GB2458019A - Biodegradable cleaner - Google Patents

Biodegradable cleaner Download PDF

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Publication number
GB2458019A
GB2458019A GB0903681A GB0903681A GB2458019A GB 2458019 A GB2458019 A GB 2458019A GB 0903681 A GB0903681 A GB 0903681A GB 0903681 A GB0903681 A GB 0903681A GB 2458019 A GB2458019 A GB 2458019A
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Prior art keywords
ester
acid
fatty acid
biodegradable
composition according
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GB0903681D0 (en
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Christopher Daniel Swales
Allen Swales
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Individual
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Individual
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/667—Neutral esters, e.g. sorbitan esters
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/266—Esters or carbonates

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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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)

Abstract

A biodegradable cleaner comprises a C3-5 alkyl ester of C12-24 fatty acid, preferably a propyl ester of a C18 fatty acid e.g._linoleic, elaidic, stearic, in particular an iso-propyl ester of a mixture of C18 fatty acids. Also disclosed is a method of cleaning a surface using said composition, and the manufacture of said composition. The composition is preferably made by transesterification, which may be acid or base catalysed.

Description

COMPOSITION
FIELD OF INVENTION
This invention relates to a novel biodegradable cleaner, to methods of preparation and compositions related thereto.
BACKGROUND TO THE INVENTION
Household and industrial cleaning products generally comprise active ingredients and/or solvents which are often hazardous and/or toxic. Thus, such products present a problem both from the use?s perspective, in that, for example, they must take precaution to ensure that the product does not come into contact with the skin. Furthermore, such products are generally environmentally unfriendly and therefore the manufacture and/or disposal of waste material is hazardous and/or expensive. Many of the active ingredients and/or solvents are carcinogenic and hazardous to health in general and may also be air pollutants or water pollution that threaten aquatic organisms and drinking water supplies.
There is therefore a need for an "environmentally friendly" cleaner which should be effective, economically viable and affordable and non-toxic to the environment generally and to humans specifically. Ideally, such a cleaner should be biodegradable and preferentially be available from renewable resources.
Thus, for example, International Patent application No. WO/2007/062497 describes a biodegradable cleaner, which comprises a mixture of or one of Ci to C2 ester of a C14 to C24 fatty acid. After use it leaves a grease residue on the treated surface, which may be removed with common soap solutions. However, the cleaner described is expensive to manufacture, for example, due to the cost and the hazardous nature of the methanol or ethanol required for esterification of the fatty acid.
US Patent 6,096,699 describes a fat and grease remover comprising a C1 to C4 ester of a C16 to C20 fatty acid, a C1 to C4 ester of lactic acid, a surfactant and a thickener.
However, the use of surfactants in the composition is generally considered to be environmentally unfriendly due. inter alia, to their interaction with water following disposal.
We have now surprisingly found a novel cleaner composition which is environmentally friendly, non-toxic, biodegradable and furthermore, may be manufactured from waste materials.
SUMMARY OF INVENTION
Therefore, one object of the present invention is to produce a novel cleaning agent which environmentally friendly, biodegradable and capable of acting as a degreasing agent.
Thus, according to a first aspect of the invention we provide a biodegradable cleaner composition comprising a C3 to C5 alkyl ester of Ci 2 C24 fatty acid.
Preferably the C3 to C5 alkyl ester is a propyl ester. The propyl ester may be n-propyl, however preferentially the propyl ester is an iso-propyl ester. The amount of the propyl ester of C18 fatty acid present may vary, but it is desirable that the C18 fatty acid propyl ester is present in an amount of from 70 to 95% w/w.
The fatty acid may preferably be a C16 to C20 fatty acid and more preferably a C18 fatty acid. It will be appreciated by the person skilled in the art that a mixture of fatty acids and alkyl esters may be utilised in the biodegradable cleaner of the invention.
Furthermore, it will be understood that reference to a C16 to C20 fatty acid shall include.
saturated and unsaturated fatty acids and straight chain and branched fatty acids. Thus. a variety of C18 fatty acids will exist. Thus, the biodegradable cleaner composition of the invention may comprise a single C18 fatty acid ester or the acid moiety may comprise a mixture of C18 fatty acids. The use of a mixture of C18 fatty acids is advantageous in that, inter alia, it reduces the number and therefore cost of processing steps. However, more importantly it is an object of the invention to provide a cleaning composition that may be prepared using recyclable materials such as used cooking oil.
Thus, the C18 fatty acid (ester) may be one or more of linoleic acid. elaidic acid and/or stearic acid. As hereinbefore described, preferentially the fatty acid comprises a mixture of fatty acids, e.g. at least two fatty acids which fatty acids are selected from the group consisting of linoleic acid, elaidic acid and stearic acid. In a preferred embodiment of the invention the C18 fatty acid is a mixture comprising Jinoleic acid and elaidic acid.
When the biodegradable cleaner of the invention comprises a mixture of linoleic acid to elaidic acid the ratio of linoleic acid to elaidic acid may vary, but may be from 2:1 to 1:1, preferably from 3:2 to 5:4. Thus, for example, the amount of linoleic acid ester present may be from 40 to 60%w/w, preferably from 45 to 55% w/w. Alternatively, the amount of elaidic acid ester present may be from 25 to 45% w/w, preferably from 30 to 40%w/w.
In a further alternative to the invention the C18 fatty acid ester may comprise stearic acid.
When the C18 fatty acid ester is stearic acid, the amount of stearic acid ester present is from 7 to 17% w/w. preferably from 10 to 14% w/w.
According to a further aspect of the invention we provide the use of a C3 to C ester of C12 to C24 fatty acid as a biodegradable cleaner.
Preferably the use comprises the use of a propyl ester. Further, preferably the fatty acid may be a C16 to C fatty acid, more preferably a C18 fatty acid.
Alternatively, we provide the use of a propyl ester of C18 fatty acid in the manufacture of a biodegradable cleaner.
Preferably the use comprises the use of a pi'opyl ester. Further, preferably the fatty acid may be a C16 to C fatty acid, more preferably a C18 fatty acid.
It will be understood buy the person skilled in the art that the use hereinbefore described may comprise the uce of propyl esters of a mixture C1 fatty acids as a biodegradable cleaner or in the manufacture of a biodegradable cleaner.
In a yet further aspect of the invention we provide a method of cleaning a surface which comprises the application of a biodegradable cleaning composition as hereinbefore described.
In a yet further aspect of the invention we provide a biodegradable cleaner formulation which comprises the propyl ester of one or more C18 fatty acids in combination with a suitable adjuvant, diluent or carrier.
It will be understood by the person skilled in the art that the composition of the invention may be manufactured by conventional methods known per Se. However, it is a further novel aspect of the present invention to provide a method of preparation of a composition as hereinbefore described which comprises the esterification and/or trans-esterification of waste oil, e.g. waste vegetable oil. Thus, according to a further aspect of the invention we provide a method for producing a composition as hereinbefore described which comprises the trans-esterification of waste vegetable with a C3 to C5 alkyl alcohol, e.g. propyl alcohol, preferably iso-propyl alcohol. The trans-esterification reaction of the invention may preferentially be carried in the presence of catalyst, e.g. a heterogeneous catalyst, such as a carbonate, e.g. potassium carbonate or a zeolite, etc. Alternatively, the catalyst may be an acid catalyst, such as, hydrochloric acid or an alkali catalyst, such as sodium hydroxide.
In the method of the invention the waste oil used may be from a variety of sources. Thus, for example, the waste oil may be selected from one or more of coconut oil, palm oil.
olive oilS canola oil. peanut oil, hemp oil, safflower oil, sunflower oilS corn oil, cotton seed oil, flax (linseed) oil, rapeseed oil, soy bean oil. jojoba oil, jatropha oil, recycled flyer oil or lard, fish oil and tallow: and mixtures thereof. It will be understood by the person skilled in the art that the source of the oil may other than waste oil, for example.
the naturally sourced oils may themselves be used.
Advantageously, the formulation of the invention may include, for example, a fragrance compound or a perfume composition. The fragrance compound or perfume composition may comprise one or more essential oils and/or active ingredients of essential oils. An essential oil includes any type of volatile oil that is obtained from a plant and possesses the odour and other characteristic properties of the plant. Examples of useful essential oils include: almond biller oil, anise oil, basil oil, bay oil, caraway oil, cardamom oil, cedar oil, celery oil, chamomile oil, cinnamon oil, citronella oil, clove oil, coriander oil, cumin oil, dill oil, eucalyptus oil, fennel oil, ginger oil, grapefruit oil, lemon oil, lime oil, mint oil, parsley oil, peppermint oil, pepper oil, rose oil, spearmint oil (menthol), sweet orange oil, thyme oil, turmeric oil, and oil of wintergreen. Examples of active ingredients in essential oils are: citronellal, methyl salicylate, ethyl salicylate, propyl salicylate, citronellol, safrole, and limonene.
A variety of suitable carriers may be sued in the formulation of the invention. Thus such a carrier may, for example, be selected form the group consisting of water, alcohol, silicone, petrolatum, lanolin; or an organic liquid carrier, such as a liquid aliphatic hydrocarbon (e.g. pentane, hexane, heptane, nonane, decane, etc) or a liquid aromatic hydrocarbon.
Other suitable carriers include silicone, petrolatum, lanolin, liquid hydrocarbons, agricultural spray oils, paraffin oil, tall oils, liquid terpene hydrocarbons and terpene alcohols, aliphatic and aromatic alcohols, esters, aldehydes, ketones, mineral oil, higher alcohols, finely divided organic and inorganic solid materials. In addition to the above-mentioned liquid hydrocarbons, the carrier can contain conventional emulsifying agents which can be used for causing the active ingredient to be dispersed in, and diluted with, water for end-use application. Still other liquid carriers can include organic solvents such as aliphatic and aromatic alcohols, esters, aldehydes, and ketones. Aliphatic monohydric alcohols include methyl, ethyl, normal-propyl, isopropyl, normal.-butyl, sec-butyl, and tert-butyl alcohols. Suitable alcohols include glycols (such as ethylene and propylene glycol) and pinacols. Suitable polyhydroxy alcohols include glycerol, arabitol, erythritol, sorbitol, and the like. Finally, suitable cyclic alcohols include cyclopentyl and cyclohexyl alcohols.
Conventional aromatic and aliphatic esters, aldehydes and ketones can be used as carriers, and occasionally are used in combination with the above-mentioned alcohols.
Still other liquid carriers include relatively high-boiling petroleum products such as mineral oil and higher alcohols (such as cetyl alcohol). Additionally, conventional or so-called "stabilizers" (e.g. tert-butyl sulfinyl dimethyl dithiocarbonate) can be used in conjunction with, or as a component of, the carrier or carriers used in a composition as made according to this invention.
In addition, the formulation of the invention may include one or more anti-oxidants.
Examples of antioxidants include alkylated diphenylamines, N-alkylated phenylenedianiines, phenyl-a-naphthylamine, alkylatedphenyl-os-naphthylamine, dimethyl quinolines,trimethyldihydroquinolines and oligomeric compositions derived therefrom, The formulation of the invention may be formulated as one or more of a liquid, a sprayable liquid, a lotion, an aerosol, a foam or a gel, etc.
DETAILED DESCRIPTION OF THE iNVENTION
Characterisation of a sample of an iso-propyl derived ester The sample was initially analysed by GC for area % of the components followed by GC-MS to identify each of the components in the mixture.
Results Iso-propyl ester GC data Retention Area Retention Name Structure % Library RMM time GC % OC time GC-Alternative name Match MS, __________ _______ Area% ___________________ ___________ ___________ _______ 20.455 10.08 5.526, Isopropyl Palmitate 1 76 298.5 ________ ______ 10.00% ________________ _________ _________ ______ 33.958 49.47 10.876, Isopropyl linoleate 2 99 322.53 50.91% (9Z, 12Z)-isopropyl octadeca-9, 12- __________ _______ ___________ dienoate 34.160 33.49 11.188, Elaidic acid, 3 93 32.54 36.59% isopropyl ester (E)-isopropyl _________ _______ __________ octadec-9-enoate 34.311 1.57 _________ Oleic acid 4 52 282.46 34.416 0.21 _________ ________________ _________ _________ 34.629 0.24 _________ _________________ _________ _________ 34.948 3.08 12.390, Octadecanoic acid 5 90 284.48 2.50% Stearic acid Or or or or Iso-propyl stearate 6 94 326.56 _________ ______ _________ Isopropyl_stearate __________ _________ 38.374 0.18 _________ ________________ _________ _________ 38.774 0.32 _________ _________________ __________ _________ 41.148 0.40 ________ _______________ ________ ________ 41.938 0.82 45.056 Unknown _________ _________ 257 43.348 0.13 __________ _________________ __________ _________
Conclusions
The majority of the sample is isopropyl linoleate (49.5%) and Elaidic acid iso-propyl ester (33.5%). The main impurity is isopropyl palmitate (10.1%) and the minor impurities are oleic acid (1.5%) and stearic acid or the isopropyl ester (3.1%). It is difficult to distinguish whether the minor impurity at 3% levels is stearic acid or the isopropyl ester as both produce very similar mass spectra. All other impurities were below 1% and difficult to characterise by GC-MS.
Whilst the method of this invention has been described with reference to certain embodiments, it will be evident to those skilled in the art that numerous modifications and variations are possible without departing from the spirit or scope of the invention as described.
Appendix 1 GC Method for Analysis of Iso-propyl ester (Temp 2 or GC 37) Column HP5 30m x 0.32 x 0.25um Colunm head pressure 10 PSI Inlet temperature 250°C Mode Split 50:1 Detector temperature 250°C Oven parameters Initial temperature 170°C Initial time 30 mins Ramp 10 °C/min Final temperature 280°C Final time 10 mins Injection volume luL Sample preparation One drop of iso-propyl ester was dissolved in 2m1 DCM OC-MS Method for Analysis of Iso-propyl ester (Iso 170) Column HP5-MS 15m x 0.25 x 0.25um Column head pressure 12 PSI Inlet temperature 250°C Mode Split 50:1 Detector Mass line 280°C Oven parameters Initial temperature 170°C Initial time 40 mins Ramp 10 °C/min Final temperature 275 °C Final time 5 mins Injection volume luL Sample preparation One drop of iso-propyl ester was dissolved in 2m1 DCM Appendix 2: GC Chromatogram rita rile 2:'CEEtC32'2LaTA'C:'1fl4 -TA& 34 l:Thfl4 flE 202-12-l4 _--4siCF4.L Sarr4ie Nar.a: isa crn.. ester Ang Gpaiat.-t-. se;-Line 24 Ang. Z:.;ttumeht: 2ntr.aient 2 l:ct�an: 7ia1 IC2 :ncn3n ate: .S C 3CY' :11: 4 all �xtcrnal A.::j.Meth:ct 2:\Cier.?: ::a:Al:2-_24 AThB ?4l:c.2l4... i7-_2-4 l?-E-4S'EMPtJi Last.nçe: ll'l4.'�=.' :Li.fl P11 r IPC'3 A?1y; M4tt:1 2:'rHE32'2\Tttl2OC 2'.M tnt. : IC. 2'22r:4" 30 24 3.c flIt Mvthc'd I:fc' : C-eneaa Eurnc.ff Metht4 30:d'c-Fin A n:-tna.2U7 14sTab3e2e0; 14eRt30?-i2 4 i4-0 4citC3O4 cia 2E000 I 500. iouoe scea
.6.t.Cjt Si cc 40 area Percent Rçcrt 3:.rtec! en: c:lttic,It -se Mult:r..:cr & ilttrn?a:tcr ntlt CLs 2: Ffl.. A. Fr:t ?tgna Peak Rertire lyre aacttt Area Hei*c Area I it snn2 FpA' pA: k I IC.45 NM 0...7 3fl.E4C...3I IC.C8$71 2.31'.Z53 Mr.S%'332S 1.i 34F44 4?.4CE3 3 34 IE MF 0.0234.43)23 201 ZIP 0.J.eC 32.VI'05 _2.411r _.363 :r'-"'----v -nr FaIe I 2 Created wlh novaPDF Prnter!w iwvaP3F comi. Please regelertrs remove th:s message Lata fle:.HEM3\2'rATA\3rt_4 TAE 34SC2i4:sP. :cz-n-4:S--4;\i3rLcfl.r is tr:i ester e.k etflt' ype Wcztt Area EeLgt area * :rr. :A's: :p?) S. 34.4 fl). JE:E r:45 L. 6 54.fl? Y 51..164 C.2C'S - MM 3624 9 6212S E.C25'4 3.
6 25.3'3 ?2 D.66e3 5 Z7i4:.553c 3....5534 4 36'4)2)04L.) C7 3 5) 4l.L4 ML:.33C...: 55'!? 5:isn.3r9 >26 D C.6 4'..S& 4.t2L3 6.61655 2 45.346 N�=: ).)455 4.22:>C r.34...s.53S5 232 _432 Z43*4.'ThCf c Pe_rt " Detailed Chromatogram A, Frafl Sgnal(20071214 STAB342OO7I2I4 T&R2007*12-14 I9Oe4*IOO24OI 0) ---___________________--p * . mm RD1 A Fiol Si,.J(O71214 STAB34\O1l214T&R27 12-14 1905 l105F2401 0) pA -"I,
ISO
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FISt A. Frail Sqai(20071214STA834120071214T&R2007.12.14 I9.0541F2t01 0)
ISO
_________
338 34 342 344 346 348 35 352 054nai

Claims (42)

  1. Claims 1. A biodegradable cleaner composition comprising a C3 to C5 alkyl ester of a C12 to C24 fatty acid.
  2. 2. A biodegradable cleaner composition according to claim 1 wherein the C3 to C5 alkyl ester is a propyl ester.
  3. 3. A biodegradable cleaner composition according to claim 2 wherein the propyl ester is an iso-propyl ester.
  4. 4. A biodegradable cleaner composition according to claim 1 wherein the C3 to C5 ester of a C12 to C fatty acid is present in an amount of from 70 to 95% w/w.
  5. 5. A biodegradable cleaner composition according to claim 1 wherein the fatty acid is a C16 to C20 fatty acid.
  6. 6. A biodegradable cleaner composition according to claim 5 wherein the fatty acid is a C13 fatty acid.
  7. 7. A biodegradable cleaner composition according to claim 6 wherein the C18 fatty acid is linoleic acid.
  8. 8. A biodegradable cleaner composition according to claim 6 wherein the C18 fatty acid is elaidic acid.
  9. 9. A biodegradable cleaner composition according to claim 6 wherein the C18 fatty acid is stearic acid.
  10. 10. A biodegradable cleaner composition according to claim 6 wherein the C18 fatty acid comprises a mixture of at least two fatty acids which fatty acids are selected from the group consisting of linoleic acid. elaidic acid and stearic acid.
  11. 11. A biodegradable cleaner composition according to claim 10 wherein the C18 fatty acid niixture comprises linoleic acid and elaidic acid.
  12. 12. A biodegradable cleaner composition according to claim 11 wherein the ratio of linoleic acid to elaidic acid is from 2:1 to 1:1.
  13. 13. A biodegradable cleaner composition according to claim 12 wherein the ratio of linoleic acid to elaidic acid is from 3:2 to 5:4.
  14. 14. A biodegradable cleaner composition according to claim 7 wherein the amount of linoleic acid ester present is from 40 to 60%wlw.
  15. 15. A biodegradable cleaner composition according to claim 14 wherein the amount of linoleic acid ester present is from 45 to 55%w/w.
  16. 16. A biodegradable cleaner composition according to claim 8 wherein the amount of elaidic acid ester present is from 25 to 45%w/w.
  17. 17. A biodegradable cleaner composition according to claim 16 wherein the amount of elaidic acid ester present is from 30 to 40%wlw.
  18. 18. A biodegradable cleaner composition according to claim 11 wherein the C18 fatty acid also comprises stearic acid.
  19. 19. A biodegradable cleaner composition according to claim 18 wherein the amount of stearic acid ester present is from 7 to 17% w/w.
  20. 20. A biodegradable cleaner composition according to claim 19 wherein the amount of stearic acid ester present is from 10 to 14% w/w.
  21. 21. The use of a C3 to C5 ester of C12 to (:24 fatty acid as a biodegradable cleaner.
  22. 22. The use according to claim 21 wherein the ester is a propyl ester.
  23. 23. The use according to claim 21 wherein the fatty acid is a C18 fatty acid.
  24. 24. The use of a (23 to C5 ester of a C12 to C2 fatty acid in the manufacture of a biodegradable deaner.
  25. 25. The use according to claim 24 wherein the ester is a propyl ester.
  26. 26. The use according to daim 24 wherein the fatty acid is a C18 fatty acid.
  27. 27. The use of the propyl esters of a mixture C13 fatty acids as a biodegradable cleaner.
  28. 28. The use of the propyl esters of a mixture C18 fatty acids in the manufacture of a biodegradable cleaner.
  29. 29. A method of cleaning a surface which comprises the application of a biodegradable cleaning composition comprising a C3 to C5 ester of a C12 to C24 fatty acid.
  30. 30. A method according to claim 29 wherein the C3 to C5 ester is the propyl ester.
  31. 31. A method according to claim 29 wherein the C12 to CM fatty acid is a C13 fatty acid.
  32. 32. A biodegradable cleaner formulation which comprises the C to C5 ester of one or more a C12 to C1 fatty acids in combination with a suitable adjuvant, diluent or carrier.
  33. 33. A biodegradable cleaner formulation according to claim 32 wherein the C3 to C5 ester is the propyl ester.
  34. 34. A biodegradable cleaner formulation according to claim 32 wherein the C12 to C24 fatty acid is a C18 fatty acid.
  35. 35. A biodegradable cleaner according to claim 32 which includes an additional scent or aromatic oil.
  36. 36. A biodegradable cleaner composition according to claim 32 wherein the formulation is in the form of an oil, a sprayable liquid, an aerosol, a foam, a cream, an ointment, a gel or a paste.
  37. 37. A method of producing a biodegradable cleaner composition comprising a C3 to C5 ester of a C12 to C fatty acid which comprises the trans-esterification of waste vegetable oil with (:12 to C34 alcohol.
  38. 38. A method according to claim 37 wherein the reaction is carried out in the presence of a catalyst.
  39. 39. A method according to claim 38 wherein the catalyst is a heterogeneous catalyst.
  40. 40. A method according to claim 38 wherein the catalyst is an acid catalyst.
  41. 41. A method according to claim 38 wherein the catalyst is an alkali catalyst.
  42. 42. A composition, use, method or formulation substantially as hereinbefore described with reference to the accompanying examples.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8617317B1 (en) 2012-07-31 2013-12-31 Ecolab Usa Inc. All-purpose cleaners with natural, non-volatile solvent
US10858573B2 (en) 2014-01-16 2020-12-08 Wilmar Trading Pte Ltd Olefinic ester compositions and their use as cleaning agents

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5380453A (en) * 1988-09-26 1995-01-10 Unichema Chemie B.V. Composition comprising alkyl esters of aliphatic (C8 -C22) monocarboxylic acids and oil in water emulsifier
EP0971012A1 (en) * 1998-07-07 2000-01-12 Institut Francais Du Petrole Use of esters of oils for cleaning surfaces contaminated with hydrocarbons
US6096699A (en) * 1999-09-03 2000-08-01 Ntec Versol, Llc Environmentally friendly solvent
US20050256022A1 (en) * 2004-05-12 2005-11-17 May Choo Y High performance cleaning agent

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5380453A (en) * 1988-09-26 1995-01-10 Unichema Chemie B.V. Composition comprising alkyl esters of aliphatic (C8 -C22) monocarboxylic acids and oil in water emulsifier
EP0971012A1 (en) * 1998-07-07 2000-01-12 Institut Francais Du Petrole Use of esters of oils for cleaning surfaces contaminated with hydrocarbons
US6096699A (en) * 1999-09-03 2000-08-01 Ntec Versol, Llc Environmentally friendly solvent
US20050256022A1 (en) * 2004-05-12 2005-11-17 May Choo Y High performance cleaning agent

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8617317B1 (en) 2012-07-31 2013-12-31 Ecolab Usa Inc. All-purpose cleaners with natural, non-volatile solvent
US10858573B2 (en) 2014-01-16 2020-12-08 Wilmar Trading Pte Ltd Olefinic ester compositions and their use as cleaning agents

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GB0804031D0 (en) 2008-04-09

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