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Methylmenthol Derivative And Cool Sensation Imparter Composition Containing Same

Abstract: The present invention addresses the problem of providing a novel methylmenthol derivative usable as a cool-sensation imparter or sense-stimulating agent which has none of an undesirable irritating feeling a peculiar odor bitterness and the like and is excellent in terms of the retention of a refreshing sensation or cool sensation. The cool-sensation imparter composition of the present invention contains a methylmenthol derivative represented by general formula (1). [In formula (1) symbol * indicates an asymmetric carbon atom X represents a hydrogen atom or a substituent and Y is an optionally substituted C6-20 aryl group.]

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Patent Information

Application #
Filing Date
08 July 2019
Publication Number
29/2019
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
patent@depenning.com
Parent Application
Patent Number
Legal Status
Grant Date
2022-02-22
Renewal Date

Applicants

TAKASAGO INTERNATIONAL CORPORATION
37-1, Kamata 5-chome, Ota-ku, Tokyo 144-8721

Inventors

1. ITOH, Hisanori
c/o TAKASAGO INTERNATIONAL CORPORATION, 4-11, Nishiyawata 1-chome, Hiratsuka-shi, Kanagawa 254-0073
2. MATSUMOTO, Takaji
c/o TAKASAGO INTERNATIONAL CORPORATION, 4-11, Nishiyawata 1-chome, Hiratsuka-shi, Kanagawa 254-0073
3. SATO, Tomoharu
c/o TAKASAGO INTERNATIONAL CORPORATION, 37-1, Kamata 5-chome, Ota-ku, Tokyo 144-8721
4. HARADA Makoto
c/o TAKASAGO INTERNATIONAL CORPORATION, 4-11, Nishiyawata 1-chome, Hiratsuka-shi, Kanagawa 254-0073
5. OTAKE, Masaya
c/o TAKASAGO INTERNATIONAL CORPORATION, 4-11, Nishiyawata 1-chome, Hiratsuka-shi, Kanagawa 254-0073
6. OTSUKA, Masashi
c/o TAKASAGO INTERNATIONAL CORPORATION, 4-11, Nishiyawata 1-chome, Hiratsuka-shi, Kanagawa 254-0073

Claims

1. A cooling agent composition comprising a methyl menthol derivative represented by the following general formula (1): [Chem. 1] wherein a symbol * indicates an asymmetric carbon atom, X represents a hydrogen atom or a substituent, and Y represents an aryl group having 6 to 20 carbon atoms which may have a substituent.

2. The cooling agent composition according to claim 1, wherein X in the general formula (1) represents a hydrogen atom, a hydroxyl group, an acetoxy group, an oxo group, or a methyl group, and Y in the general formula (1) represents a phenyl group which may have a substituent.

3. The cooling agent composition according to claim 1 or 2, wherein the general formula (1) is represented by the following structural formula (2): [Chem. 2] wherein a symbol * indicates an asymmetric carbon atom.

4. The cooling agent composition according to any one of claims 1 to 3, further comprising at least one kind of cooling substance other than the methyl menthol derivative.

5. The cooling agent composition according to claim 4, wherein the cooling substance other than the methyl menthol derivative is at least one cooling substance selected from the group consisting of: one or more kinds of compounds selected from menthol, menthone, camphor, pulegol, isopulegol, cineole, cubenol, menthyl acetate, pulegyl acetate, isopulegyl acetate, menthyl salicylate, pulegyl salicylate, isopulegyl salicylate, 3-(l-menthoxy)propane-l,2-diol, 2-methyl-3-(l-menthoxy)propane-l,2-diol, 2-(l-menthoxy)ethane-l-ol, 3-(l-menthoxy)propane-l-ol, 4-(l-menthoxy)butan-l-ol, menthyl 3-hydroxybutanoate, menthyl glyoxylate, p-menthane-3,8-diol, l-(2-hydroxy-4-methylcyclohexyl)ethanone, menthyl lactate, menthone glycerin ketal, menthyl-2-pyrrolidone-5-carboxylate, monomenthyl succinate, alkali metal salts of monomenthyl succinate, alkaline earth metal salts of monomenthyl succinate, monomenthyl glutarate, alkali metal salts of monomenthyl glutarate, alkaline earth metal salts of monomenthyl glutarate, N-{[5-methyl-2-(l-methylethyl)cyclohexyl]carbonyl}glycine, p-menthane-3-carboxylic acid glycerol ester, menthol propylene glycol carbonate, menthol ethylene glycol carbonate, p-menthane-2,3-diol, 2-isopropyl-N,2,3-trimethylbutanamide, N-ethyl-p-menthane-3-carboxamide, 3-(p-menthane-3-carboxamide) ethyl acetate, N-(4-methoxyphenyl)-p-menthane carboxamide, N-ethyl-2,2-diisopropylbutanamide, N-cyclopropyl-p-menthane carboxamide, N-(4-cyanomethylphenyl)-p-menthanecarboxamide, N-(2-pyridin-2-yl)-3-p-menthane carboxamide, N-(2-hydroxyethyl)-2-isopropyl-2,3-dimethylbutanamide, N-( 1,1-dimethyl -2-hydroxyethyl)-2,2-diethylbutanamide, cyclopropanecarboxylic acid (2-isopropyl-5-methylcyclohexyl)amide, N-ethyl-2,2-diisopropylbutanamide, N-[4-(2-amino-2-oxoethyl)phenyl]-p-menthanecarboxamide, 2-[(2-p-menthoxy)ethoxy]ethanol, 2,6-diethyl-5-isopropyl-2-methyltetrahydropyran, trans-4-tert-butylcyclohexanol, N-[4-(cyanomethyl)phenyl]-2-isopropyl-5,5-dimethylcyclohexylcarboxamide, andN-[3-hydroxy-4-methoxyphenyl]-2-isopropyl-5,5-dimethylcyclohexyl carboxamide; one or more kinds of sugar alcohols selected from xylitol, erythritol, dextrose, and sorbitol; and one or more kinds of natural products selected from Japanese mint oil, peppermint oil, spearmint oil, and eucalyptus oil.

6. A sensory stimulant composition comprising the cooling agent composition according to any one of claims 1 to 5.

7. The sensory stimulant composition according to claim 6, further comprising at least one kind of warming substance.

8. The sensory stimulant composition according to claim 7, wherein the warming substance is at least one warming substance selected from the group consisting of: one or more kinds of compounds selected from vanillyl methyl ether, vanillyl ethyl ether, vanillyl propyl ether, vanillyl isopropyl ether, vanillyl butyl ether, vanillyl amyl ether, vanillyl isoamyl ether, vanillyl hexyl ether, isovanillyl methyl ether, isovanillyl ethyl ether, isovanillyl propyl ether, isovanillyl isopropyl ether, isovanillyl butyl ether, isovanillyl amyl ether, isovanillyl isoamyl ether, isovanillyl hexyl ether, ethyl vanillyl methyl ether, ethyl vanillyl ethyl ether, ethyl vanillyl propyl ether, ethyl vanillyl isopropyl ether, ethyl vanillyl butyl ether, ethyl vanillyl amyl ether, ethyl vanillyl isoamyl ether, ethyl vanillyl hexyl ether, vanillin propylene glycol acetal, isovanillin propylene glycol acetal, ethyl vanillin propylene glycol acetal, vanillyl butyl ether acetate, isovanillyl butyl ether acetate, ethyl vanillyl butyl ether acetate, 4-(l-menthoxymethyl)-2-(3'-methoxy-4'-hydroxyphenyl)-l,3-dioxolane, 4-(l-menthoxymethyl)-2-(3'-hydroxy-4'-methoxyphenyl)-1,3-dioxolane, 4-(l-menthoxymethyl)-2-(3'-ethoxy-4'-hydroxyphenyl)-1,3-dioxolane, capsaicin, dihydrocapsaicin, nordihydrocapsaicin, homodihydrocapsaicin, homocapsaicin, bis-capsaicin, trishomocapsaicin, nornorcapsaicin, norcapsaicin, capsaicinol, vanillyl caprylamide (octylic acid vanillylamide), vanillyl pelargonamide (nonylic acid vanillylamide), vanillyl caproamide (decylic acid vanillylamide), vanillyl undecanamide (undecylic acid vanillylamide), N-trans-feruloyltyramine, N-5-(4-hydroxy-3-methoxyphenyl)-2E,4E-pentadienoylpiperidine, N-trans-feruloylpiperidine, N-5-(4-hydroxy-3-methoxyphenyl)-2E-pentenoylpiperidine, N-5-(4-hydroxyphenyl)-2E,4E-pentadienoylpiperidine, pipeline, isopiperine, chavicine, isochavicine, piperamine, piperettine, piperolein B, retrofractamide A, pipercide, guineenside, piperiline, piperamide C5:l (2E), piperamide C7:l (6E), piperamide C7:2 (2E,6E), piperamide C9:l (8E), piperamide C9:2 (2E,8E), piperamide C9:3 (2E,4E,8E), fagaramide, sanshool-I, sanshool-II, hydroxysanshool, sanshoamide, gingerol, shogaol, zingerone, methylgingerol, paradol, spilanthol, chavicine, polygodial (tadeonal), isopolygodial, dihydropolygodial, and tadeon; and one or more kinds of natural products selected from capsicum oil, capsicum oleoresin, ginger oleoresin, jambu oleoresin (Spilanthes oleracea extract), sansho extract, sanshoamide, black pepper extract, white pepper extract, and polygonum extract.

9. A flavor or fragrance composition comprising the sensory stimulant composition according to any one of claims 6 to 8.

10. The flavor or fragrance composition according to claim 9, wherein a content of the sensory stimulant composition is from 0.00001 mass% to 90 mass%.

11. A product comprising the sensory stimulant composition according to any one of claims 6 to 8, the product being any one of products selected from the group consisting of drinks, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, oral compositions, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, tobacco, quasi-drugs and pharmaceuticals.

12. The product according to claim 11, wherein a content of the sensory stimulant composition is from 0.00001 mass% to 50 mass%.

13. A product comprising the flavor or fragrance composition according to claim 9 or 10, the product being any one of products selected from the group consisting of drinks, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, oral compositions, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, tobacco, quasi-drugs and pharmaceuticals.

14. The product according to claim 13, wherein a content of the flavor or fragrance composition is from 0.00001 mass% to 50 mass%.

15. A method of manufacturing a product, comprising blending a product with the sensory stimulant composition according to any one of claims 6 to 8, wherein the product is any one of products selected from the group consisting of drinks, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, oral compositions, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, tobacco, quasi-drugs and pharmaceuticals.

16. A method of manufacturing a product, comprising blending a product with the flavor or fragrance composition according to claim 9 or 10, wherein the product is any one of products selected from the group consisting of drinks, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, oral compositions, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, tobacco, quasi-drugs and pharmaceuticals.

17. A methyl menthol derivative represented by the following general formula (1): [Chem. 3] wherein a symbol * indicates an asymmetric carbon atom, X represents a hydrogen atom or a substituent, and Y represents an aryl group having 6 to 20 carbon atoms which may have a substituent.

18. The methyl menthol derivative according to claim 17, wherein X in the general formula (1) represents a hydrogen atom, a hydroxyl group, an acetoxy group, an oxo group, or a methyl group, and Y in the general formula (1) represents a phenyl group which may have a substituent.

19. The methyl menthol derivative according to claim 17 or 18, wherein the general formula (1) is represented by the following structural formula (2): wherein a symbol * indicates an asymmetric carbon atom.

Specification

WE CLAIM:
1. A cooling agent composition comprising a methyl menthol derivative
represented by the following general formula (1): [Chem. 1]
wherein a symbol * indicates an asymmetric carbon atom, X represents a hydrogen atom or a substituent, and Y represents an aryl group having 6 to 20 carbon atoms which may have a substituent.
2. The cooling agent composition according to claim 1, wherein X in the general formula (1) represents a hydrogen atom, a hydroxyl group, an acetoxy group, an oxo group, or a methyl group, and Y in the general formula (1) represents a phenyl group which may have a substituent.
3. The cooling agent composition according to claim 1 or 2, wherein the general formula (1) is represented by the following structural formula (2):
[Chem. 2]
wherein a symbol * indicates an asymmetric carbon atom.
4. The cooling agent composition according to any one of claims 1 to 3, further
comprising at least one kind of cooling substance other than the methyl menthol derivative.

5. The cooling agent composition according to claim 4, wherein the cooling
substance other than the methyl menthol derivative is at least one cooling substance selected from the group consisting of:
one or more kinds of compounds selected from menthol, menthone, camphor, pulegol, isopulegol, cineole, cubenol, menthyl acetate, pulegyl acetate, isopulegyl acetate, menthyl salicylate, pulegyl salicylate, isopulegyl salicylate, 3-(l-menthoxy)propane-l,2-diol, 2-methyl-3-(l-menthoxy)propane-l,2-diol, 2-(l-menthoxy)ethane-l-ol, 3-(l-menthoxy)propane-l-ol, 4-(l-menthoxy)butan-l-ol, menthyl 3-hydroxybutanoate, menthyl glyoxylate, p-menthane-3,8-diol, l-(2-hydroxy-4-methylcyclohexyl)ethanone, menthyl lactate, menthone glycerin ketal, menthyl-2-pyrrolidone-5-carboxylate, monomenthyl succinate, alkali metal salts of monomenthyl succinate, alkaline earth metal salts of monomenthyl succinate, monomenthyl glutarate, alkali metal salts of monomenthyl glutarate, alkaline earth metal salts of monomenthyl glutarate, N-{[5-methyl-2-(l-methylethyl)cyclohexyl]carbonyl}glycine, p-menthane-3-carboxylic acid glycerol ester, menthol propylene glycol carbonate, menthol ethylene glycol carbonate, p-menthane-2,3-diol, 2-isopropyl-N,2,3-trimethylbutanamide, N-ethyl-p-menthane-3-carboxamide, 3-(p-menthane-3-carboxamide) ethyl acetate, N-(4-methoxyphenyl)-p-menthane carboxamide, N-ethyl-2,2-diisopropylbutanamide, N-cyclopropyl-p-menthane carboxamide, N-(4-cyanomethylphenyl)-p-menthanecarboxamide, N-(2-pyridin-2-yl)-3-p-menthane carboxamide, N-(2-hydroxyethyl)-2-isopropyl-2,3-dimethylbutanamide, N-( 1,1-dimethyl -2-hydroxyethyl)-2,2-diethylbutanamide, cyclopropanecarboxylic acid (2-isopropyl-5-methylcyclohexyl)amide, N-ethyl-2,2-diisopropylbutanamide, N-[4-(2-amino-2-oxoethyl)phenyl]-p-menthanecarboxamide, 2-[(2-p-menthoxy)ethoxy]ethanol, 2,6-diethyl-5-isopropyl-2-methyltetrahydropyran, trans-4-tert-butylcyclohexanol, N-[4-(cyanomethyl)phenyl]-2-isopropyl-5,5-dimethylcyclohexylcarboxamide, andN-[3-hydroxy-4-methoxyphenyl]-2-isopropyl-5,5-dimethylcyclohexyl carboxamide;
one or more kinds of sugar alcohols selected from xylitol, erythritol, dextrose, and sorbitol; and
one or more kinds of natural products selected from Japanese mint oil, peppermint oil, spearmint oil, and eucalyptus oil.

6. A sensory stimulant composition comprising the cooling agent composition according to any one of claims 1 to 5.
7. The sensory stimulant composition according to claim 6, further comprising at least one kind of warming substance.
8. The sensory stimulant composition according to claim 7, wherein the warming substance is at least one warming substance selected from the group consisting of:
one or more kinds of compounds selected from vanillyl methyl ether, vanillyl ethyl ether, vanillyl propyl ether, vanillyl isopropyl ether, vanillyl butyl ether, vanillyl amyl ether, vanillyl isoamyl ether, vanillyl hexyl ether, isovanillyl methyl ether, isovanillyl ethyl ether, isovanillyl propyl ether, isovanillyl isopropyl ether, isovanillyl butyl ether, isovanillyl amyl ether, isovanillyl isoamyl ether, isovanillyl hexyl ether, ethyl vanillyl methyl ether, ethyl vanillyl ethyl ether, ethyl vanillyl propyl ether, ethyl vanillyl isopropyl ether, ethyl vanillyl butyl ether, ethyl vanillyl amyl ether, ethyl vanillyl isoamyl ether, ethyl vanillyl hexyl ether, vanillin propylene glycol acetal, isovanillin propylene glycol acetal, ethyl vanillin propylene glycol acetal, vanillyl butyl ether acetate, isovanillyl butyl ether acetate, ethyl vanillyl butyl ether acetate, 4-(l-menthoxymethyl)-2-(3'-methoxy-4'-hydroxyphenyl)-l,3-dioxolane, 4-(l-menthoxymethyl)-2-(3'-hydroxy-4'-methoxyphenyl)-1,3-dioxolane, 4-(l-menthoxymethyl)-2-(3'-ethoxy-4'-hydroxyphenyl)-1,3-dioxolane, capsaicin, dihydrocapsaicin, nordihydrocapsaicin, homodihydrocapsaicin, homocapsaicin, bis-capsaicin, trishomocapsaicin, nornorcapsaicin, norcapsaicin, capsaicinol, vanillyl caprylamide (octylic acid vanillylamide), vanillyl pelargonamide (nonylic acid vanillylamide), vanillyl caproamide (decylic acid vanillylamide), vanillyl undecanamide (undecylic acid vanillylamide), N-trans-feruloyltyramine, N-5-(4-hydroxy-3-methoxyphenyl)-2E,4E-pentadienoylpiperidine, N-trans-feruloylpiperidine, N-5-(4-hydroxy-3-methoxyphenyl)-2E-pentenoylpiperidine, N-5-(4-hydroxyphenyl)-2E,4E-pentadienoylpiperidine, pipeline, isopiperine, chavicine, isochavicine, piperamine, piperettine, piperolein B, retrofractamide A, pipercide, guineenside, piperiline, piperamide C5:l (2E), piperamide C7:l (6E), piperamide C7:2 (2E,6E), piperamide C9:l (8E), piperamide C9:2 (2E,8E), piperamide C9:3 (2E,4E,8E), fagaramide, sanshool-I, sanshool-II, hydroxysanshool, sanshoamide, gingerol, shogaol, zingerone, methylgingerol, paradol,

spilanthol, chavicine, polygodial (tadeonal), isopolygodial, dihydropolygodial, and tadeon; and
one or more kinds of natural products selected from capsicum oil, capsicum oleoresin, ginger oleoresin, jambu oleoresin (Spilanthes oleracea extract), sansho extract, sanshoamide, black pepper extract, white pepper extract, and polygonum extract.
9. A flavor or fragrance composition comprising the sensory stimulant composition according to any one of claims 6 to 8.
10. The flavor or fragrance composition according to claim 9, wherein a content of the sensory stimulant composition is from 0.00001 mass% to 90 mass%.
11. A product comprising the sensory stimulant composition according to any one of claims 6 to 8, the product being any one of products selected from the group consisting of drinks, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, oral compositions, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, tobacco, quasi-drugs and pharmaceuticals.
12. The product according to claim 11, wherein a content of the sensory stimulant composition is from 0.00001 mass% to 50 mass%.
13. A product comprising the flavor or fragrance composition according to claim 9 or 10, the product being any one of products selected from the group consisting of drinks, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, oral compositions, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, tobacco, quasi-drugs and pharmaceuticals.
14. The product according to claim 13, wherein a content of the flavor or fragrance composition is from 0.00001 mass% to 50 mass%.

15. A method of manufacturing a product, comprising blending a product with the sensory stimulant composition according to any one of claims 6 to 8, wherein the product is any one of products selected from the group consisting of drinks, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, oral compositions, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, tobacco, quasi-drugs and pharmaceuticals.
16. A method of manufacturing a product, comprising blending a product with the flavor or fragrance composition according to claim 9 or 10, wherein the product is any one of products selected from the group consisting of drinks, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, oral compositions, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, tobacco, quasi-drugs and pharmaceuticals.
17. A methyl menthol derivative represented by the following general formula (1): [Chem. 3]
wherein a symbol * indicates an asymmetric carbon atom, X represents a hydrogen atom or a substituent, and Y represents an aryl group having 6 to 20 carbon atoms which may have a substituent.
18. The methyl menthol derivative according to claim 17, wherein X in the general formula (1) represents a hydrogen atom, a hydroxyl group, an acetoxy group, an oxo group, or a methyl group, and Y in the general formula (1) represents a phenyl group which may have a substituent.
19. The methyl menthol derivative according to claim 17 or 18, wherein the general formula (1) is represented by the following structural formula (2):

wherein a symbol * indicates an asymmetric carbon atom.

Documents

Application Documents

# Name Date
1 201947027272.pdf 2019-07-08
2 201947027272-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [08-07-2019(online)].pdf 2019-07-08
3 201947027272-STATEMENT OF UNDERTAKING (FORM 3) [08-07-2019(online)].pdf 2019-07-08
4 201947027272-PROOF OF RIGHT [08-07-2019(online)].pdf 2019-07-08
5 201947027272-PRIORITY DOCUMENTS [08-07-2019(online)].pdf 2019-07-08
6 201947027272-POWER OF AUTHORITY [08-07-2019(online)].pdf 2019-07-08
7 201947027272-FORM 1 [08-07-2019(online)].pdf 2019-07-08
8 201947027272-DECLARATION OF INVENTORSHIP (FORM 5) [08-07-2019(online)].pdf 2019-07-08
9 201947027272-COMPLETE SPECIFICATION [08-07-2019(online)].pdf 2019-07-08
10 201947027272-CLAIMS UNDER RULE 1 (PROVISIO) OF RULE 20 [08-07-2019(online)].pdf 2019-07-08
11 Correspondence by Agent_Form1_15-07-2019.pdf 2019-07-15
12 201947027272-FORM 3 [31-12-2019(online)].pdf 2019-12-31
13 201947027272-RELEVANT DOCUMENTS [13-07-2020(online)].pdf 2020-07-13
14 201947027272-MARKED COPIES OF AMENDEMENTS [13-07-2020(online)].pdf 2020-07-13
15 201947027272-FORM 13 [13-07-2020(online)].pdf 2020-07-13
16 201947027272-AMMENDED DOCUMENTS [13-07-2020(online)].pdf 2020-07-13
17 201947027272-FORM 18 [12-11-2020(online)].pdf 2020-11-12
18 201947027272-OTHERS [10-06-2021(online)].pdf 2021-06-10
19 201947027272-FORM 3 [10-06-2021(online)].pdf 2021-06-10
20 201947027272-FER_SER_REPLY [10-06-2021(online)].pdf 2021-06-10
21 201947027272-COMPLETE SPECIFICATION [10-06-2021(online)].pdf 2021-06-10
22 201947027272-CLAIMS [10-06-2021(online)].pdf 2021-06-10
23 201947027272-US(14)-HearingNotice-(HearingDate-17-11-2021).pdf 2021-10-18
24 201947027272-FER.pdf 2021-10-18
25 201947027272-Correspondence to notify the Controller [11-11-2021(online)].pdf 2021-11-11
26 201947027272-Written submissions and relevant documents [30-11-2021(online)].pdf 2021-11-30
27 201947027272-Retyped Pages under Rule 14(1) [30-11-2021(online)].pdf 2021-11-30
28 201947027272-2. Marked Copy under Rule 14(2) [30-11-2021(online)].pdf 2021-11-30
29 201947027272-PatentCertificate22-02-2022.pdf 2022-02-22
30 201947027272-IntimationOfGrant22-02-2022.pdf 2022-02-22
31 201947027272-RELEVANT DOCUMENTS [16-09-2023(online)].pdf 2023-09-16

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