US20070207113A1 - Personal care and cosmetic compositions comprising renewably-based, biodegradable 1,3-propanediol - Google Patents

Personal care and cosmetic compositions comprising renewably-based, biodegradable 1,3-propanediol Download PDF

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Publication number
US20070207113A1
US20070207113A1 US11/705,346 US70534607A US2007207113A1 US 20070207113 A1 US20070207113 A1 US 20070207113A1 US 70534607 A US70534607 A US 70534607A US 2007207113 A1 US2007207113 A1 US 2007207113A1
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United States
Prior art keywords
propanediol
phase
bio
personal care
pdo
Prior art date
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Abandoned
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US11/705,346
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English (en)
Inventor
Melissa Joerger
Gyorgyi Fenyvesi
Raja Hari Poladi
Irwin Palefsky
Ann Wehner
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DuPont Tate and Lyle Bio Products Co LLC
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Individual
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=38372098&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=US20070207113(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Individual filed Critical Individual
Priority to US11/705,346 priority Critical patent/US20070207113A1/en
Assigned to DUPONT TATE & LYLE BIO PRODUCTS COMPANY, LLC reassignment DUPONT TATE & LYLE BIO PRODUCTS COMPANY, LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: FENYVESI, GYORGYI, WEHNER, ANN, JOERGER, MELISSA, POLADI, RAJA HARI PRASAD R., PALEFSKY, IRWIN A.
Publication of US20070207113A1 publication Critical patent/US20070207113A1/en
Priority to US14/589,193 priority patent/US20150125403A1/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/086—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type polycarboxylic, e.g. maleic acid
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/223—Five-membered rings containing nitrogen and carbon only
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/042—Siloxanes with specific structure containing aromatic substituents
    • C10M2229/0425—Siloxanes with specific structure containing aromatic substituents used as base material
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/64—Environmental friendly compositions
    • C—CHEMISTRY; METALLURGY
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/12—Soft surfaces, e.g. textile
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/14—Hard surfaces
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W10/00—Technologies for wastewater treatment
    • Y02W10/30—Wastewater or sewage treatment systems using renewable energies
    • Y02W10/37—Wastewater or sewage treatment systems using renewable energies using solar energy

Definitions

  • compositions comprising 1,3-propanediol wherein the 1,3-propanediol in said personal care or cosmetic composition has a bio-based carbon content of about 1% to 100%.
  • the 1,3-propanediol be biologically-derived, and wherein upon biodegradation, the biologically-derived 1,3-propanediol contributes no anthropogenic CO 2 emissions to the atmosphere.
  • the 2004 Co-operative Bank's annual Ethical Consumerism Report (www.co-operativebank.co.uk) disclosed a 30.3% increase in consumer spending on ethical retail products (a general classification for environmental safe, organic and fair trade goods) between 2003 and 2004 while total consumer spending during the same period rose only 3.7%.
  • Glycols such as ethylene glycol, propylene glycol, 1,3-butylene glycol, and 2-methyl-1,3-propanediol are biodegradable compounds useful in compositions ranging from cosmetics and personal care formulations to detergents to heat transfer compositions. While biodegradability is an important factor in protecting the environment, biodegradation of glycols derived from fossil-based sources has the unavoidable consequence of releasing previously fixed CO 2 into the atmosphere. Thus, while glycols in general are advantageous for their biodegradability, the resulting global warming potential of fossil-based glycols during biodegradation is significant.
  • Carbon dioxide is singled out as the largest component of the collection of greenhouse gases in the atmosphere.
  • the level of atmospheric carbon dioxide has increased 50% in the last two hundred years. Recent reports indicate that the current level of atmospheric carbon dioxide is higher than the peak level in the late Pleistocene, the epoch before modern humans (Siegenthaler, U. et al. Stable Carbon Cycle-Climate Relationship During the Late Pleistocene, Science, Vol. 310, no. 5752 (Nov. 25, 2005), pp. 1313-1317). Therefore, any further addition of carbon dioxide to the atmosphere is thought to further shift the effect of greenhouse gases from stabilization of global temperatures to that of heating. Consumers and environmental protection groups alike have identified industrial release of carbon into the atmosphere as the source of carbon causing the greenhouse effect.
  • Greenhouse gas emission can occur at any point during the lifetime of a product. Consumers and environmental groups consider the full lifespan of a product when evaluating a product's environmental impact. Consumers look for products that do not contribute new carbon to the atmosphere considering the environmental impact of production, use and degradation. Only organic products composed of carbon molecules from plant sugars and starches and ultimately atmospheric carbon are considered to not further contribute to the greenhouse effect.
  • the present invention is directed to a personal care or cosmetic composition
  • a personal care or cosmetic composition comprising 1,3-propanediol and an acceptable carrier, wherein said 1,3-propanediol has a bio-based carbon content of at least 1%.
  • the present invention is further directed to a personal care or cosmetic composition
  • a personal care or cosmetic composition comprising 1,3-propanediol and an active, wherein said 1,3-propanediol has a bio-based carbon content of at least 1%.
  • the present invention is also directed to a personal care or cosmetic composition
  • a personal care or cosmetic composition comprising 1,3-propanediol wherein said 1,3-propanediol has an ultraviolet absorption at 220 nm of less than about 0.200 and at 250 nm of less than about 0.075 and at 275 nm of less than about 0.075.
  • the present invention is additionally directed to a personal care or cosmetic composition
  • a personal care or cosmetic composition comprising 1,3-propanediol wherein said 1,3-propanediol has a concentration of total organic impurities of less than about 400 ppm.
  • the present invention is even further directed to a personal care or cosmetic composition
  • a personal care or cosmetic composition comprising 1,3-propanediol, wherein the 1,3-propanediol in said composition has an anthropogenic CO 2 emission profile of zero upon biodegradation.
  • FIG. 1 is a graph showing CO 2 emissions for CO 2 fixation from the atmosphere during photosynthesis for renewably based 1,3-propanediol (Bio-PDO) ( ⁇ 1.7 kg CO 2 /kg product) and CO 2 release to the atmosphere during biodegradation (kg CO 2 kg product) for ethylene glycol (EG) (+1.4 kg CO 2 /kg product), propylene glycol (PG) (+1.7 kg CO 2 /kg product), fossil-based 1,3-propanediol (Chem-PDO) (+1.7 kg CO 2 /kg product), and fermentatively-derived 1,3-propanediol (Bio-PDO) (+1.7 kg CO 2 /kg product).
  • Bio-PDO 1,3-propanediol
  • FIG. 2 is a graph showing that the net emissions of CO 2 to the atmosphere for renewably based 1,3-propanediol (Bio-PDO) is zero (0).
  • FIG. 3 is a table that shows the calculations for the data shown in FIGS. 1 and 2 .
  • compositions disclosed herein comprise 1,3-propanediol, having at least 1% bio-based carbon content, as greater as up to 100% of the glycol component of the composition.
  • the 1,3-propanediol comprises substantially all of the glycol component of the composition of the invention. In another embodiment, the 1,3-propanediol comprises all of the glycol component of the composition.
  • bioPDO biologically-derived, biodegradable 1,3-propanediol
  • biologicalcally derived 1,3-propanediol biologically derived 1,3-propanediol
  • biodegradable 1,3-propanediol biologically derived 1,3-propanediol
  • biosourced biologically-derived, and biologically-derived, biodegradable 1,3-propanediol
  • biologically-produced 1,3-propanediol and similar terms as used here in refer to 1,3-propanediol derived from microorganism metabolism of plant-derived sugars composed of carbon of atmospheric origin, and not composed of fossil-fuel carbon.
  • Applicants' invention relates to personal care and cosmetic compositions comprising renewably-based, biodegradable 1,3-propanediol, in which said renewably-based, biodegradable 1,3-propanediol has an anthropogenic CO 2 emission profile of zero (0).
  • An “anthropogenic emission profile” means anthropogenic CO 2 emissions that are contributed to the atmosphere upon biodegradation of a compound or composition.
  • Biodegradable or “Biodegradability” means the capacity of a compound to be broken down by living organisms to simple, stable compounds such as carbon dioxide and water.
  • biodegradation is the process of converting organic material back into CO 2 and H 2 O through the activity of living organisms.
  • Carbon of atmospheric origin refers to carbon atoms from carbon dioxide molecules that have recently, in the last few decades, been free in the earth's atmosphere. Such carbons in mass are identifiable by the present of particular radioisotopes as described herein. “Green carbon”, “atmospheric carbon”, “environmentally friendly carbon”, “life-cycle carbon”, “non-fossil fuel based carbon”, “non-petroleum based carbon”, “carbon of atmospheric origin”, and “biobased carbon” are used synonymously herein.
  • Carbon of fossil origin refers to carbon of petrochemical origin. Such carbon has not been exposed to UV rays as atmospheric carbon has, therefore masses of carbon of fossil origin has few radioisotopes in their population. Carbon of fossil origin is identifiable by means described herein. “Fossil fuel carbon”, “fossil carbon”, “polluting carbon”, “petrochemical carbon”, “petro-carbon” and carbon of fossil origin are used synonymously herein.
  • IRMS refers to measurements of CO2 by high precision stable isotope ratio mass spectrometry.
  • carbon substrate means any carbon source capable of being metabolized by a microorganism wherein the substrate contains at least one carbon atom.
  • “Renewably-based” denotes that the carbon content of the 1,3-propanediol is from a “new carbon” source as measured by ASTM test method D 6866-05 Determining the Biobased Content of Natural Range Materials Using Radiocarbon and Isotope Ratio Mass Spectrometry Analysis, incorporated herein by reference. This test method measures the C-14/C-12 isotope ratio in a sample and compares it to the C-14/C-12 isotope ratio in a standard 100% biobased material to give percent biobased content of the sample.
  • “Biobased materials” are organic materials in which the carbon comes from recently (on a human time scale) fixated CO 2 present in the atmosphere using sunlight energy (photosynthesis).
  • this CO 2 is captured or fixated by plant life (e.g., agricultural crops or forestry materials). In the oceans, the CO 2 is captured or fixated by photosynthesizing bacteria or phytoplankton.
  • a biobased material has a C-14/C-12 isotope ratio in range of from 1:0 to greater than 0:1. Contrarily, a fossil-based material, has a C-14/C-12 isotope ratio of 0:1.
  • a small amount of the carbon dioxide in the atmosphere is radioactive.
  • This 14C carbon dioxide is created when nitrogen is struck by an ultra-violet light produced neutron, causing the nitrogen to lose a proton and form carbon of molecular weight 14 which is immediately oxidized in carbon dioxide.
  • This radioactive isotope represents a small but measurable fraction of atmospheric carbon.
  • Atmospheric carbon dioxide is cycled by green plants to make organic molecules during the process known as photosynthesis. The cycle is completed when the green plants or other forms of life metabolize the organic molecules producing carbon dioxide which is released back to the atmosphere. Virtually all forms of life on Earth depend on this green plant production of organic molecule to produce the chemical energy that facilitates growth and reproduction. Therefore, the 14C that exists in the atmosphere becomes part of all life forms, and their biological products.
  • These renewably based organic molecules that biodegrade to CO2 do not contribute to global warming as there is no net increase of carbon emitted to the atmosphere.
  • fossil fuel based carbon does not have the signature radiocarbon ratio of atmospheric carbon dioxide
  • Atmospheric origin and fixed carbon source as used herein are relative terms in that the time period of when CO2 is of atmospheric or fixed origin relates to the life cycle of the 1,3-propanediol.
  • carbon from a fossil fuel was found in the atmosphere (and, as a corollary, that atmospheric CO2 may one day be incorporated into a fixed carbon source)
  • carbon is considered to be from a fixed carbon source until it is released into the atmosphere by degradation.
  • the application of ASTM-D6866 to derive a “biobased content” is built on the same concepts as radiocarbon dating, but without use of the age equations.
  • the analysis is performed by deriving a ratio of the amount of radiocarbon (14C) in an unknown sample to that of a modern reference standard. The ratio is reported as a percentage with the units “pMC” (percent modern carbon). If the material being analyzed is a mixture of present day radiocarbon and fossil carbon (containing no radiocarbon), then the pMC value obtained correlates directly to the amount of Biomass material present in the sample.
  • the modern reference standard used in radiocarbon dating is a NIST (National Institute of Standards and Technology) standard with a known radiocarbon content equivalent approximately to the year AD 1950.
  • AD 1950 was chosen since it represented a time prior to thermo-nuclear weapons testing which introduced large amounts of excess radiocarbon into the atmosphere with each explosion (termed “bomb carbon”).
  • the AD 1950 reference represents 100 pMC.
  • a biomass content result is derived by assigning 100% equal to 107.5 pMC and 0% equal to 0 pMC. In this regard, a sample measuring 99 pMC will give an equivalent biobased content result of 93%.
  • a personal care or cosmetic composition of the invention may comprise a combination of a biologically-derived 1,3-propanediol and one or more non biologically-derived glycol components, such as, for example, chemically synthesized 1,3-propanediol.
  • a biologically-derived 1,3-propanediol and one or more non biologically-derived glycol components, such as, for example, chemically synthesized 1,3-propanediol.
  • the glycol component, and in particular, the 1,3-propanediol can comprise at least about 1% bio-based carbon content up to 100% bio-based carbon content, and any percentage therebetween.
  • a “b*” value is the spectrophotometrically determined “Yellow Blue measurement as defined by the CIE L*a*b* measurement ASTM D6290.
  • AMS accelerator mass spectrometry
  • NMR nuclear magnetic resonance
  • color and “color bodies” is meant the existence of visible color that can be quantified using a spectrocolorimeter in the range of visible light, using wavelengths of approximately 400-800 nm, and by comparison with pure water. Reaction conditions can have an important effect on the nature of color production. Examples of relevant conditions include the temperatures used, the catalyst and amount of catalyst. While not wishing to be bound by theory, we believe color precursors include trace amounts of impurities comprising olefinic bonds, acetals and other carbonyl compounds, peroxides, etc. At least some of these impurities may be detected by such methods as UV spectroscopy, or peroxide titration.
  • Color index refers to an analytic measure of the electromagnetic radiation-absorbing properties of a substance or compound.
  • Biologically-derived 1,3-propanediol useful in personal care and cosmetic compositions disclosed herein has at least one of the following characteristics: 1) an ultraviolet absorption at 220 nm of less than about 0.200 and at 250 nm of less than about 0.075 and at 275 nm of less than about 0.075; or 2) a composition having L*a*b* “b*” color value of less than about 0.15 and an absorbance at 270 n m of less than about 0.075; or 3) a peroxide composition of less than about 10 ppm; or 4) a concentration of total organic impurities of less than about 400 ppm.
  • a “b*” value is the spectrophotometrically determined Yellow Blue measurement as defined by the CIE L*a*b* measurement ASTM D6290.
  • the level of 1,3-propanediol purity can be characterized in a number of different ways. For example, measuring the remaining levels of contaminating organic impurities is one useful measure.
  • Biologically-derived 1,3-propanediol can have a purity level of less than about 400 ppm total organic contaminants; preferably less than about 300 ppm; and most preferably less than about 150 ppm.
  • ppm total organic purity refers to parts per million levels of carbon-containing compounds (other than 1,3-propanediol) as measured by gas chromatography.
  • Biologically-derived 1,3-propanediol can also be characterized using a number of other parameters, such as ultraviolet light absorbance at varying wavelengths.
  • the wavelengths 220 nm, 240 nm and 270 nm have been found to be useful in determining purity levels of the composition.
  • Biologically-derived 1,3-propanediol can have a purity level wherein the UV absorption at 220 nm is less than about 0.200 and at 240 nm is less than about 0.075 and at 270 nm is less than about 0.075.
  • Biologically-derived 1,3-propanediol can have a b* color value (CIE L*a*b*) of less than about 0.15.
  • the purity of biologically-derived 1,3-propanediol compositions can also be assessed in a meaningful way by measuring levels of peroxide.
  • Biologically-derived 1,3-propanediol can have a concentration of peroxide of less than about 10 ppm.
  • Bio-produced means organic compounds produced by one or more species or strains of living organisms, including particularly strains of bacteria, yeast, fungus and other microbes. “Bio-produced” and biologically produced are used synonymously herein. Such organic compounds are composed of carbon from atmospheric carbon dioxide converted to sugars and starches by green plants.
  • Bio-based means that the organic compound is synthesized from biologically produced organic components. It is further contemplated that the synthesis process disclosed herein is capable of effectively synthesizing other monoesters and diesters from bio-produced alcohols other than 1,3-propanediol; particularly including ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propylene glycol, dipropylene diol, tripropylene diol, 2-methyl 1,3-propanediol, neopentyl glycol and bisphenol A. “Bio-based”, and “bio-sourced”; “biologically derived”; and “bio-derived” are used synonymously herein.
  • “Fermentation” as used refers to the process of metabolizing simple sugars into other organic compounds. As used herein fermentation specifically refers to the metabolism of plant derived sugars, such sugar are composed of carbon of atmospheric origin.
  • Biologically-derived 1,3-propanediol can be obtained based upon use of the fermentation broth (“fermentatively-derived”) generated by a genetically-engineered Eschericia coli ( E. coli ) previously disclosed in, for example, U.S. Pat. No. 5,686,276.
  • E. coli Eschericia coli
  • Other single organisms, or combinations of organisms may be used to biologically produce 1,3-propanediol, using organisms that have been genetically-engineered according to methods known in the art.
  • “Fermentation” refers to a system that catalyzes a reaction between substrate(s) and other nutrients to product(s) through use of a biocatalyst.
  • the biocatalysts can be a whole organism, an isolated enzyme, or any combination or component thereof that is enzymatically active. Fermentation systems useful for producing and purifying biologically-derived 1,3-propanediol are disclosed in, for example, Published U.S. Patent Application No. 2005/0069997 incorporated herein by reference.
  • the biologically derived 1,3-propanediol (Bio-PDO) for use in the current invention, produced by the process described herein, contains carbon from the atmosphere incorporated by plants, which compose the feedstock for the production of Bio-PDO.
  • the Bio-PDO used in the compositions of the invention contains only renewable carbon, and not fossil fuel based, or petroleum based carbon. Therefore the compositions of the invention have less impact on the environment as the propanediol used in the compositions does not deplete diminishing fossil fuels and, upon degradation releases carbon back to the atmosphere for use by plants once again.
  • the present invention can be characterized as more natural and having less environmental impact than similar compositions comprising petroleum based glycols.
  • This 1,3-propanediol of the invention can be isolated from the fermentation broth and is incorporated into personal care and cosmetic compositions of the invention, by processes as are known to those of ordinary skill in the applicable art.
  • 1,3-propanediol can be incorporated into numerous compositions as a glycol component.
  • 1,3-propanediol can be part of or the sole glycol component of personal care and cosmetic compositions.
  • Bio-PDO can serve as a humectant, solvent, neutralizer, preservative, emulsifier, emollient, softening agent, handfeel effector, water activity reducer and/or fragrance enhancer.
  • the Bio-PDO typically serves as a surfactant, humectant, solvent, neutralizer, emulsifier, preservative and/or fragrance enhancer.
  • typical personal care and cosmetic compositions include, but are not limited to, lipstick, lip gloss, lip pencil, eye shadows, foundation, blush, liquid rouge, facial powder, make-up, concealer, gel eye color, mascara, lip gloss, eye pencil, lip pencil, eye make-up remover, eye liners, eye shadow, lotion eye color, gel eye color, nail polish, lipstick nail polish, gel polish removers, liquid rouges, blush, and facial powder, skin care composition, skin cleansing composition, skin cleansing bar, skin cleansing liquid, facial lotion, facial cream, cream moisturizer, body wash, body lotion; foot care products like foot cream, hand cream; deodorant and antiperspirant sticks, roll-ons, aerosols, gels, creams, pump sprays, powders, odor-masking, odor-neutralizing, odor-quenching, odor-inhibiting; cologne sticks, perfumes, shaving cream, shaving lotion, cream depilatory, lotion depilatory, wax depilatory, facial mask made with clay materials, anti-aging product, anti-w
  • Bio-PDO can be present in the aforementioned personal care and cosmetics compositions in amounts well known to those of ordinary skill in the appropriate art, typically up to about 12% by weight based on the weight of the total composition, though some compositions, for example, bath preparations may contain as much as 50% glycol, and some specialty formulations like vitamin creams can contain even higher percentages of glzycol up to as much as 65%, and deodorants up to as much as 85%.
  • Baby products such as, for example, baby shampoos, soaps, wipes, lotions, oils, powders, and creams, wherein preferred Bio-PDO concentration ranges are from about 0.1% to about 25% by weight, and more preferably from about 1% to about 10% by weight, and even more preferably 1 to 5%.
  • Bath preparations such as, for example, bath oils, tablets, and salts; bubble baths and bath capsules, wherein preferred Bio-PDO concentration ranges are from about 0.001% to about 50%, and more preferably from about 0.1% to about 10%, and even more preferably from about 1% to about 5%.
  • Eye makeup preparations such as, for example, eyebrow pencil; eyeliner; eye shadow; eye lotion; eye makeup remover; and mascara, wherein preferred Bio-PDO concentration ranges are from about 0.001% to about 75%, more preferably 0.01% to about 25%, and even more preferably, 0.05% to about 5%.
  • Fragrance preparations such as, for example, colognes and toilet waters; perfumes; powders (dusting and talcum) (excluding aftershave talc); and sachets, wherein preferred Bio-PDO concentration ranges are from about 0.001% to about 99%, more preferably from about 0.01% to about 10%, and even more preferably from about 0.05% to about 5%.
  • Hair preparations such as, for example, hair conditioners; hair sprays (aerosol fixatives); hair straighteners; permanent waves; rinses (noncoloring); shampoos (noncoloring); tonics, dressings, and other hair grooming aids; and wave sets, wherein preferred Bio-PDO concentration ranges are from about 0.001% to about 90%, more preferably from about 0.01% to about 50%, and even more preferably from about 0.05% to about 10%.
  • Hair coloring preparations such as, for example, hair dyes and colors (requiring caution statement & patch test); hair tints; hair rinses (coloring); hair shampoos (coloring); hair color sprays (aerosol); hair lighteners with color; and hair bleaches, wherein preferred Bio-PDO concentration ranges are from about 0.001% to about 50%, more preferably from about 0.1% to about 25%, and even more preferably, from about 1% to about 10%.
  • Makeup preparations such as, for example, blushers (all types); face powders; foundations; leg and body paints; lipstick; makeup bases; rouges; and makeup fixatives, wherein preferred Bio-PDO concentration ranges are from about 0.001% to about 99%, more preferably from about 0.01% to about 25%, and even more preferably from about 0.05% to about 10%.
  • Manicuring preparations such as, for example, basecoats and undercoats; cuticle softeners; nail creams and lotions; nail extenders; nail polish and enamel; and Nail polish and enamel removers, wherein preferred Bio-PDO concentration ranges are from about 0.001% to about 50%, more preferably from about 0.1% to about 10%, and even more preferably from about 1% to about 5%.
  • Oral hygiene products such as, for example, dentifrices (aerosol, liquid, pastes, and powders); and mouthwashes and breath fresheners (liquids and sprays), wherein preferred Bio-PDO concentration ranges are from about 0.001% to about 80%, and more preferably from about 1% to about 5%.
  • Bio-PDO concentration ranges are from about 0.001% to about 99%, more preferably from about 0.01% to about 50%, and even more preferably from about 0.05% to about 10%.
  • Shaving preparations such as, for example, shaving lotions, aftershave lotions; beard softeners; men's talcum; preshave lotions (all types); shaving cream (aerosol, brushless, and lather); and shaving soap (cakes, sticks, etc.), wherein preferred Bio-PDO concentration ranges are from about 0.001% to about 50%, more preferably from about 0.01% to about 10%, and even more preferably from about 0.1% to about 5%.
  • Skin care preparations such as, for example, cleansing (cold creams, cleansing lotions, liquids, and pads); depilatories; face and neck (excluding shaving preparations); body and hand (excluding shaving preparations); foot powders and sprays; hormone products; moisturizing; night; paste masks (mud packs); skin lighteners; skin fresheners; and wrinkle-smoothing products (removers), wherein preferred Bio-PDO concentration ranges are from about 0.001% to about 50%, more preferably from about 0.01% to about 15%, and even more preferably from about 0.05% to about 5%.
  • Suntan preparations such as, for example, suntan gels, creams, liquids, powders, sticks and sprays; and indoor tanning preparations; wherein preferred Bio-PDO concentration ranges are from about 0.001% to about 25%, and more preferably from about 1% to about 10%.
  • Preservatives such as, for example, parabens; salicylic acid; sorbic acid; and phenoxy elthanol, wherein preferred Bio-PDO concentration ranges are from about 0.001% to about 100%, and more preferably from about 95% to about 99.99%.
  • vehicles for skin product formulations include oil-in-water emulsion (O/W), water-in-oil emulsion (W/O), water-in-silicon (W/Si), Oleaginous emulsion, water-soluble emulsion, aqueous gel emulsion and absorption bases emulsion.
  • a typical O/W skin product formulation may include 5%-35% surfactant, 2%-15% emulsifier, 0.5%-15% Bio-PDO and 5%-60% water.
  • a typical W/O skin product formulation may include 45%-80% surfactant, 0.5%-5% emulsifier, 0.5%-15% Bio-PDO and 20%-50% water.
  • a typical O/W/O & W/O/W skin product formulation may include 18%-23% surfactant, 3%-8% emulsifier, 0.5%-15% Bio-PDO and 60%-70% water.
  • a typical W/Si & O/Si skin product formulation may include 5-35% surfactant, 2%-3% emulsifier, 0.5%-15% Bio-PDO; and 60%-80% water.
  • vehicles for hair product formulations include oil-in-water emulsion (O/W), water-in-oil emulsion (W/O), Water-in-silicon (W/Si), oleaginous, water-soluble, aqueous gel, and absorption bases, among others.
  • a typical shampoo & conditioner may include 0.1-40% surfactant; 0.1-10% Bio-PDO, and 35-55% water.
  • a typical liquid & cream color dye may include 70-80% dye base, 5-25% Bio-PDO, 0.1-5% dye intermediates, and 0.1-10% developer
  • a typical relaxer or straightener formulation may include 30-60% oil/wax, 10-60% water, 1-10% Bio-PDO, and 0.1-5.0% caustic.
  • a typical dressing formulation may include 0.01-7% film former/plasticizer, 0.01-90% Bio-PDO, 0-30% propellant and 10-90% water.
  • vehicles for oral product formulations include solid forms, such as paste, gel, cream, and ointment; and liquid forms such as washes, rinses, gargles, and sprays.
  • a typical tooth paste/gel/cream/ointment formulation may include 1-60/15-55/30-50% abrasive, 1-80/1-50/1-30% Bio-PDO; 0.01-30/0.1-15/0.5-5% thickener, 0.01-10/0.1-7.5/0.5-5% surfactant, and 0.0001-2/0.001-1/0.01-0.5% antiseptic.
  • a typical mouth wash/rinse/gargle/spray may include 0.1-55/0.5-40/1-25% Bio-PDO, 0.1-55/0.5-40/1-25% alcohol, 0.01-10/0.1-7.5/0.5-5% thickener, 0.001-2/0.01-1/0.1-0.5% surfactant, and 0.0001-5/0.001-2.5/0.01-1% antiseptic.
  • Some examples of vehicles for color cosmetic formulations include, for foundation: O/W & W/O emulsions, anhydrous powders & sticks, and oil & aqueous suspensions; for mascara: O/W & W/O emulsions and anhydrous solvent; for eyeliner: aqueous and anhydrous; for eye shadow: creams and powders; for blushers: powders; and for lip Color: gloss & matte (classical) and solvent (Volatile).
  • a typical formulation for an O/W foundation product may include 2%-15% emulsifier, 50%-75% Bio-PDO, 6%-12% pigment and 8%-12% pearlizer
  • a typical formulation for a W/O foundation product may include 4%-6% emulsifier, 50%-75% Bio-PDO, 6%-12% pigment and 8%-12% pearlizer.
  • a typical formulation for an anhydrous foundation product may include 30-60% Bio-PDO, 5-10% wax, 0.5-1.0% wetting agents, and 30-60% texturizing agent.
  • a typical formulation for a O/W, W/O mascara product may include 4%-10% emulsifier, 2%-5% thickener, 40%-60% Bio-PDO and 6%-12% pigment.
  • a typical formulation for a solvent-based mascara product may include 40-60% Bio-PDO 10-20% wax, 3-10% resin, 3-7% thickener, 5-15% colorant, and 2-10% filler.
  • a typical formulation for an eye shadow product may include 35-55% Bio-PDO, 1.5-3.5% thickener, 7-12% wax, 3-8% emollient, 5-20% colorant, and 5-20% filler.
  • a typical formulation for an eye liner product may include 50-70% water, 0.5-1.5% thickener, 4-12% Bio-PDO, 10-20% colorant, 5-10% alcohol, and 3-8% dispersant.
  • a typical formulation for a classical lipstick product may include 40-70% Bio-PDO, 8-15% wax, 2-5% plasticizer, 0.5-8% colorant, 1-6% pearlizer, 1-15% filler and 0.1-0.5% preservative.
  • a typical formulation for a volatile lipstick product may include 25-60% solvent, 1-85% Bio-PDO, 10-25% wax, 1-10% fixative, 1-15% filler and 1-15% colorant.
  • vehicles for deodorant formulations include sticks, aerosols and pump sprays, among others well known in the art.
  • a typical formulation for a stick deodorant may include 5-9% emulsifier, 1-30% Bio-PDO, 5-80% clarifying agent, and 0.1-2% deodorizer.
  • a typical formulation for an aerosol deodorant may include 0.1-2% emulsifier, 30-50% Bio-PDO, 5-80% clarifying agent, 0.1-2% deodorizer, and 40-60% propellant
  • a typical formulation for a hydroalcoholic pump spray deodorant may include 30-40% solvent, 50-70% Bio-PDO, 0.1-5% solubilizer, and 0.1-5% deodorizer.
  • a typical formulation for a Phase Inversion Temperature Emulsion (PIT) emulsion pump spray deodorant may include 0.1-10% surfactant, 0.1-15% oil, 65-85% Bio-PDO, and 0.1-5% deodorizer.
  • Some examples of vehicles for antiperspirant formulations include sticks (suspension, gel, and emulsion), roll-ons (Emulsion O/W, W/O, W/Si, Clear Hydroalcoholic and suspension), and aerosols, among others well known in the art.
  • a typical stick antiperspirant formulation may include 1-30% gel agent, 15-55% Bio-PDO, 1-20% emollient, 0-20% surfactant, and 15-55% antiperspirant.
  • a typical roll-on antiperspirant formulation may include 0-5% surfactant, 0.5-15% gel agent, 0-5% emollient, 15-25% antiperspirant and 60-85% Bio-PDO.
  • a typical aerosol antiperspirant formulation may include 0.1-2% gel agent, 5-15% antiperspirant, 5-20% Bio-PDO, and 70-80% propellant.
  • Cosmetic and personal care compositions of the invention preferably contain Bio-PDO and one or more conventional cosmetic or dermatological additives or adjuvants including, but not limited to, carriers; actives; fillers; surfactants; thixotropic agents; antioxidants; preserving agents; dyes; pigments; fragrances; thickeners; vitamins; hormones; moisturizers; UV absorbing sunscreens; UV scattering inorganic sunscreens; wetting agents; cationic, anionic, nonionic, or amphoteric polymers; and hair coloring active substances.
  • additives or adjuvants including, but not limited to, carriers; actives; fillers; surfactants; thixotropic agents; antioxidants; preserving agents; dyes; pigments; fragrances; thickeners; vitamins; hormones; moisturizers; UV absorbing sunscreens; UV scattering inorganic sunscreens; wetting agents; cationic, anionic, nonionic, or amphoteric polymers; and hair coloring active substances.
  • emollients include, but are not limited to, emollients, oil absorbents, antimicrobial agents, binders, buffering agents, denaturants, cosmetic astringents, external analgesics, film formers, humectants, opacifying agents, perfumes, pigments, skin soothing and healing agents, preservatives, propellants, skin penetration enhancers, solvents, suspending agents, emulsifiers, cleansing agents, thickening agents, solubilizing agents, waxes, inorganic and organic sunblocks, sunless tanning agents, antioxidants and/or radical scavengers, chelating agents, anti-acne agents, anti-inflammatory agents, desquamation agents/exfoliants, organic hydroxy acids, vitamins, natural extracts and inorganic particulates such as silica and boron nitride.
  • Nonexclusive examples of such materials are described in Harry's Cosmeticology, 7th Ed., Harry & Wilkinson (Hill Publishers, London 1982); in Pharmaceutical Dosage Forms—Disperse Systems; Lieberman, Rieger & Banker, Vols. 1 (1988) & 2 (1989); Marcel Decker, Inc.; in The Chemistry and Manufacture of Cosmetics, 2nd. Ed., deNavarre (Van Nostrand 1962-1965); and in The Handbook of Cosmetic Science and Technology, 1st Ed. Knowlton & Pearce (Elsevier 1993) can also be used in the present invention.
  • the active and other ingredients useful herein can in some instances provide more than one cosmetic and/or therapeutic benefit or operate via more than one mode of action.
  • Such components are particularly preferred additional ingredients, their use often saving both money and formulation space.
  • examples of such components include ethanol, isopropyl myristate, and the many components that can act as both structurants and sensory modifiers, for example silica. Therefore, classifications herein are made for the sake of convenience and are not intended to limit an ingredient to the particularly stated application or applications listed.
  • adjuvants are well known in the field of cosmetics and are described in many publications, for example see Harry's Cosmeticology, 8 th Edition, Martin Rieger, ed. Chemical Publishing, New York (2000). Amounts of adjuvants generally present in the aforementioned cosmetic and personal care compositions are well known in the art (see, e.g., co-owned, co-filed U.S. patent application entitled “Personal Care Compositions”, Attorney Docket No. CL3428 US PRV
  • compositions of the present invention preferably comprise a safe and effective amount of an acceptable carrier, suitable for topical application to the skin within which the essential materials and optional other materials are incorporated to enable the essential materials and optional components to be delivered to the skin at an appropriate concentration.
  • the carrier can thus act as a diluent, dispersant, solvent, or the like for any active ingredients which ensures that they can be applied to, and distributed evenly over, the selected target at an appropriate concentration.
  • the type of carrier utilized in the present invention depends on the types of product form desired for the composition.
  • the topical compositions useful in the subject invention may be made into a wide variety of product forms such as are known in the art. These include but are not limited to lotions, creams, gels, sticks, sprays, ointments, pastes and mousses. These product forms may comprise several types of carriers including, but not limited to, solutions, aerosols, emulsions, gels, solids and liposomes.
  • the carrier(s) of the invention contain a dermatologically acceptable, hydrophilic diluent, such as, preferably, renewably-based, biodegradable 1,3-propanediol.
  • compositions of the invention optionally comprise a safe and effective amount of an active for regulating skin condition including prophylactically and therapeutically regulating the skin condition.
  • Prophylactically regulating skin condition includes delaying, minimizing, and/or preventing visible and/or tactile discontinuities in the skin.
  • Therapeutically regulating the skin condiments includes ameliorating e.g., diminishing, minimising, and/or effacing such discontinuities. Regulating the skin condition also involves improving the skin appearance and/or feel. Also included is regulating the signs of ageing which can involve prophylactically regulating and/or therapeutically regulating one or more of such signs e.g., fine lines, wrinkles, pores etc.
  • compositions of the present invention preferably comprise from about 0.1% to about 15%, more preferably from about 0.3% to about 10%, even more preferably from about 1 to about 5% of the active.
  • vitamin B3 compound means a compound having the formula: 1
  • R is —CONH 2 (i.e., niacinamide), —COOH (i.e., nicotinic acid) or —CH 2 OH (i.e., nicotinyl alcohol); derivatives thereof; and salts of any of the foregoing.
  • vitamin B 3 compounds, or their salts, or mixtures thereof may be used herein.
  • the vitamin B 3 compound typically contains less than about 50% of the compound in a salt form.
  • “retinoid” includes all natural and/or synthetic analogues of Vitamin A or retinol-like compounds which possess the biological activity of Vitamin A in the skin as well as the geometric isomers and stereoisomers of these compounds. Again, all skin regulating materials discussed in application WO 00/24372 should be considered as suitable for use in the present invention.
  • antibacterial active acceptable for underarm application can be used in the deodorant compositions.
  • Antibacterial ingredients include those selected from the group consisting of triclosan, bacteriostatic quaternary ammonium compounds such as benzalkonium chloride, benzethonium chloride, cetyl pyridium chloride, lauryl pyridium chloride and methyl benzethonium chloride; triclocarbon; zinc phenol sulfonate; zinc ricinoleate; triethyl citrate; essential oils; and combinations thereof and the like.
  • the most preferred deodorant active is triclosan.
  • the fragrance may also have antibacterial properties.
  • a safe and effective amount of an anti-inflammatory agent may be added to the compositions of the subject invention, preferably from about 0.1% to about 5%, more preferably from about 0.1% to about 2%, of the composition.
  • the anti-inflammatory agent enhances the skin appearance benefits of the present invention, e.g., such agents contribute to a more uniform and acceptable skin tone or colour.
  • the exact amount of anti-inflammatory agent to be used in the compositions will depend on the particular anti-inflammatory agent utilised since such agents vary widely in potency.
  • Anti-inflammatory agents useful herein include steroids such as hydrocortisone; non-steroidal anti-inflammatory drugs (NSAIDS) such as ibuprofen; panthenol and ether and ester derivatives thereof e.g.
  • panthenol pantothenic acid and their ether, ester or salt derivatives and mixtures thereof; suitable levels are from about 0.1 to about 5%, preferably from about 0.5 to about 3%. Panthenol is especially preferred.
  • organic anti-microbial agents may also be advantageously employed in the methods and products of the present invention.
  • Levels of incorporation are preferably from 0.01% to 3%, more preferably from 0.03% to 0.5% by weight of the composition in which they are present, excluding any volatile propellant also present.
  • Most of the classes of agents commonly used in the art can be utilised.
  • Preferred additional organic anti-microbials are bactericides, for example quaternary ammonium compounds, like cetyltrimethylammonium salts; chlorhexidine and salts thereof; and diglycerol monocaprate, diglycerol monolaurate, glycerol monolaurate, and similar materials, as described in “Deodorant Ingredients”, S. A. Makin and M. R.
  • compositions of the invention Lowry, in “Antiperspirants and Deodorants”, Ed. K. Laden (1999, Marcel Dekker, New York). More preferred additional anti-microbials for use in the compositions of the invention are polyhexamethylene biguamide salts; 2,4,4′-trichloro,2′-hydroxy-diphen-yl ether (triclosan); and 3,7,11-trimethyldodeca-2,6,10-trienol (farnesol).
  • Inorganic anti-microbial agents may also be used in the compositions of the invention. Such materials can often function as anti-perspirant actives when present at a suitable concentration. Examples are often selected from astringent active salts, including, in particular, aluminium, zirconium and mixed aluminium/zirconium salts, including both inorganic salts, salts with organic anions and complexes. Preferred astringent salts include aluminium, zirconium and aluminium/zirconium halides and halohydrate salts, such as chlorohydrates. When included, preferred levels of incorporation are from 0.5% to 60%, particularly from 5% to 30% or 40% and especially from 5% or 10% to 30% or 35% by weight of a composition.
  • Especially preferred aluminium halohydrate salts known as activated aluminium chlorohydrates, are described in EP 6,739 (Unilever PLC and NV).
  • Zirconium aluminium chlorohydrate actives are also preferred materials, as are the so-called ZAG (zirconium-aluminium-glycine) complexes, for example those disclosed in U.S. Pat. No. 3,792,068 (Procter and Gamble Co.).
  • Zinc phenol sulphonate may also be used, preferably at up to 3% by weight of the composition.
  • compositions of the subject invention can further include an anti-oxidant/radical scavenger.
  • the anti-oxidant/radical scavenger is especially useful for providing protection against UV radiation which can cause increased scaling or texture changes in the stratum corneum and against other environmental agents which can cause skin damage. Suitable amounts are from about 0.1% to about 10%, more preferably from about 1% to about 5%, of the composition.
  • Anti-oxidants/radical scavengers such as ascorbic acid (vitamin C) and its salts, ascorbyl esters of fatty acids, ascorbic acid derivatives (e.g., magnesium ascorbyl phosphate), .beta.-carotene, tocopherol (vitamin E), tocopherol sorbate, tocopherol acetate, other esters of tocopherol, butylated hydroxy benzoic acids and their salts, gallic acid and its alkyl esters, especially propyl gallate, uric acid and its salts and alkyl esters, sorbic acid and its salts, amines (e.g., N,N-diethylhydroxylamine, amino-guanidine), sulfhydryl compounds (e.g., glutathione), dihydroxy fumaric acid and its salts, bioflavonoids, lysine, methionine, proline, superoxide dismutase, silymarin, tea
  • Preferred anti-oxidants/radical scavengers are selected from tocopherol acetate, tocopherol sorbate and other esters of tocopherol, more preferably tocopherol acetate.
  • the aforementioned compounds may, when used by themselves, give rise to a high level of tack, especially when used at the higher levels. It has been found, however, that this tacky feel can be offset by using the particulates of the present invention.
  • a chelating agent is especially useful for providing protection against UV radiation which can contribute to excessive scaling or skin texture changes and against other environmental agents which can cause skin damage.
  • a suitable amount is from about 0.01% to about 1%, more preferably from about 0.05% to about 0.5%, of the composition.
  • Exemplary chelators that are useful herein are disclosed in U.S. Pat. No. 5,487,884, incorporated herein by reference.
  • Preferred chelators useful in compositions of the subject invention are ethylenediamine tetraacetic acid (EDTA), furildioxime, and derivatives thereof.
  • colorants and preservatives for example C1-C3 alkyl parabens.
  • a safe and effective amount of a desquamation agent may be added to the compositions of the subject invention, more preferably from about 0.1% to about 10%, even more preferably from about 0.2% to about 50%/, also preferably from about 0.5% to about 4% of the composition.
  • Desquamation agents enhance the skin appearance benefits of the present invention. For example, the desquamation agents tend to improve the texture of the skin (e.g., smoothness).
  • a variety of desquamation agents are known in the art and are suitable for use herein, including organic hydroxy acids such as salicylic acid, glycolic acid, lactic acid, 5-octanoyl salicylic acid, hydroxyoctanoic acid, hydroxycaprylic acid, and lanolin fatty acids.
  • One desquamation system that is suitable for use herein comprises sulphydryl compounds and zwitterionic surfactants and is described in WO 96/01101, incorporated herein by reference.
  • Another desquamation system that is suitable for use herein comprises salicylic acid and zwitterionic surfactants and is described in WO 95/13048, incorporated herein by reference. Salicylic acid is preferred.
  • Emollients are a known class of materials in this art, imparting a soothing effect to the skin. These are ingredients which help to maintain the soft, smooth, and pliable appearance of the skin. Emollients are also known to reduce whitening on the skin and/or improve aesthetics. Examples of chemical classes from which suitable emollients can be found include:
  • fats and oils which are the glyceryl esters of fatty acids, or triglycerides, normally found in animal and plant tissues, including those which have been hydrogenated to reduce or eliminate unsaturation.
  • synthetically prepared esters of glycerin and fatty acids Isolated and purified fatty acids can be esterified with glycerin to yield mono-, di-, and triglycerides. These are relatively pure fats which differ only slightly from the fats and oils found in nature.
  • the general structure may be represented by Formula III:
  • each of R 1 , R 2 , and R 3 may be the same or different and have a carbon chain length (saturated or unsaturated) of 7 to 30.
  • Specific examples include peanut oil, sesame oil, avocado oil, coconut, cocoa butter, almond oil, safflower oil, corn oil, cotton seed oil, castor oil, hydrogenated castor oil, olive oil, jojoba oil, cod liver oil, palm oil, soybean oil, wheat germ oil, linseed oil, and sunflower seed oil;
  • hydrocarbons which are a group of compounds containing only carbon and hydrogen. These are derived from petrochemicals. Their structures can vary widely and include aliphatic, alicyclic and aromatic compounds. Specific examples include paraffin, petrolatum, hydrogenated polyisobutene, and mineral oil.
  • esters which chemically, are the covalent compounds formed between acids and alcohols.
  • Esters can be formed from organic carboxylic acids and any alcohol. Esters here are derived from monocarboxylic acids and alcohols (mono alcohols or polyols as glycols).
  • the general structure would be R 4 COORs.
  • the chain length for R 4 and R 5 can vary from 7 to 30 and can be saturated or unsaturated, straight chained or branched.
  • Esters made using compounds such as Bio-PDO or other biologically derived glycols, can also be used in these compositions.
  • the esters produced include all the appropriate conjugate mono and diesters of biologically derived 1,3 propanediol using organic carboxylic acids.
  • esters in particular that are produced include propanediol distearate and monostearate, propandiol dilaurate and monolaurate, propanediol dioleate and monooleate, propanediol divalerate and monovalerate, propanediol dicaprylate and monocaprylate, propanediol dimyristate and monomyristate, propanediol dipalmitate and monopalmitate, propanediol dibehenate and monobehenate, propanediol adipate, propanediol maleate, propanediol dioxalate, propanediol dibenzoate, propanediol diacetate, and all mixtures thereof.
  • saturated and unsaturated fatty acids which are the carboxylic acids obtained by hydrolysis of animal or vegetable fats and oils.
  • These have general structure R 6 COOH with the R 6 group having a carbon chain length between 7 and 30, straight chain or branched.
  • Specific examples include lauric, myristic, palmitic, stearic, oleic, linoleic and behenic acid.
  • saturated and unsaturated fatty alcohols including guerbet alcohols
  • R 7 OH where R 7 can be straight or branched and have carbon length of 7 to 30.
  • Specific examples include lauryl, myristyl, cetyl, isocetyl, stearyl, isostearyl, oleyl, ricinoleyl and erucyl alcohol;
  • lanolin and its derivatives which are a complex esterified mixture of high molecular weight esters of (hydroxylated) fatty acids with aliphatic and alicyclic alcohols and sterols.
  • Specific examples include lanolin, lanolin oil, lanolin wax, lanolin alcohols, lanolin fatty acids, isopropyl lanolate, ethoxylated lanolin and acetylated lanolin alcohols.
  • alkoxylated alcohols wherein the alcohol portion is selected from aliphatic alcohols having 2-18 and more particularly 4-18 carbons, and the alkylene portion is selected from the group consisting of ethylene oxide, and propylene oxide having a number of alkylene oxide units from 2-53 and, more particularly, from 2-15.
  • specific examples include PPG-14 butyl ether and PPG-53 butyl ether.
  • R 10 3 SiO(Si(R 11 ) 20 ) x Si(R 12 ) -3
  • R 10 , R 11 and R 12 can be the same or different and are each independently selected from the group consisting of phenyl and C1-C60 alkyl;
  • R 14 , R 15 and R 16 can be the same or different and are each independently selected from the group consisting of phenyl and C1-C60 alkyl; or
  • organo substituted silicon compounds of formula R 17 Si(R 18 ) 2 OSiR 193 which are not polymeric where R 17 , R 18 and R 19 can be the same or different and are each independently selected from the group consisting of phenyl and C1-C60 alkyl optionally with one or both of the terminal R groups also containing an hydroxyl group.
  • Specific examples include dimethicone, dimethiconol behenate, C30-45 alkyl methicone, stearoxytrimethylsilane, phenyl trimethicone and stearyl dimethicone.
  • Emollients of special interest include C12-15 alkyl benzoate (FINSOLV TN from Finetex Inc., Elmwood Park, N.J.), isopropyl myristate; and neopentyl glycol diheptanoate.
  • compositions according to the present invention can, illustratively, be included in amounts of 0.1-20%, preferably 1-15%, more preferably 1-10%, by weight, of the total weight of the composition.
  • compositions herein preferably contain an emulsifier and/or surfactant, generally to help disperse and suspend the discontinuous phase within the continuous aqueous phase.
  • a surfactant may also be useful if the product is intended for skin cleansing.
  • emulsifiers will be referred to under the term ‘surfactants’, thus ‘surfactant(s)’ will be used to refer to surface active agents whether used as emulsifiers or for other surfactant purposes such as skin cleansing.
  • surfactants can be used in the composition, provided that the selected agent is chemically and physically compatible with essential components of the composition, and provides the desired characteristics.
  • Suitable surfactants include non-silicone derived materials, and mixtures thereof. All surfactants discussed in application WO 00/24372 should be considered as suitable for use in the present invention.
  • compositions of the present invention preferably comprise from about 0.05% to about 15% of a surfactant or mixture of surfactants.
  • a surfactant or surfactant mixture chosen will depend upon the pH of the composition and the other components present.
  • Preferred surfactants are nonionic.
  • the nonionic surfactants that are useful herein are those that can be broadly defined as condensation products of long chain alcohols, e.g. C8-30 alcohols, with sugar or starch polymers i.e., glycosides.
  • Other useful nonionic surfactants include the condensation products of alkylene oxides with fatty acids (i.e. alkylene oxide esters of fatty acids). These materials have the general formula RCO(X) n OH wherein R is a C10-30 alkyl group, X is —OCH2CH2— (i.e. derived from ethylene glycol or oxide) or —OCH2CHCH3— (i.e.
  • nonionic surfactants are the condensation products of alkylene oxides with 2 moles of fatty acids (i.e. alkylene oxide diesters of fatty acids). These materials have the general formula RCO(X)nOOCR wherein R is a C10-30 alkyl group, X is —OCH2CH2— (i.e. derived from ethylene glycol or oxide) or —OCH2CHCH3-(i.e. derived from propylene glycol or oxide), and n is an integer from about 6 to about 100.
  • cetearyl alcohols such as those available under the trade name Montanov 68 from Seppic and Emulgade PL68/50 from Cognis UK Ltd.
  • An example of a suitable cetearyl glucoside material without added fatty alcohols is Tego® Care CG90 commercially available from Goldschmidt GmbH.
  • Other nonionic surfactants are fatty alkanolamides with the general formula R—CO—N—(CH2CH2OH)n where R is a hydrocarbon chain and n is the integer 1 or 2. The most commonly used are cocoamide DEA (diethanolamide) and cocoamide MEA (monoethanolamide).
  • hydrophilic surfactants useful herein can alternatively or additionally include any of a wide variety of cationic, anionic, zwitterionic, and amphoteric surfactants such as are known in the art. See, e.g., McCutcheon's, Detergents and Emulsifiers, North American Edition (1986), published by Allured Publishing Corporation; U.S. Pat. No. 5,011,681 to Ciotti et al., issued Apr. 30, 1991; U.S. Pat. No. 4,421,769 to Dixon et al., issued Dec. 20, 1983; and U.S. Pat. No. 3,755,560 to Dickert et al., issued Aug. 28, 1973.
  • anionic surfactants are also useful herein. See, e.g., U.S. Pat. No. 3,929,678, to Laughlin et al., issued Dec. 30, 1975.
  • anionic surfactants are also useful herein. See, e.g., U.S. Pat. No. 3,929,678, to Laughlin et al., issued Dec. 30, 1975.
  • exemplary anionic surfactants include the alkoyl isethionates (e.g., C.12-C30), alkyl and alkyl ether sulfates and salts thereof, alkyl and alkyl ether phosphates and salts thereof, alkyl methyl taurates (e.g., C12-C30), and soaps (e.g., alkali metal salts, e.g., sodium or potassium salts) of fatty acids.
  • alkoyl isethionates e.g., C.12-C30
  • alkyl and alkyl ether sulfates and salts thereof alkyl and alkyl ether phosphates and salts thereof
  • alkyl methyl taurates e.g., C
  • amphoteric and zwitterionic surfactants are also useful herein.
  • amphoteric and zwitterionic surfactants which can be used in the compositions of the present invention are those which are broadly described as derivatives of aliphatic secondary and tertiary amines in which the aliphatic radical can be straight or branched chain and wherein one of the aliphatic substituents contains from about 8 to about 22 carbon atoms (preferably C8-C18) and one contains an anionic water solubilising group, e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
  • alkyl imino acetates examples are alkyl imino acetates, and iminodialkanoates and aminoalkanoates, imidazolinium and ammonium derivatives.
  • suitable amphoteric and zwitterionic surfactants are those selected from the group consisting of betaines, sultaines, hydroxysultaines, and branched and unbranched alkanoyl sarcosinates, and mixtures thereof.
  • Fragrance is also a desirable additional component in the compositions of the invention.
  • Suitable materials include conventional perfumes, such as perfume oils and also include so-called deo-perfumes, as described in EP 545,556 and other publications. These latter materials may also qualify as additional organic anti-microbial agents.
  • Levels of incorporation are preferably up to 4% by weight, particularly from 0.1% to 2% by weight, and especially from 0.7% to 1.7% by weight of a composition. Synergies can exist between the essential components of the invention and certain fragrance components—long-lasting odor control being the result.
  • the fragrance may be selected from the group consisting of any cosmetically acceptable fragrance or fragrances acceptable for topical application.
  • the fragrance should be suitable for masking malodor, such as malodor associated with human sweat.
  • these fragrances include those comprising middle note and/or top note volatile constituents, like those selected from the group consisting of allyl amyl glycolate, dihydromyrcenol, aldehyde C-12 MNA, decanol, isobornyl acetate, LILAL®, tricyclo decenyl acetate, benzyl salicylate, and the like, and combinations thereof.
  • Humectant is also a desirable additional component which helps contribute moisturizing properties in the compositions of the invention.
  • exemplary humectants can include, but are not limited to, polyhydric alcohols (i.e. 1,2-propanediol, 1,3 and 1,4-butanediol, 2-methyl-1,3-propanediol, glycerine, and hexylene glycol) and polyols (i.e. polypropylene glycols, polyethylene glycols) and mixtures thereof.
  • a volatile propellant is an essential component of such composition.
  • the level of incorporation of the volatile propellant is typically from 30 to 99 parts by weight and particularly from 50 to 95 parts by weight.
  • Non-chlorinated volatile propellant are preferred, in particular liquefied hydrocarbons or halogenated hydrocarbon gases (particularly fluorinated hydrocarbons such as 1,1-difluoroethane and/or 1-trifluoro-2-fluoroethane) that have a boiling point of below 10.degree.C. and especially those with a boiling point below 0.degree.C.
  • liquefied hydrocarbon gases and especially C3 to C6 hydrocarbons, including propane, isopropane, butane, isobutane, pentane and isopentane and mixtures of two or more thereof.
  • Preferred propellants are isobutane, isobutane/isopropane, isobutane/propane and mixtures of isopropane, isobutane and butane.
  • propellants that can be contemplated include alkyl ethers, such as dimethyl ether or compressed non-reactive gases such air, nitrogen or carbon dioxide.
  • Certain sensory modifiers are further desirable components in the compositions of the invention.
  • Such materials are preferably used at a level of up to 20% by weight of a composition.
  • Emollients, humectants, volatile oils, non-volatile oils, and particulate solids which impart lubricity are all suitable classes of sensory modifiers.
  • Examples of such materials include cyclomethicone, dimethicone, dimethiconol, isopropyl myristate, isopropyl palmitate, talc, finely divided silica (eg. Aerosil 200), polyethylene (eg.
  • Acumist B18 polysaccharides, corn starch, C12-C15 alcohol benzoate, PPG-3 myristyl ether, octyl dodecanol, C7-C14 isoparaffins, di-isopropyl adipate, isosorbide laurate, PPG-14 butyl ether, glycerol, hydrogenated polyisobutene, polydecene, titanium dioxide, phenyl trimethicone, dioctyl adipate, and hexamethyl disiloxane.
  • Thickening Agent (Including Thickeners and Gelling Agents)
  • compositions of the present invention can also preferably comprise a thickening agent, more preferably from about 0.1% to about 10%, even more preferably from about 0.1% to about 9%, and most preferably from about 0.25% to about 8%, of a thickening agent.
  • compositions of the present invention include a thickening agent selected from carboxylic acid polymers, crosslinked polyacrylates, polyacrylamides, xanthan gum and mixtures thereof, more preferably selected polyacrylamide polymers, xanthan gum and mixtures thereof.
  • Preferred polyacrylamides are predispersed in a water-immiscible solvent such as mineral oil and the like, containing a surfactant (HLB from about 7 to about 10) which helps to facilitate water dispersibility of the polyacrylamide.
  • HLB surfactant
  • Most preferred for use herein is the non-ionic polymer under the CTFA designation: polyacrylamide and isoparaffin and laureth-7, available under the trade name Sepigel 305 from Seppic Corporation.
  • acrylic acid/ethyl acrylate copolymers and the carboxyvinyl polymers sold by the B. F. Goodrich Company under the trade mark of Carbopol resins. Suitable Carbopol resins are described in WO98/22085. All thickening agents discussed in application WO 00/24372 should be considered as suitable for use in the present invention.
  • any gelling agent used in the art of soaps or deodorants may be used in the invention.
  • These gelling agents are generally a metal salt of one or more fatty acids having a chain length of 12-22 carbon atoms.
  • the fatty acid portion of the gelling agent is preferably a relatively pure saturated or unsaturated C12-C22 fatty acid including myristic, palmitic, stearic, oleic, linoleic, linolenic, and combinations thereof.
  • Preferred gelling agents include sodium stearate, potassium stearate, sodium palmitate, potassium myristate, sodium myristate, combinations thereof and the like.
  • Structurants also may be additional component of the compositions of the invention that are highly desirable in certain product forms. Structurants, when employed, are preferably present at from 1% to 30% by weight of a composition,
  • Suitable structurants include cellulosic thickeners such as hydroxy propyl cellulose and hydroxy ethyl cellulose, and dibenzylidene sorbitol.
  • Other suitable structurants include sodium stearate, stearyl alcohol, cetyl alcohol, hydrogenated castor oil, synthetic waxes, paraffin waxes, hydroxystearic acid, dibutyl lauroyl glutamide, alkyl silicone waxes, quaternium-18 bentonite, quaternium-18 hectorite, silica, and propylene carbonate.
  • compositions of the present invention preferably also contain silicone based ingredients. Preferred examples are discussed below:
  • Organopolysiloxane oils may be used as ingredients with emollient benefits in the present compositions.
  • Suitable organopolysiloxane oils include volatile, non-volatile, or a mixture of volatile and non-volatile silicones.
  • non-volatile refers to those silicones that are liquid under ambient conditions and have a flash point (under one atmospheric of pressure) of or greater than about 100.degree.C.
  • volatile as used in this context refers to those silicone oils having a flash point of less than 100.degree.C.
  • Suitable organopolysiloxanes can be selected from a wide variety of silicones spanning a broad range of volatilities and viscosities. Non-volatile polysiloxanes are preferred. Suitable silicones are disclosed in U.S. Pat. No. 5,069,897, issued Dec. 3, 1991, which is incorporated by reference herein in its entirety.
  • organopolysiloxanes selected from the group consisting of polyalkylsiloxanes, alkyl substituted dimethicones, dimethiconols, polyalkylaryl siloxanes, and mixtures thereof. More preferred for use herein are polyalkylsiloxanes and cyclomethicones. Preferred among the polyalkylsiloxanes are dimethicones for example DC200 available from Dow Corning and SF96 available from GE Silicone.
  • emulsions of the present invention include a silicone containing emulsifier or surfactant.
  • silicone emulsifiers are useful herein. These silicone emulsifiers are typically organically modified organopolysiloxanes, also known to those skilled in the art as silicone surfactants.
  • Useful silicone emulsifiers include dimethicone copolyols. These materials are polydimethyl siloxanes which have been modified to include polyether side chains such as polyethylene oxide chains, polypropylene oxide chains, mixtures of these chains, and polyether chains containing moieties derived from both ethylene oxide and propylene oxide.
  • dimethicone copolyols examples include alkyl-modified dimethicone copolyols, i.e., compounds which contain C2-C30 pendant side chains.
  • Still other useful dimethicone copolyols include materials having various cationic, anionic, amphoteric, and zwitterionic pendant moieties.
  • compositions of the present invention can also comprise a skin lightening agent.
  • the compositions preferably comprise from about 0.1% to about 10%, more preferably from about 0.2% to about 5%, also preferably from about 0.5% to about 2%, of a skin lightening agent.
  • Suitable skin lightening agents include those known in the art, including kojic acid, arbutin, ascorbic acid and derivatives thereof, e.g., magnesium ascorbyl phosphate.
  • Further skin lightening agents suitable for use herein also include those described in WO 95/34280 and WO 95/23780; each incorporated herein by reference.
  • Inorganic sunscreens use titanium dioxide and zinc oxide. They work primarily by reflecting and scattering UV light.
  • the organics include widely used ingredients such as octyl methoxycinnamate (OMC), 4-methylbenzylidene camphor (4-MBC), avobenzone, oxybenzone, and homosalate. They work primarily by absorbing UV light and dissipating it as heat.
  • Formulators often combine inorganic and organic sunscreens for a synergistic effect. In fact, that is how most are capable of achieving very high SPF—sun protection factor—ratings. SPF is a measure of how effectively a sunscreen in a formulation limits skin exposure to the UV-B rays that burn skin. The higher the number, the more protection a sunscreen formula affords against sunburn.
  • compositions of the present invention can additionally comprise inorganic physical sunblocks.
  • suitable physical sunblocks are described in CTFA International Cosmetic Ingredient Dictionary, 6th Edition, 1995, pp. 1026-28 and 1103, Sayre, R. M. et al., “Physical Sunscreens”, 3. Soc. Cosmet. Chem., vol 41, no 2, pp. 103-109 (1990).
  • Preferred inorganic physical sunblocks are zinc oxide and titanium dioxide, and mixtures thereof.
  • the physical sunblocks are present in an amount such that the present compositions are transparent on the skin (i.e., non-whitening), preferably less than or equal to about 5%.
  • titanium dioxide when used, it can have an anatase, rutile, or amorphous structure.
  • Physical sunblock particles e.g., titanium dioxide and zinc oxide
  • a preferred titanium dioxide is commercially available from Tayca (Japan) and is distributed by Tri-K Industries (Emerson, N.J.) under the MT micro-ionised series (e.g., MT 100SAS).
  • compositions of the present invention preferably comprise from about 0.1% to about 10%, more preferably from about 0.1% to about 4%, and most preferably from about 0.5% to about 2.5%, by weight, of inorganic sunscreen.
  • Esters can function as many of the above noted ingredients. While those in those having skill in the art can readily determine which esters are most appropriate to provide a particularly desired function, applications specifically note that esters used in this invention may include the esters produced, including all the appropriate conjugate mono and diesters, from biologically-derived 1,3 propanediol using organic carboxylic acids.
  • esters in particular that are produced include propanediol distearate and monostearate, propandiol dilaurate and monolaurate, propanediol dioleate and monooleate, propanediol divalerate and monovalerate, propanediol dicaprylate and monocaprylate, propanediol dimyristate and monomyristate, propanediol dipalmitate and monopalmitate, propanediol dibehenate and monobehenate, propanediol adipate, propanediol maleate, propanediol dioxalate, propanediol dibenzoate, propanediol diacetate, and all mixtures thereof.
  • Preferred compositions have an apparent viscosity of from about water thin to about 1,000,000 mPa ⁇ s (centipoise).
  • preferred lotions have an apparent viscosity of from about 500 to about 25,000 mPa ⁇ s;
  • preferred creams have an apparent viscosity of from about 20,000 to about 250,000 mPa ⁇ s.
  • compositions containing Bio-PDO such as clear shampoos and sulfate-free shampoo, may require approximately 30% less salt to adjust the viscosity than other compositions containing comparable glycols such as propylene glycol, butylene glycol, 2-methyl-1,3 propanediol etc.
  • Body wash—Bio-PDO may help maintain and build viscosity.
  • compositions of the present invention are usually formulated to have a pH of 9.5 or below and in general have a pH in the range from about 4.5 to about 9, more preferably from about 5 to about 8.5.
  • These compositions are usually formulated to have a pH of from about 2.5 to about 5, more preferably from about 2.7 to about 4.
  • compositions and methods disclosed and claimed herein can be made and executed without undue experimentation in light of the present disclosure. While the compositions and methods of the present disclosure have been described in terms of preferred embodiments, it will be apparent to those of skill in the art that variations may be applied to the compositions and methods and in the steps or in the sequence of steps of the method described herein without departing from the concept, spirit, and scope of the invention. More specifically, it will be apparent that certain agents, which are chemically related, may be substituted for the agents described herein while the same or similar results would be achieved. All such similar substitutes and modifications apparent to those skilled in the art are deemed to be within the spirit, scope, and concept of the invention as defined by the appended claims.
  • Phase A was combined at 75° C.
  • Phase B was combined at 75° C.
  • Phase B was added to Phase A.
  • Phase C was then added to the Phase A/B.
  • Phase A/B/C was cooled to 40° C. and then Phase D was added. pH was adjusted to 7.0-7.5 with Phase C.
  • the formulation produced was a smooth white and apparently stable emulsion.
  • Freeze/thaw stability was also examined. Freeze/thaw stability was deemed acceptable.
  • the viscosity of the cosmetic emulsion containing biologically-derived 1,3-propanediol was on par with that of propylene glycol (12600 cps) and higher than that of 1,3-butylene glycol (6000 cps) or 2-methyl-1,3-propanediol (9600 cps).
  • Phase C Luvigel EM (caprylic/capric triglycerides 1.0 and sodium acrylates copolymer) Phase D Vitamin E Acetate (BASF) 0.5 Perfume q.s.
  • Viscosity approx. 25,000 mPa ⁇ s (Brookfield); pH value: 6.5
  • Procedure Add ingredients in above order at 80° C. and mix until uniform. Assure each is dissolved prior to next addition. Heat phase B to 80° C. and combine with phase A. Cool to 50° C. Add fragrance and preservative. Pour into containers while liquid and allow to set at room temperature.
  • Stepan ® IPM (Stepan) (isopropyl myristate) 3.25 Bio-PDO 4.00 Phase C Sensomer ® CI-50 (Ondeo Nalco) 3.00 (starch hydroxypropyltrimonium chloride) AA040513 Cucumber (Arylessence) (fragrance) 0.25 Preservative q.s. Sodium hydroxide q.s. to pH 6
  • Viscosity 17,600 cps, pH 6.44
  • Preparation A and preparation B are heated separately to 77 to 82 [deg]C., with constant stirring, until the contents of each part are solubilized. Add preparation A slowly to preparation B while stirring. Continue stirring until the emulsion formed is cooled to room temperature (15 to 30 [deg]C). Add sufficient purified water to obtain 100 grams of standard sunscreen preparation.
  • Phase A Simusol 165 (glyceryl stearate and PEG-100 stearate) 3.20 Montanov ® S (Seppic) (coco-glucoside and coconut alcohol) 1.30 Isodecyl neopentanoate 10.00 PVP hexadecene copolymer 5.00 Bio-PDO 5.00 Ethyl hexyl methoxycinnamate 7.50 Benzophenone-3 2.50 Ethyl hexyl salicylate 5.00 Zinc oxide 7.10 Phase B Sepicalm VG (Seppic) (sodium palmitoyl proline 3.00 and Nymphea alba flower extract) Cyclomethicone 5.00 Phase C Simulgel ® EG (Seppic) (sodium 1.00 acrylate/acryloyldimethyltaurate copolymer, isohexadecane and polysorbate 80) Phase D Tromethamine
  • Viscosity at 25° C. 2000-5000 cps; pH 7.8-8.0
  • Phase 1 Add Carbopol 940 to D.I. water with good mixing until solution is free of lumps. Add PPG-20 methyl glucose ether and Bio-PDO. Mix until completely dissolved. Heat to 165° F. In a separate container, prepare Phase 2. Heat to 165-170° F. Add Phase 2 to Phase 1 (both at 165-170° F.) with good agitation. Emulsify for 20 minutes and then begin to cool with slow agitation. At 110° F. add ingredients from Phase 3. At 90° F. stop cooling and agitation.
  • Viscosity at 25° C.: 2200-3700 cps
  • Procedure Into a vessel equipped with agitation, add first four ingredients. Mix well. Premix fragrance and Tween® 20 in a separate container. Add to the batch. Mix well. Adjust pH with citric acid, if necessary. Add dye and preservative as desired.
  • Viscosity 20 cps
  • Procedure Combine components of phase A and heat to 80° C. Add water and heat to 80° C. Cool to 30° C. and add ethanol. Adjust the pH to 7.0-8.0 with triethanolamine, if required Add fragrance, dye and preservative.
  • Sequence A was dispersed and when the gums were completely hydrated and the phase was uniform, pre-ground Sequence B (pigment phase) was added to it and mixed until both phases were completely uniform and homogeneous.
  • Sequence C was weighed in a separate vessel and heated to 75°-80° C. until all the solids were melted and the phase was uniform. Sequence A was then heated to 75°-80° C. When all the phases were all at the proper temperatures, Sequence C (oil phase) was slowly added to Sequences A & B (water phase). The emulsion was allowed to mix at 75° C. for 15 minutes and then cooled to 25° C.
  • Samples for testing were then poured off and placed at their respective stability stations in preparation for the 4 week study.
  • the color and powder fill loading in these formulations was kept constant at 11.30% dry pigment.
  • Conventional powder fill ingredients were chosen for these formulations as to eliminate any potential variability in test results.
  • Viscosity readings throughout the 4 week test period showed that there was no unusual build or decrease in viscosity.
  • Oven stability consisted of R/T, 45° C., and 2 Freeze/Thaw cycles. After 4 weeks, samples showed no signs of separation, sweating, severe loss of viscosity, change in consistency, loss of structure, odor problems, or color change at any temperature.
  • Sequence A was dispersed and when the gums were completely hydrated and the phase was uniform, pre-ground sequence B (pigment phase) was added to it and mixed until both phases were completely uniform and homogeneous.
  • Sequence C was weighed in a separate vessel and heated to 80°-85° C. until all the solids were melted and the phase was uniform. Sequence A was then heated to 75°-80° C. When all the phases were all at the proper temperatures, Sequence C (oil phase) was slowly added to Sequences A & B (water phase). The emulsion was allowed to mix at 75° C. for 15 minutes.
  • Viscosity readings throughout the 4 week test period showed that there was no unusual build or decrease in viscosity. The variations seen are very typical for a product of this type and fall within an acceptable range for a mascara type product.
  • Oven stability consisted of R/T, 45° C., and 2 Freeze/Thaw cycles. After 4 weeks, samples showed no signs of separation, sweating, severe loss of viscosity, change in consistency, loss of structure, odor problems, or color change at any temperature.
  • Phase A Disperse Carbomer in water with high speed agitation, allowing particles to wet completely. Add Bio-PDO. Heat to 70° C.
  • Phase B Combine Myristyl Myristate, glyceryl stearate, Oleic Acid, Polysorbate 61, C12-15 Alkyl Benzoate, Dimethicone, Isopropyl Palmitate, Sorbitan Stearate, Cetyl Alcohol, Synthetic Beeswax, Stearyl; Alcohol, Benzyl Alcohol, Methylparaben, Propylparaben, Butylparaben, and BHT, heat to 70° C.
  • Phase A Combine Phase A ingredients into water and heat with mixing to 75° C. Slowly add remaining Phase A ingredients. Hold temperature at 75° C. and mix slowly.
  • Phase B Combine phase B ingredients and heat to 75° C. with slow mixing. Add Phase B to Phase A and mix until uniform.
  • Phase C Add Phase C one at a time
  • Phase D Use Phase D to adjust the pH of batch to 6.0-6.5
  • phase B aqueous phase
  • Preparation Mix the ingredients of phase B (aqueous phase) and heat the mixture to 65 oC with thorough stirring to form a homogeneous aqueous phase.
  • phase A Separately mix the contents of phase A until a uniform gel is formed.
  • phase A and phase B and heat the mixture while stirring at 65 oC for 1 hour. Cool the composition and transfer into containers.
  • phase B aqueous phase
  • Preparation Mix the ingredients of phase B (aqueous phase) and heat the mixture to 65 oC with thorough stirring to form a homogeneous aqueous phase.
  • phase A Separately mix the contents of phase A until a uniform gel is formed.
  • phase B Mix phase A and phase B and heat the mixture while stirring at 65 oC for 1 hour. Cool the composition and transfer into containers.
  • Germaben II-E 0.30 INGREDIENT Weight Percent C13-15 Alkanes (Gemseal ® 25) 5.00 C15-19 Alkanes (Gemseal ® 40) 10.00 Oleth-5 13.00 DEA Oleth-3 Phosphate 5.75 Deionized Water 47.45 Bio-PDO 12.00 Glycerin 99% 6.50 Germaben II-E 0.30
  • Sequence A weigh the ingredients in Sequence A in a suitable vessel. Begin heating to 75-80° C. with good mixing. Weigh ingredients in Sequence B in a secondary vessel. Begin heating to 75-80° C. with good mixing. When both sequences are at the proper temperatures, slowly add Sequence B to Sequence A with continuous propeller mixing. Increase mixer speed as the sequences are combined. Switch to a side wiping mixer and continue mixing until the batch is smooth, uniform and homogeneous. Mix for 15 minutes and begin cooling the batch with continuous mixing. Cool the batch to 25° C. At 25° C., remove the batch and store in airtight containers. Check the viscosity and pH of the batch.
  • Phase A Combine ingredients in Phase A and begin mixing until the Phase is smooth and uniform.
  • Add Phase C to the batch with homogenizing mixing. When the batch is uniform, begin cooling the batch to 55° C. with continuous homogenizer mixing. At 55° C. add Phase D to the batch. Mix until uniform.
  • Phase E to the batch and mix until uniform.
  • Phase A ingredients in a suitable mixing vessel Mix until the Phase is uniform.
  • Grind Phase B in a micropulverizer When Phase B is free of pigment specks, add Phase B to Phase A with continuous mixing. Mix until the phases are uniform and free of lumps. Homogenize the batch for 10-15 minutes or as necessary to make Phase A & B smooth and homogeneous.
  • In a separate vessel combine Phase C ingredients and begin heating to 80-85° C. with good mixing. Begin heating Phase A to 75-80° C. When all phases are at the proper temperatures slowly add Phase C to Phases A & B with continuous mixing. Mix for 15 minutes with the batch covered to prevent water loss. Begin cooling the batch.
  • a mouthwash for infants contains, for every 100 g or mL Ingredient Weight Percent Sorbitol 3.00 Glycerol 3.00 Methylparaben 0.20 Propylparaben 0.10 Bio-PDO 4.00 Disodium EDTA 0.10 Sodium lauryl sulfate 0.40 Sodium saccharin 0.06 Petitgraine essential oil 0.02 Tea tree essential oil 0.03 Potassium sorbate 0.20 Sodium citrate 0.05 Potassium Phosphate 0.10 Citric acid 0.50 CI19140 0.02 CI47090 0.01 Water q.s. to 100
  • Mouth rinse comprising antibacterial ester, arginine derivative, surfactant, humectant Ingredient Weight Percent Ethyl lauroylarginate-HCl 0.1 Sorbitol 10.0 Glycerin 10.0 Bio-PDO 7.0 Polysorbate-20 0.8 Cocoamidopropylbetaine 0.8 Sodium saccharin 0.03 Flavor 0.10 Water q.s. to 100%
  • Binders 0.1-5.0% Na CM-cellulose Foaming components 0.1-5.0% Na lauryl sulfate Antidesiccants 1.0-15.0% Bio-PDO Preservatives 0.02-0.5% Me or Pr p-hydroxybenzoate Flavors 0.1-2.0% peppermint oil Abrasives 5.0-25% colloid silica, silica powder Solvents 0.1-90.0% Water 50.0-90.0% phosphate buffer pH 6.5-7.5 0.5-3.0% ethanol 0.1-50.0% Biologically active components 0.01-8.0% Protamin sulfate 0.1-5.0% Allantoin 0.05-1.0% Sodium fluoride 0.03-3.0% Vitamin PP 0.01-5.0% Provitamin B5 0.05-8.0%
  • Antimicrobial cream or ointment Ingredient Weight Percent Glycerol 6% Bio-PDO 5.5% Sodium lauryl sulfate 1% Cetyl alcohol 4.5% Cetyl palmitate 4% Stearic alcohol 4.5% Stearic acid 4% White petrolatum 5% Antimicrobial agent 1% Water 64.5%
  • Mouth Rinse Ingredient Weight Percent Alcohol 15% Antimicrobial agent 0.05% Flavoring oil 0.1% Bio-PDO 3% Sodium lauryl Me cocoyl taurate 0.3% Sodium citrate 0.08% Citric acid 0.02% Saccharin sodium 0.1% FD&C Green No 30.0002% Water q.s. to 100%

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US11/705,342 Abandoned US20070203323A1 (en) 2006-02-10 2007-02-12 Food compositions comprising biologically-based biodegradable 1,3-propanediol esters
US11/705,262 Abandoned US20070202062A1 (en) 2006-02-10 2007-02-12 Natural deodorant compositions comprising renewably-based, biodegradable 1,3-propanediol
US11/705,327 Abandoned US20070203276A1 (en) 2006-02-10 2007-02-12 Plasticizers comprising biologically-based mono and di esters
US11/705,275 Abandoned US20070200087A1 (en) 2006-02-10 2007-02-12 Deicing and anti-icing compositions comprising renewably-based, biodegradable 1,3-propanediol
US11/705,198 Active 2027-05-01 US7759393B2 (en) 2006-02-10 2007-02-12 Bio-derived 1,3-propanediol and its conjugate esters as natural and non irritating solvents for biomass-derived extracts, fragrance concentrates, and oils
US11/705,346 Abandoned US20070207113A1 (en) 2006-02-10 2007-02-12 Personal care and cosmetic compositions comprising renewably-based, biodegradable 1,3-propanediol
US11/705,312 Abandoned US20070213247A1 (en) 2006-02-10 2007-02-12 Detergent and liquid soap compositions comprising biologically-based mono and di esters
US11/705,212 Active 2029-08-26 US7988883B2 (en) 2006-02-10 2007-02-12 Heat transfer compositions comprising renewably-based biodegradable 1,3-propanediol
US11/705,257 Abandoned US20070207939A1 (en) 2006-02-10 2007-02-12 Compositions comprising mono and di esters of biologically-based 1,3-propanediol
US11/705,227 Abandoned US20070202073A1 (en) 2006-02-10 2007-02-12 Personal care and cosmetics compositions comprising biologically-based mono and di esters
US11/705,245 Active 2029-09-04 US7960575B2 (en) 2006-02-10 2007-02-12 Synthesis of mono and di esters from biologically-produced 1,3-propanediol
US11/705,254 Abandoned US20070241306A1 (en) 2006-02-10 2007-02-12 Biodegradable compositions comprising renewably-based, biodegradable 1,3-propanediol
US11/705,276 Abandoned US20070207940A1 (en) 2006-02-10 2007-02-12 Detergent compositions comprising renewably-based, biodegradable 1,3-propanediol
US12/427,232 Active US7972530B2 (en) 2006-02-10 2009-04-21 Deicing and anti-icing compositions comprising renewably-based, biodegradable 1,3-propanediol
US12/554,056 Abandoned US20090325853A1 (en) 2006-02-10 2009-09-04 Detergent and liquid soap compositions comprising biologically-based mono and di esters
US12/579,538 Active 2028-11-26 US8309116B2 (en) 2006-02-10 2009-10-15 Personal care and cosmetics compositions comprising biologically-based mono and di esters
US12/786,506 Active US8048920B2 (en) 2006-02-10 2010-05-25 Personal care composition containing bio-derived 1,3-propanediol and its conjugate esters
US13/238,776 Active US8436046B2 (en) 2006-02-10 2011-09-21 Detergent composition containing bio-derived 1,3-propanediol and its conjugate esters
US13/413,844 Abandoned US20130071535A1 (en) 2006-02-10 2012-03-07 Food and flavorant compositions comprising renewably-based, biodegradable 1,3-propanediol
US13/833,539 Active US8802729B2 (en) 2006-02-10 2013-03-15 Enzyme stabilized detergent compositions
US13/834,000 Active US8598231B2 (en) 2006-02-10 2013-03-15 Flavoring agents containing bio-derived 1,3-propanediol and its conjugate esters
US14/330,624 Active 2028-04-07 US9668951B2 (en) 2006-02-10 2014-07-14 Pharmaceutical compositions comprising renewably-based biodegradable 1,3-propanediol
US14/330,640 Active 2027-05-15 US9375390B2 (en) 2006-02-10 2014-07-14 Agricultural compositions comprising renewably-based biodegradable 1,3-propanediol
US14/589,193 Abandoned US20150125403A1 (en) 2006-02-10 2015-01-05 Personal care and cosmetic compositions comprising renewably-based, biodegradable 1,3-propanediol
US15/494,183 Abandoned US20170216171A1 (en) 2006-02-10 2017-04-21 Biodegradable compositions comprising renewably-based, biodegradable 1,3-propanediol
US16/013,180 Abandoned US20180303732A1 (en) 2006-02-10 2018-06-20 Biodegradable coatings and paints

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US11/705,342 Abandoned US20070203323A1 (en) 2006-02-10 2007-02-12 Food compositions comprising biologically-based biodegradable 1,3-propanediol esters
US11/705,262 Abandoned US20070202062A1 (en) 2006-02-10 2007-02-12 Natural deodorant compositions comprising renewably-based, biodegradable 1,3-propanediol
US11/705,327 Abandoned US20070203276A1 (en) 2006-02-10 2007-02-12 Plasticizers comprising biologically-based mono and di esters
US11/705,275 Abandoned US20070200087A1 (en) 2006-02-10 2007-02-12 Deicing and anti-icing compositions comprising renewably-based, biodegradable 1,3-propanediol
US11/705,198 Active 2027-05-01 US7759393B2 (en) 2006-02-10 2007-02-12 Bio-derived 1,3-propanediol and its conjugate esters as natural and non irritating solvents for biomass-derived extracts, fragrance concentrates, and oils

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US11/705,312 Abandoned US20070213247A1 (en) 2006-02-10 2007-02-12 Detergent and liquid soap compositions comprising biologically-based mono and di esters
US11/705,212 Active 2029-08-26 US7988883B2 (en) 2006-02-10 2007-02-12 Heat transfer compositions comprising renewably-based biodegradable 1,3-propanediol
US11/705,257 Abandoned US20070207939A1 (en) 2006-02-10 2007-02-12 Compositions comprising mono and di esters of biologically-based 1,3-propanediol
US11/705,227 Abandoned US20070202073A1 (en) 2006-02-10 2007-02-12 Personal care and cosmetics compositions comprising biologically-based mono and di esters
US11/705,245 Active 2029-09-04 US7960575B2 (en) 2006-02-10 2007-02-12 Synthesis of mono and di esters from biologically-produced 1,3-propanediol
US11/705,254 Abandoned US20070241306A1 (en) 2006-02-10 2007-02-12 Biodegradable compositions comprising renewably-based, biodegradable 1,3-propanediol
US11/705,276 Abandoned US20070207940A1 (en) 2006-02-10 2007-02-12 Detergent compositions comprising renewably-based, biodegradable 1,3-propanediol
US12/427,232 Active US7972530B2 (en) 2006-02-10 2009-04-21 Deicing and anti-icing compositions comprising renewably-based, biodegradable 1,3-propanediol
US12/554,056 Abandoned US20090325853A1 (en) 2006-02-10 2009-09-04 Detergent and liquid soap compositions comprising biologically-based mono and di esters
US12/579,538 Active 2028-11-26 US8309116B2 (en) 2006-02-10 2009-10-15 Personal care and cosmetics compositions comprising biologically-based mono and di esters
US12/786,506 Active US8048920B2 (en) 2006-02-10 2010-05-25 Personal care composition containing bio-derived 1,3-propanediol and its conjugate esters
US13/238,776 Active US8436046B2 (en) 2006-02-10 2011-09-21 Detergent composition containing bio-derived 1,3-propanediol and its conjugate esters
US13/413,844 Abandoned US20130071535A1 (en) 2006-02-10 2012-03-07 Food and flavorant compositions comprising renewably-based, biodegradable 1,3-propanediol
US13/833,539 Active US8802729B2 (en) 2006-02-10 2013-03-15 Enzyme stabilized detergent compositions
US13/834,000 Active US8598231B2 (en) 2006-02-10 2013-03-15 Flavoring agents containing bio-derived 1,3-propanediol and its conjugate esters
US14/330,624 Active 2028-04-07 US9668951B2 (en) 2006-02-10 2014-07-14 Pharmaceutical compositions comprising renewably-based biodegradable 1,3-propanediol
US14/330,640 Active 2027-05-15 US9375390B2 (en) 2006-02-10 2014-07-14 Agricultural compositions comprising renewably-based biodegradable 1,3-propanediol
US14/589,193 Abandoned US20150125403A1 (en) 2006-02-10 2015-01-05 Personal care and cosmetic compositions comprising renewably-based, biodegradable 1,3-propanediol
US15/494,183 Abandoned US20170216171A1 (en) 2006-02-10 2017-04-21 Biodegradable compositions comprising renewably-based, biodegradable 1,3-propanediol
US16/013,180 Abandoned US20180303732A1 (en) 2006-02-10 2018-06-20 Biodegradable coatings and paints

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WO2008123845A8 (en) 2009-04-30
US20100034761A1 (en) 2010-02-11
JP2009527469A (ja) 2009-07-30
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US20070200088A1 (en) 2007-08-30
WO2007095262A3 (en) 2008-01-10
JP6006817B2 (ja) 2016-10-12
US20130303423A1 (en) 2013-11-14
US7972530B2 (en) 2011-07-05
EP1991515A4 (en) 2013-03-06
US20090325853A1 (en) 2009-12-31
US20070207940A1 (en) 2007-09-06
US8598231B2 (en) 2013-12-03
US20130071535A1 (en) 2013-03-21
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US20070202126A1 (en) 2007-08-30
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CN105078773A (zh) 2015-11-25
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US20070202062A1 (en) 2007-08-30
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