KR101605211B1 - Phenylpropanoid compound - Google Patents

Phenylpropanoid compound Download PDF

Info

Publication number
KR101605211B1
KR101605211B1 KR1020107017672A KR20107017672A KR101605211B1 KR 101605211 B1 KR101605211 B1 KR 101605211B1 KR 1020107017672 A KR1020107017672 A KR 1020107017672A KR 20107017672 A KR20107017672 A KR 20107017672A KR 101605211 B1 KR101605211 B1 KR 101605211B1
Authority
KR
South Korea
Prior art keywords
deodorant
hydrogen atom
group
fraction
odor
Prior art date
Application number
KR1020107017672A
Other languages
Korean (ko)
Other versions
KR20100131975A (en
Inventor
마사미 미즈
도시카즈 가와이
츠요시 이케다
히로유키 미야시타
Original Assignee
미츠이 세이토 가부시키가이샤
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 미츠이 세이토 가부시키가이샤 filed Critical 미츠이 세이토 가부시키가이샤
Publication of KR20100131975A publication Critical patent/KR20100131975A/en
Application granted granted Critical
Publication of KR101605211B1 publication Critical patent/KR101605211B1/en

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L9/00—Disinfection, sterilisation or deodorisation of air
    • A61L9/01—Deodorant compositions
    • A61L9/014—Deodorant compositions containing sorbent material, e.g. activated carbon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups

Abstract

The present invention relates to phenylpropanoid compounds,
The present invention provides a compound having a deodorizing effect against odor and provides a compound represented by the following formula (1).
R 1 , R 2 , R 3 , R 4 and R 5 each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an acyl group having 1 to 4 carbon atoms, and a group represented by the following formula (2) And R 6 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an acyl group having 1 to 4 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an aldehyde group having 1 to 4 carbon atoms, And R 7 is a hydrogen atom, an alkoxy group having 1 to 4 carbon atoms, an acyl group having 1 to 4 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, and a group represented by formula (3) Gt ;, R < 8 >, R < 9 & And R 10 are each independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms and an acyl group having 1 to 4 carbon atoms, and R 11 each independently represents a hydrogen atom, an alkoxy group having 1 to 4 carbon atoms, An acyl group having 1 to 4 carbon atoms and an acyloxy group having 1 to 4 carbon atoms:
(Formula 1)

Figure 112010051079388-pct00024

(2)
Figure 112010051079388-pct00025

(Formula 3)
Figure 112010051079388-pct00026

Description

Phenylpropanoid compound {PHENYLPROPANOID COMPOUND}

The present invention relates to phenylpropanoid compounds. These compounds have a deodorizing effect on malodors, for example, S-based compounds, N-based compounds and lower fatty acids.

Recently, deodorant of natural materials has been used in various fields including food use and environment use. However, since the deodorant of a natural material contains a plurality of compounds, the effective ingredient thereof is often unclear. Therefore, in studying the use and / or the safety of the deodorant, it is required to specify a component having a deodorizing effect.

Japanese Patent Application Laid-Open No. 10-151182 discloses a deodorant material derived from sugar cane. Japanese Patent Application Laid-Open No. 2001-87365 discloses a deodorant containing distillate derived from sugar cane as an active ingredient.

Japanese Patent Application Laid-Open No. 10-151182 Japanese Patent Application Laid-Open No. 2001-87365

Thereby providing a compound having a deodorizing effect on the odor.

The present invention provides a compound represented by the following Formula 1:

Figure 112010051079388-pct00001

(Wherein R 1 , R 2 , R 3 , R 4 and R 5 each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an acyl group having 1 to 4 carbon atoms, and a group represented by the following formula ≪ / RTI >

Figure 112010051079388-pct00002

R 6 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an acyl group having 1 to 4 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an aldehyde group having 1 to 4 carbon atoms, ≪ / RTI > and < RTI ID = 0.0 >

Figure 112010051079388-pct00003

R 7 is optionally selected from the group consisting of groups represented by the acyl group, an acyloxy group and (3) having from 1 to 4 carbon atoms, a hydrogen atom, a 1-4C alkoxy group, having from 1 to 4 carbon atoms, a and, R 8, R 9, and R 10 is each independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms and an acyl group having 1 to 4 carbon atoms, and each R 11 is independently selected from the group consisting of a hydrogen atom, an alkoxy group having 1 to 4 carbon atoms, An acyl group having 1 to 4 carbon atoms, and an acyloxy group having 1 to 4 carbon atoms. Particularly, R 1 is a hydrogen atom or a group represented by the following formula (4)
(Formula 4)

Figure 112015105563112-pct00065

R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an ethynyl group or an aldehyde group, and R 7 is a hydrogen atom or a methoxy group.

Preferably R 1, R 2, R 3, R 4 and R 5 are each independently and optionally selected from the hydrogen atom, the group consisting of groups represented by the alkyl group and the formula (2) with a carbon number of 1 ~ 4, R 6 is a hydrogen atom, carbon atoms selected optionally from 1 to 4 alkyl group, an acyloxy group having from 1 to 4 carbon atoms, an alkenyl group, the group consisting of groups represented by the aldehyde group and (3) of 1 to 4 carbon atoms having 2 to 4, R 7 is a hydrogen atom, An alkoxy group having 1 to 4 carbon atoms, an acyloxy group having 1 to 4 carbon atoms, and a group represented by the formula (3), R 8 , R 9 and R 10 are each independently selected from the group consisting of a hydrogen atom and a And R 11 is each independently selected from the group consisting of a hydrogen atom, an alkoxy group having 1 to 4 carbon atoms, and an acyl group having 1 to 4 carbon atoms.

Preferably R 1, R 2 and R 5 is selected arbitrarily from the group consisting of groups represented by a hydrogen atom, an alkyl group and formula (2) having from 1 to 4 carbon atoms, each independently, R 3 And R 4 is selected from the group consisting of a hydrogen atom and an alkyl group having 1 to 4 carbon atoms, and R 6 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, and an aldehyde group having 1 to 4 carbon atoms And R 7 is selected from the group consisting of a hydrogen atom and an alkoxy group having 1 to 4 carbon atoms, and R 8 , R 9 and R 10 are each independently selected from the group consisting of a hydrogen atom and an alkyl group having 1 to 4 carbon atoms And R < 11 > are each independently selected from the group consisting of a hydrogen atom and an alkoxy group having 1 to 4 carbon atoms.

Preferably, each of R 1 , R 2 and R 5 is independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 2 carbon atoms and a group represented by formula (2), R 3 and R 4 each represent a hydrogen atom, 2, and R 6 is selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 2 carbon atoms, an alkenyl group having 2 to 3 carbon atoms, and an aldehyde group having 1 to 2 carbon atoms, and R 7 is selected from the group consisting of hydrogen An alkoxy group having 1 to 2 carbon atoms, and R 8 , R 9 and R 10 are each independently selected from the group consisting of a hydrogen atom and an alkyl group having 1 to 2 carbon atoms, and R 11 is independently selected from the group consisting of Is selected from the group consisting of a hydrogen atom and an alkoxy group having 1 to 2 carbon atoms. More preferably, R 3 and R 4 are hydrogen atoms.

Preferably, R 1 is a hydrogen atom, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an ethynyl group, and R 7 is a hydrogen atom .

Preferably, R 1 is a hydrogen atom, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an ethynyl group, and R 7 is a methoxy group .

Preferably, R 1 is a hydrogen atom, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an aldehyde group, and R 7 is a hydrogen atom.

Preferably, R 1 is a hydrogen atom, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an aldehyde group, and R 7 is a methoxy group.

Preferably, R 1 is a methyl group, R 2 is a hydrogen atom, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an ethenyl group, and R 7 is a hydrogen atom .

Preferably, R 1 is a methyl group, R 2 is a hydrogen atom, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an aldehyde group, and R 7 is a hydrogen atom.

Preferably, R 1 is a methyl group, R 2 is a hydrogen atom, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an ethynyl group, and R 7 is a methoxy group .

Preferably, R 1 is a methyl group, R 2 is a hydrogen atom, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an aldehyde group, and R 7 is a methoxy group.

Preferably, R 1 is a methyl group, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an ethenyl group, and R 7 is a hydrogen atom.

Preferably, R 1 is a methyl group, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an aldehyde group, and R 7 is a hydrogen atom.

Preferably, R 1 is a methyl group, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an ethenyl group, and R 7 is a methoxy group.

Preferably, R 1 is a methyl group, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an aldehyde group, and R 7 is a methoxy group.

Preferably R 1 is a hydrogen atom, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is ethenyl group, and R 7 is a hydrogen atom to be.

Preferably, R 1 is a hydrogen atom, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an ethenyl group, and R 7 is a methoxy group to be.

Preferably, R 1 is a hydrogen atom, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an aldehyde group, and R 7 is a hydrogen atom .

Preferably, R 1 is a hydrogen atom, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an aldehyde group, and R 7 is a methoxy group .

Preferably, R 1 is a methyl group, R 2 is a hydrogen atom, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an ethenyl group, and R 7 is a hydrogen atom to be.

Preferably, R 1 is a methyl group, R 2 is a hydrogen atom, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an aldehyde group, and R 7 is a hydrogen atom .

Preferably, R 1 is a methyl group, R 2 is a hydrogen atom, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an ethenyl group, and R 7 is a methoxy group to be.

Preferably, R 1 is a methyl group, R 2 is a hydrogen atom, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an aldehyde group, and R 7 is a methoxy group .

Preferably, R 1 is a methyl group, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an ethenyl group, and R 7 is a hydrogen atom .

Preferably, R 1 is a methyl group, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an aldehyde group, and R 7 is a hydrogen atom.

Preferably, R 1 is a methyl group, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an ethynyl group, and R 7 is a methoxy group .

Preferably, R 1 is a methyl group, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an aldehyde group, and R 7 is a methoxy group.

Preferably, R < 1 > is a group represented by the formula (3)

(Formula 3)

Figure 112010051079388-pct00004

R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an ethynyl group, and R 7 is a hydrogen atom.

Preferably, R 1 is a group represented by the formula (3), R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an ethenyl group, and R 7 Is a methoxy group.

Preferably is a group R 1 is represented by the formula 3, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an aldehyde group, and R 7 is Is a hydrogen atom.

Preferably is a group R 1 is represented by the formula 3, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an aldehyde group, and R 7 is Methoxy group.

Preferably, R 1 is a group represented by the formula (3), R 2 is a hydrogen atom, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an ethenyl group, and R 7 is a hydrogen atom.

Preferably R 1 is a group represented by the formula 3, R 2 is a hydrogen atom, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an aldehyde group, and R 7 Is a hydrogen atom.

Preferably, R 1 is a group represented by the formula (3), R 2 is a hydrogen atom, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an ethenyl group, and R 7 is a methoxy group.

Preferably R 1 is a group represented by the formula 3, R 2 is a hydrogen atom, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an aldehyde group, and R 7 Is methoxy.

Preferably, R 1 is a group represented by the formula (3), R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an ethenyl group, and R 7 Is a hydrogen atom.

Preferably is a group R 1 is represented by the formula 3, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an aldehyde group, and R 7 is Is a hydrogen atom.

Preferably, R 1 is a group represented by the formula (3), R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an ethenyl group, and R 7 Is a methoxy group.

Preferably is a group R 1 is represented by the formula 3, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an aldehyde group, and R 7 is Methoxy group.

Preferably, R 1 is a group represented by the formula (3), R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an ethenyl group, and R 7 is a hydrogen atom.

Preferably, R 1 is a group represented by the formula (3), R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an ethenyl group, and R 7 is a methoxy group.

Preferably, R 1 is a group represented by the formula (3), R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an aldehyde group, and R 7 Is a hydrogen atom.

Preferably, R 1 is a group represented by the formula (3), R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an aldehyde group, and R 7 Is a methoxy group.

Preferably, R 1 is a group represented by the formula (3), R 2 is a hydrogen atom, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an ethenyl group, and R 7 is a hydrogen atom.

Preferably, R 1 is a group represented by the formula (3), R 2 is a hydrogen atom, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an aldehyde group, and R 7 is a hydrogen atom.

Preferably, R 1 is a group represented by the formula (3), R 2 is a hydrogen atom, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an ethenyl group, and R 7 is a methoxy group.

Preferably, R 1 is a group represented by the formula (3), R 2 is a hydrogen atom, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an aldehyde group, and R 7 is a methoxy group.

Preferably, R 1 is a group represented by the formula (3), R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an ethenyl group, and R 7 is a hydrogen atom.

Preferably, R 1 is a group represented by the formula (3), R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an aldehyde group, and R 7 Is a hydrogen atom.

Preferably, R 1 is a group represented by the formula (3), R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an ethenyl group, and R 7 is a methoxy group.

Preferably, R 1 is a group represented by the formula (3), R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a hydrogen atom, R 6 is an aldehyde group, and R 7 Is a methoxy group.

Preferably, R < 8 >, R < 9 > And R 10 are each independently selected from the group consisting of a hydrogen atom and a methyl group, and R 11 is optionally selected from the group consisting of a hydrogen atom, a hydroxyl group and a methoxy group.

Preferably, R < 8 > And R 9 are each independently selected from the group consisting of a hydrogen atom and a methyl group, R 10 is a hydrogen atom, and R 11 is a hydrogen atom.

Preferably, R < 8 > And R 9 are each independently selected from the group consisting of a hydrogen atom and a methyl group, R 10 is a hydrogen atom, and R 11 is a hydrogen atom.

Preferably, in formula (3), R 8 is a hydrogen atom, R 9 is a methyl group, R 10 is a hydrogen atom, and R 11 is a hydrogen atom.

Preferably, in formula (3), R 8 is a methyl group, R 9 is a hydrogen atom, R 10 is a hydrogen atom, and R 11 is a hydrogen atom.

Preferably, R 1 in the formula ( 1) is a group represented by the following formula (4), R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an ethenyl group , And R < 7 > is a methoxy group.

Figure 112010051079388-pct00005

The phenylpropanoid compound of the present invention has a deodorizing effect on odor, for example, an S-based compound, an N-based compound and a lower fatty acid. The phenylpropanoid compound of the present invention has antioxidant ability as shown in Example 56 below. The mechanism of the deodorizing effect of the compound on the odorous substance is not clear, but the antioxidant ability is considered to be one mechanism.

1 is a view showing the entire flow of a fractionation operation,
2A is a diagram showing the structural formula of MSX-2, the assignment of 13 C-NMR and the result of HMBC,
2B is a chart showing 1 H-NMR of MSX-2,
2C is a chart showing 13 C-NMR of MSX-2,
FIG. 3A is a drawing showing the structural formula of MSX-3 and the attribution of 13 C-NMR,
3B is a chart showing 1 H-NMR of MSX-3,
3C is a chart showing 13 C-NMR of MSX-3,
4A is a diagram showing the structural formula of MSX-4, the attribution of 13 C-NMR and the result of HMBC,
4B is a chart showing 1 H-NMR of MSX-4,
4C is a chart showing 13 C-NMR of MSX-4,
5A is a diagram showing the structural formulas of MSX-6A and MSX-6B, the results of 13C -NMR assignment and HMBC of MSX-6A,
5B is a chart showing 1 H-NMR of MSX-6A,
FIG. 5C is a chart showing 13 C-NMR of MSX-6A and FIG.
6 is a graph showing the deodorizing effect of deodorant (A to F) against hydrogen sulfide.

The compounds of the present invention can be obtained by purification from natural products or by chemical synthesis. When the compounds of the present invention are obtained from natural products, for example, sugar cane can be used. The raw materials described in the following examples can be obtained, for example, according to the method described in Japanese Patent Application Laid-Open No. 2001-87365.

The phenylpropanoid compound of the present invention is used as a deodorant in various deodorization fields.

The deodorant may be used as a food, an etiquette deodorant, a deodorant for a pet, or an environmental deodorant, and may be mixed with other deodorants, flavors, alcohols, surfactants and the like. Specifically, the deodorant can be added to foods to remove unpleasant odors of food materials such as meat, fish and shellfish, leek and garlic, and other food materials. In addition, the deodorant may be used as a material for an etiquette deodorant. Here, the etiquette deodorant according to the present invention is a deodorant directly used for a person such as body odor (foot body), foot odor, hair odor and the like of bad breath, armpit and the like. The use of this deodorant means that it is used directly by people regardless of the source of the unpleasant odor. Specifically, examples include a side-arm sweat odor sprayer, a lotion powder, a mouth sprayer, a capsule for a bad breath removing mouthwash, an oral cleanser, a roasted meat on the hair, a hair spray for removing a smell of a cigarette, a shampoo, a rinse, and a hair lotion . The deodorant can also be used as a deodorant material for pet. The pet deodorant is a deodorant for unpleasant odors caused by pets such as bad breath, body odor, and odor (stool odor) of a pet. Specifically, examples include pets themselves and pet products such as sprays and capsules for removing bad breath of pets, sprays for dogs, shampoos, rinses and lotions for eliminating body odor of fur, baths for pets, cages for dogs and pets, and the like. The deodorant may also be used as a material for environmental deodorant. The environmental deodorant is a deodorant for an unpleasant odor in an object or space other than a person or a pet. Specifically, waste such as household waste or industrial waste, household waste or industrial waste collection site, domestic waste or industrial waste accumulation site, hydrogenated waste, household waste or industrial waste treatment plant, The use of water such as manure treatment plant, crematorium, slaughterhouse, dead animal processing plant, hospital, clinic, inspection center, restroom, bathroom, kitchen, etc., building and wallpaper of general indoor and indoor (odor of processing agent used for processing formalin etc.) The smell of molds such as curtains, paintings, furniture (odor of processing agents such as paints and processing), closet (shoehorn), shoemakers, air conditioners, garments, automobiles, trucks, , Restaurants, photo labs, laboratories, petrol stands, places for refilling propane gas, laundry and laundry facilities, inns, hotels, beauty salons, barber shops, Factories, barns for cattle, can be used for the construction job site.

The mode of use of the deodorant is not particularly limited and may be used in various forms, for example, as follows. Liquid aerosol spray, mist spray, liquid for sprinkler, liquid, gel, paste-like deodorant for application, and sheet-like article impregnated with cloth, paper, or nonwoven fabric. In addition, deodorant absorbed in powders and granules, deodorant adsorbed or adsorbed in particle type, pellet type, block type, tablet type gel, deodorant adsorbed to a porous carrier such as ceramic, activated carbon, bentonite, A deodorant is placed in a porous container such as a deodorant or a ceramic having deodorizing effect by vaporizing the permeated deodorant and bringing the deodorant to the outside of the container A deodorant having a deodorant effect due to vaporization of a permeated deodorant, a deodorant to be added to a bad odor source as it is in a liquid state, a deodorant to be impregnated in a sheet, a film or a filter, a wallpaper containing a deodorant on the surface or inside, a construction material, diapers, Rugs, deodorizing fibers (cloth), deodorizing leather, etc.

In addition, food, etiquette deodorant, pet deodorant, and environmental deodorant containing the deodorant may include common additives, dispersants, excipients and the like in each field.

More specifically, the following method can be adopted for preparing a mist spray type deodorant for pet odors in a home, food waste in a kitchen, kitchen garbage, and the like using the deodorant. The deodorant is added to water at a concentration of 0.001 to 50%, preferably 0.01 to 5% (volume / volume), and if necessary, a surfactant, ethanol, antimicrobial agent or the like is added to the mist spray bottle.

More specifically, the following method may be adopted for preparing the aerosol-type deodorant for food waste or toilet odor, which is strong odor in the home by using the deodorant. The deodorant is diluted with water or an aqueous ethanol solution at a concentration of 0.02 to 70%, preferably 0.2 to 10% (volume / volume), and charged into an aerosol container together with an injection gas (for example, LPG and carbon dioxide).

More specifically, the following method can be adopted for preparing a deodorant for space in which the effective component of deodorant is gradually volatilized by adsorbing or incorporating the deodorant into a gel or an appropriate carrier and the result of deodorization lasts for a long time. The deodorant may be added in a concentration of 0.05 to 20% by weight, preferably 0.5 to 10% by weight, in the presence of a gelling agent such as carrageenan, agar, locust bean gum, polyvinyl alcohol, gum arabic, gellan gum, gelatin, carboxymethylcellulose, chitin, Sodium alginate, polyacrylamide, and the like, alone or in combination, to solidify.

The deodorant can be deodorized in the room by dispersing the deodorant in the form of a fine mist. More specifically, the odor in the indoor space can be deodorized by adding the deodorant to the water of the humidifier at a concentration of 0.001 to 1% (volume / volume) and operating the humidifier.

By spraying the deodorant into the air intermittently or continuously and dispersing it on the bottom surface, it is possible to remove the odor in a place where odor is likely to occur such as pig farm, poultry farm, dairy farm, fish market, etc. At this time, the deodorant is preferably diluted with water to a concentration of 0.001 to 1% (volume / volume).

In addition, the deodorant can reduce odor when a stool, urine or feces mixture produced from swine, dairy, poultry, etc. is dispersed in a field or a ranch paper by a vacuum car or the like . The odor can be suppressed by adding the deodorant to the feces in the tank at a concentration of 0.001 to 0.5% (volume / volume) before dispersing.

In addition, a pet feces treating agent having a high deodorizing effect can be produced by using the deodorant. The fecal treatment agent for pets is prepared by adding bentonite, zeolite, wood powder, paper powder or the like as a main material to the resulting mixture, adding sodium polyacrylate, other sodium compounds, magnesium compounds and the like thereto, By adding 0.001 to 10% by weight, preferably 0.01 to 1% by weight, of a deodorant to the main material, adding an appropriate amount of water, mixing, molding and drying. This is placed in a toilet for a pet such as a cat, and the cats are disposed on the treating agent, whereby a treating agent having an excellent deodorizing effect can be obtained.

As described above, in the method of mixing and molding the deodorant with other materials, since the effective component of the deodorant does not completely volatilize during drying, the deodorant effect remains. Further, it is possible to obtain an article having a deodorizing effect even by mixing materials other than the deodorant first, and then molding and drying to absorb the deodorant in the obtained molded article.

In the following,% means weight% unless otherwise specified. The column size is indicated by the inner diameter (mm) × height (mm).

Example 1

1. Manufacture of raw materials

2800 L of compressed juice (Bx. 12.2) of sugarcane obtained in the manufacturing process of a raw sugar factory was placed in a centrifugal thin film vacuum evaporator (trade name: Everpol CEP-1, manufactured by Ohkawa Hara Shoji Co., Ltd.) at a rate of 250 L / . The fraction which was distilled off at a temperature of 90 to 95 ° C under a reduced pressure of 500 to 630 mmHg was cooled with a condenser under conditions of cooling water temperature of 25 ° C, cooling water amount of 15 m 3 / hour and a condenser area of 2 m 2. The raw material compressed juice is about 2400 L, Bx. The distillation was terminated when it reached 13.9. The obtained distillate (hereinafter referred to as primary distillate 1) was about 400 L. The color of the primary distillate 1 was almost colorless and transparent. The primary distillate 1 had a peculiar smell derived from sugar cane.

Subsequently, about 400 L of the first distillate 1 was passed through a column (column size: 26 x 200) packed with 40 mL of trade name Ambarite XAD7HP (Organo Corp.) at a flow rate of SV = 75. After completion of the passing, the water was washed at the same flow rate for about 5 minutes. The adsorbed components were eluted with an aqueous 80% ethanol solution (ethanol / water = 80/20 (volume / volume)). The liquid was passed at a flow rate of SV = 2, the first 25 ml of the eluate was discarded, and the recovery of the eluate was started. After 80 ml of 80% ethanol aqueous solution was passed through, distilled water was passed through at the same rate for extruding the components. Elution was terminated when the amount of the recovered effluent reached 100 ml. The ethanol concentration (volume / volume) of the obtained eluate (hereinafter referred to as the primary distillate 2, also referred to as the undiluted solution of the secondary distillation) was 59%, and the color was slightly lemon-colored and transparent. The primary distillate 2 had a peculiar odor derived from sugarcane.

Subsequently, the solution of the primary distillate 2 was diluted 3-fold with water and ethanol to adjust the ethanol concentration (volume / volume) to 45% (hereinafter referred to as MSX-245). 4000 ml of the above solution was placed in a rotary evaporator (Tokyo Rika Kikai Co., Ltd.) and distilled under a pressure of 90 mmHg (reduced pressure) or less and a steam temperature of 30 to 40 ° C. The residue was distilled until it was dried and solidified to obtain 2.5 g of a residue.

2. Fractionation operation

In the following fractionation operation, all the open columns were used to drop the solvent naturally. The entire flow of the sub-residue fractionation operation is shown in Fig.

A. Fraction of sub-residue

2.5 g of the residue was dissolved in a small amount of methanol and provided to a column packed with Sephardex (trademark) LH-20 (Amersham Pharmacia Japan KK) (column size 27x550; solvent methanol) did. The carrier of Sephadex LH-20 was sufficiently swollen with methanol to equilibrate it. The amount of the solvent is three times the amount of the column bed. By the fraction, fractions 1 to 6 were obtained. The solvent of each fraction was distilled off under reduced pressure. The solids (dry weight) of each fraction is as follows: Fraction 1 (55mg), Fraction 2 (285mg), Fraction 3 (474mg), Fraction 4 (710mg), Fraction 5 (397mg), Fraction 6 (96mg)

B-1. Fraction of fraction 4

The fraction 4 was dissolved in a small amount of methanol, and the solution was added to a column packed with Sephadex LH-20 (column size 27x500; solvent methanol), and fractionation was carried out. The carrier of Sephadex LH-20 was sufficiently swollen with methanol to equilibrate it. The amount of the solvent is three times the amount of the column bed. By this fraction, fraction 4-1, fraction 4-2 and fraction 4-3 were obtained. The solvent of each fraction was distilled off under reduced pressure. The solids (dry weight) of each fraction is as follows: Fraction 4-1 (227 mg), Fraction 4-2 (185 mg), Fraction 4-3 (60 mg).

B-2. Fraction of fraction 4-2

The fraction 4-2 was dissolved in a small amount of methanol, and the solution was supplied to a column packed with silica gel 60N (Kanto Chemical Co., Ltd.) (column size 20x300) and fractionated. The silica gel 60N carrier was dry-packed in the column. The solvent was eluted in the order of hexane: acetone (volume: volume) = 3: 1, 2: 1, 1: 1 and 0: The amount of each solvent is three times the amount of the column bed. By this fraction, the fraction 4-2-1, the fraction 4-2-2 and the fraction 4-2-3 were obtained. The solvent of each fraction was distilled off under reduced pressure. The solids (dry weight) of each fraction is as follows: Fraction 4-2-1 (40 mg), fraction 4-2-2 (3 mg), fraction 4-2-3 (12 mg).

C-1. Fraction of fraction 2

The fraction 2 was dissolved in a small amount of methanol, and the solution was supplied to a column packed with silica gel 60N (Kanto Chemical Co., Ltd.) (column size 20 x 300), and fractionated. The silica gel 60N carrier was dry-packed in the column. (Volume: volume) = 9: 1: 0.1, 8: 2: 0.2, 7: 3: 0.5, and 10: 1 in chloroform: methanol (volume: volume) = 20: 6: 4: 1, and finally methanol. The amount of each solvent is three times the amount of the column bed. By this fraction, fraction 2-1, fraction 2-2 and fraction 2-3 were obtained. The solvent of each fraction was distilled off under reduced pressure. The solids (dry weight) of each fraction is as follows: Fraction 2-1 (40 mg), Fraction 2-2 (145 mg), Fraction 2-3 (95 mg).

C-2. Fraction of fraction 2-2

The fraction 2-2 was dissolved in a small amount of methanol, and the solution was supplied to a column packed with Wako gel (ODS) (Wako Pure Chemical Industries, Ltd.) (column size 25x350), and fractionated. The carrier of Wako gel was dry-charged to the column. The solvent was changed to methanol: water (volume: volume) = 80:20, 85:15, 90:10, and 100: 0. The amount of each solvent is three times the amount of the column bed. By this fraction, fraction 2-2-1, fraction 2-2-2 and fraction 2-2-3 were obtained. The solvent of each fraction was distilled off under reduced pressure. The solids (dry weight) of each fraction is as follows: Fraction 2-2-1 (105 mg), fraction 2-2-2 (47 mg), fraction 2-2-3 (7 mg).

C-3. Fraction of fraction 2-2-2

The fraction 2-2-2 was dissolved in a small amount of methanol, and the solution was supplied to a column packed with silica gel 60N (Kanto Chemical Co., Ltd.) (column size 20x300) and fractionated. The silica gel 60N carrier was dry-packed in the column. The solvent was eluted in the order of hexane: acetone (volume: volume) = 10: 1, 5: 1, 3: 1, 0: The amount of each solvent is three times the amount of the column bed. By this fraction, fraction 2-2-2-1 was obtained. The solvent of the fraction was distilled off under reduced pressure. The solid content (dry weight) of fraction 2-2-2-1 was 37 mg.

D. Purification of Fraction 5

A small amount of methanol was added to the fraction 5, and the fraction 5 was dissolved by heating in a water bath at 60 占 폚 and sonicator treatment. By allowing the melt to stand at room temperature, recrystallization was carried out. Crystals precipitated by recrystallization were filtered to obtain fraction 5-1. The solvent of the fraction was distilled off under reduced pressure. The solid content (dry weight) of fraction 5-1 is 310 mg.

E-1. Fraction of fraction 3

The fraction 3 was dissolved in a small amount of methanol, and the solution was supplied to a column packed with Wako gel (ODS) (Wako Pure Chemical Industries, Ltd.) (column size 25 x 350), and fractionated. The carrier of Wako gel was dry-charged to the column. The solvent was eluted in the order of methanol: water (volume: volume) = 40:60, 50:50, 55:45, 60:40, 70:30, 80:20 and 100: 0. The amount of each solvent is three times the amount of the column bed. By this fraction, fraction 3-1 and fraction 3-2 were obtained. The solvent of each fraction was distilled off under reduced pressure. The solids (dry weight) of each fraction is as follows: Fraction 3-1 (79 mg), fraction 3-2 (396 mg).

E-2. Tablets of fraction 3-1

A small amount of methanol was added to the fraction 3-1, and the fraction 3-1 was dissolved by heating in a water bath at 60 占 폚 and a sonicator treatment. Recrystallization was carried out by allowing the melt to stand at room temperature. The crystals precipitated by the recrystallization were filtered to obtain fraction 3-1-1. The solvent of the fraction was distilled off under reduced pressure. The solid content (dry weight) of fraction 3-1-1 was 11 mg.

F. Confirmation of single item

The purity of the compounds in Fraction 5-1, Fraction 4-2-1, Fraction 4-2-2, Fraction 4-2-3, Fraction 3-1-1 and Fraction 2-2-2-1 was measured by thin layer chromatography (Pure layer) (silica gel 60F 254 (Merck)). The details are as follows. Each fraction was dissolved in a small amount of methanol, spotted on thin layer chromatography, air dried, and developed with the solvent described below. After development, 10% sulfuric acid / methanol was sprayed onto the thin layer chromatography. Thin layer chromatography was heated with a hot plate to confirm the spot.

(One). Fraction 5-1 (hereinafter referred to as MSX-1)

It was not detected by thin layer chromatography.

(2). The fraction 4-2-1 (hereinafter referred to as MSX-2)

The Rf value in the thin layer chromatography was 0.60, confirming that it was a single product. The developing solvent is hexane: acetone = 2: 1 (volume: volume). MSX-2 is a white powder.

(3). The fraction 4-2-2 (hereinafter referred to as MSX-3)

The Rf value in the thin layer chromatography was 0.25, confirming that it was a single product. The developing solvent is hexane: acetone = 2: 1 (volume: volume). MSX-3 is a white powder.

(4). The fraction 4-2-3 (hereinafter referred to as MSX-4)

The Rf value in the thin layer chromatography was 0.19, confirming that it was a single product. The developing solvent is hexane: acetone = 2: 1 (volume: volume). MSX-4 is a white powder.

(5). The fraction 3-1-1 (hereinafter referred to as MSX-5)

The Rf value in thin layer chromatography was 0.28. The developing solvent is chloroform: methanol: water = 9: 1: 0.1 (volume: volume: volume). MSX-5 is a yellow powder.

(6). The fraction 2-2-2-1 (hereinafter referred to as MSX-6)

The Rf value in thin layer chromatography is 0.40. The developing solvent is hexane: acetone = 3: 1 (volume: volume). MSX-6 is a white powder.

3. Identification (Identification)

1 H-NMR, 13 C-NMR, UV, IR and mass spectra were measured for MSX-2, MSX-3, MSX-4 and MSX-6. The analysis values are as follows.

JNM-A500 (manufactured by Nippon Denshi Co., Ltd., 500 MHz) was used for measurement of 1 H-NMR.

JNM-A500 (manufactured by Nippon Denshi Co., Ltd., 125 MHz) was used for measurement of 13 C-NMR.

The mass spectrum was measured by using JMS-DX-303HF (manufactured by Nippon Denshi K.K.). The measurement conditions are as follows; EI-MS: ionization voltage 70-75 eV; Ionization current 200 ~ 300mA; Ionization temperature 135 ~ 350 ℃

· MSX-2

FIG. 2A shows the results of the structural formula of MSX-2, the assignment of 13 C-NMR, and the result of HMBC (Heteronuclear Multiple-Bond Correlation).

The IUPAC name of MSX-2 is as follows.

3- (2-hydroxy-2- (4-hydroxy-3-methoxyphenyl) ethyl) -5-methoxystyrene

FIG. 2B is a chart of 1 H-NMR of MSX-2.

1 H-NMR (CDCl 3) δ (ppm): 3.23 (1H, dd, J = 8.8, 15.6Hz), 3.54 (1H, dd, J = 9.5, 15.6Hz), 3.86 (3H, s, OCH 3) , 3.89 (3H, s, OCH 3), 5.11 (1H, d, J = 11.0Hz), 5.58 (1H, d, J = 17.7Hz), 5.60 (1H, s, OH), 5.72 (1H, dd, (1H, s, Ph), 6.88 (1H, s, Ph), 6.88 (1H, s, Ph) (1H, s, Ph), 6.94 (1H, s, Ph).

2C is a chart of < 13 > C-NMR of MSX-2.

13 C-NMR (CDCl 3) δ (ppm): 38.6 (CH 2), 56.0 (-OCH 3), 56.0 (-OCH 3), 85.6 (CH 2 OH), 108.8 (Ar-C), 109.7 (Ar -C), 111.4 (CH 2 = ), 114.3 (Ar-C), 115.2 (Ar-C), 119.5 (Ar-C), 128.1 (Ar-C), 131.7 (Ar-C), 133.2 (Ar- C), 136.8 (= CH-), 144.3 (Ar-C), 145.7

UV? Max (CHCl 3 ) nm (?): 279 (8.1 × 10 4 ),

IR (KBr) cm- 1 : 3435 (OH), 1032 (C-C).

MS m / z 298 [MH 2 O] < + & gt ;

· MSX-3

FIG. 3A shows the structure of MSX-3 and the assignment of 13 C-NMR.

The IUPAC name of MSX-3 is as follows.

5- (2-hydroxy-2- (4-hydroxy-3-methoxyphenyl) ethyl)

FIG. 3B is a chart of 1 H-NMR of MSX-3.

1 H-NMR (CDCl 3) δ (ppm): 3.34 (1H, dd, J = 8.6, 15.9Hz), 3.66 (1H, dd, J = 9.8, 15.9Hz), 3.88 (3H, s, OCH 3) , 3.94 (3H, s, OCH 3), 5.65 (1H, s, 0H), 5.85 (1H, dd, J = 9.2, 9.2Hz), 6.90 (1H, s), 6.91 (1H, d, J = 6.7 ), 7.36 (1H, s, Ph), 7.37 (1H, s, Ph).

FIG. 3C shows a chart of 13 C-NMR of MSX-3.

13 C-NMR (CDCl 3) δ (ppm): 37.7 (CH 2), 56.0 (-OCH 3), 56.1 (-OCH 3), 86.8 (CH 2 OH), 96.2, 108.8 (Ar-C), 111.7 (Ar-C), 114.4 (Ar-C), 119.6 (Ar-C), 121.4 (Ar-C), 128.4 Ar-C), 146.1 (Ar-C), 146.8 (Ar-C), 153.7 (Ar-C), 190.5 (O = CH-).

UV? Max (CHCl 3 ) nm (?): 287 (13.6 × 10 4 ),

IR (KBr) cm -1 : 3408 (OH), 1684 (CHO).

MS m / z 316 [M] < + & gt ;

· MSX-4

Figure 4A shows the structural formula of MSX-4, the assignment of 13 C-NMR and the results of HMBC.

The IUPAC name of MSX-4 is as follows.

2- (4- (2-hydroxy-2- (4-hydroxy-3-methoxyphenyl) ethoxy) -3,5-dimethoxyphenyl) Ethyl-5-methoxystyrene

FIG. 4B is a chart of 1 H-NMR of MSX-4.

1 H-NMR (CDCl 3) δ (ppm): 3.28 (1H, dd, J = 9.2, 15.3Hz), 3.61 (1H, dd, J = 9.2, 15.9Hz), 3.68 (1H, dd, J = 9.8 , 11.0Hz), 3.87 (6H, s, OCH 3), 3.88 (3H, s, 0CH 3), 3.92 (3H, s, OCH 3), 4.34 (1H, d, J = 11.0 Hz), 4.44 (1H , s, OH), 4.85 (1H, d, J = 9.8 Hz), 5.13 (1H, d, J = 11.0 Hz), 5.59 , 5.74 (1H, t, J = 9.2 Hz), 6.65 (1H, dd, J = 11.0, 17.7 Hz), 6.68 , J = 7.9), 6.89 (1H, s, Ph), 6.92 (1H, s, Ph), 6.94 (1H, d, J = 14.7).

Fig. 4C is a chart of < 13 > C-NMR of MSX-4.

13 C-NMR (CDCl 3) δ (ppm): 29.3, 38.6 (CH 2), 56.0 (-OCH 3), 56.0 (-OCH 3), 56.2 (-OCH 3), 56.2 (-OCH 3), 72.2 (CH 2 OH), 80.1 (O-CH 2 ), 85.5 (CH 2 OH), 103.2 (Ar-C), 103.2 (CH 2 =), 114.1 ( Ar-C), 115.2 (Ar-C), 119.4 (Ar-C), 127.8 (Ar-C), 131.3 (Ar-C), 132.0 (Ar-C), 136.7 ( (Ar-C), 136.7 (= CH-), 137.4 (Ar-C), 144.3 (Ar-C), 145.2 C), < / RTI > 153.2 (Ar-C).

UV? Max (CHCl 3 ) nm (?) 279 (11.1 × 10 4 ),

IR (KBr) cm -1 : 3439 (OH), 1032 (C-C)

MS does not measure

· MSX-6

MSX-6 is a mixture of MSX-6A and MSX-6B. The IUPAC name for MSX-6A is cis-docos-12-enoic acid. The IUPAC name for MSX-6B is (Z) -octadec-9-enoic acid (oleic acid). Figure 5A shows the structural formulas of MSX-6A and MSX-6B. FIG. 5A also shows the results of 13 C-NMR assignment and HMBC of MSX-6A.

FIG. 5B is a chart of 1 H-NMR of MSX-6A.

1 H-NMR (CDCl 3) δ (ppm): 0.88 (3H, t, J = 6.4Hz, CH 3), 1.26-1.31 (20H, m, -CH 2 -), 1.63 (2H, t, J = 7.0Hz, C H 2 CH 2 COOH ), 2.01 (4H, t, J = 5.5Hz, C H 2 CH = CHC H 2), 2.34 (2H, t, J = 7.6Hz, CH 2 COOH), 5.34 ( 2H, br, s, C H = C H ).

FIG. 5C shows a chart of 13 C-NMR of MSX-6A.

13 C-NMR (CDCl 3) δ (ppm): 14.1 (CH 3 -), 22.7 (-CH 2 -), 24.7 (-CH 2 -), 27.1 (-CH 2 -), 27.2 (-CH 2 - ), 29.0 (-CH 2 -) , 29.1 (-CH 2 -), 29.2 (-CH 2 -), 29.3 (-CH 2 -), 29.4 (-CH 2 -), 29.6 (-CH 2 -), 29.7 (-CH 2 -), 29.8 (-CH 2 -), 31.9 (-CH 2 -), 34.1 (-CH 2 -), 129.7 (-CH =), 130.0 (-CH =), 180.3 (-C = O).

IR (KBr) cm -1 : 1707 (COOH)

UV and MS not measured

The structural formula of MSX-6B was obtained by comparing 1 H-NMR, 13 C-NMR and IR data of oleic acid as a reference material and MSX-6 B data (UV and MS not measured).

Example 2

Preparation of deodorant

Each of the MSX-1 to MSX-6 isolated in Example 1 was dissolved in a small amount of ethanol, and the concentration of ethanol was 45% (volume / volume) and the concentration of the compound was 1 mg / L with a mixed solvent of ethanol and water Adjusted. Each solution was adjusted to pH 6.5 to pH 8.5 with hydrochloric acid or sodium hydroxide. Each of the above-mentioned adjusting solutions is hereinafter referred to as a deodorant A, a deodorant B, a deodorant C, a deodorant D, a deodorant E and a deodorant F.

Example 3

Deodorizing Effect on Hydrogen Sulfide (Gas Chromatographic Analysis)

The hydrogen sulfide gas was prepared as follows. 0.1 ml of a 360 mM sodium sulfide solution was added to a 20 ml capacity headspace vial, and 0.1 ml of 720 mM hydrochloric acid was added slowly and mixed. This was placed in an incubate at 30 캜 for 30 minutes, and the gas was volatilized. This headspace gas was used as a test hydrogen sulfide gas.

Each of the deodorants A to F was adjusted to pH 8.0, and each 1 ml of the deodorant was placed in a new 20 ml capacity headspace vial and sealed with a stopper to prepare a sample for measurement. A 45% (volume / volume) aqueous ethanol solution containing no deodorant was used as a control sample, and a deodorant (45% (volume / volume) aqueous ethanol solution) of MSX-245 was used as a positive control.

From the vial containing the hydrogen sulfide gas for test, 0.04 ml of the headspace gas was taken with an air cylinder (0.1 ml), added to each of the measurement sample and the control sample, and incubated at 30 ° C. Thirty minutes after the initiation of the incubation, 0.1 ml of the headspace gas was taken with an air cylinder (1 ml) and analyzed by gas chromatography (gas chromatograph: G-3900 Hitachi Seisakusho, column: CP-Silica Plot, detector: conducted a FPD, the sample injection port temperature 200 ℃, detector temperature 230 ℃, column temperature 220 ℃, carrier gas pressure 200kPa, a gas pressure of O 2 60kPa, H 2 60kPa, N 2 150kPa for FPD).

The deodorization rate for hydrogen sulfide was obtained from the following equation.

Deodorization rate (%) = [(C-S) / C] 100

C: hydrogen sulfide gas concentration in the control sample vessel

S: hydrogen sulfide gas concentration in the sample container for measurement

The results are shown in Fig. As shown in FIG. 6, each deodorant prepared in Example 2 and positive control MSX-245 reduced the concentration of hydrogen sulfide gas. In particular, the deodorants B, C, D and F showed high deodorization rates. It is considered that the deodorization mechanism of the deodorant A to F with respect to hydrogen sulfide is a chemical deodorization by a compound contained in each of the deodorant A to F. [

Example 4

Deodorizing effect on isovaleric acid (sensory test)

An isovaleric acid standard solution (1,000 ppm, manufactured by Wako Pure Chemical Industries, Ltd.) was diluted with 20 ppm of distilled water to pass through an activated carbon column, and this was used as an odor solution of isovaleric acid. 0.5 ml of the above-mentioned odor solution and 0.05 ml of each of the deodorant A to F (measurement sample) were added to 2.0 ml microtube. Mixed with a Vortex mixer, and allowed to stand for 30 minutes. The samples were then mixed with a vortex mixer immediately prior to the evaluation, and the samples were subjected to sensory evaluation by 7 to 8 skilled panelists. The average value was calculated for the above evaluation result. In addition, a 45% (volume / volume) aqueous ethanol solution containing no deodorant was used as a control sample, and a deodorant of MSX-245 same as Example 3 was used as a positive control.

The deodorizing effect on isovaleric acid was judged in accordance with the six-stage odor intensity indication method of the odor prevention method shown below. The results are shown in Table 1 below.

Evaluation Criteria (Stage Strength Indication Method in Step 6)

0: odorless

1: Barely detectable odor (detection threshold)

2: A weak odor (cognitive threshold value)

3: Easily detectable odor

4: Strong odor

5: Strong odor

From Table 1 below, each deodorant A to F and positive control showed a deodorizing effect on isovaleric acid. In particular, deodorant B, C, D and F showed deodorant effect as high as 0 ~ 1 on the evaluation criteria.

Figure 112010051079388-pct00006

Example 5

Deodorizing Effect on Trimethylamine (Sensory Evaluation)

A trimethylamine standard solution (1,000 ppm, manufactured by Wako Pure Chemical Industries, Ltd.) was diluted to 20 ppm with an odorless water which had been passed through an activated carbon column, and this was used as an odor solution of trimethylamine (TMA). 0.5 ml of the above-mentioned odor solution and 0.05 ml of each of the deodorant A to F (measurement sample) were added to 2.0 ml microtube. Mixed with a Vortex mixer, and allowed to stand for 30 minutes. The samples were then mixed with a vortex mixer immediately prior to the evaluation, and the samples were subjected to sensory evaluation by 7 to 8 skilled panelists. An average value was calculated for the above evaluation. A 45% (vol / vol) aqueous ethanol solution containing no deodorant was used as a control sample, and the same MSX-245 deodorant as in Example 3 was used as a positive control.

The sensory evaluation for TMA was carried out in accordance with the method for displaying odor intensity in step 6 of the odor prevention method described in Example 4. [ The results are shown in Table 2 below.

As shown in Table 2 below, each of the deodorants A to F and the positive control showed a deodorizing effect on TMA. In particular, the deodorizers B, C, D and F showed a deodorizing effect as high as about 1: 1.

Figure 112010051079388-pct00007

Example 6

Deodorant Effect on Tobacco Odor (Sensory Test)

A 5-liter capacity Erlenmeyer flask was inverted, and a cigarette with a fire was placed at about 5 cm from the opening of the Erlenmeyer flask, and cigarette smoke was collected for about 30 to 40 seconds. A cloth (cotton towel) of 10 cm x 10 cm was placed in a triangular flask for collecting smoke, sealed quickly, and the flask was soaked in a cloth for 5 minutes while shaking the flask. Thereafter, the cloth was taken out from the flask to prepare a test cloth for tobacco odor. A 200-fold dilution of each of the deodorants A to F of the sample for measurement was sprayed five times (0.15 g / one time × 5 times = about 0.75 g) on the cloth, and then the cloth was thoroughly wrung to homogenize the deodorant on the cloth. As a control, distilled water was sprayed five times (0.15 g x 5 times = about 0.75 g) of a 200-fold dilution of the same MSX-245 deodorant as in Example 3 as a positive control, Each liquid was homogenized in the whole cloth. Sensory evaluation was carried out by 7-8 skill panel after 4-5 hours of spraying each sample. The evaluation criteria are as follows. The average was calculated for the above evaluation. The results are shown in Table 3 below.

Sensory evaluation standard

◎: The odor completely disappeared

○: The smell disappeared considerably

△: A little odor disappeared

X: not disappear

Figure 112010051079388-pct00008

As shown in Table 3, the deodorant A to F and the positive control showed a deodorizing effect on the smell of tobacco. In particular, deodorants B, C, D and F showed high deodorizing effect.

Example 7

Deodorant effect on odor of pets (sensory test)

Isovaleric acid and acetic acid were added to odorless water so as to have final concentrations of 10 ppm and 200 ppm, respectively, and mixed, and this solution was used as a pseudo-pet odor stock solution. After the stock solution of the pseudo pet odor was filled in a spray bottle, the spray bottle was sprayed seven times (0.15 g x 7 times = about 1.05 g) on a 10 cm x 10 cm cloth (cotton cloth) (test cloth). After the above spraying, the cloth was wiped well, and the crude petroleum fragrance stock solution was uniformized on the cloth and air-dried to give a test cloth. Then, the deodorant B, the deodorant C, the deodorant D and the deodorant F in the measurement sample were sprayed five times (0.15 g x 5 times = about 0.75 g) with a 200-fold dilution of the deodorant F and the deodorant F was homogenized . In addition, distilled water as a control was used as a control, and a 200-fold dilution of the same deodorant MSX-245 as that in Example 3 was sprayed on the test cloth seven times (0.15 g x 7 times = about 1.05 g) Rinse well and homogenize each liquid on the cloth. Each sample was sprayed and 4-6 hours, 1 day, 7 days, 14 days and 30 days later, sensory evaluation was performed by 7 to 8 skilled panelists. The evaluation criteria are the same as those described in Example 4, i.e., the six-stage odor intensity display method of the malodor prevention method. The average was calculated for the above evaluation. The results are shown in Table 4 below. The fabric was also stored in a sealed container (sealed aluminum pack) at room temperature until provided for evaluation.

Figure 112010051079388-pct00009

As shown in Table 4, the deodorant B, the deodorant C, the deodorant D, the deodorant F, and the positive control showed a deodorizing effect on the odor of the pet odor for about one month after 4 to 6 hours of the deodorant spraying.

Example 8

Mist spray type deodorant

The deodorant B, the deodorant C, the deodorant D and the deodorant F were each diluted with water so that the concentrations of the deodorant samples were 20% and 0.1% (both volumes / volume), respectively, and each was filled in a mist spray bottle. Each of the deodorant packed in the mist spray bottle was discomforted by the animal odor in the large dog having an animal odor, the dog sprayed on the dog house, the dog and the dog house, and the effect lasted for 7 days.

Example 9

Aerosol type deodorant

(Volume / volume) so that the concentrations of the deodorant samples of deodorant B, deodorant C, deodorant D and deodorant F were 60% and 1% (both volume / volume) Lt; / RTI > Each of the obtained mixtures was charged into an aerosol container together with injection gas (LPG and carbon dioxide). When the deodorant packed in the aerosol container was sprayed on the food garbage with odor, the odor derived from the food garbage was suppressed, and the effect lasted more than 24 hours.

Example 10

Gel deodorant

2.2 g of carrageenan and 85 g of water were added to a 200 ml beaker and heated to 70 캜 with good stirring to completely dissolve carrageenan. Subsequently, when the mixture was cooled to 50 캜, 15 g of each of the deodorant B, deodorant C, deodorant D and deodorant F was added and mixed. Thereafter, water was added and mixed so that the total weight became 100 g. The mixture was cooled and solidified to obtain a gel-like deodorant. Similarly, the gel deodorant was prepared to obtain three gel deodorants. Each of the three gel deodorants was placed in a desiccator having a capacity of 2.6 liters, sealed, and stabilized at 20 DEG C for 3 hours. Trimethylamine gas was injected into the desiccator so that the initial concentration would be about 20 ppm. After 24 hours, the trimethylamine concentration was measured with a detection tube (Model No. 180L, manufactured by Gastec Co., Ltd.) I got it. After the measurement, the gel deodorant was individually put into a 300 mL beaker and stored in a constant temperature and humidity bath at 20 DEG C and 60% humidity until the next measurement. The deodorizing effect was measured on the day when the gel deodorant was prepared, 7 days after preparation, and 14 days after preparation, and the deodorization rate was determined from the residual concentration of trimethylamine. The deodorization rate was obtained by the following formula. The average value of the deodorization rates of the three deodorants was calculated. The results are shown in Table 5 below.

Deodorization rate (%) = [1- (trimethylamine concentration at the end of measurement) / (trimethylamine concentration at the start of measurement) 占 100

Figure 112010051079388-pct00010

As shown in Table 5, the gel deodorant of this example exhibited a high deodorizing activity against trimethylamine.

Example 11

Indoor deodorization by humidifier

At the house of the elderly, especially odor-intensive room was chosen, and it became a test object. About 1.5 liters of water was added such that the deodorant B, deodorant C, deodorant D and deodorant F had a concentration of 0.05% (volume / volume) of each deodorant sample. Each of the above solutions was installed in a humidifier. The operation of the humidifier was intermittently operated at a frequency of 1 minute for 15 minutes using an intermittent timer. As a result, odor was suppressed during one day.

Example 12

Feces treatment agent for pets

Deodorant B, deodorant C, deodorant D and deodorant F were used to prepare a fecal treatment agent for each pet. The formulation of the treating agent is 50 parts of bentonite, 50 parts of wood powder, 1 part of deodorant and 50 parts of water. These raw materials were mixed with a ribbon mixer, and pellets having a diameter of 3 mm and a length of 8 to 20 mm were obtained with a disk-shaped pelleter. This was further dried with a rotary drier, and each sample was used. As a control, a sample was prepared using 1 part of water instead of the deodorant in the treatment agent.

20 g of each of the above samples was placed in a 500 mL Erlenmeyer flask, 2 ml of 0.5% ammonia water was added thereto, the stopper was closed, and incubated at 30 DEG C for 20 minutes. After the incubation, the concentration (ppm) of ammonia in the gas portion was measured with a detection tube (Model No. 3La, manufactured by Gastec Co., Ltd.). As the blank value, the ammonia concentration in the case where only ammonia was added without adding the sample was measured to calculate each deodorization rate (%). The results are shown in Table 6 below.

Figure 112010051079388-pct00011

Because bentonite absorbs ammonia to some extent, the control also has a deodorizing effect compared to the blank. The treating agent using each of the above-described deodorant agents of the embodiment of the present invention clearly exhibited a deodorizing effect more than that.

Example 13

Preparation of spray type deodorant 1 ~ 4

, 0.6% (volume / volume, the same) of each deodorant sample of deodorant B, deodorant C, deodorant D and deodorant F and 2.0% of TEGO DEO CW90 (manufactured by Gold Schmidt Co.) as zinc ricinoleate 1%), 5.0% of dipropylene glycol, 35.0% of industrial ethanol, and the remainder were mixed with water to prepare spray type deodorants 1 to 4, respectively, by a conventional method.

Example 14

Preparation of spray type deodorant 5 ~ 8

1.0% of each deodorant sample of the deodorant B, the deodorant C, the deodorant D and the deodorant F, and the product of TEGO SORB CONC. (About 0.5% as zinc ricinoleate), 5.0% of dipropylene glycol, 20.0% of industrial ethanol, and the remainder were mixed with water to prepare a spray type deodorant 5 to 8 were prepared.

Example 15

Preparation of spray type deodorant 9-12

0.6% of each of the deodorant samples of deodorant B, deodorant C, deodorant D and deodorant F and 0.6% of a plant extract other than sugar cane extract (trade name: Puril) (manufactured by Matsushita Electric Works Co., Ltd.), 20.0% Water was added to the remainder, and spray type deodorant Nos. 9 to 12 were prepared according to a conventional method.

Example 16

Preparation of spray type deodorant 13-16

0.6% of each deodorant sample of the deodorant B, the deodorant C, the deodorant D and the deodorant F, 0.6% of the plant extract other than the sugarcane extract, the product name "Smegal" (manufactured by Environmental Science Development Co., Ltd.) , And water was added to the remainder, spray type deodorants 13 to 16 were prepared according to a conventional method.

Example 17

Preparation of spray type deodorant 17-20

0.6% of each deodorant sample of the deodorant B, the deodorant C, the deodorant D and the deodorant F, 0.6% of the plant extracts other than the sugarcane extract and 0.6% of the product name "Panzil" (manufactured by Risogai Kogyo Kogyo Co., , And water was added to the remainder, spray type deodorant 17 to 20 were prepared according to a conventional method.

[Comparative Example 1]

Preparation of spray type deodorant A

In the formulation of the spray type deodorant of Example 13, a spray type deodorant was prepared by a conventional method without using the deodorant B, the deodorant C, the deodorant D and the deodorant F samples.

[Comparative Example 2]

Preparation of spray type deodorant B

In the formulation of the spray type deodorant of Example 13, 2.0% of beta -cyclodextrin was added in place of the deodorant sample of each of the deodorant B, deodorant C, deodorant D and deodorant F, and the spray agent was prepared by a conventional method, Type deodorant.

[Deodorization test 1]

The spray type deodorants 1 to 20 of Examples 13 to 17 and the spray type deodorants A to B of Comparative Examples 1 and 2 were subjected to the following tests to evaluate their deodorizing effect.

Odor evaluation boxes were prepared in which the odor intensity of hydrogen sulfide, methyl mercaptan, and isovaleric acid, which are general odors, was set to step 3 of the odor intensity intensity indication method of the odor prevention method described in Example 4. The odor evaluation for the above three kinds of odors was performed by a skilled panel according to the following evaluation method. A detailed test method is shown below.

The spray-type deodorant was sprayed to the 2000 liters capacity odor evaluation box in which the odor intensity was 3, and the odor intensity was 3 (0.3 g per spray amount). Ten skilled panelists evaluated the odor effect on the odor after one minute and ten minutes after spraying based on the odor intensity indication method of the sixth stage of the odor prevention method described in Example 4 and evaluated each panel for each spray type deodorant The average value of the values was obtained. The results are shown in Table 7 below.

Figure 112014021664941-pct00058

From Table 7, it can be seen that the spray type deodorant of Examples 13 to 17 exhibited excellent deodorizing effect after 1 minute spraying on hydrogen sulfide, methyl mercaptan, and isovaleric acid, and the effect persisted even after 10 minutes of spraying. On the other hand, in the spray type deodorant of Comparative Examples 1 and 2, sufficient deodorizing effect was not obtained even after 1 minute after spraying and 10 minutes after spraying.

Example 18

Preparation of deodorant compositions 1 to 4

0.3% of each deodorant sample of the deodorant B, deodorant C, deodorant D and deodorant F, 1.0% of the product name "Super Purilel A-10" (manufactured by Matsushita Electric Works Co., Ltd.), 4.0% of triethanolamine, 2.0%, water was added to the residue, and the pH was adjusted to 7.0 with ammonia to obtain deodorant compositions 1 to 4, respectively.

Example 19

Preparation of deodorant compositions 5 to 8

1.0% of each deodorant sample of the deodorant B, deodorant C, deodorant D and deodorant F and 0.5% of the product name "Sumeral LG (Environmental Science Inc.)", 0.6% of triethanolamine and 2.0% And water were mixed with the residue and adjusted to pH 7.0 with ammonia to obtain deodorant compositions 5 to 8, respectively.

Example 20

Preparation of deodorant compositions 9 to 12

0.3% of each deodorant sample of the deodorant B, deodorant C, deodorant D and deodorant F, 1.0% of the product name "Smegal LG" (manufactured by Environmental Science Inc.), 0.8% of triethanolamine, 2.0% Water was added to the residue and adjusted to pH 7.0 with ammonia to obtain deodorant compositions 9 to 12, respectively.

Example 21

Preparation of deodorant compositions 13 to 16

0.3% of each deodorant sample of the deodorant B, deodorant C, deodorant D and deodorant F, 3.0% of the product name "Super Purilel A-10" (manufactured by Matsushita Electric Works Co., Ltd.), 2.3% of monoethanolamine, 3.0% citric acid and water were mixed with the residue and adjusted to pH 7.0 with ammonia to obtain deodorant compositions 13 to 16, respectively.

[Comparative Example 3]

Preparation of deodorant composition

1.2% of monoethanolamine, 2.0% of citric acid and water were mixed with the residue and adjusted to pH 7.0 with ammonia to obtain a control sample.

[Deodorization Test 2]

In order to confirm the deodorizing effect of the deodorant composition of the deodorant compositions 1 to 16 and the comparative example 3 of Examples 18 to 21, deodorization test for ammonia, methyl mercaptan, isovaleric acid, and rugs used for dogs raised at home ) Was used for the deodorization test. The results are shown in Table 8 below.

Details of the test method are as follows.

≪ Test method (1): Deodorization test of ammonia >

10 mL of a sample (the deodorant composition or the control sample of Examples 18 to 21 above) was placed in a 1 L glass bottle container, and 1 mL of 1% aqueous ammonia solution was injected. After standing for 10 minutes, sensory evaluation was carried out by 10 skilled panelists to obtain an average. In addition, the evaluation criteria are based on the six-stage stink intensity intensity indication method of the odor prevention method described in Example 4.

≪ Test method (2): Deodorization test of methyl mercaptan >

10 mL of the sample was placed in a 1 L glass bottle, and 1 mL of 0.1% methylmercaptan ethanol solution was injected. After standing for 1 hour, sensory evaluation was performed by 10 skilled panelists to obtain an average. In addition, the evaluation criteria are based on the six-stage stink intensity intensity indication method of the odor prevention method described in Example 4.

≪ Test method (3): Deodorization test of isovaleric acid >

10 mL of a sample was placed in a 1 L glass bottle, and 100 μL of 1% isovaleric acid aqueous solution was injected. After standing for 1 hour, sensory evaluation was performed by 10 skilled panelists to obtain an average. In addition, the evaluation criteria are based on the six-stage stink intensity intensity indication method of the odor prevention method described in Example 4.

≪ Test method (4): Deodorization test of rug used in indoor room &

The sample was sprayed three times (about 2.5 g) on the rug used by the dog that was raised in the home, and the sensory evaluation was performed on the odor remaining on the rug. The evaluation criteria are as follows.

Sensory evaluation standard

◎: Completely foul odor

○: The odor has disappeared significantly

△: A little odor disappeared

X: Not deodorized

Figure 112014021664941-pct00059

It can be seen from Table 8 that the deodorant compositions 1 to 16 of Examples 18 to 21 exhibited excellent deodorizing effect on the indoor rug which is a source of ammonia, methyl mercaptan, isovaleric acid and odor. On the other hand, the deodorant composition of Comparative Example 3 showed almost no deodorizing effect.

Example 22

Preparation of deodorant cleaners 1 and 2

1.0% of each of the deodorant samples of deodorant B and deodorant F (volume / volume, the same applies hereinafter), and 1.0% of the product name of "Sumeral LG" (manufactured by Environmental Science Inc.) as a plant extract, 3.0% of citric acid and 0.5% of polyglycerol ester 0.5 %, Saponin 0.5%, industrial ethanol 10.0%, POE isostearyl ether 0.1%, and the residue was mixed with water and adjusted to pH 4.8 with sodium hydroxide to obtain deodorant cleaners 1 and 2, respectively.

Example 23

Preparation of deodorant cleaners 3 and 4

1.0% of each deodorant sample of the deodorant B and deodorant F and 1.0% of the product name "Sumeral LG" (manufactured by Environmental Science Development Co., Ltd.) as the plant extract and 1.0% of the product name "Super Purilel A- Water, and 2.5% of citric acid, 1.0% of propylene glycol ester, 0.5% of saponin, 10.0% of industrial ethanol, and adjusted to pH 4.8 with sodium hydroxide to obtain deodorant cleaners 3 and 4, respectively did.

Example 24

Preparation of deodorant cleaners 5 and 6

1.0% of each deodorant sample of the deodorant B and deodorant F and 0.5% of the product name "Smegal LG" (manufactured by Environmental Science Development Co., Ltd.), 2.5% of citric acid, 0.5% of saponin, 0.1% of POE isostearyl ether, , 10.0% of industrial ethanol, and water were added to the residue and adjusted to pH 4.8 with sodium hydroxide to obtain deodorant cleaners 5 and 6, respectively.

Example 25

Preparation of deodorant cleaners 7 and 8

0.5% of each deodorant sample of deodorant B and deodorant F and 1.0% of a product name of "Sumeral LG" (manufactured by Environmental Science Development Co., Ltd.) and "Super Puril A-10" (manufactured by Matsushita Electric Works Co., Ltd.) %, Citric acid 2.5%, lecithin 0.1%, saponin 0.5%, industrial ethanol 10.0%, and the remainder were mixed with water and adjusted to pH 5.0 with sodium hydroxide to obtain deodorant cleaners 7 and 8, respectively.

Example 26

Preparation of deodorant cleaners 9 and 10

1.0% of each deodorant sample of the deodorant B and deodorant F and 0.5% of the product name "Smegal LG" (manufactured by Environmental Science Development Co., Ltd.), 2.5% of citric acid, 0.5% of saponin, 0.1% of POE isostearyl ether, 10.0% of industrial ethanol, and water were added to the residue and adjusted to pH 5.8 with sodium hydroxide to obtain deodorant cleaners 9 and 10, respectively.

Example 27

Preparation of deodorant cleaners 11 and 12

0.5% of each deodorant sample of deodorant B and deodorant F and 1.0% of a product name of "Sumeral LG" (manufactured by Environmental Science Development Co., Ltd.) and "Super Puril A-10" (manufactured by Matsushita Electric Works Co., Ltd.) %, Citric acid 2.5%, lecithin 0.5% and industrial ethanol 10.0%, and the residue was mixed with water and adjusted to pH 5.0 with sodium hydroxide to obtain deodorant cleaners 11 and 12, respectively.

Example 28

Preparation of deodorant cleaners 13 and 14

0.5% of each deodorant sample of the deodorant B and deodorant F and 0.5% of the product name "Sumeral LG" (manufactured by Environmental Science Development Co., Ltd.) and 0.5% of the product name "Super Purilel A-10" (manufactured by Matsushita Electric Works, %, Citric acid 2.0%, saponin 0.1%, industrial ethanol 10.0%, and the residue were mixed with water and adjusted to pH 4.5 with sodium hydroxide to obtain deodorant cleaners 13 and 14, respectively.

Example 29

Preparation of deodorant cleaners 15 and 16

1.0% of each deodorant sample of the deodorant B and deodorant F and 1.0% of the product name "Sumeral LG" (manufactured by Environmental Science Development Co., Ltd.) as the plant extract and 1.0% of the product name "Super Purilel A- % Of citric acid, 2.0% of citric acid, 2.5% of sodium hydrogen sulfate, 5.0% of saponin and 10.0% of industrial ethanol, and the pH of the residue was adjusted to 4.8 with sodium hydroxide to prepare deodorant cleaners 15 and 16 .

[Comparative Example 4]

Preparation of deodorant cleaner (A)

1.0% citric acid, 10.0% lecithin, 10.0% industrial grade ethanol, water was added to the residue, and the pH was adjusted to 3.5 with sodium hydroxide to obtain a deodorant detergent.

[Comparative Example 5]

Preparation of deodorant cleaner (B)

0.01% of trade name "Sumeral LG" (manufactured by Environmental Science Inc.), 0.01% of trade name "Super Purilel A-10" (manufactured by Matsushita Electric Works Co., Ltd.), 3.0% of citric acid, 10.0% of industrial ethanol, Water was added and adjusted to pH 6.0 with sodium hydroxide to obtain a deodorant cleaning agent.

[Comparative Example 6]

Preparation of deodorant cleaner (C)

2.5% citric acid, 10.0% industrial ethanol, water was added to the residue, and the pH was adjusted to 4.8 with sodium hydroxide to obtain a deodorant detergent.

[Deodorization Test 3]

In order to confirm the deodorizing effect of the deodorant cleaners (A to C) of the deodorant cleaners 1 to 16 and the comparative examples 4 to 6 of Examples 22 to 29, deodorization test for ammonia, methyl mercaptan, isovaleric acid, Urine, and urine for model urine. In addition, we confirmed the cleaning effect of urine sediment and model urine. Ammonia, methyl mercaptan, and isovaleric acid were evaluated using the test methods (1) to (3) described in the above deodorizing test 2. In addition, the deodorization test and the washing test using dog urine and model urine raised at home were carried out by the following test methods.

≪ Test method (5): Deodorization test and cleaning test using urine of dogs and model urine &

1 ml of urine and model urine (0.003% bilirubin (urine pigment), 1% ammonia, 1% NaCl) was applied to the carpet and patted with a tissue lightly. Thereafter, the sample was treated (the sample was fired at the size of the golf ball on the carpet, the contaminant was floated with a brush, and lightly wiped with a tissue). Odor and remaining color were evaluated by sensory evaluation by 10 skilled panelists, and the average of the evaluations was obtained. The evaluation standards for the deodorization test were the same as those described in Example 4, i.e., the six-stage odor intensity display method of the odor prevention method. With respect to the evaluation criteria of the cleaning test, the color in the case of no treatment was taken as 5 points, and the color when the pollutant completely dropped was 1 point.

Figure 112015105563112-pct00066

As shown in Table 9, the deodorant cleaners 1 to 16 had superior deodorizing performance to ammonia, methyl mercaptan, and isovaleric acid, compared with the deodorant cleaners A to C, and also had dog urine or model urine, The deodorizing test and the cleaning test also showed excellent deodorizing performance and cleaning performance.

Example 30

Hair essence

3.2% of volatile isoparaffin, 1.5% of methylpolysiloxane, 1.5% of glycerin, 2.5% of 1,3-butylene glycol and 70% of sorbitol solution (1.0%) of deodorant sample of deodorant B, deodorant C, deodorant D and deodorant F, %, Polyethylene glycol 6000 0.5%, dioleoyl polyethylene glycol 0.05%, diisostearic acid polyglyceryl 0.5%, sodium hydroxide 0.05%, paraben 0.2%, phenoxyethanol 0.2%, edetate trisodium 0.1%, carrageenan 0.5% 0.5% of dimethyldistearyl ammonium hectorite, 0.8% of palmitic acid dextrin, 0.4% of carboxyvinyl polymer, and 1.5% of high molecular weight methylpolysiloxane (degree of polymerization = 3000). In the case of a hair essence containing fragrance, a proper amount of fragrance is added. In the case of a hair essence without fragrance, the fragrance is not added and purified water is added to the remainder to obtain hair essences A1 to A4 (with fragrance) and B1 ~ B4 (unscented) was prepared.

The hair essences A1 to A4 and B1 to B4 were tested for deodorizing effect against the smell of tobacco described in Example 6. [ As a result, all of the hair essences of this example exhibited excellent deodorizing effect (sensory evaluation:?) Against the smell of tobacco.

Example 31

Hair Mist (Dispenser)

6.0% of each deodorant sample of deodorant B, deodorant C, deodorant D and deodorant F 5.0% of PVP / VAS-630 (manufactured by GAF), 5.0% of Yucca Former AM-75 (manufactured by Mitsubishi Chemical) To prepare hair mists A to D, respectively.

These hair mists A to D were subjected to a deodorant effect test for the smell of tobacco described in Example 6. As a result, all of the hair mists of this example exhibited excellent deodorizing effect (sensory evaluation:?) Against the smell of tobacco.

Example 32

shampoo

10.5% of each deodorant sample of deodorant B, deodorant C, deodorant D and deodorant F, 1.0% of dipropylene glycol, 0.1% of monostearic acid POE (20) sorbitan, 0.7% of POE (25) 2.0% of ethylene glycol, 2.5% of coconut oil fatty acid monoethanolamide, 5.0% of POE lauryl ether sodium sulfate, 10.0% of triethanolamine POE lauryl ether sulfate, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium beta- , 0.2% of acetic acid DL-α-tocopherol, 0.3% of phenoxyethanol, 0.2% of sodium benzoate, 0.3% of lecithin 0.3%, 1.0% of citric acid, 0.8% of sodium chloride, Respectively. In the case of shampoos containing fragrance, an appropriate amount of fragrance is added. In the case of fragrance-free shampoo, purified water is added to the residue without adding any fragrance, and fragrance-added shampoo A1 to A4 and fragrance-free shampoo B1 to B4 It was prepared.

Deodorant effect tests on the smell of tobacco described in Example 6 were carried out on fragrance-added shampoos A1 to A4 and non-fragrant shampoos B1 to B4. As a result, all of the shampoos of this example exhibited excellent deodorizing effect (sensory evaluation:?) Against the smell of tobacco.

Example 33

Hypoallergenic Shampoo

5.0% of each deodorant sample of deodorant B, deodorant C, deodorant D and deodorant F, 0.5% of glycerin, 2.0% of distearyl ethylene glycol, 1.0% of coconut fatty acid monoethanolamide, 2.0% of propylene glycol laurate, Sodium cyanide, 7.0% sodium cocoyl fatty acid amide propyl betaine 6.0%, polymer JR400 (manufactured by UCC) 1.0%, citric acid 0.5%, phenoxyethanol 0.3%, sodium benzoate 0.2%, disodium edetate 0.1%, soybean lecithin 0.2% And 0.5% of potato starch (manufactured by Sensomer CI-50 CALGON). In the case of hypoallergenic shampoos containing perfumes, an appropriate amount of perfume was added. In the case of non-perfume hypoallergenic shampoos, purified water was added to the remainders without adding any perfume, and the hypoallergenic shampoos A1 to A4 and non- Polarity shampoo B1 ~ B4.

To the hypoallergenic shampoo, a deodorant effect test for the smell of tobacco described in Example 6 was carried out. As a result, all hypoallergenic shampoos of this example exhibited excellent deodorizing effect (sensory evaluation:?) Against tobacco odor.

Example 34

Cosmetics

2.0% of methylene polysiloxane, 3.0% of cetanol, 3.0% of behenyl alcohol, 4.0% of glycerin, 2.0% of diglycerin, 2.0% of 2-ethylhexanoate, 1.0% of deodorant sample of deodorant B, deodorant C, deodorant D and deodorant F, 1.0% of amino-modified polysiloxane (Doeruda SM8702C), 0.5% of high molecular weight polysiloxane (polymerization degree = 4000), 1.0% of glyceryl monostearate, 2.0% of stearyl trimethylammonium chloride, 0.1% of citric acid, , And paraben 0.2%, respectively. In the case of a cosmetic composition containing a perfume, an appropriate amount of perfume is added. In the case of an unflavoured cosmetic composition, no perfume is added, and purified water is added to the remainder to prepare cosmetic compositions A1 to A4 and unflavoured cosmetic compositions B1 to B4 did.

The above-mentioned cosmetic material was subjected to a deodorizing effect test on the smell of tobacco described in Example 6. As a result, all of the cosmetic preparations of this example exhibited excellent deodorizing effect (sensory evaluation:?) Against tobacco odor.

Example 35

Spray for hair finishing

A deodorant B, a deodorant C, a deodorant D, and a deodorant F, 1.0% of each deodorant sample, 0.5% methylphenylpolysiloxane, 0.5% 1,3-butylene glycol, 0.2% liquid lanolin, 0.5% 2-ethylhexanoate, 0.5% of ethanolamide, 0.2% of POE-hardened castor oil pyroglutamate isostearate, 0.2% of paraben, 0.5% of 2-ethylhexyl palmitoxycinnamate, 8.0% of Yucca Former 104 (manufactured by Mitsubishi Chemical Corporation) Respectively. In the case of cosmetics containing fragrance, an appropriate amount of fragrance is added. In the case of fragrance-free cosmetics, no fragrance is added, and industrial residues are blended with the residues. B4, respectively.

The stock solution and LPG were mixed with the stock solution / LPG = 55/45, and spraying processes A1 to A4 for hair finishing and spray B1 to B4 for non-fragrant hair finishing were respectively prepared by a conventional method.

The above-described hair finishing spray was subjected to a deodorant effect test for the smell of tobacco described in Example 6. As a result, all of the hair finishing spray of the present example exhibited excellent deodorizing effect (sensory evaluation:?) Against the smell of tobacco.

Example 36

Hair spray 1-4

0.5% of deodorant sample, 0.5% of 2-ethylhexanoate, 0.3% of polyoxyethylene oleyl ether, 0.1% 12.0% manufactured by Kagaku Kogyo Co., Ltd.) and industrial residue ethanol were blended to obtain a stock solution of hair spray 1, respectively. The raw liquid was mixed with LPG and DME (dimethyl ether) in a stock solution / LPG / DME = 40/10/50, and hair sprays 1 to 4 were prepared by a conventional method.

For the hair sprays 1 to 4, a deodorant effect test for the smell of tobacco described in Example 6 was carried out. As a result, all of the hair sprays 1 to 4 of this example exhibited excellent deodorizing effect (sensory evaluation:?) Against the smell of tobacco.

Example 37

Hairspray 5 ~ 8

2.0% of the deodorant B, the deodorant C, the deodorant D and the deodorant F of each deodorant sample 2.0%, the liquid paraffin 6.0%, the methylpolysiloxane 3.0%, the methylphenylpolysiloxane 2.0%, the decyltetradecanol 6.0%, the 2-ethylhexanoate 3.0% Was mixed with industrial ethanol to obtain a stock solution of hairsprays 5 to 8, respectively. The stock solution and LPG were mixed at a stock solution / LPG = 50/50, and hair sprays 5 to 8 were prepared according to a conventional method.

The hair sprays 5 to 8 were subjected to a deodorizing effect test for the smell of tobacco described in Example 6. [ As a result, all of the hair sprays 5 to 8 of the present embodiment exhibited excellent deodorizing effect (sensory evaluation:?) Against the smell of tobacco.

Example 38

Rinse

3.0% of liquid paraffin, 3.0% of methylpolysiloxane, 1.0% of cetanol, 3.0% of octyldodecanol, 0.1% of vegetable protein, 0.1% of propylene glycol, 5.0% of deodorant B, deodorant C, deodorant D and deodorant F, 0.5% polyoxyethylene hardened castor oil, 0.5% polyoxyethylene stearyl ether, 1.5% alkyl trimethylammonium chloride, 0.1% citric acid, 0.5% potassium chloride, 0.3% phenoxyethanol, 0.01% pyrithione zinc solution (50% Respectively. In the case of the rinse containing the perfume, an appropriate amount of perfume was added. In the case of the non-perfume rinse, the perfume was not added, and the rinse A1 to A4 and the non-perfume rinse B1 to B4 were prepared by adding purified water to the remainder .

The deodorizing effect test on the smell of tobacco described in Example 6 was performed on the rinse. As a result, all of the rinses of this example exhibited excellent deodorizing effect (sensory evaluation:?) Against the smell of tobacco.

Example 39

Permanent Wave No. 1-8

0.5% of deodorant sample of deodorant B, deodorant C, deodorant D and deodorant F, 4.0% of glycerin, 1.0% of lauric acid monoethanolamine, 0.5% of polyoxyethylene oleyl ether, 0.2% of lauryl trimethylammonium chloride, 0.5% of aryl trimethylammonium, 5.0% of ammonium carbonate, 20% of urea, 15.0% of ammonium thioglycolate (50%) and 0.2% of hydroxyethanediphosphonic acid (60%). In the case of a permanent waving agent containing a perfume, an appropriate amount of a perfume is added. In the case of a permanent waving agent without a perfume, no perfume is added. Purified water is added to the residue, To prepare permanent waving agents (5 to 8) as perfumes.

The permanent waving agents (1 to 8) were subjected to a deodorizing effect test for the smell of tobacco described in Example 6. As a result, all of the permanent waving agents (1 to 8) of this Example exhibited excellent deodorizing effect (sensory evaluation:?) Against the smell of tobacco.

Example 40

Permanent Wave No. 9-12

0.5% of the deodorant B, the deodorant C, the deodorant D and the deodorant F of each deodorant sample 0.5%, the methylsiloxane emulsion 5.0%, the lauryldimethylaminoacetic acid betaine 0.5%, the sodium dihydrogenphosphate 0.1%, the sodium bromate 40.0 %, 0.5% potassium dihydrogen phosphate, 0.2% sodium benzoate, and purified water were added to the residue to prepare permanent waving agents (9 to 12).

The permanent waving agents (9 to 12) were subjected to a deodorizing effect test by the sensory evaluation of tobacco odor described in Example 6. As a result, all of the products of this Example exhibited excellent deodorizing effect (sensory evaluation:?) Against tobacco odor.

Example 41

Body lotion (dispenser)

1.0% of the deodorant sample, 20.0% of industrial ethanol, 6.0% of glycerin, 3.0% of 1,3-butylene glycol and 0.8% of POE (60) hardened castor oil of Examples 3, 4, , And mugwort extract 1.0% were mixed. Purified water was added to the residue to prepare lotion lotions 1 to 4 for the body, respectively.

The cosmetic lotion for body was subjected to a deodorant effect test for the smell of tobacco described in Example 6. As a result, all of the lotion lotions 1 to 4 for the body of the present example exhibited excellent deodorizing effect (sensory evaluation:?) Against tobacco odor.

Example 42

cream

A deodorant B, a deodorant C, a deodorant D and a deodorant F, a deodorant sample of 0.1%, vaseline 2.0%, methylpolysiloxane 3.0%, cetanol 2.0%, glycerin 3.0%, 1,3-butylene glycol 5.0% 2.0% of stearic acid, 3.5% of tri-2-ethylhexanoic acid glyceryl, 0.7% of polyoxyethylene glyceryl isostearate, 2.3% of glycerin monostearate, 0.15% of potassium hydroxide, 0.01% of sodium hexametaphosphate, 0.1% of sodium hyaluronate % Magnesium ascorbyl phosphate, 2.0% paraben, 0.3% carboxyvinyl polymer, and 0.05% carboxyvinyl polymer. In the case of the cream containing the perfume, an appropriate amount of perfume is added. In the case of the non-perfume cream, the perfume is not added, and the purified water is added to the remainder to prepare the creams A1 to A4 and the non- fragrant creams B1 to B4, did.

The cream was appropriately diluted with water, and a deodorizing effect test on the smell of tobacco described in Example 6 was carried out. As a result, all of the creams of this example exhibited excellent deodorizing effect (sensory evaluation:?) Against tobacco odor.

Example 43

Gel

The deodorant B, the deodorant C, the deodorant D, and the deodorant F, 1.0% of each deodorant sample, 5.0% of ethanol, 8.0% of glycerin, 4.0% of polyoxyethylene methyl glucoside, 1.0% of POE (12) lauryl ether, 0.3% of seed, 0.5% of potassium hydroxide, 2.0% of L-ascorbic acid-2-glucoside, 0.3% of paraben and 0.6% of carboxyvinyl polymer. In the case of a gel containing a perfume, an appropriate amount of perfume was added. In the case of a non-perfumed gel, no perfume was added. Purified water was added to the residue to prepare gels A1 to A4 and unfragrant gels B1 to B4, did.

The gel was appropriately diluted with water, and a deodorizing effect test on the smell of tobacco described in Example 6 was carried out. As a result, all of the gels of this example exhibited excellent deodorizing effect (sensory evaluation:?) Against the smell of tobacco.

Example 44

Whitening cream

6.0% of deodorant sample of deodorant B, deodorant C, deodorant D and deodorant F, 6.0% of liquid paraffin, 1.0% of vaseline, 2.0% of methylpolysiloxane, 3.0% of ethanol, 0.5% of cetanol, 6.0% 6.0% of polyglycol, 1.0% of polyethylene glycol 1500, 2.0% of hardening oil, 4.0% of 2-ethylhexanoate, 1.0% of polyoxyethylene glyceryl isostearate, 1.0% of polyoxyethylene glycerin monostearate, 0.02% of sodium metaphosphate, 0.1% of arginine hydrochloride, 0.1% of DL-alpha-tocopherol acetate, 0.5% of vegetable protein, 1.0% of rosemary extract, 0.2% of sodium hyaluronate, 5.0% of arbutin, 0.3% of phenoxyethanol, 0.05% of sodium, 1.0% of 2-ethylhexyl paramethoxycinnamate, 0.1% of xanthan gum and 0.1% of carboxyvinyl polymer were blended. In the case of a whitening cream containing a perfume, an appropriate amount of a perfume is added. In the case of a non-perfume whitening cream, no perfume is added. Purified water is added to the remainder to prepare whitening creams A1 to A4 and non- Creams B1 to B4 were prepared.

The whitening cream was appropriately diluted with water, and a deodorizing effect test on the smell of tobacco described in Example 6 was carried out. As a result, all of the whitening creams of this example exhibited excellent deodorizing effect (sensory evaluation:?) Against tobacco odor.

Example 45

Deodorant Body Cleansing

, 6.0% of propylene glycol, 8.0% of sorbitol solution (70%), 2.5% of lauric acid, 4.0% of palm oil fatty acid diethanolamide, 12.0% of POE alkyl (12%), deodorant B, deodorant C, deodorant D and deodorant F L-glutamic acid triethanolamine 3.0%, N-palmitoyl fatty acid acyl-L-glutamate 3.0%, 2-amino-2-methyl-1-propanol 2.5% , 0.1% of sodium metaphosphate, 0.02% of alpha -tocopherol, 0.5% of lily extract, 0.2% of paraben, 1.0% of carboxyvinyl polymer, and purified water to form deodorant body cleansing 1 to 4, respectively.

For the deodorant body cleansing, a deodorant effect test on the smell of tobacco described in Example 6 was carried out. As a result, the deodorant body cleansing of the present example showed excellent deodorizing effect (sensory evaluation:?) Against the smell of tobacco.

Example 46

Hair Manicure

The deodorant B, the deodorant C, the deodorant D and the deodorant F were mixed with 0.5% of each deodorant sample, 10.0% of benzyl alcohol, 15.0% of N-methylpyrrolidone, 3.0% of citric acid, 1.0% of xanthan gum, 0.8% of acid dye, To prepare hair nail polishes 1 to 4, respectively.

The hair nail polishes 1 to 4 were subjected to a deodorant effect test for the smell of tobacco described in Example 6. As a result, the hair nail polish of the present example exhibited excellent deodorizing effect (sensory evaluation:?) Against tobacco odor.

Example 47

Oxide powder

The deodorant B, the deodorant C, the deodorant D and the deodorant F 0.3%, the cetanol 10.0%, the POE 15 cetyl ether 2.0%, the sodium lauryl sulfate 2.0%, the liquid paraffin 5.0% A mixture of 3.0% methylsiloxane, 3.0% monoethanolamine, 8.0% propylene glycol, 2.0% ammonium hydrogen carbonate, 0.5% ammonium thioglycolate, 0.5% methanaminophenol, 0.5% 0.5% of 5-diamine, 0.5% of paraaminooctocresol, 0.2% of polymer JR400 (manufactured by UCC) and purified water were added to the remainder to prepare Form A1 to Form A4 of oxidized salts. Purified water was mixed with 10.0% cetanol, 2.0% POE (15) cetyl ether, 2.0% sodium lauryl sulfate, 5.0% liquid paraffin, 3.0% polymethylsiloxane, 18.0% hydrogen peroxide water (35%), Lt; 0 >. Subsequently, the components A1 to A4 and the component B of the oxidized salt frit were mixed in a ratio of AX / B = 1 / 0.5 to 2 (X = 1 to 4) .

The oxidized salt cake was appropriately diluted with water, and a deodorant effect test for the smell of tobacco described in Example 6 was carried out. As a result, all of the oxidative salt fungicides 1 to 4 of the present example exhibited excellent deodorizing effect (sensory evaluation:?) Against the smell of tobacco.

Example 48

Hair dressing (Hair dressing)

0.5% of each deodorant sample of deodorant B, deodorant C, deodorant D and deodorant F, 90.0% of industrial ethanol, 2.0% of tri-2-ethylhexanoic acid glyceryl, 0.5% of POE hardened castor oil, 1.0% of diisostearic acid diglyceryl, 0.5% of lauryldimethylamine oxide, 0.1% of lactic acid, 0.03% of sodium lactate, 0.5% of sucrose extract, 0.1% of hinokitiol, 0.1% of pantothenyl ethyl ether, 0.1% of beta -glycitalic acid, %, 0.1% of pyridoxine hydrochloride, 0.1% of tocopherol acetate, 0.1% of L-menthol, and purified water were added to the remainder to prepare Hair Growing Raws 1 to 4, respectively.

The hair growth stimuli were subjected to a deodorizing effect test for the smell of tobacco described in Example 6. [ As a result, all the hair growth promoters of this example exhibited excellent deodorizing effect (sensory evaluation:?) Against the smell of tobacco.

Example 49

Limited (antiperspirant) lotion

The deodorant B, the deodorant C, the deodorant D, and the deodorant F, 1.0% of the deodorant sample, 45.0% of industrial ethanol, 0.5% of isopropanol, 0.5% of 1,3-butylene glycol, 0.7% of triethyl citrate and polyoxyethylene polyoxypropyldecyl 0.2% of tetradecyl ether, 0.2% of particulate zinc oxide-coated nylon powder, 20.0% of aluminum hydrooxychloride solution (50%), 0.1% of sodium hexametaphosphate, 0.2% of benzalkonium chloride solution (50% 0.1% of polyvinylpyrrolidone and purified water were added to the residue to prepare restricted lotions 1 to 4, respectively.

The deodorant effect test on the smell of tobacco described in Example 6 was performed on the restricted lotion. As a result, all of the restricted lotions of the present Example exhibited excellent deodorizing effect (sensory evaluation:?) Against tobacco odor.

Example 50

Deodorant spray for body

1.5% of deodorant sample of deodorant B, deodorant C, deodorant D and deodorant F, 20.0% of industrial ethanol, 5.0% of glycerin, 5.0% of dipropylene glycol, 1.0% of POE and POP decyltetradecyl ether, And the undiluted spray for the body was separately prepared. The raw liquid and nitrogen gas were mixed at a raw liquid / nitrogen gas ratio of 99.3 / 0.7, and deodorant sprays 1 to 4 for a body were prepared by a conventional method.

The deodorant spray for the body was subjected to a deodorant effect test for the smell of tobacco described in Example 6. [ As a result, all of the deodorant sprays for the body of the present example exhibited excellent deodorizing effect (sensory evaluation:?) Against tobacco odor.

Example 51

Tobacco odor Deodorant hair mists

2.0% of high molecular weight amino-modified dimethylpolysiloxane, 2.0% of propylene glycol, 2.0% of propylene glycol, POE-hardening agent, 2.0% of deodorant B, deodorant C, deodorant D and deodorant F in each deodorant sample 2.0%, industrial ethanol 50.0%, volatile isoparaffin 0.5% 0.5% of castor oil, 1.0% of hydroxypropyl-beta-cyclodextrin and purified water were added to the residue to prepare a stock solution of a cigarette smell deodorizing hair mist. The raw liquid and nitrogen gas were mixed at a raw liquid / nitrogen gas ratio of 99.2 / 0.8, and cigarette smell deodorizing hair mists 1 to 4 were prepared by a conventional method.

The deodorant effect test on the tobacco odor described in Example 6 was performed on the tobacco odor deodorant hair mist. As a result, all of the cigarette odor deodorizing hair mists of the present example exhibited excellent deodorizing effect (sensory evaluation: ⊚) against tobacco odor.

Example 52

Hair Colon

5.0% of each deodorant sample of deodorant B, deodorant C, deodorant D and deodorant F, 15.0% of industrial ethanol, and 1.0% of flushing extract, respectively. In addition, an appropriate amount of perfume was added in the case of a hair cologne containing fragrance, and no fragrance was added in the case of a fragrance free hair cologne. Purified water was added to the residue to prepare a stock solution of hair cologne. The stock solution and dimethyl ether were mixed in a stock solution / dimethyl ether = 60/40 to prepare Hair Colongs A1 to A4 and Unflavoured Hair Colons B1 to B4, respectively.

For the hair cowl, a deodorant effect test on the smell of tobacco described in Example 6 was carried out. As a result, an excellent deodorizing effect (sensory evaluation:?) Was exhibited for the smell of tobacco in this example.

Example 53

Indoor deodorant spray

3.5% of each deodorant sample of deodorant B, deodorant C, deodorant D and deodorant F, 5.0% of industrial ethanol, 2.0% of green tea extract, 0.1% of hardened castor oil of POE (60), 0.2% of diglyceryl diisostearate, To prepare a stock solution of an indoor deodorant spray. The raw liquid and nitrogen gas were mixed at a stock solution / nitrogen gas ratio of 99.4 / 0.6, and the room-temperature deodorant sprays 1 to 4 were respectively prepared by a conventional method.

For the indoor deodorant spray, a deodorant effect test for the smell of tobacco described in Example 6 was carried out. As a result, all of the room-temperature deodorant sprays of this example exhibited excellent deodorizing effect (sensory evaluation:?) Against the smell of tobacco.

Example 54

Bubble Type Body Deodorant

0.5% of deodorant, 0.5% of industrial ethanol, 0.5% of silicone oil, 1.0% of 1,3-butylene glycol, 2.0% of zinc oxide, 1.0% of sericite, POP · deodorant, 0.8% of POP cetyl ether, 0.2% of citric acid, 0.1% of L-menthol, and purified water were mixed with the residue to prepare a stock solution of foam type body deodorant. The crude liquid and LPG were mixed in a stock solution / LPG = 92/8, and foam type body deodorants 1 to 4 were respectively prepared by a conventional method.

For the foam type body deodorant, a deodorant effect test on the smell of tobacco described in Example 6 was carried out. As a result, all of the foam type body deodorant of this example exhibited excellent deodorizing effect (sensory evaluation:?) Against the smell of tobacco.

Example 55

Car deodorant

The deodorant B, the deodorant C, the deodorant D and the deodorant F were each diluted with water to a concentration of 1% (volume / volume) of each deodorant sample to prepare vehicle deodorants 1 to 4, respectively. The deodorant for vehicle was set on the liquid side of the atomizer of the dual-fluid nozzle (liquid / liquid type). The operation of the atomizer was set up in the rear seat of the test subject and continuously operated with compressed air from a pressurized compressed air (base), for example, a baby compressor (Hitachi, Ltd.) .

(Tea A) in which the smell of cigarettes smells strongly in the car (tea B), tea in which the body odor remains in the car (tea C), fragrance of fragrance left in the tea (tea D ). The vehicle deodorant was sprayed with a sprayer for 15 minutes in each test subject's car. During spraying, the air conditioner was circulated at the maximum air volume, and the deodorant was spread evenly inside the vehicle. After spraying, the car window was opened and allowed to dry outdoors (20 ~ 30 ℃, clear ~ cloudy) for several hours (3 ~ 5 hours).

The evaluation was performed by 10 skilled panelists before spraying, after spraying, immediately after spraying, after spraying (after drying) and 1 day after spraying, and the average of the evaluations was calculated. In addition, the evaluation criteria are based on the six-stage stink intensity intensity indication method of the odor prevention method described in Example 4. The results of spraying vehicle deodorant 1, spraying vehicle deodorant 2, spraying vehicle deodorant 3, and spraying vehicle deodorant 4 are shown in Tables 10, 11, 12 and Table 13.

Figure 112014021664941-pct00061

Figure 112014021664941-pct00062

Figure 112014021664941-pct00063

Figure 112014021664941-pct00064

From the above Tables 10 to 13, all of the deodorants 1 to 4 of the vehicle showed a high deodorizing effect on odors (pet odor, cigarette odor, human body odor and aromatic odor) in the vehicle.

Example 56

Antioxidant ability

The antioxidant activity of the compounds of the present invention was evaluated in accordance with the method for evaluating the 1,1-diphenyl-2-picrylhydrazine (DPPH) radical scavenging activity of Blois (Toshiyuki Kimura et al., Vol. 49 , No. 4, 257-266 (2002), Blois, MSNaturevol.181, 1199-1120 (1958)). 19.7 mg of DPPH (manufactured by Wako Junyaku) was dissolved in 100 ml of ethanol to prepare a DPPH reagent solution. 10 mg of each of MSX-1 to 6 isolated in Example 1 was dissolved in 1 ml of ethanol and the ethanol solution was diluted 10-fold with 100 mM Tris (hydroxymethyl) aminomethane hydrochloric acid buffer (pH 7.4) (Tris-Buffer) To prepare sample solutions A to F, respectively. As a positive control, catechin (和 光 純 药), which has a very strong antioxidant ability, was used. Catechins of 0 mg, 0.5 mg, 1 mg, 1.5 mg and 20 mg were dissolved in 100 ml of 100 mM Tris-Buffer to prepare 0 ppm, 5 ppm, 10 ppm, 15 ppm and 200 ppm catechin standard solutions, respectively. After 1 ml of each of the sample solutions A to F and the catechin standard solution was dispensed into the test tube, 1 ml of the DPPH reagent solution was added to each test tube and stirred. After the stirring, the test tube was allowed to stand in a dark place for 30 minutes. After 30 minutes, the test tube was removed from the dark place, and 2 ml of 200 mM Tris-Buffer was added to the test tube. Then, the test tube was well stirred, and absorbance at a wavelength of 517 nm was measured with a spectrophotometer (manufactured by Hitachi, UV-2000). A calibration curve was prepared from the absorbance of the catechin standard solution and the antioxidative capacity of each sample solution was evaluated as DPPH radical scavenging activity as " catechin g / 100 g ". The results are shown in Table 14 below.

Figure 112010051079388-pct00019

From Table 14 above, MSX-2 to MSX-4 showed high DPPH radical scavenging activity. Therefore, MSX-2 to MSX-4 have antioxidant ability.

Claims (8)

A compound represented by the formula (1):
(Formula 1)
Figure 112015105563112-pct00020

[In the above formula (1)
R 1 is a hydrogen atom or a group represented by the following formula (4)
(Formula 4)
Figure 112015105563112-pct00067

R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an ethynyl group or an aldehyde group, and R 7 is a hydrogen atom or a methoxy group. The method according to claim 1,
R 1 is a hydrogen atom, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an ethenyl group and R 7 is a hydrogen atom compound. The method according to claim 1,
R 1 is a hydrogen atom, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an aldehyde group and R 7 is a hydrogen atom . The method according to claim 1,
R 1 is a group represented by the following formula 4, R 2 is a methyl group, R 3 is a hydrogen atom, R 4 is a hydrogen atom, R 5 is a methyl group, R 6 is an ethenyl group, R 7 is a methoxy group Lt; RTI ID = 0.0 > of:
(Formula 4)
Figure 112015105563112-pct00023
 delete delete delete delete
KR1020107017672A 2008-03-31 2009-03-30 Phenylpropanoid compound KR101605211B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JPJP-P-2008-093495 2008-03-31
JP2008093495 2008-03-31

Publications (2)

Publication Number Publication Date
KR20100131975A KR20100131975A (en) 2010-12-16
KR101605211B1 true KR101605211B1 (en) 2016-03-21

Family

ID=41135469

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020107017672A KR101605211B1 (en) 2008-03-31 2009-03-30 Phenylpropanoid compound

Country Status (4)

Country Link
JP (1) JP5456659B2 (en)
KR (1) KR101605211B1 (en)
CN (1) CN101983184B (en)
WO (1) WO2009123093A1 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5825053B2 (en) * 2010-11-17 2015-12-02 ライオン株式会社 Liquid-based sweat deodorant composition
JP5927566B2 (en) * 2011-07-01 2016-06-01 株式会社村中手芸 Manufacturing method of fragrance seal
JP6034118B2 (en) * 2012-10-03 2016-11-30 一丸ファルコス株式会社 Deodorant, antibacterial agent, and skin external preparation composition containing them
JP2017118889A (en) * 2015-12-28 2017-07-06 ライオン商事株式会社 Deodorant composition
JP6965111B2 (en) * 2017-11-09 2021-11-10 三井製糖株式会社 Hair quality improvement composition
JP7134745B2 (en) * 2018-06-29 2022-09-12 サンスター株式会社 emulsion composition

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001087365A (en) 1999-06-24 2001-04-03 Mitsui Sugar Co Ltd Deodorant

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU718850B2 (en) * 1996-09-24 2000-04-20 Mitsui Sugar Co., Ltd. Deodorizing substance
JP3894462B2 (en) * 1996-09-24 2007-03-22 三井製糖株式会社 Deodorant substance

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001087365A (en) 1999-06-24 2001-04-03 Mitsui Sugar Co Ltd Deodorant

Also Published As

Publication number Publication date
JP5456659B2 (en) 2014-04-02
JPWO2009123093A1 (en) 2011-07-28
CN101983184B (en) 2013-11-20
KR20100131975A (en) 2010-12-16
WO2009123093A1 (en) 2009-10-08
CN101983184A (en) 2011-03-02

Similar Documents

Publication Publication Date Title
US7332462B2 (en) Malodor counteractant compounds
EP1345883B1 (en) Malodor counteractant compositions
US4310512A (en) Derivatives of acetic and propionic acids, compositions containing same and use as malodor counteractants
KR101605211B1 (en) Phenylpropanoid compound
JPWO2012108495A1 (en) Aging odor suppressant containing oolong tea extract and / or strawberry tea extract
EP3725941A1 (en) Perfume composition for inhibiting odor
JP5851302B2 (en) Body odor suppressor
WO2008029822A1 (en) Deodorant comprising deodorizing substance originating in sugarcane distillate as the active ingredient and method of improving odor originating in sugarcane
JP6025442B2 (en) Diketone action inhibitor
JP4249862B2 (en) Deodorants
KR101781657B1 (en) Deodorant composition comprising essential oil from plant
ES2726919T3 (en) Macrocyclic ketone as an ingredient to counteract the bad smell
JP2002275495A (en) Perfumery composition for eliminating tobacco smell
JP4660088B2 (en) Deodorant and deodorant composition, cosmetic composition and cleaning composition containing the deodorant
JP6738155B2 (en) Deodorant composition for body odor
CA1041018A (en) 4-cyclohexyl-4-methyl-2-pentanone as deodorants
JP2002325828A (en) Deodorant and use thereof
EP3648763B1 (en) 2,4-disubstituted pyridines as malodor counteracting ingredients
KR102279633B1 (en) Composition for removing aldehyde-based odor and active oxygen
JP7260246B2 (en) Deodorants
JP2017038855A (en) Deodorant
JP6527005B2 (en) Deodorant composition, external preparation for skin containing the deodorant composition
JP6130472B2 (en) Body odor suppressor
EP4094782A1 (en) Deodorant composition
WO2015118625A1 (en) Diketone activity inhibitor

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
FPAY Annual fee payment

Payment date: 20190201

Year of fee payment: 4