US3876551A - Perfumed aqueous hypochlorite composition and method for preparation of same - Google Patents

Perfumed aqueous hypochlorite composition and method for preparation of same Download PDF

Info

Publication number
US3876551A
US3876551A US304807A US30480772A US3876551A US 3876551 A US3876551 A US 3876551A US 304807 A US304807 A US 304807A US 30480772 A US30480772 A US 30480772A US 3876551 A US3876551 A US 3876551A
Authority
US
United States
Prior art keywords
amine oxide
alkali metal
composition
hypochlorite
solution
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US304807A
Inventor
Robert John Laufer
Jr John Henry Geiger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
International Flavors and Fragrances Inc
Original Assignee
International Flavors and Fragrances Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by International Flavors and Fragrances Inc filed Critical International Flavors and Fragrances Inc
Priority to US304807A priority Critical patent/US3876551A/en
Application granted granted Critical
Publication of US3876551A publication Critical patent/US3876551A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/395—Bleaching agents
    • C11D3/3956—Liquid compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/75—Amino oxides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes

Definitions

  • ABSTRACT A stable single phase aqueous alkali metal hypochlorite liquid perfumed bleach or sterilizing composition 1 Apr. 8, 197 5 1 comprising an aqueous mixture of I) an amine oxide 5 composition consisting essentially of at least one mor- E pholinoand/or dimethyl (C -C straight chain alkyl) amine oxide. in an amount greater than 55% of said 7 amine oxide composition, (2) at least one alkali metal hydroxide. (3) at least one alkali metal hypochlorite.
  • the pH of the aqueous hypochlorite solution is initially adjusted to the range of l2-l3.5 and then" the premix is combined with the pH-adjusted aqueous hypochlorite solution.
  • the resulting composition when used as a bleach or sterilizing agent causes the products to which said composition is applied to have virtually eliminated therefrom the disagreeable charac-@ teristic hypochlorite aroma; and instead, a pleasant clean fresh" or floral or woody or musk or citrusy” aroma is imparted to such treated products.
  • the hands of the individual user after using and being in direct contact with the composition will not have the disagreeable characteristic hypochIorite" aroma but instead will have a pleasant clean fresh or floral or woody or musk" or citrusy ⁇ aroma.
  • each of R1. R2, R and R are alkyl.
  • One of the features of the perfumed solutions produced in accordance with said British Patent Specification No. 886,084 was indicated to be that the solution exhibits foaming properties.
  • Another feature of British Patent Specification No. 886.084 is stated to be that the perfumed solutions covered by the invention are found to be clear and homogeneous after eight weeks storage at room temperature. Nevertheless.
  • betaines such as Ambiteric D as are discussed therein are not so broadly useful when used in the concentrations of from 0.15% up to l.07( (based on the total weight of bleach or sterilizing solution) as to have the ability to be used in conjunction with woody or floral" or clean fresh or musk or citrusy” types of perfume oils which should be incorporated into hypochlorite bleaches or sterilizers so that long lasting stable soluble single phase perfumed aqueous alkali metal hypochlorite bleach or sterilizing solutions having woody" or musk or citrusy or floral” or "clean fresh long lasting stable aromas are obtained, particularly where the quantity of perfume oil in the bleach or sterilizing is at levels of between 0.02% and 02% by weight of the total bleach or sterilizing solution.
  • U.S. Pat. No. 3,560,389 also discloses the feasibilit of using perfume oils in hypochlorite bleaches or sterilizers at Column 3, lines 37-40 but the disclosure is him ited to inclusion of various detergents in addition to amine oxides, such as lithium lauryl sulfate and sodium lauryl ether sulfate and/or is further limited to include hydrotropes such as sodium xylene sulfonate in addition to the amine oxide. Exclusion of such hydrotropes and additional detergents is desirable not only to cause Neither the South African nor the United States patents, however, indicate the advantages and usefulness. of limiting the detergents solely to amine oxides, or of; excluding from the formulation a hydrotrope or of; specifying the nature of the perfume oil useful in the perfumed bleach or sterilizing solution.
  • This invention relates to the production of perfumedj single phase aqueous alkali metal hypochlorite solutions suitable for laundry and general domestic bleach-z ing and sterilizing purposes.
  • perfumed aqueous alkali metal hypochlorite solutions which yield a long lasting per-i fume aroma (particularly those having a "woody” or “floral” or clean fresh” or “musk: or citrusy fra-E grance) and which are capable of imparting to surfaces; (e.g.
  • this invention consists of an aqueous solution of at least one alkali metal hypochlorite con-; taining a stable perfume oil and a surface active agent consisting solely of an amine oxide composition and;
  • R is straight chain alkyl having from 11 up to 13 carbon atoms and A and B are each separately methyl, or, taken together, complete a morpholino ring and having a pH in the range of 12-135
  • the chain length(s) of the R moiety (or moieties) ol the predominating alkyl dimethyl amine oxide(s) of the amine oxide composition is critical for providing an aqueous hypochlorite bleach or sterilizing solution which can be perfumed with the woody" or floral” or clean fresh” or musk” or citrusy” fragrance formulations required for our invention.
  • the concentration of the amine oxide composition required to create the transparent solution of this invention is from 0.15% up to 1.0% based on the total weight of solution. Concentrations of amine oxides less than 0.15% will not give rise to the desired single phase system containing the desired special perfume oil (having the woody" or floral or clean fresh” or musk” or citrusy” aroma) required for this invention. From a commercial standpoint concentrations of amine oxide(s) greater than 1.0% based on total weight i of hypochlorite solution are not needed and give rise to unnecessary costs.
  • the pH range of the aqueous alkali metal hypochlorite solution containing the amine oxide composition and one of the requisite perfume formulations is critical; that is. a pH of from 12 up to 13.5 is required for the composition of our invention, with the preferred pH range being between 12.5 and 12.9.
  • the requisite pH range is achieved by adding an aqueous solution of alkali metal hydroxide (e.g. from 1M up to 12.5M) to the alkali metal hypochlorite solution which has had or will have added to it the amine oxide-perfume oil premix.
  • the percentage of perfume oil having the properties which yield woody or floral or clean fresh" or musk or citrusy aroma is in the range of from 0.02% up to 0.2% based on the total final weight of aqueous alkali metal hypochlorite solution. Lower concentrations of such perfume oils will not be adequate to give rise to the desired substantial diminution or elimination of the characteristic disagreeable hypochlorite aroma (which exists on. for example. laundry and/or the hands of the individual user which have been in direct contact with the hypochlorite bleach or sterilizing solution subsequent to the use of aqueous hypochlorite solutions as a general domestic bleach or sterilizer). Quantities of perfume oil greater than 0.2% have been found to be uneconomical and unnecessary for the practice of our invention.
  • the perfume oil may be premixed with the amine oxide solubilizer and the resulting perfume oil-amine oxide premix is then mixed with the hypochlorite bleaching or sterilizing solution with stirring.
  • an aqueous alkali metal hydroxide solution is added to the mixture to bring the pH to the range of l2-13.5.
  • a pH of less than 12 is not desired since it is difficult to achieve a single phase stable system at such low pHs.
  • a pH higher than 13.5 will also create a system which (1) is unnecessarily corrosive; (2) will narrow the range of perfume oils usable in the system; and (3) will limit the particular ingredients usable in such perfume oils.
  • the aqueous alkali metal hydroxide can be added to the aqueous alkali metal hypochlorite solution before adding the amine oxide or the perfume oil.
  • the ingredients: the perfume oil, the alkali metal hydroxide and the amine oxide composition may be added or admixed in any order which is convenient to the formulator.
  • One desirable process involves first forming the amine oxide composition perfume oil premix, mixing the premix with the aqueous alkali metal hypochlorite solution and finally adjusting the pH of the solution with alkali metal hydroxide to bring the pH to within the range of l2-13.5.
  • a second more preferable process involves first adjusting the pH of the aqueous alkali metal hypochlorite solution to 12-13.5 and then admixing this solution with the afore-described premix.”
  • the alkali metal hypochlorites preferred in the practice of our invention are: sodium hypochlorite, potassium hypochlorite and lithium hypochlorite, or mixtures of same.
  • the alkali metal hydroxides preferred in the practice of this invention are lithium hydroxide, potassium hydroxide and sodium hydroxide, or, ifdesired, mixtures of such hydroxides.
  • the temperature at which the composition of our invention remains both substantially stable and commercially usable for the purposes set forth herein (that is, remains as a clear single aqueous phase and retains l the desired properties inherent in the known bleaching and sterilizing uses of aqueous alkali metal hypochlorite solutions, and (2) the properties imparted thereto as a result of using the perfume oils which impart to the aqueous alkali metal hypochlorite solutions a woodyor floral or clean fresh" or musk" or citrusy” aroma) varies from approximately 20 F up to approximately F. At temperatures below 20 F a twophase system usually occurs and at temperatures higher than 120 F the bleaching or sterilizing efficiency of the composition of our invention is diminished at an excessive rate.
  • the upper bound of the temperature range is the decomposition point of any one of the amine oxide components of the amine oxide composition and the lower bound is the least temperature where a single liquid phase including the amine oxide(s) will exist.
  • Preferred amine oxide compositions from a practical standpoint useful in the practice of our invention are the commercially available (1) dimethyl cocoamine oxide (a mixture which is dominated by dimethyl- C C straight chain alkyl amine oxide; more particularly a mixture containing approximately 70% C straight chain amine oxides, approximately 25% C of straight chain amine oxides and approximately 4% C straight chain alkyl amine oxides) and (2) N- cocomorpholine oxide, a mixture dominated by C -C straight chain alkyl morpholine oxides (specifically containing approximately 70% C straight chain alkyl morpholine oxide. approximately 25% C straight chain alkyl morpholine oxide and approximately 4% C straight chain alkyl morpholine oxide).
  • dimethyl cocoamine oxide a mixture which is dominated by dimethyl- C C straight chain alkyl amine oxide; more particularly a mixture containing approximately 70% C straight chain amine oxides, approximately 25% C of straight chain amine oxides and approximately 4% C straight chain alkyl amine oxides
  • N- cocomorpholine oxide a
  • amine oxide compositions are: Aromox DMC-W and Aromox DMMC-W which are 30% aqueous dimethyl cocoamine oxide solutions and Aromox NCMDW which is a 40% aqueous N-cocomorpholine oxide solution. each of which is produced by the Armac Division of AKZO of Chicago, Illinois. These materials are described in Brochure 6801]. published by Armour Industrial Chemicals, P.O.B. I805, Chicago. Illinois 60690.
  • Other preferred amine oxides are n-undecyl dimethyl amine oxide and n-tridecyl dimethyl amine oxide.
  • the percentage of hypochlorite ion in the composition of this invention may vary from about We up to about i671 for the desired effects to be produced using the amine oxide-perfume oil compositions covered by our invention.
  • the usual percent of alkali metal hypochlorite in solution is about 5%, the percentage of sodium hypochlorite in such materials as CLOROX the registered trademark of Clorox Corporation.
  • the perfume oil used in conjunction with the aqueous alkali metal hypochlorite solution must have such properties as to be able (1) to impart to the resulting or aqueous alkali metal hypochlorite solution either a woody or a floral' or a clean fresh" or musk" or citrusy” aroma; (2) to effect a substantial diminution or elimination of the disagreeable hypochlor-ite" aroma which is imparted to surfaces (e.g.
  • 3,373,208 such as cedryl methyl ether
  • 3,281,432 such as octahydro-l,3a,6-trimethylll-ll ,6u,ethanopentaleno-( l,2-C furan;
  • 2,889,367 such as 4-acetyl-l,l-dimethyl--tbutyl indane
  • Naphthyl ethers such as ,B-naphthyl methyl ether and B-naphthyl ethyl ether;
  • No. 780,489 such as 2,5-dimethyl-5-phenylhexanone-3.
  • a basic feature of our invention concerns the fact that the only detergent group needed or desirable in the composition of our invention is the class of morpholino and/or dimethyl C -C straight chain alkyl amine oxides. More specifically, such detergents as sodium decyl ether sulfate, sodium myristyl ether sulfate. so-
  • the subject mixture has an intense pleasant woody aroma.
  • Examples lV-XIV Aromox DMC-W and Aromox DMMC-W are 30% aqueous solutions of dimethyl cocoamine oxide; and Aromox NCMDW is a 40% aqueous solution of N-cocomorpholine oxide produced by Armac Division ofAKZO ofChicago, Illinois.
  • EXAMPLE IV Four drops of a perfume oil, the mixture of Example I, is added to 2 grams of Aromox DMC-W to produce a clear premix. The clear premix is added to 200 grams of CLOROX with stirring resulting in a clear stable single phase solution. Sufficient lM aqueous NaOH is added to bring the pH of the mixture up to 12.8. The solution remains substantially stable at 120 F for a period of 7 days.
  • the 5% aqueous sodium hypochlorite solution is used as a laundry bleach, the resulting laundry on dry-out in an atmosphere of 65% relative humidity yields substantially no characteristic hypochlorite" odor but does have a faint pleasant woody aroma. Furthermore. no such characteristic hypochlorite" aroma is retained on the hands of the individual handling such laundry in both the wet and the dry states.
  • EXAMPLE V Four drops of the perfume oil, the mixture of Example II is added to 2 grams of Aromox DMC-W to produce a clear premix. The clear premix is added to 200 grams of CLOROX with stirring resulting in a clear stable single phase solution. Sufficient 1M aqueous NaOH is added to bring the pH of the mixture up to 12.8. The solution remains substantially stable at 120 F for a period of? days.
  • the 5% aqueous sodium hypochlorite solution is used as a laundry bleach, the resulting laundry on dry-out in an atmosphere of relative humidity yields substantially no characteristic hypochlorite" odor but does have a faint pleasant clean fresh aroma. Furthermore, no such characteristic hypochlorite" aroma is retained on the hands of the individual handling such laundry in both the wet and the dry states.
  • EXAMPLE VI Four drops of the perfume oil, the mixture of Example III is added to 2 grams of Aromox DMC-W to produce a clear premix. The clear premix is added to 200 grams of CLOROX with stirring resulting in a clear stable single phase solution. Sufficient IM aqueous NaOH is added to bring the pH of the mixture up to 12.8. The solution remains substantially stable at l20 F for a period of 7 days.
  • the 5% aqueous sodium hypochlorite solution is used as a laundry bleach, the resulting laundry on dry-out in an atmosphere of 65% relative humidity yields substantially no characteristic hypochlorite" odor but does have a faint pleasant floral" aroma. Furthermore, no such characteristic hypochlorite" aroma is retained on the hands of the individual handling such laundry in both the wet and the dry states.
  • EXAMPLE VIII 1 week.
  • the resulting solution remains clear in a single phase.
  • the resulting bleached laundry on dry-out in an atmosphere of 50% relative humidity retains a clean fresh aroma; whereas without the use of the perfume oil.
  • the bleached laundry has a faint characteristic disagreeable hypochlorite aroma.
  • EXAMPLE lX Two grams of Aromox DMMC-W is admixed with eight drops of the perfume oil of Example ll. This premix is then added with stirring to 200 grams of a mixture containing 4.5% aqueous sodium hypochlorite and 4.5% aqueous lithium hypochlorite. Sufficient 4M aqueous LiOH is added to bring the pH of the solution to l3.4. The mixture is then heated to 120 F and maintained at that temperature with stirring for a period of 1 week. The resulting solution remains clear in a single phase.
  • the resulting bleached laundry on dry-out in an atmosphere of 50% relative humidity retains a "clean fresh aroma; whereas without the use of the perfume oil, the bleached laundry has a faint characteristic disagreeable hypochlorite" aroma.
  • EXAMPLE X Two grams of Aromox DMMC-W is admixed with eight drops of the perfume oil of Example I. This premix is then added with stirring to 200 grams of a mixture containing 4.5% aqueous sodium hypochlorite and 4.5% aqueous lithium hypochlorite. Sufficient 2M aqueous NaOH is added to bring the pH of the solution to l3.4. The mixture is then heated to l l F and maintained at that temperature with stirring for a period of 2 weeks. The resulting solution remains clear as a single phase when used as a laundry bleach. The resulting bleached laundry, on dry-out in an atmosphere of 50% relative humidity. retains a "woody" aroma whereas. without the use of the perfume oil of Example I, the bleached laundry has a faint characteristic disagreeable hypochlorite" aroma.
  • EXAMPLE Xl Four drops of a perfume oil, the mixture of Example I, is added to l.5grams Aromox NCMDW to produce a clear premix. The clear premix is added to 200 grams of CLOROX with stirring resulting in a clear stable single phase solution. Sufficient lM aqueous NaOH is added to bring the pH of the mixture up to [2.8. The solution remains substantially stable at 1 20 F for a period of 7 days. When the aqueous sodium hypochlorite solution is used as a laundry bleach, the resulting laundry on dry-out in an atmosphere of 65% relative humidity yields substantially no characteristic hypochlorite" odor but does have a faint pleasant woody" aroma. Furthermore, no such characteristic hypochlorite aroma is retained on the hands of the individual handling such laundry in both the wet and the dry states.
  • Example Xll Four drops of the perfume oil, the mixture of Example ll is added to 1 gram n-undecyl dimethyl amine oxide to produce a clear premix. The clear premix is added to 200 grams of CLOROX with stirring resulting in a clear stable single phase solution. Sufficient 1M aqueous NaOH is added to bring the pH of the mixture up to 12.8. The solution remains substantially stable at F for a period of 7 days.
  • the 5% aqueous sodium hypochlorite solution is used as a laundry bleach, the resulting laundry on dry-out in an atmosphere of 65% relative humidity yields substantially no characteristic hypochlorite odor but does have a faint pleasant clean fresh" aroma. Furthermore, no such characteristic hypochlorite" aroma is retained on the hands of the individual handling such laundry in both the wet and the dry states.
  • EXAMPLE Xlll Four drops of the perfume oil, the mixture of Example lll is added to l gram of n-dodecyl dimethyl amine oxide to produce a clear premix.
  • the clear premix premix is added to 200 grams of CLOROX with stirring resulting in a clear stable single phase solution.
  • Sufficient lM aqueous'NaOH is added to bring the pH of the mixture up to 12.8.
  • the solution remains substantially sta- EXAMPLE XlV
  • One gram of n-tridecyl dimethyl amine oxide is admixed with eight drops of the perfume oil of Example ll. This premix is then added with stirring to 200 grams ofa 7% aqueous solution oflithium hypochlorite.
  • bleached laundry has a faint characteristic disagreeable 1 hypochlorite aroma.
  • EXAMPLE XV A group of five individuals is requested to soak their hands in various aqueous alkali metal hypochlorite solutions, each solution being maintained at 72 F, for a period of 30 minutes. Following this period, the said individuals thoroughly rinse their hands in running tap water and carefully dry their hands. The following results concerning the aroma emanating from the hands 1 of these individuals are obtained:
  • An aqueous alkali metal hypochlorite solution free of hydrotropes comprising as a sole detergent, an amine oxide composition consisting of amine oxide having the formula:
  • R N B wherein R is straight chain alkyl; wherein more than 55% of the R moieties consists of straight chain alkyl having from 11 up to l3 carbon atoms; and wherein A and B are each separately methyl or, taken together, complete a morpholine ring and from 0.02% up to 0.2% by weight of a perfume oil capable of imparting to the said alkali metal hypochlorites solution a woody or a floral or a clean fresh" or a musl-t" or a "citrusy” fragrance.
  • said hypochlorite solution having a pH of from l2 up to 13.5.
  • composition of claim 1 wherein the amine oxide composition is selected from the group consisting of dimethyl cocoamine oxide and N-cocomorpholine oxide.
  • a process for producing a stable single phase aqueous alkali metal hypochlorite solution having a woody" or floral or clean fresh” or musk or citrusy fragrance consisting of. in order, the steps of (a) admixing an amine oxide composition consisting of amine oxide having the formula:
  • R is straight chain alkyl; wherein more than 55% of the R moieties consists of straight chain alkyl having from 1 l to 13 carbon atoms; and wherein A and B are each separately methyl or, taken together, complete a morpholine ring with a perfume oil which is capable of imparting woody" or floral or clean fresh” or musk or citrusy notes to the said aqueous hypochlorite solution to form a premix; (b) adding the premix to an aqueous alkali metal hypochlorite solution; and (c) adding to the resulting mixture an alkali metal hydroxide such that the pH of the resulting mixture is from 12 to 13.5.
  • step (a) is selected from the group consisting of dimethyl cocoamine oxide and N- cocomorpholine oxide.
  • a process for producing a stable single phase aqueous alkali metal hypochlorite solution having a woody or a floral” or a "clean fresh or a musk or a citrusy fragrance consisting, in order, as the steps of (a) adjusting the pH of an aqueous alkali metal hypochlorite solution to the range of l2-l3.5; (b) admixing an amine oxide composition consisting of at amine oxide having the formula:
  • R is straight chain alkyl; wherein more than 55% of the R moieties consists of straight chain alkyl containing from 11 up to 13 carbon atoms; and wherein A and B are each separately methyl or, taken together, completing a morpholine ring, with a perfume oil which is capable of imparting woody or floral" or fresh clean” or musk or citrusy notes to said aqueous hypochlorite solution to form a premix; and (c) adding said premix to the pH-adjusted hypochlorite solution.
  • step (b) is selected from the group consisting of dimethyl cocoamine oxide and N- cocomorpholine oxide.
  • composition of claim 2 wherein the concentration of the amine oxide is in the amount of from 0.15% up to 1.0% of the total weight of aqueous alkali metal hypochlorite solution.
  • composition of claim 9 wherein the alkali metal hypochlorite is sodium hypochlorite.
  • composition of claim 9 wherein the alkali metal hypochlorite is lithium hypochlorite.

Abstract

A stable single phase aqueous alkali metal hypochlorite liquid perfumed bleach or sterilizing composition comprising an aqueous mixture of (1) an amine oxide composition consisting essentially of at least one morpholino- and/or dimethyl (C.sub.11 -C.sub.13 straight chain alkyl) amine oxide, in an amount greater than 55% of said amine oxide composition, (2) at least one alkali metal hydroxide, (3) at least one alkali metal hypochlorite, and (4) a perfume oil compatible with the mixture capable of imparting a "woody" or a "floral" or a "clean fresh" or a "musk" or a "citrusy" note to the bleach or sterilizing composition; the said mixture having a pH in the range of from 12 to 13.5 and the said mixture excluding hydrotropes as well as all surfactants except said amine oxide; and a process for producing said mixture comprising the steps of combining an amine oxide composition consisting essentially of one or more morpholino- and/or dimethyl C.sub.11 -C.sub.13 straight chain alkyl amine oxides with a perfume oil to form an amine oxide-perfume oil premix; admixing the amine oxide - perfume oil premix with an aqueous alkali metal hypochlorite solution, and combining an alkali metal hydroxide with the solution whereby the final pH of the mixture is from 12 up to 13.5. In the alternative the pH of the aqueous hypochlorite solution is initially adjusted to the range of 12-13.5 and then the premix is combined with the pH-adjusted aqueous hypochlorite solution. The resulting composition when used as a bleach or sterilizing agent causes the products to which said composition is applied to have virtually eliminated therefrom the disagreeable characteristic "hypochlorite" aroma; and instead, a pleasant "clean fresh" or "floral" or "woody" or "musk" or "citrusy" aroma is imparted to such treated products. In addition, the hands of the individual user after using and being in direct contact with the composition will not have the disagreeable characteristic "hypochlorite" aroma but instead will have a pleasant "clean fresh" or "floral" or "woody" or "musk" or "citrusy" aroma.

Description

Laufer et al.
[I 11 3,876,55 l i PERFUMED AQUEOUS HYPOCHLORITE COMPOSITION AND METHOD FOR PREPARATION OF SAME [75] Inventors: Robert John Lauter, Colts Neck; John Henry Geiger, .Ir., Belford. both of NJ.
[73] Assignee: International Flavors 84 Fragrances Inc., New York. N.Y.
[22] Filed: Nov. 8, I972 [2l] Appl. No.: 304,807
Related US. Application Data [63] Continuation-in-part of Ser. No. 226.210. Feb. 14.
I972. abandoned.
[52] U.S. Cl. 252/98; 252/99; 252/l03; 252/l l0; 252/l 17 [SI] Int. Cl Clld 9/44 [58] Field of Search 252/95. 98. 99. 103. H0, 252/ I I7 {56] References Cited UNITED STATES PATENTS 3.368.943 2/l968 Gilbert et al 3.560.389 2/l97l Hunting 3.684.722 8/l972 Hynam et al. 3.749.673 7/l973 Jones et al. 252/99 X FOREIGN PATENTS OR APPLICATIONS 886.084 l/l962 United Kingdom 252/95 Primary Examiner-Benjamin R. Padgett Assistant Examiner-P. A. Nelson Attorney. Agent, or Firm-Arthur L. Liberman, Esq.; Harold Haidt. Esq.
[57] ABSTRACT A stable single phase aqueous alkali metal hypochlorite liquid perfumed bleach or sterilizing composition 1 Apr. 8, 197 5 1 comprising an aqueous mixture of I) an amine oxide 5 composition consisting essentially of at least one mor- E pholinoand/or dimethyl (C -C straight chain alkyl) amine oxide. in an amount greater than 55% of said 7 amine oxide composition, (2) at least one alkali metal hydroxide. (3) at least one alkali metal hypochlorite. and (4) a perfume oil compatible with the mixture capable of imparting a woody" or a floral" or a clean fresh" or a musk" or a citrusy note to the bleach or sterilizing composition; the said mixture having a 5 pH in the range of from 12 to 13.5 and the said mixture excluding hydrotropes as well as all surfactants except said amine oxide; and a 'process for producing said mixture comprising the steps of combining an amine oxide composition consisting essentially of one 'E or more morpholinoand/or dimethyl C -c straight 7 chain alk-yl amine oxides with a perfume oil to form an amine oxide-perfume oil premix; admixing the amine oxide perfume oil premix with an aqueous alkali metal hypochlorite solution, and combining an alkali metal hydroxide with the solution whereby the final pH of the mixture is from l2 up to l3.5. In the alternative the pH of the aqueous hypochlorite solution is initially adjusted to the range of l2-l3.5 and then" the premix is combined with the pH-adjusted aqueous hypochlorite solution. The resulting composition when used as a bleach or sterilizing agent causes the products to which said composition is applied to have virtually eliminated therefrom the disagreeable charac-@ teristic hypochlorite aroma; and instead, a pleasant clean fresh" or floral or woody or musk or citrusy" aroma is imparted to such treated products. In addition. the hands of the individual user after using and being in direct contact with the composition will not have the disagreeable characteristic hypochIorite" aroma but instead will have a pleasant clean fresh or floral or woody or musk" or citrusy{ aroma.
ll Claims, No Drawings PERFUMED AQUEOUS HYPOCHLORITE COMPOSITION AND METHOD FOR PREPARATION OF SAME This application is a continuation in-part of application for U.S. Pat. No. 226,2l filed on Feb. 14. l972. now abandoned.
BACKGROUND OF THE INVENTION Considerable difficulties have heretofore been encountered in compounded hypochlorite bleach or sterilizing solutions with perfume oils so that a stable longlasting single phase commercially feasible bleach or sterilizing solution has been difficult to obtain. The problem has been defined in British Patent Specifica tion No. 886.084 published on Jan. 3, 1962 wherein it is stated that a stable dispersion of hypochloriteresistant perfume in aqueous solutions of hypochlorites was formulated. British Patent Specification No. 886.084 disclosed the preparation of an aqueous solution" of a hypochlorite containing a hypochloriteresistant perfume and a surface active quaternary ammonium compound of the betaine type soluble in the hypochlorite solution. Such ammonium compounds have the generic structure:
99 R -N-C-CO I I Ru.R
wherein each of R1. R2, R and R are alkyl. One of the features of the perfumed solutions produced in accordance with said British Patent Specification No. 886,084 was indicated to be that the solution exhibits foaming properties. Another feature of British Patent Specification No. 886.084 is stated to be that the perfumed solutions covered by the invention are found to be clear and homogeneous after eight weeks storage at room temperature. Nevertheless. betaines such as Ambiteric D" as are discussed therein are not so broadly useful when used in the concentrations of from 0.15% up to l.07( (based on the total weight of bleach or sterilizing solution) as to have the ability to be used in conjunction with woody or floral" or clean fresh or musk or citrusy" types of perfume oils which should be incorporated into hypochlorite bleaches or sterilizers so that long lasting stable soluble single phase perfumed aqueous alkali metal hypochlorite bleach or sterilizing solutions having woody" or musk or citrusy or floral" or "clean fresh long lasting stable aromas are obtained, particularly where the quantity of perfume oil in the bleach or sterilizing is at levels of between 0.02% and 02% by weight of the total bleach or sterilizing solution. The need for the woody, "floral or clean fresh" or musk or citrusy" aromas to be present in such bleach or sterilizing solutions exists so that the disagreeable characteristic hypochlorite aroma is substantially diminished or eliminated altogether from aromas of the products to which the bleach or sterilizing solution is applied; particularly on dry-out. as well as from the aroma of the hands of the user where they are in direct Contact with such bleach or sterilizing solutions.
U.S. Pat. No. 3,560,389 also discloses the feasibilit of using perfume oils in hypochlorite bleaches or sterilizers at Column 3, lines 37-40 but the disclosure is him ited to inclusion of various detergents in addition to amine oxides, such as lithium lauryl sulfate and sodium lauryl ether sulfate and/or is further limited to include hydrotropes such as sodium xylene sulfonate in addition to the amine oxide. Exclusion of such hydrotropes and additional detergents is desirable not only to cause Neither the South African nor the United States patents, however, indicate the advantages and usefulness. of limiting the detergents solely to amine oxides, or of; excluding from the formulation a hydrotrope or of; specifying the nature of the perfume oil useful in the perfumed bleach or sterilizing solution.
THE INVENTION This invention relates to the production of perfumedj single phase aqueous alkali metal hypochlorite solutions suitable for laundry and general domestic bleach-z ing and sterilizing purposes. We have found that it is I" now possible to provide perfumed aqueous alkali metal; hypochlorite solutions which yield a long lasting per-i fume aroma (particularly those having a "woody" or "floral" or clean fresh" or "musk: or citrusy fra-E grance) and which are capable of imparting to surfaces; (e.g. laundry and the hands of the user which are in direct contact with the hypochlorite solutions) to whichthey are applied a pleasant woody or floral" or "clean fresh or musk or citrusy" aroma, and at the{ same time substantially diminishing or eliminating alto-15 gether the characteristic disagreeable hypochloritefl aroma therefrom.
Accordingly, this invention consists of an aqueous solution of at least one alkali metal hypochlorite con-; taining a stable perfume oil and a surface active agent consisting solely of an amine oxide composition and;
consists essentially of one or more morpholine and/or? dimethyl C,,C straight chain alkyl amine oxides hav-,[ ing the generic structure:
in an amount greater than 55% of said amine oxide composition wherein R is straight chain alkyl having from 11 up to 13 carbon atoms and A and B are each separately methyl, or, taken together, complete a morpholino ring and having a pH in the range of 12-135 The chain length(s) of the R moiety (or moieties) ol the predominating alkyl dimethyl amine oxide(s) of the amine oxide composition is critical for providing an aqueous hypochlorite bleach or sterilizing solution which can be perfumed with the woody" or floral" or clean fresh" or musk" or citrusy" fragrance formulations required for our invention.
The concentration of the amine oxide composition required to create the transparent solution of this invention is from 0.15% up to 1.0% based on the total weight of solution. Concentrations of amine oxides less than 0.15% will not give rise to the desired single phase system containing the desired special perfume oil (having the woody" or floral or clean fresh" or musk" or citrusy" aroma) required for this invention. From a commercial standpoint concentrations of amine oxide(s) greater than 1.0% based on total weight i of hypochlorite solution are not needed and give rise to unnecessary costs.
The pH range of the aqueous alkali metal hypochlorite solution containing the amine oxide composition and one of the requisite perfume formulations (which are stable to hypochlorite and which are capable of yielding and imparting the desired and required overall woody or floral or clean fresh" or musk" or citrusy" fragrance impression) is critical; that is. a pH of from 12 up to 13.5 is required for the composition of our invention, with the preferred pH range being between 12.5 and 12.9. The requisite pH range is achieved by adding an aqueous solution of alkali metal hydroxide (e.g. from 1M up to 12.5M) to the alkali metal hypochlorite solution which has had or will have added to it the amine oxide-perfume oil premix.
The percentage of perfume oil having the properties which yield woody or floral or clean fresh" or musk or citrusy aroma is in the range of from 0.02% up to 0.2% based on the total final weight of aqueous alkali metal hypochlorite solution. Lower concentrations of such perfume oils will not be adequate to give rise to the desired substantial diminution or elimination of the characteristic disagreeable hypochlorite aroma (which exists on. for example. laundry and/or the hands of the individual user which have been in direct contact with the hypochlorite bleach or sterilizing solution subsequent to the use of aqueous hypochlorite solutions as a general domestic bleach or sterilizer). Quantities of perfume oil greater than 0.2% have been found to be uneconomical and unnecessary for the practice of our invention.
Several processes may be used in order to produce a hypochlorite bleaching or sterilizing solution having the desired woody" or floral or clean fresh or musk or citrusy aromas. Thus, for example, the perfume oil may be premixed with the amine oxide solubilizer and the resulting perfume oil-amine oxide premix is then mixed with the hypochlorite bleaching or sterilizing solution with stirring. Immediately after such addition an aqueous alkali metal hydroxide solution is added to the mixture to bring the pH to the range of l2-13.5. A pH of less than 12 is not desired since it is difficult to achieve a single phase stable system at such low pHs. A pH higher than 13.5 will also create a system which (1) is unnecessarily corrosive; (2) will narrow the range of perfume oils usable in the system; and (3) will limit the particular ingredients usable in such perfume oils.
The aqueous alkali metal hydroxide can be added to the aqueous alkali metal hypochlorite solution before adding the amine oxide or the perfume oil. lndeed, the ingredients: the perfume oil, the alkali metal hydroxide and the amine oxide composition may be added or admixed in any order which is convenient to the formulator. One desirable process involves first forming the amine oxide composition perfume oil premix, mixing the premix with the aqueous alkali metal hypochlorite solution and finally adjusting the pH of the solution with alkali metal hydroxide to bring the pH to within the range of l2-13.5. A second more preferable process involves first adjusting the pH of the aqueous alkali metal hypochlorite solution to 12-13.5 and then admixing this solution with the afore-described premix."
The alkali metal hypochlorites preferred in the practice of our invention are: sodium hypochlorite, potassium hypochlorite and lithium hypochlorite, or mixtures of same. The alkali metal hydroxides preferred in the practice of this invention are lithium hydroxide, potassium hydroxide and sodium hydroxide, or, ifdesired, mixtures of such hydroxides.
The temperature at which the composition of our invention remains both substantially stable and commercially usable for the purposes set forth herein (that is, remains as a clear single aqueous phase and retains l the desired properties inherent in the known bleaching and sterilizing uses of aqueous alkali metal hypochlorite solutions, and (2) the properties imparted thereto as a result of using the perfume oils which impart to the aqueous alkali metal hypochlorite solutions a woodyor floral or clean fresh" or musk" or citrusy" aroma) varies from approximately 20 F up to approximately F. At temperatures below 20 F a twophase system usually occurs and at temperatures higher than 120 F the bleaching or sterilizing efficiency of the composition of our invention is diminished at an excessive rate.
When it is desired to (1) initially form an amine oxideperfume oil premix; (2) then combine the resulting premix with an aqueous alkali metal hypochlorite solution and then (3) adjust the pH of the resulting solution to the range of 12-1 3.5, then the following temperature of mixing ranges are considered to be within the scope of this invention:
20F-120F (c) In any event, wherever a mixing unit operation involves the aqueous alkali metal hypochlorite solution, the temperature of mixing is limited to the range of 20-120 F. Where a mixing unit operation involves the mixing of a perfume oil, the upper bound of the temperature range is limited by the stability of the least stable ingredient in the perfume oil usable in the practice of our invention; and the lower bound of said temperature range is limited by the least temperature where a single liquid phase including the perfume oil will exist. Where a unit mixing operation of the process of our invention involves the mixing of one or more amine oxides with other materials, the upper bound of the temperature range is the decomposition point of any one of the amine oxide components of the amine oxide composition and the lower bound is the least temperature where a single liquid phase including the amine oxide(s) will exist.
Preferred amine oxide compositions from a practical standpoint useful in the practice of our invention are the commercially available (1) dimethyl cocoamine oxide (a mixture which is dominated by dimethyl- C C straight chain alkyl amine oxide; more particularly a mixture containing approximately 70% C straight chain amine oxides, approximately 25% C of straight chain amine oxides and approximately 4% C straight chain alkyl amine oxides) and (2) N- cocomorpholine oxide, a mixture dominated by C -C straight chain alkyl morpholine oxides (specifically containing approximately 70% C straight chain alkyl morpholine oxide. approximately 25% C straight chain alkyl morpholine oxide and approximately 4% C straight chain alkyl morpholine oxide). Commercial examples of such amine oxide compositions are: Aromox DMC-W and Aromox DMMC-W which are 30% aqueous dimethyl cocoamine oxide solutions and Aromox NCMDW which is a 40% aqueous N-cocomorpholine oxide solution. each of which is produced by the Armac Division of AKZO of Chicago, Illinois. These materials are described in Brochure 6801]. published by Armour Industrial Chemicals, P.O.B. I805, Chicago. Illinois 60690. Other preferred amine oxides are n-undecyl dimethyl amine oxide and n-tridecyl dimethyl amine oxide.
The percentage of hypochlorite ion in the composition of this invention may vary from about We up to about i671 for the desired effects to be produced using the amine oxide-perfume oil compositions covered by our invention. The usual percent of alkali metal hypochlorite in solution is about 5%, the percentage of sodium hypochlorite in such materials as CLOROX the registered trademark of Clorox Corporation.
As stated above. the perfume oil used in conjunction with the aqueous alkali metal hypochlorite solution must have such properties as to be able (1) to impart to the resulting or aqueous alkali metal hypochlorite solution either a woody or a floral' or a clean fresh" or musk" or citrusy" aroma; (2) to effect a substantial diminution or elimination of the disagreeable hypochlor-ite" aroma which is imparted to surfaces (e.g. bleached laundry or the hands of the user which are in direct contact with the hypochlorite solution) on which known aqueous alkali metal hypochlorite solutions have been used; and (3) to impart to these surfaces with which such aqueous alkali metal hypochlorite solutions are in contact, a pleasant long lasting clean fresh" or floral" or woody" or musk orcitrusy" aroma. Examples of ingredients usable and suitable for the aforementioned purposes are as follows:
a. Materials Useful for lmparting a Woody Aroma:
1. Cedryl alkyl ethers covered by U.S. Pat. No.
3,373,208 such as cedryl methyl ether;
2. lsochroman musks covered by U.S. Pat. Nos.
3,360,530 and 3,591,528 such as 6-oxal,1,3,3,8-pentamethyl-2.3,5.6,7,8-hexahydrolH-benz(f) indene;
3. Polycyclic ethers covered by U.S. Pat. No.
3,281,432, such as octahydro-l,3a,6-trimethylll-ll ,6u,ethanopentaleno-( l,2-C furan;
4. Polycyclic ketones such as hexahydro-l,l,5,5-
tetramethyl-ZH-Z,4a-methanonaphthalen-8- (5l-l)one.
b. Materials Useful for lmparting a Clean Fresh" Aroma: 1. Acyl norbornenes such as acetyl norbornene; 2. Nitro musks such as musk xylol; 3. Long chain aliphatic nitriles such as n-dodecyl nitrile; 4. 2-t-butyl cyclohexyl acetate.
c. Materials Useful for lmparting a Floral" Aroma:
1. lndane musks covered by U.S. Pat. No.
2,889,367 such as 4-acetyl-l,l-dimethyl--tbutyl indane;
2. Naphthyl ethers such as ,B-naphthyl methyl ether and B-naphthyl ethyl ether;
3. Cyclohexyl ethyl ether;
4. Aryl alkanones as described in Canadian Pat.
No. 780,489, such as 2,5-dimethyl-5-phenylhexanone-3.
d. Materials Useful for lmparting a "Musk" Aroma:
or citrusy" aromas will not be useful for use in our invention because they are interalia, easily oxidized by the alkali metal hypochlorite in the system. Examples are l,5,9-trimethyll 2-acetyl-cyclododecatriene-l .5 ,8: and covered by British Pat. No. l,204,409.
A basic feature of our invention concerns the fact that the only detergent group needed or desirable in the composition of our invention is the class of morpholino and/or dimethyl C -C straight chain alkyl amine oxides. More specifically, such detergents as sodium decyl ether sulfate, sodium myristyl ether sulfate. so-
l,5.9-trimethyl-l 2-acetyl-cyclododecadiene-l ,8
dium lauryl ether sulfate and lithium lauryl ether sulfate are neither desired nor are they required. Furthermore the well known hydrotropes employed in prior art compositions such as the well known family of clarifyf ing agents comprising the alkali metal or alkali earth metal salts of monoor polyalkylated benzene or naphthalene sulfonates such as sodium xylene sulfonate or magnasium toluene sulfonate again are neither desired nor are they required in the compositions intended to be encompassed by the instant invention.
The following examples are given to illustrate embodiments of the invention as it is now preferred to practice it. It will be understood that these examples are illustrative and the invention is not to be considered as restricted thereto except as indicated in the appended claims.
EXAMPLE I PERFUME COMPOSITION The following mixture is prepared:
The subject mixture has an intense pleasant woody aroma.
EXAMPLE Il PERFUME COMPOSITION The following mixture is prepared:
Ingredients Parts by Weight Musk xylol |-t-hut \l- 2.-1.6-trinitro-m-xylcne| n-Dotlecyl nitrilc 2-Acetyl-5-Norhornene 50 Z-t-butyl cyclohcxyl acetate l0 Dimethyl benyyl carhinol 35 Hydratropic aldehyde dimethyl acctitl 15 The subject perfume composition has an intense clean fresh" aroma.
EXAMPLE lll PERFUME COMPOSITION The following mixture is prepared:
Ingredients Parts by Weight -t-Acctybl .l-diniethyl-o-thutyl indanc 8 Xa.l2-oxido-20-methyl-Ill-1.
I5. I O'ICIlilkIS-HUl'liIhLlZlIlO 2 2.5-dimethyl-S-phenyl-hexanone-S l2 (etlrol propyl ether 8 Yura )tlra (yclohexyl ethyl ether l0 Methvl para-cresol 5 2.h-tlimethyI-Z-octanol 25 The instant perfume composition has an intense floral" aroma.
In the following Examples lV-XIV Aromox DMC-W and Aromox DMMC-W are 30% aqueous solutions of dimethyl cocoamine oxide; and Aromox NCMDW is a 40% aqueous solution of N-cocomorpholine oxide produced by Armac Division ofAKZO ofChicago, Illinois.
EXAMPLE IV Four drops of a perfume oil, the mixture of Example I, is added to 2 grams of Aromox DMC-W to produce a clear premix. The clear premix is added to 200 grams of CLOROX with stirring resulting in a clear stable single phase solution. Sufficient lM aqueous NaOH is added to bring the pH of the mixture up to 12.8. The solution remains substantially stable at 120 F for a period of 7 days. When the 5% aqueous sodium hypochlorite solution is used as a laundry bleach, the resulting laundry on dry-out in an atmosphere of 65% relative humidity yields substantially no characteristic hypochlorite" odor but does have a faint pleasant woody aroma. Furthermore. no such characteristic hypochlorite" aroma is retained on the hands of the individual handling such laundry in both the wet and the dry states.
EXAMPLE V Four drops of the perfume oil, the mixture of Example II is added to 2 grams of Aromox DMC-W to produce a clear premix. The clear premix is added to 200 grams of CLOROX with stirring resulting in a clear stable single phase solution. Sufficient 1M aqueous NaOH is added to bring the pH of the mixture up to 12.8. The solution remains substantially stable at 120 F for a period of? days. When the 5% aqueous sodium hypochlorite solution is used as a laundry bleach, the resulting laundry on dry-out in an atmosphere of relative humidity yields substantially no characteristic hypochlorite" odor but does have a faint pleasant clean fresh aroma. Furthermore, no such characteristic hypochlorite" aroma is retained on the hands of the individual handling such laundry in both the wet and the dry states.
EXAMPLE VI Four drops of the perfume oil, the mixture of Example III is added to 2 grams of Aromox DMC-W to produce a clear premix. The clear premix is added to 200 grams of CLOROX with stirring resulting in a clear stable single phase solution. Sufficient IM aqueous NaOH is added to bring the pH of the mixture up to 12.8. The solution remains substantially stable at l20 F for a period of 7 days. When the 5% aqueous sodium hypochlorite solution is used as a laundry bleach, the resulting laundry on dry-out in an atmosphere of 65% relative humidity yields substantially no characteristic hypochlorite" odor but does have a faint pleasant floral" aroma. Furthermore, no such characteristic hypochlorite" aroma is retained on the hands of the individual handling such laundry in both the wet and the dry states.
EXAMPLE VII Aromox DMMC-W in various quantities is mixed with 0.1 gram of the perfume oil prepared in accordance with Example I. The resulting premixes are then added to 200 grams of an aqueous 5% sodium hypochlorite solution. Sufficient 12.5M aqueous NaOH is added to bring the pH of the mixture up to 13. The following results are obtained:
Clarity of hypochlorite solu- Percentage Aromox tion after addition of premix 0.23% Clear after three days 0. l5% Clear after three days 0.08% Initially slightly turbid;
two phases exist after three days.
EXAMPLE VIII 1 week. The resulting solution remains clear in a single phase. When used as a laundry bleach, the resulting bleached laundry on dry-out in an atmosphere of 50% relative humidity retains a clean fresh aroma; whereas without the use of the perfume oil. the bleached laundry has a faint characteristic disagreeable hypochlorite aroma.
EXAMPLE lX Two grams of Aromox DMMC-W is admixed with eight drops of the perfume oil of Example ll. This premix is then added with stirring to 200 grams of a mixture containing 4.5% aqueous sodium hypochlorite and 4.5% aqueous lithium hypochlorite. Sufficient 4M aqueous LiOH is added to bring the pH of the solution to l3.4. The mixture is then heated to 120 F and maintained at that temperature with stirring for a period of 1 week. The resulting solution remains clear in a single phase. When used as a laundry bleach, the resulting bleached laundry on dry-out in an atmosphere of 50% relative humidity retains a "clean fresh aroma; whereas without the use of the perfume oil, the bleached laundry has a faint characteristic disagreeable hypochlorite" aroma.
EXAMPLE X Two grams of Aromox DMMC-W is admixed with eight drops of the perfume oil of Example I. This premix is then added with stirring to 200 grams of a mixture containing 4.5% aqueous sodium hypochlorite and 4.5% aqueous lithium hypochlorite. Sufficient 2M aqueous NaOH is added to bring the pH of the solution to l3.4. The mixture is then heated to l l F and maintained at that temperature with stirring for a period of 2 weeks. The resulting solution remains clear as a single phase when used as a laundry bleach. The resulting bleached laundry, on dry-out in an atmosphere of 50% relative humidity. retains a "woody" aroma whereas. without the use of the perfume oil of Example I, the bleached laundry has a faint characteristic disagreeable hypochlorite" aroma.
EXAMPLE Xl Four drops of a perfume oil, the mixture of Example I, is added to l.5grams Aromox NCMDW to produce a clear premix. The clear premix is added to 200 grams of CLOROX with stirring resulting in a clear stable single phase solution. Sufficient lM aqueous NaOH is added to bring the pH of the mixture up to [2.8. The solution remains substantially stable at 1 20 F for a period of 7 days. When the aqueous sodium hypochlorite solution is used as a laundry bleach, the resulting laundry on dry-out in an atmosphere of 65% relative humidity yields substantially no characteristic hypochlorite" odor but does have a faint pleasant woody" aroma. Furthermore, no such characteristic hypochlorite aroma is retained on the hands of the individual handling such laundry in both the wet and the dry states.
EXAMPLE Xll Four drops of the perfume oil, the mixture of Example ll is added to 1 gram n-undecyl dimethyl amine oxide to produce a clear premix. The clear premix is added to 200 grams of CLOROX with stirring resulting in a clear stable single phase solution. Sufficient 1M aqueous NaOH is added to bring the pH of the mixture up to 12.8. The solution remains substantially stable at F for a period of 7 days. When the 5% aqueous sodium hypochlorite solution is used as a laundry bleach, the resulting laundry on dry-out in an atmosphere of 65% relative humidity yields substantially no characteristic hypochlorite odor but does have a faint pleasant clean fresh" aroma. Furthermore, no such characteristic hypochlorite" aroma is retained on the hands of the individual handling such laundry in both the wet and the dry states.
EXAMPLE Xlll Four drops of the perfume oil, the mixture of Example lll is added to l gram of n-dodecyl dimethyl amine oxide to produce a clear premix. The clear premix premix is added to 200 grams of CLOROX with stirring resulting in a clear stable single phase solution. Sufficient lM aqueous'NaOH is added to bring the pH of the mixture up to 12.8. The solution remains substantially sta- EXAMPLE XlV One gram of n-tridecyl dimethyl amine oxide is admixed with eight drops of the perfume oil of Example ll. This premix is then added with stirring to 200 grams ofa 7% aqueous solution oflithium hypochlorite. Sufficient 3M aqueous LiOH is added to bring pH of the solution to l 3.4. The mixture is then heated to 120 F and maintained at that temperature with stirring for a period of l week. The resulting solution remains clear in i a single phase. When used as a laundry bleach. the resulting bleached laundry on dry-out in an atmosphere of 50% relative humidity retains a clean fresh" aroma; whereas without the use of the perfume oil. the
bleached laundry has a faint characteristic disagreeable 1 hypochlorite aroma.
EXAMPLE XV A group of five individuals is requested to soak their hands in various aqueous alkali metal hypochlorite solutions, each solution being maintained at 72 F, for a period of 30 minutes. Following this period, the said individuals thoroughly rinse their hands in running tap water and carefully dry their hands. The following results concerning the aroma emanating from the hands 1 of these individuals are obtained:
Nature of Aroma Retained Nature of solution on Hands CLOROX" -water lzl (weight ratio) (l) A characteristic disagreeable hypochlorite aroma.
(2) Composition produced No disagreeable "hypochloaccording to Example lV- rite" aroma. Pleasant H O, l:l faint woody aroma.
(3) Composition produced Pleasant faint clean fresh" according to Example V- aroma. No disagreeable H O. l:l hypochlorite aroma.
(4) Composition produced Pleasant faint "floral" aroma. No disagreeable according to Example Vlhypochlorite aroma.
What is claimed is:
1. An aqueous alkali metal hypochlorite solution free of hydrotropes comprising as a sole detergent, an amine oxide composition consisting of amine oxide having the formula:
R N B wherein R is straight chain alkyl; wherein more than 55% of the R moieties consists of straight chain alkyl having from 11 up to l3 carbon atoms; and wherein A and B are each separately methyl or, taken together, complete a morpholine ring and from 0.02% up to 0.2% by weight of a perfume oil capable of imparting to the said alkali metal hypochlorites solution a woody or a floral or a clean fresh" or a musl-t" or a "citrusy" fragrance. said hypochlorite solution having a pH of from l2 up to 13.5.
2. The composition of claim 1 wherein the amine oxide composition is selected from the group consisting of dimethyl cocoamine oxide and N-cocomorpholine oxide.
3. A process for producing a stable single phase aqueous alkali metal hypochlorite solution having a woody" or floral or clean fresh" or musk or citrusy fragrance consisting of. in order, the steps of (a) admixing an amine oxide composition consisting of amine oxide having the formula:
wherein R is straight chain alkyl; wherein more than 55% of the R moieties consists of straight chain alkyl having from 1 l to 13 carbon atoms; and wherein A and B are each separately methyl or, taken together, complete a morpholine ring with a perfume oil which is capable of imparting woody" or floral or clean fresh" or musk or citrusy notes to the said aqueous hypochlorite solution to form a premix; (b) adding the premix to an aqueous alkali metal hypochlorite solution; and (c) adding to the resulting mixture an alkali metal hydroxide such that the pH of the resulting mixture is from 12 to 13.5.
4. The process of claim 3 wherein the pH of the resulting solution is adjusted to the range of 12.5 up to 12.9.
5. The process of claim 4 wherein the amine oxide composition used in step (a) is selected from the group consisting of dimethyl cocoamine oxide and N- cocomorpholine oxide.
6. A process for producing a stable single phase aqueous alkali metal hypochlorite solution having a woody or a floral" or a "clean fresh or a musk or a citrusy fragrance consisting, in order, as the steps of (a) adjusting the pH of an aqueous alkali metal hypochlorite solution to the range of l2-l3.5; (b) admixing an amine oxide composition consisting of at amine oxide having the formula:
wherein R is straight chain alkyl; wherein more than 55% of the R moieties consists of straight chain alkyl containing from 11 up to 13 carbon atoms; and wherein A and B are each separately methyl or, taken together, completing a morpholine ring, with a perfume oil which is capable of imparting woody or floral" or fresh clean" or musk or citrusy notes to said aqueous hypochlorite solution to form a premix; and (c) adding said premix to the pH-adjusted hypochlorite solution.
7. The process of claim 6 wherein the pH of the aqueous alkali metal hypochlorite solution is adjusted to the range of 12.5 12.9.
8. The process of claim 7 wherein the amine oxide composition used in step (b) is selected from the group consisting of dimethyl cocoamine oxide and N- cocomorpholine oxide.
9. The composition of claim 2 wherein the concentration of the amine oxide is in the amount of from 0.15% up to 1.0% of the total weight of aqueous alkali metal hypochlorite solution.
10. The composition of claim 9 wherein the alkali metal hypochlorite is sodium hypochlorite.
11. The composition of claim 9 wherein the alkali metal hypochlorite is lithium hypochlorite.

Claims (11)

1. AN AQUEOUS ALKALI METAL HYPOCHLORITE SOLUTION FREE OF HYDROTROPES COMPRISING AS A SOLE DETERGENT, AN AMINE OXIDE COMPOSITION CONSISTING OF AMINE OXIDE HAVING THE FORMULA:
2. The composition of claim 1 wherein the amine oxide composition is selected from the group consisting of dimethyl cocoamine oxide and N-cocomorpholine oxide.
3. A process for producing a stable single phase aqueous alkali metal hypochlorite solution having a "woody" or "floral" or "clean fresh" or "musk" or "citrusy" fragrance consisting of, in order, the steps of (a) admixing an amine oxide composition consisting of amine oxide having the formula:
4. The process of claim 3 wherein the pH of the resulting solution is adjusted to the range of 12.5 up to 12.9.
5. The process of claim 4 wherein the amine oxide composition used in step (a) is selected from the group consisting of dimethyl cocoamine oxide and N-cocomorpholine oxide.
6. A process for producing a stable single phase aqueous alkali metal hypochlorite solution having a "woody" or a "floral" or a "clean fresh" or a "musk" or a "citrusy" fragrance consisting, in order, as the steps of (a) adjusting the pH of an aqueous alkali metal hypochlorite solution to the range of 12-13.5; (b) admixing an amine oxide composition consisting of at amine oxide having the formula:
7. The process of claim 6 wherein the pH of the aqueous alkali metal hypochlorite solution is adjusted to the range of 12.5 -12.9.
8. The process of claim 7 wherein the amine oxide composition used in step (b) is selected from the group consisting of dimethyl cocoamine oxide and N-cocomorpholine oxide.
9. The composition of claim 2 wherein the concentration of the amine oxide is in the amount of from 0.15% up to 1.0% of the total weight of aqueous alkali metal hypochlorite solution.
10. The composition of claim 9 wherein the alkali metal hypochlorite is sodium hypochlorite.
11. The composition of claim 9 wherein the alkali metal hypochlorite is lithium hypochlorite.
US304807A 1972-02-14 1972-11-08 Perfumed aqueous hypochlorite composition and method for preparation of same Expired - Lifetime US3876551A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US304807A US3876551A (en) 1972-02-14 1972-11-08 Perfumed aqueous hypochlorite composition and method for preparation of same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US22621072A 1972-02-14 1972-02-14
US304807A US3876551A (en) 1972-02-14 1972-11-08 Perfumed aqueous hypochlorite composition and method for preparation of same

Publications (1)

Publication Number Publication Date
US3876551A true US3876551A (en) 1975-04-08

Family

ID=26920312

Family Applications (1)

Application Number Title Priority Date Filing Date
US304807A Expired - Lifetime US3876551A (en) 1972-02-14 1972-11-08 Perfumed aqueous hypochlorite composition and method for preparation of same

Country Status (1)

Country Link
US (1) US3876551A (en)

Cited By (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5269415A (en) * 1975-12-05 1977-06-09 Lion Corp Liquid deterging and bleaching agents
US4113645A (en) * 1977-07-26 1978-09-12 Polak's Frutal Works, Inc. Bleach compositions containing perfume oils
EP0021581A1 (en) * 1979-05-30 1981-01-07 Reckitt And Colman Products Limited Aqueous thickened bleach composition including alkali metal hypochlorite, and its preparation
US4292211A (en) * 1980-07-31 1981-09-29 Shaw Mudge & Company Fragrance dispersant composition
FR2548682A1 (en) * 1983-07-08 1985-01-11 Lesieur Cotelle COMPOSITION FOR AUTOMATIC CLEANING OF WC TOILET
EP0142197A2 (en) * 1983-11-04 1985-05-22 The Procter & Gamble Company Hypochlorite bleach containing surfactant and organic antifoamant
US4576728A (en) * 1983-11-11 1986-03-18 The Procter & Gamble Company Cleaning compositions
US4579677A (en) * 1978-05-16 1986-04-01 Lever Brothers Company Bleach compositions with deodorant perfumes
US4772411A (en) * 1988-01-28 1988-09-20 International Flavors & Fragrances Inc. Ethyl norbornyl alkyl ethers, organoleptic uses thereof and process for preparing same
US4789495A (en) * 1987-05-18 1988-12-06 The Drackett Company Hypochlorite compositions containing a tertiary alcohol
US4822515A (en) * 1988-01-28 1989-04-18 International Flavors & Fragrances Inc. Ethyl norbornyl alkyl ethers, organoleptic uses thereof and process for preparing same
US4828748A (en) * 1986-01-03 1989-05-09 The Drackett Company Thickened alkali metal hypochlorite compositions
US4863631A (en) * 1988-06-24 1989-09-05 International Flavors & Fragrances Inc. Dimethyl substituted alkyl nitriles, perfume and bleach compositions containing same organoleptic uses thereof and process intermediates for producing same
US4863633A (en) * 1987-08-07 1989-09-05 The Clorox Company Mitigation of stress-cracking in stacked loads of fragranced bleach-containing bottles
US4986926A (en) * 1989-04-10 1991-01-22 The Drackett Company Thickened alkali metal hypochlorite compositions
US5064650A (en) * 1988-04-19 1991-11-12 Southwest Research Institute Controlled-release salt sensitive capsule for oral use and adhesive system
US5075027A (en) * 1989-02-06 1991-12-24 Colgate Palmolive Co. Thixotropic aqueous scented automatic dishwasher detergent compositions
US5080826A (en) * 1987-08-07 1992-01-14 The Clorox Company Stable fragranced bleaching composition
US5227366A (en) * 1987-08-07 1993-07-13 The Clorox Company Mitigation of stress-cracking in fragranced bleach-containing bottles
EP0622451A1 (en) * 1993-04-26 1994-11-02 The Procter & Gamble Company Perfumed hypochlorite bleaching compositions
US5454978A (en) * 1993-04-28 1995-10-03 Calgon Corporation Inhibiting deposition of oil on surface of water-carrying system
US5578580A (en) * 1993-05-28 1996-11-26 Ascor Chimici S.R.L. Veterinary composition, feedstuff and process
US5639722A (en) * 1993-01-13 1997-06-17 The Clorox Company Acidic aqueous cleaning compositions
EP0877790A1 (en) * 1995-08-18 1998-11-18 The Procter & Gamble Company Perfumed bleaching detergent compositions
US6100228A (en) * 1993-10-29 2000-08-08 The Clorox Company Bleaching gel cleaner thickened with amine oxide, soap and solvent
WO2001044429A1 (en) * 1999-12-16 2001-06-21 Unilever N.V. Household cleaning products
WO2001096521A1 (en) * 2000-06-14 2001-12-20 Henkel Kommanditgesellschaft Auf Aktien Fabric conditioner in liquid or gel form
WO2003066790A1 (en) * 2002-02-01 2003-08-14 The Procter & Gamble Company Amine oxides as perfume solubility agents
US20060247456A1 (en) * 2003-07-28 2006-11-02 Wolfgang Steven M Stearate composition and method of production thereof
US7214652B1 (en) 2005-12-30 2007-05-08 3M Innovative Properties Company Anionic surfactant-containing hypochlorite bleach composition and methods of making and use
DE102005062008B3 (en) * 2005-12-22 2007-08-30 Henkel Kgaa Odor reduction of hypochlorite-containing agents
US20080274934A1 (en) * 2005-12-29 2008-11-06 Carlos Malet Inhibiting the corrosive properties of liquid cleaning agents containing hypochlorite
US20080305981A1 (en) * 2005-12-30 2008-12-11 Carlos Malet stability of detergents containing hypochlorite
US20080305980A1 (en) * 2005-12-30 2008-12-11 Carlos Malet Stability of detergents containing hypochlorite
US20080308766A1 (en) * 2005-12-06 2008-12-18 Carlos Malet Stability improvement of liquid hypochlorite-containing washing and cleaning compositions
US20080311224A1 (en) * 2007-06-18 2008-12-18 Meghan Gressler Long-lasting mildew stain remover and method for making same
US20080308767A1 (en) * 2005-12-07 2008-12-18 Carlos Malet Increasing the stability of liquid hypochlorite-containing washing and cleaning compositions
US20100207063A1 (en) * 2007-07-20 2010-08-19 Carlos Malet Gentle Bleach

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3368943A (en) * 1965-10-20 1968-02-13 Allan H. Gilbert alpha-alkoxyisobutyrates and alpha-halo-beta-alkoxyisovalerates in perfumes and cleaning products
US3560389A (en) * 1966-08-11 1971-02-02 Cyclo Chemicals Ltd Liquid detergent bleach composition
US3684722A (en) * 1969-08-29 1972-08-15 Lever Brothers Ltd Thickened alkali metal hypochlorite bleaching and cleaning composition
US3749673A (en) * 1971-02-22 1973-07-31 Procter & Gamble Bleach-fabric softener compositions

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3368943A (en) * 1965-10-20 1968-02-13 Allan H. Gilbert alpha-alkoxyisobutyrates and alpha-halo-beta-alkoxyisovalerates in perfumes and cleaning products
US3560389A (en) * 1966-08-11 1971-02-02 Cyclo Chemicals Ltd Liquid detergent bleach composition
US3684722A (en) * 1969-08-29 1972-08-15 Lever Brothers Ltd Thickened alkali metal hypochlorite bleaching and cleaning composition
US3749673A (en) * 1971-02-22 1973-07-31 Procter & Gamble Bleach-fabric softener compositions

Cited By (56)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5269415A (en) * 1975-12-05 1977-06-09 Lion Corp Liquid deterging and bleaching agents
US4113645A (en) * 1977-07-26 1978-09-12 Polak's Frutal Works, Inc. Bleach compositions containing perfume oils
US4579677A (en) * 1978-05-16 1986-04-01 Lever Brothers Company Bleach compositions with deodorant perfumes
EP0021581A1 (en) * 1979-05-30 1981-01-07 Reckitt And Colman Products Limited Aqueous thickened bleach composition including alkali metal hypochlorite, and its preparation
US4282109A (en) * 1979-05-30 1981-08-04 Reckitt & Colman Products Limited Aqueous hypochlorite solutions
DK155836B (en) * 1979-05-30 1989-05-22 Reckitt & Colmann Prod Ltd Aqueous Viscous Bleach Containing Alkali Metal Hypochlorite and Preparation Procedures
US4292211A (en) * 1980-07-31 1981-09-29 Shaw Mudge & Company Fragrance dispersant composition
EP0131527A1 (en) * 1983-07-08 1985-01-16 Lesieur-Cotelle Composition for the automatic cleaning of toilet bowls
US4731223A (en) * 1983-07-08 1988-03-15 Cotelle S.A. Composition for automatic cleaning of toilet bowls
FR2548682A1 (en) * 1983-07-08 1985-01-11 Lesieur Cotelle COMPOSITION FOR AUTOMATIC CLEANING OF WC TOILET
US4552680A (en) * 1983-11-04 1985-11-12 The Procter & Gamble Company Hypochlorite bleach containing surfactant and organic antifoamant
EP0142197A2 (en) * 1983-11-04 1985-05-22 The Procter & Gamble Company Hypochlorite bleach containing surfactant and organic antifoamant
EP0142197A3 (en) * 1983-11-04 1986-06-25 The Procter & Gamble Company Hypochlorite bleach containing surfactant and organic antifoamant
US4576728A (en) * 1983-11-11 1986-03-18 The Procter & Gamble Company Cleaning compositions
US4828748A (en) * 1986-01-03 1989-05-09 The Drackett Company Thickened alkali metal hypochlorite compositions
US4789495A (en) * 1987-05-18 1988-12-06 The Drackett Company Hypochlorite compositions containing a tertiary alcohol
US5080826A (en) * 1987-08-07 1992-01-14 The Clorox Company Stable fragranced bleaching composition
US4863633A (en) * 1987-08-07 1989-09-05 The Clorox Company Mitigation of stress-cracking in stacked loads of fragranced bleach-containing bottles
EP0518451A1 (en) * 1987-08-07 1992-12-16 The Clorox Company Homogeneous fragrance preblend
US5227366A (en) * 1987-08-07 1993-07-13 The Clorox Company Mitigation of stress-cracking in fragranced bleach-containing bottles
US4822515A (en) * 1988-01-28 1989-04-18 International Flavors & Fragrances Inc. Ethyl norbornyl alkyl ethers, organoleptic uses thereof and process for preparing same
US4772411A (en) * 1988-01-28 1988-09-20 International Flavors & Fragrances Inc. Ethyl norbornyl alkyl ethers, organoleptic uses thereof and process for preparing same
US5064650A (en) * 1988-04-19 1991-11-12 Southwest Research Institute Controlled-release salt sensitive capsule for oral use and adhesive system
US4863631A (en) * 1988-06-24 1989-09-05 International Flavors & Fragrances Inc. Dimethyl substituted alkyl nitriles, perfume and bleach compositions containing same organoleptic uses thereof and process intermediates for producing same
EP0347596A2 (en) * 1988-06-24 1989-12-27 INTERNATIONAL FLAVORS & FRAGRANCES INC. Bleaching composition
EP0347596A3 (en) * 1988-06-24 1991-02-06 INTERNATIONAL FLAVORS & FRAGRANCES INC. Bleaching composition
US5075027A (en) * 1989-02-06 1991-12-24 Colgate Palmolive Co. Thixotropic aqueous scented automatic dishwasher detergent compositions
US4986926A (en) * 1989-04-10 1991-01-22 The Drackett Company Thickened alkali metal hypochlorite compositions
US5639722A (en) * 1993-01-13 1997-06-17 The Clorox Company Acidic aqueous cleaning compositions
EP0622451A1 (en) * 1993-04-26 1994-11-02 The Procter & Gamble Company Perfumed hypochlorite bleaching compositions
EP0867503A2 (en) * 1993-04-26 1998-09-30 The Procter & Gamble Company Perfumed hypochlorite bleaching compositions
EP0867503A3 (en) * 1993-04-26 1999-01-20 The Procter & Gamble Company Perfumed hypochlorite bleaching compositions
US5454978A (en) * 1993-04-28 1995-10-03 Calgon Corporation Inhibiting deposition of oil on surface of water-carrying system
US5578580A (en) * 1993-05-28 1996-11-26 Ascor Chimici S.R.L. Veterinary composition, feedstuff and process
US6100228A (en) * 1993-10-29 2000-08-08 The Clorox Company Bleaching gel cleaner thickened with amine oxide, soap and solvent
EP0877790A1 (en) * 1995-08-18 1998-11-18 The Procter & Gamble Company Perfumed bleaching detergent compositions
EP0877790A4 (en) * 1995-08-18 1999-06-02 Procter & Gamble Perfumed bleaching detergent compositions
WO2001044429A1 (en) * 1999-12-16 2001-06-21 Unilever N.V. Household cleaning products
WO2001096521A1 (en) * 2000-06-14 2001-12-20 Henkel Kommanditgesellschaft Auf Aktien Fabric conditioner in liquid or gel form
WO2003066790A1 (en) * 2002-02-01 2003-08-14 The Procter & Gamble Company Amine oxides as perfume solubility agents
US20060247456A1 (en) * 2003-07-28 2006-11-02 Wolfgang Steven M Stearate composition and method of production thereof
US20060281937A1 (en) * 2003-07-28 2006-12-14 Heider Todd P Stearate composition and method
US7385068B2 (en) 2003-07-28 2008-06-10 Mallinckrodt Inc. Stearate composition and method
US7456306B2 (en) 2003-07-28 2008-11-25 Mallinckrodt Inc Stearate composition and method of production thereof
US20080308766A1 (en) * 2005-12-06 2008-12-18 Carlos Malet Stability improvement of liquid hypochlorite-containing washing and cleaning compositions
US20080308767A1 (en) * 2005-12-07 2008-12-18 Carlos Malet Increasing the stability of liquid hypochlorite-containing washing and cleaning compositions
DE102005062008B3 (en) * 2005-12-22 2007-08-30 Henkel Kgaa Odor reduction of hypochlorite-containing agents
US20080261839A1 (en) * 2005-12-22 2008-10-23 Carlos Malet Odor reduction for agents containing hypochlorite
US8008238B2 (en) 2005-12-22 2011-08-30 Henkel Ag & Co. Kgaa Odor reduction for agents containing hypochlorite
US20080274934A1 (en) * 2005-12-29 2008-11-06 Carlos Malet Inhibiting the corrosive properties of liquid cleaning agents containing hypochlorite
US7214652B1 (en) 2005-12-30 2007-05-08 3M Innovative Properties Company Anionic surfactant-containing hypochlorite bleach composition and methods of making and use
US20080305980A1 (en) * 2005-12-30 2008-12-11 Carlos Malet Stability of detergents containing hypochlorite
US7786066B2 (en) 2005-12-30 2010-08-31 Henkel Ag & Co. Kgaa Stability of detergents containing hypochlorite, phosphonate chelant, and optical brightener
US20080305981A1 (en) * 2005-12-30 2008-12-11 Carlos Malet stability of detergents containing hypochlorite
US20080311224A1 (en) * 2007-06-18 2008-12-18 Meghan Gressler Long-lasting mildew stain remover and method for making same
US20100207063A1 (en) * 2007-07-20 2010-08-19 Carlos Malet Gentle Bleach

Similar Documents

Publication Publication Date Title
US3876551A (en) Perfumed aqueous hypochlorite composition and method for preparation of same
US4390448A (en) Perfumed stable aqueous hypochlorite bleach compositions containing 2-methyl-2-octanol and thickened variation thereof
US3684722A (en) Thickened alkali metal hypochlorite bleaching and cleaning composition
US4576728A (en) Cleaning compositions
CA1156404A (en) Aqueous bleach compositions
US3686098A (en) Novel detergent composition
US3929661A (en) Liquid detergent bleaching composition
WO2007054177A1 (en) Fragrant consumer products comprising oxidizing agents
US3637511A (en) Detergent formulations
GB1120230A (en) Germicidal compositions
JPH11501982A (en) Bleaching composition with stable fragrance
JP3609845B2 (en) Method for imparting, improving, enhancing or modifying the fragrance properties of a fragrance composition or fragrance product, and fragrance composition or fragrance product
JPH0662997B2 (en) Bleaching composition containing perfume
KR930003244B1 (en) Aqueous thickened cleaning composition
US3758419A (en) Cleansing and laundering compositions
EP0347596B1 (en) Bleaching composition
US3256155A (en) Dentifrice composition
US4330425A (en) Use of mixture of aliphatic C10 branched olefin epoxides in augmenting or enhancing the aroma of articles subjected to action of aqueous hypochlorites
US4342663A (en) Use of mixture of aliphatic C10 branched olefins in augmenting or enhancing the aroma of articles subjected to action of aqueous hypochlorites
US4719042A (en) Tertiary alkyl-substituted alcohols as perfumes
DE2132898A1 (en) Foam-suppressing additives - for washing- cleaning - or water-softening compsns- selected from acetals, ketals and mercaptals
US4719041A (en) 1-alkyl/alkenyl cyclohexan-1-ols as perfumes
US4731356A (en) Unsaturated aliphatic ketone and use of same as perfuming ingredient
JP3459850B2 (en) High bulk density granular detergent composition
ES2216225T3 (en) PERFUMERY USE OF 1-METOXI-2-METHYL-3-PHENYLPROPANE, 1- (2-METOXYPROPIL) -4-METHYLBENZENE AND 3-METOXI-2-, 2,3-TRIMETHYL-1-PHENYLBUTANE.