WO2016130457A2 - Personal care compositions with acid functional silicone based structuring agents - Google Patents
Personal care compositions with acid functional silicone based structuring agents Download PDFInfo
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- WO2016130457A2 WO2016130457A2 PCT/US2016/016950 US2016016950W WO2016130457A2 WO 2016130457 A2 WO2016130457 A2 WO 2016130457A2 US 2016016950 W US2016016950 W US 2016016950W WO 2016130457 A2 WO2016130457 A2 WO 2016130457A2
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/60—Salicylic acid; Derivatives thereof
-
- 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
- A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
- A61K8/585—Organosilicon compounds
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
Definitions
- the present invention relates to personal care compositions comprising an acid functionality bearing silicone, neutralized in situ with at least one aminosilane or a partially hydroiyzed aminosilane.
- the invention provides better stability to formulation in addition to improved delivery of hydrophilic actives from the formulation.
- Aiiionicaliy modified silicones are commonly used in personal, care compositions to provide smoothness and feelings of softness.
- carboxylated silicones have been reported to exhibit humectant-like characteristics to reduce the transepidermal water loss of skin.
- U.S. Patent No, 5,993,832 discloses a cosmetic emulsions comprising of amonieally modified silicone and acidic cosmeceutical actives to have better stability, sensorial and controlled release characteristics over traditional silicone surfactants.
- R. ⁇ R S , R''. R 7 R Ill R 10 and R U are aliphatic, aromatic or fluoro containing monovalent hydrocarbon groups containing from 1 to about 60 carbon atoms:
- R 4 , R v and R' 2 are independently a monovalent group bearing an .acid functional group selected from the group consisting of -A-COOfL -A ⁇ P0 3 H, - ⁇ - ⁇ (1 ⁇ 4 ⁇ , or -A-SO 3 H,
- A is selected from the group consisting of a divalent hydrocarbon group having from about 1 to about 60 carbon atoms, optionally substituted with heteroatoms. and a divalent aryialkylene group having the generai formula -( m , ) k C ⁇ ,i-i4( : H 2 )i r ,-CH 2 CH( ⁇ Ci1 ⁇ 2 k ⁇ :. ,H4-, and -Ci l 2 Ci i:(R')(CH 2 ) C 6 !-RR ' 's
- R' is hydrogen or an aliphatic, aromatic or fluoro containing monovalent hydrocarbon group having from 3 to about 60 carbon atoms, h has a value of 0 to 20, k has a value of 0 to .10, specifically from about .0 to about 5:
- R" is a monovalent grou having from about 1 to about 20 carbon, atoms, sulfur atoms., nitrogen atoms, oxygen atoms or a group containing combinations of the above atoms; wherein the subscripts a, b, c, d, e, f and g are zero or positive and -subject to the following limitations: 2 ⁇ a+b+c+d+e+f+g ⁇ 6000, .and 0 ⁇ b+d+f;
- composition which contains an acid functionality bearing silicone neutralized in situ wi h at least, one arninosi iane or a partially hydroiyzed aminosilane provides better stability to formulation in addition to improved delivery of hydrophilic actives from the formulation.
- anionically modified silicones surprisingly showed an improved structuring of emulsions when used in presence of an amino functional si lane or their hydroiyzates, giving an additional ' utility to improve the texture of such product without bringing an additional matrix building agents such as waxes.
- these systems provide enhanced delivery of actives that are typically present in dispersed aqueous phase of the formulations.
- any compound, material or substance which is expressly or implicitly disclosed in the specification and/or recited in a claim as belonging to a group of structurally, coniposiiionally and/or functional ly related compounds, materials or substances includes individual representatives of the group and all combinations thereof.
- the personal, care composition comprises
- R ⁇ R ⁇ iV, R ' ⁇ R c R.', R 8 , R !0 and R 1 ' are aliphatic, aromatic or fluoro containing monovalent hydrocarbon groups containing from 1 to about 60 carbon atoms;
- R ' R ''1 and K u are independently a monovalent group bearing an acid functional group selected from the group consisting of -A-COOH, -A-PO 3 -A-OPO H. or -A-SO 3 H,
- A is selected from the group consisting of a divalent hydrocarbon group having from about 1 to about 60 carbon atoms, optionally substituted with heteroatoms, and a divalent arylalkylene group having the general formula -(CHR kCeil ' C s .-' HjCHCR ⁇ ' CJ ⁇ i C ⁇ -li-,
- R' is hydrogen or an aliphatic, aromatic or fluoro containing monovalent hydrocarbon group having from 1 to about 60 carbon atoms, li has a value of 0 to 20, k has a value of 0 to 10, specifically from about 0 to about 5;
- R" is a monovalent group having from about 1 to about 20 carbon atoms, sulfur atoms, nitrogen atoms, oxygen atoms or a group containing combinations of the above atoms; wherein the subscripts a, b. c, d, e, f and g are zero or positive and subject to the following limitations: 2 ⁇ a ⁇ b+c ⁇ d+e+f ⁇ g ⁇ 6000, and 0 ⁇ b+d+f:
- the poiyorganosiloxane is present in the composition in an amount ranging, from 0.01 % to 50% by weight, preferably from 0.1% to 25% and more preferably from 0.1% to 5% by weight relative to the total weight of the composition,
- R ⁇ R 6 , R', R ⁇ s , R'° , R 1 ! and R 1 are independently selected from the group consisting of methyl, ethyl, n-propyi, iso-propyi, n- butyl, isobutyl, tert- butyl, n-pentyl, iso-pentyl, neopentyl , tert- pentyl, hex l, hepty.L octyl, isooctyh 2,2,4-trimethy.ipentyL. non l, decyl, cycloa!kyl groups and aryl groups.
- aminosilane is represented b the formula
- R '" is a monovalent substituted or unsubstituted hydrocarbon, group of I to 13 carbon atoms;
- R 1 ' is a divalent aikyj or aryl group of 1 to 20 carbon atoms;
- R J t> is selected from hydrogen, ethyl, propyl and aminoethyl groups;
- R is an aliphatic organic group selected from alkyl groups, alkylether groups, alkylester groups, aikylketone groups of I. to 8 carbon atoms, an alkylcyano or an aralkyl. group of 7 to 15 carbon atoms, subscript m has a value of 0 or 1 .
- the aminosilane is the reaction product of formula II with an oxirane containing compounds such the siSamzed amino copolymers prepared by the reaction of bis-epoxy compounds with amino siianes or combination of amino silane and other suitable amines.
- the aminosilane is present in the said personal care composition in an amount ranging from 0,01 % to 25% by weight, preferably from 0.1 % to 5% by weight, relative to the total weight of the composition.
- the condensation effective aniino si lanes can be selected from alkoxy and acyloxy siianes bearing at least one amino group.
- Some examples of such siianes are ⁇ -aminopropyl triethox silane, ⁇ -aminopropyl trimethoxysiiane, y-aminopropylmethyi diethoxysilane, arninopropyimethyl dimethoxysiiane, N-(p-animoethyl)-y-aminoprppyl trimethoxysiiane, tri amino organosi lanes, Bis-[y-(t.iieihoxysilyl)propyr]amine, Bis-jy- (trimeihoxysilyijpropyljamine, N-phe.nyi ⁇ Y ⁇ ammopropyl trimethoxysiiane. N-ethyi- ⁇ - aminoisobutyl trimethoxysiiane
- the personal care formulation can be a personal care application selected from the group consisting of deodorants, antiperspirants,
- antiperspirant/deodorants shaving products, skin lotions, moisturizers, toners, bath products, cleansing products, hair care products such as shampoos, conditioners, mousses, styling gels, hair sprays, hair dyes, hair color products, hair- bleaches, waving products, hair siraighteners, manicure products such as .nail polish, nail polish remover, nail creams and lotions, cuticle softeners, protective creams such as sunscreen, insect repellent and anti-aging products, color cosmetics such as lipsticks, foundations, face powders, eye liners, eye shadows, blushes, makeup, mascaras and other personal care .(Omiulat.io.ns where silicone components have been conventionally added, as well as drug delivery systems for topical application of medicinal compositions that are to be applied to the skin.
- the personal care composition of the present invention further comprises one or more personal care ingredients.
- suitable personal care ingredients include, for example, emollients, moisturizers, humeclants, pigments, including pearlescent pigments such as, for example, bismuth oxychioride and titanium dioxide coated mica, colorants, fragrances, biocides.
- preservatives antioxidants, anti-fungal agents, antiperspirant agents, exfoliants, hormones, enzymes, medicinal compounds, vitamins, salts, electrolytes, alcohols, polyols, absorbing agents for ultraviolet radiation, botanical extracts, surfactants, silicone oils, organic oils, waxes, film formers, thickening agents such as, for example, fumed silica or hydrated silica, particulate fillers, such as for example, talc, kaolin, starch, modified starch, mica, nylon, clays, such as, for example, bentonite and organo-modifi* clays.
- Suitable personal care compositions are made by combining, in a manner kn w- in the art, such, as, for example, by mixing, one or more of the above components with the CTOSslinked ionic silicone networks. Suitable personal care compositions may be in.
- an emulsion including oii-in-water, water-in -oil and anhydrous emulsions, where in eac h o f these emulsions the silicone phase may be either the discontinuous phase or the continuous phase, as well as multiple emulsions, such as, for example, oil-in- water-in-oil emulsions and water-in-oil-in-water emulsions; such as is described above.
- an antiperspirant composition comprises the acid functional silicone of the present invention and one or more active antiperspirant agents.
- Suitable antiperspirant agents include, for example, the Category I active antiperspirant ingredients listed in the U.S. Food and Drug Administration's Oct, 10, 1993 Monograph on antiperspirant drug products for over-the-counter human use.
- a skin care composition comprises the acid functional silicone and a vehicle, such as, for example, a silicone oil or an organic oil.
- the skin care composition may. optionally, further include emollients, such as, lor example, triglyceride esters, wax esters, alkyl or alkenyl esters of tatty acids or polyhydric alcohol esters and one or more the known components conventionally used in skin care compositions, such as, for example, pigments, vitamins, such as, lor example, Vitamin A, Vitamin C and Vitamin E, sunscreen or sunblock compounds, such as, for example, titanium dioxide, zinc oxide, oxybenzone, oetylmethoxy cinnamate, butyimeihoxy dibenzoyim ethane, p-aminobenzoic acid and octyl dimethyl-p-aminobenzoic acid,
- emollients such as, lor example, triglyceride esters, wax esters, alkyl or alkeny
- a color cosmetic composition such as, for example, a lipstick, a makeup or a mascara composition
- a coloring agent such as a pigment, a water soluble dye or a liposoluble dye.
- the personal care composition is prepared by mixing the polyorganosiloxane (b). the non-aqueous phase (c), the aqueous phase (d), and optionally a surfactant (e), to form an primary emulsion, followed by the addition of the aminosilane (a).
- the personal care composition is prepared by mixing the aminosilane and the aqueous phase, and optionally a surfactant, followed by addition of the nonaqueous phase comprising the polyorganosiloxane.
- the polyorganosiloxane is present in the composition in an amount ranging from 0.01% to 50% by weight, preferably from 0.1 % to 25% and more preferabl from 0.1 % to 5% by weight relative to the total weight of the composition.
- the aminosilane is present in the composition in an amount ranging from 0.01% to 25% by weight, preferably from 0, 1 % to 5% by weight relativ to the total weight of the composition.
- HOOC(C3 ⁇ 4) l( i(CH. 20( CH3)2Sia)uwSi(CH3)2(CH2)foCOOH was prepared by hydros! lyiation of corresponding hydride functional silicone with triemthyl silyl ester of undecenoic acid at 80 ! 'C using IOppm of Pt(0) catalyst until hydrides are consumed fully as confirmed by 1 H- MR. This was followed by de protection of the silyl ester at 60°C using 2 times molar excess of ethanol for 4-6 hr. Upon stripping the material at 130°C at SOmbar pressure yields the said carboxy end- capped silicone with 0.34raeq/g of acid content and viscosity of 256ep.
- High -internal phase (HIP ) emulsions were prepared according to Table 1 by separately mixin the oil phase comprising the carboxylate sili cone of Example 1 and a primary surfactant SI! soft 1540 and the aqueous phase, followed by slow addition of the aqueous phase to oil. Once addition is complete the emulsion is. mixed for another 30 mins and the other additi ves are added and mixed for another 30 ⁇ rains to produce the emulsion. The resulting high internal phase emulsion is then characterized with rheology experiments, microscopy and stability studies at 5i !' ⁇ ( ' .
- test formulation comprising si lane-si li cone carboxylate structuring agent comprising formulation showed faster delivery of active across a model membrane.
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Abstract
The invention is directed to personal care compositions comprising an acid functionality bearing silicone neutralized in situ with at least one aminosilane or a partially hydrolyzed aminosilane. The invention provides better stability to formulation in addition to improved delivery of hydrophilic actives from the formulation.
Description
PERSONAL CARE COMPOSITIONS WITH ACID FUNCTIONAL SILICONE BASED
STRUCTURI G AGENTS
FIELD OF THE INVENTION
[OOOl j The present invention relates to personal care compositions comprising an acid functionality bearing silicone, neutralized in situ with at least one aminosilane or a partially hydroiyzed aminosilane. The invention provides better stability to formulation in addition to improved delivery of hydrophilic actives from the formulation.
BACKGROUND OF THE' INVENTION
[00021 Aiiionicaliy modified silicones are commonly used in personal, care compositions to provide smoothness and feelings of softness. For example, carboxylated silicones have been reported to exhibit humectant-like characteristics to reduce the transepidermal water loss of skin. Furthermore, U.S. Patent No, 5,993,832 discloses a cosmetic emulsions comprising of amonieally modified silicone and acidic cosmeceutical actives to have better stability, sensorial and controlled release characteristics over traditional silicone surfactants.
[0003] However, these carboxylated silicones cannot provide high level of matrix building and therefore require other additives that may result into slower active compound diffusion from a high consistency formula.
SUMMARY OF THE INVENTION
["0004'j In the present invention,, there is provided a personal care composition
comprising;
(a) at least one condensation effective aminosilane or hydrolysate thereof;
R i ! SK½
Ri2Si03¾
Q - SiO
wherein
R\ R2. R.\ RS, R''. R7 R Ill R10 and R U are aliphatic, aromatic or fluoro containing monovalent hydrocarbon groups containing from 1 to about 60 carbon atoms:
R4, Rv and R'2 are independently a monovalent group bearing an .acid functional group selected from the group consisting of -A-COOfL -A~P03H, -Α-ΟΡ(¼Η, or -A-SO3H,
wherein A is selected from the group consisting of a divalent hydrocarbon group having from about 1 to about 60 carbon atoms, optionally substituted with heteroatoms. and a divalent aryialkylene group having the generai formula -( m,)kC<,i-i4( : H2)ir,-CH2CH( {Ci½ k<:. ,H4-, and -Ci l2Ci i:(R')(CH2) C6!-RR''s
wherein R' is hydrogen or an aliphatic, aromatic or fluoro containing monovalent hydrocarbon group having from 3 to about 60 carbon atoms, h has a value of 0 to 20, k has a value of 0 to .10, specifically from about .0 to about 5:
wherein R" is a monovalent grou having from about 1 to about 20 carbon, atoms, sulfur atoms., nitrogen atoms, oxygen atoms or a group containing combinations of the above atoms; wherein the subscripts a, b, c, d, e, f and g are zero or positive and -subject to the following limitations: 2 < a+b+c+d+e+f+g < 6000, .and 0 < b+d+f;
(c) a non-aqueous phase;
(d) an aqueous phase; and
(e) optionally, one or more surfactants, active ingredients, and pigments.
BRIEF DESCRI PTION OF "THE FIGURES
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
[000.9} The inventors herein have unexpec tedly discovered a personal care composition which contains an acid functionality bearing silicone neutralized in situ wi h at least, one arninosi iane or a partially hydroiyzed aminosilane provides better stability to formulation in addition to improved delivery of hydrophilic actives from the formulation.
[0010} In the present invention, anionically modified silicones surprisingly showed an improved structuring of emulsions when used in presence of an amino functional si lane or their hydroiyzates, giving an additional 'utility to improve the texture of such product without bringing an additional matrix building agents such as waxes. Furthermore, these systems provide enhanced delivery of actives that are typically present in dispersed aqueous phase of the formulations.
0011] In the specification and claims herein, the following terms and expressions. are to be understood as indicated herein below.
[0012] ft will also be understood that any numerical range recited herein is intended to include ail sub-ranges within that range and any combination of end points of said ranges or subranges.
[0013} All methods described herein may be performed in any suitable order unless otherwise indicated or clearly contrary to context. The use herein of any and all examples or exemplification language (for example, such as), is intended merely to better illustrate the invention and does not pose a limitation on the scope of the invention unless otherwise claimed. No language in the specification should be construed as indicating any non-claimed element as essential to the practice of the invention.
[0014] It will be further understood that any compound, material or substance which is expressly or implicitly disclosed in the specification and/or recited in a claim as belonging to a group of structurally, coniposiiionally and/or functional ly related compounds, materials or substances includes individual representatives of the group and all combinations thereof.
[00,15] In one embodiment herein, the personal, care composition comprises
at least one polyorganosiloxane represented by the formula (f):
wherein:
Ms - 'R^'SiO^
M2 - R4R R6SK½
D : - R9R10SiC¾
I"2 - R'-SiOjn
wherein
R \ R \ iV, R'\ Rc R.', R8, R!0 and R1 ' are aliphatic, aromatic or fluoro containing monovalent hydrocarbon groups containing from 1 to about 60 carbon atoms;
R' R''1 and Ku are independently a monovalent group bearing an acid functional group selected from the group consisting of -A-COOH, -A-PO3 -A-OPO H. or -A-SO3H,
wherein A is selected from the group consisting of a divalent hydrocarbon group having from about 1 to about 60 carbon atoms, optionally substituted with heteroatoms, and a divalent arylalkylene group having the general formula -(CHR kCeil 'C s .-' HjCHCR^'CJ^i C^-li-,
wherein R' is hydrogen or an aliphatic, aromatic or fluoro containing monovalent hydrocarbon group having from 1 to about 60 carbon atoms, li has a value of 0 to 20, k has a value of 0 to 10, specifically from about 0 to about 5;
wherein R" is a monovalent group having from about 1 to about 20 carbon atoms, sulfur atoms, nitrogen atoms, oxygen atoms or a group containing combinations of the above atoms; wherein the subscripts a, b. c, d, e, f and g are zero or positive and subject to the following limitations: 2 < a÷b+c÷d+e+f÷g < 6000, and 0 < b+d+f:
(c) a non-aqueous phase;
(d) an aqueous phase: and
(e) optionally, one or more surfactants, active ingredients, and pi ments.
[0016] in one embodiment, the poiyorganosiloxane is present in the composition in an amount ranging, from 0.01 % to 50% by weight, preferably from 0.1% to 25% and more preferably from 0.1% to 5% by weight relative to the total weight of the composition,
10017] In a more specific embodiment, the monovalent, hydrocarbon groups R\ R';, R'\
R\ R6, R', R<s, R'° , R1 ! and R1 are independently selected from the group consisting of methyl, ethyl, n-propyi, iso-propyi, n- butyl, isobutyl, tert- butyl, n-pentyl, iso-pentyl, neopentyl , tert-
pentyl, hex l, hepty.L octyl, isooctyh 2,2,4-trimethy.ipentyL. non l, decyl, cycloa!kyl groups and aryl groups.
[00-18] in another specific embodiment, the aminosilane is represented b the formula
(ϋ ϊ:
m
(ORi ) ..m Si R15—NR16 2
wherein R '" is a monovalent substituted or unsubstituted hydrocarbon, group of I to 13 carbon atoms; R1 ' is a divalent aikyj or aryl group of 1 to 20 carbon atoms; RJ t> is selected from hydrogen, ethyl, propyl and aminoethyl groups; R is an aliphatic organic group selected from alkyl groups, alkylether groups, alkylester groups, aikylketone groups of I. to 8 carbon atoms, an alkylcyano or an aralkyl. group of 7 to 15 carbon atoms, subscript m has a value of 0 or 1 .
[001 j in another more specific embodiment, the aminosilane is the reaction product of formula II with an oxirane containing compounds such the siSamzed amino copolymers prepared by the reaction of bis-epoxy compounds with amino siianes or combination of amino silane and other suitable amines.
[0020] In one embodjmeni, the aminosilane is present in the said personal care composition in an amount ranging from 0,01 % to 25% by weight, preferably from 0.1 % to 5% by weight, relative to the total weight of the composition.
[0021] The condensation effective aniino si lanes can be selected from alkoxy and acyloxy siianes bearing at least one amino group. Some examples of such siianes are γ-aminopropyl triethox silane, γ-aminopropyl trimethoxysiiane, y-aminopropylmethyi diethoxysilane, arninopropyimethyl dimethoxysiiane, N-(p-animoethyl)-y-aminoprppyl trimethoxysiiane, tri amino organosi lanes, Bis-[y-(t.iieihoxysilyl)propyr]amine, Bis-jy- (trimeihoxysilyijpropyljamine, N-phe.nyi~Y~ammopropyl trimethoxysiiane. N-ethyi-γ- aminoisobutyl trimethoxysiiane and combinations thereof
[0022] in one embodiment, the personal care formulation can be a personal care application selected from the group consisting of deodorants, antiperspirants,
antiperspirant/deodorants, shaving products, skin lotions, moisturizers, toners, bath products, cleansing products, hair care products such as shampoos, conditioners, mousses, styling gels, hair sprays, hair dyes, hair color products, hair- bleaches, waving products, hair siraighteners,
manicure products such as .nail polish, nail polish remover, nail creams and lotions, cuticle softeners, protective creams such as sunscreen, insect repellent and anti-aging products, color cosmetics such as lipsticks, foundations, face powders, eye liners, eye shadows, blushes, makeup, mascaras and other personal care .(Omiulat.io.ns where silicone components have been conventionally added, as well as drug delivery systems for topical application of medicinal compositions that are to be applied to the skin.
[0023] in a more specific embodiment, the personal care composition of the present invention, further comprises one or more personal care ingredients. Suitable personal care ingredients include, for example, emollients, moisturizers, humeclants, pigments, including pearlescent pigments such as, for example, bismuth oxychioride and titanium dioxide coated mica, colorants, fragrances, biocides. preservatives, antioxidants, anti-fungal agents, antiperspirant agents, exfoliants, hormones, enzymes, medicinal compounds, vitamins, salts, electrolytes, alcohols, polyols, absorbing agents for ultraviolet radiation, botanical extracts, surfactants, silicone oils, organic oils, waxes, film formers, thickening agents such as, for example, fumed silica or hydrated silica, particulate fillers, such as for example, talc, kaolin, starch, modified starch, mica, nylon, clays, such as, for example, bentonite and organo-modifi* clays.
[0024] Suitable personal care compositions are made by combining, in a manner kn w- in the art, such, as, for example, by mixing, one or more of the above components with the CTOSslinked ionic silicone networks. Suitable personal care compositions may be in. the form c: an emulsion, including oii-in-water, water-in -oil and anhydrous emulsions, where in eac h o f these emulsions the silicone phase may be either the discontinuous phase or the continuous phase, as well as multiple emulsions, such as, for example, oil-in- water-in-oil emulsions and water-in-oil-in-water emulsions; such as is described above.
[0025] In one useful embodiment, an antiperspirant composition comprises the acid functional silicone of the present invention and one or more active antiperspirant agents.
Suitable antiperspirant agents include, for example, the Category I active antiperspirant ingredients listed in the U.S. Food and Drug Administration's Oct, 10, 1993 Monograph on antiperspirant drug products for over-the-counter human use. such as, for example, aluminum halides, aluminum hydroxy halides, for example, aluminum ehiorohydrate, and complexes or mixtures thereof with zircon l oxyha!ides and zirconyl hydroxyhalides, such as for example.
aluminum-zir.co.nium chlorohydrale, aluminum zirconium glycine complexes, such as, for example, aluminum zirconium tetrachl orohydrex gly.
[0026] in another useful embodiment, a skin care composition comprises the acid functional silicone and a vehicle, such as, for example, a silicone oil or an organic oil. The skin care composition may. optionally, further include emollients, such as, lor example, triglyceride esters, wax esters, alkyl or alkenyl esters of tatty acids or polyhydric alcohol esters and one or more the known components conventionally used in skin care compositions, such as, for example, pigments, vitamins, such as, lor example, Vitamin A, Vitamin C and Vitamin E, sunscreen or sunblock compounds, such as, for example, titanium dioxide, zinc oxide, oxybenzone, oetylmethoxy cinnamate, butyimeihoxy dibenzoyim ethane, p-aminobenzoic acid and octyl dimethyl-p-aminobenzoic acid,
{0027) In another useful embodiment, a color cosmetic composition, such as, for example, a lipstick, a makeup or a mascara composition comprises the crosslinked ionic silicone network, and a coloring agent, such as a pigment, a water soluble dye or a liposoluble dye. (0028J Process of Preparing the Personal Care Composition
{0029] As stated above, there is provided herein a process of preparing a personal care compos i ti on comprising :
(a) at least one condensation effective amiiiosilane or hydro!ysate thereof;
(b) at least one polyorganosiloxane represented by the formula (!) defined above
(c) a non-aqueous phase;
(d ) an aqueous phase; and
(e) optionally, one or more surfactants, active ingredients, and pigments;
wherein the personal care composition is prepared by mixing the polyorganosiloxane (b). the non-aqueous phase (c), the aqueous phase (d), and optionally a surfactant (e), to form an primary emulsion, followed by the addition of the aminosilane (a).
10030] in another embodiment, the personal care composition is prepared by mixing the aminosilane and the aqueous phase, and optionally a surfactant, followed by addition of the nonaqueous phase comprising the polyorganosiloxane.
[0031 ] In one embodiment, the polyorganosiloxane is present in the composition in an amount ranging from 0.01% to 50% by weight, preferably from 0.1 % to 25% and more preferabl from 0.1 % to 5% by weight relative to the total weight of the composition.
[0032} In another embodiment, the aminosilane is present in the composition in an amount ranging from 0.01% to 25% by weight, preferably from 0, 1 % to 5% by weight relativ to the total weight of the composition.
[0033] Various fea t ures of the invention are illustrated by the examples presented below.
EXAMPLES
[0034] Example 1: Preparation of carbox end-capped PDMS
[0035] Carboxy end capped silicone with average moieculer formula
HOOC(C¾)l( i(CH. 20( CH3)2Sia)uwSi(CH3)2(CH2)foCOOH was prepared by hydros! lyiation of corresponding hydride functional silicone with triemthyl silyl ester of undecenoic acid at 80!'C using IOppm of Pt(0) catalyst until hydrides are consumed fully as confirmed by 1 H- MR. This was followed by de protection of the silyl ester at 60°C using 2 times molar excess of ethanol for 4-6 hr. Upon stripping the material at 130°C at SOmbar pressure yields the said carboxy end- capped silicone with 0.34raeq/g of acid content and viscosity of 256ep.
(0036 J Water in Oil High Internal Phase Emulsion Formulations 1-5 (F1 -P5) using the carboxylate silicone of Example I
10037] High -internal phase (HIP ) emulsions were prepared according to Table 1 by separately mixin the oil phase comprising the carboxylate sili cone of Example 1 and a primary surfactant SI! soft 1540 and the aqueous phase, followed by slow addition of the aqueous phase to oil. Once addition is complete the emulsion is. mixed for another 30 mins and the other additi ves are added and mixed for another 30· rains to produce the emulsion. The resulting high internal phase emulsion is then characterized with rheology experiments, microscopy and stability studies at 5i !'·( '.
Table 1. Formulations 1 -5
Formulations Fl F2 F3 F4 F5
Cyclopentasi ioxane 20 20 20 20 20
Oil Silsoft 1540 from Momentive 3 3 3 3 3
Phase Performance Materials inc.
Carboxy Sate silicone of Example I 3 3 3 3 3
Water 69 69 69 69 69
Aqueous
Glycerin from Sigma Aidrieh 4 4 4 4 4 Phase
NaCl from Sigma Aidrieh 1 1 1 i 1
Other Sikjuest A-1 100 from Momentive 0.5 ' 0.180
additives Performance Materials Inc.
Triethy!amine from Sigma Aidrieh 0. 1 00
A-1 30 from Momentive Performance 0, 135
Materials nc.
1 0 8 J Rheology Measurements
[0039] Rheology measurements were performed in Haake Rheometer at 25°C -and indicated better structuring with the composition according to the present invention over the control samples.
[0040] The results are showing in Figures 1 and 2. In the figures the formulations according to present invention provide better modulus or structuring over competitive examples.
[0041 ] Microscope Images
10042] in microscopic images the internal phase droplet size was significantly reduced upon neutralization of the silicone carboxy acid of example 1 (formulation F2, F3 and F4) indicating enhance interfacial activity of the carboxy silicone. The results, are showing in Figure
[0043] Cream Formulation Comprising Actives and Release Studies
[0044] Skin cream formulations containing actives were prepared according to Table 2 in the same manner as described previously. For the study. Sodium Salicylate was used as model for water soluble active. In the Comparative Sample, a silicone cross-polymer was used as structuring agent.
Table 2.
[00451 The release studies were performed o a Franz Diffusion Cell, The formulation were applied on to a MiUipore Membrane with 40Onm pore size and then placed in between the donor and acceptor compartments and the active released across the membrane in to the acceptor compartment holding water was measured using HPLC technique.
[0046] The results are showing in Figure 4. As can be seen, from Figure 4, the test formulation comprising si lane-si li cone carboxylate structuring agent comprising formulation showed faster delivery of active across a model membrane.
0047'j These examples are to be construed as exemplary in nature only and are not intended in any way to limit the appended claims. It is contemplated that a person having ordinary skill in the art would be able to produce obvious variations of the subject matter and. disclosures herein contained that would be by reason of such ordinary skill within, the literal or equitable scope of the appended claims.
Claims
CLAIMS:
1. A personal, care composition comprising;
(a) at least one condensation effective aminosiiane or hydro iy sate thereof;
(b) at least one poiyorganosiioxane represented by the formula (I):
M ' a iVI 2 b D 1 cD2dT ! eT2 sQg (l)
wherein;
wherein
R!, R\ R', R\ R6, R"\ R8. R10 and Ri f are aliphatic, aromatic or fluoro containing monovalent hydrocarbon groups containing from 1 to about 60 carbon atoms:
R , R9 and R are independently a monovalent group bearing an acid functional group selected from the group consisting of-A-COOH, -A-PO3H, -A-OPG3H and -A-SO3H,
wherein A is selected from the grou consistin of a divalent hydrocarbon group having from about 1 to about 60 carbon atoms, optionaily substituted with heteroatoms, and a divalent aryla!kylene group having the general formula .(CHR,)kC6H4<CH2)h-,-CH2CH( ')( H2)icC<;H4-,
wherein R' is hydrogen or an aliphatic, -aromatic or fiitoro containing monovalent hydrocarbon group helving from 1 to about 60 carbon atoms, h has a value of 0 to 20, k has a value of 0 to 10;
wherein R" is a monovalent group having from about 1 to about 20 carbon atoms, sulfur atoms, nitrogen atoms, oxygen atoms or a group containing combinations of the above atoms; wherein the subscripts a, b, c, d, e, f and g are zero or positive and subject to the following limitations: 2 < a+b÷c+d+e-H g < 6000, and 0 < b+d+f;
(c) a non-aqueous phase;
(d) an aqueous phase; and
(e) optionally, one or more surfactants, active ingredients, and pigments.
2. The personal care composition of claim I wherein the monovalent hydrocarbon groups R L , RA R\ RR\ 1 °, R ;, R8, R,w , R U and R' are independently selected from the group consisting of methy l , ethyl, n-propyL iso-propyl. n-biityk isobutyl, iert-bittyl, n-pentyl, iso-pentyl, neopentyi, teri-pentyi, hexyi, heptyl, octyl. isooctyi, 2,2,4-trimeth lpenty.1. nonyl, decyl, cycioalkyl groups and aryi groups.
3. The personal care composition of claim 2 wherein the cycioalkyl groups are
independently selected from the group consisting of cyclopentyl, cyciohexyl, cycloheptyi and methylcyclohexyl groups.
4. The personal care composition of claim 2 wherein the aryi groups are independently selected from the group consisting of phenyl, naphthyl; o-, ra- and p-tolyl, xyl l, ethylphenyl and benzyl
6. The personal care composition of claim 1 wherein at least on of R4. RL~ and R1 '' is a monovalent group bearing an acid functional group selected from the group consisting of -A-COOH, -A-PO3H, -A-OPO3H and -A-SO3H.
7. The personal care composition of claim 1 wherein the aminosilaiie is represented by the formula (II):
(O )3.m Si R15 R16 2 { , ! }
wherein Rf j is a monovalent substituted. or unsubstituted hydrocarbon group of 1 to 13 carbon atoms; R " is a divalent .alkyl or aryi group of 1 to 20 carbon atoms; '" is selected from hydrogen, ethyl, propyl arid aminoethyl groups; R is an aliphatic organic group selected from alkyl groups, alkyl ether groups, alkyiester groups, alk lketone groups of 1 to 8 carbon atoms, an alkylcyano or an aralkyl group of 7 to 15 carbon atoms, subscript m has a value of 0 or 1 ,
8 , The personal care composition of claim I wherein the aminosilane i an alkoxysiianq comprising one or more primary and/or secondary amine functional groups,
9, The personal care composition of claim 1 wherein the aminosilane is chosen from γ- aminopropyl triethoxysilane, γ-aminopropy! trimethoxysilane, y-aminopropylmefhyl diethoxysilane, aminopropylmethyl dimethoxystlane, N-(P-ammoethyl)-v-amino.propyl irimethoxysilane, triami o organosilanes, Bis-l'v-Ctriethoxysily propyijamine, Bis-fy- (irimethoxysilyl)propyl]amine, N-phenyl-y-ammopropyi trimethoxysilane, N-etbyl-γ- aminoisobutyl trimethoxysilane and combinations thereof.
J 0. The personal care composition of claim 1 wherein the aminosilane is selected from the group consisting of 3-aminopropyltriethoxysilaiie, 3-aminopropyimethyldiemoxysilane. N-(2- aminoethyl)-3-aminopropyltriethoxysiiane, 3-(2-aminoethylamino)propyimethyldiethoxysi!ane and combinations thereof.
1 1. The personal, care composition of claim. 1 wherein the aminosilane is present in the composition in an amount ranging from 0.01% to 25% by weight of the personal care composition.
12. The personal care composition of claim I wherein the polyorganosi loxane is present in the composition in an amount, ranging from 0.01 % to 50% by weight of the personal care composition.
13. The personal care composition of claim .1 wherein the personal care composition further comprises solvents selected from the group consisting of ethylene glycol, ethanol, propyl alcohol, iso-propyl alcohol propylene glycol, dipropylene glycol tripropyiene glycol butylene glycol iso-butylene glycol, methyl propane diol, glycerin, sorbitol polyethylene glycol polypropylene glycol mono alkyl ethers, polyoxyalkylene copolymers and mixtures thereof.
14. The personal care composition of claim ). wherein the aqueous phase .comprises water or an aqueous solution containing personal care ingredients.
15. The personal care composition of claim ί wherein the personal care composition is an oil-in-water, a water-in-oil or a multiple emulsion.
1 . The personal care composition oi* claim 1 wherein the surfactant, is ionic, nonionic, polymeric or mixtures therefrom.
17. The personal care composition of claim 1 wherein the active ingredients include bioactives, anti-acne agents, anti-ageing agents, anti-caries agents, anti-fungal agents, antimicrobial agents, anti-oxidants, anti-cancer, anti-viral, anti-inflammatory, anti-coagulants, hemostatic agents, exfoliants, hormones, hormone analogs, enzymes, proteins, and peptides, medicinal compounds, bioeides, external, analgesics, oral care agents, oral care drugs, oxidizing agents, reducing agents, skin protectants, essential oils, insect repellents, UV light absorbing agents, solar filters, pigments, hy irating agents, vitamins and their combinations thereof.
18. A personal care application comprising the personal care composition of claim 1 wherei the personal care application is selected from the group consisting of a skin care application, a cosmetic application, a hair care application and a keratin -shaping application.
19. A process of preparing a personal care composition comprising:
(a) at least, one condensation effective amino$ilane or hydro!ysate thereof;
Df - R7RsSi ½
R1, 2, RJ, R', R(1, R', R&, RR! and Rn are aliphatic, aromatic or fluoro containing monovalent hydrocarbon groups containing -from 1. to about 60 carbon atoms;
R'f, R9 and R'u are independently a monovalent group bearing an acid functional group selected from the group consisting of -A-COOH, -A.-PO3H, -A-OP03H, or -A-SO3H,
wherein A is selected from the group consisting of a divalent hydrocarbon group having from about 1 to about 60 carbon atoms, optionally substituted with heteroatonis, and a divalent arylalkyiene group having the general formula -(CH ,)kC6H4(CH2)h-,-CH2CH(R')(CH2)kC6H4-,
wherein R' is hydrogen or an aliphatic, aromatic or fluoro containing monovalent hydrocarbon group having from I to about 60 carbon atoms, h has a value of 0 to 20, k has a value of 0 to 10;
wherein R" is a monovalent group having from about 1 to about 20 carbon atoms, sulfur atoms, nitrogen atoms, oxygen atoms or a group containing combinations of the above atoms; wherein the subscripts a, b, c, d, e, f and g are zero or positive and subject to the following limitations: 2 < a-i-b+c+d+e-t-f+g < 6000, and 0 < b+d+f
(c) a non-aqueous phase;
(d) an aqueous phase; and
(e) optionally, one of more surfactants, active ingredients, and pigments;
wherein the personal care composition is prepared by mixing the polyorganosiioxane (b). the non-aqueous phase (c), the aqueous phase ( 1), and optionally a surfactant (e), to form an primary emulsion, followed by the addition of the aminosilane (a).
20. A process of preparing a personal care composition comprising
(a) at least one condensation effective aminosilane or hydrolysate thereof;
(b) at least one polyorganosiioxane represented by the formula (I):
M aM2i,D ^D^iT ' eT2rQg (1)
wherein:
M1 - R'R^SiO, - M2 = R*R5R6Si(½
V - Ri !Si0.v2
Ί2 =· RuSi03/3
Q - Si0 /2
wherein
R', R2. R'\ R5, a6, R7, ί¾Λ Ri 0 and Rn are aliphatic, aromatic or fiuoro containing monovalent hydrocarbon groups containing from I to about 60 carbon atoms;
R4. R9 and R5 " are independently a monovalent group bearing an acid functional group selected from the group consisting of -A-COOH, -A-PO3 HL, -A-OP<¾H> or -A-$Q3B,
wherein A is selected from the group consisting of a divalent hydrocarbon group having from about 1 to about 60 carbon atoms, optionally substituted with he tero atoms, and a divalent aryiaikylene group having the general f raiuia -iCH ^fcC^i iCi-fe^- CI-feCHCR'JCCHs)!,^:^^-,
wherein R' is hydrogen or an aliphatic, aromatic or ftuoro containing monovalent hydrocarbon group having from 1 to about 60 carbon atoms, h has a value of 0 to 20, k has a value of 0 to 10;
wherein R" is a monovalent group having from about 1 to about 20 carbon atoms, sulfur atoms, nitrogen atoms, oxygen atoms or a group containing combinations of the above atoms; wherein the subscripts a, b, c, d, e, f and g are zero or positive and subject to the following limitations: 2 < a+b+c+d+e+f+g < 6000, and 0 < b+d+f;
(c) a non-aqueous phase:
(d) an aqueous phase: and
(e) optional ly, one or more surfactants, active ingredients, and pigments.
wherein the personal care composition is prepared by mixing the aminosilane (a), the aqueous phase (d), and optionally a surfactant (e), followed by the addition of the
polyorganosiloxarie (b) and the non-aqueous phase (c)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE112016000406.0T DE112016000406T5 (en) | 2015-02-11 | 2016-02-08 | Personal care compositions containing an acid functional silicone based structurant |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562114673P | 2015-02-11 | 2015-02-11 | |
| US62/114,673 | 2015-02-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2016130457A2 true WO2016130457A2 (en) | 2016-08-18 |
| WO2016130457A3 WO2016130457A3 (en) | 2016-11-24 |
Family
ID=55436175
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2016/016950 Ceased WO2016130457A2 (en) | 2015-02-11 | 2016-02-08 | Personal care compositions with acid functional silicone based structuring agents |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US9987365B2 (en) |
| DE (1) | DE112016000406T5 (en) |
| WO (1) | WO2016130457A2 (en) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5232689A (en) | 1990-12-21 | 1993-08-03 | Dow Corning Corporation | Translucent antiperspirant compositions |
| US5447997A (en) | 1994-03-11 | 1995-09-05 | General Electric Company | Silicone polyether carboxylic acids |
| FR2745715B1 (en) | 1996-03-05 | 1998-07-31 | Oreal | OIL-IN-WATER EMULSION, COMPOSITION COMPRISING SUCH AN EMULSION AND USE IN COSMETICS, PHARMACY OR HYGIENE |
| US6867317B1 (en) | 2002-12-26 | 2005-03-15 | Biosil Research Institute Inc. | Alkoxylated silicone carboxylate-polymeric cationic complexes used in personal care applications |
| WO2008046762A1 (en) | 2006-10-20 | 2008-04-24 | L'oreal | Cosmetic composition comprising an organopolysiloxane comprising at least one carboxyl group |
-
2016
- 2016-02-08 US US15/017,767 patent/US9987365B2/en active Active
- 2016-02-08 WO PCT/US2016/016950 patent/WO2016130457A2/en not_active Ceased
- 2016-02-08 DE DE112016000406.0T patent/DE112016000406T5/en not_active Withdrawn
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| WO2016130457A3 (en) | 2016-11-24 |
| US9987365B2 (en) | 2018-06-05 |
| US20160228557A1 (en) | 2016-08-11 |
| DE112016000406T5 (en) | 2017-12-14 |
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