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Process For Pongamol Enrichment Of Karanja Oil

Abstract: [0001] The invention relates to a cosmetic ingredient characterized in that it consists of a solution of at least one extract of karanja oil comprising pongamol (CAS 484 33 3) and karanjin (CAS 521 88 0) in at least one solvent chosen from the group of diesters having the following formula (I) or mixtures thereof: in which formula (I): n is between 0 and 19; R and R which may be identical or different are chosen from the group of alkyls derived from a linear or branched alcohol of empirical formula CxH2x+2O before esterification x being between 1 and 30 preferentially between 1 and 20 preferentially between 1 and 10. R" is either a hydrogen atom or a C1 C3 alkyl group. [0002] The invention also relates to a selected precipitation process to a cosmetic formulation and also to the uses thereof.

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Notices, Deadlines & Correspondence

Patent Information

Application #
Filing Date
12 February 2018
Publication Number
34/2018
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
Parent Application
Patent Number
Legal Status
Grant Date
2023-03-10
Renewal Date

Applicants

1. BIOSYNTHIS
4B rue de Foisnard 91410 Saint Cyr Sous Dourdan

Inventors

1. BERNOUD Thierry
6 Chemin Pierre Percée F 91410 Saint Cyr Sous Dourdan
2. PICCIRILLI Antoine
18 chemin de Tison 86000 Poitiers
3. MAGNE Julien
11 rue de Genebrie 86340 les Roches Premarie Andille

Specification

PROCESS FOR ENRICHMENT OF OIL PONGAMOL ARRANGE [0001] The present invention relates to the field of oleochemicals and particularly the oils used in cosmetics. [0002] More particularly, the invention relates to a process for selectively extracting the unsaponifiable components of a lipid material of vegetable origin, this renewable lipid material being karanja oil. [0003] At the end of said method, a sample is obtained, said extract (consisting of a solution) can be incorporated in cosmetic or pharmaceutical compositions. [0004] Karanja is a plant of the legume family, native to Asia. It is especially present in India, Japan, and South China. This is a shaft or a robust liana measuring 20 to 30 m. [0005] The term "Karanja" within the meaning of this application means including the following species: Pongamia glabra Pongamia pinnata pinnata Milletia, Derris indica gadelupa pinnata, Pongamia grandifolia, Robinia mitis, Tephrosia purpurea Tephrosia of Hamilton, Tephrosia falciformis, Tephrosia vogellii, Tephrosia lanceolata, etc. [0006] Different parts of the plant are used: the roots are used as dental material or as a local antiseptic, the leaves are digestive and laxative, and are also used as an antiseptic. The bark is used as an anthelmintic, and finally, the seeds are used as a source of Karanja oil. [0007] The seeds of Karanja include about 27 to 39% oil. [0008] karanja oil is obtained from seeds, by pressure or by solvent extraction. The cake, less oil-rich seeds that can also be used as feedstock. The resulting oils generally have the same physical and chemical characteristics, which is in the form of a cloudy liquid, brown to orange, and strong smell unpleasant. [0009] karanja oil mainly comprises triglycerides as well as oleic and linoleic acids, and, in smaller proportions: palmitic acid, stearic acid, linolenic acid, arachidic acid and behenic acid. [00010] karanja oil, once extracted from the seed, is widely used. In Ayurvedic pharmacopoeia, it is especially used for skin care, hair, particularly with regard to its antiseptic and anti parasitic, it is also used in the treatment of eczema, psoriasis and in the treatment of scalp. Karanja Oil is sometimes also used as an insecticide. [00011] Karanja Oil in addition to traditional uses recounted above, is also used more recently as sunscreen, alone or in combination with other sun filters in cosmetic compositions. This is due in particular to the presence of certain unsaponifiable compounds. As an indication, karanja oil includes about 2 to 5% of unsaponifiables, the most known are two diketones: the pongamol (CAS 482-33-3) and karanjine (CAS 521-88-0 ). [00012] In very general terms, the mass percentages means and pongamol karanjine in karanja oil is between 0.3 and 0.9% for pongamol and between 2 and 4% for karanjine. [00013] The weight percentages are indicative only, as they can vary widely depending on the species, the season of the sampling, etc. [00014] The sunscreen properties of karanja oil are mainly due to the presence of pongamol, the latter is a natural filter having a UV absorption spectrum similar to that of methoxydibenzoylmethane (CAS 70356-09-1) , better known under the brand name Parsol 1789®. [00015] However, karanja oil incorporation into sunscreen compositions is limited by the organoleptic characteristics of said oil. [00016] These negative organoleptic characteristics are essentially due to the presence of karanjine. [00017] The elimination of all or part of the karanjine of karanja oil, therefore, has the direct effect of increasing the amount of this oil incorporable in solar cosmetic compositions. Moreover, maintaining a sufficient mass percentage pongamol is important to maintain good solar properties. [00018] However, the selective removal of the karanjine is difficult, due to the existing relationship between the chemical karanjine and pongamol. [00019] In application WO 2014/016349 in the name of Biosynthis there is disclosed a solar composition comprising oil of karanja and other compounds, and in particular a polyester. In this application, there is no question of a selective extraction process. [00020] Dans la publication "Exhibitors Suppliers Day - USA", 1 mai 2013 (2013-05-01), pages 1-16, XP055264364 sUDPfiers-dav May 7, 2013 59 19. pdf), it comes to a stand Biosynthis, and in particular the product KARANSUN ® , product 2013 comprising no diester. [00021] WO 2014114888 in the name of Jean-Noel Thorel relates to a system of protection against UV and free radicals, based on Karanja oil association and penthaerythrityl tetra-di-t-butyl hydroxyhydrocinnamate . [00022] The publication "SPF 40 Sun Cream for the face," GNP D; MINTEL, September 1, 2008 (2008-09-01), XP002716746 relates to a commercial composition comprising oil of Karanja and the pongamol. From pongamol is added in addition to the one included in Karanja oil, Karanja oil apparently not sufficiently concentrated in pongamol. [00023] Application FR 2720643 in the name of Clarins relates to a cosmetic preparation intended to improve the condition of the skin, it is not explicitly discussed a solar product. karanja oil is exemplified as an active ingredient may have an effect on the UV. [00024] In a trade publication (Givaudan: Leading sensory innovation Pongamia extract oil and Karanja, Issue 004 April 08), the solar effects of compositions comprising pure pongamol are praised. In page 11, the pure pongamol is characterized (content of 90% minimum). [00025] In FR 2762008 in the name of PIERRE FABRE, a deodorization process of karanja oil is disclosed. Other cosmetic applications Karanja Oil are also described, including anti-wrinkle and moisturizing properties. [00026] In the Application GB 2237805 in the name of UNILEVER PLC, a method of diketone extraction is disclosed, this method comprises two steps: extraction with an organic acid and separation of molecules interfering diketone. More specifically, it is pongamol extraction. It is specified that Karanja oil, after removal of pongamol, is used for the manufacture of soaps, the final oil is relatively devoid of pongamol. Regarding pongamol, crystals form during the process, it having a melting point between 126 ° C and 127, 5 ° C, the obtained pongamol seems relatively pure. [00027] In application WO 2014195639 in the name of Valagro, a method for extracting unsaponifiable a renewable lipid material is disclosed. Example 1 is particularly concerning the selective extraction of pongamol and karanjine. The method mainly consists of two steps, a first step of solid / liquid extraction performed using a percolator with circulation and recirculation of ethanol / hexane through previously crushed and dried seeds, and that a concentration step by evaporation of the solvent. [00028] In summary, no prior art document discloses a selective extraction of economic karanjine, environmentally friendly, inexpensive and easy to implement. [00029] This is probably due to the difficulties that the expert meeting to selectively extract two molecules close to a structural point of view. [00030] I! Therefore, there is an interest for an improved selective extraction process. [00031] Surprisingly, it was demonstrated that it was possible to selectively extract the karanjine by a process having all the following positive characteristics: economical, environmentally friendly, inexpensive and easy to implement selectively solubilizing pongamol through diesters solvents that are compatible with the requirements of the cosmetics industry. [00032] Among these diesters, particularly considering the compounds of formula (I) or mixtures thereof: Formula (I) wherein: - n is between 0 and 19; R and R 'are identical or different alkyls from a estérifi cation by a linear or branched alcohol having the empirical formula C x H 2 x 20, x being between 1 and 30, preferably between 1 and 20, preferably between 1 and 10. R "is either a hydrogen atom or an alkyl group C1-C3. [00033] These diesters have higher flash points 70 ° C and therefore does not present the VOC dangers lightning points are below 70 ° C. [00034] In the context of the present invention, certain diesters are particularly preferred, such as sebacates (n = 7), the adi pasta (n = 3), succinates (n = l), the dodécanedioates (n = 9), azelates (n = 6), glutarates (n = 2), malonates (n = 0), etc. [00035] The invention relates to a cosmetic ingredient, characterized in that it consists of a solution of at least one karanja oil extract comprising pongamol (CAS 484-33-3) and karanjine (CAS 521 from -88 to 0) in at least one solvent selected from the group of the diesters of formula (I) or mixtures thereof: Formule (I) in which : n is between 0 and 19; R and R 'identical or different are selected from the group of alkyls derived from a linear or branched alcohol having the empirical formula CxH2 x 20 before estérifi cation, x being between 1 and 30, preferably between 1 and 20, preferably enter 1 and 10. R "is either a hydrogen atom or an alkyl group C1-C3. [00036] The invention also relates to a selective precipitation process of pongamol (CAS 484-33-3) in a karanja oil comprising pongamol (CAS 484-33-3) and karanjine (CAS 521-88-0 ), characterized in that it comprises: 1) at least one step of adding to said at least one karanja oil of at least one solvent selected from the group of the diesters of formula (I) or mixtures thereof: Formula (I) wherein: - n is between 0 and 19; R and R 'are identical or different alkyls from a estérifi cation by a linear or branched alcohol of gross formula C x H2x + 20, x being between 1 and 30, preferably between 1 and 20, preferably between 1 and 10 . R "is either a hydrogen atom or an alkyl group C1-C3. said addition being effective to form a light phase (supernatant) in solution form and a heavy phase as a precipitate; and, 2) at least one step for separating the two phases obtained. [00037] The invention also relates to a cosmetic formulation, characterized in that it comprises: a cosmetic ingredient according to the invention; a cosmetically acceptable vehicle. [00038] The invention also relates to the use of a cosmetic formulation according to the invention as described above, as a solar cosmetic formulation. [00039] The invention also relates to the use of a cosmetic formulation according to the invention as described above, as anti-aging cosmetic formulation. [00040] In addition to the ecological and economic interests, the method according to the invention allows the production with a process comprising fewer steps, a solution enriched with pongamol ready to be formulated directly without requiring a melting step and dissolution of hot pongamol prior to incorporation into a cosmetic formulation like this must be done when using pure pongamol. [00041] From the economic point of view, respect for the environment and cost, the process can be performed at room temperature allows a saving of resources, since no solvent is removed during the process. In addition, no toxic solvents are used, in particular, flammable solvent classified as VOCs light (flash point <70 ° C) is used. [00042] The process also enables the use of bio-based solvents such as sebacates, succinates, and azelates with a better environmental impact than their counterparts fossil. In addition, the extraction of the unsaponifiable fraction preserves triglycerides, which can in turn be recovered, because the process includes no step of saponification or of hydrolysis. [00043] From the standpoint of ease of implementation, the method includes a limited number of relatively simple steps to implement. In particular, it has no conditioning step of the seed (drying, crushing, flattening, etc.) necessitated for example by the method described in WO 2014195639 in the name of Valagro. [00044] A number of definitions are provided below. [00045] The term "Karanja oil" means any oil derived from a plant of the family karanjas. It can especially be of the following plant species: Pongamia glabra Pongamia pinnata pinnata Milletia Demis indica gadelupa pinnata, Pongamia grandifolia, Robinia mitis, Tephrosia purpurea, Tephrosia hamiltoni, Tephrosia falciformis, Tephrosia vogellii, Tephrosia lanceolata, etc. The karanja oil can be "raw", that is to say directly obtained from the seeds by cold pressing or solvent extraction with solvent removal. [00046] Karanja oil may also undergo treatments to purify it by removing such impurities, the deodorizing or discolor. [00047] It may for example be one or more distillation (s) molecular (s) and / or degummed and / or one or more deodorisation (s). [00048] The term "light phase (supernatant)" the light phase resulting from the selective precipitation step. This is a solution. It is separated from the heavy phase (precipitated) by methods well known in the art, being, for example centrifugation or filtration. The light phase (supernatant) is of particular interest, inasmuch as once separated from the heavy phase (precipitate), the light phase (supernatant) which is a solution is the cosmetic ingredient according to the invention. [00049] The term "heavy phase (precipitated)" heavy phase from the selective precipitation step. It is separated from the light phase (supernatant) by methods well known to those skilled in the art, being for example centrifugation or filtration. [00050] The term "selective precipitation" precipitation for precipitating especially of a chemical species from a mixture. In the selective precipitation method according to the invention, the karanjine is preferentially precipitated relative to pongamol. For example, when, during a precipitation step, the precipitate is composed of 61.5% of karanjine and only 4.3% of pongamol, it is a selective precipitation of the karanjine. [00051] The term "weight percent" (expressed in%) the ratio between the mass of a constituent of a mixture and the total mass of the mixture. For example, if a component i of a mixture has a mass of 1 kg, and the mixture has a mass of 100 kg, the weight percentage of component i is 1%. For example, when a cosmetic ingredient according to the invention is characterized in that the percentage by mass of pongamol in the solution (including cosmetic ingredient consists entirely) is 3%, this means that in 100 g of cosmetic ingredient / solution, there are 3 g of pongamol. [00052] The term "extraction yield", the ratio between the mass of a component before a step (e.g., a selective precipitation step) and the mass of the same component after said step. In particular it can be expressed as a percentage, and is between 0% and 100%. For example, the extraction yield of pongamol during precipitation is calculated as follows: pongamol mass in karanja oil prior to the precipitation / mass pongamol in the solution obtained after the precipitation. When speaking of "extraction efficiency in a phase", it is the ratio between the mass of a component in the phase and the mass of the same component before step leading to the formation of the phase. [00053] The term "multiplication ratio m P ongamoi / mi

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Orders

Section Controller Decision Date

Application Documents

# Name Date
1 201837005168-IntimationOfGrant10-03-2023.pdf 2023-03-10
1 201837005168-STATEMENT OF UNDERTAKING (FORM 3) [12-02-2018(online)].pdf 2018-02-12
2 201837005168-FORM 1 [12-02-2018(online)].pdf 2018-02-12
2 201837005168-PatentCertificate10-03-2023.pdf 2023-03-10
3 201837005168-PETITION UNDER RULE 137 [15-02-2023(online)].pdf 2023-02-15
3 201837005168-DRAWINGS [12-02-2018(online)].pdf 2018-02-12
4 201837005168-Written submissions and relevant documents [15-02-2023(online)].pdf 2023-02-15
4 201837005168-DECLARATION OF INVENTORSHIP (FORM 5) [12-02-2018(online)].pdf 2018-02-12
5 201837005168-PETITION UNDER RULE 138 [10-02-2023(online)].pdf 2023-02-10
5 201837005168-COMPLETE SPECIFICATION [12-02-2018(online)].pdf 2018-02-12
6 201837005168-Proof of Right (MANDATORY) [13-04-2018(online)].pdf 2018-04-13
6 201837005168-Correspondence to notify the Controller [27-01-2023(online)].pdf 2023-01-27
7 201837005168.pdf 2018-04-20
7 201837005168-FORM-26 [27-01-2023(online)].pdf 2023-01-27
8 201837005168-US(14)-ExtendedHearingNotice-(HearingDate-30-01-2023).pdf 2023-01-16
8 201837005168-Information under section 8(2) (MANDATORY) [24-05-2018(online)].pdf 2018-05-24
9 201837005168-Information under section 8(2) (MANDATORY) [24-05-2018(online)]-1.pdf 2018-05-24
9 201837005168-REQUEST FOR ADJOURNMENT OF HEARING UNDER RULE 129A [10-01-2023(online)].pdf 2023-01-10
10 201837005168-US(14)-ExtendedHearingNotice-(HearingDate-13-01-2023).pdf 2022-12-12
10 201837005168-Verified English translation (MANDATORY) [31-05-2018(online)].pdf 2018-05-31
11 201837005168-FORM-26 [10-07-2018(online)].pdf 2018-07-10
11 201837005168-REQUEST FOR ADJOURNMENT OF HEARING UNDER RULE 129A [07-12-2022(online)].pdf 2022-12-07
12 201837005168-FORM 18 [09-07-2019(online)].pdf 2019-07-09
12 201837005168-US(14)-HearingNotice-(HearingDate-15-12-2022).pdf 2022-11-15
13 201837005168-CLAIMS [01-08-2022(online)].pdf 2022-08-01
13 201837005168-FER.pdf 2022-02-02
14 201837005168-CORRESPONDENCE [01-08-2022(online)].pdf 2022-08-01
14 201837005168-OTHERS [01-08-2022(online)].pdf 2022-08-01
15 201837005168-FER_SER_REPLY [01-08-2022(online)].pdf 2022-08-01
16 201837005168-CORRESPONDENCE [01-08-2022(online)].pdf 2022-08-01
16 201837005168-OTHERS [01-08-2022(online)].pdf 2022-08-01
17 201837005168-FER.pdf 2022-02-02
17 201837005168-CLAIMS [01-08-2022(online)].pdf 2022-08-01
18 201837005168-US(14)-HearingNotice-(HearingDate-15-12-2022).pdf 2022-11-15
18 201837005168-FORM 18 [09-07-2019(online)].pdf 2019-07-09
19 201837005168-FORM-26 [10-07-2018(online)].pdf 2018-07-10
19 201837005168-REQUEST FOR ADJOURNMENT OF HEARING UNDER RULE 129A [07-12-2022(online)].pdf 2022-12-07
20 201837005168-US(14)-ExtendedHearingNotice-(HearingDate-13-01-2023).pdf 2022-12-12
20 201837005168-Verified English translation (MANDATORY) [31-05-2018(online)].pdf 2018-05-31
21 201837005168-Information under section 8(2) (MANDATORY) [24-05-2018(online)]-1.pdf 2018-05-24
21 201837005168-REQUEST FOR ADJOURNMENT OF HEARING UNDER RULE 129A [10-01-2023(online)].pdf 2023-01-10
22 201837005168-Information under section 8(2) (MANDATORY) [24-05-2018(online)].pdf 2018-05-24
22 201837005168-US(14)-ExtendedHearingNotice-(HearingDate-30-01-2023).pdf 2023-01-16
23 201837005168-FORM-26 [27-01-2023(online)].pdf 2023-01-27
23 201837005168.pdf 2018-04-20
24 201837005168-Correspondence to notify the Controller [27-01-2023(online)].pdf 2023-01-27
24 201837005168-Proof of Right (MANDATORY) [13-04-2018(online)].pdf 2018-04-13
25 201837005168-PETITION UNDER RULE 138 [10-02-2023(online)].pdf 2023-02-10
25 201837005168-COMPLETE SPECIFICATION [12-02-2018(online)].pdf 2018-02-12
26 201837005168-Written submissions and relevant documents [15-02-2023(online)].pdf 2023-02-15
26 201837005168-DECLARATION OF INVENTORSHIP (FORM 5) [12-02-2018(online)].pdf 2018-02-12
27 201837005168-PETITION UNDER RULE 137 [15-02-2023(online)].pdf 2023-02-15
27 201837005168-DRAWINGS [12-02-2018(online)].pdf 2018-02-12
28 201837005168-PatentCertificate10-03-2023.pdf 2023-03-10
28 201837005168-FORM 1 [12-02-2018(online)].pdf 2018-02-12
29 201837005168-STATEMENT OF UNDERTAKING (FORM 3) [12-02-2018(online)].pdf 2018-02-12
29 201837005168-IntimationOfGrant10-03-2023.pdf 2023-03-10

Search Strategy

1 201837005168E_02-02-2022.pdf
1 searchstrategyE_12-01-2021.pdf
2 201837005168E_02-02-2022.pdf
2 searchstrategyE_12-01-2021.pdf

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