IP Library Granted Patent US 11,224,222
Granted Patent B2
US 11,224,222 · App. 15/561,222 · Granted Jan 18, 2022

Synergistic compositions of dehydroacetic acid and methods for reducing yellowing in various end-user compositions

Inventors: Raman Premachandran (Saddle Brook, NJ); Kalpa Metha (Raritan, NJ); Jyoti Gupta (Basking Ridge, NJ); Najeeb H. Hakimi (Edison, NJ); Karen W Winkowski (Springfield, NJ)
Assignee: ISP Investments LLC
A01N43/16A01N25/02A61K8/35A61K8/498A61K8/4973A61Q5/02A61Q19/00A61K2800/524
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Quick Facts
Patent No.
US 11,224,222
App. No.
15/561,222
Granted
Jan 18, 2022
Kind
B2
Abstract

What is described herein is a stable and reduced-yellowing/non-yellowing synergistic preservative composition comprising: (i) about 0.1 wt. % to about 40 wt. % of dehydroacetic acid (DHA); and about 0.1 wt. % to about 99.9 wt. % of at least one aprotic solvent. Also described herein are aqueous and non-aqueous based preservative compositions for various end-user applications, and processes for preparing and using such compositions to reduce yellowing of DHA when added to the end-user applications.

Claims (24)

1. A stable and non-yellowing/reduced-yellowing synergistic preservative composition comprising:

i. about 8.0 wt. % of dehydroacetic acid (DHA); and

ii. about 92 wt. % of propylene carbonate (PC), wherein composition is delivered as emulsion, microemulsion, nanoemulsion, solution, dispersion, suspension, complex coacervate or concentrate,

wherein said composition is capable of inhibiting or killing Staphylococcus aureus, Escherichia coli, Aspergillus niger, Aspergillus brasiliensis and Candida albicans,

wherein the DHA does not undergo yellow coloration or undergoes reduced yellow coloration at room/ambient temperature and at 50° C. on storage and transit conditions, and

wherein said composition is stable on storage of at least 2 years at room temperature.

2. The preservative composition according to claim 1 , wherein said composition is aqueous or non-aqueous based.

3. The preservative composition according to claim 1 , wherein said composition is employed in various aqueous and non-aqueous based end-user applications comprising cosmetic products, toiletry products, personal care products, oral care products, skin care products, hair care products, household & cleaning products, Industrial and Institutional cleaning products, disinfecting products, contact lens, enzyme based formulations, wound care, sanitary products, agricultural compositions, textile industries, coating industries and/or laundry products.

4. The preservative composition according to claim 1 , wherein said composition comprises one or more additional biocides selected from the group consisting of triclosan, 2-methyl-4-isothiazolin-3-one (MIT), 1,2-Benzisothiazolin-3-one (BIT), 5-Chloro-2-methyl-4-isothiazolin-3-one (CMIT), 2-Octyl-4-isothiazolin-3-one (OIT), 3-iodo-2-propynylbutyl-carbamate (IPBC), 3-iodopropynyl-N-phenyl carbamate (IPPC), zinc pyrithione (ZnPy), bronopol, Quaternary ammonium compounds alkyl parabens, chlorophenisin, benzyl alcohol, organic acids, sorbic acid, benzoic acid, salicylic and their salts, potassium sorbate, sodium benzoate, phenoxyethanol, diazolidinyl urea, imidazolidinyl urea, sodium hydroxymethyl glycinate, Hydantoins, sodium pyrithione, capryl glycol, phenyl ethanol, phenyl propanol, ethyl hexyl glycerine, benzyl alcohol.

5. The preservative composition according to claim 1 , wherein the amount of preservative composition employed in aqueous and non-aqueous based end-user products/compositions is in the range of from about 0.01 wt. % to about 5.0 wt. % of the total composition.

6. A non-aqueous based end-user composition comprising: i. about 0.01 wt. % to about 5.0 wt. % of the preservative composition of claim 1 ; ii. about 0.01 wt. % to about 5 wt. % of at least one antioxidant or radical quencher; and iii. about 0.5 to about 2.0 wt. % of polyvinyl pyrrolidone (PVP), wherein the composition is stable, and capable of reducing yellowing of dehydroacetic acid.

7. The non-aqueous based end-user composition according to claim 6 , wherein said composition is employed in aqueous and non-aqueous based end-user applications comprising cosmetic products, toiletry products, personal care products, oral care products, skin care products, hair care products, household & cleaning products, Industrial and Institutional cleaning products, disinfecting products, contact lens, enzyme based formulations, wound care, sanitary products, agricultural compositions, textile industries, coating industries and laundry products.

8. The non-aqueous based end-user composition according to claim 6 , wherein said anti-oxidant is selected from the group consisting of phenols, hindered phenols, alkylated monophenols, alkylthiomethylphenols, hydroquinones and alkylated hydroquinones, tocopherols, hydroxylated thiodiphenyl ethers, alkylidenebisphenols, O-, N- and S-benzyl compounds, hydroxybenzylated malonates, aromatic hydroxybenzyl compounds, triazine compounds, benzylphosphonates, acylaminophenols, esters, hindered esters, tertiary butyl alcohol (TBA), benzofuranones, hydroxylamines, β-carotenes, and/or aminic antioxidants.

9. The non-aqueous based end-user composition according to claim 6 , wherein said anti-oxidant is added externally to said non-aqueous based end-user compositions having a pH of 4 to 8.

10. A method for reducing yellowing of dehydroacetic acid (DHA) present in a non-aqueous based end-user composition, wherein, the method comprises adding (a) about 0.01 wt. % to about 5.0 wt. % of a preservative composition of claim 1 (b) about 0.1 wt. % to about 5 wt. % of at least one anti-oxidant, to the non-aqueous based end user composition.

11. An aqueous based end-user composition comprising: i. about 0.01 wt. % to about 5.0 wt. % of the preservative composition of claim 1 ; ii. about 0.01 wt. % to about 5 wt. % of at least one antioxidant; iii. about 0.01 wt. % to about 5 wt. % of at least one chelating agent or sequestering agent; and iv. about 0.5 to about 2.0 wt. % of polyvinyl pyrrolidone (PVP), wherein the composition is stable, and capable of reducing yellowing of dehydroacetic acid.

12. The aqueous based end-user composition according to claim 11 , wherein said composition is employed in cosmetic products, toiletry products, personal care products, oral care products, skin care products, hair care products, household & cleaning products, Industrial and Institutional cleaning products, disinfecting products, contact lens, enzyme based formulations, wound care, sanitary products, agricultural compositions, textile industries, coating industries and laundry products.

13. A method for reducing yellowing of dehydroacetic acid (DHA) present in an aqueous based end-user composition, wherein the method comprises adding (a) about 0.01 wt. % to about 5.0 wt. % of a preservative composition of claim 1 , (b) 0.01 wt. % to about 5 wt. % of at least one aqueous soluble anti-oxidant, and (c) 0.01 wt. % to about 5 wt. % of at least one chelating agent or sequestering agent, to the non-aqueous based end-user composition.

14. The aqueous based end-user composition according to claim 11 , wherein the pH of the aqueous composition is from about 3.5 to about 8.5.

15. The aqueous based end-user composition according to claim 11 , wherein the chelating or sequestering agent is selected from the group consisting of polyols, gluconates, sorbitals, mannitols, carbonates, hydroxamates, catechols, α-amino carboxylates, alkanolamines, metal-ion sequestrants, hydroxy-carboxylic acids, aminocarboxylic acids, amino polycarboxylic acids, polyamines, polyphosphates, phosphonic acids, crown ethers, amino acids, polycarboxylic acids, cyclodextrin, phosphonates, polyacrylates, polymeric polycarboxylates, condensed phosphates, Ethylene-diamine-tetra acetic acid (EDTA), Glutamic acid diacetic acid (GLDA), a GLDA salt, a GLDA derivative, a tetrasodium or ammonium salt of GLDA, Methylglycine diacetic acid (MGDA), S,S-ethylenediaminedisuccinic acid (EDDS), Ethylene diamine-N,N′-disuccinic acid, or alkali or alkaline earth salts, Trisodium ethylene diamine-N,N-disuccinate (EDDS), (S,S)-Iminodisuccinic acid, (S,R)-Imino-disuccinic acid, hydroxyiminodisuccinic acid (HIDS), Trisodium methylglycine-N,Ndiacetate, Cysteic acid-N,N-diacetic acid, Cysteic acid-N-monoacetic acid, Alanine-N-monoacetic acid, β-Alanine-N,N-diacetic acid, (S)-α-Alanine-N,N-diacetic acid, N-[2-(3-Hydroxysuccinyl)]-L-serine, Methyliminodiacetic acid and their alkali metal salts, (S)-Aspartic acid-monoacetic acid, (S)-Aspartic acid-N,N-diacetic acid, (S)-Aspartic acid-monopropionic acid, N-(3-Hydroxysuccinyl)-aspartic acid, (S)-2-Sulfomethylaspartic acid, (S)-2-Sulfoethylaspartic acid, (S)-Glutamic acid-N,N-diacetic acid, (S)-2-Sulfomethylglutamic acid, (S)-2-Sulfoethylglutamic acid, (S)-Serine-N,N-diacetic acid, (S)-Phenylalanine-N,N-diacetic acid and alkali metal salts, Polyamino disuccinic acids, N-bis-[2-(1,2-Dicarboxyethoxy)ethyl]glycine (BCA6), N-bis-[2-(1,2-Dicarboxyethoxy)ethyl]aspartic acid (BCA5), N-bis-[2-(1,2-Dicarboxyethoxy)ethyl]-methylglycine (MCBA5), N-tris-[(1,2-Dicarboxyethoxy)ethyl]amine (TCA6), N-Methyliminodiacetic acid (MIDA), Iminodiacetic acid (IDA), N-(2-Acetamido)iminodiacetic acid (ADA), Hydroxymethyl-iminodiacetic acid, 2-(2-Carboxyethylamino)succinic acid (CEAA), 2-(2-Carboxymethylamino)succinic acid (CMAA), Diethylenetriamine-N,N″-disuccinic acid, Triethylenetetramine-N,N′″-disuccinic acid, 1,6-Hexamethylenediamine-N,N′-disuccinic acid, Tetraethylenepentamine-N,N″″-disuccinic acid, 2-Hydroxypropylene-1,3-diamine-N,N′-disuccinic acid, 1,2-Propylenediamine-N,N′-disuccinic acid, 1,3-Propylenediamine-N,N′-disuccinic acid, cis-Cyclohexanediamine-N,N′-disuccinic acid, trans-Cyclohexanediamine-N,N′-disuccinic acid, Ethylene-bis-(oxyethylenenitrilo)-N,N′-disuccinic acid, Glucoheptanoic acid, ferrous lactate, ferrous bisglycinate, ferrous citrate, ferrous acetate, ferrous fumarate, ferrous succinate, ferrous sacchrate, ferrous tartarate, ferrous glycine sulfate, ferrous glutamate, ferrous gluconate, ferrous ascorbate, ferrous polymaltose, alone or in combination.

16. The aqueous based end-user composition according to claim 11 , wherein the anti-oxidant agent and/or radical quenching agent is selected from the group consisting of phenols, hindered phenols, alkylated monophenols, alkylthiomethylphenols, hydroquinones and alkylated hydroquinones, tocopherols, hydroxylated thiodiphenyl ethers, alkylidenebisphenols, O-, N- and S-benzyl compounds, hydroxybenzylated malonates, aromatic hydroxybenzyl compounds, triazine compounds, benzylphosphonates, acylaminophenols, esters, hindered esters, tertiary butyl alcohol (TBA), benzofuranones, hydroxylamines, β-carotenes and/or aminic antioxidants.

17. A process for preparing the preservative composition of claim 6 comprising preparing a solution of: i. about 8 wt. % dehydroacetic acid (DHA); ii. about 92 wt. % of propylene carbonate (PC); iii. 0.01 wt. % to about 5.0 wt. % of at least one non-aqueous soluble anti-oxidant and/or radical quenching agent; and iv. about 0.5 to about 2.0 wt. % of polyvinyl pyrrolidone (PVP).

18. A process for preparing the composition of claim 11 comprising preparing a solution of: i. about 8 wt. % of dehydroacetic acid (DHA); ii. about 92 wt. % of propylene carbonate (PC); iii. about 0.01 wt. % to about 5.0 wt. % of at least one sequestering or chelating agent; iv. 0.01 wt. % to about 5.0 wt. % of at least one aqueous soluble anti-oxidant; and v. about 0.5 wt. % to about 2.0 wt. % of polyvinyl pyrrolidone (PVP).

19. The composition according to claim 11 , wherein said anti-oxidant and/or chelating agent is added externally to the aqueous based end-user composition having a pH of 4 to 8.

Assignments (4)
RELEASE OF SECURITY INTEREST Recorded Jan 10, 2020
From: THE BANK OF NOVA SCOTIA
To: HERCULES LLC; ISP INVESTMENTS LLC
Reel/Frame 051561/0676 →
SUPPLEMENTAL SECURITY AGREEMENT Recorded May 24, 2019
From: HERCULES LLC; ISP INVESTMENTS LLC
To: THE BANK OF NOVA SCOTIA
Reel/Frame 049286/0434 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 25, 2017
From: PREMACHANDRAN, RAMAN; MEHTA, KALPA; GUPTA, JYOTI; HAKIMI, NAJEEB H.; WINKOWSKI, KAREN
To: ISP INVESTMENTS INC.
Reel/Frame 043681/0625 →
CHANGE OF NAME Recorded Sep 25, 2017
From: ISP INVESTMENTS INC.
To: ISP INVESTMENTS LLC
Reel/Frame 043991/0100 →
Continuity (2)
Provisional Application 62138490 · Mar 26, 2015
Related Publication 20180055048A1 · Mar 1, 2018