CN101671372B - Esterification reaction synthetic method of oligomeric propylene diester and oligomeric propylene diester thereof - Google Patents
Esterification reaction synthetic method of oligomeric propylene diester and oligomeric propylene diester thereof Download PDFInfo
- Publication number
- CN101671372B CN101671372B CN2009101783258A CN200910178325A CN101671372B CN 101671372 B CN101671372 B CN 101671372B CN 2009101783258 A CN2009101783258 A CN 2009101783258A CN 200910178325 A CN200910178325 A CN 200910178325A CN 101671372 B CN101671372 B CN 101671372B
- Authority
- CN
- China
- Prior art keywords
- oligomerization
- propylene diester
- acid
- catalyst
- oligomerization acid
- Prior art date
- Legal status (The legal status 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 status listed.)
- Active
Links
Abstract
The invention discloses an esterification reaction synthetic method of oligomeric propylene diester and oligomeric propylene diester thereof. The method comprises the following steps: adding 30-48% of oligomeric acid, 1-3% of catalyst and 47-69% of propylene glycol in weight percentage into a reaction kettle; controlling the reaction temperature to 80-120 DEG C; stirring for 2-8 hours; selecting liquid catalyst or solid catalyst to be served as the catalyst; using alkali for neutralization until the pH value is neutral when the liquid catalyst is selected after the reaction is completed; and filtering and separating the solid catalyst to finally obtain the oligomeric propylene diester products when selecting the solid catalyst. The products in the invention overcome the stimulation effect of the acidic materials on the skin, strengthen the absorption of the skin, show excellent water locking and moisturizing performances, have functions of invigorating the skin and resisting aging and have good application prospects in the cosmetic industry.
Description
Technical field
The invention belongs to cosmetic material Application Areas in the fine chemistry industry, be specifically related to a kind of esterification reaction synthetic method and oligomerization acid propylene diester thereof of oligomerization acid propylene diester.
Background technology
At present; The animal, plant and the microbial polysaccharide that utilize ocean, land are as resource, and be through the oligomer biologically active factors of fine chemistry industry and biotechnology exploitation, in the ascendant in the application of cosmetic industry; Especially the oligomerization acid molecule has more tangible biological activity, and it mainly shows as:
1, sunscreen effect.This molecule has two key carboxyls and active oh group exists, and has the ability of objectionable impuritiess such as absorption radiation.And very strong oxidation-resistance and the ability of removing radical are arranged, thereby antidotal effect is remarkable.Found in recent years that the natural marine organism polysaccharide had application widely on makeup.For example chitin (Chitin), collagen protein (Collagen), carrageeman, cation guar gum, mucopolysaccharide (Mucopolysac.Harldes), effect such as have nutrition, repair and preserve moisture such as cationic cellulose (cat loniC CelluloSe); Have more the ultraviolet ability that intercepts with the as above oligomerization acid molecule of polysaccharide development of raw materials; Therefore its skin care item spread upon and can form one barrier on the skin; Can prevent the radiation of ultraviolet ray and electric welding radiation effectively, protection skin.The immune activation function that has absorbability simultaneously can activate skin surface cell, strengthens replying of cell guiding immunocyte, and performance has sterilization and collaborative fungistatic effect.
2, have nutrition, moisture-keeping functions.This molecule has overcome the defective that macromolecular substance skin can not absorb, and can be used as nutrition by skin absorption, and skin is played good health care and maintenance action.Hydroxyl in the molecule, carboxyl and other polar group can form hydrogen bond and combine a large amount of moisture with water molecules, and simultaneously, molecular chain also is interweaved and reticulates, and with the hydrogen bonded of water, play very strong water retention in addition.
3, special physiological function.This composition can change people's sensitivity cell biological function; Comprise that cancer cell multiplication effect sensitivity cell, active oxygen produce restraining effect sensitivity cell and blood sugar reduction effect sensitivity cell.Cancer and blood glucose regulation had assisting therapy and improvement effect.Also can be used for simultaneously the healing of skin wound, to the effect enhancing or the generation synergistic effect of other composition of makeup.
In a word; Contain the application of compsn in makeup of this composition and related compound, can effectively protect the relevant variation or the infringement that cause skin and mucous membrane because of the extraneous factor of sunlight, ray, atmospheric pollution, wind, cold hot and cold, moist, chemical, smog and smoking.The name of submitting in 23 days December in 1986 obtaining patented technology is called the Patent Application No. 06/945.680 and relevant application, publication of " additive that strengthens the local surfaces effect of medicine ", and especially USP 5,665; 776,5,389; 677; With 5,422, in 370; Set forth and asked for protection some compsns and share the method that strengthens makeup or pharmaceutical prepn through using carboxylic acid and acting on preparation, the basic structure of hydroxyl monocarboxylic acid that is wherein disclosed is similar with product of the present invention.But do not disclose or point out its esterification reaction product in the application.The application number that is entitled as " method that contains the compsn and the alleviation skin aging sign of monohydroxy-monobasic acid and related compound " that on April 10th, 1991 submitted to is 07/683,437 U.S. Patent application and relevant application and publication; Especially USP 5,547, and 988,5; 554; In 597 and 5,561,158; Set forth and required compsn that local use contains carboxylic acid molecules or related compound to alleviate or improves the sign of aging, comprise on skin, hair and the nail sign that the change that causes because of interior originality and exogenous aging and damage cause.
Summary of the invention
The objective of the invention is defective to above-mentioned prior art; A kind of hormesis that can overcome oligomerization acid to skin is provided; And strengthen its degree of depth lock water moisture-keeping functions, strengthen the esterification reaction synthetic method and the oligomerization acid propylene diester thereof of the oligomerization acid propylene diester of skin absorption.
The technical scheme taked of the present invention is to achieve these goals: a kind of esterification reaction synthetic method of oligomerization acid propylene diester; It is characterized in that; Comprise the steps: by weight percentage the acid of 30-48% oligomerization, 1-3% catalyzer, 47-69% Ucar 35 to be added in the reaction kettle, control reaction temperature is 80-120 ℃, stirs 2-8 hour; Said catalyzer is selected liquid catalyst or solid catalyst for use; After reaction finishes, when selecting liquid catalyst for use, need to use alkali to be neutralized to solution acid alkalinity and be neutrality; When selecting solid catalyst for use, need the filtering separation solid catalyst, finally obtain oligomerization acid propylene diester product.
Said liquid catalyst is the vitriol oil.
Said solid catalyst is selected from quicklime, kaolin, the zeyssatite any.
Said Ucar 35 is selected pharmaceutical grade 1 for use, the 2-Ucar 35.
Said neutralization bases is selected from quicklime, and is any in sodium hydroxide, the Pottasium Hydroxide.
Any in the oligomerization acid that said oligomerization acid is selected from the oligomerization acid that derives from VISOSE, the oligomerization acid that derives from seaweed gel, derive from aminoglycan.
The oligomerization acid starting material source that the present invention relates to; Be the oligomerization acid of VISOSE through the fine chemistry industry prepared; Be faint yellow powdery or lenticular white solid, water cut is lower than 2%, and the working method of product comes from patent of invention, and (publication number is: CN101532042); Simultaneously, this invention also relates to the oligomerization acids product that comes from aminoglycan and Sargassum polysaccharides.
The present invention also provides the oligomerization acid that utilizes above-mentioned compound method preparation propylene diester.
The invention has the beneficial effects as follows: utilize inventive process of the present invention to obtain a kind of novel substance structure; Numerous researchs show, the stronger biological activity of molecule performance of oligomer band carboxylic group, and product of the present invention has overcome the hormesis of acidic substance to skin; Strengthen the absorption of skin; Show good lock water performance of keeping humidity, and have activation skin and antisenility function, have a good application prospect at cosmetic industry.
Embodiment
Below in conjunction with specific embodiment the present invention is described further, but not as to qualification of the present invention.
Embodiment 1
Take by weighing 3 kilograms of oligomerization acid, 6.9 kilograms of Ucar 35,0.1 kilogram of kaolin is put into 30 liters of reaction kettles; Be warming up to 80 ℃ under stirring, reacted 8 hours, after reaction finishes; Remove by filter kaolin, unnecessary Ucar 35 is removed in underpressure distillation, can obtain oligomerization acid propylene diester product.Wherein, oligomerization acid is for coming from the oligomerization acid of VISOSE.
Embodiment 2
Take by weighing 4.8 kilograms of oligomerization acid, 4.9 kilograms of Ucar 35,0.3 kilogram of the vitriol oil is put into 30 liters of reaction kettles; Condensation reflux unit is housed on the reaction kettle, temperature measuring equipment, water trap starts stirring; Progressively be warming up to 120 ℃, reacted 2 hours, after the end, with 2 liters of repetitive scrubbings of 2% sodium hydroxide; Till potential of hydrogen is neutrality (pH value control 6.8-7.2), the moisture in the product is removed through distillation, and unreacted Ucar 35 can be removed through shunting, can obtain oligomerization acid propylene diester product.Wherein, oligomerization acid is for coming from the oligomerization acid of seaweed gel.
Embodiment 3
Take by weighing 3.8 kilograms of oligomerization acid, 6.0 kilograms of Ucar 35,0.2 kilogram in zeyssatite is put into 30 liters of reaction kettles, is warming up to 100 ℃ under stirring, and reacts 6 hours, and reaction removes by filter catalyzer after finishing, and unnecessary Ucar 35 is removed in underpressure distillation.Can obtain oligomerization acid propylene diester product.Wherein, oligomerization acid is for coming from the oligomerization acid of aminoglycan.
Embodiment 4
Take by weighing 4.5 kilograms of oligomerization acid, 5.7 kilograms of Ucar 35,0.2 kilogram of the vitriol oil is put into 30 liters of reaction kettles; Condensation reflux unit is housed on the reaction kettle, temperature measuring equipment, water trap starts stirring; Progressively be warming up to 100 ℃, reacted 3 hours, after the end, with 1 liter of liquid repetitive scrubbing of 2% Pottasium Hydroxide; Till potential of hydrogen is neutrality (pH value control 6.8-7.2), the moisture in the product is removed through distillation, and unreacted Ucar 35 can be removed through shunting, obtains oligomerization acid propylene diester product.Wherein, oligomerization acid is for coming from the oligomerization acid of VISOSE.
Embodiment 5
Take by weighing 4.8 kilograms of oligomerization acid, 5.1 kilograms of Ucar 35,0.1 kilogram in sulfuric acid is put into 30 liters of reaction kettles; Condensation reflux unit is housed on the reaction kettle, temperature measuring equipment, water trap starts stirring; Progressively be warming up to 100 ℃, react after 1 hour, in reaction kettle, throw in 0.2 kilogram of quicklime, continue reaction 2 hours; Remove by filter deposition, remaining Ucar 35 is removed in underpressure distillation, obtains oligomerization acid propylene diester product.Wherein, oligomerization acid is for coming from the oligomerization acid of aminoglycan.
Application implementation example 1: contain the lock water skin-active mask of 2% oligomerization acid propylene diester, fill a prescription as follows:
Raw material weight degree (%)
Emulsifying agent S 3.0
Vitabiosol 4.0
Azone 1.5
VE (vitamin E) 1.01
GTCC (dipotassium glycyrrhizinate) 1.0
Oligomerization acid propylene diester 2.0
Hydroxy propyl ester 0.05
MP 0.15
Wallantoin 0.2
Ucar 35 4.0
Outstanding horse BP 0.2
Essence 0.1
Water 82.79
By the mask product that this prescription forms, supplying examination person is the Ms more than 35 years old, totally 100 people, and per week uses 2 times, and a month " Invest, Then Investigate " service condition shows good product function.
The tender skin skin toner of application implementation example 2:1.5% oligomerization acid propylene diester liquid
Raw material weight degree (%)
Ucar 35 6.0
Oligomerization acid propylene diester 1.5
MP 0.12
GD-2901 (Radix Glycyrrhizae extract) 3.0
0.5%HA (mucinase) 10.0
Outstanding horse BP 0.3
CO-40 (sterilant CO) 0.3
Essence 0.1
Water 78.68
By the product that this compsn forms, supplying examination person be 18-35 Mrs year 50 people, 35-45 Mrs year 50 people, and by conventional method of use use, a month " Invest, Then Investigate " result of use shows good tender skin effect.
The good lock water performance of keeping humidity of product performance of the present invention, and have activation skin and antisenility function, solved oligomerization acid to skin defective excitatory.Have a good application prospect at cosmetic industry.
Above-described embodiment, the present invention embodiment a kind of more preferably just, common variation that those skilled in the art carries out in technical scheme scope of the present invention and replacement all should be included in protection scope of the present invention.
Claims (6)
1. the esterification reaction synthetic method of an oligomerization acid propylene diester is characterized in that, this method comprises the steps: by weight percentage the acid of 30% oligomerization, 1% catalyzer, 69% Ucar 35 to be added in the reaction kettle; Control reaction temperature is 80-120 ℃; Stirred 2-8 hour, said catalyzer is selected liquid catalyst or solid catalyst for use, after reaction finishes; When selecting liquid catalyst for use, need to use alkali to be neutralized to solution acid alkalinity and be neutrality; When selecting solid catalyst for use, need the filtering separation solid catalyst, finally obtain oligomerization acid propylene diester product; Any in the oligomerization acid that said oligomerization acid is selected from the oligomerization acid that derives from VISOSE, the oligomerization acid that derives from seaweed gel, derive from aminoglycan.
2. the esterification reaction synthetic method of oligomerization acid propylene diester according to claim 1, it is characterized in that: said liquid catalyst is the vitriol oil.
3. the esterification reaction synthetic method of oligomerization according to claim 1 acid propylene diester is characterized in that: said solid catalyst is selected from quicklime, kaolin, the zeyssatite any.
4. the esterification reaction synthetic method of oligomerization acid propylene diester according to claim 1, it is characterized in that: said Ucar 35 is selected pharmaceutical grade 1 for use, the 2-Ucar 35.
5. the esterification reaction synthetic method of oligomerization acid propylene diester according to claim 1, it is characterized in that: said neutralization bases is selected from quicklime, and is any in sodium hydroxide, the Pottasium Hydroxide.
6. the oligomerization acid propylene diester of compound method preparation according to claim 1.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009101783258A CN101671372B (en) | 2009-10-16 | 2009-10-16 | Esterification reaction synthetic method of oligomeric propylene diester and oligomeric propylene diester thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009101783258A CN101671372B (en) | 2009-10-16 | 2009-10-16 | Esterification reaction synthetic method of oligomeric propylene diester and oligomeric propylene diester thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101671372A CN101671372A (en) | 2010-03-17 |
CN101671372B true CN101671372B (en) | 2012-01-11 |
Family
ID=42018814
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2009101783258A Active CN101671372B (en) | 2009-10-16 | 2009-10-16 | Esterification reaction synthetic method of oligomeric propylene diester and oligomeric propylene diester thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN101671372B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103497260B (en) * | 2013-09-18 | 2016-09-21 | 农业部规划设计研究院 | A kind of β-oligomerization acid, its preparation method and application |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101532042A (en) * | 2008-12-05 | 2009-09-16 | 王士奎 | Method for preparing oligomeric acid potassium or oligomeric acid ammonium and application thereof |
CN101547939A (en) * | 2007-08-09 | 2009-09-30 | 株式会社纪文福德凯米发 | Propylene glycol hyaluronate ester and external preparation for skin using the same |
-
2009
- 2009-10-16 CN CN2009101783258A patent/CN101671372B/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101547939A (en) * | 2007-08-09 | 2009-09-30 | 株式会社纪文福德凯米发 | Propylene glycol hyaluronate ester and external preparation for skin using the same |
CN101532042A (en) * | 2008-12-05 | 2009-09-16 | 王士奎 | Method for preparing oligomeric acid potassium or oligomeric acid ammonium and application thereof |
Also Published As
Publication number | Publication date |
---|---|
CN101671372A (en) | 2010-03-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN103565699B (en) | A kind of black Fructus Lycii freckle removing and whitening defying age essence and preparation method thereof | |
CN106176690B (en) | Hyaluronic acid oral care film and preparation method and application | |
CN108685759A (en) | A kind of composition of hyaluronic acid substance and tetrahydropyrimidine substance | |
EP2278986B1 (en) | A product for topical administration | |
US20060210609A1 (en) | Fucoidan compositions and methods for dietary and nutritional supplements | |
CN107714504A (en) | A kind of same human-like collagen composition and its applied in cosmetics | |
EP2175833B1 (en) | Dermocosmetic compositions based on tamarind seed polysaccharide and vegetable extracts | |
CN109998937B (en) | Cosmetic series containing glycerol glucoside (alpha GG) and preparation method thereof | |
US6689349B1 (en) | Skin protection agents containing a fragment mixture produced from hyaluronic acid by hydrolysis | |
KR101936294B1 (en) | Composition comprising for skin-whitening and anti-wrinkling extract of Rumex acetosella L. or extract of Hydrangea serrata | |
CN109481377A (en) | A kind of skin barrier remediation composition and preparation method thereof | |
US20220105020A1 (en) | Hyaluronic acid skin care composition and preparation method and application thereof | |
JPH07252129A (en) | Agent for keeping corneal layer of epidermis healthy, prepared from rice | |
KR100443588B1 (en) | Cosmetic composition containing paeonia suffruticosa andrews extract and albizzia julibrissin dura extract having anti-ageing effect | |
KR20160055597A (en) | The composition of functional cosmetics containing silicic acid | |
CN101671372B (en) | Esterification reaction synthetic method of oligomeric propylene diester and oligomeric propylene diester thereof | |
CN1843325A (en) | Use of alga oligosaccharide in cosmetics | |
US20100183724A1 (en) | Hydrogel of Chitosan Carboxyalkylamide, Preparation Thereof and Cosmetic and Dermatological Use Thereof | |
KR20080068077A (en) | Fibroblast activator, method for activation of fibroblast, collagen synthesis promoter, method for promotion of collagen synthesis, skin aging-preventing agent, and method for prevention of aging of the skin | |
KR101448222B1 (en) | Cosmetic composition containing fruit vinegar | |
CN105997587A (en) | Traditional Chinese medicine skin protection cream | |
KR20210055475A (en) | A composition for improving skin beauty containing glycosaminoglycan | |
RU2308937C1 (en) | Cosmetic biologically active supplement and cosmetic lithophytocomplex on its base | |
CN104042450B (en) | Lemon skin mask and preparation method thereof | |
CN108186438A (en) | A kind of after-sun gel containing Porcine HGF and preparation method thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant |