US20070202073A1 - Personal care and cosmetics compositions comprising biologically-based mono and di esters - Google Patents

Personal care and cosmetics compositions comprising biologically-based mono and di esters Download PDF

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Publication number
US20070202073A1
US20070202073A1 US11/705,227 US70522707A US2007202073A1 US 20070202073 A1 US20070202073 A1 US 20070202073A1 US 70522707 A US70522707 A US 70522707A US 2007202073 A1 US2007202073 A1 US 2007202073A1
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United States
Prior art keywords
propanediol
personal care
ester
care composition
composition
Prior art date
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Abandoned
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US11/705,227
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English (en)
Inventor
Gyorgyi Fenyvesi
Ann Wehner
Melissa Joerger
Raja Poladi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DuPont Tate and Lyle Bio Products Co LLC
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Individual
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Family has litigation
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=US20070202073(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 US11/705,227 priority Critical patent/US20070202073A1/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.
Publication of US20070202073A1 publication Critical patent/US20070202073A1/en
Priority to US12/579,538 priority patent/US8309116B2/en
Abandoned legal-status Critical Current

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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
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/223—Five-membered rings containing nitrogen and carbon only
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • 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
    • 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
    • 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

  • the invention relates to the field of personal care products, which includes cosmetics, crèmes, shampoos, body wash, liquid soap, moisturizers, deodorants, toiletries, and skin care products. More specifically, the invention relates to personal care compositions comprising biologically-derived 1,3-propanediol esters.
  • the active ingredient is only a small portion of the product.
  • Much of these products are composed of other ingredients, adjuvants, which provide benefit to the product.
  • These adjuvants convey benefit to the product in a variety of ways.
  • Some adjuvants allow the active ingredient to be applied in a particular manner, by changing or assisting to change the concentration, feel or viscosity of the solution.
  • Such classes of this type of adjuvants are emulsifiers, conditioners, surfactants, structurants, and thickeners.
  • Other adjuvants protect the active ingredient or the product as whole from disintegrating from its desired form.
  • Humectants, temperature stabilizers and chemical stabilizers are classes of this type of adjuvant.
  • Still other adjuvants provide an aesthetic appeal to the appearance of product. Adjuvants of this type can be further classified as opacificers, colorants or pearlizing agents.
  • Greenhouse gases are gases that allow sunlight to enter the atmosphere freely. When sunlight strikes the Earth's surface, some of it is reflected back towards space as infrared radiation. Greenhouse gases absorb this infrared radiation and trap the heat in the atmosphere. Over time, the amount of energy sent from the sun to the Earth's surface should be about the same as the amount of energy radiated back into space, leaving the temperature of the Earth's surface roughly constant. However, increasing the quantity of greenhouse gases above the quantity that existed before the rise of human industrialization is thought to increase the retained heat on the Earth's surface and produce the global warming observed in the last two centuries.
  • 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. 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. Only organic products composed of carbon molecules from renewably based sources such as plant sugars and starches and ultimately atmospheric carbon are considered to not further contribute to the greenhouse effect, when compared to the same organic molecules that are petroleum or fossil fuel based.
  • Published U.S. Patent Application No. 2005/0069997 discloses a process for purifying 1,3-propanediol from the fermentation broth of a cultured E. coli that has been bioengineered to synthesize 1,3-propanediol from sugar.
  • the basic process entails filtration, ion exchange and distillation of the fermentation broth product stream, preferably including chemical reduction of the product during the distillation procedure.
  • highly purified compositions of 1,3-propanediol are also provided.
  • compositions comprising esters of 1,3-propanediol and acceptable carriers are provided.
  • the esters can have at least 3% biobased carbon, and the compositions can further comprise 1,3-propanediol that is biologically-derived.
  • processes for producing personal care compositions comprising esters of 1,3-propanediol and acceptable carriers.
  • the processes comprise providing biologically produced 1,3-propanediol, contacting the 1,3-propanediol with organic acids, which produces the esters, recovering the esters, and incorporating the esters into personal care formulations.
  • processes of making a personal care composition comprising providing an ester of 1,3 propanediol and mixing the ester with an acceptable carrier to form a personal care composition.
  • FIG. 3 is diagram of nuclear magnetic resonance spectra of the products obtained in example 4.
  • FIG. 4 is diagram of nuclear magnetic resonance spectra of the recrystallized products obtained in example 5.
  • FIG. is diagram of nuclear magnetic resonance spectra of the products obtained in example 6.
  • FIG. 6 is diagram of nuclear magnetic resonance spectra of the products obtained in example 7.
  • the transformed E. coli DH5 ⁇ containing cosmid pKP1 containing a portion of the Klebsiella genome encoding the glycerol dehydratase enzyme was deposited on 18 Apr. 1995 with the ATCC under the terms of the Budapest Treaty and is identified by the ATCC number ATCC 69789.
  • the transformed E. coli DH5 ⁇ containing cosmid pKP4 containing a portion of the Klebsiella genome encoding a diol dehydratase enzyme was deposited on 18 Apr. 1995 with the ATCC under the terms of the Budapest Treaty and is identified by the ATCC number ATCC 69790.
  • ATCC refers to the American Type Culture Collection international depository located at 10801 University Boulevard, Manassas, Va., 20110-2209, U.S.A.
  • ATCC No.” is the accession number to cultures on deposit with the ATCC.
  • Congugate esters of 1,3-propanediol are suitable, in a non-limiting way, for use in personal compositions such as liquid hand soaps, shampoos and body detergents as emulisifers, pearlizing agents, surfactants, gelling agents, structurants, thickeners, and opacifiers.
  • the esters described herein are especially desirable as components of liquid soap, shampoo, and body detergent formulations as they provide the intended functionality and can be produced from a biologically-derived compound.
  • esters of 1,3-propanediol are also useful as an active ingredient in personal care products and cosmetics as emollients. In other applications such esters are useful in the delivery, application, or effectiveness of the personal care product and cosmetic.
  • the esters act as an additive or adjuvant when used to improve the delivery, application or effectiveness of a product.
  • the esters can be used as a humectant, opacifier, pearlizing agent, gelling agent, emulsifier, surfactant, structurant, thickener, compatibilizer or solvent for cosmetics and personal care products.
  • Fatty acid monoesters and diesters of biologically-produced 1,3 propanediol are formed by esterification of biologically derived 1,3-propanediol.
  • Biologically-derived 1,3-propanediol can be obtained through catalytic conversion of non-fossil fuel carbon via fermentation with an organism that is able to synthesize 1,3-propanediol. The process provides 1,3-propanediol and its conjugate monoesters and diesters without introducing additional carbon into the atmosphere during the production, use, or disposal of the material.
  • 1,3 propanediol represents a new feedstock for useful monoesters and diesters of 1,3 propanediol. Such monoesters and diesters have not previously been produced from a biosourced monomer.
  • new compositions of matter comprising 1,3 propanediol esters derived from biosourced carbon substrates are provided. These compositions may be distinguished from similar compositions derived from all petrochemical carbon on the basis of biobased carbon content.
  • bio-PDO esters refer to monoesters and diesters produced from biologically produced 1,3-propanediol.
  • bioPDO biologically-produced PDO
  • biologically-produced 1,3-propanediol biologically-produced 1,3-propanediol
  • biologically derived 1,3-propanediol biologically derived 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.
  • 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
  • Bio-produced means organic compounds produced by one or more species or strains of living organisms, including particularly strains of bacteria, yea st, 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.
  • 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.
  • “Naturally occurring” as used herein refers to substances that are derived from a renewable source and/or are produced by a biologically-based process.
  • “Fatty acid” as used herein refers to carboxylic acids that are often have long aliphatic tails, however, carboxylic acids of carbon length 1-40 are specifically included in this definition for the purpose of describing the present invention.
  • “Fatty acid esters” as used herein are esters, which are composed of such, defined fatty acids.
  • Catalyst refers to a substance that is facilitates a chemical reaction without being either a reactant or a product of said reaction.
  • 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.
  • Haldrogenation reactor refers to any of the known chemical reactors known in the literature, including but not limited to shaker-tubes, batch autoclaves, slurry reactors, up-flow packed bed, and trickle flow packed bed reactors.
  • IRMS refers to measurements of C02 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.
  • shampoo as used herein means a composition for cleansing and conditioning hair or skin, including scalp, face, and body.
  • personal care composition refers to a substance that is in grooming.
  • These personal care compositions include, but are not limited to, skin care compositions, skin cleansing compositions, make-up, facial lotions, cream moisturizers, body washes, body lotions, liquid soap, milk bath, bronzing sticks, foot creams, hand creams, lipstick, eyeshadow, foundation, facial powders, deodorant, shaving cream compositions, nail polishes, shaving lotions, cream depilatories, lotion depilatories, facial masks made with clay materials, anti-aging products, baby shampoos, hair reconstructionors, hair conditioners, hair treatment creams, styling gels, styling foams, hair mousses, hair sprays, set lotions, blow-styling lotions, hair color lotions, and hair relaxing compositions.
  • Personal care products could be used on any animal.
  • the present invention is preferred to be used in the grooming of mammals and birds.
  • the present invention is more preferred to be use in the grooming of humans, canines, felines, and equines.
  • the present invention is most preferred to be used in the grooming of humans.
  • “Personal care product” and personal care composition are used synonymously herein.
  • 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 C02 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
  • 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 modem 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%.
  • compositions in accordance with the invention include a composition comprising an ester of 1,3-propanediol.
  • the esters can have a varying amount of biobased carbon depending on the compound used in the esterification.
  • Biologically derived 1,3-propanediol contains biobased carbon. All three carbon atoms in 1,3 propanediol are biobased carbons. If the conjugate esters are formed using carboxylic acids that contain all biobased carbon, then the resulting esters also contain all biobased carbon. If, however, the carboxylic acids contain non-biobased carbons, i.e.
  • the resulting ester will contain a percentage of biobased carbon in proportion to the number of carbons contributed from the carboxylic acid compared to the three carbons contributed from the biologically-derived 1,3-propanediol.
  • distearate propanediol contains 39 carbon atoms, 18 from each of the stearic acid carbon chains and three from the 1,3-propanediol. Accordingly, if the strearic acid is non-biobased, 36 carbons out of the total 39 in distearate propanediol are non-biobased carbon.
  • the predicted theoretical biobased content of distearate propanediol made from biologically-derived propanediol, and non-biologically derived strearic acid is approximately 7.7 percent.
  • propylene glycol dibenzoate (BENZOFLEX (R) 284, Velsicol Chem. Corp. Rosemont, Ill.) was found to have 0% bio-based carbon content.
  • propanediol dibenzoate synthesized using biologically-derived 1,3-propanediol had 19% bio-based carbon content.
  • the predicted bio-based carbon content propanediol dibenzoate made from biologically-derived 1,3 propanediol is 17.6%, which is within the standard deviation of the method.
  • the conjugate esters of biologically-derived 1,3-propanediol have biobased content values proportional to the biobased content of the acids used to form the esters.
  • the esters therefore can have biobased content of at least 3% biobased carbon, at least 6% biobased carbon, at least 10% biobased carbon, at least 25% biobased carbon, at least 50% biobased carbon, at least 75% biobased carbon, and 100% biobased carbon.
  • the ester recovered should be greater than 5% biobased carbon.
  • the ester recovered should be greater than 10% biobased carbon.
  • Biologically-derived 1,3-propanediol is collected in a high purity form.
  • Such 1,3-propanediol 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 nm 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.
  • 1,3-propanediol produced biologically via fermentation is known, including in U.S. Pat. No. 5,686,276, U.S. Pat. No. 6,358,716, and U.S. Pat. No. 6,136,576, which disclose a process using a recombinantly-engineered bacteria that is able to synthesize 1,3-propanediol during fermentation using inexpensive green carbon sources such as glucose or other sugars from plants.
  • inexpensive green carbon sources such as glucose or other sugars from plants.
  • Biologically-derived 1,3-propanediol can be obtained based upon use of the fermentation broth generated by a genetically-engineered Eschericia coli ( E. coli ), as disclosed in U.S. Pat. No. 5,686,276.
  • 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.
  • Biologically derived 1,3-propanediol contains carbon from the atmosphere incorporated by plants, which compose the feedstock for the production of biologically derived 1,3-propanediol.
  • the biologically derived 1,3-propanediol contains only renewable carbon, and not fossil fuel based, or petroleum based carbon. Therefore the use of biologically derived 1,3-propanediol and its conjugate esters has less impact on the environment as the 1,3-propanediol does not deplete diminishing fossil fuels.
  • the use of biologically derived 1,3-propanediol and its conjugate esters also does not make a net addition of carbon dioxide to the atmosphere, and thus does not contribute to greenhouse gas emissions. Accordingly, the present invention can be characterized as more natural and having less environmental impact than similar compositions comprising petroleum based glycols.
  • a composition comprising 1,3-propanediol and an ester of 1,3-propanediol is provided, where the 1,3-propanediol is biologically derived.
  • the biologically-derived 1,3-propanediol in these compositions can have at least 85% biobased carbon, at least 95% biobased carbon, or 100% biobased carbon, when assessed by the application of ASTM-D6866 as described above.
  • a sample of biologically-derived 1,3-propanediol was analysized using ASTM method D 6866-05. The results received from Iowa State University demonstrated that the above sample was 100% bio-based content.
  • ASTM-D6866 method chemical, or petroleum-based 1,3-propanediol (purchased from SHELL) was found to have 0% bio-based content.
  • Propylene glycol USP grade from ALDRICH was found to have 0% bio-based content.
  • a personal care compositions 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 1,3-propanediol use to form 1,3 propanediol esters can comprise at least about 1% bio-based carbon content up to 100% bio-based carbon content, and any percentage there between.
  • esters of biologically derived 1,3-propanediol can be synthesized by contacting biologically derived 1,3-propanediol with an organic acid.
  • the organic acid can be from any origin, preferably either a biosource or synthesized from a fossil source. Most preferably the organic acid is derived from natural sources or bio-derived having formula R1-COOH. Where in the substituent R1 can be saturated or unsaturated, substituted or unsubstituted, aliphatic or aromatic, linear or branched hydrocarbon having chain length 1 to 40 or their salts or alkyl esters.
  • the hydrocarbon chain can also have one or more functional groups such as alkene, amide, amine, carbonyl, carboxylic acid, halide, hydroxyl groups.
  • Naturally occurring organic acids produced esters containing all biobased carbon. These naturally occurring organic acids, especially those produced by a biological organism, are classified as bio-produced and the resulting ester or diester could thereby also be classified as bio-produced.
  • Naturally occurring sources of such fatty acids include coconut oil, various animal tallows, lanolin, fish oil, beeswax, palm oil, peanut oil, olive oil, cottonseed oil, soybean oil, corn oil, rape seed oil. Conventional fractionation and/or hydrolysis techniques can be used if necessary to obtain the fatty acids from such materials.
  • Appropriate carboxylic acids for producing esters of biologically-derived 1,3-propanediol generally include: (1) C1—C3 carbon containing mono carboxylic acids, including formic acid and acetic acid; (2) fatty acids, such as those acids containing four or more carbon atoms; (3) saturated fatty acids, such as butyric acid, caproic acid, valeric acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, and behenic acid; (4) unsaturated fatty acids, such as oleic acid, linoleic acid, and euricic acid; (5) polyunsaturated fatty acids, such as alpha-linolenic acid, stearidonic acid (or moroctic acid), eicosatetraenoic acid, omega-6 fatty acids, arachidonic acids, and omege-3 fatty acids, eicosapentaenoic acid (or tim
  • acids and their salts or alkyl esters are specifically useful, acetic, alginic, butyric, lauric, myristic, palmitic, stearic, arachidic, adipic, benzoic, caprylic, maleic, palmitic, sebacic, archidonic, erucic, palmitoleic, pentadecanoic, heptadecanoic, nondecanoic, octadectetraenoic, eicosatetraenoic, eicosapentaenoic, docasapentaenoic, tetracosapentaenoic, tetrahexaenoic, docosahexenoic, (alpha)-linolenic, docosahexaenoic, eicosapentaenoic, linoleic, arachidonic, oleic, erucic, formic, prop
  • a more preferred list of suitable organic acids are acetic, adipic, benzoic, maleic, sebacic, and mixtures of such acids.
  • suitable “fatty acids” meaning generally acids named containing 8-40 carbon in the carbon useful in the present invention include butyric, valeric, caproic, caprylic, pelargonic, capric, lauric, myristic, palmitic, stearic, arachidic, behenic, cerotic, oleic, linoleic, linolenic, margaric, montanic, melissic, lacceroic, ceromelissic, geddic, ceroplastic and the mixtures of such acids.
  • these acids, and their salts and alkyl esters are most preferred stearic, lauric, palmetic, oleic, 2-ethyl hexanoic, and 12-hydroxystearic and mixtures of such acids.
  • esters produced include all the appropriate conjugate mono and diesters of 1,3 propanediol using the described organic acids.
  • Some 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 dibenzoate, propanediol diacetate, and all mixtures thereof.
  • esters produced include: propanediol distearate and monostearate, propanediol dioleate and monooleate, propanediol dicaprylate and monocaprylate, propanediol dimyristate and monomyristate, and all mixtures thereof.
  • 1,3-propanediol can be contacted, preferably in the presence of an inert gas reacted with a fatty acid or mixture of fatty acids or salts of fatty acids in the absence or presence of a catalyst or mixture of two or more catalysts, at temperatures ranging from 25° C. to 400° C.
  • the catalyst can be removed preferably by dissolving and removing in deionized water. If catalyst can be removed by treating with deionized water, the reaction mixture is treated with aqueous solutions of acid or base to forms salts and removing the salts either by washing or filtering.
  • the catalyst can be an acid for non-limiting examples, sulfuric acid, or p-toluene sulfonic acid.
  • the catalyst can also be a base, for non-limiting example, sodium hydroxide.
  • the catalyst can also be a salt, for non-limiting example, potassium acetate.
  • the catalyst can also be an alkoxide , for non-limiting example, titanium tetraisopropoxide.
  • the catalyst can also be a heterogeneous catalyst, for non-limiting examples: zeolite, heteropolyacid, amberlyst, or ion exchange resin.
  • the catalyst can also be a metal salt, for non-limiting examples, tin chloride, or copper chloride,
  • the catalyst can also be an enzyme, such as those known in the art.
  • the catalyst can also be an organic acid, for a non-limiting example, formic acid.
  • the catalyst can also be an organometalic compound, for non-limiting example, n-butylstannoic acid.
  • This process can be carried out in the presence or absence of a solvent. If a solvent is not necessary to facilitate the production of fatty ester, it is preferred that the process is carried out in the absence of solvent.
  • the process can be carried out at atmospheric pressure or under vacuum or under pressurized conditions.
  • R1 and R2 is a hydrocarbon, preferably with a carbon chain length of about 1 to about 40.
  • Such hydrocarbons can be saturated or unsaturated, substituted or unsubstituted, linear or branched
  • M is hydrogen, an alkali metal or an alkyl group.
  • R1 is a hydrocarbon, preferably with a carbon chain length of about 1 to about 40.
  • Such hydrocarbons can be saturated or unsaturated, substituted or unsubstituted, linear or branched.
  • M is hydrogen, an alkali metal or an alkyl group.
  • compositions in accordance with the invention comprise esters in which R1 has one or more functional groups selected from the group consisting of alkene, amide, amine, carbonyl, carboxylic acid, halide, hydroxyl groups, ether, alkyl ether, sulfate and ethersulfate.
  • the esters can have the formula R1-C( ⁇ O)—O—CH2—CH2—CH2—O—C( ⁇ O)—R2, wherein both R1 and R2 are linear or branched carbon chains of a length between about 1 an about 40 carbons.
  • R1 and R2 can have one or more functional groups selected from the group consisting of alkene, amide, amine, carbonyl, carboxylic acid, halide, hydroxyl groups, ether, alkyl ether, sulfate and ethersulfate. Additionally, R1 and R2 can be the same carbon chain in the case of a diester.
  • any molar ratio of diol to dicarboxylic acid or its salt or its ester can be used.
  • the preferred range of the diol to dicarboxylic acid is from about 1:3 to about 2:1. This ratio can be adjusted to shift the favor of the reaction from monoester production to diester production. Generally, to favor the production of diesters slightly more than about a 1:2 ratio is used; whereas to favor the production of monoesters about a 1:1 ratio is used.
  • the ratio of diol to dicarboxylic acid can range from about 1.01:2 to about 1.1:2; however if the monoester is desired a range of ratios from about 1.01:1 to about 2:1 is used.
  • the catalyst content for the reaction can be from ippm to 60 wt % of the reaction mixture, preferably from 10 ppm to 10 wt %, more preferably from 50 ppm to 2 wt % of the reaction mixture.
  • the product may contain diesters, monoesters or combination diesters and monoesters and small percentage of unreacted acid and diol depending on the reaction conditions. Unreacted diol can be removed by washing with deionized water. Unreacted acid can be removed by washing with deionized water or aqueous solutions having base or during recrystallization.
  • Any ester of 1,3-propanediol can be made or used in accordance with the the present invention.
  • Short, middle and long chain monoesters and diesters of the 1,3-propanediol can be made. Specifically those acids containing between about 1 and about 36 carbons in the alkyl chain can be produced.
  • the following monoesters and diesters can be produced: propanediol distearate (monostearate and the mixture), propandiol dilaurate (monolaurate and the mixture), propanediol dioleate (monooleate and the mixture), propanediol divalerate (monovalerate and the mixture), propanediol dicaprylate (monocaprylate and the mixture), propanediol dimyristate (monomyristate and the mixture), propanediol dipalmitate (monopalmitate and the mixture), propanediol dibehenate (monobehenate and the mixture), propanediol adipate, propanediol maleate, propanediol dibenzoate, and propanediol diacetate.
  • compositions comprising an ester of 1,3-propanediol, wherein the 1,3-propanediol is biologically derived contain biobased carbon from the biologically derived 1,3 -propanediol. Accordingly, these esters can have varying amounts of biobased carbon, depending on what acids are used in the esterification process.
  • compositions can include esters that have at least 1% biobased carbon, at least 3% biobased carbon, at least 6% biobased carbon, at least 10% biobased carbon, at least 25% biobased carbon, at least 50% biobased carbon, at least 75% biobased carbon, or 100% biobased carbon depending on the length of the carbon chain of the organic acid used to produce the ester, whether the ester is a diester or a monoester, and whether the organic acid contained biobased carbon or fossil-fuel based carbon.
  • compositions comprising an ester of 1,3-propanediol can be produced by providing biologically produced 1,3-propanediol; contacting the 1,3-propanediol with an organic acid, wherein the ester is produced; and recovering the ester.
  • the 1,3-propanediol provided can have at least 90% biobased carbon, at least 95% biobased carbon, or 100% biobased carbon.
  • the biologically-produced 1,3-propanediol provided for the process can have at least one of the following characteristics: 1) an ultraviolet absorption of less than about 0.200 at 220 nm and less than about 0.075 at 250 nm and less than about 0.075 at 275 nm; 2) a composition having L*a*b* “b*” color value of less than about 0.15 and an absorbance of less than about 0.075 at 270 nm; 3) a peroxide composition of less than about 10 ppm; and 4) a concentration of total organic impurities of less than about 400 ppm.
  • the ester can also be produced by providing 1,3-propanediol with at least 90% biobased carbon; contacting the 1,3-propanediol with an acid, forming the ester; and recovering the ester.
  • the contacting of the 1,3-propanediol with an acid can be done in the presence of a catalyst to facilitate the esterification reaction, and the catalyst can be categorized as a member of one or more of the acids, bases, salts, alkoxides, heterogeneous, catalysts, metal salts, enzymes, organic acids, and organometalic compounds.
  • the catalyst can be sulfuric acid, or p-toluene sulfonic acid, sodium hydroxide, potassium acetate, titanium tetraisopropoxide, zeolite, heteropolyacid, amberlyst, ion exchange resin, tin chloride, or copper chloride, formic acid, or n-butylstannoic acid.
  • the monoesters and diesters of bio-derived 1,3-propanediol are useful in a variety of applications.
  • the esters are suitable for use as an emulisifer, a pearlizing agent, a surfactant, a gelling agent, a structurant, a thickener, an opacifier, an emollient, an additive, an adjuvant, a humectant, a compatibilizer, and a solvent for cosmetics and personal care products.
  • esters are also useful as a solvent for botanical products.
  • botanical products include, but are not limited to, all plants, their seeds, stems, roots, flowers, leaves, pollen, spices, oils and botanical extracts generally.
  • the esters can be used to incorporate the botanicals into personal care and cosmetic products.
  • Esters as described herein can also be used in inks as an emulsifier in cosmetic inks like tattoos or henna dyes.
  • Such esters are useful in preparation of solid or near solid personal care products such as stick deodorants, bronzing sticks, and lipsticks.
  • a personal care composition comprising an ester of 1,3-propanediol and an acceptable carrier. While the personal care compositions can include synthetic materials, they are the 1,3 propanediol esters derived from biologically-derived 1,3-propanediol are compatible with natural ingredients, or essentially natural ingredients in forming natural personal care products.
  • compositions include formulations for skin care, skin cleansing, make-up, facial lotion, moisturizer, body wash, body lotion, foot care formulation, hand cream, lipstick, lip gloss, lip pencil, eye shadow, gel eye color, eye liner, eye pencil, mascara, concealer, foundation, facial powder, liquid rouges, blush, deodorant, antiperspirant, shaving cream, shaving lotion, nail polish, gel polish removers, cuticle remover, cuticle cream, acne cream, acne cleansing scrub, toothpaste, depilatory formulation, facial mask, anti-aging formulation, shampoo, hair conditioner, hair treatment formulation, hair reconstructioner, styling gel, styling foam, hair mousse, hair spray, hair set lotion, blow-styling lotion, hair color lotion and dyes, hair bleaching cream, hair relaxing, curl activator, fragrant hair gloss, sun care formulations like sun stick and sun screen, sunless tanner, bronzing stick, soap, hand sanitizer, antibacterial hand cleaner, body scrub, hand scrub, bubble bath, bath oils, baby lotion, diaper rash cream, wet wipe, baby
  • ingredients for the personal care compositions of the invention include, among others: conditioning agents, moisturizing agents, emollients, astringents, antiperspirant compounds, biocidal compounds, sunscreens, UV absorbers, pigments, fragrances, actives, anti-aging agents, enzymes, proteins, vitamins, or mixtures thereof.
  • compositions of the present invention preferably comprise a safe and effective amount of a cosmetically 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.
  • a cosmetically 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 personal care compositions depends on the types of product form desired for the composition.
  • the topical compositions can 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 personal care compositions can have between about 0.5% and about 2% weight ester, between about 2% and about 5% weight ester, between about 5% and about 10% weight ester, between about 10% and about 20% weight ester, between about 20% and about 50% weight ester, or between about 50% and about 80% weight ester, depending on the formulation used.
  • the personal care compositions can include a glycol component.
  • the glycol component can be 1,3-propanediol.
  • 1,3 propanediol is used as the glycol component, it will be biologically-derived 1,3-propanediol.
  • This biologically-derived 1,3-propanediol can have at least 90% biobased carbon content.
  • the 1,3-propanediol has at least 95% biobased carbon content, and more preferably has 100% biobased carbon content.
  • the personal care compositions can be intended for grooming mammals or avians. More specifically, the personal care compositions can be intended for grooming humans, canines, felines, or equines.
  • a process for producing a personal care composition with an ester of 1,3-propanediol and an acceptable carrier includes providing biologically produced 1,3-propanediol and contacting the 1,3-propanediol with an organic acid. This produces the ester.
  • the process includes recovering the ester and incorporating the ester into a personal care formulation.
  • a process for producing a personal care composition includes providing an ester of 1,3-propanediol and incorporating the ester into a personal care formulation.
  • the personal care compositions preferably include a safe and effective amount of a dermatologically or cosmetically 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.
  • a dermatologically or cosmetically 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 used in the personal care compositions 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.
  • Esters of 1,3 propanediol can be present in the aforementioned personal care and cosmetics compositions in varying amounts depending on the type of formulation.
  • Baby products such as, for example, baby shampoos, soaps, wipes, lotions, oils, powders, and creams, can have a 1,3 propanediol ester concentration ranging between about 0.1% to about 25% by weight, and preferably between about 1% to about 10% by weight, and more preferably 1 to 5%.
  • Bath preparations such as, for example, bath oils, tablets, and salts; bubble baths and bath capsules, can have a 1,3 propanediol ester concentration ranging between about 0.001% to about 50%, and preferably from about 0.1% to about 10%, and 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, can have a 1,3 propanediol ester concentration ranging between about 0.001% to about 75%, preferably 0.01% to about 25%, and 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, can have a 1,3 propanediol ester concentration ranging between about 0.001% to about 99%, preferably from about 0.01% to about 10%, and 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, can have a 1,3 propanediol ester concentration ranging between about 0.001% to about 90%, preferably from about 0.01% to about 50%, and 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, can have a 1,3 propanediol ester concentration ranging between about 0.001% to about 50%, preferably from about 0.1% to about 25%, and more preferably, from about 1% to about 10%.
  • Makeup preparations can have a 1,3 propanediol ester concentration ranging between about 0.001% to about 99%, preferably from about 0.01% to about 25%, and 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, can have a 1,3 propanediol ester concentration ranging between about 0.001% to about 50%, preferably from about 0.1% to about 10%, and 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), can have a 1,3 propanediol ester concentration ranging between about 0.001% to about 80%, and more preferably from about 1% to about 5%.
  • Personal cleanliness products such as, for example, bath soaps and detergents; deodorants (underarm); antiperspirants; douches; and feminine hygiene deodorants, can have a 1,3 propanediol ester concentration ranging between about 0.001% to about 99%, preferably from about 0.01% to about 50%, and 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.), shaving lotion, can have a 1,3 propanediol ester concentration ranging between about 0.001% to about 50%, preferably from about 0.01% to about 10%, and more preferably from about 0.1% to about 5%.
  • Skin care preparations can have a 1,3 propanediol ester concentration ranging between about 0.001% to about 50%, preferably from about 0.01% to about 15%, and 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; can have a 1,3 propanediol ester concentration ranging between about 0.001% to about 75%, and preferably from about 1% to about 25%, and more preferably from about 1% to about 10%.
  • Preservatives can have a 1,3 propanediol ester concentration ranging between about 0.001% to about 100%, and more preferably from about 95% to about 99.99%.
  • 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.
  • Glycerol used in the production of 1,3-propanediol was obtained from J. T. Baker Glycerin USP grade, Lot J25608 and G19657.
  • NMR 1H NMR spectra were recorded on Bruker DRX 500 using XWINNMR version 3.5 software. Data was acquired using a 90 degree pulse (p1) and a 30 second recycle delay (d1). Samples were dissolved in deuterated chloroform and nondeuterated chloroform was used as internal standard.
  • glycerol The conversion of glycerol to bio-PDO was monitored by HPLC. Analyses were performed using standard techniques and materials available to one of skill in the art of chromatography. One suitable method utilized a Waters Maxima 820 HPLC system using UV (210 nm) and RI detection. Samples were injected onto a Shodex SH-1011 column (8 mm ⁇ 300 mm, purchased from Waters, Milford, Mass.) equipped with a Shodex SH-1011P precolumn (6 mm ⁇ 50 mm), temperature controlled at 50° C., using 0.01 N H2SO4 as mobile phase at a flow rate of 0.5 mL/min. When quantitative analysis was desired, samples were prepared with a known amount of trimethylacetic acid as external standard. Typically, the retention times of glycerol (RI detection), 1,3-propanediol (RI detection), and trimethylacetic acid (UV and RI detection) were 20.67 min, 26.08 min, and 35.03 min, respectively.
  • Monoesters and diester of bio-produced 3-propandiol may be produced by combining bio-PDO with organic acid. The combination is to be preformed in dry conditions under heat and prolong agitation with a selected catalyst. The ratio of monoester to diester produced will vary according to the molar ratio of acid to bio-PDO and the selection of catalyst.
  • esters was confirmed using 1 H nuclear magnetic resonance. Analyses were performed using standard techniques and materials available to one of skill in the art of 1 H NMR.
  • Proton Nuclear Magnetic Resonance ( 1 H NMR) Spectroscopy is a powerful method used in the determination of the structure of unknown organic compounds. It provides information concerning: the number of different types of hydrogens present in the molecule, the electronic environment of the different types of hydrogens and the number of hydrogen “neighbor” a hydrogen has.
  • the hydrogens bound to carbons attached to electron withdrawing groups tend to resonate at higher frequencies from TMS, tetramethylsilane, a common NMR standard.
  • the position of where a particular hydrogen atom resonates relative to TMS is called its chemical shift ( ⁇ ).
  • Typical chemicals shifts of fatty ester are as follows.
  • % ⁇ ⁇ Esterification Combined ⁇ ⁇ areas ⁇ ⁇ of ⁇ ⁇ peaks ⁇ ⁇ at ⁇ ⁇ 41.5 ⁇ ⁇ and ⁇ ⁇ 4.24 ⁇ 100 Combined ⁇ ⁇ areas ⁇ ⁇ of ⁇ ⁇ peaks ⁇ ⁇ at ⁇ ⁇ 3.70 , 41.5 ⁇ ⁇ and ⁇ ⁇ 4.24
  • E. coli strain ECL707 containing the K. pneumoniae dha regulon cosmids pKP1 or pKP2, the K. pneumoniae pdu operon pKP4, or the Supercos vector alone, is grown in a 5 L Applikon fermenter for the production of 1,3-propanediol from glucose.
  • the medium used contains 50-100 mM potassium phosphate buffer, pH 7.5, 40 mM (NH4)2SO4, 0.1% (w/v) yeast extract, 10 ⁇ M CoCl2, 6.5 ⁇ M CuCl2, 100 ⁇ M FeCl3, 18 ⁇ ⁇ M FeSO4, 5 ⁇ M H3BO3, 50 ⁇ M MnCl2, 0.1 ⁇ M Na2MoO4, 25 ⁇ M ZnCl2, 0.82 mM MgSO4, 0.9 mM CaCl2, and 10-20 g/L glucose. Additional glucose is fed, with residual glucose maintained in excess. Temperature is controlled at 37° C. and pH controlled at 7.5 with 5N KOH or NaOH. Appropriate antibiotics are included for plasmid maintenance. For anaerobic fermentations, 0.1 vvm nitrogen is sparged through the reactor; when the dO setpoint was 5%, 1 vvm air is sparged through the reactor and the medium is supplemented with vitamin B12.
  • Titers of 1,3-propanediol range from 8.1 to 10.9. Yields of bio-PDO (g/g) range from 4% to 17%.
  • 1,3-propanediol produced as recited in Example 1, was purified, by a multistep process including broth clarification, rotary evaporation, anion exchange and multiple distillation of the supernatant.
  • the broth was clarified using a combination of centrifugation and membrane filtration for cell separation, followed by ultrafiltration through a 1000 MW membrane.
  • the clarified broth processed in a large rotary evaporator. Approximately 46 pounds of feed material (21,000 grams) were processed to a concentrated syrup. A 60 ml portion of syrup was placed in the still pot of a 1′′ diameter distillation column. Distillation was conducted at a vacuum of 25 inches of mercury. A reflux ratio of approximately 1 was used throughout the distillation. Several distillate cuts were taken, the central of which received further processing.
  • the material was diluted with an equal volume of water, the material was loaded onto an anion exchange column (mixed bed, 80 grams of NM-60 resin), which had been water-washed.
  • bio-source 1,3-propanediol was purified using methods as in examples 1 and 2.
  • 2.58 g (0.033 moles) of biologically-derived 1,3-propanediol, 19.45 g (0.065 moles) of stearic acid (Aldrich, 95%), and 0.2125 g (0.001 moles) of p-toluenesulfonic acid (Aldrich 98.5%) were charged into glass reactor fitted with mechanical stirrer and the reactor was flushed with dry nitrogen gas to remove air and moisture for 15 min. Then reaction temperature was raised to 100° C. while thoroughly stirring the reaction mixture under nitrogen flow and continued for 210 min.
  • reaction mixture was cooled to about 35° C. and the product was transferred into a beaker.
  • the product was purified by adding 100 mL of water and thoroughly stirring at 45-60° C., to form an emulsion for 15 min. The mixture was cooled and the solid propanediol distearate was separated by filtration.
  • Bio-source 1,3-propanediol was prepared as described herein, specifically as described in Examples 1 and 2.
  • 5.2 g (0.068 moles) of biologically-derived 1,3-propanediol, 38.9 g (0.13 moles) of stearic acid (Aldrich, 95%), and 0.425 g (0.002 moles) of p-toluenesulfonic acid (Aldrich, 98.5%) were charged into glass reactor fitted with mechanical stirrer and the reactor was flushed with dry nitrogen gas to remove air and moisture for 15 min. Then reaction temperature was raised to 130° C. while thoroughly stirring the reaction mixture under nitrogen flow and continued for 195 min at 130° C.
  • the product was purified as described in Example 3.
  • the product was further purified by dissolving in chloroform and recrystallizing by adding acetone at 15° C.
  • the recrystallized product was filtered and dried.
  • reaction mixture was cooled and analyzed by NMR.
  • the product contained 39 mole % of propanediol monostearate , 19 mole % of propanediol distearate and 42 mole % 1,3-propanediol.
  • FIG. 5 depicts a graph of these data.
  • the product has 36 mole % propanediol monostearate and 64 mole % propanediol distearate.
  • reaction temperature was raised to 130° C. while thoroughly stirring the reaction mixture under nitrogen flow.
  • the reaction was continued for 4 h under nitrogen flow.
  • the nitrogen flow was shut off and vacuum was applied for 10 min before stopping the reaction.
  • the obtained product was analyzed without further purification.
  • NMR analysis confirmed the product contained 64.7 mole % of propanediol monostearate , 9.7% mole % of Propanediol distearate and 25.6 mole % 1, 3 Propanediol.
  • FIG. 7 depicts a graph of these data.
  • reaction temperature was raised to 130° C. while thoroughly stirring the reaction mixture under nitrogen flow.
  • the reaction was continued for 4 h under nitrogen flow.
  • the product was cooled and 90 mL of 0.5 wt % sodium hydroxide solution was added and agitated at 40 to 50° C. for 10 min. Then the product was filtered and thoroughly washed with deionized water and dried.
  • reaction temperature was raised to 130° C. while thoroughly stirring the reaction mixture under nitrogen flow.
  • the reaction was continued for 4 h under nitrogen flow.
  • the product was cooled and 90 mL of 0.5 wt % sodium hydroxide solution was added and agitated at 40 to 50° C. for 10 min.
  • the mixture was transferred into a separating funnel and 500 mL of deionized water added and mixture was allowed to form tow separate layers. Aqueous layer was removed.
  • liquid powder can be prepared using bio-based propanediol caprylate.
  • phase A add inulin lauryl ca rbamate to water and disperse CARBOPOL ULTREZ 10 (B. F. Goodrich Company, New York, N.Y.). Blend the mixture of phase A ingredients for about 10 minutes, until the carbomer is completely dispersed and hydrated. Under light agitation raise the temperature of the mixture to about 70° C.
  • phase B in the amount stipulated by the table, including bio-based propanediol caprylate, and heat to about 75° C.
  • phase B mixture in the amount stipulated by the table, including bio-based propanediol caprylate, and heat to about 75° C.
  • the present invention can be used to prepare a pearlized milk bath using bio-based propanediol distearate. Following the percentages in Table 2, combine UCARE polymer LR-400 with a sufficient amount water to hydrate. Then following the percentage listed in Table 2, blend in PLANTOPON 611 L (Fitz Chem Corporation, Itasca, Ill.) and LAMESOFT PO 65 (Fitz Chem Corporation, Itasca, Ill.) until the mixture reaches uniform consistency.
  • Plantopon 611 L (Sodium laureth sulfate and lauryl glucoside 22.00 and cocamidopropyl betaine)
  • Lamesoft PO 65 (Coco glucoside and glyceryl oleate 3.00 Standamox CAW (Cocamidopropylamine oxide) 3.00 Bio-based propanediol distearate 2.00 Nutrilan Milk (Hydrolyzed milk protein) 1.50 Emery 917 (Glycerin) 0.50 Ucare polymer LR-400 (Amerchol) (polyquaterium-10) 0.10 Water, preservative, fragrance, dye q.s.
  • the present invention can be use in the preparation of a gentle baby shampoo using bio-based propanediol oleate.
  • Tego Betaine L-7 (cocamidopropyl betaine) 18.5 Neosorb 70/20 (sorbitol) 16.9 Plantaren 1200 UP (lauryl glucoside) 15.9 Plantaren 818 UP (coco glucoside) 12.5 Amisoft LS-11 (sodium lauroyl glutamate) 5.0 Bio-based propanediol oleate 2.2 D-panthenol USP (D-panthenol) 1.0 Sensomer CI-50 (Ondeo Nalco) (hydroxypropyltrimonium 0.5 chloride) Crotein HKP Powder (keratin amino acid) 0.4 Fragrance 0.1 Preservative q.s.
  • the present application can be used in the preparation of a moisturizing body wash using bio-based propanediol stearate.
  • a moisturizing body wash start by obtaining the list of ingredients in the proportional amounts listing in Table 4.
  • JORDAPON CI BASF Corporation, Mount Olive, N.J.
  • AVANEL S150 CGN BASF Corporation, Mount Olive, N.J.
  • PEG-150 distearate PEG-150 distearate
  • Cocamidopropyl betaine Cocamidopropyl betaine
  • Cocamide MEA Cocamide MEA
  • bio-based propanediol stearate in approximately half of the total water required for the desired volume.
  • the present invention can be used in the preparation of a deep penetrating hair reconstructor using bio-based propanediol dicaprylate.
  • a hair reconstructor To prepare such a hair reconstructor obtain the ingredients as listed in and in the relative quantities as depicted in Table 5. Then, mix the DEHYQUART L 80 (Cognis GMBH, Dusseldorf, DE) CETIOL CC (Cognis GMBH, Dusseldorf, DE), DC 949 (Dow Corning, Midland Mich.), GLUADIN WLM (Cognis GMBH, Dusseldorf, DE), perfume, and preservative, i.e. all the components of table 5, phase A. Agitate the component of phase A until completely homogeneous.
  • the present invention can be used to prepare a bronzing stick using both bio-based propandiol myristate and bio-based propanediol diprylate.
  • To prepare such a bronzing stick obtain all the ingredients in the proportions indicated in Table 6.
  • phase B mix together the Colorona bronze cosmetic pigment (Rona Cosmetics GmBH, Darmstadt DE), Timiron MP-10 cosmetic pigment (Rona Cosmetics GmBH, Darmstadt DE), Colorona copper cosmetic pigment (Rona Cosmetics GmBH, Darmstadt DE), and Biron LF-2000 cosmetic pigment (Rona Cosmetics GmBH, Darmstadt DE), i.e. all the components of Table 6, phase B.
  • the phase B components have been thoroughly mixed, blend them into the already combined phase A and phase C mixture, while continuing to heat at 85° C. After the phase B mixture has been thoroughly combined with phase A and phase C and homogeny has reached, allow the mixture to cool to between about 70° C. and about 80° C. While the mixture is between about 70° C.
  • Poly(diallyldimethylammonium chloride), 20 wt % in water was blended with PLANTOPON 611 L, polyglucoside, bio-based 1,3-propanediol oleate and cocamide DMA in the proportional amounts listed in Table until the mixture reaches uniform consistency. Then glycerin, milk protein , bio-based 1,3-propanediol oleate, bio-based 1,3-propanediol distearate were added and mixed well until the mixture is again of uniform consistency. Measure the pH and if necessary adjust with citric acid to reach a final pH of between about 6 to about 7. Finally add preservative, dye, fragrance and enough water to reach the desired volume.
  • the final viscosity of the mixture should be between about 5,000 cPs to about 10,000 cPs.
  • Blend 213 1 47.0 Sodium Laureth Sulfate Cocamidopropyl Betaine Cocamide DEA PEG-150 Distearate Cocamidopropyl Betaine 1 4.0 Cocamide DEA 1 3.0 bio-based 1,3-propanediol distearate 2.0 Poly(diallyldimethylammonium chloride), (20 wt % in water) 4 5.0 Polysorbate-60 2 2.0 Panthenol 0.5 Vitamin E acetate 0.1 Disodium EDTA 0.5 Preservative 0.5 D.I Water, Fragrance q.s. 1 The Chemistry Store.com, Cayce, SC 2 Somerset Cosmetic Co. LLC, Renton, WA 3 Fitz Chem Corporation, Itasca, IL 4 Sigma-Aldrich, Milwaukee, WI
  • Phase A Mix the ingredients of Phase A. Heat the mixture to about 70° C. under continuous agitation. Maintain 70° C. until the mixture has reached homogeneous.
  • phase A mixture In a separate container, mix together the TiO 2 , and pigment(s) and blend them into the phase A mixture, while continuing to heat at 70° C. After the phase B mixture has been thoroughly combined with phase A and homogeny has reached, allow the mixture to cool to about 50° C., pour the mixture into molds to create sticks. Allow the mixture to fully cool to room temperature before removing the formed sticks from the molds.
  • Biologically-derived 1,3-propanediol 1.0 Water 44.5 Bio-based 1,3-propanediol stearate 0.5 Irgasan 6 0.2 Tetrasodium EDTA (5 wt %) 2.0 Citric acid (50 wt %) QS Fragrance 0.2 1 DuPont Tate & Lyle Bio Products 2 The Chemistry Store.com, Cayce, SC 3 Somerset Cosmetic Co. LLC, Renton, WA 4 Stephan Co. Northfield, IL 5 Noveon, Cleveland, OH 6 Sigma-Aldrich, Milwaukee, WI
  • phase A Combine components of phase A mix and heat to 75° C.
  • phase B Combine phase B with phase A. Cool it to 45° C.
  • Add components of phase C Mix it thoroughly.
  • Add components of phase D and E. Mix it until viscosity developed.
  • EXAMPLE 23 Skin Cream Ingredients Wt % Water 73.3 Stearic Acid 15.0 Petroleum jelly 2.0 Biologically-derived 1,3-propanediol 5.00 Bio-based 1,3-propanediol monoisostearate 3.0 Polyoxyethylene cetyl ether 1.0 Perfume q.s.

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US77219406P 2006-02-10 2006-02-10
US77211206P 2006-02-10 2006-02-10
US77211106P 2006-02-10 2006-02-10
US84694806P 2006-09-25 2006-09-25
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US11/705,227 Abandoned US20070202073A1 (en) 2006-02-10 2007-02-12 Personal care and cosmetics compositions comprising biologically-based mono and di esters
US11/705,198 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
US11/705,276 Abandoned US20070207940A1 (en) 2006-02-10 2007-02-12 Detergent 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
US11/705,346 Abandoned US20070207113A1 (en) 2006-02-10 2007-02-12 Personal care and cosmetic compositions comprising renewably-based, biodegradable 1,3-propanediol
US11/705,275 Abandoned US20070200087A1 (en) 2006-02-10 2007-02-12 Deicing and anti-icing compositions comprising renewably-based, biodegradable 1,3-propanediol
US11/705,212 Active 2029-08-26 US7988883B2 (en) 2006-02-10 2007-02-12 Heat transfer compositions comprising renewably-based biodegradable 1,3-propanediol
US11/705,342 Abandoned US20070203323A1 (en) 2006-02-10 2007-02-12 Food compositions comprising biologically-based biodegradable 1,3-propanediol esters
US11/705,254 Abandoned US20070241306A1 (en) 2006-02-10 2007-02-12 Biodegradable 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
US11/705,262 Abandoned US20070202062A1 (en) 2006-02-10 2007-02-12 Natural deodorant 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
US11/705,245 Active 2029-09-04 US7960575B2 (en) 2006-02-10 2007-02-12 Synthesis of mono and di esters from biologically-produced 1,3-propanediol
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
US13/834,000 Active US8598231B2 (en) 2006-02-10 2013-03-15 Flavoring agents containing bio-derived 1,3-propanediol and its conjugate esters
US13/833,539 Active US8802729B2 (en) 2006-02-10 2013-03-15 Enzyme stabilized detergent compositions
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
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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
US11/705,276 Abandoned US20070207940A1 (en) 2006-02-10 2007-02-12 Detergent 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
US11/705,346 Abandoned US20070207113A1 (en) 2006-02-10 2007-02-12 Personal care and cosmetic compositions comprising renewably-based, biodegradable 1,3-propanediol
US11/705,275 Abandoned US20070200087A1 (en) 2006-02-10 2007-02-12 Deicing and anti-icing compositions comprising renewably-based, biodegradable 1,3-propanediol
US11/705,212 Active 2029-08-26 US7988883B2 (en) 2006-02-10 2007-02-12 Heat transfer compositions comprising renewably-based biodegradable 1,3-propanediol
US11/705,342 Abandoned US20070203323A1 (en) 2006-02-10 2007-02-12 Food compositions comprising biologically-based biodegradable 1,3-propanediol esters
US11/705,254 Abandoned US20070241306A1 (en) 2006-02-10 2007-02-12 Biodegradable 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
US11/705,262 Abandoned US20070202062A1 (en) 2006-02-10 2007-02-12 Natural deodorant 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
US11/705,245 Active 2029-09-04 US7960575B2 (en) 2006-02-10 2007-02-12 Synthesis of mono and di esters from biologically-produced 1,3-propanediol
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
US13/834,000 Active US8598231B2 (en) 2006-02-10 2013-03-15 Flavoring agents containing bio-derived 1,3-propanediol and its conjugate esters
US13/833,539 Active US8802729B2 (en) 2006-02-10 2013-03-15 Enzyme stabilized detergent compositions
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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