WO2012145621A1 - Ethers with monocationic polyhydroxyl functionality - Google Patents

Ethers with monocationic polyhydroxyl functionality Download PDF

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Publication number
WO2012145621A1
WO2012145621A1 PCT/US2012/034441 US2012034441W WO2012145621A1 WO 2012145621 A1 WO2012145621 A1 WO 2012145621A1 US 2012034441 W US2012034441 W US 2012034441W WO 2012145621 A1 WO2012145621 A1 WO 2012145621A1
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Prior art keywords
compound
monocationic
personal care
ethers
care compositions
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PCT/US2012/034441
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French (fr)
Inventor
Joseph L. Deavenport
Nicole A. Brehm
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Dow Global Technologies Llc
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Priority to CN201280019397.8A priority Critical patent/CN103562176B/en
Priority to EP12718534.6A priority patent/EP2678308B1/en
Priority to US14/006,746 priority patent/US9220670B2/en
Priority to JP2014506574A priority patent/JP6006293B2/en
Priority to BR112013026601-5A priority patent/BR112013026601B1/en
Publication of WO2012145621A1 publication Critical patent/WO2012145621A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use

Definitions

  • the present invention relates to novel monocationic polyhydroxyl compounds and their uses in personal care compositions.
  • Polyhydroxyl compounds, or polyols have a number of uses, from raw materials used in the manufacture of urethane foams to humectants for personal care products like shaving foams, lotions, and shampoos.
  • Quaternary ammonium compounds are also useful in a number of applications, such as for disinfectants, surfactants, fabric softeners, and conditioners in shampoos.
  • the present invention provides compounds, including salts, of the Formula (I):
  • n 1, 2, 3, 4, 5, or 6;
  • Ria, Rib, R 2a , R 2 b, Rta, and R 4 are, independently at each occurrence, H, optionally substituted C1-C6 alkyl;
  • R3a, R3b and R5 are, independently, optionally substituted C1-C6 alkyl.
  • optional substituent means that the groups in question are either unsubstituted or substituted with one or more groups, radicals or moieties, selected from halogen, hydroxy, amino or carboxy.
  • the substituents may be the same or different.
  • the optional substituent is selected to produce a cosmetically acceptable compound.
  • Cosmetically acceptable refers to ingredients typically used in personal care compositions, and is intended to underscore that materials that are toxic, irritating, or unpleasant smelling when present in the amounts typically found in personal care compositions are not contemplated as part of the present invention.
  • the optional substituent is hydroxy.
  • Alkyl means a saturated monovalent linear or branched aliphatic hydrocarbon radical. Representative examples include, but are not limited to methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, sec-butyl, pentyl, isopentyl, neopentyl, hexyl, isohexyl, and the like.
  • cycloalkyl denotes a saturated monocyclic or bicyclic cycloalkyl group.
  • cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and the like.
  • the cycloalkyl is cyclohexyl or cyclopentyl.
  • Salts means that a counter-ion is present, preferably halogen, more preferably CI " .
  • m is 2, 3, or 4.
  • m is 2.
  • Rj a and R 3 ⁇ 4 are H at each occurrence.
  • at least one P ⁇ a is -CH 3 , -CH2OH, or -CH2CH 3 .
  • Rj a and R 3 ⁇ 4 may cooperate, along with the carbon to which they are attached, to form a cycloalkyl group.
  • R5 is -CH2CH2OH.
  • R 2a and R 2b are each H.
  • R 3a and R 3 ⁇ 4 are the same. Examples of such embodiments include those where R 3a and R 3 ⁇ 4 are each -CH 3 , those where R 3a and R 3 ⁇ 4 are each -CH2CH 3 , and those where R 3a and R 3 ⁇ 4 are each -CH2CH2OH.
  • R 3a and R 3 ⁇ 4 are not the same. Examples of such embodiments include those where R 3a is -CH2CH2OH. In one embodiment, R 3a is
  • R 3b is -(CH 2 ) 3 CH 3 .
  • Non-limiting examples of compounds of Formula I include the reaction products of 3- chloro-l,2-propanediol and amino ether alcohols. Non- limiting examples of these include 2- (2-dimethylamino)ethoxyethanol, 2-[2-(diethylamino)ethoxy]ethanol, 2-[2-(dimethylamino)- l-methylethoxy]ethanol, and Ethyl(2-hydroxyethyl)[2-(2-hydroxyethoxy)ethyl] amine.
  • the present invention provides methods for providing
  • humectancy in a personal care composition comprising including the compound of Formula I into the personal care composition.
  • the ingredients used, and their proportions and manner of addition, are familiar to those versed in conventional personal care compositions, including, optionally, cosmetically acceptable emollients, moisturizers, conditioners, oils, sunscreens, surfactants, emulsifiers, preservatives, rheology modifiers, colorants, preservatives, pH adjustors, propellants, reducing agents, fragrances, foaming or de-foaming agents, tanning agents, depilatory agents, astringents, antiseptics, deodorants, antiperspirants, insect repellants, bleaches, lighteners, anti-dandruff agents, adhesives, polishes, strengtheners, fillers, barrier materials, or biocides.
  • the present invention provides hair care compositions containing the compound of Formula I.
  • the present invention provides skin care compositions containing the compound of Formula I.
  • a 250 mL round bottom, jacketed, flask was equipped with a magnetic stir bar and placed on a stir-plate. The temperature was set to about 25 °C and monitored with a thermocouple. 48.84 g 2-(2-dimethylamino)ethoxyethanol (98% purity, 0.36 mole) was combined with 49.05 g deionized water and allowed to mix for about fifteen minutes before commencing the addition of 40.32 g 3-chloro-l,2-dihydroxypropane (99.6% purity, 0.36mole) over lhour at 25 °C. The reaction solution was allowed to stir for about 1 hour at 25 °C and then for about 4 hours at 45 °C (hot digest). After the hot digest step was completed, the circulation bath was turned off and solution was allowed to cool. At this time, the pH was adjusted to 7.1 with 0.02 moles of HC1.
  • the title compound is prepared substantially according to the protocol of Example 1, except that the conditions and amounts of reactants may vary, typically a 1 : 1 mol ratio with a slight excess of 3-chloro-l,2-propanediol, but which factors are well within the skill of one ordinarily skilled in the art.
  • the title compound is prepared substantially according to the protocol of Example 1 , except that the conditions and amounts of reactants may vary, typically a 1:1 mol ratio with a slight excess of 3-chloro-l,2-propanediol, but which factors are well within the skill of one ordinarily skilled in the art.
  • the title compound is prepared substantially according to the protocol of Example 1, except that the conditions and amounts of reactants may vary, typically a 1 : 1 mol ratio with a slight excess of 3-chloro-l,2-propanediol, but which factors are well within the skill of one ordinarily skilled in the art.
  • compositions having otherwise conventional ingredients.
  • the compositions are evaluated by trained panelists, with each panelist being asked to compare the inventive compositions to a conventional composition.
  • wet and dry feel preference and wet and dry combability is measured by asking the panelists to feel and comb two hair tresses of European virgin brown hair, commercially available from International Hair Importers and Products Inc. NY (USA), one hair tress treated with an inventive composition, the other hair tress treated with a conventional composition. Each panelist is asked to compare the tresses and state which tress is smoother to comb / feel. The answer "same" is not allowed. The reported number is the percent of panelists preferring one over the other.
  • panelists apply a sample (one inventive composition, one conventional composition) to a designated area on their right or left forearm. Initially, each sample is evaluated for ease of application, play time, evenness of deposit, coverage, speed of adsorbtion, shine, matte, skin moistness, heaviness, amount of grease, amount of tack, quickness of drying, overall skin feel, and overall appearance. After a designated time, each sample is again evaluated, this time for coverage, evenness of coverage, shine, matte, skin moistness, heaviness, and overall appearance.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)

Abstract

Described are novel monocationic polyhydroxyl compounds and their uses in personal care compositions.

Description

ETHERS WITH MONOCATIONIC
POLYHYDROXYL FUNCTIONALITY
Field
The present invention relates to novel monocationic polyhydroxyl compounds and their uses in personal care compositions.
Background
Polyhydroxyl compounds, or polyols, have a number of uses, from raw materials used in the manufacture of urethane foams to humectants for personal care products like shaving foams, lotions, and shampoos.
Quaternary ammonium compounds are also useful in a number of applications, such as for disinfectants, surfactants, fabric softeners, and conditioners in shampoos.
Despite the number of available conventional compounds, there is a strong need for novel compounds with properties to differentiate performance or offer synergistic effects in areas of interest, particularly in personal care compositions.
Detailed Description
In one embodiment, the present invention provides compounds, including salts, of the Formula (I):
Figure imgf000002_0001
(I) wherein:
wherein:
m is 1, 2, 3, 4, 5, or 6;
Ria, Rib, R2a, R2b, Rta, and R4 , are, independently at each occurrence, H, optionally substituted C1-C6 alkyl; and
R3a, R3b and R5 are, independently, optionally substituted C1-C6 alkyl.
The term "optionally substituted" as used herein means that the groups in question are either unsubstituted or substituted with one or more groups, radicals or moieties, selected from halogen, hydroxy, amino or carboxy. When the groups in question are substituted with more than one substituent, the substituents may be the same or different. In one embodiment, the optional substituent is selected to produce a cosmetically acceptable compound.
"Cosmetically acceptable" refers to ingredients typically used in personal care compositions, and is intended to underscore that materials that are toxic, irritating, or unpleasant smelling when present in the amounts typically found in personal care compositions are not contemplated as part of the present invention. In one embodiment, the optional substituent is hydroxy.
"Alkyl" means a saturated monovalent linear or branched aliphatic hydrocarbon radical. Representative examples include, but are not limited to methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, sec-butyl, pentyl, isopentyl, neopentyl, hexyl, isohexyl, and the like.
The term "cycloalkyl" denotes a saturated monocyclic or bicyclic cycloalkyl group. Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and the like. In one embodiment, the cycloalkyl is cyclohexyl or cyclopentyl.
Salts means that a counter-ion is present, preferably halogen, more preferably CI". In one embodiment, m is 2, 3, or 4. Preferably, m is 2.
In some embodiments, Rja and R¾ are H at each occurrence. In some embodiments, at least one P^a is -CH3, -CH2OH, or -CH2CH3. Alternatively, Rja and R¾ may cooperate, along with the carbon to which they are attached, to form a cycloalkyl group.
In a preferred embodiment, R5 is -CH2CH2OH.
In one embodiment, R]a and are each H.
In one embodiment, R2a and R2b are each H.
In some embodiments, R3a and R¾ are the same. Examples of such embodiments include those where R3a and R¾ are each -CH3, those where R3a and R¾ are each -CH2CH3, and those where R3a and R¾ are each -CH2CH2OH.
Alternatively, in some embodiments, R3a and R¾ are not the same. Examples of such embodiments include those where R3a is -CH2CH2OH. In one embodiment, R3a is
-CH2CH2OH and R3b is -(CH2)3CH3.
Non-limiting examples of compounds of Formula I include the reaction products of 3- chloro-l,2-propanediol and amino ether alcohols. Non- limiting examples of these include 2- (2-dimethylamino)ethoxyethanol, 2-[2-(diethylamino)ethoxy]ethanol, 2-[2-(dimethylamino)- l-methylethoxy]ethanol, and Ethyl(2-hydroxyethyl)[2-(2-hydroxyethoxy)ethyl] amine.
In one embodiment, the present invention provides methods for providing
humectancy in a personal care composition, comprising including the compound of Formula I into the personal care composition. The ingredients used, and their proportions and manner of addition, are familiar to those versed in conventional personal care compositions, including, optionally, cosmetically acceptable emollients, moisturizers, conditioners, oils, sunscreens, surfactants, emulsifiers, preservatives, rheology modifiers, colorants, preservatives, pH adjustors, propellants, reducing agents, fragrances, foaming or de-foaming agents, tanning agents, depilatory agents, astringents, antiseptics, deodorants, antiperspirants, insect repellants, bleaches, lighteners, anti-dandruff agents, adhesives, polishes, strengtheners, fillers, barrier materials, or biocides.
In one embodiment, the present invention provides hair care compositions containing the compound of Formula I.
In one embodiment, the present invention provides skin care compositions containing the compound of Formula I.
Examples
The following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.
Example 1
Reaction of 3-chloro-l,2-propanediol and 2-[2-(dimethylamino)ethoxy]ethanol to afford 2,3- dihydroxy-N-(2-(2-hydroxyethoxy )ethyl)-N,N-dimethylpropan-l -aminium chloride
H
Figure imgf000005_0001
A 250 mL round bottom, jacketed, flask was equipped with a magnetic stir bar and placed on a stir-plate. The temperature was set to about 25 °C and monitored with a thermocouple. 48.84 g 2-(2-dimethylamino)ethoxyethanol (98% purity, 0.36 mole) was combined with 49.05 g deionized water and allowed to mix for about fifteen minutes before commencing the addition of 40.32 g 3-chloro-l,2-dihydroxypropane (99.6% purity, 0.36mole) over lhour at 25 °C. The reaction solution was allowed to stir for about 1 hour at 25 °C and then for about 4 hours at 45 °C (hot digest). After the hot digest step was completed, the circulation bath was turned off and solution was allowed to cool. At this time, the pH was adjusted to 7.1 with 0.02 moles of HC1.
13C NMR spectra acquired from a Bruker 300MHz spectrometer (samples prepared as -30 wt in D20) confirmed the title compound: DEPT NMR (250 MHz, D20) 54.9, 62.7, 66.1, 66.5, 66.7, 68.5, 69.3, 74.1
Example 2
Reaction of 3-chloro-l,2-propanediol and 2-[2-(diethylamino)ethoxy]ethanol to afford N,N- diethyl-2, 3-dihydroxy-N-(2-(2-hydroxyethoxy )ethyl)propan-l -aminium chloride
H
Figure imgf000006_0001
The title compound is prepared substantially according to the protocol of Example 1, except that the conditions and amounts of reactants may vary, typically a 1 : 1 mol ratio with a slight excess of 3-chloro-l,2-propanediol, but which factors are well within the skill of one ordinarily skilled in the art.
Example 3
Reaction of 3-chloro-l,2-propanediol and Ethyl(2-hydroxyethyl)[2-(2- hydroxyethoxy)ethyl] amine to afford N-ethyl-2, 3-dihydroxy-N-(2-(2-hydroxyethoxy )ethyl)-N- (2-hydroxyethyl)propan-l -aminium chloride
Figure imgf000007_0001
The title compound is prepared substantially according to the protocol of Example 1 , except that the conditions and amounts of reactants may vary, typically a 1:1 mol ratio with a slight excess of 3-chloro-l,2-propanediol, but which factors are well within the skill of one ordinarily skilled in the art.
Example 4
Reaction of 3-chloro-l,2-propanediol and 2-[2-(dimethylamino)-l-methylethoxy]ethanol to afford 2, 3-dihydroxy-N-(2-(2-hydroxyethoxy )propyl)-N,N-dimethylpropan-l -aminium chloride
Figure imgf000007_0002
The title compound is prepared substantially according to the protocol of Example 1, except that the conditions and amounts of reactants may vary, typically a 1 : 1 mol ratio with a slight excess of 3-chloro-l,2-propanediol, but which factors are well within the skill of one ordinarily skilled in the art.
Example 5
Compounds prepared substantially according to the Examples 1-4 are made and formulated into personal care compositions having otherwise conventional ingredients. The compositions are evaluated by trained panelists, with each panelist being asked to compare the inventive compositions to a conventional composition.
For hair care compositions, wet and dry feel preference and wet and dry combability is measured by asking the panelists to feel and comb two hair tresses of European virgin brown hair, commercially available from International Hair Importers and Products Inc. NY (USA), one hair tress treated with an inventive composition, the other hair tress treated with a conventional composition. Each panelist is asked to compare the tresses and state which tress is smoother to comb / feel. The answer "same" is not allowed. The reported number is the percent of panelists preferring one over the other.
For skin care compositions, panelists apply a sample (one inventive composition, one conventional composition) to a designated area on their right or left forearm. Initially, each sample is evaluated for ease of application, play time, evenness of deposit, coverage, speed of adsorbtion, shine, matte, skin moistness, heaviness, amount of grease, amount of tack, quickness of drying, overall skin feel, and overall appearance. After a designated time, each sample is again evaluated, this time for coverage, evenness of coverage, shine, matte, skin moistness, heaviness, and overall appearance.
It is understood that the present invention is not limited to the embodiments specifically disclosed and exemplified herein. Various modifications of the invention will be apparent to those skilled in the art. Such changes and modifications may be made without departing from the scope of the appended claims. Moreover, each recited range includes all combinations and subcombinations of ranges, as well as specific numerals contained therein. Additionally, the disclosures of each patent, patent application, and publication cited or described in this document are hereby incorporated herein by reference, in their entireties.

Claims

Claims
1. A compound, including salts, of the Formula (I):
Figure imgf000009_0001
(I)
wherein:
m is 1, 2, 3, 4, 5, or 6;
Ria, Rib, R2a, R2b, Rta, and R4b, are, independently at each occurrence, H, optionally substituted C1-C6 alkyl; and
R3a, R3b and R5 are, independently, optionally substituted C1-C6 alkyl.
2. The compound of Claim 1, wherein m is 2, 3, or 4.
3. The compound of Claim 1, wherein at least one Rta is C¾.
4. The compound of Claim 1 , wherein Rta is -CH2OH.
5. The compound of Claim 1, wherein R¾ is -CH2C]¾.
6. The compound of Claim 1, wherein Rja and Rtb cooperate to form a cyclohexyl group.
7. The compound of Claim 1, wherein R5 is -CH2CH2OH.
8 The compound of Claim 1, wherein R]a and are each H.
9. The compound of Claim 1 , wherein R2a and R2b are each H.
10. The compound of Claim 1, wherein R3a and R3 are the same.
11. The compound of Claim 10, wherein R3a and R3 are each -C¾.
12. The compound of Claim 10, wherein R3a and R3 are each -CH2C]¾.
13. The compound of Claim 10, wherein R3a and R3b are each -CH2CH2OH.
14. The compound of Claim 1, wherein R3a and R3b are not the same.
15. The compound of Claim 14, wherein R3a is -CH2CH2OH.
16. The compound of Claim 15, wherein R3b is -(CH2)3C]¾.
17. A method for providing humectancy in a personal care composition, comprising including the compound of claim 1 into the personal care composition.
18. A hair care composition containing the compound of claim 1.
19. A skin care composition containing the compound of claim 1.
PCT/US2012/034441 2011-04-21 2012-04-20 Ethers with monocationic polyhydroxyl functionality WO2012145621A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CN201280019397.8A CN103562176B (en) 2011-04-21 2012-04-20 There is the ether of single cation polyhydroxy degree of functionality
EP12718534.6A EP2678308B1 (en) 2011-04-21 2012-04-20 Ethers with monocationic polyhydroxyl functionality
US14/006,746 US9220670B2 (en) 2011-04-21 2012-04-20 Ethers with monocationic polyhydroxyl functionality
JP2014506574A JP6006293B2 (en) 2011-04-21 2012-04-20 Ethers with monocationic hydroxyl functionality
BR112013026601-5A BR112013026601B1 (en) 2011-04-21 2012-04-20 COMPOUND, METHOD FOR PROVIDING MOISTURE TO A PERSONAL CARE COMPOSITION, HAIR CARE COMPOSITION AND SKIN CARE COMPOSITION

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US201161477851P 2011-04-21 2011-04-21
US61/477,851 2011-04-21

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EP (1) EP2678308B1 (en)
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BR (1) BR112013026601B1 (en)
WO (1) WO2012145621A1 (en)

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