JPS6197025A - Treatment of substance - Google Patents

Abstract

PURPOSE:To make the difficult-to-dissolve-in-water substance such as the medicines, soluble and to blend them stably by using cyclodextrin polymer having >=20g/100ml-water solubility for water of 25 deg.C to treat the substance. CONSTITUTION:Cyclodextrin polymer having >=20g/100ml-water solubility for water of 25 deg.C is added to the difficult-to-dissolve-in-water substance and blended with each other to stabilize it. As the cyclodextrin polymer, the following compd. shown by a formula I (in the formula (n) is an integer of 3-4) is suitable which is obtained by subjecting cyclodextrin to crosslinking polymerization with epichlorohydrin. This method can be applied to difficult-to-dissolve-in-water substances by which inclusion compds. are formed with cyclodextrin polymer but the utilization for various kinds of medicines, perfumes and dyestuffs is especially effective.

Description

Detailed Description of the Invention [Industrial Application Field] The present invention involves adding and mixing a cyclodextrin polymer to a substance that is poorly soluble in water, converting this substance into a water-soluble one, and improving its physical properties and/or Or it relates to a treatment method that changes chemical properties.

[Conventional technology]

In general, various pharmaceuticals, quasi-drugs, cosmetics, foods, etc. contain vitamins, hormones, fragrances, etc.
Sweeteners and the like are included, and these are usually stirred or kneaded with other ingredients using water as a medium to form the above-mentioned pharmaceuticals.

[Problem that the invention seeks to solve]

However, many of the above-mentioned components are poorly soluble in water (for this reason, even if it is known that a high-quality product can be obtained by blending these components uniformly and at high concentrations, it is difficult to compare the components after blending. There is a problem in that the product is separated from other components within a short period of time, causing unevenness in the composition of the product, and the quality of the product is significantly reduced, making it impossible to fully achieve the intended purpose of use.

By the way, cyclodextrin, which is a cyclic oligosaccharide,
It has been known since ancient times that various substances can be included in the hydrophobic cavity to change various physical properties of these substances, such as water solubility, fat solubility, and ionic dissociation constant. Research is being actively conducted on stabilizing these substances and improving their solubility.

Cyclodextrins currently have three types of homologs (α.

β, T-form) are used, but the β-form is most commonly used because it has a wide range of inclusion targets and is easily available. have been reported many times. However, β is
Due to its low solubility in water, its solubilization effect is limited, and it has been difficult to solubilize the substance to be solubilized at a high concentration and incorporate it into products.

[Means for solving problems]

The present inventors have discovered that the cyclodextrin polymer obtained by crosslinking cyclodextrin with, for example, epichlorohydrin not only has the inherent inclusion ability of cyclodextrin, but also that the polymer with a low degree of polymerization is water-soluble and can be mixed with water at any desired ratio. As a result of various studies based on the empirical fact that the polymer is mixed with the water-insoluble vitamins, hormones, etc. mentioned above, these substances become water-soluble. Not only is it reformed, but at the same time, depending on the substance, substances that are unstable to oxygen in the air, heat, or sunlight can be changed to stable ones, and substances that easily volatilize can be prevented from dissipating. Heading This invention is arrived at.

The present invention is characterized in that a cyclodextrin polymer, for example, a cyclodextrin polymer represented by the following formula, which is a cross-linked polymer of cyclodextrin with epichlorohydrin, is added to and blended into a substance that is sparingly soluble in water to stabilize it. This is a method for treating substances that are

The cyclodextrin polymer has a water solubility, that is, a solubility in water of 20% in the 100° range of water at 25°C.
The degree of polymerization n in the above chemical formula is preferably 3 to 4 (the smaller this value is, the higher the water solubility of the cyclodextrin polymer itself and the solubilization effect of the substance are). .

The present invention can be applied to all substances that are sparingly soluble in water and form clathrate compounds with cyclodextrin polymers, but it is particularly effective for use in various pharmaceuticals, fragrances, pigments, flavoring agents, etc. Specific effects include, for example: ■ Maintenance of uniform dissolution or dispersion of water-insoluble or poorly water-soluble substances in aqueous solvents (prevention of separation from aqueous solvents), ■ Oxygen in the air, Prevention of physical or chemical changes caused by heat and sunlight; ■ Improving the preservation of volatile substances.

Specific examples of target substances for which particularly advantageous results can be obtained when the present invention is applied are listed below.

First, pharmaceuticals include non-steroidal anti-inflammatory drugs, steroidal anti-inflammatory drugs, bactericides, vitamins, chemotherapy drugs,
Hormone drugs are typical examples.

Among these, non-steroidal anti-inflammatory analgesics include aspirin, aspirin aluminum, salicylamide, salicyrosalicylic acid, mefenamic acid, flufenamic acid, diclozenaf sodium, flufenamic acid aluminum, tolfenamic acid, oxyphenbutacin. , clofezone, ketophenylbutacin, phenylbutacin, alclofenac, ibuprofen, naproxen, flurbiprofen, ketoprofen, fenbufen, mevirizole, perixal citrate, azapropacin, indomethacin, graphenine, ergotamine tartrate, bucolome, pentazocine, methiazine acid, protidine Acid, Clidanac, Sulindac, Niflumic Acid, Pranoprofen, Fenoprofen Calcium, Piroxicam Feprazone, Fentiazac, Acemethacin, Pendazac, Dimethylisopropylazulene, Glycyrrhetinic Acid, Bufexamac, Butyl Flufenamate, Ibuprofen Piconol, Methyl Salicylate ,
Glycol salicylate, and other corticosteroids include fluonocinolone acetonide, fluoroside, fluoromesolone, beclomethasone propionate, dexamethacin, dexamethacin acetate, fludroxycortide, betamethacin valerate, betamethacin dipropionate, and triamcinolone acetonide. , prednisolone, methylprednisolone, methylprednisolone acetate, hydrocortisone, hydrocortisone acetate, hydrocortisone butyrate, diflucortolone valerate, clobetasol propionate,
Examples of fungicides include amcinonide, haldinonide, prednisolone acetate valerate, hydrocortisone propionate butyrate, and cloipetacin butyrate. Examples of fungicides include chlorhexidine, chlorhexidine hydrochloride, dequalinium chloride, hexachlorophene, bithionol, and nitromethacin.

Further vitamins include, for example, vitamin A oil, ergocalciferol, dihydrotachysterol, alfacalcidol, prosultiamine, fursultiamine, octothiamine, thiamine disulfide, bisbenthiamine, bisbutiamine, benphothiamine, and cycothiamine. , riboflavin, riboflavin butyrate, pyridoxal phosphate, folic acid, mecobalamin, biotin/tocopherol calcium succinate, tocopherol acetate, 61-α-tocopherol nicotinate, phytonadione, menatetrenone, etc. Chemotherapeutic agents include, for example, sulfiso Xazole, sulfisomidine, sulfamethizole, sulfamethoxazole, sulfamonomethoxine, sulfadimethoxine, sulfazenazole, sulfarene, salazosulfapyridine, nalidixic acid, pyromidic acid, pipemidic acid trihydrate, nitro There are furantoin, cinoxamine, etc., and examples of hormones include testosterone propionate, testosterone enanthate, methyltestosterone, fluoxymesterone, dromostanolone propionate, estradiol benzoate, estradiol dipropionate, estradiol valerate, and cypion. Acid estradiol, ethinyl estradiol, mestranol, estriol, estriol tripropionate, estriol acetate benzoate, hexestrol, progesterone, hydroxyprogesterone caproate, pregnanediol, cydrogesterone, methoxyprogesterone acetate, chlormadinone acetate, dimethisterone, norethisterone, These include allylestrenol, gestorone caproate, oxendrone, and prostaglandin.

Examples of fragrances to which the method of the present invention can be effectively applied include natural animal fragrances, natural plant fragrances, single fragrances extracted and separated from these, or synthesized from other substances, and mixed fragrances.

Among these, natural animal fragrances include mako, reimako, sea cat, and ryunada, while natural plant fragrances include asarum oil, anise oil, avinis oil, balm oil, arnica oil, angelica oil, Ylang-ylang oil, iris oil, fennel oil, orange oil, mustard oil, cananga oil, cypress oil, caraway oil,
Cardamom oil, Gua root oil, Guayawood oil, Kupepa oil,
Cumin oil, Kuromoji oil, Cinnabar oil, Geranium oil, Perfume oil, Gothic oil, Copaiba balsam oil, Coriander oil, Sassosasafras oil, Salvia oil, Perilla oil, Cedarwood oil, Citronella oil (Ceylon), Citronella oil (Java) )
, shibres oil, jasmine oil, camphor oil, raw silkworm oil, calamus oil, cinnamon oil, cedar oil, spike oil, spearmint oil, western oil, omuko oil, thyme oil, tuberose oil, clove oil, ginger -grass oil, turpentine oil, orange blossom oil, wintergreen oil, true balsam oil, cypress oil,
bitter mugwort oil, meat bean oil, patchouli oil, perchun oil,
Seiga oil, rose oil, palmarosa oil, cypress oil, cypress oil, red japonica oil, japonica oil, sandalwood oil, butygrain oil, Pei oil, henopodium oil, vetiva oil, bergamotu oil, Peruvian balsam oil, hemruida oil, Bored rose oil, camphor oil, camphor oil, mandarin oil, megusabatsuka oil, eucalyptus oil, oil tree oil, lime oil, lavender oil, linaloe oil, lemongrass oil, lemon oil, rosemary oil, Japanese mustard oil, etc. For single fragrances, hydrocarbons and their derivatives include Bromostyrol, Cadinene,
Camphene+Cedrene+Diphen
ylmethane, dipentene.

Limonene, Pellandrene, P
inene is alcohol
C,, Alcohol C,.

Alcohol C1o, Alcohol C,...
Alcohol Caz.

Benzyl alcohol, Borneol,
Ced, renol, Cedrol.

C1tronello1. Cum1nic alco
hol.

α-Cyclogeraniol, β-Cyclog
eraniol.

Dimethylbenzylcarbinol, F
arnesol, geraniol.

Hydrocinnamic alcohol+ 1
-Boneol, Lavandulol.

, Linalool, A-Menthol, M
ethylphenylcarbinol.

Nerol+ i-Pl-Pule, Nerolid
ol.

Phenylethylalcohol, Rhod
inol, 5 antalol.

Terpineol is ester, Acetyl-i-eugenol
+A11yl-salicylate, Amyl-ac
etate + Amyl-butyrate, Amylh
eptine carboxylate + Amyl-ni
treat, Amyl-phenylacetate+
Amyl-salicylate+ 8myl-va
lerianate.

Benzyl-acetate+ Benzyl-b
enzoate benzyl-butyratel
Benzyl-cinnamate+Benzyl-
format, Benzyl-propionate
+Benzyl-valerian'ate+ Bo
rnyl-acetate.

Butyl-phenylacetate, Cinna
myl-acetate+Cinnamyl-cinn
aiate+ C1tronellyl-aceta
Te.

Citronellyl-formate, C1tro
nellyl-i-valerianate+ Cy
clohexyl-acetate.

Dietyl-sebacate, Dimeth
yl-antranilate+Ethyl-acet
ate, Ethyl-antranilate, Eth
yl-benzoatet Ethyl-butyr
ate, EthJl-cinnamate.

Ethyl-formate, Ethyl-iv
alerianate+ Ethyl-1aurat
e, Ethyl-myristate, Eth
yl-nonylate.

Ethyl-octin-carbonate, 1
Ethyl-enanthate.

Ethyl-phenylacetate, Eth
yl-salicylate.

Ethyl-valerianate, Gerany
l-acetate, Geranyl-benzoa
te, Geranyl-butyrate, G
eranyl-formate.

Geranyl-i-valerianate+G
eranyl-propionate.

Heptyl-heptoate, Hexyl-f
ormate, i-Amyl-butyrate,
i-Amyl-caproate, 1-Bor
nyl-acetate+1-Butyl-acetate
te, 1-Butyl-benzoatet 1
-Butyl-butyratel 1-Butyl
-phenylacetate, 1-Butyl-
salicylate + Linalyl-acet
ate, Linalyl-butyrate,
Linalyl-i-bytyrate+ Lina
Lyl-propionate, Menthyl-
acetate, Menthyl-i-valer
ianate, Methyl-anthranil
ate, Methyl-benzoate, M
ethyl-butyrate, Methyl-c
inmate.

Methyl-heptine-carbonate,
Methyl-heptoate.

Methyl-hexine-carbonate+
Methyl-nonine-carbonate,
Menthl-octine-carbonate
, Methyl-phenylacetate, M
ethyl-salicylate, neryl-ac
etate, 0ctyl-acetate, 0ctyl
-butyrate.

Phenacyl-butyrate, Phenyle
thyl-acetate.

Phenylethyl-butyrate, Phen
ylethyl-formate.

Phenylethyl-phenylacetate
, Phenylethyl-propionate, P
hen'ylethyl-salicylate, Rh
odinyl-acetate+ Rhodinyl
-butyrate, Rhodinyl-forwat
e+ Terpinyl-acetate, Terp
inyl-butyrate.

Terpinyl-formate, Terpiny
l-propionate is A as an aldehyde.
1dehydr6C,.

Aldehyde C,, Aldehyde C,,.

Aldehyde Ca4 (Peach), Aldehyde
hyde C, 6 (Strawberry) + Alde
hyde Cps, α-Amyl cinnami
c aldehyde.

Anisic aldehyde (Aubepine)
, Benzaldehyde.

Cinnamic aldehyde, C1tral
, C1tronellal.

Cum1nic aldehyde, Ethylva
Nillin (Bourbonal).

He1iotropin, Hydroccinnami
c aldehyde.

Hydrotropic aldehyde, Hyd
roxy-citronellal.

Perillaldehyde, Phenylace
taldehyde.

Phenylacetaldehyde-dimeth
ylacetal.

Phenylacetaldehyde-glycer
inaceta2. Vanilline, but as a ketone, Acetophenone+o-An
+1noacetophenone, Benzoph
Enone.

Benzylideneacetone, Camph
or, Carvone.

C1betone, Cyclohexadecano
ne.

Cyclotetradecanone, Cyclo
tridecanone+Ethylamyl ket
one (Octanone-3), Exalton (
Cyclopentadecanone), Fenc
hone+α-1one.

β-Ionone+ β-Ironone, Jastao
ne, ffi-Menthone.

p-Methoxy-acetophenone, M
ethyl-acetophenone+Methyl
-n-amyl ketone (Heptanone
-2), Methyl-heptenone, M
ethyl-ionone, Methyl-β-na
phthyl ketone (Nerolin), Me
thyl nonyl ketone.

Methylquinonyl ketone, Mu
scone+ Musk ketone+Piperi
tone+ Pulegone, Thujone(T
anacetone), but as an ether, Anet
hole+C1neole (Eucalyptol),
p-Cresyloxide.

Diphenyloxide, Gerany'1me
thyleLher.

l5osafrole, Methyl-chavi
col(Estragol)+Methyl-euge
no1. Methyl-i-eugenol.

Musk ambrette, β-Naphth
ol butylether.

β-Naphthol ethylenether (Ner
olin)+β-Naphthol a+ethyle
ther, Phenyl-p-cresyloxi
de, Phenyl glycol methylen
ether.

Phenyl glycolethyleneeth
er, 5afrol+p-Tolymethyleth
er, but as a phenol, Amyloxyis
o-eugenol+Carvacrol+Euge
nol, iso-Eugenol, Thymol
7><% As the lactone, Exaltolide,
Coumarin, as an acid, Benzoic a
cid+ C1nnasic acid.

Phenylacetic acid and other nitrogen compounds include Indole.

Musk
O (Red No. 5), Naphthol Yellow S (Yellow No. 1),
Yellow OB (Yellow No. 3), Tartrazine (Yellow No. 4), Rhodamine B Stearate (Red No. 215), Tetrachlorofluorescene (Red No. 216), Tetrachlorotetrabromofluorescene (Red No. 218), Tetra Bromofluorescene (red No. 223), dibromofluorescene (orange No. 201), fluorescene (yellow No. 201)
), Quinoline Yellow SS (Yellow No. 204), Quinizarine Green SS (Green No. 202), Scarlet Red (Red No. 501), Sudan Blue B (Blue No. 403)
and so on.

Further, as a flavoring agent, it is effective to use it as a sweetener, and in particular, it is effective to use it as a dihydrochalcone. Specific examples of dihydrochalcones include prunin dihydrochalcone, neohesveridine dihydrochalcone, naringin dihydrochalcone, hesperetin dihydrochalcone glucoside, hesperetin:;hydrochalcone xyloside, hesperetin dihydrochalcone galactoside, and naringenin dihydrochalcone rhamnosil. Galactoside, etc.

〔Example〕

Kaekomai 1 (Dentifrice containing a stable blend of hesveridine dihydrochalcone monoglycoside) Toothpaste A was produced according to a conventional method.

β-cyclodextrin polymer (trimer to tetramer) 0.9
5 parts by weight were dissolved in 4.0 parts by weight of water, and 0.05 parts by weight of hesveridine dihydrochalcone monoglycoside was added and stirred to prepare a composite solution B.

B was added to A and kneaded to obtain a dentifrice in which hesveridin dihydrochalcone monoglycoside was stably blended.

Mouth rinse for preventing bad breath β-cyclodextrin polymer (trimer to tetramer) 13.
5 parts by weight were dissolved in 15.0 parts by weight of purified water, 1.5 parts by weight of peppermint fragrance was added and stirred to obtain peppermint fragrance/cyclodextrin polymer composite solution A.

β-cyclodextrin polymer (trimer to tetramer) 1.6
Part by weight was dissolved in 5.0 parts by weight of purified water, and 0.4 parts by weight of chlorhexidine hydrochloride was added and stirred to obtain chlorhexidine hydrochloride/cyclodextrin polymer composite solution B.

A and B were mixed and dissolved in C to obtain a mouthwash for preventing bad breath.

This product can be expected to have a high halitosis prevention effect due to the solubilized blend of fragrance 0 and chlorhexidine hydrochloride, and the cyclodextrin inclusion effect of halitosis components.

- Dissolve 2.952 parts by weight of 2.952 parts by weight of 2.952 parts by weight of 2.952 parts by weight of 2.952 parts by weight of Prostaglandin E and 0.0 parts by weight of purified water. 048 parts by weight were added and stirred to prepare prostaglandin E+/cyclodextrin polymer composite solution A.

It is produced by mixing and dissolving B, adding A thereto, kneading the mixture, and freeze-drying the mixture.

This product has a thickness of 0.5 to 2 am and is used as an orthodontic orthodontic promoter by pasting it on the gingiva. In addition, one side may be coated with a support such as a nonwoven fabric or an insoluble film for the purpose of prolonging the application time in the oral cavity.

Ryori■↓ (Topical preparation containing steroidal anti-inflammatory agent) Dissolve 19 parts by weight of β-cyclodextrin polymer (tri-tetramer) in 20 parts by weight of purified water, add 1 part by weight of hydrocortisone.
Add parts by weight and stir to prepare hydrocortisone/cyclodextrin polymer complex solution A.

It is manufactured by adding A to gel ointment B prepared by a conventional method and adding it to the base.

Daiyo-Il (Non-steroidal anti-inflammatory Jingaiku topical preparation) 27 parts by weight of β-cyclodextrin polymer (trimer to tetramer) was dissolved in 20 parts by weight of purified water, 3 parts by weight of indomethacin was added and stirred, and indomethacin・Prepare a cyclodextrin polymer complex solution.

It is manufactured by adding A to gel ointment B prepared by a conventional method and adding it to the base.

Tocopherol acetate/cyclodextrin 0.18 parts by weight of β-cyclodextrin polymer (tri-tetramer) is dissolved in 2.0 parts by weight of purified water, and 0.18 parts by weight of tocopherol acetate/cyclodextrin β-cyclodextrin polymer (trimer to tetramer) is dissolved in 2.0 parts by weight of purified water.
02 parts by weight were added and stirred to prepare tocopherol acetate/cyclodextrin polymer complex solution A.

After adding and dissolving A into eye drops B prepared by a conventional method, the eye drops are sterilized and filtered through a strained pore filter.

Sf (Hair cleansing agent stably containing a disinfectant and a dandruff remover) Add 10 parts by weight of water to 17 parts by weight of β-cyclodextrin polymer (trimer to tetramer), then add 3 parts by weight of dinkomazine and stir. In this way, a dinkomazine/cyclodextrin polymer composite slurry A is prepared.

Slurry B of hexachlorophene/cyclodextrin polymer composite is prepared by adding 5 parts by weight of water to 9 parts by weight of β-cyclodextrin polymer (trimer to tetramer), and further adding 1 part by weight of hexachlorophene and stirring. .

A and B are added to C mixed and dissolved in a conventional manner, and the mixture is homogenized to produce a hair cleansing agent.

Yuko Oshi (bath additive with stable combination of pigments and fragrances) β-cyclodextrin polymer (3 to 41 units) 4.5
Dissolve 5 parts by weight in 5.0 parts by weight of water to remove 0 fluorescein.
．． Add 45 parts by weight and stir to prepare fluorescein/cyclodextrin polymer composite solution A-.

β-cyclodextrin polymer (trimer to tetramer) 4.6
Dissolve part by weight in 5.0 parts by weight of water and add 0 jasmine fragrance.
．． Add 4 parts by weight and stir to prepare perfume/cyclodextrin polymer complex solution B.

3 parts by weight of carboxymethylcellulose sodium to 4 parts by weight of water
A solution containing A and B added to 0 parts by weight was added to a mixture of 45 parts of sodium sulfate and 45 parts of sodium polyphosphate, and after charging, it was made into granules using an extrusion granulator, and a granular bath agent was obtained. Manufacture.

Further, after freeze-drying A and B to form a composite powder, the mixture is mixed with sodium sulfate and sodium polyphosphate, and a granular bath agent is produced by dry granulation according to a conventional method.

Inujoshu (liquid detergent with a stable blend of fragrances) β-cyclodextrin polymer (trimer to tetramer) 4.5
Dissolve 10.0 parts by weight of water and add 0.0 parts by weight of lemon fragrance.
Add 5 parts by weight and stir to prepare perfume/cyclodextrin polymer composite solution A.

A is added to a mixed solution of each of B to produce a liquid detergent in which a fragrance is stably blended.

Daiarashi Kaido L (Antiperspirant that stably contains bactericides and fragrances and releases them continuously) 10 parts by weight of water with β-cyclodextrin polymer (4 to 4 parts by weight)
Hexamer) and a floral fragrance are added and stirred to obtain a floral fragrance/cyclodextrin polymer complex solution A. This is freeze-dried to produce a floral fragrance/cyclodextrin polymer composite powder.

β-cyclodextrin polymer (4 to 6 parts by weight) in 5 parts by weight of water
Hexachlorophene/cyclodextrin polymer complex solution B is obtained by adding o and i parts of hexachlorophene and hexachlorophene and stirring. This is freeze-dried to produce a hexachlorophene/cyclodextrin polymer composite powder.

Mix the powders of A and B with C and prepare a spray set of antiperspirant according to a conventional method.

110" - (Hygiene material with sustained sterilization and deodorizing effects) Add 0.1 parts by weight of hexachlorophene and 0.9 parts by weight of β-cyclodextrin polymer (4-6 mer) to 5 parts by weight of water and stir. Then, hexachlorophene/cyclodextrin polymer complex solution A is obtained. This is freeze-dried to produce a composite powder.

0.5 parts by weight of a floral fragrance and 4.5 parts by weight of β-cyclodextrin polymer (4 to 6 polymers) are added to 10 parts by weight of water and stirred to obtain a floral fragrance/cyclodextrin polymer composite solution B.

This is freeze-dried to produce a composite powder.

The composition of C was heated to 60°C, and 1.0 parts by weight of the powder of A and 5.0 parts of the powder of B were kneaded to 94 parts by weight of the polymerized product, and a fragrance and a bactericide were added. Manufactures polymer absorbents for sanitary materials.

By incorporating Honjima into sanitary products, etc., the deodorizing effect and bactericidal effect will be sustained, and a high deodorizing effect can be expected by including odorous substances with the inclusion action of cyclodextrin.

Heaven a;? Ixz (Nutrition drink containing oil-soluble vitamins) 2.0 parts of β-cyclodextrin polymer (4 parts hexamer) and 5.0 parts purified water.
A complex solution is prepared by adding dissolved prescribed amounts of vitamin A oil, folic acid, tocopherol acetate, and ergocasiferol to 0 parts and stirring.

A is added to B, in which each component is mixed and dissolved, and dissolved to produce a drink.

〔Effect of the invention〕

The method of the present invention is characterized by solubilizing and stably blending poorly water-soluble substances with a cyclodextrin polymer cross-linked with epichlorohydrin, which is different from conventional solubilization with β-cyclodextrin. Due to the low solubility of β-cyclodextrin in water, only a very small amount of the substance could be solubilized, but in the present invention, by using a water-soluble cyclodextrin polymer, a large amount of the substance can be solubilized and incorporated into the product. It became possible to do so.

The present invention can be applied to pharmaceuticals, quasi-drugs, cosmetics, foods, household goods, dyes, photographic materials, agricultural chemicals, etc. Therefore, it is possible to stabilize these substances in the above sense. Therefore, the present invention has the remarkable effect that it is possible to produce pharmaceutical products of higher grade and quality in various aspects than conventional products through a simple process.

Procedural amendment form) % form % 1, Indication of case 1981 Patent application No. 21733
No. 2 No. 2, Title of the invention Substance processing method 3, Relationship with the case of the person making the amendment Name of patent applicant (676) Lion Co., Ltd. 4
, Agent 5, Date of amendment order: January 29, 1985 (shipment date) 6, Subject of amendment: Detailed description of the invention in the specification Patent application 1982-2173.32 Amendment in the specification of the present application 1. Correct the following from line 12 on page 11 to line 17 on page 16.

[Bro+mostyrol
)+ Cadinene + Ca+mphene + Cedrene
), diphenylmethane
ne) + Dipentene (Dipe++tene) +
Limonene, Ferlandrene (P
hellandrene) +pinene (Pinene)
However, as an alcohol, benzyl alcohol (Ben
Zyl alcohol + Borneol
eol) + Cedrenol + Cedrol.

Citronellol, Cuminic alcohol,
α-Cyclogeraniol (α-Cyclogeraniol)
iol) + β-cyclogeraniol (β-Cyc
logeraniol) + dimethylbenzylcarbinol (Di+methylbenzylcarbin)
ol) + Farnesol +
Geraniol.

Hydrocinnamic alcohol (Hydrocinn)
amicalcohol), i-borneol (i
-Boneol) + Lavenderol (Lavandu)
lol) + linalool,
It-Menthol (1-Menthol).

Methylphenylcarpinol
lcarbinol, ) Nerol +
i-Pulegol.

Nerolidol + Phenylethyl alcohol
ol) + Phodinol +
Santalo + Terpineol - As an ester, Acetyl-1-eugenol (Acetyl-i-eugenol)
nol) + allyl salicylate (AIlyl-sa
licylate) + Amyl-ac
etate) + Amyl-butyrate
yrate) + amilhep.

Tinecarboxylate (AmylhepLinecar)
boxylate) + Amyl-nit
rate) + amyl phenylacetate (Amyl
-phenylacetate) + Amyl-salicylate, Amyl-valerianate + Benzyl-acetate + 8enzyl-benzoate, 68
Benzyl-butyrate+
Benzyl-cinnamate
te) + Benzyl formate (Benzyl-format
e) + Benzyl-propionate (Benzyl-pro
pionate) +Benzyl valerate (Benzyl-
valerianate), pronyl acetate (B
ornyl-acetate) + butyl-phenylacetate
+Cinnasyl-acetate
tate) + cinnamyl cinnamate (Cin
naBl-cinnamaLe), citronellyl-acetate
) + citronellylforme) (Citronell
yl-formata), Citronellil-i-valerinate (Citronellil-i-valeri)
anaLe) + Cyclohethyl acetate (Cyclo
hexyl-acetate) + diacetyl (Diac
etyl) + diethyl sebacate (Diethyl-
sebacate), dimethyl anthranilate (D
isethyl-antranilate) + Ethyl-acetate + Ethyl-antranilate
+ Ethyl benzoate (E thy I-benz
oate) + Ethyl-butyra
te), ethylcinnamate (Ethyl-cinnamate)
amate) + Ethyl-forIla
te), i-ethyl valerate (Ethyl-i-val
ertanate) + ethyl laurate (Ethy
l-1auraLe).

Ethyl-myristate
) (Ethyl-nonyl)
ate), ethyl octyne carbonate (Ethyl-
octin-carbonate) + ethyl enate)
(Ethyl-enanthate) + ethyl phenyl lactate) (II! thy l -pheny
1acetate), ethyl salicylate (Eth
yl-salicylate) + ethyl valerate (Et
byl-valerianate), Geranyl-acetate *Geranyl-benzoate
+Geranyl-butyrate
te).

Geranyl-format
e) +Geranyl i-valerinate (Geranyl
-i-valerianate).

Geranyl-propionate
onate) +Heptyl heptate
-heptoate), hexyl formate (He
xyl-formate) + i-amylbutyrate (
i-A+myl-butyrate)+i-amylcaproate (i-A+wyl-caproate),
i-pronyl acetate (i-Bornyl-acetate)
tate) + i-Butyl acetate (i-Butyl
-acetate) + i-butylbenzoate (i
-Butyl-benzoataLi (i-Butyl-buLyrate), i-
Butyl-phenylacetate (i-Butyl-phenyl)
ylacetate), i-butyl salicylate (
t-Butyl-salicylate), Linalyl-acetate +
Linalyl acetate (Linalyl-butyr)
ate), linalyl i-butyrate (linalyl i-butyrate),
-i-bytyrateL linalyl propionate (L
inalyl-propionateL Menthyl-acetate + Methyl-1-valerine
ianaLe) + methyl anthranilate (Methy
l-anthranilate).

Methyl-benzoate
) l Methyl-butyrate (Methyl-butyra
te), methyl cinnamate (Methyl-cin
namate) + Methyl cinnamate fuite (Me
thyl-heptine-carbonate) +
Methyl-heptate
, Methyl-he
xine-carbonate) + Methyl-nonine-carbonate
ate) + methyl octyne carbonate (Menth
l-octine-carbonate) + methylphenylacetate) (Methyl-phenylac
etate) +Methyl-salicylate
alicylate) + nerilua, cetate (Ne
ryl-acetate) 1 octyl acetate (O
ctyl-acetate), octyl butyrate (
Octyl-butyrate), Phenacyl-butyrate
+Phenylethylbutyrate (PhenyleLhyl
-acetateL Phenylethyl butyrate (Ph
enylthyl-butyrate) + phenylethyl-formate
mate) + phenylethylfer acetate (P
(henylethyl-phenylacetate)
, Fs, Nylethylpropionate (Phenshi1e
thyl-propionate) + Phenylethyl-salicylate
late), ropeinyl acetate CRhodiny
l-acetate) + ropeinylbutyrate (
Rhodinyl-bu tyra to), Rhodoinyl formate (Rhodinyl-bu tyra to), Rhodinyl-butyra to
+ats), Terpinylacetate (Terpiny
l-acetate) + tervinylbutyrate (Te
rpinyl-butyrate), Terpinyl-formate + Terpinyl-propionate
ionate), but the aldehyde is α-amyl cinnamic aldehyde (α-AIlyl cinna+eic aldehyde).
yde).

Anisic aldehyde
e) (＾ubepine) + benzaldehyde (B
enzaldehyde + cinnamic aldehyde + citral (C4tral) + citronellal (C4trone)
llal) + Cumic aldehyde (Cuminic
aldehydeL Ethylvanillin (Ethylva)
Nillin (Bourbonal), Heliotropin + Hydrotropic aldehyde (Bourbonal)
hydrotropic aldehyde (hyde), hydrotropic aldehyde (Hy
drotropic aldehyde) + hydroxycitronellal (llydroxy-citron)
perylaldehyde + perylaldehyde
dehyde) + phenylacetaldehyde (P
henylacetaldehyde) + phenylacetaldehyde-dimethyl acetal (Pbenylacetaldehyde-dimet)
hylacatal), phenylacetaldehyde glycerinacetal (phenylacetaldehyde)
yde-glyc@rinacetal), vanillin (Vanilline), and as a ketone, acetophenone (Acetopher
+one) +0-aminoacetophenone (o-Ami
noacetophenone).

Benzophenone + Benzylideneacet
one) + Camphor + Carbone + Tibeton (C4veton)
e) + Cyclohexadecanone (Cyclohexad
ecanone) + cyclotetradecanone (Cyclone)
, otetradecanone), Cyclotridecanone +
Ethyl amyl ketone
ne) (Octanone-3), Cyclopentadecanone +
Fenchone + α-ionone (a-1onone) l β-ionone (β
-1onone) + β-irone (β-1rone)
+Jasone, j! -Menhone (j!-MenLhone).

p-Methoxy-acetophenone (p-NethoxV-
acetophenone), MeLhyl-acetophenone + Methyl-n-amyl ketone
ketone) (Ileptanone-2), Methyl-heptanone (Methyl-heptanone), Methyl ionone (Methyl-4onone), Methyl-β-naphthyl ketone (Methyl-β-naph)
thyl ketone (Nerolin), Methyl nonyl ketone (Nerolin)
e), Methylquinolylketone (Methylquinolylketone)
nyl ketone), Muscone
+ Musk ketone, Piperitone + Brebon (Pul)
egone) + Thujone (T
anace tone), but the ether is anethole.
+Cineole (Eucalypt)
ol) + p-chrysaloxide (p-Cresν1
oxide), diphenyl oxide)
loxide) + geranyl methyl ether (Gera
nylsethylether) + Isosafrole, Methylchapicol (N
ethyl-chavicol) (Estragol)
) + methyl eugenol (Meth, yl-euge
nol), Methyl-1-eugenol (Methyl-
4-eugenol) + Musk Amp Left (Mus
k aa + brette) + β-naphthol butyl ether (β-Napt + thol butyleth
er), β-naphthol ethyl ether (β-Naph
thol ethylenether) (Nerolin)
.

β-Naphthol methyl ether (β-Naphthol
setbylether), Phenyl-p-cresyloxide
+ Phenyl glycol methylene ether (Phen
yl glycol methyleneether).

Phenyl glycol ethylene ether (Phenylg
lycolethyleneether) + Safrol.

p-Trimethyl ether (p-TolymeLhyle)
Lhar), but as a phenol, amyloxyisoeugenol (Amyloxyiso-eugenol)
+ Carvacrol + Eugenol + Isoeugenol
so-Eugenol) + Thymol
However, as a lactone, exalitride (Exalto
ride).

Coumarin (Cousarin), as an acid, benzoic acid (Benzoic acid),
Cinna+*ic acid + Phenylacetic aci
d), and other nitrogen compounds include Indole *Musk
2, page 21, line 10, replace rP, E, G, J with "
"Polyethylene glycol" is corrected.

3, rGaen13J on page 26, line 18 is changed to “Blue 3
Correct it to "No.".

that's all

Claims (2)

[Claims] (1) A method for treating a substance characterized by using a cyclodextrin polymer. (2) As the cyclodextrin polymer, 25°C
The treatment method according to claim 1, wherein the solubility in water is 20 g/100 ml (water) or more.