Alkyl ketal esters as dispersants and slip agents for particulate solids, methods of manufacture, and uses thereof

• US 8,962,597 B2
• Filed: 03/31/2014
• Issued: 02/24/2015
• Est. Priority Date: 05/10/2010
• Status: Expired due to Fees

• Current Assignee: GFBiochemicals Limited
• Original Assignee: Segetis Inc (GFBiochemicals Italy SpA)
• Inventors: Rieth, Lee Richard, Yontz, Dorie J., Morante, Nicholas
• Primary Examiner(s): BASQUILL, SEAN M
• Application Number:
  US14/230,396
• Publication Number:
  US 20140294744A1
• Time in Patent Office: 330 Days
• Field of Search: 514/63, 540/145, 424/9.1, 424/400
• US Class Current: 514/63
• CPC Class Codes: A01N 25/00 Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application , e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
• CPC Class Codes: A61K 2800/49 Solubiliser, Solubilising system
• CPC Class Codes: A61K 47/22 Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
• CPC Class Codes: A61K 8/25 Silicon; Compounds thereof
• CPC Class Codes: A61K 8/29 Titanium; Compounds thereof
• CPC Class Codes: A61K 8/31 Hydrocarbons
• CPC Class Codes: A61K 8/34 Alcohols
• CPC Class Codes: A61K 8/35 Ketones, e.g. benzophenone
• CPC Class Codes: A61K 8/368 with carboxyl groups directly bound to carbon atoms of aromatic rings
• CPC Class Codes: A61K 8/4953 containing pyrimidine ring derivatives, e.g. minoxidil
• CPC Class Codes: A61K 8/4973 with oxygen as the only hetero atom
• CPC Class Codes: A61K 8/498 having 6-membered rings or their condensed derivatives, e.g. coumarin
• CPC Class Codes: A61K 8/922 of vegetable origin
• CPC Class Codes: A61K 8/925 of animal origin
• CPC Class Codes: A61K 8/927 of insects, e.g. shellac
• CPC Class Codes: A61K 8/9789 Magnoliopsida [dicotyledons]
• CPC Class Codes: A61P 17/10 Anti-acne agents
• CPC Class Codes: A61P 31/00 Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
• CPC Class Codes: A61P 31/10 Antimycotics
• CPC Class Codes: A61Q 1/02 Preparations containing skin colorants, e.g. pigments preparations in powder form A61Q1/12
• CPC Class Codes: A61Q 1/04 : for lips
• CPC Class Codes: A61Q 1/06 : Lipsticks
• CPC Class Codes: A61Q 1/10 : for eyes, e.g. eyeliner, mascara
• CPC Class Codes: A61Q 1/12 : Face or body powders for grooming, adorning or absorbing
• CPC Class Codes: A61Q 15/00 : Anti-perspirants or body deodorants deodorisation of air A61L9/00
• CPC Class Codes: A61Q 17/04 : Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• CPC Class Codes: A61Q 3/00 : Manicure or pedicure preparations
• CPC Class Codes: A61Q 5/10 : Preparations for permanently dyeing the hair
• CPC Class Codes: A61Q 9/04 : Depilatories
• CPC Class Codes: C08K 5/156 : having two oxygen atoms in the ring
• CPC Class Codes: C09D 7/45 : Anti-settling agents

Abstract

Disclosed herein is a dispersion comprising a liquid or semi-solid continuous phase, a dispersed solid phase comprising a plurality of organic, inorganic or inorganic-organic particles, and an alkyl ketal ester having the structure

wherein a is 0 or an integer of 1 to 12, specifically 1 to 6, more specifically 1 to 4; b is 0 or 1; R² is a divalent C_1-8 group optionally substituted with up to 5 hydroxyl groups; and R¹ is C_1-6 alkyl, and wherein at least a portion of the alkyl ketal ester is present in the continuous phase, on a surface of at least some of the dispersed particles, or a combination thereof.

Claims

1. A dispersion comprising

a liquid or semi-solid continuous phase,

a dispersed solid phase comprising a plurality of organic, inorganic or inorganic-organic particles, and

an alkyl ketal ester having the structure

2. The dispersion of claim 1, wherein R¹ is methyl.

3. The dispersion of claim 1, wherein R¹ is ethyl.

4. The dispersion of claim 1, wherein R¹ is n-propyl.

5. The dispersion of claim 1, wherein R¹ is n-butyl.

6. A coating composition comprising the dispersion of claim 1, wherein

the continuous phase is a liquid continuous phase, and

the plurality of solid particles comprises solid pigment particles.

7. The coating composition of claim 6 wherein the alkyl ketal ester is present in the dispersion in an amount from 1 to 400% by weight of plurality of solid particles.

8. The coating composition of claim 6 wherein the dispersed pigment particles have an average D50 particle size from 100 nanometers to 25 micrometers.

9. The coating composition of claim 6, comprising, based on the total weight of the coating composition,

from 20 to 90% by weight of the liquid continuous phase,

from 0.5 to 45% by weight of the solid pigment particles,

from 0.5 to 60% by weight of the alkyl ketal ester, and

from 5 to 80% by weight of an organic binder composition.

10. The dispersion of claim 1, wherein the continuous phase is a semi-solid.

11. The dispersion of claim 10, wherein the semi-solid is a wax.

12. A cosmetic comprising the dispersion of claim 1, wherein

the continuous phase comprises a cosmetically acceptable wax, film-forming polymer, emollient, or a combination thereof, and

the plurality of solid particles comprises cosmetically acceptable solid pigment particles.

13. The cosmetic of claim 12 in the form of a semi-solid, comprising, based on the total weight of the cosmetic,

from 25 to 80% by weight of the continuous phase,

from 5 to 50% by weight of the solid pigment particles, and

from 0.1 to 50% of the weight of the alkyl ketal ester.

14. The cosmetic of claim, 13, wherein the cosmetic is an eye product, skin product, lip product, or nail product.

15. The cosmetic of claim 12, in the form of a fluid or gel, comprising, based on the total weight of the cosmetic,

from 25 to 80% by weight of water, a volatile organic solvent, or a combination thereof,

from 2 to 35% of the cosmetically acceptable wax, film-forming polymer, emollient, or combination thereof,

from 2 to 30% by weight of the solid pigment particles, and

from 1 to 40% by weight of the alkyl ketal ester.

16. The cosmetic of claim 15, wherein the cosmetic is an eye product, lip product, skin product or nail product.

17. The cosmetic of claim 12, in the form of a wet foundation comprising, based on the total weight of the cosmetic,

from 30-75% by weight water,

from 1 to 35% by weight of the cosmetically acceptable emollient, from 2 to 25% by weight of the solid pigment particles, and

from 0.5 to 35% by weight of the alkyl ketal ester,

wherein the continuous phase is an aqueous phase or an oily phase.

18. The cosmetic of claim 12, in the form of a lip product comprising, based on the total weight of the cosmetic,

from 1 to 25% by weight of the cosmetically acceptable wax;

from 30 to 95% by weight of one or more other hydrophobic materials; and

from 0.05 to 25% by weight of the solid pigment particles.

23. A method of forming the dispersion of claim 1, comprising combining the continuous phase, plurality of solid particles, and alkyl ketal ester to form the dispersion.

24. The method of claim 23, wherein the combining comprises wetting the plurality of solid particles with the alkyl ketal ester;

then combining the wetted particles with the continuous phase.

25. The method of claim 23, wherein the combining comprises combining the continuous phase and the alkyl ketal ester;

and adding the plurality of solid particles to the combination of the continuous phase and the alkyl ketal ester.

19. A particulate solid, comprising

a plurality of solid particles;

and

an alkyl ketal ester at least partially coating at least some of the particles, the alkyl ketal ester having the structure;

20. The particulate solid of claim 19 wherein the alkyl ketal ester is present in an amount from 1 to 100% by weight of plurality of the plurality of solid particles.

21. The particulate solid of claim 19, wherein the plurality of solid particles comprise pigment particles, and the alkyl ketal ester is sorbed onto at least a portion of a surface of at least a portion of the pigment particles.

22. A powder cosmetic comprising the particulate solid of claim 19 and comprising, based on the total weight of the powder cosmetic,

from 50 to 95% by weight of the solid pigment particles, and

from 1 to 15% by weight of the alkyl ketal ester.