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US20020094938A1 - Photo-labile pro-fragrance conjugates - Google Patents

Photo-labile pro-fragrance conjugatesDownload PDF

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Publication number
US20020094938A1
US20020094938A1US10/001,029US102901AUS2002094938A1US 20020094938 A1US20020094938 A1US 20020094938A1US 102901 AUS102901 AUS 102901AUS 2002094938 A1US2002094938 A1US 2002094938A1
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US
United States
Prior art keywords
substituted
unsubstituted
mixtures
fragrance
pro
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US10/001,029
Inventor
Robert Dykstra
Gregory Miracle
Lon Gray
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Co
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Procter and Gamble Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to US10/001,029priorityCriticalpatent/US20020094938A1/en
Application filed by Procter and Gamble CofiledCriticalProcter and Gamble Co
Publication of US20020094938A1publicationCriticalpatent/US20020094938A1/en
Priority to US10/693,733prioritypatent/US6987084B2/en
Priority to US11/148,688prioritypatent/US7109153B2/en
Priority to US11/446,649prioritypatent/US20060223726A1/en
Priority to US11/654,085prioritypatent/US7262156B2/en
Priority to US11/880,028prioritypatent/US7368415B2/en
Priority to US12/077,624prioritypatent/US7534751B2/en
Priority to US12/411,566prioritypatent/US20090186790A1/en
Priority to US12/603,066prioritypatent/US20100040569A1/en
Priority to US12/768,805prioritypatent/US20100210495A1/en
Priority to US12/903,418prioritypatent/US20110028367A1/en
Priority to US13/046,842prioritypatent/US20110165101A1/en
Abandonedlegal-statusCriticalCurrent

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Abstract

The present invention relates to photo-labile pro-fragrance conjugates comprising:
a) a photo-labile unit which upon exposure to electromagnetic radiation is capable of releasing a pro-fragrance unit; and
b) a pro-fragrance unit, which when so released is either
i) a pro-fragrance compound capable of releasing a fragrance raw material; or
ii) a fragrance raw material.
The present invention relates to systems for delivering fragrances to a situs, and to laundry detergent compositions, fine fragrances, personal care and hair care compositions comprising said systems.

Description

Claims (34)

What is claimed is:
1. A photo-labile pro-fragrance conjugate comprising:
a) a photo-labile unit which upon exposure to electromagnetic radiation is capable of releasing a pro-fragrance unit; and
b) a pro-fragrance unit, which when so released is either
i) a pro-fragrance compound capable of releasing a fragrance raw material; or
ii) a fragrance raw material.
Figure US20020094938A1-20020718-C00062
wherein each R4is independently selected from the group consisting of:
i) hydrogen;
ii) C1-C22substituted or unsubstituted, branched or unbranched alkyl;
iii) C2-C22substituted or unsubstituted, branched or unbranched alkenyl;
iv) C2-C20substituted or unsubstituted, branched or unbranched hydroxyalkyl;
v) C7-C20substituted or unsubstituted alkylenearyl;
vi) C3-C20substituted or unsubstituted cycloalkyl;
vii) C6-C20aryl;
viii) C5-C20heteroaryl units comprising one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, and mixtures thereof;
ix) two R4units can be taken together to form one or more aromatic or non-aromatic, heterocyclic or non-heterocyclic, single rings, fused rings, bicyclo rings, spiroannulated rings, or mixtures thereof, said rings comprising from 3 to 20 carbon atoms and one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, and mixtures thereof;
x) and mixtures thereof;
G1and G2are each independently hydrogen, C1-C20linear or branched hydrocarbyl, —Y, —C(O)Y, and mixtures thereof; Y is C6-C10substituted or unsubstituted cyclic alkyl.
Figure US20020094938A1-20020718-C00070
wherein Z is oxygen or sulfur; m is from 1 to 3; R5units are selected from:
a) C6-C22substituted or unsubstituted linear alkyl
b) C6-C22substituted or unsubstituted branched alkyl;
c) C6-C22substituted or unsubstituted linear alkenyl;
d) C6-C22substituted or unsubstituted branched alkenyl;
e) C6-C22substituted or unsubstituted cycloalkyl;
f) C6-C22substituted or unsubstituted branched cycloalkyl;
g) C6-C22substituted or unsubstituted cycloalkenyl;
h) C6-C22substituted or unsubstituted branched cycloalkenyl;
i) C6-C22substituted or unsubstituted aryl;
j) C6-C22substituted or unsubstituted heterocyclicalkyl;
k) C6-C22substituted or unsubstituted heterocyclicalkenyl;
l) and mixtures thereof;
R6units comprise hydrogen or R5;
R7is independently selected from the group consisting of:
a) R6;
b) hydroxyl;
c) a carbonyl comprising unit having the formula:
—(CH2)xCOR8
wherein R8is:
i) —OH;
ii) —OR9wherein R9is hydrogen, C1-C15substituted linear alkyl, C11-C15 unsubstituted linear alkyl, C1-C15substituted branched alkyl, C11-C15unsubstituted branched alkyl, C2-C22substituted or unsubstituted linear alkenyl, C3-C22substituted or unsubstituted branched alkenyl, or mixtures thereof,
iii) —N(R10)2wherein R10is hydrogen, C1-C6substituted or unsubstituted linear alkyl, C3-C6substituted or unsubstituted branched alkyl, or mixtures thereof;
iv) C1-C22substituted or unsubstituted linear alkyl;
v) C1-C22substituted or unsubstituted branched alkyl;
vi) C2-C22substituted or unsubstituted linear alkenyl;
vii) C3-C22substituted or unsubstituted branched alkenyl;
viii) C3-C22substituted or unsubstituted cycloalkyl;
ix) C6-C22substituted or unsubstituted aryl;
x) C6-C22substituted or unsubstituted heterocyclicalkyl;
xi) C6-C22substituted or unsubstituted heterocyclicalkenyl;
the index x is from 0 to 22;
d) alkyleneoxy units having the formula:
—[C(R11)2]y[C(R11)2C(R11)2O]zR11
wherein each R11is independently;
i) hydrogen;
ii) —OH;
iii) C1-C4alkyl;
iv) or mixtures thereof; two R11units can be taken together to form a C3-C6spiroannulated 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; any two R7units can be taken together to form:
i) a carbonyl moiety;
ii) a C3-C6spiroannulated 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.
Figure US20020094938A1-20020718-C00076
wherein each R1is independently hydrogen, a unit which can substitute for hydrogen, C1-C12substituted or unsubstituted hydrocarbyl unit; said units which can substitute for hydrogen are selected from the group consisting of;
i) —NHCOR30;
ii) —COR30;
iii) —COOR30;
iv) —COCH=CH2;
v) —C(=NH)NH2;
vi) —N(R30)2;
vii) —NHC6H5;
viii) =CHC6H5;
ix) —CON(R30)2;
x) —CONHNH2;
xi) —NHCN;
xii) —OCN;
xiii) —CN;
xiv) F, Cl, Br, l, and mixtures thereof;
xv) =O;
xvi) —OR30;
xvii) —NHCHO;
xviii) —OH;
xix) —NHN(R3)2;
xx) =NR30;
xxi) =NOR30;
xxii) —NHOR30;
xxiii) —CNO;
xxiv) —NCS;
xxv) =C(R30)2;
xxvi) —SO3M;
xxvii) —OSO3M;
xxviii) —SCN;
xxix) —P(O)H2;
xxx) —PO2;
xxxi) —P(O)(OH)2;
xxxii) —SO2NH2;
xxxiii) —S02R30;
xxxiv) —NO2;
xxxv) —CF3, —CCl3, —CBr3;
xxxvi) and mixtures thereof; wherein R30is hydrogen, C1-C20linear or branched alkyl, C6-C20aryl, C7-C20alkylenearyl, and mixtures thereof; M is hydrogen, or a salt forming cation;
each R2is independently hydrogen, C1-C12alkyl, and mixtures thereof; X is selected from the group consisting of —OH, —NHR12, and mixtures thereof;
R12is H, C1-C12alkyl, and mixtures thereof;
B is selected from the group consisting of:
Figure US20020094938A1-20020718-C00077
Figure US20020094938A1-20020718-C00078
Figure US20020094938A1-20020718-C00080
wherein each R4is independently selected from the group consisting of:
i) hydrogen;
ii) C1-C22substituted or unsubstituted, branched or unbranched alkyl;
iii) C2-C22substituted or unsubstituted, branched or unbranched alkenyl;
iv) C2-C20substituted or unsubstituted, branched or unbranched hydroxyalkyl;
v) C7-C20substituted or unsubstituted alkylenearyl;
vi) C3-C20substituted or unsubstituted cycloalkyl;
vii) C6-C20aryl;
viii) C5-C20heteroaryl units comprising one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, and mixtures thereof;
ix) two R4units can be taken together to form one or more aromatic or non-aromatic, heterocyclic or non-heterocyclic, single rings, fused rings, bicyclo rings, spiroannulated rings, or mixtures thereof, said rings comprising from 3 to 20 carbon atoms and one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, and mixtures thereof;
x) and mixtures thereof; G1and G2are each independently hydrogen, C1-C20linear or branched hydrocarbyl, —Y, —C(O)Y, and mixtures thereof; Y is C6-C10substituted or unsubstituted cyclic alkyl.
Figure US20020094938A1-20020718-C00086
wherein Z is oxygen or sulfur; m is from 1 to 3; R5units are selected from:
a) C6-C22substituted or unsubstituted linear alkyl
b) C6-C22substituted or unsubstituted branched alkyl;
c) C6-C22substituted or unsubstituted linear alkenyl;
d) C6-C22substituted or unsubstituted branched alkenyl;
e) C6-C22substituted or unsubstituted cycloalkyl;
f) C6-C22substituted or unsubstituted branched cycloalkyl;
g) C6-C22substituted or unsubstituted cycloalkenyl;
h) C6-C22substituted or unsubstituted branched cycloalkenyl;
i) C6-C22substituted or unsubstituted aryl;
j) C6-C22substituted or unsubstituted heterocyclicalkyl;
k) C6-C22substituted or unsubstituted heterocyclicalkenyl;
l) and mixtures thereof;
R6units comprise hydrogen or R5;
R7is independently selected from the group consisting of:
a) R6;
b) hydroxyl;
c) a carbonyl comprising unit having the formula:
—(CH2)xCOR8
wherein R8is:
i) —OH;
ii) —OR9wherein R9is hydrogen, C1-C15substituted linear alkyl, C11-C15unsubstituted linear alkyl, C1-C15substituted branched alkyl, C11-C15unsubstituted branched alkyl, C2-C22substituted or unsubstituted linear alkenyl, C3-C22substituted or unsubstituted branched alkenyl, or mixtures thereof,
iii) —N(R10)2wherein R10is hydrogen, C1-C6substituted or unsubstituted linear alkyl, C3-C6substituted or unsubstituted branched alkyl, or mixtures thereof;
iv) C1-C22substituted or unsubstituted linear alkyl;
v) C1-C22substituted or unsubstituted branched alkyl;
vi) C2-C22substituted or unsubstituted linear alkenyl;
vii) C3-C22substituted or unsubstituted branched alkenyl;
viii) C3-C22substituted or unsubstituted cycloalkyl;
ix) C6-C22substituted or unsubstituted aryl;
x) C6-C22substituted or unsubstituted heterocyclicalkyl;
xi) C6-C22substituted or unsubstituted heterocyclicalkenyl;
the index x is from 0 to 22;
d) alkyleneoxy units having the formula:
—[C(R11)2]y[C(R11)2C(R11)2O]zR11
wherein each R11is independently;
i) hydrogen;
ii) —OH;
iii) C1-C4alkyl;
iv) or mixtures thereof;
two R11units can be taken together to form a C3-C6spiroannulated 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; any two R7units can be taken together to form:
i) a carbonyl moiety;
ii) a C3-C6spiroannulated 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.
Figure US20020094938A1-20020718-C00088
iii) and mixtures thereof;
wherein each R4is independently selected from the group consisting of:
i) hydrogen;
ii) C1-C22substituted or unsubstituted, branched or unbranched alkyl;
iii) C2-C22substituted or unsubstituted, branched or unbranched alkenyl;
iv) C2-C20substituted or unsubstituted, branched or unbranched hydroxyalkyl;
v) C7-C20substituted or unsubstituted alkylenearyl;
vi) C3-C20substituted or unsubstituted cycloalkyl;
vii) C6-C20aryl;
viii) C5-C20heteroaryl units comprising one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, and mixtures thereof;
ix) two R4units can be taken together to form one or more aromatic or non-aromatic, heterocyclic or non-heterocyclic, single rings, fused rings, bicyclo rings, spiroannulated rings, or mixtures thereof, said rings comprising from 3 to 20 carbon atoms and one or more heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, and mixtures thereof;
x) and mixtures thereof; G1and G2are each independently hydrogen, C1-C20linear or branched hydrocarbyl, —Y, —C(O)Y, and mixtures thereof; Y is C6-C10substituted or unsubstituted cyclic alkyl;
Z is oxygen or sulfur; m is from 1 to 3;
R5units are selected from:
a) C6-C22substituted or unsubstituted linear alkyl
b) C6-C22substituted or unsubstituted branched alkyl;
c) C6-C22substituted or unsubstituted linear alkenyl;
d) C6-C22substituted or unsubstituted branched alkenyl;
e) C6-C22substituted or unsubstituted cycloalkyl;
f) C6-C22substituted or unsubstituted branched cycloalkyl;
g) C6-C22substituted or unsubstituted cycloalkenyl;
h) C6-C22substituted or unsubstituted branched cycloalkenyl;
i) C6-C22substituted or unsubstituted aryl;
j) C6-C22substituted or unsubstituted heterocyclicalkyl;
k) C6-C22substituted or unsubstituted heterocyclicalkenyl;
l) and mixtures thereof;
R6units comprise hydrogen or R5;
R7is independently selected from the group consisting of:
a) R6;
b) hydroxyl;
c) a carbonyl comprising unit having the formula:
—(CH2)xCOR8
wherein R8is:
i) —OH;
ii) —OR9wherein R9is hydrogen, C1-C15substituted linear alkyl, C11-C15unsubstituted linear alkyl, C1-C15substituted branched alkyl, C1-C15unsubstituted branched alkyl, C2-C22substituted or unsubstituted linear alkenyl, C3-C22substituted or unsubstituted branched alkenyl, or mixtures thereof,
iii) —N(R10)2wherein R10is hydrogen, C1-C6substituted or unsubstituted linear alkyl, C3-C6substituted or unsubstituted branched alkyl, or mixtures thereof;
iv) C1-C22substituted or unsubstituted linear alkyl;
v) C1-C22substituted or unsubstituted branched alkyl;
vi) C2-C22substituted or unsubstituted linear alkenyl;
vii) C3-C22substituted or unsubstituted branched alkenyl;
viii) C3-C22substituted or unsubstituted cycloalkyl;
ix) C6-C22substituted or unsubstituted aryl;
x) C6-C22substituted or unsubstituted heterocyclicalkyl;
xi) C6-C22substituted or unsubstituted heterocyclicalkenyl;
the index x is from 0 to 22;
d) alkyleneoxy units having the formula:
—[C(R11)2]y[C(R11)2C(R11)2O]zR11
wherein each R11is independently;
i) hydrogen;
ii) —OH;
iii) C1-C4alkyl;
iv) or mixtures thereof;
two R11units can be taken together to form a C3-C6spiroannulated 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;
any two R7units can be taken together to form:
i) a carbonyl moiety;
ii) a C3-C6spiroannulated 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.
US10/001,0292000-11-082001-11-02Photo-labile pro-fragrance conjugatesAbandonedUS20020094938A1 (en)

Priority Applications (12)

Application NumberPriority DateFiling DateTitle
US10/001,029US20020094938A1 (en)2000-11-082001-11-02Photo-labile pro-fragrance conjugates
US10/693,733US6987084B2 (en)2000-11-082003-10-24Photo-labile pro-fragrance conjugates
US11/148,688US7109153B2 (en)2000-11-082005-06-09Photo-labile pro-fragrance conjugates
US11/446,649US20060223726A1 (en)2000-11-082006-06-05Photo-labile pro-fragrance conjugates
US11/654,085US7262156B2 (en)2000-11-082007-01-17Photo-labile pro-fragrance conjugates
US11/880,028US7368415B2 (en)2000-11-082007-07-19Photo-labile pro-fragrance conjugates
US12/077,624US7534751B2 (en)2000-11-082008-03-20Photo-labile pro-fragrance conjugates
US12/411,566US20090186790A1 (en)2000-11-082009-03-26Photo-labile pro-fragrance conjugates
US12/603,066US20100040569A1 (en)2000-11-082009-10-21Photo-labile pro-fragrance conjugates
US12/768,805US20100210495A1 (en)2000-11-082010-04-28Photo-labile pro-fragrance conjugates
US12/903,418US20110028367A1 (en)2000-11-082010-10-13Photo-labile pro-fragrance conjugates
US13/046,842US20110165101A1 (en)2000-11-082011-03-14Photo-labile pro-fragrance conjugates

Applications Claiming Priority (2)

Application NumberPriority DateFiling DateTitle
US24681100P2000-11-082000-11-08
US10/001,029US20020094938A1 (en)2000-11-082001-11-02Photo-labile pro-fragrance conjugates

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US10/001,029AbandonedUS20020094938A1 (en)2000-11-082001-11-02Photo-labile pro-fragrance conjugates
US10/693,733Expired - Fee RelatedUS6987084B2 (en)2000-11-082003-10-24Photo-labile pro-fragrance conjugates
US11/148,688Expired - Fee RelatedUS7109153B2 (en)2000-11-082005-06-09Photo-labile pro-fragrance conjugates
US11/446,649AbandonedUS20060223726A1 (en)2000-11-082006-06-05Photo-labile pro-fragrance conjugates
US11/654,085Expired - Fee RelatedUS7262156B2 (en)2000-11-082007-01-17Photo-labile pro-fragrance conjugates
US11/880,028Expired - Fee RelatedUS7368415B2 (en)2000-11-082007-07-19Photo-labile pro-fragrance conjugates
US12/077,624Expired - LifetimeUS7534751B2 (en)2000-11-082008-03-20Photo-labile pro-fragrance conjugates
US12/411,566AbandonedUS20090186790A1 (en)2000-11-082009-03-26Photo-labile pro-fragrance conjugates
US12/603,066AbandonedUS20100040569A1 (en)2000-11-082009-10-21Photo-labile pro-fragrance conjugates
US12/768,805AbandonedUS20100210495A1 (en)2000-11-082010-04-28Photo-labile pro-fragrance conjugates
US12/903,418AbandonedUS20110028367A1 (en)2000-11-082010-10-13Photo-labile pro-fragrance conjugates
US13/046,842AbandonedUS20110165101A1 (en)2000-11-082011-03-14Photo-labile pro-fragrance conjugates

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Application NumberTitlePriority DateFiling Date
US10/693,733Expired - Fee RelatedUS6987084B2 (en)2000-11-082003-10-24Photo-labile pro-fragrance conjugates
US11/148,688Expired - Fee RelatedUS7109153B2 (en)2000-11-082005-06-09Photo-labile pro-fragrance conjugates
US11/446,649AbandonedUS20060223726A1 (en)2000-11-082006-06-05Photo-labile pro-fragrance conjugates
US11/654,085Expired - Fee RelatedUS7262156B2 (en)2000-11-082007-01-17Photo-labile pro-fragrance conjugates
US11/880,028Expired - Fee RelatedUS7368415B2 (en)2000-11-082007-07-19Photo-labile pro-fragrance conjugates
US12/077,624Expired - LifetimeUS7534751B2 (en)2000-11-082008-03-20Photo-labile pro-fragrance conjugates
US12/411,566AbandonedUS20090186790A1 (en)2000-11-082009-03-26Photo-labile pro-fragrance conjugates
US12/603,066AbandonedUS20100040569A1 (en)2000-11-082009-10-21Photo-labile pro-fragrance conjugates
US12/768,805AbandonedUS20100210495A1 (en)2000-11-082010-04-28Photo-labile pro-fragrance conjugates
US12/903,418AbandonedUS20110028367A1 (en)2000-11-082010-10-13Photo-labile pro-fragrance conjugates
US13/046,842AbandonedUS20110165101A1 (en)2000-11-082011-03-14Photo-labile pro-fragrance conjugates

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KR (1)KR100541785B1 (en)
CN (1)CN100595266C (en)
AR (1)AR032481A1 (en)
AT (1)ATE521691T1 (en)
AU (2)AU2571002A (en)
BR (1)BR0115192A (en)
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