US20070203276A1 - Plasticizers comprising biologically-based mono and di esters - Google Patents

Plasticizers comprising biologically-based mono and di esters Download PDF

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Publication number
US20070203276A1
US20070203276A1 US11/705,327 US70532707A US2007203276A1 US 20070203276 A1 US20070203276 A1 US 20070203276A1 US 70532707 A US70532707 A US 70532707A US 2007203276 A1 US2007203276 A1 US 2007203276A1
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Prior art keywords
propanediol
ester
composition
carbon
biologically
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Gyorgyi Fenyvesi
Raja Hari Prasad Poladi
Ann Wehner
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DuPont Tate and Lyle Bio Products Co LLC
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Priority to US11/705,327 priority Critical patent/US20070203276A1/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, POLADI, RAJA HARI PRASAD R., WEHNER, ANN
Publication of US20070203276A1 publication Critical patent/US20070203276A1/en
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/223—Five-membered rings containing nitrogen and carbon only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/042—Siloxanes with specific structure containing aromatic substituents
    • C10M2229/0425—Siloxanes with specific structure containing aromatic substituents used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/64—Environmental friendly compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/12—Soft surfaces, e.g. textile
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/14—Hard surfaces
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W10/00—Technologies for wastewater treatment
    • Y02W10/30—Wastewater or sewage treatment systems using renewable energies
    • Y02W10/37—Wastewater or sewage treatment systems using renewable energies using solar energy

Definitions

  • the field of this invention relates to plasticizers generally, and more specifically to conjugate esters of 1,3-propandiol are plasticizers.
  • a plasticizer is a component that is added to a material (usually a resin or elastomer) to make that material softer, more flexible and easier to process.
  • Plasticizers for plastics are additives, most commonly phthalates, which give hard plastics like PVC the desired flexibility and durability. They are often based on esters of polycarboxylic acids with linear or branched aliphatic alcohols of moderate chain length. Plasticizers work by embedding themselves between the chains of polymers, spacing them apart (increasing of the “free volume”), and thus significantly lowering the glass transition temperature for the plastic and making it softer.
  • Plasticizers are usually small molecules, the molecular weights in the range of 100-1000.
  • the most widely plastized polymer is poly(vinyl chloride) (PVC) because of its excellent plasticizer compatibility.
  • PVC poly(vinyl chloride)
  • Plasticizers are generally used for thermoplastic materials, but small amounts of plasticizers can be used in thermosets to improve the impact resistance of the polymers.
  • plasticizer added to a polymer varies depending on the effect required. A small addition of plasticizer may be made to improve the workability of the polymer melt. This contrasts with larger additions made with the specific intention of completely transforming the properties of the product.
  • plasticizers are known carcinogens and endocrine disruptors. Accordingly, safer plasticizers with better biodegradability and less biochemical effects are desired. Additionally, plasticizers that do not contribute to greenhouse gas emissions during production or degradation are also desirable.
  • 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 composition comprising an ester of 1,3-propanediol and a polymer is provided, and the ester is an ester of biologically-derived 1,3-propanediol.
  • the ester can have at least 3% biobased carbon, at least 6% biobased carbon, or at least 10% biobased carbon.
  • the composition can further comprise biologically-derived 1,3-propanediol.
  • a process for producing a plastic material comprising an ester of 1,3-propanediol. The process comprises providing an ester of 1,3-propanediol; and mixing the ester with a polymer.
  • 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.
  • compositions comprising a plasticizer are provided.
  • the plasticizers provided are mono and di esters of 1,3-propanediol.
  • the 1,3-propanediol used in forming the esters is biologically-derived.
  • the 1,3-propanediol esters made from biologically-derived 1,3-propanediol contain some biobased carbon.
  • Compositions and methods for producing compositions comprising a polymer and a plasticizer are also provided.
  • the 1,3-propanediol esters provided herein are effective in a variety of polymers.
  • the polymer compositions can be made into shaped items, foams, films, including both cast and biaxially oriented films, using conventional equipment.
  • the steps involved are typically: preparing a dry blend of polymer, melt-blending the polymers, extruding the polymers to form pellets (including other shapes such as flakes), re-melting the pellets, extruding the pellets through a die, and can be carried out at temperatures in the range of about 160° C. to about 300° C.
  • Polyvinyl chloride is a commonly plasticized polymer. Highly flexible PVC is used in a wide range of application as floor tiles, sheet flooring, carpet backing, and in different medical devices. More than 90% of the plasticizer volume is used by the PVC industry. Without plasticizers, PVC has very limited applications as a polymeric material.
  • the 1,3-propanediol ester plasticizers can also be used in other polymers including acrylic polymers. These are mostly acrylic ester polymers and methacrylic ester polymers. Highly flexible coatings are produced with acrylics containing plasticizers.
  • the compatibilities of a plasticizer with acrylics is up to about 10 wt % of plasticizer, however, for low molecular weight plasticizers higher compatibility level can be achieved.
  • Ester plasticizers according to the invention can also be used in the production of nylon.
  • Plasticizers can improve the processing of nylon polymers. The high degree of crystallization of nylon polymers allow to use low level of plasticizers.
  • Polyesters are also often produced with plasticizers. Examples of polyesters include: poly(ethylene terephthalate) (PET, or 2GT), poly(trimethylene terephthalate) (PTT, or 3GT), poly(tetramethylene terephthalate (PBT, or 4GT), poly(lactic acid) (PLA).
  • PET poly(ethylene terephthalate)
  • PTT poly(trimethylene terephthalate)
  • PBT poly(tetramethylene terephthalate
  • PDA poly(lactic acid)
  • Plasticizers in amounts up to 15-20% can be used as processing aids and external lubricants in the production of polyesters.
  • polysaccharides such as starch and cellulose
  • plasticizers in amounts up to 50% to process elastomeric materials.
  • Polyolefins also benefit from the 1,3-propanediol ester plasticizers. Polyolefins are compatible with plasticizers up to about 5%. Small amounts of plasticizers, up to about 5%, are also commonly used with polystyrenes to increase flexibility.
  • fluoroplastics have improved elongation and increased softness when 1,3-propanediol ester plasticizers are used up to about 250/%. Rubber materials also benefit from plasticizers. Ester plasticizers can be used with latex rubber, nitrile rubber, and chloropene to reduce glass transition temperature (Tg). Plasticizers, up to about 20%, may improve binding properties, toughness,and flexibility of polyvinyl butyral (PVB) resins.
  • PVB polyvinyl butyral
  • a primary plasticizer when added to a polymer, causes elongation and softness will be increased.
  • a secondary plasticizer when added to the polymer alone, does not bring about these changes and may have limited compatibility with the polymer, however, when added to the polymer in combination with a primary plasticizer, the secondary plasticizer enhances the plasticizing performance of the primary plasticizer.
  • the 1,3-propanediol esters described herein are appropriately used as either primary or secondary plasticizers.
  • plasticizers especially plasticizers comprising esters of 1,3-propanediol.
  • plasticizers comprising esters of 1,3-propanediol.
  • One application of plasticizers is in PVC suspensions.
  • vinyl chloride is suspended in water and polymerized using a water soluble initiator.
  • the polymers produced in the suspension have particles that are highly porous and therefore are able to absorb large amounts of plasticizers.
  • 1,3-propanediol ester plasticizers are in plastisols.
  • Microsuspension polymerization and dispersion polymerization can be used to produce plastisols.
  • Much lower particle size resins are produced using this technology compared to the suspension method.
  • Mixing the filler, blending resin, dispersion resin with plasticizer will create a paste or plastisol.
  • Mono esters and mixtures of different monoesters can be used in plastisols (as secondary plasticizers) and diesters can be used as primary plasticizers.
  • the plasticizer concentration can vary from about 10 to about 100%, based on polymer weight.
  • esters formed from biologically-based 1,3-propanediol are similar to esters produced from chemically derived 1,3-propanediol
  • the toxicity of the bio-derived esters can be lower than the toxicity of chemically derived esters.
  • the manufacturing process does not contribute fossil-fuel based carbon to the atmosphere, thus decreasing the amount of greenhouse gas emissions while providing identical, or improved functionality.
  • the polymeric compositions made with the 1,3-propanediol esters as plasticizers can include anywhere between about 0.01% and about 100% ester depending on the application. Accordingly, the composition can comprise between about 0.01% and about 5% ester, between about 5% and about 15% ester, between about 15% and about 25% ester, between about 25% and about 50% ester, and between about 50% and about 100% ester.
  • 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, 1,2-propylene glycol, dipropylene diol, tripropylene diol, 2-methyl 1,3-propanediol, neopentyl glycol and bisphenol A. “Bio-based”, and “bio-sourced”; “biologically derived”; and “bio-derived” are used synonymously herein.
  • “Fermentation” as used refers to the process of metabolizing simple sugars into other organic compounds. As used herein fermentation specifically refers to the metabolism of plant derived sugars, such sugar are composed of carbon of atmospheric origin.
  • Carbon of atmospheric origin refers to carbon atoms from carbon dioxide molecules that have recently, in the last few decades, been free in the earth's atmosphere. Such carbons in mass are identifiable by the present of particular radioisotopes as described herein. “Green carbon”, “atmospheric carbon”, “environmentally friendly carbon”, “life-cycle carbon”, “non-fossil fuel based carbon”, “non-petroleum based carbon”, “carbon of atmospheric origin”, and “biobased carbon” are used synonymously herein.
  • Carbon of fossil origin refers to carbon of petrochemical origin. Such carbon has not been exposed to UV rays as atmospheric carbon has, therefore masses of carbon of fossil origin has few radioisotopes in their population. Carbon of fossil origin is identifiable by means described herein. “Fossil fuel carbon”, “fossil carbon”, “polluting carbon”, “petrochemical carbon”, “petro-carbon” and carbon of fossil origin are used synonymously herein.
  • “Naturally occurring” as used herein refers to substances that are derived from a renewable source and/or are produced by a biologically-based process.
  • “Fatty acid” as used herein refers to carboxylic acids that are often have long aliphatic tails, however, carboxylic acids of carbon length 1-40 are specifically included in this definition for the purpose of describing the present invention.
  • “Fatty acid esters” as used herein are esters, which are composed of such, defined fatty acids.
  • Catalyst refers to a substance that is facilitates a chemical reaction without being either a reactant or a product of said reaction.
  • NMR nuclear magnetic resonance
  • color and “color bodies” is meant the existence of visible color that can be quantified using a spectrocolorimeter in the range of visible light, using wavelengths of approximately 400-800 nm, and by comparison with pure water. Reaction conditions can have an important effect on the nature of color production. Examples of relevant conditions include the temperatures used, the catalyst and amount of catalyst. While not wishing to be bound by theory, we believe color precursors include trace amounts of impurities comprising olefinic bonds, acetals and other carbonyl compounds, peroxides, etc. At least some of these impurities may be detected by such methods as UV spectroscopy, or peroxide titration.
  • Color index refers to an analytic measure of the electromagnetic radiation-absorbing properties of a substance or compound.
  • Haldrogenation reactor refers to any of the known chemical reactors known in the literature, including but not limited to shaker-tubes, batch autoclaves, slurry reactors, up-flow packed bed, and trickle flow packed bed reactors.
  • IRMS refers to measurements of 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 biobased content of distearate propanediol made from biologically-derived propanediol, and non-biologically derived strearic acid is 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 plasticizer 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 used 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 R 1 —COOH. Where in the substituent R 1 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, butyric, lauric, myristic, palmitic, stearic, arachidic, adipic, benzoic, caprylic, maleic, palmitic, sebacic, archidonic, erucic, palmitoleic, pentadecanoic, heptadecanoic, nondecanoic, octadectetraenoic, eicosatetraenoic, eicosapentaenoic, docasapentaenoic, tetracosapentaenoic, tetrahexaenoic, docosahexenoic, (alpha)-linolenic, docosahexaenoic, eicosapentaenoic, linoleic, arachidonic, oleic, erucic, formic, propionic, vale
  • a more preferred list of suitable organic acids are acetic, adipic, benzoic, maleic, sebacic, and mixtures of such acids.
  • suitable “fatty acids” meaning generally acids named containing 8-40 carbon in the carbon useful in the present invention include butyric, valeric, caproic, caprylic, pelargonic, capric, lauric, myristic, palmitic, stearic, arachidic, behenic, cerotic, oleic, linoleic, linolenic, margaric, montanic, melissic, lacceroic, ceromelissic, geddic, ceroplastic and the mixtures of such acids.
  • these acids, and their salts and alkyl esters are most preferred stearic, lauric, palmetic, oleic, 2-ethyl hexanoic, and 12-hydroxystearic and mixtures of such acids.
  • esters produced include all the appropriate conjugate mono and diesters of 1,3 propanediol using the described organic acids.
  • Some esters in particular that are produced include propanediol distearate and monostearate, propandiol dilaurate and monolaurate, propanediol dioleate and monooleate, propanediol divalerate and monovalerate, propanediol dicaprylate and monocaprylate, propanediol dimyristate and monomyristate, propanediol dipalmitate and monopalmitate, propanediol dibehenate and monobehenate, propanediol adipate, propanediol maleate, propanediol dibenzoate, propanediol diacetate, and all mixtures thereof.
  • esters produced include: propanediol distearate and monostearate, propanediol dioleate and monooleate, propanediol dicaprylate and monocaprylate, propanediol dimyristate and monomyristate, and all mixtures thereof.
  • 1,3-propanediol can be contacted, preferably in the presence of an inert gas reacted with a fatty acid or mixture of fatty acids or salts of fatty acids in the absence or presence of a catalyst or mixture of two or more catalysts, at temperatures ranging from 25° C. to 400° C.
  • the catalyst can be 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.
  • R 1 and R 2 is a hydrocarbon, preferably with a carbon chain length of about 1 to about 40.
  • Such hydrocarbons can be saturated or unsaturated, substituted or unsubstituted, linear or branched
  • M is hydrogen, an alkali metal or an alkyl group.
  • R1 and R2 can have one or more functional groups selected from the group consisting of alkene, amide, amine, carbonyl, carboxylic acid, halide, hydroxyl groups, ether, alkyl ether, sulfate and ethersulfate. Additionally, R1 and R2 can be the same carbon chain in the case of a diester.
  • any molar ratio of diol to dicarboxylic acid or its salt or its ester can be used.
  • the preferred range of the diol to dicarboxylic acid is from about 1:3 to about 2:1. This ratio can be adjusted to shift the favor of the reaction from monoester production to diester production. Generally, to favor the production of diesters slightly more than about a 1:2 ratio is used; whereas to favor the production of monoesters about a 1:1 ratio is used.
  • the ratio of diol to dicarboxylic acid can range from about 1.01:2 to about 1.1:2; however if the monoester is desired a range of ratios from about 1.01:1 to about 2:1 is used.
  • the catalyst-content for the reaction can be from 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.
  • Any ester of 1,3-propanediol can be made or used in accordance with the the present invention.
  • Short, middle and long chain monoesters and diesters of the 1,3-propanediol can be made. Specifically those acids containing between about 1 and about 36 carbons in the alkyl chain can be produced.
  • 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 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 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.
  • % wt.” means percent by weight; “qs” means as much as suffices; “EDTA” means ethylenediamine tetraacetate; “° C.” means degrees Centigrade; “° F.” is degrees Fahrenheit, “Bio-PDO” means biologically-derived 1,3-propanediol; “ppm” is parts per million; “AU” is absorbance unit; “nm” is nanometer(s); “GC” is gas chromatograph; “APHA” is American Public Health Association; “cps” is centipoise; “f/t” is freeze/thaw; “mP ⁇ s” is millipascal seconds; “D.I.” is deionized.
  • 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.
  • Monoesters and diester of bio-produced 1,3-propandiol may be produced by combining bioPDO with organic acid. The combination is to be performed in dry conditions under heat and prolonged agitation with a selected catalyst. The ratio of monoester to diester produced will vary according to the molar ratio of acid to bioPDO 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%.
  • 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.
  • 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.
  • biosource 1,3-propanediol was purified using methods as in examples 1 and 2.
  • 2.58 g (0.033 moles) of biosource 1,3-propanediol, 19.45 g (0.065 moles) of stearic acid (Aldrich, 95%), and 0.2125 g (0.001 moles) of p-toluenesulfonic acid (Aldrich 98.5%) were charged into glass reactor fitted with mechanical stirrer and the reactor was flushed with dry nitrogen gas to remove air and moisture for 15 min. Then reaction temperature was raised to 100° C. while thoroughly stirring the reaction mixture under nitrogen flow and continued for 210 min.
  • reaction mixture was cooled to about 35° C. and the product was transferred into a beaker.
  • the product was purified by adding 100 mL of water and thoroughly stirring at 45-60° C., to form an emulsion for 15 min. The mixture was cooled and the solid propanediol distearate was separated by filtration.
  • Bio-PDO biologically-derived 1,3-propanediol (produced and purified as described in Published U.S. Patent Application No. 2005/0069997) (“Bio-PDO”) is compared, in several purity aspects, to two separate commercially-obtained preparations of chemically-produced 1,3-propanediol (Source A and B).
  • the unit ppm of total organic impurities means parts per million of total organic compounds in the final preparation, other than 1,3-propanediol, as measured by a gas chromatograph with a flame ionization detector. Results are reported by peak area. A flame ionization detector is insensitive to water, so the total impurity is the sum of all non 1,3-propanediol organic peaks (area %) ratioed to the sum of all area % (1,3-propanediol included).
  • the term “organic materials” refers to the contaminants containing carbon.
  • 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.
  • Bio-source 1,3-propanediol was prepared as described herein, specifically as described in Examples 1 and 2.
  • 5.2 g (0.068 moles) of biosource 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.
  • PLA poly(lactic acid)
  • the matrix polymer used was poly(lactic acid) (PLA)4040D from Cargill, Inc., Minnetonka, Minn.
  • the esters were synthesized from biologically-derived 1,3-propanediol. The production, purification, and characterization of the esters is described above.
  • the commercially available plasticizer ester used was propylene glycol dibenzoate for comparison.
  • PLA resin was dried in a vacuum oven at 80° C. for 16 hours, then was melt extruded with various amount of plasticizer on a 28-mm twin screw extruder, commercial unit (Werber-Pfleiderer, Ramsey, N.J.). The plasticizers were transferred by an injection pump. Plasticizers solid at room temperature were melted prior usage. Pellets of the PLA and plasticizer blend were dried under vacuum at 80° C. prior to film extrusion process. The dried pellets were extruded through a standard die, quenched by passing through a water chilled roll, cooled to room temperature and wound. Films of various thickness were prepared, and data of physical properties for 4 mil thick films are in Table 1 below.
  • polyesters including PLA
  • plasticizers can act as processing aids.
  • Table 1-3 show that using aliphatic esters of 1,3-propanediol (propanediol-di-ethylhexanoate) can increase the elongation break of PLA almost 100% compared to commercially available plasticizers.
  • the performance of Propanediol-dibenzoate is comparable to the commercial ester plasticizer.
  • PVC poly(vinyl chloride)
  • the 1,3 propanediol ester was synthesized in methods comparable to those disclosed herein.
  • the 1,3 propanediol ester used was propanediol dibenzoate and the commercial product used was propylene glycol (1,2-propanediol) dibenzoate, available as Benzoflex 284 (R) from Velsicol, Rosemont, Ill.
  • Poly(vinyl chloride)(PVC) Geon® 2188GC was obtained from PolyOne, Cleveland, Ohio.
  • the polymer was mixed with 1,3 propanediol ester and commercial ester material in an industrial mixer at 60 rpm for 15 minutes. The temperature was kept between 170-175° C. for the mixing. After the mixing the polymer was cooled, ground and dried at 80° C. in vacuum under a nitrogen blanket.
  • the polymers were press molded with a mold size of 220 mm ⁇ 150 mm.
  • the specimen test geometry (Type (5) bars) followed the ASTM D638 requirements. Physical measurements were run on the test bars (ASTM D638) on an Instron Corporation Tensile Tester, Model no. 1125 (Instron Corp., Norwood Mass.). The level of plasticizer used and the physical test data are incorporated in Table 4.

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

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