US2002155985A1PendingUtilityA1
Fragrance pro-accords and aldehyde and ketone fragrance libraries
Priority: Oct 23, 1998Filed: Mar 12, 2001Published: Oct 24, 2002
Est. expiryOct 23, 2018(expired)· nominal 20-yr term from priority
C07D 263/06A61Q 13/00A61K 2800/57A61K 8/49
44
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Claims
Abstract
The present invention relates to novel heterocyclic pro-fragrances, preferably oxazolidines, tertahydro-1,3-oxazines, thiazolidines, or tetrahydro-1,3-thiazines, more preferably oxazolidines, or tertahydro-1,3-oxazines, most preferably oxazolidines, which are capable of sustained release of fragrance raw material ketones and aldehydes and to fragrance delivery systems which comprise said pro-fragrances.
Claims
exact text as granted — not AI-modifiedwhat is claimed is:
1 . A pro-fragrance having the formnula:
wherein said pro-fragrance or pro-accord releases an aldehyde or a ketone fragrance raw material, wherein X is oxygen or sulfur; R is:
a) C 6 -C 22 substituted or unsubstituted linear alkyl;
b) C 6 -C 22 substituted or unsubstituted branched alkyl;
c) C 6 -C 22 substituted or unsubstituted linear alkenyl;
d) C 6 -C 22 substituted or unsubstituted branched alkenyl;
e) C 6 -C 22 substituted or unsubstituted cycloalkyl;
f) C 6 -C 22 substituted or unsubstituted branched cycloalkyl;
g) C 6 -C 22 substituted or unsubstituted cycloalkenyl;
h) C 6 -C 22 substituted or unsubstituted branched cycloalkenyl;
i) C 6 -C 22 substituted or unsubstituted aryl;
j) C 6 -C 22 substituted or unsubstituted heterocyclicalkyl;
k) C 6 -C 22 substituted or unsubstituted heterocyclicalkenyl;
l) and mixtures thereof;
R 1 is:
a) hydrogen;
b) C 1 -C 10 substituted or unsubstituted linear alkyl;
c) C 3 -C 10 substituted or unsubstituted branched alkyl;
d) C 2 -C 10 substituted or unsubstituted linear alkenyl;
e) C 3 -C 10 substituted or unsubstituted branched alkenyl;
f) C 3 -C 15 substituted or unsubstituted cycloalkyl;
g) C 4 -C 15 substituted or unsubstituted branched cycloalkyl;
h) C 4 -C 15 substituted or unsubstituted cycloalkenyl;
i) C 5 -C 15 substituted or unsubstituted branched cycloalkenyl;
j) C 6 -C 15 substituted or unsubstituted aryl;
k) C 6 -C 22 substituted or unsubstituted heterocyclicalkyl;
l) C 6 -C 22 substituted or unsubstituted heterocyclicalkenyl;
m) and mixtures thereof;
R and R 1 can be taken together to form a substituted or unsubstituted ring having in the ring from 3 to 10 carbon atoms;
each R 2 , R 3 , and each R 4 and R 5 pair are independently:
a) R 1 ;
b) hydroxyl;
c) a carbonyl comprising unit having the formula:
—(CH 2 ) x COR 7
wherein R 7 is:
i) —OH;
ii) —OR 8 wherein R 8 is hydrogen, C 1 -C 15 substituted or unsubstituted linear alkyl, C 1 -C 15 substituted or unsubstituted branched alkyl, C 2 -C 22 substituted or unsubstituted linear alkenyl, C 3 -C 22 substituted or unsubstituted branched alkenyl, or mixtures thereof, wherein said substitution is not halogen;
iii) —N(R 9 ) 2 wherein R 9 is hydrogen, C 1 -C 6 substituted or unsubstituted linear alkyl, C 3 -C 6 substituted or unsubstituted branched alkyl, or mixtures thereof;
iv) C 1 -C 22 substituted or unsubstituted linear alkyl;
v) C 1 -C 22 substituted or unsubstituted branched alkyl;
vi) C 2 -C 22 substituted or unsubstituted linear alkenyl;
vii) C 3 -C 22 substituted or unsubstituted branched alkenyl;
viii) C 3 -C 22 substituted or unsubstituted cycloalkyl;
ix) C 6 -C 22 substituted or unsubstituted aryl;
x) C 6 -C 22 substituted or unsubstituted heterocyclicalkyl;
xi) C 6 -C 22 substituted or unsubstituted heterocyclicalkenyl;
the index x is from 1 to 22;
d) alkyleneoxy units having the formula:
—(CR 10 R 11 ) y (CHR 12 CHR 13 O) z R 14
wherein each R 10 , R 11 , and R 12 is independently;
i) hydrogen;
ii) —OH;
iii) C 1 -C 4 alkyl;
iv) or mixtures thereof;
R 13 is:
i) hydrogen;
ii) C 1 -C 4 alkyl;
iii) or mixtures thereof;
R 14 is:
i) hydrogen;
ii) C 1 -C 4 alkyl;
iii) or mixtures thereof;
R 10 and R 11 can be taken together to form a C 3 -C 6 spiroannulated ring, carbonyl unit, or mixtures thereof; y has the value from 0 to 10, z has the value from 1 to 50;
e) and mixtures thereof;
R 6 is:
a) C 1 -C 10 substituted linear alkyl;
b) C 3 -C 10 substituted branched alkyl;
c) C 2 -C 10 substituted or unsubstituted linear alkenyl;
d) C 3 -C 10 substituted or unsubstituted branched alkenyl;
e) C 3 -C 15 substituted cycloalkyl;
f) C 4 -C 15 substituted or unsubstituted branched cycloalkyl;
g) C 4 -C 15 substituted or unsubstituted cycloalkenyl;
h) C 5 -C 15 substituted or unsubstituted branched cycloalkenyl;
i) C 6 -C 15 substituted aryl;
j) C 6 -C 22 substituted or unsubstituted heterocyclicalkyl;
k) C 6 -C 22 substituted or unsubstituted heterocyclicalkenyl;
l) a carbonyl comprising unit having the formula:
—(CH 2 ) x COR 7
wherein R 7 is:
i) —OH;
ii) —OR 8 wherein R 8 is hydrogen, C 1 -C 15 substituted linear alkyl, C 11 -C 15 unsubstituted linear alkyl, C 1 -C 15 substituted branched alkyl, C 11 -C 15 unsubstituted branched alkyl, C 2 -C 22 substituted or unsubstituted linear alkenyl, C 3 -C 22 substituted or unsubstituted branched alkenyl, or mixtures thereof, wherein said substitution is not halogen or thioalkyl;
iii) —N(R 9 ) 2 wherein R 9 is hydrogen, C 1 -C 6 substituted or unsubstituted linear alkyl, C 3 -C 6 substituted or unsubstituted branched alkyl, or mixtures thereof;
iv) C 1 -C 22 substituted or unsubstituted linear alkyl;
v) C 1 -C 22 substituted or unsubstituted branched alkyl;
vi) C 2 -C 22 substituted or unsubstituted linear alkenyl;
vii) C 3 -C 22 substituted or unsubstituted branched alkenyl;
viii) C 3 -C 22 substituted or unsubstituted cycloalkyl;
ix) C 6 -C 22 substituted or unsubstituted aryl;
x) C 6 -C 22 substituted or unsubstituted heterocyclicalkyl;
xi) C 6 -C 22 substituted or unsubstituted heterocyclicalkenyl; the index x is from 0 to 22;
m) alkyleneoxy units having the formula:
—(CR 10 R 11 ) y (CHR 12 CHR 13 O) z R 14
wherein each R 10 , R 11 , and R 12 is independently;
i) hydrogen;
ii) —OH;
iii) C 1 -C 4 alkyl;
iv) or mixtures thereof;
R 13 is:
i) hydrogen;
ii) C 1 -C 4 alkyl;
iii) or mixtures thereof;
R 14 is:
i) hydrogen;
ii) C 1 -C 4 alkyl;
iii) or mixtures thereof;
R 10 and R 11 can be taken together to form a C 3 -C 6 spiroannulated ring, carbonyl unit, or mixtures thereof; y has the value from 0 to 10, z has the value from 1 to 50;
n) and mixtures thereof;
any two R 2 , R 3 , R 4 , R 5 , or R 6 units can be taken together to form:
i) a carbonyl moiety;
ii) a C 3 -C 6 spiroannulated ring;
iii) a heterocyclic aromatic ring comprising from 5 to 7 atoms;
iv) a non-heterocyclic aromatic ring comprising from 5 to 7 atoms;
v) a heterocyclic ring comprising from 5 to 7 atoms;
vi) a non-heterocyclic ring comprising from 5 to 7 atoms;
vii) or mixtures thereof; and
the index n is an integer from 1 to 3.
2 . A compound according to claim 1 wherein R is C 8 -C 12 unsubstituted linear alkyl, C 8 -C 12 unsubstituted branched alkyl, C 8 -C 15 unsubstituted linear alkenyl, C 8 -C 15 unsubstituted branched alkenyl, C 6 -C 15 unsubstituted cycloalkyl, C 7 -C 15 unsubstituted branched cycloalkyl, C 10 -C 20 unsubstituted cycloalkenyl, C 10 -C 20 unsubstituted branched cycloalkenyl, C 6 -C 15 substituted or unsubstituted aryl, C 6 -C 15 unsubstituted heterocyclicalkyl, and mixtures thereof, R 6 is hydrogen.
3 . A compound according to either claim 1 or 2 wherein said aldehyde which is released is selected from the group consisting of 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-l-carboxaldehyde, phenylacetaldehyde, methylnonyl acetaldehyde, 2-phenylpropan-l-al, 3-phenylprop-2-en- 1-al, 3-phenyl-2-pentylprop-2-en- 1-al, 3-phenyl-2-hexylprop-2-enal, 3-(4-isopropylphenyl)-2-methylpropan-1-al, 3-(4-ethylphenyl)-2,2-dimethylpropan-1-al, 3-(4-tert-butylphenyl)-2-methyl-propanal, 3-(3,4-methylenedioxyphenyl)-2-methylpropan-1-al , 3-(4-ethylphenyl)-2,2-dimethylpropanal, 3-(3-isopropylphenyl)butan-1-al, 2,6-dimethylhep-5-en-1-al, n-decanal, n-undecanal, n-dodecanal, 3,7-dimethyl-2,6-octadien-1-al, 4-methoxybenzaldehyde, 3-methoxy-4-hydroxybenz-aldehyde, 3-ethoxy-4-hydroxybenzaldehyde, 3,4-methylenedioxy-benzaldehyde, 3,4-dimethoxybenzaldehyde, and mixtures thereof.
4 . A compound according to any of claims 1 - 3 having the formula:
wherein R 2 , R 3 , R 4 , and R 5 is the same as defined herein above, R 15 , R 16 , and R 17 are each independently:
a) C 1 -C 22 substituted or unsubstituted linear alkyl, preferably methyl or ethyl, more preferably methyl;
b) C 3 -C 22 substituted or unsubstituted branched alkyl;
c) C 2 -C 22 substituted or unsubstituted linear alkenyl;
d) C 3 -C 22 substituted or unsubstituted branched alkenyl;
e) C 3 -C 22 substituted or unsubstituted cycloalkyl;
f) C 4 -C 22 substituted or unsubstituted branched cycloalkyl;
g) C 4 -C 22 substituted or unsubstituted cycloalkenyl;
h) C 4 -C 22 substituted or unsubstituted branched cycloalkenyl;
i) C 6 -C 22 substituted or unsubstituted aryl;
_) C 6 -C 22 substituted or unsubstituted heterocyclicalkyl;
k) C 6 -C 22 substituted or unsubstituted heterocyclicalkenyl;
l) any two R 15 , R 6 , and R 17 units can be taken together to form a substituted or unsubstituted ring having from 3-10 carbon atoms;
m) and mixtures thereof.
5 . A compound according to any of claims 1 - 4 having the formula:
wherein R 3 is hydrogen, C 1 -C 15 substituted linear alkyl, Cli-C, 5 unsubstituted linear alkyl, C 1 -C 15 substituted branched alkyl, C 1 -C 15 unsubstituted branched alkyl, C 2 -C 22 substituted or unsubstituted linear alkenyl, C 3 -C 22 substituted or unsubstituted branched alkenyl, or mixtures thereof; R 16 and R 17 are each selected from the group consisting of methyl, C 6 -C 15 substituted or unsubstituted alkylenearyl, R 16 and R 17 are taken together to form a substituted or unsubstituted cycloalkenyl ring, and mixtures thereof.
6 . A fragrance delivery system comprising:
A) from 1% by weight, of a pro-fragrance component comprising:
i) at least 1% by weight, of an aldehyde or ketone releasing pro-fragrance component, said pro-fragrance having the formula:
wherein said pro-fragrance or pro-accord releases an aldehyde or a ketone fragrance raw material, wherein X is oxygen or sulfur; R is:
a) C 6 -C 22 substituted or unsubstituted linear alkyl; b) C 6 -C 22 substituted or unsubstituted branched alkyl; c) C 6 -C 22 substituted or unsubstituted linear alkenyl; d) C 6 -C 22 substituted or unsubstituted branched alkenyl; e) C 6 -C 22 substituted or unsubstituted cycloalkyl; f) C 6 -C 22 substituted or unsubstituted branched cycloalkyl; g) C 6 -C 22 substituted or unsubstituted cycloalkenyl; h) C 6 -C 22 substituted or unsubstituted branched cycloalkenyl; i) C 6 -C 22 substituted or unsubstituted aryl; j) C 6 -C 22 substituted or unsubstituted heterocyclicalkyl; k) C 6 -C 22 substituted or unsubstituted heterocyclicalkenyl; l) and mixtures thereof;
R 1 is:
a) hydrogen; b) C 1 -C 10 substituted or unsubstituted linear alkyl; c) C 3 -C 10 substituted or unsubstituted branched alkyl; d) C 2 -C 10 substituted or unsubstituted linear alkenyl; e) C 3 -C 10 substituted or unsubstituted branched alkenyl; f) C 3 -C 15 substituted or unsubstituted cycloalkyl; g) C 4 -C 15 substituted or unsubstituted branched cycloalkyl; h) C 4 -C 15 substituted or unsubstituted cycloalkenyl; i) C 5 -C 15 substituted or unsubstituted branched cycloalkenyl; j) C 6 -C 15 substituted or unsubstituted aryl; k) C 6 -C 22 substituted or unsubstituted heterocyclicalkyl; l) C 6 -C 22 substituted or unsubstituted heterocyclicalkenyl; R and R 1 can be taken together to form a substituted or unsubstituted ring having in the ring from 3 to 10 carbon atoms; and each R 2 , R 3 , R 6 and each R 4 and R 5 pair are independently: a) R 1 ; b) hydroxyl; c) a carbonyl comprising unit having the formula: —(CH 2 ) x COR 7 wherein R 7 is:
i) —OH;
ii) OR 8 wherein R 8 is hydrogen, C 1 -C 15 substituted or unsubstituted linear alkyl, C 1 -C 15 substituted or unsubstituted branched alkyl, C 2 -C 22 substituted or unsubstituted linear alkenyl, C 3 -C 22 substituted or unsubstituted branched alkenyl, or mixtures thereof;
iii) —N(R 9 ) 2 wherein R 9 is hydrogen, C 1 -C 6 substituted or unsubstituted linear alkyl, C 3 -C 6 substituted or unsubstituted branched alkyl, or mixtures thereof;
iv) C 1 -C 22 substituted or unsubstituted linear alkyl;
v) C 1 -C 22 substituted or unsubstituted branched alkyl;
vi) C 2 -C 22 substituted or unsubstituted linear alkenyl;
vii) C 3 -C 22 substituted or unsubstituted branched alkenyl;
viii) C 3 -C 22 substituted or unsubstituted cycloalkyl;
ix) C 6 -C 22 substituted or unsubstituted aryl;
x) C 6 -C 22 substituted or unsubstituted heterocyclicalkyl;
xi) C 6 -C 22 substituted or unsubstituted heterocyclicalkenyl;
the index x is from 0 to 22;
d) alkyleneoxy units having the formula: —(CR 10 R 11 ) y (CHR 12 CHR 13 O) z R 14 wherein each R 10 , R 11 , and R 12 is independently;
i) hydrogen;
ii) —OH;
iii) C 1 -C 4 alkyl;
iv) or mixtures thereof;
R 13 is: i) hydrogen; ii) C 1 -C 4 alkyl; iii) or mixtures thereof; R 14 is: i) hydrogen; ii) C 1 -C 4 alkyl; iii) or mixtures thereof; R 10 and R 11 can be taken together to form a C 3 -C 6 spiroannulated ring, carbonyl unit, or mixtures thereof; y has the value from 0 to 10, z has the value from 1 to 50; e) any two R 2 , R 3 , R 4 , R 5 , or R 6 units can be taken together to form:
i) a carbonyl moiety;
ii) a C 3 -C 6 spiroannulated ring;
iii) a heterocyclic aromatic ring comprising from 5 to 7 atoms;
iv) a non-heterocyclic aromatic ring comprising from 5 to 7 atoms;
v) a heterocyclic ring comprising from 5 to 7 atoms;
vi) a non-heterocyclic ring comprising from 5 to 7 atoms;
vii) or mixtures thereof;
f) and mixtures thereof; and the index n is an integer from 1 to 3;
ii) optionally from 1% by weight, of one or more pro-accords formed from at least one fragrance raw material, wherein said pro-accord is selected from the group consisting of acetals, ketals, orthoesters, orthocarbonates, and mixtures thereof, each pro-accord releasing upon hydrolysis said fragrance raw material from which it is formed, said fragrance raw materials selected from the group consisting of primary, secondary, and tertiary alcohols, aldehydes, ketones, esters, carbonates, and mixtures thereof, provided each pro-accord:
a) is formed from at least one fragrance raw material having a molecular weight greater than or equal to 100 g/mol;
b) has a fragrance release half-life of greater than or equal to 0.1 hours at pH 5.3 and less than or equal to 12 hours at pH 2.5 when measured in NaH 2 PO 4 buffer;
iii) the balance carriers, stabilizers, and other adjunct ingredients; and
B) optionally from 1% by weight, a fragrance raw material component comprising:
i) optionally at least 1% by weight, of a mixture of one or more base note fragrances;
ii) optionally at least 1% by weight, of a mixture of one or more top or middle note fragrances;
iii) optionally the balance carriers, fixatives, and other adjunct ingredients.
7 . A fine fragrance or perfume composition comprising:
i) at least 0.01% by weight, of an aldehyde or ketone releasing pro-fragrance component, said pro-fragrance having the formula: wherein said pro-fragrance or pro-accord releases an aldehyde or a ketone fragrance raw material, wherein X is oxygen or sulfur; R is:
a) C 6 -C 22 substituted or unsubstituted linear alkyl;
b) C 6 -C 22 substituted or unsubstituted branched alkyl;
c) C 6 -C 22 substituted or unsubstituted linear alkenyl;
d) C 6 -C 22 substituted or unsubstituted branched alkenyl;
e) C 6 -C 22 substituted or unsubstituted cycloalkyl;
f) C 6 -C 22 substituted or unsubstituted branched cycloalkyl;
g) C 6 -C 22 substituted or unsubstituted cycloalkenyl;
h) C 6 -C 22 substituted or unsubstituted branched cycloalkenyl;
i) C 6 -C 22 substituted or unsubstituted aryl;
j) C 6 -C 22 substituted or unsubstituted heterocyclicalkyl;
k) C 6 -C 22 substituted or unsubstituted heterocyclicalkenyl;
l) and mixtures thereof;
R 1 is:
a) hydrogen;
b) C 1 -C 10 substituted or unsubstituted linear alkyl;
c) C 3 -C 10 substituted or unsubstituted branched alkyl;
d) C 2 -C 10 substituted or unsubstituted linear alkenyl;
e) C 3 -C 10 substituted or unsubstituted branched alkenyl;
f) C 3 -C 15 substituted or unsubstituted cycloalkyl;
g) C 4 -C 15 substituted or unsubstituted branched cycloalkyl;
h) C 4 -C 15 substituted or unsubstituted cycloalkenyl;
i) C 5 -C 15 substituted or unsubstituted branched cycloalkenyl;
j) C 6 -C 15 substituted or unsubstituted aryl;
k) C 6 -C 22 substituted or unsubstituted heterocyclicalkyl;
l) C 6 -C 22 substituted or unsubstituted heterocyclicalkenyl;
R and R 1 can be taken together to form a substituted or unsubstituted ring having in the ring from 3 to 10 carbon atoms; and each R 2 , R 3 , R 6 and each R 4 and R 5 pair are independently:
a) R 1 ;
b) hydroxyl;
c) a carbonyl comprising unit having the formula:
—(CH 2 ) x COR 7
wherein R 7 is:
i) —OH;
ii) —OR 8 wherein R 8 is hydrogen, C 1 -C 15 substituted or unsubstituted linear alkyl, C 1 -C 15 substituted or unsubstituted branched alkyl, C 2 -C 22 substituted or unsubstituted linear alkenyl, C 3 -C 22 substituted or unsubstituted branched alkenyl, or mixtures thereof;
iii) -N(R 9 ) 2 wherein R 9 is hydrogen, C 1 -C 6 substituted or unsubstituted linear alkyl, C 3 -C 6 substituted or unsubstituted branched alkyl, or mixtures thereof;
iv) C 1 -C 22 substituted or unsubstituted linear alkyl;
v) C 1 -C 22 substituted or unsubstituted branched alkyl;
vi) C 2 -C 22 substituted or unsubstituted linear alkenyl;
vii) C 3 -C 22 substituted or unsubstituted branched alkenyl;
viii) C 3 -C 22 substituted or unsubstituted cycloalkyl;
ix) C 6 -C 22 substituted or unsubstituted aryl;
x) C 6 -C 22 substituted or unsubstituted heterocyclicalkyl;
xi) C 6 -C 22 substituted or unsubstituted heterocyclicalkenyl; the index x is from 0 to 22;
d) alkyleneoxy units having the formula:
—(CR 10 R 11 ) y (CHR 12 CHR 13 O) z R 14
wherein each R 10 , R 11 , and R 12 is independently;
i) hydrogen;
ii) —OH;
iii) C 1 -C 4 alkyl;
iv) or mixtures thereof;
R 13 is:
i) hydrogen;
ii) C 1 -C 4 alkyl;
iii) or mixtures thereof;
R 14 is:
i) hydrogen;
ii) C 1 -C 4 alkyl;
iii) or mixtures thereof;
R 10 and R 11 can be taken together to form a C 3 -C 6 spiroannulated ring, carbonyl unit, or mixtures thereof; y has the value from 0 to 10, z has the value from 1 to 50; e) any two R 2 , R 3 , R 4 , R 5 , or R 6 units can be taken together to form:
i) a carbonyl moiety;
ii) a C 3 -C 6 spiroannulated ring;
iii) a heterocyclic aromatic ring comprising from 5 to 7 atoms;
iv) a non-heterocyclic aromatic ring comprising from 5 to 7 atoms;
v) a heterocyclic ring comprising from 5 to 7 atoms;
vi) a non-heterocyclic ring comprising from 5 to 7 atoms;
vii) or mixtures thereof;
f) and mixtures thereof; and the index n is an integer from 1 to 3;
ii) optionally from 1% by weight, of one or more pro-accords which comprise n fragrance raw materials but which release n+1 fragrance raw materials;
iii) optionally from 1% by weight, of one or more pro-fragrances selected from the group consisting of acetals, ketals, orthoesters, orthocarbonate, b-ketoesters, and mixtures thereof;
iv) optionally from 1% by weight, of one or more fragrance raw materials; and
v) optionally one or more carriers, fixatives, stabilizers, or adjunct ingredients.
8 . A perfume composition having extended fragrance character impressions comprising:
A) a pro-accord component comprising:
i) at least 0.01% by weight, of an aldehyde or ketone releasing pro-fragrance component, said pro-fragrance having the formula:
wherein said pro-fragrance or pro-accord releases an aldehyde or a ketone fragrance raw material, wherein X is oxygen or sulfur; R is:
a) C 6 -C 22 substituted or unsubstituted linear alkyl;
b) C 6 -C 22 substituted or unsubstituted branched alkyl;
c) C 6 -C 22 substituted or unsubstituted linear alkenyl;
d) C 6 -C 22 substituted or unsubstituted branched alkenyl;
e) C 6 -C 22 substituted or unsubstituted cycloalkyl;
f) C 6 -C 22 substituted or unsubstituted branched cycloalkyl;
g) C 6 -C 22 substituted or unsubstituted cycloalkenyl;
h) C 6 -C 22 substituted or unsubstituted branched cycloalkenyl;
i) C 6 -C 22 substituted or unsubstituted aryl;
j) C 6 -C 22 substituted or unsubstituted heterocyclicalkyl;
k) C 6 -C 22 substituted or unsubstituted heterocyclicalkenyl;
l) and mixtures thereof;
R 1 is:
a) hydrogen;
b) C 1 -C 10 substituted or unsubstituted linear alkyl;
c) C 3 -C 10 substituted or unsubstituted branched alkyl; p 2 d) C 2 -C 10 substituted or unsubstituted linear alkenyl;
e) C 3 -C 10 substituted or unsubstituted branched alkenyl;
f) C 3 -C 15 substituted or unsubstituted cycloalkyl;
g) C 4 -C 15 substituted or unsubstituted branched cycloalkyl; p 2 h) C 4 -C 15 substituted or unsubstituted cycloalkenyl;
i) C 5 -C 15 substituted or unsubstituted branched cycloalkenyl;
j) C 6 -C 15 substituted or unsubstituted aryl;
k) C 6 -C 22 substituted or unsubstituted heterocyclicalkyl;
l) C 6 -C 22 substituted or unsubstituted heterocyclicalkenyl;
R and R 1 can be taken together to form a substituted or unsubstituted ring having in the ring from 3 to 10 carbon atoms; and each R 2 , R 3 , R 6 and each R 4 and R 5 pair are independently:
a) R;
b) hydroxyl;
c) a carbonyl comprising unit having the formula:
—(CH 2 ) x COR 7
wherein R 7 is:
i) —OH;
ii) —OR 8 wherein R 8 is hydrogen, C 1 -C 15 substituted or unsubstituted linear alkyl, C 1 -C 15 substituted or unsubstituted branched alkyl, C 2 -C 22 substituted or unsubstituted linear alkenyl, C 3 -C 22 substituted or unsubstituted branched alkenyl, or mixtures thereof;
iii) —N(R 9 ) 2 wherein R 9 is hydrogen, C 1 -C 6 substituted or unsubstituted linear alkyl, C 3 -C 6 substituted or unsubstituted branched alkyl, or mixtures thereof;
iv) C 1 -C 22 substituted or unsubstituted linear alkyl;
v) C 1 -C 22 substituted or unsubstituted branched alkyl;
vi) C 2 -C 22 substituted or unsubstituted linear alkenyl;
vii) C 3 -C 22 substituted or unsubstituted branched alkenyl; viii) C 3 -C 22 substituted or unsubstituted cycloalkyl;
ix) C 6 -C 22 substituted or unsubstituted aryl;
x) C 6 -C 22 substituted or unsubstituted heterocyclicalkyl;
xi) C 6 -C 22 substituted or unsubstituted heterocyclicalkenyl;
the index x is from 0 to 22; d) alkyleneoxy units having the formula: —(CR 10 R 11 ) y (CHR 12 CHR 13 O) z R 14 wherein each R 10 , R 11 , and R 12 is independently;
i) hydrogen;
ii) —OH;
iii) C 1 -C 4 alkyl;
iv) or mixtures thereof;
R 13 is:
i) hydrogen;
ii) C 1 -C 4 alkyl;
iii) or mixtures thereof;
R 14 is:
i) hydrogen;
ii) C 1 -C 4 alkyl; p 2 iii) or mixtures thereof;
R 10 and R 11 can be taken together to form a C 3 -C 6 spiroannulated ring, carbonyl unit, or mixtures thereof; y has the value from 0 to 10, z has the value from 1 to 50; e) any two R 2 , R 3 , R 4 , R 5 , or R 6 units can be taken together to form:
i) a carbonyl moiety;
ii) a C 3 -C 6 spiroannulated ring;
iii) a heterocyclic aromatic ring comprising from 5 to 7 atoms;
iv) a non-heterocyclic aromatic ring comprising from 5 to 7 atoms;
v) a heterocyclic ring comprising from 5 to 7 atoms;
vi) a non-heterocyclic ring comprising from 5 to 7 atoms;
vii) or mixtures thereof;
f) and mixtures thereof; and the index n is an integer from 1 to 3;
ii) from 0.1% by weight, of one or more pro-accords formed from at least one fragrance raw material, wherein said pro-accord is selected from the group consisting of acetals, ketals, orthoesters, orthocarbonates, and mixtures thereof, each pro-accord releasing upon hydrolysis said fragrance raw material from which it is formed, said fragrance raw materials selected from the group consisting of primary, secondary, and tertiary alcohols, aldehydes, ketones, esters, carbonates, and mixtures thereof, provided each pro-accord:
a) is formed from at least one fragrance raw material having a molecular weight greater than or equal to 100 g/mol; b) has a fragrance release half-life of greater than or equal to 0.1 hours at pH 5.3 and less than or equal to 12 hours at pH 2.5 when measured in NaH 2 PO 4 buffer;
iii) the balance carriers, stabilizers, and other adjunct ingredients; and
B) a fragrance raw material component comprising:
i) a mixture of base note fragrances;
ii) one or more top or middle note fragrances;
ii) the balance carriers, fixatives, and other adjunct ingredients.
9 . A method for preparing a fragrance delivery system or a pro-fragrance component of a fragrance delivery system comprises the steps of:
a) admixing one or more precursors of the formula: wherein X is oxygen or sulfur; each R 2 , R 3 , R 6 and each R 4 and R 5 pair are independently: a) hydrogen; b) C 1 -C 10 substituted or unsubstituted linear alkyl; c) C 3 -C 10 substituted or unsubstituted branched alkyl; d) C 2 -C 10 substituted or unsubstituted linear alkenyl; e) C 3 -C 10 substituted or unsubstituted branched alkenyl; f) C 3 -C 15 substituted or unsubstituted cycloalkyl; g) C 4 -C 15 substituted or unsubstituted branched cycloalkyl; h) C 4 -C 15 substituted or unsubstituted cycloalkenyl; i) C 5 -C 15 substituted or unsubstituted branched cycloalkenyl; j) C 6 -C 15 substituted or unsubstituted aryl; k) C 6 -C 22 substituted or unsubstituted heterocyclicalkyl; l) C 6 -C 22 substituted or unsubstituted heterocyclicalkenyl; m) hydroxyl; n) a carbonyl comprising unit having the formula: —(CH 2 ) x COR 7 wherein R 7 is:
i) —OH;
ii) —OR 8 wherein R 8 is hydrogen, C 1 -C 15 substituted or unsubstituted linear alkyl, C 1 -C 15 substituted or unsubstituted branched alkyl, C 2 -C 22 substituted or unsubstituted linear alkenyl, C 3 -C 22 substituted or unsubstituted branched alkenyl, or mixtures thereof;
iii) —N(R 9 ) 2 wherein R 9 is hydrogen, C 1 -C 6 substituted or unsubstituted linear alkyl, C 3 -C 6 substituted or unsubstituted branched alkyl, or mixtures thereof;
iv) C 1 -C 22 substituted or unsubstituted linear alkyl;
v) C 1 -C 22 substituted or unsubstituted branched alkyl;
vi) C 2 -C 22 substituted or unsubstituted linear alkenyl;
vii) C 3 -C 22 substituted or unsubstituted branched alkenyl;
viii) C 3 -C 22 substituted or unsubstituted cycloalkyl;
ix) C 6 -C 22 substituted or unsubstituted aryl;
x) C 6 -C 22 substituted or unsubstituted heterocyclicalkyl;
xi) C 6 -C 22 substituted or unsubstituted heterocyclicalkenyl; the index x is from 0 to 22;
o) alkyleneoxy units having the formula:
—(CR 10 R 11 ) y (CHR 12 CHR 13 O) z R 14
wherein each R 10 , R 11 , and R 12 is independently;
i) hydrogen;
ii) —OH;
iii) C 1 -C 4 alkyl;
iv) or mixtures thereof;
R 13 is:
i) hydrogen;
ii) C 1 -C 4 alkyl;
iii) or mixtures thereof;
R 14 is
i) hydrogen;
ii) C 1 -C 4 alkyl;
iii) or mixtures thereof;
R 10 and R 11 can be taken together to form a C 3 -C 6 spiroannulated ring, carbonyl unit, or mixtures thereof; y has the value from 0 to 10, z has the value from 1 to 50; p) any two R 2 , R 3 , R 4 , R 5 , or R 6 units can be taken together to form:
i) a carbonyl moiety;
ii) a C 3 -C 6 spiroannulated ring;
iii) a heterocyclic aromatic ring comprising from 5 to 7 atoms;
iv) a non-heterocyclic aromatic ring comprising from 5 to 7 atoms;
v) a heterocyclic ring comprising from 5 to 7 atoms;
vi) a non-heterocyclic ring comprising from 5 to 7 atoms;
vii) or mixtures thereof,
q) and mixtures thereof; and the index n is an integer from 1 to 3; with one or more fragrance raw materials; b) optionally adding a catalyst; and c) optionally isolating one or more heterocyclic pro-fragrances.Join the waitlist — get patent alerts
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