JPS61196960A - Functional substance release agent - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed Description of the Invention] [Industrial Field of Application] The present invention relates to a functional substance releasing agent, and more specifically, to a fragrance, agrochemical,
The present invention relates to a functional substance releasing agent that releases functional substances such as medicines at a controlled rate.

[Conventional technology]

It is known that polymerizable acetals of functional substances such as fragrances and vitamins that have hydroxyl groups, whether monomers or l-rimers, are easily hydrolyzed and gradually release functional substances [Kamogawa et al. Butt, Chem. ,Soc,
Jpn, + 4, 1917 (197, 6), same ■,
846 (1979):l.

[Problem that the invention seeks to solve]

However, the above-mentioned acetal releases aldehyde as well as functional substances, which is undesirable from both the sense of smell and health.

The present invention was discovered as a result of repeated research in search of a monofunctional substance releasing agent that does not produce harmful substances.

[Means for solving problems]

The present invention is a functional substance releasing agent comprising a sulfonic acid ester of a functional substance having a hydroxyl group (hereinafter simply referred to as functional substance).

The functional substance in the present invention is a compound having a hydroxyl group that is used in fragrances, agricultural chemicals, medicines, and the like.

Fragrances include citronellol, t-menthol, borneol, 2-phenethyl alcohol, geraniol,
Terpene alcohols such as nerol, 3.7-cystyloctanol, eugenol, ineugenol, p-
Alcohols with aromatic rings such as anisyl alcohol and cinnamyl alcohol are included.

Pesticides include herbicides such as 2,4-dichlorophenoxyethanol, 2,4,5-trichlorophenoxyethanol, and pentachlorophenol, plant growth regulators such as gibberellin, antibiotic fungicides such as kasugamycin, polyoxin, actidione, etc. Insecticides such as 2,4-sheet o-6-cyclohexylphenol, 1,1-bis(p-10ruphenyl)ethanol, 1,1-bis(p-chlorophenyl)-2,2,2-trichloroethanol , 2-ethyl-1°3-hexanediol, insect repellents such as 2-butyl-2-ethyl-1,3-propanediol, trans-10,cis-12-hexadecadiene-
There are 7 eromones such as 1-ol and 10-acetoxy-7-cis hexadecenol.

As a medicine, vitamin A, A2, B, %B2, B
Vitamins such as 2, B, 2, BIS, Cs D, hormones such as corticosterone, androsterone, testosterone, estrone, and estradiol, purines,
These include physiologically active substances such as inositol, and disinfectants such as salicylic acid, phenol, cresol, and ethylene glycol monosalicylate.

Sulfonic acids include aliphatic sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, dodecanesulfonic acid, benzenesulfonic acid, toluenesulfonic acid, xylene sulfonic acid, cumenesulfonic acid, octylbenzenesulfonic acid, and Pinzenesulfonic acid, dodecylbenzenesulfonic acid, naphthalenesulfonic acid, butylnaphthalenesulfonic acid, styrenesulfonic acid, α-
There are aromatic sulfonic acids such as methylstyrene sulfonic acid.

The sulfonic acid ester of the functional substance in the present invention can be easily produced by reacting the functional substance with sulfonylchloride.

When the sulfonic acid ester of the functional substance is an ester of polymerizable sulfonic acid such as styrene sulfonic acid,
It can be homopolymerized or copolymerized with other monomers.

Other monomers to be copolymerized include unsaturated hydrocarbons such as ethylene, propylene, butene, octene, butadiene, and styrene, methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, and octyl (meth)acrylate. ) Acrylic acid esters and methacrylic acid esters such as acrylate, dodecyl (meth)acrylate, hydroxyethyl (meth)acrylate, glycidyl (meth)acrylate, unsaturated carboxylic acids and their salts such as acrylic acid, methacrylic acid, maleic acid, etc. Those commonly used in polymerization, such as acrylamide, methacrylamide, acrylonitrile, vinyl acetate, and vinylpyrrolidone, are used, and either hydrophilic or hydrophobic monomers may be used.

[Effect]

The sulfonic acid ester of the functional substance is hydrolyzed by water to release the functional substance.

Depending on the stability to water, the sulfonic acid ester of the present invention gradually releases the functional substance by moisture in the air, by contact with water, or by heating with water.

〔Effect of the invention〕

The functional substance releasing agent of the present invention can gradually release a functional substance, so in the case of an air freshener, the fragrance can be maintained for a long period of time, and in the case of an agricultural chemical, the efficacy can be maintained, In this case, the medicinal efficacy can be maintained for a long time.

In addition, depending on the structure of the sulfonic acid and the functional substance, it is possible to create a variety of sulfonic acid esters, ranging from those that are susceptible to unstable hydrolysis to those that are not susceptible to stable hydrolysis, so that they can have a long-lasting effect that suits the purpose. Functional substance releasing agents can be created.

In the case of polymerizable sulfonic acid esters such as styrene sulfonic acid esters, their affinity for water can be adjusted by homopolymerization or copolymerization with hydrophilic or hydrophobic monomers, resulting in hydration. The ease of disassembly can be adjusted.

〔Example〕

The invention will be illustrated by manufacturing examples and examples.

In addition, CH indicates weight %.

Production Examples 1 to 11 are examples of sulfonic acid esters of fragrance alcohols that are aromatic agents, Production Examples 12 and 13 are examples of sulfonic acid esters of functional substances that have herbicidal effects as pesticides, and Production Example 1 = 1 This is an example of the obtained hydrophilic copolymer of sulfonic acid ester.

Example 1 is a hydrolysis test of the sulfonic acid ester obtained in Production Examples 1 to 13, and Example 2 is a hydrolysis test of the sulfonic acid ester polymer obtained in Production Example 14. Example 3
is a test that shows the difference in fragrance persistence between fragrance alcohol and its sulfonic acid ester.

Preparation Example 1 Citronellyl p-styrenesulfonate Citronellol 3,7 (24 mmol), 4-lit-t-butylcatechol 0. IP and anhydrous Vitdin 60
4.9 J' (24 mmol) ft of p-styrenesulfonyl chloride was slowly added to 1 ml of ice-cooled mixed solution with stirring, and after continued stirring for 3 hours, it was placed in a refrigerator for 24 hours.
Saved time. Next, the reaction mixture was poured into 300ml of ice water, stirred for a while, and then poured into 200ml of ethyl ether.
Extraction was carried out twice using 1 liter each. After washing the extract with 10 tons of cooled aqueous hydrochloric acid solution and 200 tons of aqueous hydrochloric acid solution, 1
The residue was washed with 100ml of hexane, then dehydrated by adding anhydrous sodium sulfate, and the solvent was removed using a rotary evaporator at 30"C. Next, the residue was dissolved in 100ml of hexane, and 0.1J' of activated carbon was added. The mixture was stirred and filtered, and the solution F was cooled to -70° C. to form a precipitate. The supernatant was discarded and the residue was vacuum dried to give a clear liquid in a yield of 39%.

Elemental analysis (C18H2603S) Measured value C: 67.11chi, H: 8.07 coefficient calculated value
C: 67.05, H: 8.13 IR (CH Hiro) 3000-2800 (alkyl), 1600 (aryl) i 1350, 1160 (S=0).

980.920 (vinyl) knee 1 'H-NMR (CD C10) δ 0.7-2.5 (m, 16H, alkyl).

4.05 (t+ 2H, CH20), 5.0 (b
, IH.

(CH3)2C=Cdan”), 5.4 (d,
IH, CH2=CH).

5.8 (d, IH, C di=CH), 6.5-7.
1 (q, I H, CH2=Cdan), 7.4-8.0
(q+ 4H1 complete H) Mass spectrometry (m/e) 322 (MF), 1103 (100) Preparation example 2 t-menthyl p-styrene sulfonate t-menthol 3. OJ' (19 mmol) and p-styrenesulfonyl chloride4. A reaction was carried out in the same manner as in Production Example 1 using OJ' (20 mmol), and the white solid was
Obtained with a yield of 4%.

Melting point 90-92°C Elemental analysis (C, 8H2603'PL) measurement value C:
67.19%, H near, 99 coefficient calculated value C: 67.0
5chi, H: 8.13chi I R (CIt(ct3") 3000-2800 (alkyl) 1600 (aryl'); 1.360.1160 (S==O); 985,9
00 (vinyl) -1'H-NMR (CD C13) δ 0.4-2.5 (m, 18H, alkyl)・
4.4 <b, IH, ncuo->, 5.4 < d
+IHtCH=CH);5.8(d,IH,”!z
=cH); 6.5-7.1 (q, IH, CH2”C
dan) i7.4-8.0 (qy 4H, aryl H)
Mass spectrometry Cm/e) 322 (M+) IJ Preparation Example 3 Bornyl p-styrene sulfonate Borneol 3.3 J' (21 mmol) and p-styrene sulfonate 4.47' (22 mmol) were used in the same manner as in Production Example 1. The reaction was carried out and a white solid was obtained in a yield of 48 pieces.

Melting point 57-58°C Elemental analysis (C18H24o3s) Measured value C: 67.50% pH: 7.52
'A calculated value C: 67.47%, H near, 55% I
R(CHC10) 3000-2800(alkyl)・1600(aryl)i 1360. 1160 (S=O) 1990.
910 (Vini A/) an''H-NMR (CD
C10) δ 0.6 2.5 (ff1. 16Ht alkyl)・4.7 <b+ IH,">cHo->;
5.5 < a, IH, C horse=CH)i 6.0
(d, IHICH=CH); 6.6-7.2 (q+
IH, CH2=Cdan); 7.5-8.1 (q,
4H, Real H) Mass spectrometry (m/e) 320 (M'') M Preparation Example 42-7 Ethyl P-Styrene Sulfonate 2-Phenethyl Alcohol 5. OJ' (41 M!J
mole) and p-styrenesulfonyl chloride 13J' (6
The reaction was carried out in the same manner as in Production Example 1 using 4 mmol). The residue obtained by removing the solvent using a rotary evaporator was dissolved in hexane 1QQd and left in a -20'C freezer for several hours, causing precipitation. The supernatant was collected by decantation and cooled to -70'C to precipitate the product, which was vacuum dried to give a pale brown viscous liquid with a yield of 87%.

Elemental analysis (C+6H+a 03S) Measured value C: 66.63 t, H: 5.60 t Calculated value C
・66゜64chi, H:5.59qbI R (CHC13
) 3100-2800(alkyl)・1600(aryl)i1360,1140(S=0);980.910(
vinyl) α-1')i -N M R δ 3.0 (t, 2H, Cdan2CH□0)i4.3(
t.

2H, CH2C,! l! 2o), 5.5 (d,
I H# CH=CH); 5.9 (d, IH, CH
=CH)i6.6-7,1 (q, L H,0M2
-Cdan), 7.0-8.0 (m, 9H, aryl H) Mass spectrometry (tn/e) 288 (M+) Production example 53.7-dimethyloctyl p-styrenesulfonate 13.7-dimethyloctanol While stirring an ice-cooled mixed solution of 3.27' (20 mmol), triethylamine 3.0/(30 mmol), phenothiazine 0.2 t, and anhydrous benzene 60 d, p-styrenesulfonyl chloride 4.
IJ' (20 mmol) was slowly added, stirred for 5 hours, and then stored in a refrigerator for 24 hours. Then, the reaction mixture was filtered, the p solution was freeze-dried, and then
K was dissolved and activated carbon was added. The product was precipitated by cooling the P solution to -70"C. It was dried in vacuo to give a viscous liquid in a yield of 54"C.

Elemental analysis (C,, H2803S) Measured value C: 66.97 coefficient, ) t: 8.17 coefficient calculated value
C: 66.63 tH: 8.70 IR (CHC10
) 3050-2800 (alkyl)・1595 (aryl)・1360.1160 (S=O)・990.920
(Bi=h) cm-'H-NMR (CDC1,) δ 06-1.8 (m, 19H, alkyl) 4.0 (t
, 2H, CH2O); 5.3 (d, IH, C=CH); 5.6 (d, LH, C=CH);
) i6.5 (q, IH, CI (2=Cdan);
7.1-7.8 (q.

4H, aryl H) Mass spectrometry (m/e) 324 (M+) Production example 62-methoxy-4-(2-propenyl)phenyl p-styrenesulfonate eugenol 3°3J' (20 mmol) and p-styrenesulfonyl chloride 4 The reaction was carried out in the same manner as in Production Example 5 using .17 (20 mm! J moles), and the viscous liquid
It was obtained in a yield of .

Elemental analysis (C,,H,04S) Measured value C: 65.05chi, H: 5.53 coefficient calculated value C
: 65.44, H: 5.49 IR (CH(4) 2950-2800 (alkyl) 1595 (aryl) i 1360, 1140 (S=O) i9B0.900
(Vinyl) 儂-1 jH-NMR (CDCl3'') δ 3.3 (d, 2H, CH3=CHCH); 3
．． 5 (s, 3H+ 0CH3); 5.0 (d,
2H+ CH.

=CHCH2), 5.4 (d, L H, C horse = C
HAr), 5.8 (d, IH, Cdan2=CHAr)
; 5.95 (b, I H, CH2=CdanCH2)
i 6.4-7.1 (m, 4H, CH2=CdanA
r, ATH) i 7.2-7.8 (q, 4H, A
rH) Mass spectrometry (m/e) 330 (M+) Production example 7 2-methquin-4-(1-propenyl)phenyl p-styrenesulfonate isoeugenol 3.3J' (20 mmol) and p-styrenesulfonyl chloride 4. The reaction was carried out in the same manner as in Production Example 5 using 1 t (20 mmol) to obtain a viscous liquid with a yield of 45%.

Elemental analysis (C,8H0,04S) Measured value C: 65.27 t, H: 5.50 t calculated value
C: 65.44%, H: 5.49% IR (CHCL3
) 2950-2800 (alkyl) 1595 (aryl) i 1365.1140 (S=O) i 950.905 (
vinyl) cllll-''H-NMR (CDC2,) δ 1.8 (d, 3H, CH3); 3.5 (s
, 3H.

0CH8) ;5.4 (d, IH, CH=CH);5
．． 8(d, IH, CH2=CH); 6.0-7.2
(m.

6I(, CH2=CH, CH3CH=CH, ArH)i
7.2-7.9 (q, 4H, ArH) Mass spectrometry C
tn/e) 330 (M+) Production example s p-anisyl p-styrene sulfonate 16.87' (200 mmol) and anhydrous benzene 5
Q ml while mixing under water cooling, add 4. ml of p-styrenesulfonyl chloride. I J' (20 mmol) was added slowly. The mixture was stirred at 5°C for 8 hours and stored in the refrigerator for 48 hours. The reaction mixture was then filtered;
After freeze-drying the F solution, it was dissolved in 7100 πl of hexane, and 0.19 g of activated carbon was added. The mixture was filtered and the P solution was cooled to -70C to precipitate the product. When this was dried under vacuum, a viscous liquid was obtained with a yield of 69%.

Elemental analysis (C16HI6048) Measured value C: 63.47%, H: 5.27% Calculated value C: 63.14%, H: 5.30%I R (CH
Cta) 3000-2800 (alkyl); 1600 (aryl); 1370.1140 (S=O); 980.910 (
vinyl) α-1′H-NMR (CDCt3) δ 3.75 (s, 3H-OCH3);
4.4 (s, 2H, CH20); 5.45 (d,
IH, CH2=CH): 5.8 (d, IH1CH2=
CH) ; 6.5-6.9 (q, I H, CH2=C
H); 6.7 8.0 (m, 8H, ArH) Production Example 9 Cinnamyl p-styrene sulfonate/namyl alcohol 2.7y (20 mmol) and p-
Styrene sulfonyl chloride l' 4.1 y (20 mi I
When the reaction was carried out in the same manner as in Production Example 8 using J mol), a viscous liquid was obtained with a yield of 59%.

Elemental analysis (Cl7H16038) Measured value C: 68.03%, H: 5.36chi Calculated value C: 67.98%, H: s, 37chi I R (C
HCl3) 3000-2800 (furkyl); l 590 (
7 reels); 1370, 1160 (S=O)
-1'H-NMR (CDC43) of , 980.910 (vinyl) δ 4.3 (d, 2H%CH20), 5.6 (d, IH
, (42=CH); 5.9(d, I H, CH2=C
H); 6.2 7.1 (m, 3H, CH=C
Pi, CH2=CH); 7.2-8.2 (m, 9H,
ArH) Production Example 10 Geranyl p-styrene sulfonate geraniol 7.7y (50 mmol), sodium hydride (50y dispersion>
4.8 F (1'00 mmol) and 100a+/ of anhydrous ether were stirred for 15 hours at 20C in the absence of moisture under a blanket of nitrogen. The obtained dispersion was mixed with -IO
p-styrenesulfonyl chloride 1
Add a solution of Oy (50 mmol) in anhydrous ether.
Stirred at 0C for 2 hours and then at 20C for 1 hour. The reaction mixture was filtered and the F solution was evaporated in an evaporator. The residue was dissolved in hexane and cooled to -700 to precipitate the product.

This was dried under vacuum to give a clear liquid with a yield of 41%.

Elemental analysis (Cl8H2403S) Measured value C: 67.88%, H: 7.50% calculated value
C: 67.50%, I(: 7.50%I R(CH
Cl3) 3000-2800 (furkyl); 1600 (7
reel); 1380.1140 (S=O); 990.9
10 (vinyl) cm 1 'H-NMR (CDCl2) δ 1.5-2.3 (m, 13H, CH3, C
H2); 4.1 (d, 2H, CH20); 4.9
-5.6 (m.

2H, =CH-), 5.6 (d, IH, vinyl), 6.
0 (d, IH, vinyl), 6.8 (q, IH.

beer); 7.5-8.3 (q, 4H, ArH)i
t analysis (m/e) 320 (M”) Production Example 11 Citronellyl p-)luenesulfonate Using citronellol 3.5y (20 mmol) and p-toluenesulfonyl p9F4.15r (20 mmol), Production Example 1 and Perform the same reaction and make 4 transparent limbs.
It was obtained in a yield of 0.0%.

Elemental analysis (Cl7H2603S) Measured value C: 65.45%, H: 8.61% Calculated value C: 65.77chi, H: 8.44chi I R (CH
Cl3) 3000-2800 (furkyl); 1600 (aryl); 1350, 1160 (S=O)
"''H-NMR (CDC43) δ 0.7-2.5 (m, 19H, alkyl), 4.05 (t, 2H, CH20), 5.0 (b
, I.H.

(CH3)2C=CH), 7.4-8.0 (q, 4
H, aryl H) Mass spectrometry (m/e) 310 (M+) Production example 12 2-(2,4-dichlorophenoxy)ethyl p-styrenesulfonate 2.4-dichlorophenoxyethanol 3.9y (19
mmol) and p-styrenesulfonyl chloride 4.0
A reaction was carried out in the same manner as in Production Example 1 using y (20 mmol). For extraction, use 100ml each of benzene instead of ether.
The product was analyzed twice using column chromatography (Wakogel C-3
00, silica gel) to produce a clear liquid with a concentration of 31%
It was obtained in a yield of .

Elemental analysis (Cl6H1404S Cl2) measurement value C
: 51.23chi, H: 3.83% calculated value C: 5
1.33 CH, H: 3.74 CH IR (CHCl3) 1600 (aryl); 1360.1170 (S=O)
;990.910(vini7+z)cm''H-NMR(
CDC43) δ 43(d, 41'(,2CHHz); 5.5 (d
, IH% Cdan2=CH); 5.9 (d, IH,
C and 2=CH); 6.7 (q,] H, CH2=Cdan)
; 6.7-8.0 (m, 7H, ArH) Mass spectrometry (m/e) 374 (M”) Production example 13 2-(2,4,5-)lychlorophenoxy)ethyl p-styrene sulfonate 2.4.5-Trichlorophenoxytanol 4.6y (
19 mmol) and p-styrenesulfonyl chloride4.
A reaction was carried out in the same manner as in Production Example 12 using 0 y (20 mmol) to obtain a transparent liquid with a yield of 36%.

Elemental analysis (C16H1304S C13) measurement value C:
46.55%, H: 3.45ch calculated value C: 46.
83%, H: 3.17 CH IR (CHCL3) 1580 (aryl); 1340.1150 (S20)
;980.900 (vinyl) Cl11''H-N
M R δ 4.3 (d, 4H12CH2); 5.5
(d, IH, CH2=CH); 5.9 (d
, I H, CH2=CH); 6.7 (q, l
H, CH2=C and); 6.8. -8.0 (m, 6H%
ArH) Mass spectrometry (m/e) 410 (M+) ILMt Example 14 p-styrene sulfonate ester obtained in p-styrene sulfonate copolymer production examples 1 to 4, to, 12 and 13 (3 mmol) N-vinyl-
2-pyrrolid 77.49 (67 mmol) and α,
A solution of C1-azobisisobutylnitrile (5 nitrile based on the total amount of monomers) in anhydrous dioxa 710 at was placed in a glass ampoule, evacuated and filled with nitrogen.
I worked hard. Polymerization was carried out at 50C for 72 hours, and the resulting copolymer was precipitated in ether and washed twice with ether. The results obtained are shown in Table 1. Table 1 ON-Vinyl Ru 2
- All pyrrolidone copolymers were dioxane-water (5:1
'4 quantitative ratio). In the IR spectrum, all copolymers are 2930 and 2860 (!l11-1
The absorption of the vinyl polymer skeleton of 980-1000 and 900-920α-1 had disappeared.

Note = 1) Elemental analysis Calculated from N content.

The charging ratio during the copolymerization reaction was 4.3 molar ratio 2) In dimethylformamide 250 Example 1 Sulfonic acid ester of the functional substance obtained in Production Examples 1 to 13 2
20ml of millimoles of tetrahydrofuran - 10ml of water! ! /
4-t-butylcatechol from IO Misaki was added to the mixed solution and left at 20C. After 24 hours, 48 hours and one week, 10v/each was taken out, washed with water and extracted with ether. At this time, the sulfonic acid ester and the functional substance generated by hydrolysis are extracted into ether. Ether:.i was dried over anhydrous tonahelium sulfate and the ether was evaporated on a rotary evaporator. The hydrolysis rate was determined from the ratio of the remaining vinyl group to the total amount of the sulfonic acid ester of the remaining functional substance and the liberated functional substance from 'H-NMR of the residual functional substance. For the sulfonic acid esters of Production Examples 12 and 13, the same test was also conducted at 75C in a mixed solution of 25 m/5 parts of dioxane and 5 parts of water.

The results are shown in Table 2. Power 11 Water 5+ due to the structure of functional substances
Although the decomposition rate is low, functional substances are gradually released through hydrolysis;
(It can be seen that it is released. Also, for substances that are difficult to hydrolyze at 20 tl', the rate of hydrolysis can be increased by increasing the temperature.

Table 2 Note: 1) Dioxane 259, water, 5 tel mixed solution Example 2 Dioxane 25111, water, 5 tel mixed solution of p-styrene sulfonic acid ester copolymer 17' obtained in Production Example 14 at 20"C and 75 Leave at °C for 24 hours.
After 48 hours and one week, 10#l/each was taken out, diluted with water and extracted with ether. At this time, the copolymer is insoluble in ether, and only the functional substance liberated by hydrolysis is extracted. The ether layer was dried over anhydrous sodium sulfate, and the ether was evaporated on a rotary evaporator. The weight of the residual functional substance produced by hydrolysis was measured to determine the hydrolysis rate.

The results are shown in Table 3. The rate of hydrolysis of copolymers also varies depending on the structure of the functional substance, and the rate of hydrolysis can be increased by increasing the temperature.

Table 3 Example 3 0.57' for the citronellyl p-styrene sulfonate obtained in Production Example 1 and the raw material citronellol, respectively.
was placed in a Petri dish with a diameter of 5α and left at room temperature of about 20°C. Citronellol gradually volatilized and its aroma disappeared after 3 days, but citronellyl p-styrene sulfonate still emitted its aroma even after 30 days. It can be seen that the sulfonic acid ester of the present invention is a long-lasting functional substance releasing agent.

Claims (1)

[Claims] 1. A functional substance releasing agent comprising a sulfonic acid ester of a functional substance having a hydroxyl group. 2. The functional substance releasing agent according to claim 1, wherein the sulfonic acid ester is an aliphatic sulfonic acid ester or an aromatic sulfonic acid ester. 3. The functional substance releasing agent according to claim 2, wherein the aromatic sulfonic acid ester is a styrene sulfonic acid ester. 4. The functional substance releasing agent according to claim 1, wherein the sulfonic acid ester is a polymer. 5. The functional substance releasing agent according to claim 4, wherein the polymer is a homopolymer or copolymer of styrene sulfonic acid ester. 6. The functional substance releasing agent according to claim 1, wherein the functional substance having a hydroxyl group is a fragrance, an agricultural chemical, or a medicine. 7. Claim 6, wherein the fragrance is citronellol, l-menthol, borneol, 2-phenethyl alcohol, 3,7-dimethyloctanol, eugenol, isoeugenol, p-anisyl alcohol, cinnamyl alcohol, or geraniol. Functional substance release agent. 8. The functional substance releasing agent according to claim 6, wherein the agricultural chemical is 2,4-dichlorophenoxyethanol or 2,4,5-trichlorophenoxyethanol.