CA1231046A - Composition of matter containing imidazolidinyl urea and parabens - Google Patents
Composition of matter containing imidazolidinyl urea and parabensInfo
- Publication number
- CA1231046A CA1231046A CA000433967A CA433967A CA1231046A CA 1231046 A CA1231046 A CA 1231046A CA 000433967 A CA000433967 A CA 000433967A CA 433967 A CA433967 A CA 433967A CA 1231046 A CA1231046 A CA 1231046A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- weight
- imidazolidinyl urea
- parabens
- propylparaben
- 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.)
- Expired
Links
Classifications
-
- 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
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- 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
- 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
-
- 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
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/524—Preservatives
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Emergency Medicine (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Dermatology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
Abstract
ABSTRACT:
A composition of matter exhibiting activity against bacteria, yeasts and molds comprising 29 to 31%, by weight, imidazolidinyl urea, 10 to 12%, by weight, methylparaben, 2 to 4%, by weight, propylparaben, and 55 to 57%, by weight, propylene glycol. The composition is readily incorporated into a variety of products requiring preservation from contaminating microorganisms.
A composition of matter exhibiting activity against bacteria, yeasts and molds comprising 29 to 31%, by weight, imidazolidinyl urea, 10 to 12%, by weight, methylparaben, 2 to 4%, by weight, propylparaben, and 55 to 57%, by weight, propylene glycol. The composition is readily incorporated into a variety of products requiring preservation from contaminating microorganisms.
Description
COMPOSITION OF MATTER CONTAINING
IMIDAZOLIDINYL UREA AUDI PARABENS
BACKGROUND OF THE INVENTION
It is widely recognized in the art of cosmetic preservation that the combination of imidaæolidinyl urea and parabens constitute a highly effective preservative system against bacteria, yeasts and molds. Imidazolidinyl urea is the name given to a bactericidal compound prepared as described in Example IV of United States Patent 3,248,285 and has been given a Chemical Abstract Service Registry No. 39236-46-~. Paraben is the generic name for the family of esters of p-hydroxybenæoic acid which exhibit anti-microbial activity.
Typically, the imidazolidinyl urea-paraben system is formed from equal parts by weight of imidaæolidinyl urea and paraben. A system containing imidazolidinyl urea, methyl paraben and propylparaben in the weight ratio of 3:2:1 is perhaps the most common combination employed for cosmetic preservation.
However, imidazolidinyl urea is soluble in water whereas methyl and propel paraben are only very slightly water soluble. Accordingly, the preparation of a presser-votive system based upon these compounds which is compel-isle in a variety of products requiring preservation against contamination by microorganisms, including aqueous s
IMIDAZOLIDINYL UREA AUDI PARABENS
BACKGROUND OF THE INVENTION
It is widely recognized in the art of cosmetic preservation that the combination of imidaæolidinyl urea and parabens constitute a highly effective preservative system against bacteria, yeasts and molds. Imidazolidinyl urea is the name given to a bactericidal compound prepared as described in Example IV of United States Patent 3,248,285 and has been given a Chemical Abstract Service Registry No. 39236-46-~. Paraben is the generic name for the family of esters of p-hydroxybenæoic acid which exhibit anti-microbial activity.
Typically, the imidazolidinyl urea-paraben system is formed from equal parts by weight of imidaæolidinyl urea and paraben. A system containing imidazolidinyl urea, methyl paraben and propylparaben in the weight ratio of 3:2:1 is perhaps the most common combination employed for cosmetic preservation.
However, imidazolidinyl urea is soluble in water whereas methyl and propel paraben are only very slightly water soluble. Accordingly, the preparation of a presser-votive system based upon these compounds which is compel-isle in a variety of products requiring preservation against contamination by microorganisms, including aqueous s
- 2 based products, is a problem.
As heretofore practiced, the three components of the preservative system are incorporated into emulsion-type products, i.e., creams and lotions, in three separate steps. The propylparaben is first dissolved in the oil phase of the emulsion since it is soluble in numerous oils, but insoluble in water. On the other hand, the methyl par-amen is typically dissolved in the aqueous phase which requires continuous heating since the methylparaben crystals dissolve very slowly in water. Heating the water accelerates the dissolution slightly. Imidazolidinyl urea is dissolved readily in the aqueous phase with only simple stirring.
Alternatively, the methyl and propel parabens may be redissolved in a solvent in which they are mutually compatible, typically an organic solvent such as alcohol or propylene glycol. The resulting solution is then incur-prorated into the product. Imidazolidinyl urea is then dissolved into the aqueous phase of the emulsion.
Other methods of dissolving parabens involve dissolving them in boiling water or first preparing the sodium salts of the parabens which are water soluble. Both methods are costly, time consuming and cause destruction of some of the parabens.
Attempts to incorporate a blended mixture of imidazolidinyl urea, methylparaben and propylparaben directly into an emulsion have failed due to the insole-ability of imidazolidinyl urea in oil and paraben in water, so that the blended mixture fails to dissolve completely in either phase. Likewise, attempts to incorporate a blended mixture of the compounds into an aqueous-based (non-emulsion) product have been unsuccessful due to the insolubility of parabens in water.
SUMMARY OF THE INVENTION
The present invention is based upon the discovery
As heretofore practiced, the three components of the preservative system are incorporated into emulsion-type products, i.e., creams and lotions, in three separate steps. The propylparaben is first dissolved in the oil phase of the emulsion since it is soluble in numerous oils, but insoluble in water. On the other hand, the methyl par-amen is typically dissolved in the aqueous phase which requires continuous heating since the methylparaben crystals dissolve very slowly in water. Heating the water accelerates the dissolution slightly. Imidazolidinyl urea is dissolved readily in the aqueous phase with only simple stirring.
Alternatively, the methyl and propel parabens may be redissolved in a solvent in which they are mutually compatible, typically an organic solvent such as alcohol or propylene glycol. The resulting solution is then incur-prorated into the product. Imidazolidinyl urea is then dissolved into the aqueous phase of the emulsion.
Other methods of dissolving parabens involve dissolving them in boiling water or first preparing the sodium salts of the parabens which are water soluble. Both methods are costly, time consuming and cause destruction of some of the parabens.
Attempts to incorporate a blended mixture of imidazolidinyl urea, methylparaben and propylparaben directly into an emulsion have failed due to the insole-ability of imidazolidinyl urea in oil and paraben in water, so that the blended mixture fails to dissolve completely in either phase. Likewise, attempts to incorporate a blended mixture of the compounds into an aqueous-based (non-emulsion) product have been unsuccessful due to the insolubility of parabens in water.
SUMMARY OF THE INVENTION
The present invention is based upon the discovery
- 3 - I
of a composition which is readily incorporated into emulsions and aqueous-based products in amounts which are effective to preserve the product against bacteria, yeasts and molds. The composition is comprised of:
29 to 31%, by weight, imidazolidinyl urea, I 9 duo 12%, by weight, methylparaben, I 2 to 4%, by weight, propylparaben; and 55 to 57%, by weight propylene glycol.
The most preferred composition of the invention consists of:
30~, by weight, imidazolidinyl urea, 11~, by weight, methylparaben, 3%, by weight, propylparaben; and 56%, by weight propylene glycol.
DETAILED DESCRIPTION OF THE INVENTION
The composition of the invention differs from previous imidazolidinyl urea-paraben preservative systems in several significant ways. It contains significantly less parabens than conventional systems, but remains effect-ivy against bacteria, yeasts, and molds. It is soluble in water in amounts up to approximately 1.7%, by weight.
Generally speaking, an amount of about 1% by weight is an effective amount for preserving against microbial con tam-inaction. In contrast, a preservative system consisting ofimidazolidinyl urea, methylparaben and propylparaben, in a weight ratio of 3:2:1, is not soluble in water at a concentration of 1% by weight. Hence, the complicated processing methods previously described are required to incorporate this system into a product while the compost-lion of the invention can be incorporated in one simple step.
The composition of the invention, therefore, provides several advantages over existing preservative systems containing imidazolidinyl urea and parabens. In addition to simplifying the process for incorporating
of a composition which is readily incorporated into emulsions and aqueous-based products in amounts which are effective to preserve the product against bacteria, yeasts and molds. The composition is comprised of:
29 to 31%, by weight, imidazolidinyl urea, I 9 duo 12%, by weight, methylparaben, I 2 to 4%, by weight, propylparaben; and 55 to 57%, by weight propylene glycol.
The most preferred composition of the invention consists of:
30~, by weight, imidazolidinyl urea, 11~, by weight, methylparaben, 3%, by weight, propylparaben; and 56%, by weight propylene glycol.
DETAILED DESCRIPTION OF THE INVENTION
The composition of the invention differs from previous imidazolidinyl urea-paraben preservative systems in several significant ways. It contains significantly less parabens than conventional systems, but remains effect-ivy against bacteria, yeasts, and molds. It is soluble in water in amounts up to approximately 1.7%, by weight.
Generally speaking, an amount of about 1% by weight is an effective amount for preserving against microbial con tam-inaction. In contrast, a preservative system consisting ofimidazolidinyl urea, methylparaben and propylparaben, in a weight ratio of 3:2:1, is not soluble in water at a concentration of 1% by weight. Hence, the complicated processing methods previously described are required to incorporate this system into a product while the compost-lion of the invention can be incorporated in one simple step.
The composition of the invention, therefore, provides several advantages over existing preservative systems containing imidazolidinyl urea and parabens. In addition to simplifying the process for incorporating
- 4 -parabens into the product, the composition of the invention avoids destruction of paraben, reduces the time for prep-axing a preserved product, reduces energy costs and eliminates the need to inventory three separate preserve-live compounds.
The composition of the invention is particularly attractive for use in cosmetic products because it can be added at any stage in the cosmetic manufacturing process including the cooling stage after the cosmetic has been completely formulated. It is readily incorporated in aqueous-based products, emulsions and solid formulations, in a single weighing. Typical cosmetic products which are effectively preserved by the composition of the invention are creams, lotions, shampoos, hair conditioners, eyeliners and other eye make-up products.
In addition to cosmetics, the composition of the invention may be used to preserve almost any substance which is susceptible to microbial contamination including foodstuffs and pharmaceutical formulations. While effect-ivy amounts vary depending upon the product being preserved generally the amount of the composition of the invention incorporated into a product will not exceed 1.0~, by weight.
The invention, therefore, also relates to a method of preserving products susceptible to microbial contamina-lion by incorporating therein an effective amount of the composition of the invention, and the products so preserved.
To prepare the composition of the invention the imidazolidinyl urea and methyl and propylparabens are blended into propylene glycol in amounts to achieve the final concentrations. Generally, it is preferred to add the imidazolidinyl urea first to the propel glycol, possibly at a slightly elevated temperature to facilitate dozily-lion. Thereafter, the parabens are added. Heating is typically discontinued when the parabens are added to avoid destruction of paraben. Further details of the manner of making and using the composition are found in the Examples which follow, it being understood that their purpose is solely illustrative and in no way intended to limit the scope of the invention.
Example Preparation of composition -In a 5-liter, three-necked, round-bottom flask equipped with stirrer, condenser, thermometer, and heating mantle was put 2240 g. of propylene glycol. The tempera-lure of the propylene glycol was maintained at 70C by heating while a total of 1200 g. of imidazolidinyl urea (Germ all 115) was added. Heating was discontinued, and 440 g. of methylparaben and 120 g. of propylparaben was added to the stirred solution. The bath temperature dropped from 70C to 57C, and was maintained above 55C
until all the parabens had dissolved tl5-30 minutes).
The solution was filtered to give a clear colorless liquid filtrate.
Example II
Antimicrobial activity of composition after dilution with 99 parts of water -(a) Activity against bacteria (Pseudomonas aeruginosa) A 0.5 ml Alcott (containing approximately 107 organisms per ml) of a 24-hour AWOKE. broth culture of Pseudomonas aeruginosa (ATTICS 9027) was added to 4.5 ml of test solution (1 part composition parts water) and mixed well. The test solution was then stored at 35C in an incubator for three days. A 0.1 ml Alcott was aseptically removed from the test solution and placed into a tube containing AWOKE. broth with Lithuania. The inoculated subculture tube was incubated at 35C for two days and then examined for presence of growth.
The subculture showed no growth, indicating complete kill of Pseudomonas aeruginosa in the test soul-lion.
(b) Activity against yeast (Candid albicans) The same procedure was used as in (a) above, except that Suborned Liquid Medium with Lithuania was used in place of AWOKE. broth with Lithuania The subculture after two days incubation showed no growth, indicating complete kill of Candid albicans (ATTICS 10231) in the test solution.
(c) Activity against mold (Aspergillus Niger - The growth of a 7-10 day slant of Aspergillus Niger (ATTICS 16404) was washed off with 10 ml of sterile saline solution. A 0.5 ml Alcott of this suspension was added to 4.5 ml of the test solution (1 part composition:
99 parts water) and mixed well. The test solution was stored at room temperature (25C) for three days. A 0.1 ml Alcott was removed and placed into Suborned Liquid Medium with Lithuania, and incubated for 7 days at room temperature (25C) and then examined for presence of growth.
The subculture showed no growth, indicating complete kill of Aspergillus Niger in the test solution.
While the invention has now been described in terms of certain preferred embodiments, and exemplified with respect thereto, those of skill in the art will readily appreciate that various modifications, changes, omissions, and substitutions may be made without departing from the spirit of the invention. It is, therefore, intended that the present invention be limited solely by the scope of the following claims.
The composition of the invention is particularly attractive for use in cosmetic products because it can be added at any stage in the cosmetic manufacturing process including the cooling stage after the cosmetic has been completely formulated. It is readily incorporated in aqueous-based products, emulsions and solid formulations, in a single weighing. Typical cosmetic products which are effectively preserved by the composition of the invention are creams, lotions, shampoos, hair conditioners, eyeliners and other eye make-up products.
In addition to cosmetics, the composition of the invention may be used to preserve almost any substance which is susceptible to microbial contamination including foodstuffs and pharmaceutical formulations. While effect-ivy amounts vary depending upon the product being preserved generally the amount of the composition of the invention incorporated into a product will not exceed 1.0~, by weight.
The invention, therefore, also relates to a method of preserving products susceptible to microbial contamina-lion by incorporating therein an effective amount of the composition of the invention, and the products so preserved.
To prepare the composition of the invention the imidazolidinyl urea and methyl and propylparabens are blended into propylene glycol in amounts to achieve the final concentrations. Generally, it is preferred to add the imidazolidinyl urea first to the propel glycol, possibly at a slightly elevated temperature to facilitate dozily-lion. Thereafter, the parabens are added. Heating is typically discontinued when the parabens are added to avoid destruction of paraben. Further details of the manner of making and using the composition are found in the Examples which follow, it being understood that their purpose is solely illustrative and in no way intended to limit the scope of the invention.
Example Preparation of composition -In a 5-liter, three-necked, round-bottom flask equipped with stirrer, condenser, thermometer, and heating mantle was put 2240 g. of propylene glycol. The tempera-lure of the propylene glycol was maintained at 70C by heating while a total of 1200 g. of imidazolidinyl urea (Germ all 115) was added. Heating was discontinued, and 440 g. of methylparaben and 120 g. of propylparaben was added to the stirred solution. The bath temperature dropped from 70C to 57C, and was maintained above 55C
until all the parabens had dissolved tl5-30 minutes).
The solution was filtered to give a clear colorless liquid filtrate.
Example II
Antimicrobial activity of composition after dilution with 99 parts of water -(a) Activity against bacteria (Pseudomonas aeruginosa) A 0.5 ml Alcott (containing approximately 107 organisms per ml) of a 24-hour AWOKE. broth culture of Pseudomonas aeruginosa (ATTICS 9027) was added to 4.5 ml of test solution (1 part composition parts water) and mixed well. The test solution was then stored at 35C in an incubator for three days. A 0.1 ml Alcott was aseptically removed from the test solution and placed into a tube containing AWOKE. broth with Lithuania. The inoculated subculture tube was incubated at 35C for two days and then examined for presence of growth.
The subculture showed no growth, indicating complete kill of Pseudomonas aeruginosa in the test soul-lion.
(b) Activity against yeast (Candid albicans) The same procedure was used as in (a) above, except that Suborned Liquid Medium with Lithuania was used in place of AWOKE. broth with Lithuania The subculture after two days incubation showed no growth, indicating complete kill of Candid albicans (ATTICS 10231) in the test solution.
(c) Activity against mold (Aspergillus Niger - The growth of a 7-10 day slant of Aspergillus Niger (ATTICS 16404) was washed off with 10 ml of sterile saline solution. A 0.5 ml Alcott of this suspension was added to 4.5 ml of the test solution (1 part composition:
99 parts water) and mixed well. The test solution was stored at room temperature (25C) for three days. A 0.1 ml Alcott was removed and placed into Suborned Liquid Medium with Lithuania, and incubated for 7 days at room temperature (25C) and then examined for presence of growth.
The subculture showed no growth, indicating complete kill of Aspergillus Niger in the test solution.
While the invention has now been described in terms of certain preferred embodiments, and exemplified with respect thereto, those of skill in the art will readily appreciate that various modifications, changes, omissions, and substitutions may be made without departing from the spirit of the invention. It is, therefore, intended that the present invention be limited solely by the scope of the following claims.
Claims (3)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A composition of matter comprising:
29 to 31%, by weight, imidazolidinyl urea, 9 to 12%, by weight, methylparaben, 2 to 4%, by weight, propylparaben, and 55 to 57%, by weight, propylene glycol.
29 to 31%, by weight, imidazolidinyl urea, 9 to 12%, by weight, methylparaben, 2 to 4%, by weight, propylparaben, and 55 to 57%, by weight, propylene glycol.
2. A composition of matter consisting of:
30%, by weight, imidazolidinyl urea, 11%, by weight, methylparaben,
30%, by weight, imidazolidinyl urea, 11%, by weight, methylparaben,
3%, by weight, propylparaben, and 56%, by weight, propylene glycol.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40601782A | 1982-08-06 | 1982-08-06 | |
| US406,017 | 1982-08-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1231046A true CA1231046A (en) | 1988-01-05 |
Family
ID=23606197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000433967A Expired CA1231046A (en) | 1982-08-06 | 1983-08-05 | Composition of matter containing imidazolidinyl urea and parabens |
Country Status (4)
| Country | Link |
|---|---|
| CA (1) | CA1231046A (en) |
| DE (1) | DE3328372A1 (en) |
| FR (1) | FR2531336B1 (en) |
| GB (1) | GB2126089B (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8969390B2 (en) | 2009-05-23 | 2015-03-03 | Clariant Finance (Bvi) Limited | Composition containing sorbitan monocaprylate and antimicrobial substances |
| US9295626B2 (en) | 2011-08-04 | 2016-03-29 | Clariant International Ltd. | Compositions comprising isosorbide monoester and N-hydroxypyridones |
| US9358199B2 (en) | 2011-08-04 | 2016-06-07 | Clariant International Ltd. | Use of isosorbide diesters as thickeners |
| US9445595B2 (en) | 2011-08-04 | 2016-09-20 | Clariant International Ltd. | Composition containing isosorbide monoester and isosorbide diester |
| US9555117B2 (en) | 2011-08-04 | 2017-01-31 | Clariant International Ltd. | Use of isosorbide monoesters as thickeners |
| US9596849B2 (en) | 2009-05-23 | 2017-03-21 | Clariant International Ltd. | Composition containing sorbitan monocaprylate and alcohol |
| US9730450B2 (en) | 2011-08-04 | 2017-08-15 | Clariant International Ltd. | Use of isosorbide monoesters as antimicrobial active substances |
| US10406135B2 (en) | 2011-08-04 | 2019-09-10 | Clariant International Ltd. | Compositions containing isosorbide monoester and alcohols that contain at least one aromatic group |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3508928A1 (en) * | 1985-03-13 | 1986-09-18 | Giulini Chemie Gmbh, 6700 Ludwigshafen | COMBINATION FOR ANTIMICROBIAL AND ANTIOXIDATIVE STABILIZATION OF EXTERNA AND PERSONAL CARE PRODUCTS |
| FR2579463B1 (en) * | 1985-03-26 | 1988-01-29 | Bensimon Claudine | THERAPEUTIC COMPOSITION BASED ON IMIDAZOLIDINYLUREA FOR THE TREATMENT OF SKIN MANIFESTATIONS OF ACNE |
| DK234589A (en) * | 1988-05-16 | 1989-11-17 | Daleco Protech Partners Lp | STABILIZER COMPOSITION AND STABILIZING Aqueous Systems |
-
1983
- 1983-08-05 CA CA000433967A patent/CA1231046A/en not_active Expired
- 1983-08-05 GB GB08321167A patent/GB2126089B/en not_active Expired
- 1983-08-05 DE DE19833328372 patent/DE3328372A1/en not_active Withdrawn
- 1983-08-05 FR FR8312984A patent/FR2531336B1/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8969390B2 (en) | 2009-05-23 | 2015-03-03 | Clariant Finance (Bvi) Limited | Composition containing sorbitan monocaprylate and antimicrobial substances |
| US9596849B2 (en) | 2009-05-23 | 2017-03-21 | Clariant International Ltd. | Composition containing sorbitan monocaprylate and alcohol |
| US9295626B2 (en) | 2011-08-04 | 2016-03-29 | Clariant International Ltd. | Compositions comprising isosorbide monoester and N-hydroxypyridones |
| US9358199B2 (en) | 2011-08-04 | 2016-06-07 | Clariant International Ltd. | Use of isosorbide diesters as thickeners |
| US9445595B2 (en) | 2011-08-04 | 2016-09-20 | Clariant International Ltd. | Composition containing isosorbide monoester and isosorbide diester |
| US9555117B2 (en) | 2011-08-04 | 2017-01-31 | Clariant International Ltd. | Use of isosorbide monoesters as thickeners |
| US9730450B2 (en) | 2011-08-04 | 2017-08-15 | Clariant International Ltd. | Use of isosorbide monoesters as antimicrobial active substances |
| US9968536B2 (en) | 2011-08-04 | 2018-05-15 | Clariant International Ltd. | Composition comprising isosorbide monoesters and isosorbide diesters |
| US10406135B2 (en) | 2011-08-04 | 2019-09-10 | Clariant International Ltd. | Compositions containing isosorbide monoester and alcohols that contain at least one aromatic group |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2531336B1 (en) | 1987-10-02 |
| GB2126089A (en) | 1984-03-21 |
| GB8321167D0 (en) | 1983-09-07 |
| DE3328372A1 (en) | 1984-03-01 |
| GB2126089B (en) | 1985-11-06 |
| FR2531336A1 (en) | 1984-02-10 |
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