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US 7,018,978 B2Granted
Fragrance pro-accords and aldehyde and ketone fragrance libraries
AssigneeThe Procter & Gamble Company
InventorsGregory Scot Miracle, Kenneth Nathan Price
Life of this patent
Estimating the term…
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.
Claims10
A molecule having formula:
- wherein:
- A.) X is oxygen or sulfur;
- B.) R and R1 are identical to the R and R1 of an aldehyde or ketone having the following fomula:
- wherein said aldehyde or ketone is selected from the group consisting of p-methyl phenylacetaldehyde, 2,4-decadienal, 2-octenal, 2-methyldecanal, undec-8-enal, methylnonyl acetaldehyde, 3-(4-t-butylphenyl)-propanal, 3-(4-methoxyphenyl)-2-methylpropanal, 3-(3,4-methylenedioxyphenyl)-2-methylpropanal, 3-(4-ethylpheny)-2,2-dimethylpropanal, 3-methyl-5-phenylpentanal, 2-ethyl-2-heptenal, 2,6-dimethyl-5-heptenal, 3,7-dimethyl-7-hydroxyoctan-1-al, 6-nonenal, 2,4-nonadienal, 2,6-nonadienal, 2-methyl decanal, 4-decenal, 9-decenal, 2,6,10-trimethyl-9-undecenal, bourgenonal, citronellyl oxyacetaldehyde, florhydral, 3-(4-hydroxy-4-methyl-pentyl)-3-cyclohexene-1-carboxaldehyde, 4-(4-hydroxy-4-methyl-pentyl)-3-cyclohexene-1-carboxaldehyde, 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde, γ-methyl ionone, α-iso-methyl ionone, α-irone, 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone, cis-jasmone, dihydrojasmone, α-ionone, β-ionone, l-carvone, 2-[2-(4-methyl-3-cyclohexenyl-1-yl)propyl]cyclopentan-2-one, allyl ionone, 1-(2-methyl-5-isopropyl-2-cyclohexenyl)-1-propanone, o-t-butylcyclohexanone, fenchone, α-damascone, β-damascone, δ-damascone, γ-damascone, β-damascenone, and methyl-7,3-dihydro-2H-1,5-benzodioxepine-3-one;
- C.) each R2, R3, and each R4 and R5 pair are independently:
- a.) H;
- b.) hydroxyl;
- c.) a carbonyl comprising unit having the formula:
- —(CH2)xCOR7
- wherein R7 is:
- (i) —OH;
- (ii) —OR8 wherein R8 is hydrogen, a substituted or unsubstituted, linear or branched moiety selected from the group consisting of C1–C15 alkyl, C2–C22 alkenyl, or mixtures thereof, wherein said substitution is not halogen;
- (iii) —N(R9)2 wherein R9 is hydrogen, C1–C6 substituted or unsubstituted linear alkyl, C3–C6 substituted or unsubstituted branched alkyl, or mixtures thereof;
- (iv) a substituted or unsubstituted, linear or branched moiety selected from the group consisting of C1–C22 alkyl, C2–C22 alkenyl, C3–C22 cycloalkyl,
- (v) a substituted or unsubstituted moiety selected from the group consisting of C6–C22 aryl, C6–C22 heterocyclicalkyl, C6–C22 heterocyclicalkenyl;
- the index x is from 1 to 22;
- d.) alkyleneoxy units having the formula:
- —(CR10R11)y(CHR12CHR13O)zR14
- wherein each R10, R11, and R12 is independently hydrogen, —OH, C1–C4 alkyl or mixtures thereof;
- each R13 and R14 is independently hydrogen, C1–C4 alkyl or mixtures thereof;
- R10 and R11 can be taken together to form a C3–C6 spiroannulated ring, carbonyl unit, or mixtures thereof;
- y has the value from 0 to 10, z has the value from 1 to 50;
- e.) a substituted or unsubstituted, linear or branched moiety selected from the group consisting of C1–C10 alkyl, C2–C10 alkenyl;
- f.) a substituted or unsubstituted moiety selected from the group consisting of C3–C15 cycloalkyl, C4–C15 cycloalkenyl, C6–C15 aryl, C6–C22 heterocyclicalkyl, C6–C22 heterocyclicalkenyl
- g.) a substituted or unsubstituted branched moiety selected from the group consisting of C4–C15 cycloalkyl, C5–C15 cycloalkenyl
- h.) and mixtures thereof;
- D.) R6 is:
- a.) C1–C10 substituted linear alkyl;
- b.) C3–C10 substituted branched alkyl;
- c.) C2–C10 substituted or unsubstituted linear alkenyl;
- d.) a substituted or unsubstituted branched moiety selected from the group consisting of C3–C10 alkenyl, C4–C15 cycloalkyl, C5–C15 cycloalkenyl;
- e.) a substituted moiety selected from the group consisting of C3–C15 cycloalkyl, C6–C15 aryl;
- f.) a substituted or unsubstituted moiety selected from the group consisting of C4–C15 cycloalkenyl, C6–C22 heterocyclicalkyl, C6–C22 heterocyclicalkenyl;
- g.) a carbonyl comprising unit having the formula:
- —(CH2)xCOR7
- wherein R7 is:
- (i)—OH;
- (ii) —OR8 wherein R8 is hydrogen, C1–C15 substituted linear alkyl, C11–C15 unsubstituted linear alkyl, C1–C15 substituted branched alkyl, C11–C15 unsubstituted branched alkyl, C2–C22 substituted or unsubstituted linear alkenyl, C3–C22 substituted or unsubstituted branched alkenyl, or mixtures thereof, wherein said substitution is not halogen or thioalkyl;
- (iii) —N(R9)2 wherein R9 is hydrogen, C1–C6 substituted or unsubstituted linear alkyl, C3–C6 substituted or unsubstituted branched alkyl, or mixtures thereof;
- (iv) a substituted or unsubstituted, linear or branched moiety selected from the group consisting of C1–C22 alkyl, C2–C22 alkenyl;
- (v) a substituted or unsubstituted moiety selected from the group consisting of C3–C22 cycloalkyl, C6–C22 aryl, C6–C22 heterocyclicalkyl, C6–C22 heterocyclicalkenyl;
- the index x is from 0 to 22;
- h.) alkyleneoxy units having the formula:
- —(CR10R11)y(CHR12CHR13O)zR14
- wherein each R10, R11, and R12 is independently hydrogen, —OH, C1–C4 alkyl or mixtures thereof;
- each R13 and R14 is independently hydrogen, C1–C4 alkyl or mixtures thereof, R10 and R11 can be taken together to form a C3–C6 spiroannulated ring, carbonyl unit, or mixtures thereof;
- y has the value from 0 to 10, z has the value from 1 to 50;
- i.) and mixtures thereof;
- E.) any two R2, R3, R4, R5, or R6 units can be taken together to form:
- a.) a carbonyl moiety;
- b.) a C3–C6 spiroannulated ring;
- c.) a heterocyclic aromatic ring comprising from 5 to 7 atoms;
- d.) a non-heterocyclic aromatic ring comprising from 5 to 7 atoms;
- e.) a heterocyclic ring comprising from 5 to 7 atoms;
- f.) a non-heterocyclic ring comprising from 5 to 7 atoms;
- g.) or mixtures thereof;
- and
- F.) the index n is 1 or 2.
55 more elements
A perfume comprising a molecule having the formula:
- wherein:
- A.) X is oxygen or sulfur;
- B.) R and R1 are identical to the R and R1 of an aldehyde or ketone having the following fomula:
- wherein said aldehyde or ketone is selected from the group consisting of p-methyl phenylacetaldehyde, cis-4-heptenal, 3,7-dimethyloctanal, 2,4-decadienal, tridecanal, tetradecanal, 3-phenylbutanal, 2,4-heptadienal, octanal, 2-octenal, 3,7-dimethyl-2,6-octadien-1-al, 3,7-dimethyl-6-octenal, 2-methyldecanal, undecenal, undec-8-enal, dodecanal, cinnamic aldehyde, heliotropin, vanillin, ethyl vanillin, methylnonyl acetaldehyde, 3-(4-t-butylphenyl)-propanal, 3-(4-methoxyphenyl)-2-methylpropanal, 3-(4-isopropylphenyl)-2-methylpropanal, 3-(3,4-methylenedioxyphenyl)-2-methylpropanal, 3-(4-ethylpheny)-2,2-dimethylpropanal, 3-methyl-5-phenylpentanal,
- the index x is from 1 to 22;
- d.) alkyleneoxy units having the formula:
- —(CR10R11)y(CHR12CHR13O)zR14
- wherein each R10, R11, and R12 is independently hydrogen, —OH, C1–C4 alkyl or mixtures thereof;
- each R13 and R14 is independently hydrogen, C1–C4 alkyl or mixtures thereof;
- R10 and R11 can be taken together to form a C3–C6 spiroannulated ring, carbonyl unit, or mixtures thereof;
- y has the value from 0 to 10, z has the value from 1 to 50;
- e.) a substituted or unsubstituted, linear or branched moiety selected from the group consisting of C1–C10 alkyl, C2–C10 alkenyl;
- f.) a substituted or unsubstituted moiety selected from the group consisting of C3–C15 cycloalkyl, C4–C15 cycloalkenyl, C6–C15 aryl, C6–C22 heterocyclicalkyl, C6–C22 heterocyclicalkenyl
- g.) a substituted or unsubstituted branched moiety selected from the group consisting of C4–C15 cycloalkyl, C5–C15 cycloalkenyl
- h.) and mixtures thereof;
- D.) R6 is:
- a.) C1–C10 substituted linear alkyl;
- b.) C3–C10 substituted branched alkyl;
- c.) C2–C10 substituted or unsubstituted linear alkenyl;
- d.) a substituted or unsubstituted branched moiety selected from the group consisting of C3–C10 alkenyl, C4–C15 cycloalkyl, C5–C15 cycloalkenyl;
- e.) a substituted moiety selected from the group consisting of C3–C15 cycloalkyl, C6–C15 aryl;
- f.) a substituted or unsubstituted moiety selected from the group consisting of C4–C15 cycloalkenyl, C6–C22 heterocyclicalkyl, C6–C22 heterocyclicalkenyl;
- g.) a carbonyl comprising unit having the formula:
- —(CH2)xCOR7
- wherein R7 is:
- (i) —OH;
- (ii) —OR8 wherein R8 is hydrogen, C1–C15 substituted linear alkyl, C11–C15 unsubstituted linear alkyl, C1–C15 substituted branched alkyl, C11–C15 unsubstituted branched alkyl, C2–C22 substituted or unsubstituted linear alkenyl, C3–C22 substituted or unsubstituted branched alkenyl, or mixtures thereof, wherein said substitution is not halogen or thioalkyl;
- (iii) —N(R9)2 wherein R9 is hydrogen, C1–C6 substituted or unsubstituted linear alkyl, C3–C6 substituted or unsubstituted branched alkyl, or mixtures thereof;
- (iv) a substituted or unsubstituted, linear or branched moiety selected from the group consisting of C1–C22 alkyl, C2–C22 alkenyl;
- (v) a substituted or unsubstituted moiety selected from the group consisting of C3–C22 cycloalkyl, C6–C22 aryl, C6–C22 heterocyclicalkyl, C6–C22 heterocyclicalkenyl;
- the index x is from 0 to 22;
- h.) alkyleneoxy units having the formula:
- —(CR10R11)y(CHR12CHR13O)zR14
- wherein each R10, R11, and R12 is independently hydrogen, —OH, C1–C4 alkyl or mixtures thereof;
- each R13 and R14 is independently hydrogen, C1–C4 alkyl or mixtures thereof, R10 and R11 can be taken together to form a C3–C6 spiroannulated ring, carbonyl unit, or mixtures thereof;
- y has the value from 0 to 10, z has the value from 1 to 50;
- i.) and mixtures thereof;
- E.) any two R2, R3, R4, R5, or R6 units can be taken together to form:
- a.) a carbonyl moiety;
- b.) a C3–C6 spiroannulated ring;
- c.) a heterocyclic aromatic ring comprising from 5 to 7 atoms;
- d.) a non-heterocyclic aromatic ring comprising from 5 to 7 atoms;
- e.) a heterocyclic ring comprising from 5 to 7 atoms;
- f.) a non-heterocyclic ring comprising from 5 to 7 atoms;
- g.) or mixtures thereof;
- and
- F.) the index n is 1.
44 more elements
A perfume comprising a molecule having the formula:
- wherein:
- A.) X is oxygen or sulfur;
- B.) R and R1 are identical to the R and R1 of an aldehyde or ketone having the following fomula:
- wherein said aldehyde or ketone is selected from the group consisting of phenylacetaldehyde, p-methyl phenylacetaldehyde, heptanal, cis-4-heptenal, 3,7-dimethyloctanal, 2,4-decadienal, tridecanal, tetradecanal, phenylbutanal, 3-phenyl, 2,4-heptadienal, octanal, 2-octenal, 3,7-dimethyl-2,6-octadien-1-al, 3,7-dimethyl-6-octenal, undecanal, 2-methyldecanal, undecenal, undec-8-enal, dodecanal, cinnamic aldehyde, heliotropin, vanillin, ethyl vanillin, methylnonyl acetaldehyde, 3-(4-t-butylphenyl)-propanal, 3-(4-methoxyphenyl)-2-methylpropanal, 3-(4-isopropylphenyl)-2-methylpropanal, 3-(3,4-methylenedioxyphenyl)-2-methylpropanal, 3-(4-ethylpheny)-2,2-dimethylpropanal, 3-methyl-5-phenylpentanal, 2-ethyl-2-heptenal, 2,6-dimethyl-5-heptenal, 3,7-dimethyl-7-hydroxyoctan-1-al, nonanal, 6-nonenal, 2,4-nonadienal, 2,6-nonadienal, decanal, 2-methyl decanal, 4-decenal, 9-decenal, 2,6,10-trimethyl-9-undecenal, anisaldehyde, bourgenonal, citronellyl oxyacetaldehyde, cyclamen aldehyde, florhydral, benzaldehyde, 3-(4-hydroxy-4-methyl-pentyl)-3-cyclohexene-1-carboxaldehyde, 4-(4-hydroxy-4-methyl-pentyl)-3-cyclohexene-1-carboxaldehyde, 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde, and p-methylphenoxyacetaldehyde, γ-methyl ionone, α-iso-methyl ionone, methyl β-naphthyl ketone, acetophenone, α-irone, 4-t-pentyl cyclohexanone, 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanone, cis-jasmone, dihydrojasmone, α-ionone, β-ionone, dihydro-β-ionone, l-carvone, 2-[2-(4-methyl-3-cyclohexenyl-1-yl)propyl]cyclopentan-2-one, allyl ionone, 1-(2-methyl-5-isopropyl-2-cyclohexenyl)-1-propanone, p-t-butylcyclohexanone, o-t-butylcyclohexanone, ethyl amyl ketone, fenchone, α-damascone, β-damascone, δ-damascone, γ-damascone, β-damascenone, menthone and methyl-7,3-dihydro-2H-1,5-benzodioxepine-3-one;
- C.) each R2, R3, and each R4 and R5 pair are independently:
- a.) H;
- b.) hydroxyl;
- c.) a carbonyl comprising unit having the formula:
- —(CH2)xCOR7
- wherein R7 is:
- (i) —OH;
- (ii) —OR8 wherein R8 is hydrogen, a substituted or unsubstituted, linear or branched moiety selected from the group consisting of C1–C15 alkyl, C2–C22 alkenyl, or mixtures thereof, wherein said substitution is not halogen;
- (iii) —N(R9)2 wherein R9 is hydrogen, C1–C6 substituted or unsubstituted linear alkyl, C3–C6 substituted or unsubstituted branched alkyl, or mixtures thereof;
- (iv) a substituted or unsubstituted, linear or branched moiety selected from the group consisting of C1–C22 alkyl, C2–C22 alkenyl, C3–C22 cycloalkyl,
- (v) a substituted or unsubstituted moiety selected from the group consisting of C6–C22 aryl, C6–C22 heterocyclicalkyl, C6–C22 heterocyclicalkenyl;
- the index x is from 1 to 22;
- d.) alkyleneoxy units having the formula:
- —(CR10R11)y(CHR12CHR13O)zR14
- wherein each R10, R11, and R12 is independently hydrogen, —OH, C1–C4 alkyl or mixtures thereof;
- each R13 and R14 is independently hydrogen, C1–C4 alkyl or mixtures thereof;
- R10 and R11 can be taken together to form a C3–C6 spiroannulated ring, carbonyl unit, or mixtures thereof;
- y has the value from 0 to 10, z has the value from 1 to 50;
- e.) a substituted or unsubstituted, linear or branched moiety selected from the group consisting of C1–C10 alkyl, C2–C10 alkenyl;
- f.) a substituted or unsubstituted moiety selected from the group consisting of C3–C15 cycloalkyl, C4–C15 cycloalkenyl, C6–C15 aryl, C6–C22 heterocyclicalkyl, C6–C22 heterocyclicalkenyl
- g.) a substituted or unsubstituted branched moiety selected from the group consisting of C4–C15 cycloalkyl, C5–C15 cycloalkenyl
- h.) and mixtures thereof;
- D.) R6 is:
- a.) C1–C10 substituted linear alkyl;
- b.) C3–C10 substituted branched alkyl;
- c.) C2–C10 substituted or unsubstituted linear alkenyl;
- d.) a substituted or unsubstituted branched moiety selected from the group consisting of C3–C10 alkenyl, C4–C15 cycloalkyl, C5–C15 cycloalkenyl;
- e.) a substituted moiety selected from the group consisting of C3–C15 cycloalkyl, C6–C15 aryl;
- f.) a substituted or unsubstituted moiety selected from the group consisting of C4–C15 cycloalkenyl, C6–C22 heterocyclicalkyl, C6–C22 heterocyclicalkenyl;
- g.) a carbonyl comprising unit having the formula:
- —(CH2)xCOR7
- wherein R7 is:
- (i) —OH;
- (ii) —OR8 wherein R8 is hydrogen, C1–C15 substituted linear alkyl, C11–C15 unsubstituted linear alkyl, C1–C15 substituted branched alkyl, C11–C15 unsubstituted branched alkyl, C2–C22 substituted or unsubstituted linear alkenyl, C3–C22 substituted or unsubstituted branched alkenyl, or mixtures thereof, wherein said substitution is not halogen or thioalkyl;
- (iii) —N(R9)2 wherein R9 is hydrogen, C1–C6 substituted or unsubstituted linear alkyl, C3–C6 substituted or unsubstituted branched alkyl, or mixtures thereof;
- (iv) a substituted or unsubstituted, linear or branched moiety selected from the group consisting of C1–C22 alkyl, C2–C22 alkenyl;
- (v) a substituted or unsubstituted moiety selected from the group consisting of C3–C22 cycloalkyl, C6–C22 aryl, C6–C22 heterocyclicalkyl, C6–C22 heterocyclicalkenyl;
- the index x is from 0 to 22;
- h.) alkyleneoxy units having the formula:
- —(CR10R11)y(CHR12CHR13O)zR14
- wherein each R10, R11, and R12 is independently hydrogen, —OH, C1–C4 alkyl or mixtures thereof;
- each R13 and R14 is independently hydrogen, C1–C4 alkyl or mixtures thereof, R10 and R11 can be taken together to form a C3–C6 spiroannulated ring, carbonyl Unit, or mixtures thereof;
- y has the value from 0 to 10, z has the value from 1 to 50;
- i.) and mixtures thereof;
- E.) any two R2, R3, R4, R5, or R6 units can be taken together to form:
- a.) a carbonyl moiety;
- b.) a C3–C6 spiroannulated ring;
- c.) a heterocyclic aromatic ring comprising from 5 to 7 atoms;
- d.) a non-heterocyclic aromatic ring comprising from 5 to 7 atoms;
- e.) a heterocyclic ring comprising from 5 to 7 atoms;
- f.) a non-heterocyclic ring comprising from 5 to 7 atoms;
- g.) or mixtures thereof;
- and
- F.) the index n is 2.
55 more elements
A method for preparing a fragrance delivery system comprises the step of:
- A.) combining at least 2 materials from a first group comprising materials having the formula:
- wherein X is oxygen or sulfur;
- each R2, R3, R6 and each R4 and R5 pair are independently:
- a.) hydrogen;
- b.) C1–C10 substituted or unsubstituted linear alkyl;
- c.) C3–C10 substituted or unsubstituted branched alkyl;
- d.) C2–C10 substituted or unsubstituted linear alkenyl;
- e.) C3–C10 substituted or unsubstituted branched alkenyl;
- f.) C3–C15 substituted or unsubstituted cycloalkyl;
- g.) C4–C15 substituted or unsubstituted branched cycloalkyl;
- h.) C4–C15 substituted or unsubstituted cycloalkenyl;
- i.) C5–C15 substituted or unsubstituted branched cycloalkenyl;
- j.) C6–C15 substituted or unsubstituted aryl;
- k.) C6–C22 substituted or unsubstituted heterocyclicalkyl;
- l.) C6–C22 substituted or unsubstituted heterocyclicalkenyl;
- m.) hydroxyl;
- n.) a carbonyl comprising unit having the formula:
- —(CH2)xCOR7
- wherein R7 is:
- (i) —OH;
- (ii) —OR8 wherein R8 is hydrogen, C1–C15 substituted or unsubstituted linear alkyl, C1–C15 substituted or unsubstituted branched alkyl, C2–C22 substituted or unsubstituted linear alkenyl, C3–C22 substituted or unsubstituted branched alkenyl, or mixtures thereof;
- (iii) —N(R9)2 wherein R9 is hydrogen, C1–C6 substituted or unsubstituted linear alkyl, C3–C6 substituted or unsubstituted branched alkyl, or mixtures thereof;
- (iv) C1–C22 substituted or unsubstituted linear alkyl;
- (v) C1–C22 substituted or unsubstituted branched alkyl;
- (vi) C2–C22 substituted or unsubstituted linear alkenyl;
- (vii) C3–C22 substituted or unsubstituted branched alkenyl;
- (viii) C3–C22 substituted or unsubstituted cycloalkyl;
- (ix) C6–C22 substituted or unsubstituted aryl;
- (x) C6–C22 substituted or unsubstituted heterocyclicalkyl;
- (xi) C6–C22 substituted or unsubstituted heterocyclicalkenyl;
- the index x is from 0 to 22;
- o.) alkyleneoxy units having the formula:
- —(CR10R11)y(CHR12CHR13O)yR14
- wherein each R10, R11, and R12 is independently;
- (i) hydrogen;
- (ii) —OH;
- (iii) C1–C4 alkyl;
- (iv) or mixtures thereof;
- R13 is:
- (i) hydrogen;
- (ii) C1–C4 alkyl;
- (iii) or mixtures thereof;
- R14 is:
- (i) hydrogen;
- (ii) C1–C4 alkyl;
- (iii) or mixtures thereof;
- R10 and R11 can be taken together to form a C3–C6 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 R2, R3, R4, R5, or R6 units can be taken together to form:
- (i) a carbonyl moiety;
- (ii) a C3–C6 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;
- the index n is an integer from 1 to 3;
- with at least 1 material from a second group comprising one or more fragrance raw materials;
- or combining at least 1 material from said first group with at least 2 materials from said second group,
- B.) optionally adding a catalyst;
- and
- C.) optionally isolating one or more heterocyclic pro-fragrances.
59 more elements
Dependencies are inferred from the claim text.