CN104883882B - The manufacture method of antimicrobial composition - Google Patents
The manufacture method of antimicrobial composition Download PDFInfo
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- CN104883882B CN104883882B CN201380067208.9A CN201380067208A CN104883882B CN 104883882 B CN104883882 B CN 104883882B CN 201380067208 A CN201380067208 A CN 201380067208A CN 104883882 B CN104883882 B CN 104883882B
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- isopropyl methyl
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/345—Alcohols containing more than one hydroxy group
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
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Abstract
The method that the present invention provides a kind of excellent antimicrobial composition of dissolubility manufactured in water.The manufacture method of the antimicrobial composition includes：In the presence of aqueous medium, the process that is heated at 110~180 DEG C to (A) phenolic antiseptic and (B) polyalcohol.
Description
Technical field
The present invention relates to a kind of method for manufacturing antimicrobial composition.
Background technology
Antibacterial material be in order to prevent the pollution of the product as caused by microorganism or rotten or prevention infectious disease etc.,
And widely coordinated in the products such as cosmetics, pharmaceuticals, food, commodity, from qualitative control or it is sanitarian in terms of
Set out highly useful.It is known that the phenolic antiseptic such as isopropyl methyl phenol or parabens have it is excellent
Antibacterial action.
Phenolic antiseptic is at normal temperatures mostly solid and is insoluble in water.Its using form be usually dissolve in ethanol come
Use, but use feeling is easily damaged because ethanol stimulates skin.In addition, the composition that can be applied is restricted.
Therefore, carrying out research makes the antibacterial material of slightly water-soluble be solubilized into the technology in water, proposes to have to make glucose etc.
Sugar is incorporated into the isopropyl-methyl-benzene phenose glycosides (patent document 1) that isopropyl methyl phenol forms.In addition, report has using surface
Activating agent makes the method for triclosan micellization (non-patent literature 1)；And make isopropyl first with surfactant and wetting agent
Method (patent document 2) of base phenol solubilising etc..
Prior art literature
Patent document
Patent document 1：Japanese Unexamined Patent Publication 2005-82506 publications
Patent document 2：Japanese Unexamined Patent Publication 2011-98919 publications
Non-patent literature
Non-patent literature 1：C.Grove etc., " J.Cosmet.Sci. ", 2003, volume 54, p.537
The content of the invention
The antibacterial agent combination that the present invention provides a kind of manufacture method of antimicrobial composition, obtained by the manufacture method
Thing and the cosmetics containing the antimicrobial composition, the manufacture method of the antimicrobial composition include：In depositing for aqueous medium
Under, the process that is heated at 110~180 DEG C to (A) phenolic antiseptic and (B) polyalcohol.
Embodiment
However, although dissolubility of the isopropyl-methyl-benzene phenose glycosides in water is high, because manufacturing process is complicated, therefore
Cost is higher.Therefore, replace isopropyl methyl phenol economically not preferred using isopropyl-methyl-benzene phenose glycosides.In addition,
Method on making antibacterial material solubilising using surfactant, sufficient dissolubility and antibacterial effect can not be obtained by having
Situation.
Therefore, the present invention provides a kind of novel method of the excellent antimicrobial composition of dissolubility manufactured in water.
The present inventors have carried out various researchs to the solubilization technique of phenolic antiseptic, and its result is found：By water-based
In the presence of medium, more than 110 DEG C at a temperature of the phenolic antiseptic and polyalcohol are heated, with common phenol
The solubility of class antiseptic is compared, and the concentration of ordinary dissolution of phenolic antiseptic increases tremendously；In addition, the composition through the processing is
Just the precipitation of phenolic antiseptic can also be suppressed at room temperature and maintain highly dissoluble；Further, even if being diluted by composition
In the case of desired concentration, the precipitation of phenolic antiseptic can also be suppressed, and stability is higher.
According to the present invention it is possible to the antimicrobial composition that dissolubility of the qurer manufacture in water is excellent.By using this
Antimicrobial composition, it is possible to reduce or the use of ethanol is avoided, it is, therefore, possible to provide the less water system product of skin irritatin.
In the manufacture method of the antimicrobial composition of the present invention, including：In the presence of aqueous medium, 110~180
The process heated at DEG C to (A) phenolic antiseptic and (B) polyalcohol.
As (A) phenolic antiseptic used in the present invention, the phenolic antiseptic of slightly water-soluble, example can be preferably used
Relative to the solubility of water it is below 0.5g/L such as at 25 DEG C, is further below 0.3g/L, is further below 0.2g/L
Phenolic antiseptic.Here, solubility represents the grams for the solute being dissolved in 1L solution, unit is [g/L].
Specifically, can enumerate：Triclosan, chlorothymol (chlorothymol), carvacrol (carvacrol),
The chlorophenols antiseptic such as chlorophenol, Dichlorophenol, hexachlorophene, chloroxylenol, chloreresol；O-phenyl phenol, isopropyl methyl phenol
Deng.Wherein, preferably triclosan, isopropyl methyl phenol, more preferably isopropyl methyl phenol.Phenolic antiseptic can be with
For a kind, or mixture of more than two kinds.
(B) polyalcohol used in the present invention is the general name that the alcohols that the hydrogen of more than 2 of hydrocarbon forms is instead of with hydroxyl,
Such as it can enumerate：The aklylene glycol classes such as ethylene glycol, propane diols, 1,3- propane diols, 1,3 butylene glycol；Diethylene glycol, dipropyl
The polyalkylene glycols such as glycol, polyethylene glycol, polypropylene glycol；Glycerols such as glycerine, diglycerol, triglycerin etc..Wherein, from phenol
The solubilsed viewpoint of class antiseptic is set out, preferably ethylene glycol, propane diols, 1,3-BDO, DPG, polyethylene glycol, sweet
Oil, more preferably diglycerol, propane diols, 1,3-BDO, glycerine.The weight average molecular weight of polyethylene glycol is preferably 200~20,
000。
Polyalcohol may be used singly or in combination of two or m.
Aqueous medium used in the present invention refers to the aqueous solution of water and organic solvent.As water, can illustrate：Originally
Water, distilled water, ion exchange water, pure water.As organic solvent, as long as being the organic solvent equably mixed with water, then simultaneously
It is not particularly limited.As organic solvent, preferably carbon number is less than 4 monohydric alcohol, more preferably propyl alcohol and ethanol,
From the viewpoint of it can be applied to cosmetics, more preferably ethanol.
If using organic solvent, (A) phenolic antiseptic uprises relative to the solubility of water, but from the stimulation to skin
From the viewpoint of, preferably reduce usage amount.The concentration of organic solvent in aqueous be preferably 0~60 mass % (below only
It is designated as " % "), more preferably 0~30%, more preferably 0~10%, more preferably 0~1%, more preferably essence
It is above 0%, is free of organic solvent.
On (A) phenolic antiseptic, can make its be dispersed in the dissolving of (B) polyalcohol is formed in an aqueous medium it is polynary
In alcoholic solution, heating is supplied to the state of slurry, (A) phenolic antiseptic can also will be made temporarily to be dissolved in (B) polynary
After the solution formed in alcohol is mixed with aqueous medium, there is provided to heating.
When being supplied to heating, prepare at the heating containing aqueous medium, (A) phenolic antiseptic and (B) polyalcohol
Raw material is managed, is heated.
The content of (A) phenolic antiseptic in heating raw material different, side generally from mobility according to its species
Face is set out, preferably more than 0.5g/L, more preferably more than 0.7g/L, more preferably more than 1g/L, is more preferably
More than 1.1g/L, more preferably more than 1.2g/L, more preferably more than 1.3g/L, more preferably more than 1.4g/L, separately
Outside, preferably below 100g/L, more preferably below 75g/L, more preferably below 50g/L, more preferably 30g/L with
Under, more preferably below 20g/L, more preferably below 10g/L, more preferably below 9g/L.Additionally, it is preferred that it is 0.5
~100g/L, more preferably 0.7~75g/L, more preferably 1~50g/L, more preferably 1.1~30g/L, more
Preferably 1.2~20g/L, more preferably 1.3~10g/L, more preferably 1.4~9g/L.
It is different according to its species to heat the content of (B) polyalcohol in raw material, generally goes out in terms of mobility
Hair, preferably more than 1g/L, more preferably more than 5g/L, more preferably more than 10g/L, more preferably more than 12g/L,
More preferably more than 15g/L, more preferably more than 20g/L, additionally, it is preferred that being below 800g/L, more preferably 700g/
Below L, more preferably below 600g/L, more preferably below 300g/L, more preferably below 100g/L, more preferably
For below 50g/L.Additionally, it is preferred that be 1~800g/L, more preferably 5~700g/L, more preferably 10~600g/L,
More preferably 12~300g/L, more preferably 15~100g/L, more preferably 20~50g/L.
, relative to composition (B) mass ratio [(A)/(B)], obtained on heating composition (A) in raw material after cooling
From the viewpoint of the dissolubility of the antimicrobial composition obtained, preferably more than 0.001, more preferably more than 0.003 are more excellent
Elect more than 0.005, more preferably more than 0.01, more preferably more than 0.02, more preferably more than 0.025 as, in addition,
Preferably less than 0.2, more preferably less than 0.15, more preferably less than 0.13, more preferably less than 0.12, it is more excellent
Elect less than 0.11, more preferably less than 0.1 as.Additionally, it is preferred that it is 0.001~0.2, more preferably 0.003~0.15, more
Add preferably 0.005~0.13, more preferably 0.01~0.12, more preferably 0.02~0.11, more preferably 0.025
~0.1.
In the manufacture method of the present invention, from the viewpoint of the antibacterial activity for maintaining (A) phenolic antiseptic, preferably reduce
The usage amount of surfactant.The content for heating the surfactant in raw material is preferably 0~1g/L, and more preferably 0
~0.5g/L, more preferably 0~0.1g/L, more preferably it is essentially 0g/L, is free of surfactant.
The method heated in the presence of aqueous medium to (A) phenolic antiseptic and (B) polyalcohol has no spy
Do not limit, known method can be applied.
On the temperature of heating, improved from the dissolubility of (A) phenolic antiseptic with from the viewpoint of heat endurance, being
110~180 DEG C, more preferably 110~170 DEG C, more preferably 120~160 DEG C, more preferably 120~150 DEG C.
The method of heating can for example be enumerated：Vapor, electricity.
Pressure during heating is preferably 0~10MPa, more preferably 0.1~8MPa in terms of gauge pressure, more preferably
For 0.1~6MPa, more preferably 0.2~6MPa, more preferably 0.2~4MPa, more preferably 0.25~2MPa, more
Preferably 0.3~1.5MPa, more preferably 0.3~0.6MPa.In addition, gauge pressure is the pressure using atmospheric pressure as 0MPa.Separately
Outside, it is preferably set to more than the saturated vapour pressure of water.Gas can be used during pressurization, as the gas that can be used, such as can
To enumerate：Inert gas, vapor, nitrogen, helium etc..It can also be adjusted during pressurization without using gas by counterbalance valve.
Heat such as can also by batch process, semi-batch process, flow through methods either method implement.Wherein, calmly
Set out in terms of heating treatment time easy to control, preferably flow through methods.
It is excellent from the viewpoint of the dissolubility raising and heat endurance from (A) phenolic antiseptic on the time of heating
It is 0.1~30 minute to be selected in aqueous medium and reach after the temperature of above-mentioned heating, more preferably 0.2~15 minute, more
Preferably 0.5~8 minute.
In the case where being carried out by flow through methods, time of heating is used by by the HTHP portion of reactor
The feed speed of volume divided by aqueous medium and the mean residence time calculated.
The flow velocity of aqueous medium in the case where being carried out by flow through methods according to the volume of reactor and difference, such as
In the case that reactor volume is 500L, the flow velocity of above-mentioned aqueous medium is preferably 15~5,000L/ minutes, more preferably 30
~2,500L/ minute, more preferably 60L/ minutes minute~1,000L/.
In the manufacture method of the present invention, obtained heating liquid will be heated by, which preferably including, is cooled to 90
Below DEG C, be preferably less than 50 DEG C, more preferably less than 30 DEG C of process.Obtaining the situation of liquid antimicrobial composition
Under, preferably more than 0 DEG C, more preferably more than 10 DEG C.
The cooling velocity for the heating liquid that time according to needed for self-heating treatment temperature is reduced to 90 DEG C calculates is preferred
For 0.2 DEG C/more than s, more preferably 0.5 DEG C/more than s, more preferably 1 DEG C/more than s, more preferably 3 DEG C/more than s,
More preferably 5 DEG C/more than s.Cooling velocity is bigger, can more improve the solubility of phenolic antiseptic.Therefore, cooling velocity
The upper limit is simultaneously not particularly limited, but the viewpoint such as restriction from manufacturing equipment, such as preferably 100 DEG C/below s, more preferably
For 50 DEG C/below s.
Further, from the steady dissolution aspect of the antimicrobial composition obtained, preferably carry out at self-heating
Undissolved and the solid content of residual process is removed in reason liquid.As the method for removing solid content, there is no particular restriction, such as can
To be carried out by centrifuging or being decanted, filter.
Thus the antimicrobial composition obtained although the content of (A) phenolic antiseptic is higher, but even if at room temperature
The precipitation of phenolic antiseptic can also be suppressed.In addition, the dissolubility in water is excellent.
On the content of the composition (A) in the antimicrobial composition of the present invention, from mobility or usability aspect,
Preferably more than 0.5g/L, more preferably more than 1g/L, more preferably more than 1.5g/L, more preferably more than 2g/L.
For the antimicrobial composition of the present invention, the meltage in water of the composition (A) at 25 DEG C be preferably 0.5g/L with
On, more preferably more than 0.7g/L, more preferably more than 1g/L, more preferably more than 1.1g/L, it is more preferably
More than 1.2g/L, more preferably more than 1.3g/L, more preferably more than 1.4g/L, more preferably more than 1.5g/L, more
Add preferably more than 2g/L, additionally, it is preferred that be below 100g/L, more preferably below 75g/L, more preferably 50g/L with
Under, more preferably below 30g/L, more preferably below 20g/L, more preferably below 10g/L, more preferably 9g/L
Below.Additionally, it is preferred that be 0.5~100g/L, more preferably 0.7~75g/L, more preferably 1~50g/L, it is more excellent
Elect 1.1~30g/L, more preferably 1.2~20g/L, more preferably 1.3~10g/L, more preferably 1.4~9g/L as.
On the present invention antimicrobial composition (A) phenolic antiseptic relative to (B) polyalcohol mass ratio [(A)/
(B)], from the viewpoint of the stability of antimicrobial composition, preferably more than 0.005, more preferably more than 0.01, more
Preferably more than 0.012, more preferably more than 0.015, more preferably more than 0.02, more preferably more than 0.025, more
Add preferably more than 0.03, additionally, it is preferred that be less than 0.2, more preferably less than 0.18, more preferably less than 0.15, more
Add preferably less than 0.12, more preferably less than 0.1, more preferably less than 0.09.Additionally, it is preferred that be 0.005~0.2,
More preferably 0.01~0.2, more preferably 0.012~0.18, more preferably 0.015~0.15, more preferably
For 0.02~0.12, more preferably 0.025~0.1, more preferably 0.03~0.09.
In the antimicrobial composition of the present invention, the content of organic solvent is preferably 0~60%, more preferably 0~
30%, more preferably 0~10%, more preferably 0~1%.
In the antimicrobial composition of the present invention, carbon number is that the content of less than 4 monohydric alcohol is preferably 0~60%,
More preferably 0~30%, more preferably 0~10%, more preferably 0~1%, further preferably not carbon containing original
Subnumber is less than 4 monohydric alcohol.
In the antimicrobial composition of the present invention, the content of surfactant is preferably 0~0.1%, and more preferably 0
~0.5%, more preferably 0~0.01%, further preferably without surfactant.
The antimicrobial composition of the present invention can be used in the various products such as cosmetics, pharmaceuticals, food, commodity.Especially
It is useful in the product for be used in water system that it, which is,.As cosmetics or pharmaceuticals, can enumerate：Cleaning agent, toner, color make-up
Apply some make up, it is sun-proof apply some make up, acne apply some make up, deodorization applies some make up, shampoo, dentifrice, collutory, mouth wass
Deng.
The antimicrobial composition of the present invention can also be diluted to use according to the purposes of product with water etc..On dilute
The concentration of antimicrobial composition after releasing, from the viewpoint of bactericidal effect, preferably 0.1~3g/L, more preferably 0.2~
2g/L, more preferably 0.5~1.5g/L.The antimicrobial composition of the present invention is characterised by：Although resist with common phenols
The solubility of microbial inoculum is compared, and the concentration of ordinary dissolution of phenolic antiseptic increases tremendously, can still be diluted to desired concentration, i.e.,
Just the precipitation of phenolic antiseptic can also be suppressed in this case, and stability is higher.
Following presentation embodiments of the present invention and preferred embodiment.
A kind of manufacture methods of antimicrobial composition of the ＞ of ＜ 1, wherein, including：In the presence of aqueous medium, 110~
The process heated at 180 DEG C to (A) phenolic antiseptic and (B) polyalcohol.
The manufacture method of antimicrobial compositions of the ＞ of ＜ 2 as described in the ＞ of ＜ 1, wherein, (A) phenolic antiseptic is at 25 DEG C
Solubility in water is preferably below 0.5g/L compound, and preferably above-mentioned solubility is below 0.3g/L compound, is entered
One step is preferably the compound that above-mentioned solubility is below 0.2g/L.
The manufacture method of antimicrobial compositions of the ＞ of ＜ 3 as described in the ＞ of ＜ 1 or the ＞ of ＜ 2, wherein, (A) phenolic antiseptic is excellent
Elect as selected from triclosan, chlorothymol, carvacrol, chlorophenol, Dichlorophenol, hexachlorophene, chloroxylenol, chloreresol, adjacent phenyl
It is one kind or two or more in phenol and isopropyl methyl phenol, more preferably in triclosan and isopropyl methyl phenol
One kind or two or more, more preferably isopropyl methyl phenol.
The manufacture method of antimicrobial compositions of the ＞ of ＜ 4 as any one of the ＞ of the ＞ of ＜ 1 to ＜ 3, wherein, (B) is polynary
Alcohol be preferably selected from it is one kind or two or more in aklylene glycol class, polyalkylene glycols and glycerols, more preferably
It is one kind or two or more in ethylene glycol, propane diols, 1,3-BDO, DPG, polyethylene glycol, glycerine and diglycerol,
More preferably propane diols, 1,3 butylene glycol, glycerine.
The manufacture method of antimicrobial compositions of the ＞ of ＜ 5 as any one of the ＞ of the ＞ of ＜ 1 to ＜ 4, wherein, added
In the process of heat treatment, (A) phenolic antiseptic is preferably more than 0.001 relative to the mass ratio [(A)/(B)] of (B) polyalcohol,
More preferably more than 0.003, more preferably more than 0.005, more preferably more than 0.01, more preferably 0.02 with
On, more preferably more than 0.025, additionally, it is preferred that be less than 0.2, more preferably less than 0.15, more preferably 0.13
Hereinafter, more preferably less than 0.12, more preferably less than 0.11, more preferably less than 0.1, additionally, it is preferred that being 0.001
~0.2, more preferably 0.003~0.15, more preferably 0.005~0.13, more preferably 0.01~0.12, more
Preferably 0.02~0.11, more preferably 0.025~0.1.
The manufacture method of antimicrobial compositions of the ＞ of ＜ 6 as any one of the ＞ of the ＞ of ＜ 1 to ＜ 5, wherein, added
In the process of heat treatment, in the heating raw material comprising aqueous medium, (A) phenolic antiseptic and (B) polyalcohol, preferably contain
There are (A) more than phenolic antiseptic 0.5g/L, more preferably more preferably more than 0.7g/L, more than 1g/L, more preferably
For more than 1.1g/L, more preferably more than 1.2g/L, more preferably more than 1.3g/L, more preferably more than 1.4g/L,
Additionally, it is preferred that contain (A) below phenolic antiseptic 100g/L, more preferably below 75g/L, more preferably 50g/L with
Under, more preferably below 30g/L, more preferably below 20g/L, more preferably below 10g/L, more preferably 9g/L
Hereinafter, additionally, it is preferred that containing 0.5~100g/L, more preferably 0.7~75g/L, more preferably 1~50g/L, more preferably
For 1.1~30g/L, more preferably 1.2~20g/L, more preferably 1.3~10g/L, more preferably 1.4~9g/L.
The manufacture method of antimicrobial compositions of the ＞ of ＜ 7 as any one of the ＞ of the ＞ of ＜ 1 to ＜ 6, wherein, added
In the process of heat treatment, in the heating raw material comprising aqueous medium, (A) phenolic antiseptic and (B) polyalcohol, preferably contain
There are (B) more than polyalcohol 1g/L, more preferably more preferably more than 5g/L, more preferably more than 10g/L, 12g/L
More than, more preferably more than 15g/L, more preferably more than 20g/L, additionally, it is preferred that contain below 800g/L, it is further excellent
Elect below 700g/L, more preferably below 600g/L, more preferably below 300g/L as, more preferably 100g/L with
Under, more preferably below 50g/L, additionally, it is preferred that contain 1~800g/L, preferably 5~700g/L, more preferably 10~
600g/L, more preferably 12~300g/L, more preferably 15~100g/L, more preferably 20~50g/L.
The manufacture method of antimicrobial compositions of the ＞ of ＜ 8 as any one of the ＞ of the ＞ of ＜ 1 to ＜ 7, wherein, aqueous medium
The preferably aqueous solution of water or organic solvent, more preferably water or carbon number are the aqueous solution of less than 4 monohydric alcohol, are entered
One step is preferably the aqueous solution of water or ethanol, more preferably water.
The manufacture method of antimicrobial compositions of the ＞ of ＜ 9 as described in the ＞ of ＜ 8, wherein, having in the aqueous solution of organic solvent
The concentration of solvent is preferably 0~60 mass %, preferably 0~30 mass %, more preferably 0~10 mass %, more
Preferably 0~1 mass %, more preferably without organic solvent.
The manufacture method of antimicrobial compositions of the ＞ of ＜ 10 as any one of the ＞ of the ＞ of ＜ 1 to ＜ 9, wherein, carrying out
In the process of heating, in the heating raw material comprising aqueous medium, (A) phenolic antiseptic and (B) polyalcohol, preferably
Contain 0~1g/L of surfactant, more preferably 0~0.5g/L, more preferably 0~0.1g/L, or be more preferably free of
Surfactant.
The manufacture method of antimicrobial compositions of the ＞ of ＜ 11 as any one of the ＞ of the ＞ of ＜ 1 to ＜ 10, wherein, at heating
The temperature of reason is 110~180 DEG C, preferably 110~170 DEG C, more preferably 120~160 DEG C, more preferably 120~
150℃。
The manufacture method of antimicrobial compositions of the ＞ of ＜ 12 as any one of the ＞ of the ＞ of ＜ 1 to ＜ 11, wherein, further
Including the obtained process for heating liquid cooling will be heated.
The manufacture method of antimicrobial compositions of the ＞ of ＜ 13 as any one of the ＞ of the ＞ of ＜ 1 to ＜ 12, wherein, it will add
In the process that heat treatment solution is cooled down, self-heating treatment temperature to 90 DEG C of cooling velocity is preferably 0.2 DEG C/more than s, is entered
One step is preferably 0.5 DEG C/more than s, more preferably 1 DEG C/more than s, more preferably 3 DEG C/more than s, more preferably 5
DEG C/more than s, additionally, it is preferred that being 100 DEG C/below s, more preferably 50 DEG C/below s.
A kind of antimicrobial compositions of the ＞ of ＜ 14, wherein, by the manufacture method any one of the ＞ of the ＞ of ＜ 1 to ＜ 13 and
Obtain.
Antimicrobial compositions of the ＞ of ＜ 15 as described in the ＞ of ＜ 14, wherein, (A) phenolic antiseptic in antimicrobial composition
Content is preferably more than 0.5g/L, more preferably more than 1g/L, more preferably more than 1.5g/L, more preferably 2g/L
More than.
Antimicrobial compositions of the ＞ of ＜ 16 as described in the ＞ of ＜ 14 or the ＞ of ＜ 15, wherein, water of (A) phenolic antiseptic at 25 DEG C
In meltage be preferably more than 0.5g/L, more preferably more than 0.7g/L, more preferably more than 1g/L, more preferably
For more than 1.1g/L, more preferably more than 1.2g/L, more preferably more than 1.3g/L, more preferably more than 1.4g/L,
More preferably more than 1.5g/L, more preferably more than 2g/L, additionally, it is preferred that being below 100g/L, more preferably
Below 75g/L, more preferably below 50g/L, more preferably below 30g/L, more preferably below 20g/L, it is more excellent
Below 10g/L, more preferably below 9g/L are elected as, additionally, it is preferred that being 0.5~100g/L, more preferably 0.7~75g/
L, more preferably 1~50g/L, more preferably 1.1~30g/L, more preferably 1.2~20g/L, more preferably 1.3
~10g/L, more preferably 1.4~9g/L.
Antimicrobial compositions of the ＞ of ＜ 17 as any one of the ＞ of the ＞ of ＜ 14 to ＜ 16, wherein, (A) phenolic antiseptic phase
Mass ratio [(A)/(B)] for (B) polyalcohol is preferably more than 0.005, and more preferably more than 0.01, be more preferably
More than 0.012, more preferably more than 0.015, more preferably more than 0.02, more preferably more than 0.025, more preferably
For more than 0.03, additionally, it is preferred that being less than 0.2, more preferably less than 0.18, more preferably less than 0.15 are more excellent
Elect less than 0.12, more preferably less than 0.1, more preferably less than 0.09 as, additionally, it is preferred that being 0.005~0.2, enter one
Step is preferably 0.01~0.2, more preferably 0.012~0.18, more preferably 0.015~0.15, more preferably 0.02
~0.12, more preferably 0.025~0.1, more preferably 0.03~0.09.
Antimicrobial compositions of the ＞ of ＜ 18 as any one of the ＞ of the ＞ of ＜ 14 to ＜ 17, wherein, in antimicrobial composition
The content of organic solvent be preferably 0~60 mass %, more preferably 0~30 mass %, more preferably 0~10 matter
Measure %, more preferably 0~1 mass %.
Antimicrobial compositions of the ＞ of ＜ 19 as any one of the ＞ of the ＞ of ＜ 14 to ＜ 18, wherein, in antimicrobial composition
Carbon number be less than 4 the content of monohydric alcohol be preferably 0~60 mass %, more preferably 0~30 mass %, more
Preferably 0~10 mass %, more preferably 0~1 mass %, more preferably without monohydric alcohol.
Antimicrobial compositions of the ＞ of ＜ 20 as any one of the ＞ of the ＞ of ＜ 14 to ＜ 19, wherein, in antimicrobial composition
The content of surfactant be preferably 0~0.1 mass %, more preferably 0~0.5 mass %, more preferably 0~
0.01 mass %.
A kind of cosmetics of the ＞ of ＜ 21, wherein, contain the antimicrobial composition any one of the ＞ of the ＞ of ＜ 14 to ＜ 20.
A kind of deodorizations of the ＞ of ＜ 22 apply some make up, wherein, contain the antiseptic group any one of the ＞ of the ＞ of ＜ 14 to ＜ 20
Compound.
A kind of acne of the ＞ of ＜ 23 apply some make up, wherein, contain the antiseptic group any one of the ＞ of the ＞ of ＜ 14 to ＜ 20
Compound.
A kind of cleaning agents of the ＞ of ＜ 24, wherein, contain the antimicrobial composition any one of the ＞ of the ＞ of ＜ 14 to ＜ 20.
Embodiment
[quantifying for isopropyl methyl phenol]
The high performance liquid chromatograph manufactured using Hitachi, and the post Cadenza of Imtakt companies manufacture is installed
CD-C18(3 μm), carried out at 40 DEG C of column temperature by gradient method.Mobile phase A liquid is
0.05mol/L acetic acid aqueous solutions, B liquid are acetonitrile, and liquor charging is carried out with 1.0mL/ minutes.Gradient condition is as described below.
Sample injection rate is 10 μ L, is detected by wavelength 283nm absorbance to quantify.
[estimation of stabilitys of dilution product]
By isopropyl methyl phenol composition or liquid portion with the isopropyl-methyl-benzene in composition or in liquid portion
Phenol concentration is diluted as 0.05 mass % or 0.1 mass % mode using water, is preserved 1 month at 25 DEG C.Observe dilute
The precipitation situation of the precipitation of product is released, as the outward appearance after preservation.
[raw material]
Isopropyl methyl phenol (IPMP, Osaka Kasei Co., Ltd.'s manufacture, purity 100%)
1,3-BDO (1,3-BG, KH Neochem Co., Ltd.s manufacture, purity 100%)
Diglycerol (DG, the manufacture of this pharmaceutical industries of slope Co., Ltd., purity 100%)
Propane diols (PG, ADEKA Corp.'s manufacture, purity 100%)
DPG (DPG, Asahi Glass Co., Ltd's manufacture, purity 100%)
Polyethylene glycol (PEG, Sanyo Chemical Industries, Ltd.'s manufacture, purity 100%)
Ethylene glycol (EG, Kao Corp's manufacture, purity 100%)
Glycerine (Gly, Kao Corp's manufacture, purity 100%)
Embodiment 1
Isopropyl methyl phenol and 1,3 butylene glycol are added to distillation in a manner of respectively becoming 1.43g/L, 47.5g/L
In water, using internal volume by 190mL stainless steel batch-type reactor (manufacture of Dong high pressures Co., Ltd.) to what is obtained
Slurry is heated.Kept for 1 minute after reaching 150 DEG C, and be rapidly cooled to room temperature (25 DEG C) (0.5 DEG C of cooling velocity/
s).Pressure in heating is 0.4MPa.Liquid is heated in rapid extraction after cooling, utilizes the PTFE mistakes that aperture is 0.2 μm
Filter is filtered, and obtains isopropyl methyl phenol composition.
By treatment conditions, the isopropyl methyl phenol concentration in composition and 1,3 butylene glycol are measured obtained by
As a result and the outward appearance after the preservation of dilution product is shown in Table 1 (following, identical in embodiment).
Embodiment 2
Isopropyl methyl phenol and diglycerol are added to distilled water in a manner of respectively becoming 1.46g/L, 47.5g/L
In, heated in the same manner as example 1, obtain isopropyl methyl phenol composition.
Embodiment 3
Isopropyl methyl phenol and propane diols are added to distilled water in a manner of respectively becoming 1.43g/L, 47.5g/L
In, heated in the same manner as example 1, obtain isopropyl methyl phenol composition.
Embodiment 4
Isopropyl methyl phenol and DPG are added to distilled water in a manner of respectively becoming 1.43g/L, 47.5g/L
In, heated in the same manner as example 1, obtain isopropyl methyl phenol composition.
Embodiment 5~7
By isopropyl methyl phenol and polyethylene glycol (molecular weight 1540,4000,20000) with respectively become 1.43g/L,
47.5g/L mode is added in distilled water, is heated in the same manner as example 1, obtains isopropyl methyl
Phenol composition.
Embodiment 8
Isopropyl methyl phenol and ethylene glycol are added to distilled water in a manner of respectively becoming 1.66g/L, 47.5g/L
In, heated in the same manner as example 1, obtain isopropyl methyl phenol composition.
Embodiment 9
Isopropyl methyl phenol and glycerine are added in distilled water in a manner of respectively becoming 1.66g/L, 47.5g/L,
Heated in the same manner as example 1, obtain isopropyl methyl phenol composition.
Embodiment 10
Isopropyl methyl phenol is dissolved in 1,3 butylene glycol in a manner of what is made turns into 35g/L.With the stream of lysate
The rapid-result flow velocity for 5ml/ minutes, distilled water turns into the mode of 95ml/ minutes, and lysate is supplied into internal volume with distilled water is
In 100mL stainless steel flow through reactors (manufacture of Dong high pressures Co., Ltd.), heated at 150 DEG C (flat
The equal holdup time is 1 minute).Pressure is 0.5MPa (gauge pressure) by outlet side valve regulation.At autoreactor outlet extraction heating
Liquid is managed, room temperature (25 DEG C) is cooled to by heat exchanger, is run through after the metal sintered filter that aperture is 0.5 μm, profit
Pressure is recovered to atmospheric pressure with outlet valve, obtains isopropyl methyl phenol composition.According to being cooled to 90 DEG C cold from 150 DEG C
But the cooling velocity calculated by the time is 2 DEG C/s.
Comparative example 1
Not adding ingredient (B) polyalcohol, isopropyl methyl phenol 1.5g/L is dispersed in distilled water, with embodiment 1
Identical mode obtains isopropyl methyl phenol composition.By treatment conditions and dense to the isopropyl methyl phenol in composition
Result obtained by degree is measured is shown in Table 2.
Comparative example 2
Isopropyl methyl phenol and 1,3 butylene glycol are added to distillation in a manner of respectively becoming 1.43g/L, 47.5g/L
In water, after slurry 50g stirrings (agitator, 500rpm) 3 days, solid content is separated by filtration.By to different in liquid portion
Result obtained by hydroxypropyl methyl phenol concentration and 1,3 butylene glycol concentration are measured is shown in Table 2.
Comparative example 3
Isopropyl methyl phenol and diglycerol are added to distilled water in a manner of respectively becoming 1.46g/L, 47.5g/L
In, after slurry 50g stirrings (agitator, 500rpm) 3 days, it is separated by filtration solid content.By to the isopropyl in liquid portion
Result obtained by ylmethyl phenol concentration and diglycerol concentration are measured is shown in Table 2.
Comparative example 4
Isopropyl methyl phenol and propane diols are added to distilled water in a manner of respectively becoming 1.43g/L, 47.5g/L
In, after slurry 50g stirrings (agitator, 500rpm) 3 days, it is separated by filtration solid content.By to the isopropyl in liquid portion
Result obtained by ylmethyl phenol concentration and PG concentration are measured is shown in Table 2.
Comparative example 5
By isopropyl methyl phenol and polyethylene glycol (molecular weight 4000) in a manner of respectively becoming 1.43g/L, 47.5g/L
Added in distilled water, after slurry 50g stirrings (agitator, 500rpm) 3 days, solid content is separated by filtration.Will be to liquid
Result obtained by isopropyl methyl phenol concentration and Polyethylene glycol in part are measured is shown in Table 2.
[table 2]
Embodiment 11
Isopropyl methyl phenol and propane diols are added to distilled water in a manner of respectively becoming 1.66g/L, 47.5g/L
In, heated using the stainless steel batch-type reactor (manufacture of Dong high pressures Co., Ltd.) that internal volume is 190mL.
Kept for 5 minutes after reaching 120 DEG C, and be rapidly cooled to room temperature (25 DEG C) (0.7 DEG C/s of cooling velocity).Pressure in heating
For 0.14MPa.Liquid is heated in rapid extraction after cooling, is filtered, obtained different using the PTFE filters that aperture is 0.2 μm
Hydroxypropyl methyl phenol composition.Carried out by treatment conditions, to the isopropyl methyl phenol concentration in composition and PG concentration
Result obtained by measure and the outward appearance after the preservation of dilution product are shown in Table 3 (following, identical in embodiment).
Embodiment 12
Heating-up temperature is set as 135 DEG C, 5 minutes will be set as the retention time, in addition, with identical with embodiment 11
Mode handled, obtain isopropyl methyl phenol composition.
Embodiment 13
Heating-up temperature is set as 140 DEG C, 1 minute will be set as the retention time, in addition, with identical with embodiment 11
Mode handled, obtain isopropyl methyl phenol composition.
Embodiment 14
Heating-up temperature is set as 145 DEG C, 1 minute will be set as the retention time, in addition, with identical with embodiment 11
Mode handled, obtain isopropyl methyl phenol composition.
Embodiment 15
Heating-up temperature is set as 150 DEG C, 1 minute will be set as the retention time, in addition, with identical with embodiment 11
Mode handled, obtain isopropyl methyl phenol composition.
Comparative example 6
Heating-up temperature is set as 80 DEG C, 5 minutes will be set as the retention time, in addition, with identical with embodiment 11
Mode handled, obtain isopropyl methyl phenol composition.By treatment conditions and to the isopropyl-methyl-benzene in composition
Result obtained by phenol concentration and PG concentration are measured is shown in Table 3.
Comparative example 7
Heating-up temperature is set as 100 DEG C, 5 minutes will be set as the retention time, in addition, with identical with embodiment 11
Mode handled, obtain isopropyl methyl phenol composition.By treatment conditions and to the isopropyl-methyl-benzene in composition
Result obtained by phenol concentration and PG concentration are measured is shown in Table 3.
Embodiment 16
Isopropyl methyl phenol and propane diols are added in distilled water in a manner of respectively becoming 1.81g/L, 100g/L,
Heated in the same manner as example 1, obtain isopropyl methyl phenol composition.By treatment conditions, to combination
After isopropyl methyl phenol concentration and PG concentration in thing are measured resulting result and the preservation for diluting product
Outward appearance is shown in Table 4.
Comparative example 8
Isopropyl methyl phenol and propane diols are added in distilled water in a manner of respectively becoming 1.81g/L, 100g/L,
After slurry 50g stirrings (agitator, 500rpm) 3 days, solid content is separated by filtration.By to the isopropyl first in liquid portion
Result obtained by base phenol concentration and PG concentration are measured is shown in Table 4.
Embodiment 17
Isopropyl methyl phenol and propane diols are added in distilled water in a manner of respectively becoming 2g/L, 300g/L, with
Mode same as Example 1 is heated, and obtains isopropyl methyl phenol composition.By treatment conditions, to composition
In isopropyl methyl phenol concentration and PG concentration be measured obtained by result and dilute outer after the preservations of product
Sight is shown in Table 4.
Comparative example 9
Isopropyl methyl phenol and propane diols are added in distilled water in a manner of respectively becoming 2g/L, 300g/L, will
Slurry 50g stirred (agitator, 500rpm) after 3 days, was separated by filtration solid content.By to the isopropyl methyl in liquid portion
The outward appearance that phenol concentration and PG concentration are measured after resulting result and the preservation for diluting product is shown in Table 4.
Embodiment 18
Isopropyl methyl phenol and propane diols are added in distilled water in a manner of respectively becoming 5g/L, 400g/L, with
Mode same as Example 1 is heated, and obtains isopropyl methyl phenol composition.By treatment conditions, to composition
In isopropyl methyl phenol concentration and PG concentration be measured obtained by result and dilute product preservation after outward appearance
It is shown in Table 4.
Comparative example 10
Isopropyl methyl phenol and propane diols are added in distilled water in a manner of respectively becoming 5g/L, 400g/L, will
Slurry 50g stirred (agitator, 500rpm) after 3 days, was separated by filtration solid content.By to the isopropyl methyl in liquid portion
The outward appearance that phenol concentration and PG concentration are measured after resulting result and the preservation for diluting product is shown in Table 4.
Embodiment 19
Isopropyl methyl phenol and propane diols are added in distilled water in a manner of respectively becoming 20g/L, 500g/L, with
Mode same as Example 1 is heated, and obtains isopropyl methyl phenol composition.By treatment conditions, to composition
In isopropyl methyl phenol concentration and PG concentration be measured obtained by result and dilute outer after the preservations of product
Sight is shown in Table 4.
Comparative example 11
Isopropyl methyl phenol and propane diols are added in distilled water in a manner of respectively becoming 20g/L, 500g/L, will
Slurry 50g stirred (agitator, 500rpm) after 3 days, was separated by filtration solid content.By to the isopropyl methyl in liquid portion
The outward appearance that phenol concentration and PG concentration are measured after resulting result and the preservation for diluting product is shown in Table 4.
Embodiment 20
Isopropyl methyl phenol and propane diols are added in distilled water in a manner of respectively becoming 50g/L, 600g/L, with
Mode same as Example 1 is heated, and obtains isopropyl methyl phenol composition.By treatment conditions, to composition
In isopropyl methyl phenol concentration and PG concentration be measured obtained by result and dilute outer after the preservations of product
Sight is shown in Table 4.
Comparative example 12
Isopropyl methyl phenol and propane diols are added in distilled water in a manner of respectively becoming 50g/L, 600g/L, will
Slurry 50g stirred (agitator, 500rpm) after 3 days, was separated by filtration solid content.By to the isopropyl methyl in liquid portion
The outward appearance that phenol concentration and PG concentration are measured after resulting result and the preservation for diluting product is shown in Table 4.
Embodiment 21
Isopropyl methyl phenol and 1,3 butylene glycol are added to distillation in a manner of respectively becoming 1.81g/L, 100g/L
In water, carry out heating acquisition isopropyl methyl phenol composition in the same manner as example 1.By treatment conditions, right
Isopropyl methyl phenol concentration and 1,3 butylene glycol concentration in composition are measured resulting result and dilute the guarantor of product
Outward appearance after depositing is shown in Table 5.
Comparative example 13
Isopropyl methyl phenol and 1,3 butylene glycol are added to distillation in a manner of respectively becoming 1.81g/L, 100g/L
In water, after slurry 50g stirrings (agitator, 500rpm) 3 days, solid content is separated by filtration.By to different in liquid portion
Result obtained by hydroxypropyl methyl phenol concentration and 1,3 butylene glycol concentration are measured is shown in Table 5.
Embodiment 22~24
By 1,3 butylene glycol in a manner of as 300g/L and by isopropyl methyl phenol with respectively become 2g/L, 5g/L,
10g/L mode is added in distilled water, carries out heating acquisition isopropyl methyl phenol in the same manner as example 1
Composition.By treatment conditions, gained is measured to the isopropyl methyl phenol concentration in composition and 1,3 butylene glycol concentration
To result and dilute product preservation after outward appearance be shown in Table 5.
Comparative example 14
Isopropyl methyl phenol and 1,3 butylene glycol are added to distilled water in a manner of respectively becoming 5g/L, 300g/L
In, after slurry 50g stirrings (agitator, 500rpm) 3 days, it is separated by filtration solid content.By to the isopropyl in liquid portion
The outward appearance that ylmethyl phenol concentration and 1,3 butylene glycol concentration are measured after resulting result and the preservation for diluting product is shown in
In table 5.
Embodiment 25~27
By 1,3 butylene glycol to respectively become 5g/L, 10g/ in a manner of as 400g/L and by isopropyl methyl phenol
L, 20g/L mode is added in distilled water, is heated in the same manner as example 1, obtains isopropyl methyl
Phenol composition.It is measured by treatment conditions, to the isopropyl methyl phenol concentration in composition and 1,3 butylene glycol concentration
Outward appearance after the preservation of resulting result and dilution product is shown in Table 5.
Comparative example 15
Isopropyl methyl phenol and 1,3 butylene glycol are added to distilled water in a manner of respectively becoming 10g/L, 400g/L
In, after slurry 50g stirrings (agitator, 500rpm) 3 days, it is separated by filtration solid content.By to the isopropyl in liquid portion
The outward appearance that ylmethyl phenol concentration and 1,3 butylene glycol concentration are measured after resulting result and the preservation for diluting product is shown in
In table 5.
Embodiment 28~32
By 1,3 butylene glycol to respectively become 10g/L, 20g/ in a manner of as 500g/L and by isopropyl methyl phenol
L, 25g/L, 27.5g/L, 30g/L mode are added in distilled water, are heated in the same manner as example 1,
Obtain isopropyl methyl phenol composition.By treatment conditions, to the isopropyl methyl phenol concentration and 1,3- fourths two in composition
The outward appearance that determining alcohol is measured after resulting result and the preservation for diluting product is shown in Table 6.
Comparative example 16
Isopropyl methyl phenol and 1,3 butylene glycol are added to distillation in a manner of respectively becoming 27.5g/L, 500g/L
In water, after slurry 50g stirrings (agitator, 500rpm) 3 days, solid content is separated by filtration.By to different in liquid portion
The outward appearance that hydroxypropyl methyl phenol concentration and 1,3 butylene glycol concentration are measured after resulting result and the preservation for diluting product is shown
In table 6.
Embodiment 33~36
By 1,3 butylene glycol to respectively become 20g/L, 30g/ in a manner of as 600g/L and by isopropyl methyl phenol
L, 40g/L, 50g/L mode are added in distilled water, are heated in the same manner as example 1, obtain isopropyl
Ylmethyl phenol composition.Enter by treatment conditions, to the isopropyl methyl phenol concentration in composition and 1,3 butylene glycol concentration
Result obtained by row measure and the outward appearance after the preservation of dilution product are shown in Table 6.
Comparative example 17
Isopropyl methyl phenol and 1,3 butylene glycol are added to distilled water in a manner of respectively becoming 50g/L, 600g/L
In, after slurry 50g stirrings (agitator, 500rpm) 3 days, it is separated by filtration solid content.By to the isopropyl in liquid portion
The outward appearance that ylmethyl phenol concentration and 1,3 butylene glycol concentration are measured after resulting result and the preservation for diluting product is shown in
In table 6.
Can be clear and definite by table 1~6, the more isopropyl methyl phenol combination of the content of isopropyl methyl phenol can be obtained
It thing, can significantly increase the solubility of isopropyl-methyl-benzene phenol.
In addition, the isopropyl methyl phenol composition obtained in embodiment 1~36 is preserved 1 month at room temperature, as a result
Precipitation is not separated out, keeps stable dissolved state.Further, as shown in table 1~6, even if will obtained in embodiment 1~36
Isopropyl methyl phenol composition be diluted to desired concentration in the case of, also without separating out precipitation, and keep stable
Dissolved state.In contrast, in the case where not carrying out the heating of the present invention, as shown in comparative example, by isopropyl first
In the case that base phenol composition is diluted to desired concentration, after being saved it can be found that the precipitation of precipitation, confirms stability
Difference.
Embodiment 37
Polymeric aluminum chloride 10g, polyoxy second are added in the isopropyl methyl phenol composition 4.08g manufactured in embodiment 31
Alkene rilanit special 0.2g, spices 0.05g, pure water is added, so as to prepare 100g deodorant liquid.Composition is as described below.
Embodiment 38
1,3 butylene glycol 6g, oleyl alcohol are added in the isopropyl methyl phenol composition 78.74g manufactured in embodiment 1
0.1g, POE (20) oleyl alcohol ether 0.4g, methyl p-hydroxybenzoate 0.2g, dipotassium glycyrrhizinate 0.2g, spices 0.04g, add pure
Water, so as to prepare 100g acne toner.Composition is as described below.
Embodiment 39
Using as the stearic acid 12g of oil phase, myristic acid 14g, laurate 5g, jojoba oil 3g, D-sorbite
14.047g, glycerine 10g, 1,3-BDO 10g are dissolved by heating, and are maintained at 70 DEG C.Potassium hydroxide 5g is dissolved in implementation
In the isopropyl methyl phenol composition 21.053g manufactured in example 18, oil phase is stirred while slowly adding.Further plus
Enter N methyl taurine 4g and stir 10 minutes, be sufficiently carried out after neutralization reaction, add POE (20) glycerin monostearate
1.9g.Slowly cooling (placing cooling) is to 25 DEG C, so as to prepare hand cleanser.Composition is as described below.
Claims (20)
1. a kind of manufacture method of antimicrobial composition, wherein,
Including：In the presence of aqueous medium, (A) phenolic antiseptic is set to be relative to mass ratio i.e. (A)/(B) of (B) polyalcohol
0.001~0.2, the process heated at 110~180 DEG C to (A) phenolic antiseptic and (B) polyalcohol.
2. the manufacture method of antimicrobial composition as claimed in claim 1, wherein,
(A) compound that phenolic antiseptic is below 0.5g/L for the solubility in 25 DEG C of water.
3. the manufacture method of antimicrobial composition as claimed in claim 1 or 2, wherein,
(A) phenolic antiseptic is selected from triclosan, chlorothymol, carvacrol, chlorophenol, Dichlorophenol, hexachlorophene, xylene dichloride
It is one kind or two or more in phenol, chloreresol, o-phenyl phenol and isopropyl methyl phenol.
4. the manufacture method of antimicrobial composition as claimed in claim 1 or 2, wherein,
(A) phenolic antiseptic is one kind or two or more in triclosan and isopropyl methyl phenol.
5. the manufacture method of antimicrobial composition as claimed in claim 1 or 2, wherein,
(A) phenolic antiseptic is isopropyl methyl phenol.
6. the manufacture method of antimicrobial composition as claimed in claim 1 or 2, wherein,
(B) polyalcohol is in ethylene glycol, propane diols, 1,3 butylene glycol, DPG, polyethylene glycol, glycerine and diglycerol
It is one kind or two or more.
7. the manufacture method of antimicrobial composition as claimed in claim 1 or 2, wherein,
(B) polyalcohol is one kind or two or more in propane diols, 1,3 butylene glycol, glycerine.
8. the manufacture method of antimicrobial composition as claimed in claim 1 or 2, wherein,
In the process heated, the heating of aqueous medium, (A) phenolic antiseptic and (B) polyalcohol is being included
Contain 0.5~100g/L of (A) phenolic antiseptic in raw material.
9. the manufacture method of antimicrobial composition as claimed in claim 1 or 2, wherein,
In the process heated, the heating of aqueous medium, (A) phenolic antiseptic and (B) polyalcohol is being included
Contain 1~800g/L of (B) polyalcohol in raw material.
10. the manufacture method of antimicrobial composition as claimed in claim 1 or 2, wherein,
Aqueous medium is the aqueous solution of water or organic solvent.
11. the manufacture method of antimicrobial composition as claimed in claim 10, wherein,
The concentration of organic solvent in the aqueous solution of organic solvent is 0~60 mass %.
12. the manufacture method of antimicrobial composition as claimed in claim 1 or 2, wherein,
The aqueous solution for the monohydric alcohol that aqueous medium is water or carbon number is less than 4.
13. the manufacture method of antimicrobial composition as claimed in claim 1 or 2, wherein,
In the process heated, the heating of aqueous medium, (A) phenolic antiseptic and (B) polyalcohol is being included
Contain 0~1g/L of surfactant in raw material.
14. the manufacture method of antimicrobial composition as claimed in claim 1 or 2, wherein,
Obtained heating liquid will be heated by further comprising is cooled down with 0.2 DEG C/more than s cooling velocity
Process.
15. a kind of antimicrobial composition, wherein,
Obtained by the manufacture method any one of claim 1~14,
Mass ratio as (A) phenolic antiseptic relative to (B) polyalcohol, (A)/(B) are 0.005~0.2.
16. antimicrobial composition as claimed in claim 15, wherein,
The content of (A) phenolic antiseptic in antimicrobial composition is more than 0.5g/L.
17. the antimicrobial composition as described in claim 15 or 16, wherein,
(A) meltage of the phenolic antiseptic in 25 DEG C of water is more than 0.5g/L.
18. the antimicrobial composition as described in claim 15 or 16, wherein,
The content for the monohydric alcohol that carbon number in antimicrobial composition is less than 4 is 0~1 mass %.
19. the antimicrobial composition as described in claim 15 or 16, wherein,
The content of surfactant in antimicrobial composition is 0~0.1 mass %.
20. a kind of cosmetics, wherein,
Contain the antimicrobial composition any one of claim 15~19.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012279811 | 2012-12-21 | ||
| JP2012-279811 | 2012-12-21 | ||
| PCT/JP2013/084306 WO2014098231A1 (en) | 2012-12-21 | 2013-12-20 | Method for manufacturing antimicrobial composition |
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| Publication Number | Publication Date |
|---|---|
| CN104883882A CN104883882A (en) | 2015-09-02 |
| CN104883882B true CN104883882B (en) | 2017-11-17 |
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| CN201380067208.9A Active CN104883882B (en) | 2012-12-21 | 2013-12-20 | The manufacture method of antimicrobial composition |
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| JP (2) | JP5872528B2 (en) |
| CN (1) | CN104883882B (en) |
| TW (1) | TWI603743B (en) |
| WO (1) | WO2014098231A1 (en) |
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| CN106132389B (en) * | 2014-04-09 | 2020-07-14 | 花王株式会社 | Method for producing composition containing hardly water-soluble aromatic compound |
| JP5908635B1 (en) * | 2015-04-08 | 2016-04-26 | 花王株式会社 | Cosmetics |
| JP6634284B2 (en) * | 2015-12-25 | 2020-01-22 | 日油株式会社 | Concentrated antimicrobial composition |
| JP6611646B2 (en) * | 2016-03-23 | 2019-11-27 | 花王株式会社 | Cosmetics |
| EP3733155B1 (en) * | 2017-12-27 | 2022-11-23 | Kao Corporation | Method for manufacturing composition that includes poorly water-soluble aromatic compound |
| WO2019230210A1 (en) | 2018-05-31 | 2019-12-05 | Ｖｂジャパンテクノロジー株式会社 | Antiviral and antibacterial composition and aqueous solution |
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Also Published As
| Publication number | Publication date |
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| CN104883882A (en) | 2015-09-02 |
| JP5872528B2 (en) | 2016-03-01 |
| WO2014098231A1 (en) | 2014-06-26 |
| TW201429499A (en) | 2014-08-01 |
| JP2014139164A (en) | 2014-07-31 |
| JP6276787B2 (en) | 2018-02-07 |
| TWI603743B (en) | 2017-11-01 |
| JP2016056200A (en) | 2016-04-21 |
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