CN1251034A - Use of low molecular oligomer esters of alpha-hydroxy acids and/or aromatic of o-hydroxy acids in cosmetic formulations - Google Patents
Use of low molecular oligomer esters of alpha-hydroxy acids and/or aromatic of o-hydroxy acids in cosmetic formulations Download PDFInfo
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- CN1251034A CN1251034A CN98803176A CN98803176A CN1251034A CN 1251034 A CN1251034 A CN 1251034A CN 98803176 A CN98803176 A CN 98803176A CN 98803176 A CN98803176 A CN 98803176A CN 1251034 A CN1251034 A CN 1251034A
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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
-
- 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
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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
- A61K8/37—Esters of carboxylic acids
-
- 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
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
-
- 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
- A61Q19/08—Anti-ageing preparations
-
- 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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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
- A61K2800/28—Rubbing or scrubbing compositions; Peeling or abrasive compositions; Containing exfoliants
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Cosmetics (AREA)
Abstract
The invention relates to the use of low molecular oligomer esters of alpha-hydroxy acids and/or aromatic o-hydroxy acids in cosmetic formulations, wherein the corresponding alpha-hydroxy acid and/or aromatic o-hydroxy acid is controllably released by hydrolysis during use.
Description
The present invention relates to the application of oligoester in cosmetic formulations of low-molecular-weight, alpha-hydroxy acid and/or aromatic of o-hydroxy acids.
In recent years, people have furtherd investigate the activity of alpha-hydroxy acid (abbreviating " AHAs " as) in the modern beauty art, and alpha-hydroxy acid is used as anti-aging material.These acid often are called as fruit acid, and this title has been pointed out their natural origin.The example of most important fruit acid has glycolic (deriving from Caulis Sacchari sinensis), and lactic acid (deriving from yogurt), citric acid (deriving from the Citrus fruit), tartaric acid (deriving from wine), malic acid (deriving from Fructus Mali pumilae) also have acetone acid (deriving from papaya fruit).But, aromatic of o-hydroxy acids (for example salicylic acid) also has same effect.
The clinical activity of these AHAs and therapeutic activity be at first in the eighties research in this century, and the dermatologist is used for the treatment of extremely exsiccant skin and chronic eczema with them to be higher than 12% concentration from that time.In this respect, proved that now these acid have other effect to skin.In therapeutic process, it is more smooth, more soft that skin becomes, and dirt has disappeared and skin seems more healthy.
In fact, the effect of AHAs is the softening colloid that the skin of epidermis is kept together.This just quickens the normal desquamation of dead bark skin cell and thin surface skin striped polishes in this process.
The salicylic acid that is used to treat acne, psoriasis, wart or the dandruff for a long time also has very big importance as keratolysis and ceratoplasty working substance in cosmetics, because its application produces slight decortication effect to skin.
Be full of a large amount of cosmetics on the market now, they comprise this class AHAs and aromatic of o-hydroxy acids, are called as the product that wrinkle resistant cream or anti-aging product or conduct make skin regeneration.
Except the decortication effect of having described, then think AHA about another theory of the model of action of alpha-hydroxy acid and aromatic of o-hydroxy acids
SChafe only is so it causes the skin mild swelling to polish.If implying this effect in the anti-aging effect really, the application of these free acids and advantage thereof must cause serious problems so, especially about long-term effect.
This free acid is mixed cosmetics carrier also have other shortcoming.At first, lower pH can cause considerable incompatible reaction; Secondly, this acid soluble in water is very fast after application can be washed off again.
The product (derivant of AHAs does not cause that pH greatly reduces during beginning, and this AHAs can therefrom slowly be discharged for a long time) that comprises the derivant of these AHAs should be desirable.
So, the objective of the invention is will be in the cosmetics AHAs commonly used become this form, promptly it is water insoluble and mainly be the greatly reduction that does not cause pH, and effectively AHAs for a long time from wherein slowly being discharged.
Have now found that alpha-hydroxy acid and/or aromatic of o-hydroxy acids can the water-insoluble oligomerization products of esterified one-tenth, then they just can be in the presence of water hydrolysis and discharge monomer A HAs.
So, the invention provides the application of oligoester in cosmetic formulations of low-molecular-weight, alpha-hydroxy acid and/or aromatic hydroxy acid, corresponding alpha-hydroxy acid and/or aromatic of o-hydroxy acids in application by hydrolysis by controllable release.
In general, this base polymer and oligomer are known.For example, the polymeric ester of height of known selected rudimentary hydroxy acid (especially lactic acid) can be tolerated well by health and for example be used as the health compatibility and the absorbefacient suture material of health in operation technique, and it was degraded and is excreted in the time of several weeks or several months.
Describe average oligomeric degree among the DE 36 20 685 and be at most 100 oligoester, especially lactic acid and/or the oligoester of glycolic.The document has been described the application in covering application on human skin or zoodermic compositions as absorbability carrier and/or film former of these esters.
Yet, this quasi-oligomer discharges free hydroxyl group acid in cosmetic formulations application was never described.
Oligomer of the present invention is characterised in that, the average oligomeric degree of selected acid is about at the most 30, preferably about at the most 10.
The polyester oligomer of hydroxy carboxylic acid can directly pass through the polycondensation preparation of hydroxy carboxylic acid or hydroxy carboxylic acid mixture in principle, but usefully, add the reaction promoter that is used to regulate oligomeric degree in a known way for the concrete oligomeric degree of adjusting, wherein monohydric alcohol or polyhydric alcohol or organic acid here may be particularly suitable.It is in fact common just as reactive site that two kinds of described monomeric or oligomer form the group (promptly be on the one hand hydroxyl, be carboxyl on the other hand) of esters.
Specifically, in preferred embodiments, have 4 at the most, especially have at the most that the alcohol of 3 hydroxyls is suitable, this makes monohydric alcohol may have special importance on the one hand, and on the other hand, dihydroxylic alcohols, especially trihydroxylic alcohol may play a crucial role.Under the situation about in the end mentioning, described alcohol is glycerol especially, and it is by causing extremely different products with the reaction of AHA oligomer.The example of the alcohol that other is suitable has: ethylene glycol, propylene glycol, 1,3 butylene glycol, trimethylolpropane, low molecular poly, polypropylene glycol, 1,5-pentanediol or alternatively more polyhydric alcohol.
In the common application field of carboxylic acid, on the one hand the carboxylic acid that tolerates on the physiology (under this situation especially monocarboxylic acid) may be significant, but also may be polyfunctional carboxylic acids, for example dicarboxylic acids or tricarboxylic acids.
Oligomeric hydroxy carboxylic acid or their derivant are by original known method preparation.Certainly, (promptly under 's the situation and under the situation at reaction promoter) in all cases, not only can use each free active component of mentioned type, and can use those derivants, they form required polyester oligomer by original known mode under the condition of esterification or transesterification.So for example alcohol ester is exactly suitable, in addition, also can use easy-to-handle dimerisation products, for example the dimerisation products of lactic acid and/or glycolic, i.e. lactide and/or Acetic acid, hydroxy-, bimol. cyclic ester.
Polycondensation reaction normally by raw material being heated to above the temperature of fusing point, preferably in the presence of catalyst (especially esterification catalyst), is carried out under the anhydrous condition in inert gas atmosphere under this situation.The amount of catalyst for application and type decided operative temperature and reaction duration.Because the conversion ratio of this reaction generally almost is 100%, so end product has and can easily control by the interpolation of reactant.The polycondensation reaction of the type is well known to those skilled in the art.So need not list the reaction condition of wide range here in detail.
The present invention also provides and has been used for the low-molecular-weight oligomer that cosmetic formulations comprises alpha-hydroxy acid and/or aromatic of o-hydroxy acids, they are by monomer alpha-hydroxy acid and/or aromatic of o-hydroxy acids or its reactive derivative and monohydric alcohol or polyhydric alcohol or organic acid prepared in reaction, corresponding alpha-hydroxy acid and/or aromatic of o-hydroxy acids in application by hydrolysis from these oligomer by controllable release.
The chemical compound that alpha-hydroxy acid of using and o-hydroxy acids are preferably listed below: glycolic and lactic acid, these two all appears in the metabolism of Living Organism, and all processed by health and secrete, the lactic acid of Ying Yonging is its racemic object form or alternatively is the form of its optical antimer or as any required mixture of this optical antimer here; Alpha-hydroxy butanoic acid, Alpha-hydroxy valeric acid, citric acid, tartaric acid, malic acid, propylene carbonate, 6-caprolactone, salicylic acid, m-hydroxybenzoic acid, P-hydroxybenzoic acid, gallate, racemic tartaric acid, diphenylglycollic acid, mandelic acid or acetone acid alternatively.
Preferred alcohol acid and/or lactic acid or its dimerisation products very especially in this situation.
In the important embodiment of the present invention, used pleionomer.This expression has only independent a kind of alpha-hydroxy acid or its a kind of reactive derivative or has only independent a kind of o-hydroxy acids or its a kind of reactive derivative (for example have only lactic acid or have only salicylic acid) is used to prepare described oligoester.
In another embodiment preferred of the present invention, used assorted oligomer.This is illustrated in the polycondensation reaction of this oligomerization product of preparation, has used two or more different alpha-hydroxy acids and/or aromatic of o-hydroxy acids.Therefore, also may use alpha-hydroxy acid and for example salicylic mixture as monomer.
Particularly preferred oligomer is for example synthetic from following monomer: glycerol, lactide and Acetic acid, hydroxy-, bimol. cyclic ester; Ethylene glycol, lactic acid and glycolic; Propylene glycol, lactide and Acetic acid, hydroxy-, bimol. cyclic ester; Glycerol and lactide; Glycerol, glycolic and hydroxybutyric acid; Ethylene glycol and hydroxypentanoic acid; Glycerol and ethyl lactate; Glycerol, propylene carbonate and glycolic; Ethylene glycol and lactide; Ethylene glycol, glycolic and ethyl lactate; Glycerol, glycolic and 6-caprolactone.
In this respect, for example to look like be such to the product of glycerol, lactide and Acetic acid, hydroxy-, bimol. cyclic ester:
Wherein the k+l+m sum preferably is less than or equal to 12, particularly preferably is less than or equal to 6 (based on lactides).
The above-claimed cpd of listing is a small amount of candidate of particularly preferred product and the unrestricted character of determining.
Assorted oligomer has favourable performance usually, because they show lower crystallization tendency and associated cloud point.In addition, because higher water absorption and hydrolysis rate, they can more promptly be degraded.
On the other hand, this more rapidly hydrolysis rate cause this fact, promptly corresponding oligomer product is very sensitive to hydrolysis, thereby unstable in the aqueous cosmetic formulations of routine.Therefore be necessary to prepare water-free preparation.A favorable method that addresses this problem is that the optional anhydrous AHA oligomer preparation that contains proper auxiliary agent is separated preparation with the second kind of aqueous components that comprises auxiliary agent commonly used in the cosmetic formulations.Just before the application of the cosmetic formulations of making, directly these two kinds of components are mixed.But the mixed system that this advantageous applications was learnt from (medicine) technology originally (for example being used to mix the system of bone cement, reaction cement or moulding material) carries out.An example of being worth mentioning is the dual chamber syringe with attached static mixer that is equipped with, and it is well known by persons skilled in the art.With regard to these mixed systems, also may regulate simply and change the mixing ratio of oligomer with water.Therefore, for example 1: 10～1: 1 mixing ratio is possible.For example, the mixed system that derives from MIXPACSystems AG also is suitable.
Therefore, the present invention also provides the cosmetic formulations that comprises a cover two or more independent components ready for using, wherein a kind of component comprises in the claim 1～7 anhydrous formulation of at least one oligomer product, optional other auxiliary agent that contains, then comprise the aqueous cosmetics preparation as another kind of component, optional other auxiliary agent and the additive of using always in this class cosmetic formulations that contain.
So, the advantage of using described low dimerization product is, mainly is that pH does not greatly reduce, otherwise Diazolidinyl Urea.Yet in the hydrolysis on the spot of described low poly structure, monomer A HAs and aromatic of o-hydroxy acids are released gradually, can cause then known they to the advantageous effects of skin.In addition, might admix these relatively large oligomer (they are as the donor of described free acid) certainly, show that this effect significantly is better than using free AHA
SEffect.
Be used to prepare the optional certainly a large amount of known and confirmed materials of component of corresponding cosmetic formulations.The oligoester of alpha-hydroxy acid and/or aromatic of o-hydroxy acids can easily be mixed with skin nursing component and the auxiliary agent used always, and this advantageously depends on anhydrous formulation.
With regard to described independently preparation, preparation may contain the anhydrous formulation of the described oligomer of proper auxiliary agent or additive on the one hand, then prepares the cosmetic formulations that comprises skin nursing component commonly used on the other hand.For example, in the preparation of O/W emulsifiable paste, described oligomer can be present in the oil phase, and water is preparation separately then.Perhaps, can also as one mutually preparation do not contain the oligomer mixture of any additives, all the other components that are usually used in skin care formulation then are present in second aqueous phase.Under each situation, just before application, mix these two independently phases then.
Some component and additives commonly used can be listed below:
Aliphatic alcohol, fatty acid ester (especially fatty acid triglycercide), fatty acid, lanoline, natural or synthetic oil or wax, emulsifying agent, for example Tegacid special, Teginacids, Tego Care (derive from Th.Goldschmidt, Essen), Cremophors (BASF, Ludwigshafen), Emulgins (Henkel, D ü sseldorf), Hostacerin DGS or alternatively Hostaphat (Hoechst), randomly aromatic oil, lower alcohol, dihydroxylic alcohols or polyhydric alcohol, thickening agent (for example silicon dioxide) in addition.
Cosmetic formulations of the present invention may comprise about 5% to up to the oligomer product near 100% amount, and the application of pure oligomer also is possible.The preferred content of oligoester is 5%～50% in the finished product.
Suppose that those skilled in the art can as above describe and need not describe in further detail in broadest utilization.So it is embodiment preferred only is regarded as descriptive disclosing, restrictive anything but.
It is for referencial use that all applications listed in the text up and down, patent and disclosed whole disclosure are all incorporated the application into.
The following examples are used for setting forth the present invention.
Embodiment 1
In the normal experiment device, in nitrogen and under stirring with 4mol L-lactide and the fusing of 1mol glycerol, then at 1 hour internal heating to 190 ℃.Allow this be reflected at and carried out under 188～192 ℃ 5 hours, discharge this glycerol-oligomeric-lactide product while hot.Added 0.5%o-phosphoric acid (o-phosphoric acid) (based on the amount of lactide) as catalyst.
Embodiment 2
In the normal experiment device, in nitrogen and under stirring with 1mol glycerol, 2mol L-lactide and 1mol Acetic acid, hydroxy-, bimol. cyclic ester at one hour internal heating to 195 ℃.Allow this mixture reaction 5 hours then, discharge this glycerol-oligomeric-lactide-Acetic acid, hydroxy-, bimol. cyclic ester (1: 2: 1) while hot.The catalyst that adds is an o-phosphoric acid, and consumption is 0.5% based on lactide and Acetic acid, hydroxy-, bimol. cyclic ester total amount.The residual content of glycerol≤2%.
Embodiment 3
As embodiment 2, make the reaction of 1mol glycerol and 3mol Acetic acid, hydroxy-, bimol. cyclic ester, generate glycerol-oligomeric-Acetic acid, hydroxy-, bimol. cyclic ester.Here the catalyst of Tian Jiaing is diethyl ether solution (the 2.5g SnCl of 7ml of stannous chloride (Sn (II) chloride)
2Solution in the 100oml ether).
Embodiment 4
In conventional device for carrying out said, in nitrogen and under stirring with 1mol ethylene glycol and 1.5mol DL-lactic acid 6 hours internal heating to up to 150 ℃～200 ℃.Then this system is cooled to 150 ℃ and evacuation carefully, finishes conversion under holding in the palm at 200 ℃ and 10.After 30 minutes, under about 150 ℃, discharge product while hot.
Embodiment A
The preparation of skin nursing emulsifiable paste
The I phase:
Under 60 ℃, will consist of 1: 1.5 the low polylactide (by preparing like that among the embodiment 4) of ethylene glycol and the glycerol that consisted of 1: 5 hangs down polylactide (by preparing like that among the embodiment 1) and mixes equably with 40: 60 ratios.Under this temperature, mixture is forwarded in the 10ml chamber of 1: 1 dual chamber syringe.After the cooling, this mixture has sweet shape denseness.
The II phase:
This water comprises:
3.0% 1,2-propylene glycol (Art.No.107478) (1)
1.2% antiseptic (1)
0.25% 4-methyl hydroxybenzoate sodium salt (Art.No.106756) (1)
2.0% Tween 80 (emulsifying agent) (1)
Add mutually suitable of viscosity that polyacrylic acid sodium salt makes II phase under the room temperature and I.Then II is imported mutually second chamber of described dual chamber syringe.Seal this dual chamber syringe with normal mode.
Source of supply:
(1)Merck?KGaA，Darmstadt
Claims (8)
1. the application of oligoester in cosmetic formulations of low-molecular-weight, alpha-hydroxy acid and/or aromatic of o-hydroxy acids, corresponding alpha-hydroxy acid and/or aromatic of o-hydroxy acids in application by hydrolysis by controllable release.
2. the application of claim 1 is characterized in that, described low-molecular-weight oligomer is by monomer alpha-hydroxy acid and/or aromatic of o-hydroxy acids or also have its reactive derivative and monohydric alcohol or polyhydric alcohol or organic acid reaction acquisition.
3. claim 1 or 2 application is characterized in that, have used pleionomer, and they are only to use a kind of monomer alpha-hydroxy acid or aromatic of o-hydroxy acids preparation.
4. claim 1 or 2 application, base is characterised in that, has used assorted oligomer, they are to use two or more different monomer alpha-hydroxy acids and/or aromatic of o-hydroxy acids preparation.
5. the application of one of claim 1～4 is characterized in that, preferably with oligomeric reaction product and monohydric alcohol or the polyhydric alcohol or the organic acid reaction of lactic acid, glycolic and/or adjacent salicylic acid or its reactive derivative.
6. the application of one of claim 1～5 is characterized in that, has used about at the most 30, preferred about at the most 10 the oligomer of average oligomeric degree.
7. be used for cosmetic formulations, comprise the low-molecular-weight oligomer of alpha-hydroxy acid and/or aromatic of o-hydroxy acids, wherein said oligomer is by monomer alpha-hydroxy acid and/or aromatic of o-hydroxy acids or its reactive derivative and monohydric alcohol or polyhydric alcohol or organic acid prepared in reaction, corresponding alpha-hydroxy acid and/or aromatic of o-hydroxy acids in application by hydrolysis from these oligomer by controllable release.
8. the cosmetic formulations that comprises a cover two or more independent components ready for using, wherein a kind of component comprises in the claim 1～7 anhydrous formulation of at least one oligomer product, optional other auxiliary agent that contains, then comprise the aqueous cosmetics preparation as another kind of component, optional other auxiliary agent and the additive of using always in this class cosmetic formulations that contain.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19714765.8 | 1997-04-10 | ||
| DE19714765A DE19714765A1 (en) | 1997-04-10 | 1997-04-10 | Use of low molecular weight, oligomeric esters of alpha-hydroxy acids and / or aromatic o-hydroxy acids in cosmetic formulations |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1251034A true CN1251034A (en) | 2000-04-19 |
Family
ID=7825977
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN98803176A Pending CN1251034A (en) | 1997-04-10 | 1998-04-07 | Use of low molecular oligomer esters of alpha-hydroxy acids and/or aromatic of o-hydroxy acids in cosmetic formulations |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0973496A1 (en) |
| JP (1) | JP2001521508A (en) |
| KR (1) | KR20000076112A (en) |
| CN (1) | CN1251034A (en) |
| AU (1) | AU7429598A (en) |
| CA (1) | CA2283517A1 (en) |
| DE (1) | DE19714765A1 (en) |
| HU (1) | HUP0001693A2 (en) |
| PL (1) | PL335423A1 (en) |
| WO (1) | WO1998044903A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105411870A (en) * | 2006-07-06 | 2016-03-23 | 斯蒂潘公司 | Alkyl lactyllactates and processes of making the same |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7833543B2 (en) | 1995-06-07 | 2010-11-16 | Durect Corporation | High viscosity liquid controlled delivery system and medical or surgical device |
| US6413536B1 (en) * | 1995-06-07 | 2002-07-02 | Southern Biosystems, Inc. | High viscosity liquid controlled delivery system and medical or surgical device |
| US20040001889A1 (en) | 2002-06-25 | 2004-01-01 | Guohua Chen | Short duration depot formulations |
| WO2004054542A2 (en) | 2002-12-13 | 2004-07-01 | Durect Corporation | Oral drug delivery system comprising high viscosity liquid carrier materials |
| ES2602273T3 (en) | 2004-09-17 | 2017-02-20 | Durect Corporation | Prolonged local anesthetic composition containing Saib |
| US20070027105A1 (en) | 2005-07-26 | 2007-02-01 | Alza Corporation | Peroxide removal from drug delivery vehicle |
| WO2008006076A2 (en) * | 2006-07-06 | 2008-01-10 | Stepan Company | Alkyl lactyllactates and processes of making the same |
| WO2008006058A2 (en) | 2006-07-06 | 2008-01-10 | Stepan Company | Alkyl lactyllactate solvent compositions |
| PL2117521T3 (en) | 2006-11-03 | 2012-11-30 | Durect Corp | Transdermal delivery systems comprising bupivacaine |
| WO2009075782A1 (en) | 2007-12-06 | 2009-06-18 | Durect Corporation | Methods useful for the treatment of pain, arthritic conditions, or inflammation associated with a chronic condition |
| US20100260844A1 (en) | 2008-11-03 | 2010-10-14 | Scicinski Jan J | Oral pharmaceutical dosage forms |
| JP5219093B2 (en) * | 2009-11-14 | 2013-06-26 | 公益財団法人北九州産業学術推進機構 | Lactic acid oligomer and molded article thereof |
| WO2014144975A1 (en) | 2013-03-15 | 2014-09-18 | Durect Corporation | Compositions with a rheological modifier to reduce dissolution variability |
| JP2015093854A (en) * | 2013-11-12 | 2015-05-18 | 株式会社クレハ | Aqueous composition and method for inhibiting hydrolysis |
| KR20220140711A (en) | 2020-01-13 | 2022-10-18 | 듀렉트 코퍼레이션 | Reduced Impurity Sustained Release Drug Delivery Systems and Related Methods |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3620685A1 (en) * | 1986-06-20 | 1987-12-23 | Henkel Kgaa | NEW AGENTS FOR COVERING INJURED AND / OR INJURED AREAS OF HUMAN OR ANIMAL SKIN |
| US5091171B2 (en) * | 1986-12-23 | 1997-07-15 | Tristrata Inc | Amphoteric compositions and polymeric forms of alpha hydroxyacids and their therapeutic use |
| DE19520237A1 (en) * | 1995-06-02 | 1996-12-05 | Beiersdorf Ag | Cosmetic or dermatological preparations containing oligomers or polymers of alpha-hydroxycarboxylic acids |
-
1997
- 1997-04-10 DE DE19714765A patent/DE19714765A1/en not_active Withdrawn
-
1998
- 1998-04-07 EP EP98921437A patent/EP0973496A1/en not_active Withdrawn
- 1998-04-07 CN CN98803176A patent/CN1251034A/en active Pending
- 1998-04-07 PL PL98335423A patent/PL335423A1/en unknown
- 1998-04-07 WO PCT/EP1998/002013 patent/WO1998044903A1/en not_active Application Discontinuation
- 1998-04-07 JP JP54238398A patent/JP2001521508A/en active Pending
- 1998-04-07 CA CA002283517A patent/CA2283517A1/en not_active Abandoned
- 1998-04-07 HU HU0001693A patent/HUP0001693A2/en unknown
- 1998-04-07 AU AU74295/98A patent/AU7429598A/en not_active Abandoned
- 1998-04-07 KR KR1019997008200A patent/KR20000076112A/en not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105411870A (en) * | 2006-07-06 | 2016-03-23 | 斯蒂潘公司 | Alkyl lactyllactates and processes of making the same |
| CN105411870B (en) * | 2006-07-06 | 2018-12-25 | 斯蒂潘公司 | Alkyl lactyllactate and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2283517A1 (en) | 1998-10-15 |
| KR20000076112A (en) | 2000-12-26 |
| EP0973496A1 (en) | 2000-01-26 |
| JP2001521508A (en) | 2001-11-06 |
| HUP0001693A2 (en) | 2000-09-28 |
| PL335423A1 (en) | 2000-04-25 |
| AU7429598A (en) | 1998-10-30 |
| WO1998044903A1 (en) | 1998-10-15 |
| DE19714765A1 (en) | 1998-10-15 |
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