WO2015144328A1 - Associations de principes actifs à effet photoprotecteur constituées d'acide phénylène-1,4-bis-(2-benz­imi­dazyl)-3,3'-5,5'-tétrasulfonique et/oude sels d'acide phénylène-1,4-bis-(2-benz­imi­dazyl)-3,3'-5,5'-tétrasulfonique et de dérivés phénoliques à bas poids moléculaire et préparations cosmétiques ou dermatologiques contenant ces associations de principes actifs - Google Patents

Associations de principes actifs à effet photoprotecteur constituées d'acide phénylène-1,4-bis-(2-benz­imi­dazyl)-3,3'-5,5'-tétrasulfonique et/oude sels d'acide phénylène-1,4-bis-(2-benz­imi­dazyl)-3,3'-5,5'-tétrasulfonique et de dérivés phénoliques à bas poids moléculaire et préparations cosmétiques ou dermatologiques contenant ces associations de principes actifs Download PDF

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Publication number
WO2015144328A1
WO2015144328A1 PCT/EP2015/051546 EP2015051546W WO2015144328A1 WO 2015144328 A1 WO2015144328 A1 WO 2015144328A1 EP 2015051546 W EP2015051546 W EP 2015051546W WO 2015144328 A1 WO2015144328 A1 WO 2015144328A1
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WO
WIPO (PCT)
Prior art keywords
bis
phenylene
benzimidazyl
tetrasulfonic acid
acid
Prior art date
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PCT/EP2015/051546
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German (de)
English (en)
Inventor
Julia Pruns
Guido Heinsohn
Thomas Raschke
Jan Batzer
Bente Nissen
Original Assignee
Beiersdorf Ag
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Filing date
Publication date
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Publication of WO2015144328A1 publication Critical patent/WO2015144328A1/fr

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Classifications

    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • A61K2800/434—Luminescent, Fluorescent; Optical brighteners; Photosensitizers

Definitions

  • the present invention relates to sunscreen active ingredient combinations of phenylene-1, 4-bis (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid and / or phenylene-1,4-bis (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid salts and low molecular weight phenol derivatives as well as cosmetic or dermatological preparations, containing these drug combinations.
  • UVC range rays with a wavelength less than 290 nm
  • UVB range rays in the range between 290 nm and 320 nm, the so-called UVB range, cause erythema simple sunburn or even more or less severe burns.
  • UVA range it is important to have filter substances available, since its rays can also cause damage. It has long been erroneously assumed that the long-wave UV-A radiation with a wavelength between 320 nm and 400 nm has only a negligible biological effect and that consequently the UV-B rays are responsible for most photodamage on human skin. However, numerous studies have since proven that UV-A radiation is far more dangerous than UV-B radiation in terms of triggering photodynamic, especially phototoxic and chronic skin changes. Also, the damaging effect of UVB radiation by UV-A radiation can be enhanced.
  • UV-A radiation is sufficient to rapidly damage the collagen and elastin fibers, which are essential for the structure and firmness of the skin.
  • the appearance of light-aged skin may include wrinkles and wrinkles and an irregular, ragged relief, and the areas affected by photodamaging may be irregularly pigmented Brown spots, keratoses, and even carcinomas or malignant melanoma are possible, as well as a premature aging of the skin due to UV exposure, as well as lower Langerhans cell activity and mild, chronic inflammation.
  • UV-A radiation About 90% of the ultraviolet radiation reaching the Earth consists of UVA rays. While UV-B radiation varies widely depending on many factors (for example, time of day or latitude), UV-A radiation remains relatively constant day after day regardless of year, daytime or geographical factors. At the same time, most of the UV-A radiation penetrates into the living epidermis, while about 70% of the UV-B rays are retained by the horny layer.
  • UV-A rays for example by applying sunscreen filter substances in the form of a cosmetic or dermatological formulation to the skin, is therefore of fundamental importance.
  • the light absorption behavior of sunscreen filter substances is very well known and documented, especially as in most industrialized countries there are positive lists for the use of such substances, which apply quite strict standards to the documentation.
  • the extinction values can at most provide a guide, because interactions with ingredients of the skin or the surface of the skin itself can lead to uncertainties.
  • IPD immediate pigment darkening
  • a value is determined which indicates how much longer the skin protected with the sunscreen can be irradiated with UV-A radiation until the same pigmentation occurs as with the unprotected skin.
  • concentration of known sunscreen filter substances which show a high filtering effect especially in the UV-A range, is often limited especially in combination with other substances present as solids. It therefore prepares certain formulation-technical difficulties to achieve higher sun protection factors or UV-A protection performance.
  • sunscreen filter substances are generally expensive and since some sunscreens are also difficult to incorporate in higher concentrations in cosmetic or dermatological preparations, it was an object of the invention to arrive at preparations in a simple and inexpensive manner, which at unusually low concentrations of conventional UV- Nevertheless, A-sunscreen filters can achieve an acceptable or even high UV-A protection performance.
  • the UV radiation can also lead to photochemical reactions, in which case the photochemical reaction products intervene in the skin metabolism.
  • photochemical reaction products are free-radical compounds, for example hydroxy radicals.
  • Undefined radical photoproducts which are formed in the skin itself, can also show uncontrolled sequelae due to their high reactivity.
  • singlet oxygen a non-radical excited state of the oxygen molecule can occur on UV irradiation, as well as short-lived epoxides and many others.
  • Singlet oxygen for example, is distinguished from the normally present triplet oxygen (radical ground state) by increased reactivity. However, there are also excited, reactive (radical) triplet states of the oxygen molecule.
  • antioxidants and / or radical scavengers may additionally be incorporated into the cosmetic or dermatological formulations.
  • UVA and UVB filters are summarized in most industrialized countries in the form of positive lists such as Appendix 7 of the Cosmetics Regulation.
  • An advantageous water-soluble UV filter are the phenylene-1, 4-bis (2-benzimidazyl) -3, 3'-5,5'-tetrasulfonic acid or its water-soluble salts, in particular the tetrasodium salt.
  • the phenylene-1,4-bis (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid has the following chemical structure:
  • a disadvantage of this substance is that it fluoresces bluish upon irradiation with ultraviolet light. If there are any remains of this substance on the skin, embarrassing lighting effects can be perceived in the case of black light irradiation, which is often used in discotheques and bars.
  • the objects are achieved by combinations of active compounds of phenylene-1,4-bis (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid and / or phenylene-1,4-bis (2-benzimidazyl) - 3,3'-5,5'-tetrasulfonic acid salts and low molecular weight phenol derivatives as well as cosmetic or dermatological preparations containing these active substance combinations.
  • Advantageous combinations of active compounds according to the invention are those in which weight ratios of the total amount of phenylene-1,4-bis (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid and / or phenylene-1,4-bis (2 benzimidazyl) -3,3'-5,5'-tetrasulfonic acid salts to the amount of be selected from low molecular weight phenols in the range of 10 to 1 to 1 to 10, preferably from 5 to 1 to 1 to 5, particularly preferably from 3 to 1 to 1 to 3.
  • Preparations in which low molecular weight phenols are present in weight concentrations selected from the range of 0.001% to 5%, preferably from 0.01 to 2%, particularly preferably from 0.1% to 1%, in each case based on the total weight of the preparations, are likewise particularly advantageous embodiments of the present invention.
  • the one or more low molecular weight phenols are selected from the group of compounds containing the following structural element:
  • R can represent a hydrogen atom or a branched or unbranched alkyl radical of 1 to 25 carbon atoms.
  • a further advantageous embodiment of the invention is obtained when the low molecular weight phenol derivative is selected from the group of parabens.
  • R ' may represent a hydrogen atom or a branched or unbranched alkyl radical of 1 to 25 carbon atoms.
  • the low molecular weight phenol derivatives are selected from the group of salicylic acid derivatives, of which some representatives are known, which can also absorb UV radiation.
  • salicylic acid, phenoxyethanol and benzyl alcohol are advantageous low molecular weight phenol derivatives in the context of the present invention.
  • the unwanted fluorescence of the emulsions containing phenylene-1,4-bis- (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid or phenylene-1,4-bis- (2-benzimidazyl) - Contain 3,3'- 5,5'-tetrasulfonic acid salts significantly reduced, as shown in Fig. 1 impressive.
  • O / W emulsions containing various low molecular weight phenol derivatives, as exemplified in example formulations 1, 2 and 3, were coated on PMMA tablets (5 ⁇ 5 cm area) with a layer thickness of 1.3 mg / cm 2 .
  • Roughness WW5 Schoönberg, Hamburg
  • the fluorescence of the plates under UV light compared.
  • the tablets were irradiated with a UV lamp (lamp Vilber VL-8.LM, 312 nm and 365 nm) and the fluorescent tablets photographed with a digital camera.
  • the preparations according to the present invention preferably contain at least one further UV-A, UV-B and / or broad-spectrum filter substance.
  • the formulations may, although not necessary, optionally also contain one or more organic and / or inorganic pigments as UV filter substances, which may be present in the water and / or the oil phase.
  • the preparations according to the invention may also advantageously be in the form of so-called oil-free cosmetic or dermatological emulsions which contain a water phase and at least one UV filter substance which is liquid at room temperature as further phase.
  • ICI homomenthylsalicylate
  • Preferred inorganic pigments are metal oxides and / or other sparingly water-soluble or insoluble metal compounds, in particular oxides of titanium ( ⁇ i ⁇ 2 ), zinc (ZnO), iron (eg Fe 2 O 3 ), zirconium (ZrO 2 ), silicon ( SiO 2 ), manganese (for example MnO), aluminum (Al 2 O 3 ), cerium (for example Ce 2 O 3 ), mixed oxides of the corresponding metals and mixtures of such oxides and the barium sulfate (BaSO 4 ).
  • the pigments can also be used advantageously in the form of commercially available oily or aqueous predispersions.
  • dispersants and / or solubilizers can be added to these predispersions.
  • the pigments may advantageously be surface-treated ("coated"), in which case a hydrophilic, amphiphilic or hydrophobic character is to be formed or retained, for example or hydrophobic inorganic and / or organic layer
  • a hydrophilic, amphiphilic or hydrophobic character is to be formed or retained, for example or hydrophobic inorganic and / or organic layer
  • the various surface coatings may also contain water for the purposes of the present invention.
  • Inorganic surface coatings for the purposes of the present invention may consist of aluminum oxide (Al 2 O 3 ), aluminum hydroxide Al (OH) 3, or aluminum oxide hydrate (also: alumina, CAS No .: 1333-84-2), sodium hexametaphosphate (NaPO 3 ). 6 , sodium metaphosphate (NaPO 3 ) n, silicon dioxide (SiO 2 ) (also: silica, CAS No .: 7631 -86-9), or iron oxide (Fe 2 O 3 ). These inorganic surface coatings may be present alone, in combination and / or in combination with organic coating materials.
  • Organic surface coatings for the purposes of the present invention may consist of vegetable or animal aluminum stearate, vegetable or animal stearic acid, lauric acid, dimethylpolysiloxane (also: dimethicone), methylpolysiloxane (methicone), simethicone (a mixture of dimethylpolysiloxane with an average chain length of 200 to 350 dimethylsiloxane Units and silica gel) or alginic acid.
  • These organic surface coatings may be present alone, in combination and / or in combination with inorganic coating materials.
  • Zinc oxide particles which are suitable according to the invention and predispersions of zinc oxide particles are obtainable from the following companies under the following commercial names:
  • Suitable titanium dioxide particles and predispersions of titanium dioxide particles are available from the following companies under the following trade names:
  • UV-A filter substances for the purposes of the present invention are dibenzoylmeter derivatives, in particular 4- (tert-butyl) -4'-methoxydibenzoylmethane (CAS No. 70356-09-1), which has been sold by Givaudan under the trademark Parsol ® 1789 and sold by Merck under the trade name Eusolex® 9020.
  • UV filter substances in the context of the present invention are sulfonated, water-soluble UV filters, such as. B .:
  • Sulfonic acid derivatives of 3-Benzylidencamphers such as. B. 4- (2-oxo-3-bomylidenemethyl) benzene sulfonic acid, 2-methyl-5- (2-oxo-3-bomylidenemethyl) sulfonic acid and salts thereof.
  • Advantageous UV filter substances for the purposes of the present invention are also so-called broadband filters, i. Filter substances that absorb both UV-A and UV-B radiation.
  • Advantageous broadband filters or UV-B filter substances are, for example, triazine derivatives, such as. B.
  • Diethylhexylbutylamidotriazone (INCI: diethylhexylbutamidotriazone), available under the trade designation UVASORB HEB from Sigma 3V;
  • Advantageous broadband filter according to the present invention is further the 2- (2H-benzotriazol-2-yl) -4-methyl-6- [2-methyl-3- [1,3,3,3-tetramethyl-1] [(trimethylsilyl) oxy] disiloxanyl] propyl] phenol (CAS No .: 155633-54-8) with the INCI name Drometrizole Trisiloxane, which is available under the trade name Mexoryl® XL from Chimex.
  • the other UV filter substances can be oil-soluble or water-soluble.
  • Advantageous oil-soluble UV-B and / or broadband filter substances in the context of the present invention are, for. B .:
  • 3-benzylidene camphor derivatives preferably 3- (4-methylbenzylidene) camphor, 3-benzylidene camphor;
  • Cinnamic acid derivatives preferably 2-ethylhexyl methoxycinnamate (CAS No .: 5466-77-3), which is available under the trade name Parsol MCX from Givaudan.
  • 4-aminobenzoic acid derivatives preferably (2-ethylhexyl) -4-dimethylaminobenzoate, 4- (dimethylamino) benzoic acid amyl ester;
  • benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone
  • Advantageous water-soluble filter substances are z. B .:
  • Sulfonic acid derivatives of 3-Benzylidencamphers such as. B. 4- (2-oxo-3-bomylidenemethyl) benzene sulfonic acid, 2-methyl-5- (2-oxo-3-bomylidenemethyl) sulfonic acid and salts thereof.
  • a further light stabilizer filter substance to be advantageously used according to the invention is ethylhexyl 2-cyano-3,3-diphenylacrylate (octocrylene), which is available from BASF under the name Uvinul® N 539T.
  • Particularly advantageous preparations in the context of the present invention which are distinguished by a high or very high UV-A and / or UV-B protection, preferably contain, in addition to the filter substance (s) according to the invention further UV-A and or broadband filters, in particular dibenzoylmethane derivatives [for example 4- (tert-butyl) -4'-methoxydibenzoylmethane], phenylene-1,4-bis (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid and / or their salts, the 1, 4-di (2-oxo-10-sulfo-3-bomylidenemethyl) benzene and / or its salts, each individually or in any combination with each other.
  • the list of said UV filters which can be used in the context of the present invention is of course not intended to be limiting.
  • the preparations of the invention contain the substances which absorb UV radiation in the UV-A and / or UV-B range, in a total amount of z. B. 0, 1 wt .-% to 30 wt .-%, preferably 0.5 to 20 wt .-%, in particular 1, 0 to 15.0 wt .-%, each based on the total weight of the preparations to cosmetic To provide preparations that protect the hair or the skin from the entire range of ultraviolet radiation.
  • the cosmetic and dermatological preparations according to the invention may comprise cosmetic adjuvants such as are conventionally used in such preparations, e.g. Preservatives, bactericides, perfumes, anti-foaming agents, dyes, pigments having a coloring effect, thickeners, moisturizing and / or moisturizing substances, fats, oils, waxes, emulsifiers or other common ingredients of a cosmetic or dermatological formulation, such as alcohols, Polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
  • cosmetic adjuvants such as are conventionally used in such preparations, e.g. Preservatives, bactericides, perfumes, anti-foaming agents, dyes, pigments having a coloring effect, thickeners, moisturizing and / or moisturizing substances, fats, oils, waxes, emulsifiers or other common ingredients of a cosmetic or dermatological formulation, such as alcohols, Polyols, polymers, foam stabilize
  • antioxidants An additional content of antioxidants is generally preferred. According to the invention, all antioxidants which are suitable or customary for cosmetic and / or dermatological applications can be used as favorable antioxidants.
  • the antioxidants are selected from the group consisting of amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (eg urocanic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L-carnosine and their derivatives (eg anserine), carotenoids, carotenes (eg ⁇ -carotene, ⁇ -carotene, lycopene) and their derivatives, chlorogenic acid and its derivatives, lipoic acid and its derivatives (eg dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (eg thioredoxin, Glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitol,
  • vitamin C and derivatives eg ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (eg vitamin E acetate), vitamin A and derivatives (vitamin A palmitate) as well as benzoic resin coniferyl benzoate, Rutinic acid and its derivatives, ⁇ -glycosylrutin, ferulic acid, furfurylidene glucitol, carnosine, butylhydroxytoluene, butylated hydroxyanisole, nordihydroguaiacetic acid, nordihydroguiaretic acid, trihydroxybutyrophenone, uric acid and its derivatives, mannose and its derivatives, zinc and its derivatives (eg ZnO, ZnSO 4 ) Selenium and its derivatives (eg selenium methionine), stilbenes and their derivatives (eg stilbene oxide, trans-stilbene oxide) and the according to the invention
  • the amount of the aforementioned antioxidants (one or more compounds) in the preparations is preferably 0.001 to 30 wt .-%, particularly preferably 0.05 to 20 wt .-%, in particular 1-10 wt .-%, based on the total weight of Preparation.
  • vitamin E and / or its derivatives represent the antioxidant (s)
  • vitamin A or vitamin A derivatives, or carotenes or derivatives thereof are the antioxidant (s), it is advantageous if their respective concentrations are within the range of 0.001-10% by weight, based on the total weight of the formulation, of to choose.
  • the lipid phase of the preparations according to the invention containing one or more light-protective compounds of aluminum according to the invention, which contain the structural motif of dibenzoylmethane, can advantageously be selected from the following substance group:
  • Oils such as triglycerides of capric or caprylic acid, but preferably castor oil; Fats, waxes and other natural and synthetic fatty substances, preferably esters of fatty acids with lower C-number alcohols, for example with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with lower C-number alkanoic acids or with fatty acids; benzoates;
  • Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof.

Abstract

Associations de principes actifs à effet photoprotecteur constituées d'acide phénylène-1,4-bis-(2-benz­imi­dazyl)-3,3'-5,5'-tétrasulfonique et/oude sels d'acide phénylène-1,4-bis-(2-benz­imi­dazyl)-3,3'-5,5'-tétrasulfonique et d'un ou de plusieurs dérivés phénoliques à bas poids moléculaire.
PCT/EP2015/051546 2014-03-26 2015-01-27 Associations de principes actifs à effet photoprotecteur constituées d'acide phénylène-1,4-bis-(2-benz­imi­dazyl)-3,3'-5,5'-tétrasulfonique et/oude sels d'acide phénylène-1,4-bis-(2-benz­imi­dazyl)-3,3'-5,5'-tétrasulfonique et de dérivés phénoliques à bas poids moléculaire et préparations cosmétiques ou dermatologiques contenant ces associations de principes actifs WO2015144328A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102014104260.3A DE102014104260A1 (de) 2014-03-26 2014-03-26 Lichtschutzwirksame Wirkstoffkombination aus Phenylen-1,4-bis-(2-benzimidazyl)-3,3'-5,5'-tetrasulfonsäure und/oder Phenylen-1,4-bis-(2-benzimidazyl)-3,3'-5,5'-tetrasulfonsäuresalzen und niedermolekularen Phenolderivaten sowie kosmetische oder dermatologische Zubereitungen, diese Wirkstoffkombinationen enthaltend
DE102014104260.3 2014-03-26

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WO2015144328A1 true WO2015144328A1 (fr) 2015-10-01

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ANONYMOUS: "GNPD - Cream SPF 50+", 1 July 2013 (2013-07-01), XP055177156, Retrieved from the Internet <URL:http://www.gnpd.com/sinatra/recordpage/2131714/from_search/gNiDUmdtKB/> [retrieved on 20150317] *
ANONYMOUS: "GNPD - Gold Label Premium Blemish Base SPF 45/PA+++", 1 June 2013 (2013-06-01), XP055177153, Retrieved from the Internet <URL:http://www.gnpd.com/sinatra/recordpage/2104968/from_search/gNiDUmdtKB/> [retrieved on 20150317] *
ANONYMOUS: "GNPD - Hand Cream SPF 15", 1 April 2013 (2013-04-01), XP055177151, Retrieved from the Internet <URL:http://www.gnpd.com/sinatra/recordpage/2005313/from_search/gNiDUmdtKB/> [retrieved on 20150317] *
ANONYMOUS: "GNPD - Sun Cream SPF50+ PA+++", 1 July 2013 (2013-07-01), XP055177145, Retrieved from the Internet <URL:http://www.gnpd.com/sinatra/recordpage/2122952/from_search/gNiDUmdtKB/> [retrieved on 20150317] *
ANONYMOUS: "GNPD - Sun Cream", 1 August 2001 (2001-08-01), XP055177116, Retrieved from the Internet <URL:http://www.gnpd.com/sinatra/recordpage/109200/from_search/u7ku23xdGJ/> [retrieved on 20150317] *
ANONYMOUS: "GNPD - Sun Milk SPF 30", 1 October 2012 (2012-10-01), XP055177149, Retrieved from the Internet <URL:http://www.gnpd.com/sinatra/recordpage/1896378/from_search/gNiDUmdtKB/> [retrieved on 20150317] *
ANONYMOUS: "GNPD - Sun Protect BB Base SPF 50 PA+++", 1 June 2012 (2012-06-01), XP055177147, Retrieved from the Internet <URL:http://www.gnpd.com/sinatra/recordpage/1820206/from_search/gNiDUmdtKB/> [retrieved on 20150317] *
ANONYMOUS: "GNPD - Sun Protect SPF 30 Day Cream", 1 September 2013 (2013-09-01), XP055177143, Retrieved from the Internet <URL:http://www.gnpd.com/sinatra/recordpage/2179673/from_search/gNiDUmdtKB/> [retrieved on 20150317] *

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US10244793B2 (en) 2005-07-19 2019-04-02 Juul Labs, Inc. Devices for vaporization of a substance
US10638792B2 (en) 2013-03-15 2020-05-05 Juul Labs, Inc. Securely attaching cartridges for vaporizer devices
GB2558805A (en) * 2013-12-23 2018-07-18 Juul Labs Inc Vaporization device systems and methods
GB2558805B (en) * 2013-12-23 2018-10-03 Juul Labs Uk Holdco Ltd Vaporization device systems and methods
US11752283B2 (en) 2013-12-23 2023-09-12 Juul Labs, Inc. Vaporization device systems and methods
US10993471B2 (en) 2013-12-23 2021-05-04 Juul Labs, Inc. Vaporization device systems and methods
US10986867B2 (en) 2013-12-23 2021-04-27 Juul Labs, Inc. Vaporization device systems and methods
US10667560B2 (en) 2013-12-23 2020-06-02 Juul Labs, Inc. Vaporizer apparatus
US10912331B2 (en) 2013-12-23 2021-02-09 Juul Labs, Inc. Vaporization device systems and methods
US10701975B2 (en) 2013-12-23 2020-07-07 Juul Labs, Inc. Vaporization device systems and methods
US10709173B2 (en) 2014-02-06 2020-07-14 Juul Labs, Inc. Vaporizer apparatus
US11019685B2 (en) 2014-02-06 2021-05-25 Juul Labs, Inc. Vaporization device systems and methods
US11452177B2 (en) 2014-02-06 2022-09-20 Juul Labs, Inc. Vaporization device systems and methods
US10865001B2 (en) 2016-02-11 2020-12-15 Juul Labs, Inc. Fillable vaporizer cartridge and method of filling
US11751605B2 (en) 2016-02-11 2023-09-12 Juul Labs, Inc. Securely attaching cartridges for vaporizer devices
US10912333B2 (en) 2016-02-25 2021-02-09 Juul Labs, Inc. Vaporization device control systems and methods
USD913583S1 (en) 2016-06-16 2021-03-16 Pax Labs, Inc. Vaporizer device
USD849996S1 (en) 2016-06-16 2019-05-28 Pax Labs, Inc. Vaporizer cartridge
USD929036S1 (en) 2016-06-16 2021-08-24 Pax Labs, Inc. Vaporizer cartridge and device assembly
USD851830S1 (en) 2016-06-23 2019-06-18 Pax Labs, Inc. Combined vaporizer tamp and pick tool
USD836541S1 (en) 2016-06-23 2018-12-25 Pax Labs, Inc. Charging device
USD887632S1 (en) 2017-09-14 2020-06-16 Pax Labs, Inc. Vaporizer cartridge

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