CN101641313A - 1 of biological origin, ammediol and conjugate esters thereof are as natural and non-irritating solvent - Google Patents
1 of biological origin, ammediol and conjugate esters thereof are as natural and non-irritating solvent Download PDFInfo
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Abstract
The invention provides and comprise 1, ammediol and extract the composition of product, and 1 in the composition, ammediol is the biology origin.The method of extracting extract from the source also is provided.These methods comprise provides 1, the ester of ammediol and with 1, and mix in the ester of ammediol and source.This is used for extract is entered ester from the source extraction.This method also comprises separates with ester the source with extract.The present invention also provides and has comprised 1, the composition of the ester of ammediol and extraction product.In these compositions, ester can have at least 3% bio-based carbon.
Description
The cross reference of related application
[001] the application requires the interests of following application: the U.S. Provisional Application No.60/772 that on February 10th, 2006 submitted to, 471; The U.S. Provisional Application No.60/772 that on February 10th, 2006 submitted to, 194, the U.S. Provisional Application No.60/772 that on February 10th, 2006 submitted to, 193, the U.S. Provisional Application No.60/772 that on February 10th, 2006 submitted to, 111, the U.S. Provisional Application No.60/772 that on February 10th, 2006 submitted to, the U.S. Provisional Application No.60/772 that on February 10th, 120,2006 submitted to, 110, the U.S. Provisional Application No.60/772 that on February 10th, 2006 submitted to, the U.S. Provisional Application No.60/846 that on September 25th, 112,2006 submitted to, 948, the U.S. Provisional Application No.60/853 that on October 24th, 2006 submitted to, the U.S. Provisional Application No.60/859 that on November 15th, 920,2006 submitted to, 264; The U.S. Provisional Application No.60/872 that on December 4th, 2006 submitted to, the U.S. Provisional Application No.60/880 that on January 17th, 705 and 2007 submitted to, 824, disclosing wherein specially incorporated this paper into as a reference in full.
Technical field
[002] the present invention relates to comprise the composition of solvent and extract, and use the method for solvent from the material extraction compound.
Background technology
[003] human consumer and manufacturer more and more pay close attention to the environmental influence of all products.Work for environmental influence understanding is the worldwide affairs of being assert by government department.Be that the whole world is made great efforts to facilitate and had precedence over cost and efficient is considered the example that safer environment is produced at present by the Kyoto Protocol amendment of the UNFCCC (United Nations Framework Convention on Climate Change) (UNFCCC) of 156 country's signatures.Particularly when being applied to product such as personal care product, makeup, treatment product and cosmetic treatment product, the human consumer more and more has selectivity to the source of the product that they bought.The consumption expenditure that 2004Co-operativeBank ' s annual Ethical Consumerism Report (www.co-operativebank.co.uk) discloses on the retail product that is meeting the specification between 2003 to 2004 (considering the general classification of trade goods environmental safety, organic and fair) increases by 30.3%, and total consumption expenditure only increases by 3.7% in the same period.
[004] one of pure environmental concerns of human consumer's maximum is Global warming effect and the greenhouse gases that promote this effect.Greenhouse gases are to allow daylight freely to enter atmospheric gas.When sun exposure when the earth surface, its some be reflected back to space as ir radiation.Greenhouse gases absorb these ir radiations and catch heat in the atmosphere.Along with the past of time, the about energy that should equal to be got back to by radiation space of energy from sun emission arrival earth surface makes that the temperature of earth surface is generally constant.Yet the amount of greenhouse gases increases and surpasses its amount before human industrialization, and this just has been considered to increase the reservation heat on the earth surface and has caused viewed Global warming in nearest twoth century.
[005] carbonic acid gas comes out as the composition of the maximum in the various greenhouse gases in the atmosphere is selected.The level of atmospheric carbon dioxide has increased by 50% in nearest 200 years.Think that any further increase carbonic acid gas promotes stable the moving to global temperatures heating direction of greenhouse gases effect from global temperatures in atmosphere.Human consumer and environmental protection mechanism have determined that all industrial release carbon is the source that causes the carbon of Greenhouse effect in atmosphere.When comparing as the identical organic molecule of oil or fossil fuel, only the organic products that is made of carbon molecule and final big gas carbon from renewable base source such as plant sugar and starch is considered to further not promote Greenhouse effect.
[006] except increasing the carbonic acid gas in atmosphere, the industrial process of present propandiols also produces pollutent and refuse, and they comprise sulfuric acid, hydrochloric acid, hydrofluoric acid, phosphoric acid especially, tartrate, acetate, basic metal, alkaline-earth metal, transition metal and heavy metal comprise iron, cobalt, nickel, copper, silver, molybdenum, tungsten, vanadium, chromium, rhodium, palladium, osmium, iridium, rubidium and platinum (United States Patent (USP) 2,434,110,5,034,134,5,334,778 and 5,10,036).
[007] product that need provide environmental influence to reduce for all production is particularly considered atmospheric carbon load.The environmental advantages that also has for manufacturers provides the product in renewable base source.In addition, need confirmed its to produce carbon dioxide level or the increase solvent seldom that does not increase in the present environment.
[008] laid-open U.S. Patents application No.2005/0069997 discloses a kind of purifying that is used for and has derived from the Bioengineered to synthesize 1 from sugar, 1 of the colibacillary fermenting broth of ammediol, the method for ammediol of cultivation.Primary process requires to have the filtration of meat soup product stream, and ion-exchange and distillation are preferably included in the chemical reduction of product in the still-process.Also provide highly purified 1, the composition of ammediol.
[009] is used for personal care, animal care, beauty treatment, treatment, medicine, trophicity treatment, aromatherapy, the preparation of essence and cosmetic treatment can be benefited from and be used as for example tensio-active agent in the composition, wetting Agent for Printing Inks, solvent, neutralizing agent, emulsifying agent, the glycols of sanitas and/or flavor potentiator and fixing agent.Usually, the diol component in the personal care application comprises propylene glycol, 1,3 butylene glycol, or 2-methyl isophthalic acid, ammediol.Because production cost and relative low purity, 1 of routine is not although even it is not to be identical character better that ammediol shows with above-mentioned glycol comparison yet, use 1 of routine, ammediol usually yet in these compositions.
[0010] in addition, under the extract or fragrant enriched material or fragrant oil condition of preparation introduced plant, vegetables, proteins/peptides, marine products class, algae or the newborn class of personal care, animal care, beauty treatment, treatment, medicine, trophicity treatment, aromatherapy, essence and cosmetic treatment, the human consumer pays close attention to the quality and the environmental influence of described product.At present, the extract of plant, vegetables, proteins/peptides, marine products class, algae and newborn class and fragrant enriched material adopt chemical solvents such as propylene glycol, the 2-methyl isophthalic acid, and ammediol, butyleneglycol, dipropylene glycol, synthetic glycerine and ethanol are used for extraction process.Under many circumstances, the chemical solvents combination with one another is used.Although these chemical solventss are appropriate solvent, they have the inherent defective, because they are petroleum base component but not " All Pure Nature " product.In addition, the safety assessment of these solvents provides their evidence (Cosmetic Ingredient Review Expert Panel (1994) Final Report on the SafetyAssessment of Propylene Glycol and Polypropylene Glycols.J.Am.CollegeToxicol., 13 (6): 437-491) that can cause skin irritation.
[0011] essential oil that extracts from plant is widely used in beauty treatment and personal care formulations.Extraction is used for food and non-food product industry from the colorant of plant.Medicinal plant extract just is being used to treat different illnesss.Although can use some kinds of methods to be used for extracting spices, essence, colorant and activeconstituents, solvent extraction is a kind of method that is widely adopted.The selective extraction of required composition is extracted the stability of composition, and composition and separating of unwanted solvent is the principal element of extracting.When using volatile solvent to extract activeconstituents, in preparation, need to remove described solvent before this composition of use such as ethanol.When removing when desolvating, some activeconstituentss may be unsettled and decompose.
Summary of the invention
[0012] the invention provides and comprise 1, ammediol and extract the composition of product, and 1 in the composition, ammediol is the biology origin.The present invention also provides the method for extracting extract from extraction source.These methods comprise provides 1, ammediol ester and with 1, the ammediol ester mixes with described extraction source.This is used for extract is entered ester from the extraction source extraction.This method also comprises from ester and extract separation and Extraction source.The present invention also provides and has comprised 1, the composition of ammediol ester and extraction product.In these compositions, ester can have at least 3% bio-based carbon.
Detailed Description Of The Invention
[0013] applicant introduces all especially and is quoted from the full content of document in the disclosure.In addition, when giving output, concentration or other value or parameter as scope, preferable range, or during the inventory of upper limit preferred value and lower limit preferred value, can be regarded as is concrete disclosed all scopes that formed by any a pair of any higher limit or preferred value and any lower value or preferred value, and no matter whether this scope is disclosed separately.When having described numerical range in this article, except as otherwise noted, otherwise this scope is intended to comprise its endpoint value, and all integers and mark in this scope.Scope of the present invention is not intended to and is limited to the particular value of being set forth when scope is defined.
[0014] is used to dilute and the solvent that extracts natural extract synthetic petroleum base organic solvent normally.Plant, vegetables, proteins/peptides, the marine products class, the extract of algae and newborn class has another name called essential oil, is the attractive component in many compositions.These essential oils are given product with aromatoising substance, activeconstituents and other function, such as feel, and flexibility, oilness, healing, refrigerant property, refresh oneself microbial resistance, convergency, nail is strengthened, and promotes skin histology and hair health, cleaning, stimulate, bleach the sending of antioxidant, and releiving property of skin (soothing).Essential oil is plant/vegetables, proteins/peptides, and lipid, the marine products class, the ethereal oil of algae or newborn class material, they are obtained by distillation or solvent extraction.
[0015] 1 of the biology origin, ammediol and conjugate esters thereof (conjugate ester) can be used as the solvent that extracts essential oil and other extract from the extract source.It is 10% near 100% the plant milk extract and the solvent systems of essence enriched material and volatile oil that 1 of biological origin, ammediol and conjugate esters thereof can be used as concentration range.
[0016] in addition, 1 of biology origin, ammediol and conjugate esters thereof can be used as the solvent of dilution or solubilising extract in composition.1 of biology origin, ammediol and conjugate esters thereof are unique as solvent, because they are natural origin, and therefore attractive for the human consumer who avoids synthesis of chemicals.
[0017] 1 of the biology origin, ammediol and conjugate esters thereof provide the non-irritating solvent that is used to extract and dilute plant, vegetables, proteins/peptides, marine products class, algae, newborn class substrate or essence enriched material and volatile oil.In one aspect of the invention, solvent is made up of the All Pure Nature component, and term as used herein " All Pure Nature " is meant the product of being made by naturally occurring composition.Specifically, 1 of biology origin, ammediol comprises non-petroleum base carbon.
[0018] 1 of the biology origin of this paper discussion, the conjugate esters of ammediol comprises 1 of biology origin, the monoesters of ammediol and diester.
[0019] 1 of the biology origin, ammediol or its ester conjugate (conjugate) are as the chemical solvents that extracts or dilute plant milk extract or essence enriched material or volatile oil.The method of extracting extract from the extract source comprises: (a) provide 1, ammediol, 1, ammediol ester or its mixture; (b) with 1, ammediol, 1, ammediol ester or its mixture mix with extraction source, so extract extract from this extraction source and enter the ester; (c) from extract and 1, ammediol, 1, separation and Extraction source in ammediol ester or its mixture.
[0020] extracting method comprises that use exsiccant substrate is as the vegetable material with solvent impregnated mistake.In current perfume industry, dipping is the modal and most economical important technology that is used to extract aromatoising substance.In the method, starting material are immersed in the solvent, this solvent can dissolve required aromatoising substance or other extract.Dipping time be some branches hour to the several months.Dipping is generally used for from wooden or filamentary material and animal-origin extraction aromatic compound.This technology also can be used for extracting volatility material odorous too strong or the easy sex change owing to heat for distillation.
[0021] or, solvent is permeable to be leached from biomass or substrate up to enough soluble materials through substrate material.By coarse filtration, filter or centrifugal the substrate chip is separated with extract.
[0022] another technology from raw material extraction compound is a supercritical extraction.This technology uses low-heat to reduce the degraded of extract.Postcritical CO2 can be used in this extractive technique.
[0023], extracts and also can be undertaken by other extractive technique (comprising distillation) according to the present invention.1 of biology origin, ammediol and conjugate esters thereof can be used as solvent in the distillation extraction technology.In this technology, be commonly used to from plant such as white orange blossom and Rose, obtain aromatic compound, with raw material heating, and the recovery aromatic compound that condenses by the distillatory steam.The distillation method comprises vapor distillation, wherein uses steam to evict volatile aromatic compound from from vegetable material, stays the condensation product that is known as the water-sol.Distillation comprises that also destructive distillation is a destructive distillation, and wherein raw material is heated under the condition of carrier free solvent.In this case, 1 of biology origin, ammediol and conjugate esters thereof are used as the solvent of dilution aromatic compound after extraction.
[0024] in another extracting method, is called milling process,, and collects the oil of extruding extrusion of raw material physics or compression.This method is considered to extraction method, and is normally used for extracting from the skin of citrus fruit compound most, has the oil of feasibility because enough this methods that makes are contained in these sources.Fragrance of a flower absorption method is that another kind is suitable for using 1 of biology origin, ammediol, the extraction method of its conjugate esters or its mixture.
[0025] 1 of the biology origin, ammediol and conjugate esters thereof can be used as to extract uses solvent, and can be used as a kind of component in comprising the composition of plant milk extract.Plant origin includes but not limited to all plants, seed, stem, root, flower, leaf, pollen end, spices and oil.A kind of extract type that is suitable for extracting or dilutes is the medicinal herbs extracts.
[0026] the medicinal herbs extract is the liquor of medicinal herbs and solvent.Dry or fresh medicinal herbs and solvent are made up, remove solid matter then, only stay oil with the medicinal herbs of solvent.This method is known as extraction method, and this method obtains the medicinal herbs extract.
[0027] the medicinal herbs extract is as dietary supplement or alternative medicine is sold and curing, be used in the cooking or the beverage seasoning usually.They also are used in personal care product such as skin and hair is used in the product.
[0028] a spot of carbonic acid gas has radioactivity in the atmosphere.The generation of this 14C carbonic acid gas is to take place under following situation: nitrogen is clashed into by the neutron that ultraviolet ray generates, and causing nitrogen to lose proton and forming molecular weight is 14 carbon, and it is oxidized to carbonic acid gas at once.But this radio isotope accounts for the small portion of big gas carbon occupies measurable share.Atmospheric carbon dioxide is made organic molecule during being called photosynthetic process and is circulated known by green plants.When generating carbonic acid gas (it is released and turns back in the atmosphere), finishes the life metabolism organic molecule of green plants or other form this circulation.In fact the life of form of ownership depends on this green plants and produces organic molecule to obtain to promote growth and regenerated chemical energy on the earth.Therefore, be present in the part that 14C in the atmosphere becomes all life forms and biologic thereof.These biological degradations obtain CO
2Renewable basic organic molecule do not promote Global warming because atmospheric carbon emission is not had a net increase of length.By contrast, fossil fuel carbon does not have the radiocarbon C14 ratio of significant atmospheric carbon dioxide.
[0029] evaluation of renewable basic carbon can be undertaken by standard test methods in the material.Use radiocarbon C14 and isotopic ratio mass spectroscopy, can measure the bio-based content of material.ASTMInternational, formal title is U.S.'s test and materialogy meeting (American Society forTesting and Materials), has established the standard method of the bio-based content that is used for evaluating material.This ASTM method is known as ASTM-D6866.
[0030] uses ASTM-D6866 and obtain " bio-based content " and be based upon identical with radiocarbon dating conceptively, and do not use the age formula.The ratio of the amount of the radiocarbon C14 in the amount of this analysis by deriving the radiocarbon C14 (14C) in unknown sample and the current reference standard carries out.This than the report value represent that with percentage ratio unit is " pMC " (contemporary carbon %).If analyzed material is the current radiocarbon C14 and the mixture of fossil-carbon (not comprising radiocarbon C14), then the amount of the biological material that exists in the pMC value of Huo Deing and the sample is directly related.
[0031] the current reference standard of using in radiocarbon dating is NIST (national standard and technology meeting, National Institute of Standards and Technology) standard is used the known radiocarbon C14 content that is about as much as nineteen fifty in Christian era.Select nineteen fifty in Christian era to be and testing the time before by the thermonuclear weapon of a large amount of excessive radiocarbon C14 (being called " bomb carbon (bomb carbon) ") of in the atmosphere introducing of exploding at every turn because it has been represented.AD nineteen fifty reference value is 100pMC.
[0032] twice that 1963 year almost reach standard level of " the bomb carbon " in the atmosphere before testing the peak period and stopping test protocols.Its distribution in atmosphere is an approximation since it occurs, and for for the plant and animal of having survived since nineteen fifty in Christian era, the value of performance is greater than 100pMC.It reduces as time goes by gradually, and present value is near 107.5pMC.This means that fresh biological material such as cereal can provide the radiocarbon C14 sign near 107.5pMC.
[0033] fossil-carbon and current carbon are combined into the desaturation (dilution) that will cause current pMC content in the material.107.5pMC represents current biological material by supposition, and 0pMC represents petroleum derivative, and the pMC observed value of these materials will reflect the ratio of two types of components.100% material from current soybean will provide the radiocarbon C14 sign near 107.5pMC.If this material is by 50% petroleum derivative institute desaturation, then it will provide the radiocarbon C14 sign near 54pMC.
[0034] by specifying 100% to equal 107.5pMC and 0% and equal 0pMC, obtains the biomass content result.In this, observed value is that the sample of 99pMC will provide and be equivalent to 93% bio-based content results.
[0035] according to ASTM-D6866 material described herein is estimated.The mean value of quoting in this report comprises that 6% absolute range (at every end ± 3% of bio-based content value) is to make an explanation to the variation of component radiocarbon C14 sign end value.Suppose all material be current or fossil sources and required result be the amount of the bio-based component in " being present in " this material, rather than in manufacturing processed the amount of the bio-based materials of institute's " use ".
[0036] the applicant uses is used for describing 1 of biology origin obtained by the method for the present invention, the term of ammediol " purifying in fact " expression comprises having 1 of at least a following feature, the composition of ammediol: 1) the ultraviolet light absorption value at 220nm is lower than about 0.200, be lower than about 0.075 and be lower than about 0.075 with ultraviolet light absorption value in the ultraviolet light absorption value of 275nm at 250nm; Or 2) L that has of composition
*a
*b
*" b
*" colour is lower than about 0.15 and be lower than about 0.075 in the absorbancy of 270nm; Or 3) the superoxide composition is lower than about 10ppm; Or 4) concentration of total organic impurity is lower than about 400ppm.
[0037] " b
*" value be with spectrophotometry by CIE L
*a
*b
*Measuring method ASTMD6290 defined " yellow blue observed value ".Abbreviation " AMS " is meant accelerator mass-spectrometry.
[0038] abbreviation " IRMS " is meant the CO that measures than mass-spectrometry by the high precision stable isotope
2Observed value.
[0039] " biology generates " is meant by one or more living organism species or strain, comprises the organic compound that specific bacterium, yeast, fungi and other microbial strain generate." biological generation ", " the biology origin " and " biology generates " are used with the free burial ground for the destitute in this article.This organic compound is by forming from atmospheric carbon dioxide and by the carbon that green plants changes into sugar and starch.
[0040] " biologically-based " is meant that organic compound is synthetic from the organic constituent that biology generates.Further considered that synthetic method disclosed herein can be effectively from removing 1, the alcohol that the biology outside the ammediol generates synthesizes other monoesters and diester; Described alcohol comprises ethylene glycol especially, glycol ether, and triglycol ,-, dipropylene glycol, tripropylene glycol, 2-methyl isophthalic acid, ammediol, neopentyl glycol and dihydroxyphenyl propane." bio-based " and " biogenetic derivation "; " the biology origin " and " biological origin " are used with the free burial ground for the destitute in this article.
[0041] " atmosphere source carbon " used herein is meant from being the carbon atom of free carbon dioxide molecule origin earth atmosphere in decades recently.This carbon can be identified by specific radioisotopic existence as herein described aspect quality." green carbon ", " big gas carbon ", " environmental friendliness carbon ", " the life cyclic carbon, " non-fossil fuel carbon ", " non-petroleum base carbon ", " carbon in atmosphere source " and " bio-based carbon " can use with the free burial ground for the destitute at this paper.
[0042] " sweetener " is to be added to food, beverage, and makeup are used for improving the material of the taste of these compositions in medicine or the medicine.Oils such as orange oil is considered to sweetener.
[0043] composition of the present invention comprises and comprises 1, ammediol ester and extract the composition of product.This ester has the bio-based carbon of different amounts according to the difference of the compound that uses in the esterification.1 of biology origin, ammediol contain bio-based carbon.This 1, three carbon atoms of all in the ammediol are bio-based carbon.If conjugate esters uses the carboxylic-acid that comprises all bio-based carbon to form, the ester that then obtains also contains all bio-based carbon.Yet, if carboxylic-acid comprises abiotic basic carbon, promptly, derive from the carbon in fossil oil source, the ester that then obtains will contain the bio-based carbon of certain percentage ratio, and it is than by 1 of biology origin, and three carbon of ammediol contribution are with proportional by the carbon number of carboxylic acid contribution.
[0044] for example, the propylene glycol SUNSOFT Q-182S contains 39 carbon atoms, derives from 18 carbon of each stearic acid carbochain and derives from 1,3 carbon of ammediol.Therefore, if stearic acid is non-bio-based, then 36 carbon in 39 carbon altogether of propylene glycol SUNSOFT Q-182S are non-bio-based carbon.Bio-based content prediction value by the propylene glycol SUNSOFT Q-182S of the stearate acid preparation of the propylene glycol of biology origin and abiology origin is 7.7%.
[0045] using during the ASTM-D6866 method analyzes, (BENZOFLEX (R) 284, Velsicol Chem.Corp.Rosemont IL) have 0% bio-based carbon content to find the propylene glycol dibenzoate.To using 1 of biology origin, the same analysis of ammediol synthetic propylene glycol dibenzoate shows to have 19% bio-based carbon content.By 1 of biology origin, the bio-based carbon content predictor of the propylene glycol dibenzoate of ammediol preparation is 17.6%, and it is in the standard deviation scope of described method.
[0046] if the stearic acid in the foregoing description is a bio-based, the propylene glycol SUNSOFT Q-182S that then obtains will have 100% bio-based content.Therefore, 1 of biology origin, the bio-based content value that the conjugate esters of ammediol has is proportional with the bio-based content of the acids that is used to form ester.Therefore, the bio-based content that this ester can have is at least 3% bio-based carbon, at least 6% bio-based carbon, at least 10% bio-based carbon, at least 25% bio-based carbon, at least 50% bio-based carbon, at least 75% bio-based carbon and 100% bio-based carbon.
[0047] comprise extract and 1, the composition of ammediol conjugate esters can have about 0.1% to about 5% ester, about ester of 0.5% to 25%, about 25% to about 50% ester, about 50% to about 75% ester and about 75% to about 99% ester, and about 99% to about 100% ester.
[0048] composition of the present invention also comprises and contains 1, the composition of ammediol and extract.1 of these compositions, ammediol have at least 95% bio-based carbon, perhaps, 1, ammediol has 100% bio-based carbon.Comprise extract and 1, the composition of ammediol can have about 0.1% to about 5% 1, ammediol, about 0.5% to 25% 1, ammediol, about 25% to about 50% 1, ammediol, about 50% to about 75% 1, ammediol and about 75% to about 99% 1, ammediol.
[0049] composition of the present invention also comprises and contains 1, ammediol and 1, the conjugate esters of ammediol and the composition of extract.1 of these compositions, ammediol have at least 95% bio-based carbon, perhaps, 1, ammediol has 100% bio-based carbon.Comprise extract and 1, ammediol and 1, the composition of the mixture of the conjugate esters of ammediol can have about 0.1% to about 5% mixture, about 0.5% to about 25% mixture, about 25% to about 50% mixture, about 50% to about 75% mixture and about 75% to about 99% mixture.
The mixture of [0050] two pure and mild ester can be very effective in extraction, and this mixture can be than the more activeconstituents of independent solvent extraction.Using solvent mixture to extract more activeconstituents from vegetable material is because ester (particularly diester) is nonpolar, and diol component is a polar.Therefore, the mixture of use ester and glycol can be easily from the plant extract lipophilic composition.In some cases, the density of ester can be higher than the density of glycol far away, and after pickling process, " cake " (extract of ester) can easily solidify and be separated with glycol.In addition, ester can be a volatile compound, thereby and in extract ester can easily be evaporated and obtain coagulating fragrant body, volatile oil, absolute oil, or the fragrance of a flower is inhaled and carried oil (enfleurage).
[0051] 1, ammediol, 1, conjugate esters of ammediol and composition thereof is when being used as solvent and thinner with other appropriate solvent (comprising water) effectively when being used in combination.
1 of biology origin, ammediol
[0052] the present invention relates to comprise the extract of plant, vegetables, proteins/peptides, marine products class, algae or newborn class or the composition of essence enriched material or volatile oil, wherein use 1 of biology origin, ammediol or its ester conjugate are as the chemical solvents that is used to extract or dilute plant, vegetables, proteins/peptides, marine products class, algae or newborn class extract or essence enriched material or volatile oil." the biology origin " is meant by one or more living organism species or strain, comprises specific bacterium, yeast, fungi and other microbial strain synthetic 1, ammediol.Herein disclosed is and can be used on shampoo or health with 1 of the biology origin in the detergent composition, ammediol.
[0053] 1 of the biology origin, ammediol is collected with high-purity forms.This 1, ammediol has at least a following feature: 1) be lower than about 0.200 and be lower than about 0.075 and be lower than about 0.075 in the ultraviolet light absorption value of 275nm in the ultraviolet light absorption value of 250nm in the ultraviolet light absorption value of 220nm; Or 2) L that has of composition
*a
*b
*" b
*" colour is lower than about 0.15 and be lower than about 0.075 in the absorbancy of 270nm; Or 3) the superoxide composition is lower than about 10ppm; Or 4) concentration of total organic impurity is lower than about 400ppm." b
*" value is with spectrophotometry, by CIEL
*a
*b
*The blue observed value of the defined yellow of measuring method ASTM D6290.
[0054] 1, the purity level of ammediol can characterize by many different methods.For example, the reservation level of measurement contaminative organic impurity is a kind of useful measure.1 of biology origin, the purity level that ammediol can have are the total organic pollutants that is lower than about 400ppm; Preferably be lower than about 300ppm; Most preferably be lower than about 150ppm.The total organic purity of term ppm is meant the ppm level of the carbon compound measured by vapor-phase chromatography (rather than 1, ammediol).
[0055] 1 of the biology origin, ammediol also can use many other parameters, characterizes such as the ultraviolet absorptivity under different wave length.220nm, 240nm and 270nm wavelength are considered to can be used for measuring the purity level of composition.1 of biology origin, the purity level that ammediol can have be, wherein is lower than about 0.200 and be lower than about 0.075 and be lower than about 0.075 in the UV of 270nm absorbancy in the UV of 240nm absorbancy in the UV of 220nm absorbancy.
[0056] 1 of the biology origin, the b that ammediol can have
*Colour (CIE L
*a
*b
*) be lower than about 0.15.
[0057] 1 of the biology origin, the purity of ammediol composition also can be estimated by the method for significant measurement peroxide level.1 of biology origin, the concentration of the superoxide that ammediol can have is lower than about 10ppm.
[0058] it is believed that, above-mentioned that be used for the biology origin and purified 1, the purity level parameter of ammediol (the same or similar method of those disclosed method among use and the U.S. Patent application No.2005/0069997), this composition with from from oil source through 1 of chemical purification, 1 of ammediol preparation, the ammediol composition differentiates.
[0059] by 1 of biology of fermentations generation, ammediol is known, is included in United States Patent (USP) 5,686,276, United States Patent (USP) 6,358,716, with United States Patent (USP) 6,136, in 576, it discloses and has used the sugar that during fermentation can use cheap green carbon source such as glucose or other plant origin to synthesize 1, the method for the recombined engineering bacterium of ammediol.Every piece of content of these patents is incorporated into this paper as a reference especially.1 of biology origin, ammediol can be based on using at United States Patent (USP) 5,686, and the disclosed fermenting broth that is generated by genetically engineered large intestine Chinese mugwort Xi Shi bacillus (E.coli) obtains in 276.Can use other single creature body or the combination of organism to come biological student to become 1, ammediol, employing is carried out genetically engineered organism according to means known in the art and is carried out." fermentation " is meant such system, and it comes reaction between catalytic substrate and other nutritive substance by using biological catalyst.Biological catalyst can be full organism, isolating enzyme, or have any its combination or the composition of enzymatic activity.Can be used for generating with purifying biological and learn 1 of origin, the fermentation system of ammediol is open in laid-open U.S. Patents application No.2005/0069997 for example incorporated herein by reference.
[0060] bacillus coli DH 5 alpha that contains clay pKP1 (the klebsiella genome that contains some encoding glycerol dehydratase) through changing according to budapest treaty (Budapest Treaty) April 18 nineteen ninety-five by the ATCC preservation, and ATCC No. is ATCC 69789.The bacillus coli DH 5 alpha that contains clay pKP4 (the klebsiella genome that contains some coding dioldehydrase) through changing according to budapest treaty April 18 nineteen ninety-five by preservation, and ATCC No. is ATCC 69790." ATCC " used herein is meant the international depositary institution of American type culture collection, and the address is 10801University Boulevard, Manassas, VA, 201102209, U.S.A.." ATCC No. " is the accession number that by ATCC preservation culture the time culture is provided.
[0061] by 1 of methods described herein generation and biology origin used in this invention, ammediol (bio-PDO) comprises the carbon that derives from atmosphere and merged by plant, and it is configured for generating 1 of biology origin, the raw material of ammediol.This shows that Bio-PDO only contains renewable carbon, and does not contain fossil fuel carbon or petroleum base carbon.Therefore use 1 of biology origin, ammediol and conjugate esters thereof are less to the influence of environment, because this propylene glycol does not consume the fossil oil that is reducing.Use 1 of biology origin, therefore ammediol and conjugate esters thereof do not promote greenhouse gas emission not to atmosphere net increase carbonic acid gas yet.Therefore, the invention is characterized in and compare more natural with the analogous composition that comprises the petroleum base glycol and have lower environmental influence.
[0062] in addition, because 1 of the biology origin of in composition as herein described, using, the purity of ammediol is higher than PDO and other glycol of chemosynthesis, preferentially is used by its glycols such as propylene glycol commonly used to make introducing can cause the risk of irritating impurity to be lowered.
[0063] in one embodiment of the invention, provide to comprise 1, ammediol and extract the composition of product, wherein 1, ammediol is the biology origin.When adopting aforesaid ASTM-D6866 to estimate, 1 of biology origin, ammediol can have at least 85% bio-based carbon, at least 95% bio-based carbon, or 100% bio-based carbon.
[0064] 1 of the biology origin, the sample of ammediol uses ASTM method D 6866-05 to analyze.Result from Hawkeye State university has shown that above-mentioned sample is 100% bio-based content.In separate analysis, also use the ASTM-D6866 method to chemistry or petroleum-based 1, ammediol (available from SHELL) is analyzed, and finds that it has 0% bio-based content.Find that propylene glycol (the USP level derives from ALDRICH) has 0% bio-based content.
[0065] other the renewable base or the glycol of biology origin contained in this paper, particularly such as ethylene glycol or 1,2 propylene glycol, and glycol ether, triglycol or the like can be used in extract of the present invention or the composition.
[0066] may have some situation, extract wherein of the present invention or extract composition and can comprise 1 of biology origin, the diol component of ammediol and one or more abiology origin be such as 1 of for example chemosynthesis, the combination of ammediol.In this case, except bio-based carbon content, if confirmable words may be difficult to also determine that how much percentage ratio of diol component is the biology origin by the calculating diol component.In this, in extraction solvent of the present invention and extract composition, be used as solvent or be used to form 1, the ammediol ester adopted 1, ammediol, can comprise at least about 1% bio-based carbon content to maximum 100% the bio-based carbon content and any percentage ratio wherein.
1 of biology origin, the ester conjugate of ammediol
[0067] 1 of the biology origin, the ester of ammediol " bio-PDO " can be synthetic by bio-PDO is contacted with organic acid.Organic acid can be from any source, preferably from biogenetic derivation or synthetic from fossil sources.Most preferably, organic acid has following formula structure: R from natural origin or biological origin
1R
2-COOH.Substituent R wherein
1Can be saturated or unsaturated, replace or unsubstituted, aliphatic series or hydrocarbon aromatics, straight or branched, chain length is 1-40, or its salt or alkyl ester.Substituent R wherein
2Can be H or COOH.Hydrocarbon chain also can have one or more such as following functional group: alkene, acid amides, amine, carbonyl, carboxylic acid, halogenide, hydroxyl.Generate the ester that contains all biological base carbon from naturally occurring organic acid.These naturally occurring organic acids, particularly those that generate by organism are classified as and biologically generate class, and the ester that obtains or diester also are classified as the biological class that generates thus.The naturally occurring source of this lipid acid comprises Oleum Cocois, different animal tallows, lanolin, fish oil, beeswax, plam oil, peanut oil, sweet oil, oleum gossypii seminis, soybean oil, Semen Maydis oil, rapeseed oil.Can use conventional fractionation and/or technology for hydrolyzing to obtain lipid acid if necessary from these materials.
[0068] be used to generate 1 of biology origin, the suitable carboxylic-acid of the ester of ammediol generally includes: (1) contains the monocarboxylic acid class of C1-C3 carbon, comprises formic acid and acetate; (2) lipid acid is such as those acids that contain four or a plurality of carbon atoms; (3) saturated fatty acids, such as butyric acid, caproic acid, valeric acid, sad, capric acid, lauric acid, tetradecanoic acid, palmitinic acid, stearic acid, eicosanoic acid, and docosoic; (4) unsaturated fatty acids, such as oleic acid, linolic acid, and sinapinic acid (euricic acid); (5) polyunsaturated fatty acid, such as alpha-linolenic acid, therapic acid (or moroctic acid, 8,12,15-tetraenoic acid (moroctic acid)), eicosatetraenoic acid, ω-6 lipid acid, arachidonic acid, and omega-fatty acid, timnodonic acid (or twenty carbon-5,8,11,14,17-pentaene acid (timnodonicacid)), clupanodonic acid (or 22 carbon-4,8,12,15, and docosahexenoic acid (or 22 carbon-4,7 19-pentaene acid (clupanodonicacid)),, 10,13,16,19-acid (cervonicacid)); (6) hydroxy aliphatic acids is such as 2-hydroxylinolic acid and castor oil acid (recinoleicacid); Phenyl alkane fatty acid, as 11-phenyl undecanoic acid, 13-phenyl tridecanoic acid and 15-phenyl tridecanoic acid; (7) cyclohexyl fatty acid is as 11-cyclohexyl undecanoic acid and 13-cyclohexyl tridecanoic acid.
[0069] following acids and salt thereof or alkyl ester are particularly useful: acetate, butyric acid, lauric acid, tetradecanoic acid, palmitinic acid; stearic acid, eicosanoic acid, hexanodioic acid, phenylformic acid is sad; toxilic acid, palmitinic acid, sebacic acid, arachidonic acid, sinapinic acid; Zoomeric acid, pentadecylic acid, margaric acid, nondecylic acid, therapic acid; eicosatetraenoic acid, timnodonic acid, clupanodonic acid, the acid of tetracosa carbon pentaene, four caproic acids; docosahexenoic acid, (α)-linolenic acid, docosahexenoic acid, timnodonic acid, linolic acid; arachidonic acid, oleic acid, sinapinic acid, formic acid, propionic acid; valeric acid, caproic acid, capric acid, propanedioic acid; Succinic Acid, pentanedioic acid, hexanodioic acid, pimelic acid; suberic acid, nonane diacid, tartrate, Citric Acid; Whitfield's ointment, acetylsalicylic acid, n-nonanoic acid ， docosoic; hexacosanoic acid, pearly-lustre resin acid, montanic acid, myricyl acid; lacceroic acid, ceromelissic acid, geddic acid, ceroplastic scid; undecylenic acid, ricinolic acid, and eleostearic acid, and the mixture of this acid.Suitable organic acid more preferably inventory is an acetate, hexanodioic acid, phenylformic acid, toxilic acid, sebacic acid and these sour mixtures.The more preferably inventory of suitable " lipid acid " typically refers to the acids that can be used for containing in the carbon of the present invention 8-40 carbon, comprises butyric acid, valeric acid, caproic acid is sad, n-nonanoic acid, capric acid, lauric acid, tetradecanoic acid, palmitinic acid, stearic acid, eicosanoic acid ， docosoic, hexacosanoic acid, oleic acid, linolic acid, linolenic acid, the pearly-lustre resin acid, montanic acid, myricyl acid, lacceroic acid, ceromelissic acid, geddic acid, ceroplastic scid and these sour mixtures.In these acid, these acid and salt thereof and alkyl ester be stearic acid most preferably, lauric acid, palmitinic acid, oleic acid, 2 ethyl hexanoic acid and 12-oxystearic acid and these sour mixtures.
The ester class of [0070] being produced comprises 1, all suitable compound monoesters and diester that ammediol uses described organic carboxyl acid class to form.Some esters that generate comprise propylene glycol SUNSOFT Q-182S and monostearate especially, a propylene glycol dilaurate and a lauric acid ester, Rikemal PO 200 and monooleate, propylene glycol two valerates and a valerate, a propylene glycol dicaprylate and an octanoate, propylene glycol two myristinates and a nutmeg acid esters, propylene glycol dipalmitate and monopalmitate, propylene glycol Er docosoic ester and Yi docosoic ester, the propylene glycol adipic acid ester, propylene glycol maleic acid ester, propylene glycol dibenzoate, propylene-glycol diacetate, and their all mixtures.
[0071] especially, the ester that generates comprises: propylene glycol SUNSOFT Q-182S and monostearate, Rikemal PO 200 and monooleate, a propylene glycol dicaprylate and an octanoate, propylene glycol two nutmeg acid esters and a nutmeg acid esters, and their all mixtures.
[0072] common 1, ammediol can be preferably under the condition that rare gas element exists, in the existence of catalyzer or two or more mixture of catalysts or not under the existence condition, under 25 ℃ to 400 ℃ temperature, the mixture of contact lipid acid or lipid acid or soap and with its reaction.
[0073], forms water and in inert gas flow or under vacuum, remove to anhydrate to drive and react completely at period of contact.Can remove any volatile by product similarly.When reacting completely, can stop heating and cooling.
[0074] can be preferably by dissolving in deionized water with remove catalyzer.If can remove catalyzer by handling with deionized water, then reaction mixture is handled with formation salt with the aqueous solution of acid or alkali, and by washing or remove by filter salt.
[0075] is further purified to obtain highly purified fatty acid ester, the preferred highly purified fatty acid ester that obtains to be used for medicinal application, can be undertaken by as described below: be dissolved in the solvent, this solvent easy dissolved fat acid esters and dissolve minimal fatty acid ester at a lower temperature under comparatively high temps, and at low temperatures in adding or do not add under the condition of other solvent and carry out recrystallization.
[0076] catalyzer can be acid, and its non-limitative example is sulfuric acid or tosic acid.Catalyzer is alkali also, and non-limitative example is a sodium hydroxide.Catalyzer is salt also, and non-limitative example is a potassium acetate.Catalyzer is alkoxide also, and non-limitative example is a titanium tetraisopropylate.Catalyzer is heterogeneous catalyst also, and non-limitative example is: zeolite, heteropolyacid, macroporous resin, or ion exchange resin.Catalyzer is metal-salt also, non-limitative example tin chloride or cupric chloride.Catalyzer is enzyme also, as known in the art those.Catalyzer is organic acid also, and non-limitative example is a formic acid.At last, catalyzer is organometallic compound also, and non-limitative example is a n-butylstannoic acid.
[0077] this method can be carried out under the condition that has or do not exist solvent.If solvent is not to promote that the fatty acid ester generation is necessary, then preferred this method is carried out under the condition that does not have solvent.
[0078] this method can be carried out under barometric point or under the vacuum or under the pressurized conditions.
Reaction 1 (diester)
R wherein
1And R
2Be that preferred carbon chain length is about 1 to about 40 hydrocarbon.This hydrocarbon can be saturated or unsaturated, replacement or unsubstituted, straight or branched.
M is a hydrogen, basic metal or alkyl.
Reaction 2 (monoesters)
R wherein
1Be that preferred carbon chain length is about 1 to about 40 hydrocarbon.This hydrocarbon can be saturated or unsaturated, replacement or unsubstituted, straight or branched.M is a hydrogen, basic metal or alkyl.
[0079] composition of the present invention comprises that wherein R1 has one or more esters that are selected from following functional group: alkene, acid amides, amine, carbonyl, carboxylic acid, halogenide, hydroxyl, ether, alkyl oxide, sulfuric ester and ether sulfuric ester.This ester can have following formula structure: R1-C (=O)-O-CH2-CH2-CH2-O-C (=O)-R2, wherein R1 and R2 are that chain length is the about 1 straight or branched carbochain to about 40 carbon.R1 and R2 can have one or more following functional groups that are selected from: alkene, acid amides, amine, carbonyl, carboxylic acid, halogenide, hydroxyl, ether, alkyl oxide, sulfuric ester and ether sulfuric ester.In addition, R1 can be identical carbochain with R2 under the situation of diester.
[0080] can use any mol ratio of glycol to dicarboxylic acid or its salt or its ester.Glycol is about 1: 3 to about 2: 1 to the preferable range of dicarboxylic acid.Can adjust this ratio moves to the direction that generates diester to help reacting from generating monoesters.Usually, in order to help the generation of diester, use slightly greater than about 1: 2 ratio; And, use about 1: 1 ratio in order to help the generation of monoesters.Usually, surpass the monoesters product if wish diester product, then glycol can be about 1.01: 2 to about 1.1: 2 to the ratio of dicarboxylic acid; Yet,, use about 1.01: 1 to about 2: 1 ratio if wish the monoesters product.
[0081] catalyst content of reaction usefulness can be the 1ppm of reaction mixture to 60 weight %, preferred 10ppm is to 10 weight %, more preferably 50ppm is to 2 weight %.
[0082] product can comprise diester, and monoesters, or the combination of diester and monoesters, and a spot of unreacted acid and glycol are according to the difference of reaction conditions and different.Unreacted glycol can be by being removed with deionized water wash.Unreacted acid can be by with deionized water or alkaliferous solution washing or be removed during recrystallization.
[0083] 1, any ester of ammediol can be prepared according to the present invention or use.Can prepare 1, the monoesters of the short chain of ammediol, medium chain and long-chain and diester.Particularly can prepare and in alkyl chain, contain 1 those ester classes of having an appointment to about 36 carbon.More particularly, can prepare following monoesters and diester: propylene glycol SUNSOFT Q-182S (monostearate and mixture), propylene glycol dilaurate (a lauric acid ester and a mixture), Rikemal PO 200 (monooleate and mixture), propylene glycol two valerates (valerate and mixture), propylene glycol dicaprylate (octanoate and mixture), propylene glycol two nutmeg acid esters (a nutmeg acid esters and a mixture), propylene glycol dipalmitate (monopalmitate and mixture), propylene glycol Er docosoic ester (Yi docosoic ester and mixture), propylene glycol adipic acid ester, propylene glycol maleic acid ester, propylene glycol dibenzoate, and propylene-glycol diacetate.
[0084] for containing extract and 1, ammediol, 1, the conjugate esters of ammediol or the composition of its mixture, extract can be compound or the one group of compounds that extracts from source material.In some applications, extract extracts from natural source, as plant-sourced.The example of suitable natural extract comprises plant milk extract, vegetable extract, protein extract, lipid extracts, marine products class extract, Algae Extract and newborn class extract.
[0086] section of preferred plant and tree comprises: Anacardiaceae (Anacardiaceae), Araeceae (Araceae), acorn nut Ochnaceae (Balanopaceae), Balsaminaceae (Balsaminaceae), Begoniaceae (Begoniaceae), Boraginaceae (Boraginaceae), Buxaceae (Buxaceae), Caricaceae (Caricaceae), Curcurbitaceae (Cucurbitaceae), guttiferae (Clusiaceae), Daphniphyllaceae (Daphniphyllaceae), Ericaceae (Ericaceae), Euphorbiaceae (Euphorbiaceae), pulse family (Fabaceae), Fagaceae (Fagaceae), Hippocastanaceae (Hippocastanaceae), jade hairpin section (Hostaceae), Hydrangeaceae (Hydrangeaceae), Labiatae (Labiateae), the careless section (Lilaeaceae) of different post, Magnoliaceae (Magnoliaceae), Moringaceae (Moringaceae), Myristicaceae (Myristicaceae), Myrtaceae (Myrtaceae), Oleaceae (Oleaceae), the orchid family (Orchidaceae), the green section of three lobes (Peperomiaceae), Pinaceae (Pinaceae), Primulaceae (Primulaceae), and Rutaceae (Rutaceae).
[0087] comprises as plant of extracting the source and the preferred species of tree: pink blossom ocean alpine yarrow (Achilleamillefolium), horse-chestnut (Aesculus chinensis), garlic (Allium sativum), sweet wormwood (Artemisia apiacea), babassu butterfat (Astrocaryum murumuru), peach fruit palmitic acid (Bactris gasipaes), wax gourd (Benincasa hispida), circular cone Stem of Oriental Bittersweet (Celastruspaniculatus), Iceland's lichens (Cetraria islandica), goosefoot (Chenopodiumquinoa), red bark tree (Cinchona succirubra), Citrus bergamia (Citrus bergamia), sweet orange (Citrus sinensis), coriander (Coriandrum sativum), fur pine algae (Codiumtomentosum), myrrh (Commiphora molmol), YESHANZA (Crataegus cuneata), cucumber (Cucumis sativus), blue gum (Eucalyptus globulus), Gleditsia officinalis (Gleditsiasinensis), Gnetum amazonicum, Chinese Hibiscu (Hibiscus rosa-sinensis), Jasminum officinale L. (Jasminum officinale), the flower bud of Chinese Honeysuckle (Lonicera caprifolium) of overgrowing, honeysuckle (Lonicera japonica), tomato (Lycopersicon esculentum), apple (Malus pumila), german chamomile (Matricaria recutita), Maximiliana maripa, short leaf Punetree (Melaleucahypericifolia), angle times aphid (Melaphis chinensis), Mentha piperita (Mentha piperita), Mouriri apiranga, Nasturtium officinale (Nasturtium officinale), lotus (Nelumbo nucifera), root of Redsepal Eveningprimrose (Oenothera biennis), the tuber of dwarf lilyturf (Ophiopogon japonicus), avocado (Perseaamericana), Paffia paniculata, golden cypress (Phellodendron amurense), phyllanthus emblica (Phyllanthus emblica), pea (Pisum sativum), tormentil (Potentillaerecta), red sandalwood (Pterocarpus santalinus), glutinous rehmannia (Rehmannia chinensis), weld mignonette (Reseda luteola), black Semen sojae atricolor (Ribes nigrum), Rosa centifolia L (Rosacentifolia), black pine (Rubus thunbergii), spondias amara (Spondias amara), benzoin (Styrax benzoin), and thyme (Thymus vulgaris).
[0088] extraction source also comprises algae.Algae section as extraction source also comprises Acrochaeticaceae, Characeae (Characeae), Codiaceae (Codiaceae), Fucaceae (Fucaceae), Laminariaceae (Laminariaceae), Lemaneaceae (Lemaneaceae), be subordinate to Ulvaceae (Ulvaceae), and Pamariaceae.Preferred algae species comprises Lemanea fluviatilis (red algae), (L.), Ascophyllum nodosum (brown alga), Lemanea fluviatilis, Lemanea fucina (red algae), Ulva lactuca (green alga), palmate sea-tangle (Laminaria digitata), wedge base sea-tangle (Laminariaochroleuca).
[0089] extraction source also comprises the Mycophyta member.For extraction, can use Holobasidiomycetes (Homobasidiomycetes) (or false truffle (true mushrooms)).Some exemplary Agaricus edibilis comprise: polyporaceae (Meripilaceae), Tricholomataceae (Tricholomataceae), and Ganodermataceae (Ganodermataceae) (maitake, shiitake, reishi mushroom).The concrete kind comprises: Agaricus bisporus (Agaricus bisporus), Agaricus campestris, needle mushroom (Flammulina velutipes), Hypsizygus tessulatus, mushroom (Lentinus edodes), pin phellinus linteus (Phellinus linteus), pleurotus sapidus (Pleurotus cornucopiae), oyster cap fungus (Pleurotus ostreatus), white fungus (Tremella fuciformis), Sparassis crispa (Sparassiscrispa), kahikatea reveals bacterium (Tuber magnatum), and straw mushroom (Volvariella volvacea).
[0090] the isolating species of bryophyte from vegitabilia's (it comprises liver moss) can be used as extraction source, and also can use some lichens species to be used for extracting.
[0091] marine source such as plant, algae, planktonic organism, and fish are used to produce extract.Protein and lipid extracts source comprise plant, animal, fish, and people's (as placenta) material.The breast class can be used as the extract source and is used for separating and proteins concentrate, peptide and lipid.
[0092] openly can implement disclosed herein and claimed all compositions and method need not to carry out unsuitable test according to of the present invention.Although described composition of the present disclosure and method according to preferred version, but it will be apparent to one skilled in the art that, can carry out various variations to composition and method in the step of methods described herein or in the sequence of steps, and not break away from notion of the present invention, spirit and scope.More particularly, obviously the reagent that some chemistry is relevant can be used for substituting reagent as herein described, and can realize identical or similar result.Conspicuous for those skilled in the art all similarly substitute and modify and all think and be in by the defined spirit of the present invention of appended claims, in scope and the notion.
Embodiment
[0093] the present invention further describes in following examples.Very clear, these embodiment although represented preferred version of the present invention, only provide with exemplary approach.From above-mentioned discussion and these embodiment, those skilled in the art can learn essential characteristic of the present invention, and under the condition that does not break away from the spirit and scope of the present invention, can carry out multiple change and modification makes its suitable multiple use and condition to the present invention.
[0094] unless otherwise mentioned, otherwise all the components that uses in the preparation personal care composition of describing in following examples is a commercial source.
[0095] in addition, the implication of the abbreviation of use is as follows: " weight % " is meant weight percentage, and " qs " is meant in right amount; " EDTA " is meant edetate; " ℃ " be meant degree centigrade; " °F " be meant Fahrenheit temperature, " Bio-PDO " is meant 1 of biology origin, ammediol; " ppm " is with respect to per 1,000,000 parts umber; " AU " is absorbance unit; " nm " is nanometer; " GC " is gas-chromatography; " APHA " is American Public Health Association (APHA); " cps " is centipoise; " f/t " is freeze/thaw, and " mPas " is the milli pascal second; " D.I. " is deionization.
General method:
[0096] recombinant DNA and the molecule clone technology of the standard of using in an embodiment are the known of this area and are described in the following document: Sambrook, J., Fritsch, E.F and Maniatis, T., Molecular Cloning:A Laboratory Manual, Cold Spring Harbor LaboratoryPress, Cold Spring Harbor, N.Y., 1989, T.J.Silhavy, M.L.Bennan, and L.W.Enquist, Experiments with Gene Fusions, Cold Spring HarborLaboratory, Cold Spring Harbor, N.Y., 1984, and Ausubel, F.M. etc., CurrentProtocols in Molecular Biology, Greene Publishing Assoc. and Wiley-Interscience, N.Y., 1987.
[0097] material of keeping and growing and the method that is suitable for bacterial cultures also is well known in the art.The technology that is applicable in following examples is found in following document: Manual of Methods forGeneral Bacteriology, Phillipp Gerhardt, R.G.E.Murray, Ralph N.Costilow, Eugene W.Nester, Willis A.Wood, Noel R.Krieg and G.BriggsPhillips compile, American Society for Microbiology, Washington, DC., 1994, perhaps Thomas D.Brock in Biotechnology:A Textbook of IndustrialMicrobiology, second edition, Sinauer Associates, Inc., Sunderland, MA, 1989.
[0098] unless otherwise mentioned, be used for the growth of bacterial cell and all reagent of keeping, restriction enzyme and material derive from: Aldrich Chemicals (Milwaukee, WI), and BD DiagnosticSystems (Sparks, MD), Life Technologies (Rockville, MD), or SigmaChemical Company (St.Louis, MO).
[0099] be used to generate 1, the glycerine of ammediol derives from J.T.Baker Glycerin USP level, lot number J25608 and G19657.
[00100] dsc: using Universal V31A TA instrument, is record DSC thermogram under 10 ℃ of/minute conditions in constant nitrogen gas stream and heating and cooling speed.
[00101] NMR: on Bruker DRX 500, use XWINNMR 3.5 version softwares record 1H NMR spectrum.Use 90 degree pulses (p1) and recirculation in 30 seconds to postpone (d1) and obtain data.Sample is dissolved in deuterochloroform and uses non-deuterochloroform as interior mark.
The separation of Bio-PDO and evaluation
[00102] glycerine is monitored by HPLC to the conversion of bio-PDO.Use standard technique and the obtainable material of field of chromatography technician to analyze.A kind of appropriate means adopts WatersMaxima 820HPLC system, uses UV (210nm) and RI to detect.With sample be expelled to Shodex SH-1011 post (8mmx300mm, available from Waters, Milford, MA), it is equipped with Shodex SH-1011P pre-column (6mmx50mm), and temperature is controlled at 50 ℃, use 0.01NH2SO4 as moving phase, flow velocity is 0.5mL/ minute.When wishing quantitative analysis, use the trimethylacetic acid of known quantity to prepare sample as external standard.Usually, glycerine (RI detection), 1, the retention time of ammediol (RI detection) and trimethylacetic acid (UV and RI detect) is respectively 20.67min, 26.08min, and 35.03min.
[00103] generation of bio-PDO confirms by GC/MS.Use the obtainable material of technician in standard technique and GC/MS field to analyze.A kind of appropriate means adopts HewlettPackard 5890 serial II gas chromatographs, and itself and Hewlett Packard 5971 series mass are selected detector (EI) and HP-INNOWax post (30m length, 0.25mm internal diameter, 0.25 micron membranes thickness) combination.From glycerine generate 1, the retention time of ammediol and mass spectrum and true 1, the comparing of ammediol (m/e:57,58).
From 1 of biology generation, ammediol prepares bio-based monoesters and diester
[00104] 1 of biological generation, the monoesters of ammediol and diester can mix with organic acid by bio-PDO and prepare.Under drying conditions, mixing under the heating and under the agitation condition that uses selected catalyzer prolonging.The monoesters that generates and the beguine of diester are according to acid different and different to the molar ratio of bio-PDO and selection of catalysts.
[00105] generation of ester is used
1The H nucleus magnetic resonance confirms.Use standard technique and
1The obtainable material of H NMR those skilled in the art is analyzed.
[00106] proton magnetic resonance (PMR) (
1H NMR) Wave Spectrum is to identify the effective ways of the structure of unknown organic compound.It provides about following information: be present in the number of the dissimilar hydrogen in the molecule, the number of the hydrogen that the electronic environment of dissimilar hydrogen and hydrogen have " neighbour ".
[00107] tends to leave TMS (the NMR standard substance that tetramethylsilane is common) at the upper frequency low-resonance with the carbon bonded hydrogen that is connected with electron-withdrawing group.Wherein specific hydrogen atom is known as the chemical shift (δ) of this hydrogen atom with respect to the position of TMS resonance.The typical chemical shift of fatty acid ester is as follows.
For terminal CH
3, δ=0.88
For (CH
2-C
H 2-CH
2), (C
H 2-CH
2-C=O) and (O-CH
2-C
H 2-CH
2-O) methylene radical, δ respectively=1.26,1.61 and 1.97.
For the methylene radical (C adjacent with ester
H 2-C=O), δ=2.28
For ester (C (=O)-O-C
H 2-), δ=4.15.
Proton N MR can be with the proton (C corresponding to end group
H 2 -OH) proton (the C of (δ=3.7) and middle ester group
H 2 -O-C (=O)-) distinguishes (for diester and monoesters, δ respectively=4.15 and 4.24) and therefore might identify ester and can monitor reaction by the integral area at these two peaks relatively.
Embodiment 1
Under fermentation conditions D-glucose is to 1, the conversion of ammediol
[00108] coli strain ECL707, contain klebsiella pneumoniae (K.pneumoniae) dha regulon clay pKP1 or pKP2, klebsiella pneumoniae pdu operon pKP4, or independent Supercos carrier, in 5L Applikon fermentor tank, grow, be used for generating 1 from glucose, ammediol.
[00109] substratum of Shi Yonging contains the potassium phosphate buffer agent of 50-100mM, and pH 7.5,40mM (NH4) 2SO4,0.1% (w/v) yeast extract, 10 μ M CoCl2,6.5 μ MCuCl2,100 μ M FeCl3,18 μ M FeSO4,5 μ M H3BO3,50 μ M MnCl2,0.1 μ M Na2MoO4,25 μ M ZnCl2,0.82mM MgSO4,0.9mM CaCl2 and 10-20g/L glucose.Add other glucose, it is excessive that remaining glucose keeps.Temperature is controlled at 37 ℃, uses the KOH of 5N or NaOH to control pH 7.5.Introduce suitable microbiotic and be used for the maintenance of plasmid.For anaerobically fermenting, with the nitrogen bubble reactor of 0.1vvm; When dO fixed point is 5%, with 1vvm air bubbling reactor, and with culture medium supplemented with vitamin B12.
[00110] 1, the titre of ammediol (g/L) is 8.1 to 10.9.The yield of bio-PDO (g/g) is 4% to 17%.
Embodiment 2
1 of biogenetic derivation, the purifying of ammediol
[00111] laid-open U.S. Patents application No.2005/0069997 disclose the intestinal bacteria that purifying derives from cultivation (its through Bioengineered with synthetic 1, ammediol) from sugar fermenting broth 1, the method for ammediol.Primary process requires the filtration of fermenting broth product flow, and ion-exchange and distillation are preferably included in the chemical reduction of the product during the distillation.
[00112] as 1 of generation as described in the embodiment 1, ammediol is by the multistep process purifying: comprise the meat soup clarification, rotary evaporation, the multiple distillation of anionresin and supernatant liquor.
[00113] in the ending of fermentation, use cellular segregation meat soup to be clarified with centrifugal and combination membrane filtration, carry out ultrafiltration by the 1000MW film then.Clarifying meat soup is processed in large-scale rotatory evaporator.About 46 pounds charging (21,000 gram) obtains spissated syrup through processing.The syrup of 60 milliliters of parts is placed 1 inch (still kettle of 1 ") diameter distillation column.Distillation is carried out under the vacuum of 25 inches of mercury.During whole distillation, use and be about 1 reflux ratio.Obtain several distillment cuts, cut is accepted further processing in the middle of it.This material dilutes with isopyknic water, and this material is loaded into (mixed bed, the NM-60 resin of 80 grams) on the anion-exchange column, and post washes with water.With the speed pumps water of 2 ml/min, per 9 minutes collection fractions.The odd number fraction is analyzed, and fraction 3-9 comprises 3G.The fraction that comprises 3G is collected and experiences microdistillation to reclaim the pure 1 of some grams, ammediol monomer (its method polymerization according to embodiment 2-8 obtains monoesters and diester).
Embodiment 3
Use tosic acid as Preparation of Catalyst propylene glycol SUNSOFT Q-182S
[00114] for from 1 of biogenetic derivation, ammediol and stearic acid prepare the propylene glycol SUNSOFT Q-182S, use 1 of method purifying biological source among the embodiment 1 and 2, ammediol.With 1 of the biogenetic derivation of 2.58g (0.033 mole), ammediol, stearic acid (the Aldrich of (19.45g 0.065 mole), 95%), and the tosic acid (Aldrich 98.5%) of 0.2125g (0.001 mole) joins in the glass reactor that mechanical stirrer is housed, this reactor is washed to remove air and moisture with drying nitrogen, kept 15 minutes.Temperature of reaction is elevated to 100 ℃ then, and while abundant stirred reaction mixture under nitrogen gas stream also continues 210 minutes.
[00115] after reaction is finished, reaction mixture is cooled to about 35 ℃, with transferred product in beaker.By adding 100 ml waters and fully stirring 15 minutes formation emulsions with purified product at 45-60 ℃.With the mixture cooling and by filtering separation solid propylene glycol SUNSOFT Q-182S.
[00116] product passes through
1H nuclear magnetic resonance, stave is levied (CDCl
3(deuterochloroform)): δ=0.88 (t, C
H 3-CH
2, 6H), 1.26 (t, CH
2-C
H 2-CH
2, 28H), 1.61 (t, C
H 2-CH
2-C=O, 4H), 1.97 (t ,-O-CH
2-C
H 2-CH
2-O, 2H), 2.28 (t, C
H 2-C=O, 4H), 4.15 (t, C (=O)-O-C
H 2-4H) and DSC (Tm=66.4 ℃ and Tc=54.7 ℃).
Embodiment 4
1 of biology origin, the purity of ammediol characterizes
[00117] in following table 1,1 of biology origin, 1 of the chemical preparation of ammediol (as preparation and purifying as described in the laid-open U.S. Patents application No.2005/0069997) (" Bio-PDO ") and two independent commercial acquisitions, ammediol preparation (source A and B) is comparing aspect several purity.
Table 1
| Unit | Source A | Source B | ??Bio-PDO | |
| Total organic impurity | ??ppm | ??570 | ??695 | ??80 |
| The UV absorbancy, 220nm, | ??AU | ??0.25 | ??1.15 | ??0.12 |
| The UV absorbancy, 250nm, | ??AU | ??0.123 | ??0.427 | ??0.017 |
| The UV absorbancy, 275nm | ??AU | ??0.068 | ??0.151 | ??0.036 |
| The UV absorbancy, 350nm | ??AU | ??0.013 | ??0.007 | ??0.001 |
| Superoxide | ??ppm | ??67 | ??43 | ??2 |
| ??CIE?L *a *b *ASTM?D6290 | ??b * | ??0.411 | ??0.03 | ??0.1 |
| Carbonyl | ??ppm | ??147 | ??175 | ??1 |
[00118] about the biology by laid-open U.S. Patents application No.2005/0069997 disclosed method purifying generate 1, the typical characteristics of the purity aspect of the sample of ammediol is provided in the following table 2.
[00119] ppm of unit of total organic impurity be meant in final preparation rather than 1, per 1,000,000 parts umber of the total organic compound in the ammediol is measured by the gas chromatograph that uses flame ionization detector.The result reports by peak area.Flame ionization detector is insensitive to water, makes that total impurities is all non-1, the organic peak of ammediol (area %) and to all areas %'s and ratio (comprising 1, ammediol).Term " organic materials " is meant carbon based pollutants.
[00120] go up and to show, with 1 of the chemistry generation of commercial acquisition, the ammediol preparation is compared, and disclosed purification process provides 1 of highly purified biology origin, ammediol.
Embodiment 5
1 of biology origin, the skin irritation of ammediol and sensitization feature
[00121] in the human skin paster test with about 100 objects, 5,25 and 50% PDO does not cause that any showing stimulates or the skin reaction of sensitization.Second individual's skin paster test, the PDO of 25,50 and 75% concentration under pH 7, or 75% PDO under pH 4 and 9 do not produce any clinically significant skin irritation or sensitivity response.Based on these research, think that PDO is not skin irritant or sensitizing agent in the people.In the test of the second individual's skin paster, also under 25,50 and 75% (pH 7), tested propylene glycol (1,2-propylene glycol or PG), and the PG of all three kinds of concentration is the skin tests stimulator and the accumulation stimulator of human skin.
[00122] embodiment 6-8 is portentous and based on following description: D ' Amelio, Frank S Sr.;
Botanicals:A Phytocosmetic Desk ReferenceCRC press, 1999, the 299-304 page or leaf.
Embodiment 6
Be used for natural, the high foaming of daily use, gentle shampoo
| ??％ | In proper order | ?? Raw material | The INCI title |
| ??1.00 | ??1 | Deionized water | Water |
| ??0.00 | ??1 | Saponin | Saponin |
| ??0.00 | ??1 | Cocamidopropyl betaine | Cocamidopropyl betaine |
| ??.00 | ??1 | Coconut oleoyl amine DEA 1: 1 | Coconut oleoyl amine DEA |
| ??.10 | ??1 | Herba Equiseti Arvinsis extract, 5: 1BIO-PDO | Herba Equiseti Arvinsis extract |
| ??.10 | ??1 | The daisy leaf extract, 5: 1BIO-PDO | The daisy leaf extract |
| ??.10 | ??1 | Rosemary extract, 5: 1BIO-PDO | Rosemary extract |
| ??.10 | ??1 | Chamomile extract, 5: 1BIO-PDO | The german chamomile extract |
| ??.5. | ??2 | 50% aqueous sodium hydroxide solution | Sodium hydroxide |
| ??.50 | ??3 | Aculyn 22 viscosifying agents 1 | Acrylate/polyoxyethylene octadecyl-20 ether metacrylic acid ester multipolymer |
| ??5.00 | ??4 | ??Plantaren?2000 2 | The decyl polyglucose |
| ??.10 | ??Lipovol?A 3 | ??Avacado?Oll | |
| ??.5. | ??5 | 25% aqueous citric acid solution | Citric acid |
| ??0.00 | ??6 | ??UCARE?Polymsr?LR30M(1.3％) 4 | Polyquaternium-10 |
| ??.00 | ??7 | ??Llpamlde?MEAA 4 | Ethanamide MEA |
[00123] note: it is 5 parts 1,3 propylene glycol of biology origin and 1 part dehydrated plant (20% 1: 1 extract) that 5: 1 Bio-PDO is defined as
[00124] process:
1. each composition combination that at room temperature will order 1, the stirring of using at a slow speed middling speed is to prevent aeration, up to becoming even.
???????????????????
1Rohm&Haas
2Henkel
3Lipo?Chemicals，Inc.
4Amerchol
2. the constituent adjustment pH to 9.2 of use order 2.
3. interpolation order 3 and continuation are stirred at leisure, until polymer disperses fully.
4. each composition of interpolation order 4 also mixes until become evenly at leisure.
5. the constituent adjustment pH to 5.5 of use order 5.
6. interpolation order 6 is also mixed until become evenly at leisure.
Interpolation order 7 and mixing are until become evenly at leisure.
Embodiment 7
The scent of All Pure Nature (blooming) bathing oil
| ％ | Sequentially | Raw material | The INCI title |
| 15.96 | 1 | Lipovol ALM 5 | Sweet Almond Oil |
| 63.54 | 1 | Lipovol SES 1 | Sesame oil |
| 5.00 | 1 | Lipolan R 1 | Lanolin oil |
| 5.00 | 1 | Lipopeg 2-DL | The PEG-4 dilaurate |
| 10.00 | 1 | Lipocol 0-2 1 | Polyoxyethylene oleyl ether-2 |
| 0.10 | 1 | Nipasol | Nipasol |
| 0.10 | 1 | Vitamin E USP-FCC6 | Vitamin E |
| 0.10 | 2 | Arnica 5∶1BIO-PDO | Arnica dried flower order extract |
| 0.10 | 2 | Chamomile 5∶1BIO-PDO | Chamomile extract |
| 0.10 | 2 | Comfrey 5∶1BIO-PDO | Daisy extract |
| q.s. | 3 | D﹠C Green#6 (BIO-PDO solution O.5%) | D&C Green#6 |
[00125] process:
1. under vigorous stirring, incite somebody to action each composition mixing of order 1 and be heated to 557 ℃, until Nipasol dissolves fully, be cooled to 30 ℃.
????????????????????????
5Lipo?Chemicals，Inc.
6Roche?Vitamins?and?Fine?Chemicals
2. at 30 ℃, each composition of batch (-type) interpolation order 2 also is cooled to 25 ℃.
At 25 ℃, interpolation order 3 is until obtain required gloss.
Embodiment 8
The moisture spraying humidizer of high moisturizing
| ％ | Sequentially | Raw material | The INCI title |
| 92.70 | 1 | Deionized water | Water |
| 2.00 | 1 | Lipocare HA/EC 7 | Echinaceine (Echinacin) |
| 5.00 | 1 | Liponic EG-1 1 | Polyoxyethylene glyceryl ether-26 |
| 0.10 | 1 | 5: 1 BIO-PDO of ulmus fulva extract8 | The ulmus fulva extract |
| 0.10 | 1 | 5: 1 BIO-PDO of C chamomile extract2 | The german chamomile extract |
| 0.10 | 1 | Gansu Province ox seedling (Wild Alum) extract 5: 1BIO-PDO2 | Geranium extract |
[00126] process:
Under vigorous stirring, at room temperature merge each composition, until batch of material is transparent and even.
Embodiment 9
Mixture by Bio-PDO and Bio-PDO ester extracts yellow chamomile pollen end
[00127] according to submitting on February 10th, 2006 and U.S. Provisional Patent Application incorporated herein by reference is 60/772,112 synthetic, purifying and characterized ester based on the 1,3-PD of biology origin.
?????????????????????????????????????????
7Lipo?Chemicals，Inc.
8BloBotanica/Lipo?Chemicals，Inc.
[00128] 1,3-PD of biology origin and 1,3-PD conjugate esters are used for extracting yellow chamomile pollen end (Martricaria recutita derives from Egypt, dealer-Mountain Rose Herbs, OR).
[00129] yellow chamomile powder and mixed being incorporated on the shaking table of 1,3-PD were flooded 30 minutes, then in mixture, add the 1,3-PD ester and temperature is elevated to 90 ℃, and continued dipping other 2 hours. With the GHP film of filtration of material by 0.2 micron, analyze filtrate by LC/MS, show and contain the compound that is extracted.
Embodiment 10
Extract yellow chamomile pollen end by Bio-PDO
[00130] according to the 1,3-PD conjugate esters of synthetic biology origin described in the embodiment 9, and this ester (Bio-PDO diethyl capronate) is used for extracting yellow chamomile pollen end (Mountain Rose Herbs, OR).
[00131] yellow chamomile powder and mixed being incorporated in of ester are flooded 2,4,6 hours on the shaking table. With the GHP film of filtration of material by 0.2 micron, analyze (UV/Vis spectrophotometer by UV/VIS, Varian (Australia), model: Cary 5000) filtrate, and spectroscopic data shows that the dip time of the effect of the compound that is extracted and use is proportional.
Embodiment 11
Extract red rose by the Bio-PDO ester
[00132] according to 1 of synthetic biology origin described in the embodiment 9, the ammediol conjugate esters, and the red rose (Rosa centifolia, Mountain Rose Herbs, OR) that this ester (Bio-PDO diethyl capronate) is used for extracting drying.
[00133] rose and mixed being incorporated in of ester of drying are flooded 2,4,6 hours on the shaking table. With the GHP film of filtration of material by 0.2 micron, and by UV/VIS analysis filtrate.
Embodiment 12
Extract edible seaweed by the Bio-PDO ester
[00134] is used for extracting dry edible seaweed (the local market of farm produce) according to the 1,3-PD conjugate esters of synthetic biology origin described in the embodiment 9, and with this ester (Bio-PDO diethyl capronate).
[00135] edible seaweed and mixed being incorporated in of ester of drying are flooded 2,4,6 hours on the shaking table. With the GHP film of filtration of material by 0.2 micron, and by UV/VIS analysis filtrate
Embodiment 13
Use the plant extract of Bio-PDO/ carbinol mixture
[00136] process: be immersed in the dry Jasmines (Jasminum officinale, Mountain Rose Herbs, OR) of 5 grams in the mixture of Bio-PDO/ methyl alcohol (70%: 30%) and flooded 24 hours. With the GHP film of filtration of material by 0.2 micron, and by LC/MS analysis filtrate. LC/MS spectrum shows that active component is effectively extracted.
Embodiment 14
Use the mixture of Bio-PDO/ deionized water to extract honeysuckle
[00137] process: be immersed in the dry honeysuckles (honeysuckle, from China, the dealer is Mountain Rose Herbs, OR) of 5 grams in the mixture of Bio-PDO/ deionized water (50%: 50%) and flooded 24 hours. With the GHP film of filtration of material by 0.2 micron, and by LC/MS analysis filtrate. LC/MS spectrum shows that active component is effectively extracted.
Embodiment 15
Use the mixture of Bio-PDO/ deionized water to extract eucalyptus leaves
[00138] process: be immersed in the dry eucalyptus leaveses (blue gum, from France, the dealer is Mountain Rose Herbs, OR) of 5 grams in the mixture of Bio-PDO/ deionized water (50%: 50%) and flooded 24 hours. With the GHP film of filtration of material by 0.2 micron, and by LC/MS analysis filtrate. LC/MS spectrum shows that active component is effectively extracted.
Embodiment 16
Use the mixture of Bio-PDO/ deionized water to extract the sandalwood red powder
[00139] process: with the dry sandalwood red powder red sandalwoods of 5 grams, from Africa, the dealer is Mountain Rose Herbs, OR) be immersed in the mixture of Bio-PDO/ deionized water (50%: 50%) and flooded 24 hours. With the GHP film of filtration of material by 0.2 micron, and by LC/MS analysis filtrate. LC/MS spectrum shows that active component is effectively extracted.
Comparative example 1
1,3-PD and the propane diols of comparative biology origin in vegetable material extracts
[00140] Bio-1, ammediol and propane diols are used for from Jasmine, yellow chamomile pollen end (german chamomile), myrrh glue extracts composition in cutting benzoin powder and the yellow wax. Use LC-MS and GC-MS to analyze the composition that is extracted. Qualitative analysis has confirmed to use the identical of the 1,3-PD composition that extracts and the composition that uses propane diols to extract. In addition, use bio-1,3 propane diols, and use bio-1, ammediol is identical with the composition that carbinol mixture extracts.
[00141] main component of chamomile extract is Bisabolol terpene alcohol oxide (for the en-in-bicyclic ethers), and the apigenin glucosides. Use 1,3-PD and propane diols (1,2 propane diols, the comparison yield of these active components Aldrich) is as shown in table 1:
Table 1
| Extract product | Bio-1, the ammediol area | The propane diols area | Difference % |
| Bisabolol terpene alcohol oxide | 9217821 a | 8760424 a | 5.2 |
| The apigenin glucosides | 3972525 b | 3549734 b | 11.2 |
| The en-in-bicyclic ethers | 9394370 b | 7261956 b | 29.2 |
[00142] a:GC-MS analyzes, and b:LC-MS analyzes
[00143] table 1 has represented the GC-MS/LC-MS peak area of the composition that use 1,3-PD and propane diols extract. Compare with the extraction of using propane diols, use Bio-1, the extraction process of ammediol, the en-in-cyclic ethers extracts high 29.4wt%, and the apigenin glucosides extracts high 11.2wt%, and Bisabolol terpene alcohol oxide extracts high 5.2wt%.
Comparative example 2
[00144] yellow chamomile pollen end (5 gram) solvent mixture (Bio-PDO/ deionized water, 1: 1 ratio, and the mixture of 1,2-PD (Propylene glycol, Aldrich)/deionized water, 1: 1 ratio) with 50 grams is mixed. Mixture stirred 24 hours. Filter and analyze extract.
Table 2
Relatively use the yellow chamomile of Bio-PDO and propane diols to extract
| Product | The Bio-PDO/ water area | The propylene glycol/water area | Difference % |
| Bisabolol terpene alcohol oxide | 25176422 | 14409166 | 75 |
| Apigenin | 2374215 | 556691 | 326 |
| The apigenin glucosides | 658824 | 420412 | 57 |
| En-in-two cyclic ethers | 1842764 | 866635 | 113 |
[00145] in the table 2 data representation use Bio-PDO/ water and use the GC-MS/LC-MS peak area of the composition that the mixture of propylene glycol/water extracts. With use that propane diols extracts those compare, use the Bio-PDO/ aqueous mixtures, Bisabolol terpene alcohol oxidation object height 75wt%, the high 326wt % of apigenin, the high 113wt% of en-in-cyclic ethers, the high 57wt% of apigenin glucosides.
Comparative example 3
[00146] yellow chamomile pollen end (Mountain Rose Herb, OR) (5 gram) mixed with the Bio-PDO of 50 grams, also the yellow chamomile powder with 5 grams mixes with deionized water. Impregnation mixture 24 hours filters and analyzes extract by LC/MS.
Table 3: relatively use the yellow chamomile of Bio-PDO and water to extract
| Product | The Bio-PDO/ area | H 2The O/ area | Difference % |
| Apigenin | 63.32 | 125.53 | -50.4 |
| The apigenin glucosides | 134.58 | 0 | |
| En-in-two cyclic ethers | 1340.74 | 0 |
[00147] compare with the extraction of using Bio-PDO, can not extract apigenin glucosides and en-in-bicyclic ethers when using deionized water, higher but apigenin extracts.
Claims (37)
1. comprise 1, the composition of ammediol ester and extraction product.
2. the composition of claim 1, wherein said ester has at least 3% bio-based carbon.
3. the composition of claim 1, wherein said ester has at least 6% bio-based carbon.
4. the composition of claim 1, wherein said ester has at least 10% bio-based carbon.
5. the composition of claim 1, wherein said ester has at least 25% bio-based carbon.
6. the composition of claim 1, wherein said ester has at least 50% bio-based carbon.
7. the composition of claim 1, wherein said ester has at least 75% bio-based carbon.
8. the composition of claim 1, wherein said ester has 100% bio-based carbon.
9. the composition of claim 1, wherein said ester have following formula structure: R1-C (=O)-O-CH2-CH2-CH2-OH, wherein R1 is that chain length is the about 1 straight or branched carbochain to about 40 carbon.
10. the composition of claim 9, wherein R1 has one or more following functional groups that are selected from: alkene, acid amides, amine, carbonyl, carboxylic acid, halogenide, hydroxyl, ether, alkyl oxide, sulfuric ester and ether sulfuric ester.
11. the composition of claim 1, wherein said ester have following formula structure: R1-C (=O)-O-CH2-CH2-CH2-O-C (=O)-R2, wherein R1 and R2 are that chain length is the about 1 straight or branched carbochain to about 40 carbon.
12. the composition of claim 11, wherein R1 and R2 have one or more following functional groups that are selected from: alkene, acid amides, amine, carbonyl, carboxylic acid, halogenide, hydroxyl, ether, alkyl oxide, sulfuric ester and ether sulfuric ester.
13. the composition of claim 11, wherein R1 is identical carbochain with R2.
14. the composition of claim 1, wherein ester is selected from:
I. propylene glycol SUNSOFT Q-182S, monostearate and composition thereof;
Ii. propylene glycol dilaurate, a lauric acid ester and composition thereof;
Iii. Rikemal PO 200, monooleate and composition thereof;
Iv. propylene glycol two valerates, a valerate and composition thereof;
V. propylene glycol dicaprylate, an octanoate and composition thereof;
Vi. propylene glycol two nutmeg acid esters, a nutmeg acid esters and composition thereof;
Vii. propylene glycol dipalmitate, monopalmitate and composition thereof;
Viii. propylene glycol Er docosoic ester, Yi docosoic ester and composition thereof;
Ix. propylene glycol adipic acid ester;
X. propylene glycol maleic acid ester;
Xi. propylene glycol dibenzoate;
Xii. propylene-glycol diacetate; With
Xiii. its mixture.
15. the composition of claim 14, wherein ester is selected from:
A. propylene glycol SUNSOFT Q-182S, monostearate and composition thereof;
B. Rikemal PO 200, monooleate and composition thereof;
C. propylene glycol dicaprylate, an octanoate and composition thereof;
D. propylene glycol two nutmeg acid esters, a nutmeg acid esters and composition thereof; With
E. its mixture.
16. the composition of claim 1, wherein extracting product is natural extract.
17. the composition of claim 16, wherein natural extract is a plant milk extract.
18. the composition of claim 1, wherein extract is selected from: plant milk extract, vegetable extract, protein extract, lipid extracts, marine products class extract, Algae Extract, newborn class extract.
19. the composition of claim 1 further comprises 1, ammediol.
20. the composition of claim 19, wherein 1, ammediol has at least 95% bio-based carbon.
21. the composition of claim 20, wherein 1, ammediol has 100% bio-based carbon.
22. from the method for extraction source extraction extract, this method may further comprise the steps:
(a) provide 1, the ester of ammediol;
(b) with 1, the ammediol ester mixes with extraction source, extract is extracted from extraction source enter the ester; With
(c) separation and Extraction source from ester and extract.
23. the method for claim 22 comprises further that with 1 ammediol mixes with ester and extraction source.
24. the method for claim 23, wherein 1, ammediol has at least 95% bio-based carbon.
25. the method for claim 22, wherein said ester have following formula structure: R1-C (=O)-O-CH2-CH2-CH2-OH, wherein R1 is that chain length is the about 1 straight or branched carbochain to about 40 carbon.
26. the method for claim 22, wherein said ester have following formula structure: R1-C (=O)-O-CH2-CH2-CH2-O-C (=O)-R2, wherein R1 and R2 are that chain length is the about 1 straight or branched carbochain to about 40 carbon.
27. the method for claim 26, wherein R1 is identical carbochain with R2.
28. the method for claim 22, wherein ester is selected from:
I. propylene glycol SUNSOFT Q-182S, monostearate and composition thereof;
Ii. propylene glycol dilaurate, a lauric acid ester and composition thereof;
Iii. Rikemal PO 200, monooleate and composition thereof;
Iv. propylene glycol two valerates, a valerate and composition thereof;
V. propylene glycol dicaprylate, an octanoate and composition thereof;
Vi. propylene glycol two nutmeg acid esters, a nutmeg acid esters and composition thereof;
Vii. propylene glycol dipalmitate, monopalmitate and composition thereof;
Viii. propylene glycol Er docosoic ester, Yi docosoic ester and composition thereof;
Ix. propylene glycol adipic acid ester;
X. propylene glycol maleic acid ester;
Xi. propylene glycol dibenzoate;
Xii. propylene-glycol diacetate; With
Xiii. its mixture.
29. the method for claim 22, wherein extract is an essential oil.
30. the method for claim 22, wherein extract is the medicinal herbs extracts.
31. comprise 1, ammediol and extract the composition of product, wherein 1, ammediol is the biology origin.
32. the composition of claim 31, wherein 1, ammediol has at least 85% bio-based carbon.
33. the composition of claim 31, wherein 1, ammediol has at least 95% bio-based carbon.
34. the composition of claim 31, wherein 1, ammediol has 100% bio-based carbon.
35. the composition of claim 31, wherein extracting product is natural extract.
36. the composition of claim 35, wherein natural extract is a plant milk extract.
37. the composition of claim 31, wherein extract is selected from: plant milk extract, vegetable extract, protein extract, marine products class extract, Algae Extract, newborn class extract.
Applications Claiming Priority (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77211106P | 2006-02-10 | 2006-02-10 | |
| US60/772,193 | 2006-02-10 | ||
| US60/772,194 | 2006-02-10 | ||
| US60/772,110 | 2006-02-10 | ||
| US60/772,112 | 2006-02-10 | ||
| US60/772,111 | 2006-02-10 | ||
| US60/772,120 | 2006-02-10 | ||
| US60/772,471 | 2006-02-10 | ||
| US60/846,948 | 2006-09-25 | ||
| US60/853,920 | 2006-10-24 | ||
| US60/859,264 | 2006-11-15 | ||
| US60/872,705 | 2006-12-04 | ||
| US60/880,824 | 2007-01-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101641313A true CN101641313A (en) | 2010-02-03 |
Family
ID=41615725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200780011093A Pending CN101641313A (en) | 2006-02-10 | 2007-02-12 | 1 of biological origin, ammediol and conjugate esters thereof are as natural and non-irritating solvent |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101641313A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103476914A (en) * | 2011-04-13 | 2013-12-25 | Elc管理公司 | Conditioning agents for personal care compositions |
| US9242930B2 (en) | 2011-04-13 | 2016-01-26 | Elc Management Llc | Mild anionic surfactants suitable for personal care compositions |
| CN107820457A (en) * | 2015-06-30 | 2018-03-20 | 吉列有限责任公司 | Lubrication for razor cartridge |
| CN108884343A (en) * | 2015-11-12 | 2018-11-23 | A·扎克 | Inkjet ink composition |
| CN113507917A (en) * | 2019-02-04 | 2021-10-15 | 西姆莱斯有限公司 | Active agent for skin and hair care having physicochemical modification property |
-
2007
- 2007-02-12 CN CN200780011093A patent/CN101641313A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103476914A (en) * | 2011-04-13 | 2013-12-25 | Elc管理公司 | Conditioning agents for personal care compositions |
| US9242930B2 (en) | 2011-04-13 | 2016-01-26 | Elc Management Llc | Mild anionic surfactants suitable for personal care compositions |
| CN107820457A (en) * | 2015-06-30 | 2018-03-20 | 吉列有限责任公司 | Lubrication for razor cartridge |
| CN108884343A (en) * | 2015-11-12 | 2018-11-23 | A·扎克 | Inkjet ink composition |
| CN113507917A (en) * | 2019-02-04 | 2021-10-15 | 西姆莱斯有限公司 | Active agent for skin and hair care having physicochemical modification property |
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