WO2006097929A2 - Soaps from organic residues and method of producing the same - Google Patents

Soaps from organic residues and method of producing the same Download PDF

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Publication number
WO2006097929A2
WO2006097929A2 PCT/IL2006/000338 IL2006000338W WO2006097929A2 WO 2006097929 A2 WO2006097929 A2 WO 2006097929A2 IL 2006000338 W IL2006000338 W IL 2006000338W WO 2006097929 A2 WO2006097929 A2 WO 2006097929A2
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WO
WIPO (PCT)
Prior art keywords
oil
soap
olive
additionally
water
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/IL2006/000338
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English (en)
French (fr)
Other versions
WO2006097929A3 (en
Inventor
Gregory Pipko
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Caper Naum Vista Olive Oil Market Ltd
Original Assignee
Caper Naum Vista Olive Oil Market Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Caper Naum Vista Olive Oil Market Ltd filed Critical Caper Naum Vista Olive Oil Market Ltd
Priority to EP06711320.9A priority Critical patent/EP1868560A4/en
Priority to JP2008501488A priority patent/JP5198246B2/ja
Priority to MX2007011308A priority patent/MX2007011308A/es
Priority to AU2006224152A priority patent/AU2006224152B2/en
Priority to US11/908,889 priority patent/US20080207480A1/en
Priority to CA002600940A priority patent/CA2600940A1/en
Publication of WO2006097929A2 publication Critical patent/WO2006097929A2/en
Publication of WO2006097929A3 publication Critical patent/WO2006097929A3/en
Anticipated expiration legal-status Critical
Priority to US12/965,982 priority patent/US8778863B2/en
Ceased legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D9/00Compositions of detergents based essentially on soap
    • C11D9/04Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/045Compositions of detergents based essentially on soap containing compounding ingredients other than soaps containing substances which prevent the deterioration of soaps, e.g. light or heat stabilisers or antioxidants
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D13/00Making of soap or soap solutions in general; Apparatus therefor
    • C11D13/02Boiling soap; Refining
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/08Liquid soap, e.g. for dispensers; capsuled

Definitions

  • the present invention generally relates to soaps obtained from organic residues and to a method of producing such soaps.
  • Soap was made by mixing animal fats with lye, such as ashes of a wood fire.
  • many of the soaps are mixtures of sodium or potassium salts of fatty acids which can be derived from oils or fats by reacting them with an alkali such as sodium or potassium hydroxide at elevated temperatures.
  • Vegetable oil as such as olive oil, is produced by pressing it out of oil-bearing seeds, usually by hydraulic power presses.
  • the residual product is a dense cake of crushed and compressed seed husks. This dense slab is provided in some extent for animal feed wherein most of it is decomposed or regarded as either costless or valuable agricultural effluent.
  • United States Patent 4,483,742 to Bridle discloses liquid soaps for use in paper re-cycling and other industrial cleaning or scouring processes.
  • the liquid soap comprises an aqueous partially saponified mixture comprising 1 part of pine oil (a mixture of terpene alcohols and hydrocarbons) and from 1 to 20 parts of a soap-making fatty acid, such as tall oil or distilled oil.
  • the mixture is preferably saponified by use of 30% sodium hydroxide solution.
  • the liquid soap may contain less than 10% water .
  • United States Patent 6,380,153 to Carlson discloses methods of producing surfactant compositions are disclosed in which processed plant material is used to enhance the saponification process to produce surfactant compositions having enhanced surfactant, mechanical cleaning and emollient characteristics.
  • United States Patent no. 6,020,509 to Weerasooriya discloses a process for producing a surfactant composition by partially saponifying an alkoxylated triglyceride having the formula: comprising an alkali metal hydroxide such as sodium hydroxide and recovering a surfactant composition comprising soap and moisturizing agents comprised of alkoxylated monoglycerides and unreacted alkoxylated triglycerides.
  • a soap made of said dense slab or 'cake' of crushed and compressed seed husks is still a long felt need.
  • This method comprising hydrolyzing one or more natural oils so as water-soluble soap is obtained and dispersing organic residues in a water miscible solution until a homogeneous soap composition phase is obtained.
  • said method further comprises steps of admixing preservatives, additives, fillers etc.
  • the soap is preferably comprising ingredients selected from preservatives, additives, fillers etc.
  • the present invention provide a environmental friendly and cost effective means of recycling dense cake of crushed and compressed seed husks, in the manner that natural or at least partially natural soaps are obtained.
  • soap refers hereinafter to any soap, detergent, surface-active agents, surfactants, rinsing agents and to any cleansing agents used for personal or minor cleaning.
  • the term is related to either soaps in solid moulded or solid provided in a pellet form, or a liquid (flowing) soap.
  • Said soap is referring to any type of soap, including, yet not limited to shampoo, body or hand-cleansing composition, toothpaste or any other soap form used for human or veterinary hygiene, utilized in industrial applications, applicable for laundry cleaning etc.
  • Organic residues' refers hereinafter to organic biomass, residual product which is a dense slab or 'cake' of crushed and/or compressed seed husks; and especially to olive, olive see, olive tree, olive leaf extracts, products and by- products.
  • the method according to the preset invention is an improvement of traditional methods that were historically enveloped with olive press. It is known in the art that an olive press works by applying pressure to olive paste to separate the liquid oil and vegetation water from the solid material. The oil and vegetation water are then separated by standard decantation. This method is still widely used today, and it's still a valid way of producing high quality olive oil if adequate precautions are taken. First the olives are ground into an olive paste, using large grindstones.
  • the olive paste generally stays under the stones for about half an hour, this has three objectives, namely to guarantee that the olives are well ground, to allow enough time for the olive drops to join to form the largest droplets of oil and to allow the fruit enzymes to produce some of the oil aromas and taste.
  • olive oil mills use a modern crushing method with a traditional press. After grinding, the olive paste is spread on fiber disks, which are stacked on top of each other, then placed into the press.
  • the disks were made of hemp or coconut fiber, but nowadays they're made of synthetic fibers which are easier to clean and maintain. These disks are then put on a hydraulic piston, forming a pile.
  • the applied hydraulic pressure can go to 400 atm.
  • water is run down the sides of the disks to increase the speed of percolation.
  • the liquids are then separated either by a standard process of decantation or by the means of a faster vertical centrifuge.
  • the traditional method is a valid form of producing high quality olive oil, if after each extraction the disks are properly cleaned from the remains of paste; if not the leftover paste will begin to ferment thereby producing inconsistencies of flavours (called defects) that will contaminate the subsequently produced olive oil.
  • defects inconsistencies of flavours
  • a similar problem can affect the grindstones, that in order to assure perfect quality, also require cleaning after each usage.
  • the present invention overcomes drawbacks of traditional process, such as difficult cleaning, non-continuous process introducing waiting periods thus exposing the olive paste to the action of oxygen and light, requirement for extensive manual labor and longer time period from harvest to pressing.
  • Some aspects of the invention utilizes methods of olive oil extraction uses an industrial decanter, e.g., decanter centrifugation, to separate all the phases by centrifugation.
  • an industrial decanter e.g., decanter centrifugation
  • the olives are crushed by the use of a rotating mechanical mill that grinds the olives in to a fine paste.
  • This paste is then malaxed for 30 to 40 min in order allow the small olive droplets to agglomerate.
  • the aromas are created in these two steps through the action of fruit enzymes.
  • the paste is pumped in to an industrial decanter where the phases will be separated. To facilitate the extraction process with the paste there is a certain quantity of water added.
  • the decanter is a large capacity horizontal centrifuge rotating around 3000 rpm, the high centrifugal force created allows the phases to be readily separated according to their different densities (solids > vegetation water > oil). Inside the decanters rotating conical drum there is a coil that rotates a few rpm slower, pushing the solid materials out of the system. The three phases are separated according to their densities. The separated oil and vegetation water are then rerun trough a vertical centrifuge, working around 6000 rpm that will separate the small quantity of vegetation water still contained in oil and vice versa.
  • the present invention also overcomes various disadvantages of the modern process, namely: the process of the present invention is respectfully inexpensive, less technical labor required, it requires low energy consumption, pomace is utilized and re-used, lesser amount of vegetable water is to be disposed of etc.
  • a novel method of producing soaps from organic residues comprising the steps of hydrolyzing at least one natural oil so as water-soluble soap is obtained and dispersing organic residues in a water miscible solution until a homogeneous soap composition phase is obtained.
  • hydrolyzing is provided in basic conditions, e.g., at pH ranging from about 7.5 to 12.5. It is according to another embodiment of the present invention wherein the above- mentioned method additionally comprising admixing of glycerol.
  • organic residues are selected from olive oil, olive products, olive tree products, olive oil production residuals, wine production residues, fruit or vegetable residues, canned food industries or any combination thereof.
  • the water-soluble soap is at least partially displaced by one or more synthetic surface-active agents.
  • the synthetic surface-active agents are selected from sulfonates, such as dodecyl benzene sulfonate and its derivatives; alkyl sulfate anionic surfactants; laurates, such as sodium laurate, sodium lauryl sulfates; ethanolamines, such as ethanolamine lauryl sulfate; polyethanolmides and mixture of ethanolamides of lauric acid or any mixture thereof.
  • Synthetic surface-active agents as defined above may be selected from anionic surfactants, such as alkyl benzene sulfonates, or sulfonates comprising potassium, sodium, ammonium, hydrogen or the like: sodium dodecyl benzene sulfonate and sodium tridecyl benzene sulfonate, commercially available surfactants selected from “Ardet” AB- 40 (sodium dodecyl sulfonate), “Conco” AAS-50S (ammonium dodecyl benzene sulfonate), “Conco” ATR-98S (hydrogen tridecyl benzene sulfonate), "Memkal” NOBS (sodium nonyl benzene sulfonate), “Sole-Fonate” 102 (calcium dodecyl benzene sulfonate) etc.
  • anionic surfactants such as alkyl benzene
  • anionic surfactants comprising alkyl phosphates, and alkyl sulphosuccinates e.g., sodium dioctyl sulphosuccinate and sodium di(tertiary)nonyl sulphosuccinate.
  • alkyl sulphosuccinates are the octyl and nonyl ester type.
  • Other anionic surfactants are selected from secondary alkyl sulfate type, monoglyceride sulfate, isethionates, acyl sarcosines, and its derivatives.
  • Amphoteric surfactants are potentially useful for the present invention and selected from coco amido alkyl betaine, acyl peptides and acyl amino acids.
  • Alkyl sulfate anionic surfactants are preferably those derived from lauryl and myristyl alcohols, and its derivatives, such as alkyl polyethylene glycol sulfates (alkyl ether sulfates), e.g., lauryl polyethylene glycol sulfate.
  • Ethanolamines are selected according to one preferred embodiment of the present invention monoethanolamine (MEA), diethanolamine (DEA) and triethanolamine (TEA) It is according to another embodiment of the present invention wherein the synthetic surface-active agents are selected from anionic surfactants, especially those derived from lauryl and myristyl alcohols
  • preservatives are preferably, yet not exclusively selected from biocides, bactericides or fungicides.
  • said method additionally comprising at least one step of admixing boric acid and/or borates; said borates are preferably selected from sodium, potassium, magnesium, calcium, barium manganese, ferrous borates or any combination thereof.
  • etheric oils are preferably obtained form fruits or vegetables selected from linen blossoms (etheric oils with quercitin and farnesol) St. Johns wort oil (for example, olive oil extracts) calendula, arnica (for example oily extracts of blossoms with etheric oils, polar extracts with flavonoid lemon balm (for example flavone and etheric oils), sage (for example etheric oils with thymol) niseseed
  • etheric oils with trans-anethol carnation oil (for example etheric oil with eugenol), camomile (camazulene, alpha-bisabolol, myrtols, (limonine, alpha-pinene, cineol), peppermint oil (for example, oil with menthol) caraway seed (for example, oil with carvone) larch (for example oil with alpha-pinene) Juniper, rosemarin, eucalyptus oil, lavender, fir needle oil, bergamo oil, citrus oil, lemon balm, marjoram, thyme, basil
  • preservatives selected from methyl- and/or propyl-paraben.
  • the aforesaid etheric oils are obtaind from fruits and vegetables, selected from sage, Rosemarie, lemon, bergamot, tea tree, mint, pine, sandalwood, patchouli, lemon grass, peppermint, grapefruit, oridanium, manuka, eucalyptus, geranium, clove, cinnamon, Melissa or any combination thereof.
  • additives are preferably, yet not exclusively, selected from perfuming agents, stabilizers, thickfires, emulsifiers, vitamins, radical scavengers, conditioners, antioxidants, lipophilic or hydrophilic plant extracts or any combination thereof.
  • the fillers or viscosity regulators are preferably selected from calcium carbonate, talc, dolomite, perlyte, magnesium carbonate or a mixture thereof.
  • water-soluble soap is obtained by hydrolyzing fats selected from vegetable oil, tallow, animal fats, cod liver oil, with sodium hydroxide or potassium hydroxide.
  • Said method may further comprise at least one step of admixing the obtained soap without separating the biomass with etheric oil.
  • Vegetable oil may comprised of immuno stimulants: echinacea purpuria (alcoholic extracts, fresh plant juice, pressed juice), elutheriococcus genticosus; alkaloids: rauwolfia, (for example, prajmaline evergreen, (for example vincamine); and phytopharmaceuticals, such as aloe, horse chestnuts (for example aescin), garlic (for example, garlic oil), pineapple (for example, bromelaein) ginseng (for example, ginsenoside), marythistle fruit (for example, extracts standardized on silbmarin), mouse thorn root (for example ruscogenine), Valeriana (for example valepotriate, and tincture valerainae nigh), Kava Kava (for example Cavalactone), hop blossom (hop bitters), extract of passiflorae, gentian (for example ethanol extract), anthraquinone containing drug extracts, (for example, aloin
  • the aforesaid method additionally comprising a step of reacting sodium or potassium hydroxide with oleic acid, tall oils, stearic or a combination thereof.
  • the soap additionally comprising fillers.
  • the fillers or viscosity regulators are preferably selected from calcium carbonate, talc, dolomite, perlyte, magnesium carbonate or a mixture thereof.
  • soap additionally comprising preservatives.
  • the preservatives are selected from boric acid and/or borates.
  • the borates are preferably selected from sodium, potassium, magnesium, calcium, barium manganese, ferrous borates or any combination thereof.
  • the concentration of the borate-containing compositions is varied from about 0.1% to 5.0%; and preferably from about 0.15% to 0.5% (weight percent).
  • the preservatives are selected from biocides, bactericides or fungicides.
  • the preservatives may comprise etheric oils.
  • the etheric oils are preferably but not exclusively obtained form fruits or vegetables selected from linen blossoms (etheric oils with quercitin and farnesol) St.
  • Johns wort oil for example, olive oil extracts) calendula, arnica (for example oily extracts of blossoms with etheric oils, polar extracts with flavonoid lemon balm (for example flavone and etheric oils), sage (for example etheric oils with thymol) niseseed (etheric oils with trans-anethol), carnation oil (for example etheric oil with eugenol), camomile (camazulene, alpha-bisabolol, myrtols, (limonine, alpha-pinene, cineol), peppermint oil (for example, oil with menthol) caraway seed (for example, oil with carvone) larch (for example oil with alpha-pinene) Juniper, rosemary, eucalyptus oil, lavender, fir needle oil, bergamot oil, citrus oil, lemon balm, marjoram, thyme, basil (stomatica or herbs) and fennel.
  • preservatives are selected from methyl- and/or propyl-paraben.
  • the etheric oils are obtained from fruits and vegetables selected from sage, Rosemarie, lemon ,bergamot, tea tree, mint, pine, sandalwood, patchouli, lemon grass, peppermint, grapefruit, oridanium, manuka, eucalyptus, geranium, clove, cinnamon, Melissa or a combination thereof.
  • the concentration of etheric oils is preferably ranging from about 0.1 to 5.0% (weight percent).
  • the soap as defined in any of the above additionally comprising additives, and/or it is additionally comprised natural soaps and/or glycerol.
  • the organic residues are obtained from oil cake mill.
  • the oil obtained from the oil cake mill is preferably selected from olive oil, Soya oil, linseed oil, sunflower oil or a mixture thereof.
  • the soap is additionally comprised of water immiscible and/or water miscible process products or by-products obtained from the oil cake milling.
  • the products obtained from the oil cake milling are preferably, and according to yet another embodiment of the present invention, ingredients of crushed seeds, especially olive crushed pips or seeds.
  • organic residues are alternatively obtained from organic residues of juice production or wood flow.
  • the method of producing olive soap as defined in any of the above comprises steps selected in anon- limiting manner from: a. cleansing olives, e.g., rinsing it with water; b. grinding or crushing the olives to paste; c. mixing to increase olive oil yield; d. separating or decanting the oil and water from pomace; e. separating a the oil from polyphenols rich water and optionally recycling the same; f. hydrolyzing said oil so as water soluble soap is obtained; and, g. dispersing said pomace organic residues in a water miscible solution until a homogeneous soap composition phase is obtained.
  • the method further comprising step or steps of removing at least a portion of the pits from the olive flash before the olives are grinded to paste so as a pits-free olive oil is obtained.
  • pits-free olive oil refers to an olive oil free of pits' fragments and form pits' ingredients. It is according to another embodiment of the present invention wherein the method further comprising step or steps of removing at least a portion of the pits from the olive flash before the olives are grinded to paste and admixing said pits with the pomace.
  • the method further comprising step or steps of removing at least a portion of the pits from the olive flash before the olives are grinded to paste and admixing the pits with the obtained soap. It is according to another embodiment of the present invention wherein the method further comprising step or steps of admixing said polyphenols rich waters with the soap until a homogeneous soap composition phase is obtained.
  • the method further comprising step or steps of admixing said etheric oils with the soap until a homogeneous soap composition phase is obtained. It is according to another embodiment of the present invention wherein the step or steps of separating of the oil and water from pomace is provided by either a tri-phases decanter or a two-phases decanter.
  • a pits-free olive oil is provided.
  • the oil is characterized by being free of pits' fragments and of pits' ingredients and oils
  • glycerol (15g) was admixed with stearine (15Og) at 75C until the stearine dissolved.
  • ETA (4Og) is further admixed by a means of a homogenizer.
  • a water solution of Na 2 B 4 O 7 (5Og, 0.3%) is admixed with sodium hydroxide.
  • the glycerol-stearine solution homogenized with E-70.
  • Olive seed pressing product (20Og) was further admixed with effective measure of a mixture of pine oil and clove oil.
  • soap was produced hydrolyzing at least one natural oil so as water soluble soap is obtained; dispersing organic residues in a water miscible solution until a homogeneous soap composition phase is obtained.
  • Said soap comprising water 15Og, NaOH 3.5g, Borax 0.2% 0.3g, stearin 2Og, ETA-70 2Og, glycin 6Og, dense cake of crushed and compressed olive seed husks 25Og, tea tree oil 1.25g, lemon grass 1.25g and magnesium carbonate HOg.
  • Another soap was produced in a method according to the present invention, and comprising water 150g, NaOH 3.5g, lauramide 2g, Borax 0.2% 0.3g, stearin 2Og, ETA- 70 18g, glycin 6Og, dense cake of crushed and compressed olive seed husks 29Og, tea tree oil 1.45g, cinnamon oil 1.45g and perlite 9Og.
  • a liquid soap was further produced in a method according to the present invention, and comprising water 15g, olive oil 15g, coconut oil 5g, lauramide 5g, potassium hydroxide
  • pine oil 2g 5.45g, pine oil 2g, orange oil 3g, soy oil wash 5Og, dolomite 4Og.
  • Another soap was produced in a method according to the present invention, and comprising water 300g, NaOH 7.1g, lauramide 38g, Borax 0.2% 0.3g, glycerin 6Og, stearic acid 38g, ETA-70 18g, glycin 6Og, dense cake of crushed and compressed olive seed husks 44Og, pine oil 8.8g, clove oil 2.68g, and talc 80g.
  • Another soap was produced in a method according to the present invention, and comprising water 150g, NaOH 3.5g, lauramide 38g, Borax 0.2% 3g, stearin 2Og, ETA-70
  • Another soap was produced in a method according to the present invention, and comprising water 150g, NaOH 3.5g - 3.7g, lauramide 2-2.5g, Borax 0.2% 0.3g, stearin

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Biochemistry (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
PCT/IL2006/000338 2005-03-17 2006-03-15 Soaps from organic residues and method of producing the same Ceased WO2006097929A2 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
EP06711320.9A EP1868560A4 (en) 2005-03-17 2006-03-15 SOAPS FROM ORGANIC REST AND MANUFACTURING METHOD THEREFOR
JP2008501488A JP5198246B2 (ja) 2005-03-17 2006-03-15 有機残渣から作られた石鹸およびその製造方法
MX2007011308A MX2007011308A (es) 2005-03-17 2006-03-15 Jabones de residuos organicos y metodos para producirlos.
AU2006224152A AU2006224152B2 (en) 2005-03-17 2006-03-15 Soaps from organic residues and method of producing the same
US11/908,889 US20080207480A1 (en) 2005-03-17 2006-03-15 Soaps From Organic Residues And Method Of Producing Same
CA002600940A CA2600940A1 (en) 2005-03-17 2006-03-15 Soaps from organic residues and method of producing the same
US12/965,982 US8778863B2 (en) 2005-03-17 2010-12-13 Soaps from organic residues and method of producing the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IL167500 2005-03-17
IL167500A IL167500A (en) 2005-03-17 2005-03-17 Soaps from residues from the processing of plant materials and method of producing the same

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US11/908,889 A-371-Of-International US20080207480A1 (en) 2005-03-17 2006-03-15 Soaps From Organic Residues And Method Of Producing Same
US12/965,982 Continuation-In-Part US8778863B2 (en) 2005-03-17 2010-12-13 Soaps from organic residues and method of producing the same

Publications (2)

Publication Number Publication Date
WO2006097929A2 true WO2006097929A2 (en) 2006-09-21
WO2006097929A3 WO2006097929A3 (en) 2006-11-30

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PCT/IL2006/000338 Ceased WO2006097929A2 (en) 2005-03-17 2006-03-15 Soaps from organic residues and method of producing the same

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US (1) US20080207480A1 (enExample)
EP (1) EP1868560A4 (enExample)
JP (1) JP5198246B2 (enExample)
CN (1) CN101160113A (enExample)
AU (1) AU2006224152B2 (enExample)
CA (1) CA2600940A1 (enExample)
IL (1) IL167500A (enExample)
MX (1) MX2007011308A (enExample)
WO (1) WO2006097929A2 (enExample)

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EP2471545A4 (en) * 2009-05-11 2014-04-02 Herrero Maria Pilar Mateo SAPONIFIED OLEA EUROPAEA MICROENCAPSULATED COMPOSITION, ITS USE AND PROCESS FOR OBTAINING THE SAME
CN104178383A (zh) * 2014-09-09 2014-12-03 青岛润鑫伟业科贸有限公司 一种红酒手工皂的制作方法
WO2018182762A1 (en) * 2017-03-31 2018-10-04 Healthpro Brands, Inc. Method of increasing water soluble nutrient extraction from plant matter

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CN102186341B (zh) * 2008-10-20 2013-12-25 荷兰联合利华有限公司 抗菌组合物
MX2012003563A (es) 2009-09-24 2012-04-30 Unilever Nv Agente desinfectante que comprende eugenol, terpineol y timol.
KR101140728B1 (ko) 2010-03-18 2012-05-03 김포시(농업기술센터) 순무 종자유를 함유하는 순무 세제 조성물
CN103354741B (zh) 2010-12-07 2016-01-13 荷兰联合利华有限公司 口腔护理组合物
BRPI1101133A2 (pt) * 2011-03-31 2013-06-04 Natura Cosmeticos Sa composiÇço cosmÉtica para limpeza da pele contendo àleos de origem vegetal, seu processo de fabricaÇço, bem como seu uso
WO2013064360A2 (en) 2011-11-03 2013-05-10 Unilever N.V. A personal cleaning composition
US10532022B2 (en) * 2014-07-21 2020-01-14 The United States Of America, As Represented By The Secretary Of Agriculture Whole stablized olive mill process water, production thereof and uses thereof
CN107384636B (zh) * 2017-08-02 2019-11-19 上海中翊日化有限公司 一种相对温和的透明皂基清洁制剂
CN111793534A (zh) * 2020-07-17 2020-10-20 华容县新发农业开发有限公司 一种红豆杉香皂及其制备方法和应用

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EP1868560A4 (en) 2014-06-11
JP2008533271A (ja) 2008-08-21
AU2006224152B2 (en) 2012-04-26
US20080207480A1 (en) 2008-08-28
IL167500A (en) 2010-12-30
WO2006097929A3 (en) 2006-11-30
CN101160113A (zh) 2008-04-09
CA2600940A1 (en) 2006-09-21
JP5198246B2 (ja) 2013-05-15
EP1868560A2 (en) 2007-12-26
MX2007011308A (es) 2008-03-18
AU2006224152A1 (en) 2006-09-21

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