JP6604797B2 - Hydrophilizing agent - Google Patents

Description

  The present invention relates to a hydrophilizing agent.

  In general, when the surface of the substrate is hydrophilized, water droplets attached to the substrate are spread uniformly. As a result, adhesion of hydrophobic pollutants such as combustion products, oils and fats and sealant elution components contained in exhaust gas from urban dust, automobiles, etc., and even when the hydrophobic pollutants adhere, rain, washing or water Removal by a simple operation such as wiping becomes possible. In addition, it is expected to improve adhesion to a substrate, adhesion, plating characteristics, antistatic properties and the like.

  In the medical field, it is expected that the cultured cells can be easily collected by making the culture vessel for transplanted cells hydrophilic. It is also expected to prevent blood coagulation by hydrophilizing the components of the blood purification apparatus.

  As one method for making the substrate surface hydrophilic, a method of forming a mixture of a resin and a hydrophilizing agent (hereinafter referred to as a kneading method) is known. The kneading method has an advantage that the production of a molded product is simpler than the method of applying a hydrophilizing agent to the substrate surface. As such a hydrophilizing agent, for example, there is a method using a sulfonate and an amine compound (Patent Document 1).

JP-A-9-272758

  However, the hydrophilizing agent of Patent Document 1 has a problem that the hydrophilicity decreases with time, and the initial hydrophilicity in a low temperature environment is low. Therefore, an object of the present invention is to provide a hydrophilizing agent that maintains hydrophilicity for a long period of time and is excellent in initial hydrophilicity in a low temperature environment.

  In order to solve the above problems, the hydrophilizing agent according to the present invention contains an esterified product (A) of an alkylene oxide adduct of saccharide and a monocarboxylic acid having 1 to 24 carbon atoms, and the alkylene oxide adduct of the saccharide. And the sum of the content of saccharide residues and the content of oxyethylene groups in the esterified product (A) of monocarboxylic acid having 1 to 24 carbon atoms is 20 to 95% by mass.

  The esterified product (A) of the saccharide alkylene oxide adduct and a monocarboxylic acid having 1 to 24 carbon atoms preferably has an average hydroxyl value of 70 to 700 mgKOH / g.

  The esterified product (A) of the saccharide alkylene oxide adduct and a monocarboxylic acid having 1 to 24 carbon atoms preferably has an average of 0.5 to 2.5 ester groups in one molecule.

  The number average molecular weight of the esterified product (A) of the saccharide alkylene oxide adduct and a monocarboxylic acid having 1 to 24 carbon atoms is preferably 600 to 5,000.

  The resin molded product according to the present invention contains the hydrophilic agent and the resin (B).

  According to the present invention, a hydrophilizing agent that maintains hydrophilicity for a long period of time and is excellent in initial hydrophilicity in a low temperature environment can be obtained.

  Hereinafter, preferred embodiments of the present invention will be described.

  The hydrophilizing agent of this embodiment contains an esterified product (A) of an alkylene oxide adduct of saccharides and a monocarboxylic acid having 1 to 24 carbon atoms.

  Examples of the saccharide in the esterified product (A) of an saccharide alkylene oxide adduct and a monocarboxylic acid having 1 to 24 carbon atoms used in the present invention include sugars and sugar alcohols. Examples of the sugar include monosaccharides such as glucose, fructose, galactose and mannose, disaccharides such as sucrose, lactose, maltose and trehalose, polysaccharides such as cellulose, amylose and chitin. Examples of the sugar alcohol include sorbitol, mannitol, maltitol, and erythritol. Of these, disaccharides and sugar alcohols are preferred, and sucrose is more preferred because of its relatively low viscosity and ease of handling and the ability to maintain hydrophilicity for a longer period.

  Examples of the alkylene oxide in the esterified product (A) of the saccharide alkylene oxide adduct and C1-C24 monocarboxylic acid used in the present invention include ethylene oxide, propylene oxide, butylene oxide, styrene oxide, glycidol, tetrahydrofuran and the like. Is mentioned. Among these, at least one selected from ethylene oxide and propylene oxide is preferable because hydrophilicity can be maintained for a longer period of time, and initial hydrophilicity in a low-temperature environment is more excellent, and a combination of ethylene oxide and propylene oxide Is more preferable. When ethylene oxide and propylene oxide are used in combination, the ratio (molar ratio) of ethylene oxide / propylene oxide is preferably 1/9 to 9/1, more preferably 2/8 to 8/2. Preferably, it is 3/7 to 7/3. When ethylene oxide and propylene oxide are used in combination, a random adduct or a block adduct may be used. Among these, since the hydrophilicity can be maintained for a longer period and the initial hydrophilicity under a low temperature environment is more excellent, a block adduct is preferable, and a block addition of ethylene oxide and propylene oxide in this order is more preferable. .

  The addition amount of the alkylene oxide is preferably 3 to 100 mol per mol of saccharide. By being within the above range, the hydrophilicity can be maintained for a longer period, and the initial hydrophilicity in a low-temperature environment becomes more excellent. The addition amount of the alkylene oxide is more preferably 5 to 50 mol, and further preferably 7 to 30 mol.

  Examples of the monocarboxylic acid having 1 to 24 carbon atoms in the esterified product (A) of the saccharide alkylene oxide adduct and the monocarboxylic acid having 1 to 24 carbon used in the present invention include acetic acid, propionic acid, butyric acid, Herbic acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, pentadecylic acid, palmitic acid, palmitoleic acid, margaric acid, stearic acid, oleic acid, vaccenic acid, linoleic acid, linolenic acid, Examples include aliphatic carboxylic acids such as eleostearic acid, arachidic acid, arachidonic acid, behenic acid, lignoceric acid, and nervonic acid. Among these, the aliphatic carboxylic acid preferably has 6 to 22 carbon atoms, more preferably 8 to 20 carbon atoms, and more preferably 12 to 18 carbon atoms because initial hydrophilicity in a low temperature environment is more excellent. Is more preferable.

  Moreover, as said C1-C24 monocarboxylic acid, aromatic carboxylic acids, such as benzoic acid, toluic acid, methoxybenzoic acid, and naphthalene carboxylic acid, can also be used, for example. Among these, the aromatic carboxylic acid preferably has 6 to 22 carbon atoms, more preferably 6 to 20 carbon atoms, and more preferably 6 to 18 carbon atoms because the initial hydrophilicity in a warm environment is more excellent. Is more preferable.

  The esterified product (A) of the saccharide alkylene oxide adduct and a monocarboxylic acid having 1 to 24 carbon atoms preferably has an average hydroxyl value of 70 to 700 mgKOH / g. By being within the above range, the hydrophilicity can be maintained for a longer period, and the initial hydrophilicity in a low-temperature environment becomes more excellent. The average hydroxyl value is more preferably 150 to 600 mgKOH / g, and further preferably 200 to 500 mgKOH / g. The average hydroxyl value can be measured according to JIS K0070.

  The esterified product (A) of the alkylene oxide adduct of saccharides and a monocarboxylic acid having 1 to 24 carbon atoms preferably has a number average molecular weight of 600 to 5,000. By being within the above range, the hydrophilicity can be maintained for a longer period, and the initial hydrophilicity in a low-temperature environment becomes more excellent. The number average molecular weight is more preferably 700 to 3000, and still more preferably 800 to 2000.

  The esterified product (A) of the saccharide alkylene oxide adduct and the monocarboxylic acid having 1 to 24 carbon atoms preferably has an average degree of esterification of 0.5 to 2.5. By being within the above range, the hydrophilicity can be maintained for a longer period, and the initial hydrophilicity in a low-temperature environment becomes more excellent. The average degree of esterification is more preferably 0.7 to 2.0, and further preferably 0.9 to 1.5. In addition, in this specification, an average esterification degree shows the average value of a C1-C24 monocarboxylic acid ester group contained in 1 molecule. In this specification, the average degree of esterification indicates the average number of ester groups contained in one molecule.

  In the esterified product (A) of an saccharide alkylene oxide adduct and a monocarboxylic acid having 1 to 24 carbon atoms used in the present invention, the total content of saccharide residues and oxyethylene groups is 20 to 95 mass. %. By setting it within the above range, the hydrophilicity can be maintained over a long period of time, and the initial hydrophilicity in a low-temperature environment becomes more excellent. The sum of the content of saccharide residues and the content of oxyethylene groups is preferably 25 to 90 mass%, more preferably 30 to 85 mass%. In the present specification, the saccharide residue indicates a group obtained by removing a hydroxyl group substituted with an alkylene oxide or a monocarboxylic acid having 1 to 24 carbon atoms from a saccharide.

  The esterified product (A) of an saccharide alkylene oxide adduct and a C 1-24 monocarboxylic acid used in the present invention preferably contains 0 to 60% by mass of an oxyethylene group. By setting it within the above range, the hydrophilicity can be maintained over a long period of time, and the initial hydrophilicity in a low-temperature environment becomes more excellent. The oxyethylene group content is more preferably 0 to 50% by mass.

  The esterified product (A) of an alkylene oxide adduct of saccharides and a monocarboxylic acid having 1 to 24 carbon atoms used in the present invention is, for example, an alkylene oxide adduct of saccharides by adding alkylene oxide to the saccharide. A method of performing an esterification reaction with a monocarboxylic acid having 1 to 24 (Production Method 1), and a monocarboxylic acid ester of a saccharide by an esterification reaction with a saccharide and a monocarboxylic acid having 1 to 24 carbon atoms, (Production method 2), etc. Among these, the manufacturing method 1 is preferable because the hydrophilicity can be maintained for a longer period and the initial hydrophilicity in a low temperature environment is more excellent.

  Hereinafter, the said manufacturing method 1 is demonstrated.

  Examples of the method of adding alkylene oxide to saccharide include, for example, a method of introducing alkylene oxide into a reaction vessel at 70 to 120 ° C. and 0 to 0.3 MPa in the presence of saccharide and a catalyst, and reacting with saccharide. A known method can be used.

  As the saccharide used for the alkylene oxide addition reaction, saccharide alone can be used, but from the viewpoint of reducing the viscosity of the reaction solution, it is preferable to use saccharide dissolved in a compound capable of dissolving saccharide. Examples of such compounds that can dissolve saccharides include hydroxyl-containing compounds other than saccharides such as water, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, glycerin, and trimethylolpropane. Of these, water is preferable because of its high solubility in sugars and easy distillation after the addition reaction. Moreover, it is preferable that the usage-amount of the compound which can melt | dissolve saccharides is 20 mass parts or less with respect to 100 mass parts of saccharides from a viewpoint of raising the ratio of the alkylene oxide added to saccharides.

  The catalyst used for the alkylene oxide addition reaction is not particularly limited. For example, alkali metals such as potassium hydroxide and sodium hydroxide, alkaline earth metals such as calcium hydroxide and magnesium hydroxide, diethanolamine, triethylamine and the like. Amines, cationic polymerization catalysts, double metal cyanide complex catalysts, and the like. The usage-amount of a catalyst is 0.01-5.0 mass parts with respect to 100 mass parts of saccharides, for example.

  The saccharide alkylene oxide addition reaction product may be further purified. By performing the purification treatment, the hydrophilicity can be maintained for a longer period. Examples of such purification treatment include adsorbent treatment and distillation treatment. Among these, the adsorbent treatment is preferable because the production process is easy.

  The adsorbent treatment method is not particularly limited. For example, the saccharide alkylene oxide addition reaction product and the adsorbent are mixed using a stirrer or the like, and the saccharide alkylene oxide addition reaction product is added to the adsorbent packed column. The method of making it pass is mentioned. Among these, since the operation is simple, a method of mixing the saccharide alkylene oxide addition reaction product and activated carbon is preferable. In addition, when using a solvent such as water or an organic solvent, the adsorbent may be added after mixing with the saccharide alkylene oxide addition reaction product in advance, or the saccharide alkylene oxide addition after dispersing the adsorbent in the solvent. It may be mixed with the reactants.

  The adsorbent is for adsorbing and removing impurities contained in the saccharide alkylene oxide addition reaction product. Such an adsorbent may be in the form of powder, granules, or pellets, and is preferably in the form of powder. Examples of such an adsorbent include activated carbon, zeolite, and the like. Particularly, since the heat resistance of the hydrophilizing agent is more excellent, activated carbon is preferable, and the pH in a 1% by mass aqueous suspension is 4 to 11. Activated carbon is more preferable, and activated carbon having a pH of 4.5 to 7.5 is more preferable.

  The amount of the adsorbent used is not particularly limited, but is preferably 0.1 to 20.0 parts by mass, and 1.0 to 10.0 parts by mass with respect to 100 parts by mass of the alkylene oxide addition reaction product. More preferably. By making the usage-amount of adsorption agent in the said range, a manufacturing process will become a simpler thing.

  Moreover, it is preferable to use a solvent in the adsorbent treatment. By using the solvent, the viscosity of the alkylene oxide addition reaction product is reduced, and the purification treatment can be easily performed.

  Moreover, in the said adsorption agent process, you may use various additives, such as antioxidant and a ultraviolet absorber other than the said solvent.

  The esterification reaction of the alkylene oxide adduct of saccharide obtained by the above method with a monocarboxylic acid having 1 to 24 carbon atoms can be carried out by a known method. For example, a method in which an alkylene oxide adduct of saccharide and a monocarboxylic acid having 1 to 24 carbon atoms are reacted under conditions of 70 ° C. to 180 ° C. and 1 kPa to 100 kPa in the presence of a catalyst.

  The monocarboxylic acid having 1 to 24 carbon atoms may be a compound that can form a monocarboxylic acid ester group, and a monocarboxylic acid derivative can be used. Examples of such monocarboxylic acid derivatives include monocarboxylic acid halides such as monocarboxylic acid chloride and monocarboxylic acid bromide, and monocarboxylic acid esters such as monocarboxylic acid methyl ester and monocarboxylic acid ethyl ester. Among these, since the coloring of the esterified product (A) of an alkylene oxide adduct of saccharides and a monocarboxylic acid having 1 to 24 carbon atoms can be further suppressed, it is preferable to use a monocarboxylic acid ester.

  The resin molded product according to the present invention contains an esterified product (A) and a resin (B) of an alkylene oxide adduct of the saccharide and a monocarboxylic acid having 1 to 24 carbon atoms. The resin molded article preferably contains an esterified product (A) of an saccharide alkylene oxide adduct and a monocarboxylic acid having 1 to 24 carbon atoms and a resin (B) in a mixed state.

  Examples of the resin (B) that can be used in the present invention include polystyrene resins, polyester resins, polyolefin resins, polycarbonate resins, polylactic acid resins, polyvinyl chloride resins, polysulfone resins and other thermoplastic resins, phenol resins, urea resins, Examples thereof include thermosetting resins such as melamine resin and epoxy resin. Of these, thermoplastic resins are preferred.

  The content of the esterified product (A) of the alkylene oxide adduct of saccharides and the monocarboxylic acid having 1 to 24 carbon atoms in the resin molded product of the present invention is 0.1% relative to 100 parts by mass of the resin (B). It is preferable that it is 1-10 mass parts. By setting it within the above range, higher hydrophilicity can be maintained over a long period of time. The content is more preferably 0.5 to 5.0 parts by mass.

  The method for producing the resin molded article of the present invention is not particularly limited as long as it is a method capable of mixing the esterified product (A) of the saccharide alkylene oxide adduct and the monocarboxylic acid having 1 to 24 carbon atoms and the resin (B). . Examples of such a method include a method of mixing using a kneading machine such as an open type twin-screw kneader or a kneader.

  In the production method, the mixing temperature of the esterified product (A) of the saccharide alkylene oxide adduct and the monocarboxylic acid having 1 to 24 carbon atoms and the resin (B) is preferably 140 to 240 ° C. By being within the above range, the esterified product (A) of the saccharide alkylene oxide adduct and the monocarboxylic acid having 1 to 24 carbon atoms and the resin (B) can be mixed more uniformly. The hydrophilicity can be maintained over a long period of time, and the initial hydrophilicity in a low temperature environment is more excellent.

  The resin molded article of the present invention may contain known additives in addition to the esterified product (A) and the resin (B) of an alkylene oxide adduct of saccharides and a monocarboxylic acid having 1 to 24 carbon atoms. Examples of such additives include antioxidants, ultraviolet absorbers, flame retardants, and the like.

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

  In this example, as an esterified product (A) of an saccharide alkylene oxide adduct and a monocarboxylic acid having 1 to 24 carbon atoms, the saccharide alkylene oxide adduct and carbon atoms 1 to 1 obtained in Production Examples 1 to 11 below. Esterified products (a-1) to (a-11) with 24 monocarboxylic acids were used.

(Production Example 1)
A stainless steel autoclave was charged with 342 g (1 mol) of sucrose, 70 g of water, and 3 g of potassium hydroxide, and the inside of the reactor was purged with nitrogen. The temperature was raised to 80 ° C. to dissolve sucrose, then the temperature was raised to 100 ° C., and 441 g (10 mol) of ethylene oxide was introduced while keeping the internal pressure at 0.3 MPa or less. After the introduction, the reaction was further carried out at 100 ° C. for 2 hours. 500 g of this reaction product and 150 g of water were mixed and adjusted to 50 ° C., and acetic acid was further added to adjust the pH to 6. Subsequently, 50 g of powdered activated carbon (trade name: Strong Shirasagi A (manufactured by Nippon Enviro Chemicals, 1% aqueous solution pH: 4.9) was added and stirred for 2 hours at 50 ° C. Thereafter, the activated carbon was removed by filtration. By removing water at 90 ° C. under reduced pressure, an ethylene oxide (10 mol) adduct of sucrose was obtained.
Subsequently, 391 g of the sucrose ethylene oxide (10 mol) adduct, 107 g of methyl laurate (trade name: Pastel M-12, manufactured by Lion Specialty Chemicals) and 1.5 g of potassium carbonate were charged into a stainless steel autoclave. The reactor was purged with nitrogen. The temperature was raised to 100 ° C., and the mixture was reacted for 5 hours under reduced pressure (2.7 kPa). Next, after cooling to 70 ° C., the pressure is returned to 1 atm, and 2.4 g of lactic acid is added to neutralize potassium carbonate, whereby an esterified product of sucrose ethylene oxide (10 mol) adduct and lauric acid (a- 1) was obtained.

(Production Example 2)
The same procedure as in Production Example 1 was carried out except that 464 g (8 mol) of propylene oxide was used in place of ethylene oxide, and an esterified product of sucrose with a propylene oxide (8 mol) adduct and lauric acid (a-2) Got.

(Production Example 3)
The same operation as in Production Example 1 was performed except that 224 g of methyl stearate (trade name: Pastel M-180, manufactured by Lion Specialty Chemicals) was used instead of methyl laurate, and ethylene oxide of sucrose (10 mol) ) An esterified product (a-3) of an adduct and stearic acid was obtained.

(Production Example 4)
Instead of methyl laurate,
Except for using 134 g of methyl oleate (trade name: Pastel M-181, manufactured by Lion Specialty Chemicals), the same operation as in Production Example 1 was carried out, and an ethylene oxide (10 mol) adduct of sucrose and oleic acid Esterified product (a-4) was obtained.

(Production Example 5)
The same operation as in Production Example 1 was carried out except that the amount of methyl laurate used was 86 g, to obtain an esterified product (a-5) of sucrose ethylene oxide (10 mol) adduct and lauric acid.

(Production Example 6)
A stainless steel autoclave was charged with 342 g (1 mol) of sucrose, 70 g of water, and 3 g of potassium hydroxide, and the inside of the reactor was purged with nitrogen. The temperature was raised to 80 ° C. to dissolve sucrose, then the temperature was raised to 100 ° C., and 352 g (8 mol) of ethylene oxide was introduced while maintaining the internal pressure at 0.3 MPa or less. After the introduction, the reaction was further carried out at 100 ° C. for 2 hours. Subsequently, 464 g (8 mol) of propylene oxide was introduced while maintaining the internal pressure at 0.3 MPa or less. After the introduction of propylene oxide, the reaction was carried out at 100 ° C. for 2 hours. The reaction product 500 and 150 g of water were mixed and adjusted to 50 ° C., and acetic acid was further added to adjust the pH to 6. Subsequently, 50 g of powdered activated carbon (trade name: Strong Shirasagi A (manufactured by Nippon Enviro Chemicals, 1% aqueous solution pH: 4.9) was added and stirred for 2 hours at 50 ° C. Thereafter, the activated carbon was removed by filtration. By removing water at 90 ° C. under reduced pressure, an ethylene oxide (8 mol) propylene oxide (8 mol) block adduct of sucrose was obtained.
Subsequently, in a stainless steel autoclave, 580 g of the above sucrose ethylene oxide (8 mol) propylene oxide (8 mol) block adduct, 107 g of methyl laurate (trade name: Pastel M-12, manufactured by Lion Specialty Chemicals), Potassium carbonate 1.5 g was charged, and the inside of the reactor was purged with nitrogen. The temperature was raised to 100 ° C., and the mixture was reacted for 5 hours under reduced pressure (2.7 kPa). Next, after cooling to 70 ° C., the pressure is returned to 1 atm, and 2.4 g of lactic acid is added to neutralize the potassium carbonate, whereby sucrose ethylene oxide (8 mol) propylene oxide (8 mol) block adduct, lauric acid, Esterified product (a-6) was obtained.

(Production Example 7)
The same operation as in Production Example 6 was carried out except that the amount of ethylene oxide used was changed to 441 g (10 mol) and the amount of propylene oxide used was changed to 291 g (5 mol), and sucrose ethylene oxide (10 mol) propylene oxide (5 Mol) An esterified product (a-7) of a block adduct and lauric acid was obtained.

(Production Example 8)
The same operation as in Production Example 6 was carried out except that the amount of ethylene oxide used was changed to 220 g (5 mol) and the amount of propylene oxide used was changed to 581 g (10 mol), and sucrose ethylene oxide (5 mol) propylene oxide (10 Mol) An esterified product (a-8) of a block adduct and lauric acid was obtained.

(Production Example 9)
The same procedure as in Production Example 6 was performed except that 150 g of methyl stearate (trade name: Pastel M-180, manufactured by Lion Specialty Chemicals) was used instead of methyl laurate, and ethylene oxide of sucrose (8 mol) ) An esterified product (a-9) of propylene oxide (8 mol) block adduct and stearic acid was obtained.

(Production Example 10)
Instead of methyl laurate, the same operation as in Production Example 6 was performed except that 149 g of methyl oleate (trade name: Pastel M-181, manufactured by Lion Specialty Chemicals) was used, and sucrose ethylene oxide (8 mol) An esterified product (a-10) of propylene oxide (8 mol) block adduct and oleic acid was obtained.

(Production Example 11)
The same operation as in Production Example 6 was conducted except that the amount of methyl laurate used was 214 g, and an esterified product of sucrose ethylene oxide (8 mol) propylene oxide (8 mol) block adduct and lauric acid (a-11) Got.

  Average esterification degree, average hydroxyl value of esterified products (a-1) to (a-11) of alkylene oxide adducts of saccharides obtained in Production Examples 1 to 11 and monocarboxylic acids having 1 to 24 carbon atoms ( Table 1 shows the OHV), the content of oxyethylene groups (EO content), the sum of the content of saccharide residues and the content of oxyethylene groups (content of saccharides and EO), and the number average molecular weight.

(Measurement method of average hydroxyl value)
It measured according to JIS K0070.

(Measurement method of number average molecular weight)
The number average molecular weight in terms of polyethylene was calculated by GPC method under the following conditions.
[Measurement condition]
Measurement sample: 1 wt% tetrahydrofuran solution
Apparatus: LC-10AD (trade name, manufactured by Shimadzu Corporation)
Column: GPC KF-801, GPC KF-801 and GPC KF-803 (trade names, all manufactured by Showa Denko KK) connected in series Mobile phase: Tetrahydrofuran (flow rate: 0.8 mL / min)
Column temperature: 25 ° C

Moreover, the following were used as raw materials other than the esterified product (A) of an alkylene oxide adduct of saccharides and a monocarboxylic acid having 1 to 24 carbon atoms.
・ Resin (B)
(B-1) Low density polyethylene (trade name: Novatec LL UF442, manufactured by Nippon Polyethylene)
・ Other ingredients (C)
(C-1) A mixture obtained by dissolving 60 g of sodium lauryl sulfate (trade name: EMAL 0, manufactured by Kao Corporation) and 40 g of lauryl monoethanolamide in 30 g of methanol and distilling off the methanol (c-2) Sodium alkylbenzenesulfonate ( (Product name: Raipon PS-230, manufactured by Lion Corporation) 80 g and lauryldiethanolamine 20 g were dissolved in 50 g of methanol, and the methanol was distilled off.

(Examples 1 to 13)
At a ratio shown in Table 2, the esterified product (A) and the resin (B) of an alkylene oxide adduct of saccharides and a monocarboxylic acid having 1 to 24 carbon atoms at 150 ° C. using an open biaxial kneader. Kneaded for 10 minutes. The obtained kneaded product was press-molded at 150 ° C. in a mold (diameter 10 cm, thickness 1 mm) to prepare a test piece. Using this test piece, the hydrophilicity was evaluated by the following method. The results are shown in Table 2.

(Hydrophilic)
The obtained test piece was left still for a predetermined period (1 day, 14 days, or 30 days) in a constant temperature and humidity chamber (set temperature: 60 ° C., set humidity: 70% RH). Using this test piece, the contact angle (degree) by the tangent method was measured according to JIS R3257.

(Initial hydrophilicity in low temperature environment)
The surface of the obtained test piece was wiped off with a cloth soaked with ethanol, and then allowed to stand for 1 day in a constant temperature and humidity chamber (5 ° C., 70% RH). Using this test piece, the contact angle (degree) by the tangent method was measured according to JIS R3257.

(Comparative Examples 1 and 2)
The same operation as in Example 1 was carried out except that the other component (c-1) or (c-2) shown in Table 2 was used without using the saccharide alkylene oxide adduct (A). The results are shown in Table 2.

  As is apparent from Table 2, the hydrophilizing agent of the present invention can maintain hydrophilicity for a long period of time and is excellent in initial hydrophilicity in a low temperature environment. In particular, when an esterified product of an saccharide ethylene oxide propylene oxide block adduct and a C 1-24 monocarboxylic acid is used as in Examples 6 to 13, the above effects are more excellent. On the other hand, when the alkylene oxide adduct (A) of saccharide is not used as in Comparative Examples 1 and 2, the hydrophilicity greatly decreases in a short period, and the initial hydrophilicity in a low temperature environment is inferior.

The hydrophilizing agent of the present invention can be used as a hydrophilizing agent used for resins and the like because it can maintain excellent hydrophilicity over a long period of time and is more excellent in initial hydrophilicity in a low temperature environment.

Claims (5)

A hydrophilizing agent containing an esterified product (A) of an alkylene oxide adduct of a saccharide and a monocarboxylic acid having 1 to 24 carbon atoms,
The total of the content of saccharide residues and the content of oxyethylene groups in the esterified product (A) of the saccharide alkylene oxide adduct and a monocarboxylic acid having 1 to 24 carbon atoms is 20 to 95% by mass. The
A hydrophilizing agent, wherein the saccharide is sucrose .   2. The hydrophilizing agent according to claim 1, wherein the esterified product (A) of the alkylene oxide adduct of saccharides and a monocarboxylic acid having 1 to 24 carbon atoms has an average hydroxyl value of 70 to 700 mgKOH / g.   The hydrophilizing agent according to claim 1 or 2, wherein the esterified product (A) of the alkylene oxide adduct of saccharides and a monocarboxylic acid having 1 to 24 carbon atoms has an average degree of esterification of 0.5 to 2.5. .   The number average molecular weight of the esterified product (A) of the alkylene oxide adduct of saccharides and a monocarboxylic acid having 1 to 24 carbon atoms is 600 to 5000, Hydrophilization according to any one of claims 1 to 3. Agent.   The resin molded product containing the hydrophilizing agent and resin (B) of any one of Claims 1-4.