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1. 发明授权

US4036774A Fragrant soap compositions containing alpha-substituted acetaldehyde and ketone 失效
标题翻译：含有α-取代乙醛和酮的香皂组合物
公开(公告)号：US4036774A
公开(公告)日：1977-07-19
申请号：US741141
申请日：1976-11-11
申请人： Anton van Ouwerkerk , Bernard J. Chant , Arthur L. Liberman
发明人： Anton van Ouwerkerk , Bernard J. Chant , Arthur L. Liberman
IPC分类号： A23G4/00 , A23G4/06 , A23L27/20 , A24B15/34 , C11B9/00 , C11D3/50 , C11D9/44
CPC分类号： A23G4/06 , A23L27/20 , A23L27/203 , A23L27/204 , A24B15/34 , C11B9/0034 , C11B9/0061 , C11D3/0084
摘要： Processes and compositions are described for the use in perfume aroma augmenting, modifying, altering and enhancing compositions and as perfume and perfumed article aroma imparting materials of mixtures of (i) 2,2,6-trimethyl-1-cyclohexen-1-ylacetaldehyde (hereinafter referred to as "beta-cyclohomocitral") produced by a process which either (A) comprises the steps of:I. Oxidizing beta-ionone having the formula: ##STR1## with a peralkanoic acid having the formula: ##STR2## (wherein R is H, methyl or ethyl) in the presence of buffer and in the absence of dimethyl formamide, to form 2,2,6-trimethyl-1-cyclohexen-1-ylvinylacetate (hereinafter referred to as "beta-ionone enol ester") having the formula: ##STR3## ii. Hydrolyzing said beta-ionone enol ester using a basic hydrolysis agent to form beta-cyclohomocitral having the structure: ##STR4## or (B) oxidizing beta-ionone with hydrogen peroxide in the presence of inorganic base to form beta-cyclohomocitral directly, and (ii) one or two phenyl C.sub.6 ketone which may be either or both 2,5-dimethyl-5-phenyl hexanone-4 (hereinafter termed "4-damascol") or 2,5-dimethyl-5-phenyl hexen-1-one-4 (hereinafter termed "damascol") having the generic structure: ##STR5## wherein the dashed line represents either a carbon-carbon single bond or a carbon-carbon double bond. Addition of mixtures of beta-cyclohomocitral and one or both phenyl C.sub.6 ketones is indicated to modify, augment, impart or enhance in perfumes as well as in perfumed articles rosey, woody, camphoraceous, green and earthy notes.
摘要翻译：描述了用于香料香气增强，改性，改性和增强组合物的方法和组合物，以及（i）2,2,6-三甲基-1-环己烯-1-基乙醛（ⅰ）的混合物的香料和香料制品香气赋予材料，（A）包括以下步骤：

2. 发明授权

US4620945A Mixtures of one or more t-mercapto terpene isomers and .alpha.-terpineol, .beta.-phenylethyl alcohol, 3-methyl-1-phenyl-pentanol-5 and/or butanoyl cyclohexane derivatives, organoleptic uses thereof and process for preparing same 失效
标题翻译：一种或多种t-巯基萜烯异构体和α-萜品醇，β-苯乙醇，3-甲基-1-苯基 - 戊醇-5和/或丁酰基环己烷衍生物的混合物，其感官用途及其制备方法
公开(公告)号：US4620945A
公开(公告)日：1986-11-04
申请号：US644053
申请日：1984-08-24
申请人： Braja D. Mookherjee , Bernard J. Chant , William J. Evers , Richard A. Wilson , Michael J. Zampino , Manfred H. Vock
发明人： Braja D. Mookherjee , Bernard J. Chant , William J. Evers , Richard A. Wilson , Michael J. Zampino , Manfred H. Vock
IPC分类号： C07D331/02 , C11B9/00 , A61K7/46
CPC分类号： C07D331/02 , C11B9/0034
摘要： Described are organoleptic utilities of mixtures of t-mercapto terpene isomers defined according to the generic structure: ##STR1## wherein one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines is a carbon-carbon single bond taken further together with .alpha.-terpineol having the structure: ##STR2## .beta.-phenylethyl alcohol having the structure: ##STR3## 3-methyl-1-phenyl-pentanol-5 having the structure: ##STR4## and/or butanoyl cyclohexane derivatives defined according to the generic structure: ##STR5## wherein one of the dashed lines is a carbon-carbon double bond or two of the dashed lines represent carbon-carbon double bonds but that when two of the dashed lines represent carbon-carbon double bonds, the carbon-carbon double bonds are conjugated.
摘要翻译：描述了根据通用结构定义的t-巯基萜烯异构体混合物的感官效用：其中一条虚线是碳 - 碳双键，另一条虚线是碳 - 碳单键取代进一步与具有以下结构的α-萜品醇结合：具有以下结构的具有以下结构的β-苯乙醇：具有以下结构的3-甲基-1-苯基 - 戊醇-5：具有以下结构的化合物：和/或丁酰基环己烷衍生物涉及通用结构：其中虚线中的一条为碳 - 碳双键，或两条虚线表示碳 - 碳双键，但当虚线中的两条代表碳 - 碳双键时，碳 - 碳双键共轭。

3. 发明授权

US4446125A Use of isomeric farnesene product-by-process for augmenting or enhancing the aroma or taste of foodstuffs, chewing gums, medicinal products and toothpastes 失效
标题翻译：使用异构法呢烯产品逐步增加或增强食品，口香糖，药用产品和牙膏的香气或味道
公开(公告)号：US4446125A
公开(公告)日：1984-05-01
申请号：US461476
申请日：1983-01-27
申请人： Braja D. Mookherjee , Robert W. Trenkle , Bernard J. Chant , Anton V. Ouwerkerk , Venkatesh Kamath , Cynthia J. Mussinan
发明人： Braja D. Mookherjee , Robert W. Trenkle , Bernard J. Chant , Anton V. Ouwerkerk , Venkatesh Kamath , Cynthia J. Mussinan
IPC分类号： C07C1/24 , C11B9/00 , A23L1/226
CPC分类号： C11B9/0007 , C07C1/24 , C07C2527/055
摘要： Described are isomeric mixtures of farnesene prepared by dehydrating nerolidol using potassium bisulfate or paratoluene sulfonic acid and then distilling the resultant product at particular temperature ranges and particular pressure ranges in order to prepare a composition of matter useful for augmenting or enhancing the fresh green, herbaceous aroma and taste nuances of foodstuffs, chewing gums, medicinal products and toothpastes.
摘要翻译：描述了通过使用硫酸氢钾或对甲苯磺酸脱水橙花叔醇制备的法呢烯异构体混合物，然后在特定温度范围和特定压力范围内蒸馏所得产物，以制备用于增强或增强新鲜绿色草本香气的物质组合物并品尝食品，口香糖，药用产品和牙膏的细微差别。

4. 发明授权

US4536583A Process for preparing mixtures containing 8,9-epithio-1-p-menthene 失效
标题翻译：制备含有9,9-环硫-1-对薄荷烯的混合物的方法
公开(公告)号：US4536583A
公开(公告)日：1985-08-20
申请号：US519371
申请日：1983-08-01
申请人： Braja D. Mookherjee , Bernard J. Chant , William J. Evers , Richard A. Wilson , Michael J. Zampino , Manfred H. Vock
发明人： Braja D. Mookherjee , Bernard J. Chant , William J. Evers , Richard A. Wilson , Michael J. Zampino , Manfred H. Vock
IPC分类号： C07D331/02 , C11B9/00 , A61K7/46
CPC分类号： C07D331/02 , C11B9/0034
摘要： Described is a process for preparing a mixture of t-mercapto terpenes defined according to the structure: ##STR1## and .alpha.-terpineol defined according to the structure: ##STR2## including the step of reacting the compound defined according to the structure: ##STR3## with an alkali metal thiocyanate defined according to the structure: ##STR4## wherein M represents alkali metal such as sodium, potassium or lithium in the presence of a phase transfer catalyst. The resulting product is then treated with lithium aluminum hydride followed by aqueous mineral acid to form a mixture of .alpha.-terpineol and the compound defined according to the structure: ##STR5## which mixture is useful for its organoleptic properties.
摘要翻译：描述了根据以下结构定义的t-巯基萜烯的混合物的方法：根据以下结构定义的：ι和α-萜品醇：包括使根据以下结构定义的化合物反应的步骤：碱金属硫氰酸盐根据以下结构定义：其中M在相转移催化剂存在下表示碱金属如钠，钾或锂。然后将所得产物用氢化铝锂处理，然后用无机酸水溶液处理，以形成α-萜烯醇和根据以下结构定义的化合物的混合物：该组合物可用于其感官特性。

5. 发明授权

US4028279A Novel fragrance compositions containing 2,6,6 trimethyl-1-cyclohexen-1-yl acetaldehyde and phenyl C.sub.6 ketone 失效
标题翻译：含有2,6,6三甲基-1-环己烯-1-基乙醛和苯基C（HD 6 {B酮）的新型香料组合物
公开(公告)号：US4028279A
公开(公告)日：1977-06-07
申请号：US601727
申请日：1975-08-04
申请人： Anton Van Ouwerkerk , Bernard J. Chant , Arthur L. Liberman
发明人： Anton Van Ouwerkerk , Bernard J. Chant , Arthur L. Liberman
IPC分类号： A23G4/00 , A23G4/06 , A24B15/34 , C11B9/00
CPC分类号： A23G4/06 , A24B15/34 , C11B9/00 , C11D3/0084
摘要： Processes and compositions are described for the use in perfume aroma augmenting, modifying, altering and enhancing compositions and as perfume and perfumed article aroma imparting materials of mixtures of (i) 2,2,6-trimethyl-1-cyclohexen-1-ylacetaldehyde.BACKGROUND OF THE INVENTIONThe present invention relates to mixtures of (i) either or both of the phenyl C.sub.6 ketones, 2,5,-dimethyl-5-phenyl hexanone-4 (hereinafter referred to as "4-damascol") and 2,5,-dimethyl-5-phenyl hexen-1-one-3 (hereinafter termed "damascol") and(ii) 2,2,6-trimethyl-1-cyclohexen-1-ylacetaldehyde (hereinafter termed "beta-cyclohomocitral) produced by interalia, a novel process described and claimed in copending application for U.S. Pat. No. 507,414 on Sept. 19, 1974 now U.S. Pat. No. 3,956,393, issued on May 4, 1976, and copending application for U.S. Pat. No. 594,100 filed on July 8, 1975 and novel compositions using such mixtures of phenyl C.sub.6 ketone and beta-cyclohomocitral to alter, modify, enhance (or impart) aromas in (or to) perfumes, perfume compositions and/or perfumed articles.There has been considerable work performed relating to substances which can be used to impart (or alter, modify or enhance) fragrances to (or in) perfumed compositions, perfumes, or perfumed articles. These substances are used to diminish the use of natural materials, some of which may be in short supply and/or to provide more uniform properties in the finished product. Woody, rosey, camphoraceous, green and earthy notes are desirable in several types of perfume compositions, perfumes and perfumed articles.Arctander, "Perfume and Flavor Chemicals," 1969 discloses the use in perfume compositions and flavors of "cyclocitral", "dehydro-beta-cyclocitral", "iso-cyclocitral", "alpha-cyclocitrylidene acetaldehyde" and "beta-cyclotrylidene acetaldehyde", thus:(I) "760: CYCLOCITRALAlpha-cyclocitral= (2,2,6-trimethyl-5-cyclohexen-1-carboxaldehyde). Beta-cyclocitral= (2,2,6-trimethyl-6-cyclohexen-1-carboxaldehyde). Both isomers are known and have been produced separately. ##STR1## Very rarely offered commercially. These particular cyclocitrals have little or no interest to the creative perfumer, but they have served as part of many pieces of proof that isomers (alpha-beta) do often have different odors."(II) ("761: ISO-CYCLOCITRALA mixture of two chemicals: 3,5,6-trimethyl-3-cyclohexen-1-carboxaldehyde (meta-cyclocitral). ##STR2## 2,4,6-TRIMETHYL-4-CYCLOHEXEN-1-CARBOXALDEHYDE (SYMMETRIC-ISO-CYCLOCITRAL). ##STR3## Powerful, and diffusive, foliage-green, "dark" weedy and dry odor, sometimes described as "Flower-shop odor". The earthy and wet-green notes are quite natural in high dilution and resemble the odor of stems from plants and flowers fresh from the soil.Finds use in perfume compositions where it blends excellently with Oakmoss products (compensates for sweetness and lifts the topnote), with Ionones (freshness), Geranium and Galbanum (enhances the green and "vegetable" notes), etc. . . . "(iii) "762: alpha CYCLOCITRYLIDENE ACETALDEHYDE ##STR4## Mild, floral-woody, somewhat oily-herbaceous odor, remotely reminiscent of Rose with similarity to the odor of hydrogenated Ionones.Suggested for use in perfume compositions. It brings a certain amount of floral lift to Rose compositions, and performs fairly well even in soap. However, the cost of the rarely offered and never readily available lots are rather discouraging to the perfumer, and it is most conceivable that this material can be left out of the perfumer's library without any great loss. . . . " (iv) "763: beta-CYCLOCITRYLIDENE ACETALDEHYDE 2,6,6-trimethyl-1-cyclohexenyl-beta-acrolein. ##STR5## Sweet-woody, rather heavy odor, resembling that of beta-Ionone. More fruity than really floral, but not as tenacious as the Ionone.Suggested for use in perfume compositions, but since it does not offer any new or unusual odor characteristics, and it cannot be produced in economical competition to beta-Ionone, there is little or no chance that it will ever become a standard shelf ingredient for the perfumer. . . . "(v) "896: DEHYDRO-beta-CYCLOCITRAL (Safranal) 2,6,6-trimethyl-4,4-cyclohexadiene-1-carboxaldehyde ##STR6## Very powerful, sweet, green-floral and somewhat tobacco-herbaceous odor of good tenacity. In extreme dilution reminiscent of the odor of Safran (Saffron).Interesting material for fresh topnotes, as a modifier for aldehydic-citrusy notes, as a green-floral topnote in flower fragrances, etc. It blends excellently with the aliphatic Aldehydes, with Oakmoss products and herbaceous oils. . . . "Safranal and beta-cyclocitral are disclosed as volatile constituents of Greek Tobacco by Kimland et al., Phytochemistry 11 (309) 1972. Beta-cyclocitral is disclosed as a component of Burley Tobacco flavor by Demole and Berthet, Helv. Chim. Acta. 55 Fasc-6, 1866 (1972).
摘要翻译：描述了用于香料香气增强，改性，改变和增强组合物以及作为（i）2,2,6-三甲基-1-环己烯-1-基乙醛的混合物的香料和香料制品香气赋予材料的方法和组合物。

6. 发明授权

US4584128A Mixture of one or more t-mercapto terpene isomers and .alpha.-terpineol organoleptic uses thereof 失效
标题翻译：一种或多种t-巯基萜烯异构体和α-萜品醇感官用途的混合物
公开(公告)号：US4584128A
公开(公告)日：1986-04-22
申请号：US644117
申请日：1984-08-24
申请人： Braja D. Mookherjee , Bernard J. Chant , William J. Evers , Richard A. Wilson , Michael J. Zampino , Manfred H. Vock
发明人： Braja D. Mookherjee , Bernard J. Chant , William J. Evers , Richard A. Wilson , Michael J. Zampino , Manfred H. Vock
IPC分类号： C07D331/02 , C11B9/00 , A61K7/46
CPC分类号： C11B9/0034 , C07D331/02
摘要： Described are mixtures of t-mercapto terpene isomers defined according to the generic structure: ##STR1## wherein one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines is a carbon-carbon single bond taken further together with .alpha.-terpineol having the structure: ##STR2##
摘要翻译：描述了根据通用结构定义的t-巯基萜烯异构体的混合物：其中一条虚线是碳 - 碳双键，另一条虚线是碳 - 碳单键，进一步与具有以下结构的α-萜品醇：

7. 发明授权

US4391717A Use of isomeric farnesene product-by-process for augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles 失效
标题翻译：使用异构法呢烯法逐步增加或增强香水组合物，古龙水和香水制品的香气
公开(公告)号：US4391717A
公开(公告)日：1983-07-05
申请号：US375534
申请日：1982-05-06
申请人： Braja D. Mookherjee , Robert W. Trenkle , Bernard J. Chant , Anton V. Ouwerkerk , Venkatesh Kamath , Cynthia J. Mussinan
发明人： Braja D. Mookherjee , Robert W. Trenkle , Bernard J. Chant , Anton V. Ouwerkerk , Venkatesh Kamath , Cynthia J. Mussinan
IPC分类号： C11B9/00 , D06M13/00 , D06M13/16
CPC分类号： C11B9/0007 , D06M13/005 , C07C2527/055 , Y10S428/905
摘要： Described are isomeric mixtures of farnesene prepared by dehydrating nerolidol using potassium bisulfate or paratoluene sulfonic acid and then distilling the resultant product at particular temperature ranges and particular pressure ranges in order to prepare a composition of matter useful for augmenting or enhancing waxy, white-flowery (magnolia-like, tuberose, gardenia-like) aromas with citrusy (lemon/lime), pettitgrain-like undertones and green top notes in perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, dryer-added fabric softener articles, cosmetic powders and the like).
摘要翻译：描述了通过使用硫酸氢钾或对甲苯磺酸脱水橙花叔醇制备的法呢烯的异构体混合物，然后在特定温度范围和特定压力范围内蒸馏所得产物，以制备用于增强或增强蜡质，白花（香柠檬，晚香玉，栀子花）芳香与柠檬/柠檬（柠檬/石灰），香草组合物，香水和香水制品（例如固体或液体阴离子，阳离子，非离子或两性离子洗涤剂，织物柔软剂组合物，干燥剂添加的织物柔软剂制品，化妆品粉末等）。

8. 发明授权

US4390444A Use of isomeric mixtures of farnesene for augmenting or enhancing the aroma of detergent compositions 失效
标题翻译：使用法呢烯的异构体混合物来增强或增强洗涤剂组合物的香气
公开(公告)号：US4390444A
公开(公告)日：1983-06-28
申请号：US375532
申请日：1982-05-06
申请人： Braja D. Mookherjee , Robert W. Trenkle , Bernard J. Chant , Anton V. Ouwerkerk , Venkatesh Kamath , Cynthia J. Mussinan
发明人： Braja D. Mookherjee , Robert W. Trenkle , Bernard J. Chant , Anton V. Ouwerkerk , Venkatesh Kamath , Cynthia J. Mussinan
IPC分类号： C11B9/00 , C11D3/50
CPC分类号： C11D3/50 , C11B9/0007 , C07C2527/055
摘要： Described are isomeric mixtures of farnesene prepared by dehydrating nerolidol using potassium bisulfate or paratoluene sulfonic acid and then distilling the resultant product at particular temperature ranges and particular pressure ranges in order to prepare a composition of matter useful for augmenting or enhancing waxy, white-flowery (magnolia-like, tuberose, gardenia-like) aromas with citrusy (lemon/lime), pettitgrain-like undertones and green top notes in perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, dryer-added fabric softener articles, cosmetic powders and the like).
摘要翻译：描述了通过使用硫酸氢钾或对甲苯磺酸脱水橙花叔醇制备的法呢烯的异构体混合物，然后在特定温度范围和特定压力范围内蒸馏所得产物，以制备用于增强或增强蜡质，白花（香柠檬，晚香玉，栀子花）芳香与柠檬/柠檬（柠檬/石灰），香草组合物，香水和香水制品（例如固体或液体阴离子，阳离子，非离子或两性离子洗涤剂，织物柔软剂组合物，干燥剂添加的织物柔软剂制品，化妆品粉末等）。

9. 发明授权

US4376068A Use of isomeric farnesene product-by-process for augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles 失效
公开(公告)号：US4376068A
公开(公告)日：1983-03-08
申请号：US292392
申请日：1981-08-13
申请人： Braja D. Mookherjee , Robert W. Trenkle , Bernard J. Chant , Anton van Ouwerkerk , Venkatesh Kamath , Cynthia J. Mussinan
发明人： Braja D. Mookherjee , Robert W. Trenkle , Bernard J. Chant , Anton van Ouwerkerk , Venkatesh Kamath , Cynthia J. Mussinan
IPC分类号： C07C1/24 , C11B9/00 , A61K7/46
CPC分类号： C11B9/0007 , C07C1/24 , C07C2527/055
摘要： Described are isomeric mixtures of farnesene prepared by dehydrating nerolidol using potassium bisulfate or paratoluene sulfonic acid and then distilling the resultant product at particular temperature ranges and particular pressure ranges in order to prepare a composition of matter useful for augmenting or enhancing waxy, white-flowery (magnolia-like, tuberose, gardenia-like) aromas with citrusy (lemon/lime), pettitgrain-like undertones and green top notes in perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, dryer-added fabric softener articles, cosmetic powders and the like).

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