Branched chain-containing fluorine-containing compounds

Abstract

An object of the present application is to provide a novel branched-chain-containing fluorine compound. This object is achieved by a branched-chain-containing fluorine compound represented by formula (1). [In the formula, L represents a prescribed carbon-containing linking portion, Rf is the same or different at each occurrence and represents a fluoroalkyl group which can have one or more ether bonds; Y is the same or different at each occurrence and represents a prescribed divalent linking group or a valence bond; R Y represents a hydrogen atom or an organic group; L represents a carbon-containing linking portion of (n1 + n2) valence having one or more carbon atoms; n1 represents a number of 1 or more; n2 represents a number of 1 or more; n1 + n2 is a number of 3 to 6; X is the same or different at each occurrence and represents a divalent linking group or a valence bond; A is the same or different at each occurrence and represents -ArSO3M; M is the same or different at each occurrence and represents a hydrogen atom, -NR4, or a metal salt; and R represents a hydrogen atom or a C1-C4 organic group.

Description

[0001] This application is a divisional application of the same patent application number 201780056503.2, filed on September 13, 2017. Technical Field

[0002] This invention relates to branched fluorine compounds. Background Technology

[0003] In the prior art, as a branched fluorinated compound, Patent Document 1 discloses a branched fluorinated compound that can be effectively used as a surfactant.

[0004] Existing technical documents Patent documents Patent Document 1: Booklet No. WO2014 / 012661 Summary of the Invention

[0005] The technical problem that the invention aims to solve However, there is still a need to develop new types of branched fluorinated compounds that can be effectively used as fluorinated surfactants (especially interface promoters, viscosity reducers, dispersants, or emulsifiers).

[0006] Means for solving technical problems The inventors of this invention conducted in-depth research and discovered that the above-mentioned technical problems can be solved by using the branched fluorine compound shown in formula (1), thereby completing this invention. [In the formula,] L represents the trivalent carbon-containing linker shown in formula (1) (L-1-1), the tetravalent carbon-containing linker shown in formula (2) (L-1-2), the pentavalent carbon-containing linker shown in formula (3) (L-1-3), the hexavalent carbon-containing linker shown in formula (L-1-4), the tetravalent carbon-containing linker shown in formula (5) (L-2), or the (n1+n2) valent carbon-containing linker shown in formula (L-3). (where R) L The same or different occurrences each time indicate a hydrogen atom, alkyl group, -NH2, or -NHR. RL -OH or -OR RL And R RL (represents organic groups) (where R) L The same or different occurrences each time indicate a hydrogen atom, alkyl group, -NH2, or -NHR. RL -OH or -OR RL And RRL (represents organic groups) (where R) L Represents hydrogen atoms, alkyl groups that may have more than one substituent, -NH2, -NHR RL -OH or -OR RL And R RL (represents organic groups) [In the formula, ring D represents an aromatic ring or a non-aromatic heterocycle]; The fact that Rf is the same or different each time it appears indicates that a fluoroalkyl group can have more than one ether bond; Y is the same or different each time it appears, indicating that (1) it is selected from -O-, -COO-, -OCO-, -CONR. Y - and -NR Y The divalent linker or (2) valence bond in CO- (but when L is the trivalent carbon-containing linker shown in formula (L-1-1) or the tetravalent carbon-containing linker shown in formula (L-1-2), Y is not -COO- or -OCO-). R Y The fact that they appear the same or different each time indicates a hydrogen atom or an organic group; L represents a carbon-containing bonding portion with a (n1+n2) valence of one or more carbon atoms; n1 represents a number greater than or equal to 1; n2 represents a number greater than or equal to 1; n1 + n2 are numbers from 3 to 6; X may be the same or different each time it appears, indicating a 2-valent linker or valence bond; A may be the same or different each time it appears, representing -ArSO3M, -SO3M, -SO4M, -PO3M or -COOM; M may be the same or different each time it appears, representing a hydrogen atom, -NR4, or a metal salt; Furthermore, R may be the same or different each time it appears, representing a hydrogen atom or a C1-C4 organic group.

[0007] The present invention includes the following methods.

[0008] Item 1. A branched fluorine compound represented by formula (1), [In the formula,] L represents the trivalent carbon-containing linker shown in formula (1) (L-1-1), the tetravalent carbon-containing linker shown in formula (2) (L-1-2), the pentavalent carbon-containing linker shown in formula (3) (L-1-2), the hexavalent carbon-containing linker shown in formula (4) (L-1-2), the tetravalent carbon-containing linker shown in formula (5) (L-2), or the (n1+n2) valent carbon-containing linker shown in formula (6) (L-3). (where R) L The same or different occurrences each time indicate a hydrogen atom, an alkyl group that can have more than one substituent, -NH2, or -NHR. RL -OH or -OR RL And R RL (represents organic groups) (where R) L The same or different occurrences each time indicate a hydrogen atom, an alkyl group that can have more than one substituent, -NH2, or -NHR. RL -OH or -OR RL And R RL (represents organic groups) (where R) L Represents hydrogen atoms, alkyl groups that may have more than one substituent, -NH2, -NHR RL -OH or -OR RL And R RL (Represents organic groups) [In the formula, ring D represents an aromatic ring or a non-aromatic heterocycle]; The fact that Rf is the same or different each time it appears indicates that a fluoroalkyl group can have more than one ether bond; Y is the same or different each time it appears, indicating that (1) it is selected from -O-, -COO-, -OCO-, -CONR. Y - and -NR Y The divalent linker or (2) valence bond in CO- (but when L is the trivalent carbon-containing linker shown in formula (L-1-1) or the tetravalent carbon-containing linker shown in formula (L-1-2), Y is not -COO- or -OCO-). R Y The fact that they appear the same or different each time indicates a hydrogen atom or an organic group; L represents a carbon-containing bonding portion with a (n1+n2) valence of one or more carbon atoms; n1 represents a number greater than or equal to 1; n2 represents a number greater than or equal to 1; n1 + n2 are numbers from 3 to 6; X may be the same or different each time it appears, indicating a 2-valent linker or valence bond; A may be the same or different each time it appears, representing -ArSO3M, -SO3M, -SO4M, -PO3M or -COOM; M may be the same or different each time it appears, representing a hydrogen atom, -NR4, or a metal salt; Furthermore, R represents a hydrogen atom and an organic group of C1-C4.

[0009] Item 2. As described in item 1, the branched fluorine-containing compound, wherein, L represents the trivalent carbon-containing linker shown in formula (L-1-1) above or the tetravalent carbon-containing linker shown in formula (L-1-2) above. Furthermore, Y is the same or different each time it appears, and (1) is selected from -O-, -CONR. Y - and -NR Y The divalent linker or (2) valence bond in CO-.

[0010] Item 3. As described in item 2, the branched fluorinated compound, wherein X is an alkylene chain or a valence bond.

[0011] Item 4. As described in item 3, the branched fluorine-containing compound, wherein X is a valence bond.

[0012] Item 5. As described in item 1, the branched fluorine-containing compound, wherein, L is the tetravalent carbon-containing linker shown in the above formula (L-2); Furthermore, at least one Y is -O-, -COO-, -OCO-, or -CONR. Y - or - NR Y CO-.

[0013] Item 6. The branched fluorinated compound as described in any one of items 1 to 4, wherein, n1 is 1 or 2; Furthermore, n2 is 2.

[0014] The present invention also includes the following methods.

[0015] Item 7. A surfactant containing any one of the branched fluorinated compounds described in items 1 to 6.

[0016] Item 8. An aqueous dispersant containing any one of the branched fluorine compounds described in items 1 to 6.

[0017] The effects of the invention According to the present invention, a novel branched fluorine compound is provided.

[0018] In one embodiment of the invention, the branched fluorinated compound can be effectively used as an emulsifier. Detailed Implementation

[0019] the term Unless otherwise specified, all symbols and abbreviations used in this specification shall be understood in accordance with the text of this specification as having the commonly used meanings in the technical field to which this invention pertains.

[0020] In this specification, the expression “containing” is intended to include expressions “essentially constituted by” and “composed of”.

[0021] Unless otherwise specified, the procedures, treatments or operations described in this instruction manual can be performed at room temperature.

[0022] In this instruction manual, room temperature refers to a temperature in the range of 10 to 40°C.

[0023] In this specification, the expression "Cn-Cm" (where n and m are numbers) means, as commonly understood by those skilled in the art, that the number of carbon atoms is n or more and m or less.

[0024] Unless otherwise specified, examples of "halogen atoms" in this specification include fluorine, chlorine, bromine, and iodine.

[0025] In this specification, "organic group" means a group containing one or more carbon atoms, or a group formed by removing one hydrogen atom from an organic compound.

[0026] Examples of this "organic group" include: Alkyl groups that can have more than one substituent Alkenes that can have one or more substituents Alkyne groups can have more than one substituent. Cycloalkyl groups can have more than one substituent. Cycloalkenyl groups can have more than one substituent. Cycloalkadienyl groups can have more than one substituent. Aryl groups can have one or more substituents. Aryl groups can have one or more substituents. Non-aromatic heterocyclic groups that can have more than one substituent Heteroaryl groups that can have one or more substituents cyano, Aldehyde group R a O-、 R a CO-、 R a SO2−, R a OCO-、and R a OSO2- (In these formulas, R) a Independently: Alkyl groups that can have more than one substituent Alkenes that can have one or more substituents Alkyne groups can have more than one substituent. Cycloalkyl groups can have more than one substituent. Cycloalkenyl groups can have more than one substituent. Cyclodiene groups can have more than one substituent. Aryl groups can have one or more substituents. Aryl groups can have one or more substituents. It can be a non-aromatic heterocyclic group with more than one substituent, or (It can be a heteroaryl group with more than one substituent).

[0027] In this instruction manual, Alkyl groups that can have more than one substituent Alkenes that can have one or more substituents Alkyne groups can have more than one substituent. Cycloalkyl groups can have more than one substituent. Cycloalkenyl groups can have more than one substituent. Cyclodiene groups can have more than one substituent. Aryl groups can have one or more substituents. Aryl groups can have one or more substituents. Non-aromatic heterocyclic groups that can have more than one substituent, and Examples of substituents in heteroaryl groups that may have more than one substituent include: Nitro, hydroxyl, halogen atom, cyano, aliphatic group, aryl, heterocyclic group, acyl, acyloxy, amide, aliphatic oxy, aryloxy, heterocyclic oxy, aliphatic oxycarbonyl, aryloxycarbonyl, heterocyclic oxycarbonyl, carbamoyl, aliphatic sulfonyl, arylsulfonyl, heterocyclic sulfonyl, aliphatic sulfonyloxy, arylsulfonyloxy, heterocyclic sulfonyloxy, aminosulfonyl, aliphatic sulfonamide, arylsulfonamide, heterocyclic sulfonamide, amino, aliphatic amino, arylamino Substituents include: aliphatic oxycarbonylamino, aryloxycarbonylamino, heterocyclic oxycarbonylamino, aliphatic sulfinyl, arylsulfinyl, aliphatic thio, aryl thio, sulfonyl, carboxyl, aliphatic oxyamino, aryloxyamino, carbamoylamino, aminosulfonylamino, halogen atom, aminosulfonylcarbamoyl, carbamoylaminosulfonyl, dialiphatic oxyphosphinyl and diaryloxyphosphinyl (sometimes the group consisting of these substituents is called substituent group A). Furthermore, the preferred features include: (a) Halogen atoms, (b) hydroxyl group (c) Nitro, and (d) Cyano group.

[0028] The term "aryl" in the above substituent group A refers to aryl or aryl moiety.

[0029] The term "aliphatic" in the above substituent group A refers to an aliphatic group or aliphatic part.

[0030] In the substituents or portions thereof of the above substituent group A, the "aliphatic (group or portion)" may have more than one substituent, and may be saturated or unsaturated.

[0031] The substituent can be any substituted group from the substituent group A above.

[0032] Examples include hydroxyl, aliphatic oxygen, carbamoyl, aliphatic oxygen carbonyl, aliphatic thio, amino, aliphatic amino, amide, and carbamoylamino.

[0033] The "aliphatic (group or part)" is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms. Examples include methyl, ethyl, vinyl, cyclohexyl, and carbamoylmethyl.

[0034] In the substituents or portions thereof of the above-mentioned substituent group A, the "aryl (group or portion)" may condense with one or more rings (e.g., 3-8 membered non-aromatic heterocycles, 5- or 6 membered aromatic heterocycles, C3-C8 non-aromatic carbon rings), and may have substituents.

[0035] The substituent can be any substituted group from the substituent group A above.

[0036] Examples include nitro, halogen, aliphatic oxygen, carbamoyl, aliphatic oxygen carbonyl, aliphatic thio, amino, aliphatic amino, amide, and carbamoylamino.

[0037] The "aryl group (or part)" is preferably an aryl group with 6 to 12 carbon atoms, and more preferably an aryl group with 6 to 10 carbon atoms.

[0038] Examples include phenyl, 4-nitrophenyl, 4-acetaminophenyl, and 4-methanesulfonylphenyl.

[0039] In the substituents or portions thereof of the substituent group A above, the "heterocyclic group (group or portion)" may have substituents, may be saturated or unsaturated, and may form a fused ring. That is, the "heterocyclic group (group or portion)" may be the above-mentioned non-aromatic heterocyclic group or the above-mentioned heteroaryl group.

[0040] The substituent can be any substituted group from the substituent group A above.

[0041] Examples include halogen atoms, hydroxyl groups, aliphatic oxygen groups, carbamoyl groups, aliphatic oxygen carbonyl groups, aliphatic thio groups, amino groups, aliphatic amino groups, amide groups, and carbamoylamino groups.

[0042] In the substituents or portions thereof of the substituent group A above, the "heterocyclic group (group or portion)" is preferably a 5- to 14-membered heterocyclic group with 2 to 12 carbon atoms bonded via carbon atoms, and more preferably a 5- to 14-membered heterocyclic group with 2 to 10 carbon atoms bonded via carbon atoms.

[0043] Examples include 2-tetrahydrofuranyl and 2-pyrimidinyl.

[0044] In the substituents or portions thereof of the substituent group A above, the "acyl group (group or portion)" can be an aliphatic carbonyl group, an aryl carbonyl group, or a heterocyclic carbonyl group, and can have substituents.

[0045] The substituent can be any substituted group from the substituent group A above.

[0046] Examples include hydroxyl, halogen, aryl, aliphatic oxygen, carbamoyl, aliphatic oxygen carbonyl, aliphatic thio, amino, aliphatic amino, amide, and carbamoylamino.

[0047] The "acyl group (or part)" is preferably an acyl group with 2 to 8 carbon atoms, and more preferably an acyl group with 2 to 4 carbon atoms.

[0048] Examples include acetyl, propionyl, benzoyl, and 3-pyridine carbonyl.

[0049] In the substituents or portions thereof of the substituent group A above, the "carbamoyl group (or portion)" may have substituents.

[0050] The substituent can be any substituted group from the substituent group A above.

[0051] Examples include aliphatic groups, aryl groups, and heterocyclic groups.

[0052] The "carbamoyl group" is preferably a non-substituted carbamoyl group or an alkyl carbamoyl group with a total carbon number of 2 to 9 (preferably 2 to 5).

[0053] Examples include N-methylcarbamoyl, N,N-dimethylcarbamoyl, and N-phenylcarbamoyl.

[0054] In this instruction manual, Cycloalkyl groups can have more than one substituent. Cycloalkenyl groups can have more than one substituent. Cyclodiene groups can have more than one substituent. Aryl groups can have one or more substituents. Aryl groups can have one or more substituents. Non-aromatic heterocyclic groups that can have more than one substituent, and Examples of substituents in heteroaryl groups that may have more than one substituent may further include: (e) Alkyl groups that may have one or more substituents (f) Alkenes that may have one or more substituents, and (g) An alkynyl group may have one or more substituents.

[0055] Unless otherwise specified, "alkyl" in this specification can be linear or branched.

[0056] In this specification, unless otherwise specified, preferred examples of "alkyl" include C1-C20 alkyl, C1-C8 alkyl, C1-C7 alkyl, C1-C6 alkyl and C1-C5 alkyl.

[0057] Unless otherwise specified, specific examples of "alkyl" in this specification include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, hexyl, heptyl, octyl, nonyl, and decyl.

[0058] Those skilled in the art will naturally understand that, in this specification, specific examples of "C1-C8 alkyl" include groups with 1 to 8 carbon atoms in the specific examples of the aforementioned alkyl groups. It includes branched or straight-chain C1-C8 alkyl groups, this is for clarity only.

[0059] In this instruction manual, "Fluoroalkyl groups that can have more than one ether bond" can be: Fluoroalkyl groups with one or more ether-containing oxygen atoms can be inserted.

[0060] Examples of them include: (1) An alkyl group substituted with one or more fluorine atoms; and (2) An alkyl group having one or more ether bonds and being substituted by one or more fluorine atoms.

[0061] In this specification, "fluoroalkyl" includes perfluoroalkyl.

[0062] In this specification, specific examples of "fluoroalkyl" include CF3-, C2F5-, C3F7-, C2F5CH2-, H(CF2CF2)2CH2- and H(CF2CF2)3CH2-.

[0063] In this specification, specific examples of "fluoroalkyl groups having one or more ether bonds" include CF3OC2F4-, CF3OC3F6-, CF3OC4F8-, and CF3OC5F-. 10 -, CF3OC2F4OC2F4-, C2F5OC2F4-, C2F5OC3F6-, C2F5OC4F8-, C2F5OC2F4OC2F4-, C3F7O(CF2)2-, C3F7OCF(CF3)-, C3F7OC3F6- and C4F9OC2F4-.

[0064] Unless otherwise specified, examples of "alkenyl" in this specification include straight-chain or branched alkenyl groups with 2 to 10 carbon atoms, such as vinyl, 1-propen-1-yl, 2-propen-1-yl, isopropenyl, 2-buten-1-yl, 4-penten-1-yl, and 5-hexen-1-yl.

[0065] Unless otherwise specified, examples of "alkynyl" in this specification include straight-chain or branched alkynyl groups with 2 to 10 carbon atoms, such as ethynyl, 1-propyn-1-yl, 2-propyn-1-yl, 4-pentyn-1-yl, and 5-hexyn-1-yl.

[0066] Unless otherwise specified, examples of "cycloalkyl" in this specification include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl with 3 to 10 carbon atoms.

[0067] Unless otherwise specified, examples of "cycloalkenyl" in this specification include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, and other cycloalkenyl groups with 3 to 10 carbon atoms.

[0068] Unless otherwise specified, examples of "cyclodienyl" in this specification include cyclobutadienyl, cyclopentadienyl, cyclohexadienyl, cycloheptadienyl, cyclooctadienyl, cyclononadienyl, cyclodecadienyl, and other cyclodienyl groups with 4 to 10 carbon atoms.

[0069] Unless otherwise specified in this specification, "aryl" can be monocyclic, bicyclic, tricyclic, or tetracyclic.

[0070] Unless otherwise specified, "aryl" in this specification can be an aryl group with 6 to 18 carbon atoms.

[0071] Unless otherwise specified, examples of "aryl" in this specification include phenyl, 1-naphthyl, 2-naphthyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, and 2-anthrayl.

[0072] Unless otherwise specified, examples of "aryl group" in this specification include benzyl, phenethyl, diphenylmethyl, 1-naphthylmethyl, 2-naphthylmethyl, 2,2-diphenylethyl, 3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl, 2-biphenylmethyl, 3-biphenylmethyl and 4-biphenylmethyl.

[0073] Unless otherwise specified in this specification, "non-aromatic heterocyclic group" can be monocyclic, bicyclic, tricyclic, or tetracyclic.

[0074] Unless otherwise specified in this specification, a "non-aromatic heterocyclic group" is, for example, a non-aromatic heterocyclic group that contains 1 to 4 heteroatoms selected from oxygen, sulfur, and nitrogen atoms in addition to carbon atoms as the cyclic atom.

[0075] Unless otherwise specified, "non-aromatic heterocyclic groups" in this specification may be saturated or unsaturated.

[0076] Unless otherwise specified, examples of "non-aromatic heterocyclic groups" in this specification include tetrahydrofuranyl, oxazolidinyl, imidazolinyl (e.g., 1-imidazolinyl, 2-imidazolinyl, 4-imidazolinyl), aziridinepropyl (e.g., 1-aziridinepropyl, 2-aziridinepropyl), aziridinebutyl (e.g., 1-aziridinebutyl, 2-aziridinebutyl), pyrrolidinyl (e.g., 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl), piperidinyl (e.g., 1-piperidinyl, 2-piperidinyl, 3-piperidinyl), aziridineheptyl (e.g., 1-aziridineheptyl, 2-aziridineheptyl, 3-aziridineheptyl, 4-aziridineheptyl), aziridineoctyl (e.g., 1-aziridineoctyl, 2-aziridineoctyl, 3-aziridineoctyl, 4-aziridineoctyl), and piperazine (e.g., 1,4-piperazine). -1-yl, 1,4-piperazin-2-yl), diazapyridine (e.g., 1,4-diazapyr-1-yl, 1,4-diazapyr-2-yl, 1,4-diazapyr-5-yl, 1,4-diazapyr-6-yl), diazacyclooctyl (e.g., 1,4-diazacyclooctane-1-yl, 1,4-diazacyclooctane-2-yl, 1,4-diazacyclooctane-5-yl, 1 ,4-diazacyclooctane-6-yl, 1,5-diazacyclooctane-1-yl, 1,5-diazacyclooctane-2-yl, 1,5-diazacyclooctane-3-yl), tetrahydropyranyl (e.g., tetrahydropyran-4-yl), morpholinyl (e.g., 4-morpholinyl), thiomorpholinyl (e.g., 4-thiomorpholinyl), 2-oxazolylyl, dihydrofuranyl, dihydropyranyl, and dihydroquinolinyl, etc.

[0077] Unless otherwise specified in this specification, "heteroaryl" can be, for example, a 5- to 18-membered heteroaryl group that is monocyclic, bicyclic, tricyclic, or tetracyclic.

[0078] Unless otherwise specified, "heteroaryl" in this specification refers to a heteroaryl group that, in addition to carbon atoms, contains 1 to 4 heteroatoms selected from oxygen, sulfur, and nitrogen atoms as cyclic atoms. The number of carbon atoms in this "heteroaryl" group can be, for example, 3 to 17.

[0079] Unless otherwise specified, "heteroaryl" in this specification includes both "monocyclic heteroaryl" and "aromatic condensed heterocyclic group".

[0080] Unless otherwise specified in this specification, examples of "monocyclic heteroaryl" include pyrrole (e.g., 1-pyrrole, 2-pyrrole, 3-pyrrole), furanyl (e.g., 2-furanyl, 3-furanyl), thiophene (e.g., 2-thiophene, 3-thiophene), pyrazolyl (e.g., 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl), imidazole (e.g., 1-imidazole, 2-imidazole, 4-imidazole), isoxazolyl (e.g., 3-isooxazolyl, 4-isooxazolyl, 5-isooxazolyl), oxazolyl (e.g., 2-oxazolyl, 4-oxazolyl, 5-oxazolyl), and isothiazolyl (e.g., 3-isothhiazolyl, 4-isothhiazolyl). 5-Isothiazolyl), thiazolyl (e.g., 2-thiazolyl, 4-thiazolyl, 5-thiazolyl), triazolyl (e.g., 1,2,3-triazol-4-yl, 1,2,4-triazol-3-yl), oxadiazolyl (e.g., 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl), thiadiazolyl (e.g., 1,2,4-thiadiazolyl-3-yl, 1,2,4-thiadiazolyl-5-yl), tetrazolyl, pyridinyl (e.g., 2-pyridinyl, 3-pyridinyl, 4-pyridinyl), pyrazinyl (e.g., 3-pyrazinyl, 4-pyrazinyl), pyrimidinyl (e.g., 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl), pyrazinyl, etc.

[0081] Unless otherwise specified in this specification, examples of "aromatic condensed heterocyclic groups" include isoindolyl (e.g., 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl), indolyl (e.g., 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl), and benzo[b]furanyl (e.g., 2-benzo[b]furanyl, 3-benzo[b]furanyl, ... 4-benzo[b]furanyl, 5-benzo[b]furanyl, 6-benzo[b]furanyl, 7-benzo[b]furanyl), benzo[c]furanyl (e.g., 1-benzo[c]furanyl, 4-benzo[c]furanyl, 5-benzo[c]furanyl), benzo[b]thiophenyl (e.g., 2-benzo[b]thiophenyl, 3-benzo[b]thiophenyl, 4-benzo[b]thiophenyl, 5-benzo[b]thiophenyl, 6-benzo[b]thiophenyl, 7-benzo[b]thiophenyl), benzene [c]thiophene (e.g., 1-benzo[c]thiophene, 4-benzo[c]thiophene, 5-benzo[c]thiophene), indazole (e.g., 1-indazole, 2-indazole, 3-indazole, 4-indazole, 5-indazole, 6-indazole, 7-indazole), benzimidazole (e.g., 1-benzimidazole, 2-benzimidazole, 4-benzimidazole, 5-benzimidazole), 1,2-benzisoxazolyl (e.g., 1,2-benzisoxazol-3-yl, 1,2-benzisoxazolyl) Azoxyl-4-yl, 1,2-benzisoxazol-5-yl, 1,2-benzisoxazol-6-yl, 1,2-benzisoxazol-7-yl), benzoxazolyl (e.g., 2-benzoxazolyl, 4-benzoxazolyl, 5-benzoxazolyl, 6-benzoxazolyl, 7-benzoxazolyl), 1,2-benzisothiazolyl (e.g., 1,2-benzisothiazol-3-yl, 1,2-benzisothiazol-4-yl, 1,2-benzisothiazol-5-yl, 1,2-benzisothiazol-6-yl, 1,2-Benzothiazolyl-7-yl), benzothiazolyl (e.g., 2-benzothiazolyl, 4-benzothiazolyl, 5-benzothiazolyl, 6-benzothiazolyl, 7-benzothiazolyl), isoquinolinyl (e.g., 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl), quinolinyl (e.g., 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 8-quinolinyl), zonalyl (e.g., 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 8-quinolinyl), zonalyl (e.g., 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 8-quinolinyl), zonalyl (e.g., 2-benzothiazolyl ...benzothiazolyl, 4-quinolinyl, 5-quinolinyl, 8-quinolinyl), zonalylyl (e.g., Examples include 3-terpinel, 4-terpinel, 5-terpinel, 6-terpinel, 7-terpinel, 8-terpinel), phthalazinyl (e.g., 1-phthalazinyl, 4-phthalazinyl, 5-phthalazinyl, 6-phthalazinyl, 7-phthalazinyl, 8-phthalazinyl), quinazolinyl (e.g., 2-quinazolinyl, 4-quinazolinyl, 5-quinazolinyl, 6-quinazolinyl, 7-quinazolinyl, 8-quinazolinyl), and quinoxalinyl (e.g., 2-...). Quinoxalyl, 3-quinoxalyl, 5-quinoxalyl, 6-quinoxalyl, 7-quinoxalyl, 8-quinoxalyl), pyrazolo[1,5-a]pyridyl (e.g., pyrazolo[1,5-a]pyridin-2-yl, pyrazolo[1,5-a]pyridin-3-yl, pyrazolo[1,5-a]pyridin-4-yl, pyrazolo[1,5-a]pyridin-5-yl, pyrazolo[1,5-a]pyridin-6-yl) The compounds include pyrazolo[1,5-a]pyridin-7-yl and imidazo[1,2-a]pyridinyl (e.g., imidazo[1,2-a]pyridin-2-yl, imidazo[1,2-a]pyridin-3-yl, imidazo[1,2-a]pyridin-5-yl, imidazo[1,2-a]pyridin-6-yl, imidazo[1,2-a]pyridin-7-yl, imidazo[1,2-a]pyridin-8-yl), etc.

[0082] Unless otherwise specified, examples of aromatic rings in this specification include aromatic carbon rings and aromatic heterocycles.

[0083] Unless otherwise specified, examples of aromatic carbocyclic rings in this specification include benzene rings, naphthalene rings, and anthracene rings.

[0084] Unless otherwise specified, examples of aromatic heterocycles in this specification include: (1) Five-membered or six-membered aromatic heterocycles can be listed, and specific examples include furan ring, thiophene ring, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, pyrazole ring, 1,2,3-oxadiazole ring, 1,2,4-oxadiazole ring, 1,3,4-oxadiazole ring, furazon ring, 1,2,3-thiadiazole ring, 1,2,4-thiadiazole ring, 1,3,4-thiadiazole ring, 1,2,3-triazole ring, 1,2,4-triazole ring, tetrazolium ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, etc. (2) A ring formed by the condensation of two of the above-mentioned 5- or 6-membered aromatic heterocycles; and (3) A ring formed by the condensation of one of the above-mentioned 5- or 6-membered aromatic heterocycles with a benzene ring.

[0085] Unless otherwise specified, examples of non-aromatic heterocycles can be listed in this specification: 3- to 8-membered non-aromatic heterocycles containing 1 to 4 heteroatoms selected from oxygen, sulfur, and nitrogen atoms in addition to carbon atoms as cyclic atoms. Specific examples include: ethylene oxide, aziridine, oxacyclobutane, thiohexacyclobutane, pyrrolidine, dihydrofuran, tetrahydrofuran, tetrahydrothiophene, imidazoline, oxazolidine, isoxazoline, piperidine, dihydropyran, tetrahydropyran, tetrahydrothioran, morpholine, thiomorpholine, piperazine, dihydrooxazine, tetrahydrooxazine, dihydropyrimidine, tetrahydropyrimidine, aziridine-heptane, oxacyclobutane, thiohexacyclobutane, oxacyclobutane, oxacyclobutane, oxacyclobutane, oxacyclobutane, and thiohexacyclobutane.

[0086] Examples of "alkali metals" in this specification include lithium, sodium, potassium, rubidium, and cesium.

[0087] In this specification, "alkylene chain" can be a divalent group formed by removing one hydrogen atom from the aforementioned alkyl group.

[0088] compound The compounds of the present invention are branched fluorine compounds represented by the above formula (1) [sometimes referred to as compound (1) in this specification].

[0089] The symbols in equation (1) are explained below.

[0090] L represents the trivalent carbon-containing linker shown in formula (1) (L-1-1), the tetravalent carbon-containing linker shown in formula (2) (L-1-2), the pentavalent carbon-containing linker shown in formula (3) (L-1-3), the hexavalent carbon-containing linker shown in formula (4) (L-1-4), the tetravalent carbon-containing linker shown in formula (5) (L-2), or the aromatic carbon-containing linker shown in formula (6) (L-3) (n1+n2). (where R) L The same or different occurrences each time indicate a hydrogen atom, an alkyl group that can have more than one substituent, -NH2, or -NHR. RL -OH or -OR RL And R RL (represents organic groups) (where R) L The same or different occurrences each time indicate a hydrogen atom, an alkyl group that can have more than one substituent, -NH2, or -NHR. RL-OH or -OR RL And R RL (Indicates substituents) (where R) L Represents hydrogen atoms, alkyl groups that may have more than one substituent, -NH2, -NHR RL -OH or -OR RL And R RL (represents organic groups) [In the formula, ring D represents an aromatic ring].

[0091] R in these structural formulas L The "alkyl" in "alkyl that may have more than one substituent" shown may be the same or different, and is preferably a C1-C10 alkyl.

[0092] Among the carbon-containing connecting parts shown in formulas (L-1-1), (L-1-2), (L-1-3), and (L-1-4), the trivalent carbon-containing connecting part shown in formula (L-1-1) or the tetravalent carbon-containing connecting part shown in formula (L-1-2) is preferred.

[0093] n1 is a number greater than or equal to 1 (preferably a number between 1 and 5).

[0094] n1 can be, for example, 1, 2, 3 or 4 (preferably 1 or 2, more preferably 2).

[0095] n² is a number greater than or equal to 1 (preferably a number between 1 and 5).

[0096] n2 can be, for example, 1, 2, 3 or 4 (preferably 1 or 2, more preferably 2).

[0097] n1 + n2 can be, for example, 3, 4, 5 or 6 (preferably 3 or 4).

[0098] In another preferred embodiment of the invention, L is the connecting part shown in the above formula (L-1-1), above formula (L-1-2), above formula (L-2), or above formula (L-3); n1 is 1 or 2; Furthermore, n2 is 2.

[0099] In another preferred embodiment of the invention, L is the connecting portion shown in the above formula (L-1-2), the above formula (L-2), or the above formula (L-3) [preferably the above formula (L-1-2)]. n1 + n2 equals 4; and... (a) n1 is 3 and n2 is 1, or (b) n1 is 1 and n2 is 3.

[0100] In another preferred embodiment of the invention, L is the connecting part shown in the above formula (L-1-3) or the above formula (L-3) [preferred formula (L-1-3)]; n1 + n2 is 5; and (a) n1 is 4 and n2 is 1. (b) n1 is 3 and n2 is 2. (c) n1 is 2 and n2 is 3, or (d) n1 is 1 and n2 is 4.

[0101] In another preferred embodiment of the invention, L is the connecting part shown in the above formula (L-1-4) or the above formula (L-3) [preferably the above formula (L-1-4)]. n1 + n2 equals 6; and (a) n1 is 5 and n2 is 1. (b) n1 is 4 and n2 is 2. (c) n1 is 3 and n2 is 3. (d) n1 is 2 and n2 is 4, or (e) n1 is 1 and n2 is 5.

[0102] In another preferred embodiment of the invention, L is the connecting part shown in the above formula (L-1-2), the above formula (L-2), or the above formula (L-3); n1 is 3; and n2 is 1.

[0103] The directions of some structural formulas of the above formulas (L-1-1), (L-1-2), (L-2), or (L-3) may be the same as or different from the direction of the structural formula of formula (1).

[0104] Therefore, those skilled in the art will readily understand that each asterisk (*) in the above formulas (L-1-1), (L-1-2), (L-2), or (L-3) independently represents the binding site with Rf-Y- or -X-A.

[0105] The compound (1) having the carbon-containing linker shown in formula (L-1-1) in its preferred embodiment has two groups: Rf-Y- and has the structure shown in formula (1-L-1-1A). [The symbols in the formula have the same meaning as above.] The compound (1) having the carbon-containing linker shown in formula (L-1-1) in a preferred embodiment has two groups: -X-A and has the structure shown in formula (1-L-1-1B). [The symbols in the formula have the same meaning as above.] The compound (1) having the carbon-containing linker shown in formula (L-1-2) in a preferred embodiment has two groups: Rf-Y- and two groups: -X-A, and has the structure shown in formula (1-L-1-2). [The symbols in the formula have the same meaning as above.] The compound (1) having the carbon-containing linker shown in formula (L-2) has, in a preferred embodiment, two groups: Rf-Y- and two groups: -X-A, and a carbon-containing linker from the benzene ring, having the structure shown in formula (1-2). [The symbols in the formula have the same meaning as above.] The fact that Rf is the same or different each time it appears indicates that it can be a fluoroalkyl group with more than one ether bond.

[0106] Rf may be the same or different each time it appears, preferably a C1-C20 fluoroalkyl group that can have one or more ether bonds, more preferably a C1-C8 fluoroalkyl group that can have one or more ether bonds, even more preferably a C1-C7 fluoroalkyl group that can have one or more ether bonds, further preferably a C1-C6 fluoroalkyl group that can have one or more ether bonds, and particularly preferably a C1-C5 fluoroalkyl group that can have one or more ether bonds.

[0107] Rf is preferably a fluoroalkyl group containing a C1-C5 perfluoroalkyl group [which may have more than one ether bond].

[0108] Y is the same or different each time it appears, indicating that (1) it is selected from -O-, -COO-, -OCO-, -CONR. Y - and -NR YThe divalent linker or (2) valence bond in CO-. However, when L is the linker shown in the above formula (L-1-1) or the above formula (L-1-2), Y is not -COO- or -OCO-.

[0109] In a preferred embodiment of the present invention L represents the trivalent carbon-containing linker shown in formula (L-1-1) above or the tetravalent carbon-containing linker shown in formula (L-1-2) above. Furthermore, Y is preferably the same or different each time it appears (preferably the same each time it appears), and is (1) selected from -O-, -CONR. Y - and -NR Y The divalent linker or (2) valence bond in CO-.

[0110] Compounds produced by this method exhibit exceptional stability, particularly under acidic or alkaline conditions.

[0111] R Y Whether the occurrence is the same or different (preferably the same each time) indicates a hydrogen atom or an organic group.

[0112] R Y Preferably, the atom is the same or different each time it appears (preferably the same each time it appears), and is methyl, trifluoromethyl or hydrogen atom.

[0113] R Y More preferably, it is a hydrogen atom.

[0114] Y is more preferably the same or different each time it appears (preferably the same each time it appears), and is -CONH-, -NHCO- or -O-.

[0115] X may be the same or different each time it appears, indicating a divalent linker or valence bond.

[0116] X is preferably the same or different each time it appears (preferably the same each time it appears), and is an alkylene chain or a valence bond.

[0117] X is more preferably a valence bond.

[0118] In a preferred embodiment of the present invention, L is the tetravalent carbon-containing linker shown in formula (L-2) above; and, At least one Y is -O-, -COO-, -OCO-, or -CONR. Y - or - NR Y CO-.

[0119] In a preferred embodiment of the present invention n1 is 1 or 2; Furthermore, n2 is 2.

[0120] A may be the same or different each time it appears (preferably the same each time it appears), and can be -ArSO3M, -SO3M, -SO4M, -PO3M or -COOM.

[0121] A is preferably -COOM or -SO3M, and more preferably -COOM.

[0122] M may be the same or different each time it appears (preferably the same each time it appears), representing a hydrogen atom, -NR4, or a metal salt.

[0123] The R may be the same or different each time it appears, representing a hydrogen atom or a C1-C4 organic group.

[0124] M is preferably -NH4.

[0125] A particularly preferred embodiment of the compound of the present invention comprises the following compounds: The shown is a branched fluorine compound.

[0126] [In the formula,] The fact that Rf is the same or different each time it appears indicates that a fluoroalkyl group can have more than one ether bond; Y is the same or different each time it appears, indicating (1) a divalent linker selected from -O-, -CONH- and -NHCO- or (2) a valence bond; X represents a valence bond; Furthermore, A represents -COONH4].

[0127] Another particularly preferred embodiment of the compound of the present invention is the following compound: The shown is a branched fluorine compound.

[0128] [In the formula,] The fact that Rf is the same or different each time it appears indicates that a fluoroalkyl group can have more than one ether bond; Y is the same or different each time it appears, indicating (1) a divalent linker selected from -O-, -CONH- and -NHCO- or (2) a valence bond; X represents a valence bond; Furthermore, A represents -COONH4].

[0129] Another particularly preferred embodiment of the compound of the present invention is the following compound: The shown is a branched fluorine compound.

[0130] [In the formula,] The fact that Rf is the same or different each time it appears indicates that a fluoroalkyl group can have more than one ether bond; Y is the same or different each time it appears, indicating (1) a divalent linker selected from -O-, -CONH- and -NHCO- or (2) a valence bond; X represents a valence bond; Furthermore, A represents -COONH4].

[0131] Methods for synthesizing compounds The compounds of the present invention can be synthesized by known methods or similar methods, or combinations thereof.

[0132] Specifically, for example, the compound (1) of the present invention, in which A is -COONH4, can be synthesized by adding an ammonia-methanol solution to the compound of formula (1) in which A is -COOH. The compound of formula (1) in which A is -COOH can be manufactured by known methods or obtained commercially.

[0133] Specifically, for example, compounds (1) having a carbon-containing linker as shown in formulas (L-1-1), (L-1-2), (L-2), or (L-3) can be synthesized by reacting a base with a carboxylic acid or its ester having the carbon-containing linker [e.g., dihydroxysuccinic acid (tartaric acid), methyl dihydroxysuccinate, monoaminosuccinic acid (aspartic acid), or diaminosuccinic acid, diethyl malonate] as needed, followed by the addition of a fluorinated compound (e.g., CF3COOCOCF3, CF3COOCH3, C3F7OCF(CF3)COOCH3, CF2=CFOCF2CF2CF3, and CF3CF2CF2CF2CH2CH2I) as an electrophilic agent. Such carboxylic acids or their esters can be manufactured by known methods or obtained commercially.

[0134] The compounds of this invention can appropriately reduce the surface tension of water.

[0135] The compounds of the present invention are suitable for use as surfactants.

[0136] The compounds of the present invention are suitable for use as interface promoters (especially interface promoters in coatings, lacquer or adhesives).

[0137] The compounds of the present invention are also suitable for use as viscosity reducers, for example.

[0138] The compounds of the present invention are also suitable for use as dispersants, particularly aqueous dispersants.

[0139] The compounds of the present invention are also suitable for use as emulsifiers, for example.

[0140] surfactants The present invention also provides surfactants containing the compounds of the present invention described above. The compounds of the present invention can be the active ingredient of the surfactant.

[0141] One aspect of the present invention may be a surface activation method that includes the step of using the compound of the present invention.

[0142] The surfactants of this invention may contain substances other than the compounds of this invention. Examples of such substances include hydrocarbon surfactants.

[0143] Examples of this hydrocarbon-based surfactant include: Formula: R-Y-M (where R is a C6-C17 alkyl group, Y is -ArSO3-, -SO3-, -SO4-, -PO3-, or -COO-, Ar is an aryl group, and M is H-) ＋ Na ＋ K ＋ or NH4 ＋ ) compounds.

[0144] Specific examples of this hydrocarbon-based surfactant include sodium dodecyl sulfate.

[0145] Such hydrocarbon-based surfactants can be obtained commercially, for example.

[0146] Hydrocarbon surfactants include anionic hydrocarbon surfactants, nonionic hydrocarbon surfactants, and cationic surfactants.

[0147] As hydrocarbon surfactants, the following surfactants, which also include surfactants that are commercially available, can be cited as examples.

[0148] [1] Examples of anionic hydrocarbon surfactants include: (1) Highly branched chain-like C10 tertiary carboxylic acid Versatic 10 (trade name, Resolution Performance Products). (2) Linear alkyl polyether sulfonate sodium Avanel S series (trade name, BASF) (3) Sulfosuccinate surfactant Lankropol K8300 (trade name, Akzo Nobel SurfaceChemistry), (4) Diisodecyl sulfosuccinate Na salt (i) Emulsogen SB10 (trade name, Clariant), and (ii) Polirol (trade name) TR / LNA (trade name, Cesapinia Chemicals), (5) SilSense PE-100 silicone (trade name, Noveon Consumer Specialties) and SilSense CA-A silicone (trade name, Noveon Consumer Specialties), and siloxane-based and anionic hydrocarbon surfactants. (6) Sodium dodecyl sulfate (SDS).

[0149] [2] Examples of nonionic hydrocarbon surfactants as hydrocarbon surfactants can be listed as follows: (1) Octylphenol ethoxylated compounds Triton X (trade name, Dow Chemical Company) series, (2) Branched alcohol ethoxylated compounds Tergitol 15-S (trade name, Dow Chemical Company) series, (3) Branched secondary alcohol ethoxylated compounds Dow Tergitol TMN (trade name, Dow Chemical Company) series, (4) Ethylene oxide / propylene oxide copolymers, Tergitol L (trade name, Dow Chemical Company) series, (5) Pluronic R (trade name, BASF) series of difunctional block copolymers, and (6) Tridecaneol alkoxy compounds TDA (trade name, BASF) series.

[0150] [3] Cationic surfactants that are hydrocarbon surfactants can be listed as cetyltrimethylammonium bromide (CTMAB).

[0151] The present invention also provides an aqueous dispersant containing the compounds of the present invention described above. The compounds of the present invention can be the active ingredient in this aqueous dispersant.

[0152] One aspect of the present invention may be a method for dispersing a target substance in an aqueous system, including the step of using the compound of the present invention.

[0153] Example The present invention will now be described in more detail with reference to embodiments, but the present invention is not limited thereto.

[0154] The following explains the meanings of the symbols and abbreviations used in the embodiments.

[0155] AIBN: Azobisisobutyronitrile <Synthesis example> Synthesis example 1 Allyl bromide (1.7 eq.) and silver oxide (2.0 eq.) were added to a diethyl ether solution (100 mL) of diethyl tartrate (4.9 g), and the mixture was stirred at 50 °C for 2 hours. The mixture was then stirred at room temperature for 7 days. The reaction solution was filtered, and the filtrate was concentrated to obtain the compound. 1 (6.3 g, 92%).

[0156] In the compound 1 The solution obtained by adding C4F9I (2.4 eq.) and AIBN (0.2 eq.) to (2.3 g) was heated at 80 °C for 18 hours. After the reaction was complete, water was added, and the mixture was extracted with chloroform. The solvent was removed from the extract by distillation to obtain the compound. 2 (6.0 g, 76%).

[0157] Water and NMP were added to sodium bicarbonate (2.0 eq.) and sodium dithionite (2.0 eq.), and the mixture was stirred. Then, the compound was added dropwise. 2 (6.0 g), stirred for 12 hours. Hydrochloric acid aqueous solution was added to the reaction mixture, and extraction was performed using dichloromethane. The solvent was removed from the extract by distillation to obtain the compound. 3 (2.2 g, 49%).

[0158] In compounds 3 A methanol solution (2.2 g) was added to 10 mL of sodium hydroxide aqueous solution (2.0 eq.), and the mixture was stirred at room temperature for 12 hours. The product was then extracted with ethyl acetate after adding hydrochloric acid aqueous solution. The solvent was removed from the extract by distillation to obtain the compound. 4 (1.4 g, 71%).

[0159] In compounds 4 Ammonia methanol solution (2.0 eq.) was added to a methanol solution (1.4 g) in 10 mL, and the mixture was stirred at room temperature for 1 hour. After the reaction was complete, the solvent was removed by distillation to obtain the compound. 5 (1.5 g, quant.)

[0160] Synthesis example 2 CF3COOCH3 (1.3 eq.) and triethylamine (2.0 eq.) were added to a methanol solution (13 g) of monoaminosuccinic acid (10 mL), and the mixture was stirred at room temperature for 17 hours. A 1N hydrochloric acid aqueous solution was added to the reaction mixture, and the solution was extracted with ethyl acetate. The solvent was removed by distillation from the extract, and the crude product was recrystallized to give the compound. 8 (10 g, 44%).

[0161] In compounds8 Ammonia methanol solution (4.0 eq.) was added to a methanol solution (10 g) in 10 mL, and the mixture was stirred at room temperature for 1 hour. The solvent was then removed by distillation to obtain the compound. 9 (12 g, quant.)

[0162] Synthesis example 3 Using monoaminosuccinic acid (6.5 g) as a starting material, the compound was synthesized according to a method similar to that of Synthesis Example 2 above, but under the conditions described in the above scheme. 6 (5.6 g, 26%), then, the compound was obtained. 7 (5.7 g, 95%).

[0163] Synthesis example 4 Trifluoroacetic anhydride (17 eq.) was added to a THF solution (5.0 mL) of diamine succinate (0.17 g), and the mixture was stirred for 24 hours. The reaction product was concentrated, dissolved in water, and extracted with ethyl acetate. The solvent was removed by distillation, and the crude product was recrystallized to give the compound. 10 (0.13 g, 29%).

[0164] In compounds 10 3M ammonia-methanol solution (4.0 eq.) was added to a methanol solution (0.13 g) in 2.0 mL, and the mixture was stirred at room temperature for 1 hour. The solvent was then removed by distillation to obtain the compound. 11 (0.08 g, quamt.).

[0165] Synthesis Example 4a Perfluoropropionic anhydride (13.5 eq.) was added to a THF solution (0.37 g) of diamine succinate (7.5 mL), and the mixture was stirred for 24 hours. The reaction product was concentrated, dissolved in water, and extracted with ethyl acetate. The solvent was removed by distillation, and the crude product was recrystallized to give the compound. 15 (0.21 g, 20%).

[0166] In compounds 15 3M ammonia-methanol solution (4.0 eq.) was added to a methanol solution (0.05 g) in 2.0 mL, and the mixture was stirred at room temperature for 1 hour. The solvent was then removed by distillation to obtain the compound. 16 (0.004 g, 73%).

[0167] Synthesis example 5 Potassium carbonate (3.0 eq.) and H(CF₂CF₂)₃CH₂OH (3.0 eq.) were added to a DMSO solution of 2.1 g of 4,5-dichlorophthalonitrile (5.0 mL), and the mixture was stirred at room temperature for 11 days. Water was added to the product, and the solution was extracted with dichloromethane. The solvent was removed by distillation, and the product was then recrystallized to give the compound. 12 (0.7 g, 9.0%).

[0168] In compounds 12 Sulfuric acid (9.0 mL) and water (3.0 mL) were added, and the mixture was stirred at 150 °C for 3 hours. After the reaction was complete, 150 mL of water was added to the product, and the mixture was filtered. The crude product was recrystallized to obtain the compound. 13 (0.42 g, 36%).

[0169] In compounds 13 Ammonia-methanol solution (4.0 eq.) was added to a methanol solution (10 mL), and the mixture was stirred at room temperature for 1 hour. The solvent was then removed by distillation to obtain the compound. 14 (0.21 g, 61%).

[0170] Surface tension measurement The determination is performed using ultrapure water solvent according to the traditional Wilhelmy method (slip method).

[0171] The results are shown in the table below.

Claims

1. A branched fluorine compound of formula (1), characterized in that: In equation (1), L represents the tetravalent carbon-containing linker shown in formula (L-1-2). In equation (L-1-2), R L The same or different occurrences each time indicate a hydrogen atom, an alkyl group that can have more than one substituent, -NH2, or -NHR. RL OR RL And R RL Indicates an organic group. Rf may be the same or different each time it appears, indicating a C1-C8 fluoroalkyl group; Y is the same or different each time it appears, indicating that (1) it is selected from -O-, -CONR. Y - and -NR Y The divalent linker or (2) valent bond in CO-; R Y The fact that they appear the same or different each time indicates a hydrogen atom or an organic group; L represents a carbon-containing bonding portion with a (n1+n2) valence of one or more carbon atoms; n1 represents a number greater than or equal to 1; n2 represents a number greater than or equal to 1; n1 + n2 equals 4; X represents a valence bond; A may be the same or different each time it appears, representing -ArSO3M, -SO3M, -SO4M, -PO3M or -COOM; M may be the same or different each time it appears, representing a hydrogen atom, -NR4, or a metal salt; Furthermore, R represents a hydrogen atom and an organic group of C1-C4.

2. The branched fluorine compound as described in claim 1, characterized in that, n1 is 1 and n2 is 3, or n1 is 2 and n2 is 2, or n1 is 3 and n2 is 1.

3. A surfactant containing the branched fluorinated compound as described in claim 1 or 2.

4. An aqueous dispersant containing the branched fluorine compound as described in claim 1 or 2.

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