2) United States Patent sadovsky et al. ($4) NEUTRALIZATION OF ODORS (71) Applicant: SADOVSKY LYD., Ashkelon (IL) (72) Inventors: Shmuel Sadovsky, Ashkelon (IL): U Bach, Efrat (IL) (93) Assignee: Sadoysky Ltd., Ashkolon (IL) (*) Notice: Subject to any disclaimer, the term of this pateat is extended or adjusted under 35 USC. 184(b) by 9 days. (21) Appl Nos 180833,838 (22) PCT Filed: Dee. 7, 2018 (86) PCT No, § 371 (X0), (2) Date: PCTAL2015/51186 Jun. 6, 2017 (87) PCT Pub. Nos WO2016/092541 PCT Pub. Date: Jun. 16, 2016 63) Prior Publication Data US 2018/0268158 AL Sep, 20, 2018 G0) Foreign Application Priority Data Dee. 7, 2014 iL) 236099 (1) Inch. AGI 913 (2006.01) GIL 9/12 (2005.01), AGIL 9/14 (2005.01) ‘AGI 97012 (2006.01) AGI 905, (006.01), AOLL 218 (2006.01), (2) US. AGLL 9/14 (2013.01): “AGLL 2/18 (2013.01); AOUL 9022 (2013.01) AGIL 9905 (2013.01), ABIL, 2208/21 (2013.01); Co2F 2308/02 (2013.01) Field of Classification Seareh None ‘See application file for compet seateh history (56) References Cited USS. PATENT DOCUMENTS 71974 Van Viahakis S003, Malceny AGL 9012 95 285 'US010376607B2 (10) Patent No.: (4s) Date of Patent: US 10,376,607 B2 Aug. 13, 2019 20090108969 AL 6/2005 Caswell ta Sonaone24s AL 42004 Masaya 2n0avi014s) AL $2004 Schur duonzoltas Al* 93600 Brady orb sx a310 20060216365 AL 972006 Masi etal Soavioresssi Al 73007 Natta et anno017878% AL 72009 rows a donourisie Al $200) Atom ta 2000032466) AL_ 122009 Legendre eal #2476. 20120007754 AL 42012 Vlad etal 412015. Mavi et a POREIGN PATENT DOCUMENTS 2 S007s17 A L190 » Tosies9 A 21905 2000069083 32000 Wo aoosoeso4s At 73008 wo aorsoeo6ay At "T2015 (OTHER PUBLICATIONS How to Kill Mosquito Larva in Stanng Water With Household Produsts” htps www nker com 13406092 nara: semaly acceso Dec. 62018; tiles dat Aug. 28,2017 (Year. Technical Dat Shest for TERGITOL!™ NP-10 Surfctat from Dow, acceso De. 6, 2018 (Yur 2018) Technical Data Soc for TERGITOL™ NPS Surfactant fom Dow sccered Dec. 6, 2018 (ar 2018)* ‘Kedaohman, Adopt a. "A potential study on clove ol cugeno! aod eugensl acetate us dice fel bio-adtves ad thet perfor ‘mance on one eyliner engine” Transport 25.1 {2010} 66-76 Gear 2010)" * cited by examiner Primary Examiner (74) Attornes, Agent, or Firm Malley, Nissa M Westerberg McAndrews, Held & on ABSTRACT The present disclosure provides compositions comprising at Jeastone eugenol-contaning odor neutralizing agent and at Teast one flm forming agent for teating, reducing or net tralizing malodors. 17 Claims, No DrawingsUS 10,376,607 B2 1 NEUTRALIZATION OF ODORS ‘This application is led pursuant to 35 US.C. 371 as a US. National Phase application of Intemational Patent Application No. PCT/IL2015I051186, which was filed Dee. 7, 2015, claiming the benefit of priority to Israel Patent Application No. 236099, which was fled on Sep. Dee. 7, 2014. The content of each of the aforementioned patent applications is incorporated herein by reference in its irety. ‘TECHNOLOGICAL FIELD ‘The invention relates to a composition and method for neutralization of odors. BACKGROUND ‘The teatmeat of malodors in domestic and industrial areas ha attracted some attention in the recent decades Most solutions avilable in the market today address dhe ‘asue of masking or eliminating malodors in the gascous phase by applying aerosols or sprays which contain fae srances, of synthetic or natural source (1, oF neutralizing ‘chemical agents [2] inthe gas phase. Such soutions do not ‘addeess the problem of treatment of wastewater in the liquid phase inorder to eliminate malodocons which are associated with volatile compounds originating fom within the waste- Por domestic uses, standard containers allowing the release of a measured amount of disinfecting and surface- ‘ctive compounds are typically used [3]. Although providing a dlsinfecting ect and often comprising fmgrance com ponents these produets do not treat the volatile compounds ‘causing’ malodors, but are mulher used for masking the malodors once the volatile compounds have been released from the water into the gas phase “Therefor, there exists a need for odor-neutealizing com= positions that reduce the content of malodorous volatile ‘compounds above aqueous reservoirs by treatment of said volatile compounds in the water phase, as well as those presenti the gaseous phase above the Water. Preferably, such compositions are reguired to be also environmentlly= fiiendly and of low cost REFERENCES References considered tobe relevant as background to the presently disclosed subject matter ar listed below: {1 197031669 2] Wo 2005063045 1B] US. Pat. No. 3,824,633 ‘Acknowledgement ofthe above references herein is not to be inferred as meaning that these are in any way relevant to the patentability of the presently disclosed subjeet matter. SUMMARY OF THE INVENTION The inventors of the present invention have found that ‘compositions comprising certain essential oils provide sat jsfactory odor neutralization without the need to employ ‘environmentally untiendly materials. The odor newealizing, ‘effect may be obtained by sing relatively small quantities of ‘9 neutealizing composition, either when applied as a spray above a liquid phase to he treated (for example, by spraying) ‘or when applied directly into the Figuid phase. 0 o 2 In one of its aspects, the invention provides an odor neutralizing composition comprising at least one eugenol- containing odor neutralizing agent and at Teast one film orming agent “The term “odor neutralization” of any lingual variations thereof, refers to reducing, minimizing, or eliminating mal- ‘odors from a gas phase, which may, by some embodiments, be present abowve an aqueous phase, ein which the source ‘of the malodors is present or contained (not necessarily in a dissolved state). Such malodors are often caused by release of volatile sulphur-based or nitrogen-containing compounds Irom the aqueous phase into the gas phase, Without wishing to be bonnd by theory, the aetive eompanents of the com: position of the invention, ic. the odor neutralizing apt, associates physically with the volatile compounds in the aqueous phase (Iypically be fomning micelles), thereby redveing their volatilization. In addition, the novtalizing agent may react chemically with the volatile compounds, thereby preventing, their volatilization into the gaseous phase, Therefore, neuralization also refers wo a reduotion in fhe concentration of these volatile compounds, inthe gas phase, 10a level below the seeatetecton limit (threshold) ff the oman nose, The eugenol-containing neutralizing agent used in com- positions of the invention may be any type of natural or Syntlietic composition of aister comprising eugene. some embodiments, the neutralizing agent is eugenol (4-Al- Jyl-2-methoxypbenol in pure (neat) form, Tn other embodiments, the atleast one odor neutralizing agent i at least one eugenol-containing “essential ol” i. ' hydrophobic liquid containing volatile aroma compounds, ‘usually obtained from vegetative origin. Such essential ils may be obiained by any method known in the ar, such as isillation, solvent extraction, expression, ete. Without ‘wishing to be bound by theory, once in the aqueous phase to be treated, the essential ol forms micellar structures, encap- sulating the volatile compounds, thereby drastically edue- ing theie volaliy, In some embodiments, sad at least one engenol-contain- ‘ng essential oil is selected from Myriacea eis, Artemicia oils, Cimmamonum oils, Miristica ils, Ocioum oil, Ili ‘ium oils, and Melisa oil. In other embodiments, the at Teast one essential ol is sclectd from Sizygium aromaticun oil (clove oi), Arthemisia absindhum oil (wormwood oil), Cinnamomum cassia oil (C. aromaticum oil), Cinmamomum verum oil (tre cinnamon cil), Cimamomum amata oil dian bay leat ell), Morstca fragrans vil (outmeg oil Geimum Besilicum cil (s001 basil oil), Ocimum gratis ‘mum oil (Alican basil oi), Ocimum temufioram il (tsi oil), Qeimaom sanctum oi (holy basi il, lium anisatumy cil Japanese star anise ol), Melissa fcinalis oi (lemon bale oil neshun graveolens oil (Dill oil, Plmenta rac cemosa cil, Vanilla fragrans oil, ad Apium graveolens cil (celery oil) Tn some embodiments, suid at least one essential oil is 3 clove-hased essential ol According to some embodiments, the composition com- prises said atleast one cdlor neutralizing agent in a content ‘of between about Ind 20 wt % ofthe composition, ie. 12, 3,4, 5,6,7,8,9, 10,11, 12, 13, 14, 15, 16,17, 18, 19 0¢ 30 \W156 of the composition. in such embodiments, dhe content ‘ofthe odor neutralizing agent may be between 1 and 15 wt % of the composition, In other such embodiments, the conten ofthe odor neutralizing agent may be bebween $ and 15 wt % of the composition ‘The term film-forming agent is meant to encompass ‘compounds (or mixtures of compounds) whieh function toUS 10,376,607 B2 3 orm a film onto the surface of the Tiquid to be treated (e water, thereby forming a barrier between the liguid and the aseous enviroament above it, The film-forming agent ors a molectlar or bi-molecular layer at the surface ofthe Tiguid, thereby functioning as a substantially impermeable barrier, preventing transport of volatile spocies from the Tiguid phase to the gaseous phase Tn some embodiments the film-forming agent is MLO (mosquito larveidal oi). The MLO may comprise at least nonylphenol ethoxylate NPA, sorbitan oleate, silicon oil and hydroweated light naphthenic and heavy parafins. ‘According 10 some embodiments, the composition com- prises said film-forming agent in a content of atleast 1%, Typically hetween about | and 30 wt ofthe composition nother embodiments, the film-forming agent ina content of between about 2 and 25 wt % of the composition, In some embodiments, the composition may further com= prise at least one viscosty-contrlling agent. The viscosity- ‘controlling agent provides a desired viscosity to the com- Position. Ia aocordance with some embodiments, the at last ‘one viscosity-contolling agent is selected from acrylate! ‘erylomethyltaurate copolymers, hydroxylated acrylate! sorylomethyltaurate copolymers, polyacrylates. poly- isobutenes, and polysorbates. In such embodiments, the at last one viseosity-control= Ting agent_may be hydroxyethy|-aerylatelsodiumacry- Joyldimethylaurate copolymer (Sepinov-EMT™). ‘In other embodiments, the atleast one viseosity-control- Jing agent may comprise atleast octydodocanal, octykdo- ‘decyl xyloside, PEG 30 dipolyhydroxy stearate or any ‘combination thereof (Fasynov"™) According to some embodiments, the composition com- prises said at least one viseosity-contoling agent in a ‘content of between about 0.5 aad 1.5 wt % of the compo= sition. In some other embodiments, the content of the Viseosity-contelling agent may’be between about 0:5 and 1 + % of the composition. According to some embodiments, the composition may farther comprise atleast one active 'By some embodiments, the at least one additive may be scloted from alkylphenolethoxylates, fatty aleobols,alen- hol ethoxylates, alcohol ethoxysulfates, polyoxyethylene lyeol alkyl elles, polyoxypropylene glyco! alkyl thers lucoside allyl ethers, glycerol alk] esters polyoxyethylene lyeo! octylphenol ethers (Triton X-100), polyoxyethylene lycol sorbitan alkyl esters (polysorbate), sorbitan alkyl testers, cocamide MEAIDEA, block copolymers of polyeth- yylene_ glycol and polypropylene glyeo!_(poloxamers) According to other embodiments, the additive is selected from nonylphenol ethoxylate (NPIO) oF Ci.pCyq alcohol cethoxylate. In some other embodiments, the additive is nonylphenoletloxylate (NP1O}. In yet other embodiments, the additive # C, Cy aleohol ethoxylate ‘By some embodiments, the additive is an emulsifier. The term emulsifier denotes surfactant compounds, encompass- ing any agent that s capable of lowering the surface tension ‘ofa liquid, allowing for the formation of a homogeneous rixtute of at least one typeof lguid with atleast one other ‘ype of liquid (e. to form a mixture ofthe essential oil and wate). ‘Without wishing to be bound by theory, the emulsifier molecules coat the surface ofthe oi (i.e. eugenol) droplets, creating @ steric hindance andlor clectostatic repulsion berwoen the coated droplets, thereby facilitating the droplets dispersion in the aqueous medium. Such emulsifiers may thus be selected trom an electrostatic stabilizer, a steric abilizer, and an electosteric stabilizer. The emulsifiers 0 o 4 nay be surface-ative materials, usually having atleast one voluminous pendent group, electrostatic charge or being of high polarity ‘Tn some embodiments, the at least one emulsifier is ‘ypieally a non-ionie suefactant, which may be selocted from alkylphenol ethoxylates, fatty alcohols, alcoho! ethoxylates, leo ethoxysolfates, polyoxyethylene glycol alkyl ethers, polyoxypropylene glycol alkyl ethers, glucoside alkyl ethers glycerol alkyl esters polyoxyethylene glycol octyl phenol ethers (Triton X-100), polyoxyethylene glycol sor Ditan alkyl esters (polysorbate), sorbitan alkyl estes, coe- amide MEA/DEA, block copolymers of polyethylene glycol and polypropylene glycol (poloxamers). Tn some embodiments, said at least one additive is an cemulsiier which is selected from nonylpheno! ethoxylate (NPIO) and Cy4-C alcohol ethoxylate ‘In some embodiments, the composition i in lguid form. In suc embodiments, the at least one additive is an emul- sifler, which may be present in @ content of between about 3 and 35 wt % of the composition, According io such fembodinients, the at least one emulsifier is nonylphenol ethoxylate (NP1O) and the atleast one eugenol-containing ‘odor neutalizing agent is eugenol Tn some embodiments, the emulsifier in present in a content of between about 3 and 30 wt %, between about 3 ‘and 25 wt % or even between about 3 and 20 wt % of the ‘composition. In other embodiments, the emulsifier in present ina content of bewween about 4 and 35 9%, between about Sand 35 wt % or even between about 7 and 35 wt % ofthe ‘composition, ‘When in liquid form, the composition of the invention may also comprise water, which in some embodiments may be in. content of hetween about 50 and 90 wt % ofthe entre composition, In other embodiments the liquid composition ‘may comprise water ina content of between about 55 and 0 ‘wt, between about 60 and 90 wt %, oF even between about {65 and 90 wt % of the entire composition. In some other «embodiments, the liguid composition may eomprise water in A content of between about S0 and 85 wi %, betcen about ‘SO and 80 wt %, oF even between about $O and 75 wt % af the entire composition, ‘Liquid compositions of the invention may be in a form selected from an emulsion, « guid and s paste, character ined by a viseosity of between about 200 and 6300 eps (centipoises), Emulsion is meant to denote thermody cally stable Tiguid systems, self-assembled into droplets oF ‘other strictures ofthe essential ol and water the presence of surfactants (eg. the emulsifier), The emulsion may be one ‘as know inthe art, soe as microemulsion, mini-ension, ‘nano-emulson, a double emulsion, Iyoteopic liquid crystals, fr any combination thereof or any other type of miero- oF ‘nanostructured liquid According to some embodiments, the composition may further comprise a thickener, which may optionally be sclectod from glyceryl caprylte,glyeery| eaprate and com: binations thereof. The thickener is often added to compos tion, typically Figuid compositions, is order 10 obtain the desired viscosity. Liquid compositions ofthe invention may be formulated for application by spraying or aeosolizing, ‘Compositions of the invention may also be formulated as a substantially solid fom, The team substantially sotid ‘means to encompass all solid forms, ie. emulsions in solid orm, gels, waxy solids, soapy solids, ete. In some embodi- ‘ments, the composition may be in a form selected from a block, panicles, Makes, beads, drops, spheres, or any other solid form. Within the context ofthe present disclosure, the ‘erm substantially solid is also meant fo encompass carrierUS 10,376,607 B2 5 substrates at least partially coated with the solid composi tions as disclosed herein: suet as plastic beads or blocks ‘outed with the solid compositions disclosed herein. Perfo rated substrates or foam structures carrying solid composi tions disclosed herein within atleast part of their peefors- tions and/or foam pores are also contemplated within the scope of the present disclosure, ‘When in solid form, the at Jeast one additive may be preset in conten! of between about 40 and 90 wt % ofthe ‘Composition, In other embodiments, the solid composition ‘may’ comprise said atleast one additive in a conteat of between about 40 and 85 1%, between about 40 and 80 wt %, or even between about 40 and 75 wi % of the compo= sition. In some other embodiment, the solid composition may comprise sad a least one additive in a content of between about 45 and 90 wt, between about $0 and 90 wt 96, oF even between about $5 and 90 wi % of the compo- Tin some embodiments, the a least one additive is selected Jom selected from alkyiphenolethoxylates,faty alcohols aleohol ethoxylates, alcohol ethoxysullates, polyoxyethyl: ‘ene glycol alkyl ethers, polyoxypropylene glycol alkyl ‘ethers, glucoside alkyl ethers, glycerol alkyl esters polyox ‘ethylene glyeol oetylphenol ethers (Tsiton X-100).polyoxs~ ethylene glycol sorbitan alkyl esters (polysorbate), sorbitan alkyl esters, cocamide MEA/DEA, block copolymers of polyethylene glycol and polypropylene giyeol(poloxamers) In other embodiments, the at least on additive in the solid ‘composition is C.-C tleohol ethoxylate "According to some embodiments, said at feast one ad live is C\yC), alcohol elhoxslate und said at least one ‘eugesol-containing odor neuirlizing agent is eugenal ‘i onder to obtain the desired viscosity andl stabilize is solid form, the composition may further comprise at least ‘one polyphosphate compound, which by some embodi ments, may'be present in content of between I and 25% of the composition, In other embodiments, the atleast one polyphosphate compound may he present in a content of Between 4 and 25% of the composition. In some embodi- ments, the polyphosphate eomponnd may be sodium triphosphate, ‘As noted above, the neutralization effect may be obiained by using atively small quantities ofthe composition ofthe invention. The quantity of composition released into the liguid to be treated is determined by the dynamic solubility ‘of the composition. Ths, in some embodiments, the solid compositions ofthe ‘invention havea controlled dynamie solubility in an aqueous phase to be treated inthe range of between about 0.01 t0 1 rams ofthe composition per 10 ters of sad aqueous phase fo be treated, ‘The term dynamic solubility relates tothe solobilty of «| ‘composition when exposed to & moving liquid phase. i. ‘aqueous phase, Thus, the term denotes the solubility ofthe ‘composition when a predetermined volume of figuid phase, ‘eg. 10 liter of water, is Mlown over the composition for 8 predetermined period of time (such as a few seconds). In some embodiment, this period of time i in a range of between about 0-5 and $ Seconds. In other embodiments, the period of time may be ina range of about land 2 seconds In some embodiments, the dynamic solubility of the ‘composition is in the range of between about 0.01 to 0.5 rams ofthe composition per 10 ters of sacl aqueous phase to be treated when coming. in contact with the composition ora period of time of between 0.5 to 5 seconds. In some ‘embodiments, the dynamic solubility of the composition is in the range of between about 0.01 to O.l grams of the ‘composition per 10 liters of said aqueous phase to be treated ‘when coming in coataet with the composition Tora period of Time of between 0.5 to 5 seconds, 0 o 6 According {© some embodiments, the composition solid form may comprise up to 15 wt % of water. Ia some embodiments, the solid composition comprises. between bout 5 and 15st % of water ‘Compositions of the invention may further comprise ‘addtional components to render the composition with at least one other property, such as distinct odor distinet color, tc. For this purpose, in Some embodiments, the composition ‘may further comprise at least one other alive selected from a peefume agent, coloring agent, a preservative, carrer oil, a water-soluble disinfecting agent and combinations thereof. Another aspect ofthe invention provides an odor neutral ‘ing composition comprising water, at least one eugenol- containing odor neutralizing agent, test one ennui, at east one film-forming agent and at least one viscosity- ‘controling agent. Tn further aspect, the invention provides an odor net ‘calizng composition comprising water, al least one euge- sol-coalaining odor neuiaizing agent, a least one emul fier, at least one film-foming agent and at least one viscosty-contrlling agent, the composition having eon- trolled dynamic sokubility in an aqueotis phase to be treated “Another aspect of the invention provides a capsule com= prising a water-dissolvable shll, the shell encapsulating @ ‘omposition ofthe invention as herein described ‘he invention also provides, in another of its aspects, process for the manufacture of & composition comprising ‘water, at least one eugenol-ontaining odor neutralizing ‘gent, at Teast ane emnlsifer, at least on fln-forming agent fad at least one viscosity-controling agent, the process comprising (a) mixing, at a first mixing speed, at lest one odor ‘neutralizing agent, least one film-forming agent, and at least one viseosity-contolling agent to obtain a mixtures (b) mixing, ata second speed atleast one emulsifier and ‘water to obtain a solution; and (6) adding said solution into said mixture under mixing ‘conditions permitting homogenization, to obtain a com- position ofthe invention, According to some embodiments, sad mixing conditions are @ mixing speed of between about 1,000 and 5,000 rpm (rotations per minute), “According to other embodiments, said frst mixing speed being between about 5,000 and 15,000 rpm, ‘According to further embodiments, ssid Second mixing speed being between about 5 and 25 rpm, ‘Mixing may be cared out by any type of suitable ‘equipment known tos person of skill inthe ar, such as, but ot limited 1, pneumatic mixing paddles, electric mixing paddles, homogenizer, planetary mixers, sigma-blade mix- er, rotating drum, ete Ta another aspect, the invention provides an odor neutral- ‘ing liquid composition comprising. water, at least one ‘eugeno}-containing odor neutralizing agent, a feast one film forming agent, and optionally atleast one solvent Tn some embodiments, the engenol-containing odor neu twalizng agent in liquid form is selected from eugenol in pure form, at least one essential oil, and. combinations {hereol The essential oil utilized in the liquid composition may be any ane of the oils mentioned hereinabove, ‘Tn some embodiments, the edor neutralizing liquid com- position comprises odor neutralizing agent content of Between about 1 and 20 wt Yo af the composition, ‘When prevent inthe liquid odor newilizing composition of the invention, the at least one solvent may, in some embodiments, be & C, ,tleabol.