WO2023199939A1 - 組成物 - Google Patents
組成物 Download PDFInfo
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- WO2023199939A1 WO2023199939A1 PCT/JP2023/014846 JP2023014846W WO2023199939A1 WO 2023199939 A1 WO2023199939 A1 WO 2023199939A1 JP 2023014846 W JP2023014846 W JP 2023014846W WO 2023199939 A1 WO2023199939 A1 WO 2023199939A1
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/395—Bleaching agents
- C11D3/3951—Bleaching agents combined with specific additives
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/28—Heterocyclic compounds containing nitrogen in the ring
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/39—Organic or inorganic per-compounds
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/395—Bleaching agents
- C11D3/3953—Inorganic bleaching agents
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/395—Bleaching agents
- C11D3/3956—Liquid compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/02—Inorganic compounds
- C11D7/04—Water-soluble compounds
- C11D7/06—Hydroxides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/32—Organic compounds containing nitrogen
- C11D7/3281—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
Definitions
- the present invention relates to compositions, methods of preserving compounds, methods of oxidation, methods of bleaching, use of certain compositions as oxidizing agents, and use of certain compositions as bleaching agents.
- An oxidizing agent composition is a composition containing a compound (oxidizing agent) that has an oxidizing effect on other substances. This oxidation effect can be recognized as phenomena such as decolorization, bleaching, and discoloration for colored substances. Oxidizing agent compositions can be used for a variety of purposes, including bleaching hard items such as baths, toilets, and kitchens, removing mold, bleaching textile products such as clothing, decomposing substances that cause dirt and odors, disinfecting, bleaching pulp, and scouring fibers. It is used for various purposes.
- stains that occur in the living environment are dealt with by cleaning, bleaching, sterilizing, etc. for purposes such as maintaining aesthetic appearance and hygiene.
- stains in hard-to-clean areas such as toilets, bathrooms, bathtubs, and water pipes are difficult to remove using only detergents containing surfactants as the main ingredient, and bleach is often used.
- dark stains on bathroom bathtubs, tile joints, door frames, window frames, controllers, and triangular corners in the kitchen are caused by pigments produced by molds such as Cladosporium bacteria, and cleansers and surfactants. Since it is difficult to remove it by itself, the commonly used method is to remove it using the bleaching action of an aqueous sodium hypochlorite solution.
- mold removers using sodium hypochlorite have excellent bleaching and cleaning performance, but are highly irritating to the eyes and skin, and have a distinctive chlorine-based odor, making them difficult to use in small bathrooms. Care must be taken, and there is also the problem that toxic gas will be generated if mixed with acidic cleaning agents by mistake.
- JP-A-3-220298 discloses a bleach composition for hard surfaces that uses hydrogen peroxide, an alkaline agent, and a bleach activator in combination.
- Japanese Patent Laid-Open No. 2009-155292 discloses a composition that exhibits high sterilizing and sterilizing effects and is composed of a peroxide that generates hydrogen peroxide when dissolved in water, a chelating agent, a copper compound, and a binder compound. Disclosed.
- JP-A No. 2002-80894 discloses a highly viscous composition 1 containing hydrogen peroxide, an organic thickener, an organic chelating agent, and water, an inorganic alkali, an organic thickener, and a bleaching active composition.
- a bleaching agent composition is described in which a high viscosity composition 2 containing a bleaching agent and water is mixed at the time of use.
- Oxygen bleaching agents for example, react with hydrogen peroxide, which is an oxidizing agent, with an organic acid ester, which is a bleaching activator, to generate bleaching active species (organic peracid, etc.) and bleach the target object. Oxidize and bleach.
- an oxygen-based bleach it is desirable that the bleach activator can be stably supplied in the form of an aqueous solution from the viewpoint of ease of handling.
- the present invention provides a composition that can be used as a bleach activator for oxygen bleaching agents and is stable in the form of an aqueous solution.
- the present invention provides (A) one or more compounds selected from the following general formula (A1) and the following general formula (A2) [hereinafter referred to as component (A)], and water. and is acidic.
- R 1 is an alkyl group having 1 to 24 carbon atoms and which may contain a hetero atom.
- R12 is a group containing a carbon atom and a heteroatom of an ion that pairs with N + of the pyridine ring, and may contain a heteroatom different from the above heteroatom, and has a total carbon number of 1 to 24 .
- L is n halogen atoms, n is 1, 2 or 3, and L is bonded to n different carbon atoms at any one of the 2nd, 4th and 6th positions of the pyridine ring.
- a ⁇ is an anion.
- a group other than L may be bonded to carbon atoms other than the carbon atom to which L is bonded.
- the present invention also relates to a method for preserving a compound, in which component (A) is preserved in acidic water.
- the present invention also relates to an oxidation method in which a treatment liquid prepared from the composition of the present invention is brought into contact with an object in the presence of hydrogen peroxide.
- the present invention also relates to a bleaching method in which a treatment liquid prepared from the composition of the present invention is brought into contact with an object in the presence of hydrogen peroxide.
- the present invention also relates to the use of the composition of the present invention for producing an oxidizing agent.
- the present invention also relates to the use of the composition of the present invention for producing a bleaching agent.
- a composition that can be used as a bleach activator for oxygen bleaching agents and is stable in the form of an aqueous solution.
- an organic acid ester as a bleach activator for hydrogen peroxide, which is an oxygen bleaching agent.
- the reaction to generate bleaching active species proceeds relatively efficiently in alkaline conditions, but progresses slowly in neutral conditions. Therefore, bleaching agents and oxidizing agents that use peracids such as hydrogen peroxide tend to have lower bleaching and oxidizing power in neutral conditions.
- the composition of the present invention is used in combination with hydrogen peroxide, excellent effects can be obtained without reducing the oxidizing power and bleaching power of hydrogen peroxide even when the composition is neutral.
- composition of the present invention has excellent stability is not necessarily clear, but active esters, which are common bleach activators, are inactive because their active ester groups are protonated and activated under acidic conditions. It tends to be stable. On the other hand, this is presumed to be because component (A) of the present invention does not have an active ester group and is not activated even under acidic conditions.
- component (A) of the composition of the present invention is a common organic oxidant. This is presumed to be because active species are sufficiently formed even if it is neutral due to its high reactivity to hydrogen peroxide compared to acid precursors. In addition, under acidic conditions, the reactivity of component (A) with hydrogen peroxide is extremely low, and it is presumed that component (A) can exist stably even if hydrogen peroxide coexists in the composition of the present invention. Ru.
- the mechanism of the present invention is not limited to these.
- Component (A) is one or more compounds selected from the compound represented by the general formula (A1) and the compound represented by the general formula (A2).
- R 1 is an alkyl group having 1 to 24 carbon atoms and which may contain a hetero atom.
- the number of carbon atoms in the alkyl group of R 1 is 1 or more, further 8 or more, further 12 or more, and 24 or less, further 20 or less, and further 18 or less.
- the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, and a phosphorus atom.
- R 1 When R 1 is an alkyl group containing a hetero atom, the number of carbon atoms in R 1 may be the total number of carbon atoms in the carbon chain excluding the hetero atom. R 1 may be an alkyl group having 1 or more and 24 or less carbon atoms that does not contain a hetero atom.
- R 1 is an alkyl group containing a hetero atom
- examples of -R 1 include -CH 2 -(CH 2 ) n11 -Y 1 -(CH 2 ) n12 -CH 3 .
- Y 1 is a heteroatom
- n11 and n12 are each an integer of 0 to 22, and the sum of n11 and n12 is 0 to 22.
- R 12 contains a carbon atom and a heteroatom of an ion that pairs with N + of the pyridine ring, and may contain a heteroatom different from the above heteroatom, and has a total carbon number of 1
- the above is a group of 24 or less.
- the ion possessed by R 12 and N + of the pyridine ring form a betaine structure.
- Examples of -R 12 include -CH 2 -R 121 -Y 2 -R 122 .
- Y 2 is an anion of a heteroatom
- R 121 and R 122 are each a single bond or an alkyl group that may contain a heteroatom different from Y 2 , and the sum of R 121 and R 122 The number of carbon atoms is 0 or more and 22 or less.
- examples of -R 12 include -CH 2 -(CH 2 ) n21 -(Y 3 ) n22 -(CH 2 ) n23 -SO 3 - .
- n21 and n23 are each an integer of 0 or more and 23 or less, the sum of n21 and n23 is 0 or more and 23 or less, Y3 is a heteroatom, and n22 is 0 or 1.
- L is n halogen atoms
- n is 1, 2 or 3
- L is any of the 2-position, 4-position and 6-position of the pyridine ring. It is bonded to n different carbon atoms.
- the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, with a chlorine atom being preferred. Note that the position numbers of the pyridine ring are as follows.
- a - is an anion.
- the anion of A ⁇ may be either an organic anion or an inorganic anion.
- Examples of the A ⁇ anion include anions that are conjugate bases of acids with a pKa of 5 or less.
- Examples of A - anions include sulfonate ions such as trifluoromethanesulfonate ion ( -OTf ), paratoluenesulfonate ion ( -OTs ), and methanesulfonate ion ( -OMs ), and methylsulfate ion ( -OSO ).
- Alkyl sulfate ions such as 3 Me
- halide ions such as chloride ions (Cl ⁇ ) and bromide ions (Br ⁇ )
- fluoroborate ions such as tetrafluoroborate ions (BF 4 ⁇ )
- fluororoborate ions such as tetrafluoroborate ions (BF 4 ⁇ )
- fluorophosphate ions such as (PF 6 ⁇ )
- imide ions such as bis(trifluoromethanesulfonic acid) imide ions ((CF 3 SO 2 ) 2 N ⁇ )
- fluoroacetate ions such as trifluoroacetate ions (CF 3 COO ⁇ ).
- a ⁇ is preferably an anion selected from ⁇ OTf , ⁇ OSO 3 Me, ⁇ OTs , ⁇ OMs , Cl ⁇ and Br ⁇ .
- carbon atoms other than the carbon atom to which L is bonded are groups other than L, such as -COO-R 2 , -CONH-R 3 , bonding with a group such as -CON(R 4 )(R 5 ) (R 2 , R 3 , R 4 , R 5 are each an alkyl group having 3 or more carbon atoms which may include a heteroatom substitution) You may do so.
- Component (A) includes one or more compounds selected from the compounds represented by the following general formula (A1-1) and the compounds represented by the following general formula (A2-1).
- R 1 is an alkyl group having 1 to 24 carbon atoms and which may contain a hetero atom.
- R12 is a group containing a carbon atom and a heteroatom of an ion that pairs with N + of the pyridine ring, and may contain a heteroatom different from the above heteroatom, and has a total carbon number of 1 to 24 .
- L is n halogen atoms, n is 1 or 2, and L is bonded to any n different carbon atoms at the 2nd, 4th, and 6th positions of the pyridine ring.
- Z is a group selected from -COO-R 2 , -CONH-R 3 and -CON(R 4 )(R 5 ), and R 2 , R 3 , R 4 , and R 5 each represent a heteroatom. It is an alkyl group having 3 or more carbon atoms which may be included. Z is bonded to a different carbon atom from the carbon atom to which L is bonded among the carbon atoms of the pyridine ring. A ⁇ is an anion. Among the carbon atoms of the pyridine ring, groups other than L and Z may be bonded to carbon atoms other than those to which L and Z are bonded. ]
- R 1 , L, A ⁇ and R 12 are as described in the general formula (A1) and the general formula (A2), respectively. They are the same.
- n is 1 or 2.
- Z is a group selected from -COO-R 2 , -CONH-R 3 and -CON(R 4 )(R 5 ), and Z is bonded to a different carbon atom from the carbon atom to which L is bonded among the carbon atoms of the pyridine ring.
- R 2 , R 3 , R 4 , and R 5 are selected from the viewpoint of improving oxidative decomposition activity (hereinafter also simply referred to as oxidative decomposition activity) when the composition of the present invention is incorporated into an oxidizing agent, a bleaching agent, etc.
- Each is an alkyl group having 3 or more carbon atoms, further 8 or more carbon atoms, further 12 or more carbon atoms, and 24 or less carbon atoms, further 18 or less carbon atoms, which may contain a hetero atom.
- the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, and a phosphorus atom.
- R 2 , R 3 , R 4 and R 5 are alkyl groups containing a hetero atom
- the number of carbon atoms in R 2 , R 3 , R 4 and R 5 is the total number of carbon atoms in the carbon chain excluding the hetero atom. It's good.
- Compounds of general formula (A1-1) and general formula (A2-1) are such that carbon atoms other than the carbon atoms to which L and Z are bonded among the carbon atoms of the pyridine ring are groups other than L and Z, such as nitro It may be bonded to a trifluoromethyl group, a sulfonyl group, a cyano group, a carboxyl group, a methoxy group, a dimethylamino group, or the like.
- component (A) a compound represented by (A1-2) can be mentioned.
- R 1 is an alkyl group having 1 to 24 carbon atoms that may contain a hetero atom
- L is n halogen atoms
- n is 1, 2, or 3
- L is is bonded to n different carbon atoms at any one of the 2nd, 4th and 6th positions of the pyridine ring
- a - is an anion.
- component (A) a compound represented by (A2-2) can be mentioned.
- L is n halogen atoms, n is 1, 2, or 3, and L is bonded to any n different carbon atoms at the 2-position, 4-position, or 6-position of the pyridine ring. are doing.
- R 11 is an alkylene group having 1 or more and 24 or less carbon atoms that may contain a hetero atom.
- R 11 is an alkylene group having 1 to 24 carbon atoms and which may contain a hetero atom.
- the number of carbon atoms in R 11 is, for example, 2 or more, 3 or more, 20 or less, 18 or less, 16 or less, 14 or less, 12 or less, 10 or less, 8 or less, 6 or less, and 4 or less.
- the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, and a phosphorus atom.
- R 11 is an alkylene group containing a hetero atom
- the number of carbon atoms in R 11 may be the total number of carbon atoms in the carbon chain excluding the hetero atom.
- R 11 may be an alkylene group having 1 or more and 24 or less carbon atoms that does not contain heteroatom substitution.
- Component (A) includes the compound represented by the general formula (A1-1), the compound represented by the general formula (A1-2), the compound represented by the general formula (A2-1), and the compound represented by the general formula (A2-1). It may be one or more compounds selected from the compounds represented by the general formula (A2-2), and furthermore, the compound represented by the general formula (A1-1) and the general formula (A2-2). It may be one or more compounds selected from the compounds represented.
- composition of the present invention contains component (A) in an amount of, for example, 0.01% by mass or more, further 0.1% by mass or more, further 1% by mass or more, and 20% by mass, from the viewpoint of improving oxidative decomposition activity.
- the content is preferably 10% by mass or less, further preferably 5% by mass or less.
- the composition of the present invention contains water.
- water examples include ion exchange water and tap water. Water can be used in an amount to bring the total composition of the composition of the invention to 100% by weight.
- the composition of the present invention may contain water, for example, 50% by mass or more, further 80% by mass or more, further 90% by mass or more, and 99% by mass or less, further 95% by mass or less, further 90% by mass or less. Can be done.
- the composition of the present invention can contain (B) hydrogen peroxide [hereinafter referred to as component (B)].
- component (B) hydrogen peroxide
- the composition of the present invention contains component (B) in an amount of, for example, 0.01% by mass or more, further 1% by mass or more, further 3% by mass or more, from the viewpoint of excellent safety.
- the content is preferably at least 30% by mass, more preferably at most 20% by mass, and even more preferably at most 10% by mass.
- the content of component (B) relative to 1 part by mole of the content of component (A) is, for example, 1 part by mole. More preferably, the amount is 22 mol parts or more, 33 mol parts or more, 100 mol parts or less, further 55 mol parts or less, and further preferably 44 mol parts or less.
- composition of the present invention preferably contains a bleach activation aid as component (C).
- component (A) of the present invention When component (A) of the present invention is combined with component (B) and component (C), the oxidative decomposition effect and bleaching effect are improved. Although the reason is not necessarily clear, it is inferred as follows. Component (A) reacts with hydrogen peroxide under neutral conditions to produce peracid species, which react with the dye, resulting in bleaching. Here, it is thought that there is no difference between the solution system and the cloth system in the first step where component (A) and hydrogen peroxide react. On the other hand, the next step, where the peracid species and stain pigment molecules react, differs greatly between solution systems and cloth systems.
- component (C) such as iminium salt, which is generally used as a catalyst for Davis oxidation, receives active oxygen from peracid species and generates stable peracid species.
- active oxygen contained in peracid species derived from unstable component (A) is transferred to component (C) by using component (C), for example, an iminium salt, and stable oxidizing active species are generated. This enables the oxidative decomposition and bleaching of the pigments present on the fabric.
- component (C) examples include a compound represented by the following general formula (C-1) [hereinafter referred to as component (C-1)].
- Z is an alkyl group having 1 to 24 carbon atoms which may contain a heteroatom, nitro, halo, cyano, amino, aminoalkyl, thioalkyl, sulfoalkyl, carboxyester, hydroxy, and carboxamide. is a selected group, and n is a number from 0 to 9.
- R 1c is an alkyl group having 1 to 24 carbon atoms which may contain a heteroatom, and A - is an anion.
- a - is an anion.
- the anion of A ⁇ may be either an organic anion or an inorganic anion.
- Examples of the A ⁇ anion include anions that are conjugate bases of acids with a pKa of 5 or less.
- Examples of A - anions include sulfonate ions such as trifluoromethanesulfonate ion ( -OTf ), paratoluenesulfonate ion ( -OTs ), and methanesulfonate ion ( -OMs ), and methylsulfate ion ( -OSO ).
- Alkyl sulfate ions such as 3 Me
- halide ions such as chloride ions (Cl ⁇ ) and bromide ions (Br ⁇ )
- fluoroborate ions such as tetrafluoroborate ions (BF 4 ⁇ )
- hexafluorophosphate ions Fluorophosphate ions such as (PF 6 ⁇ ), imide ions such as bis(trifluoromethanesulfonic acid) imide ions ((CF 3 SO 2 ) 2 N ⁇ ), and fluoroacetate ions such as trifluoroacetate ions (CF 3 COO ⁇ ).
- a ⁇ is preferably an anion selected from ⁇ OTf , ⁇ OSO 3 Me, ⁇ OTs , ⁇ OMs , BF 4 ⁇ , Cl ⁇ , and Br ⁇ .
- component (C-1) is preferably a quaternary imine salt, more specifically a substituted or unsubstituted isoquinolinium salt, and more preferably a 3,4-dihydroisoquinolinium salt.
- salt more preferably N-methyl-3,4-dihydroisoquinolinium salt, even more preferably N-methyl-3,4-dihydroisoquinolinium p-toluenesulfonate and N-methyl -3,4-dihydroisoquinolinium tetrafluoroborate, and even more preferably N-methyl-3,4-dihydroisoquinolinium tetrafluoroborate.
- the composition of the present invention contains component (C) and further contains component (C-1)
- the composition contains component (C) and further contains component (C-1), for example, 0.01% by mass.
- the content may be 0.1% by mass or more, further 0.5% by mass or more, 20% by mass or less, further 10% by mass or less, and further 5% by mass or less.
- component (C) based on 1 mole part of the content of component (A), and further (
- the content of component C-1) is, for example, 0.01 mole or more, further 0.1 mole or more, further 1 mole or more, and 100 mole or less, further 10 mole or less, and further 2 mole parts. It is preferable that it is below.
- the composition of the present invention preferably contains component (B) and component (C).
- component (B) component (C)
- component (C) component (C)
- C-1 component (C-1)
- the content of component (B) per 1 mole part is, for example, 1 mole part or more, further 22 mole parts or more, further 33 mole parts or more, and 100 mole parts or less, further 55 mole parts or less, and further 44 mole parts. It may be the following.
- composition of the present invention can contain any other components in addition to component (B) and component (C).
- optional components include, for example, chelating agents, thickeners, surfactants, polymers, and the like.
- component (B) may be blended as a hydrogen peroxide solution.
- a predetermined component is blended in a form containing water, such as a hydrogen peroxide solution, the water contained in that form becomes part or all of the water component in the liquid composition of the present invention.
- composition of the present invention is suitable for use as an oxidizing agent. That is, for example, the composition of the present invention can be used together with hydrogen peroxide as an oxidizing agent or used for the production of an oxidizing agent. Furthermore, the composition of the present invention is suitable for use as a bleaching agent. Thus, for example, the composition of the invention can be used together with hydrogen peroxide as a bleaching agent or for the production of a bleaching agent.
- the concentration of component (A) is, for example, 0.0001% by mass or more, further 0.001% by mass or more, further 0.01% by mass or more. It may be at least 10% by mass, further at most 1% by mass, and even at most 0.1% by mass.
- the concentration of component (B) when used, for example, as an oxidizing agent or a bleaching agent is, for example, 0.001% by mass or more, and even 0.
- the content may be .01% by weight or more, further 0.1% by weight or more, and 30% by weight or less, further 3% by weight or less, and even 1% by weight or less.
- the concentration of component (C) when used, for example, as an oxidizing agent or a bleaching agent is, for example, 0.0001% by mass or more, and even 0.
- the content may be .001% by mass or more, further 0.01% by mass or more, and 10% by mass or less, further 1% by mass or less, and even 0.1% by mass or less.
- the composition of the present invention may be in any form such as a liquid composition or a gel composition.
- the composition of the present invention is preferably in liquid form.
- the composition of the present invention can also be obtained, for example, by mixing a solid agent containing component (A) with water. That is, the present invention provides a kit for an acidic composition containing component (A) and water, which is configured to include a solid agent containing component (A).
- the composition of the present invention may have a pH at 25°C of, for example, 2 or more, further 3 or more, and less than 7, further 6 or less, and further 5 or less.
- a pH adjuster may be included to achieve such a pH.
- pH adjusters include hydrogen phosphates such as disodium hydrogen phosphate and potassium dihydrogen phosphate, organic acids such as lactic acid, succinic acid, gluconic acid, citric acid, acetic acid, and tartaric acid, phosphoric acid, boric acid, and hydrochloric acid.
- inorganic acids such as sulfuric acid, sulfonic acids such as para-toluenesulfonic acid, camphorsulfonic acid, and methanesulfonic acid.
- pH adjusting agents may be selected in combination with buffering capacity.
- the composition of the present invention can be used to treat objects such as bleaching hard articles such as baths, toilets, and kitchens, removing mold, bleaching clothing, decomposing substances that cause stains and odors, disinfecting, killing viruses, and bleaching pulp. It can be used in a variety of applications where the oxidizing action has a useful effect on.
- the composition of the present invention can be used, if necessary, in combination with hydrogen peroxide or the like to form, for example, a bleach composition, a bleach cleaning agent composition, a mold remover composition, a decolorizing agent composition, a deodorant composition, a disinfectant composition. It can be used as a compound, virucidal composition, etc.
- the composition of the present invention is preferably used for bleaching or bleach cleaning. Furthermore, it is preferably used for bleaching or bleaching and cleaning hard articles.
- the invention provides the use of the composition of the invention for the production of oxidizing agents.
- the invention also provides the use of the compositions of the invention for the production of bleaching agents. If the composition of the present invention has a composition suitable for oxidation or bleaching, the composition can be used as it is to produce an oxidizing agent or a bleaching agent.
- the oxidizing agent or bleaching agent may contain component (A) in an amount of, for example, 0.0001% by mass or more, further 0.001% by mass or more, furthermore 0.01% by mass or more, from the viewpoint of improving the oxidative decomposition activity of component (A). , and preferably contains 10% by mass or less, further 1% by mass or less, further preferably 0.1% by mass or less.
- the composition can contain component (A) within this range.
- the oxidizing agent or bleaching agent preferably contains component (B).
- the oxidizing agent or bleaching agent contains component (B) in an amount of, for example, 0.001% by mass or more, further 0.01% by mass or more, further 0.1% by mass or more, and 30% by mass or less, further 3% by mass.
- the content is preferably at most 1% by mass, more preferably at most 1% by mass.
- the composition can contain component (B) within this range.
- the oxidizing agent or bleaching agent may contain component (C).
- the oxidizing agent or bleaching agent contains component (C) in an amount of, for example, 0.0001% by mass or more, further 0.001% by mass or more, further 0.01% by mass or more, and 10% by mass or less, further 1% by mass.
- the content is preferably 0.1% by mass or less, more preferably 0.1% by mass or less.
- the molar parts of component (C) relative to 1 molar part of component (A) and the molar parts of component (A) relative to 1 molar part of component (C) may each contain component (C) within the above ranges. preferable.
- the composition can contain component (C) within this range.
- the present invention provides an oxidation method in which a treatment liquid prepared from the composition of the present invention is brought into contact with an object in the presence of hydrogen peroxide.
- the present invention also provides a bleaching method in which a treatment liquid prepared from the composition of the present invention (hereinafter also referred to as the treatment liquid of the present invention) is brought into contact with an object in the presence of hydrogen peroxide.
- the treatment liquid of the present invention is preferably a treatment liquid containing component (A), component (B), and water.
- the treatment liquid of the present invention is also preferably a treatment liquid containing component (A), component (B), component (C), and water. If the composition of the present invention has a composition suitable for oxidation and bleaching, the composition can be used as it is as the treatment liquid of the present invention.
- the treatment liquid of the present invention is prepared by mixing a composition containing component (A) but not containing component (B) with a compound that is a source of component (B) or a composition containing component (B). It may also be prepared by When component (C) is used, it may be mixed in any way, and one or both of the two compositions may contain component (C).
- the treatment liquid of the present invention comprises the composition of the present invention containing the component (A) and water, and a component (B) and/or a source of the component (B), such as peroxide that produces hydrogen peroxide in water. It can be obtained by mixing the compound with water, component (C), etc., if necessary.
- Peroxides that generate hydrogen peroxide in water include inorganic peroxides and hydrogen peroxide adducts, preferably percarbonates, tripolyphosphate/hydrogen peroxide adducts, and pyrophosphate/peroxide adducts.
- Hydrogen oxide adducts urea/hydrogen peroxide adducts, sulfate/hydrogen peroxide adducts, perborate, persilicate, peroxide salts, and more preferably sodium percarbonate, sodium tripolyphosphate/ Hydrogen peroxide adduct, sodium pyrophosphate/hydrogen peroxide adduct, urea/hydrogen peroxide adduct, or 4Na 2 SO 4.2H 2 O 2 , sodium perborate monohydrate, sodium perborate tetrahydrate compounds, sodium persilicate, sodium peroxide, calcium peroxide, etc.
- the composition, the component (B) and/or the source of the component (B), and optionally water, (C) can also be obtained by mixing other components.
- a pH adjuster such as a phosphate buffer that also functions as a buffer may be added to adjust the pH of the treatment solution to 3 or higher, 5 or higher, for example. Furthermore, it may be adjusted to 6 or more, 12 or less, further 10 or less, and further 8 or less.
- the treatment liquid of the present invention contains component (A) in an amount of, for example, 0.0001% by mass or more, further 0.001% by mass or more, furthermore 0.01% by mass or more, and 10% by mass or more, from the viewpoint of improving oxidative decomposition activity.
- the content is preferably at most 1% by mass, more preferably at most 1% by mass, and further preferably at most 0.1% by mass.
- the treatment liquid of the present invention contains component (B) in an amount of, for example, 0.001% by mass or more, further 0.01% by mass or more, further 0.1% by mass or more, and 30% by mass or less, furthermore 3% by mass or less. , and may further contain 1% by mass or less.
- the treatment liquid of the present invention contains component (C) in an amount of, for example, 0.0001% by mass or more, further 0.001% by mass or more, furthermore 0.01% by mass or more, and 10% by mass or more, from the viewpoint of improving oxidative decomposition activity. It can be contained in an amount of not more than 1% by mass, further not more than 1% by mass, and further not more than 0.1% by mass.
- the objects to be subjected to the oxidation method and the bleaching method include, for example, hard articles such as baths, toilets, and kitchens, and textile products such as clothing.
- the composition of the present invention can be brought into contact with the object by dipping, coating, spraying, or the like in the presence of hydrogen peroxide. There are no limitations on the contact time or contact temperature when the composition of the present invention and the object are brought into contact.
- the treatment liquid of the present invention can contain any of the components described in the composition of the present invention.
- the pH of the treatment liquid of the present invention may be, for example, 3 or more, further 5 or more, further 6 or more, and 12 or less, further 10 or less, and further 8 or less.
- This pH is the pH at the temperature at which the oxidation or bleaching method of the invention is carried out, but may be, for example, the pH at 25°C.
- excellent oxidizing power or bleaching power can be obtained in the presence of hydrogen peroxide even at a pH near neutrality.
- the present invention provides a method for preserving a compound (hereinafter also referred to as the preservation method of the present invention) in which component (A) is preserved in acidic water.
- the matters described for the composition of the present invention can be appropriately applied to the preservation method of the present invention.
- Specific examples and preferred examples of component (A) in the preservation method of the present invention are also the same as in the composition of the present invention.
- the preservation method of the present invention may be a method of preserving component (A) or the composition of the present invention.
- the content of component (A) in acidic water is, for example, 0.01% by mass or more, further 0.1% by mass or more, further 1% by mass or more, and 20% by mass or less, Furthermore, it may be 10% by mass or less, furthermore, 5% by mass or less.
- component (A) is preserved in acidic water.
- the acidic water used for storage may have a pH of, for example, 2 or more, further 3 or more, and less than 7, further 6 or less, and further 5 or less.
- a pH adjuster may be included to achieve such a pH.
- pH adjusters include hydrogen phosphates such as disodium hydrogen phosphate and potassium dihydrogen phosphate, organic acids such as lactic acid, succinic acid, gluconic acid, citric acid, acetic acid, and tartaric acid, phosphoric acid, boric acid, and hydrochloric acid.
- inorganic acids such as sulfuric acid, sulfonic acids such as para-toluenesulfonic acid, camphorsulfonic acid, and methanesulfonic acid.
- pH adjusting agents may be selected in combination with buffering capacity. Note that this pH is the pH in a state including optional components such as component (A) and component (B).
- the preservation method of the present invention can be carried out in the presence of components other than component (A).
- the optional ingredients mentioned in the composition of the present invention can be added to acidic water for preservation.
- component (B) is allowed to coexist, in the preservation method of the present invention, the content of component (B) in acidic water is, for example, 0.01% by mass or more, further 1% by mass or more, furthermore 3% by mass or more, The content may be 30% by mass or less, further 20% by mass or less, and further 10% by mass or less.
- component (A) in acidic water in the coexistence of component (C), a bleach activation aid.
- component (C) a bleach activation aid.
- the content of component (C) in acidic water is, for example, 0.01% by mass or more, further 0.1% by mass or more, further 1% by mass.
- the content may be 20% by mass or less, further 10% by mass or less, and further 5% by mass or less.
- the preservation method of the present invention can be used, for example, as a method for preserving the composition of the present invention, the composition of the present invention that is used as an oxidizing agent, or the composition of the present invention that is used as a bleaching agent.
- the temperature of the acidic water is not particularly limited, but may be, for example, 0°C or higher, further 25°C or higher, 60°C or lower, and further 50°C or lower.
- the preservation period is not particularly limited, but may be, for example, one day or more, further 14 days or more, and 730 days or less, further 365 days or less.
- component (A) for example, water, component (A), optional components (B), (C), and other optional components are placed in a predetermined container, and the liquid is acidified, preferably Component (A) can be stored by adjusting the pH within the above range.
- the shape and capacity of the container are not limited.
- the container preferably has a means for sealing the opening, such as a lid or a stopper.
- (A) contains one or more compounds selected from the compound represented by the following general formula (A1) and the compound represented by the following general formula (A2) [hereinafter referred to as component (A)], and water, A composition that is acidic.
- R 1 is an alkyl group having 1 to 24 carbon atoms and which may contain a hetero atom.
- R12 is a group containing a carbon atom and a heteroatom of an ion that pairs with N + of the pyridine ring, and may contain a heteroatom different from the above heteroatom, and has a total carbon number of 1 to 24 .
- L is n halogen atoms, n is 1, 2 or 3, and L is bonded to n different carbon atoms at any one of the 2nd, 4th and 6th positions of the pyridine ring.
- a ⁇ is an anion.
- a group other than L may be bonded to carbon atoms other than the carbon atom to which L is bonded.
- the number of carbon atoms in the alkyl group of R 1 is 1 or more, further 8 or more, further 12 or more, and 24 or less, further 20 or less, and further 18 or less, as described in ⁇ 1>. composition.
- R 1 is an alkyl group containing a hetero atom, furthermore -CH 2 -(CH 2 ) n11 -Y 1 -(CH 2 ) n12 -CH 3 , and Y 1 is a hetero atom-containing alkyl group.
- -R 12 is -CH 2 -R 121 -Y 2 -R 122
- Y 2 is a heteroatom anion
- R 121 and R 122 are single bonds.
- the total number of carbon atoms of R 121 and R 122 is 0 or more and 22 or less, described in any of ⁇ 1> to ⁇ 5>.
- -R 12 is -CH 2 -(CH 2 ) n21 -(Y 3 ) n22 -(CH 2 ) n23 -SO 3 -
- n21 and n23 are each 0 or more is an integer of 23 or less
- the sum of n21 and n23 is 0 or more and 23 or less
- Y3 is a heteroatom
- n22 is 0 or 1, described in any of ⁇ 1> to ⁇ 5>.
- L is a halogen atom selected from a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and further is a chlorine atom, ⁇ 1> to ⁇ 7>
- a - is an anion selected from a sulfonate ion, an alkyl sulfate ion, a halide ion, a fluoroborate ion, a fluorophosphate ion, an imide ion, and a fluoroacetate ion;
- carbon atoms other than the carbon atom to which L is bonded among the carbon atoms of the pyridine ring are bonded to a group other than L;
- carbon atoms other than the carbon atom to which L is bonded are -COO-R 2 , -CONH-R 3 , and -CON(R 4 )(R 5 ) (here, R 2 , R 3 , R 4 and R 5 are each bonded to a group selected from the group consisting of an alkyl group having 3 or more carbon atoms which may include a heteroatom substitution, according to any one of ⁇ 1> to ⁇ 11>.
- Component (A) is a compound represented by the following general formula (A1-1), a compound represented by the following general formula (A1-2), the following general formula (A2-1), and the following general formula (A2- 2) is one or more compounds selected from the compounds represented by formula (A1-1) below, compounds represented by general formula (A1-2) below, and the general formula below.
- R 1 is an alkyl group having 1 to 24 carbon atoms and which may contain a hetero atom.
- L is n halogen atoms, n is 1 or 2, and L is bonded to any n different carbon atoms at the 2nd, 4th, and 6th positions of the pyridine ring.
- Z is a group selected from -COO-R 2 , -CONH-R 3 and -CON(R 4 )(R 5 ), and R 2 , R 3 , R 4 , and R 5 each represent a heteroatom. It is an alkyl group having 3 or more carbon atoms which may be included.
- Z is bonded to a different carbon atom from the carbon atom to which L is bonded among the carbon atoms of the pyridine ring.
- a ⁇ is an anion.
- groups other than L and Z may be bonded to carbon atoms other than those to which L and Z are bonded.
- R 1 is an alkyl group having 1 to 24 carbon atoms that may contain a hetero atom
- L is n halogen atoms
- n is 1, 2, or 3
- L is bonded to n different carbon atoms at any of the 2nd, 4th and 6th positions of the pyridine ring
- a - is an anion.
- R 12 includes a carbon atom and a heteroatom of an ion that pairs with N + of the pyridine ring, and may contain a heteroatom different from the above heteroatom, and It is a group of number 1 or more and 24 or less.
- L is n halogen atoms, n is 1 or 2, and L is bonded to any n different carbon atoms at the 2nd, 4th, and 6th positions of the pyridine ring.
- Z is a group selected from -COO-R 2 , -CONH-R 3 and -CON(R 4 )(R 5 ), and R 2 , R 3 , R 4 , and R 5 each represent a heteroatom.
- Z is bonded to a different carbon atom from the carbon atom to which L is bonded among the carbon atoms of the pyridine ring.
- a ⁇ is an anion.
- groups other than L and Z may be bonded to carbon atoms other than those to which L and Z are bonded.
- R 11 is an alkylene group having 1 to 24 carbon atoms and which may contain a hetero atom.
- L is n halogen atoms, n is 1 or 2, and L is bonded to any n different carbon atoms at the 2nd, 4th, and 6th positions of the pyridine ring.
- a group other than L may be bonded to carbon atoms other than the carbon atom to which L is bonded.
- the heteroatom of R 1 is at least one selected from nitrogen atom, oxygen atom, sulfur atom, and phosphorus atom, ⁇ 13> or The composition described in ⁇ 14>.
- R 1 is any one of ⁇ 13> to ⁇ 15>, which is an alkyl group having 1 to 24 carbon atoms and not containing a hetero atom. Composition as described.
- R 1 is an alkyl group containing a hetero atom, and further -CH 2 -(CH 2 ) n11 -Y 1 -(CH 2 ) n12 -CH 3 , Y 1 is a heteroatom, n11 and n12 are each an integer of 0 to 22, the sum of n11 and n12 is 0 to 22, ⁇ 13> to ⁇ 15>
- -R 12 is -CH 2 -R 121 -Y 2 -R 122
- Y 2 is a heteroatom anion
- R 121 and R 122 are a single bond. or an alkyl group which may contain a heteroatom different from Y 2
- the total number of carbon atoms of R 121 and R 122 is 0 or more and 22 or less, described in any one of ⁇ 13> to ⁇ 17> composition.
- -R 12 is -CH 2 -(CH 2 ) n21 -(Y 3 ) n22 -(CH 2 ) n23 -SO 3 -
- n21 and n23 are each, An integer of 0 to 23, the sum of n21 and n23 is 0 to 23, Y3 is a heteroatom, and n22 is 0 or 1, described in any of ⁇ 13> to ⁇ 17>. composition.
- L is a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
- a - is an anion selected from an organic anion and an inorganic anion, as described in any one of ⁇ 13> to ⁇ 20> composition.
- a - is an anion that is a conjugate base of an acid with a pKa of 5 or less, and is any one of ⁇ 13> to ⁇ 21>. Composition as described.
- a - is a sulfonate ion, an alkyl sulfate ion, a halide ion, a fluoroborate ion, a fluorophosphate ion, an imide ion, and a fluoroacetate ion.
- trifluoromethanesulfonate ion ( -OTf ), paratoluenesulfonate ion ( -OTs ), methanesulfonate ion ( -OMs ), methylsulfate ion ( -OSO3Me ), chloride compound ion (Cl ⁇ ), bromide ion (Br ⁇ ), tetrafluoroborate ion (BF 4 ⁇ ), hexafluorophosphate ion (PF 6 ⁇ ), bis(trifluoromethanesulfonic acid) imide ion ((CF 3 SO 2 ) 2 N ⁇ ), and an anion selected from trifluoroacetate ion (CF 3 COO ⁇ ), and further selected from ⁇ OTf, ⁇ OSO 3 Me, ⁇ OTs, ⁇ OMs, Cl ⁇ , and Br ⁇
- CF 3 COO ⁇ an anion selected from trifluor
- the number of carbon atoms in R 11 is 2 or more, further 3 or more, and 20 or less, further 18 or less, further 16 or less, further 14 or less, further 12 or less, further 10 or less, and further The composition according to any one of ⁇ 13> to ⁇ 24>, which has a molecular weight of 8 or less, further 6 or less, and further 4 or less.
- R 11 contains a hetero atom, and the hetero atom is at least one selected from nitrogen atom, oxygen atom, sulfur atom, and phosphorus atom, ⁇ 13> to ⁇ 25>
- R 1 is a methyl group
- L is a chlorine atom
- n is 1, and L is bonded to the carbon atom at the 2-position of the pyridine ring
- Z is a group selected from -COO-R 2 and -CONH-R 3
- Z is bonded to the 3-position of the pyridine ring
- a - is -OTf, ⁇ 13> to ⁇ 27 >The composition described in any one of >.
- R 1 is a methyl group
- L is a chlorine atom
- n is 1, and L is bonded to the carbon atom at the 2-position of the pyridine ring
- Z is -COO-R 2
- Z is bonded to the 3-position of the pyridine ring
- R 2 is a butyl group
- a - is -OTf
- R 1 is a methyl group
- L is a chlorine atom
- n is 1, and L is bonded to the carbon atom at the 2-position of the pyridine ring
- Z is -CONH-R 3
- Z is bonded to the 3-position of the pyridine ring
- R 3 is a butyl group
- a - is -OTf
- R 1 is a dodecyl group
- L is a chlorine atom
- n is 1, and L is bonded to the carbon atom at the 2-position of the pyridine ring
- a - is -OTf, the composition according to any one of ⁇ 13> to ⁇ 30>.
- R 11 is an alkylene group having 3 carbon atoms
- L is a chlorine atom
- n is 1, and L is bonded to the carbon atom at the 2-position of the pyridine ring.
- Component contains 0.01% by mass or more, further 0.1% by mass or more, further 1% by mass or more, and 20% by mass or less, further 10% by mass or less, further 5% by mass or less, ⁇ 1
- ⁇ 34> Any of ⁇ 1> to ⁇ 33> containing water at least 50% by mass, further at least 80% by mass, further at least 90% by mass, and at most 99% by mass, further at most 95% by mass, and further at most 90% by mass.
- the component (B) is contained at least 0.01% by mass, further at least 1% by mass, at least 3% by mass, and at most 30% by mass, further at most 20% by mass, and further at most 10% by mass. Composition as described.
- component (A) per 1 mole part of component (B) is 22 mole parts or more, further 33 mole parts or more, and 100 mole parts or less, further 55 mole parts or less, and further 44 mole parts or less.
- ⁇ 35> or ⁇ 36> is 22 mole parts or more, further 33 mole parts or more, and 100 mole parts or less, further 55 mole parts or less, and further 44 mole parts or less.
- Z is an alkyl group having 1 to 24 carbon atoms which may contain a heteroatom, nitro, halo, cyano, amino, aminoalkyl, thioalkyl, sulfoalkyl, carboxyester, hydroxy, and carboxamide. is a selected group, and n is a number from 0 to 9.
- R 1c is an alkyl group having 1 to 24 carbon atoms which may contain a heteroatom, and A - is an anion.
- ⁇ 41> Contains component (C) 0.01% by mass or more, further 0.1% by mass or more, further 1% by mass or more, and 20% by mass or less, further 10% by mass or less, further 5% by mass or less, ⁇ 39 > or the composition described in ⁇ 40>.
- component (C) relative to 1 mole part of component (A) is 0.01 mole part or more, further 0.1 mole part or more, further 1 mole part or more, and 100 mole part or less, and further The composition according to any one of ⁇ 39> to ⁇ 41>, wherein the amount is 10 mole parts or less, and further 2 mole parts or less.
- ⁇ 43> Contains component (B) and component (C), and the content of component (B) per 1 mole part of component (C) is 1 mole part or more, further 22 mole parts or more, furthermore 33 mole parts or more. , and the composition according to any one of ⁇ 38> to ⁇ 42>, which contains 100 mole parts or less, further 55 mole parts or less, and further 44 mole parts or less.
- composition according to any one of ⁇ 1> to ⁇ 43> which has a pH at 25° C. of 2 or more, further 3 or more, and less than 7, further 6 or less, and further 5 or less.
- composition according to any one of ⁇ 1> to ⁇ 44>, which contains a pH adjuster which contains a pH adjuster.
- the pH adjuster is a hydrogen phosphate selected from disodium hydrogen phosphate and potassium dihydrogen phosphate, an organic acid selected from lactic acid, succinic acid, gluconic acid, citric acid, acetic acid, and tartaric acid, phosphoric acid, and boron.
- the composition described in ⁇ 45> which is a pH adjuster selected from an inorganic acid selected from acid, hydrochloric acid, and sulfuric acid, and a sulfonic acid selected from paratoluenesulfonic acid, camphorsulfonic acid, and methanesulfonic acid. thing.
- ⁇ 48> The composition described in any one of ⁇ 1> to ⁇ 46>, which is used as a bleaching agent.
- An oxidation method comprising bringing a treatment liquid prepared from the composition according to any one of ⁇ 1> to ⁇ 48> into contact with an object in the presence of hydrogen peroxide.
- a bleaching method comprising bringing a treatment liquid prepared from the composition according to any one of ⁇ 1> to ⁇ 48> into contact with an object in the presence of hydrogen peroxide.
- ⁇ 51> The method described in ⁇ 49> or ⁇ 50>, wherein the treatment liquid contains component (A), component (B), and water.
- the treatment liquid contains component (B) in an amount of 0.001% by mass or more, further 0.01% by mass or more, further 0.1% by mass or more, and 30% by mass or less, further 3% by mass or less, and further 1% by mass. % or less, the method described in ⁇ 51>.
- the treatment liquid contains component (A) in an amount of 0.0001% by mass or more, further 0.001% by mass or more, further 0.01% by mass or more, 10% by mass or less, further 1% by mass or less, further 0.
- the treatment liquid contains 80% by mass or more, further 90% by mass or more, further 95% by mass or more, and 99.99% by mass or less, further 98% by mass or less, further 95% by mass or less, ⁇ 49 >The method described in any one of ⁇ 53>.
- ⁇ 55> The method according to any one of ⁇ 49> to ⁇ 54>, wherein the pH of the treatment liquid is 3 or more, further 5 or more, further 6 or more, and 12 or less, further 10 or less, and further 8 or less.
- component (A) One or more compounds selected from the compound represented by the following general formula (A1) and the compound represented by the following general formula (A2) [hereinafter referred to as component (A)] are stored in acidic water. , how to preserve compounds.
- R 1 is an alkyl group having 1 to 24 carbon atoms and which may contain a hetero atom.
- R12 is a group containing a carbon atom and a heteroatom of an ion that pairs with N + of the pyridine ring, and may contain a heteroatom different from the above heteroatom, and has a total carbon number of 1 to 24 .
- L is n halogen atoms, n is 1, 2 or 3, and L is bonded to n different carbon atoms at any one of the 2nd, 4th and 6th positions of the pyridine ring.
- a ⁇ is an anion.
- a group other than L may be bonded to carbon atoms other than the carbon atom to which L is bonded.
- the content of component (A) in the water is 0.01% by mass or more, further 0.1% by mass or more, further 1% by mass or more, and 20% by mass or less, further 10% by mass or less, and further 5% by mass. % or less, a method for preserving the compound described in ⁇ 56>.
- ⁇ 58> The method for preserving the compound described in ⁇ 56> or ⁇ 57>, wherein component (A) is preserved in water with a pH of 2 or more, further 3 or more, and less than 7, further 6 or less, and further 5 or less.
- the pH adjuster is a hydrogen phosphate selected from disodium hydrogen phosphate and potassium dihydrogen phosphate, an organic acid selected from lactic acid, succinic acid, gluconic acid, citric acid, acetic acid, and tartaric acid, phosphoric acid, and boron.
- the compound described in ⁇ 59> which is a pH adjuster selected from an inorganic acid selected from acids, hydrochloric acid, and sulfuric acid, and a sulfonic acid selected from para-toluenesulfonic acid, camphorsulfonic acid, and methanesulfonic acid. How to save.
- component (B) hydrogen peroxide
- component (B) in the water is 0.01% by mass or more, further 1% by mass or more, further 3% by mass or more, and 30% by mass or less, further 20% by mass or less, and further 10% by mass or less.
- the preservation method is a method for preserving the composition described in any one of ⁇ 1> to ⁇ 48>, and further the composition for oxidizing agent or the composition for bleaching agent, ⁇ 56> to The preservation method described in any of ⁇ 62>.
- ⁇ 64> The preservation method according to any one of ⁇ 56> to ⁇ 63>, wherein the temperature of the acidic water is 0°C or higher, further 25°C or higher, 60°C or lower, and further 50°C or lower.
- ⁇ 65> The preservation method according to any one of ⁇ 56> to ⁇ 64>, wherein the preservation period is 1 day or more, further 14 days or more, and 730 days or less, and further 365 days or less.
- A contains a compound represented by the following general formula (A1-1) [hereinafter referred to as component (A)], (B) hydrogen peroxide [hereinafter referred to as component (B)], and water, and is acidic.
- An oxidation or bleaching method in which a treatment liquid prepared from a liquid composition is brought into contact with an object, the method comprising: The treatment liquid has a pH of 5 or more and 10 or less, The treatment liquid contains component (A) from 0.0001% by mass to 1% by mass, The treatment liquid contains component (B) from 0.001% by mass to 3% by mass, The treatment liquid contains 80% by mass or more and 99.99% by mass or less of water, Oxidation or bleaching methods.
- R 1 is a methyl group
- L is a chlorine atom
- n is 1
- L is bonded to the carbon atom at the 2-position of the pyridine ring
- Z is -COO- R 2
- Z is bonded to the carbon atom at the 3-position of the pyridine ring
- R 2 is a butyl group
- a ⁇ is ⁇ OTf .
- (A) contains a compound represented by the following general formula (A1-1) [hereinafter referred to as component (A)], (B) hydrogen peroxide [hereinafter referred to as component (B)], and water, and is acidic.
- An oxidation or bleaching method in which a treatment liquid prepared from a liquid composition is brought into contact with an object, the method comprising: The treatment liquid has a pH of 5 or more and 10 or less, The treatment liquid contains component (A) from 0.0001% by mass to 1% by mass, The treatment liquid contains component (B) from 0.001% by mass to 3% by mass, The treatment liquid contains 80% by mass or more and 99.99% by mass or less of water, Oxidation or bleaching methods.
- R 1 is a methyl group
- L is a chlorine atom
- n is 1
- L is bonded to the carbon atom at the 2-position of the pyridine ring
- Z is -CONH- R 3
- Z is bonded to the carbon atom at the 3-position of the pyridine ring
- R 3 is a butyl group
- a ⁇ is ⁇ OTf .
- A contains a compound represented by the following general formula (A1-2) [hereinafter referred to as component (A)], (B) hydrogen peroxide [hereinafter referred to as component (B)], and water, and is acidic.
- An oxidation or bleaching method in which a treatment liquid prepared from a liquid composition is brought into contact with an object, the method comprising: The treatment liquid has a pH of 5 or more and 10 or less, The treatment liquid contains component (A) from 0.0001% by mass to 1% by mass, The treatment liquid contains component (B) from 0.001% by mass to 3% by mass, The treatment liquid contains 80% by mass or more and 99.99% by mass or less of water, Oxidation or bleaching methods.
- R 1 is a dodecyl group
- L is a chlorine atom
- n is 1
- L is bonded to the carbon atom at the 2-position of the pyridine ring
- a - is -OTf It is.
- A contains a compound represented by the following general formula (A2-2) [hereinafter referred to as component (A)], (B) hydrogen peroxide [hereinafter referred to as component (B)], and water, and is acidic.
- An oxidation or bleaching method in which a treatment liquid prepared from a liquid composition is brought into contact with an object, the method comprising: The treatment liquid has a pH of 5 or more and 10 or less, The treatment liquid contains component (A) from 0.0001% by mass to 1% by mass, The treatment liquid contains component (B) from 0.001% by mass to 3% by mass, The treatment liquid contains 80% by mass or more and 99.99% by mass or less of water, Oxidation or bleaching methods.
- R 11 is an alkylene group having 3 carbon atoms, L is a chlorine atom, n is 1, L is bonded to the carbon atom at the 2-position of the pyridine ring, and A - is - OTf. ]
- A contains a compound represented by the following general formula (A1-1) [hereinafter referred to as component (A)], (B) hydrogen peroxide [hereinafter referred to as component (B)], and water, and is acidic.
- An oxidizing or bleaching treatment liquid prepared from a liquid composition comprising: The treatment liquid has a pH of 5 or more and 10 or less at 25°C, The treatment liquid contains component (A) from 0.0001% by mass to 1% by mass, The treatment liquid contains component (B) from 0.001% by mass to 3% by mass, The treatment liquid contains 80% by mass or more and 99.99% by mass or less of water, Processing liquid for oxidation or bleaching.
- R 1 is a methyl group
- L is a chlorine atom
- n is 1
- L is bonded to the carbon atom at the 2-position of the pyridine ring
- Z is -COO- R 2
- Z is bonded to the carbon atom at the 3-position of the pyridine ring
- R 2 is a butyl group
- a ⁇ is ⁇ OTf .
- A contains a compound represented by the following general formula (A1-1) [hereinafter referred to as component (A)], (B) hydrogen peroxide [hereinafter referred to as component (B)], and water, and is acidic.
- An oxidizing or bleaching treatment liquid prepared from a liquid composition comprising: The treatment liquid has a pH of 5 or more and 10 or less at 25°C, The treatment liquid contains component (A) from 0.0001% by mass to 1% by mass, The treatment liquid contains component (B) from 0.001% by mass to 3% by mass, The treatment liquid contains 80% by mass or more and 99.99% by mass or less of water, Processing liquid for oxidation or bleaching.
- R 1 is a methyl group
- L is a chlorine atom
- n is 1
- L is bonded to the carbon atom at the 2-position of the pyridine ring
- Z is -CONH- R 3
- Z is bonded to the carbon atom at the 3-position of the pyridine ring
- R 3 is a butyl group
- a ⁇ is ⁇ OTf .
- A contains a compound represented by the following general formula (A1-2) [hereinafter referred to as component (A)], (B) hydrogen peroxide [hereinafter referred to as component (B)], and water, and is acidic.
- An oxidizing or bleaching treatment liquid prepared from a liquid composition comprising: The treatment liquid has a pH of 5 or more and 10 or less at 25°C, The treatment liquid contains component (A) from 0.0001% by mass to 1% by mass, The treatment liquid contains component (B) from 0.001% by mass to 3% by mass, The treatment liquid contains 80% by mass or more and 99.99% by mass or less of water, Processing liquid for oxidation or bleaching.
- R 1 is a dodecyl group
- L is a chlorine atom
- n is 1
- L is bonded to the carbon atom at the 2-position of the pyridine ring
- a - is -OTf It is.
- A contains a compound represented by the following general formula (A2-2) [hereinafter referred to as component (A)], (B) hydrogen peroxide [hereinafter referred to as component (B)], and water, and is acidic.
- An oxidizing or bleaching treatment liquid prepared from a liquid composition comprising: The treatment liquid has a pH of 5 or more and 10 or less at 25°C, The treatment liquid contains component (A) from 0.0001% by mass to 1% by mass, The treatment liquid contains component (B) from 0.001% by mass to 3% by mass, The treatment liquid contains 80% by mass or more and 99.99% by mass or less of water, Processing liquid for oxidation or bleaching.
- R 11 is an alkylene group having 3 carbon atoms, L is a chlorine atom, n is 1, L is bonded to the carbon atom at the 2-position of the pyridine ring, and A - is - OTf. ]
- a treatment liquid for oxidation or bleaching which contains % by mass or more and 99.99% by mass or less, and has a pH of 5 or more and 10 or less at 25°C.
- R 1 is a methyl group
- L is a chlorine atom
- n is 1
- L is bonded to the carbon atom at the 2-position of the pyridine ring
- Z is -COO- R 2
- Z is bonded to the carbon atom at the 3-position of the pyridine ring
- R 2 is a butyl group
- a ⁇ is ⁇ OTf .
- a treatment liquid for oxidation or bleaching which contains % by mass or more and 99.99% by mass or less, and has a pH of 5 or more and 10 or less at 25°C.
- R 1 is a methyl group
- L is a chlorine atom
- n is 1
- L is bonded to the carbon atom at the 2-position of the pyridine ring
- Z is -CONH- R 3
- Z is bonded to the carbon atom at the 3-position of the pyridine ring
- R 3 is a butyl group
- a ⁇ is ⁇ OTf .
- a treatment liquid for oxidation or bleaching which contains % by mass or more and 99.99% by mass or less, and has a pH of 5 or more and 10 or less at 25°C.
- R 1 is a dodecyl group
- L is a chlorine atom
- n is 1
- L is bonded to the carbon atom at the 2-position of the pyridine ring
- a - is -OTf It is.
- a treatment liquid for oxidation or bleaching which contains % by mass or more and 99.99% by mass or less, and has a pH of 5 or more and 10 or less at 25°C.
- R 11 is an alkylene group having 3 carbon atoms, L is a chlorine atom, n is 1, L is bonded to the carbon atom at the 2-position of the pyridine ring, and A - is - OTf. ]
- A contains a compound represented by the following general formula (A1-1) [hereinafter referred to as component (A)], (B) hydrogen peroxide [hereinafter referred to as component (B)], and water, and is acidic.
- a method for producing a processing liquid for oxidation or bleaching using a certain liquid composition comprising: The treatment liquid has a pH of 5 or more and 10 or less at 25°C, The treatment liquid contains component (A) from 0.0001% by mass to 1% by mass, The treatment liquid contains component (B) from 0.001% by mass to 3% by mass, The treatment liquid contains 80% by mass or more and 99.99% by mass or less of water, optionally mixing said liquid composition with water; A method for producing a treatment liquid for oxidation or bleaching.
- R 1 is a methyl group
- L is a chlorine atom
- n is 1
- L is bonded to the carbon atom at the 2-position of the pyridine ring
- Z is -COO- R 2
- Z is bonded to the carbon atom at the 3-position of the pyridine ring
- R 2 is a butyl group
- a ⁇ is ⁇ OTf .
- A contains a compound represented by the following general formula (A1-1) [hereinafter referred to as component (A)], (B) hydrogen peroxide [hereinafter referred to as component (B)], and water, and is acidic.
- a method for producing a processing liquid for oxidation or bleaching using a certain liquid composition comprising: The treatment liquid has a pH of 5 or more and 10 or less at 25°C, The treatment liquid contains component (A) from 0.0001% by mass to 1% by mass, The treatment liquid contains component (B) from 0.001% by mass to 3% by mass, The treatment liquid contains 80% by mass or more and 99.99% by mass or less of water, optionally mixing said liquid composition with water; A method for producing a treatment liquid for oxidation or bleaching.
- R 1 is a methyl group
- L is a chlorine atom
- n is 1
- L is bonded to the carbon atom at the 2-position of the pyridine ring
- Z is -CONH- R 3
- Z is bonded to the carbon atom at the 3-position of the pyridine ring
- R 3 is a butyl group
- a ⁇ is ⁇ OTf .
- A contains a compound represented by the following general formula (A1-2) [hereinafter referred to as component (A)], (B) hydrogen peroxide [hereinafter referred to as component (B)], and water, and is acidic.
- a method for producing a processing liquid for oxidation or bleaching using a certain liquid composition comprising: The treatment liquid has a pH of 5 or more and 10 or less at 25°C, The treatment liquid contains component (A) from 0.0001% by mass to 1% by mass, The treatment liquid contains component (B) from 0.001% by mass to 3% by mass, The treatment liquid contains 80% by mass or more and 99.99% by mass or less of water, optionally mixing said liquid composition with water; A method for producing a treatment liquid for oxidation or bleaching.
- R 1 is a dodecyl group
- L is a chlorine atom
- n is 1
- L is bonded to the carbon atom at the 2-position of the pyridine ring
- a - is -OTf It is.
- A contains a compound represented by the following general formula (A2-2) [hereinafter referred to as component (A)], (B) hydrogen peroxide [hereinafter referred to as component (B)], and water, and is acidic.
- a method for producing a processing liquid for oxidation or bleaching using a certain liquid composition comprising: The treatment liquid has a pH of 5 or more and 10 or less at 25°C, The treatment liquid contains component (A) from 0.0001% by mass to 1% by mass, The treatment liquid contains component (B) from 0.001% by mass to 3% by mass, The treatment liquid contains 80% by mass or more and 99.99% by mass or less of water, optionally mixing said liquid composition with water; A method for producing a treatment liquid for oxidation or bleaching.
- R 11 is an alkylene group having 3 carbon atoms, L is a chlorine atom, n is 1, L is bonded to the carbon atom at the 2-position of the pyridine ring, and A - is - OTf. ]
- an intermediate of the above compound was synthesized according to the following scheme.
- the synthesis was performed using a 200 mL three-necked eggplant flask.
- the obtained organic layer was washed with water and a saturated aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate.
- Ta The 1 H NMR measurement results of the compound were as follows.
- an intermediate of the above compound was synthesized according to the following scheme.
- the synthesis was performed using a 200 mL three-necked eggplant flask.
- the obtained organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated using a rotary evaporator to obtain a crude product.
- the 1 H NMR measurement results of the compound were as follows.
- Synthesis example 3 3-(2-chloropyridin-1-ium-1-yl)propane-1-sulfonate (Table 1-1) Compounds such as Examples 1-3) were synthesized according to the following scheme. The synthesis was performed using a 200 mL one-necked eggplant flask.
- 1,3-propanesultone (4.03g, 33.02mmol, 0.75 eq.) was added to 2-chloropyridine (5g, 44.03mmol), and the mixture was stirred at 60°C for 5 hours. Acetone was added to the final solution, and the resulting crystals were collected by filtration and dried under reduced pressure to obtain 4.98 g of the title compound (21.14 mmol, yield 64%).
- the 1 H NMR measurement results of the compound were as follows.
- Synthesis example 4 2-chloro-1-(dodecyl)pyridin-1-ium trifluoromethane sulfonate (2-chloro-1-(dodecyl)pyridin-1-ium trifluoromethane sulfonate (such as Example 1-4 in Table 1-1) Compound) was synthesized using the following scheme. The synthesis was performed using a 100 mL three-necked eggplant flask.
- ⁇ Reagent> The reagents used in Examples, Comparative Examples, Reference Examples, and Comparative Reference Examples are as follows. ⁇ Phosphoric acid (85%): Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. ⁇ Disodium hydrogen phosphate: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. ⁇ Potassium dihydrogen phosphate: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.
- ⁇ Diphosphoric acid Sodium hydrogen manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., sodium 3-(trimethylsilyl)-1-propane-1,1,2,2,3,3-d6-sulfonate: manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., ethanol (99.5%): manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. ⁇ Curcumin: manufactured by Fuji Film Wako Pure Chemical Industries, Ltd. ⁇ Acetonitrile: manufactured by Fuji Film Wako Pure Chemical Industries, Ltd. ⁇ Hydrogen peroxide (30%): manufactured by Fuji Film Wako Pure Chemical Industries, Ltd. Manufactured by the company The number in parentheses is the effective amount. The amounts in the table are effective amounts.
- the liquid compositions of Examples in Table 1-1 can be used as raw materials for oxidizing agents or bleaching agents.
- the carbonate buffer was the same as in Comparative Example 1 (Storage Stability Evaluation 2).
- a 6% hydrogen peroxide solution (aqueous solution of component (B)) was added to the cup so that the amount of component (B) was 0.03% by mass.
- the bleach activation aid is 2-methyl-3,4-dihydroisoquinolin-2-ium tetrafluoroborate, which is synthesized by the following method. It is a compound that has been After stirring at 150 to 200 rpm for 10 minutes, the contaminated cloth was removed and rinsed twice with tap water in a basin. After rinsing, the cloth was dehydrated for 2 minutes using a dehydrator, and the contaminated cloth was air-dried. The bleaching rate was calculated using the following formula from the previously measured reflectance Z value before washing, the Z value of the white cloth, and the Z value after washing. The results are shown in Table 4. A spectrophotometer SE 6000 (manufactured by Nippon Denshoku Kogyo Co., Ltd.) was used to measure the reflectance.
- R 0 Z value of reflectance of white cloth
- R S Z value of reflectance of contaminated cloth before cleaning
- R W Z value of reflectance of contaminated cloth after cleaning
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- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Detergent Compositions (AREA)
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| EP23788357.4A EP4509486A1 (en) | 2022-04-13 | 2023-04-12 | Composition |
| CN202380033930.4A CN119032148A (zh) | 2022-04-13 | 2023-04-12 | 组合物 |
| US18/856,265 US20250250514A1 (en) | 2022-04-13 | 2023-04-12 | Composition |
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| EP (1) | EP4509486A1 (https=) |
| JP (1) | JP7397242B1 (https=) |
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| WO (1) | WO2023199939A1 (https=) |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62166346A (ja) * | 1986-01-20 | 1987-07-22 | Konishiroku Photo Ind Co Ltd | カラ−画像形成方法 |
| JPH03220298A (ja) | 1990-01-24 | 1991-09-27 | Kao Corp | 硬表面用漂白剤組成物 |
| JP2002080894A (ja) | 2000-09-04 | 2002-03-22 | Settsu Seiyu Kk | 漂白剤組成物 |
| WO2008050732A1 (fr) * | 2006-10-23 | 2008-05-02 | Takeda Pharmaceutical Company Limited | Dérivé de l'iminopyridine et son utilisation |
| JP2009155292A (ja) | 2007-12-27 | 2009-07-16 | Lion Corp | 殺菌・除菌用組成物 |
| JP2013001699A (ja) * | 2011-06-21 | 2013-01-07 | Api Corporation | ピリジン−n−オキシド類の製造方法 |
| JP2017538759A (ja) * | 2014-12-19 | 2017-12-28 | ロレアル | ケラチン物質を処理するための特定のピリジニウム塩の使用、組成物、および実施方法 |
-
2023
- 2023-04-12 CN CN202380033930.4A patent/CN119032148A/zh active Pending
- 2023-04-12 EP EP23788357.4A patent/EP4509486A1/en active Pending
- 2023-04-12 US US18/856,265 patent/US20250250514A1/en active Pending
- 2023-04-12 WO PCT/JP2023/014846 patent/WO2023199939A1/ja not_active Ceased
- 2023-04-12 JP JP2023547090A patent/JP7397242B1/ja active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62166346A (ja) * | 1986-01-20 | 1987-07-22 | Konishiroku Photo Ind Co Ltd | カラ−画像形成方法 |
| JPH03220298A (ja) | 1990-01-24 | 1991-09-27 | Kao Corp | 硬表面用漂白剤組成物 |
| JP2002080894A (ja) | 2000-09-04 | 2002-03-22 | Settsu Seiyu Kk | 漂白剤組成物 |
| WO2008050732A1 (fr) * | 2006-10-23 | 2008-05-02 | Takeda Pharmaceutical Company Limited | Dérivé de l'iminopyridine et son utilisation |
| JP2009155292A (ja) | 2007-12-27 | 2009-07-16 | Lion Corp | 殺菌・除菌用組成物 |
| JP2013001699A (ja) * | 2011-06-21 | 2013-01-07 | Api Corporation | ピリジン−n−オキシド類の製造方法 |
| JP2017538759A (ja) * | 2014-12-19 | 2017-12-28 | ロレアル | ケラチン物質を処理するための特定のピリジニウム塩の使用、組成物、および実施方法 |
Non-Patent Citations (1)
| Title |
|---|
| SANDMANN, G. ; KOWALCZYK-SCHRODER, S. ; TAYLOR, H.M. ; BOGER, P.: "Quantitative structure-Activity relationship of fluridone derivatives with phytoene desaturase", PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, ACADEMIC PRESS., US, vol. 42, no. 1, 1 January 1992 (1992-01-01), US , pages 1 - 6, XP024866842, ISSN: 0048-3575, DOI: 10.1016/0048-3575(92)90067-A * |
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| Publication number | Publication date |
|---|---|
| JPWO2023199939A1 (https=) | 2023-10-19 |
| US20250250514A1 (en) | 2025-08-07 |
| CN119032148A (zh) | 2024-11-26 |
| JP7397242B1 (ja) | 2023-12-12 |
| EP4509486A1 (en) | 2025-02-19 |
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