US20070213247A1 - Detergent and liquid soap compositions comprising biologically-based mono and di esters - Google Patents

Detergent and liquid soap compositions comprising biologically-based mono and di esters Download PDF

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Publication number
US20070213247A1
US20070213247A1 US11/705,312 US70531207A US2007213247A1 US 20070213247 A1 US20070213247 A1 US 20070213247A1 US 70531207 A US70531207 A US 70531207A US 2007213247 A1 US2007213247 A1 US 2007213247A1
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Prior art keywords
propanediol
detergent
detergent composition
ester
acid
Prior art date
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Abandoned
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US11/705,312
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English (en)
Inventor
Gyorgyi Fenyvesi
Raja Hari Poladi
Ann Wehner
Robert Miller
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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=US20070213247(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 US11/705,312 priority Critical patent/US20070213247A1/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, MILLER, ROBERT, WEHNER, ANN, POLADI, RAJA HARI PRASAD R.
Publication of US20070213247A1 publication Critical patent/US20070213247A1/en
Priority to US12/554,056 priority patent/US20090325853A1/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

  • This invention relates to detergent compositions comprising conjugate esters of 1,3-propanediol. Specifically, the invention relates to detergent compositions comprising conjugate esters of biologically-derived 1,3-propanediol.
  • 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.
  • a detergent composition comprising a 1,3-propanediol ester and a hydrotrope is provided.
  • the detergent composition can further comprise a surfactant, or a glycol component.
  • Detergent compositions comprising a glycol component can have 1,3-propanediol as the glycol component.
  • Also provided is a process for producing a detergent composition comprising an ester of 1,3-propanediol, and the 1,3-propanediol is biologically-derived.
  • the process comprises providing 1,3-propanediol with at least 90% biobased carbon, contacting the 1,3-propanediol with an organic acid, forming the ester, recovering the ester, and incorporating the ester into a detergent 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.
  • Figure is diagram of nuclear magnetic resonance spectra of the products obtained in example 6.
  • 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 the composition of liquid soaps and liquid detergents as emulisifers, pearlizing agents, surfactants, gelling agents, structurant, thickener, or opacifiers.
  • the esters described herein are especially desirable as components of detergent formulations as they provide the intended functionality and can be produced from a biologically-derived compound.
  • 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, 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, -, 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 4-40 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 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.
  • 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
  • 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%.
  • 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 analyzed 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 bio-PDO 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 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, phthalic, sebacic, archidonic, erucic, palmitoleic, pentadecanoic, heptadecanoic, nondecanoic, octadectetraenoic, eicosatetraenoic, eicosapentaenoic, docasapentaenoic, tetracosapentaenoic, tetrahexaenoic, docosahexenoic, (alpha)-linolenic, docosahexaenoic, eicosapentaenoic, linoleic, arachidonic, oleic, erucic,
  • 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, propanediol diphthalate and monophthalate, 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, branched, cyclic or aromatic.
  • M is hydrogen, an alkali metal or an alkyl group.
  • R1 is a hydrocarbon, preferably with a carbon number of about 1 to about 40.
  • Such hydrocarbons can be saturated or unsaturated, substituted or unsubstituted, linear, branched, cyclic or aromatic.
  • 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 number between about 1 an about 40.
  • 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 carboxylic acid or its salt or its ester can be used.
  • the preferred range of the diol to carboxylic 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 1 ppm 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 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 detergent compositions according to the invention comprise a 1,3-propanediol ester and a hydrotrope.
  • the compositions can further comprise a surfactant.
  • the detergent compositions include a glycol component, and the glycol component can be 1,3-propanediol, among others.
  • the detergent compositions can also include water.
  • the 1,3 propanediol can be biologically produced through a fermentation process.
  • the 1,3-propanediol can have at least 90% biobased carbon, at least 95% biobased carbon, or 100% biobased carbon.
  • the 1,3-propanediol esters in the detergent compositions can have 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, or 100% biobased carbon.
  • the detergent compositions can include between about 0.1% to about 50% 1,3 propanediol ester. In other embodiments, the compositions can have between about 0.1% to about 15% 1,3 propanediol ester, between about 0.3% to about 5% 1,3 propanediol ester, between about 5% to about 30% 1,3 propanediol ester, between about 30% to about 60% 1,3 propanediol ester, or between about 60% to about 80% 1,3 propanediol ester.
  • the 1,3 propanediol esters can be included in detergent compositions for a variety of purposes. These esters operate as hydrotropes, staibilizers, builders, emulisifers, conditioners, pearlizing agents, surfactants, gelling agents, structurants, thickeners, and opacifiers, depending on the specific formulation.
  • diamines which are useful in improving cleaning performance; surfactants, which improve cleaning performance; glycols, which enhance physical and enzymatic stability; hydrotropes, which serve as phase stabilizers; suds stabilizers, which extend suds volume and duration; builders, which support detergent action; enzymes, which improve cleaning performance; buffers, which serve to adjust the pH; alkali inorganic salts, which support detergent action; perfumes, which remove iron and manganese.
  • Some appropriate detergent compositions include liquid soaps, liquid detergents, household cleaning products, and industrial cleaning products.
  • Some specific detergents that are appropriate for use with 1,3-propanediol esters include hand dish-washing detergents, machine dish-washing detergents, solid block detergents, solid laundry detergents, liquid laundry detergents, light-duty liquid detergents, heavy-duty liquid detergents, organic or inorganic clothing softeners, laundry bar soaps, and car wash detergents.
  • Also provided is a process for producing a detergent composition comprising an ester of 1,3-propanediol, where the 1,3-propanediol is biologically-derived.
  • This process includes: providing 1,3-propanediol with at least 90% biobased carbon and contacting the 1,3-propanediol with an organic acid, which forms the ester. The ester is then recovered and incorporated into a detergent composition.
  • the detergent compositions containing esters of 1,3-propanediol can take a variety of physical forms including granular, gel, tablet, bar and liquid forms. These compositions include a so-called concentrated granular detergent composition adapted to be added to a washing machine by means of a dispensing device placed in the machine drum with the soiled fabric load.
  • Exemplary detergents include, but are not limited to, hand dish-washing detergents; machine dish-washing detergents, including solid block detergents; solid laundry detergents, liquid laundry including light-duty liquid detergents (LDLD) and heavy-duty liquid detergents (HDLD); organic or inorganic clothing softeners, laundry bar soaps and car wash detergent, among others.
  • hand dish-washing detergents including solid block detergents; solid laundry detergents, liquid laundry including light-duty liquid detergents (LDLD) and heavy-duty liquid detergents (HDLD); organic or inorganic clothing softeners, laundry bar soaps and car wash detergent, among others.
  • machine dish-washing detergents including solid block detergents
  • solid laundry detergents liquid laundry including light-duty liquid detergents (LDLD) and heavy-duty liquid detergents (HDLD)
  • LDLD light-duty liquid detergents
  • HDLD heavy-duty liquid detergents
  • organic or inorganic clothing softeners laundry bar soaps and car wash detergent, among others.
  • the detergent compositions of the invention can comprise any form known or used in the art, such as powders, liquids, granules, gels, pastes, tablets, small bags, bars, and double-partitioned containers, sprays or foamed detergents and other homogenous or multi-phase daily detergent product forms.
  • the products can be manually used or coated, and/or can be used in a constant or freely variable amount of use, or by automatic charge means, or can be used in electric products such as washing machines.
  • These products can have a wide range of pH of, e.g., from 2 to 12 or more, and several tens gram-equivalent, per 100 g of the formulation, of NaOH may be added.
  • These products can have a wide range of preliminary alkalinity. Both high suds and low suds detergents are included.
  • Light-Duty Liquid Detergents include LDLD compositions containing magnesium ions for improving surface activity and/or organic diamines and/or various foam stabilizers and/or suds boosters, such as amine oxides and/or skin feeling improvers of surfactant and relaxing agents and/or enzyme types including protease, and/or sterilizers.
  • Heavy-Duty Liquid Detergents compositions include all of so-called “structured” or multi-phase and “non-structured” or isotropic liquid types, and generally include aqueous or non-aqueous bleaching agents, and/or enzymes, or do not include bleaching agents and/or enzymes.
  • Heavy-duty granular detergents compositions include both of a so-called “compact” or coagulated, or non-spray dried type and a so-called “flocculated” or spray dried type. These compositions include both of a phosphate addition type and a phosphate non-addition type.
  • Such detergents can include a type comprising a more general anionic surfactant as a substrate, or may be a so-called “highly nonionic surfactant” type comprising a generally nonionic surfactant held on an absorbent, for example, in or on the surface of a zeolites or other porous inorganic salt.
  • Softener (STW) compositions include various types of granular or liquid products that are softened by laundry, and can generally include organic (such as quaternary) or inorganic (such as clay) softeners.
  • Bar Soap (BS & HW) compositions include laundry bars and include both of a type comprising a synthetic detergent and a soap as substrates and a type containing a softener.
  • Such compositions include compositions manufactured by general soap manufacture techniques, such as pressure molding, or techniques that are no so general, such as casting and absorption of surfactant into a porous support.
  • Other hand wash detergents are also included.
  • Fabric softeners include both of the conventional liquid and concentrated liquid types and kinds to be added by dryers or supported by a substrate. Other fabric softeners include those that are solid.
  • SPC Special purpose cleaners
  • detergents including the following products are also considered detergents for purposes of this invention: house-hold dry detergent modes, pre-treatment products of laundry bleaching agents, pre-treatment products for fabric protection, liquid higher fabric detergent types, especially high suds products, liquid bleaching agents including both of chlorine type and oxygen bleaching agent type, disinfectants, detergent aids, pre-treatment types including, for example, bleaching additives and “stain-stick” or special sudsing type cleaners, and anti-fading treatment by sunlight.
  • SHC Specialty household cleanser
  • SHC Specialty household cleanser
  • All purpose cleansing in the form of creams, gels, liquids, and floor cleaners all-purpose sprays such as for cleaning glass surfaces
  • wipes including all-purpose wipes, glass cleaners, floor cleaners and disinfectants
  • bathroom, shower and toilet cleaners mildew cleaners and bleach.
  • Detergent compositions of the invention can contain from 0.01 to 99% by weight of one or more of any of the following general auxiliary components: builders, surfactants, enzymes, polymers, bleaching agents, bleach surfactants, catalyst components, various active components or special components such as dispersant polymers, color speckles, silver protecting agents, anti-fogging agents and/or corrosion inhibitors, dyes, fillers, sterilizers, alkaline agents, hydrotropic agents, antioxidants, enzyme stabilizers, pro-perfumes, perfumes, plasticizers, carriers, processing aids, pigments, and solvents for liquid formulations.
  • auxiliary components builders, surfactants, enzymes, polymers, bleaching agents, bleach surfactants, catalyst components, various active components or special components such as dispersant polymers, color speckles, silver protecting agents, anti-fogging agents and/or corrosion inhibitors, dyes, fillers, sterilizers, alkaline agents, hydrotropic agents, antioxidants, enzyme stabilizers, pro-perfumes, perfumes,
  • detergent components are included for converting a composition containing only the minimum essential components into a composition useful for the desired detergent purpose. It is recognized that those skilled in the art can readily determine which detergent components are required for desired detergent applications.
  • detergent compositions of the invention may contain any known detergent surfactant, and such surfactants are well known to those having skill in the art.
  • detergent surfactants of the invention can include anionic, nonionic, zwitter-ionic or amphoteric, betaine, and diamine are, surfactants that are known to be useful in detergent applications.
  • the chain length of the hydrophobic moiety is typically in the general range of from C8 to C20, and especially in the case of laundering with cold water, the chain length is often preferably in the range of from C8 to C18.
  • the detergent composition of the invention may use enzymes for various purposes such as removal of protein-based, carbohydrate-based, or triglyceride-based soils from substrates, transfer inhibition of refugee dyes in fabric laundering, and fabric restoration.
  • “Detergent enzymes” as used herein mean all enzymes having advantageous effects in washing, soil removal, and others in laundering.
  • Builder compositions are preferably those that control the hardness of minerals in washing water, especially Ca and/or Mg, thus simplifying the removal and/or dispersal of granular soils from the surface, while also optionally imparting an alkaline agent and/or buffering action.
  • the builder may function as an absorbent for the surfactant.
  • some compositions can be formulated in a completely water-soluble form, which may be either organic or inorganic, depending on the intended utility.
  • Suitable silicate builders include water-soluble types and hydrated solid types, and include other kinds such as those having a chain, layer or steric structure, amorphous solid silicates, and those as prepared such that they are used as not particularly structured liquid detergents.
  • Aluminosilicate builders so-called zeolites, are particularly useful in granular detergents, but can be incorporated into pastes or gels.
  • the aluminosilicates may be crystalline or amorphous, or may be natural or synthetic.
  • the composition of the invention may optionally contain detergent builders in place of or in addition to the foregoing silicates and aluminosilicates.
  • the builders can be made to function in various mechanisms so as to form soluble or insoluble complexes with mineral ions by ion exchange or by providing mineral ions with the surface more adherent than the surface of the material to be cleaned.
  • the amount of the builder can be varied widely depending on the final utility and physical form of the composition.
  • suitable builders can be selected from the group consisting of phosphates and polyphosphates, especially sodium salts, carbonates, bicarbonates, sodium carbonate, organic mono-, di-, tri-, and tetracarboxylates, especially water-soluble non-surfactant carboxylates in acid, sodium, potassium or alkanolammonium forms, and aliphatic and aromatic type-containing oligomers or water-soluble low-molecular polymer carboxylates.
  • these builders can be complemented by all of fillers or carriers that are important in the techniques of detergent compositions including borates or sulfates, especially sodium sulfate, and other stabilized surfactants and/or builders.
  • builder mixtures can be used.
  • the builder mixture optionally comprises two or more usual builders, and is complemented by a chelating agent, a pH buffer, or a filler.
  • phosphorus-containing builders include polyphosphates, represented by tripolyphosphates, pyrophosphates, and glassy polymer metaphosphates, of alkali metals and ammonium and alkanolammoniums, and phosphonates.
  • Suitable carbonate builders include carbonates of an alkaline earth metal or an alkali metal, inclusive of carbonate minerals such as sodium bicarbonate and sodium carbonate, complex salts of sodium carbonate or potassium carbonate, and calcium carbonate.
  • the “organic detergent builders” suitable for the use along with the alkylaryl sulfonate surfactant include polycarboxylate compounds including water-soluble non-surfactant dicarboxylates and tricarboxylates. More generally, the builder polycarboxylate has plural carboxylate groups, preferably at least three carboxylates.
  • the carboxylate builder can be incorporated in an acidic or partially neutral, neutral or excessively basic form. In the case of the salt form, salts of alkali metals such as sodium, potassium, and lithium, or alkanolammonium salts are preferred.
  • the polycarboxylate builder includes ether polycarboxylates.
  • Nitrogen containing builders including amino acids such as lysine, or lower alcohol amines like mono, di-, and tri-ethanolamine, try(hydroxymethyl)amino methane, 2-amino-2-methylpropanol, and disodium glutamate.
  • amino acids such as lysine, or lower alcohol amines like mono, di-, and tri-ethanolamine, try(hydroxymethyl)amino methane, 2-amino-2-methylpropanol, and disodium glutamate.
  • Citric acid salts such as citric acid and soluble salts thereof are a polycarboxylate builder important for, for example, heavy-duty liquid detergents (HDL) because they are available from resources that can be regenerated and are biodegradable.
  • the citric acid salts can also be used in granular compositions especially in combination of zeolites and/or layered silicates. Oxydisuccinic acid salts are especially useful in such compositions and combinations.
  • any builders known in this field can be incorporated generally in an amount of from about 0.1 to about 50% by weight, more preferably 0.5 to 30% by weight and most preferably 1 to 25% by weight.
  • the invention comprises an “oxygen bleaching agent” as a part or whole of the detergent composition.
  • oxygen bleaching agent Any known oxidizing agents can be used.
  • oxidizing agent bleaching agents such as systems of generating hydrogen peroxide by oxygen or an enzyme, or hypohalogenic acid salts, for example, chlorine bleaching agents such as hyposulfites, can also be used.
  • peroxide-based general oxygen bleaching agents include hydrogen peroxide, inorganic peroxohydrates, organic peroxohydrates, and organic peroxy acids including hydrophilic or hydrophobic mono- or di-peroxy acids. These components may be peroxycarboxylic acids, perpoxyimide acids, amidoperoxycarboxylic acids, or salts thereof including their calcium, magnesium or mixed cationic salts.
  • peracids can be used in a liberated form or as precursor materials called “bleach surfactant” or “bleach promoters”, which release peracids corresponding to hydrolysis in the case of a combination with a supply source of hydrogen peroxide.
  • Inorganic peroxides suproxides, organic hydroperoxides such as cumene hydroperoxide and t-butyl hydroperoxide, and inorganic peroxo acids and salts thereof, such as peroxosulfates, are also useful as the oxygen bleaching agent.
  • Mixed oxygen bleaching agent systems are generally effective as in mixtures of oxygen bleaching agents with known bleach surfactant, organic catalysts, enzyme catalysts, or mixtures thereof. Further, these mixtures can further contain brighteners, light bleaching agents, and dye transfer inhibitors of types that are well known in this field.
  • Hydroperoxides and peroxohydrates are organic salts, or more generally, inorganic salts that can readily release hydrogen peroxide.
  • the peroxohydrates are a general example of a “hydrogen peroxide source” and include perborates, percarbonates, perphosphates, and persilicates.
  • Preferred peroxohydrates include all of sodium carbonate hydroperoxide and equivalent commercially available “percarbonate” bleaching agents, and so-called sodium perborate hydrates, and sodium pyrrophosphate hydroperoxide can also be used.
  • Urea hydroperoxides are also useful as the peroxohydrate.
  • inorganic peroxohydrates organic peroxohydrates, hydrophilic or hydrophobic mono- or diperacids, organic peracids including peroxycarboxylic acids, peroxyimide acids, and amidoperoxycarboxylic acids, salts of calcium, magnesium, or mixed cationic salts.
  • any oxygen bleaching agents are added in such formulations preferably in ranges from about 0 to 15%, and most preferably from about 0.2 to 12%
  • Bleach Surfactant can be used as well.
  • useful bleach surfactants include amides, imides, esters, and acid anhydrides. Mixtures of bleach surfactants can be also used.
  • the bleach surfactant can be used in an amount of up to 20% by weight, and preferably from 0.1 to 10% by weight of the composition.
  • Transition Metal Bleaching Agent Catalysts can also be used in the invention.
  • manganese compounds can be optionally used as the bleaching compound to have a catalytic action.
  • cobalt bleaching catalysts ones that are known may be used.
  • suitable hydrogen peroxide generating mechanisms include combinations of C1 to C4 alkanol oxidases and C1 to C4 alkanols, especially a combination of methanol oxidase (MOX) and ethanol.
  • MOX methanol oxidase
  • Bleaching-related other enzymatic materials such as peroxidases, haloperoxidases, and oxidases, superoxide molecular displacement enzymes, catalases, and their reinforcing agents, or more generally, inhibitors can be optionally used in the composition.
  • All known organic bleaching agent catalysts, oxygen transfer agents, or precursors thereof are also useful herein. These materials include their compounds themselves and/or precursors thereof, such as all of ketones suitable for manufacture of dioxiranes, and and/or dioxirane precursors or all different atom-containing analogues of dioxiranes. As preferred examples of such components, are especially included hydrophilic or hydrophobic ketones that manufacture the dioxiranes on the spot, along with monoperoxysulfate.
  • oxygen bleaching agents that are preferably used along with the oxygen transfer agent or precursor include percarboxylic acids and salts, percarbonic acids and slats, peroxy monosulfuric acid and salts, and mixtures thereof.
  • composition of the invention can optionally comprise one or more soil releasing agents.
  • the polymeric soil releasing agent is characterized by having hydrophilic segments to hydrophilize the surface of hydrophobic fibers such as polyester and nylon and hydrophobic segments to deposit upon hydrophobic fibers and remain adhered thereto through completion of the laundry cycle to function as an anchor for the hydrophilic segments. This can enable stains occurring sequent to treatment with the soil releasing agent to be more easily cleaned in later washing procedures.
  • the soil releasing agent generally accounts for from about 0.01 to about 10% by weight of the composition.
  • composition of the invention can also optionally contain water-soluble ethoxylated amines having clay soil removal and anti-redeposition properties.
  • Granular detergent compositions containing these compounds typically contain from about 0.01% to about 10.0% by weight of the water-soluble ethoxylated amines, and liquid detergent compositions typically contain about 0.01% to about 5% by weight of the water-soluble ethoxylated amines.
  • Preferred soil release and anti-redeposition agents are ethoxylated tetraethylenepentamine.
  • Other preferred soil release removal/anti-redeposition agents are ethoxylated amine polymers, zwitter-ionic polymers, and amine oxides.
  • Other soil release removal and/or anti-redeposition agents that are known in this field can also be used in the composition of the invention.
  • Another type of the preferred anti-redeposition agent includes carboxy methyl cellulose (CMC)-based components.
  • Polymeric dispersing agents can be effectively used in an amount of from about 0.01 to about 10% by weight of the composition of the invention especially in the presence of zeolite and/or layered silicate builders.
  • Suitable polymeric dispersing agents include polymeric polycarboxylates and polyethylene glycols, although others known in the art can also be used. It is believed that polymeric dispersing agents enhance overall detergent builder performance, when used in combination with other builders (including lower molecular weight polycarboxylates) by crystal growth inhibition, particulate soil release, peptization, and anti-redeposition.
  • Polymeric polycarboxylate materials can be prepared by polymerizing or copolymerizing suitable unsaturated monomers, preferably in their acid forms.
  • Unsaturated monomeric acids that can be polymerized to form suitable polymeric polycarobyxlates include acrylic acid, maleic acid (or maleic anhydride), fumaric acid, itaconic acid, aconitic acid, mesaconic acid, citraconic acid, and methylenemalonic acid.
  • Polymeric polycarboxylates can be derived from acrylic acid.
  • acrylic acid-based polymers that are useful herein are the water-soluble salts of polymerized acrylic acid.
  • the average molecular weight of such polymers in the acid form range from about 1,000 to 500,000, preferably from about 2,000 to 250,000, and more preferably from about 3,000 to 100,000.
  • Water-soluble salts of such acrylic acid polymers can include, for example, the alkali metal, ammonium and substituted ammonium salts.
  • Acrylic acid/maleic acid-based copolymers may also be used as a preferred component of the dispersing/anti-redeposition agent.
  • Such materials include the water-soluble salts of copolymers of acrylic acid and maleic acid.
  • the average molecular weight of such copolymers in the acid form preferably ranges from about 2,000 to 100,000, more preferably from about 3,000 to 80,000, and most preferably from about 4,000 to 70,000.
  • the ratio of acrylate to maleate segments in such copolymers generally ranges from about 9:1 to about 1:9, and more preferably from about 8:2 to 3:7.
  • Water-soluble salts of such acrylic acid/maleic acid copolymers can include, for example, the alkali metal, ammonium and substituted ammonium salts.
  • Copolymers of acrylic acid and/or maleic acid and a polyalkylene glycol can also be used as a preferred component of the dispersing/anti-redeposition agent.
  • the copolymers are preferably graft polymers of acrylic acid and/or maleic acid and a polyalkylene glycol, copolymers of acrylic acid and/or maleic acid and an alkylene oxide adduct of allyl alcohol or isoprenol, and copolymers of acrylic acid and/or maleic acid and a polyalkylene glycol acrylate or methacrylate, and more preferably graft polymers of acrylic acid and/or maleic acid and a polyalkylene glycol and copolymers of acrylic acid and/or maleic acid and an alkylene oxide adduct of allyl alcohol or isoprenol.
  • the average molecular weight of the copolymers preferably ranges from about 2,000 to 100,000, more preferably from about 3,000 to 80,000, and most preferably from about 4,000 to 70,000.
  • Acrylic acid/acrylamide based copolymers may also be used as a preferred component of the dispersing/anti-redeposition agent.
  • the average molecular weight of such copolymers in the acid form preferably ranges from about 3,000 to 100,000, more preferably from about 4,000 to 20,000, and most preferably from about 4,000 to 10,000.
  • the acrylamide content in such copolymers generally is less than about 50%, preferably less than about 20%, and most preferably about 1 to about 15%, by weight of the polymer.
  • PEG polyethylene glycol
  • PEG can exhibit dispersing agent performance as well as act as a clay soil removal/anti-redeposition agent.
  • Typical molecular weight ranges for these purposes range from about 500 to about 100,000, preferably from about 1,000 to about 50,000, and more preferably from about 1,500 to about 10,000.
  • Polyasparatate and polyglutamate dispersing agents may also be used, especially in conjunction with zeolites builders.
  • Dispersing agents such as polyasparatate preferably have a (weight average) molecular weight of about 10,000.
  • polymeric dispersing agents known in this field can be incorporated generally in an amount of from about 0.01 to about 15%, more preferably from 0.05 to 10%, then most preferably 0.1 to 5%.
  • any optical brighteners or other brightening or whitening agents known in this field can be incorporated generally in an amount of from about 0.01 to about 1.2% by weight. Such optical brighteners are often used in the case where the detergent is designed for fabric washing or processing applications.
  • the composition of the invention may also include one or more materials effective for inhibiting the transfer of dyes from one fabric to another during the cleaning process.
  • dye transfer inhibiting agents include polyvinylpyrrolidone polymers, polyamide N-oxide polymers, copolymers of N-vinylpyrrolidone and N-vinylimidazole, manganese phthalocyanine, peroxidases, and mixtures thereof. If used, these agents generally comprise from about 0.01 to about 10% by weight, preferably from about 0.01 to about 5% by weight, and more preferably from about 0.05 to about 2% by weight of the composition.
  • optical brightener selected for use in the invention exhibits especially effective dye transfer inhibition performance benefits when used in combination with the polymeric dye transfer inhibiting agent.
  • the combination of such selected polymeric materials with such selected optical brightener provides significantly better dye transfer inhibition in aqueous wash solutions than does either of these two detergent composition components when used alone.
  • the detergent compositions according to the invention may also optionally contain one or more chelating agents, especially chelating agents for transition metal coming from others.
  • the transition metals generally seen in washing solutions include water-soluble, colloidal or granular iron and/or manganese and may sometimes associate as oxides or hydroxides.
  • Preferred chelating agents are chelating agents that effectively inhibit such transition metals, especially inhibit such transition metals or their compounds to adhere to fabrics, and/or inhibit non-preferred redox reaction occurred in the washing medium and/or on the interface of the fabric or hard surface.
  • the general chelating agents can be selected from the group consisting of amino carboxylates, amino phosphates, polyfunctionally-substituted aromatic chelating agents, and mixtures thereof.
  • compositions according to the invention may also contain water-soluble methyl glycine diacetic acid salts as a chelating agent that can effectively be used together with insoluble builders such as zeolites and layered silicates.
  • the chelating agent generally accounts for from about 0.1 to about 15% by weight of the composition. More preferably, if utilized, the chelating agent accounts for from about 0.1 to about 3.0% by weight.
  • compositions of the invention In the case where washing is required in intended utilities, especially washing by washing machines, compounds for reducing or suppressing the formation of suds can be incorporated into the composition of the invention.
  • high sudsing may be desired, and such components can be omitted. Suds suppression can be of particularly importance in the so-called “high concentration cleaning process” and in front-loading European-style washing machines (so-called drum type washing machines).
  • composition of the invention generally comprises from 0% by weight to about 10% by weight of suds suppressors.
  • Various through-the-wash fabric softeners can optionally be used in an amount of from about 0.5 to about 10% by weight to provide fabric softener benefits concurrently with fabric cleaning.
  • Clay softeners can be used in combination with amine and cationic softeners.
  • known fabric softeners including those of biodegradation type can be used in modes including the pre-treatment, main cleaning, post-laundry, and addition into washing machines and dryers.
  • Perfumes and perfumery ingredients useful in the compositions and processes comprise a wide variety of natural and synthetic chemical ingredients, including, but not limited to, aldehydes, ketones, and esters. Also, included are various natural extracts and essences that can comprise complex mixtures of ingredients such as orange oil, lemon, oil, rose extract, lavender, musk, patchouli, balsamic essence, sandalwood oil, pine oil, and cedar. Finished perfumes typically comprise from about 0.01 to about 2% by weight of the detergent composition, and individual perfumery ingredients can comprise from about 0.0001 to about 90% by weight of a finished perfume composition.
  • a wide variety of other ingredients useful in detergent compositions can be included in the composition, including other ingredients, carriers, hydrotropes, processing aids, dyes or pigments, solvents for liquid formulations, and soil fillers for bar compositions.
  • suds boosters such as C10 to C16 alkanolamides can be incorporated into the composition, typically in an amount of from 1% by weight to 10% by weight.
  • C10 to C14 monoethanol and diethanol amides illustrate a typical class of such suds boosters.
  • Use of such suds boosters with high sudsing adjuvant surfactants such as the amine oxides, betaines and sultanines noted above is also advantageous.
  • water-soluble magnesium and/or calcium salts can be added typically in an amount of from 0.1% by weight to 2% by weight, to provide additional suds.
  • detergent ingredients employed in the composition can optionally be further stabilized by absorbing the ingredients onto a porous hydrophobic substrate, then coating the substrate with a hydrophobic coating.
  • the detergent ingredient is admixed with a surfactant before being absorbed into the porous substrate.
  • the detergent ingredient is released from the substrate into the aqueous washing liquor, where it performs its intended detergent function.
  • the liquid detergent composition can contain water and other solvents as diluents.
  • Low-molecular weight primary or secondary alcohols exemplified by methanol, ethanol, propanol, and isopropanol are suitable.
  • Monohydric alcohols are preferred for stabilizing the surfactant, but polyols such as those having from 2 to about 6 carbon atoms and from 2 to about 6 hydroxyl groups (such as 1,3-propanediol, ethylene glycol, glycerin, and propylene glycol) can also be used.
  • the composition can contain such diluents in an amount of from 5% by weight to 90% by weight, and preferably from 10% by weight to 50% by weight.
  • the detergent composition is preferably formulated such that, during use in aqueous cleaning operations, the wash water has a pH of from about 6.5 to about 12.5, preferably from 7 to 12, and more preferably from about 7.0 to about 11.
  • Laundry products are typically at a pH of from 9 to 11.
  • Techniques for controlling the pH at recommended usage levels include the use of buffers, alkalis, and acids.
  • the physical stability of liquid products may be improved and the thickness of the liquid product may be altered by the addition of a cross linking polyacrylate thickener to the liquid detergent product as a thixotropic thickener.
  • Liquid detergent products are preferably low foaming, readily soluble in the washing medium and most effective at pH values best conducive to improved cleaning performance, such as in a range of desirably from about pH 6.5 to about pH 12.5, and preferably from about pH 7.0 to about pH 12.0, more preferably from about pH 8.0 to about pH 12.0, and most preferably, less than about 9.0 pH.
  • the pH adjusting components are desirably selected from sodium or potassium hydroxide, sodium or potassium carbonate or sesquicarbonate, sodium or potassium silicate, boric acid, sodium or potassium bicarbonate, sodium or potassium borate, and mixtures thereof.
  • NaOH or KOH are the preferred ingredients for increasing the pH to within the above ranges.
  • Other preferred pH adjusting ingredients are sodium carbonate, potassium carbonate, and mixtures thereof.
  • the liquid nonionic surfactant detergents that can be used to practice the present invention are preferably are alkyl ethoxylates in non-chlorine bleach liquid ADW compositions.
  • a non-chlorine bleach stable surfactant is SLF18.®. manufactured by BASF Corporation.
  • chlorine bleach stable low foaming surfactants are preferred and such surfactants are present in a range of from about 0.1% to about 10% by weight of the liquid composition.
  • Such surfactants are generally known to one skilled in the art and need not be elaborated here, for purposes of brevity.
  • An example of a chlorine bleach stable surfactant is Dowfax.® anionic surfactant available from the Dow Chemical Company.
  • nonionic surfactant examples include polyoxyalkylene alkyl ethers, polyoxyalkylene fatty acid esters, polyoxyalkylene sorbitan esters, polyoxyalkylene sorbitan fatty acid esters, polyoxyalkylene sorbitol fatty acid esters, polyoxyalkylene glycerin fatty acid esters, monoglycerides, sorbitan fatty acid esters, fatty acid monoethanolamides, fatty acid diethanolamides and alkyl polyglucosides.
  • amphoteric surfactants include acetic acid betaines, amidoacetic acid betaines, sulfobetaines, amidosulfobetaines, phosphobetaines, alkylamine oxides, and amidoamine oxides.
  • fatty acid amidopropylbetaines such as cocamidopropyl betaine and lauramidopropyl betaine are preferred.
  • imidazoline derived amphoterics disodium cocoa amphodiproprionate.
  • the surfactant is preferably contained in an amount of from 5 to 50 wt. %, more preferably from 10 to 30 wt. %, even more preferably from 10 to 20 wt. % based on the detergent composition of the present invention, from the viewpoints of foaming property, liquid properties during use and detergency.
  • the detergent composition of the present invention may contain silicones for further improvement in the conditioning effects.
  • the silicones include dimethylpolysiloxanes (viscosity: 5 mm.sup.2/s to 20 million mm.sup.2/s), amino-modified silicones, polyether-modified silicones, methylphenylpolysiloxanes, fatty acid-modified silicones, alcohol-modified silicones, alkoxy-modified silicones, epoxy-modified silicones, fluorine-modified silicones, cyclic silicones and alkyl-modified silicones, of which dimethylpolysiloxanes are preferred.
  • the content of the silicone in the detergent composition of the present invention is preferably from 0.01 to 10 wt. %.
  • the detergent composition of the present invention may contain other conditioning components such as a cationic polymer (cationic cellulose, cationic guar gum, or the like). Their content in the detergent composition of the present invention is preferably from 0.1 to 5 wt. %.
  • the detergent composition of the present invention may contain, in addition, components employed ordinarily for detergent compositions according to the intended use.
  • components employed ordinarily for detergent compositions according to the intended use.
  • humectants such as propylene glycol, glycerin, diethylene glycol monoethyl ether, sorbitol and panthenol
  • colorants such as dyes and pigments
  • viscosity regulators such as methyl cellulose, polyethylene glycol and ethanol
  • plant extracts antiseptics; bactericides; chelating agents; vitamin preparations; anti-inflammatory agents; perfumes; ultraviolet absorbers; and antioxidants.
  • the detergent composition has a particle size distribution such that no more than 10 wt % by weight of the composition, has a particle size greater than 850 micrometers, and no more than 10 wt % by weight of the composition, has a particle size less than 250 micrometers.
  • the composition optionally comprises one or more adjunct components.
  • the adjunct components are typically selected from the group consisting of other anionic surfactants, cationic surfactants, non-ionic surfactants, zwitterionic surfactants, other builders, polymeric co-builders such as polymeric polycarboxylates, bleach, other hydrotropes, chelants, enzymes, anti-redeposition polymers, soil-release polymers, polymeric soil-dispersing and/or soil-suspending agents, dye-transfer inhibitors, fabric-integrity agents, fluorescent whitening agents, suds suppressors, fabric-softeners, flocculants, cationic fabric-softening components, perfumes and combinations thereof.
  • a suitable adjunct component may be an anionic surfactant other than the alkyl alkoxylated sulphate surfactant and the linear alkyl benzene sulphonate surfactant.
  • Suitable other anionic surfactants are branched or linear C 8 -C 18 alkyl sulphate surfactants.
  • An especially suitable other anionic surfactants are methyl branched C 8 -C 18 alkyl sulphate surfactants.
  • a suitable adjunct component may be an anionic surfactant other than the alkyl alkoxylated sulphate surfactant and the linear alkyl benzene sulphonate surfactant.
  • Suitable other anionic surfactants are branched or linear C 8 -C 18 alkyl sulphate surfactants.
  • An especially suitable other anionic surfactants are methyl branched C 8 -C 18 alkyl sulphate surfactants.
  • a suitable adjunct component may be a hydrotrope other than the alkoxylated alkyl alcohol.
  • Suitable hydrotropes include sodium cumene sulphate, sodium toluene sulphate and sodium xylene sulphate.
  • the lamellar-phase gel laundry composition of the invention comprises from 1 to 8%, more preferably from 3 to 6%, by weight of a gelling agent.
  • a fatty alcohol gelling agent can be used, such as 1-decanol, 1-dodecanol, 2-decanol, 2-dodecanol, 2-methyl-1-decanol, 2-methyl-1-dodecanol, 2-ethyl-1-decanol, and mixtures thereof.
  • Commercially available materials that are particularly suitable for use as gelling agent include Neodol 23 or Neodol 25 produced by Shell Chemical Co., Exxal 12 or Exxal 13 produced by Exxonmobil Chemical Co. and Isalchem 123 or Lialchem 123 produced by Sasol Chemical Co.
  • the gelling agent may also suitably be a non-neutralised fatty acid having the formula R 3 —(COOH)—R 4 , wherein R 3 and R 4 are independently selected from hydrogen and saturated or unsaturated, linear or branched C 1 -C 22 alkyl groups, whereby the total number of carbon atoms in the fatty acid is between 10 and 23.
  • a fatty acid gelling agent is preferably selected from oleic acid, lauric acid, myristic acid, palmitic acid, stearic acid, linoleic acid, linolenic acid and mixtures thereof.
  • the gelling agent may suitably be a naturally obtainable fatty acid selected from tallow, coconut, and pal kernel fatty acids.
  • the anionic surfactant that may be present in the gel composition of the invention is preferably selected from the group consisting of linear alkyl benzene sulphonates, alkyl sulphonates, alkylpolyether sulphates, alkyl sulphates and mixtures thereof.
  • the surfactant system in the gel composition of the invention may also contain a nonionic surfactant.
  • Nonionic detergent surfactants are well-known in the art. They normally consist of a water-solubilizing polyalkoxylene or a mono- or d-alkanolamide group in chemical combination with an organic hydrophobic group derived, for example, from alkylphenols in which the alkyl group contains from about 6 to about 12 carbon atoms, dialkylphenols in which primary, secondary or tertiary aliphatic alcohols (or alkyl-capped derivatives thereof), preferably having from 8 to 20 carbon atoms, monocarboxylic acids having from 10 to about 24 carbon atoms in the alkyl group and polyoxypropylene.
  • alkylphenols in which the alkyl group contains from about 6 to about 12 carbon atoms
  • dialkylphenols in which primary, secondary or tertiary aliphatic alcohols (or alkyl-capped derivatives thereof), preferably having from 8 to 20 carbon atoms
  • monocarboxylic acids having from 10 to about 24 carbon atoms in the al
  • fatty acid mono- and dialkanolamides in which the alkyl group of the fatty acidradical contains from 10 to about 20 carbon atoms and the alkyloyl group having from 1 to 3 carbon atoms.
  • the alkyl group of the fatty acidradical contains from 10 to about 20 carbon atoms and the alkyloyl group having from 1 to 3 carbon atoms.
  • Builders in this embodiment that may be used according to the present invention include conventional alkaline detergent builders, inorganic or organic, which can be used at levels of from 0% to 50% by weight of the gel composition, preferably from 1% to 35% by weight.
  • inorganic detergency builders examples include water soluble alkali metal phosphates, polyphosphates, borates, silicates, and also carbonates and bicarbonates. Specific examples of such builders are sodium and potassium triphosphates, pyrophosphates, orthophosphates, hexametaphosphates, tetraborates, silicates, and carbonates.
  • suitable organic detergency builders are: (1) water-soluble amino polycarboxylates, e.g. sodium and potassium ethylenediaminetetraacetates, nitrilotriacetates and N-(2 hydroxyethyl)-nitrilodiacetates; (2) water-soluble salts of phytic acid, e.g. sodium and potassium phytates; (3) water-soluble polyphosphonates, including specifically sodium and potassium salts of ethane-1-hydroxy-1,1-diphosphonic acid; sodium and potassium salts of methylene diphosphonic acid; sodium and potassium salts of ethylene diphosphonic acid; and sodium and potassium salts of ethane-1,1,2-triphosphonic acid.
  • water-soluble amino polycarboxylates e.g. sodium and potassium ethylenediaminetetraacetates, nitrilotriacetates and N-(2 hydroxyethyl)-nitrilodiacetates
  • water-soluble salts of phytic acid e
  • polycarboxylate builders can be used satisfactorily, including water-soluble salts of mellitic acid, citric acid, and carboxymethyloxysuccinic acid, salts of polymers of itaconic acid and maleic acid, tartrate monosuccinate, and tartrate disuccinate.
  • the detergency builder includes carboxylates, polycarboxylates, aminocarboxylates, carbonates, bicarbonates, phosphates, phosphonates, silicates, borates and mixtures thereof.
  • Amorphous and crystalline zeolites or aluminosilicates can also be suitably used as detergency builder in gel compositions.
  • Suitable enzymes for use in the detergent compositions of the invention include proteases, amylases, lipases, cellulases, peroxidases, and mixtures thereof, of any suitable origin, such as vegetable, animal bacterial, fungal and yeast origin. Preferred selections are influenced by factors such as pH-activity, thermostability, and stability to active bleach detergents, builders and the like. In this respect bacterial and fungal enzymes are preferred such as bacterial proteases and fungal cellulases.
  • Enzymes are normally incorporated into detergent composition at levels sufficient to provide a “cleaning-effective amount”.
  • cleaning effective amount refers to any amount capable of producing a cleaning, stain removal, soil removal, whitening, or freshness improving effect on the treated substrate. In practical terms for normal commercial operations, typical amounts are up to about 5 mg by weight, more typically 0.01 mg to 3 mg, of active enzyme per gram of detergent composition. Stated otherwise, the composition of the invention may typically comprise from 0.001 to 5%, preferably from 0.01 to 1% by weight of a commercial enzyme preparation.
  • Protease enzymes are usually present in such commercial preparations at levels sufficient to provide from 0.005 to 0.1 Anson units (AU) of activity per gram of composition. Higher active levels may be desirable in highly concentrated detergent formulations.
  • AU Anson units
  • proteases are the subtilisins that are obtained from particular strains of B. subtilis and B. licheniformis.
  • One suitable protease is obtained from a strain of Bacillis, having maximum activity throughout the pH-range of 8-12, developed and sold as ESPERASE®.®. by Novozymes of Industries A/S of Denmark.
  • proteases include ALCALASE®., EVERLASE®., LIQUANASE®., and SAVINASE®., and POLARZYME®. from Novozymes, from PURAFECT®., and PROPERASE®., from Genencor International and MAXATASE®. from International Bio-Synthetics, Inc., The Netherlands.
  • Suitable lipase enzymes for use in the composition of the invention include those produced by microorganisms of the Pseudomonas group, such as Pseudomonas stutzeri ATCC 19.154, as disclosed in GB-1,372,034.
  • a very suitable lipase enzyme is the lipase derived from humicola lanuginosa and available from Novozymes, Denmark Nordisk under the tradename LIPOLASE®.
  • Other suitable lipase enzames are LIPEX®. from Novozymes.
  • Suitable cellulose enzymes for use in the composition of the invention include those produced by microorganism of the Aspergillus sp. Suitable cellulose enzymes are available under tradename CAREZYME®., CELLUZYME®., from Novozymes, PURADAX®., AND PRIMAFAST®LUNA from Genencor International.
  • Alpha-amylase enzymes can be produced by microorganism of Bacillus sp. and are available under the tradename as TERMAMYL®., STAINZYME®., DURAMYL®., from Novozymes, Denmark. Alpha-amylase enzyme is available as PURASTAR®. from Genencor International.
  • Mannanase enzymes are available under tradename MANNAWAY®., from Novozymes, Denmark and PURABRITE® from Genencor International.
  • T-BLEND EVERLASE/DURAMYL/LIPEX® T-BLEND SAVINASE/CAREZYME®.
  • T-BLEND SAVINASE/LIPEX® T-BLEND SAVINASE/LIPOLASE®.
  • T-BLEND SAVINASE/STAINZYME® T-BLEND SAVINASE/TERMAMYL®.
  • T-BLEND SAVINASE/TERMAMYL/CELLUZYME® from Novozymes, Denmark.
  • the surfactant system of the invention may optionally contain a cationic surfactant.
  • alkaline buffers may be added to the compositions of the invention, including monethanolamine, triethanolamine, borax, and the like.
  • an organic solvent may suitably be present in the gel composition of the invention, preferably at a concentration of up to 10% by weight.
  • soil suspending or anti-redeposition agents e.g. polyvinyl alcohol, fatty amides, sodium carboxymethyl cellulose or hydroxy-propyl methyl cellulose.
  • Optical brighteners for cotton, polyamide and polyester fabrics, and anti-foam agents such as silicone oils and silicone oil emulsions may also be used.
  • soil release polymers are soil release polymers, dye transfer inhibitors, polymeric dispersing agents, suds suppressors, dyes, perfumes, colourants, filler salts, antifading agents and mixtures thereof.
  • Anionic sulfonate surfactants suitable for use herein include the salts of alkylbenzene sulfonates, alkyl ester sulfonates, primary or secondary alkane sulfonates, olefin sulfonates, sulfonated polycarboxylic acids, alkyl glycerol sulfonates, fatty acyl glycerol sulfonates, fatty oleyl glycerol sulfonates, and any mixtures thereof.
  • Anionic sulfate surfactants suitable for use in the compositions of the invention include linear and branched primary and secondary alkyl sulfates, alkyl ethoxysulfates, fatty oleoyl glycerol sulfates, and alkyl phenol ethylene oxide ether sulfates.
  • Suitable anionic carboxylate surfactants include alkyl ethoxy carboxylates, alkyl polyethoxy polycarboxylate surfactants and soaps (“alkyl carboxyls”).
  • Detergent compositions often include water.
  • the proportion of water in the compositions generally is in the range of 35% to 85%, preferably 50% to 80% by weight of the usual composition.
  • Amine oxides useful in the present invention include long-chain alkyl amine oxides, ie., those compounds having the formula: R 3 (OR 4 ) x —(NO)—(R 5 ) 2
  • R 3 is selected from an alkyl, hydroxyalkyl, acylamidopropyl and alkyl phenyl group, or mixtures thereof, containing from 8 to 26 carbon atoms, preferably 8 to 16 carbon atoms;
  • R 4 is an alkylene or hydroxyalkylene group containing from 2 to 3 carbon atoms, preferably 2 carbon atoms, or mixtures thereof;
  • x is from 0 to 3, preferably 0;
  • each R 5 is an alkyl or hydroxyalkyl group containing from 1 to 3, preferably from 1 to 2 carbon atoms, or a polyethylene oxide group containing from 1 to 3, preferably 1, ethylene oxide groups.
  • the R 5 groups can be attached to each other, e.g., through an oxygen or nitrogen atom, to form a ring structure.
  • amine oxide surfactants in particular include C 10 -C 18 alkyl dimethyl amine oxides and C 8 -C 12 alkoxy ethyl dihydroxyethyl amine oxides and alkyl amido propyl amine oxide.
  • examples of such materials include dimethyloctylamine oxide, diethyldecylamine oxide, bis-(2-hydroxyethyl)dodecylamine oxide, dimethyldodecylamine oxide, dodecylamidopropyl dimethylamine oxide and dimethyl-2-hydroxyoctadecylamine oxide.
  • Preferred are C 10 -C 18 alkyl dimethylamine oxide, and C 10 -C 18 acylamido alkyl dimethylamine oxide.
  • the betaines useful in the present invention are those compounds having the formula R(R 1 ) 2 N + R 2 COO ⁇ wherein R is a C 6 -C 18 hydrocarbyl group, preferably C 10 -C 16 alkyl group, each R 1 is typically C 1 -C 3 , alkyl, preferably methyl, and R 2 is a C 1 -C 5 hydrocarbyl group, preferably a C 1 -C 5 alkylene group, more preferably a C 1 -C 2 alkylene group.
  • betaines examples include coconut acylamidopropyldimethyl betaine; hexadecyl dimethyl betaine; C 12 -C 14 acylamidopropylbetaine; C 12 -C 18 acylamidohexyldiethyl betaine; 4-[C 14 -C 16 acylmethylamidodiethylammonio]-1-carboxybutane; C 16 -C 18 acylamidodimethylbetaine; C 12 -C 16 acylamidopentanediethyl-betai-ne; C 12 -C 16 acylmethyl-amidodimethylbetaine, and coco amidopropyl betaine.
  • Preferred betaines are C 12 -C 18 dimethylamoniohexanoate and the C 10 -C 18 acylamidopropane (or ethane) dimethyl (or diethyl) betaines.
  • sulfobetaines sultaines of formula R(R 1 ) 2 N+R 2 SO 3 —, wherein R is a C 6 -C 18 Hydrocarbyl group, preferably a C 10 -C 16 alkyl group, more preferably a C 12 -C 13 alkyl group; each R 1 is typically C 1 -C 3 alkyl, preferably methyl and R 2 is a C 1 -C 6 hydrocarbyl group, preferably a C 1 -C 3 alkylene or, preferably, hydroxyalkylene group.
  • Suitable sultaines are C 12 -C 14 dihydroxyethylammonio propane sulfonate, and C 16 -C 18 dimethylammonio hexane sulfonate, with C 12 -C 14 amido propyl ammonio-2-hydroxypropyl sultaine being preferred.
  • Detergent compositions can include an alkanolamide compound such as an alkyl monoalkanol amide, an alkyl dialkanol amide, and mixtures thereof.
  • an alkanolamide compound such as an alkyl monoalkanol amide, an alkyl dialkanol amide, and mixtures thereof.
  • Detergent formulations include a hydrotrope selected from the group consisting of ethanol, isopropanol, sodium xylene sulfonate, propylene glycol, sodium cumene sulfonate, urea, polyethylene glycol and mixtures thereof.
  • Detergent compositions can include a solvent selected from the group consisting of alcohols (ethanol, isopropanol) glycols (1,3-propanediol, propylene glycol, polyethylene glycol) polyols and polyethers (dipropylene glycol, dipropylene glycol methyl ether), and mixtures thereof.
  • a solvent selected from the group consisting of alcohols (ethanol, isopropanol) glycols (1,3-propanediol, propylene glycol, polyethylene glycol) polyols and polyethers (dipropylene glycol, dipropylene glycol methyl ether), and mixtures thereof.
  • Detergent compositions can include an inorganic or organic salt or oxide of a multivalent cation, particularly Mg ++ which has phase stabilization properties.
  • the multivalent cation salt or oxide provides several benefits including improved cleaning performance in dilute usage, particularly in soft water areas, and minimized amounts of perfume required to obtain the microemulsion state.
  • Magnesium sulfate either anhydrous or hydrated (e.g., heptahydrate), is preferred as the magnesium salt. Good results also have been reported with magnesium oxide, magnesium chloride, magnesium acetate, magnesium propionate and magnesium hydroxide. These magnesium salts can be used with formulations at neutral or acidic pH since magnesium hydroxide will not precipitate at these pH levels.
  • magnesium is the typical cation from which the salts (inclusive of the oxide and hydroxide) are formed
  • other polyvalent metal ions also can be used provided that their salts are nontoxic and are soluble in the aqueous phase of the system at the desired pH level.
  • the liquid cleaning composition of this invention may, if desired, also contain other optional components either to provide additional effect or to make the product more attractive to the consumer.
  • Colorants or dyes in amounts up to 0.5% by weight; preservatives or antioxidizing agents, such as formalin, 5-bromo-5-nitro-dioxan-1,3; 5-chloro-2-methyl-4-isothaliazolin-3-one, 2,6-di-tert.butyl-p-cresol, etc., in amounts up to 2% by weight; and pH adjusting agents, such as sulfuric acid or sodium hydroxide, as needed.
  • preservatives or antioxidizing agents such as formalin, 5-bromo-5-nitro-dioxan-1,3; 5-chloro-2-methyl-4-isothaliazolin-3-one, 2,6-di-tert.butyl-p-cresol, etc.
  • pH adjusting agents such as sulfuric acid or sodium hydroxide, as needed.
  • the optional ingredients are selected from the group consisting of hydrotropes, perfumes, colorants, pH adjusting agents, preservatives, biocidal agents, inorganic salts, opacifiers, viscosity modifiers, and mixtures thereof
  • 1,3 propanediol esters as described herein are also suitable, in a non-limiting way, for use in the composition of liquid soaps and liquid detergents as emulisifers, pearlizing agents, surfactants, gelling agents, structurants, thickeners, or opacifiers.
  • the esters containing about 1 to about 24 carbons in the alkyl chain are particularly useful in liquid detergent applications.
  • Such liquid soaps and liquid detergents can be directs to any animal, especially avians, reptiles and mammals.
  • the preferred applications are directed to humans, canine, feline and equine species.
  • the most preferred applications are directed to human species.
  • esters of the instant application may be used for powder detergents, such as powder dishwasher detergent, and textiles detergents.
  • esters are also useful as a solvent in detergents, especially for botanical products.
  • Such detergent compositions comprising botanical products include botanicals directed to plants, their seeds, stems, roots, flowers, leaves, pollen, spices, and oils.
  • esters in the detergent compositions described herein may also function as an antimicrobial agent.
  • Light-duty liquid detergents are for dishwashing (by hand) and liquid detergents for textile, delicate garments—usually the exposure times are relatively short, about 20 minutes and the use concentrations are low, about 0.15%. Esters in these compositions provide benefit as non-ionic surfactants.
  • Heavy-duty liquid detergents are for textile applications (for washing machines).
  • the fatty acid esters are useful as the non-ionic surfactants.
  • the non-ionic surfactants (beside the anionic surfactants) are primarily responsible for wetting the surfaces of fabrics as well as the soil (reducing surface and interfacial tension), helping to lift the stains off the fabric surface, and stabilizing dirt particles and/or emulsifying grease droplets.
  • Esters in these compositions provide additional benefits as aesthetic ingredients and help to create a microemulsion.
  • Fatty acid esters of 1,3 propanediol can also function as non-ionic cosofteners.
  • glycol fatty acid esters deliver good softness and static control without any drawback.
  • cream cleaners as fatty acid esters, including esters of 1,3 propanediol, provide microemulsion characteristics that benefit cream cleaners and detergents.
  • Gel cleaners can also be formulated within the esters of 1,3 propanediol for the same reasons.
  • 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 325608 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 1,3-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 bio-source 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.
  • FIG. 1 depicts a graph of these data.
  • Chemical 1,3-propanediol (Shell Chemical, LP Houston, Tex.) was prepared as described herein, specifically as described in Examples 1 and 2.
  • 5.2 g (0.068 moles) of 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.
  • FIG. 6 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 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.
  • Examples 11 are prophetic and similar to compositions described in the following patents, U.S. Pat. Nos. 4,620,976; 4,654,163; 6,165,955; 6,417,146 B1; and 6,894,013 B2, herein specifically incorporated by reference.
  • Detergents Comprising Esters Formed from Biologically Derived 1,3-Propanediol Fatty acid 1,3 propanediol ester: 5.0-30.0% 1,3 propanediol distearate Fatty acid alkanolamide: 2.0-20.0%
  • coconut oil acid monoethanolamide Surfactant: 0.1-10.0% Sodium lauryl triglycol ether-sulfosuccinate Coconut-alkyldimethylamine oxide Sodium salt 0.1-3.0% Mono- or Di-valent Water up to 100.00
  • Liquid Detergent Comprising Esters Formed from Biologically Derived 1,3-Propanediol Fatty acid 1,3 propanediol ester: 5.0-30.0% 1,3 propanediol distearate Fatty acid alkanolamide: 2.0-20.0% Cocomonoethanolamide
  • Nonionic surfactant 0.1-10.0% C 10-12 -Fatty polyol alkyl ester Water up to 100.0%
  • Liquid Detergent Comprising Esters Formed from Biologically Derived 1,3-Propanediol Fatty acid 1,3 propanediol ester: 5.0-40.0% 1,3 propanediol distearate Nonionic surfactant: 3.0-30.0% Laureth-7 Amphoteric surfactant: 0.0-10.0% Cocoamidopropyl betaine Cocoamphoacetate Glycol: 0.0-15.0% Propylene glycol (1,2 and/or 1,3) Water up to 100.0%
  • the fatty acid 1,3 propanediol ester functions as a pearlizing agent
  • the nonionic surfactant functions as an emulsifier and stabilizer
  • the amphoteric surfactant functions as a co-emulsifier to enhance pearlizing effect
  • the glycol functions as an emulsifier as well.
  • Liquid Detergent Comprising Esters Formed from Biologically Derived 1,3-Propanediol Fatty acid glycol ester sulfate (A) 10.0-60.0% Propanediol lauric acid sulfate sodium salt Additional surfactant (B) 90.0-40.0% (anionic, nonionic, cationic, amphoteric, and/or zwitterionic) Sodium laureth sulfate Water up to 100.0%
  • Foaming behavior may be tested by, preparing a 10% by weight aqueous surfactant solution (21° dH+1% by weight sebum) and determining the foam volume by Standard DIN 53902, Part 1. Test solutions can be made using weight ratios of A (10.0-60.0%) and B (90.0-40.0%).
  • the fatty acid glycol ester sulfates may exhibit advantageous properties: 1) foam booster for other surfactants, 2) foam stability in the presence of hard water and/or oil, 3) improve formulation of surfactants with poor solubility in cold water, 4) contribute to cleaning performance, 5) dermatologically safe, 6) readily biodegradable, and 7) free of nitosamines.
  • Liquid Detergent Comprising Esters Formed from Biologically Derived 1,3-Propanediol Surfactant: 1.0-50.0% (anionic, nonionic, or amphoteric) Sodium POE (3) lauryl ether sulfate Lauryl amidopropylbetaine Coconut oil fatty acid monothanol amide POE (12) lauryl ether Fatty acid 1,3 propanediol ester: 0.3-5.0% 1,3 propanediol distearate Glyceryl ether 0.1-10.0% N-Octyl glyceryl ether Water up to 100.0%
  • compositions using the 1,3 propanediol ester will have a pearly luster, and are excellent in the dispersion stability of a pearlent.
  • Procedure Combine all ingredients together, heating the mixture to 80° C. and allowing the ingredients to melt, and then cooling the melt to 30° C. with stirring.

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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
US11/705,245 Active 2029-09-04 US7960575B2 (en) 2006-02-10 2007-02-12 Synthesis of mono and di esters from biologically-produced 1,3-propanediol
US11/705,257 Abandoned US20070207939A1 (en) 2006-02-10 2007-02-12 Compositions comprising mono and di esters of biologically-based 1,3-propanediol
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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
US11/705,257 Abandoned US20070207939A1 (en) 2006-02-10 2007-02-12 Compositions comprising mono and di esters of biologically-based 1,3-propanediol
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