Substantive water-soluble cationic UV-absorbing compounds

• US 5,601,811 A
• Filed: 08/01/1994
• Issued: 02/11/1997
• Est. Priority Date: 08/01/1994
• Status: Expired due to Term

• Current Assignee: Croda, Inc. (Croda International Plc (Technology Investment Group))
• Original Assignee: Croda, Inc. (Croda International Plc (Technology Investment Group))
• Inventors: Gallagher, Kevin F., Pereira, Abel G.
• Primary Examiner(s): VENKAT, JYOTHSNA A
• Application Number:
  US08/283,575
• Time in Patent Office: 925 Days
• Field of Search: 424/401, 424/59, 424/701, 424/709, 514/618, 514/619, 514/620
• US Class Current: 424/709
• CPC Class Codes: A61K 8/42 Amides
• CPC Class Codes: A61Q 17/04 Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• CPC Class Codes: A61Q 5/02 Preparations for cleaning the hair
• CPC Class Codes: A61Q 5/12 Preparations containing hair conditioners
• CPC Class Codes: C07C 233/40 having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
• CPC Class Codes: C07C 235/34 having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
• CPC Class Codes: C07C 237/20 the carbon skeleton containing six-membered aromatic rings

Abstract

Substantive UV-absorbing cinnamido amine cationic quaternary salts are disclosed. Detergent and household cleaning product compositions and hair and skin personal care product compositions, as well as sunscreen and tanning lotion compositions, containing the compounds of the present invention are also described.

Claims

1. A composition comprising one or more active ingredients and a cinnamido alkyl amine cationic quaternary salt having the formula:

##STR7## wherein R₁ is hydrogen;

R₂ is selected from the group consisting of hydrogen, --R₆ --OH and alkyl groups containing up to 18 carbon atoms, and R₃ and R₄ are independently selected from the group consisting of --R₆ --OH and alkyl groups containing up to 18 carbon atoms, wherein R₆ is a polyalkylene oxide containing up to 20 moles of an alkylene oxide selected from the group consisting of ethylene oxide, propylene oxide and mixtures thereof;

R₅ is selected from the group consisting of alkyl groups containing up to 18 carbon atoms and benzyl groups;

n is an integer between 1 and 18, inclusive; and

x-- is an anion.

2. The composition of claim 1, wherein said one or more active ingredients are selected from the group consisting of aqueous and oily moisturizers, film-forming agents, emulsifiers, thickening agents, skin and hair conditioning agents, humectants, surfactants, emollients and rheological modifiers.

3. The composition of claim 2, wherein said one or more active ingredients comprise one or more detergents selected from the group consisting of anionic detergents, cationic detergents, nonionic detergents and amphoteric detergents.

4. The composition of claim 1, wherein said one or more active ingredients are present in an amount up to about 25% w/w of said composition.

5. The composition of claim 1, wherein said cinnamide alkyl amine catonic quaternary salt is present in an amount in the range of from about 0.5% to about 10% w/w of said composition.

6. The composition of claim 1, wherein R₂ of said cinnamido alkyl amine cationic quaternary salt is hydrogen.

7. The composition of claim 1, wherein R₃, R₄ and R₅ of said cinnamido alkyl amine cationic quaternary salt are all methyl groups.

8. The composition of claim 1, wherein n of said cinnamido alkyl amine cationic quaternary salt is 3.

11. The composition of claim 1, wherein said cinnamido alkyl amine cationic quaternary salt is water-soluble or water-dispersible, and said composition comprises a solution or dispersion in water.

9. A composition comprising one or more active ingredients and a his cinnamido amine cationic quaternary salt having the formula:

##STR8## wherein each R₁ is independently selected from the group consisting of hydrogen, halogen, alkoxy groups containing from one up to 22 carbon atoms, NO₂, NH₂, OH and N,N'"'"'-dialkylamino groups containing from two up to 22 carbon atoms;

each R₂ is independently selected from the group consisting of hydrogen, --R₆ --OH and alkyl groups containing up to 18 carbon atoms, and R₃ is selected from the group consisting of --R₆ --OH, alkyl groups containing up to 18 carbon atoms and cinnamido alkyl groups having the formula;

##STR9## wherein R₆ is a polyalkylene oxide containing up to 20 moles of an alkylene oxide selected from the group consisting of ethylene oxide, propylene oxide and mixtures thereof;

R₅ is selected from the group consisting of alkyl groups containing up to 18 carbon atoms and benzyl groups;

n is an integer between 1 and 18, inclusive; and

X^- is an anion.

10. The composition of claim 9, wherein all R₁ groups and all R₂ groups are hydrogen, both R₃ and R₅ are methyl groups, and n is 3.

16. The composition of claim 9, wherein said one or more active ingredients are selected from the group consisting of aqueous and oily moisturizers, film-forming agents, emulsifiers, thickening agents, skin and hair conditioning agents, humectants, surfactants, emollients and rheological modifiers.

17. The composition of claim 16, wherein said one or more active ingredients comprise one or more detergents selected from the group consisting of anionic detergents, cationic detergents, nonionic detergents and amphoteric detergents.

18. The composition of claim 9, wherein said one or more active ingredients are present in an amount up to about 25% w/w of said composition.

19. The composition of claim 9, wherein said one or more active ingredients are present in an amount in the range of from about 0.5% to about 10% w/w of said composition.

12. An aqueous solution or dispersion comprising water and up to about 90% w/w of a water-soluble cinnamido alkyl amine cationic quaternary salt having the formula:

##STR10## wherein R₁ is hydrogen;

R₂ is selected from the group consisting of hydrogen, --R₆ --OH and alkyl groups containing up to 18 carbon atoms, and R₃ and R₄ are independently selected from the group consisting of --R₆ --OH and alkyl groups containing up to 18 carbon atoms, wherein R₆ is a polyalkylene oxide containing up to 20 moles of an alkylene oxide selected from the group consisting of ethylene oxide, propylene oxide and mixtures thereof;

R₅ is selected from the group consisting of alkyl groups containing up to 18 carbon atoms and benzyl groups;

n is an integer between 1 and 18, inclusive; and

x-- is an anion.

13. The solution or dispersion of claim 12, further comprising an inert vehicle selected from the group consisting of lower alkanols having from 1 to 4 carbon atoms and glycols having from 3 to 8 carbon atoms, wherein said vehicle is present in a weight ratio to the water of said aqueous solution between about 1:

2 and about 4;

1.

14. The aqueous solution or dispersion of claim 13, comprising equal parts by weight of said water and said inert vehicle.

15. The aqueous solution or dispersion of claim 13, wherein said lower alkanols and glycols are selected from the group consisting of methanol, ethanol, isopropanol, butanol, hexylene glycol, 1,3-butylene glycol, 1,2- and 1,3-propane diol, 2-methyl 1,3-propane diol, propylene glycol and diethylene glycol.

20. A composition comprising one or more active ingredients and a cinnamido amine cationic quaternary salt, wherein said quaternary salt has the formula:

##STR11## wherein R₁ is selected from the group consisting of halogen, NO₂, NH₂, OH and N,N'"'"'-dialkylamino groups containing from two up to 22 carbon atoms;

R₂ is selected from the group consisting of hydrogen, --R₆ --OH and alkyl groups containing up to 18 carbon atoms, and R₃ and R₄ are independently selected from the group consisting of --R₆ --OH and alkyl groups containing up to 18 carbon atoms, wherein R₆ is a polyalkylene oxide containing up to 20 moles of an alkylene oxide selected from the group consisting of ethylene oxide, propylene oxide and mixtures thereof;

R₅ is selected from the group consisting of alkyl groups containing up to 18 carbon atoms and benzyl groups;

n is an integer between 1 and 18, inclusive; and

x-- is an anion.