Strategic Technologies
Other Bleach Activators
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U.S. Patents:
Alkoxylated peracid activators
Patent # 5,705,091 containing 5 claims, issued 01/06/1998. Bleaching compositions are provided that comprise peracid activators. The peracid activators are ester derivatives of a carboxylic acid where the oxygen is covalently bound through a polyhydroxy linking group to a leaving group that is displaceable in a peroxygen bleaching solution by perhydroxide anion. When the peracid activator is combined with a source of peroxygen in aqueous solution, then a stain removing peracid is formed. One embodiment of the peracid activator has the structure [Figure] where R' is a branched or linear C4-12 alkyl, n is 1 to about 7, and L is a leaving group.
Delayed onset active oxygen bleach composition
Patent # 5,130,044 containing 11 claims, issued 07/14/1992. Peroxygen bleach compositions which can be used together with oxygen-sensitive wash aids are disclosed. Combination products comprising these bleach compositions together with the oxygen sensitive wash aids are disclosed as well as are methods of laundering employing them. The bleach compositions include a peroxygen source, a surface active or hydrotropic bleach activator or catalyst therefor and a quaternary ammonium salt. As compared to equivalent compositions not containing the quaternary ammonium salt, these bleach compositions are characterized by a delayed onset of active oxygen production when they are added to wash solutions. When these bleach compositions are used in combination with oxygen-sensitive wash aids, the sensitive wash aids have an initial period when they can act before the active oxygen level rises to a level that it interferes with their action. The bleach compositions of this invention which contain the added quaternary ammonium salt are also characterized by achieving higher ultimate levels of active oxygen than do equivalent compositions which do not contain the ammonium salt.
Delayed onset active oxygen bleach composition
Patent # 5,130,045 containing 6 claims, issued 07/14/1992. Peroxygen bleach compositions which can be used together with oxygen-sensitive wash aids are disclosed. Combination products comprising these bleach compositions together with the oxygen sensitive wash aids are disclosed as well as are methods of laundering employing them. The bleach compositions include a peroxygen source, a surface active or hydrotropic bleach activator or catalyst therefor and a quaternary ammonium salt. As compared to equivalent compositions not containing the quaternary ammonium salt, these bleach compositions are characterized by a delayed onset of active oxygen production when they are added to wash solutions. When these bleach compositions are used in combination with oxygen-sensitive wash aids, the sensitive wash aids have an initial period when they can act before the active oxygen level rises to a level that it interferes with their action. The bleach compositions of this invention which contain the added quaternary ammonium salt are also characterized by achieving higher ultimate levels of active oxygen than do equivalent compositions which do not contain the ammonium salt.
Patent # 5,478,356 containing 29 claims, issued 12/26/1995. Cyanoamine activators give excellent bleaching performance when combined with a peroxygen source and dissolved in solution. Activators include imides wherein each activator has two acyl groups attached to a common nitrogen and to a cyclic moiety, with the nitrogen being cyano substituted. The two acyl groups form intermediate peroxy groups in the presence of a peroxygen source in solution. Preferred activators include N-cyanophthalimide and N-cyanosuccinimide.
Stable peracid bleaching compositions: organic peracid, magnesium sulfate and controlled amounts of water
Patent # 5,089,167 containing 23 claims, issued 02/18/1992. In one embodiment, the invention provides a stable peracid bleach composition comprising discrete granules which comprise peracid, namely, diperoxydodecanedioic acid. In another preferred embodiment, enzymes are present in the composition separate from the discrete peracid granules. In both the enzyme-containing and non-enzyme containing compositions, peracid and exotherm control agents are combined in a discrete granule in which the amount of water is carefully controlled to result in, respectively, maximum peracid and enzyme stability. Standard bleaching composition adjuncts such as fillers, brighteners, pH control agents and the like may be included in the compositions apart from the discrete peracid granules.
Patent # 5,211,874 containing 17 claims, issued 05/18/1993. In one embodiment, the invention provides a stable peracid bleach composition comprising discrete granules, which comprise peracid, namely, diperoxydodecanedioic acid. In another preferred embodiment, enzymes are present in the composition separate from the discrete peracid granules. In both the enzyme-containing and non-enzyme containing compositions, peracid and exotherm control agents are combined in a discrete granule in which the amount of water is carefully controlled to result in, respectively, maximum peracid and enzyme stability. Standard bleaching composition adjuncts such as fillers, brighteners, pH control agents and the like may be included in the compositions apart from the discrete peracid granules.
Patent # 5,093,021 containing 14 claims, issued 03/03/1992. Methods and compositions for increased stability of enzymes in oxidant dry bleach. Enzyme stability is adversely affected by increased temperature, humidity, and the presence of strong oxidants, such as peracids. The instant invention provides enzyme stability in the presence of oxidant bleaches by coating or encapsulating the enzyme, while providing enzyme solubility suitable for use in bleach mixtures upon introduction to an aqueous medium. Particularly, alkali and neutral materials act as protection agents, which neutralize oxidant species before the contact and denature the enzyme. Other standard bleaching composition adjuncts such as builders, fillers, buffers, brighteners, fragrances, and the like may be included in the enzyme-containing oxidant bleach composition in addition to the discrete coated enzyme granules.
Patent # 5,167,854 containing 8 claims, issued 12/01/1992. The invention relates to a bleaching composition containing an oxidant bleach and enzyme granules, in which enzyme stability is prolonged without undue loss of solubility despite intimate contact of said enzyme granules and said oxidant bleach, comprising: an oxidant bleach, selected from the group consisting of alkali-metal peroborates, alkali metal percarbonates, hydrogen peroxide adducts, and mixtures thereof and hydrolase enzyme granules comprising a hydrolase enzyme core and a water soluble alkali metal silicate coating substantially encapsulating said core, said coating including at least one protective agent, said agent being selected from the group consisting of transition metals; reducing agents; and mixtures thereof. Sodium percarbonate is a preferred oxidant, while transition metals combined with a sodium silicate coating provide enhanced storage stability to the enzymes thereby coated.
Patent # 5,254,287 containing 7 claims, issued 10/19/1993. The invention relates to a bleaching composition containing an oxidant bleach and enzyme granules, in which enzyme stability is prolonged without undue loss of solubility despite intimate contact of said enzyme granules with said oxidant bleach. In the invention, an oxidant is selected from the group consisting of alkali metal perborates, alkali metal percarbonates, hydrogen peroxide adducts, and mixtures thereof, and combined with an enzyme which is coated substantially completely by a water soluble polymer, in which an additive selected from the group consisting of reducing agents, a transition metal, and mixtures thereof is incorporated to enhance enzyme stability.
Patent # 4,964,870 containing 22 claims, issued 10/23/1990. The invention provides novel peracid precursors representative of which is the structure: [Figure] wherein R1 is alkyl of 1 to 20 carbon atoms; R2 is OH, --O--R3, or [Figure] and X1, X2, Y and Z are individually selected from H, SO3--, CO2--, NO2, NR45+, halogen, R6 and mixtures thereof; wherein R3 of --O--R3 is alkyl of 1 to 20 carbon atoms; R4 of [Figure] is alkyl of 1 to 20 carbon atoms; R5 of NR45+ is selected from H, alkyl of 1 to 24 carbon atoms and mixtures thereof; and R6 is alkyl of 1 to 20 carbon atoms. In one embodiment of the invention, the novel peracid precursors are combined with a source of hydrogen peroxide and sufficient quantities of buffer to impact an alkaline pH when the composition is placed in aqueous solution. Preferred embodiments of the invention include wherein R2 is hydroxy, and R1 is alkyl of 1 to 20 carbon atoms (monoester); and wherein R2 is [Figure] and R1 and R4 are alkyls of 1 to 20 carbon atoms (diester) and may be either symmetrical (i.e., R1 =R4) or mixed (i.e., R1 .noteq.R4). The mixed diester embodiment appears to provide benefits of mixed hydrophobic/hydrophilic peracid generation to oxidize both hydrophobic and hydrophilic soils. Various detergent adjuncts known to those skilled in the art may be added, such as surfactants, builders, fragrances, antimicrobial compounds and the like.
Patent # 4,790,952 containing 20 claims, issued 12/13/1988. A number of novel peracid precursors each have the general structure: wherein: Z is a leaving group, the conjugate acid of the leaving group being in the range of from about 4 to 15; R is a substituted or unsubstituted alkyl or alkenyl group having from about 1 to 18 carbon atoms; and M is hydrogen or an alkali or alkaline earth metal. A method is also disclosed for synthesizing a product as represented above wherein succinic anhydride, including an R constituent as defined above is dissolved in a water-miscible, non-nucleophilic solvent and an acid including a Z constituent as defined above is neutralized and deprotonated to form a nucleophile, the substituted anhydride and the nucleophile being combined to form the product. The product is a component in a dry bleach product, optionally including other adjuncts.
Patent # 4,960,925 containing 44 claims, issued 10/02/1990. A number of novel peracid precursors each have the general structure: wherein: Z is a leaving group, the conjugate acid of the leaving group being in the range of from about 4 to 15; R is a substituted or unsubstituted alkyl or alkenyl group having from about 1 to 18 carbon atoms; and M is hydrogen or an alkali or alkaline earth metal. A method is also disclosed for synthesizing a product as represented above wherein succinic anhydride, including an R constituent as defined above is dissolved in a water-miscible, non-nucleophilic solvent and an acid including a Z constituent as defined above is neutralized and deprotonated to form a nucleophile, the substituted anhydride and the nucleophile being combined to form the product. The product is a component in a dry bleach product, optionally including other adjuncts.
Patent # 4,956,117 containing 17 claims, issued 09/11/1990. A perhydrolysis system is provided which includes peroxyacid precursors and a source of peroxygen. Upon dissolution in water these compositions provide high yields of a novel peroxyacid having the structure where R is hydrogen or an alkyl of not more than 5 carbon atoms. The precursors may include hydroxyl nitrogen derivatives as leaving groups, since the .alpha.-substituted phenoxy moiety enhances carbonyl reactivity toward perhydroxyl anion.
Patent # 5,049,305 containing 12 claims, issued 09/17/91. A perhydrolysis system is provided which includes peroxyacid precursors and a source of peroxygen. Upon dissolution in water these compositions provide high yields of a novel peroxyacid having the structure where R is hydrogen or an alkyl of not more than 5 carbon atoms. The precursors may include hydroxyl nitrogen derivatives as leaving groups, since the .alpha.-substituted phenoxy moiety enhances carbonyl reactivity toward perhydroxyl anion.
Patent # 4,778,618 containing 24 claims, issued 10/18/1988. The invention provides novel bleaching compositions comprising peracid precursors with the general structure with R, R', R" and L as defined in the specification. Novel peracids and precursors are also herein disclosed. These peracid precursors provide new, proficient and cost-effective compounds for fabric bleaching.
Patent # 4,959,187 containing 20 claims, issued 09/25/1990. The invention provides novel bleaching compositions comprising peracid precursors with the general structure with R, R', R" and L as defined in the specification. Novel peracids and precursors are also herein disclosed. These peracid precursors provide new, proficient and cost-effective compounds for fabric bleaching.
Patent # 5,002,691 containing 20 claims, issued 03/26/1991. The present invention provides stable bleach activator granules comprising: a) a peroxygen bleach activator having the structure: wherein R is C1-20 branched or straight chain alkyl, alkoxylated alkyl, cycloalkyl, alkenyl, aryl, substituted aryl, alkylaryl; R' and R" are independently H, C1-4 alkyl, aryl; and L is a leaving group; b) a pliable binding material selected from materials having a melting completion temperature of greater than about 40° C.; and, optionally, c) a filler material. These bleach activator granules are combined with a detergent base, which contains an oxidant bleach to provide an activated oxidant detergent composition.
Patent # 5,112,514 containing 9 claims, issued 05/12/1992. The present invention provides stable bleach activator granules comprising: a) a peroxygen bleach activator having the structure: wherein R is C1-20 branched or straight chain alkyl, alkoxylated alkyl, cycloalkyl, alkenyl, aryl, substituted aryl, alkylaryl; R' and R" are independently H, C1-4 alkyl, aryl; and L is a leaving group; b) a pliable binding material selected from materials having a melting completion temperature of greater than about 40° C.; and, optionally, c) a filler material. These bleach activator granules are combined with a detergent base, which contains an oxidant bleach to provide an activated oxidant detergent composition.
Patent # 5,269,962 containing 26 claims, issued 12/14/1993. The present invention provides stable bleach activator granules comprising: (a) a peroxygen bleach activator having the structure: wherein R is C1-20 branched or straight chain alkyl, alkoxylated alkyl, cycloalkyl, alkenyl, aryl, substituted aryl, alkylaryl; R' and R" are independently H, C1-4 alkyl, aryl; and L is a leaving group; b) a pliable binding material selected from materials having a melting completion temperature of greater than about 40° C.; and c) a solubilizing aid selected from the group consisting of magnesium sulfate, alkali aryl sulfonate, polyvinyl pyrrolidone or mixtures thereof. The invention can also include additional stiffeners, such as calcium or magnesium silicate, or silica.
Patent # 5,391,812 containing 13 claims, issued 02/21/1995. Polyglycolate compounds are provided having the general structure wherein n is an integer from 2 to about 10; R is C1-20 linear or branched alkyl, alkoxylated alkyl, cycloalkyl, aryl, alkylaryl, substituted aryl; R' and R" are independently H, C1-20 alkyl, aryl, C1-20 alkylaryl, substituted aryl, and NR3.alpha.+, wherein R.alpha. is C1-30 alkyl; and L is a leaving group displaceable in a peroxygen bleaching solution by perhydroxide anion. When this compound is combined with a source of peroxygen in aqueous solution, then a plurality of stain removing peracids are formed. Such peracids are formed substantially sequentially beginning with the carbonyl adjacent to the leaving group L. Thus, a first stain removing peracid having the structure will be formed in amounts approaching quantitative yield.
Patent # 5,545,748 containing 2 claims, issued 08/13/1996. Polyglycolate compounds are provided having the general structure wherein n is an integer from 2 to about 10; R is C1-20 linear or branched alkyl, alkoxylated alkyl, cycloalkyl, aryl, alkylaryl, substituted aryl; R' and R" are independently H, C1-20 alkyl, aryl, C1-20 alkylaryl, substituted aryl, and NR3.alpha.+, wherein R.alpha. is C1-30 alkyl; and L is a leaving group displaceable in a peroxygen bleaching solution by perhydroxide anion. When this compound is combined with a source of peroxgen in aqueous solution, then a plurality of stain removing peracids are formed. Such peracids are formed substantially sequentially beginning with the carbonyl adjacent to the leaving group L. Thus, a first stain removing peracid having the structure will be formed in amounts approaching quantitative yield.
Thickened peracid precursor compositions
Patent # 4,900,469 containing 18 claims, issued 02/13/1990. A thickened cleaning composition for laundry products incorporates low levels of a fluorescent whitening agent or dye, a surfactant, an acidic pH adjusting agent and an insoluble peracid precursor. At the acidic pH, the fluorescent whitening agent precipitates as a colloidal particle, and is stabilized by associating with the surfactant, resulting in thickening. The precursor is stably suspended in its inactive form in the thickener, and provides oxidizing power as the corresponding peracid is formed when added to an alkaline wash or rinse solution. The composition preferably is formulated with an acidic soluble bleach source and most preferably with a peroxygen bleach.
Patent # 4,655,781 containing 25 claims, issued 04/07/1987. This invention provides stable peroxyacid bleaching compositions comprising: (a) a surface active peroxyacid, and (b) at least one surfactant which forms a mixed micelle in aqueous solution with said peroxyacid; wherein said aqueous solution contains a detergent concentration of about 0.1 to 3.0 grams/liter.
Buffers and other typical cleaning adjuncts known to those skilled in the art may be included. The invention also provides a method of stabilizing the decomposition rate of surface-active peroxyacids.
Patent # 5,415,796 containing 24 claims, issued 05/16/1995. The invention provides a stable, liquid, substantially nonaqueous detergent comprising: at least one imidoperacid with the structure [Figure] wherein R is C1-20 alkylene, R1 and R2 are individually H or C1-6 alkyl or alkenyl, or R1 and R2 join to form a heterocycle, said imidoperacid being solubilized in a liquid nonionic surfactant. The stable liquid detergent has excellent oxidant and phase stability and, if enzymes are present, maintains proficient enzyme activity.
Liquid hydrogen peroxide/peracid precursor bleach: acidic aqueous medium containing solid peracid precursor activator
Patent # 4,772,290 containing 15 claims, issued 09/20/1988. Storage-stable, low temperature-active liquid hydrogen peroxide laundry bleaching compositions are provided. The compositions contain a dispersion of a solid particulate peracid activator in acidic aqueous hydrogen peroxide. The activator is insoluble at the acidic conditions of storage but dissolves and activates the hydrogen peroxide at the alkaline conditions of use in laundry. Optionally the bleaching compositions can contain optical brighteners, surfactants, and/or fabric softeners.
Patent # 5,792,385 containing 23 claims, issued 08/11/1998. A stable liquid peracid precursor composition for delivering a bleaching and cleaning material is provided in which the liquid peracid precursor composition combines a dispersion medium, which comprises a stabilizing effective amount of a liquid matrix and an emulsifier, and a dispersed phase that comprises a peracid precursor. The bleaching and cleaning material comprises either a hydrophobic or hydrotropic generated mono- or diperoxyacid, or mixtures thereof.
Patent # 5,776,877 containing 6 claims, issued 07/07/1998. A stable liquid peracid precursor composition for delivering a bleaching and cleaning material is provided in which the liquid peracid precursor composition combines a dispersion medium which comprises a stabilizing effective amount of a liquid matrix and an emulsifier, and a dispersed phase that comprises a peracid precursor. The bleaching and cleaning material comprises either a hydrophobic or hydrotropic generated mono- or diperoxyacid, or mixtures thereof.
Patent # 5,681,805 containing 38 claims, issued 10/28/1997. A stable liquid peracid precursor composition for delivering a bleaching and cleaning material is provided in which the liquid peracid precursor composition combines a dispersion medium, which comprises a stabilizing effective amount of a liquid matrix and an emulsifier, and a dispersed phase that comprises a peracid precursor. The bleaching and cleaning material comprises either a hydrophobic or hydrotropic generated mono- or diperoxyacid, or mixtures thereof.
Patent # 5,954,998 containing 23 claims, issued 09/21/1999. A stable liquid peracid precursor composition for delivering a bleaching and cleaning material is provided in which the liquid peracid precursor composition combines a dispersion medium, which comprises a stabilizing effective amount of a liquid matrix and an emulsifier, and a dispersed phase that comprises a peracid precursor. The bleaching and cleaning material comprises either a hydrophobic or hydrotropic generated mono- or diperoxyacid, or mixtures thereof.
Patent # 5,877,136 containing 14 claims, issued 03/02/1999. A stable liquid peracid precursor composition for delivering a bleaching and cleaning material is provided in which the liquid peracid precursor composition combines a dispersion medium, which comprises a stabilizing effective amount of a liquid matrix and an emulsifier, and a dispersed phase that comprises a peracid precursor. The bleaching and cleaning material comprises either a hydrophobic or hydrotropic generated mono- or diperoxyacid, or mixtures thereof.
Patent # 5,977,044 containing 30 claims, issued 11/01/1999. A stable liquid peracid precursor composition for delivering a bleaching and cleaning material is provided in which the liquid peracid precursor composition combines a dispersion medium which comprises a stabilizing effective amount of a liquid matrix and an emulsifier, and a dispersed phase that comprises a peracid precursor. The bleaching and cleaning material comprises either a hydrophobic or hydrotropic generated mono- or diperoxyacid, or mixtures thereof.
Patent # 5,877,137 containing 14 claims, issued 03/02/1999. A stable liquid peracid precursor composition for delivering a bleaching and cleaning material is provided in which the liquid peracid precursor composition combines a dispersion medium, which comprises a stabilizing effective amount of a liquid matrix and an emulsifier, and a dispersed phase that comprises a peracid precursor. The bleaching and cleaning material comprises either a hydrophobic or hydrotropic generated mono- or diperoxyacid, or mixtures thereof.
Patent # 5,591,378 containing 19 claims, issued 01/07/1997. Substituted benzonitrile activators give excellent bleaching performance when combined with a peroxygen source and dissolved in solution. These substituted benzonitrile activators give best bleaching performance when the activators are multiply substituted with electron-withdrawing groups.
Patent # 5,707,542 containing 8 claims, issued 01/13/1998. Substituted benzonitrile activators give excellent bleaching performance when combined with a peroxygen source and dissolved in solution. These substituted benzonitrile activators give best bleaching performance when the activators are multiply substituted with electron-withdrawing groups.
Patent # 4,957,647 containing 9 claims, issued 09/18/1990. The invention provides novel bleaching compositions comprising peracid precursors having oxynitrogen leaving groups. Peracid precursors containing these leaving groups provide new, proficient and cost-effective compounds for fabric bleaching. These compounds have the general structures: where R is a straight or branched chain C1-20 alkyl, alkoxyl, cycloalkyl and mixtures thereof; R1 contains at least one carbon atom which is singly bonded directly to N; n is an integer from 1 to 6 and X is methylene or a heteroactom; or wherein n is the same as in (I); but R2 contains a carbon atom doubly bonded directly to N, and, either X is a heteroatom or nothing, and R is C4-17 alkyl.
Patent # 5,087,385 containing 10 claims, issued 02/11/1992. The invention provides novel bleaching compositions comprising peracid precursors having oxynitrogen leaving groups. Peracid precursors containing these leaving groups provide new, proficient and cost-effective compounds for fabric bleaching. These compounds have the general structures: wherein R is a straight or branched chain C1-20 alkyl, alkoxyl, cycloalkyl and mixtures thereof; R1 contains at least one carbon atom which is singly bonded directly to N; n is an integer from 1 to 6 and X is methylene or a heteroatom; or wherein n is the same as in (I); but R2 contains a carbon atom doubly bonded directly to N, and, either X is a heteroatom or nothing, R is C4-17 alkyl or both
Patent # 5,328,634 containing 10 claims, issued 07/12/1997. The invention provides novel bleaching compositions comprising peracid precursors having oxynitrogen leaving groups. Peracid precursors containing these leaving groups provide new, proficient and cost-effective compounds for fabric bleaching. These compounds have the general structures: wherein R is a straight or branched chain C1-20 alkyl, alkoxyl, cycloalkyl and mixtures thereof; R1 contains at least one carbon atom which is singly bonded directly to N; n is an integer from 1 to 6 and X is methylene or a heteroatom; or wherein n is the same as in (I); but R2 contains a carbon atom doubly bonded directly to N, and, either X is a heteroatom, R is C4-17 alkyl or both.
Patent # 5,380,457 containing 6 claims, issued 01/10/1995. The invention provides novel bleaching compositions comprising peracid precursors having oxynitrogen leaving groups. Peracid precursors containing these leaving groups provide new, proficient and cost-effective compounds for fabric bleaching. These compounds have the general structures: wherein R is a straight or branched chain C1-20 alkyl, alkoxyl, cycloalkyl and mixtures thereof; R1 contains at least one carbon atom which is singly bonded directly to N; n is an integer from 1 to 6 and X is methylene or a heteroatom; or wherein n is the same as in (I); but R2 contains a carbon atom doubly bonded directly to N, and, either X is a heteroatom or nothing R is C4-17 alkyl or both.
Method for preparing 1,4-diaminoanthraquinones and intermediates thereof
Patent # 4,661,293 containing 8 claims, issued 04/28/1987. Aminoanthraquinones are generally useful as dyes and coloring agents. But known methods of synthesizing unsymmetrically substituted 1,4-diaminoanthraquinones are tedious and complex. A simple and efficient method is provided for preparing 1,4-diaminoanthraquinones, particularly unsymmetrically substituted 1,4-diaminoanthraquinones, by means of novel monoamino-monotosyl-anthraquinones.
Method for preparing 1,4-diaminoanthraquinones and intermediates thereof
Patent # 4,746,461 containing 11 claims, issued 05/24/1988. Aminoanthraquinones are generally useful as dyes and coloring agents. But known methods of synthesizing unsymmetrically substituted 1,4-diaminoanthraquinones are tedious and complex. A simple and efficient method is provided for preparing 1,4-diaminoanthraquinones, particularly unsymmetrically substituted 1,4-diaminoanthraquinones, by means of novel monoamino-monotosyloxy-anthraquinones.
Patent # 5,091,560 containing 13 claims, issued 02/25/1992. A method for synthesizing an acyloxycarboxylic acid by providing a reaction chamber, establishing sources of an alpha.-hydroxycarboxylic acid and an acid chloride, and repeatedly contacting substantially equal molar amounts of the .alpha.-hydroxycarboxylic acid and the acid chloride within the reaction chamber. The acyloxycarboxylic acid so synthesized is useful as a starting material for conversion to various esters which, when placed in aqueous solution with a source of hydrogen peroxide, result in a peracid and are useful for bleaching applications.
Patent # 5,710,296 containing 15 claims, issued 01/20/1998. A method for preparing phenyl esters in high yields under mild reaction conditions is provided. Particularly preferred phenyl esters prepared in accordance with the inventive method are alkanyloxy-benzene compounds having a C2-18 alkyl. The method is practiced by reacting a carboxylic acid with an acid halide either in the presence of or followed by the addition of a phenol.
Patent # 6,127,536 containing 20 claims, issued 10/03/2000. An improved synthesis for preparing a tetraamido-macrocyclic ligand, such as 5,6-Benzo-3,8,11,13-tetraoxo-2,2,9,9-tetramethyl-12,12-diethyl-1,4,7,10-tetraazacyclotridecane, H4, in greatly improved yield and in a commercially viable manner, comprising the steps of dissolving a quantity of a 1,2-bis(2-aminoalkanamido)benzene in a solution comprised of ethyl acetate and methylene chloride to yield a first reaction solution; dissolving a quantity of a malonyl dihalide in an ethyl acetate solution to yield a second reaction solution; adding the first reaction solution and the second reaction solution to a reaction vessel containing a third reaction solution comprised of refluxing ethyl acetate solution and an acid scavenger to form a reaction mixture; and isolating a solid product comprised of the tetraamido-macrocycle directly from the reaction mixture by filtration.
Process for preparing phenyl esters of substituted acids
Patent # 4,985,180 containing 11 claims, issued 01/15/1991. Phenyl esters of substituted acids are prepared by a two-step process, in which a phenol derivative is first treated with an acid halide to yield a phenyl ester intermediate and the intermediate is reacted with an appropriate nucleophile.
Patent # 5,069,828 containing 9 claims, issued 12/03/1991. An improved process for preparing benzenesulfonate salts, such as 4-nonanoyloxybenzenesulfonic acid, sodium salt, from an appropriately substituted acid chloride or chloroformate and a hydroxybenzenesulfonic acid in which the reaction is conducted in the presence of a phase transfer catalyst selected from quaternary ammonium and quaternary phosphonium salts.
Process for preparing benzenesulfonate salts
Patent # 5,153,341 containing 8 claims, issued 10/06/1992. An improved process for preparing alkanoyloxyacetyloxybenzenesulfonate salts in which phenyl esters of alkanoyloxyacetic acids (alkanoyloxyacetyloxybenzenes) are sulfonated to yield novel alkanoyloxyacetyloxybenzenesulfonic acids which on neutralization, yield the corresponding alkanoyloxyacetyloxybenzenesulfonate salts.
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