
※２：合成例２に記載される反応性希釈剤
※３：合成例３に記載される反応性希釈剤
※４：合成例４に記載される反応性希釈剤
※５：比較合成例１に記載される反応性希釈剤
※６：比較合成例２に記載される反応性希釈剤
※７：比較合成例３に記載される反応性希釈剤
※８：リシノレイン酸メチル（商品名「Ｋ−ＰＯＮ１８０」；小倉合成工業(株)製）
※９：ポリプロピレングリコール（商品名「ニューポールＰＰ−１０００」；三洋化成工業(株)製）

* See Tables 1 to 4 for 1 to 9 * 1: Reactive diluent described in Synthesis Example 1 * 2: Reactive diluent described in Synthesis Example 2 * 3: Reactivity described in Synthesis Example 3 Diluent * 4: Reactive diluent described in Synthesis Example 4 * 5: Reactive diluent described in Comparative Synthesis Example 1 * 6: Reactive diluent described in Comparative Synthesis Example 2 * 7: Comparison Reactive diluent described in Synthesis Example 3 * 8: Methyl ricinoleate (trade name “K-PON180”; manufactured by Ogura Gosei Co., Ltd.)
* 9: Polypropylene glycol (trade name “New Pole PP-1000”; manufactured by Sanyo Chemical Industries, Ltd.)

By using the reactive diluent of the present invention, it is possible to obtain a polyurethane cured product excellent in workability and productivity of the polyol for urethane, and further excellent in heat resistance and stability over time. As an elastomer, an adhesive, a paint, a binder, and the like, it can be suitably used particularly as a solvent-free acrylic urethane paint and a urethane resin sealing material for electrical insulation.

Claims (4)

  Polyglycerin (average polymerization degree 2 to 10) and alkylene oxide (alkylene oxide having 2 to 4 carbon atoms, addition mole number is 4 to 80) and saturated or unsaturated fatty acid having a straight chain or branched chain ( Reactive diluent of polyol for urethane containing polyglycerin polyoxyalkylene fatty acid ester whose esterification rate obtained by reacting 2-18 carbon atoms is 20-80%.   The reactive diluent according to claim 1, wherein the viscosity at 25 ° C. is 10 to 1000 mPa · s.   The reactive diluent according to claim 1, wherein the hydroxyl value is 50 to 400 mg KOH / g.   A polyurethane composition comprising the reactive diluent according to claim 1, a polyol and an isocyanate.