MXPA99001728A - Fragrance delivery systems - Google Patents
Fragrance delivery systemsInfo
- Publication number
- MXPA99001728A MXPA99001728A MXPA/A/1999/001728A MX9901728A MXPA99001728A MX PA99001728 A MXPA99001728 A MX PA99001728A MX 9901728 A MX9901728 A MX 9901728A MX PA99001728 A MXPA99001728 A MX PA99001728A
- Authority
- MX
- Mexico
- Prior art keywords
- carbon atoms
- substituted
- unsubstituted
- branched
- alkyl
- Prior art date
Links
- 239000003205 fragrance Substances 0.000 title claims abstract description 183
- 239000000203 mixture Substances 0.000 claims abstract description 272
- 239000002994 raw material Substances 0.000 claims abstract description 77
- 239000003599 detergent Substances 0.000 claims abstract description 32
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 267
- -1 β-naphthyl Chemical group 0.000 claims description 79
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 239000001257 hydrogen Substances 0.000 claims description 53
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- 239000004615 ingredient Substances 0.000 claims description 39
- 239000004094 surface-active agent Substances 0.000 claims description 33
- 125000003342 alkenyl group Chemical group 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 150000002431 hydrogen Chemical group 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000000304 alkynyl group Chemical group 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 239000011780 sodium chloride Substances 0.000 claims description 21
- 239000002304 perfume Substances 0.000 claims description 20
- 150000001298 alcohols Chemical class 0.000 claims description 19
- 239000000969 carrier Substances 0.000 claims description 19
- 125000005275 alkylenearyl group Chemical group 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000000654 additive Substances 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 238000004140 cleaning Methods 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 15
- 210000003491 Skin Anatomy 0.000 claims description 14
- 230000000996 additive Effects 0.000 claims description 14
- 150000001768 cations Chemical class 0.000 claims description 14
- 239000000975 dye Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 102000004190 Enzymes Human genes 0.000 claims description 12
- 108090000790 Enzymes Proteins 0.000 claims description 12
- 239000003974 emollient agent Substances 0.000 claims description 10
- 239000002736 nonionic surfactant Substances 0.000 claims description 10
- 230000003287 optical Effects 0.000 claims description 10
- 125000000129 anionic group Chemical group 0.000 claims description 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000007844 bleaching agent Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000003381 stabilizer Substances 0.000 claims description 7
- 239000003945 anionic surfactant Substances 0.000 claims description 6
- 125000004429 atoms Chemical group 0.000 claims description 6
- 125000002091 cationic group Chemical group 0.000 claims description 6
- 239000002738 chelating agent Substances 0.000 claims description 6
- 239000002270 dispersing agent Substances 0.000 claims description 6
- 230000001965 increased Effects 0.000 claims description 6
- 230000014759 maintenance of location Effects 0.000 claims description 6
- 230000002335 preservative Effects 0.000 claims description 6
- 239000003755 preservative agent Substances 0.000 claims description 6
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N 2,3-Dihydrogeraniol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims description 5
- RRAFCDWBNXTKKO-UHFFFAOYSA-N Eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 5
- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Chemical compound COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 claims description 5
- 239000004166 Lanolin Substances 0.000 claims description 5
- 229940039717 Lanolin Drugs 0.000 claims description 5
- 239000003082 abrasive agent Substances 0.000 claims description 5
- 239000012190 activator Substances 0.000 claims description 5
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 5
- 230000000111 anti-oxidant Effects 0.000 claims description 5
- 239000003963 antioxidant agent Substances 0.000 claims description 5
- 239000000945 filler Substances 0.000 claims description 5
- 230000000855 fungicidal Effects 0.000 claims description 5
- 239000000417 fungicide Substances 0.000 claims description 5
- 230000002070 germicidal Effects 0.000 claims description 5
- 239000003752 hydrotrope Substances 0.000 claims description 5
- 235000019388 lanolin Nutrition 0.000 claims description 5
- GLZPCOQZEFWAFX-UHFFFAOYSA-N (E)-Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 4
- BCFOOQRXUXKJCL-UHFFFAOYSA-M 4-amino-4-oxo-2-sulfobutanoate Chemical compound NC(=O)CC(C([O-])=O)S(O)(=O)=O BCFOOQRXUXKJCL-UHFFFAOYSA-M 0.000 claims description 4
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 4
- OOCCDEMITAIZTP-QPJJXVBHSA-N Cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 claims description 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N Phenethyl alcohol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 230000002708 enhancing Effects 0.000 claims description 4
- 239000002979 fabric softener Substances 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 239000002562 thickening agent Substances 0.000 claims description 4
- DGEPZINOUXMMAS-UHFFFAOYSA-N (2,4-dimethylcyclohexyl)methanol Chemical compound CC1CCC(CO)C(C)C1 DGEPZINOUXMMAS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 3
- 239000003093 cationic surfactant Substances 0.000 claims description 3
- 230000001143 conditioned Effects 0.000 claims description 3
- 239000003623 enhancer Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- DMXUBGVVJLVCPB-UHFFFAOYSA-N (2,4,6-trimethylcyclohex-3-en-1-yl)methanol Chemical compound CC1CC(C)=CC(C)C1CO DMXUBGVVJLVCPB-UHFFFAOYSA-N 0.000 claims description 2
- XGRCZWYTJSFHET-UHFFFAOYSA-N (2,4-dimethylcyclohex-3-en-1-yl)methanol Chemical compound CC1C=C(C)CCC1CO XGRCZWYTJSFHET-UHFFFAOYSA-N 0.000 claims description 2
- KHWTYGFHPHRQMP-UHFFFAOYSA-N (4-propan-2-ylcyclohexyl)methanol Chemical compound CC(C)C1CCC(CO)CC1 KHWTYGFHPHRQMP-UHFFFAOYSA-N 0.000 claims description 2
- WSTQLNQRVZNEDV-CSKARUKUSA-N (E)-4-methyldec-3-en-5-ol Chemical compound CCCCCC(O)C(\C)=C\CC WSTQLNQRVZNEDV-CSKARUKUSA-N 0.000 claims description 2
- NEHPIUGJDUWSRR-UHFFFAOYSA-N 1-(4-propan-2-ylcyclohexyl)ethanol Chemical compound CC(C)C1CCC(C(C)O)CC1 NEHPIUGJDUWSRR-UHFFFAOYSA-N 0.000 claims description 2
- FYMOBFDUZIDKMI-UHFFFAOYSA-N 2,2-dimethyl-3-(3-methylphenyl)propan-1-ol Chemical compound CC1=CC=CC(CC(C)(C)CO)=C1 FYMOBFDUZIDKMI-UHFFFAOYSA-N 0.000 claims description 2
- SXGYZCMGVZKIPJ-UHFFFAOYSA-N 2-methyl-4-phenylpentan-1-ol Chemical compound OCC(C)CC(C)C1=CC=CC=C1 SXGYZCMGVZKIPJ-UHFFFAOYSA-N 0.000 claims description 2
- OXYRENDGHPGWKV-UHFFFAOYSA-N 3-methyl-5-phenylpentan-1-ol Chemical compound OCCC(C)CCC1=CC=CC=C1 OXYRENDGHPGWKV-UHFFFAOYSA-N 0.000 claims description 2
- YXTHWTPUTHTODU-UHFFFAOYSA-M 3-oxodecanoate Chemical compound CCCCCCCC(=O)CC([O-])=O YXTHWTPUTHTODU-UHFFFAOYSA-M 0.000 claims description 2
- HDQVGGOVPFQTRB-UHFFFAOYSA-N 6,8-dimethylnonan-2-ol Chemical compound CC(C)CC(C)CCCC(C)O HDQVGGOVPFQTRB-UHFFFAOYSA-N 0.000 claims description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
- 230000001153 anti-wrinkle Effects 0.000 claims description 2
- 239000003518 caustics Substances 0.000 claims description 2
- 239000000645 desinfectant Substances 0.000 claims description 2
- 239000002480 mineral oil Substances 0.000 claims description 2
- 235000010446 mineral oil Nutrition 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- AMXYRHBJZOVHOL-UHFFFAOYSA-N nona-2,6-dien-1-ol Chemical compound CCC=CCCC=CCO AMXYRHBJZOVHOL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 239000006096 absorbing agent Substances 0.000 claims 1
- 230000000844 anti-bacterial Effects 0.000 claims 1
- 230000001166 anti-perspirant Effects 0.000 claims 1
- 239000003213 antiperspirant Substances 0.000 claims 1
- 239000003899 bactericide agent Substances 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 239000003349 gelling agent Substances 0.000 claims 1
- 230000002045 lasting Effects 0.000 claims 1
- 239000003883 ointment base Substances 0.000 claims 1
- 239000003380 propellant Substances 0.000 claims 1
- 125000005531 substituted alkyleneoxy group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 230000001629 suppression Effects 0.000 claims 1
- 239000007788 liquid Substances 0.000 abstract description 17
- 239000006210 lotion Substances 0.000 abstract description 15
- 239000002781 deodorant agent Substances 0.000 abstract description 6
- 239000006071 cream Substances 0.000 abstract description 4
- 239000002453 shampoo Substances 0.000 abstract description 4
- 230000002459 sustained Effects 0.000 abstract description 3
- 235000020127 ayran Nutrition 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 83
- 239000000243 solution Substances 0.000 description 52
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 239000003921 oil Substances 0.000 description 38
- 235000019198 oils Nutrition 0.000 description 37
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 36
- 239000000463 material Substances 0.000 description 35
- 235000019441 ethanol Nutrition 0.000 description 34
- 238000007792 addition Methods 0.000 description 31
- 150000002148 esters Chemical class 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- GLZPCOQZEFWAFX-JXMROGBWSA-N β-Geraniol Chemical compound CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 22
- 239000012071 phase Substances 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 19
- 229910052786 argon Inorganic materials 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 238000002390 rotary evaporation Methods 0.000 description 18
- 235000014113 dietary fatty acids Nutrition 0.000 description 17
- 239000000194 fatty acid Substances 0.000 description 17
- 150000004665 fatty acids Chemical class 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
- 239000006260 foam Substances 0.000 description 15
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 15
- ZCSHNCUQKCANBX-UHFFFAOYSA-N Lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 14
- 238000010828 elution Methods 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 238000002156 mixing Methods 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 239000011734 sodium Substances 0.000 description 13
- 235000007586 terpenes Nutrition 0.000 description 13
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- 150000002576 ketones Chemical class 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 235000015424 sodium Nutrition 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 150000003505 terpenes Chemical class 0.000 description 12
- 229910000323 aluminium silicate Inorganic materials 0.000 description 11
- 239000012267 brine Substances 0.000 description 11
- 239000004744 fabric Substances 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000003208 petroleum Substances 0.000 description 11
- 235000019645 odor Nutrition 0.000 description 10
- 229920005646 polycarboxylate Polymers 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- LYGORGFXVWVMSM-UHFFFAOYSA-N 3,7-dimethyl-1$l^{4},2,8-trithiabicyclo[3.3.0]octa-1(5),3,6-triene Chemical compound S1C(C)=CC2=S1SC(C)=C2 LYGORGFXVWVMSM-UHFFFAOYSA-N 0.000 description 9
- 239000000686 essence Substances 0.000 description 9
- 230000000670 limiting Effects 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000010792 warming Methods 0.000 description 9
- 239000005792 Geraniol Substances 0.000 description 8
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 8
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 description 8
- 229930008393 geraniol Natural products 0.000 description 8
- 229940113087 geraniol Drugs 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- ULDHMXUKGWMISQ-VIFPVBQESA-N (+)-(4S)-carvone Chemical compound CC(=C)[C@H]1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-VIFPVBQESA-N 0.000 description 7
- 230000001154 acute Effects 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 239000012230 colorless oil Substances 0.000 description 7
- XSNQECSCDATQEL-UHFFFAOYSA-N dihydromyrcenol Chemical compound C=CC(C)CCCC(C)(C)O XSNQECSCDATQEL-UHFFFAOYSA-N 0.000 description 7
- 229930008394 dihydromyrcenol Natural products 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- BPQQTUXANYXVAA-UHFFFAOYSA-N silicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 6
- UWKAYLJWKGQEPM-LBPRGKRZSA-N Linaloyl acetate Natural products CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 150000008051 alkyl sulfates Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 description 6
- 229930007744 linalool Natural products 0.000 description 6
- XNLBCXGRQWUJLU-UHFFFAOYSA-N naphthalene-2-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CC=C21 XNLBCXGRQWUJLU-UHFFFAOYSA-N 0.000 description 6
- 239000000123 paper Substances 0.000 description 6
- 229920001888 polyacrylic acid Polymers 0.000 description 6
- 150000004760 silicates Chemical class 0.000 description 6
- BZKBCQXYZZXSCO-UHFFFAOYSA-N sodium hydride Chemical compound [H-].[Na+] BZKBCQXYZZXSCO-UHFFFAOYSA-N 0.000 description 6
- 235000000346 sugar Nutrition 0.000 description 6
- 241000220317 Rosa Species 0.000 description 5
- MWOOGOJBHIARFG-UHFFFAOYSA-N Vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 150000007942 carboxylates Chemical class 0.000 description 5
- 229930007075 carvone Natural products 0.000 description 5
- 239000004927 clay Substances 0.000 description 5
- 229910052570 clay Inorganic materials 0.000 description 5
- 239000003240 coconut oil Substances 0.000 description 5
- 235000019864 coconut oil Nutrition 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000010457 zeolite Substances 0.000 description 5
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 4
- ULDHMXUKGWMISQ-UHFFFAOYSA-N 1-carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 4
- QZRKIGAZHXSODT-UHFFFAOYSA-M 3-naphthalen-2-yl-3-oxopropanoate Chemical compound C1=CC=CC2=CC(C(=O)CC(=O)[O-])=CC=C21 QZRKIGAZHXSODT-UHFFFAOYSA-M 0.000 description 4
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-phenylpropan-1-ol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
- UFLHIIWVXFIJGU-ARJAWSKDSA-N Cis-3-Hexen-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 description 4
- BJHIKXHVCXFQLS-UYFOZJQFSA-N Fructose Natural products OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 description 4
- GUBGYTABKSRVRQ-YOLKTULGSA-N Maltose Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)O[C@H]1CO)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 GUBGYTABKSRVRQ-YOLKTULGSA-N 0.000 description 4
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N Squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 4
- 241000209149 Zea Species 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- PSQYTAPXSHCGMF-BQYQJAHWSA-N beta-ionone Natural products CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 235000005824 corn Nutrition 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
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- 229930007850 β-damascenone Natural products 0.000 description 1
Abstract
The present invention relates to a fragrance delivery system which comprises one or more pro-accords, preferably&bgr;-ketoester pro-accords, which are capable of releasing mixtures of fragrance raw materials. The pro-accords which comprise the fragrance delivery systems are useful in delivering sustained fragrances to personal care items inter alia deodorants, body lotions or creams, sun tan lotions, shampoos, as well as liquid and granular laundry detergent compositions and hard surface cleaners.
Description
SYSTEMS OF ASSORTMENT OF FRAGRANCE
This application claims priority under the title
, United States Code 119 (c) according to provisional application Serial No. 60 / 024,117, filed on August 19, 1996.
FIELD OF THE INVENTION
The present invention relates to fragrance delivery systems suitable for use in personal care and personal hygiene articles, colognes, lotions, laundry detergent compositions, and hard surface cleaning compositions. The fragrance delivery systems comprise one or more pro-harmony molecules, each molecule capable of releasing one or more fragrance raw materials. Additionally, each pro-harmony is capable of releasing a different harmony (mixtures of fragrance raw materials) if it is used in a different type of composition (for example, laundry detergent versus deodorant with dial applicator).
BACKGROUND OF THE INVENTION
Humans have applied essences and fragrances to their skin since ancient times and have used fragrances and essences to expand the aesthetic quality of their environment among others, clothing and domestic space. Originally these aesthetically pleasing materials were commonly isolated in crude forms, such as resins, gums or essential oils from natural sources, among others, barks, roots, leaves and fruits of indigenous plants. These resins, gums and oils were applied directly to the body or diluted with water or another solvent, including in some cases, wine. With the advent of modern chemistry, the individual components responsible for the odor properties of these resins, gums and oils were isolated and subsequently characterized. In addition to the common "perfume vehicles", among others, fine perfumes, colognes, cologne waters, aftershave lotions, and a wide variety of personal care and hygiene items, fragrances and scents are also released on clothing during the washing procedure. It is well known that mixtures of fragrance raw materials or perfumes deposited on a surface lose intensity and can change their character over time, mainly due to factors such as differential evaporation and surface penetration. Many attempts have been made to minimize these drawbacks, but without notable success. Particularly, efforts have been made to prolong the diffusion, as well as to improve other characteristics of the fragrance materials, for example by increasing the concentration of fragrance raw materials or by the use of additives such as silicones, glycerol, polyethylene glycols and the like. . These additions, however, have not been adequate to increase the longevity of the scent of the fragrance. Accordingly, there remains a need in the art for a fragrance delivery system that can be formulated into any type of product used to release an aesthetically pleasing fragrance, inter alia, in personal care and hygiene products, and in detergent compositions. for laundry, including additives for rinsing and drying. Additionally, the fragrance released must have a sustained perception, consequently, the fragrance must be released slowly.
THE BACKGROUND TECHNIQUE
The following patents relate to the subject matter of fragrance ingredients. US 5,626,852 of Suffis and co-inventors, issued May 6, 1997; US 5,378,468 to Suffis and co-inventors, issued January 3, 1995; US 5,266,592 to Grub and co-inventors, issued November 30, 1993; US 5,081,111 to Akinoso and co-inventors, issued on January 14, 1992; US 4,994,266 to Wells, issued February 19, 1991; US 4,524,018 of Yemoto and co-inventors, issued June 18, 1985; US 3,849,326 to Jaggers and co-inventors, issued November 19, 1974; US 3,799,932 of Jaggers and co-inventors, issued December 18, 1973; JP 07-179,328 published July 18, 1995; JP OS-230496 published September 7, 1993; WO 96/38528 published December 5, 1996; WO 96/14827 published May 23, 1996; WO 95/04809 published February 16, 1995; and WO 95/16660 published June 22, 1995. Additionally, reference is included herein as P.M. Muller, D. Lamparsky Perfumes Art, Science & Technology Blackie Academic & Professional, (New York, 1994).
BRIEF DESCRIPTION OF THE INVENTION
The present invention covers the aforementioned needs inasmuch as it has been surprisingly discovered that a mixture of perfume or fragrance raw materials (harmonies) can be released from a pro-harmony precursor molecule, and that those pro-harmonies can serve as a system of fragrance supply in which a variety of fragrance mixtures are released depending on. the structure and design of the pro-armonia molecule. These pro-harmonies provide sustained retention of fragrance and perfume when applied to human skin, either directly or through an article for personal care or personal hygiene, such items for personal care and hygiene include, among others, deodorants, lotions or creams for the body, ointments, balms, ointments, antiseptics, tanning lotions, or shampoos. Additionally, the pro-harmonies of the present invention can be released onto the fabrics so that after the wash cycle has ended, the prorbanezes release the fragrance raw materials. The proto-harmonies described herein comprise fragrances in the form of stable and releasable "pro-fragrance". Additionally, the formulator can design compounds according to the present invention which can release different fragrance raw materials depending on the conditions of use. The pro-harmonies can be formulated in any product to be supplied, directly or indirectly, to human skin, clothing, or hard surfaces in which an aesthetically pleasing essence is desired. Once in contact with human skin, fabric or a surface, the pro-harmony becomes a primary fragrance mix at a rate that provides extended fragrance benefits. The fragrance delivery systems of the present invention may be a mixture of any number of pro-harmonies and may cover any desired fragrance or volatility "characteristic". The first aspect of the present invention relates to compositions that are applied to skin, fabrics, or hard surfaces, said compositions having increased fragrance retention and fragrance longevity. The appropriate compositions of the present invention are among other deodorants, body lotions or creams, suntan lotions, shampoos, granular and liquid laundry detergent compositions, fabric softeners for adding to rinse or dry, and hard surface cleaners, comprising one or more pro-armonia compounds with the formula:
wherein R is an alkoxy derived from an alcohol fragrance raw material; R1, R2 and R3 are each independently hydrogen, substituted or unsubstituted linear alkyl of 1 to 30 carbon atoms, unsubstituted or substituted branched alkyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkyl of 3 to 30 carbon atoms carbon, substituted or unsubstituted linear alkenyl of 2 to 30 carbon atoms, branched or unsubstituted branched alkenyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkenyl of 3 to 30 carbon atoms, linear alkynyl substituted or unsubstituted substituted from 2 to 30 carbon atoms, unsubstituted or substituted branched alkynyl of 3 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, substituted or unsubstituted alkylene of 2 to 20 carbon atoms, alkylenoxyalkyl substituted or unsubstituted of 3 to 20 carbon atoms, substituted or unsubstituted alkylenearyl of 7 to 20 carbon atoms, substituted or unsubstituted alkylenenoxy of 6 to 20 carbon atoms e carbon and mixtures thereof; provided that at least one of Rl, R2, R3 is a unit with the formula:
wherein R4, R5 and R6 are each independently hydrogen, substituted or unsubstituted linear alkyl of 1 to 30 carbon atoms, substituted or unsubstituted branched alkyl of 3 to 30 carbon atomsunsubstituted or substituted cyclic alkyl of 3 to 30 carbon atoms, linear substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, branched or unsubstituted branched alkoxy of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkoxy of 3 to 30 carbon atoms, unsubstituted or substituted linear alkenyl of 2 to 30 carbon atoms, branched or unsubstituted branched alkenyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkenyl of 3 to 30 carbon atoms, alkynyl linear substituted or unsubstituted of 2 to 30 carbon atoms, branched or unsubstituted substituted alkynyl of 3 to 30 carbon atoms, substituted or unsubstituted alkylenearyl of 6 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms of carbon, or R4, R5 and R6 can be taken together to form substituted or unsubstituted aryl of 6 to 30 carbon atoms; and mixtures thereof. The compositions of the present invention comprise at least about 0.01%, preferably from about 0.01% to 15%, more preferably from about 1% to 5%, much more preferably from about 0.01% to 1% by weight, of one or more of the β-ketoesters described herein. The present invention also relates to the use of the fragrance delivery system of the present invention to release fragrance harmonies when pro-harmonies are applied to a site if the pro-harmonies are released by a vehicle or carrier. The vehicle or carrier may be a liquid such as water, or an article containing a pro-harmony β-ketoester and is treated with an agent that catalyzes the release of the fragrance raw materials. These and other objects, features and advantages will become apparent to those skilled in the art from a reading of the following detailed description and the appended claims. All percentages, ratios and proportions indicated are by weight, unless otherwise specified. All temperatures are in degrees Celsius (° C) unless otherwise specified. All the documents cited, in their relevant part, are incorporated here by reference.
DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to a fragrance delivery system which deposits one or more "pro-harmony" fragrance compounds on the skin, hair, fabric, ceramic mosaic, linoleum, or other substrate during use or which may be applied to an article of manufacture in which pro-harmony is activated to release one or more fragrance raw materials. Because the pro-harmonies comprising the fragrance delivery system of the present invention generally have a higher molecular weight than non-combined fragrance raw materials and other "pro-fragrance type" compounds (ie, pro-fragrances that they only release a single equivalent of a fragrance raw material), these constitute a means for the effective delivery of two or more fragrance raw materials, which results in an improved longevity of the fragrance raw materials on the substrate.
Blends of fragrance materials are known to those skilled in the art of fragrances and perfumes as "harmonies." The term "harmony" as used herein, is defined as "a mixture of two or more ^ fragrance raw materials" which are Artistically combined to impart a pleasant fragrance, smell, scent, or characteristic. " For the purposes of the present invention, "fragrance raw materials" are defined herein as compounds that impart an odor, fragrance, scent, or aroma either alone or in combination with other "fragrance raw materials" that are considered aesthetically pleasing, preferably said compounds have a molecular weight of at least 100 g / mol. For the purposes of the present invention the term "pro-fragrance" is defined as "a β-ketoester that releases an alcohol of fragrance raw material" while a "pro-harmony" is defined as a "β-ketoester which liberates two or more fragrance raw materials ". For the purposes of the present invention, however, since a material that is "pro-fragrance" in one embodiment, can serve as "pro-harmony" in a different embodiment, the term "pro-fragrance" is used interchangeably with the term "pro-armonia" and each term can be used to equally indicate pro-fragrance molecules of ñ-ketoester, pro-harmony molecules of ß-ketoester, or both collectively. Typically the "fragrance raw materials" comprise among other alcohols, ketones, aldehydes, esters, ethers, nitriles, and cyclic alkenes and acyclics, especially terpenes. A list of common "fragrance raw materials" can be found in various reference sources, for example, "Perfume and Flavor Chemicals", Vols. I and II; Steffen Arclander Allured Pub. Co. (1994) and "Perfumes: Art, Science and Technology" Müller, P. M. and Lamparsky, D., Blackie Academic and Professional (1994) both incorporated herein by reference. As an example, but not by way of limitation, the fragrance harmonies released by the pro-harmonies of the present invention have "spirit", "character" or "note", which are described among others, such as rose, jasmine, lilac, Field lily, violet, orange, peach, watermelon, and lemon, or pro-harmony can release fragrance raw materials that provide a "fresh" or "clean" note, for example, linalool or dihydro ircenol. The harmony may be "modified" or "combined" in addition by the inclusion of pro-fragrances that provide acute or intermediate modifier notes which, as an additional benefit provided by the present invention, may be incorporated into the pro-harmony. For example, a "rose essence" can be combined with a "green" modifier to "change the character of the fragrance harmony". For the purposes of the present invention, only fragrance raw materials with a molecular weight of at least 100 g / mol are considered "preferred fragrance raw materials" according to the present invention. Therefore, low molecular weight materials among other methanol, ethanol, methyl acetate, ethyl acetate, and methyl formate, which are common components of the fragrance harmonies, are less preferred fragrance raw materials. However, the formulator may wish to release these materials of lower molecular weight (less than 100 g / mol molecular weight) as carriers, astringents, diluents, balancers, fixatives, or as other suitable additive materials. For the purposes of the present invention, the "sharp note" fragrance raw materials are defined as "fragrances having a high vapor pressure, and when applied to a paper pad, the vaporization takes place in 2 hours, and no scent residue; essentially, the initial impression of the perfume formulation is provided by sharp notes ".
For the purposes of the present invention, the "intermediate note" fragrance raw materials are defined as "fragrances having an average vapor pressure, and when applied to a paper pad, the aroma remains from about 2 hours until about 6 hours, essentially, the intermediate notes provide the support of the perfume formulation ". For the purposes of the present invention, the "grave note" fragrance raw materials are defined as "fragrances having a low vapor pressure and high retention, and when applied to a paper pad, the aroma remains for more than 6 hours, essentially, the serious notes provide the characteristic of the perfume formulation, the terms "acute note", "intermediate note" and
"Grade note" are well known to those skilled in the art of compositions containing fragrances. However, the reference to a specific fragrance raw material as "sharp note" in the present invention means that other experts in the techniques of fragrance-containing compositions may not categorize the same ingredient as an "intermediate note". The same applies to fragrance raw materials referred to as "intermediate notes" and "serious notes".
THE PRO-HARMONIES
The fragrance delivery systems of the present invention comprise one or more pro-harmonies with the formula:
wherein R is an alkoxy derived from an alcohol of fragrance raw material. Non-limiting examples of fragrance raw material alcohols include 2,4-dimethyl-3-cyclohexene-1-methanol (Floralol), 2,4-dimethyl-cyclohexane-methanol (dihydrofloralol), 5,6-dimethyl-1-methylethylbicyclo (2.2.1) hept-5-ene-2-methanol (Arbozole), a, a, -4-trimethyl-3-cyclohexen-l-methanol (a-terpinol), 2,4,6-trimethyl-3- cyclohexen-l-methanol (isociclogeraniol), 4- (l-methylethyl) -cyclohexane-methanol (Mayol), Oc-3, 3-trimethyl-2-norboranmethanol, 1,1-dimethyl-1- (4-methylcyclohex-3) enyl) methanol, 2-phenylethanol, 2-cyclohexylethanol, 2- (o-methylphenyl) -ethanol, 2- (m-methylphenyl) ethanol, 2- (p-ethylphenyl) ethanol, 6,6-dimethylbicyclo- (3.1. 1) hept-2-en-2-ethanol (nopol), 2- (4-methylphenoxy) -ethanol, 3,3-dimethyl-A2-β-norbornane ethanol (patchomenta), 2-methyl-2-cyclohexylethanol, 1 - (4-isopropylcyclohexyl) -ethanol, 1-phenylethanol, 1,1-dimethyl-2-phenylethanol, 1,1-dimethyl-2- (4-methyl-phenyl) ethanol, 1-phenylpropanol, 3-phenylpropanol, 2 -phenylpropanol (hydrotropic alcohol), 2- (cyclododecyl) propan -1-ol (Hydroxy-ambrano), 2, 2-d? Methyl-3- (3-methylphenyl) -propan-1-ol
(Majantol), 2-methyl-3-phenylpropanol, 3-phenyl-2-propen-l-ol
(cinnamyl alcohol), 2-methyl-3-phenyl-2-propen-1-ol (methyl-cinnamyl alcohol), an-pentyl-3-phenyl-2-propen-1-ol (cc-amyl-cinnamyl alcohol), 3 ethyl -hydroxy-3-phenylpropionate, 2- (4-methylphenyl) -2-propanol, 3- (4-methylcyclohex-3-ene) butanol, 2-methyl-4- (2, 2, 3-trimethyl-3) -cyclopentan-1-yl) butanol, 2-ethyl-4- (2,2,3-trimethyl-cyclopent-3-enyl) -2-buten-1-ol, 3-methyl-2-buten-1-ol (prenol), 2-methyl-4- (2, 2, 3-trimethyl-3-cyclopentan-1-yl) -2-buten-l-ol, ethyl 3-hydroxybutyrate, 4-phenyl-3-buten- 2-ol, 2-methyl-4-phenylbutan-2-ol, 4- (4-hydroxyphenyl) butan-2-one, 4- (4-hydroxy-3-methoxyphenyl) -butan-2-one, 3-methyl -pentanol, 3-methyl-3-penten-l-ol, l- (2-propenyl) cyclopentan-l-ol (plinol), 2-methyl-4-phenylpentanol
(Pamplefleur), 3-methyl-5-phenylpentanol (phenoxanol), 2-methyl-5-phenylpentanol, 2-methyl-5- (2,3-di-ethyltricyclo (2.2.1.0 (2'6)) hept-3 il) -2-penten-l-ol (santalol), 4-methyl-l-phenyl-2-pentanol, 5- (2,2,3-trimethyl-3-cyclopentenyl) -3-metipryntan-2-ol ( sandalore), (1-methyl-bicyclo (2.1.1) hepten-2-yl) -2-methylpent-l-en-3-ol, 3-methyl-l-phenylpentan-3-ol, 1, 2, - dimethyl-3- (1-methylethyl) cyclopentan-1-ol, 2-isopropyl-5-methyl-2-hexenol, cis-3-hexen-1-ol, trans-2-hexen-l-ol, 2-isopropenyl -4-methyl-4-hexen-1-ol (Lavanduloi), 2-ethyl-2-prenyl-3-hexenol, 1-hydroxymethyl-4-iso-propenyl-cyclohexene (Dihydrocuminyl alcohol),: -methyl- 4-isopropenylcyclohex-6-en-2-ol (carvenol), 6-methyl-3-isopropenylcyclohexan-1-ol
(dihydrocarvenol),: -methyl-4-iso-propenylcyclohexan-3-ol, 4-isopropyl-l-methylcyclohexan-3-ol, 4-tert-butylcyclohexanol, 2-tert-butylcyclohexanol, 2-tert-butyl- 4-methylcyclohexanol (rootanol), 4-isopropyl-cyclohexanol, 4-methyl-1- (1-ethylethyl) -3-cyclohexen-1-ol, 2- (5,6,6-trimethyl-2-norbornyl) cyclohexanol, isobornylcyclohexanol, 3,3,5-trimethylcyclohexanol, l-methyl-4-isopropylcyclohexan-3-ol, 1-methyl-4-isopropylcyclohexan-8-ol (dihydroterpinol), 1,2-dimethyl-3- (l-methylethyl) cyclohexan-1-ol, heptanol, 2,4-dimethylheptan-1-ol, 6-heptyl-5-hepten-2-ol (isolinalool), 2,4-dimethyl-2,6-heptadienol, 6,6-dimethyl -2-oxymethyl-bicyclo (3.11) hept-2-ene (mirtenol), 4-methyl-2,4-heptadien-ol, 3,4,5,6,6-pentamethyl-2-heptanol, 3, 6-dimethyl-3-vinyl-5-hepten-2-ol, 6,6-dimethyl-3-hydroxy-2-methylenebicyclo (3.1.1) heptane, 1,7,7-trimethylbicyclo (2.2.1) heptan-2-ol (dimetol), 2,6,6 trimethylbicyclo (1.3.3) eptan-2-ol, octanol, 2-octenol, 2-methyloctan-2-ol, 2-methyl-6-methylene-7- octen-2-ol (mircenol ), 7-methyloctan-l-ol, 3, 7-dimethyl-6-octenol,
3, 7-dimethyl-7-octenol, 3, 7-dimethyl-6-octen-l-ol
(citronellol), 3, 7-dimethyl-2,6-octadien-l-ol (geraniol), 3,7-dimethyl-2,6-octadien-l-ol (nerol), 3, 7-dimethyl-7- methoxyoctan-2-ol (osirol), 3, 7-dimethyl-l, 6-octadien-3-ol
(linalool), 3,7-dimethyloctan-l-ol (pelargol), 3,7-dimethyloctan-3-ol (etrahydrolinalool), 2, 4, -octadien-1-ol,
3,7-dimethyl-6-octen-3-ol (dihydrolinalool), 2,6-dimethyl-7-octen-2-ol (dihydromyrcenol), 2,6-dimethyl-5,7-octadien-2-ol, 4,7-dimethyl-4-vinyl-6-octen-3-ol, 3-methyloctan-3-ol, 2,6-dimethyloctan-2-ol, 2,6-dimethyloctan-3-ol, 3,6- dimethyloctan-3-ol, 2,6-dimethyl-7-octen-2-ol, 2,6-dimethyl-3,5-octadien-2-ol (muguol), 3-methyl-l-octen-3-ol , 7-hydroxy-3, 7, dimethyloctanal, 3-nonanol, 2,6-nonadien-l-ol, cis-6-nonen-1-ol, 6, 8-dimethylnonan-2-ol, 3- (hydroxymethyl) -2-nonanone, 2-nonen-l-ol, 2, 4-nonadien-l-ol, 3, 7-dimethyl-l, 6-nonadien-3-ol, decanol, 9-decenol, 2-benzyl-M -dioxa-5-ol, 2-decen-1-ol, 2, 4-decadien-l-ol, 4-methyl-3-decen-5-ol, 3,7,9-trimethyl-1,6-decadien -3-ol (isobutyl-linalool), undecanol, 10-undecen-l-ol, 2-dodecen-l-ol, 2,4-dodecanedien-l-ol, 2,7, ll-trimethyl-2,6, 10-dodecatrien-l-ol (farnesol), 3,7,11-trimethyl-1, 6, 10-dodecatrien-3-ol (nerolidol), 3,7,11,15-tetramethylhexadec-2-en-l- ol (phytol), 3,7,11,15-tetramethylhexadec-l-en-3-ol (iso phytol), benzyl alcohol, alcohol p-methoxybenzyl (anisyl alcohol), para-cyme-7-ol (cuminyl alcohol), 4-methylbenzyl alcohol, 3,4-methylenedioxybenzyl alcohol, methyl salicylate, benzyl salicylate, cis-3-hexenyl salicylate, salicylate n-pentyl, 2-pentylethyl salicylate, n-hexyl salicylate, 2-methyl-5-isopropylphenoi, 4-ethyl-2-methoxyphenol, 4-allyl-2-methoxyphenol eugenol), 2-methoxy-4- (1 -propenyl) phenol (isoeugenol), 4-allyl-2,6-dimethoxy-phenoxy, 4-tert-butylphenol, 2-ethoxy-4-methylphenol, 2-methyl-4-vinylphenol, 2-isopropyl-5-methylphenol ( thymol), pentyl ortho-hydroxybenzoate, ethyl 2-hydroxybenzoate, 2,4-dihydroxy-3,6-dimethylbenzoate methyl, 3-hydroxy-5-methoxy-1-methylbenzene, 2-tert-butyl-4 -methyl-1-hydroxybenzene, l-ethoxy-2-hydroxy-4-propenylbenzene, 4-hydroxytoluene, 4-hydroxy-3-methoxybenzaldehyde, 2-ethoxy-4-hydroxy-benzaldehyde, decahydro-2-naphthol, 2, 5 , 5-trimethyl-octahydro-2-naphthol, 1,3,3-trimethyl-2-norbornazole (phenchol), 3a, 4, 5, 6, 7, 7a-hexahydro-2,4-dimethyl-4, 7- methane o-lH-inden-5-ol, 3a, 4, 5, 6, 7, 7a-hexahydro-3, 4-dimethyl-4,7-methano-lH-inden-5-ol, 2-methyl-2- vinyl-5- (l-hydroxy-l-methylethyl) tetrahydrofuran, ß-caryophyllenyl alcohol, vanillin and mixtures thereof. More preferably, the fragrance raw material alcohol is selected from the group consisting of cis-3-hexen-1-ol, hawtanol (mixture of 2- (o-methylphenyl) -ethanol, 2- (m-methylphenyl) ethanol, and - (p-methylphenyl) ethanol), heptan-1-ol, decan-1-ol, 2,4-dimethylcyclohexanemethanol, 4-methylbutan-1-ol, 2,4-b-methyl-3-cyclohexene-1 methanol, 4- (1-methylethyl) cyclohexane ethanol, 3- (hydroxy-methyl) -2-nonanone, octan-1-ol, 3-phenylpropanol, Rhodinol 70 (mixture of 3,7-dimethyl-7-octenol, 3 , 7-dimethyl-6-octenol), 9-decen-l-ol, OR-3, 3-trimet? I -? - norborane-methanol, 3-cyclohexylpropan-l-ol, 4-methyl-l-feml- 2-pentanol, 3,6-dimethyl-3-vinyl-5-hepten-2-ol, phenyl ethyl methanol; propyl benzylmethanol, 1-methyl-4-isopropenylcyclohexan-3-ol, 4-isopropyl-1-methylcyclohexan-3-ol (menthol), 4-tert-butylcyclohexanol, 2-tert-butyl-4-methylcyclohexanol, 4-isopropyl-cyclohexanol , trans-decahydro-β-naphthol, 2-tert-butylcyclohexanol, 3-phenyl-2-propen-1-ol, 2,7,7-trimethyl-2,6,6-dodecatrien-1-ol, 3.7 -dimethyl-2, 6-octadien-l-ol (geraniol), 3, 7-dimethyl-2, 6-octadien-1-ol (nerol), 4-methoxybenzyl alcohol, benzyl alcohol, 4-allyl-2-methoxyphenol , 2-methoxy-4- (1-propenyl) phenol, vanillin, ethyl vanillin, and mixtures thereof. R1, R2 and R3 are independently hydrogen, substituted or unsubstituted linear alkyl of 1 to 30 carbon atoms, unsubstituted or substituted branched alkyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkyl of 3 to 30 carbon atoms , substituted or unsubstituted linear alkenyl of 2 to 30 carbon atoms, branched or unsubstituted branched alkenyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic ainyl of 3 to 30 carbon atoms, substituted or unsubstituted linear alkynyl of 2 to 30 carbon atoms, unsubstituted or substituted branched alkynyl of 3 to 30 carbon atoms, aryl of 6 to 30 carbon atoms, unsubstituted substituted alkylexy of 2 to 20 carbon atoms, substituted or unsubstituted alkylene-alkyl of 3 at 20 carbon atoms, substituted or unsubstituted alkylenearyl of 7 to 20 carbon atoms, substituted or unsubstituted alkylenearyl of 6 to 20 carbon atoms, and mixtures thereof, provided that at least one Rl, R2 or R3 is a unit with the formula:
wherein R 4, R 5, and R 6 are each independently hydrogen, substituted or unsubstituted linear alkyl of 1 to 30 carbon atoms, unsubstituted or substituted branched alkyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkyl of 1 at 30 carbon atoms, substituted or unsubstituted linear alkoxy of 2 to 30 carbon atoms, branched or unsubstituted branched alkoxy of 3 to 30 carbon atoms, unsubstituted or substituted cyclic alkoxy of 3 to 30 carbon atoms, linear alkenyl substituted or unsubstituted of 2 to 30 carbon atoms, unsubstituted or substituted branched alkenyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkenyl of 3 to 30 carbon atoms, substituted or unsubstituted linear alkynyl of 2 to 30 carbon atoms, substituted or unsubstituted branched alkynyl of 3 to 30 carbon atoms, substituted or unsubstituted alkylenearyl of 6 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, or R4, R5 and R6 can be taken together to form substituted or unsubstituted aryl of 6 to 30 carbon atoms; and mixtures thereof. Preferably at least two units R1, R2 or R3 are hydrogen. In one embodiment of the present invention, preferably the units R4, R5 and R6 are each hydrogen. Further, preferably when two units R 4, R 5 and R 6 are hydrogen, the remaining unit is substituted or unsubstituted linear alkyl of 1 to 20 carbon atoms, substituted or unsubstituted branched alkyl of 3 to 20 carbon atoms, substituted cyclic alkyl or unsubstituted from 3 to 20 carbon atoms, more preferably methyl. Also preferably R4, R5 and R6 are taken together to form a substituted or unsubstituted aryl unit of 6 to 30 carbon atoms, preferably phenyl and substituted or unsubstituted naphthyl. For the purposes of the present invention, the term "substituted" as applied to linear alkyl, branched alkyl, cyclic alkyl, linear alkenyl, branched alkenyl, cyclic alkenyl, branched alkoxy, cyclic alkoxy, alkynyl, and branched alkynyl, is defined as "carbon chains comprising substituents other than chain branches of carbon atoms", for example, other than branched alkyl units (eg, isopropyl, isobutyl). Non-limiting examples of "substituents" include hydroxy, alkoxy of 1 to 12 carbon atoms, preferably methoxy; branched alkoxy of 3 to 12 carbon atoms, preferably isopropoxy; cyclic alkoxy of 3 to 12 carbon atoms, preferably methoxy; branched alkoxy of 3 to 12 carbon atoms, preferably isopropoxy; cyclic alkoxy of 3 to 12 carbon atoms, nitrile, halogen, preferably chlorine and bromine, more preferably chlorine; nitro; morpholino; cyano; carboxyl; non-limiting examples of which are -CHO; -C02"M +, -C02R9; -CONH2, -CONHR9; -CONR92; wherein R9 is a linear or branched alkyl of 1 to 12 carbon atoms; S03-Mt; OS03-M; -N (Ri0):, - and N + (Ri?), X ~ wherein each RIO is independently hydrogen or alkyl of 1 to 4 carbon atoms, and mixtures thereof, wherein M is hydrogen or a water-soluble cation, and X is chlorine, bromine , iodo, or other water soluble anion For the purposes of the present invention, substituted or unsubstituted alkyleneoxy units are defined as the portions having the formula:
R8 I - (CHCH0) R7
wherein R7 is hydrogen; R8 is hydrogen, methyl, ethyl, and mixtures thereof; the subscript x is from 1 to about 10. For the purposes of the present invention the substituted or unsubstituted alkyleneoxyalkyl is defined as the portions having the formula:
R8 I - (CH2CHO) x (CH2) and R7
wherein R7 is hydrogen, alkyl of 1 to 18 carbon atoms, alkoxy of 1 to 4 carbon atoms, and mixtures thereof. R8 is hydrogen, methyl, ethyl and mixtures thereof, the subscript x is from 1 to about 10 and the subscript y is from 2 to about 18. For the purposes of the present invention, the substituted or unsubstituted aryl units they are defined as the phenyl portions that have the formula:
R7
Rß
or the a- and ß-naphthyl portions having the formula:
wherein R7 and R8 may be substituted in any ring, alone or in combination, and R7 and R8 are each independently hydrogen, hydroxy, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms, branched alkoxy of 3 to 6 carbon atoms, nitrile, halogen, nitro, morpholino, cyano, carboxyl (-CHO; -C02-M +; C02R9; -CONH2; -CONHR9; -ConR92; wherein R9 is linear or branched alkyl of 1 to 12 carbon atoms), -S03"M +, OS03-M +, -N (R10) 2, and -N * (R10) 3X- wherein each RIO is independently hydrogen, alkyl of 1 to 4 carbon atoms, or mixtures thereof, R7 and R8 are preferably hydrogen, alkyl of 1 to 6 carbon atoms, C02-Mt, -SO - * - M ', - S03-Mt, and mixtures thereof more preferably R7 or R8 is hydrogen and the other portion is from 1 to 6 carbon atoms, where M is hydrogen or a water-soluble cation and X is chlorine, bromine, iodine, or other water-soluble anion. from others to Water-soluble nions include organic species such as fumarate, succinate, tartrate, oxalate and the like, inorganic species including sulfate, bisulfate, phosphate and the like. For purposes of the present invention, substituted or unsubstituted alkylenearyl units are defined as portions having the formula:
wherein R7 and R8 are each independently hydrogen, hydroxy, alkoxy of 1 to 4 carbon atoms, nitrile, halogen, nitro, carbonyl (-CHO; -C02-M +; -C02R9; -CONH2; - CONHR9; -CONR92; wherein R9 is linear or branched alkyl of 1 to 12 carbon atoms), amino, alkylamino, and mixtures thereof, p is from 1 to about 14; M is hydrogen or a water-soluble cation. For the purposes of the present invention, the alkylenoxyaryl units are defined as the portions having the formula:
wherein R7 and R8 are each independently hydrogen, hydroxy, alkoxy of 1 to 4 carbon atoms, nitrile, halogen, nitro, carboxyl (-CH0; -C02-Mt; -C02R3; -CONH ?; CONHR9; -CONR92; wherein R9 is linear or branched alkyl of 1 to 12 carbon atoms), amino, alkylamino, and mixtures thereof, q is from 1 to about 14; M is hydrogen or a water-soluble cation. Surprisingly, the pro-harmonies comprising the fragrance delivery systems of the present invention are capable of releasing at least one fragrance raw material, preferably the pro-harmonies release two or more fragrance raw materials. For example, the 3-7-dimethyl-l, 6-octadien-3-yl 3- (ß-naphthyl) -3-oxo-propionate proarmony, having the formula:
frees, depending on the conditions of use, at least two fragrance raw materials including linalool, ß-naphthylmethyl ketone, myrcene, a-terpinolene, and A-3-carene. The pro-harmonies comprising the fragrance delivery systems of the present invention are capable of releasing their fragrance compounds by more than a single chemical mechanism, a point that is key to the variety of fragrance raw materials that are released from a only composed pro-harmony. Accordingly, depending on the wishes of the formulator, the pro-harmonies of the present invention are capable of releasing a different mixture of fragrance raw materials depending on the release of the release medium. For example, the 3- (ß-naphtenyl) -3-oxo-propionate 3,7-dimethyl-l, 6-octadien-3-yl proarmony produces a different harmony when the release of fragrance raw material is experienced in water , that when said pro-harmony is subjected to the high temperature typical of an automatic clothes dryer or an iron. Typically the pro-harmonies of the present invention release a mixture of alcohols, esters, ketones, hydrocarbon materials, especially terpenes, with aesthetically pleasing qualities, and mixtures thereof. For the purposes of the present invention, the term "hydrocarbyl material" is defined as a compound that essentially comprises only carbon and hydrogen among other alkanes, alkenes, and alkynes, whether linear, cyclic, branched, - combinations thereof. An example of a hydrocarbyl material that is capable of being released by a pro-harmony of the present invention is mircene. For the purposes of the present invention the term "terpene" is used to designate hydrocarbons among others myrcene, thymonene and Ot-terpinene. However, experts in both the perfume technique and organic chemistry recognize that geraniol and nerol which are included in the list of "fragrance raw material alcohols" above, are also terpenes. Throughout the present specification the term "terpene" is used interchangeably with "hydrocarbyl" and when "terpene" is used widely, it refers to all alcohols, ketones, alkenes, etc., which are generally considered terpenes, and when the term "terpene" is used in a strict sense, it refers primarily to alkanes, alkenes, etc., which typically have 10 carbon atoms (terpenes) or 15 carbon atoms (sesquiterpenes). The formulator can, however, adjust the conditions of use so that the simple fragrance raw materials are released by the pro-harmony. For example, a β-ketoester pro-fragrance prepared from dihydromyrcenol and capable of releasing dihydromyrcenol as well as other fragrance raw materials can be formulated in a composition that allows only the release of dihydromyrcenol until the conditions of use are changed or adjusted in such a way that the other fragrance raw materials can be supplied. Additionally, the pro-harmonies can be prepared in such a way that they release different fragrance raw materials under different conditions. For example, while a garment is drying, a harmony of fragrance is released, and a second harmony of fragrance is released when the garment is dry and hung in a closet. Examples of alcohols releasable by the pro-harmonies are those described above and are typically the fragrance raw material alcohols used to form the predecessor compounds. However, during the fragrance raw material release process, the fragrance raw material alcohols are capable of undergoing further modifications, including isomerization and / or rearrangement. Consequently, in addition to the original alcohol used to form the predecessor pro-harmony ester, the additional alcohols can be formed by transformations that occur during the release process. Depending on the selections that the formulator makes when designing the pro-harmony molecules in the formulation of a fragrance delivery system according to the present invention, these transformations can take place to a greater or lesser degree. Non-limiting examples of releasable terpenes by the pro-harmonies of the present invention include the hydrocarbyl materials myrcene, ocimene, β-farnesene, cis-alkylene, trans-alkylene, carvomentene, limonene, terpinene, gamma-terpinene, terpinolene, a -frenlandrene, β-phellandrene, 2-carene, 3-carene, α-pinene, β-pinene, camphene, and other terpenes, for example, (-) - (2S, 4R) -2- (2-methyl-1) - propenyl) -4-methyltetrahydropyran (cis-rose oxide), (-) - (2S, 4S) -2- (2- (2-methyl-1-propenyl) -4-methyltetrahydropyran (trans-rose oxide) , 2-methyl-2-vinyl-5- (OE-hydroxyisopropyl) tetrahydrofuran (linalool oxide), and mixtures thereof.
Non-limiting examples of ketones that are releasable by the pro-harmonies of the fragrance delivery systems of the present invention are a-damascone, ß-damascone, d-damascone, ß-damascenone, muscone, 3,3-dimethylbutanone, methylphenyl ketone (acetophenone), 4-phenylbutan-2-one (benzylacetone), 2-acetyl-3, 3-dimethylnorbornane (camek dh), 6, 7-dihydro-l, 1, 2, 3, 3-pentamethyl- (5H) -maanone tcash were), 4- (1, 3) -benzodioxol-5-yl-3-buten-2-one, casanone), 4- (3,4-methylenedioxyphenyl) -2-butanone (dulcimi), 3 -octanone, 6-acetyl-l, 2, 3, 4-tetrahydronaphthalencetona (florantone t), ethyl-2-n-hexyl acetoacetate (gelsone), 2,6-dimethylundeca-2,6-dien-10-one, 6, 10-dimethyl-5, 9-undecadien-2-one, 3,3-dimethylcyclohexylmethylketone (herbac), 4- (2,6,6-trimethyl-l-cyclohexen-1-yl) -3-buten-2 -one (ß-ionone), 4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one (α-ionone), 3-methyl-4- (2, 6, 6-trimethyl-l-cyclohexen-l-yl) -3-buten-2-one (U-methylionone), 4- (2,6,6-trimethyl-2-cyclone) ohexen-1-yl) -3-methyl-3-buten-2-one (gamma-methionionone), 3-methyl-4- (2,6-trimethyl-2-cyclohexen-1-yl) -3-buten- 2-one (Irisantem), 4- (2,3,5-trimethyl-4-cyclohexen-1-yl) -3-buten-2-one (iritone), 4-methyl- (2,5,6,6) -tetramethyl-2-cyclohexen-l-yl) -3-buten-2-one (a-ionone), 1,2,3,4,5,6,7,8-octahydro-2, 3, 8, 8 -tetramethyl-2-acetonaphthone 'isociclomona e), 7-acet? ll, 2, 3, 4, 5, 6, 7, 8-octah? dro-1, 1, 6, 7-tetramet? lnaphthalene (Iso E Super ©), acetyldiammine (Koavone®), ethylamyl ketone, 2-acetonaphthone, cear- ^ - enylmethyl ketone (methycryril), 2,3,6-methylmethoxyl-4- (1,1-methoxetone) (methylcyclo cytronic), hexahydroacetophenone
(methylcyclohexyl ketone), 6-methyl-3,5-heptadien-2-one, 6-methyl-5-hepten-s-one, 2-octanone, 3- (hydroxymethyl) -2-nonanone, 4- acet? ^ - l, ld? met? l-6-ter-but? l? ndano (mdanona de mosgo), 2,6-d? n? trc-3, 5-d? met? l-4-acet ? l-ter-but? lbenceno
(moss ketone), l-para-menten-6-? l propanone (nerona), para-methoxyacetophenone (acetamsol), 6-acetyl-l, 1, 2, 3, 3, 5-hexametilindane (Phantolid®), 7-acetyl-l, 1, 3, 4, 4, 6-hexadimetiltetralma (Tonalid®, Musk Plus®), 5-acetyl-3-? Soprop? L-1, 1,2,6-tetramet? L mdano ( Traseolide 70®), methyl-2, 6, 10-trimet? L-2, 5, 9-c? Clododecatr? Ene-l-? L ketone
(Trimofix O®), methylcedrilone (Vertofix Coeur®), 4- (4-hydroxy? -3-methox? Phen?) -2-butanone, cis-jasmone, dihydrojasmone, α-ionone, ß-ionone, dihydro- β-ionone, 4- (4-hydroxyphenyl) butan-2-one, 1-carvone, 5-cyclohexadecen-l-one, decatone, 2- (2- (4-methyl-3-cyclohexenyl-1-yl) propyl ) cyclopentan-2-one, 2-sec-butylcyclohexanone, allylonone, α-ketone, geranylacetone, 1- (2-methyl-5-isopropyl-2-cyclohexenyl) -1-propanone, acetyl diisoamylene, methyl cyclocitrin, 4-s -pentylcyclohexanone, pt-butylcyclohexanone, ot-butyicyclohexanone, menthone, methyl-7, 3-dihydro-2H-1, 5-benzoa? oxepin-3-one, fencona, methyl hydroxynaphthyl ketone, and mixtures thereof. In accordance with the present invention all the isomers of a fragrance raw material either in the form of the harmony or the fragrance raw material liberated, are suitable for use in the present invention. When optical isomers are possible, the fragrance raw materials may be included as the separate chemical isomer or as the combined racemic mixture. For example, 3,7-dimethyl-6-octen-1-ol, commonly known to those skilled in the art as β-citronlol or cefrole, comprises a pair of optical isomers, R- (+) - β-citronellol and S - (-) - ß-citronellol. Each of these materials separately or as a racemic pair are suitable for use as fragrance raw materials in the present invention. However, those skilled in the art of fragrances, by using the present invention, should not neglect the olfactory differences that individual optical isomers, mixtures of optical isomers or mixtures of positional isomers impart. By way of example, carvone, 2-methyl-5- (1-methyletenyl) -2-cyclohexene-1-one, exists as 2 isomers: d-carvone and 1-carvone. The d-carvone is found in caraway oil and emits a fragrance completely different from 1-carvone, which is found in the oil of peppermint. According to the present invention, a pro-harmony releasing d-carvone will result in an essence or fragrance different from one that liberates 1-carvone. The same applies for 1-carvona. In addition, the isomers, such as the cis / trans isomers, for example, nerol (3,7-dimethyl-cis-2,6-octadien-1-ol) and geraniol (3,7-dimethyl-trans-2,6- octadien-l-ol), are well known to those skilled in the art of perfumery, and these two terpene alcohols, which are commonly presented as mixtures, have different fragrance characteristics. Consequently, when formulating fragrance raw materials containing mixtures of isomers such as nerol / geraniol, the formulator must also take into account that different sources of raw material have different proportions of isomers. An example of a preferred pro-harmony is 3- (7-dimethyl-l, 6-octadien-3-yl 3- (β-naphthyl) -3-oxo-propionate with the formula:
which releases at least the alcohol raw material of fragrance linalool, which has the formula:
and the ketone raw material of fragrance, methylnaphthyl ketone, with the formula:
A further example of a preferred pro-harmony includes 2,6-dimethyl-7-octen-2-yl 3- (4-methoxyphenyl) -3-oxo-propionate, having the formula:
which releases at least the alcohol of fragrance raw material, dihydromyrcenol, with the formula:
and the ketone raw material of fragrance, methyl-4-methoxyphenyl ketone, which has the formula:
Further non-limiting examples of preferred pro-harmonies include 3,7-dimethyl-l, 6-octadien-3-yl 3- (a-naphthyl) -3-oxo-propionate acetate, ((1-naphthol) acetate of linalyl), which has the formula:
3- (4-methoxyphenyl) -3-oxo-propionate of 2,6-dimethyl-7-octen-2-yl, (3- (4-methoxyphenyl) -3-oxo-proponic acid dihydromyrcenyl ester, which has the formula:
3- (4-Nitrophenyl) -3-oxo-prop-onate of 2,6-dimethyl-7-octen-2-yl, (3- (4-nitrophenyl) -3-oxo-propionic acid dihydromircenyl ester, with the formula:
3- (2,6-Dimethyl-7-octen-2-yl 3- (ß-naphthyl) -3-oxo-propionate, dihydromyrcenyl ((2-naphthoyl) -acetate) having the formula:
(3- (4-methoxyphenyl) -3-oxo-propionate of 3, 7-dimethyl-l, 6-octadien-3-yl, (3- (4-methoxyphenyl) -3-oxo-proponic acid linalyl ester ), of the formula:
3- (β-Naphthyl) -3-oxo-propionate of (α, α-4-trimethyl-3-cyclohexenyl) methyl, ((2-naphthoyl) a-terpinyl acetate), with the formula:
3-ß-naphthyl-3-oxopropionate of 9-decen-1-yl, (9-decen-1-yl) (2-naphthoyl) acetate, alternatively known as rosalva 2'-acetonaphthone, with the formula:
3,7-dimethyl-l, 6-octadien-3-yl, 3- (nonanyl) -3-oxoproponate, ((nonanoyl) linalyl acetate), alternatively known as octyl- ((linalyl) α-acetyl) ketone, with the formula:
Additional non-limiting examples of preferred fragrances comprising the fragrance delivery systems of the present invention include cis-3-hexen-1-yl 3- (ß-naphthyl) -3-oxo-propionate, 3- (nonanil) -2,6-dimethyl-7-octen-2-yl-3-oxo-propionate, 3-oxo-butyrate
2, 6-dimethyl-7-octen-2-yl, 3,7-dimethyl-1,6-octadien-3-yl, 3- (ß-naphthyl) -3-oxo-2-3-oxo-butyrate methylpropionate
2, 6-dimethyl-7-octen-2-yl, 3- (ß-naphthyl) -3-oxo-2,2-dimethylpropionate of 3,7-dimethyl-l, 6-octadien-3-yl, 3- (3,7-dimethyl-l, 6-octadien-3-yl, 3- (β-naphthyl) -3-oxo-propionate of 3,7-dimethyl- 3-oxo-2-methylpropionate 2,6-octadienyl, 3-heptyl-3-oxo-propionate of 3,7-dimethyl-2,6-octadienyl, and mixtures thereof. Without the desire to be limited by theory, the process by which the pro-harmonies of the present invention release their fragrance raw materials is not limited to a single trajectory. In fact, the same molecule, under identical conditions, can have different equivalent trajectories by which the same or different compounds are released. For example, both the nerol and the geraniol can be released from an ester formed only by geraniol, if the conditions under which the transformation of geraniol to nerol can occur, are present during use. These conditions can be built into the molecule by the formulator, or they can be provided by the surrounding medium (eg, the formulation). Additionally, during the process of releasing fragrance raw materials, both the ketone portion and the alcohol portion of the pro-harmonies are capable of carrying out chemical transformations that provide a blend of fragrance notes not subject to inclusion in the products. original harmonies. For example, a pro-harmony ester containing the alcohol raw material of fragrance citronellol, can potentially release a mixture of rose oxides according to the following scheme:
provided that adequate conditions of rearrangement are present during use. The formulator is not limited to the supply of a type of fragrance, for example a fragrance raw material of acute, intermediate or severe note. Instead, a mix of high notes, a mix of high and low notes, or any combination of high, low, or high notes can be released in any suitable ratio. As described above, those skilled in the art of preparing fragrance-containing compositions have categorized the fragrances into three types based on their relative volatility: acute, intermediate and severe notes. Additionally, fragrances are categorized by the odor they produce: some of these description terms (descriptors) are broad and others relatively specific. For example "floral" is a term that connotes smells associated with flowers, while the term "lilac" is more specific. The descriptors used by those skilled in the art of perfumes and fragrances are among others "rose", "floral", "green", "citrus", "spices", "honey" and "moss". The sources of these notes are not limited to a chemical class; alcohols can produce essences of "rose", "green" and "moss", while "rose" essences may contain alcohols, ketones, terpenes, aldehydes, etc. Acute, intermediate and severe notes can serve different purposes in the fragrance mix and when formulated properly, produce a "balanced fragrance" composition. Based on volatility, these notes are described by those skilled in the art in the following manner: serious notes have the longest aroma duration; the intermediate notes have a medium volatility; and the high notes are the most volatile.
The compositions described below, as well as others chosen by the formulator, comprise a fragrance delivery system utilizing the pro-harmonies of the present invention to successfully release a "balanced fragrance" profile. It is also recognized by those skilled in the art that descriptors that refer to aesthetic perceptions as "acute", "intermediate" and "serious" notes are relative terms. A fragrance raw material characterized as a sharp note by a formulator usually has the same classification among many other perfumers. The same is true for intermediate and serious grades, however, occasionally a formulator can classify a given fragrance raw material as an intermediate note instead of a sharp note, or vice versa, but this fact does not diminish the usefulness of a given compound or his absolute identity. Acute, intermediate and serious notes are now combined reproducibly to produce perfumes, colognes, aftershave lotions, cologne waters, etc. for application on the skin, which have unique and pleasant odor characteristics. However, in addition to this pleasant fragrance, a fragrance delivery system that is used to release an essence to a perfume, cologne, personal care item, laundry detergent composition or hard surface cleaner, must fill a number of technical requirements. . It must be strong enough, it must be persistent, and it must retain its "essential character" during its period of evaporation. Apart from the changes made to the proharmony molecules in order to modify the fragrance profiles provided by the fragrance delivery systems of the present invention, modifications of these pro-harmonies can be made for the purpose of increasing the substantivity of the materials. The formulator by selecting a suitable unit Rl, R2 or R3, or by selection of R4, R5 and R6, can influence the degree and proportion at which the pro-harmony is deposited on the fabric or other surface. Those skilled in the art of formulating detergent compositions will recognize that the terms "substantive" and "substantivity" refer to the propensity of a compound to adhere to, associate with, or deposit on a surface, preferably the surface of the fabric. Therefore, more substantive compounds adhere more easily to the surface of the fabric. However, the substantive compounds, in general, do not react with the surface on which they are deposited. An example of a pro-harmony that is modified to provide greater substantivity with the fabric is 3- (ß-naphthyl) -) -2- (methoxypentaethyleneoxy) -3-oxo-propionate from
2,6-dimethyl-7-octen-2-yl (dihydromyrcenyl ((2-naphthoyl) (2-E5-methoxy) acetate), of the formula:
In addition to the substitution at the β-carbon atom, substitution can be made at other sites in the pro-harmony molecule, for example, 3- (methoxytriethylaxy) -3-oxo-butyrate of 3,7-dimethyl-1, 6. -octadien-3-yl, (methoxy E3) linalyl acetate of the formula:
is a modified pro-harmony to increase the substantivity in cloth. The pro-Armenians of the present invention are useful in articles of personal care and hygiene, including among other creams and lotions, make-up, tanning lotions, balms, ointments, depilatory agents, all of which may also contain one or more ingredients pharmaceutically assets; hair care items, such as shampoos and hair mops and sprays; Laundry detergent compositions including heavy duty liquids and granules, light duty liquids, laundry bars, pastes and gels; hard surface cleaning compositions. The pro-harmonies of the present invention are also suitable for use in fine fragrances, colognes, cologne waters, aftershave lotions and the like, wherein the slow release of the fragrance raw material is important.
The formulator is not limited by the present invention to supplying the pro-harmonies of the present invention by means of a carrier article, that is, by means of compositions for laundry, hand cream, lotions, etc. The pro-harmonies of the present invention are suitable for providing a durable fragrance or mixture of fragrances to articles including paper or paper-type materials. Examples of these include sanitary napkins, diapers, paper towels, items for incontinence mediation, and the like. The formulator may formulate a fragrance delivery system that contains pro-harmonies that are stable, that is, do not begin to decompose until they are put into operation by a "catalyst". The catalyst, depending on the structure of the pro-harmony, can add humidity, a relative change in pH, or an increase in temperature. For example, if water alone is a suitable catalyst to initiate the release of fragrance raw materials from a harmony, a paper towel that has been impregnated with the pro-harmonies can be moistened and then used to release the fragrance in one place. Additionally, the formulator may use the fragrance delivery system of the present invention as a means to indicate that a condition exists. For example, a specific liquid can be stored or transported in a cardboard, container or container, which can be prone to damage or slow leakage. The package or other packaging of the package can be impregnated with the fragrance delivery system of the present invention and upon contact of the liquid material with the pro-harmonies then release a fragrance raw material with a low intensity unpleasant odor that alerts the user about the adulteration that the package or container has suffered. The following are non-limiting examples of compositions in which the pro-harmonies of the present invention are suitable for use.
COMPOSITIONS DETERGENTS FOR LAUNDRY
In its basic form, the present invention relates to laundry detergent compositions containing the fragrance delivery system described above. For example, a laundry composition comprising: a) at least about 0.01%, preferably from about 0.01% to 15%, more preferably from about 0.1% to about 10%, much preferable about 1% to 5% by weight, of one or more pro-harmonies described above; b) at least about 0.01% by weight, preferably from about 0.1% to 60%, more preferably from about 0.1% to 30% by weight, of a detergent surfactant selected from the group consisting of anionic, cationic surfactants, nonionic, zwitterionic, ampholytic, and mixtures thereof, preferably said surfactant is an anionic surfactant, and c) the remainder, carriers and additive ingredients.
SURFACTORY SYSTEMS
The cleaning compositions herein can contain at least about 0.01% by weight of a surfactant selected from the group consisting of anionic, cationic, nonionic, ampholytic and zwitterionic surfactants. Preferably in the solid (i.e. granulated) and viscous semi-solid (i.e. gelatin, paste, etc.) systems of the present invention, the surfactant is preferably present in a degree of about 0.1% to 60%, more preferably 0.1% to about 30% by weight of the composition. Non-limiting examples of surfactants useful here typically at levels of from about 1% to 55%, by weight, include the alkylbenzenesulfonates of 11 to 18 carbon atoms; "LAS") and the primary alkyl, branched and branched chain sulfates from 10 to 20 carbon atoms ("AS"), the secondary (2,3) alkyl sulfates of 10 to 13 carbon atoms of the formula CH3 (CH2) x (CHOS03-M +) CH3 and CH3 (CH2) and (CHOS03-M +) CH2CH3 wherein xy (y + 1) are integers of at least about 7, preferably at least about 9, and M is a water-soluble cation, especially sodium, unsaturated sulfates such as oleyl sulfate, alkyl alkoxysulfates of 10 to 18 carbon atoms ("AexS"; especially ethoxysulfates EO 1-7), alkoxycarboxylates of alkyl of 10 to 18 carbon atoms (especially the carboxylates EO 1-5), glycerol ethers of 10 to 18 carbon atoms, alkyl polyglycosides of 10 to 18 carbon atoms and their corresponding sulphated polyglycosides, and the esters of alpha-sulfonated fatty acids of 12 to 18 carbon atoms. If desired, conventional non-ionic and amphoteric surfactants such as alkyl ethoxylates of 12 to 18 carbon atoms ("AE" including the so-called narrow peak alkyl ethoxylates and alkyl phenoalkoxylates of 6 to 12 carbon atoms (especially ethoxylates and ethoxy / propoxy mixtures), betaines and sulfobetaines of 12 to 18 carbon atoms ("sultaines"), amine oxides of 10 to 18 carbon atoms, and the like, can also be included in the compositions in general. of N-alkyl polyhydroxy fatty acids of 10 to 18 carbon atoms are highly preferred, especially the N-methylglucamides of 12 to 18 carbon atoms, see WO 9,206, 1554. Other surfactants derived from sugar include the amides of N-alkoxydolidroxy acids. fatty acids, such as N- (3-methoxypropyl) glucamide of 10 to 18 carbon atoms N-propyl-a N-hexyl glucamides of 12 to 18 carbon atoms can be used for low foam. conventional soaps of 10 to 20 carbon atoms can be used. If a high level of foam is desired, soaps of 10 to 16 carbon atoms of branched chain can be used. Especially useful are mixtures of anionic and nonionic surfactants. Other useful conventional surfactants are described below and are described in ordinary texts. The anionic surfactants can be broadly described as water-soluble salts, particularly the alkali metal salts, of organic-sulfur reaction products having in their molecular structure an alkyl radical containing from about 8 to 22 carbon atoms and a radical selected from the group consisting of sulphonic acid ester and sulfuric acid radicals. (The alkyl portion of the higher acyl radicals is included in the term alkyl). Important examples of the anionic synthetic detergents which can form the surfactant component of the compositions of the present invention are sodium or potassium alkyl sulfates, especially those obtained by sulfation of higher alcohols (8 to 18 carbon atoms) produced by reduction of tallow glycerides or coconut oil; sodium or potassium alkylbenzenesulfonates, in which the alkyl group contains about
9 to about 15 carbon atoms, (the alkyl radical can be a straight or branched aliphatic chain); sodium alkyl glyceryl ether sulfonates, especially those ethers of higher alcohols derived from tallow and coconut oil; sulphates and sodium sulfonates monoglycerides of coconut oil fatty acids; sodium or potassium salts or sulfuric acid ester resulting from the reaction of one mole of a higher fatty alcohol (for example tallow or coconut alcohols) and about 1 to 10 moles of ethylene oxide; sodium or potassium salts of alkylphenol ethylene oxide ether sulfates with about 1 to 10 ethylene oxide units per molecule and in which the alkyl radicals contain from 8 to 12 carbon atoms; the reaction products of fatty acids are derivatives of sodium or potassium salts of coconut oil of fatty acid amides of a methyl tauride in which the fatty acids, for example, are coconut oil and beta-acetoxy or beta- sodium or potassium acetamido-anesulfonates where aican has 8 to 22 carbon atoms. Additionally, the secondary alkyl sulphates can be used by the formulator alone or in combination with other surfactant materials and the following identifies and illustrates the differences between sulphated surfactants and otherwise conventional alkyl sulfate surfactants. The following are non-limiting examples of these ingredients: Conventional primary alkyl sulfates
(AS), as illustrated above, have the general formula ROS03-M + wherein R is typically a linear hydrocarbyl group of 8 to 22 carbon atoms and M is a water-soluble cation. Branched chain primary alkyl sulfate surfactants (ie, branched chain "PAS") having 8 to 22 carbon atoms are also known; see, for example, European Patent Application 439,316, Smith and co-inventors, filed January 21, 1991. Conventional secondary alkyl sulfate surfactants are those materials that have the sulfate portion distributed randomly along the structure Main hydrocarbyl of the molecule. These materials can be represented by the structure
CH. (CH:) r. (CH0S03-Mr) (CH2)? R.CH3
where m and n are integers of 2 or more and the sum of m + n is typically close to 9 to 17, and M is a water soluble cation. The above-mentioned secondary alkyl sulfates are those prepared by the addition of H2SO4 to the olefins. A typical synthesis using alpha-olefins and sulfuric acid is discussed in US Pat. No. 3,234,258, Morris, issued February 8, 1966 or in US Pat. No. 5,075,041, Lutz, issued December 24, 1991. See also U.S. Patent No. 5,349,101, to Lutz and co-inventors, issued September 20, 1994; US patent 5,389,277, issued by Prieto on February 14, 1995.
3- The preferred surfactants of the present invention are the anionic surfactants, however, other surfactants useful herein are described below. The compositions of the present invention may also comprise at least about 0.01%, preferably at least 0.1%, more preferably from about 1% to 30%, of a nonionic detergent surfactant. Preferred nonionic surfactants such as alkyl ethoxylates ("AE") of 12 to 18 carbon atoms, including so-called narrow peak alkyl ethoxylates and alkylphenol alkoxylates of 6 to 12 carbon atoms (especially ethoxylates and ethoxy / propoxy mixtures), alkylene oxide block condensates of alkylphenols of 6 to 12 carbon atoms, alkylene oxide condensates of alkanols of 8 to 22 carbon atoms and polymers of ethylene oxide / propylene oxide blocks ( Pluronic ™ - BASF Corp.), likewise semipolar nonionics (eg, amine oxides and phosphine oxides) can be used in the present compositions. An extensive discussion of these types of surfactants is found in US Patent 3,929,678, Laughlin and co-inventors, issued December 30, 1975, incorporated herein by reference.
Aiquilpolysaccharides such as those discussed in US patent 4,565,647 of Filling (incorporated herein by reference) are also preferred nonionic surfactants in the compositions of the invention. More preferred nonionic surfactants are polyhydroxy fatty acid amides having the formula:
O R8 R7-C-N-Q
wherein R7 is alkyl of 3 to 31 carbon atoms, preferably straight-chain alkyl or alkenyl of 7 to 19 carbon atoms, more preferably straight-chain alkyl or alkenyl of 11 to 15 carbon atoms, or mixtures thereof; R8 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, hydroxyalkyl of 1 to 4 carbon atoms, preferably methyl or ethyl, more preferably methyl. Q is a polyhydroxyalkyl portion with a linear alkyl chain with at least 3 hydroxyls directly connected to the chain, or an alkoxylated derivative thereof; the preferred alkoxy is ethoxy or propoxy, and mixtures thereof. The preferred Q is derived from a reducing sugar in a reductive amination reaction. More preferably, Q is a glyceryl portion. Suitable reducing sugars include glucose, fructose, maltose, lactose, galactose, mannose and xylose. It can be used as raw materials, corn syrup with high dextrose content, corn syrup with high fructose content, and corn syrup with high maltose content as well as the individual sugars mentioned above. These corn syrups can produce a mixture of sugar components for Q. It should be understood that this in no way is intended to exclude other suitable raw materials. Q is more preferably selected from the group consisting of -CH2 (CH0H) pCH20H.CH (CH: 0H) (CHOH) n-lCH20H. -CH2 (CHOH) 2-CHOR ') (CHOH) CH2OH, and alkoxylated derivatives thereof, wherein n is an integer from 3 to 5, inclusive, and R' is hydrogen or a cyclic or aliphatic monosaccharide. The most preferred substituents for the Q portion are the glycityls wherein n is 4, particularly -CH2 (CHOH) CH2OH. R7CO-N < it can be, for example, cocamide, stearamide, oleamide, lauramide, myristamide, capricamide, palmitamide, seboamide, etc. R8 can be, for example, methyl, ethyl, propyl isopropyl, butyl, 2-hydroxyethyl, or 2-hydroxypropyl.
Q can be i-deoxyglucityl, 2-deoxa-fructityl, 1-deoxy-maltityl, 1-deoxy lactityl, 1-deoxygalactityl, 1-deoxyrnanityl, 1-deoxy-maltotriotityl, etc. A particularly suitable surfactant of this type for use in the compositions herein, is alkyl-N-methylglucomide, a compound of the above formula wherein R7 is alkyl (preferably from 11 to 17 carbon atoms), R8 is methyl and Q is 1-deoxyglucyltyl. Other surfactants derived from sugars include the amides of N-alkoxy polyhydroxy fatty acids, such as N- (3-methoxypropyl) glucamide of 10 to 18 carbon atoms. N-propyl to N-hexyl glucamides of 12 to 18 carbon atoms can be used for low foam. Conventional soaps of 10 to 20 carbon atoms can also be used. If much foam is desired, branched chain soaps of 10 to 16 carbon atoms can be used.
ADDITIVE INGREDIENTS FOR LAUNDRY
The following are non-limiting examples of additive ingredients useful in laundry compositions of the present invention, said additive ingredients include builders, optical brighteners, whiteness enhancers, bleach catalysts, bleach activators, soil release polymers, transfer agents dyes, dispersants, enzymes, foam suppressants, dyes, perfumes, dyes, inert salts, hydrotropes, enzymes, photoactivators, fluorescent agents, fabric conditioners, hydrolyzable surfactants, preservatives, antioxidants, chelators, stabilizers, anticaking agents, anti-aging agents wrinkles, germicides, fungicides, anti-corrosive agents and mixtures thereof. Detergency builders - Builders may optionally be included in the compositions herein to assist in the control of mineral hardness. Both inorganic and organic improvers can be used. Builders are typically used in laundry detergent compositions to aid in the removal of particulate grime. The level of builder can vary widely depending on the final use of the composition and its desired physical form. When present, the compositions will typically contain from about 5% to about 50%, more typically about 5% to 30%, by weight, of detergency builder. Granulated formulations typically contain from about 10% to 80%, more typically about 15% to 50% by weight, of builder. However, this does not mean that the highest or lowest levels of detergency builder are excluded. Inorganic or phosphorus-containing builders include, but are not limited to, alkali metals, ammonium and alkanolammonium salts of polyphosphates (exemplified by tripolyphosphates, pyrophosphates, and vitreous polymeric metaphosphates), phosphonates, phytic acid, silicates, carbonates (including bicarbonates and sesquicarbonates), sulfates and aluminosilicates. However, phosphate-free builders are required in some places. It is important to note that the compositions herein work surprisingly well even in the presence of so-called "weak" builders (when compared to phosphates) as citrate, or in the so-called "improver-improver" situation which can occur with zeolite or layered silicate builders. Examples of silicate builders are alkali metal silicates, particularly those having a SiO2: Na2O ratio in the 1.6: 1 to 3.2: 1 scale and layered silicates, such as the layered sodium silicates described in US Patent 4,664,839. issued on May 12, 1987 to HP Rieck. NaSKS-6 is the trade name of a crystalline layered silicate marketed by Hoechst (commonly abbreviated here as "SKS-6"). Unlike zeolite builders, the Na SKS-6 silicate builder does not contain aluminum. The NaSKS-6 has the form of stratified silicate with delta-Na? SiOs morphology. It can be prepared by methods such as those described in German patents DE-A-3, 417, 649 and DE-A-3, 742, 043. SKS-6 is a highly preferred layered silicate for use herein, but others of these layered silicates, such as those having the general formula NaMSix02x + l-yH20 wherein M is sodium or hydrogen, x is a number from 1.9 to 4, preferably 2, e and is a number from 0 to 20, preferably 0, can be used in the present. Other diverse layered silicates from Hoechst include NaSKS-5. NaSKS-11, in alpha, beta and gamma forms. As indicated above, delta-Na2Si05 (NaSKS-6 form) is most preferred for use herein. Other silicates may also be useful, such as, for example, magnesium silicate, which may serve as an agent in the granular formulations, as a stabilizing agent in oxygen bleaches, and as a component of foam control systems. Examples of carbonate builders are the alkali metal and alkaline earth metal carbonates, such as those discussed in German patent application 2,321,001 published on November 15,
1973. Aluminosilicate builders are useful in the present invention. Aluminosilicate builders are of great importance in heavy duty commercially available granular detergent compositions, and can also be a significant detergency builder ingredient in liquid detergent formulations. The aluminosilicate builders include those that have the empirical formula:
[Mz (zA102) and] .xH20
where z and e are integers of at least 6, the molar ratio of zay is on the scale of 1.0 to about 0.5, and x is an integer of about 15 to about 264. Useful aluminosilicate ion exchange materials are available commercially These aluminosilicates can be of crystalline or amorphous structure and can be aluminosilicates present in nature or synthetically derived. A method for producing aluminosilicate ion exchange materials is discussed in US Pat. No. 3,985,669, to Krummel and co-inventors, issued October 12, 1976. Preferred crystalline aluminosilicate ion exchange synthetic materials useful herein, are available under the designations Zeolite A, Zeolite P (B), Zeolite MAP and Zeolite X. In an especially preferred embodiment, the crystalline aluminosilicate ion exchange material has the formula:
Nai2 [(A102) 12 (Si02) 12)] -xH20
where x is from about 20 to about 30. especially around 27. This material is known as Zeolite A. Dehydrated zeolites (x = 0-10) can also be used. Preferably, the aluminosilicate has a particle size of about 0.1-10 microns in diameter. Organic builders suitable for the purposes of the present invention include, but are not limited to, a wide variety of polycarboxylate compounds. As used herein, "polycarboxylate" refers to compounds with a plurality of carboxylate groups, preferably at least 3 carboxylates. The polycarboxylate builder generally can be added in the form of a neutralized salt. When used in salt form, alkali metal salts, such as sodium, potassium and lithium, or alkanolammonium salts, are preferred. Included among polycarboxylate builders is a variety of useful material categories. An important category of polycarboxylate builders comprises the ether polycarboxylates, including oxydisuccinate, as discussed in Berg patent US 3,128,287, issued April 7, 1964, and Lamberti patent US 3,635,830 and co-inventors, issued January 18. 1972. See also the "TMS / TDS" detergency builders of US Pat. No. 4,663,071, issued to Bush and co-inventors, on May 5, 1987. Suitable ether polycarboxylates also include cyclic compounds, particularly alicyclic compounds, such as those described in US Pat. US Patent 3,923,679; 3,835,163; 4,158,635; 4,120,874 and 4,102,903. Other useful builders include ether hydroxypolycarboxylates, maleic anhydride copolymers with ethylene or methyl vinyl ether, 1,3,5-trihydroxybenzene -2, 4,6-trisulfonic acid, and carboxymethyloxysuccinic acid, the various alkali metal salts, ammonium salts and of substituted ammonium of polyacetic acids such as ethylenediaminetetraacetic acid and nitrilotriacetic acid, also polycarboxylates such as mellitic acid, oxydisuccinic acid, polymaleic acid, benzene-1,3,5-tricarboxylic acid, carboxymethyloxysuccinic acid, and soluble salts thereof. Citrate builders, for example, citric acid and soluble salts thereof (particularly sodium salt), are polycarboxylate builders of particular importance for heavy duty liquid detergent formulations because of their availability from renewable resources and their biodegradability. Citrates can also be used in granular compositions, especially in combination with zeolite and / or layered silicate builders. Oxydisuccinates are also especially useful in these compositions and combinations. Also suitable in the detergent compositions of the present invention are the 3,3-dicarboxy-4-oxa-1, 6-hexanedioates and the related compounds discussed in Bush's US Patent 4,566,984, issued January 28, 1986. The improvers of useful succinic acid detergency include the alkyl- and alkenyl-succinic acids of 5 to 20 carbon atoms and the salts thereof. A particularly preferred compound of this type is dodecenylsuccinic acid. Specific examples of succinate builders include: iauryl succinate, myristylsuccinate, palmityl succinate, 2-dodecenylsuccinate (the preferred one), 2-pentadecenylsuccinate, and the like. Iauryl succinates are the preferred builders of this group, and are described in European patent application 86200690.5 / 0200263, published on November 5, 1986. Other suitable polycarboxylates are discussed in US Patent 4,144,226, Crutchfield and co-inventors , issued March 13, 1979 and US Pat. No. 3,308,067, Diehl, issued March 7, 1967. See also US Pat. No. 3,723,322 to Diehl. Fatty acids, for example monocarboxylic acids of 12 to 18 carbon atoms, can also be incorporated into the compositions alone or in combination with the aforementioned detergency builders, especially the citrate and / or succinate builders, to provide additional enhancing activity. This use of fatty acids will generally result in a decrease in the foam, which should be taken into account by the formulator. In situations where phosphorus-based builders can be used, and especially in the formulation of bars used for hand-washing operations, the various alkali metal phosphates can be used as well-known sodium tripolyphosphates, pyrophosphate and sodium orthophosphate. . Phosphonate builders such as 1,1-diphosphonate of 1-hydroxetane and other known phosphonates can also be used (see, for example, US Patents 3,159,581; 3,213,030; 3,422,021; 3,400,148 and 3,422,137). Other Ingredients - A wide variety of other ingredients useful in detergent compositions can be included in the compositions herein, including other active ingredients, carriers, hydrotropes, processing aids, dyes or pigments, solid fillers for stick compositions, etc. Other optional ingredients include enzymes, bleaches, bleach activators, bleach catalysts, photoactivators, dyes, fluorescers, fabric conditioners, hydrolyzable surfactants, optical brighteners, preservatives, antioxidants, chelators, stabilizers, aqueous washing liquid, where its detergent function. To illustrate this technique in more detail, a porous hydrophobic silica (trademark SIPERNAT DIO, DeGUSSA) is mixed with a proteolytic enzyme solution containing 3 - 5% nonionic surfactant of ethoxylated alcohol of 13 to 15 carbon atoms (SO 7). Typically, the enzyme / surfactant solution is 2.5 times the weight of the silica. The resulting powder is dispersed with stirring in silicone oil (various viscosities of silicone oil can be used in the range of 500-12,500). The resulting dispersion in silicone oil is emulsified or otherwise added to the final detergent matrix. By these means, ingredients such as the aforementioned enzymes, bleaches, whiteness activators, whiteness catalysts, photoactivators, dyes, fluorescers, cloth conditioners or hydrolyzable surfactants can be "protected" for use in detergent compositions. The detergent compositions herein will preferably be formulated such that, during use in cleaning operations in aqueous medium, the wash water will have a pH of about 6.5 to 11, preferably about 7.5 and 10.5 Laundry products typically have a pH of 9-11. Techniques for controlling pH at recommended use levels include the use of regulators, alkalis, acids, etc., and are well known to those skilled in the art. The following are non-limiting examples of fragrance delivery system and the pro-harmonies comprising said system.
CLEANING COMPOSITIONS OF HARD SURFACES
The pro-harmonies of the present invention are useful for releasing a pleasant essence or fragrance on a hard surface that has been cleaned. The slow release of the fragrance raw material provides a prolonged sensation of "freshness". The hard surface cleaners of the present invention may be in any form, inter alia, liquid, semi-solid, gelatinous, or solid. The cleaner can be a scrubbing cleaner and therefore contain an abrasive material. The hard surface cleaning compositions according to the present invention having increased perfume retention, as well as high surface gloss and low scratch, comprise: a) at least about 0.1%, preferably at least 0.5% by weight, of a sulfosuccinamate with the formula:
wherein R1 and R2 are hydrogen or -S03M2 if R1 is equal to R2; R3 is butyl when R4 is ethyl and R3 is pentyl when R4 is propyl; M and M2 are independently hydrogen or a cation forming salt; b) at least about 0.1%, preferably at least 0.5% by weight, of a nonionic surfactant having the formula
CH3 (CH2) xCH20 (CH2CH20) yH
where x is from around 6 to about 12, and is around 3.5 to about 10; c) at least about 0.01%, preferably from about 0.01% to 15%, more preferably from about 0.1% to 10%, much preferable from about 0.2% to 1% by weight, of one or more 68
anti-shrinking agents, anti-wrinkle agents, soil release agents, germicides, fungicides, dispersants and anti-corrosion agents. If high foam production is desired, foam reinforcers such as alkanolamides of 10 to 16 carbon atoms can be incorporated into the compositions, typically at levels of 1% -10%. The monoethanol- and diethanolamides illustrate a typical class of these foam boosters. The use of these foam reinforcers with high foam producing additive surfactants, such as the amines, amines, betaines and sultaines mentioned above, is also advantageous. If desired, the soluble magnesium salts such as MgC12, MgSO4, and the like, can be added at levels of, typically, 0.1% -2% to provide additional foam and improve the performance of fat removal. Various detergent ingredients employed in the present compositions can be further stabilized by absorbing said ingredients in a porous hydrophobic substrate, then covering said substrate with a hydrophobic layer. Preferably, the detergent ingredient is mixed with a surfactant before being absorbed by the porous substrate. In use, the detergent ingredient is released from the substrate in harmonies according to the present invention; and d) the remainder, carriers and additive ingredients, said additive ingredients selected from the group consisting of abrasives, detergency builders, bleaches, whiteness enhancers, clays, detergent surfactants, thickeners, dispersants, enzymes, pigments, dyes, filler salts, hydrotropes, enzymes, preservatives, antioxidants, chelators, stabilizers, germicides, fungicides, solvents, photo-disinfectants, and mixtures thereof. This example of a preferred hard surface cleaning composition described above in accordance with the present invention comprises either the dianionic surfactants of N-2-ethylhexyl sulfosuccinamate, N-2-propylheptyl sulfosuccinamate, or mixtures thereof, which have the formula:
wherein R1 and R2 are selected from hydrogen or the -SO3M 'portion, conditioned however that R1 and R2 are not equal, that is when R1 is hydrogen, R2 must be -SO3M, and vice versa. selected from hydrogen or a salt-forming cation Three carbon atoms in the previous molecule are chiral centers, that is, individually have the ability to form optical isomers or enantiomers., when two or more of these chiral carbon atoms are taken together they can form diastereomeric pairs or combinations. For the purposes of the present invention, the N-2-ethylhexyl sulfosuccinate is drawn in such a way that each chiral center is shown in its racemic form. For the purposes of the present invention all isomeric forms of N-2-ethylhexyl sulfosuccinate are suitable for use in the compositions of the present invention. M and M2 can be hydrogen or a salt-forming cation depending on the chosen synthesis method and the final pH of the hard surface cleaner. Examples of salt-forming cations are lithium, sodium, potassium, calcium, magnesium, quaternary alkylamines with the formula:
R3 I R6-N "-R4 I R5 wherein R3, R4, R5 and R6 are independently hydrogen, alkylene of 1 to 22 carbon atoms, branched alkylene of 4 to 22 carbon atoms, alkanol of 1 to 6 carbon atoms , alkenylene of 1 to 22 carbon atoms, branched alkenylene of 4 to 22 carbon atoms, and mixtures thereof A different salt forming cation may be chosen for the carboxylate portion (-CO? ') which is chosen for the sulphonate portion (-S03"). Preferred cations are ammonium (R3, R4, R5 and R6 equal to hydrogen), sodium, potassium, mono-, di-, and trialkanolammonium, and mixtures thereof. The monoalkanolammonium compounds of the present invention have R 3 equal to alkanol of 1 to 6 carbon atoms, R 4, R 5 and R 6 equal to hydrogen; the dialkanolammonium compounds of the present invention have R3 and R4 equal to alkanol of 1 to 6 carbon atoms, R5 and R6 equal to hydrogen; the trialkanolammonium compounds of the present invention have R3, R4 and R5 equal to alkanol of 1 to 6 carbon atoms, R6 equal to hydrogen. Preferred alkanolammonium salts of the present invention are the mono-, di- and tri-ammonium quaternary compounds having the formulas:
H3N + CHCH: OH, H.N + (CH: CH; 0H), HN + (CH2CH20H) 3
It is preferred that M and M2 are hydrogen, sodium, potassium and the alkanolammonium salts of 2 carbon atoms mentioned above; the most preferred are hydrogen and sodium.
THE NON-IONIC SURGICAL AGENT
The hard surface cleaning compositions of the present invention preferably further comprise a nonionic surfactant having the formula
CH3 (CH :) xCH20 (CH2CH2O) yH
wherein x is about 6 to 12, preferably about 8 to 10; "y" is about 3.5 to 10, preferably about 4 to 7. For the purposes of the present invention the subscript "y" refers to the average degree of ethoxylation obtained when an appropriate alcohol is contacted with a source of portions. ethyleneoxy, and consequently represents all the fractional parts within a scale of 3.5 to 10.
Other preferred hard surface cleaning compositions include solid scouring powders containing abrasives such as perlite or sodium carbonate, cleaning foams, and liquids in which the carrier material may comprise liquids other than water.
THE FRAGRANCE SUPPLY SYSTEM
In its most basic form the fragrance delivery system of the present invention comprises one or more proharmonies, preferably mixed with a suitable carrier or vehicle for the delivery of the pro-harmony or mixture of pro-harmonies to a site. The release of a durable fragrance at a site can be achieved by formulating a composition containing: a) at least about 0.01%, preferably about 0.01% to 15%, more preferably about 0.1% to 5%, much preferable about 0.2% to 1% by weight of one or more β-ketoesters according to the present invention; and b) the remainder contains a carrier, said carrier selected from the group consisting of water, alcohols of 1 to 3 carbon atoms, polyhydric alcohols of 2 to 8 carbon atoms, cationic and water-soluble anionic polymers, polyethylene glycols, and mixtures thereof. same; and applying said composition to the site. For example, the formulation can be sprayed directly onto clothes that need "cooling"; to the air of a room, or can be applied to the fabric of an upholstery article. Examples of suitable carriers include among others water, methanol, ethanol, isopropanol, and propylene glycol. Additionally, water-soluble polymers, for example water-soluble cationic polymer and water-soluble anionic polymers, can be used in the composition of the present invention to provide additional fragrance release benefits.
CATIONIC POLYMERS. FOR EXAMPLE, POLYAMINES
Water-soluble cationic polymers, for example, those containing amino functionalities, amido functionalities, and mixtures thereof, are useful in the present invention for controlling certain acid-type odors and consequently broadening the perception of fragrance raw materials. which are released by the proharmonies of the present invention.
b. ANIONIC POLYMERS. FOR EXAMPLE, POLYACRYLIC ACID
Similarly, water-soluble anionic polymers, for example, polyacrylic acids and their water-soluble salts, are useful in the present invention to control certain amine-type odors that may be present at the site when the pro-harmonies are released. . Preferred polyacrylic acids and their alkali metal salts have an average molecular weight of less than about 20,000. more preferably less than 5,000. Polymers containing sulfonic acid groups, phosphoric acid groups, phosphonic acid groups, and their water-soluble salts, and mixtures thereof, and mixtures with carboxylic acid and carboxylate groups are also suitable. Water-soluble polymers containing both cationic and anionic functionalities are also suitable. Examples of these polymers are described in US Pat. No. 4,909,986, issued March 20, 1990 to N. Kobayashi and A. Ka azoe, incorporated herein by reference. Another example of water-soluble polymers containing cationic and anionic functionalities is a copolymer of dimethyldiallylammonium chloride and acrylic acid, commercially available under the tradename Merquat 280® from Calgon. The following are non-limiting examples of the pro-harmonic β-keto esters of the present invention and the use thereof.
EXAMPLE 1 PREPARATION OF 3- (β-NAFTHYL) -3-OXOPROPIONATE OF 3,7-DIMETHYL-1, 6-OCTADIEN-3-ILO
Lithium diisopropylamide (101.0 mL of a 2.0 M solution, 0.202 mol) was placed in a three-necked round bottom flask equipped with a magnetic stirrer, internal thermometer, inlet for argon, and addition funnel. The flask is placed in a dry ice-acetone bath. 3,7-Dimethyl-l, 6-octadien-3-yl acetate is dissolved in an amount of (18.66 g, 0.095 mol) in THF (5 mL) and the resulting solution is added to the flask for 45 minutes. Once the addition is complete, the mixture is stirred for an additional 15 minutes, before being treated with a solution of 2-naphthoyl chloride in amount of (17.43 g, 0.090 mol) dissolved in THF (25 mL) for 30 minutes. The mixture is heated to -20 ° C and stirred at that temperature for 18 hours. After warming to 0 ° C, the mixture is quenched with 20% HCl (53 mL). The mixture is poured into a separatory funnel containing ether (150 mL) and water (250 mL). The aqueous layer is extracted with ether (150 mL). The combined organic layers are washed with saturated NaHCO3 solution (2x100 mL), water (2x150 mL) and brine (150 mL), dried over MgSO4 and filtered. The solvent is removed by rotary evaporation to obtain an orange / red oil. The oil is purified by column chromatography (elution with 5% ethyl acetate dissolved in petroleum ether) to obtain an oil. The purity of the product is determined by thin layer chromatography and GC analysis and the mass spectrometric structure is confirmed, NMR with ΔH and 13C.
EXAMPLE 2 PREPARATION OF 3- (4-METOXYPENYL) -3-QXOPROPIONATE OF 2,6-DIMETHYL-7-OCTEN-2-ILO
N-isopropylcyclohexylamine (25.00 g, 0.177 mol) and THF in an amount of 200 mL are placed in a three-necked round bottom flask equipped with magnetic stirrer, internal thermometer, inlet for argon, and addition funnel.
The flask is placed in an ice-methanol bath cooled to -5 ° C and its content is treated with n-butyllithium in the amount of (70.8 mL of a 2.50 M solution, 0.177 mol). The mixture is stirred for 20 minutes and cooled to -78 ° C. Dissolve 2,6-dimethyl-7-octen-2-yl acetate (dihydromyrcenyl acetate) in amount of (17.55 g, 0.089 mol) in THF (10 mL) and the resulting solution is added to the flask for 45 minutes. After the addition is complete, the mixture is stirred for an additional 15 minutes before being treated with a solution of p-methoxybenzoyl chloride in amount of (15.10 g, 0.090 mol) dissolved in THF (25 ml) for 30 minutes and then Stir for 1 hour. The mixture is warmed to 0 ° C and then treated with 90 mL of 20% HCl one hour later. The mixture is poured into a separatory funnel containing ether (100 ml) and water (200 ml). The aqueous layer is extracted with ether (100 ml). The combined organic layers are washed with saturated NaHCO 3 solution (2x100 ml), water (2x100 ml) and brine (100 ml), dried over MgSO4 and filtered. The solvent is removed by rotary evaporation to obtain an orange / red oil. The oil is purified by column chromatography (elution with 5% ethyl acetate dissolved in petroleum ether) to obtain an oil. The purity of the product is determined by thin layer chromatography and GC analysis and the structure is confirmed by mass spectrometry, NMR with 1H and 13C.
EXAMPLE 3 PREPARATION OF 2,6-DIMETHYL-7-OCTEN-2-ILO 3- (4-NITROPHENYL) -3-OXOPROPIONATE
Lithium dusopropylamide (121.0 mL of a 2.0 M solution, 0.243 mol) is placed in a 500-L three-necked flask and round phonao equipped with a magnetic stirrer, internal thermometer, argon inlet, and addition funnel. The flask is placed in a dry ice-acetone bath. Dissolve 2,6-dimethyl-7-octen-2-yl acetate (22.66 g, 0.114 mol) in THF (5 mL) and the resulting solution is added to the flask for 45 minutes. Once the addition is complete, the mixture is stirred for an additional 15 minutes, before being treated with a solution of 4-nitrobenzoyl chloride (20.00 g, 0.108 mol) dissolved in THF (25 mL) for 30 minutes. The mixture is heated to -20 ° C and stirred at that temperature for 18 hours. After warming to 0 ° C, the mixture is rapidly cooled with 20% HCl (70 mL). The mixture is poured into a separatory funnel containing ether (150 L) and water (250 L). The aqueous layer is extracted with ether (150 mL). The combined organic layers are washed with saturated NaHCO3 solution (2x100 L), water (2x150 mL) and brine (150 mL), dried over MgSO4 and filtered. The solvent is removed by rotary evaporation to obtain an orange / red oil. The oil is purified by column chromatography (elution with 2% ethyl acetate / petroleum ether) to obtain a colorless oil with 1 H and 13 C NMR spectra consistent with the desired product.
EXAMPLE 4 PREPARATION OF 3- (β-NAFTHYL) -3-QXOPROPIONATE OF 2,6-DIMETHYL-7-QCTEN-2-ILO
Lithium diisopropylamide (121.0 mL of a 2.0 M solution, 0.201 mol) was placed in a 500 mL three-necked round bottom flask equipped with a magnetic stirrer, internal thermometer, argon inlet, and addition funnel. The flask is cooled to -78 ° C. Dissolve 2,6-dimethyl-7-octen-2-yl acetate in amount of (18.75 g, 0.095 mol) in THF (5 mL) and the resulting solution is added to the flask for 45 minutes. Once the addition is complete, the mixture is stirred for an additional 15 minutes, before being treated with a solution of 2-naphthoyl chloride in amount of (17.00 g, 0.089 mol) dissolved in THF (25 mL) for 30 minutes. The mixture is heated to -20 ° C and stirred at that temperature for 18 hours. After warming to 0 ° C, the mixture is rapidly cooled with 20% HCl (55 mL). The mixture is poured into a separatory funnel containing ether (150 mL) and water (250 mL). The aqueous layer is extracted with ether (150 mL). The combined organic layers are washed with saturated NaHCO3 solution (2x100 mL), water (2x150 mL) and brine (150 L), dried over MgSO4 and filtered. The solvent is removed by rotary evaporation to obtain an orange / red oil. The oil is purified by column chromatography (elution with 2% ethyl acetate dissolved in petroleum ether) to obtain an oil. The purity of the product is determined by thin layer chromatography and GC analysis and the structure confirmed by mass spectrometry, 1 H and 13 C NMR.
EXAMPLE 5 PREPARATION OF 3- (4-METOXYPENYL) -3-OXOPROPIONATE OF 3,7-DIMETHYL-1, 6-OCTADIEN-3-ILO
Lithium diisopropylamide (119.0 mL of a 2.0 M solution, 0.238 mol) was placed in a 500 mL, three-neck, round bottom flask equipped with a magnetic stirrer, internal thermometer, argon inlet, and addition funnel. The flask is cooled to -78 ° C. 3,7-Dimethyl-l, 6-octadien-3-yl acetate (22.04 g, 0.112 mol) is dissolved in THF (5 mL) and the resulting solution is added to the flask for 45 minutes. Once the addition is complete, the mixture is stirred for an additional 15 minutes, before being treated with a solution of p-anisoyl chloride (35.00 g, 0.106 mol) dissolved in THF (30 mL) for 30 minutes. The mixture is heated to -20 ° C and stirred at that temperature for 18 hours. After warming to 0 ° C, the mixture is rapidly quenched with 20% HCl (80 mL). The mixture is poured into a separating funnel containing ether (150 mL) and water
(250 mL). The aqueous layer is extracted with ether (150 mL). The combined organic layers are washed with saturated NaHCO3 solution (2x100 mL), water (2x150 mL) and brine (150 L), dried over MgSO4 and filtered. The solvent is removed by rotary evaporation to obtain an oil. The oil is purified by column chromatography
(elution with 2% ethyl acetate / petroleum ether) to obtain a colorless oil with 1 H and 13 C NMR spectra consistent with the desired product.
EXAMPLE 6 PREPARATION OF 3- (β-NAFTHYL) -3-OXOPROPIONATE OF (α, α-4- TRIMETHYL-3-CYCLOHEXENYL) METHYL
Lithium diisopropylamide (171.0 mL of a 2.0 M solution, 0.342 mol) was placed in a 1000 mL, three-neck, round bottom flask equipped with a magnetic stirrer, internal thermometer, argon inlet, and addition funnel. The flask is cooled to -78 ° C. Acetate (a, 4-trimethyl-3-c-clohexenyl) methyl (30.00 g, 0.153 mol) in THF (10 mL) is dissolved and the resulting solution is added to the flask for 45 minutes. Once the addition is complete, the mixture is stirred for an additional 15 minutes, before being treated with a solution of 2-naphthoyl chloride (29.00 g, 0.152 mol) dissolved in THF (50 mL) for 30 minutes. The mixture is heated to -20 ° C and stirred at that temperature for 18 hours. After warming to 0 ° C, the mixture is rapidly cooled with 20% HCl (105 mL). The mixture is poured into a separatory funnel containing ether (150 mL) and water (250 mL). The aqueous layer is extracted with ether (150 mL). The combined organic layers are washed with saturated NaHCO3 solution (2x100 mL), water (2x150 L) and brine (150 mL), dried over MgSO4 and filtered. The solvent is removed by rotary evaporation to obtain an oil. The oil is purified by column chromatography (elution with 2% ethyl acetate / petroleum ether) to obtain a semi-white solid which is triturated in cold n-pentane to obtain a white powder with 1H NMR spectra and C consistent with the desired product.
EXAMPLE 7 PREPARATION OF 3- (α-NAFTHYL) -3-OXOPROPIONATE OF 3,7-DIMETHYL-1, 6-OCTADIEN-3-ILO
Lithium diisopropylamide (96.3 mL of a 2.0 M solution, 0.193 mol) was placed in a 500 L, three-necked, round bottom flask equipped with a magnetic stirrer, internal thermometer, argon inlet, and addition funnel. The flask is cooled to -78 ° C. 3,7-Dimethyl-l, 6-octadien-3-yl acetate (17.81 g, 0.091 mol) is dissolved in THF (5 mL) and the resulting solution is added to the flask for 45 minutes. Once the addition is complete, the mixture is stirred for an additional 15 minutes, before being treated with a solution of 1-naphthoyl chloride (16.82 g, 0.086 mol) dissolved in THF (25 mL) for 30 minutes. The mixture is heated to -20 ° C and stirred at that temperature for 18 hours. After warming to 0 ° C, the mixture is rapidly cooled with 20% HCl (53 mL). The mixture is poured into a separatory funnel containing ether (150 mL) and water (250 mL). The aqueous layer is extracted with ether (150 mL). The combined organic layers are washed with saturated NaHCO3 solution (2x100 mL), water (2x150 mL) and brine (150 mL), dried over MgSO4 and filtered. The solvent is removed by rotary evaporation to obtain an oil. The oil is purified by column chromatography (elution with 2% ethyl acetate / petroleum ether) to obtain a colorless oil with 1 H and 13 C NMR spectra consistent with the desired product.
EXAMPLE 8 PREPARATION OF 3- (ß-NAFTHYL) -3-OXOPROPIONATE OF CIS-3- HEXEN-1-ILO
Lithium diisopropylamide (133.0 mL of a 2.0 M solution, 0.266 mol) was placed in a 500 mL, three-neck, round bottom flask equipped with a magnetic stirrer, internal thermometer, argon inlet, and addition funnel. The flask is cooled to -78 ° C. 3-Hexenyl cis acetate (17.80 g, 0.125 mol) is dissolved in THF (10 mL) and the resulting solution is added to the flask for 45 minutes.
Once the addition is complete, the mixture is stirred for an additional 15 minutes, before being treated with a solution of 2-naphthoyl chloride (22.51 g, 0.118 mol) dissolved in THF (30 mL) for 30 minutes. The mixture is heated to -20 ° C and stirred at that temperature for 18 hours. After warming to 0 ° C, the mixture is rapidly cooled with 20% HCl (70 mL). The mixture is poured into a separatory funnel containing ether (150 L) and water (250 mL). The aqueous layer is extracted with ether (150 mL). The combined organic layers are washed with saturated NaHCO3 solution (2x100 mL), water (2x150 L) and brine (150 mL), dried over MgSO4 and filtered. The solvent is removed by rotary evaporation to obtain an oil. The oil is purified by column chromatography (elution with 2% ethyl acetate / petroleum ether) to obtain a colorless oil with 1 H and 13 C NMR spectra consistent with the desired product.
EXAMPLE 9 PREPARATION OF 3- (ß-NAFTIL) -3-OXOPROPIONATE OF 9-DECEN-I- ILO
Lithium diisopropylamide (79.8 mL of a 2.0 M solution, 0.160 mol) was placed in a 250 mL, three-neck, round bottom flask equipped with a magnetic stirrer, internal thermometer, argon inlet, and addition funnel. The flask is cooled to -78 ° C. Dissolve 9-decen-1-yl acetate (14.91 g, 0.075 mol) in THF (5 L) and the resulting solution is added to the flask for 45 minutes. Once the addition is complete, the mixture is stirred for an additional 15 minutes, before being treated with a solution of 2-naphthoyl chloride (13.80 g, 0.071 mol) dissolved in THF (25 mL) for 30 minutes. The mixture is heated to -20 ° C and stirred at that temperature for 18 hours. After warming to 0 ° C, the mixture is quenched with 20% HCl (47 mL). The mixture is poured into a separatory funnel containing ether (150 mL) and water (250 mL). The aqueous layer is extracted with ether (150 mL). The combined organic layers are washed with saturated NaHCO 3 solution (2x100 L), water (2x150 L) and brine (150 mL), dried over MgSO 4 and filtered. The solvent is removed by rotary evaporation to obtain an orange / red oil. The oil is purified by column chromatography (elution with 2% ethyl acetate / petroleum ether) to obtain a colorless oil with 1 H and 13 C NMR spectra consistent with the desired product.
EXAMPLE 10 PREPARATION OF 3- (NONANIL) -3-OXOPROPIONATE OF 3,7-DIMETHYL-1, 6-OCTADIEN-3-ILO
Lithium diisopropylamide (133.7 mL of a 2.0 M solution, 0.267 mol) was placed in a 500 mL three-necked round bottom flask equipped with a magnetic stirrer, internal thermometer, argon inlet, and addition funnel. The flask is cooled to -78 ° C. 3,7-Dimethyl-1,6,6-octadien-3-yl acetate (24.73 g, 0.126 mol) is dissolved in THF (40 mL) and the resulting solution is added to the flask for 45 minutes. Once the addition is complete, the mixture is stirred for an additional 15 minutes, before being treated with a solution of nonanoyl chloride (21.88 g, 0.119 mol) for 30 minutes. The mixture is heated to -20 ° C and stirred at that temperature for 18 hours. After heating to 0 ° C, the mixture is rapidly cooled with 20% HCl (60 L). The mixture is poured into a separatory funnel containing ether (150 L) and water (250 mL). The aqueous layer is extracted with ether (150 L). The combined organic layers are washed with saturated NaHCO3 solution (2x100 mL), water (2x150 L) and brine (150 mL), dried over MgSO4 and filtered. The solvent is removed by rotary evaporation to obtain an orange / red oil. The oil is purified by column chromatography (elution with 2% ethyl acetate / petroleum ether) to obtain a colorless oil with 1 H and 13 C NMR spectra consistent with the desired product.
EXAMPLE 11 PREPARATION OF 3- (NONANIL) -3-OXOPROPIONATE OF 2,6-DIMETHYL-7-OCTEN-2-ILO
Place lithium dusopropylamide (75.7 mL of a 2.0 M solution), 0.151 mol) in a 500 mL three-necked flask with round bottom, equipped with magnetic stirrer, internal thermometer, argon inlet, and addition funnel. The flask is cooled to -78 ° C. Dissolve 2,6-d? Met? L-7-octen-2-? Lo (14.14 g, 0.071 mol) in THF (20 L) and the resulting solution is added to the flask for 45 minutes. Once the addition is complete, the mixture is stirred for an additional 15 minutes, before being treated with a solution of nonanoyl chloride (12.38 g, 0.067 mol) for 30 minutes. The mixture is heated to -20 ° C and stirred at that temperature for 18 hours. After warming to 0 ° C, the mixture is rapidly cooled with 20% HCl (55 mL). The mixture is poured into a separatory funnel containing ether (150 mL) and water (250 mL). The aqueous layer is extracted with ether (150 L). The combined organic layers are washed with saturated NaHCO 3 solution (2x100 mL), water
(2x150 mL) and brine 1150 mL), dried over MgSO4 and filtered. The solvent is removed by rotary evaporation to obtain an orange / red oil. The oil is purified by column chromatography (elution with 2% ethyl acetate / petroleum ether) to obtain a colorless oil with 1 H and 13 C NMR spectra consistent with the desired product.
EXAMPLE 12 PREPARATION OF 3-OXQBUTIRATE OF 3, 7-DIMETHYL-1, 6-OCTADIEN-3-ILO
A mixture of linalool (100 g, 0.648 mol) and 4-dimethylaminopyridine (0.40 g, 3.20 mmol) in a 500 mL three-necked round bottom flask, equipped with condenser, argon inlet, addition funnel, magnetic stirrer and Internal thermometer is heated to 55 ° C. Diethylene (54.50 g, 0.648 mol) is added dropwise over the course of 30 minutes. The mixture has a slight exotherm and turns yellow to red during this time. After mixing an additional hour at 50 ° C, the mixture is cooled to room temperature. At this point, the NMR analysis indicates that the reaction is complete. The material of this lot is taken to the next step. Purification of an early sample from this route by flash chromatography (elution with dichloromethane) results in the desired product in 93% yield and almost colorless.
EXAMPLE 13 PREPARATION OF 3-OXOBUTIRATE OF 3, 7-DIMETHYL-1, 6-OCTADIEN-3-ILO
A mixture of dihydromyrcenol (37.88 g, 0.240 mol) and 4-dimethylaminopyridine (0.16 g, 1.30 mmol) in a 100 mL three-necked round bottom flask, equipped with condenser, argon inlet, addition funnel, magnetic stirrer and Internal thermometer is heated to 50-60 ° C. Dihetene (20.16 g, 0.240 mol) is added dropwise over the course of 15 minutes. The mixture has a slight exotherm and turns yellow to red during this time. After mixing an additional hour at 50 ° C, the mixture is cooled to room temperature. At this point, the NMR analysis indicates that the reaction is complete. Purification of the resulting mixture by flash chromatography (elution with dichloromethane) results in the desired product in 95% yield and almost colorless.
EXAMPLE 14 PREPARATION OF 3- (β-NAFTHYL) -3-OXOPROPIONATE OF 3,7-DIMETHYL-1, 6-OCTADIEN-3-ILO
Raw 3,7-dimethyl-l, 6-octadien-3-yl 3-oxobutyrate from the above is placed in a 3-neck three-necked round bottom flask equipped with condenser, argon inlet, addition funnel, stirrer magnetic and internal thermometer. The contents are dissolved in 350 mL of dichloromethane and treated with calcium hydroxide powder (50.44 g, 0.681 mol). The mixture is stirred at 30 ° C for 30 minutes and then heated to 40 ° C. A 2-naphthoyl chloride (142.12 g, 0.746 mol) dissolved in 20 ml is added dropwise over 15 minutes. of dichloromethane. The mixture continues to be heated at this temperature for 1 hour. Ammonium chloride (36.41 g, 0.681 mol) dissolved in 250 ml is added. of water, to the reaction mixture and the pH is adjusted to about 9 with 28% ammonium hydroxide. After mixing for 30 minutes at 35 ° C the pH is adjusted to about 1 with 20% HCl. The mixture is transferred to a separatory funnel containing diethyl ether (500 mL) and water (500 mL). The sediments are separated and the organic phase is washed with saturated NaHCO 3 solution (2 x 500 mL), dried over MgSO 3, filtered and concentrated by rotary evaporation to give a reddish yellow oil. At this point a light yellow solid precipitates from the mixture. An equal volume of hexane is added and the solids are collected by filtration and drying. The NMR analysis indicates that the solid is 2-naphthalic acid. The eluent is again concentrated by rotary evaporation to obtain a red oil. The oil is placed in an equal volume of dichloromethane, passed through a plug of silica gel (400 g.) And eluted with dichloromethane. The mixture is concentrated by rotary evaporation and purified by Kugelrohr distillation (40 ° C, 0.10 mm Hg, 30 min) to yield 173.26 g (76.3%) of the product as a red oil; This product is a mixture of a molar ratio of 1:10 of linalyl acetoacetate to (2-naphthoyl) linalyl acetate. A portion of this material is purified by column chromatography (elution with 2.5% ethyl acetate in hexanes) to give the desired product as a light yellow oil.EXAMPLE 15 PREPARATION OF 3- (ß-NAFTIL) -3-0X0-2, 2-DIMETHYLPROPIONATE OF 3,7-DIMETHYL-6-OCTADIEN-3-ILO
Sodium hydride (2.30 g, 0.057 mol,
60%) and tetrahydrofuran (50 mL) in a 250 mL three-necked round bottom flask equipped with magnetic stirrer, ice bath, addition funnel, internal thermometer and argon inlet. The contents of the flask are cooled to 0 ° C. 3- (7-Dimethyl-l, 6-octadien-3-yl 3- (ß-naphthyl) -3-oxopropionate (8.94 g, 0.025 mol) is dissolved in 50 ml. of tetrahydrofuran and added dropwise to the flask within 30 minutes. During the addition, the mixture emits gas. After mixing for 1 hour, methyl iodide (7.24 g, 0.051 mol) is added to the reaction mixture. Mixing is continued for 2 hours at 0 ° C and then at room temperature for 18 hours. The mixture is neutralized with 20% HCl and extracted with diethyl ether. The organic layers are washed with saturated NaHCO 3 solution, with water, dried over MgSO 4, filtered, concentrated by rotary evaporation and purified by flash chromatography to yield the desired compound. The structure is confirmed by NMR with ΔH and 13 C.
EXAMPLE 16 PREPARATION OF 3- (ß-NAFTHYL) -3-OXO-2-METHYLPROPIONATE OF 3,7-DIMETHYL-6-OCTADIEN-3-ILO
Sodium hydride (3.92 g, 0.098 mol,
60%) and tetrahydrofuran (100 mL) in a 250 mL three-necked flask with round bottom, provided with magnetic stirrer, ice bath, addition funnel, internal thermometer and argon inlet. The contents of the flask are cooled to 0 ° C. 3- (7-Dimethyl-l, 6-octadien-3-yl 3- (-naphthyl) -3-oxopropionate (15.28 g, 0.444 mol) is dissolved in 50 ml. of tetrahydrofuran and added dropwise to the flask within 30 minutes. During the addition, the mixture emits gas. After mixing for 1 hour, methyl iodide (10.65 g, 0.075 mol) is added to the reaction mixture. Mixing is continued for 2 hours at 0 ° C and then at room temperature for 18 hours. The mixture is neutralized with 20% HCl and extracted with diethyl ether. The organic layers are washed with saturated NaHCO 3 solution, water, dried over MgSO 4, filtered, concentrated by rotary evaporation and purified by flash chromatography to produce the desired compound. The structure is confirmed by 1 H and 13 C NMR.
EXAMPLE 17 PREPARATION OF 3- (HEXYL) -3-OXO-PROPIONATE OF 3,7-DIMETHYL- 1, 6-OCTADIEN-3-ILO
3,7-Dimethyl-l, 6-octadien-3-yl 3-oxo-butyrate (30.00 g, 0.126 mol), dichloromethane (50 mL) and methyl ethyl ketone (10 L) are placed in a 500 mL three-flask. necks and round bottom, equipped with internal thermometer, addition funnel, condenser and argon inlet. Calcium hydroxide (9.80 g, 0.132 mol, powder) is added to the flask and the suspension is stirred for 1 hour. Heptanoyl chloride (17.84 g, 0.120 mol) in 10 ml of dichloromethane is added after maintaining the reaction temperature between 35-40 ° C for 15 minutes. The reaction continues, mixing at 35-40 ° C for 2 hours. Ammonium chloride (7.06 g, 0.132 mol) dissolved in 20 mL of water is added to the flask. After 20 minutes, HCl solution is added until the pH of -10 is reached. After 1 hour, the mixture is poured into 300 ml of dichloromethane. The combined organic layers are washed with saturated NaHCO 3 solution, water, dried over MgSO 4, filtered, concentrated by rotary evaporation and purified by flash chromatography to yield the desired compound. The structure is confirmed by NMR with ΔH and 13 C.
EXAMPLE 18 PREPARATION OF 3-0X0-2-BENCILBUTIRATE OF 3, 7-DIMETHYL-6-OCTADIEN-3-ILO
Potassium carbonate (3.92 g, 0.228 mol) is placed
3,7-dimethyl-l, 6-octadien-3-yl 3-oxo-butyrate (4.80 g, 0.030 mol), benzyl chloride (4.80 g, 0.038 mol) and acetone (15 mL) in a bottom flask round, 50 mL, equipped with magnetic stirrer, condenser and argon inlet. The mixture is refluxed for 18 hours. The cooled mixture is filtered and concentrated by rotary evaporation. The resulting oil is purified on silica gel to produce the desired compound. The structure is confirmed by thin-layer chromatography and 1H and 13 C NMR. Other methods of preparing β-ketoesters can be found in US 5, Meier 194,671, issued March 16, 1993, included here as a reference. The following are examples of laundry detergent granular composition containing the fragrance delivery system of the present invention.
TABLE I in weight Ingredients 19 20 21 22
1. Sludge-removing polymer according to US Patent 4,968,451, Schiebel and co-inventors, issued November 6, 1990 2. Pro-harmonies according to example 1 3. Pro-harmonies according to example 2 4. The rest Up to 100% can, for example, include minor ingredients such as optical brightener, perfume, foam suppressant, dirt dispersant, protease, lipase, cellulase, chelating agents, dirt transfer inhibiting agents, additional water, and fillers, including CaCO3 , talc, silicates, etc. The following are examples of liquid laundry detergent compositions containing the fragrance delivery system of the present invention
TABLE II% by weight
Ingredients 23 24 25 26 27
1. E9 alkyl ethoxylate of 12 to 13 carbon atoms, marketed by Shell Oil Co. 2. Slisma of Bacillus amyloliquefaciens as described in WO 95/10615 published April 20, 1995, for Genencor International. 3. Derivative of Humicola lanuginosa and marketed by Novo 4. Discussed in WO 9510603 A and available from Novo
. Pro-harmony according to example 3 6. Copolymer of terephthalate as discussed in US patent 4,968,451, Scheibel and co-inventors, issued on November 6, 1990.
EXAMPLE 28
The following is an example of a solid bleaching composition containing pro-harmonies according to the present invention.
TABLE III Ingredients% by weight
Nonanoyloxybenzenesulfonate 7.0
1. Diethylenetriaminepentaacetic acid 2. Dihydromyrcenol 3. Pro-harmony according to example 7
EXAMPLE 29
The following is an example of a liquid bleaching composition containing a pro-harmony of the present invention.
TABLE III Ingredients% by weight
1. Dipotassium salt of 4,4-bis (4-phenyl-2-Hl, 2,3-triazolyl) - (2) -stilben-2,2-disulfonic acid 2. A mixture of linalool (29%) tetrahydrolinalool (30) %), Galaxolide (30%) and laceral dimetre of citral (20%) 3. Pro-harmony according to example 3.
CONDITIONING LOTION FOR SKIN
An example of a skin care composition of the present invention comprises an ester with a total number of carbon atoms of more than about 28, for example lauryl laurate, lauryl myristate, iristyl myristate, behenyl caprylate, cetearyl palmitate, behenyl stearate, more preferable cetearyl palmitate and cetyl stearate. The present compositions in addition to the esters described above, contain an emollient material in an amount such that the amount of more emollient ester is about 0.2% to about 25% of the total composition, preferably about 4% to 18%. One function of the emollient is to ensure that the ester is sufficiently plasticized to allow it to take a film-like state on the skin. The emollient in the present compositions is selected from the group consisting of fatty alcohols, esters having less than about 24 carbon atoms in total (e.g., isopropyl palmitate), branched chain esters having more than about 24 atoms carbon (for example cetearyl octonate), squalane, liquid or solid paraffins, mixtures of fatty acids and squalane, mixtures of fatty acids and liquid or solid paraffins and mixtures thereof. The aforementioned esters, which have less than 24 carbon atoms or branched esters having more than 24 atoms, if used as emollients should preferably be used in an amount equal to about one third of the length of the ester chain. The particular emollient selected depends in part on the particular ester selected since the correct plasticization, as indicated above, is desired. The emollient for the esters having more than 28 carbon atoms is preferably selected from the group consisting of squalane, liquid or solid parafams and mixtures of fatty alcohols with squalane or parafams. The fatty alcohols and fatty acids typically useful in the present compositions include those having from 12 to 22 carbon atoms, such as cetyl alcohol, myristyl alcohol, stearyl alcohol, stearic acid and palmitic acid. Paraffins include, for example, mineral oil, petrolatum and paraffin wax. The use of distilled water in the present compositions is preferred.
OPTIONAL COMPONENTS
OIL PHASE COMPONENTS
In addition to the long chain esters, the emollients and emulsifiers described above, the oily phase of the present compositions may contain a variety of materials including: (a) Esters that do not meet the requirements for the long chain ester and are not present as emollients, supra, such as oleyl oleate, isostearyl isostearate, isopropyl lanolate, isopropyl myristate, butyl stearate, myristyl lactate and 2-ethylhexyl palmitate; (b) Oils such as castor oil, jojoba oil, cottonseed oil, peanut oil and sesame oil; (c) Waxes such as ceresin wax, carnauba wax, beeswax and castor wax; (d) Lanolin, its derivatives and components such as acetylated lanolin, lanolin alcohols and lanolin fatty acids. The lanolin fatty acids are described in US Pat. No. Re.29, 814, dated October 24, 1978, by W. E. Synder incorporated herein by reference. (e) Polyalkylenes such as hydrogenated polyisobutene and polyethylene; and (f) Sterols such as cholesterol and phytosterol. These optional oily phase materials may comprise up to about 80% of the oily phase, preferably up to about 35%. When used at these levels, the optional components do not impair the occlusive nature of the compositions and increase the overall cosmetic function of the composition.
AQUEOUS PHASE COMPONENTS
The aqueous phase of the compositions may contain many different materials, including: (a) Humectants, such as sorbitol, glycerin, propylene glycol, alkoxylated glucose and hexanetriol at a level of about 1% a (b) Thickening agents, such as carboxyvinyl polymers, ethylcellulose, polyvinyl alcohol, carboxymethylcellulose, vegetable gums and clays such as Veegum MR, (magnesium aluminum silicate, RT Vanderbilt, Inc.) at a level of about 0.01% to 6%; (c) Proteins and polypeptides at a level of about 0.1% to 3%; (d) Preservatives such as methyl, ethyl, propyl and butyl esters of hydroxybenzoic acid (Paraben-Mallinckrodt Chemical Corporation) EDTA and imidazolidinyl urea (Germall 115-Sutton Laboratories) at a level of about 0.2% to 2.5%; and (e) An alkaline agent such as sodium hydroxide to neutralize, if desired, part of the fatty acids or thickeners that may be present. All percentages of these additional aqueous phase components are with respect to the total composition. The present compositions may also contain agents suitable for aesthetic purposes such as dyes. The compositions of the present invention are preferably substantially free of materials that adversely affect their performance. Accordingly, some ingredients, such as polyethylene glycols are preferably present only at levels below about 1% of the total composition. The pH of the present compositions is preferably in the approximate range of 7.5-10.
THE METHOD OF PREPARATION
The compositions of the present invention generally have a lotion consistency and may be in the form of oil-in-water or water-in-oil emulsions; the first being the preferred one due to its more pleasant cosmetic properties. The compositions of the present invention are preferably made by the method comprising the steps of: a) Preparing the oily phase; b) Prepare the aqueous phase; and c) Add the oily phase to the aqueous phase. Step (a) is carried out by heating the aqueous phase materials to a temperature approximately equal to that of the oily phase. The emulsion is formed by slowly adding the oily phase prepared in step
(a) to the aqueous phase prepared in step (b) with mixing.
The pro-harmonies comprising the fragrance delivery system or other ingredients may be added to the phase in which they are soluble before mixing the two phases or they may be added directly to the mixed aqueous and oily phases. In addition to compositions containing fragrances for use on human skin, the pro-accords of the present invention are also suitable for use in any application for odor control or fragrance mediation. An example of this odor control capability are waste pickers, odor control items useful for covering cages, mangers, and other domestic animal housing areas.
For example, US 5,339,769 to Toth and co-inventors, issued August 23, 1994, describes a process for making an absorbent composition in which the pro-harmony materials of the present invention can be well accommodated. An example of suitable material for collecting waste comprising the pro-harmonies of the present invention can be formed by the following process. A Glatt fluid bed granulator is loaded with 1,0000 g of bentonite clay (90% of particles greater than 420 microns) and 10 g of a cellulosic ether (Methocel ™ K15M Premium, a cellulose ether having a viscosity of 15,000 centipoise (cps) as a 2% aqueous solution). The granulator is turned on and the temperature of the product is brought to about 40 ° C (exit temperature). When the outlet temperature reaches around 40 ° C, atomized water is sprayed on the moving powders inside the granulator. During the granulation process, the inlet air temperature is maintained from 70 ° C to 80 ° C; the air atomization pressure is 1.96-2.46 kg / cm2; and the spray cycle is 45 seconds with a stirring time of 15 seconds. The clay agglomerates / cellulose ether swell over time. The water hydrates the cellulosic ether polymer which produces adhesion to form the granule.
At this time, it is more advantageous to introduce pro-harmony materials and other aesthetic fragrances. The granule formation promotes the aggregation of the small particles of the inert substrate, for example, clay particles of about 50 to 600 microns. The formation of a granule significantly reduces the quality of the powder in the final product while the waste collector forms an agglomerate when it is moistened. In an alternative mode of the clay-based waste collection box with mixed items / proharmony, once the clay particles have been formed, a concentrated solution, or an alcohol-based carrier mixture of the pro-harmonies can be released to the surface of the granule by convenient means. A stick deodorant gel of the present invention containing the composition given below, and which is essentially free of water, is prepared as follows:
TABLE V% by weight
Ingredients 30 31 32
Dipropylene glycol 39.85 51.95 75.10
Sodium Stearate 5.50 5.50 5.50
1. In powder form commercially available from Olin. 2. Pro-harmony blend comprising 75% of the pro-harmony form of example 3 and 25% of the pro-harmony of example 6. All the above materials, except the pro-harmony fragrance, are mixed vigorously and heated to about 121 ° C until the mixture is clear. The mixture is then cooled to about 80 ° C and the proharmony is added by stirring. The mixture is poured into bar molds and cooled to room temperature to form the stick deodorant compositions of the present invention. A personal cleansing composition is prepared by combining the following ingredients using conventional blending techniques.
TABLE VI in weight Disputable as Pemulen® from B.F. Goodrich Corporation 2. Available as Carbomer © 954 from B.F. Goodrich Corporation 3. As a 50% aqueous solution 4. Light mineral oil available as Drakeol 5 from Penreco, Dickenson, TX. 5. Pro-harmony according to example 3 6. Pro-harmony according to example 11 The above examples 33-36 can be appropriately prepared as follows. In a suitable vessel, the ingredients of phase A are mixed at room temperature to form a dispersion and heated with stirring at 70-80 ° C. In a separate container, the ingredients of phase B are heated with stirring at 70-80 ° C. Phase B is then added to phase A with mixing to form an emulsion. Next, phase C is added to neutralize the composition. The ingredients of phase D are added with mixing, followed by cooling to 45-50 ° C. The ingredients of phase E are then added with stirring, followed by cooling to 40 ° C. Phase F is heated with mixing at 40 ° C, and added to the emulsion, which is cooled to room temperature. The resulting cleaning composition is useful for cleaning the skin. The emulsion is demulsified on contact with the skin. The following non-limiting examples illustrate the hard surface cleaners containing the fragrance delivery system of the invention.
TABLE VII% by weight
1 . SOKALAN CP-9 2. Pro-harmony according to example 3
TABLE VIII% by weight
Pro-harmony according to example 3. Pro-harmony according to example 7.
Claims (6)
1. - A fragrance supply system characterized in that it comprises one or more proharmony compounds having the formula: wherein R is alkoxy derived from an alcohol fragrance raw material; R1, R2 and R3 are each independently hydrogen, substituted or unsubstituted linear alkyl of 1 to 30 carbon atoms, unsubstituted or substituted branched alkyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkyl of 3 to 30 carbon atoms carbon, substituted or unsubstituted linear alkenyl of 2 to 30 carbon atoms, branched or unsubstituted branched alkenyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkenyl of 3 to 30 carbon atoms, linear alkynyl substituted or unsubstituted substituted by 2 to 30 carbon atoms, unsubstituted or substituted branched alkynyl of 3 to 30 carbon atoms, substituted or unsubstituted alkylenearyl of 6 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, alkylenoxy substituted or unsubstituted of 2 to 20 carbon atoms, substituted or unsubstituted alkylene-alkyl of 3 to 20 carbon atoms, substituted or unsubstituted alkylenearyl of 7 to 20 carbon atoms carbon, substituted or unsubstituted alkylenediaryl of 6 to 20 carbon atoms, and mixtures thereof; where at least one of Rl, R2 or R3 is a unit having the formula: wherein R4, R5 and R6 are each independently hydrogen, substituted or unsubstituted linear alkyl of 1 to 10 carbon atoms, substituted or unsubstituted branched alkyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkyl of 3 to 30 carbon atoms, substituted or unsubstituted linear alkoxy of 1 to 30 carbon atoms, branched or unsubstituted branched alkoxy of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkoxy of 3 to 30 carbon atoms, substituted linear alkenyl or unsubstituted from 2 to 30 carbon atoms, unsubstituted or substituted branched alkenyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkenyl of 3 to 30 carbon atoms, unsubstituted or substituted linear alkynyl of 2 to 30 atoms carbon, substituted or unsubstituted branched alkynyl of 3 to 30 carbon atoms, substituted or unsubstituted alkylenearyl of 6 to 30 carbon atoms; or R4, R5 and R6 can be taken together to form a substituted or unsubstituted aryl of 6 to 30 carbon atoms; and mixtures thereof.
2. A composition according to claim 1 further characterized in that Rl has the formula: R2, R3, R4 and R5 are given hydrogen; and R6 is hydrogen, substituted or unsubstituted linear alkyl of 1 to 16 carbon atoms, substituted or unsubstituted branched alkyl of 3 to 16 carbon atoms, and mixtures thereof.
3. A composition according to claim 1 further characterized in that Rl has the formula: R2 and R3 are each hydrogen, R4, R5 and R6 are taken together to form substituted or unsubstituted phenyl of 6 to 30 carbon atoms, naphthyl, and mixtures thereof.
4. A composition according to claim 1 characterized in that said β-ketoester is selected from the group consisting of 3- (ß-naphthyl) -3-oxo-propionate of 3, 7-d? Met? Ll, 6-octad ? in-3-? lo, 3- (4-methoxyphenyl) -3-oxo-pro-dionate and 2,6-d? met? l-7-octen-2-? lo, 3- (4-n? trofen? l) -2,6-d? met? l-7-octen-2-yl, 3- (? -naphthii) -3-oxo-prop? onate of 2,6-d? met ? l-7-octen-2-ylo, 3- (4-methox? phen? l) -3-oxo-prop? onate of 3, 7-d? met? ll, 6-octad? en-3? lo, 3- (ß-naphthyl) -3-oxo-prop-onate of (a, a-4-trimet? l-3-c? clohexen? l) methyl, 3- (a-naphthyl) -3-oxo 3,7-d? met? ll, 6-octad? in-3-? lo, 3- (ß-naphthyl) -3-oxo-prop? onate of cis-3-hexen-l-? lo, 3- (7-dimethyl) -3-oxo-propionate of 9-deca-1-α, 3- (nonanil) -3-oxoproponate of 3, 7-dimet-1, 6-octad-en-3 -? lo, 3- (nonanil) -3-oxopropionate of 2,6-dimethyl-7-octen-2-? lo, 3-oxo-butyrate of 2,6-d? met? l-7-octen-2 -?the3,7-dimethyl-l, 6-octad? En-3-yl, 3- (β-naphthyl) -3-oxo-2-methidopropionate 3,6-oxo-butyrate -dimethyl-7-octen-2-yl, 3- (ß-naphthyl) -3-oxo-2, 2-d? methylprop-onate of 3, 7-dimet? ll, 6-octad? en-3-yl 3- (7-d? Methyl-l, 6-octadien-3-yl 3- (ß-naphthyl) -3-oxo-2-propionate 3- (ß-naphthyl) -3-oxo-2-methylpropionate of 3, 7-dimethyl-2,6-octadienyl, 3-heptyl-3-oxo-propionate of 3,7-dimethyl-2,6-octadienyl, and mixtures thereof.
5. A composition according to claim 1, further characterized in that it also comprises additive ingredients, said additive ingredients are selected from the group consisting of detergency builders, optical brighteners, bleaches, whiteness enhancers, bleach catalysts, bleach activators, slurry-blocking polymers, dye transfer agents, dispersants, enzymes, suds suppressors, dyes, perfumes, dyes, filler salts, hydrotropes, enzymes, photoactivators, fluorescers, fabric conditioners, hydrolyzable surfactants, preservatives, antioxidants, chelators , stabilizers, anti-shrinkage agents, anti-wrinkle agents, germicides, fungicides, anti-corrosive agents, pharmaceutical active ingredients and mixtures thereof.
6. A composition according to claim 1 further characterized in that at least one pro-harmony is able to release at least one fragrance raw material selected from the group consisting of 4- (l-methylethyl) cyclohexanemethanol, 2,4-dimethyl -3-cyclohexen-l-ylmethanol, (2,4-dimethylcyclohex-1-yl) methanol, (2,4,6-trimethyl-3-cyclohexen-1-yl) methanol, 2-phenylethanol, 1- (4- isopropylcyclohexyl) -ethanol, 2,2-dimethyl-3- (3-methylphenyl) propan-1-ol, 3-phenyl-2-propen-1-ol, 2-methyl-4- (2,2,3-trimethyl) -3-cyclopenten-l-yl) -2-buten-l-ol, 3-methyl-5-phenylpentan-1-ol, 3-met l-5- (2, 2, 3-trimethyl-3-cyclopenten -yl) -4-penten-2-ol, 2-methyl-4-phenylpentan-l-ol, cis-3-hexenl-ol, 3, 7-dimethyl-6-octen-l-ol, 3, 7- dimethyl-2,6-octadien-l-ol, 7-methoxy-3,7-dimethyloctan-2-oi, 6,8-dimethylnonan-2-ol, cis-6-nonen-l-oi, 2,6- nonadien-l-ol, 4-methyl-3-decen-5-ol, benzyl alcohol, 2-methoxy-4- (1-propenyl) phenol, 2-methoxy-4- (2-propenyl) phenol, and mixtures of the same. 1 . - A laundry detergent composition characterized in that it comprises: a) at least about 0.01%, preferably from about 0.01% to 15%, more preferably from about 1% to 5%, much more preferable from about 0.1% to 1 % by weight, of a β-ketoester having the formula: wherein R is alkoxy derived from an alcohol fragrance raw material; R1, R2 and R3 are each independently hydrogen, substituted or unsubstituted linear alkyl of 1 to 30 carbon atoms, unsubstituted or substituted branched alkyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkyl of 3 to 30 carbon atoms of carbon, substituted or unsubstituted linear alkenyl of 2 to 30 carbon atoms, branched or unsubstituted branched alkenyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkenyl of 3 to 30 carbon atoms, linear alkynyl substituted or unsubstituted substituted from 2 to 30 carbon atoms, unsubstituted or substituted branched alkynyl of 3 to 30 carbon atoms, substituted or unsubstituted aiquilenaryl of 6 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbono atoms, alkylenoxy substituted or unsubstituted of 2 to 20 carbon atoms, substituted or unsubstituted alkylene-xalkyl of 3 to 20 carbon atoms, substituted or unsubstituted alkylenearyl of 7 to 20 carbon atoms arbono, substituted or unsubstituted alkylenediaryl of 6 to 20 carbon atoms, and mixtures thereof; conditioned to the fact that at least one of Rl, R2 or R3 is a unit that has the formula: wherein R 4, R 5 and R 6 are each independently hydrogen, substituted or unsubstituted linear alkyl of 1 to 30 carbon atoms, unsubstituted or substituted branched alkyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkyl of 3 to 30 carbon atoms, substituted or unsubstituted linear alkoxy of 1 to 30 carbon atoms, branched or unsubstituted branched alkoxy of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkoxy of 3 to 30 carbon atoms, substituted linear alkenyl or unsubstituted of 2 to 30 carbon atoms, unsubstituted or substituted branched alkenyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkenyl of 3 to 30 carbon atoms, substituted or unsubstituted linear alkynyl of 2 to 30 atoms of carbon, substituted or unsubstituted branched alkynyl of 3 to 30 carbon atoms, substituted or unsubstituted alkylenearyl of 6 to 30 carbon atoms, or R4, R5 and R6 can be taken together to form substituted or unsubstituted aryl of 6 to 30 carbon atoms; and mixtures thereof; b) at least about 0.01% by weight, preferably about 0.1% to about 60%, more preferably from about 0.1% to 30% by weight, of a detergent surfactant selected from the group consisting of anionic, cationic surfactants , nonionic, zwitterionic, ampholytic, and mixtures thereof, preferably said surfactant is an anionic surfactant; and c) the rest, carriers and additive ingredients. 8. A composition for application to the skin with increased retention of fragrance and fragrance longevity, characterized in that it comprises: a) at least about 0.01%, preferably about 0.01% to 15%, more preferably about 1% at 5%, much more preferably from about 0.1% to 1% by weight, of a β-ketoester having the formula: wherein R is alkoxy derived from an alcohol fragrance raw material; R1, R2 and R3 are each independently hydrogen, substituted or unsubstituted linear alkyl of 1 to 30 carbon atoms, unsubstituted or substituted branched alkyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkyl of 3 to 30 carbon atoms carbon, substituted or unsubstituted linear alkenyl of 2 to 30 carbon atoms, branched or unsubstituted branched alkenyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkenyl of 3 to 30 carbon atoms, linear alkynyl substituted or unsubstituted substituted from 2 to 30 carbon atoms, unsubstituted or substituted branched alkynyl of 3 to 30 carbon atoms, substituted or unsubstituted alkylenepn of 6 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, alkylenoxy unsubstituted or substituted by 2 to 20 carbon atoms, substituted or unsubstituted alkylene-xalkyl of 3 to 20 carbon atoms, substituted or unsubstituted alkylenearyl of 7 to 20 carbon atoms rbono, substituted or unsubstituted alkylenediaryl of 6 to 20 carbon atoms, and mixtures thereof; conditioned that at least one of Rl, R2, or R3 is a unit that has the formula: wherein R 4, R 5 and R 6 are each independently hydrogen, substituted or unsubstituted linear alkyl of 1 to 30 carbon atoms, unsubstituted or substituted branched alkyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkyl of 3 to 30 carbon atoms, substituted or unsubstituted linear alkoxy of 1 to 30 carbon atoms, branched or unsubstituted branched alkoxy of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkoxy of 3 to 30 carbon atoms, substituted linear alkenyl or unsubstituted of 2 to 30 carbon atoms, unsubstituted or substituted branched alkenyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkenyl of 3 to 30 carbon atoms, substituted or unsubstituted linear alkynyl of 2 to 30 atoms of carbon, substituted or unsubstituted branched alkynyl of 3 to 30 carbon atoms, substituted or unsubstituted alkylenearyl of 6 to 30 carbon atoms, or R4, R5 and R6 can be taken together to form unsubstituted or substituted aryl of 6 to 30 carbon atoms; and mixtures thereof; b) at least about 0.01% by weight, of one or more additive ingredients selected from the group consisting of surfactants, emollients, bactericides, gelling agents, spreaders, propellants, dyes, colorants, ointment bases, lanolin, antiperspirants, mineral oil talc, abrasives, optical brighteners, phase stabilizing agents, absorbers, pharmaceutical active ingredients, and mixtures thereof; and c) the rest, carriers. 9. A composition for the release of a lasting fragrance or harmony characterized in that it comprises: a) at least about 0.01%, preferably about 0.01% to 15%, more preferably about 1% to 5%, much preferable to 0.1% to 1% by weight, of a β-ketoester having the formula: wherein R is alkoxy derived from an alcohol of fragrance raw material; R1, R2 and R3 are independently hydrogen, substituted or unsubstituted linear alkyl of 1 to 30 carbon atoms, unsubstituted or substituted branched alkyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkyl of 3 to 30 carbon atoms , substituted or unsubstituted linear alkenyl of 2 to 30 carbon atoms, unsubstituted or substituted branched alkenyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkenyl of 3 to 30 carbon atoms, substituted or unsubstituted linear alkynyl of 2 to 30 carbon atoms, unsubstituted or substituted branched alkynyl of 3 to 30 carbon atoms, substituted or unsubstituted alkylenearyl of 6 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, substituted alkylenoxy or unsubstituted from 2 to 20 carbon atoms, substituted or unsubstituted alkylene-xalkyl of 3 to 20 carbon atoms, substituted or unsubstituted alkylenearyl of 7 to 20 carbon atoms, substituted or unsubstituted lyalkyloxyaryl of 6 to 20 carbon atoms, and mixtures thereof; conditional on R1, R2 or R3 being a unit that has the formula: wherein R4, R5 and R6 are independently hydrogen, substituted or unsubstituted linear alkyl of 1 to 30 carbon atoms, unsubstituted or substituted branched alkyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkyl of 3 to 30 carbon atoms carbon, substituted or unsubstituted linear alkoxy of 1 to 30 carbon atoms, branched or unsubstituted branched alkoxy of 3 to 30 carbon atoms, unsubstituted or substituted cyclic alkoxy of 3 to 30 carbon atoms, linear alkenyl substituted or unsubstituted substituted from 2 to 30 carbon atoms, unsubstituted or substituted branched alkenyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkenyl of 3 to 30 carbon atoms, substituted or unsubstituted linear alkynyl of 2 to 30 carbon atoms , substituted or unsubstituted branched alkynyl of 3 to 30 carbon atoms, substituted or unsubstituted alkylenearyl of 6 to 30 carbon atoms, or R4, R5 and R6 can be taken together to form substituted or unsubstituted aryl of 6 to 30 carbon atoms. ; and mixtures thereof; and b) the remainder comprises a carrier, said carrier selected from the group consisting of water, alcohols of 1 to 3 carbon atoms, polyhydric alcohols of 2 to 8 carbon atoms, cationic and water-soluble anionic polymers, polyethylene glycols, and mixtures thereof. same. 10. A hard surface cleaning composition with fragrance retention and fragrance longevity on increased hard surfaces, further characterized in that it comprises: a) at least about 0.1%, preferably at least about 0.5% by weight, of a surfactant detergent compatible with hard surface cleaners; b) at least about 0.01%, preferably about 0.01% to 15%, more preferably about 1% to 5%, much preferable about 0.1% to 1% by weight, of a β-ketoester having the formula: wherein R is a substituted or unsubstituted linear alkyl of 1 to 30 carbon atoms, unsubstituted or substituted branched alkyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkyl of 3 to 30 carbon atoms, substituted linear alkenyl or unsubstituted of 2 to 30 carbon atoms, unsubstituted or substituted branched alkenyl of 3 to 30 carbon atoms, substituted or unsubstituted cyclic alkenyl of 3 to 30 carbon atoms, substituted or unsubstituted linear alkynyl of 2 to 30 atoms carbon, substituted or unsubstituted branched alkynyl of 3 to 30 carbon atoms, substituted or unsubstituted alkylenearyl of 6 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, and mixtures thereof; R1 is an alkoxy unit derived from an alcohol fragrance raw material, R2 and R3 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted linear alkyl of 1 to 20 carbon atoms, unsubstituted or substituted branched alkyl of 3 at 20 carbon atoms, substituted or unsubstituted alkyleneoxy of 2 to 20 carbon atoms, substituted or unsubstituted alkylene-alkyl of 3 to 20 carbon atoms, substituted or unsubstituted alkylenearyl of 7 to 20 carbon atoms, substituted or unsubstituted alkylenenoxyaryl from 6 to 20 carbon atoms, and mixtures thereof; and c) the rest, carriers and additive ingredients. 11. A composition according to claim 10, further characterized in that it also comprises at least about 0.1%, preferably at least 0.5% by weight, of a sulfosuccinamate having the formula: wherein R1 and R2 are hydrogen or SO3M2 provided that R1 is not equal to R2; R3 is butyl when R4 is ethyl and R3 is pentyl when R4 is propyl; M and M2 are independently hydrogen or a salt-forming cation. 12. A composition according to claim 11 characterized in that it further comprises at least about 0.1%, preferably 0.5% by weight, of a nonionic surfactant having the formula CH3 (CH2) xCH20 (CH2CH20) and H wherein x is about 6 to 12, "and" is about 3.5 to 10. 13. A composition according to claim 10. further characterized in that it also comprises carriers and additive ingredients, said ingredients being selected additives from the group consisting of abrasives, detergency builders, bleaches, bleach activators, clays, detergent surfactants, thickeners, dispersants, enzymes, dyes, dyes, filler salts, hydrotropes, enzymes, preservatives, antioxidants, chelators, stabilizers, germicides, fungicides, solvents, photo-disinfectants, and mixtures thereof.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US024117 | 1996-08-19 | ||
US60/024,117 | 1996-08-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
MXPA99001728A true MXPA99001728A (en) | 1999-09-20 |
Family
ID=
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