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Sunscreen Compositions Incorporating Kopsalate As An Spf Booster With Strong Photo Stabilization Activity

Abstract: The present invention provides a novel sunscreen composition referred as Kopsalate comprising of one or more compounds of an Isosorbide 2, 5 disalicylate. The Isosorbide 2, 5 disalicylate has a minimal variation in UV absorbance after and before exposure to sunlight and the UV absorbance. This minimal variation in UV absorbance after and before exposure to sunlight shows that the compound is photo stable. The novel sunscreen composition has a better sun protection factor (SPF) compared to all other salicylates. The novel sunscreen composition has a higher molecular weight compared to conventionally available sunscreen products. Further, the novel sunscreen composition has a property of SPF boosting function of sunscreen composition.

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Patent Information

Application #
Filing Date
14 November 2016
Publication Number
20/2018
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
senthil@intepat.com
Parent Application
Patent Number
Legal Status
Grant Date
2021-11-05
Renewal Date

Applicants

Kop Research Centre Pvt Ltd
Usha Krishna Tower, Plot No.36B, Road No. 3 & 5, Jigani Industrial Area, Anekal Taluk, Bangalore 560105 (IN)

Inventors

1. HEMANTH KUMAR, KALVI
C/o. KOP Research Centre Pvt Ltd ‘Usha Krishna Tower’, Plot No.36B, Road No.3 & 5, Jigani Industrial Area, Anekal Taluk, Bangalore 560 105
2. RAJAKUMAR, Ramamoorthy
C/o. KOP Research Centre Pvt Ltd ‘Usha Krishna Tower’, Plot No.36B, Road No.3 & 5, Jigani Industrial Area, Anekal Taluk, Bangalore 560 105
3. RAVI KUMAR, Lagumaddepalli Nanjunda Reddy
C/o. KOP Research Centre Pvt Ltd ‘Usha Krishna Tower’, Plot No.36B, Road No.3 & 5, Jigani Industrial Area, Anekal Taluk, Bangalore 560 105
4. RANGANATHAN, Koottungalamadhom Ramaswamy
C/o. KOP Research Centre Pvt Ltd ‘Usha Krishna Tower’, Plot No.36B, Road No.3 & 5, Jigani Industrial Area, Anekal Taluk, Bangalore 560 105
5. JEYARAMAN Govindarajalu
C/o. KOP Research Centre Pvt Ltd ‘Usha Krishna Tower’, Plot No.36B, Road No.3 & 5, Jigani Industrial Area, Anekal Taluk, Bangalore 560 105
6. NEERAJA, Sharad Sabnis
C/o. KOP Research Centre Pvt Ltd ‘Usha Krishna Tower’, Plot No.36B, Road No.3 & 5, Jigani Industrial Area, Anekal Taluk, Bangalore 560 105

Specification

Claims:1. A novel sunscreen composition comprising of one or more compounds of formula A; wherein the composition comprises an Isosorbide 2, 5 disalicylate.

2. The novel sunscreen composition of claim 1, wherein the Isosorbide 2, 5 disalicylate is a white colored, odorless powder material.
3. The novel sunscreen composition of claim 1, wherein the Isosorbide 2, 5 disalicylate is photo stable; wherein a difference between UV absorbance after and before exposure to sunlight is less and the UV absorbance is in the range of 0.12 to 0.13.
4. The novel sunscreen composition of claim 1, wherein the Isosorbide 2, 5 disalicylate has a sun protection factor (SPF) in the range of 13 to 13.5.
5. The novel sunscreen composition of claim 1, wherein the Isosorbide 2, 5 disalicylate has an UV spectroscopic absorbance is in the range of 230-250 E1%/1 cm.
6. The novel sunscreen composition of claim 1, wherein the Isosorbide 2, 5 disalicylate has a molecular weight in the range of 380 to 400.
7. The novel sunscreen composition of claim 1, wherein the Isosorbide 2, 5 disalicylate is soluble in OMC and insoluble in water.
8. The novel sunscreen composition of claim 1, wherein the Isosorbide 2, 5 disalicylate has considerable SPF boosting function when formulated with other UV absorbers.
9. The novel sunscreen composition of claim 1, wherein the Isosorbide 2, 5 disalicylate has considerable photo-stabilization of photo sensitive sunscreens.
10. The novel sunscreen composition of claim 9, wherein the Isosorbide 2, 5 disalicylate can be used as organic UB blocker in face powders.

, Description:Sunscreen compositions incorporating KOPSALATE as an SPF booster with Strong Photo-stabilization activity.

FIELD OF INVENTION
[0001] The embodiment herein generally relates to a sunscreen composition with SPF (sun Protection factor) booster having photo-stabilization activity . More particularly, the invention provides a SPF booster with photo-stabilization activity made of novel salicylate compound referred as Kopsalate. Further, the novel salicylate compound has remarkable properties that are essential for manufacturing the sunscreen compositions.
BACKGROUND AND PRIOR ART
[0002] Commonly people maintain their personality by applying skin lightening lotions, sunscreen creams, lotions and so on. These sunscreen lotions and creams can absorb or reflect some of the ultraviolet (UV) radiation from sun and thus help the person by protecting against sunburn. Chemicals used in sunscreen application must have essential properties such as UV absorbance, solubility in OMC, biodegradability, SPF, photo stability and so on.
[0003] Mainly, Salicylates are used in sunscreens lotion preparation. Hence the salicylates are having acceptable essential properties for manufacturing sunscreen compositions. Commonly used Salicylates are Homosalate, Octyl Salicylate, and TEA Salicylate. In which, Homosalate is the chemical that is used by FDA as a standard one for measuring sun protection factor (SPF). These Salicylates have been used for a long time to protect against UV radiations.
[0004] However, the quality of the sunscreen is usually measured by the SPF values. Hence, these SPF values can measure how well a sunscreen can protect skin from UVB rays. The UVB rays are a kind of radiation that causes sunburn, damages skin, and can even be a carcinogen for a human skin.
[0005] Therefore, there is a need to develop a novel sunscreen composition having salicylates as a compound and that must have a better photo stability and ultra violet (UV) rays absorbance with SPF boosting function. Further, there is a need for a novel sunscreen composition which has to be soluble in OMC and insoluble in water. Furthermore, there is a need for a novel sunscreen composition which has a higher SPF with photo-stabilization activity compared to other composition used for the same purpose.
OBJECTS OF THE INVENTION
[0006] Some of the objects of the present disclosure are described herein below:
[0007] A main object of the present invention is to provide a novel sunscreen composition referred as a Kopsalate having salicylates along with biomass derived polyols and their derivatives.
[0008] Another object of the present invention is to provide a novel sunscreen composition having higher molecular weight compared to the generally used compositions for manufacturing sunscreen compositions.
[0009] Still another object of the present invention is to provide a novel sunscreen composition having better ultra violet (UV) rays absorbance.
[00010] Yet another object of the present invention is to provide a novel sunscreen composition having better biodegradability.
[00011] Another object of the present invention is to provide a novel sunscreen composition having better photo stability.
[00012] Another object of the present invention is to provide a novel sunscreen composition having better SPF boosting function.
[00013] Another object of the present invention is to provide a novel sunscreen composition that can be soluble in OMC and insoluble in water.
[00014] Another object of the present invention is to provide a novel sunscreen compositions with salicylates for using face powders for more UV absorbance and high SPF boosting function.
[00015] The other objects and advantages of the present invention will be apparent from the following description when read in conjunction with the accompanying drawings, which are incorporated for illustration of preferred embodiments of the present invention and are not intended to limit the scope thereof.
SUMMARY OF THE INVENTION
[00016] In view of the foregoing, an embodiment herein provides a novel sunscreen composition referred as Kopsalate having disalicylates along with an Isosorbide. More specifically, the invention provides a novel sunscreen composition comprising of one or more compounds of an Isosorbide 2, 5 disalicylate; wherein the Isosorbide 2,5 disalicylate is a white colored, odorless powder material. The Isosorbide 2, 5 disalicylate has a minimal variation in UV absorbance after and before exposure to sunlight and the UV absorbance is in the range of 0.12 to 0.13. This minimal variation in UV absorbance after and before exposure to sunlight shows that the compound is photo stable.
[00017] According to an embodiment, the novel sunscreen composition has a sun protection factor (SPF) in the range of 13 to 13.5. Further, the novel sunscreen composition has an UV spectroscopic absorbance is in the range of 230-250 (E1%/1 cm). The novel sunscreen composition has a higher molecular weight compared to conventionally available sunscreen products. The molecular weight of the novel sunscreen composition is in the range of 380 to 400. Further, the novel sunscreen composition has a property of solubility in OMC. However, the novel sunscreen composition is insoluble in water.
[00018] According to an embodiment, the novel sunscreen composition has better SPF boosting function along with good photo-stabilization activity.
[00019] These and other aspects of the embodiments herein will be better appreciated and understood when considered in conjunction with the following description and the accompanying drawings. It should be understood, however, that the following descriptions, while indicating preferred embodiments and numerous specific details thereof, are given by way of illustration and not of limitation. Many changes and modifications may be made within the scope of the embodiments herein without departing from the spirit thereof, and the embodiments herein include all such modifications.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[00020] The embodiments herein and the various features and advantageous details thereof are explained more fully with reference to the non-limiting embodiments and detailed in the following description. Descriptions of well-known components and processing techniques are omitted so as to not unnecessarily obscure the embodiments herein. The examples used herein are intended merely to facilitate an understanding of ways in which the embodiments herein may be practiced and to further enable those of skill in the art to practice the embodiments herein. Accordingly, the examples should not be construed as limiting the scope of the embodiments herein.
[00021] As mentioned above, there is a need for a novel sunscreen which has a . The embodiments herein achieve this by providing a novel sunscreen composition having disalicylates along with an Isosorbide.
[00022] According to an embodiment, a novel sunscreen composition having disalicylates along with an Isosorbide. More specifically, the invention provides a novel sunscreen composition referred as Kopsalate comprising of one or more compounds of an Isosorbide 2, 5 disalicylate; wherein the Isosorbide 2,5 disalicylate is a white colored, odorless powder material. The Isosorbide 2, 5 disalicylate has a minimal variation in UV absorbance after and before exposure to sunlight and the UV absorbance is in the range of 0.12 to 0.13. This minimal variation in UV absorbance after and before exposure to sunlight shows that the compound is photo stable.
[00023] According to an embodiment, the novel sunscreen composition has a sun protection factor (SPF) in the range of 13 to 13.5. Further, the novel sunscreen composition has an UV spectroscopic absorbance is in the range of 230-250 (E1%/1 cm). The novel sunscreen composition has a higher molecular weight compared to conventionally available sunscreen products. The molecular weight of the novel sunscrren composition is in the range of 380 to 400. Further, the novel sunscreen composition has a property of solubility in OMC. However, the novel sunscreen composition is insoluble in water. Further, the kopsalate has a better moisturizing property.
[00024] According to an embodiment the sunscreen compositions with kopsalate of the present invention is intended for topical use and can be administered as gel, cream, lotion, ointment solution, spray, shining liquid lip-stick or in hair conditioners. The composition may further contain other therapeutic agents and conventionally used vehicles and excipients such as fragrances, stabilizers colors etc.
[00025] According to an embodiment, the chemical structure of Kopsalate is provided as in formula A. The
[00026] Kopsalate comprising of one or more compounds of an Isosorbide 2, 5 disalicylate.

[00027] The examples used herein are intended merely facilitate an understanding of ways in of ways in which the embodiments herein may be practiced and to further enable those skilled in the art, to practice embodiments herein. Accordingly, the examples should not be construed as limiting the scope of the embodiments herein.
[00028] Example 1. A 3000 mL four-neck flask was fitted with an over-head paddle stirrer, a thermometer, a gas inlet tube and a long air condenser. The flask was charged with 1500 mL commercial toluene, isosorbide (146 g, 1.0 mole), salicylic acid (414.0 g, 3 mole) and P-Toluenesulphonic acid(1.0 g). The mixture was stirred and refluxed at 110oC under a slow steam of argon gas until salicylic acid disappears in TLC examination . during the reaction, 40 g (2.05 mole) of water was collected from the reaction mass. After stirring for 12 hours, the reaction mass cooled to room temperature and washed with toluene until the solid on the filter was colorless and the yellow filtrate evaporated to dryness to leave a yellow gummy solid. The solid was purified from ethyl acetate, dried over anhydrous sodium sulfate and evaporated down again to give a white colored solid 150 g.
[00029] Example 2. Composition containing kopsalate prepared in Example 1, is shown in Table 1 for Shining liquid lipstick.
S.No Ingredient Amount %
1 Propylene glycol dibenzoate 20
2 Caprylic /capric triglyceride 15
3 Kopsalate 3
4 Caprylyl methicone 12
5 Red 6 lake 2
6 Iron oxide red 1.2
7 Bis hydroxyl ethoxy propyl demthicone 1
8 Mica 1.2
9 Tio2 0.5
10 Isododecane Q.S.
11 C 30-45 alkyl dimethyl silyl propyl silseqquioxane 8

[00030] Example 3. Compositions containing kopsalate prepared in Example 1, is shown in table 2 for BB cream.
Phase No Ingredient Wt.% Trade name /supplier Uses
A 1 Aqua Q.S Inhouse
2 Pullulan 0.08 Kopulan/KOPL Thickening agent/ Sensory modifier
3 Ammonium Acyrloyl dimethyltaurate /VP Copolymer 0.3 Aristoflex AVC / Clariant Gelling agent
4 Propylene Glycol 1.5 S D fine Humectant
B 5 Cetostearyl Alcohol 0.5 S D fine Emulsifier
6 Diiisopropyl Adipate 2 Subhash chemicals Emollient/plasticizer
7 Cyclopentasiloxane 7 Mascot /Dow corning Sensory modifier
8 Glyceryl Stearate and PEG-100 Stearate 3 Arlacel 165 /Croda Emulsifier
9 Sucrose Distearate 2 Lubrizol Emulsifier
10 Ethyl Hexyl Glycerin 1 Kopcerin/KOPL Skin conditioning
11 Cetearyl Ethylhexonate (and) Iso propyl Myristrate 2.5 Crodamol CAP
Croda/Mascot Emollient /Spread ability enhancer
12 Capyrlic Capric Triglyceride 2 Prodachem Emollient
13 Cetyl glucoside & Cetearyl alcohol 3 Emulgade pl 68/50 /BASF Emulsifier
14 Ethyl hexyl triazone 1.5 Koptrizon /KOPL UV-B filter
15 Diethylhexylbutamido triazone 1 Kopcotrizinol/KOPL UV filter
16 Avobenzone 1 Kopbenzone /KOPL UV-A filter
Kopsalate 4
17 Lavanya Chandni CI77891 (Titanium dioxide) 0.8 Neelikon colors UV filter
18 Lavanya Sooraj (Yellow Pigment ) CI77492 0.05 Neelikon colors Colorant
19 Lavanya Brown (light)CI77491 0.1 Neelikon colors Colorant
20 Zinc oxide 0.5 S D fine UV–B Filter
D 24 Phenoxyethanol 0.2 S d fine Preservative
25 Silicone 3031 2 Mascot /Dow corning Sensory modifier
26 Sodium hyaluronate (1% sol) 0.5 Kopuran/KOPL Moisturizer
27 Perfume 0.6 Ultra International Fragrance
E 28 Citric acid (50% sol) Q,S S D fine pH adjuster

[00031] Example 4. Compositions containing kopsalate prepared in Example 1, is shown in table 3 for Sunscreen cream.

S.No Ingredient Amount %
Phase A

1.
Glycerol AR 3
2. Distilled water Q.S.
3 Ethylenediamine tetra acetic acid (EDTA) 0.1
4. Carbopol Ultrez 21 Polymer 0.3
5. Aristoflex AVC 0.4
6 Kopguard 1.0
7 Phenoxy ethanol 0.1
Phase B
8 Ethyl hexyl glycerin 1.0
9 Cetostearyl alcohol 2
10. Aracel 165 –FL-(TH) 2
11. Cetyl Alcohol 2
12. White soft Paraffine 1
13. Emulium Delta 3
14 Octyl methoxycinnamate 7.5
15 Caprylic capric triglyceride 3
16. i) Oxybenzone 5
17. ii) KOPSALATE 5
18. Dimethicone /KF-96A-350CS 1
19. Fragrance 0.4
20. Amp ultra pc Adjust pH upto to 5.70

Experimental Results:
[00032] According to an embodiment, table 1 shows the comparison of Kopsalate with other salicylates based on their absorbance property, molecular weight, UV spectra absorbance. Further, the table shows the comparison of Kopsalate with other salicylates related to their physical properties. In that, Kopsalate shows better absorption and has a molecular weight of approximately 400. Specifically, the Kopsalate shows UV spectra absorption of 230-250. The nature of the Kopsalate is a white colored, odorless crystalline solid. Regarding the solubility property, the Kopsalate can be soluble in OMC and insoluble in water.


S. No Compound Absorption / ? max (nm) Molecular weight UV Sp. Absorbance (E 1%/1cm) Nature Solubility
1 Octyl salicylate 305 250 165-185 Liquid -
2 Homosalate 305 262 170-180 Liquid -
3 Kopsalate 309 App. 400 230-250 White/ odorless crystalline solid Soluble in OMC and
insoluble in water

Table. 1. Comparison of Kopsalate with other salicylates related to physical properties.
[00033] According to an embodiment, table.2 shows comparative photo stability study on Kopsalate with other compositions already in use for manufacturing sunscreen products.
S. No Sample UV Absorbance before exposure to sunlight UV Absorbance After exposure to sunlight Remarks
1 Kopsalate 0.124 0.121 Photo stable
2 Avobenzone 0.544 0.224 unstable
3 Octyl salicylate 0.088 0.70 Less UV B absorbance and less stable compared to KOPSALATE
4 Formula A
(KOPSALATE 4%, Avobenzone 3 %, Benzophenone 5%, OMC 7.5%) 1.602 1.339
5 Formula B
(Avobenzone 3 %, Benzophenone 5%, OMC 7.5%) 1.349 1.250 Less efficient compared to Formula A
Table. 2. Comparison of Kopsalate with other salicylates related to physical properties.
[00034] According to an embodiment, table. 3 show the value of study yielded a sun protection factor (SPF), Boots star rating and PA rating for a sample Kopsalate.
Sample SPF Boots Star Rating PA rating
Kopsalate 13.34 No rating +
Table. 3. The value SPF, Boots star rating and PA rating for Kopsalate.
[00035] According to an embodiment, table. 4 show the ISOSA Sun protection factor (SPF) comparison with other salicylates. Compared to other salicylates, Kopsalate shows more SPF rating.
Sample SPF Remarks
Kopsalate 13.34 Studied from scientific research centre. The Kelkar Education Trust.
Homosalate (HS) 4.47 Reference a) & b)
2, Ethylhexylsalicylate (EHS) 7.1 Reference c)
Table. 4. The ISOSA Sun protection factor (SPF) comparison with other salicylates.
[00036] The foregoing description of the specific embodiments will so fully reveal the general nature of the embodiments herein that others can, by applying current knowledge, readily modify and/or adapt for various applications such specific embodiments without departing from the generic concept, and, therefore, such adaptations and modifications should and are intended to be comprehended within the meaning and range of equivalents of the disclosed embodiments. It is to be understood that the phraseology or terminology employed herein is for the purpose of description and not of limitation. Therefore, while the embodiments herein have been described in terms of preferred embodiments, those skilled in the art will recognize that the embodiments herein can be practiced with modification within the spirit and scope of the embodiments as described herein.

Documents

Application Documents

# Name Date
1 Power Of Attorney_14-11-2016.pdf 2016-11-14
2 Form5 As Filed_14-11-2016.pdf 2016-11-14
3 Form3 As Filed_14-11-2016.pdf 2016-11-14
4 Form2(TitlePage)_14-11-2016.pdf 2016-11-14
5 Description(Complete)_14-11-2016.pdf 2016-11-14
6 Claims_14-11-2016.pdf 2016-11-14
7 Abstract_14-11-2016.pdf 2016-11-14
8 201641038782-FORM 18 [14-11-2020(online)].pdf 2020-11-14
9 201641038782-FER_SER_REPLY [02-08-2021(online)].pdf 2021-08-02
10 201641038782-COMPLETE SPECIFICATION [02-08-2021(online)].pdf 2021-08-02
11 201641038782-CLAIMS [02-08-2021(online)].pdf 2021-08-02
12 201641038782-ABSTRACT [02-08-2021(online)].pdf 2021-08-02
13 201641038782-Correspondence to notify the Controller [08-09-2021(online)].pdf 2021-09-08
14 201641038782-Response to office action [08-10-2021(online)].pdf 2021-10-08
15 201641038782-US(14)-HearingNotice-(HearingDate-14-09-2021).pdf 2021-10-17
16 201641038782-US(14)-ExtendedHearingNotice-(HearingDate-24-09-2021).pdf 2021-10-17
17 201641038782-FER.pdf 2021-10-17
18 201641038782-PatentCertificate05-11-2021.pdf 2021-11-05
19 201641038782-Marked Up Claims_Granted 381295_05-11-2021.pdf 2021-11-05
20 201641038782-IntimationOfGrant05-11-2021.pdf 2021-11-05
21 201641038782-Description_Granted 381295_05-11-2021.pdf 2021-11-05
22 201641038782-Claims_Granted 381295_05-11-2021.pdf 2021-11-05
23 201641038782-Abstract_Granted 381295_05-11-2021.pdf 2021-11-05
24 201641038782-RELEVANT DOCUMENTS [14-09-2022(online)].pdf 2022-09-14
25 201641038782-RELEVANT DOCUMENTS [20-09-2023(online)].pdf 2023-09-20

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