IP Library › Granted Patent US 8,002,847
Granted Patent B2
US 8,002,847 · App. 12/671,448 · Granted Aug 23, 2011

Composition for oxidation dyeing keratin fibres comprising a cationic cellulose ether, a weakly oxyethylenated sorbitan fatty acid ester and oxidation dyes

Assignee: L 'Oreal S.A.
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Quick Facts
Patent No.
US 8,002,847
App. No.
12/671,448
Granted
Aug 23, 2011
Kind
B2
Abstract

The present invention relates to a dye composition comprising, in a medium suitable for dyeing: A) one or more particular cationic cellulose ether(s), B) one or more weakly oxyethylenated sorbitan fatty acid ester(s), and C) one or more oxidation dye(s). The present invention also relates to a process for dyeing keratin fibers using such a composition, and also to the use of this composition for dyeing keratin fibers.

Claims (138)

1. Dye composition for keratin fibers, comprising, in a medium suitable for dyeing:

A) one or more cationic cellulose ether(s) comprising from 4000 to 10 000 anhydroglucose units, said anhydroglucose units being substituted with at least:

(i) one substituent of formula [R 4 R 5 R 6 R 9 N + ](X 2 − ), in which:

R 4 and R 5 represent, independently of one another, a methyl or ethyl group,

R 6 represents a linear or branched C 8 -C 24 alkyl group or an aralkyl group in which the linear or branched alkyl part is C 8 -C 24 ,

R 9 represents a divalent group which allows the attachment to the anhydroglucose group and which is chosen from —(B) q —CH 2 —CHOH—CH 2 — and —CH 2 CH 2 —,

q denoting 0 or 1,

B denoting a divalent group —(CH 2 CH 2 O) n′ —,

n′ being an integer ranging from 1 to 100,

X 2 − represents an anion; and

(ii) one substituent of formula [R 1 R 2 R 3 R 8 N + ](X 1 − ), in which:

R 1 , R 2 and R 3 represent, independently of one another, a methyl or ethyl group,

R 8 represents a divalent group which allows the attachment to the anhydroglucose group and which is chosen from -(A) p -CH 2 —CHOH—CH 2 — and —CH 2 CH 2 —,

p denoting 0 or 1,

A denoting a divalent group —(CH 2 CH 2 O) n —,

n being an integer ranging from 1 to 100,

X 1 − represents an anion;

B) one or more weakly oxyethylenated sorbitan fatty acid ester(s); and

C) one or more oxidation dye(s).

2. Dye composition according to claim 1 , wherein the cationic cellulose ether is formed from at least one unit (IV) and at least one of the following units (I), (II) or (III):

with the proviso that:

the total number of units (I)+(II)+(III)+(IV) is between 4000 and 10 000;

the ratio of units [(III)+(IV)]/[(I)+(II)+(III)+(IV)] ranges from 0.0003 to 0.8;

the ratio of units [(II)+(IV)]/[(I)+(II)+(III)+(IV)] ranges from 0.02 to 0.9;

the integers n and n′, independently of one another, range from 0 to 5;

R 1 , R 2 , R 3 , R 4 and R 5 represent, independently of one another, a methyl or ethyl group;

R 6 represents a linear or branched C 8 - C 24 , alkyl group or an aralkyl group in which the linear or branched alkyl part is C 8 -C 24 ;

X 1 − and X 2 − represent anions chosen, independently of one another, from phosphate, nitrate, sulphate and halide ions.

3. Dye composition according to claim 2 , wherein R 6 represents a linear or branched alkyl group containing from 12 to 15 carbon atoms.

4. Dye composition according to claim 1 , wherein the concentration of cationic cellulose ether(s) ranges from 0.01% to 10% by weight.

5. Cosmetic composition according to claim 1 , wherein the oxyethylenated sorbitan fatty acid ester comprises fewer than 10 ethylene oxide units.

6. Cosmetic composition according to the claim 5 , wherein the oxyethylenated sorbitan fatty acid ester comprises from 2 to 9 ethylene oxide units.

7. Cosmetic composition according to claim 1 , wherein the fatty acid of the oxyethylenated sorbitan ester is a linear fatty acid.

8. Cosmetic composition according to claim 1 , wherein the fatty acid of the oxyethylenated sorbitan ester is a saturated fatty acid.

9. Cosmetic composition according to claim 1 , wherein the concentration of oxyethylenated sorbitan fatty acid ester(s) ranges from 1% to 20% by weight, relative to the total weight of the composition.

10. Dye composition according to claim 1 , wherein that the oxidation dye is chosen from benzene, heterocyclic and naphthalene oxidation dyes.

11. Dye composition according to claim 10 , wherein the oxidation dye is chosen from cationic or noncationic benzene bases, heterocyclic bases, benzene couplers, heterocyclic couplers and naphthalene couplers.

12. Dye composition according to claim 11 , wherein the oxidation dye is a benzene oxidation base chosen from para-phenylenediamines, bisphenylalkylenediamines, para-aminophenols, ortho-aminophenols, and addition salts thereof.

13. Dye composition according to claim 12 , wherein the benzene oxidation base is a para-phenylenediamine chosen from para-phenylenediamine, para-toluylenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,5-dimethyl-para-phenylenediamine, N,N-dimethyl-para-phenylenediamine, N,N-diethyl-para-phenylenediamine, N,N-dipropyl-para-phenylenediamine, 4-amino-N,N-diethyl-3-methylaniline, N,N-bis(β-hydroxyethyl)-para-phenylenediamine, 4-N,N-bis(β-hydroxyethyl)amino-2-methylaniline, 4-N,N-bis(β-hydroxyethyl)amino-2-chloroaniline, 2-β-hydroxyethyl-para-phenylenediamine, 2-fluoro-para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N-(β-hydroxypropyl)-para-phenylenediamine, 2-hydroxymethyl-para-phenylenediamine, N,N-dimethyl-3-methyl-para-phenylenediamine, N,N-(ethyl,β-hydroxyethyl)-para-phenylenediamine, N-(β,γ-dihydroxypropyl)-para-phenylenediamine, N-(4′-aminophenyl)-para-phenylenediamine, N-phenyl-para-phenylenediamine, 2-β-hydroxyethyloxy-para-phenylenediamine, 2-β-acetylaminoethyloxy-para-phenylenediamine, N-(β-methoxyethyl)-para-phenylenediamine, 4-aminophenylpyrrolidine, 2-thienyl-para-phenylenediamine, 2-β-hydroxyethylamino-5-aminotoluene, 3-hydroxy-1-(4′-aminophenyl)pyrrolidine, and addition salts thereof.

14. Dye composition according to claim 12 , wherein the benzene oxidation base is a bisphenylalkylenediannine chosen from N,N′-bis(β-hydroxyethyl)-N,N′-bis(4′-aminophenyl)-1,3diaminopropanol, N,N′-bis(β-hydroxyethyl)-N,N′-bis(4′-aminophenyl)ethylenediamine, N,N′-bis(4-aminophenyl)tetramethylenediamine, N,N′-bis(β-hydroxyethyl)-N,N′-bis(4-aminophenyl)tetramethylenediamine, N,N′-bis-(4-methylanninophenyl)tetramethylenediarnine, N,N′-bis(ethyl)-N,N′-bis(4′-amino,3′-methylphenyl)ethylenediamine, 1,8-bis(2,5-diaminophenoxy)-3,6-dioxaoctane, and addition salts thereof.

15. Dye composition according to claim 12 , wherein the benzene oxidation base is a para-aminophenol chosen from para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-(β-hydroxyethylaminomethyl)phenol, 4-amino-2-fluorophenol, and addition salts thereof.

16. Dye composition according to claim 12 , wherein the benzene oxidation base is an ortho-aminophenol chosen from 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol, 5-acetamido-2-aminophenol, and addition salts thereof.

17. Dye composition according to claim 11 , wherein the oxidation dye is a benzene oxidation base chosen from cationic para-phenylenediamines, cationic para-aminophenols, cationic ortho-phenylenediamines, cationic ortho-aminophenols or double cationic bases of the family of bis(aminophenyl)alkylenediamines, bearing at least one quaternary nitrogen atom.

18. Dye composition according to claim 17 , wherein the cationic benzene oxidation base is a para-phenylenediamine, at least one of the amine functions of which is a tertiary amine, bearing at least one pyrrolidine nucleus, the para-phenylenediamine molecule having at least one quaternized nitrogen atom.

19. Dye composition according to claim 18 , wherein the cationic para-phenylenediamine is chosen from the following compounds:

[1-(4-aminophenyl)pyrrolidin-3-yl]trimethylammonium; chloride,

[1-(4-aminophenyl)pyrrolidin-3-yl]dimethyltetradecylammonium; bromide,

3-[1-(4-aminophenyl)pyrrolidin-3-yl]-1-methyl-3H-imidazol-1-ium; chloride,

[1-(4-aminophenyl)pyrrolidin-3-yl]-(2-hydroxyethyl)dimethylammonium; chloride,

[1-(4-aminophenyl)pyrrolidin-3-yl]dimethyl-(3-trimethylsilanylpropyl)ammonium; chloride,

[1-(4-aminophenyl)pyrrolidin-3-yl]-(3-trimethylammoniumhexyl)dimethylammonium; dichloride,

{2-[1(4-aminophenyl)pyrrolidin-3-yloxy]ethyl}trimethylammonium; chloride,

1-{2-[1-(4-aminophenyl)pyrrolidin-3-yloxy]ethyl}-1-methylpyrrolidinium; chloride,

3-{3-[1-(4-aminophenyl)pyrrolidin-3-yloxy]propyl}-1-methyl-3H-imidazol-1-ium; chloride,

1-{2-[1-(4-aminophenyl)pyrrolidin-3-yloxy]ethyl}-1-methylpiperidinium; chloride,

3-{3-[1-(5-trimethylsilanylethyl-4-amino-3-trimethylsilany1ethylphenyl)pyrrolidin-3-yloxy]propyl}-1 -methyl-3H-imidazol-1-ium; chloride,

[1-(4-amino-3-methylphenyl)pyrrolidin-3-yl]trimethylammonium; chloride,

[1-(4-amino-3-methylphenyl)pyrrolidin-3-yl]dimethyltetradecylammonium; chloride,

3-[1-(4-amino-3-methylphenyl)pyrrolidin-3-yl]-1-methyl-3H-imidazol-1-ium; chloride,

[1-(4-amino-3-methylphenyl)pyrrolidin-3-yl]-(2-hydroxyethyl)dimethylammonium; chloride,

[1-(4-amino-3-methylphenyl)pyrrolidin-3-yl]dimethyl-(3-trimethylsilanylpropylammonium; chloride,

[1-(4-amino-3-methylphenyl)pyrrolidin-3-yl]-(3-trimethylammoniumhexyl)dimethylammonium; dichloride,

{2-[1-(4-amino-3-methylphenyl)pyrrolidin-3-yloxy] ethyl}-trimethylammonium; chloride,

1-{2-[1-(4-amino-3-methylphenyl)pyrrolidin-3-yloxy]ethyl}-1-methylpyrrolidinium; chloride,

3-{3-[1-(4-amino-3-methylphenyl)pyrrolidin-3-yloxy]propyl}-1-methyl-3H-imidazol-1-um; chloride,

1-{2-[1-(4-amino-3-methylphenyl)pyrrolidin-3-yloxy]ethyl}-1-methylpiperidinium; chloride,

[1-(4-amino-3-trimethylsilanylethylphenyl)pyrrolidin-3-yl]-trimethylammonium; chloride,

3[1-(4-amino-3-trimethylsilanylethylphenyl)pyrrolidin-3-yl]-1-methyl-3H-imidazol-1-ium; chloride,

3-{3[1-(4-amino-3-trimethylsilanylethylphenyl)pyrrolidin-3-yl-oxy]propyl}-1-methyl-3H-imidazol-1-ium; chloride,

[1-(5-trimethylsilanylethyl-4-amino-3-trimethylsilanylethylphenyl)pyrrolidin-3-yl]trimethylammonium; chloride,

3-[1-(5-trimethylsilanylethyl-4-amino-3-trimethylsilanylethylphenyl)pyrrolidin-3-yl]-1-methyl-3H-imidazol- 1 -ium; chloride,

1′-(4-aminophenyl)-1-methyl[1,3′]-bipyrrolidinyl-1-ium; chloride,

1′-(4-amino-3-methylphenyl)-1-methyl[1,3′]-bipyrrolidinyl-1-ium; chloride,

3-{[1-(4-aminophenyl)pyrrolidin-3-ylcarbamoyl]methyl}-1-methyl-3H-imidazol-1-ium; chloride,

3-{[1-(4-amino-3-methylphenyl)pyrrolidin-3-ylcarbamoyl]methyl}-1-methyl-3H-imidazol-1-ium; chloride,

3[1-(4-aminophenyl)pyrrolidin-3-yl]-1 -(3-trimethylsilanylpropyl)-3H-imidazol-1-ium; chloride,

3[1 -(4-aminophenyl)pyrrolidin-3-yl]-1 -(3-trimethylsilanylpropyl)-3H-imidazol-1-ium; chloride,

[1-(4-aminophenyl)pyrrolidin-3-yl]ethyldimethylammonium; chloride,

[1-(4-aminophenyl)pyrrolidin-3-yl]ethyldimethylammonium; iodide,

[1-(4-aminophenyl)pyrrolidin-3-yl]propyldimethylammonium; iodide,

[1-(4-aminophenyl)pyrrolidin-3-yl]propyldimethylammonium; bromide,

[1-(4-aminophenyl)pyrrolidin-3-yl]propyldimethylammonium; methosulphate,

[1-(4-aminophenyl)pyrrolidin-3-yl]butyldimethylammonium; iodide,

[1-(4-aminophenyl)pyrrolidin-3-yl]pentyldimethylammonium; iodide

[1-(4-aminophenyl)pyrrolidin-3-yl]hexyldimethylammonium; iodide,

[1-(4-aminophenyl)pyrrolidin-3-yl]heptyldimethylammonium; iodide,

[1-(4-aminophenyl)pyrrolidin-3-yl]octyldimethylammonium; iodide,

[1-(4-aminophenyl)pyrrolidin-3-yl]decyldimethylammonium; iodide,

[1-(4-aminophenyl)pyrrolidin-3-yl]hexadecyldimethylammonium; iodide,

[1-(4-aminophenyl)pyrrolidin-3-yl]hydroxyethyldimethylammonium; chloride, and

[1-(4-aminophenyl)pyrrolidin-3-yl]hydroxyethyldimethylammonium; iodide.

20. Dye composition according to claim 11 , wherein the oxidation dye is a heterocyclic oxidation base chosen from pyridines, pyrimidines, pyrazoles, condensed pyrazolopyrimidines, pyrazolotriazoles, pyrazolotetrazoles, pyrazolopyridazines, pyrazolothiazoles, pyrazoloimidazoles, pyrazolobenzimidazoles, pyrazoloquinolines, aminopyrolidines, aminopyrazolines, mono- or diaminotetraquinolines, diamino- or triaminoquinolines, aminoindazoles, diaminouracils, aminoindolenines, hydrazones, julolidine or lilolidine, and also derivatives thereof and addition salts thereof.

21. Dye composition according to claim 20 , wherein the heterocyclic base is chosen from pyridines, pyrimidines, pyrazoles and pyrazolopyrimidines.

22. Dye composition according to claim 21 , wherein the heterocyclic base is chosen from 4,5-diaminopyrazoles.

23. Dye composition according to claim 11 , wherein the oxidation dye is a benzene coupler chosen from meta-aminophenols, meta-phenylenediamines, meta-diphenols, and addition salts thereof.

24. Dye composition according to claim 23 , wherein the benzene coupler is a meta-aminophenol chosen from the compounds of formula (V) below:

in which:

R 7 represents a hydrogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 monohydroxyalkyl group or a C 2 -C 4 polyhydroxyalkyl group;

R 8 represents a hydrogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 alkoxyl group or a halogen atom chosen from chlorine, bromine or fluorine;

R 9 represents a hydrogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 alkoxyl group, a C 1 -C 4 monohydroxyalkyl group, a C 2 -C 4 polyhydroxyalkyl group, a C 1 -C 4 monohydroxyalkoxyl group or a C 2 -C 4 polyhydroxyalkoxyl group; and from addition salts thereof.

25. Dye composition according to claim 24 , wherein the compound of formula (V) is chosen from meta-aminophenol, 5-amino-2-methoxyphenol, 5-amino-2-(betahydroxyethyloxy)phenol, 5-amino-2-methylphenol, 5-N-(β-hydroxyethyl)amino-2-methylphenol, 5-N-(beta-hydroxyethyl)amino-4-methoxy-2-methylphenol, 5-amino-4-methoxy-2-methylphenol, 5amino-4-chloro-2-methylphenol, 5-amino-2,4-dimethoxyphenol, 5-(gamma-hydroxypropylamino)-2-methylphenol, and addition salts thereof.

26. Dye composition according to claim 23 , wherein the benzene coupler is a meta-phenylenediamine chosen from the compounds of formula (VI) below:

in which:

R 10 represents a hydrogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 monohydroxyalkyl group or a C 2 -C 4 polyhydroxyalkyl group;

R 11 and R 12 , which may be identical or different, represent a hydrogen atom, a C 1 -C 4 alkyl group, a C 1 -C 4 monohydroxyalkoxyl group or a C 2 -C 4 polyhydroxyalkoxyl group;

R 13 represents a hydrogen atom, a C 1 -C 4 alkoxyl group, a C 1 -C 4 aminoalkoxyl group, a C 1 -C 4 monohydroxyalkoxyl group, a C 2 -C 4 polyhydroxyalkoxyl group or a 2,4-diaminophenoxyalkoxyl group; and from addition salts thereof.

27. Dye composition according to claim 26 , wherein the compound of formula (VI) is chosen from 2,4diaminobenzene, 3,5-diamino-1-ethyl-2-methoxybenzene, 3,5-diamino-2-methoxy-1-methylbenzene, 2,4-diamino-1-ethoxybenzene, 1,3-bis(2,4-diaminophenoxy)propane, bis(2,4-diaminophenoxy)methane, 1-(beta-aminoethyloxy)-2,4-diaminobenzene, 2-amino-1-(beta-hydroxyethyloxy)-4-methylaminobenzene, 2,4-diamino-1-ethoxy-5-methylbenzene, 2,4-diamino-5-(beta-hydroxyethyloxy)-1-methylbenzene, 2,4-diamino-1-(beta,gamma-dihydroxypropyloxy)benzene, 2,4-diamino-1-(beta-hydroxyethyloxy)benzene, 2-amino-4-N-(beta-hydroxyethyl)amino-1-methooxybenzene, and addition salts thereof.

28. Dye composition according to claim 23 , wherein the benzene coupler is a meta-diphenol chosen from the compounds of formula (VII) below:

in which:

R 14 and R 15 , which may be identical or different, represent a hydrogen atom, a C 1 -C 4 alkyl group or a halogen atom chosen from chlorine, bromine or fluorine; and from addition salts thereof.

29. Dye composition according to claim 28 , wherein the compound of formula (VII) is chosen from 1,3-dihydroxybenzene, 2-methyl-1,3-dihydroxybenzene, 4-chloro-1,3dihydroxybenzene, 2-chloro-1,3-dihydroxybenzene, and addition salts thereof.

30. Dye composition according to claim 11 , wherein the oxidation dye is a heterocyclic coupler chosen from azole-containing heterocyclic couplers, pyridine couplers, thiophenes, indolines, indoles, benzofurans, 8-amino-6-methoxyquinolines, 4-hydroxyquinolones, benzodioxoles, hydroxybenzamides, sesamol and its derivatives, benzomorpholines, and also addition salts thereof.

31. Dye composition according to claim 30 , wherein the heterocyclic coupler is an indole chosen from 6-hydroxyindole, 5,6-hydroxyindole, 4-hydroxyindole, derivatives thereof, and addition salts thereof.

32. Dye composition according to claim 30 , wherein the heterocyclic coupler is a benzomorpholine chosen from 6-hydroxybenzomorpholine, 6-aminobenzomorpholine, and addition salts thereof.

33. Dye composition according to claim 11 , wherein the oxidation dye is a naphthalene coupler chosen from alpha-naphthol, substituted naphthalenes of formula (VIII) below, and addition salts thereof:

in which:

R 5 represents a hydrogen atom or a —CO—R group In which R represents a C 1 -C 4 alkyl group;

R 6 represents a hydrogen atom, a hydroxyl group, a C 1 -C 4 alkyl group or an —SO 3 H group;

R 7 represents a hydrogen atom or a hydroxyl group;

it being understood that at least one of groups R 5 to R 7 is other than a hydrogen atom.

34. Dye composition according to claim 33 , wherein the naphthalene coupler is chosen from:

-alpha-naphtho1,

-1,7-dihydroxynaphthalene,

-2,7-dihydroxynaphthalene,

-2,5-dihydroxynaphthalene,

-2,3-dihydroxynaphthalene,

-1-acetoxy-2-methylnaphthalene,

-1-hydroxy-2-methylnaphthalene,

-1-hydroxy-4-naphthalenesulphonic acid, and addition salts thereof.

35. Dye composition according to claim 1 , wherein the concentration of oxidation dye(s) ranges from 0.005% to 15% by weight, relative to the total weight of the composition.

36. Dye composition according to claim 1 , further comprising one or more direct dye(s) chosen from nitrobenzene dyes, azo direct dyes, methine direct dyes, and addition salts thereof.

37. Dye composition according to claims 1 , further comprising one or more adjuvant(s) chosen from additional anionic, cationic, nonionic, amphoteric or zwitterionic surfactants -other than the sorbitan fatty acid esters defined in one of claims 5 to 8 , or mixtures thereof; additional nonionic, amphoteric, zwitterionic, anionic or cationic polymers -other than the cationic cellulose ethers defined in one of claims 1 to 3 , or mixtures thereof; antioxidants; penetrating agents; sequestrant agents; fragrances; buffers; dispersants; conditioning agents; film-forming agents; ceramides; preservatives; opacifiers; vitamins; amino acids; oligopeptides; peptides; modified or unmodified, hydrolysed or nonhydrolysed proteins; enzymes; branched or unbranched fatty acids and fatty alcohols; animal, plant or mineral waxes; hydroxylated organic acids; UV screens; antioxidants and free-radical scavengers; anti-dandruff agents; agents for regulating seborrhoea; calmatives; mineral, plant or animal oils; polyisobutenes and poly(alpha-olefins); pigments; acids, bases, plasticizers, mineral fillers, pearlescent agents, flakes; antistatic agents and reducing agents.

38. Cosmetic composition according to claim 1 , further comprising at least one thickener.

39. Dye composition according to claim 1 , wherein the pH of the composition ranges from 3 to 12.

40. Dye composition according to one of claim 1 , further comprising at least one oxidizing agent chosen from hydrogen peroxide, urea peroxide, alkali metal bromates, persalts, peracids and oxidase enzymes.

41. Process for oxidation dyeing keratin fibers, wherein a dye composition as defined in claim 1 is applied to the fibers in the presence of at least one oxidizing agent for a period of time sufficient to develop the desired colour.

42. Multicompartment device, comprising at least a first compartment containing a dye composition as defined in claim 1 and at least a second compartment containing at least one oxidizing agent.

43. Use of the composition defined in claim 1 for dyeing keratin fibers.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2010
From: AUDOUSSET, MARIE-PASCALE; SCHOLSSER, ISABELLE
To: L'OREAL S.A.
Reel/Frame 024696/0366 →
Priority Claims (1)
FR 07 56858 · Jul 31, 2007 · national
Continuity (2)
Provisional Application 60935742 · Aug 29, 2007
Related Publication 20100275388A1 · Nov 4, 2010