GB2105727A - Allantoin amino acid compositions - Google Patents
Allantoin amino acid compositions Download PDFInfo
- Publication number
- GB2105727A GB2105727A GB08216733A GB8216733A GB2105727A GB 2105727 A GB2105727 A GB 2105727A GB 08216733 A GB08216733 A GB 08216733A GB 8216733 A GB8216733 A GB 8216733A GB 2105727 A GB2105727 A GB 2105727A
- Authority
- GB
- United Kingdom
- Prior art keywords
- allantoin
- amino acids
- collagen amino
- amino acid
- complexes
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- 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
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
- A61K8/65—Collagen; Gelatin; Keratin; Derivatives or degradation products thereof
-
- 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
-
- 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
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/75—Anti-irritant
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
- A61Q1/06—Lipsticks
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/12—Face or body powders for grooming, adorning or absorbing
-
- 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
- A61Q19/007—Preparations for dry skin
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
Abstract
Allantoin can be complexed with collagen amino acids to form allantoin collagen amino acid complexes. These complexes may be used in medicinal and cosmetic compositions.
Description
SPECIFICATION
Allantoin amino acid compositions
Allantoin possesses soothing, pain-relieving, keratolytic, moisturizing and anti-irritant properties. It also stimulates cell proliferation.
Allantoin has been complexed with individual amino acids in the past. Allantoin and complexes of sulfur containing amino acids such as methionine are disclosed in U.S. Patent No.
3,107,252. Allantoin pantothenic acid complexes are disclosed in U.S. Patent No. 3,275,643.
Allantoin biotin complexes are disclosed in U.S.
Patent No. 3,290,324. Allantoin glycine complexes are disclosed in U.S. Patent No.
3,927,021. Allantoin complexes with basic amino acids are disclosed in U.S. Patent No. 4,038,287.
The complexes disclosed in the foregoing patents are useful in medicinal and cosmetic compositions.
The present invention seeks to provide alternative allantoin complexes having beneficial properties.
The present invention provides complexes of allantoin and collagen amino acids. Aluminium salts of allantoin and collagen amino acid complexes are also provided by the invention, as are medicinal and cosmetic compositions containing the complexes of the invention.
Collagen is a protein made up of amino acids joined in a chain by peptide linkages. Collagen amino acids useful in the present invention are derived from animal protein, and typically have the following composition of amino acid residues:
Amino acid wt.% present
Alanine 8-11 Arginine 7.8-9 Aspartic Acid 5.7-9 Cystine/cystein 0.1-0.9 Glycine 20-30.5 Glutamic Acid 1 1 1.7 Histidine 0.7-1 Hydroxylysine 0.7-1.2 Hydroxyproline 12.1-14.5 Iso-leucine 1.3-1.8 Leucine 2.8-3.5 Lysine 3.9-5.2 Methionine 0.7-0.9 Phenylalanine 1.1-2.6 Proline 13.8-18 Serine 2.9-4.1 Threonine 1.8-2.6 Tyrosine 0.2-1 Valine 2.1-3.4 The collagen amino acids most useful in the present invention are highly refined hydrolysates.
That is, collagen derived from a variety of different sources is hydrolyzed by conventional techniques with either acid, alkali or enzyme hydrolysis to produce collagen amino acids of the foregoing composition having an average molecular weight of from about 100,000 to about 200,000. The hydrolyzed collagen amino acids which may be used to form the complexes of this invention are usually liquids having a pH of about 5 to about 6.5 and containing at least about 70% by weight free amino acids and about 38% to 42% by weight "protein".
Special reaction conditions are not required to form the desired complexes. A procedure may be used in which allantoin or an aluminium salt of allantoin is combined with liquid collagen amino acids and uniformly mixed to form a wet mass.
The wet mass is then dried at about 82 to 990C (180 to 2100F) until the product is dry and has a relatively constant weight. Drying is usually carried out for from four to six hours, and may be accomplished with any suitable means, including spray drying. The dry complexes are powders having a melting point of about 220O to 2230C.
According to the present invention, allantoin or an aluminium salt of allantoin may be combined with collagen amino acids in a weight ratio of from about 50 to about 80 parts of allantoin or its aluminium salt to about 20 to about 50 parts of collagen amino acids.
It has been found that the allantoin collagen amino acid complexes are remarkably beneficial when used in pharmaceutical or cosmetic compositions for topical application. For example, the complexes exhibit moisture absorptive properties which are greater than would have been expected from a mere addition of allantoin with collagen amino acids. This greater than additive effect exists over a range of relative humidity, and can be demonstrated by comparing moisture absorption isotherms for allantoin and for collagen amino acids with the moisture isotherm of the allantoin collagen amino acids of this invention.
Topical application of pharmaceutical and cosmetic compositions containing from about 0.5 to about 5% by weight of the allantoin collagen amino acid complexes have been found useful for a variety of applications. It has been found, for example, that on application of topical compositions containing the complexes of the invention that a portion of the allantoin collagen amino acid complex penetrates the skin providing moisture to the stratum corneum. At the same time, the portion of the allantoin collagen amino acid which does not penetrate the skin but remains on the skin surface exerts hygroscopic properties and provides moisture to the skin surface.The complex also provides de-briding or sloughing action on dead skin cells fostering heaiing of minor skin abrasions or lacerations and providing a smooth, mildly astringent, but yet comfortable moist skin feeling. This dual effect on and beneath the skin surface is of significant benefit in a wide variety of cosmetic and pharmaceutical compositions, and emphasizes the unexpected nature of the invention.
The following examples demonstrate the preparation of the complexes of this invention as well as compositions containing the complexes.
The examples are illustrative only, and not intended to limit the scope of the invention.
Example 1
80g. allantoin are thoroughly mixed with 20 g.
collagen amino acids to form a uniform wet mass.
The resultant mixture is then dried at 82 to 990C for several hours forming a white powder.
Allantoin collagen amino acid complex is formed which is soluble to the extent of 3 to 4%, by weight, in water and 1 to 2% in 95%, by volume, alcohol.
Example 2
70 g. allantoin are thoroughly mixed with 30 g.
collagen amino acids to form a uniform wet mass.
The resultant mixture is then dried at 82 to 99OC for several hours forming a white powder.
Allantoin collagen amino acid complex is formed which is soluble to the extent of 2 to 3%, by weight, in water, and 1 to 2% in 95%, by volume, alcohol.
Example 3
50 g. allantoin are thoroughly mixed with 50 g.
collagen amino acids to form a uniform wet mass.
The resultant mixture is then dried at 82 to 990C
for several hours forming a white powder.
Allantoin collagen amino acid complex is formed
which is soluble to the extent of 1%, by weight, in
water, and 0.5% in 95%, by volume, alcohol.
Example 4
80 g. of aluminium chlorhydroxy allantoinate
are thoroughly mixed with 20 g. collagen amino
acids to form a uniform wet mass. The resultant
mixture is then dried at 82 to 99 OC for several
hours forming a white powder. Allantoin collagen
amino acid complex is formed which is soluble to the extent of 3 to 4%, by weight, in water, and 1
to 2% in 95%, by volume, alcohol.
Example 5
70 g. of aluminium chlorhydroxy allantoinate
are thoroughly mixed with 30 g. collagen amino
acids to form a uniform wet mass. The resultant
mixture is then dried at 82 to 990C for several
hours forming a white powder. Allantoin collagen
amino acid complex is formed which is soluble to
the extent of 2 to 3%, by weight, in water, and 1
to 2% in 95%, by volume, alcohol.
Example 6
50 g. of aluminium chlorhydroxy allantoinate
are thoroughly mixed with 50 g. of collagen amino acids to form a uniform wet mass. The
resultant mixture is then dried at 82 to 99 OC for several hours forming a white powder. Allantoin collagen amino acid complex is formed which is soluble to the extent of 1%, by weight, in water, and 0.5% in 95%, by volume, alcohol.
Example 7
80 g. aluminium dihydroxy allantoinate are thoroughly mixed with 20 g. collagen amino acids to form a uniform wet mass. The resultant mixture is then dried at 82 to 990C for several hours forming a white powder. Allantoin collagen amino complex is formed which is soluble to the extent of 3 to 4%, by weight, in water, and 1 to 2% in 95%, by volume, alcohol.
Example 8
70 g. of aluminium dihydroxy allantoinate are thoroughly mixed with 30 g. collagen amino acids to form a uniform wet mass. The resultant mixture is then dried at 82 to 990C for several hours forming a white powder. Allantoin collagen amino acid complex is formed which is soluble to the extent of 2 to 3%, by weight, in water, and 1 to 2% in 95%, by volume, alcohol.
Example 9
50 g. of aluminium dihydroxy allantoinate are thoroughly mixed with 50 g. collagen amino acids to form a uniform wet mass. The resultant mixture is then dried at 82 to 990C for several hours forming a white powder. Allantoin collagen amino acid complex is formed which is soluble to the extent of 1%, by weight, in water, and 0.5% in 95%, by volume, alcohol.
The following formulations were made to demonstrate the usefulness of allantoin collagen amino acid complexes.
Dry skin lotion
Ingredients Weight Percent
Myrj 52 1.5
Ceraphyl 368 5
Span 65 0.3
Super Hartolan 0.5
Cetyl Alcohol 0.75
Glyceral Monostearate 5
Tegosept P 0.1
Silicone 200 1 Polymer JR 400 0.25
Propylene Glycol 4.8
Deionized Water 70
Germall 115 0.1
Tegosept M 0.2
Allantoin 0.1
Carbopol 941 2.5 disp. 0.1
Menthol 0.05
Verley Aldehyde 4390 HA 0.25
Ethyl Vanillin 0.002
Ethylene Brasilyate 0.001
Deionized Water 6
Allantoin collagen
Amino Acid complex of
Example 1 4
Lipstick
Ingredient Weight percent
Westol 350 15.0
Castor Oil 5.9
K7061 DSCRed#21 0.1
A6205 Red Iron Oxide 1.73 #5305 DSC Orange #5 1.2 Cl 4-034 DSC Red #21 Al. Lake 0.98 #6607 D & Red #7 0.750 1985R Umber 0.450
K7081 D & Orange #17 0.3
K7040 D8C Red #19 0.250
Titanium Dioxide 328 4
Westol 350 17.2
Modulan 2.9
Novol 9.7
Ceraphyl 50 8.8
Ceraphyl 424 7.3
Candelilla Wax 16.4
Carnauba Wax 0.9
Beeswax 0.9 Multiwax 445 1.9
Silicone Copolymer F0755 0.9
Tenoxll 0.1
Tegosept P 0.1
Tegosept B 0.1
Allantoin 0.1
Germall 115 0.01
Alpha Tocopherol Acetate 0.1 Crotein IPX 0.1
Nopsol A7d 1000/200 0.1
Wheat Germ Oil 0.1
Allantoin Collagen
Amino Acid Complex of
Example 1 1
Perfume Oil FL5995 0.2
Vanilla (50%) 0.1
Lip gloss
Ingredient Weight Percent
Tegosept B .15
Snowhite Petrolatum 31.9
Acetylated Lanolin 36.9
Lanolin Oil 1 5.2 Paraffin Wax 5.6
Acetylated Glycerides 4
Octyl Dimethyl Paba 0.5 Tenox Vl 0.1
Tegosept P 0.1
Snowhite Petrolatum 4.75 D & Red #6 0.01
Citrus Floral Essence FS272 0.25
Allantoin Collagen
Amino Acid Complex of
Example 1 0.25
Night Cream
Ingredient Weight Percent
Hydrosylated Lanolin 0.5
White Beeswax 7.4
Lanolin 26.4
Lanolin Alcohol 1
Yellow Petrolatum 25
Sorbitan Sesquioleate 2.7
Mineral Oil 14.6
Tegosept P 0.1
Tegosept M 0.3
Sodium Borate USP 0.5
Deionized Water 19.6 Lemon #1 0.4
Vitamin A Palmitate 0.05
Imidazolydinyl Urea 0.1
Allantoin Collagen
Amino Acid Complex of
Example 2 0.5
Mascara
Ingredient Weight percent
Beeswax 24.4
Lanolin Wax 15
Makon White Flake 1.5
Ozokerite Wax 3
Carnauba Wax 0.5
C10-13 Isoparaffin 48.
Lecithin 1.0
Tegosept P 0.1
Silica 1.30 Magnesium Trisilicate 3.5
Hydrolyzed Animal Protein 0.5
Aluminium Dihydroxy
Allantoinate 0.2
Allantoin Proteinate 0.2
Imidazolidinyl Urea 0.01 33-134 Black Iron Oxide 0.2
Allantoin Collagen
Amino Acid Complex of
Example 3 0.5
Eye stick
Ingredient Weight percent
Stearyl Heptanoate 0.9
Ozokerite Wax 6
Candelilla Wax 2.5
Carnauba Wax 3.0
Mineral Oil 85.13
Tegosept P 0.1 TegoseptB 0.1
Vitamin A8D 1000/200 0.01
Alpha Tocopheryl Acetate 0.1
Cetearyl Octanoate 0.9
Imidazolydinyl Urea 0.01
A6205 Red Oxide .1% Westol 350 0.5
Carotene (0.1% in IMPM) 0.25
Allantoin Collagen
Amino Acid Complex of
Example 1 0.5
Pressed powder
Ingredient Weight percent
Allantoin Collagon
Amino Acid
Amino Acid Complex of
Example 1 0.5 # ;2673 Cosmetic Brown 0.3 #2817R Brown Iron Oxide 0.5 Cm 624 Cosmetic Yellow 0.3 #15002 Cosmetic Red 0.3
Titanium Dioxide #328 2
Talc 86.6
Perfume 1 Isoproypl Myristate 3
Magnesium Carbonate 2.6 Zine Stearate 3
BHA 0.05
Tegosept M 0.1
Captan 0.1
Claims (6)
1. Complexes of allantoin and collagen amino acids.
2. Aluminium salts of complexes of allantoin and collagen amino acids.
3. Complexes of allantoin and collagen amino acids, and aluminium salts thereof, containing allantoin or its aluminium salt and collagen amino acids in a weight ratio of from 3:50 to 80:20.
4. A process for the production of a complex of allantoin or an aluminium salt thereof and collagen amino acids, wherein collagen is hydrolysed to form collagen amino acids having an average molecular weight of 100,000 to 200,000 and a pH of from 5 to 6.5, the collagen amino acids thus formed are mixed with allantoin or its aluminium salt and the resulting complex is recovered.
5. Pharmaceutical and cosmetic compositions containing a therapeutically effective amount of a complex as claimed in any of claims 1 to 3 or produced by a process as claimed in claim 4.
6. A composition as claimed in claim 5 and substantiall as hereinbefore described.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28736481A | 1981-07-27 | 1981-07-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2105727A true GB2105727A (en) | 1983-03-30 |
| GB2105727B GB2105727B (en) | 1985-04-17 |
Family
ID=23102575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08216733A Expired GB2105727B (en) | 1981-07-27 | 1982-06-09 | Allantoin amino acid compositions |
Country Status (4)
| Country | Link |
|---|---|
| CA (1) | CA1187486A (en) |
| DE (1) | DE3224988A1 (en) |
| FR (1) | FR2510563A1 (en) |
| GB (1) | GB2105727B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2208928A (en) * | 1987-08-21 | 1989-04-19 | G C Dental Ind Corp | Materials for patch testing |
| US4996044A (en) * | 1985-03-21 | 1991-02-26 | Revlon, Inc. | Lipstick formulation and method |
| GB2292080A (en) * | 1994-08-09 | 1996-02-14 | Revlon Consumer Prod Corp | Cosmetic formulations having keratolytic and/or anti-acne activity their preparation and use |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU562620B2 (en) * | 1982-02-24 | 1987-06-18 | Charles Of The Ritz Group Ltd. | Allantoin-hydrolyzed animal protein product |
| DE4429747A1 (en) * | 1994-08-22 | 1996-02-29 | Willige Zimzik Elfriede | Cosmetic ointment and cream bases |
-
1982
- 1982-03-31 CA CA000399963A patent/CA1187486A/en not_active Expired
- 1982-06-09 GB GB08216733A patent/GB2105727B/en not_active Expired
- 1982-07-03 DE DE19823224988 patent/DE3224988A1/en not_active Withdrawn
- 1982-07-26 FR FR8212989A patent/FR2510563A1/en active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4996044A (en) * | 1985-03-21 | 1991-02-26 | Revlon, Inc. | Lipstick formulation and method |
| GB2208928A (en) * | 1987-08-21 | 1989-04-19 | G C Dental Ind Corp | Materials for patch testing |
| GB2208928B (en) * | 1987-08-21 | 1992-04-08 | G C Dental Ind Corp | "patch test materials for the detection of metal allergies" |
| GB2292080A (en) * | 1994-08-09 | 1996-02-14 | Revlon Consumer Prod Corp | Cosmetic formulations having keratolytic and/or anti-acne activity their preparation and use |
| GB2292080B (en) * | 1994-08-09 | 1998-11-25 | Revlon Consumer Prod Corp | Cosmetic formulations having keratolytic and/or anti-acne activity,their preparations and use |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2510563A1 (en) | 1983-02-04 |
| GB2105727B (en) | 1985-04-17 |
| FR2510563B3 (en) | 1984-06-08 |
| DE3224988A1 (en) | 1983-02-10 |
| CA1187486A (en) | 1985-05-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Free format text: IN PAT.BUL.5035,PAGE 2122 FOR 2105727 READ 2015727 |
|
| 711A | Proceeding under section 117(1) patents act 1977 | ||
| PCNP | Patent ceased through non-payment of renewal fee |