IP Library Granted Patent US 7,067,499
Granted Patent B2
US 7,067,499 · App. 10/407,660 · Granted Jun 27, 2006

Cationic polymer composition and its use in conditioning applications

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 7,067,499
App. No.
10/407,660
Granted
Jun 27, 2006
Kind
B2
Abstract

A composition of a cationic polygalactomannan or a derivative of cationic polygalactomannans is provided that has a mean average molecular weight (Mw) having a lower limit of 5,000 and an upper limit of 200,000 and has a light transmittance in a 10% aqueous solution of greater than 80% at a light wavelength of 600 nm and a protein content of less than 1.0% by weight of polysaccharide, and aldehyde functionality content of at least of 0.01 meq/gram. This composition is prepared in continuous or batch processes using either oxidizing reagents or combination of hydrolytic reagents and oxidizing reagents. This composition is used in personal care and household care products.

Claims (56)

1. A composition comprising at least one cationic polygalactomannan or a derivative of cationic polygalactomannans where the derivative moiety on the cationic derivatized polygalactomannan is selected from the group consisting of alkyl, hydroxyalkyl, alkylhydroxyalkyl, and carboxymethyl wherein the alkyl has a carbon chain containing from 1 to 22 carbons and the hydroxyalkyl is selected from the group consisting of hydroxyethyl, hydroxypropyl, and hydroxybutyl, wherein the at least one cationic polygalactomannan or derivative of cationic polygalactomannans have a mean average molecular weight (Mw) having a lower limit of 5,000 and an upper limit of 200,000 and having a light transmittance in a 10% aqueous solution of greater than 80% at a light wavelength of 600 nm and a protein content of less than 1.0% by weight of polysaccharide, and aldehyde functionality content of at least 0.01 meq/gram.

2. The composition of claim 1 wherein the composition has a cationic degree of substitution (DS) lower limit of about 0.001 and an upper limit of about 2.0.

3. The composition of claim 1 , wherein the cationic degree of substitution (DS) has a lower limit amount of 0.01 cationic DS.

4. The composition of claim 2 , wherein the cationic degree of substitution (DS) has an upper limit of about 1.0.

5. The composition of claim 1 , wherein the polygalactomannan is selected from the group consisting of guar and locust bean.

6. The composition of claim 1 , wherein the cationic moiety is selected from quaternary ammonium compounds.

7. The composition of claim 6 , wherein the quaternary ammonium compound is selected from the group consisting of 3-chloro-2-hydroxypropyltrimethylammonium chloride, 2,3-epoxy-propyltrimethylammonium chloride, 3-chloro-2-hydroxypropyltrimethylammonium bromide, 2,3-epoxy-propyltrimethylammonium bromide; glycidyltrimethylammonium chloride, glycidyltriethylammonium chloride, gylcidyltripropylammonium chloride, glycidylethyldimethylammonium chloride, glycidyldiethylmethylammonium chloride, and their corresponding bromides and iodides; 3-chloro-2-hydroxypropyltrimethylammonium chloride, 3-chloro-2-hydroxypropyltriethylammonium chloride, 3-chloro-2-hydroxypropyltripropylammonium chloride, 3-chloro-2-hydroxypropylethyldimethylammonium chloride, and their corresponding bromides and iodides; and halides of imidazoline ring containing compounds.

8. The composition of claim 1 , wherein the light transmittance is greater than 90%.

9. The composition of claim 1 , wherein the light transmittance is greater than 95%.

10. The composition of the claim 1 , wherein the protein content in the composition is less than about 0.5% by weight of polysaccharide.

11. The composition of claim 1 , wherein the Mw has a lower limit of 20,000.

12. The composition of claim 1 , wherein the Mw has a lower limit of 35,000.

13. The composition of claim 1 , wherein the Mw has a lower limit of 50,000.

14. The composition of claim 1 , wherein the Mw has an upper limit of 100,000.

15. The composition of claim 1 , wherein the Mw has an upper limit of 70,000.

16. The composition of claim 1 , further comprising a member selected from the group consisting of colorant, preservative, antioxidant, alpha or beta hydroxy acid, emulsifier, functional polymer, viscosifying agent, alcohol, fat or fatty compound, antimicrobial compound, zinc pyrithione, silicone material, hydrocarbon polymer, emollients, oil, surfactants, suspending agents, and mixtures thereof.

17. The composition of claim 16 , wherein the functional polymer is selected from the group consisting of anionic, hydrophobically-modified, and amphoteric acrylic acid copolymers, vinylpyrrolidone homopolymers and copolymers, cationic vinylpyrrolidone copolymers, nonionic, cationic, anionic, and amphoteric cellulosic polymers, acrylamide homopolymers, cationic, anionic, amphoteric, and hydrophobically-modified acrylamide copolymer, polyethylene glycol polymer and copolymer, hydrophobically-modified polyether, hydrophobically-modified polyetheracetal, hydrophobically-modified polyetherurethane, an associative polymer, hydrophobically-modified cellulosic polymer, polyethyleneoxide-propylene oxide copolymer, and a nonionic, anionic, hydrophobically-modified, amphoteric, and cationic polysaccharides, chitosan, and mixtures thereof.

18. The composition of claim 17 , wherein the nonionic, cationic, anionic, and amphoteric cellulosic polymers are selected from the group consisting of hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, carboxymethylcellulose, hydrophobically-modified carboxymethylcellulose, cationic hydroxyethylcellulose, cationic hydrophobically-modified hydroxyethyl cellulose, hydrophobically modified hydroxyethylcellulose, hydrophobically-modified hydroxypropylcellulose, cationic hydrophobically-modified hydroxypropyl cellulose, cationic carboxymethylhydroxyethylcellulose, and cationic hydroxypropylcellulose.

19. The composition of claim 17 , wherein the nonionic, anionic, hydrophobically modified, amphoteric, and cationic polysaccharides are selected from the group consisting of carboxymethyl guar, alginates, hydroxypropyl guar, hydrophobically-modified guar, carboxymethyl guar hydroxypropyltrimethylammonium chloride, guar hydroxypropyltrimethylammonium chloride, and hydroxypropyl guar hydroxypropyltrimethylammonium chloride.

20. The composition of claim 16 , wherein the viscosifying agent is selected from the group consisting of NaCl, NH 4 Cl, KCl, and fatty alcohols, fatty acid esters, fatty acid amides, fatty alcohol polyethyleneglycol ethers, sorbitol polyethyleneglycol ethers, cocamidopropyl betaine, clays, silicas, cellulosic polymers, xanthan, and mixtures thereof.

21. The composition of claim 16 , wherein the silicone material is selected from the group consisting of cyclosiloxane, linear siloxane, and copolymers thereof containing polyol, amino, or functional groups selected from the groups consisting of polyethyleneoxy and/or polypropyleneoxy groups optionally containing C 6 –C 24 alkyl groups, substituted or unsubstituted amine groups, thiol groups, alkoxylated groups, hydroxyl groups and acyloxyalkl groups in the siloxane structure, and mixtures thereof.

22. The composition of claim 16 , wherein the silicone material is selected from the group consisting of polyalkylsiloxanes, polyarylsiloxanes, polyalkylarylsiloxanes, and mixtures thereof.

23. The composition of claim 22 , wherein the polyalkylsiloxane is selected from the group consisting of polydimethylsiloxane, polydimethylsiloxane hydroxylated at the end of the chain, and mixtures thereof.

24. The composition of claim 16 , wherein the surfactant is anionic, amphoteric, or nonionic.

25. A process comprising (a) reacting at least one cationic polygalactomannan or cationic derivatized polygalactomannan where the derivative moiety on the cationic derivatized polygalactomannan is selected from the group consisting of alkyl, hydroxyalkyl, alkylhydroxyalkyl, and carboxymethyl wherein the alkyl has a carbon chain containing from 1 to 22 carbons and the hydroxyalkyl is selected from the group consisting of hydroxethyl, hydroxpropyl, and hydroxybutyl, with at least one reagent that reduces the Mw to less than 200,000 that includes water soluble color bodies and water insoluble material, and (b) removing water insoluble material to produce the composition of claim 1 .

26. The process of claim 25 , wherein the cationic A polyglactomannan or cationic derivatized polygalactomannan is treated with the reagent in aqueous medium to produce an aqueous dispersion of the treated polygalactomannan, and the water insoluble material is removed from the dispersion to produce a clarified solution of the composition of claim 1 .

27. The process of claim 25 or 26 , wherein the reagent is an oxidizing reagent selected from the group consisting of peroxides, persulfates, permanganates, perchlorates, hypochlorite, oxygen, and biochemical oxidants.

28. The process of claim 27 wherein the peroxide is hydrogen peroxide.

29. The process of claim 27 , wherein the biochemical oxidizing reagent is an oxygenase.

30. The process of claim 29 , wherein the oxygenase is galactose oxidase.

31. The process of claim 26 , wherein the reagent further comprises a hydrolytic reagent.

32. The process of claim 31 , wherein said hydrolytic reagent is selected from the group considering of hydrolytic enzymes.

33. The process of claim 32 wherein said hydrolytic enzyme is selected from the group consisting of hemicellulases.

34. The process of claim 33 , wherein the hemicellulase is mannanase.

35. The process of claim 31 , wherein said hydrolytic reagent is an organic or mineral acid.

36. The process of claim 25 , further comprising removing the water soluble color bodies.

37. The process of claim 26 , further comprising removing the water soluble color bodies to produce a colorless, clarified aqueous solution.

38. The process of claim 37 , wherein the water soluble color bodies are removed by addition of sodium metabisulfite, sodium bisulfite, sodium hypochlorite or sodium chlorite.

39. The process of claim 37 , wherein the water soluble color bodies are removed by addition of activated carbon, followed by a separation step.

40. The process of claim 37 , wherein the water soluble color bodies are removed by addition of molecular sieves, followed by a separation step.

41. The process of claim 26 , further comprising recovering the derivatized polygalactomannan in dry form from the aqueous solution.

42. The process of claim 25 or 26 , wherein the cationic polygalactomannan or cationic derivatized polygalactomannan is in the form of powder, flour, or splits.

43. A household care composition comprising the composition of claim 1 .

44. The household care composition of claim 43 further comprising at least one other active household ingredient.

45. The household care composition of claim 44 , wherein the active household ingredient is selected from the group consisting of insect repellent agent, pet deodorizer agent, pet shampoo active, industrial grade bar and liquid soap active, dishwashing soap active, all purpose cleaner active, disinfecting agent, rug and upholstery cleaning active, laundry softener active, laundry detergent active, toilet bowl cleaning agent, fabric sizing agent, dust collection agent, antiredeposition agent, textile cleaning agent, and lubricating agent.

46. The household care composition of claim 44 , wherein the composition also includes at least one additional ingredient selected from the group consisting of colorant, preservative, antioxidant, bleaching agent, emulsifier, functional polymer, viscosifying agent, alcohol, fat or fatty compound, oil, surfactant, fragrance, suspending agent, silicone material, and mixtures thereof.

47. A personal care composition comprising the composition of claim 1 .

48. The personal care composition of claim 47 further comprising at least one other active personal care ingredient.

49. The personal care composition of claim 48 , wherein the active personal care ingredient is selected from the group consisting of perfumes, skin coolants, emollients, deodorants, antiperspirants actives, moisturizing agents, cleansing agents, sunscreen actives, hair treatment agents, oral care agents, denture adhesive agents, shaving actives, beauty aids, and nail care active.

50. The personal care composition of claim 47 or 48 , wherein the composition is a product selected from the group consisting of hair care, skin care, sun care, nail care, and oral care.

51. The composition of claim 50 , wherein the hair care product comprises a conditioning agent selected from the group consisting of silicone materials, hydrocarbon oils, panthenol and derivatives thereof selected from the group consisting of panthenyl ethyl ether, panthenyl hydroxypropl steardimonium chloride, and pantothenic acid and mixtures thereof.

52. The composition of claim 50 , wherein the skin care product comprises a conditioning agent selected from the group of consisting of silicone materials, hydrocarbon oils, panthenol and derivatives thereof selected from the group consisting of panthenyl ethyl ether, panthenyl hydroxypropyl steardimonium chloride, and pantothenic acid and mixtures thereof.

53. The composition of claim 50 , wherein the hair care product or skin care product comprises up to 5% by weight the composition of claim 1 and has a light transmittance value greater than 95%.

54. The personal care composition of claim 48 , wherein the composition also includes at least one additional ingredient selected from the group consisting of colorant, preservative, antioxidant, alpha or beta hydroxy acid, emulsifier, functional polymer, viscosifying agent, alcohol, fat or fatty compound, antimicrobial compound, zinc pyrithione, silicone material, hydrocarbon polymer, emollient, oil, surfactant, flavor, fragrance, medicaments, rejunvenating agents, suspending agents, and mixture thereof.

55. The composition of claim 1 , further comprising water in an amount of 50–95% by weight of the total composition.

56. The composition of claim 55 further comprising at least one additional ingredient selected from the group consisting of antimicrobial compound, fragrances, flavors, colorants, and mixtures thereof.

Assignments (10)
RELEASE OF SECURITY INTEREST Recorded Jan 10, 2020
From: THE BANK OF NOVA SCOTIA
To: AVOCA LLC; HERCULES LLC; ISP INVESTMENTS LLC; PHARMACHEM LABORATORIES LLC
Reel/Frame 051557/0504 →
SECURITY AGREEMENT Recorded Jul 3, 2017
From: AVOCA, INC.; HERCULES LLC; ISP INVESTMENTS LLC; PHARMACHEM LABORATORIES, INC.
To: THE BANK OF NOVA SCOTIA, AS ADMINISTRATIVE AGENT
Reel/Frame 043084/0753 →
CHANGE OF NAME Recorded May 18, 2017
From: HERCULES INCORPORATED
To: HERCULES LLC
Reel/Frame 042497/0331 →
RELEASE OF PATENT SECURITY AGREEMENT Recorded Mar 18, 2013
From: THE BANK OF NOVA SCOTIA
To: ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; AQUALON COMPANY; ISP INVESTMENTS INC.; HERCULES INCORPORATED
Reel/Frame 030025/0320 →
SECURITY AGREEMENT Recorded Sep 16, 2011
From: ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; HERCULES INCORPORATED; AQUALON COMPANY; ISP INVESTMENT INC.
To: THE BANK OF NOVA SCOTIA, AS ADMINISTRATIVE AGENT
Reel/Frame 026918/0052 →
RELEASE OF PATENT SECURITY AGREEMENT Recorded Sep 15, 2011
From: BANK OF AMERICA, N.A.
To: ASHLAND, INC.; ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; AQUALON COMPANY; HERCULES INCORPORATED
Reel/Frame 026927/0247 →
SECURITY AGREEMENT Recorded Apr 14, 2010
From: ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; AQUALON COMPANY; HERCULES INCORPORATED
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 024225/0289 →
RELEASE OF SECURITY INTEREST Recorded Apr 13, 2010
From: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
To: ASHLAND LICENSING AND INTELLECTUAL PROPERTY LLC; AQUALON COMPANY; HERCULES INCORPORATED
Reel/Frame 024218/0928 →
SECURITY AGREEMENT Recorded Dec 3, 2008
From: ASHLAND LICENSING AND INTELLECTUAL PROPERTY...; AQUALON COMPANY; HERCULES INCORPORATED
To: BANK OF AMERICA, N.A. AS ADMINISTRATIVE AGENT
Reel/Frame 021924/0001 →
PATENT TERMINATION CS-014683-0542 Recorded Dec 1, 2008
From: CREDIT SUISSE, CAYMAN ISLANDS BRANCH
To: HERCULES INCORPORATED
Reel/Frame 021901/0464 →