IP Library Granted Patent US 9,701,929
Granted Patent B2
US 9,701,929 · App. 14/604,779 · Granted Jul 11, 2017

Consumer product compositions comprising organopolysiloxane emulsions

Inventors: Yonas Gizaw (West Chester, OH); Steven Daryl Smith (Fairfield, OH); Robert Joseph McChain (Cincinnati, OH); Rajan Keshav Panandiker (West Chester, OH); Carola Barrera (West Chester, OH); Peter Herbert Koenig (Montgomery, OH); Sumanth Narahari Jamadagni (West Chester, OH)
Assignee: The Procter & Gamble Company
C11D3/3742A61K8/898A61Q5/02A61Q5/12A61Q17/005A61Q19/00A61Q19/10A61K2800/5426C08G77/26C08L83/08
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Quick Facts
Patent No.
US 9,701,929
App. No.
14/604,779
Granted
Jul 11, 2017
Kind
B2
Abstract

Consumer product compositions providing enhanced hydrophobic benefit agent deposition. The benefit agent is provided as a benefit agent/deposition aid emulsion, where the benefit agent is physically adsorbed to the deposition aid before the emulsion is added to the balance of ingredients.

Claims (95)

1. A benefit agent emulsion comprising a benefit agent and a cationic deposition aid, wherein said cationic deposition aid is an organopolysiloxane having the formula:

M w D x T y Q z

wherein:

M =[SiR 1 R 2 R 3 O 1/2 ], [SiR 1 R 2 G 1 O 1/2 ], [SiR 1 G 1 G 2 O 1/2 ], [SiG 1 G 2 G 3 O 1/2 ], or combinations thereof;

D =[SiR 1 R 2 O 2/2 ], [SiR 1 G 1 O 2/2 ], [SiG 1 G 2 O 2/2 ] or combinations thereof;

T =[SiR 1 O 3/2 ], [SiG 1 O 3/2 ] or combinations thereof;

Q =[SiO4/2];

w =is an integer from 1 to (2+y+2z);

x =is an integer from 5 to 15,000;

y =is an integer from 0 to 98;

z =is an integer from 0 to 98;

R 1 , R 2 and R 3 are each independently selected from the group consisting of H, OH, C 1 -C 32 alkyl, C 1 -C 32 substituted alkyl, C 5 -C 32 or C 6 -C 32 aryl, C 5 -C 32 or C 6 -C 32 substituted aryl, C 6 -C 32 alkylaryl, C 6 -C 32 substituted alkylaryl, C 1 -C 32 alkoxy, C 1 -C 32 substituted alkoxy, C 1 -C 32 alkylamino, and C 1 -C 32 substituted alkylamino;

at least one of M, D, or T incorporates at least one moiety G 1 , G 2 or G 3 ; and G 1 , G 2 , and G 3 are each independently selected from the formula:

wherein:

X comprises a divalent radical selected from the group consisting of C 1 -C 32 alkylene, C 1 -C 32 substituted alkylene, C 5 -C 32 or C 6 -C 32 arylene, C 5 -C 32 or C 6 -C 32 substituted arylene, C 6 -C 32 arylalkylene, C 6 -C 32 substituted arylalkylene, C 1 -C 32 alkyleneamino, and C 1 -C 32 substituted alkyleneamino;

each R 4 comprises identical or different monovalent radicals independently selected from the group consisting of H, C 1 -C 32 alkyl, C 1 -C 32 substituted alkyl, C 5 -C 32 or C 6 -C 32 aryl, C 5 -C 32 or C 6 -C 32 substituted aryl, C 6 -C 32 alkylaryl, and C 6 -C 32 substituted alkylaryl;

E comprises a divalent radical selected from the group consisting of C 1 -C 32 alkylene, C 1 -C 32 substituted alkylene, C 5 -C 32 or C 6 -C 32 arylene, C 5 -C 32 or C 6 -C 32 substituted arylene, C 6 -C 32 arylalkylene, C 6 -C 32 substituted arylalkylene, C 1 -C 32 alkyleneamino, and C 1 -C 32 substituted alkyleneamino;

E′ comprises a divalent radical selected from the group consisting of C 1 -C 32 alkylene, C 1 -C 32 substituted alkylene, C 5 -C 32 or C 6 -C 32 arylene, C 5 -C 32 or C 6 -C 32 substituted arylene, C 6 -C 32 arylalkylene, C 6 -C 32 substituted arylalkylene, C 1 -C 32 alkoxy, C 1 -C 32 substituted alkoxy, C 1 -C 32 alkyleneamino, and C 1 -C 32 substituted alkyleneamino;

p is an integer independently selected from 1 to 50;

n is an integer independently selected from 1 or 2;

wherein at least one of G 1 , G 2 , or G 3 is positively charged, A −t is a suitable charge balancing anion or anions such that the total charge, k, of the charge-balancing anion or anions is equal to and opposite from the net charge on the moiety G 1 , G 2 or G 3 , where t is an integer independently selected from 1, 2, or 3; and k <(p*2/t) +1; such that the total number of cationic charges balances the total number of anionic charges in the organopolysiloxane molecule;

wherein at least one E does not comprise an ethylene moiety; and

wherein at least one E or E′ are independently selected from the group consisting of:

wherein:

each R 6 comprises a divalent radical independently selected from the group consisting of C 1 -C 32 alkylene C 1 -C 32 substituted alkylene C 5 -C 32 or C 6 -C 32 arylene, C 5 -C 32 or C 6 -C 32 substituted arylene, C 6 -C 32 arylalkylene, C 6 -C 32 substituted arylalkylene, C 1 -C 32 alkoxy, C 1 -C 32 substituted alkoxy, C 1 -C 32 alkyleneamino, C 1 -C 32 substituted alkyleneamino, ring-opened epoxide, and ring-opened glycidyl, with the proviso that if R 6 does not comprise a repeating alkylene oxide moiety then R 6 can further comprise a heteroatom selected from the group consisting of P, N, and O;

each R 9 comprises an identical or different monovalent radical independently selected from the group consisting of H, C 1 -C 32 alkyl, C 1 -C 32 substituted alkyl, C 5 -C 32 or C 6 -C 32 aryl, C 5 -C 32 or C 6 -C 32 substituted aryl, C 6 -C 32 alkylaryl, and C 6 -C 32 substituted alkylaryl; and

u is an integer independently selected from 3 to 32:

wherein said cationic organopolysiloxane deposition aid is adsorbed onto the benefit agent; 1 and wherein said benefit agent is hydrophobic.

2. The emulsion of claim 1 , wherein the siloxyl residue of said organopolysiloxane has a molecular weight of from 1,000 to 30,000 Daltons.

3. The emulsion of claim 1 , further wherein said organopolysiloxane has a charge density of from 0.1 meq/g to 8 meq/g, and the siloxyl residue of said organopolysiloxane has a molecular weight of from 1,000 to 30,000 Daltons.

4. The emulsion of claim 1 , wherein said benefit agent comprises a material selected from the group consisting of a silicone, a vinyl polymer, a polyether, a material comprising a hydrocarbon wax, a hydrocarbon liquid, a fluid sugar polyester, a fluid sugar polyether, and mixtures thereof.

5. The emulsion of claim 1 , where the ratio of benefit agent to organopolysiloxane is from 1000:1 to 1:1; or from 500:1 to 5:1; or from 250:1 to 5:1; or from 100:1 to 5:1; or from 100:1 to 10:1.

6. The emulsion of claim 1 , where the ratio of benefit agent to organopolysiloxane is from 40:1 to 20:1; or from 30:1 to 15:1.

7. A consumer product composition comprising: 1 (a) emulsion of claim 1 ; and 1 (b) an auxiliary composition.

8. The consumer product composition of claim 7 , wherein said composition comprises surfactant selected from the group consisting of cationic, anionic, amphoteric, non-ionic, and combinations thereof.

9. The consumer product composition of claim 7 , wherein said auxiliary composition comprises surfactant selected from the group consisting of cationic, anionic, amphoteric, non-ionic, and combinations thereof.

10. The consumer product composition of claim 7 , wherein said emulsion comprises a benefit agent selected from the group consisting of a silicone, a vinyl polymer, a polyether, a material comprising a hydrocarbon wax, a hydrocarbon liquid, a fluid sugar polyester, a fluid sugar polyether, and mixtures thereof.

11. The consumer product composition of claim 7 , comprising a second benefit agent selected from the group consisting of clays, metal oxides, silicones, and microcapsules.

12. The consumer product composition of claim 10 , wherein said silicone benefit agent is selected from the group consisting of a polydimethylsiloxane, an aminosilicone, a cationic silicone, a silicone polyether, a cyclic silicone, a silicone resin, a fluorinated silicone and mixtures thereof.

13. The consumer product composition of claim 12 , wherein:

a) said polydimethylsiloxane has a viscosity from 10 centistokes (cSt) to 2,000,000 cSt; from 50 cSt to 1,000,000 cSt; from 500 cSt to 100,000 cSt; or from 750 cSt to 1000 cSt;

b) said aminosilicone has a viscosity from 100 cSt to 300,000 cSt; from 500 cSt to 200,000 cSt; from 750 cSt to 50,000 cSt; or from 1000 cSt to 5000 cSt;

c) said cationic silicone has a viscosity from 100 cSt to 1,000,000 cSt; from 500 cSt to 500,000 cSt; from 750 cSt to 50,000 cSt; or from 1000 cSt to 5000 cSt;

d) said silicone polyether has a viscosity from 100 cSt to 1,000,000 cSt; from 500 cSt to 500,000 cSt; from 750 cSt to 50,000 cSt; or from 1000 cSt to 5000 cSt;

e) said cyclic silicone has a viscosity from 10 cSt to 10,000 cSt; from 50 cSt to 5,000 cSt; from 100 cSt to 2,000 cSt; or from 200 cSt to 1000 cSt;

(f) said silicone resin has a viscosity from 10 cSt to 10,000 cSt; from 50 cSt to 5,000 cSt; from 100 cSt to 2,000 cSt; or from 200 cSt to 1000 cSt; and

g) said fluorinated silicone has a viscosity from 100 cSt to 300,000 cSt; from 500 cSt to 200,000 cSt; from 750 cSt to 50,000 cSt; or from 1000 cSt to 5000 cSt.

14. The composition of claim 12 , wherein said silicone benefit agent has the structure:

[R″ 1 R″ 2 R″ 3 SiO 1/2 ] (c+2) [(R″ 4 Si(X—Z)O 2/2 ] g [R″ 4 R″ 4 SiO 2/2 ] r [R″ 4 SiO 3/2 ] c

wherein:

c is an integer from 0 to 98; in one aspect c is an integer from 0 to 48; in one aspect, c is 0;

g is an integer from 0 to 200; in one aspect, g is an integer from 0 to 50; when g =0, at least one of R″ 1 R″ 2 or R″ 3 =X″—Z″,

r is an integer from 4 to 5,000; in one aspect r is an integer from 10 to 4,000; in another aspect r is an integer from 50 to 2,000;

R″ 1 , R″ 2 and R″ 3 are each independently selected from the group consisting of H, OH, C 1 -C 32 alkyl, C 1 -C 32 substituted alkyl, C 5 -C 32 or C 6 -C 32 aryl, C 5 -C 32 or C 6 -C 32 substituted aryl, C 6 -C 32 alkylaryl, C 6 -C 32 substituted alkylaryl, C 1 -C 32 alkoxy, C 1 -C 32 substituted alkoxy and X″—Z″;

each R″ 4 is independently selected from the group consisting of H, OH, C 1 -C 32 alkyl, C 1 -C 32 substituted alkyl, C 5 -C 32 or C 6 -C 32 aryl, C 5 -C 32 or C 6 -C 32 substituted aryl, C 6 -C 32 alkylaryl, C 6 -C 32 substituted alkylaryl, C 1 -C 32 alkoxy and C 1 -C 32 substituted alkoxy;

for each X″—Z″,

X″ comprises a divalent alkylene radical comprising 2-12 carbon atoms; and 3 at least one Z″ in the said organosiloxane is selected from the group consisting of R″ 5 ;

each additional Z″ in said organosilicone is independently selected from the group comprising of H, C 1 -C 32 alkyl, C 1 -C 32 substituted alkyl, C 5 -C 32 or C 6 -C 32 aryl, C 5 -C 32 or C 6 -C 32 substituted aryl, C 6 -C 32 alkylaryl, C 6 -C 32 substituted alkylaryl, R″ 5 ,

each R″ 5 is independently selected from the group consisting of H; C 1 -C 32 alkyl; C 1 -C 32 substituted alkyl, C 5 -C 32 or C 6 -C 32 aryl, C 5 -C 32 or C 6 -C 32 substituted aryl or C 6 -C 32 alkylaryl, or C 6 -C 32 substituted alkylaryl, —(CHR″ 6 —CHR″ 6 —O—) b —CHR″ 6 —CHR″ 6 -L and a siloxyl residue;

b is an integer from 0 to 500, in one aspect b is an integer from 0 to 200, one aspect b is an integer from 0 to 50;

each R 6 is independently selected from H or a C 1 -C 18 alkyl;

wherein each L is independently selected from —O—C(O)—R 7 or —O—R 7 ;

each R 7 is independently selected from the group consisting of H; C 1 -C 32 alkyl; C 1 -C 32 substituted alkyl, C 5 -C 32 or C 6 -C 32 aryl, C 5 -C 32 or C 6 -C 32 substituted aryl, C 6 -C 32 alkylaryl, and C 6 -C 32 substituted aryl, and a siloxyl residue;

each T″ is independently selected from H;

 wherein

each v in said organosilicone is an integer from 1 to 10, in one aspect, v is an integer from 1 to 5 and the sum of all v indices in each Z in the said organosilicone is an integer from 1 to 30 or from 1 to 20 or from 1 to 10, with the proviso that the total moieties T in a molecule does not exceed 6.

15. The composition of claim 14 , wherein the organosilicone comprises a pendant aminosilicone or terminal aminosilicone.

16. The composition of claim 15 , wherein the organosilicone comprises a pendant aminosilicone having the structure:

[R″ 1 R″ 2 R″ 3 SiO 1/2 ] (c+2) [(R″ 4 Si(X—K)O 2/2 ] g [R″ 4 R″ 4 SiO 2/2 ] r [R″ 4 SiO 3/2 ] c

wherein:

c is an integer from 0 to 98; in one aspect c is an integer from 0 to 48; in one aspect, c is 0;

g is an integer from 0 to 200, in one aspect g is an integer from 0 to 50; when g =0, at least one of R″ 1 , R″ 2 or R″ 3 is X″—K″;

h is an integer from 4 to 5,000; in one aspect h is an integer from 10 to 4,000; in another aspect h is an integer from 50 to 2,000;

R″ 1 , R″ 2 and R″ 3 are each independently selected from the group consisting of H, OH, C 1 -C 32 alkyl, C 1 -C 32 substituted alkyl, C 5 -C 32 or C 6 -C 32 aryl, C 5 -C 32 or C 6 -C 32 substituted aryl, C 6 -C 32 alkylaryl, C 6 -C 32 substituted alkylaryl, C 1 -C 32 alkoxy, C 1 -C 32 substituted alkoxy and X″—K″;

each R″ 4 is independently selected from the group consisting of H, OH, C 1 -C 32 alkyl, C 1 -C 32 substituted alkyl, C 5 -C 32 or C 6 -C 32 aryl, C 5 -C 32 or C 6 -C 32 substituted aryl, C 6 -C 32 alkylaryl, C 6 -C 32 substituted alkylaryl, C 1 -C 32 alkoxy and C 1 -C 32 substituted alkoxy;

for each X—K X comprises a divalent alkylene radical comprising 2-12 carbon atoms, in one aspect, each divalent alkylene radical is independently selected from the group consisting of —(CH 2 ) s — wherein s is an integer from 2 to 8, or an integer from 2 to 4; and

each K is selected independently from the group consisting of ,

each Q″ is independently a H or a C 1 -C 32 , linear or branched, substituted or unsubstituted hydrocarbon, with the proviso that when K″ is a quat, Q″ cannot be an amide, imine, or urea moiety and if Q″ is an amide, imine, or urea moiety, then any additional Q″ bonded to the same nitrogen as said amide, imine, or urea moiety must be H or a C 1 -C 6 alkyl, in one aspect, said additional Q″ is H;

X is defined as above;

for K″ A h− is a suitable charge balancing anion. In one aspect A h− is selected from the group consisting of Cl − , Br − ,I − , methylsulfate, toluene sulfonate, carboxylate and phosphate ; 2 and at least one Q″ in said organosilicone is independently selected from

—CH 2 —CH(OH)—CH 2 —R″ 5 ;

for cationically charged K″, A″ h− is a suitable charge balancing anion, in one aspect A″ h− is selected from the group consisting of Cl—, Br—,I−, methylsulfate, toluene sulfonate, carboxylate and phosphate,

wherein each R″ 5 is independently selected from the group consisting of H, C 1 -C 32 alkyl, C 1 -C 32 substituted alkyl, C 5 -C 32 or C 6 -C 32 aryl, C 5 -C 32 or C 6 -C 32 substituted aryl, C 6 -C 32 alkylaryl, C 6 -C 32 substituted alkylaryl, —(CHR 6 —CHR 6 —O—) b -L and a siloxyl residue;

each R 6 is independently selected from H, C 1 -C 18 alkyl

each L is independently selected from —C(O)—R 7 or R 7 ;

R 7 is independently selected from the group consisting of H, C 1 -C 32 alkyl, C 1 -C 32 substituted alkyl, C 5 -C 32 or C 6 -C 32 aryl, C 5 -C 32 or C 6 -C 32 substituted aryl, C 6 -C 32 alkylaryl, C 6 -C 32 substituted alkylaryl and a siloxyl residue;

b is an integer from 0 to 500, in one aspect b is an integer from 1 to 200; in one aspect b is an integer from 1 to 50.

17. The composition of claim 16 , wherein the pendant aminosilicone has a molecular weight from 1000 Daltons to 1,000,000 Daltons; from 10,000 Daltons to 100,000 Daltons; or from 15,000 Daltons to 50,000 Daltons.

18. The consumer product composition of claim 7 , comprising from 0.1% to 25%, or from 0.1% to 20%, or from 0.1% to 15, or from 0.1% to 10%, or from 0.1% to 5%, or from 0.1% to 1% or from 0.25% to 25%, or from 0.5% to 20%, or from 1% to 15%, of said emulsion by weight.

19. The consumer product composition of claim 7 , wherein said consumer product composition is in the form selected from the group consisting of shampoo, conditioners, body wash, detergent, fabric enhancers, antimicrobial wash, and hard surface cleaner.

20. The consumer product composition of claim 7 , comprising a hydrophobic benefit agent selected from the group consisting of silicone, fragrance, emollient, antimicrobial agent, sunscreen, lipid, oil, hydrocarbon, wax, hydrophobically-modified pigment, inorganic compound, and mixtures thereof.

21. A method of providing hair conditioning, skin moisturizing, fabric softening, or a fabric anti-wrinkle property, comprising contacting a substrate selected from the group consisting of hair, skin, and fabric with the composition of claim 7 .

22. A method of depositing a hydrophobic benefit agent onto a substrate, comprising contacting said substrate with the composition of claim 7 .

23. The consumer product composition of claim 7 , wherein said consumer product composition is in the form selected from the group consisting of conditioners, body wash, detergent, and fabric enhancers.

24. The emulsion of claim 1 , wherein said organopolysiloxane has a charge density of from 0.1 meq/g to 12 meq/g, or from 0.2 to 7 meq/g, or from 0.4 to 5.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2015
From: GIZAW, YONAS; SMITH, STEVEN DARYL; MCCHAIN, ROBERT JOSEPH; PANANDIKER, RAJAN KESHAV; BARRERA, CAROLA; KOENIG, PETER HERBERT; JAMADAGNI, SUMANTH NARAHARI
To: THE PROCTER & GAMBLE COMPANY
Reel/Frame 034811/0147 →
Continuity (2)
Continuation PCTUS2013052589 · Jul 29, 2013
Related Publication 20150140052A1 · May 21, 2015