Environmentally acceptable bleach catalyst delivery composition
A chelate-based catalyst delivery composition with a water-soluble polymer and non-ionic surfactant addresses stability and absorption issues in oxidative bleaching, ensuring effective and biodegradable bleaching performance in detergent compositions.
Patent Information
- Application Number
- GB2023009904
- Authority / Receiving Office
- GB · GB
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2023-06-29
- Publication Date
- 2025-01-08
AI Technical Summary
Existing oxidative bleaching catalysts, such as MnMe3-TACN, are not biodegradable and face stability issues in high pH environments, leading to uneven distribution and absorption challenges in detergent compositions, particularly in fabric washing where they may not remain effective or absorb onto fabrics as intended.
A catalyst delivery composition comprising a chelate of a transition metal, preferably manganese, in the form of a hexadentate complex with a water-soluble organic polymer like PVA, providing controlled release and enhanced stability, and a non-ionic surfactant for improved absorption onto fabric surfaces.
The composition ensures stable and effective release of the oxidative bleaching catalyst at lower temperatures, maintaining absorption on fabric surfaces and improving detergency, while being environmentally friendly and biodegradable.
Abstract
Description
The present invention relates to delivery compositions for environmentally acceptable oxidative bleaching catalysts for the purposes of delivering an environmentally acceptable oxidative bleaching catalysts into an in use composition and method of use. An example delivery composition format is a granule. Background Oxidative bleaching is widely used in industry and in the home. Uses in industry include bleaching paper pulp and raw cotton; and in the home for the cleaning of laundry and dishwashing. Oxidative bleach in the form of hydrogen peroxide and sources of hydrogen peroxide, such perborate and percarbonate can provide satisfactory bleaching but this is usually required to occur at elevated temperature, are such as above 60°C and up to boiling point. It is well established that catalysts may be used to enable oxidative bleaches to be effective at lower temperatures, such as ambient temperature. Other adjunct to oxidative bleaches are what are termed activators, which differ from catalysts in that they are used in the stoichiometric amounts. Examples include TAED, Tetra acetyl ethylene diamine, NTA, nitrilo tri acetic acid and NOBS, sodium nonanoyloxybenzenesulfonate. The species form per acetic acid which has a lower activation energy and enables bleaching also at low temperatures. Other components useful in removing coloured species, a common function of oxidative bleaches, are enzymes. Enzymes commonly used are amylase for starch and protease for proteins. Such enzymes typically function effectively at relatively low temperatures and may usefully be used in conjunction with oxidative bleaches provided the oxidative bleach is effective at low temperature. As can be appreciated from the above there is a complex interplay between different components of a bleaching system and optimising those interactions is fundamental to effective cleaning and similar oxidative processes. A particularly significant component of this is the preservation of the active component prior to use. Bleaching compositions are typically distributed in concentrated form which must be capable of being stored for, typically, many months whereas in a washing situation bleaching action is required in a relatively short time and particularly relevant to bleach catalysts at a low temperature. There is therefore a problem of providing a delivery mechanism for oxidative bleach catalysis. Oxidative bleaching catalysts are used in a variety of detergent compositions and particularly in automatic dishwashing or fabric washing detergent compositions. Whilst oxidative bleaching catalysts may be incorporated in a fabric washing detergent composition this does not guarantee that the oxidative bleaching catalyst will either remain stable over time, given that fabric washing compositions are typically prepared having a pH greater than pH 7, often at a pH of approximately 10. There is therefore a need for fabric washing detergent compositions compatible with environmentally acceptable oxidative bleaching catalysts. Further, particularly in concentrated and granular detergent compositions, compositions are typically provided to an end user for use as a diluted or dissolved solution, the pH that an oxidative bleaching catalyst is exposed to prior to use can be particularly high and this can give rise to issues of storage stability. There is therefore a need for improved delivery compositions compatible with environmentally acceptable oxidative bleaching catalysts, particularly those structures defined in this present application. Oxidative bleaches relevant to the present invention came to prominence in the form of ligands chelated to manganese, in particular the ligand Me3-TACN, Octahydro-1,4,7-trimethyl-1H-1,4,7-triazonine, which is complexed with manganese to form MnMe3-TACN, Bis(N,N',N"-trimethyl-1,4,7-triazacyclononane)-trioxo-dimanganese (IV) di(hexafluorophosphate) monohydrate, referred to by either the abbreviation or the tradenames Dragon™ and WeylClean™. This material, whilst widely used and effective either as the catalyst or in the form of the ligand, is effectively not biodegradable. Given that catalyst materials are effective in small amounts then persistence of such low temperature active materials in the environment is undesirable. Similarly, whilst oxidative bleaching catalysts may be incorporated into fabric washing detergent compositions this does not guarantee that the oxidative bleaching catalyst will absorb onto a fabric being washed. The function of a detergent composition is to absorb on the surfaces of fabrics and preferentially adhere, such that oils and other residues are removed. This is carried out by the means of surfactants, surfactants typically being classified as anionic, non-ionic and cationic. There is therefore the challenge of formulating a fabric washing detergent composition to incorporate an oxidative bleaching catalyst such that the oxidative bleaching catalyst can remain absorbed on a fabric surface after a washing process, washing process typically being followed up by a rinsing process. There is therefore a need for a fabric washing detergent composition capable of delivering environmentally acceptable oxidative bleaching catalysts during a washing process and giving them in place after such a process. Therefore, there is a need for delivery compositions which enable environmentally acceptable oxidative bleaching catalysts, particularly those structures defined in the present application which provide, typically delayed, release of the oxidative bleaching catalyst at a point in a method of washing were the oxidative bleaching catalyst has a higher probability of absorption onto a fabric. Alternatively, particularly rapid release of the oxidative bleaching catalyst may also be advantageous as the oxidative bleaching catalyst can absorb one fabric before significant concentration of surfactant, for example, is present in a washing method so as to compete with the oxidative bleaching catalyst for absorption onto a fabric. Fabric washing detergent compositions are provided in a number of different formats, such as compositions relevant for hand washing, machine washing, uncoloured garments and coloured garments. Compositions which provide an oxidising agent and widely used and these can also give rise to stability problems regarding environmentally acceptable oxidative bleaching catalysts, such as those structures defined in the present application. There is therefore a need for delivery compositions which mitigate or ameliorate issues caused by oxidising agents in fabric washing detergent compositions. The aforementioned problems are particularly present regarding environmentally acceptable oxidative bleaching catalysts as these structures are often chemically complex, present in small amounts and therefore inherently of high surface area to volume in a composition and specifically to environmentally acceptable compositions often have labile groups intended to be degraded so as to provide biodegradability, such groups are typically more labile in the presence of a high pH, oxidising agent or combinations thereof. Further, due to the typically low levels of oxidative bleaching catalyst used in detergent compositions, such as levels as low as 0.01% is important that the oxidative bleaching catalyst is not present in high concentrations, such as individual granules, since this can give rise to uneven distribution, particularly if exacerbated due to settling of a granular mixture, for example, during transportation. There is therefore a need for delivery compositions which enable even distribution, along with other relevant detergents ingredients into a detergent composition, particularly a fabric washing detergent composition and in particular a granular, solids fabric washing detergent composition. There is therefore a need for a delivery composition to enable an environmentally acceptable beach catalyst to be incorporated into a composition which is storage stable yet also effective in use. A catalyst with greater compatibility to other components used in end-use applications, such as domestic laundry and dishwashing is desirable. The invention The present invention in its various aspects is as set out in the appended claims. The present invention provides a catalyst delivery composition comprising a chelate as a solid or solid solution in the form of a particle or sheet, the composition comprising from 1 to 50% of the chelate, from 1 to 50% of a water-soluble organic polymer and optionally an inorganic solid in the form of an alkali metal salt of from 1 to 98% the chelate comprising a compound (L) as defined below as the ligand of a transition metal element (M), the ligand being a compound (L) of structural formula 1 as presented below. The catalyst delivery composition of the present invention includes, a chelate comprising a compound (L) as defined below as the ligand of a transition metal element (M), the chelate being in solid form either as a solid or in solid solution in the form of a particle or sheet the composition comprising from 1 to 50% of the chelate, from 1 to 50% of a water-soluble organic polymer and optionally an inorganic solid in the form of an alkali metal salt of from 1 to 98%. All percentages being by weight. The transition metal element M is preferably Mn more preferably in the 2+ oxidation state. The catalyst delivery composition preferably has an in-use pH of the catalyst delivery composition is in the range from pH 8 to 10. This is defined by the pH of a 10g / I solution of the delivery composition. The present invention includes a detergent composition comprising the catalyst delivery composition. The detergent composition is preferably a dishwashing composition. The present invention in addition to providing an alternative bleach catalyst also provides specific advantages, particularly relevant to dishwashing detergent compositions. Specifically, chelates forming a component of the present invention with the detersive surfactants are, in general, more hydrophobic and, in general less water-soluble than the most prominent corner used oxidative bleaching catalyst,MnMe3-TACN, Bis(N,N',N"- trimethyl-1,4,7-triazacyclononane)-trioxo-dimanganese (IV) di(hexafluorophosphate) monohydrate. This gives rise to 2 advantages in detergent compositions, namely that the catalyst in the form of the chelates can dissolve progressively during a detergency operation, such as dishwashing and therefore provide a constant level of catalyst rather than a high level at the beginning of a wash, which is particularly the coldest, with decreasing activity during the wash. This is facilitated by the presence of surfactant to enable the surface of the chelate, in a solid state, to be whetted and thereby facilitate dissolution kinetics. A further advantage is that the hydrophobicity of the chelates provides additional adsorption onto hydrophobic surfaces, such as greasy surfaces, enabling those services to be oxidised and in conjunction with associated factors for removal into the bulk of the washing liquor provides improved detergency. It is therefore preferred that the delivery composition of the present invention comprises a surfactant. The chelate is preferably a hexadentate complex. The chelate preferably comprises two ligands chelated to 1 transition metal element. The chelate preferably comprises one or more further ligands. A further ligand is an inorganic anion or a carboxylic acid. The chelate preferably consists of two such further ligands. The further ligands are preferably selected from H2O, a halide or an organic acid. The further ligands are preferably selected from, H2O, Cl’ and acetic acid. The chelate of the present invention is preferably a chelate of a transition metal. Preferred transition metals are Iron (Fe): Manganese (Mn): Copper (Cu): and Cobalt (Co). Preferred transition metal ions are iron(ll) or iron(lll); manganese(ll) or manganese(lll); copper(ll); cobalt(ll) or cobalt(l 11). The preferred transition metal is preferably manganese or cobalt, most preferably manganese, still more preferably manganese (II) or (III). The chelate of the present invention is preferably a chelate of the transition metal element manganese, preferably wherein Mn is in the 3+, (III) oxidation state. In the present invention the water-soluble organic polymer is preferably used to encapsulate the chelate or to act as a solvent to provide a solid solution of the chelate, this providing controlled release and improved stability. Water-soluble organic polymers of the present invention are: Polyvinyl alcohol (PVA), Polyvinylpyrrolidone (PVP), Cellulose derivatives, such as hydroxypropyl methylcellulose (HPMC) or carboxymethyl cellulose (CMC), Polyethylene glycol (PEG). The preferred water-soluble organic polymer is PVA. PVA is highly water-soluble, allowing for the easy dissolution of the encapsulating film during the dishwashing process. The PVA is preferably present as a film, such as may be used to provide sachets or packaging for other components, such as in most preferably, a source of oxidative be shuts as a jumper oxide, for example sodium percarbonate. The use of PVA particularly a PVA film can provide controlled release of the encapsulated ingredients. It has been found that the water-soluble organic polymers provide greater storage stability of the detergent delivery composition of the present invention and specifically of the chelate therein. The most preferred for this purpose is PVA. The preferred molecular weight of the water-soluble organic polymer is in the range PVAs with molecular weights ranging from 10,000 to 200,000 as measured using size exclusion chromatography using a polystyrene standard. The preferred molecular weight range is 50,000 to 150,000, this enables rapid water solubility but effective protection for the chelate against degradation, particularly in high pH storage environments. It has been particularly found the chelate’s of the present invention, as evidenced by information herein, are capable of absorbing onto representative detergent services such as cutlery and crockery and laundry fabrics, such as exemplified by cotton, and do so in the presence of detersive surfactants. Detersive surfactants having the primary function of removing residues from the surface of the fabric therefore it is unexpected that chelate’s of the present invention show sufficient absorption to provide an effective bleaching of surfaces. Surfactant In the present invention the detersive surfactant comprises an anionic or non-ionic surfactant. It has been found that anionic non-ionic surfactants unable effective absorption of chelate’s of the present invention onto services being cleaned. Relevant compositions therefore preferably have only non-ionic and non-ionic surfactant in the composition. The surfactant may preferably be a non-ionic surfactant. It has been found that non-ionic surfactants provide a preferred base detergent composition for the D position of chelate’s of the present invention. Relevant compositions therefore have only non-ionic surfactant as the detersive surfactant in the composition. Non-ionic Surfactants Low-foaming non-ionic surfactants from the group of alkoxylated alcohols may be employed. These surfactants are ethoxylated primary alcohols, specifically those with 8 to 18 carbon atoms and an average of 1 to 12 moles of ethylene oxide (EO) per mole of alcohol. The alcohol residue in these surfactants can be linear or methyl-branched at position 2, or it may consist of a mixture of linear and methyl-branched residues, which is common in oxo alcohol residues. Alternatively, non-ionic surfactants prepared from alcohols of natural origin, such as coconut, palm, tallow fat, or oleyl alcohol, with 12 to 18 carbon atoms and an average of 2 to 8 moles of EO per mole of alcohol are preferred. The preferred ethoxylated alcohols include C12-14 alcohols with 3 to 4 EO, C9-12 alcohols with 7 EO, C13-15 alcohols with 3, 5, 7, or 8 EO, 012-18 alcohols with 3, 5, or 7 EO, and mixtures thereof, such as a combination of C12-14 alcohol with 3 EO and 012-19 alcohol with 5 EO. Tallow fatty alcohols with more than 12 EO are particularly preferred, with a range of 60 to 100 EO, and even more preferably 70 to 90 EO. Among the non-ionic surfactants, those from the group of alkoxylated alcohols, especially mixed alkoxylated alcohols and EO-PO-EO non-ionic surfactants, are highly favoured due to their foam control properties. EO being ethylene oxide and PO being propylene oxide. In machine dishwash detergent compositions, the composition should preferably contain 0.1 to 22% by weight of a non-ionic surfactant or a combination of two or more non-ionic surfactants. The preferred total amount of non-ionic surfactant is between 1 and 17% by weight, more preferably between 4 and 15% by weight, and most preferably between 6 and 12% by weight. These levels are considered optimal. The non-ionic surfactant should be present in amounts ranging from 25 to 90% by weight of the surfactant system. The non-ionic detersive surfactant for use in the present invention may be one or more of a rhamnolipid or sophorolipid. Commercial examples of such surfactants include BioLoop 56L, BioLoop 56L-PG, BioLoop 68L, BioLoop 68L-PG, BioLoop 84Land BioLoop 84L-PG. Anionic surfactants In case of a machine dishwash detergent composition, when present the amount of anionic surfactant is preferably is at most 4 wt. %, and more preferably at most 2 wt. % and even more preferably at most 1 wt. %. Examples of suitable anionic surfactants are sodium lauryl sulphate and methyl ester sulphonates or. Preferably the detergent composition comprises no or essentially no anionic surfactant. Water softeners and builders Builder I water softener materials suitable for use detergent compositions of the present invention include a) calcium sequestrant materials, b) precipitating materials, c) calcium ionexchange materials and d) mixtures thereof. Suitable calcium ion-exchange builder materials include the various types of water-insoluble crystalline or amorphous aluminosilicates, such as zeolites in particular, Zeolite Y, Zeolite X, Zeolite C, Zeolite B (also known as zeolite P), Zeolite A. The builder may be crystalline aluminosilicate, preferably an alkali metal aluminosilicate, more preferably a sodium aluminosilicate. The builder materials preferably have a calcium ion exchange capacity of at least 50 mg CaO / g. The ratio of surfactants to any aluminosilicate in the present invention is preferably greater than 5:2, more preferably greater than 7:2. Also present maybe an alkali metal carbonate this is preferably present in the composition. The preferred amount of alkali carbonate in the composition is from 3 to 74 wt.%, more preferably from 10 to 50 wt.% and even more preferably from 20 to 40 wt.%. This level of alkali carbonate provides good Ca2+ and Mg2+ ion sequestration for most types of water hardness levels , and so as to reduce the likelihood of an exchange with the transition metal iron of the chelate providing good buffering capacity. The preferred alkali carbonates are sodium- and / or potassium carbonate of which sodium carbonate is particularly preferred. The alkali carbonate present in the composition of the invention can be present as such or as part of a more complex ingredient (e.g. sodium carbonate in sodium percarbonate). It has been found that such chelate’s provide better absorption onto services being cleaned by the detersive composition. Not wishing to be bound by theory is understood that some degree of positive charge on the chelate occasion by the amine can interact with negatively charged services, is conventionally understood to be the case, and articles being washed. In the present invention the detersive surfactant preferably comprises a cationic or zwitterionic surfactant. It has been found that these can provide improved chelate deposition when used in relevant detergent compositions of the present invention. It is hypothesised that chelate co-adsorb is with cationic surfactant onto surfaces being washed. In compositions utilising a positively charged surfactant, such as a cationic or zwitterionic 5 surfactant the chelate of the present invention comprises a ligand with an auxiliary substitution comprising an alcohol chain. The alcohol chain is preferably It has been found that these provide improved chelate deposition, possibly because of combination between the negatively charged chelate and the positively charged surfactant providing improved service absorption. This is particularly beneficial for detersive 10 composition such as fabric softeners. In the present invention the in-use pH of the detergent composition is preferably in the range from pH 8 to 10. This is particularly beneficial to give absorption of ionisable chelate’s on the present invention. 15 In the present invention the detergent composition may preferably be a dishwashing detergent composition. Example compositions are tabulated below. Ingredients Tablets Tablets 2 Powder Bleach catalyst (this invention) 0.001-0.5 0.001-0.5 0.001-0.5 Bleach activator 0-5 1-2 Oxygen-based bleaching agents 10-20 15-40 5-10 Surfactants <5 <5 1-5 Builders (Alkali silicates & carbonates) 5-30 0-55 50-85 Builders (Organic sequestrants) 0-45 0-45 Builders (Polycarboxylates) 2-7 <5 Colourants <1 <1 <1 Enzymes <1 0-10 1-3 Enzyme coating (e.g., NaCI) 1-10 1 Fragrance <0.5 <1 <1 Glass protectors, silver protectors 0-1 Lime scale inhibitor 0-10 Bulking agents balance to 100% Various formats of dishwashing detergent composition may be used with the present invention, such as tablet, sachet and powder. A preferred format is of a multicomponent format, such as a multi-layer tablet. Preferably the chelate of the present invention is present in a component separate from a source of peroxide bleach, such as sodium percarbonate. In general, compositions of the present invention preferably comprise the detersive surfactant, an optional oxidising agent, and an optional bleach activator. Specifically, whilst the presence of an oxidative bleach is required for the chelate of the present invention to act as a catalyst detergent system the invention can be provided in component form, such as in the well-known Baukasten system and are therefore not necessarily mandatory. Suitable oxidising agents are: Sodium percarbonate; sodium perborate; sodium perphosphate; sodium hypochlorite; hydrogen peroxide; sodium dichloroisocyanurate (NaDCC); sodium chlorite; potassium monopersulfate (MPS); sodium carbonate peroxyhydrate and sodium persulfate. The preferred oxidising agents are sodium percarbonate and sodium perborate for use in the present invention. Most preferably sodium percarbonate. These oxidising agents are most preferably used when a solid science composition is used. When a liquid composition is used then hydrogen peroxide itself may be incorporated directly in the composition. Suitable bleach activators are: Tetraacetylethylenediamine (TAED); Tetraacetylglycoluril (TAGU); Tetraacetylhexanediamine (TAHD); N,N,N',N'-Tetramethyl-6-dodecylamidinouronium chloride (DADMAC); N,N,N',N'-Tetrabenzyl-6-dodecylamidinouronium chloride (BADMAC); N,N,N',N'-Tetrabenzyloxycarbonyl-6-dodecylamidinouronium chloride (BODMAC); N,N-Diacetyl-4,5-diazafluoren-9-one (DADHF); N,N'-Diacetyl-4,5-diazafluoren-9-yl peroxybenzoate (DADPA); 1,5-Diacetyl-2,4-dioxohexahydro-1,3,5-triazine (DADHT) and N,N-Diacetyl-3,5-dimethyl-1,4-dioxohexahydro-1,3,5-triazine (DADHT-DM). The preferred beach activator is TAED for use in the present invention. The detergent composition of the present invention may also include a sequestrant. The undesired decomposition of peroxides species can occur when the water used for a detergency operation comprises transition metals in the water supply. There is therefore a balance to be made between removing those unwanted transition metal ions and removal of the transition metal iron of the chelate of the present invention. It has been surprisingly found that a number of common sequestrants, such as used up to a one-to-one rate ratio with the catalyst of the present invention in a detergent composition of the present invention may not hinder the catalyst of the present invention significantly. Relevant sequestrants are: Ethylenediaminetetraacetic acid (EDTA); Nitrilotriacetic acid (NTA); Diethylenetriaminepentaacetic acid (DTPA); Hydroxyethyl ethylenediaminetriacetic acid (HEDTA); Diethylene glycol monobutyl ether-N,N-diacetic acid (DGBE-NDA); 1-Hydroxyethylidene-1,1-diphosphonic acid (HEDP); Aminopolycarboxylic acids (APCA) derivatives, such as iminodisuccinic acid (IDS); Methylglycinediacetic acid (MGDA); Gluconic acid. In the present invention the detergent composition may be a laundry detergent composition, such as includes fabric softeners, whitening agents, pre-treatment agents as well as conventional solid, liquid, gel, pouch detergent compositions every duty, light duty ‘whites’ and ‘colours’ detergent compositions. In the present invention the detergent composition may be a fabric washing detergent composition may also be selected from one or more of a a laundry fabric softener, a bleach or a booster laundry aid (such as a bleaching aid or whitening agent). In the present invention the detergent composition preferably further comprises a proteolytic enzyme and the chelate comprises an amide linkage. It has been found that some degree of hydrolysis of the chelate can occur thus generating additional species for absorption. This is particularly useful where the physical form of the one hydrolysed chelate is convenient for dosage, such as a physical form where hours the hydrolysed chelate visor species which will otherwise be volatile or at least present in a liquid form on suitable for a given form of delivery. This is particularly relevant with pouch type detergents were the liquid form of the chelate can act as a plasticiser and we can such pouches, particularly pouches intended for dissolution. The detergent composition of the present invention preferably further comprises a lipolytic enzyme in the chelate comprises an ester linkage. It has been found that some degree of hydrolysis of the chelate can occur thus generating additional species for absorption. This is particularly useful where the physical form of the one hydrolysed chelate is convenient for dosage, such as a physical form where hours the hydrolysed chelate visor species which will otherwise be volatile or at least present in a liquid form on suitable for a given form of delivery. This is particularly relevant with pouch type detergents were the liquid form of the chelate can act as a plasticiser and we can such pouches, particularly pouches intended for dissolution. In the present invention the chelate preferably comprises a linker L, m is 2 or more and X’ or X” is O of NH to provide said amide or ester linkage. This enables hydrolysis as mentioned above, particularly in combination with enzymes, but also when present in a high pH, such as of a pH from 8 to 10 were, during washing the chelate cam hydrolyse giving rise the aforementioned benefits. The detergent composition of the present invention may be in the physical form of the detergent composition is a powder (granulate), liquid, a gel, a pouch, a tablets or solid sheet. Preferably the physical form is as a solid. This is particularly so with chelate’s where m is 3 or more and L is a polymer. This provides an chelate in a solid form compatible with other solids and not subject to hydrolysis in the undiluted state, when dilated such as for use during washing the detergent composition components, such as enzymes or pH creating agents can give rise to hydrolysis releasing chelate into the washing composition. Detergents compositions representative of the present invention All figures are % by weight. Laundry Powder composition: Ingredients Conventional Compact 5 10 15 Anionic and nonionic Builders Cobuilders Bleaching agents Bleach activators Antiredeposition agents Corrosion inhibitors Bleach Stabilizers Foam regulators Enzymes Chelate Minors, water Bulk density, g / L 8-15 10-30 surfactants 20-50 20-40 1-5 1-7 10-25 10-20 1-3 2-8 1 1 2-6 2-6 0-1 0-1 0.1-1 0.1-2.0 0.3-1.0 0.5-2.0 0.01-0.2 0.01-0.2 balance to 100% 500-650 600-900 20 25 30 Detergent Tablet composition: Ingredients Surfactants Bleaching agents TAED Zeolite 1 Sodium triphosphate Layered silicate Sodium polycarboxylate Disinteg rants Enzymes Chelate Minors, water Laundry Powder composition: Zeolite-based, % Phosphate-based, % 13-18 15-18 13-15 12-16 3-7 4-7 15-30 25-45 0-9 0-9 2-3 2 5-17 0-12 2-4 2-3 0.01-0.2 0.01-0.2 balance to 100% Ingredient Homogeneous Structured Anionic surfactants 7-18 10-25 Nonionic surfactants 15-30 6-10 Soaps 10-25 4-8 5 Builders 0-5 15-30 Solubilizers 0-12 0-5 Alcohols 5-12 0-5 Enzymes 0-2.5 0-1.5 Chelate 0.005-1.0 0.005-1.0 10 Minors, water balance to 100% Fabric bleach detergent composition Ingredient Powder Liquid Anionic surfactants 5-15 2-10 15 Nonionic surfactants 0-1 3-5 Builders 60-75 Bleach 3-15 3-4 Filler 5-20 Chelate 0.02-1.0 0.01-1.0 20 Enzymes 0-1 Minors, water balance to 100% Examples Procedure and composition 25 The liquid laundry detergent formulations of the cleaning tests in the subsequent Examples were prepared having the generic formulation as described in Table 1 with the chelate as noted in Table 2 and were prepared by standard liquid laundry formulation preparation procedures. 30 Control, conventional chelate not being biodegradable 2,2'-Stilbenedisulfonic acid, CAS number 16090-02-1,4,4'-Bis[(4-anilino-6-morpholino-1,3,5-triazin-2-yl)amino]stilbene-2,2'-disulfonic acid disodium salt (example commercial names Blancophor BBH, DAS 1 or DMA-X) Table 1 Ingredient Commercial Name wt% Linear alkyl benzene sulfonate 8.0 Sodium lauryl ethoxysulfate 2.0 Non-ionic surfactant 4.0 Sodium percarbonate 15.0 Chelate — 0.2 Deionized water — to 100 Cleaning methodology 5 The primary cleaning performance of the liquid laundry detergent formulations of the Examples are assessed in a Terg-o-tometer of SR Lab Instruments (4 x 1 L vessels) agitated at 90 cycles per minute with the conditions noted in Table 3. Fabric swatches are of 5cm square. Table 3 Parameter Setting Temperature 25 °C Water hardness 300 ppm, Ca / Mg = 2 / 1 Fabric Types (3 in each vessel) Stained Cotton 400 Stains Tea, Curry, Clean cotton Wash time 16 minutes Rinse time 3 minutes Liquid laundry detergent dosage 0.5 g / L The catalyst delivery composition may preferably be in granular form Creating granules of chelate, may be achieved by one or more of the following granulation techniques: Spray Drying: In this method, a solution or suspension containing the chelate is atomized into fine droplets and sprayed into a drying chamber. This is preferably carried out as a co-solution with an alkali metal salt The droplets are rapidly dried using hot air or a heated gas, resulting in the formation of granules. The process can be optimized by selecting appropriate drying conditions, such as temperature, airflow, and droplet size, to obtain granules of the desired size and properties. Fluid Bed Granulation: Fluid bed granulation involves the formation of granules by spraying a solution or suspension of the manganese-based catalyst onto fluidized particles. The fluidized particles act as nuclei, and the catalyst solution or suspension is sprayed onto them, leading to the formation of granules through the agglomeration of the particles. The process is typically carried out in a fluid bed granulator, where heated air is used to fluidize the particles and facilitate drying and granule formation. Extrusion: Extrusion is a technique commonly used for the formation of cylindrical or pellet-shaped granules. In this method, a mixture of the manganese-based catalyst and suitable excipients, such as binders or fillers, is forced through an extruder. The extruder applies pressure and shearing forces to the mixture, leading to the formation of cohesive granules. The extrudates are then dried and further processed if needed to obtain the desired granule size. Wet Granulation: Wet granulation involves the formation of granules by wetting the chelate and other excipients, such as an alkali metal salt with a liquid binder in the form of a solution of watersoluble organic polymer. The mixture is then agitated or kneaded to form cohesive wet granules. The wet granules are subsequently dried, sieved, and processed as required to obtain granules suitable for use in detergent compositions. It's important to note that the selection of the granulation method will depend on factors such as the properties of the catalyst and other ingredients, the desired granule characteristics (size, shape, density), and the processing capabilities available. Process optimization, including binder selection, drying conditions, and particle size control, may be necessary to achieve the desired granule properties. Other applications of the catalyst delivery compositions as defined in the present invention: Fabrics Chelate’s of the present invention may be used in fabric manufacturing. Chelate’s of the present invention may be used in finishing processes for cotton. Preferably in the treatment of griege (loom-state) cloth into finished fabric. Chelate’s of the present invention may be used in melt spinning thing synthetic fibres. Paper Chelate’s of the present invention may be used in paper manufacturing. Preferably during “wet” manufacturing processes as detergent compositions. Chelate’s of the present invention may be used in paper finishing as detergent compositions. Chelate’s of the present invention may be used to treat cellulose fibre before paper manufacture as detergent compositions. Cosmetics Chelate’s of the present invention may be used in conjunction with emollient to provide cosmetics compositions as detergent compositions. Chelate’s the present invention may be used to produce skin whitening detergent compositions. Chelate’s the present invention may be used to produce toothpaste as detergent compositions The advantages of the chelate’s cosmetics are that they provide an increase bleaching of cosmetics whilst retaining low levels of hydrogen peroxide and do so in an environmentally acceptable format. The compound (L) of structural formula as provided in the statement of the present invention, as above, is now defined. The ligand of the present invention required for forming the chelate of the present invention which is used in the detergent composition of the present invention is selected from one or more compounds (L) of structural formula 1: Formula 1 wherein m is 1 or 2; n is 1 or 2; R independently represents H, CH3, C2H5, C3H7, C4H9 and OH; preferably H, CH(CH3)2, C(CH3)3, CH2CH3 and OH; most preferably H; or OR1 wherein R1 represents CH3(CH2)v , wherein v is 0 to 17; or NR22, wherein: R represents H, CH3(CH2)w , wherein w is 0 to 17; preferably 0; R2 represents (CH2)2- OH; and R is preferably in positions 4, 5 or 6, and in those positions; R can represent (CH2)xCH3 , wherein x is 4 to 17: preferably 0; R’ represents H, CH3, CH2CH3, CH(CH3)2, (CH2)yOH or (CH2)yCOOH, wherein y is 0 to 17; and preferably H: R” represents H, CH3, CH2CH3, CH2OH, CH2CH2OH, CH2OCH3 or CH2CH2OCH3; and preferably H: R’” represents H; or an ester wherein R’” represents C=O) ( R4); R4 represents(CH2)z - R5, wherein z is from 1 to 18 and R5 is H, OH or COOH; preferably OH: or an ether, wherein R’” represents - R - R ; R7 represents C1 to 04 alkyl; preferably methylene; R8 represents H, CH3, OH or COOH: or CH(OH)CH2OH. A number of other chemical structures are presented in this document, for convenience they are not referred to as “formula” but simply by the number. The compounds of the present invention may have utility as ligands suitable for chelating metal ions for the provision of environmentally acceptable bleach catalysts and catalysts so obtained. The compounds are based upon a common structural element of (4,5-Dihydro-1,3-oxazol-2-yl)benzene and more preferably upon a o-(4,5-Dihydro-1,3-oxazol-2-yl)phenol core (dihydro-oxazol-phenol or DOP) structure: Formula 2 which may be ring substituted with ancillary groups, esterified or etherified. The compound may be optionally substituted with ancillary groups Ancillary groups are considered to be groups which do not fundamentally alter the chelating ability of the compound. However, ancillary groups are helpful in enabling the hydrophobicity, hydrophilicity and steric hindrance of the catalytic centre to be tailored. They are also helpful in adjusting those parameters to enhance the biodegradability of the ligand. In general, shorter alcohol chains and argyle chains with a hydrophilic element are preferred so as to enable those characteristics to be achieved without presenting often poorly degradable long alcohol chains. As such, R preferably represents OH or NH2to provide a more hydrophilic structure with improved biodegradability, most preferably OH. In addition, an ether amine may preferably be present, providing the more labile ether amine functionality between an alkyl (chain) and the benzene ring in which case R1 represents CH3(CH2)v, wherein v is 0 to 17; or v is preferably 6 to 12 thus providing hydrophobicity without the potential for evolution of volatile short alkyl components, such as during high alkaline washing operation in which catalyst may be used; R2 represents CH3(CH3)w , wherein w is 0 to 17; or R1 or R2 represents (CH2)2 - OH. The terminal hydroxy group improves biodegradability and ensures high water solubility. When an ancillary group is present on the benzene (phenolic) ring it is preferably present in positions 4, 5 or 6, more preferably 5 or 6 (to illustrate): This is understood to provide better bleaching by the chelate, particularly on hydrophobic services as the catalytic centre is less hindered what the overall complex is more hydrophobic. In this light, when R is in positions 4, 5 or 6, R can represent (CH2)xCH3 , wherein x is 0 to 17, x is preferably 6 to 12 thus providing hydrophobicity without the potential for evolution of volatile short alkyl components, such as during high alkaline washing operation in which catalyst may be used. The compound may be esterified or etherified. A preferred subset is provided by the selection: R represents H, CH3, OH, OCH3, or N(CH3)2; R’ represents H, CH3, CH2OH or (CH2)2COOH; R’” represents H or - (R7)-O- R8; R5 is COOH R7 Represents a bond; z’ is preferably 1 and R9, is COOH Providing structures which are particularly biodegradable. An example structure being: As such R’” may be an ester, this improves the biodegradability of the compound. R’” is preferably an ether, this provides a compound more stable in an alkaline environment, such as during the washing process. The ester or ether may be distanced from the benzene ring by means of a spacer chain R6, R7, respectively. This spacer chain may enable a wider range of metal ions to be chelated, such as Co in addition to Mn, ions. R’” may comprise an alkyl chain, this may provide a degree of hydrophobicity to the ligand and thereby to a chelate created using the ligand. This can be advantageous in enabling catalytic bleaching of hydrophobic substrates. The ligand compounds are chelated with metal ions to form catalysts, such as may be suitable for catalysing oxidative bleaching. The compounds are biodegradable and thus prevent catalyst build up in the environment. The 4,5-Dihydro-1,3-oxazol-2-yl ring may also be substituted. R’ preferably represents H, CH3, CH2CH3, CH(CH3)2, (CH2)yOH or (CH2)yCOOH, wherein x is 0 to 17: y is preferably 6 to 12. R” preferably represents H, CH3, CH2CH3, CH2OH, CH2CH2OH, CH2OCH3or CH2CH2OCH3: most preferably one or both of R’, R” are H. This is particularly desirable when one or more of the other ancillary substituents represents an alkyl chain. Combinations of substituents: Preferred combinations of substituents are as follows: m is 1 in R is 0 to 5, w is 0 to 5 and x is 0 to 5. R” represents H or CH3 these ligands are readily synthesised, biodegradable and effective as catalysts in chelate form with manganese to provide catalysis of oxidative bleaching. A preferred subset is provided by the selection: R represents H, CH3, OH, OCH3, or N(CH3)2; R’ represents H, CH3, CH2OH or (CH2)2COOH; R’” represents H or-(C=O)- R4 with z being 2 or 4. Providing structures which are particularly biodegradable. For the same reasons, a further preferred combination is wherein m is 1 R wherein v is 6 to 17, w is 6 to 17 and x is 6 to 17 R” represents H. These more hydrophobic ligands provide greater recovery in sewage sludge and are thus less readily to be found as catalysts in chelate form with manganese to provide catalysis of oxidative bleaching, particularly of hydrophobic substrates, such as hydrophobic stains. In the present invention n is preferably 1. In the present invention n may be 2, as such potentially providing a more hydrophobic ligand, particularly when in conjunction with the previously mentioned hydrophobic variations of R. In the present invention m is preferably 1. As can be seen the structure comprises the common structural element: Formula 2 this structure may be referred to as o-(4,5-Dihydro-1,3-oxazol-2-yl)phenol or more formally as 2-(4,5-dihydro-1,3-oxazol-2-yl)phenol. For simplicity of communication the structural unit is referred to by the label DOP, dihydro-oxazol-phenol in this document. In the present invention a number of groups of specific compounds are preferred, these groupings represent families of readily synthesised compounds having good, calculated, good biodegradability characteristics and an ability to chelate transition metal ions, particularly manganese ions. These are: a) The present invention wherein n = 1; m = 1; R’ is H or CH3; R” is H or CH3; R’” is H and the compound has a structure selected from those set out in the table of claim 8. b) The present invention wherein n = 1; m = 1; R’ is H or CH3; R” is H or CH3; R’” is H and the compound has a structure selected from those set out in the table of claim 9. c) The present invention wherein n = 1; m = 1; R is N(CH2)2-OH) ; R’ is CH3; R” is CH3; R’” is H and the compound has a structure selected from those set out in the table of claim 10. d) The present invention wherein n = 1; m = 1; R’ is H or CH(CH3)2; R” is H; R’” is H and the compound has a structure selected from those set out in the table of claim 11. e) The present invention wherein n = 1; m = 1; R’ isCH2OH; R” is H; R’” is H and the compound has a structure selected from those set out in the table of claim f) The present invention wherein n = 1; m = 1; R’ is (CH2)2COOH; R” is H; R’” is H and the compound has a structure selected from those set out in the table of claim g) The present invention wherein n = 2; m = 1; R’ is H; R” is H; R’” is H and the compound has a structure selected from those set out in the table of claim 14. In the event that any of the compounds set out in claims 8 to 14 does not conform to the abbreviated list of requirements for the substituent and the compound still remains part of the invention. The requirements in each claim are presented for clarity of presentation. h) The present invention wherein and the compound has a structure selected from those set out in the table of claim 15. e) The present invention wherein and the compound has a structure selected from those set out in the table of claim 16. Preparation The compound of the present invention may be prepared by known synthetic techniques. Given the wide range of compounds (ligands) within the scope of the present invention a general scheme, more specific scheme and a particular synthesis are provided, from which the skilled person is able to reasonably adapts the procedure for any given specific compound preparation. The preferred synthetic route or compounds of the present invention uses the scheme: ——OR reagent and / or f T catalyst H Amide reagent and / or catalyst Oxazohne as can be seen the reaction of a carboxylic acid or its derivatives like its methyl ester or its nitrile with an alpha substituted beta hydroxy amine can take place in two separate stages or “one pot”, i.e. telescoping both stages and produces the basic oxazoline unit of the present invention. Such raw materials are available from sustainable sources, such as biological or bio-derived feedstocks. The above reaction scheme is related to the Pinner reaction for the condensation of a carboxylic acid with an a-substituted p-hydroxy amine to form an oxazoline. Reagents and catalysts include but are not restricted to Thionyl chloride (SOCI2), Oxalyl chloride (C2O2CI2), p-Toluene sulfonic acid, Methane sulfonic acid, Trifluoromethanesulfonic acid, Trifluoroacetic acid, Hydrogen chloride. An outline scheme is as follows, the skilled person adapting these as may be required. Example reaction conditions : the following reagents are provided: An aromatic carboxylic acid relevant to the structure intended (see table below) An a-Substituted p-hydroxy amine relevant to the structure intended (see table below) Thionyl Chloride (SOCI2)can be used as a reagent in both stages, first to form in-situ the acyl chloride from the carboxylic acid which will then react with the amine, then to form a chloride from the alcohol, more reactive toward cyclisation. A suitable solvent for the reaction is usually anhydrous (water-free) and polar. Suitable solvents include dichloromethane (CH2CI2) or chloroform (CHCI3). These solvents help dissolve the reagents and promote the reaction. Alternative solvents available from renewable feedstocks include: Tetrahydrofuran (THF, C4H8O): having lower toxicity compared to dichloromethane and chloroform and derivable from renewable resources through the hydrogenation of furfural, which is obtained from lignocellulosic biomass. Methyl tert-butyl ether (MTBE, C5Hi2O) which also has lower toxicity and is derivable from renewable feedstocks such as isobutene, which can be produced from biomass-based sources. 2-Methyltetrahydrofuran (2-MeTHF, CsHwO), which has similar properties to THF and can be produced from renewable feedstocks, such as biomass-derived sugars or furfural. The reaction is typically carried out at a moderately low temperature, around 0-10°C. This range helps control the reaction rate and minimize undesired side reactions. An outline Reaction Procedure is as follows: In a dry and inert atmosphere (e.g., under nitrogen), combine the carboxylic acid and a-substituted p-hydroxy amine in the chosen solvent. Add a catalytic amount of a base, such as triethylamine (EtsN), to neutralize the hydrogen chloride formed during the reaction. Gradually add thionyl chloride (SOCI2) to the reaction mixture, typically dropwise, while maintaining the reaction temperature. Stir the reaction mixture for a specific period, usually several hours, to ensure completion of the reaction. Quench the reaction by adding a suitable quenching agent, such as ice or water, to destroy any excess thionyl chloride and neutralize the remaining acidic components. Extract the product from the reaction mixture using a suitable solvent or perform further purification steps, such as column chromatography or recrystallization. Skilled person will adapt the specific reaction conditions using their common general knowledge. A more specific example procedure, such as, for compound 1000 is as follows A mixture of methyl ester functionalized phenol (1 eq) and hydroxyalkylamine (1.05 eq) is heated to 130°C and the methanol of reaction is distilled until no further distillation is observed and the reaction is complete. The resulting residue is then cooled to room temperature and suspended in dichloromethane, methyl tert-butyl ether or methyltetrahydrofuran(4 vol). After cooling to 5°C, thionyl chloride (1.1eq) is then added dropwise to the mixture. After complete addition the reaction is stirred for 16h at 25°C. Resulting solids are then filtered and neutralized with 10% NaHCO3 solution before being extracted with methyl tert-butyl ether (3X1 vol). Organic extract is then concentrated to dryness under vacuum to give the target ligand structure. A specific synthesis of compound (1000) A mixture of methyl salicylate (273.9g, 1.8mol) and ethanolamine (115.8g, 1.9mol) is heated to 130°C and the methanol of reaction is distilled until no further distillation is observed and the reaction is complete. The resulting residue is then cooled to room temperature and suspended in dichloromethane (1L, 4 vol). After cooling to 5°C, thionyl chloride (237.5g, 2.0mol) is then added dropwise to the mixture. After complete addition the reaction is stirred for 16h at 25°C. Resulting solids are then filtered and neutralized with 10% NaHCO3 solution before being extracted with methyl tert-butyl ether (3 X 150mL). Organic extract is then concentrated to dryness under vacuum to give to give product as a red oil which crystallizes to peach / pink solid on standing. Solids ground to give a peach / pink powder in 68% yield (292.5g, 1.22mol). Analytical Data: GC purity: 99.5%; FT-IR: nC=N 1636cm1; *H NMR (Methanol-ch, 300 = MHz, S): 7.56 (dd, 1H), 7.29 (ddd, 1H), 6.89 (dd, 1H), 6.79 (ddd, 1H), 4.28 (t, 2H), 3.93ppm (t, 2H); ^H} NMR (methanol-ch, 75MHz, S): 165.87, 159.45, 132.90, 127.75, 118.32, 116.01, 110.57, 66.61, 52.91 ppm; Elemental analysis: C 65.66%, H 5.45%, N 8.62% Example combinations of reagents to produce compounds of the present invention is provided in the following table: Amine Substrate h2n—oh h2n^0H h2n-0°h .OH .OH o Ro o \ 1000 1100 1200 1300 1400 o=( o 1002 1102 1202 1302 1402 0 HO^^^OH 1006 1106 1206 1306 1406 OH 0 1008 1108 1208 1308 1408 o 1011 1111 1211 1311 1411 0 h2n^^^oh 1022 1122 1222 1322 1422 Chelate The present invention includes, a chelate comprising a compound (L) of any of claims 1 to 9 as the ligand of a transition metal element (M). The chelate is preferably a hexadentate complex. The chelate is preferably comprising two ligands chelated to 1 transition metal element. The chelate preferably comprises one or more further ligands not being the ligands of the invention. The chelate preferably consists of two further ligands not being the ligands of the invention. The further ligands are preferably selected from H20, carbonate, hydroxide, a halide or an organic acid. The further ligands are preferably selected from, H20, Cl and acetate. The chelate of the present invention is preferably a chelate of a transition metal. Preferred transition metals are Iron (Fe): Manganese (Mn): Copper (Cu): and Cobalt (Co). Preferred transition metal ions are iron(ll) or iron(lll); manganese(ll) or manganese(lll); copper(ll); cobalt(ll) or cobalt(lll). The preferred transition metal is preferably Manganese or Cobalt, most preferably manganese, still more preferably manganese (II) or (III). The chelate of the present invention is preferably a chelate of the transition metal element manganese, preferably wherein Mn is in the 3+, (III) oxidation state. The mode of action of the prepared chelate of Mn in the 3+ oxidation state is to reversibly cycle between the Mn 3+ and Mn 4+ oxidation states during bleaching, confirmed to be chemically reversible by cyclic voltammetry (+0.5V) / v Chelate preparation Given the wide range of chelates within the scope of the present invention a general scheme, more specific scheme and a particular synthesis are provided, from which the skilled person is able to reasonably adapts the procedure for any given specific chelate preparation. An outline scheme for preparation of the chelate of the present invention is as follows: provide the ligand: o-(4,5-Dihydro-1,3-oxazol-2-yl)phenol and the metal salt: Manganese(ll) chloride tetrahydrate (MnCI2 4H2O) Prepare a solution of the ligand. Dissolve a suitable amount of o-(4,5-Dihydro-1,3-oxazol-2-yl) phenol in ethanol or dimethylformamide, to form a clear solution. A concentration in the range 0.1 to 0.5mol / l may be used. In a separate container, dissolve the manganese(ll) chloride tetrahydrate (MnCI2 4H2O) in ethanol, to form a manganese salt solution. The concentration of the manganese salt can be adjusted to provide a twofold excess of the ligand Slowly add the ligand solution to the manganese salt solution while stirring. The addition of the ligand solution should be done dropwise or with continuous stirring to ensure effective mixing. The process is carried out in the temperature range 40 to 80 degrees Celsius (°C). After the addition is complete, continue stirring the reaction mixture for three several hours, to allow the ligand to coordinate with the manganese ions and form the desired manganese-based catalyst complex. Progress of the reaction may be monitored by UV visible spectroscopy. Meanwhile, prepare a solution of acetic acid in a suitable solvent, ethanol. Adjust the concentration of the acetic acid solution based on the desired catalyst composition. Slowly add the acetic acid solution to the reaction mixture while maintaining stirring, such as over a period of one hour. The addition of the acetic acid should be done dropwise or with continuous stirring. Once the desired reaction time has elapsed, the manganese-based catalyst can be isolated by techniques such as filtration, precipitation, or solvent evaporation. Finally, the isolated catalyst can be washed, dried, and stored in a sealed container for future use in oxidative bleaching reactions. A specific representative procedure for the synthesis of a chelate according to the present invention, such as for the chelate of compound 1000 used in the bleach catalysis methods below is: Oxazoline ligand 1000 (180mmol, 2 eq) was dissolved in MeOH (900ml, 30 vol). Solid manganese acetate tetrahydrate (21.9g, 90 mmol, 1eq) was then charged to the ligand solution to give an instant colour change to dark green / black. After 0.25h stirring the mixture is concentrated in vacuo to give an initial residue. Material is then resuspended in 900ml and concentrated to dryness twice more to give the final catalyst complex. A specific synthesis of 1000-Mn Complex Oxazoline ligand 1000 (30g, 180mmol, 2eq) was dissolved in MeOH (900ml, 30 vol). Solid manganese acetate tetrahydrate (21.9g, 90 mmol, 1eq) was then charged to the ligand solution to give an instant colour change to dark green / black. After 0.25h stirring the mixture is concentrated in vacuo to give an initial residue. Material is then resuspended in 900ml and concentrated to dryness twice more to give the final catalyst complex. Sample ground in pestle and mortar to give catalyst as a green-brown free-flowing powder (41.3g). Analytical Data’. FT-IR: nC=N 1621cm1; UV-Vis: Imax = 264nm, 216nm; ICP: 13% Mn content; Elemental analysis: C 53.40%, H 4.59%, N 5.77% SXRD Structure: Table 1 Crystal data and structure refinement for 1000 complex. Identification code 1000 complex Empirical formula C22H23MnN2O8 Formula weight 498.36 Temperature / K 120.00 Crystal system triclinic Space group P-1 a / A 6.3884(2) b / A 9.4519(3) c / A 9.5141(3) a / ° 80.7500(10) P / ° 71.9660(10) v / ° 71.0250(10) Volume / A3 515.42(3) Z 1 1.606 Pcalcg / cm3 p / mm1 0.696 F(000) 258.0 Crystal size / mm3 0.21x0.11x0.025 Radiation Mo Ka (X = 0.71073) 20 range for data collection / 0 6.634 to 63.994 Index ranges -9 < h < 9, -14 < k < 14, -14 < 1 < 14 Reflections collected 20885 Independent reflections 3567 [Rint = 0.0297, Rsigma = 0.0202] Data / restraints / parameters 3567 / 0 / 196 Goodness-of-fit on F2 1.147 Final R indexes [l>=2o (1)] Ri = 0.0288, wR2 = 0.0740 Final R indexes [all data] Ri = 0.0303, wR2 = 0.0747 Largest diff, peak / hole / e A3 0.42 / -0.28 [Text Wrapping Break] Table 2 Fractional Atomic Coordinates (xlO4) and Equivalent Isotropic Displacement Parameters (A2xl03) for 1000 complex. Ueq is defined as 1 / 3 of the trace of the orthogonalised Uu tensor. Atom X y z U(eq) Mnl 5000 0 5000 11.33(6) 01 3351.5(15) 86.0(9) 3657.1(9) 15.44(15) 02 6453.7(15) 3569.2(9) 2133.1(10) 17.11(16) 03 1935.7(15) 1609.3(9) 6456.8(10) 18.09(17) 04 1294.2(16) 3730.8(10) 5057.3(10) 21.68(19) N1 6171.8(16) 1663.2(10) 3833.1(10) 12.28(16) Cl 7428(2) 2444.9(13) 4339.4(13) 16.5(2) C2 7728(2) 3690.5(14) 3120.8(14) 18.3(2) C3 5673.4(18) 2372.2(12) 2646.5(12) 12.33(18) C4 4365.4(19) 2016.4(12) 1828.2(12) 12.74(18) C5 3303.0(19) 867.9(12) 2378.6(12) 13.06(18) C6 2054(2) 561.2(13) 1532.7(13) 17.0(2) C7 1914(2) 1343.6(15) 192.5(14) 20.5(2) C8 2949(2) 2494.8(15) -338.7(13) 20.7(2) C9 4139(2) 2829.8(13) 480.8(13) 16.8(2) CIO 767.6(19) 2914.4(12) 6254.1(12) 14.35(19) Cll -1368(2) 3587.6(15) 7449.5(14) 20.6(2) Table 3 Anisotropic Displacement Parameters (A2xl03) for 1000 complex. The Anisotropic displacement factor exponent takes the form: -2n2[h2a*2Un+2hka*b*Ui2+...]. Atom Un U22 U33 U23 Ui3 Ui2 Mnl 12.13(11) 11.27(10) 12.29(11) 1.92(7) -5.81(8) -4.64(8) 01 18.1(4) 16.4(4) 15.7(4) 4-1(3) -9-5(3) -8.1(3) 02 19.2(4) 15.5(4) 20.2(4) 4.3(3) -8.5(3) -9-5(3) 03 17.9(4) 13.9(4) 17.9(4) -0.7(3) -3.2(3) -0.5(3) 04 21.5(4) 14.7(4) 19.2(4) 2.0(3) 0.0(3) 0.5(3) Nl 11.6(4) 11.9(4) 14.2(4) -0.8(3) -4.6(3) -3.6(3) Cl 18.6(5) 16.3(5) 19.0(5) 0.4(4) -8.6(4) -8.5(4) C2 19.9(5) 16.0(5) 23.5(5) 1.0(4) -9.5(4) -8.9(4) C3 10.6(4) 10.8(4) 14.1(4) -1.0(3) -2-1(3) -2.3(3) C4 12.5(4) 13.0(4) 12.3(4) -0.9(3) -3.5(3) -3.1(3) C5 13.2(4) 12.3(4) 13.5(4) -0.1(3) -5.1(4) -2.5(3) C6 20.2(5) 16.4(5) 17.9(5) 0.1(4) -9.4(4) -6.7(4) C7 25.2(6) 22.4(6) 18.3(5) 0-2(4) -11.7(5) -8.3(5) C8 26.0(6) 24.4(6) 14.2(5) 3-2(4) -9.1(4) -9-3(5) C9 19.0(5) 17.8(5) 13.5(5) 1-7(4) -4.7(4) -6.3(4) CIO 13.7(4) 13.5(4) 16.3(5) -2.6(4) -4.8(4) -3.1(4) Cll 17-7(5) 18.4(5) 19.1(5) -1.8(4) -0.5(4) -0.8(4) Table 4 Bond Lengths for 1000 complex. Atom Atom Length / A Atom Atom Length / A Mnl Ol1 1.8687(8) Nl Cl 1.4699(14) Mnl 01 1.8687(8) Nl C3 1.2906(14) Mnl 03 2.2646(8) Cl C2 1.5289(17) Mnl O31 2.2646(8) C3 C4 1.4447(15) Mnl Nl1 1.9884(9) C4 C5 1.4105(15) Mnl Nl 1.9884(9) C4 C9 1.4075(15) 01 C5 1.3215(13) C5 C6 1.4113(15) 02 C2 1.4587(14) C6 C7 1.3802(16) 02 C3 1.3437(13) C7 C8 1.4004(18) 03 CIO 1.2368(13) C8 C9 1.3741(17) 04 CIO 1.2862(14) CIO Cll 1.5057(17) il-X,-Y,l-Z Table 5 Bond Angles for 1000 complex. Atom Atom Atom Angle / " Atom Atom Atom Angle / " Ol1 Mnl 01 180.0 C3 Nl Cl 108.94(9) Ol1 Mnl 03i 91.76(4) Nl Cl C2 103.19(9) Ol1 Mnl 03 88.24(4) 02 C2 Cl 104.53(9) 01 Mnl 03 91.76(4) 02 C3 C4 117.21(9) 01 Mnl 03i 88.24(4) Nl C3 02 115.94(10) Ol1 Mnl NV 90.50(4) Nl C3 C4 126.85(10) 01 Mnl Nl 90.50(4) C5 C4 C3 120.34(10) 01 Mnl NV 89.50(4) C9 C4 C3 119.68(10) Ol1 Mnl Nl 89.50(4) C9 C4 C5 119.98(10) 031 Mnl 03 180.0 01 C5 C4 124.11(10) Nl Mnl 03i 87.83(3) 01 C5 C6 117.80(10) NV Mnl 03 87.83(3) C4 C5 C6 118.06(10) NV Mnl 03i 92.17(3) C7 C6 C5 120.90(11) Nl Mnl 03 92.17(3) C6 C7 C8 120.72(11) NV Mnl Nl 180.00(3) C9 C8 C7 119.29(11) C5 01 Mnl 131.43(7) C8 C9 C4 121.01(11) C3 02 C2 107.16(9) 03 CIO 04 122.79(11) CIO 03 Mnl 133.84(8) 03 CIO Cll 119.13(11) Cl Nl Mnl 124.20(7) 04 CIO Cll 118.08(10) C3 Nl Mnl 126.09(8) il-X,-Y,l-Z Table 6 Hydrogen Bonds for 1000 complex. D H A d(D-H) / A d(H-A) / A d(D-A) / A D-H-A / ° 04 H4 O41 1.2196(9) 1.2196(9) 2.4393(17) 180.000(0) i-X,l-Y,l-Z Table 7 Selected Torsion Angles for 1000 complex. A B C D Angle / " A B C D Angle / " 02 C3 Nl Mnl 172.74(7) C5 Ol Mnl Nl1 -173.60(10) Cl Nl C3 02 2.44(13) C5 Ol Mnl N1 6.40(10) C3 C4 C5 Ol 2.14(17) C5 C4 C3 02 -173.81(10) C3 C4 C5 C6 -179.74(10) C5 C4 C3 Nl 5.85(17) C4 C3 Nl Mnl -6.92(16) C6 C5 Ol Mnl 173.10(8) C4 C3 Nl Cl -177.22(10) C6 C5 C4 C9 0.76(16) C4 C5 Ol Mnl -8.77(17) C9 C4 C3 02 5.69(15) C5 Ol Mnl 03 98.59(10) C9 C4 C3 Nl -174.64(11) C5 Ol Mnl O31 -81.41(10) C9 C4 C5 Ol -177.37(10) Table 8 Hydrogen Atom Coordinates (AxlO4) and Isotropic Displacement Parameters (A2xlO3) for 1000 complex. Atom X y z U(eq) H1A 8850(30) 1780(19) 4441(19) 22(4) H1B 6490(30) 2840(20) 5300(20) 25(4) H2A 9270(30) 3540(20) 2540(20) 22(4) H2B 7030(30) 4640(20) 3470(20) 23(4) H4 0 5000 5000 47(9) H6 1330(30) -200(19) 1913(19) 21(4) H7 1040(30) 1100(20) -340(20) 25(4) H8 2800(30) 3050(20) -1280(20) 33(5) H9 4860(30) 3610(20) 140(20) 26(4) H11A -2340(50) 4450(30) 7160(30) 65(8) HUB -990(50) 3610(30) 8300(30) 76(9) H11C -2230(50) 2930(30) 7740(30) 74(9) 5 Experimental Representative catalysts of the present invention were tested as follows: Bleach Catalyst UV-Vis test method Bleaching efficiency of prepared catalyst complexes is tested by monitoring the reduction in absorbance at 630nm of a naphthol blue black dye solution by UV-Vis. Four stock solutions are 10 prepared before testing; i) pH 10.5 buffer solution prepared by adding a 0.5M sodium bicarbonate solution to IL 0.5IVI sodium carbonate solution until the desired pH is achieved; ii) 0.75M H2O2 comprising of 72.9g 35% H2O2 made IL volume with D.L water; iii) Naphthol blue black dye solution comprising of 0.028g naphthol blue black made to IL volume with D.L water and iv) a lmmol solution of the catalyst with respects to Mn metal stoichiometry made up in D.L water. 15 To measure bleaching performance 20pl of the prepared 0.75M H2O2 solution is first charged to a lml cuvette, followed by 20pl of the lmmol catalyst solution. The cuvette is then placed in the UV-Vis apparatus and measurement is started, lml of the naphthol blue black dye solution and 2.25ml of buffer solution are then charged sequentially. Percentage bleaching is calculated as the percent reduction in absorbance at 630nm 0.5h from the point of highest absorbance. The maximum observed rate is taken from the point of greatest gradient observed on the UV-Vis trace. 5 Comparison to existing catalysts Catalyst Total bleaching 0.5h Max. obs. Bleach rate MnCI2.2H2O 13% -0.005 Mn(OAc)2.4H2O 55% -0.002 Mn (II) oxalate 57% -0.025 MnMe3-TACN prepared as per literature 75% -0.100 1000 complex 75% -0.244 Ligand ratio comparison (chloride counterion) 1000: Mn Total bleaching 0.5h Max. obs. Bleach rate 1 49% -0.180 2 68% -0.277 3 72% -0.280 Mn counterion comparison Mn counter ion Total bleaching 0.5h Max. obs. Bleach rate Cl 68% -0.277 COa 34% -0.006 AcO 75% -0.244 CLO 40% -0.053 F6P 79% -0.085 Structure Variations Ligand structure Total bleaching 0.5h Max. obs. Bleach rate 1000 75% -0.244 1002 86% -0.308 1006 >30% 1008 59% -0.032 1010 >30% 1011 66% -0.124 1022 >30% 1100 >30% 1102 >30% 1106 >30% 1108 >30% 1010 >30% 1111 >30% 1122 >30% 1200 35% -0.153 1300 53% -0.092 1400 >30% As can be seen above chelates of representative ligands of the present invention are effective in promoting oxidative bleaching. 5 Bleach Catalyst stain removal test Standard pre-stained tiles from Center for Test materials (CFT, The Netherlands) were used for this test to demonstrate stain removal in automatic dishwashing application. Bleach performance test by stain removal from pre-stained tile pieces is achieved by dissolving 4.2g sodium carbonate and 0.7g 10 sodium bicarbonate in IL in deionized water at 40°C. When testing catalysts in solution, 5mL of a prepared lmmol solution in deionized water is charged to the mixture; for solid catalyst testing a mass equivalent to 5mmol is charged directly to the stirred mixture. The stain test plate of interest is then half submerged in the stirred mixture before adding 5ml of a 0.75M H2O2 solution. Test pieces are submerged for a total of 10 minutes from the addition of H2O2 before rinsing with D.L water and 15 allowing to dry. Catalyst charged as a solution Stain No cat. blank Mn(0Ac)2 Dragon 1000 1002 DM14-highly discriminative tea V.Poor Poor V. Good V. Good V. Good DM11-tea V.Poor Poor Good Good Good DM81-coffee V. Poor Poor Good Moderate Good DM82-espresso V.Poor Poor Moderate Moderate Moderate DM51-red wine V. Poor Poor Good Good Good DM62 - curry V.Poor Poor Poor Moderate Moderate Catalyst charged as a solid Stain No cat. blank Mn(0Ac)2 Dragon 1000 1002 DM14 — highly discriminative tea V.Poor Poor V. Good Excellent Excellent DM11-tea V.Poor Poor Good Good Good DM81-coffee V. Poor Poor Good Good V. Good DM82-espresso V. Poor Poor Moderate Good Good DM51-red wine V.Poor Poor Good V. Good V. Good DM62 - curry V.Poor Poor Poor V. Good V. Good 10 As can be seen, the presence of a catalyst enables bleaching to take place and they Ligand is required, beyond a simple anion in conjunction with the manganese to provide any bleaching. The use of a chelate the commercially available MnMe3-TACN, Bis(N,N',N"-trimethyl-1,4,7-triazacyclononane)-trioxo-dimanganese (IV) di(hexafluorophosphate) monohydrate provides effective bleaching and the ligands of the present invention provide improvements of this. The improvements are particular striking when the solid catalyst is used. General In the event that a compound of the present invention appears to disclose a noncanonical 5 valence (such as a variance of 5 carbon) instructor should be interpreted by the additional deletion of protons to provide a canonical valence. For the purposes of the present description the compounds of the present invention may also be described as ligands even if not actually chelating a metal ion.
Claims
Claims,A catalyst delivery composition comprising a chelate asa. a solid or solid solution inb. the form of a particle or sheetc. the composition comprising from 1 to 50% by weight of the chelate,d. from 1 to 50% by weight of a water-soluble organic polymer ande. optionally an inorganic solid in the form of an alkali metal salt of from 1 to 98%f. the chelate comprising a compound (L) as defined below as the ligand of a transition metal element (M), the ligand being a compound (L) of structural formula 1:formula 1whereinm is 1 or 2;n is 1 or 2;R independently represents H, CH3, C2H5, C3H7, C4H9 and OH; preferably H, CH(CH3)2, C(CH3)3, CH2CH3 and OH; most preferably H;or OR1 wherein R1 represents CH3(CH2)v , wherein v is 0 to 17;or NR22, wherein:R represents H, CH3(CH2)w , wherein w is 0 to 17; preferably 0;R2 represents (CH2)2- OH;and R is preferably in positions 4, 5 or 6, and in those positions;R can represent (CH2)xCH3 , wherein x is 4 to 17: preferably 0;R’ represents H, CH3, CH2CH3, CH(CH3)2, (CH2)yOH or (CH2)yCOOH, wherein y is 0 to 17; and preferably H:R” represents H, CH3, CH2CH3, CH2OH, CH2CH2OH, CH2OCH3 or CH2CH2OCH3; and preferably H:R’” represents H;or an ester wherein R’” represents C=O) ( R4);R4 represents(CH2)z - R5, wherein z is from 1 to 18 and R5 is H, OH or COOH; preferably OH:or an ether, wherein R’” represents - R - R ;R7 represents C1 to 04 alkyl; preferably methylene;R8 represents H, CH3, OH or COOH:or CH(0H)CH20H.
2. The compound of claim 1 wherein:in R any v is 0 to 5, any w is 0 to 5 and any x is 0 to 5;R’ and R” independently represent H or CH3;R’” represents H.
3. The compound of claim 1 wherein:R wherein at least one of v, w and z is 6 to 17; preferably at least two of v, w and z is 6 to 17; most preferably any v is 6 to 17, any w is 6 to 17 and any x is 6 to 17;R’ and R” independently represent H or CH3; preferably H;R’” represents H.
4. The compound of claim 1 wherein:R represents H, CH3, OH, OCH3, or N(CH3)2;R’ represents H, CH3, CH2OH or (CH2)2COOH;R” represents HR’” provides an ether.
5. The compound of any of claims 1 or 4 wherein n is 1.
6. The compound of any of claims 1 to 4 wherein n is 2.
7. The compound of any preceding claim wherein m is 1.
8. The compound claim 1 wherein the compound has the structure selected from:Patent code Structure SMILES IUPAC name 1000 OC(=CC=C1)C(=C1)C(=NC1)O Cl o-(4,5-Dihydro-l,3-oxazol-2-yl)phenol 1001 y^OH OC(=C(C)C=C1)C(=C1)C(=NC1 )OC1 3-(4,5-Dihydro-l,3-oxazol-2-yl)-2-cresol 1002 O-A OC(=CC1C)C(=CC=1)C(=NC1) OC1 4-(4,5-Dihydro-l,3-oxazol-2-yl)-3-cresol 1003 IS? OC(=CC=C1C)C(=C1)C(=NC1) OC1 3-(4,5-Dihydro-l,3-oxazol-2-yl)-4-cresol 1004 OC(=CC1)C(=C(C)C=1)C(OC1) =NC1 2-(4,5-Dihydro-l,3-oxazol-2-yl)-3-cresol 1005 0-\ Y^OH OH OC(=C(O)C=C1)C(=C1)C(OC1) =NC1 3-(4,5-Dihydro-l,3-oxazol-2-yl)pyrocatechol 1006 O"\ XV HO^^^OH OC(=CC1O)C(=CC=1)C(OC1)= NCI 4-(4,5-Dihydro-l,3-oxazol-2-yl)resorcinol 1007 0"\ OC(=CC=C1O)C(=C1)C(OC1)= NCI 2-(4,5-Dihydro-l,3-oxazol-2-yl)hydroquinone 1008 OH O^. de OC(=CC=C1)C(=C1O)C(=NC1) OC1 2-(4,5-Dihydro-l,3-oxazol-2-yl)resorcinol 1009 Ko \= / \ OC(=C(C=C1)OC)C(=C1)C(=N C1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-6-methoxyphenol 1010 Q-A .Xv O— OH OC(=CC1OC)C(=CC=1)C(OC1) =NC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-5-methoxyphenol 1011 0^. ^^OH OC(=CC1)C(=CC=1OC)C(=NC1 )OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-4-methoxyphenol 1012 Q-°\ ¥ OC(=CC1)C(=C(C=1)OC)C(=N C1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-3-methoxyphenol 1013 Y^OH HO^^0 OC(C(=CC1)C(OC2)=NC2)=C( C=1)OCCO 6-(4,5-Dihydro-l, 3-oxazol-2-yl)-2-(2-hydroxyethoxy)phenol 1014 o' X OC(=CC1OCCO)C(=CC=1)C(O C1)=NC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-5-(2-hydroxyethoxy)phenol1015 OC(=CC=C1OCCO)C(=C1)C(= NC1)OC1 2-(4,5-Dihydro-l,3-oxazol-2-yl)-4-(2-hydroxyethoxy)phenol 1016 o-x dr OC(=CC=C1)C(=C1OCCO)C(O C1)=NC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-3-(2-hydroxyethoxy)phenol 1017 r Y^OH OC(C(=CC1)C(OC2)=NC2)=C( C=1)OCCOC 6-(4,5-Dihydro-l, 3-oxazol-2-yl)-2-(2-methoxyethoxy)phenol 1018 0--\ rr OC(=CC(=C1)OCCOC)C(=C1)C (OC1)=NC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-5-(2-methoxyethoxy)phenol 1019 OC(=CC1)C(=CC=1OCCOC)C(= NC1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-4-(2-methoxyethoxy)phenol 1020 ^'O'^o 0^. dr OC(=CC=C1)C(=C1OCCOC)C(= NC1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-3-(2-methoxyethoxy)phenol 1021 0-\ fY^ Y^OH nh2 OC(C(=CC1)C(OC2)=NC2)=C( N)C=1 6-Amino-2-(4,5-dihydro-l,3-oxazol-2-yl)phenol 1022 0-\ HsN^-^OH OC(=CC(N)=C1)C(=C1)C(OC1) =NC1 5-Amino-2-(4,5-dihydro-l,3-oxazol-2-yl)phenol 1023 °-A h2n^An> OC(=CC=C1N)C(=C1)C(=NC1) OC1 4-Amino-2-(4,5-dihydro-l,3-oxazol-2-yl)phenol 1024 nh2 o-\ dl N Y^OH OC(=CC=C1)C(=C1N)C(OC1)= NCI 3-Amino-2-(4,5-dihydro-l,3-oxazol-2-yl)phenol 1025 M- / \= / \ OC(C(=CC1)C(OC2)=NC2)=C( C=1)N(C)C 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-6-(dimethylamino)phenol 1026 Q-A rdN 1 OC(=CC1N(C)C)C(=CC=1)C(O C1)=NC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-5-(dimethylamino)phenol 1027 1 r OC(=CC1)C(=CC=1N(C)C)C(= NC1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-4-(dimethylamino)phenol 1028 O"\ ddN OC(=CC1)C(C(=NC2)OC2)=C( C=1)N(C)C 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-3-(dimethylamino)phenol 1029 Q-A cdN Y^OH OC(=C(C=C1)N(CCO)CCO)C(= C1)C(OC1)=NC1 2-{[3-(4,5-Dihydro-l, 3-oxazol-2-yl)-2- hydroxyphenyl](2- hydroxyethyl)amino}ethanol 1030 _o ho^ju N HO^ OC(=CC1N(CCO)CCO)C(=CC= 1)C(OC1)=NC1 2-{[4-(4,5-Dihydro-l, 3-oxazol-2-yl)-3- hydroxyphenyl](2- hydroxyethyl)amino}ethanol 1031 HO^ ^Nrr ^-^OH OC(=CC=C1N(CCO)CCO)C(=C 1)C(=NC1)OC1 2-{[3-(4,5-Dihydro-l, 3-oxazol-2-yl)-4- hydroxyphenyl](2- hydroxyethyl)amino}ethanol 1032 H0 dr OC(=CC1)C(C(=NC2)OC2)=C( C=1)N(CCO)CCO 2-{[2-(4,5-Dihydro-l, 3-oxazol-2-yl)-3- hydroxyphenyl](2- hydroxyethyl)amino}ethanol1033 o-\ COC(=CC=C1)C(=C1)C(=NC1) OC1 2-(o-Methoxyphenyl)-4,5-dihydro-l,3-oxazole 1034 CCOC(=CC=C1)C(=C1)C(OC1) =NC1 2-(o-Ethoxyphenyl)-4,5-dihydro-l,3-oxazole 1035 R o X OCCOC(=CC1)C(=CC=1)C(=NC 1)OC1 2-[o-(4,5-Dihydro-l,3-oxazol-2-yl)phenoxy]ethanol 1036 ft o / COCCOC(=CC1)C(=CC=1)C(=N C1)OC1 2-[o-(2-Methoxyethoxy)phenyl]-4,5-dihydro-l,3-oxazole 1037 o-x Oft" o OCCOCCOC(=CC1)C(=CC=1)C (OC1)=NC1 2-{2-[o-(4,5-Dihydro-l,3-oxazol-2-yl)phenoxy]ethoxy}ethanol 1038 R o Q \ COCCOCCOC(=CC=C1)C(=C1) C(OC1)=NC1 2-{o-[2-(2- Methoxyethoxy)ethoxy]phenyl}-4,5-dihydro-l,3-oxazole 1039 OH OC(CO)COC(=CC1)C(=CC=1)C (=NC1)OC1 3-[o-(4,5-Dihydro-l,3-oxazol-2-yl)phenoxy]-l,2-propanediol 1040 O OC(=O)COC(=CC=C1)C(=C1)C (OC1)=NC1 [o-(4,5-Dihydro-l,3-oxazol-2-yl)phenoxy]acetic acid 1041 X o ft OC(=O)CCOC(=CC1)C(=CC=1) C(OC1)=NC1 3-[o-(4,5-Dihydro-l,3-oxazol-2-yl)phenoxy]propionic acid9. The compound claim 1 wherein the compound has the structure selected from:Patent code Structure SMILES IUPAC name 1100 °RZ_ OC(=CC=C1)C(=C1)C(=NC1(C) C)OC1 o-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1101 o^ / Y^OH OC(C(=CC1)C(OC2)=NC2(C)C) =C(C)C=1 3-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)-2-cresol 1102 o-ar OC(=CC1C)C(=CC=1)C(OC1)= NC1(C)C 4-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)-3-cresol 1103 OC(=CC=C1C)C(=C1)C(=NC1( C)C)OC1 3-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)-4-cresol 1104 OC(=CC1)C(C(OC2)=NC2(C)C) =C(C=1)C 2-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)-3-cresol 1105 O-X / Y^oh OH OC(C(=CC1)C(OC2)=NC2(C)C) =C(C=1)O 3-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)pyrocatechol 1106 Q'A / HO'^^OH OC(=CC=C1C(OC2)=NC2(C)C) C=C1O 4-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)resorcinol 1107 OC(C=C(C1O)C(OC2)=NC2(C) C)=CC=1 2-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol- 2-yl)hydroquinone1108 oh O'~V OC(C=C1)=C(C(=NC2(C)C)OC 2)C(O)=C1 2-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)resorcinol 1109 O'A / y^OH OC(=C(OC)C=C1)C(=C1)C(OC 1)=NC1(C)C 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-6-methoxyphenol 1110 / o R 8 v OC(=CC(=C1)OC)C(=C1)C(OC 1)=NC1(C)C 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-5-methoxyphenol 1111 °^\ OC(=CC=C1OC)C(=C1)C(=NC1 (C)C)OC1 2-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol- 2-yl)-4-methoxyphenol 1112 fM" OC(=CC1)C(=C(C=1)OC)C(=N C1(C)C)OC1 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-3-methoxyphenol 1113 0"^ / cRn Y^oh Hox'Xx° OC(=C(OCCO)C=C1)C(=C1)C( OC1)=NC1(C)C 6-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol- 2-yl)-2-(2-hydroxyethoxy)phenol 1114 %’ o OC(=CC(=C1)OCCO)C(=C1)C( =NC1(C)C)OC1 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-5-(2-hydroxyethoxy)phenol 1115 °A / R^OH OC(=CC1)C(=CC=1OCCO)C(= NC1(C)C)OC1 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-4-(2-hydroxyethoxy)phenol 1116 R o I OC(=CC=C1)C(=C1OCCO)C(= NC1(C)C)OC1 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-3-(2-hydroxyethoxy)phenol 1117 cRn ^Y^OH OC(C(=CC1)C(=NC2(C)C)OC2) =C(C=1)OCCOC 6-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol- 2-yl)-2-(2-methoxyethoxy)phenol 1118 R o \ OC(=CC1OCCOC)C(=CC=1)C(= NC1(C)C)OC1 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-5-(2-methoxyethoxy)phenol 1119 R* > / OC(=CC1)C(=CC=1OCCOC)C(= NC1(C)C)OC1 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-4-(2-methoxyethoxy)phenol 1120 R o \ OC(=CC1)C(=C(C=1)OCCOC)C (OC1)=NC1(C)C 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-3-(2-methoxyethoxy)phenol 1121 0^ / (fR Y^OH nh2 OC(=C(N)C=C1)C(=C1)C(=NC1 (C)C)OC1 6-Amino-2-(4,4-dimethyl-4,5-dihydro- l,3-oxazol-2-yl)phenol 1122 0^ / H2N / ^x^OH OC(=CC1N)C(=CC=1)C(=NC1( C)C)OC1 5-Amino-2-(4,4-dimethyl-4,5-dihydro- l,3-oxazol-2-yl)phenol 1123 °^\ / H’NvRAr NC(=CC=C1O)C=C1C(=NC1(C) C)OC1 4-Amino-2-(4,4-dimethyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1124 nh2 o^ / tfS^ n ^^OH NC(C=CC1)=C(C=1O)C(OC1)= NC1(C)C 3-Amino-2-(4,4-dimethyl-4,5-dihydro- l,3-oxazol-2-yl)phenol 1125 O'A / cR y^OH OC(C(=CC1)C(=NC2(C)C)OC2) =C(C=1)N(C)C 6-(Dimethylamino)-2-(4,4-dimethyl-4,5- dihydro-l,3-oxazol-2-yl)phenol 1126 °^\Z XX^N —^OH 1 OC(=CC1N(C)C)C(=CC=1)C(O C1)=NC1(C)C 5-(Dimethylamino)-2-(4,4-dimethyl-4,5- dihydro-l,3-oxazol-2-yl)phenol1127 1 OC(=CC1)C(=CC=1N(C)C)C(O C1)=NC1(C)C 4-(Dimethylamino)-2-(4,4-dimethyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1128 OC(=CC=C1)C(=C1N(C)C)C(O C1)=NC1(C)C 3-(Dimethylamino)-2-(4,4-dimethyl-4,5- dihydro-l,3-oxazol-2-yl)phenol10. The compound claim 1 wherein the compound has the structure selected from:1129 O-\ / C^N OC(=C(C=C1)N(CCO)CCO)C(= C1)C(=NC1(C)C)OC1 2-{[3-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)-2-hydroxyphenyl](2-hydroxyethyl)amino}ethanol 1130 HO^ OC(=CC(=C1)N(CCO)CCO)C(= C1)C(OC1)=NC1 2-{[4-(4,5-Dihydro-l,3-oxazol-2-yl)-3- hydroxyphenyl](2- hydroxyethyl)amino}ethanol 1131 nc / ^ o-\ OC(=CC=C1N(CCO)CCO)C(=C 1)C(=NC1)OC1 2-{[3-(4,5-Dihydro-l,3-oxazol-2-yl)-4- hydroxyphenyl](2- hydroxyethyl)amino}ethanol 1132 H0 OC(=CC=C1)C(=C1N(CCO)CC O)C(OC1)=NC1 2-{[2-(4,5-Dihydro-l,3-oxazol-2-yl)-3- hydroxyphenyl](2- hydroxyethyl)amino}ethanol11. The compound claim 1 wherein the compound has the structure selected from:Patent code Structure SMILES IUPAC name 1200 OC(=CC=C1)C(=C1)C(OC1)=N C1C(C)C o-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1201 Y^OH OC(=C(C)C=C1)C(=C1)C(OC1) =NC1C(C)C 3-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-2-cresol 1202 O-\ / OC(=CC(=C1)C)C(=C1)C(=NC1 C(C)C)OC1 4-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-3-cresol 1203 O-\ / OC(=CC1)C(=CC=1C)C(OC1)= NC1C(C)C 3-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-4-cresol 1204 OC(=CC=C1)C(=C1C)C(=NC1C (C)C)OC1 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-3-cresol 1205 OH OC(=C(O)C=C1)C(=C1)C(=NC 1C(C)C)OC1 3-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)pyrocatechol 1206 HO^^OH OC(=CC1O)C(=CC=1)C(=NC1C (C)C)OC1 4-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)resorcinol1207 OC(=CC=C1O)C=C1C(=NC1C( C)C)OC1 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)hydroquinone 1208 OH O-\ / OC(C=C1)=C(C(=NC2C(C)C)O C2)C(=C1)O 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)resorcinol 1209 o Ko \= / \ OC(C(=CC1)C(=NC2C(C)C)OC 2)=C(C=1)OC 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-6-methoxyphenol 1210 o / OC(=CC(=C1)OC)C(=C1)C(OC 1)=NC1C(C)C 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-5-methoxyphenol 1211 OC(=CC=C1OC)C(=C1)C(=NC1 C(C)C)OC1 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-4-methoxyphenol 1212 R° OC(=CC1)C(C(=NC2C(C)C)OC 2)=C(C=1)OC 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-3-methoxyphenol 1213 O-A / y^0H HO^^0 OC(=C(C=C1)OCCO)C(=C1)C( OC1)=NC1C(C)C 2-(2-Hydroxyethoxy)-6-(4-isopropyl-4,5- dihydro-l,3-oxazol-2-yl)phenol 1214 5 o OC(=CC(=C1)OCCO)C(=C1)C( OC1)=NC1C(C)C 5-(2-Hydroxyethoxy)-2-(4-isopropyl-4,5- dihydro-l,3-oxazol-2-yl)phenol 1215 Q-X / OC(=CC=C1OCCO)C(=C1)C(= NC1C(C)C)OC1 4-(2-Hydroxyethoxy)-2-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1216 8 R° 5 OC(=CC=C1)C(=C1OCCO)C(O C1)=NC1C(C)C 3-(2-Hydroxyethoxy)-2-(4-isopropyl-4,5- dihydro-l,3-oxazol-2-yl)phenol 1217 Y^OH OC(=C(C=C1)OCCOC)C(=C1)C (OC1)=NC1C(C)C 6-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-2-(2-methoxyethoxy)phenol 1218 1' o ) \ OC(=CC(=C1)OCCOC)C(=C1)C (OC1)=NC1C(C)C 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-5-(2-methoxyethoxy)phenol 1219 OC(=CC=C1OCCOC)C(=C1)C( OC1)=NC1C(C)C 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-4-(2-methoxyethoxy)phenol 1220 J 5 o \ OC(=CC=C1)C(=C1OCCOC)C(= NC1C(C)C)OC1 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-3-(2-methoxyethoxy)phenol 1221 0^. / Y^OH nh2 OC(C(=CC1)C(=NC2C(C)C)OC 2)=C(N)C=1 6-Amino-2-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1222 H2N'^^OH OC(=CC(N)=C1)C(=C1)C(OC1) =NC1C(C)C 5-Amino-2-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1223 o—\ / NC(C=C(C1O)C(=NC2C(C)C)O C2)=CC=1 4-Amino-2-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1224 NH2 / NC(C=CC1)=C(C=1O)C(OC1)= NC1C(C)C 3-Amino-2-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1225 Q-\ / ilX^ y^OH OC(=C(C=C1)N(C)C)C(=C1)C( OC1)=NC1C(C)C 6-(Dimethylamino)-2-(4-isopropyl-4,5- dihydro-l,3-oxazol-2-yl)phenol1226 / 1 OC(=CC(=C1)N(C)C)C(=C1)C( OC1)=NC1C(C)C 5-(Dimethylamino)-2-(4-isopropyl-4,5- dihydro-l,3-oxazol-2-yl)phenol 1227 OC(=CC=C1N(C)C)C(=C1)C(= NC1C(C)C)OC1 4-(Dimethylamino)-2-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1228 OC(=CC1)C(=C(C=1)N(C)C)C( OC1)=NC1C(C)C 3-(Dimethylamino)-2-(4-isopropyl-4,5- dihydro-l,3-oxazol-2-yl)phenol 1229 HO^^ OC(=C(C=C1)N(CCO)CCO)C(= C1)C(OC1)=NC1C(C)C 2-{(2-Hydroxyethyl)[2-hydroxy-3-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenyl]amino}ethanol 1230 HO^ OC(=CC(=C1)N(CCO)CCO)C(= C1)C(=NC1C(C)C)OC1 2-{(2-Hydroxyethyl)[3-hydroxy-4-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenyl]amino}ethanol 1231 OC(=CC1)C(=CC=1N(CCO)CC O)C(=NC1C(C)C)OC1 2-{(2-Hydroxyethyl)[4-hydroxy-3-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenyl]amino}ethanol 1232 --5 OC(=CC1)C(=C(C=1)N(CCO)C CO)C(OC1)=NC1C(C)C 2-{(2-Hydroxyethyl)[3-hydroxy-2-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenyl]amino}ethanol12. The compound claim 1 wherein the compound has the structure selected from:Patent code Structure SMILES IUPAC name 1300 O-X OH OC(=CC=C1)C(=C1)C(=NC1CO )OC1 o-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]phenol 1301 O""\ OH y^OH OC(=C(C)C=C1)C(=C1)C(=NC1 CO)OC1 3-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]-2-cresol 1302 o-A / h OC(=CC(C)=C1)C(=C1)C(=NC1 CO)OC1 4-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]-3-cresol 1303 O-\ OH ^^OH OC(=CC=C1C)C(=C1)C(=NC1C O)OC1 3-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]-4-cresol 1304 1 O-\ ,OH ^^OH OC(=CC1)C(C(=NC2CO)OC2)= C(C)C=1 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]-3-cresol 1305 °-X OH Y^OH OH OC(C(=CC1)C(OC2)=NC2CO)= C(C=1)O 3-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]pyrocatechol 1306 HO — OH OC(=CC1O)C(=CC=1)C(OC1)= NC1C0 4-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]resorcinol 1307 o-x OH X^^OH OC(=CC=C1O)C=C1C(=NC1CO )OC1 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]hydroquinone 1308 OH O^X^OH (fS^N ^^OH OC(C=CC1)=C(C=1O)C(=NC1C O)OC1 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]resorcinol1309 OH Y^OH OC(=C(OC)C=C1)C(=C1)C(=N C1CO)OC1 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]-6-methoxyphenol 1310 O-A OH OC(=CC(=C1)OC)C(=C1)C(=N C1CO)OC1 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]-5-methoxyphenol 1311 Q-y ZOH Xr OC(=CC=C1OC)C(=C1)C(OC1) =NC1CO 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]-4-methoxyphenol 1312 OH ^^OH OC(=CC1)C(=C(C=1)OC)C(=N C1CO)OC1 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]-3-methoxyphenol 1313 0^\ OH Y^OH HO^° OC(=C(OCCO)C=C1)C(=C1)C( =NC1CO)OC1 2-(2-Hydroxyethoxy)-6-[4- (hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]phenol 1314 O-\ OH HO XX^ OC(=CC(=C1)OCCO)C(=C1)C( =NC1CO)OC1 5-(2-Hydroxyethoxy)-2-[4-(hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]phenol 1315 O-y ZOH HO^^Y^p n2"~^ ^^OH OC(=CC=C1OCCO)C(=C1)C(O C1)=NC1CO 4-(2-Hydroxyethoxy)-2-[4-(hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]phenol 1316 HQ o—\ OH OC(=CC=C1)C(=C1OCCO)C(= NC1CO)OC1 3-(2-Hydroxyethoxy)-2-[4-(hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]phenol 1317 °^\ / 01-1 Y^OH OC(=C(C=C1)OCCOC)C(=C1)C (=NC1CO)OC1 6-[4-(Hydroxymethyl)-4,5-dihydro-l,3- oxazol-2-yl]-2-(2-methoxyethoxy)phenol 1318 O-\ OH jY -'°^^O'Xx5:!4^OH OC(=CC1OCCOC)C(=CC=1)C(= NC1CO)OC1 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3- oxazol-2-yl]-5-(2-methoxyethoxy)phenol 1319 o-y oh ^^OH OC(=CC1)C(=CC=1OCCOC)C( OC1)=NC1CO 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3- oxazol-2-yl]-4-(2-methoxyethoxy)phenol 1320 \ O % OC(=CC=C1)C(=C1OCCOC)C(= NC1CO)OC1 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3- oxazol-2-yl]-3-(2-methoxyethoxy)phenol 1321 OH cc Y^OH nh2 OC(=C(N)C=C1)C(=C1)C(=NC1 CO)OC1 6-Amino-2-[4-(hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl] phenol 1322 O^\ OH jV* H2N^^OH OC(=CC1N)C(=CC=1)C(OC1)= NC1C0 5-Amino-2-[4-(hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl] phenol 1323 o^\ OH ^^OH NC(=CC=C1O)C=C1C(OC1)=N C1C0 4-Amino-2-[4-(hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl] phenol 1324 nh2 oy zoh fVN ^^OH NC(C=C1)=C(C(=C1)O)C(OC1) =NC1CO 3-Amino-2-[4-(hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl] phenol 1325 0^. OH Y^OH OC(C(=CC1)C(OC2)=NC2CO)= C(C=1)N(C)C 6-(Dimethylamino)-2-[4- (hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]phenol 1326 0-\ OH XX^N ^N^-^OH 1 OC(=CC1N(C)C)C(=CC=1)C(O C1)=NC1CO 5-(Dimethylamino)-2-[4- (hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]phenol1327 1 O-\ OH ACC ^^OH OC(=CC1)C(=CC=1N(C)C)C(O C1)=NC1CO 4-(Dimethylamino)-2-[4-(hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]phenol 1328 ,OH OC(=CC1)C(C(=NC2CO)OC2)= C(C=1)N(C)C 3-(Dimethylamino)-2-[4- (hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]phenol 1329 O-A OH y^OH AL HO^^ —^OH OC(C(=CC1)C(=NC2CO)OC2)= C(C=1)N(CCO)CCO 2-[(2-Hydroxyethyl){2-hydroxy-3-[4-(hydroxymethyl)-4,5-dihydro-l,3- oxazol-2-yl]phenyl}amino]ethanol 1330 O-\ OH CA ho^A^oh HO^ OC(=CC1N(CCO)CCO)C(=CC= 1)C(=NC1CO)OC1 2-[(2-Hydroxyethyl){3-hydroxy-4-[4-(hydroxymethyl)-4,5-dihydro-l,3- oxazol-2-yl]phenyl}amino]ethanol 1331 HO^ O^\OH ”^C0 OC(=CC=C1N(CCO)CCO)C(=C 1)C(OC1)=NC1CO 2-[(2-Hydroxyethyl){4-hydroxy-3-[4-(hydroxymethyl)-4,5-dihydro-l,3- oxazol-2-yl]phenyl}amino]ethanol 1332 ^^OH OC(=CC1)C(C(=NC2CO)OC2)= C(C=1)N(CCO)CCO 2-[(2-Hydroxyethyl){3-hydroxy-2-[4-(hydroxymethyl)-4,5-dihydro-l,3- oxazol-2-yl]phenyl}amino]ethanol13. The compound claim 1 wherein the compound has the structure selected from:Patent code Structure SMILES IUPAC name 1400 OH 0 H T OC(=CC=C1)C(=C1)C(=NC1CC C(O)=O)OC1 3-[2-(o-Hydroxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1401 OH ( y^OH OC(=C(C)C=C1)C(=C1)C(OC1) =NC1CCC(O)=O 3-[2-(2-Hydroxy-3-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1402 OH / —V 0 —^OH OC(=CC(=C1)C)C(=C1)C(=NC1 CCC(=O)O)OC1 3-[2-(2-Hydroxy-4-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1403 OH Av ° —^OH OC(=CC=C1C)C(=C1)C(OC1)= NC1CCC(O)=O 3-[2-(2-Hydroxy-5-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1404 OH ° OC(=CC1)C(=C(C=1)C)C(=NC1 CCC(O)=O)OC1 3-[2-(2-Hydroxy-6-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1405 OH 0-A z—K Y^OH OH OC(C(=CC1)C(=NC2CCC(O)=O )OC2)=C(C=1)O 3-[2-(2,3-Dihydroxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1406 OH O-X jCX^0 HO OH OC(=CC(=C1)O)C(=C1)C(=NC 1CCC(=O)O)OC1 3-[2-(2,4-Dihydroxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1407 OH o-y 0 ^^OH OC(=CC=C1O)C=C1C(OC1)=N C1CCC(=O)O 3-[2-(2,5-Dihydroxyphenyl)-4,5-dihydro- l,3-oxazol-4-yl]propionic acid1408 pH OH o-\ / —Z dr ° OC(C=CC1)=C(C=1O)C(OC1)= NC1CCC(=O)O 3-[2-(2,6-Dihydroxyphenyl)-4,5-dihydro- l,3-oxazol-4-yl]propionic acid 1409 OH Q'A z-Z cr ° OC(C(=CC1)C(=NC2CCC(=O)O )OC2)=C(C=1)OC 3-[2-(2-Hydroxy-3-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1410 OH o^\ Zv JCT ° OC(=CC(=C1)OC)C(=C1)C(OC 1)=NC1CCC(=O)O 3-[2-(2-Hydroxy-4-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1411 OH O^\ y^ 0 OC(=CC1)C(=CC=1OC)C(OC1) =NC1CCC(=O)O 3-[2-(2-Hydroxy-5-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1412 PH o °A / v dr 0 OC(=CC1)C(C(=NC2CCC(=O)O )OC2)=C(C=1)OC 3-[2-(2-Hydroxy-6-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1413 OH °A e^N Y^OH HO""^0 OC(=C(OCCO)C=C1)C(=C1)C( =NC1CCC(O)=O)OC1 3-{2-[2-Hydroxy-3-(2- hydroxyethoxy)phenyl]-4,5-dihydro-l,3-oxazol-4-yl}propionic acid 1414 pl- °A ZZ\ - '^'^O'^'^OH OC(=CC(=C1)OCCO)C(=C1)C( =NC1CCC(O)=O)OC1 3-{2-[2-Hydroxy-4-(2- hydroxyethoxy)phenyl]-4,5-dihydro-l,3-oxazol-4-yl}propionic acid 1415 0 o-\ / -^ ^^OH OC(=CC=C1OCCO)C(=C1)C(O C1)=NC1CCC(O)=O 3-{2-[2-Hydroxy-5-(2- hydroxyethoxy)phenyl]-4,5-dihydro-l,3-oxazol-4-yl}propionic acid 1416 HO.____ PH ^^0 O-A y- / OC(-CC-C1)C(-C1OCCO)C(O C1)=NC1CCC(O)=O 3-{2-[6-Hydroxy-2-(2- hydroxyethoxy)phenyl]-4,5-dihydro-l,3-oxazol-4-yl}propionic acid 1417 OH ¢0 ° OC(=C(C=C1)OCCOC)C(=C1)C (OC1)=NC1CCC(=O)O 3-{2-[2-Hydroxy-3-(2- methoxyethoxy)phenyl]-4,5-dihydro- l,3-oxazol-4-yl}propionic acid 1418 p °*\ / - / rA ° OC(=CC1OCCOC)C(=CC=1)C( OC1)=NC1CCC(=O)O 3-{2-[2-Hydroxy-4-(2- methoxyethoxy)phenyl]-4,5-dihydro- l,3-oxazol-4-yl}propionic acid 1419 OH y— r^oH OC(=CC1)C(=CC=1OCCOC)C(= NC1CCC(O)=O)OC1 3-{2-[2-Hydroxy-5-(2- methoxyethoxy)phenyl]-4,5-dihydro- l,3-oxazol-4-yl}propionic acid 1420 O / x / 0H r ° —^OH OC(=CC=C1)C(=C1OCCOC)C( OC1)=NC1CCC(=O)O 3-{2-[6-Hydroxy-2-(2- methoxyethoxy)phenyl]-4,5-dihydro- l,3-oxazol-4-yl}propionic acid 1421 OH O^X y^-K er 0 Y^OH nh2 OC(C(=CC1)C(OC2)=NC2CCC( =O)O)=C(C=1)N 3-[2-(3-Amino-2-hydroxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1422 OH °^V Zv jcr 0 ^n^^^oh OC(=CC1N)C(=CC=1)C(=NC1C CC(=O)O)OC1 3-[2-(4-Amino-2-hydroxyphenyl)-4,5- dihydro-l,3-oxazol-4-yl]propionic acid 1423 OH o^Y 0 ^^OH NC(=CC=C1O)C=C1C(=NC1CC C(O)=O)OC1 3-[2-(5-Amino-2-hydroxyphenyl)-4,5- dihydro-l,3-oxazol-4-yl]propionic acid1424 OH nh2 z—Z dr 0 NC(C=C1)=C(C(=C1)O)C(=NC1 CCC(=O)O)OC1 3-[2-(2-Amino-6-hydroxyphenyl)-4,5- dihydro-l,3-oxazol-4-yl]propionic acid 1425 OH Q'A z-A cr ° OC(C(=CC1)C(OC2)=NC2CCC( =O)O)=C(C=1)N(C)C 3-{2-[3-(Dimethylamino)-2- hydroxyphenyl]-4,5-dihydro-l,3-oxazol- 4-yl}propionic acid 1426 OH Q-\ z—Z jCC ° 1 OC(=CC(=C1)N(C)C)C(=C1)C(= NC1CCC(=O)O)OC1 3-{2-[4-(Dimethylamino)-2- hydroxyphenyl]-4,5-dihydro-l,3-oxazol- 4-yl}propionic acid 1427 OH । 0 ^^OH OC(=CC=C1N(C)C)C(=C1)C(= NC1CCC(O)=O)OC1 3-{2-[5-(Dimethylamino)-2- hydroxyphenyl]-4,5-dihydro-l,3-oxazol- 4-yl}propionic acid 1428 PH z—Z 0 ^^OH OC(=CC=C1)C(=C1N(C)C)C(O C1)=NC1CCC(O)=O 3-{2-[2-(Dimethylamino)-6- hydroxyphenyl]-4,5-dihydro-l,3-oxazol- 4-yl}propionic acid 1429 OH O-\ z—Z cc 0 Y^OH ho^^n^^oh OC(=C(C=C1)N(CCO)CCO)C(= C1)C(=NC1CCC(=O)O)OC1 3-(2-{3-[Bis(2-hydroxyethyl)amino]-2-hydroxyphenyl}-4,5-dihydro-l,3-oxazol-4-yl)propionic acid 1430 OH O-\ r- / ■— HO^^J OC(=CC(=C1)N(CCO)CCO)C(= C1)C(=NC1CCC(O)=O)OC1 3-(2-{4-[Bis(2-hydroxyethyl)amino]-2-hydroxyphenyl}-4,5-dihydro-l,3-oxazol-4-yl)propionic acid 1431 _ OH HO'Y O-\ Z^Z 0 OC(=CC=C1N(CCO)CCO)C(=C 1)C(OC1)=NC1CCC(=O)O 3-(2-{5-[Bis(2-hydroxyethyl)amino]-2-hydroxyphenyl}-4,5-dihydro-l,3-oxazol-4-yl)propionic acid 1432 H0 "°—J o-\ z-T 0 OC(=CC1)C(C(=NC2CCC(=O)O )OC2)=C(C=1)N(CCO)CCO 3-(2-{2-[Bis(2-hydroxyethyl)amino]-6-hydroxyphenyl}-4,5-dihydro-l,3-oxazol-4-yl)propionic acid14. The compound claim 1 the compound has the structure selected from:Patent code Structure SMILES IUPAC name 1500 Or OC(=CC1)C(=CC=1)C(=NCC1) OC1 o-(5,6-Dihydro-4H-l,3-oxazin-2-yl)phenol 1501 O^h y^OH OC(=C(C)C=C1)C(=C1)C(OCC1 )=NC1 3-(5,6-Dihydro-4H-l,3-oxazin-2-yl)-2-cresol 1502 OC(=CC1C)C(=CC=1)C(=NCC1 )OC1 4-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-cresol 1503 OC(=CC=C1C)C(=C1)C(=NCC1 )OC1 3-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-4-cresol1504 OC(=CC1)C(C(=NCC2)OC2)=C (C=1)C 2-(5,6-Dihydro-4H-l,3-oxazin-2-yl)-3-cresol 1505 Y^oh OH OC(=C(O)C=C1)C(=C1)C(=NC C1)OC1 3-(5,6-Dihydro-4H-l,3-oxazin-2-yl)pyrocatechol 1506 HO'^-^OH OC(=CC(O)=C1)C(=C1)C(=NC C1)OC1 4-(5,6-Dihydro-4H-l,3-oxazin-2-yl)resorcinol 1507 OC(C=C(C1O)C(=NCC2)OC2)= CC=1 2-(5,6-Dihydro-4H-l,3-oxazin-2-yl)hydroquinone 1508 OH i5X OC(C=CC1)=C(C=1O)C(=NCC1 )OC1 2-(5,6-Dihydro-4H-l,3-oxazin-2-yl)resorcinol 1509 qY CX y^OH OC(=C(OC)C=C1)C(=C1)C(=N CC1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-6-methoxyphenol 1510 ¾ o / OC(=CC1OC)C(=CC=1)C(OCC1 )=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-5-methoxyphenol 1511 O^l XOy OC(=CC=C1OC)C(=C1)C(=NCC 1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-4-methoxyphenol 1512 0^1 OC(=CC=C1)C(=C1OC)C(OCC1 )=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-methoxyphenol 1513 X HO^° OC(=C(C=C1)OCCO)C(=C1)C( =NCC1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-6-(2-hydroxyethoxy)phenol 1514 0^1 HO XX^ OC(=CC1OCCO)C(=CC=1)C(O CC1)=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-5-(2-hydroxyethoxy)phenol 1515 X. OC(=CC1)C(=CC=1OCCO)C(= NCC1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-4-(2-hydroxyethoxy)phenol 1516 I o R° OC(=CC=C1)C(=C1OCCO)C(O CC1)=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-(2-hydroxyethoxy)phenol 1517 X OC(C(=CC1)C(OCC2)=NC2)=C (C=1)OCCOC 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-6-(2-methoxyethoxy)phenol 1518 oX o xx^ —^OH OC(=CC(=C1)OCCOC)C(=C1)C (=NCC1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-5-(2-methoxyethoxy)phenol 1519 I / OC(=CC=C1OCCOC)C(=C1)C(= NCC1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-4-(2-methoxyethoxy)phenol 1520 ^°'^0 0^> ^^OH OC(=CC1)C(=C(C=1)OCCOC)C (OCC1)=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-(2-methoxyethoxy)phenol 1521 °Y cX Y^OH nh2 OC(=C(N)C=C1)C(=C1)C(=NC C1)OC1 6-Amino-2-(5,6-dihydro-4H-l,3-oxazin-2-yl)phenol1522 h2n^^oh OC(=CC(N)=C1)C(=C1)C(OCC 1)=NC1 5-Amino-2-(5,6-dihydro-4H-l,3-oxazin-2-yl)phenol 1523 NC(=CC=C1O)C=C1C(OCC1)= NCI 4-Amino-2-(5,6-dihydro-4H-l,3-oxazin-2-yl)phenol 1524 NH2 O'^i NC(C=C1)=C(C(O)=C1)C(=NC C1)OC1 3-Amino-2-(5,6-dihydro-4H-l,3-oxazin-2-yl)phenol 1525 \ / =\ o \-o 1 OC(=C(C=C1)N(C)C)C(=C1)C( OCC1)=NC1 2-(5,6-Dihydro-4H-l,3-oxazin-2-yl)-6-(dimethylamino)phenol 1526 —^OH 1 OC(=CC1N(C)C)C(=CC=1)C(O CC1)=NC1 2-(5,6-Dihydro-4H-l,3-oxazin-2-yl)-5-(dimethylamino)phenol 1527 1 xrW OC(=CC1)C(=CC=1N(C)C)C(= NCC1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-4-(dimethylamino)phenol 1528 OC(=CC1)C(=C(C=1)N(C)C)C(= NCC1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-(dimethylamino)phenol 1529 Cv Y^OH HO^—'Nj---^OH OC(=C(C=C1)N(CCO)CCO)C(= C1)C(OCC1)=NC1 6-[Bis(2-hydroxyethyl)amino]-2-(5,6-dihydro-4H-l,3-oxazin-2-yl)phenol 1530 » rx® HO^ OC(=CC(=C1)N(CCO)CCO)C(= C1)C(=NCC1)OC1 5-[Bis(2-hydroxyethyl)amino]-2-(5,6-dihydro-4H-l,3-oxazin-2-yl)phenol 1531 HO^ ^YY^ OC(=CC=C1N(CCO)CCO)C(=C 1)C(OCC1)=NC1 4-[Bis(2-hydroxyethyl)amino]-2-(5,6-dihydro-4H-l,3-oxazin-2-yl)phenol 1532 6X OC(=CC1)C(C(=NCC2)OC2)=C (C=1)N(CCO)CCO 3-[Bis(2-hydroxyethyl)amino]-2-(5,6-dihydro-4H-l,3-oxazin-2-yl)phenol15. The compound claim 1 wherein the compound has the structure selected from:Patent code Structure SMILES IUPAC name 1000 OC(=CC=C1)C(=C1)C(=NC1)O Cl o-(4,5-Dihydro-l,3-oxazol-2-yl)phenol 1001 Y^OH OC(=C(C)C=C1)C(=C1)C(=NC1 )OC1 3-(4,5-Dihydro-l,3-oxazol-2-yl)-2-cresol 1002 °-A OC(=CC1C)C(=CC=1)C(=NC1) OC1 4-(4,5-Dihydro-l,3-oxazol-2-yl)-3-cresol 1003 o"\ OC(=CC=C1C)C(=C1)C(=NC1) OC1 3-(4,5-Dihydro-l,3-oxazol-2-yl)-4-cresol 1004 OC(=CC1)C(=C(C)C=1)C(OC1) =NC1 2-(4,5-Dihydro-l,3-oxazol-2-yl)-3-cresol1009 \= / \ OC(=C(C=C1)OC)C(=C1)C(=N C1)OC1 2-(4,5-Dihydro-l,3-oxazol-2-yl)-6-methoxyphenol 1010 °-A xx" O — OH OC(=CC1OC)C(=CC=1)C(OC1) =NC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-5-methoxyphenol 1011 OC(=CC1)C(=CC=1OC)C(=NC1 )OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-4-methoxyphenol 1012 5 <5 OC(=CC1)C(=C(C=1)OC)C(=N C1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-3-methoxyphenol 1025 0 O \= / \ OC(C(=CC1)C(OC2)=NC2)=C( C=1)N(C)C 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-6-(dimethylamino)phenol 1026 O-A ,jCv 1 OC(=CC1N(C)C)C(=CC=1)C(O C1)=NC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-5-(dimethylamino)phenol 1027 %? OC(=CC1)C(=CC=1N(C)C)C(= NC1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-4-(dimethylamino)phenol 1028 O-\ K—^OH OC(=CC1)C(C(=NC2)OC2)=C( C=1)N(C)C 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-3-(dimethylamino)phenol 1100 oy / [TX^ OC(=CC=C1)C(=C1)C(=NC1(C) C)OC1 o-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1101 O^ / QAn OC(C(=CC1)C(OC2)=NC2(C)C) =C(C)C=1 3-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)-2-cresol 1102 o-y jRX^N OC(=CC1C)C(=CC=1)C(OC1)= NC1(C)C 4-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)-3-cresol 1103 X. X7 OC(=CC=C1C)C(=C1)C(=NC1( C)C)OC1 3-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)-4-cresol 1104 OC(=CC1)C(C(OC2)=NC2(C)C) =C(C=1)C 2-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol- 2-yl)-3-cresol 1109 X. O-o \= / \ OC(=C(OC)C=C1)C(=C1)C(OC 1)=NC1(C)C 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-6-methoxyphenol 1110 / o R 8 v OC(=CC(=C1)OC)C(=C1)C(OC 1)=NC1(C)C 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-5-methoxyphenol 1111 °^\ 'YR OC(=CC=C1OC)C(=C1)C(=NC1 (C)C)OC1 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-4-methoxyphenol 1112 °~\L fV'" OC(=CC1)C(=C(C=1)OC)C(=N C1(C)C)OC1 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-3-methoxyphenol 1125 o-X / rX'N y^OH OC(C(=CC1)C(=NC2(C)C)OC2) =C(C=1)N(C)C 6-(Dimethylamino)-2-(4,4-dimethyl-4,5- dihydro-l,3-oxazol-2-yl)phenol1126 0-^ / —^OH 1 OC(=CC1N(C)C)C(=CC=1)C(O C1)=NC1(C)C 5-(Dimethylamino)-2-(4,4-dimethyl-4,5- dihydro-l,3-oxazol-2-yl)phenol 1127 1 XT OC(=CC1)C(=CC=1N(C)C)C(O C1)=NC1(C)C 4-(Dimethylamino)-2-(4,4-dimethyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1128 OC(=CC=C1)C(=C1N(C)C)C(O C1)=NC1(C)C 3-(Dimethylamino)-2-(4,4-dimethyl-4,5- dihydro-l,3-oxazol-2-yl)phenol 1400 pH O"\ CT ° OC(=CC=C1)C(=C1)C(=NC1CC C(O)=O)OC1 3-[2-(o-Hydroxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1401 OH O^N ° OC(=C(C)C=C1)C(=C1)C(OC1) =NC1CCC(O)=O 3-[2-(2-Hydroxy-3-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1402 OH °-\ ,—z xr 0 OC(=CC(=C1)C)C(=C1)C(=NC1 CCC(=O)O)OC1 3-[2-(2-Hydroxy-4-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1403 pH °^v cd ° OC(=CC=C1C)C(=C1)C(OC1)= NC1CCC(O)=O 3-[2-(2-Hydroxy-5-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1404 OH 6^" ° OC(=CC1)C(=C(C=1)C)C(=NC1 CCC(O)=O)OC1 3-[2-(2-Hydroxy-6-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1409 PH er ° Y^OH / ° OC(C(=CC1)C(=NC2CCC(=O)O )OC2)=C(C=1)OC 3-[2-(2-Hydroxy-3-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1410 OH O^X / -^ nd ° OC(=CC(=C1)OC)C(=C1)C(OC 1)=NC1CCC(=O)O 3-[2-(2-Hydroxy-4-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1411 OH °^\ / x ^yv^v ° OC(=CC1)C(=CC=1OC)C(OC1) =NC1CCC(=O)O 3-[2-(2-Hydroxy-5-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1412 PH 0 0"\ / v 6r 0 ^^OH OC(=CC1)C(C(=NC2CCC(=O)O )OC2)=C(C=1)OC 3-[2-(2-Hydroxy-6-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1425 pH O-\ yY o'"" 0 Y^OH x-N\ OC(C(=CC1)C(OC2)=NC2CCC( =O)O)=C(C=1)N(C)C 3-{2-[3-(Dimethylamino)-2- hydroxyphenyl]-4,5-dihydro-l,3-oxazol- 4-yl}propionic acid 1426 OH O~A / —Z xir 0 ^n'^-^oh 1 OC(=CC(=C1)N(C)C)C(=C1)C(= NC1CCC(=O)O)OC1 3-{2-[4-(Dimethylamino)-2- hydroxyphenyl]-4,5-dihydro-l,3-oxazol- 4-yl}propionic acid 1427 OH ^^OH OC(=CC=C1N(C)C)C(=C1)C(= NC1CCC(O)=O)OC1 3-{2-[5-(Dimethylamino)-2- hydroxyphenyl]-4,5-dihydro-l,3-oxazol- 4-yl}propionic acid 1428 . PH tt / —Z cX ° OC(=CC=C1)C(=C1N(C)C)C(O C1)=NC1CCC(O)=O 3-{2-[2-(Dimethylamino)-6- hydroxyphenyl]-4,5-dihydro-l,3-oxazol- 4-yl}propionic acid1500 OC(=CC1)C(=CC=1)C(=NCC1) OC1 o-(5,6-Dihydro-4H-l,3-oxazin-2-yl)phenol 1501 OC(=C(C)C=C1)C(=C1)C(OCC1 )=NC1 3-(5,6-Dihydro-4H-l,3-oxazin-2-yl)-2-cresol 1502 OC(=CC1C)C(=CC=1)C(=NCC1 )OC1 4-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-cresol 1503 o' \-o 1 zO OC(=CC=C1C)C(=C1)C(=NCC1 )OC1 3-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-4-cresol 1504 OC(=CC1)C(C(=NCC2)OC2)=C (C=1)C 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-cresol 1509 \ / =\ o' o 1 zO OC(=C(OC)C=C1)C(=C1)C(=N CC1)OC1 2-(5,6-Dihydro-4H-l,3-oxazin-2-yl)-6-methoxyphenol 1510 ¾ o / OC(=CC1OC)C(=CC=1)C(OCC1 )=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-5-methoxyphenol 1511 0^1 OC(=CC=C1OC)C(=C1)C(=NCC 1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-4-methoxyphenol 1512 ? OC(=CC=C1)C(=C1OC)C(OCC1 )=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-methoxyphenol 1525 o^j [□X y^OH OC(=C(C=C1)N(C)C)C(=C1)C( OCC1)=NC1 2-(5,6-Dihydro-4H-l,3-oxazin-2-yl)-6-(dimethylamino)phenol 1526 1 OC(=CC1N(C)C)C(=CC=1)C(O CC1)=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-5-(dimethylamino)phenol 1527 1 'XX OC(=CC1)C(=CC=1N(C)C)C(= NCC1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-4-(dimethylamino)phenol 1528 60 OC(=CC1)C(=C(C=1)N(C)C)C(= NCC1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-(dimethylamino)phenol16. The compound claim 1 wherein the compound has the structure selected from:Patent code Structure SMILES IUPAC name 1000 o OC(=CC=C1)C(=C1)C(=NC1)O Cl o-(4,5-Dihydro-l,3-oxazol-2-yl)phenol 1001 cX y^OH OC(=C(C)C=C1)C(=C1)C(=NC1 )OC1 3-(4,5-Dihydro-l,3-oxazol-2-yl)-2-cresol1002 o-x OC(=CC1C)C(=CC=1)C(=NC1) OC1 4-(4,5-Dihydro-l,3-oxazol-2-yl)-3-cresol 1003 'AAn Y^OH OC(=CC=C1C)C(=C1)C(=NC1) OC1 3-(4,5-Dihydro-l,3-oxazol-2-yl)-4-cresol 1004 OC(=CC1)C(=C(C)C=1)C(OC1) =NC1 2-(4,5-Dihydro-l,3-oxazol-2-yl)-3-cresol 1009 0-4 — o Ko \= / \ OC(=C(C=C1)OC)C(=C1)C(=N C1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-6-methoxyphenol 1010 O-\ xx^ XO^—^OH OC(=CC1OC)C(=CC=1)C(OC1) =NC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-5-methoxyphenol 1011 OC(=CC1)C(=CC=1OC)C(=NC1 )OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-4-methoxyphenol 1012 o—\ OC(=CC1)C(=C(C=1)OC)C(=N C1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-3-methoxyphenol 1400 PH O^\ Av — 0 |[ T —^OH OC(=CC=C1)C(=C1)C(=NC1CC C(O)=O)OC1 3-[2-(o-Hydroxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1401 OH o^\ / —( cc ° y^OH OC(=C(C)C=C1)C(=C1)C(OC1) =NC1CCC(O)=O 3-[2-(2-Hydroxy-3-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1402 OH °^\ / — / 0 OC(=CC(=C1)C)C(=C1)C(=NC1 CCC(=O)O)OC1 3-[2-(2-Hydroxy-4-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1403 OH °^V Av ° OC(=CC=C1C)C(=C1)C(OC1)= NC1CCC(O)=O 3-[2-(2-Hydroxy-5-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1404 OH r ° OC(=CC1)C(=C(C=1)C)C(=NC1 CCC(O)=O)OC1 3-[2-(2-Hydroxy-6-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1409 PH o-x Av 0 XT OH A OC(C(=CC1)C(=NC2CCC(=O)O )OC2)=C(C=1)OC 3-[2-(2-Hydroxy-3-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1410 / o k 0-^0 I OC(=CC(=C1)OC)C(=C1)C(OC 1)=NC1CCC(=O)O 3-[2-(2-Hydroxy-4-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1411 OH °^\ Z~^ xOyy^N^ 0 OC(=CC1)C(=CC=1OC)C(OC1) =NC1CCC(=O)O 3-[2-(2-Hydroxy-5-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1412 PH dr 0 ^^OH OC(=CC1)C(C(=NC2CCC(=O)O )OC2)=C(C=1)OC 3-[2-(2-Hydroxy-6-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid1500 OC(=CC1)C(=CC=1)C(=NCC1) OC1 o-(5,6-Dihydro-4H-l,3-oxazin-2-yl)phenol 1501 OC(=C(C)C=C1)C(=C1)C(OCC1 )=NC1 3-(5,6-Dihydro-4H-l,3-oxazin-2-yl)-2-cresol 1502 OC(=CC1C)C(=CC=1)C(=NCC1 )OC1 4-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-cresol 1503 Ya o' \-o 1 OC(=CC=C1C)C(=C1)C(=NCC1 )OC1 3-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-4-cresol 1504 6Y1 OC(=CC1)C(C(=NCC2)OC2)=C (C=1)C 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-cresol 1509 \ / =\ ° Ya o' o 1 OC(=C(OC)C=C1)C(=C1)C(=N CC1)OC1 2-(5,6-Dihydro-4H-l,3-oxazin-2-yl)-6-methoxyphenol 1510 o / OC(=CC1OC)C(=CC=1)C(OCC1 )=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-5-methoxyphenol 1511 0^1 OC(=CC=C1OC)C(=C1)C(=NCC 1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-4-methoxyphenol 1512 OC(=CC=C1)C(=C1OC)C(OCC1 )=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-methoxyphenol17. The catalyst delivery composition of any of any of claims 1 to 16 wherein the transition metal element (M) is Mn.
18. The catalyst delivery composition of claim 17 wherein M is Mn in the 3+ oxidation state.
19. The catalyst delivery composition of any preceding claim in which the chelate is in a solid solution of the water-soluble organic polymer.
20. The catalyst delivery composition of claim 19 were in the catalyst delivery composition is in the form of a sheet material.
21. The catalyst delivery composition of any of claims 1 to 18 were in the chelate is in the form of a solid and mixed with an alkali metal salt and bound together in granulate form by means of the water-soluble organic polymer.
22. The catalyst delivery composition of any preceding claim in which the water-soluble organic polymer is selected from Polyvinyl alcohol (PVA), Polyvinylpyrrolidone (PVP), Cellulose derivatives, such as hydroxypropyl methylcellulose (HPMC) or carboxymethyl cellulose (CMC), Polyethylene glycol (PEG).
23. The catalyst delivery composition of any preceding claim wherein the chelate is present in a detergent composition comprising an oxidative bleach.
24. The catalyst delivery composition of claim 23 wherein the chelate is separate from the oxidative bleach, such as sodium percarbonate, which is a source of hydrogen peroxide.
25. The catalyst delivery composition of any preceding claim wherein the composition is a dishwashing detergent composition.Amendments to the claims have been filed as followsClaims,1. A catalyst delivery composition comprising a chelate as a solid or solid solution in the form of a particle or sheet the composition comprising from 1 to 50% by weight of the chelate, from 1 to 50% by weight of a water-soluble organic polymer and optionally an inorganic solid in the form of an alkali metal salt of from 1 to 98%, the chelate comprising a compound (L) as defined below as the ligand of a transition metal element (M), the ligand being a compound (L) of structural formula 1:formula 116 08 23whereinm is 1 or 2;n is 1 or 2;R independently represents H, CH3, C2H5, C3H7, C4H9 and OH; or OR1 wherein R1 represents CH3(CH2)v , wherein v is 0 to 17; or NR22, wherein:R represents H, CH3(CH2)w , wherein w is 0 to 17;R2 represents (CH2)2- OH;and when R is in positions 4, 5 or 6,R can further represent (CH2)xCH3 , wherein x is 4 to 17:R’ represents H, CH3, CH2CH3, CH(CH3)2, (CH2)yOH or (CH2)yCOOH, wherein y is 0 to 17;R” represents H, CH3, CH2CH3, CH2OH, CH2CH2OH, CH2OCH3 or CH2CH2OCH3;R’” represents H;or an ester wherein R’” represents C=O) ( R4);R4 represents (CH2)z - R5, wherein z is from 1 to 18 and R5 is H, OH or COOH; preferably OH:or an ether, wherein R’” represents - R7- R8;R7 represents C1 to 04 alkyl;R8 represents H, CH3, OH or COOH:or CH(OH)CH2OH.16 08 232. The catalyst delivery composition of claim 1 wherein:in R any v is 0 to 5, any w is 0 to 5 and any x is 0 to 5;R’ and R” independently represent H or CH3;R’” represents H.
3. The catalyst delivery composition of claim 1 wherein:R wherein at least one of v, w and z is 6 to 17; preferably at least two of v, w and z is 6 to 17; most preferably any v is 6 to 17, any w is 6 to 17 and any x is 6 to 17;R’ and R” independently represent H or CH3;R’” represents H.
4. The catalyst delivery composition of claim 1 wherein:R represents H, CH3, OH, OCH3, or N(CH3)2;R’ represents H, CH3, CH2OH or (CH2)2COOH;R” represents HR’” provides an ether.
5. The catalyst delivery composition of any of claims 1 or 4 wherein n is 1.
6. The catalyst delivery composition of any of claims 1 to 4 wherein n is 2.
7. The catalyst delivery composition of any preceding claim wherein m is 1.
8. The catalyst delivery composition claim 1 wherein the compound has the structure selected from:16 08 23Patent code Structure SMILES IUPAC name 1000 o-x OC(=CC=C1)C(=C1)C(=NC1)O Cl o-(4,5-Dihydro-l,3-oxazol-2-yl)phenol 1001 y^OH OC(=C(C)C=C1)C(=C1)C(=NC1 )OC1 3-(4,5-Dihydro-l,3-oxazol-2-yl)-2-cresol 1002 o-A jOAn OC(=CC1C)C(=CC=1)C(=NC1) OC1 4-(4,5-Dihydro-l,3-oxazol-2-yl)-3-cresol 1003 °-\ —^OH OC(=CC=C1C)C(=C1)C(=NC1) OC1 3-(4,5-Dihydro-l,3-oxazol-2-yl)-4-cresol 1004 OC(=CC1)C(=C(C)C=1)C(OC1) =NC1 2-(4,5-Dihydro-l,3-oxazol-2-yl)-3-cresol 1005 0-x OH OC(=C(O)C=C1)C(=C1)C(OC1) =NC1 3-(4,5-Dihydro-l,3-oxazol-2-yl)pyrocatechol 1006 O"\ HO^^^OH OC(=CC1O)C(=CC=1)C(OC1)= NCI 4-(4,5-Dihydro-l,3-oxazol-2-yl)resorcinol 1007 O"\ OC(=CC=C1O)C(=C1)C(OC1)= NCI 2-(4,5-Dihydro-l, 3-oxazol-2-yl)hydroquinone 1008 OH OC(=CC=C1)C(=C1O)C(=NC1) OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)resorcinol 1009 o-4_O Ko \= / \ OC(=C(C=C1)OC)C(=C1)C(=N C1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-6-methoxyphenol 1010 °—\ xy1 O— OH OC(=CC1OC)C(=CC=1)C(OC1) =NC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-5-methoxyphenol 1011 yYn> OC(=CC1)C(=CC=1OC)C(=NC1 )OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-4-methoxyphenol 1012 o-x OC(=CC1)C(=C(C=1)OC)C(=N C1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-3-methoxyphenol 1013 Y^OH OC(C(=CC1)C(OC2)=NC2)=C( C=1)OCCO 6-(4,5-Dihydro-l, 3-oxazol-2-yl)-2-(2-hydroxyethoxy)phenol 1014 o' X OC(=CC1OCCO)C(=CC=1)C(O C1)=NC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-5-(2-hydroxyethoxy)phenol 1015 OC(=CC=C1OCCO)C(=C1)C(= NC1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-4-(2-hydroxyethoxy)phenol 1016 O-\ 6^n —^OH OC(=CC=C1)C(=C1OCCO)C(O C1)=NC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-3-(2-hydroxyethoxy)phenol16 08 231017 Y^OH OC(C(=CC1)C(OC2)=NC2)=C( C=1)OCCOC 6-(4,5-Dihydro-l,3-oxazol-2-yl)-2-(2-methoxyethoxy)phenol 1018 q o \ OC(=CC(=C1)OCCOC)C(=C1)C (OC1)=NC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-5-(2-methoxyethoxy)phenol 1019 T / OC(=CC1)C(=CC=1OCCOC)C(= NC1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-4-(2-methoxyethoxy)phenol 1020 ----- 0-\ OC(=CC=C1)C(=C1OCCOC)C(= NC1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-3-(2-methoxyethoxy)phenol 1021 N Y^OH nh2 OC(C(=CC1)C(OC2)=NC2)=C( N)C=1 6-Amino-2-(4,5-dihydro-l,3-oxazol-2-yl)phenol 1022 o-\ jCv HzN^-^OH OC(=CC(N)=C1)C(=C1)C(OC1) =NC1 5-Amino-2-(4,5-dihydro-l,3-oxazol-2-yl)phenol 1023 O-A OH OC(=CC=C1N)C(=C1)C(=NC1) OC1 4-Amino-2-(4,5-dihydro-l,3-oxazol-2-yl)phenol 1024 nh2 o^\ dx N ^^OH OC(=CC=C1)C(=C1N)C(OC1)= NCI 3-Amino-2-(4,5-dihydro-l,3-oxazol-2-yl)phenol 1025 O-4 o \= / \ OC(C(=CC1)C(OC2)=NC2)=C( C=1)N(C)C 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-6-(dimethylamino)phenol 1026 0-\ 1 OC(=CC1N(C)C)C(=CC=1)C(O C1)=NC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-5-(dimethylamino)phenol 1027 Xt? OC(=CC1)C(=CC=1N(C)C)C(= NC1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-4-(dimethylamino)phenol 1028 O-X dv OC(=CC1)C(C(=NC2)OC2)=C( C=1)N(C)C 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-3-(dimethylamino)phenol 1029 O-A cdN Y^OH _N. OC(=C(C=C1)N(CCO)CCO)C(= C1)C(OC1)=NC1 2-{[3-(4,5-Dihydro-l, 3-oxazol-2-yl)-2- hydroxyphenyl](2- hydroxyethyl)amino}ethanol 1030 HO^ OC(=CC1N(CCO)CCO)C(=CC= 1)C(OC1)=NC1 2-{[4-(4,5-Dihydro-l, 3-oxazol-2-yl)-3- hydroxyphenyl](2- hydroxyethyl)amino}ethanol 1031 no'Y o^\ ^-^OH OC(=CC=C1N(CCO)CCO)C(=C 1)C(=NC1)OC1 2-{[3-(4,5-Dihydro-l, 3-oxazol-2-yl)-4- hydroxyphenyl](2- hydroxyethyl)amino}ethanol 1032 H0 ddN OC(=CC1)C(C(=NC2)OC2)=C( C=1)N(CCO)CCO 2-{[2-(4,5-Dihydro-l, 3-oxazol-2-yl)-3- hydroxyphenyl](2- hydroxyethyl)amino}ethanol 1033 & Xo o COC(=CC=C1)C(=C1)C(=NC1) OC1 2-(o-Methoxyphenyl)-4,5-dihydro-l,3-oxazole 1034 Q C CCOC(=CC=C1)C(=C1)C(OC1) =NC1 2-(o-Ethoxyphenyl)-4,5-dihydro-l,3-oxazole1035 R o X OCCOC(=CC1)C(=CC=1)C(=NC 1)OC1 2-[o-(4,5-Dihydro-l,3-oxazol-2-yl)phenoxy]ethanol 1036 o / COCCOC(=CC1)C(=CC=1)C(=N C1)OC1 2-[o-(2-Methoxyethoxy)phenyl]-4,5-dihydro-l,3-oxazole 1037 o-\ o OCCOCCOC(=CC1)C(=CC=1)C (OC1)=NC1 2-{2-[o-(4,5-Dihydro-l,3-oxazol-2-yl)phenoxy]ethoxy}ethanol 1038 R o Q \ COCCOCCOC(=CC=C1)C(=C1) C(OC1)=NC1 2-{o-[2-(2- Methoxyethoxy)ethoxy]phenyl}-4,5-dihydro-l,3-oxazole 1039 X o R OC(CO)COC(=CC1)C(=CC=1)C (=NC1)OC1 3-[o-(4,5-Dihydro-l,3-oxazol-2-yl)phenoxy]-l,2-propanediol 1040 o OC(=O)COC(=CC=C1)C(=C1)C (OC1)=NC1 [o-(4,5-Dihydro-l,3-oxazol-2-yl)phenoxy]acetic acid 1041 R l? o X OC(=O)CCOC(=CC1)C(=CC=1) C(OC1)=NC1 3-[o-(4,5-Dihydro-l,3-oxazol-2-yl)phenoxy]propionic acid16 08 239. The catalyst delivery composition claim 1 wherein the compound has the structure selected from:Patent code Structure SMILES IUPAC name 1100 cA OC(=CC=C1)C(=C1)C(=NC1(C) C)OC1 o-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1101 o^ / rA Y^OH OC(C(=CC1)C(OC2)=NC2(C)C) =C(C)C=1 3-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)-2-cresol 1102 —^OH OC(=CC1C)C(=CC=1)C(OC1)= NC1(C)C 4-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)-3-cresol 1103 O-W_ RrA OC(=CC=C1C)C(=C1)C(=NC1( C)C)OC1 3-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)-4-cresol 1104 OC(=CC1)C(C(OC2)=NC2(C)C) =C(C=1)C 2-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol- 2-yl)-3-cresol 1105 o-\ / rA Y^OH OH OC(C(=CC1)C(OC2)=NC2(C)C) =C(C=1)O 3-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)pyrocatechol 1106 o-x / xA HO^^^OH OC(=CC=C1C(OC2)=NC2(C)C) C=C1O 4-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)resorcinol 1107 OC(C=C(C1O)C(OC2)=NC2(C) C)=CC=1 2-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol- 2-yl)hydroquinone 1108 0H O-A / ^ (fY"N OC(C=C1)=C(C(=NC2(C)C)OC 2)C(O)=C1 2-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)resorcinol16 08 231109 O"A / y^OH OC(=C(OC)C=C1)C(=C1)C(OC 1)=NC1(C)C 2-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol- 2-yl)-6-methoxyphenol 1110 / o R s v OC(=CC(=C1)OC)C(=C1)C(OC 1)=NC1(C)C 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-5-methoxyphenol 1111 o-x 'VR OC(=CC=C1OC)C(=C1)C(=NC1 (C)C)OC1 2-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol- 2-yl)-4-methoxyphenol 1112 fY OC(=CC1)C(=C(C=1)OC)C(=N C1(C)C)OC1 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-3-methoxyphenol 1113 o~"\ / cRn Y^0H HO^^0 OC(=C(OCCO)C=C1)C(=C1)C( OC1)=NC1(C)C 6-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol- 2-yl)-2-(2-hydroxyethoxy)phenol 1114 0^ / OC(=CC(=C1)OCCO)C(=C1)C( =NC1(C)C)OC1 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-5-(2-hydroxyethoxy)phenol 1115 °-y OC(=CC1)C(=CC=1OCCO)C(= NC1(C)C)OC1 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-4-(2-hydroxyethoxy)phenol 1116 I o R° OC(=CC=C1)C(=C1OCCO)C(= NC1(C)C)OC1 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-3-(2-hydroxyethoxy)phenol 1117 OCy cA y^oH OC(C(=CC1)C(=NC2(C)C)OC2) =C(C=1)OCCOC 6-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol- 2-yl)-2-(2-methoxyethoxy)phenol 1118 R o \ OC(=CC1OCCOC)C(=CC=1)C(= NC1(C)C)OC1 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-5-(2-methoxyethoxy)phenol 1119 R > / OC(=CC1)C(=CC=1OCCOC)C(= NC1(C)C)OC1 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-4-(2-methoxyethoxy)phenol 1120 \ o R OC(=CC1)C(=C(C=1)OCCOC)C (OC1)=NC1(C)C 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-3-(2-methoxyethoxy)phenol 1121 O^\y cR Y^OH nh2 OC(=C(N)C=C1)C(=C1)C(=NC1 (C)C)OC1 6-Amino-2-(4,4-dimethyl-4,5-dihydro- l,3-oxazol-2-yl)phenol 1122 °^v h2n^^ / ^oh OC(=CC1N)C(=CC=1)C(=NC1( C)C)OC1 5-Amino-2-(4,4-dimethyl-4,5-dihydro- l,3-oxazol-2-yl)phenol 1123 o^ / R^'OH NC(=CC=C1O)C=C1C(=NC1(C) C)OC1 4-Amino-2-(4,4-dimethyl-4,5-dihydro- l,3-oxazol-2-yl)phenol 1124 nh2 o^ / ^^OH NC(C=CC1)=C(C=1O)C(OC1)= NC1(C)C 3-Amino-2-(4,4-dimethyl-4,5-dihydro- l,3-oxazol-2-yl)phenol 1125 o-X / fR" Y^OH OC(C(=CC1)C(=NC2(C)C)OC2) =C(C=1)N(C)C 6-(Dimethylamino)-2-(4,4-dimethyl-4,5- dihydro-l,3-oxazol-2-yl)phenol 1126 0^ / rx^ 1 OC(=CC1N(C)C)C(=CC=1)C(O C1)=NC1(C)C 5-(Dimethylamino)-2-(4,4-dimethyl-4,5- dihydro-l,3-oxazol-2-yl)phenol 1127 1 —^OH OC(=CC1)C(=CC=1N(C)C)C(O C1)=NC1(C)C 4-(Dimethylamino)-2-(4,4-dimethyl-4,5-dihydro-l,3-oxazol-2-yl)phenol1128 OC(=CC=C1)C(=C1N(C)C)C(O C1)=NC1(C)C 3-(Dimethylamino)-2-(474-dimethyl-475- dihydro-l,3-oxazol-2-yl)phenol10. The catalyst delivery composition claim 1 wherein the compound has the structure selected from:1129 0-\ / y^OH OC(=C(C=C1)N(CCO)CCO)C(= C1)C(=NC1(C)C)OC1 2-{[3-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)-2-hydroxyphenyl](2-hydroxyethyl)amino}ethanol 1130 HO^ OC(=CC(=C1)N(CCO)CCO)C(= C1)C(OC1)=NC1 2-{[4-(4,5-Dihydro-l,3-oxazol-2-yl)-3- hydroxyphenyl](2- hydroxyethyl)amino}ethanol 1131 OC(=CC=C1N(CCO)CCO)C(=C 1)C(=NC1)OC1 2-{[3-(4,5-Dihydro-l,3-oxazol-2-yl)-4- hydroxyphenyl](2- hydroxyethyl)amino}ethanol 1132 H0 OC(=CC=C1)C(=C1N(CCO)CC O)C(OC1)=NC1 2-{[2-(4,5-Dihydro-l,3-oxazol-2-yl)-3- hydroxyphenyl](2- hydroxyethyl)amino}ethanol16 08 2311. The catalyst delivery composition claim 1 wherein the compound has the structure selected from:Patent code Structure SMILES IUPAC name 1200 QC' OC(=CC=C1)C(=C1)C(OC1)=N C1C(C)C o-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1201 y^OH OC(=C(C)C=C1)C(=C1)C(OC1) =NC1C(C)C 3-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-2-cresol 1202 O-\ / OC(=CC(=C1)C)C(=C1)C(=NC1 C(C)C)OC1 4-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-3-cresol 1203 OT / OC(=CC1)C(=CC=1C)C(OC1)= NC1C(C)C 3-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-4-cresol 1204 OC(=CC=C1)C(=C1C)C(=NC1C (C)C)OC1 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-3-cresol 1205 o-y / Y'OH OH OC(=C(O)C=C1)C(=C1)C(=NC 1C(C)C)OC1 3-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)pyrocatechol 1206 HO^^OH OC(=CC1O)C(=CC=1)C(=NC1C (C)C)OC1 4-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)resorcinol16 08 231207 OC(=CC=C1O)C=C1C(=NC1C( C)C)OC1 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)hydroquinone 1208 OH O-\ / OC(C=C1)=C(C(=NC2C(C)C)O C2)C(=C1)O 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)resorcinol 1209 o Ko \= / \ OC(C(=CC1)C(=NC2C(C)C)OC 2)=C(C=1)OC 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-6-methoxyphenol 1210 o / OC(=CC(=C1)OC)C(=C1)C(OC 1)=NC1C(C)C 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-5-methoxyphenol 1211 OC(=CC=C1OC)C(=C1)C(=NC1 C(C)C)OC1 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-4-methoxyphenol 1212 R° OC(=CC1)C(C(=NC2C(C)C)OC 2)=C(C=1)OC 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-3-methoxyphenol 1213 O-A / y^0H HO^^0 OC(=C(C=C1)OCCO)C(=C1)C( OC1)=NC1C(C)C 2-(2-Hydroxyethoxy)-6-(4-isopropyl-4,5- dihydro-l,3-oxazol-2-yl)phenol 1214 5 o OC(=CC(=C1)OCCO)C(=C1)C( OC1)=NC1C(C)C 5-(2-Hydroxyethoxy)-2-(4-isopropyl-4,5- dihydro-l,3-oxazol-2-yl)phenol 1215 Q-X / OC(=CC=C1OCCO)C(=C1)C(= NC1C(C)C)OC1 4-(2-Hydroxyethoxy)-2-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1216 8 R° 5 OC(=CC=C1)C(=C1OCCO)C(O C1)=NC1C(C)C 3-(2-Hydroxyethoxy)-2-(4-isopropyl-4,5- dihydro-l,3-oxazol-2-yl)phenol 1217 Y^OH OC(=C(C=C1)OCCOC)C(=C1)C (OC1)=NC1C(C)C 6-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-2-(2-methoxyethoxy)phenol 1218 1' o ) \ OC(=CC(=C1)OCCOC)C(=C1)C (OC1)=NC1C(C)C 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-5-(2-methoxyethoxy)phenol 1219 OC(=CC=C1OCCOC)C(=C1)C( OC1)=NC1C(C)C 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-4-(2-methoxyethoxy)phenol 1220 J 5 o \ OC(=CC=C1)C(=C1OCCOC)C(= NC1C(C)C)OC1 2-(4-lsopropyl-4,5-dihydro-l,3-oxazol-2-yl)-3-(2-methoxyethoxy)phenol 1221 0^. / Y^OH nh2 OC(C(=CC1)C(=NC2C(C)C)OC 2)=C(N)C=1 6-Amino-2-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1222 H2N'^^OH OC(=CC(N)=C1)C(=C1)C(OC1) =NC1C(C)C 5-Amino-2-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1223 o—\ / NC(C=C(C1O)C(=NC2C(C)C)O C2)=CC=1 4-Amino-2-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1224 NH2 / NC(C=CC1)=C(C=1O)C(OC1)= NC1C(C)C 3-Amino-2-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1225 Q-\ / ilX^ y^OH OC(=C(C=C1)N(C)C)C(=C1)C( OC1)=NC1C(C)C 6-(Dimethylamino)-2-(4-isopropyl-4,5- dihydro-l,3-oxazol-2-yl)phenol1226 0-\ / 1 OC(=CC(=C1)N(C)C)C(=C1)C( OC1)=NC1C(C)C 5-(Dimethylamino)-2-(4-isopropyl-4,5- dihydro-l,3-oxazol-2-yl)phenol 1227 OC(=CC=C1N(C)C)C(=C1)C(= NC1C(C)C)OC1 4-(Dimethylamino)-2-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1228 OC(=CC1)C(=C(C=1)N(C)C)C( OC1)=NC1C(C)C 3-(Dimethylamino)-2-(4-isopropyl-4,5- dihydro-l,3-oxazol-2-yl)phenol 1229 HO^^ OC(=C(C=C1)N(CCO)CCO)C(= C1)C(OC1)=NC1C(C)C 2-{(2-Hydroxyethyl)[2-hydroxy-3-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenyl]amino}ethanol 1230 HO^ OC(=CC(=C1)N(CCO)CCO)C(= C1)C(=NC1C(C)C)OC1 2-{(2-Hydroxyethyl)[3-hydroxy-4-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenyl]amino}ethanol 1231 OC(=CC1)C(=CC=1N(CCO)CC O)C(=NC1C(C)C)OC1 2-{(2-Hydroxyethyl)[4-hydroxy-3-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenyl]amino}ethanol 1232 --5 OC(=CC1)C(=C(C=1)N(CCO)C CO)C(OC1)=NC1C(C)C 2-{(2-Hydroxyethyl)[3-hydroxy-2-(4-isopropyl-4,5-dihydro-l,3-oxazol-2-yl)phenyl]amino}ethanol16 08 2312. The catalyst delivery composition claim 1 wherein the compound has the structure selected from:Patent code Structure SMILES IUPAC name 1300 o-x OH OC(=CC=C1)C(=C1)C(=NC1CO )OC1 o-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]phenol 1301 O""\ OH OC(=C(C)C=C1)C(=C1)C(=NC1 CO)OC1 3-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]-2-cresol 1302 o^J^ —^OH OC(=CC(C)=C1)C(=C1)C(=NC1 CO)OC1 4-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]-3-cresol 1303 O-\ OH ^^OH OC(=CC=C1C)C(=C1)C(=NC1C O)OC1 3-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]-4-cresol 1304 1 O-X ,OH —^OH OC(=CC1)C(C(=NC2CO)OC2)= C(C)C=1 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]-3-cresol 1305 o-x OH Y^OH OH OC(C(=CC1)C(OC2)=NC2CO)= C(C=1)O 3-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]pyrocatechol 1306 HO — OH OC(=CC1O)C(=CC=1)C(OC1)= NC1C0 4-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]resorcinol 1307 O-A OH HO^pJ^N>^ X^^OH OC(=CC=C1O)C=C1C(=NC1CO )OC1 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3- oxazol-2-yl]hydroquinone 1308 OH O-X^OH ^^OH OC(C=CC1)=C(C=1O)C(=NC1C O)OC1 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]resorcinol16 08 231309 OH Y^OH OC(=C(OC)C=C1)C(=C1)C(=N C1CO)OC1 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]-6-methoxyphenol 1310 O-A OH OC(=CC(=C1)OC)C(=C1)C(=N C1CO)OC1 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]-5-methoxyphenol 1311 Q-y ZOH Xr OC(=CC=C1OC)C(=C1)C(OC1) =NC1CO 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]-4-methoxyphenol 1312 OH ^^OH OC(=CC1)C(=C(C=1)OC)C(=N C1CO)OC1 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]-3-methoxyphenol 1313 0^\ OH Y^OH HO^° OC(=C(OCCO)C=C1)C(=C1)C( =NC1CO)OC1 2-(2-Hydroxyethoxy)-6-[4- (hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]phenol 1314 O-\ OH HO XX^ OC(=CC(=C1)OCCO)C(=C1)C( =NC1CO)OC1 5-(2-Hydroxyethoxy)-2-[4-(hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]phenol 1315 O-y ZOH HO^^Y^p n2"~^ ^^OH OC(=CC=C1OCCO)C(=C1)C(O C1)=NC1CO 4-(2-Hydroxyethoxy)-2-[4-(hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]phenol 1316 HQ o—\ OH OC(=CC=C1)C(=C1OCCO)C(= NC1CO)OC1 3-(2-Hydroxyethoxy)-2-[4-(hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]phenol 1317 °^\ / 01-1 Y^OH OC(=C(C=C1)OCCOC)C(=C1)C (=NC1CO)OC1 6-[4-(Hydroxymethyl)-4,5-dihydro-l,3- oxazol-2-yl]-2-(2-methoxyethoxy)phenol 1318 O-\ OH jY -'°^^O'Xx5:!4^OH OC(=CC1OCCOC)C(=CC=1)C(= NC1CO)OC1 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3- oxazol-2-yl]-5-(2-methoxyethoxy)phenol 1319 o-y oh ^^OH OC(=CC1)C(=CC=1OCCOC)C( OC1)=NC1CO 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3- oxazol-2-yl]-4-(2-methoxyethoxy)phenol 1320 \ O % OC(=CC=C1)C(=C1OCCOC)C(= NC1CO)OC1 2-[4-(Hydroxymethyl)-4,5-dihydro-l,3- oxazol-2-yl]-3-(2-methoxyethoxy)phenol 1321 OH cc Y^OH nh2 OC(=C(N)C=C1)C(=C1)C(=NC1 CO)OC1 6-Amino-2-[4-(hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl] phenol 1322 O^\ OH jV* H2N^^OH OC(=CC1N)C(=CC=1)C(OC1)= NC1C0 5-Amino-2-[4-(hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl] phenol 1323 o^\ OH ^^OH NC(=CC=C1O)C=C1C(OC1)=N C1C0 4-Amino-2-[4-(hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl] phenol 1324 nh2 oy zoh fVN ^^OH NC(C=C1)=C(C(=C1)O)C(OC1) =NC1CO 3-Amino-2-[4-(hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl] phenol 1325 0^. OH Y^OH OC(C(=CC1)C(OC2)=NC2CO)= C(C=1)N(C)C 6-(Dimethylamino)-2-[4- (hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]phenol 1326 O-\ OH XX^N ^N^-^OH 1 OC(=CC1N(C)C)C(=CC=1)C(O C1)=NC1CO 5-(Dimethylamino)-2-[4- (hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]phenol1327 1 O-\ OH ACC ^^OH OC(=CC1)C(=CC=1N(C)C)C(O C1)=NC1CO 4-(Dimethylamino)-2-[4-(hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]phenol 1328 ,OH OC(=CC1)C(C(=NC2CO)OC2)= C(C=1)N(C)C 3-(Dimethylamino)-2-[4- (hydroxymethyl)-4,5-dihydro-l,3-oxazol-2-yl]phenol 1329 O-A OH Y^OH AL HO^^ —^OH OC(C(=CC1)C(=NC2CO)OC2)= C(C=1)N(CCO)CCO 2-[(2-Hydroxyethyl){2-hydroxy-3-[4-(hydroxymethyl)-4,5-dihydro-l,3- oxazol-2-yl]phenyl}amino]ethanol 1330 O-\ OH CA ho^A^oh HO^ OC(=CC1N(CCO)CCO)C(=CC= 1)C(=NC1CO)OC1 2-[(2-Hydroxyethyl){3-hydroxy-4-[4-(hydroxymethyl)-4,5-dihydro-l,3- oxazol-2-yl]phenyl}amino]ethanol 1331 HO^Y O^\OH ”^C0 OC(=CC=C1N(CCO)CCO)C(=C 1)C(OC1)=NC1CO 2-[(2-Hydroxyethyl){4-hydroxy-3-[4-(hydroxymethyl)-4,5-dihydro-l,3- oxazol-2-yl]phenyl}amino]ethanol 1332 ^^OH OC(=CC1)C(C(=NC2CO)OC2)= C(C=1)N(CCO)CCO 2-[(2-Hydroxyethyl){3-hydroxy-2-[4-(hydroxymethyl)-4,5-dihydro-l,3- oxazol-2-yl]phenyl}amino]ethanol13. The catalyst delivery composition claim 1 wherein the compound has the structure selected from:16 08 23Patent code Structure SMILES IUPAC name 1400 oh oT1 OC(=CC=C1)C(=C1)C(=NC1CC C(O)=O)OC1 3-[2-(o-Hydroxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1401 OH y^OH OC(=C(C)C=C1)C(=C1)C(OC1) =NC1CCC(O)=O 3-[2-(2-Hydroxy-3-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1402 OH 0 —^OH OC(=CC(=C1)C)C(=C1)C(=NC1 CCC(=O)O)OC1 3-[2-(2-Hydroxy-4-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1403 OH Av ° OC(=CC=C1C)C(=C1)C(OC1)= NC1CCC(O)=O 3-[2-(2-Hydroxy-5-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1404 OH ° OC(=CC1)C(=C(C=1)C)C(=NC1 CCC(O)=O)OC1 3-[2-(2-Hydroxy-6-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1405 OH O^A Cv 0 Y^OH OH OC(C(=CC1)C(=NC2CCC(O)=O )OC2)=C(C=1)O 3-[2-(2,3-Dihydroxyphenyl)-4,5-dihydro- l,3-oxazol-4-yl]propionic acid 1406 OH o-x HO OH OC(=CC(=C1)O)C(=C1)C(=NC 1CCC(=O)O)OC1 3-[2-(2,4-Dihydroxyphenyl)-4,5-dihydro- l,3-oxazol-4-yl]propionic acid 1407 OH o-y / -^ 0 ^^^OH OC(=CC=C1O)C=C1C(OC1)=N C1CCC(=O)O 3-[2-(2,5-Dihydroxyphenyl)-4,5-dihydro- l,3-oxazol-4-yl]propionic acid16 08 231408 pH OH o-\ / —Z dr ° OC(C=CC1)=C(C=1O)C(OC1)= NC1CCC(=O)O 3-[2-(2,6-Dihydroxyphenyl)-4,5-dihydro- l,3-oxazol-4-yl]propionic acid 1409 OH Q'A z-Z cr ° Y^OH OC(C(=CC1)C(=NC2CCC(=O)O )OC2)=C(C=1)OC 3-[2-(2-Hydroxy-3-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1410 OH o^\ Zv JCT ° OC(=CC(=C1)OC)C(=C1)C(OC 1)=NC1CCC(=O)O 3-[2-(2-Hydroxy-4-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1411 OH O^\ y^ 0 OC(=CC1)C(=CC=1OC)C(OC1) =NC1CCC(=O)O 3-[2-(2-Hydroxy-5-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1412 PH o °A / v dr 0 OC(=CC1)C(C(=NC2CCC(=O)O )OC2)=C(C=1)OC 3-[2-(2-Hydroxy-6-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1413 OH °A e^N Y^OH HO""^0 OC(=C(OCCO)C=C1)C(=C1)C( =NC1CCC(O)=O)OC1 3-{2-[2-Hydroxy-3-(2- hydroxyethoxy)phenyl]-4,5-dihydro-l,3-oxazol-4-yl}propionic acid 1414 pl- °A ZZ\ - '^'^O'^'^OH OC(=CC(=C1)OCCO)C(=C1)C( =NC1CCC(O)=O)OC1 3-{2-[2-Hydroxy-4-(2- hydroxyethoxy)phenyl]-4,5-dihydro-l,3-oxazol-4-yl}propionic acid 1415 O o-\ / -^ ^^OH OC(=CC=C1OCCO)C(=C1)C(O C1)=NC1CCC(O)=O 3-{2-[2-Hydroxy-5-(2- hydroxyethoxy)phenyl]-4,5-dihydro-l,3-oxazol-4-yl}propionic acid 1416 HO.____ PH O-A y- / OC(-CC-C1)C(-C1OCCO)C(O C1)=NC1CCC(O)=O 3-{2-[6-Hydroxy-2-(2- hydroxyethoxy)phenyl]-4,5-dihydro-l,3-oxazol-4-yl}propionic acid 1417 OH ¢0 ° OC(=C(C=C1)OCCOC)C(=C1)C (OC1)=NC1CCC(=O)O 3-{2-[2-Hydroxy-3-(2- methoxyethoxy)phenyl]-4,5-dihydro- l,3-oxazol-4-yl}propionic acid 1418 p °*\ / - / rA ° OC(=CC1OCCOC)C(=CC=1)C( OC1)=NC1CCC(=O)O 3-{2-[2-Hydroxy-4-(2- methoxyethoxy)phenyl]-4,5-dihydro- l,3-oxazol-4-yl}propionic acid 1419 OH y— r^oH OC(=CC1)C(=CC=1OCCOC)C(= NC1CCC(O)=O)OC1 3-{2-[2-Hydroxy-5-(2- methoxyethoxy)phenyl]-4,5-dihydro- l,3-oxazol-4-yl}propionic acid 1420 O / x / 0H r ° —^OH OC(=CC=C1)C(=C1OCCOC)C( OC1)=NC1CCC(=O)O 3-{2-[6-Hydroxy-2-(2- methoxyethoxy)phenyl]-4,5-dihydro- l,3-oxazol-4-yl}propionic acid 1421 OH O^X y^-K er 0 Y^OH nh2 OC(C(=CC1)C(OC2)=NC2CCC( =O)O)=C(C=1)N 3-[2-(3-Amino-2-hydroxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1422 OH °^V Zv jcr 0 ^n^^^oh OC(=CC1N)C(=CC=1)C(=NC1C CC(=O)O)OC1 3-[2-(4-Amino-2-hydroxyphenyl)-4,5- dihydro-l,3-oxazol-4-yl]propionic acid 1423 OH o^Y 0 ^^OH NC(=CC=C1O)C=C1C(=NC1CC C(O)=O)OC1 3-[2-(5-Amino-2-hydroxyphenyl)-4,5- dihydro-l,3-oxazol-4-yl]propionic acid16 08 231424 OH nh2 z—Z dr 0 NC(C=C1)=C(C(=C1)O)C(=NC1 CCC(=O)O)OC1 3-[2-(2-Amino-6-hydroxyphenyl)-4,5- dihydro-l,3-oxazol-4-yl]propionic acid 1425 OH Q'A z-A cr ° Y^OH OC(C(=CC1)C(OC2)=NC2CCC( =O)O)=C(C=1)N(C)C 3-{2-[3-(Dimethylamino)-2- hydroxyphenyl]-4,5-dihydro-l,3-oxazol- 4-yl}propionic acid 1426 OH Q-\ z—Z jCC ° 1 OC(=CC(=C1)N(C)C)C(=C1)C(= NC1CCC(=O)O)OC1 3-{2-[4-(Dimethylamino)-2- hydroxyphenyl]-4,5-dihydro-l,3-oxazol- 4-yl}propionic acid 1427 OH । 0 ^^OH OC(=CC=C1N(C)C)C(=C1)C(= NC1CCC(O)=O)OC1 3-{2-[5-(Dimethylamino)-2- hydroxyphenyl]-4,5-dihydro-l,3-oxazol- 4-yl}propionic acid 1428 PH z—Z 0 ^^OH OC(=CC=C1)C(=C1N(C)C)C(O C1)=NC1CCC(O)=O 3-{2-[2-(Dimethylamino)-6- hydroxyphenyl]-4,5-dihydro-l,3-oxazol- 4-yl}propionic acid 1429 OH O-\ z—Z cc 0 Y^OH ho^^n^^oh OC(=C(C=C1)N(CCO)CCO)C(= C1)C(=NC1CCC(=O)O)OC1 3-(2-{3-[Bis(2-hydroxyethyl)amino]-2-hydroxyphenyl}-4,5-dihydro-l,3-oxazol-4-yl)propionic acid 1430 OH O-\ r- / ■— HO^^J OC(=CC(=C1)N(CCO)CCO)C(= C1)C(=NC1CCC(O)=O)OC1 3-(2-{4-[Bis(2-hydroxyethyl)amino]-2-hydroxyphenyl}-4,5-dihydro-l,3-oxazol-4-yl)propionic acid 1431 _ OH HO'Y O-\ Z^Z 0 OC(=CC=C1N(CCO)CCO)C(=C 1)C(OC1)=NC1CCC(=O)O 3-(2-{5-[Bis(2-hydroxyethyl)amino]-2-hydroxyphenyl}-4,5-dihydro-l,3-oxazol-4-yl)propionic acid 1432 H0 "°—J o-\ z-T 0 OC(=CC1)C(C(=NC2CCC(=O)O )OC2)=C(C=1)N(CCO)CCO 3-(2-{2-[Bis(2-hydroxyethyl)amino]-6-hydroxyphenyl}-4,5-dihydro-l,3-oxazol-4-yl)propionic acid14. The catalyst delivery composition claim 1 the compound has the structure selected from:Patent code Structure SMILES IUPAC name 1500 Or OC(=CC1)C(=CC=1)C(=NCC1) OC1 o-(5,6-Dihydro-4H-l,3-oxazin-2-yl)phenol 1501 O^h y^OH OC(=C(C)C=C1)C(=C1)C(OCC1 )=NC1 3-(5,6-Dihydro-4H-l,3-oxazin-2-yl)-2-cresol 1502 OC(=CC1C)C(=CC=1)C(=NCC1 )OC1 4-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-cresol 1503 OC(=CC=C1C)C(=C1)C(=NCC1 )OC1 3-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-4-cresol16 08 231504 OC(=CC1)C(C(=NCC2)OC2)=C (C=1)C 2-(5,6-Dihydro-4H-l,3-oxazin-2-yl)-3-cresol 1505 Y^oh OH OC(=C(O)C=C1)C(=C1)C(=NC C1)OC1 3-(5,6-Dihydro-4H-l,3-oxazin-2-yl)pyrocatechol 1506 HO'^-^OH OC(=CC(O)=C1)C(=C1)C(=NC C1)OC1 4-(5,6-Dihydro-4H-l,3-oxazin-2-yl)resorcinol 1507 OC(C=C(C1O)C(=NCC2)OC2)= CC=1 2-(5,6-Dihydro-4H-l,3-oxazin-2-yl)hydroquinone 1508 OH i5X OC(C=CC1)=C(C=1O)C(=NCC1 )OC1 2-(5,6-Dihydro-4H-l,3-oxazin-2-yl)resorcinol 1509 qY CX y^OH OC(=C(OC)C=C1)C(=C1)C(=N CC1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-6-methoxyphenol 1510 ¾ o / OC(=CC1OC)C(=CC=1)C(OCC1 )=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-5-methoxyphenol 1511 O^l XOy OC(=CC=C1OC)C(=C1)C(=NCC 1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-4-methoxyphenol 1512 0^1 OC(=CC=C1)C(=C1OC)C(OCC1 )=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-methoxyphenol 1513 X HO^° OC(=C(C=C1)OCCO)C(=C1)C( =NCC1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-6-(2-hydroxyethoxy)phenol 1514 0^1 HO XX^ OC(=CC1OCCO)C(=CC=1)C(O CC1)=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-5-(2-hydroxyethoxy)phenol 1515 X. OC(=CC1)C(=CC=1OCCO)C(= NCC1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-4-(2-hydroxyethoxy)phenol 1516 I o R° OC(=CC=C1)C(=C1OCCO)C(O CC1)=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-(2-hydroxyethoxy)phenol 1517 X OC(C(=CC1)C(OCC2)=NC2)=C (C=1)OCCOC 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-6-(2-methoxyethoxy)phenol 1518 oX o xx^ —^OH OC(=CC(=C1)OCCOC)C(=C1)C (=NCC1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-5-(2-methoxyethoxy)phenol 1519 I / OC(=CC=C1OCCOC)C(=C1)C(= NCC1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-4-(2-methoxyethoxy)phenol 1520 ^°'^0 0^> ^^OH OC(=CC1)C(=C(C=1)OCCOC)C (OCC1)=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-(2-methoxyethoxy)phenol 1521 °Y cX Y^OH nh2 OC(=C(N)C=C1)C(=C1)C(=NC C1)OC1 6-Amino-2-(5,6-dihydro-4H-l,3-oxazin-2-yl)phenol16 08 231522 h2n^^oh OC(=CC(N)=C1)C(=C1)C(OCC 1)=NC1 5-Amino-2-(5,6-dihydro-4H-l,3-oxazin-2-yl)phenol 1523 NC(=CC=C1O)C=C1C(OCC1)= NCI 4-Amino-2-(5,6-dihydro-4H-l,3-oxazin-2-yl)phenol 1524 NH2 O'^i NC(C=C1)=C(C(O)=C1)C(=NC C1)OC1 3-Amino-2-(5,6-dihydro-4H-l,3-oxazin-2-yl)phenol 1525 \ / =\ o \-o 1 OC(=C(C=C1)N(C)C)C(=C1)C( OCC1)=NC1 2-(5,6-Dihydro-4H-l,3-oxazin-2-yl)-6-(dimethylamino)phenol 1526 —^OH 1 OC(=CC1N(C)C)C(=CC=1)C(O CC1)=NC1 2-(5,6-Dihydro-4H-l,3-oxazin-2-yl)-5-(dimethylamino)phenol 1527 1 xrW OC(=CC1)C(=CC=1N(C)C)C(= NCC1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-4-(dimethylamino)phenol 1528 OC(=CC1)C(=C(C=1)N(C)C)C(= NCC1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-(dimethylamino)phenol 1529 Cv Y^OH HO^—'Nj---^OH OC(=C(C=C1)N(CCO)CCO)C(= C1)C(OCC1)=NC1 6-[Bis(2-hydroxyethyl)amino]-2-(5,6-dihydro-4H-l,3-oxazin-2-yl)phenol 1530 HO^ OC(=CC(=C1)N(CCO)CCO)C(= C1)C(=NCC1)OC1 5-[Bis(2-hydroxyethyl)amino]-2-(5,6-dihydro-4H-l,3-oxazin-2-yl)phenol 1531 HO^ OC(=CC=C1N(CCO)CCO)C(=C 1)C(OCC1)=NC1 4-[Bis(2-hydroxyethyl)amino]-2-(5,6-dihydro-4H-l,3-oxazin-2-yl)phenol 1532 6X OC(=CC1)C(C(=NCC2)OC2)=C (C=1)N(CCO)CCO 3-[Bis(2-hydroxyethyl)amino]-2-(5,6-dihydro-4H-l,3-oxazin-2-yl)phenol15. The catalyst delivery composition claim 1 wherein the compound has the structure selected from:Patent code Structure SMILES IUPAC name 1000 °-\ OC(=CC=C1)C(=C1)C(=NC1)O Cl o-(4,5-Dihydro-l,3-oxazol-2-yl)phenol 1001 Y^OH OC(=C(C)C=C1)C(=C1)C(=NC1 )OC1 3-(4,5-Dihydro-l,3-oxazol-2-yl)-2-cresol 1002 °-A OC(=CC1C)C(=CC=1)C(=NC1) OC1 4-(4,5-Dihydro-l,3-oxazol-2-yl)-3-cresol 1003 °"A OC(=CC=C1C)C(=C1)C(=NC1) OC1 3-(4,5-Dihydro-l,3-oxazol-2-yl)-4-cresol16 08 231004 OC(=CC1)C(=C(C)C=1)C(OC1) =NC1 2-(4,5-Dihydro-l,3-oxazol-2-yl)-3-cresol 1009 o-4_O Mo \= / \ OC(=C(C=C1)OC)C(=C1)C(=N C1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-6-methoxyphenol 1010 O-A O — OH OC(=CC1OC)C(=CC=1)C(OC1) =NC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-5-methoxyphenol 1011 °^\ OC(=CC1)C(=CC=1OC)C(=NC1 )OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-4-methoxyphenol 1012 5 <5 OC(=CC1)C(=C(C=1)OC)C(=N C1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-3-methoxyphenol 1025 0 o RO \= / \ OC(C(=CC1)C(OC2)=NC2)=C( C=1)N(C)C 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-6-(dimethylamino)phenol 1026 0-\ rO 1 OC(=CC1N(C)C)C(=CC=1)C(O C1)=NC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-5-(dimethylamino)phenol 1027 %? OC(=CC1)C(=CC=1N(C)C)C(= NC1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-4-(dimethylamino)phenol 1028 O-\ —AOH OC(=CC1)C(C(=NC2)OC2)=C( C=1)N(C)C 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-3-(dimethylamino)phenol 1100 R 8 v OC(=CC=C1)C(=C1)C(=NC1(C) C)OC1 o (4,4 Dimethyl 4,5 dihydro 1,3 oxazol 2-yl)phenol 1101 o^ / rO y^OH OC(C(=CC1)C(OC2)=NC2(C)C) =C(C)C=1 3-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)-2-cresol 1102 o-a^ OC(=CC1C)C(=CC=1)C(OC1)= NC1(C)C 4-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)-3-cresol 1103 OC(=CC=C1C)C(=C1)C(=NC1( C)C)OC1 3-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)-4-cresol 1104 6R OC(=CC1)C(C(OC2)=NC2(C)C) =C(C=1)C 2-(4,4-Dimethyl-4,5-dihydro-l,3-oxazol-2-yl)-3-cresol 1109 O"A / fR' Y^OH OC(=C(OC)C=C1)C(=C1)C(OC 1)=NC1(C)C 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-6-methoxyphenol 1110 o / OC(=CC(=C1)OC)C(=C1)C(OC 1)=NC1(C)C 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-5-methoxyphenol 1111 °Y OC(=CC=C1OC)C(=C1)C(=NC1 (C)C)OC1 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-4-methoxyphenol 1112 fR" OC(=CC1)C(=C(C=1)OC)C(=N C1(C)C)OC1 2-(4,4-Dimethyl-4,5-dihydro-l, 3-oxazol- 2-yl)-3-methoxyphenol16 08 231125 O'A / Y^OH OC(C(=CC1)C(=NC2(C)C)OC2) =C(C=1)N(C)C 6-(Dimethylamino)-2-(4,4-dimethyl-4,5- dihydro-l,3-oxazol-2-yl)phenol 1126 O^ cd ^N^^^OH 1 OC(=CC1N(C)C)C(=CC=1)C(O C1)=NC1(C)C 5-(Dimethylamino)-2-(4,4-dimethyl-4,5- dihydro-l,3-oxazol-2-yl)phenol 1127 1 'C OC(=CC1)C(=CC=1N(C)C)C(O C1)=NC1(C)C 4-(Dimethylamino)-2-(4,4-dimethyl-4,5-dihydro-l,3-oxazol-2-yl)phenol 1128 eC OC(=CC=C1)C(=C1N(C)C)C(O C1)=NC1(C)C 3-(Dimethylamino)-2-(4,4-dimethyl-4,5- dihydro-l,3-oxazol-2-yl)phenol 1400 pH O'\ / or ° OC(=CC=C1)C(=C1)C(=NC1CC C(O)=O)OC1 3-[2-(o-Hydroxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1401 OH °^\ cr 0 Y^OH OC(=C(C)C=C1)C(=C1)C(OC1) =NC1CCC(O)=O 3-[2-(2-Hydroxy-3-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1402 OH O^\ / —A jC ° OC(=CC(=C1)C)C(=C1)C(=NC1 CCC(=O)O)OC1 3-[2-(2-Hydroxy-4-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1403 pH °^V / C CN ° OC(=CC=C1C)C(=C1)C(OC1)= NC1CCC(O)=O 3-[2-(2-Hydroxy-5-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1404 PH OH OC(=CC1)C(=C(C=1)C)C(=NC1 CCC(O)=O)OC1 3-[2-(2-Hydroxy-6-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1409 pH od'~ 0 Y^OH / ° OC(C(=CC1)C(=NC2CCC(=O)O )OC2)=C(C=1)OC 3-[2-(2-Hydroxy-3-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1410 OyO C 5 0 o / OC(=CC(=C1)OC)C(=C1)C(OC 1)=NC1CCC(=O)O 3-[2-(2-Hydroxy-4-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1411 OH O^\ / -^ ^°yy^n^ 0 OC(=CC1)C(=CC=1OC)C(OC1) =NC1CCC(=O)O 3-[2-(2-Hydroxy-5-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1412 PH 6r 0 OC(=CC1)C(C(=NC2CCC(=O)O )OC2)=C(C=1)OC 3-[2-(2-Hydroxy-6-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1425 pH Q'A / X cd’ 0 Y^OH XNX OC(C(=CC1)C(OC2)=NC2CCC( =O)O)=C(C=1)N(C)C 3-{2-[3-(Dimethylamino)-2- hydroxyphenyl]-4,5-dihydro-l,3-oxazol- 4-yl}propionic acid 1426 OH °-\ / — / .cd 0 '^nx^ / ^oh 1 OC(=CC(=C1)N(C)C)C(=C1)C(= NC1CCC(=O)O)OC1 3-{2-[4-(Dimethylamino)-2- hydroxyphenyl]-4,5-dihydro-l,3-oxazol- 4-yl}propionic acid16 08 231427 OH 0 OC(=CC=C1N(C)C)C(=C1)C(= NC1CCC(O)=O)OC1 3-{2-[5-(Dimethylamino)-2- hydroxyphenyl]-4,5-dihydro-l,3-oxazol- 4-yl}propionic acid 1428 pH o^y dv 0 OC(=CC=C1)C(=C1N(C)C)C(O C1)=NC1CCC(O)=O 3-{2-[2-(Dimethylamino)-6- hydroxyphenyl]-4,5-dihydro-l,3-oxazol- 4-yl}propionic acid 1500 OY OC(=CC1)C(=CC=1)C(=NCC1) OC1 o-(5,6-Dihydro-4H-l,3-oxazin-2-yl)phenol 1501 y^OH OC(=C(C)C=C1)C(=C1)C(OCC1 )=NC1 3-(5,6-Dihydro-4H-l,3-oxazin-2-yl)-2-cresol 1502 OC(=CC1C)C(=CC=1)C(=NCC1 )OC1 4-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-cresol 1503 oz \-o 1 zO OC(=CC=C1C)C(=C1)C(=NCC1 )OC1 3-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-4-cresol 1504 OC(=CC1)C(C(=NCC2)OC2)=C (C=1)C 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-cresol 1509 °y (Y y^OH OC(=C(OC)C=C1)C(=C1)C(=N CC1)OC1 2-(5,6-Dihydro-4H-l,3-oxazin-2-yl)-6-methoxyphenol 1510 ¾ o / OC(=CC1OC)C(=CC=1)C(OCC1 )=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-5-methoxyphenol 1511 OC(=CC=C1OC)C(=C1)C(=NCC 1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-4-methoxyphenol 1512 0^1 OC(=CC=C1)C(=C1OC)C(OCC1 )=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-methoxyphenol 1525 °Y Oy Y^OH OC(=C(C=C1)N(C)C)C(=C1)C( OCC1)=NC1 2-(5,6-Dihydro-4H-l,3-oxazin-2-yl)-6-(dimethylamino)phenol 1526 yy ^N^Y^OH 1 OC(=CC1N(C)C)C(=CC=1)C(O CC1)=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-5-(dimethylamino)phenol 1527 1 Y OOy OC(=CC1)C(=CC=1N(C)C)C(= NCC1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-4-(dimethylamino)phenol 1528 YY o'Y Y OC(=CC1)C(=C(C=1)N(C)C)C(= NCC1)OC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-(dimethylamino)phenol16. The catalyst delivery composition claim 1 wherein the compound has the structure selected from:Patent code Structure SMILES IUPAC name16 08 231000 o-\ ^^OH OC(=CC=C1)C(=C1)C(=NC1)O Cl 0-(4,5-Dihydro-l,3-oxazol-2-yl)phenol 1001 y^OH OC(=C(C)C=C1)C(=C1)C(=NC1 )OC1 3-(4,5-Dihydro-l,3-oxazol-2-yl)-2-cresol 1002 °-A OC(=CC1C)C(=CC=1)C(=NC1) OC1 4-(4,5-Dihydro-l,3-oxazol-2-yl)-3-cresol 1003 OC(=CC=C1C)C(=C1)C(=NC1) OC1 3-(4,5-Dihydro-l,3-oxazol-2-yl)-4-cresol 1004 OC(=CC1)C(=C(C)C=1)C(OC1) =NC1 2-(4,5-Dihydro-l,3-oxazol-2-yl)-3-cresol 1009 O_o ° \= / \ OC(=C(C=C1)OC)C(=C1)C(=N C1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-6-methoxyphenol 1010 <T—^OH OC(=CC1OC)C(=CC=1)C(OC1) =NC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-5-methoxyphenol 1011 ?A OC(=CC1)C(=CC=1OC)C(=NC1 )OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-4-methoxyphenol 1012 o-\ OC(=CC1)C(=C(C=1)OC)C(=N C1)OC1 2-(4,5-Dihydro-l, 3-oxazol-2-yl)-3-methoxyphenol 1400 PH O-\ / - / O h T —^OH OC(=CC=C1)C(=C1)C(=NC1CC C(O)=O)OC1 3-[2-(o-Hydroxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1401 OH / —( CC^ ° y^OH OC(=C(C)C=C1)C(=C1)C(OC1) =NC1CCC(O)=O 3-[2-(2-Hydroxy-3-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1402 OH 0 —^OH OC(=CC(=C1)C)C(=C1)C(=NC1 CCC(=O)O)OC1 3-[2-(2-Hydroxy-4-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1403 OH °^v Av ° OC(=CC=C1C)C(=C1)C(OC1)= NC1CCC(O)=O 3-[2-(2-Hydroxy-5-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1404 OH ° OC(=CC1)C(=C(C=1)C)C(=NC1 CCC(O)=O)OC1 3-[2-(2-Hydroxy-6-tolyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1409 PH °"\ / - / cr 0 Y^OH OC(C(=CC1)C(=NC2CCC(=O)O )OC2)=C(C=1)OC 3-[2-(2-Hydroxy-3-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1410 OH A~ / iX"N ° OC(=CC(=C1)OC)C(=C1)C(OC 1)=NC1CCC(=O)O 3-[2-(2-Hydroxy-4-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1411 OH xOyy^N^ 0 OC(=CC1)C(=CC=1OC)C(OC1) =NC1CCC(=O)O 3-[2-(2-Hydroxy-5-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid16 08 231412 PH 0 OC(=CC1)C(C(=NC2CCC(=O)O )OC2)=C(C=1)OC 3-[2-(2-Hydroxy-6-methoxyphenyl)-4,5-dihydro-l,3-oxazol-4-yl]propionic acid 1500 (□X OC(=CC1)C(=CC=1)C(=NCC1) OC1 o-(5,6-Dihydro-4H-l,3-oxazin-2-yl)phenol 1501 (Oy y^OH OC(=C(C)C=C1)C(=C1)C(OCC1 )=NC1 3-(5,6-Dihydro-4H-l,3-oxazin-2-yl)-2-cresol 1502 jCv OC(=CC1C)C(=CC=1)C(=NCC1 )OC1 4-(5,6-Dihydro-4H-l,3-oxazin-2-yl)-3-cresol 1503 OC(=CC=C1C)C(=C1)C(=NCC1 )OC1 3-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-4-cresol 1504 cY OC(=CC1)C(C(=NCC2)OC2)=C (C=1)C 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-cresol 1509 CY OC(=C(OC)C=C1)C(=C1)C(=N CC1)OC1 2-(5,6-Dihydro-4H-l,3-oxazin-2-yl)-6-methoxyphenol 1510 ¾ o / OC(=CC1OC)C(=CC=1)C(OCC1 )=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-5-methoxyphenol 1511 ^^'OH OC(=CC=C1OC)C(=C1)C(=NCC 1)OC1 2-(5,6-Dihydro-4H-l,3-oxazin-2-yl )-4-methoxyphenol 1512 OC(=CC=C1)C(=C1OC)C(OCC1 )=NC1 2-(5,6-Dihydro-4H-l, 3-oxazin-2-yl)-3-methoxyphenol17. The catalyst delivery composition of any of any of claims 1 to 16 wherein the transition metal element (M) is Mn.
18. The catalyst delivery composition of claim 17 wherein M is Mn in the 3+ oxidation state.
19. The catalyst delivery composition of any preceding claim in which the chelate is in a solid solution of the water-soluble organic polymer.
20. The catalyst delivery composition of claim 19 were in the catalyst delivery composition is in the form of a sheet material.
21. The catalyst delivery composition of any of claims 1 to 18 were in the chelate is in the form of a solid and mixed with an alkali metal salt and bound together in granulate form by means of the water-soluble organic polymer.
22. The catalyst delivery composition of any preceding claim in which the water-soluble organic polymer is selected from Polyvinyl alcohol (PVA), Polyvinylpyrrolidone (PVP), Cellulose derivatives, such as hydroxypropyl methylcellulose (HPMC) or carboxymethyl cellulose (CMC), Polyethylene glycol (PEG).
23. The catalyst delivery composition of any preceding claim wherein the chelate is present in a detergent composition comprising an oxidative bleach.
24. The catalyst delivery composition of claim 23 wherein the chelate is separate from the oxidative bleach, such as sodium percarbonate, which is a source of hydrogen peroxide.
25. The catalyst delivery composition of any preceding claim wherein the composition is a dishwashing detergent composition.
Citation Information
Patent Citations
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