Compounds containing alkyl-cyano-borate or alkyl-cyano-fluoroborate anions
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C08F-016/12
C08F-012/02
C08F-010/00
C07C-255/00
C07D-233/00
C07D-295/00
C07D-305/00
C07F-005/02
H01G-009/20
H01M-010/0525
H01M-010/0568
H01M-014/00
출원번호
US-0131990
(2012-07-06)
등록번호
US-9058935
(2015-06-16)
우선권정보
EP-11005798 (2011-07-15)
국제출원번호
PCT/EP2012/002859
(2012-07-06)
§371/§102 date
20140110
(20140110)
국제공개번호
WO2013/010641
(2013-01-24)
발명자
/ 주소
Ignatyev, Nikolai (Mykola)
Schulte, Michael
Kawata, Kentaro
Goto, Tomohisa
Sprenger, Jan
Finze, Maik
Frank, Walter
출원인 / 주소
Merc Patent GmbH
대리인 / 주소
Millen, White, Zelano, Branigan, P.C.
인용정보
피인용 횟수 :
0인용 특허 :
3
초록
The invention relates to new compounds containing alkyl/alkenyl-cyano-borate or alkyl/alkenyl-cyano-fluoroborate anions, their preparation and their use, in particular as part of electrolyte formulations for electrochemical or optoelectronic devices.
대표청구항▼
1. A compound of formula I [Kt]z+z[(R1)4-x-y-vB(CN)x(NC)yFv]− I in which R1 in each case independently denotes a straight-chain or branched alkyl group having 1 to 20 C atoms, which optionally contains at least one Cl, Br or I atom, at least one CN group and/or one or more oxygen or sulphur atoms,
1. A compound of formula I [Kt]z+z[(R1)4-x-y-vB(CN)x(NC)yFv]− I in which R1 in each case independently denotes a straight-chain or branched alkyl group having 1 to 20 C atoms, which optionally contains at least one Cl, Br or I atom, at least one CN group and/or one or more oxygen or sulphur atoms, a straight-chain or branched alkenyl group having 2 to 20 C atoms having one or more double bonds, which optionally contains at least one Cl, Br or I atom and/or one or more oxygen or sulphur atoms, a straight-chain or branched alkinyl group having 1 to 20 C atoms having one or more triple bonds, which optionally contains at least one Cl, Br or I atom and/or one or more oxygen or sulphur atoms and optionally may have a double bond, or unsubstituted phenyl,z is 1, 2, 3 or 4,x is 1, 2 or 3,y is 0, 1 or 2,v is 0, 1 or 2,the sum of x+y+v is 2 or 3,Ktz+ denotes an inorganic cation selected from NO+, H+, Li+, Na+, K+, Rb+, Cs+, Mg2+, Cu+, Cu2+, Zn2+, Ag+, Ca2+, Y+3, Yb+3, La+3, Sc+3, Ce+3, Nd+3, Tb+3, Sm+3 or complex (ligands containing) metal cations which include rare-earths, transitions or noble metals or an organic cation selected from (a) a tritylium cation, in which the phenyl groups may be substituted by straight-chain or branched alkyl groups having 1 to 20 C atoms, straight-chain or branched alkenyl having 2 to 20 C atoms and one or more double bonds or straight-chain or branched alkynyl having 2 to 20 C atoms and one or more triple bonds,(b) an oxonium cation of formula (1) or a sulfonium cation of formula (2)) [(Ro)3O]+ (1)[(Ro)3S]+ (2),where Ro each, independently of one another, denotes a straight-chain or branched alkyl group having 1-8 C atoms, non-substituted phenyl or phenyl which is substituted by R1*, OR′, N(R′)2, CN or halogen and in case of sulfonium cations of formula (2) additionally denotes each independently (R′″)2N, R′ is independently of each other H, non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl, R1* is independently of each other non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl, and R′″ is independently of each other straight-chain or branched C1 to C6 alkyl,(c) an ammonium cation, which conforms to the formula (3) [NR4]+ (3),where R in each case, independently of one another, denotes H, OR′, N(R′)2, with the proviso that a maximum of one R in formula (3) is OR′ or N(R′)2, straight-chain or branched alkyl having 1-20 C atoms, straight-chain or branched alkenyl having 2-20 C atoms and one or more double bonds, straight-chain or branched alkynyl having 2-20 C atoms and one or more triple bonds, saturated, partially or fully unsaturated cycloalkyl having 3-7 C atoms, which may be substituted by straight-chain or branched alkyl groups having 1-6 C atoms,where one or two R may be fully substituted by halogens, and one or more of the substituents R may be partially substituted by halogens, and/or by —OH, —OR′, —CN, —N(R′)2, —C(O)OH, —C(O)OR′, —C(O)R′, —C(O)N(R′)2, —SO2N(R′)2, —C(O)X, —SO2OH, —SO2X, —NO2, —SR′, —S(O)R′, or —SO2R′ and where one or two non-adjacent carbon atoms in R which are not in the α-position may each be replaced by —O—, —S—, —S(O)—, —SO2—, —SO2O—, —C(O)—, —C(O)O—, —N+(R′)2—, —P(O)R′O—, —C(O)NR′—, —SO2NR′—, —OP(O)R′O—, —P(O)(N(R′)2)NR′—, —P(R′)2═N— or —P(O)R′—,R′ in each case independently is H, non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl, andX in each case, independently of one another, is halogen;(d) a phosphonium cation, which conforms to the formula (4) [P(R2)4]+ (4),where R2 in each case, independently of one another, denotes H, OR′ or N(R′)2, straight-chain or branched alkyl having 1-20 C atoms, straight-chain or branched alkenyl having 2-20 C atoms and one or more double bonds, straight-chain or branched alkynyl having 2-20 C atoms and one or more triple bonds, saturated, partially or fully unsaturated cycloalkyl having 3-7 C atoms, which may be substituted by straight-chain or branched alkyl groups having 1-6 C atoms,where one or two R2 may be fully substituted by halogens, and one or more of the substituents R2 may be partially substituted by halogens, and/or by —OH, —OR′, —CN, —N(R′)2, —C(O)OH, —C(O)OR′, —C(O)R′, —C(O)N(R′)2, —SO2N(R′)2, —C(O)X, —SO2OH, —SO2X, —NO2, —SR′, —S(O)R′, or —SO2R′, and where one or two non-adjacent carbon atoms in R2 which are not in the α-position may each be replaced by —O—, —S—, —S(O)—, —SO2—, —SO2O—, —C(O)—, —C(O)O—, —N+(R′)2—, —P(O)R′O—, —C(O)NR′—, —SO2NR′—, —OP(O)R′O—, —P(O)(N(R′)2)NR′—, —P(R′)2═N— or —P(O)R′—,R′ in each case independently is H, non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl, andX in each case independently is halogen,(e) a uronium cation, which conforms to the formula (5) [C(NR3R4)(OR5)(NR6R7)]+ (5),where R3 to R7 each, independently of one another, denote H, where H is excluded for R5, straight-chain or branched alkyl having 1 to 20 C atoms, straight-chain or branched alkenyl having 2-20 C atoms and one or more double bonds, straight-chain or branched alkynyl having 2-20 C atoms and one or more triple bonds, saturated, partially or fully unsaturated cycloalkyl having 3-7 C atoms, which may be substituted by straight-chain or branched alkyl groups having 1-6 C atoms,where one or two of the substituents R3 to R7 may be fully substituted by halogens, and one or more of the substituents R3 to R7 may be partially substituted by halogens, and/or by —OH, —OR′, —N(R′)2, —CN, —C(O)OH, —C(O)OR′, —C(O)R′, —C(O)N(R′)2, —SO2N(R′)2, —C(O)X, —SO2OH, —SO2X, —SR′, —S(O)R′, —SO2R′, or —NO2, and where one or two non-adjacent carbon atoms in R3 to R7 which are not in the α-position may each be replaced by —O—, —S—, —S(O)—, —SO2—, —SO2O—, —C(O)—, —C(O)O—, —N+(R′)2—, —P(O)R′O—, —C(O)NR′—, —SO2NR′—, —OP(O)R′O—, —P(O)(N(R′)2)NR′—, —P(R′)2═N— or —P(O)R′—,R′ in each case independently is H, non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl, andX in each case independently is halogen,(f) a thiouronium cation, which conforms to the formula (6) [C(NR3R4)(SR5)(NR6R7)]+ (6),where R3 to R7 each, independently of one another, denote H, where H is excluded for R5, straight-chain or branched alkyl having 1 to 20 C atoms, straight-chain or branched alkenyl having 2-20 C atoms and one or more double bonds, straight-chain or branched alkynyl having 2-20 C atoms and one or more triple bonds, saturated, partially or fully unsaturated cycloalkyl having 3-7 C atoms, which may be substituted by straight-chain or branched alkyl groups having 1-6 C atoms,where one or two of the substituents R3 to R7 may be fully substituted by halogens, and one or more of the substituents R3 to R7 may be partially substituted by halogens, and/or by —OH, —OR′, —N(R′)2, —CN, —C(O)OH, —C(O)OR′, —C(O)R′, —C(O)N(R′)2, —SO2N(R′)2, —C(O)X, —SO2OH, —SO2X, —SR′, —S(O)R′, —SO2R′, or —NO2, and where one or two non-adjacent carbon atoms in R3 to R7 which are not in the α-position may each be replaced by —O—, —S—, —S(O)—, —SO2—, —SO2O—, —C(O)—, —C(O)O—, —N+(R′)2—, —P(O)R′O—, —C(O)NR′—, —SO2NR′—, —OP(O)R′O—, —P(O)(N(R′)2)NR′—, —P(R′)2═N— or —P(O)R′—,R′ in each case independently is H, non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl, andX in each case independently is halogen,(g) a guanidinium cation, which conforms to the formula (7) [C(NR8R9)(NR10R11)(NR12R13)]+ (7),where R8 to R13 each, independently of one another, denote H, —CN, N(R′)2, —OR′, straight-chain or branched alkyl having 1 to 20 C atoms, straight-chain or branched alkenyl having 2-20 C atoms and one or more double bonds, straight-chain or branched alkynyl having 2-20 C atoms and one or more triple bonds, saturated, partially or fully unsaturated cycloalkyl having 3-7 C atoms, which may be substituted by straight-chain or branched alkyl groups having 1-6 C atoms,where one or two of the substituents R8 to R13 may be fully substituted by halogens and one or more of the substituents R8 to R13 may be partially substituted by halogens, and/or by —OH, —OR′, —N(R′)2, —CN, —C(O)OH, —C(O)OR′, —C(O)R′, —C(O)N(R′)2, —SO2N(R′)2, —C(O)X, —SO2OH, —SO2X, —SR′, —S(O)R′, —SO2R′, or —NO2, and where one or two non-adjacent carbon atoms in R8 to R13 which are not in the α-position may each be replaced by —O—, —S—, —S(O)—, —SO2—, —SO2O—, —C(O)—, —C(O)O—, —N+(R′)2—, —P(O)R′O—, —C(O)NR′—, —SO2NR′—, —OP(O)R′O—, —P(O)(N(R′)2)NR′—, —P(R′)2═N— or —P(O)R′—, whereR′ in each case independently is H, non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl, andX in each case independently is halogen;(h) a heterocyclic cation which conforms to the formula (8) [HetN]z+ (8)where HetNz+ denotes a heterocyclic cation selected from where the substituents R1′ to R4′ each, independently of one another, denote H, straight-chain or branched alkyl having 1-20 C atoms, straight-chain or branched alkenyl having 2-20 C atoms and one or more double bonds, straight-chain or branched alkynyl having 2-20 C atoms and one or more triple bonds, andR2′ each, independently of one another, additionally denotes F, Cl, Br, I, —CN, —OR′, —N(R′)2, —P(O)(R′)2, —P(O)(OR′)2, —P(O)(N(R′)2)2, —C(O)R′, —C(O)OR′, —C(O)X, —C(O)N(R′)2, —SO2N(R′)2, —SO2OH, —SO2X, —SR′, —S(O)R′, —SO2R′ or NO2, with the proviso that R1′, R3′, R4′ are in this case independently of each other H and/or a straight-chain or branched alkyl having 1-20 C atoms, straight-chain or branched alkenyl having 2-20 C atoms and one or more double bonds, where one to three substituents R1′ to R4′ may be fully substituted by halogens, and one or more substituents R1′ to R4′ may be partially substituted by halogens, and/or by —OH, —OR′, N(R′)2, —CN, —C(O)OH, —C(O)OR′, —C(O)R′, —C(O)N(R′)2, —SO2N(R′)2, —C(O)X, —SO2OH, —SO2X, —SR′, —S(O)R′, —SO2R′, or —NO2, but where R1′ and R4′ cannot simultaneously be fully substituted by halogens, andwhere, in the substituents R1′ to R4′, one or two non-adjacent carbon atoms which are not bonded to the heteroatom may each be replaced by —O—, —S—, —S(O)—, —SO2—, —SO2O—, —C(O)—, —C(O)O—, —N+(R′)2—, —P(O)R′O—, —C(O)NR′—, —SO2NR′—, —OP(O)R′O—, —P(O)(N(R′)2)NR′—, —P(R′)2═N— or —P(O)R′—,R′ in each case independently is H, non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl, andX in each case independently is halogen, or(i) a iodonium cation which conforms to the formula (9) where the aryl group Ar denotes each independently of each other aryl with 6 to 30 C atoms which is non-substituted or substituted with at least a straight-chain or branched alkyl group having 1 to 20 C atoms, a straight-chain or branched alkenyl group having 2 to 20 C atoms and one or more double bonds, a straight-chain or branched alkynyl group having 2 to 20 C atoms and one or more triple bonds, R1*, NO2, SR′, N(R′)2, CN and/or halogen, andR′ each independently is H, non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl,R1* each independently is non-fluorinated, partially fluorinated or perfluorinated straight-chain or branched C1- to C18-alkyl, saturated C3- to C7-cycloalkyl, non-substituted or substituted phenyl, andhalogen is F, Cl, Br or I,with the proviso that potassium (18-crone-6) tricyano-n-octylborate and tetraethylammonium phenyl-tricyanoborate are excluded. 2. A compound according to claim 1, wherein R1 in each case independently is a straight-chain or branched alkyl group having 1 to 4 C atoms, which optionally contains at least one Br atom or at least one CN group or at least one oxygen atom or a straight-chain or branched alkenyl having 2 to 4 C atoms. 3. A process for the preparation of a compound according to claim 1 in which [Kt]z+ is an alkali metal cation, z denotes 1 and the sum of x+y+v denotes 3, which denotes a compound of formula I-1, [Me]+[(R1)4-x-y-zB(CN)x(NC)yFv]− I-1, in which [Me]+ denotes an alkali metal cation and R1, x, y and v have the meanings according to claim 1, said process comprising: reacting a compound of formula II [Me]+[(R1)BF3]− II in which [Me1]+ denotes an alkali metal cation and R1 has a meaning according to claim 1, with a trialkylsilylcyanide, in which the alkyl groups are each independently of one another straight-chain or branched alkyl having 1 to 8 C atoms. 4. A process for the preparation of a compound according to claim 1 in which [Kt]z+ is an organic cation and the sum of x+y+v denotes 3, said process comprising: reacting a compound of formula III [Kt]z+[(R1)BF3]− III in which [Kt]z+ denotes the organic cation and R1 has a meaning according to claim 1, with a trialkylsilylcyanide, in which the alkyl groups are each independently of one another straight-chain or branched alkyl having 1 to 8 C atoms. 5. A process for the preparation of a compound according to claim 1 in which [Kt]z+ is alkali metal cation, z denotes 1 and the sum of x+y+v denotes 2, said process comprising: reacting a compound of formula IV (R1)2BOCH3 IV in which R1 has a meaning according to claim 1, with a trialkylsilylcyanide in the presence of an alkali metal fluoride, wherein the alkyl groups within the trialkylsilylcyanide are each independently of one another straight-chain or branched alkyl having 1 to 8 C atoms. 6. A process for the preparation of a compound according to claim 1 in which [Kt]z+ is another cation than the used alkali metal cation in the starting material in a salt-exchange reaction, said process comprising: reacting an alkali metal salt of formula I-1 [Me]+[(R1)4-x-y-zB(CN)x(NC)yFv]− I-1 in which [Me]+ is an alkali metal cation and R1, x, y, v and the sum of x+y+v have the meanings according to claim 1, with a compound of formula V KtA V, in which Kt has a meaning of an organic cation or an inorganic cation other than the alkali metal cation of the compound of formula I-1, andA denotes F−, Cl−, Br−, I−, OH−, [HF2]−, [CN]−, [SCN]−, [R1COO]−, [R1OC(O)O]−, [R1SO3]−, [R2COO]−, [R2SO3]−, [R1OSO3]−, [BF4]−, [PF6]−, [HSO4]1−, [NO3]−, [(R2)2P(O)O]−, [R2P(O)O2]2−, [(R1O)2P(O)O]−, [(R1O)P(O)O2]2−, [(R1O)R1P(O)O]−, tosylate, malonate which may be substituted by straight-chain or branched alkyl groups having 1 to 4 C atoms, [HOCO2]− or [CO3]2− (merely for the synthesis of other compounds of formula I-1 having another alkali metal cation than the starting material),R1 is each independently of another a straight-chain or branched alkyl group having 1 to 12 C atoms, andR2 is each independently of one another a straight-chain or branched perfluorinated alkyl group having 1 to 12 C atoms and where electroneutrality should be taken into consideration in the formula of the salt KtA. 7. An electrolyte formulation comprising at least one compound according to claim 1. 8. An electrochemical and/or optoelectronic device comprising an electrolyte formulation according to claim 7. 9. A catalyst, conducting salt, electrolyte, surfactant, phase-transfer catalyst, entrainer, extractant, antistatic additive, plasticizer, heat-transfer-medium, modifier for membranes and textile materials, lubricant, or hydraulic fluid comprising a compound according to claim 1 in which [Kt]z+ is an organic cation or H+ and z is 1, 2, 3 or 4. 10. An electrolyte according to claim 7, in which [Kt]zt is Li+ as conducting salt and/or component of electrolytes. 11. A catalyst, conducting salt, electrolyte, surfactant, phase-transfer catalyst, or antistatic additive comprising a compound according to claim 1 in which [Kt]z+ is an inorganic cation. 12. A process according to claim 6, in which [Kt]z+ is an organic cation and z is 1, 2, 3 or 4. 13. A cationic polymerization initiator, photo-polymerization initiator or photo-acid generator comprising a compound according to claim 1 in which [Kt]z+ is a cation of formula (2), (5), (6), (9), tritylium, pyrylium, 1-benzopyrylium or 2-benzopyrylium. 14. A curable composition comprising at least one compound according to claim 1 with cations of formula (2), (5), (6), (9), tritylium, pyrylium, 1-benzopyrylium or 2-benzopyrylium, and at least one polymerizable compound. 15. A compound according to claim 1, wherein R1 in each case independently denotes a straight-chain or branched alkyl group having 1 to 20 C atoms, which optionally contains at least one Cl, Br or I atom, at least one CN group and/or one or more oxygen or sulphur atoms,a straight-chain or branched alkenyl group having 2 to 20 C atoms having one or more double bonds, which optionally contains at least one Cl, Br or I atom and/or one or more oxygen or sulphur atoms, ora straight-chain or branched alkinyl group having 1 to 20 C atoms having one or more triple bonds, which optionally contains at least one Cl, Br or I atom and/or one or more oxygen or sulphur atoms and optionally may have a double bond. 16. A compound according to claim 1, wherein said compound is potassium methyldicyanofluoroborate, potassium methyltricyanoborate, potassium methyldicyanoisocyanoborate, potassium n-butyldicyanoisocyanoborate, potassium n-butyltricyanoborate, 1-ethyl-3-methylimidazolium n-butyltricyanoborate, potassium allyltricyanoborate, 1-ethyl-3-methylimidazolium methyldicyanofluoroborate, 1-ethyl-3-methylimiazolium methylcyanodifluoroborate, 1-ethyl-3-methylimidazolium tricyano-methylborate, 1-butyl-3-methylimidazolium methyltricyanoborate, triethylsulfonium methyltricyanoborate, methyldiphenylsulfonium methyltricyanoborate, triphenylsulfonium methyltricyanoborate, diphenyliodonium methyltricyanoborate, 2,4,6-triphenylpyrylium methyltricyanoborate, triphenylcarbenium methyltricyanoborate, 1-ethyl-3-methyl-imidazolium vinyltricyanoborate, butylmethylpyrrolidinium tricyanomethylborate, tetrabutylammonium tricyanomethylborate, tetraphenylphosphonium diethyldicyanoborate, 1-ethyl-3-methylimidazolium vinyldicyano-isocyanoborate, potassium methyldicyano-fluoroborate, 1-ethyl-3-methylimidazolium methyldicyanofluoroborate, 1-butyl-1-methylpyrrolidinium methyldicyanofluoroborate, potassium cyanomethyldicyanofluoroborate, 1-ethyl-3-methylimidazolium cyanomethyldicyanofluoroborate, 1-ethyl-3-methylimidazolium cyanomethylcyanodifluoroborate, potassium diethyldicyanoborate, 1-butyl-3-methylimidazolium diethyldicyanoborate, N-butyl-N-methylpyrrolidinium diethyldicyanoborate, or N-butylpyridinium diethyldicyanoborate. 17. A compound according to claim 1, wherein said compound is of formula IA: [Kt]z+z[(R1)B(CN)2F]− IA,wherein [Kt]z+, z and R1 have the meanings defined in claim 1. 18. A compound according to claim 1, wherein said compound is of formula IB: [Kt]z+z[(R1)B(CN)3]− IB,wherein [Kt]z+, z and R1 have the meanings defined in claim 1. 19. A compound according to claim 1, wherein said compound is of formula IC: [Kt]z+z[(R1)B(CN)2(NC)]− IC,wherein [Kt]z+, z and R1 have the meanings defined in claim 1. 20. A compound according to claim 1, wherein said compound is of formula ID: [Kt]z+z[(R1)B(CN)F2]− ID,wherein [Kt]z+, z and R1 have the meanings defined in claim 1. 21. A compound according to claim 1, wherein said compound is of formula IE: [Kt]z+z[(R1)2B(CN)2]− IE,wherein [Kt]z+, z and R1 have the meanings defined in claim 1. 22. A compound according to claim 1, wherein said cation is of formula (2) and is selected from diethyl-methylsulfonium, triethylsulfonium, triphenylsulfonium, diphenyltolylsulfonium, diphenylethylsulfonium, diphenyl-2,2,2-trifluorethyl sulfonium, diphenyl-2-ethoxy-ethylsulfonium, diphenyl-2-chlorethylsulfonium, diphenyl-3-brompropylsulfonium, diphenyl-3-chlorpropylsulfonium, diphenyl-3-cyanopropylsulfonium, diphenylallylsulfonium, diphenyl-4-pentenylsulfonium, diphenylpropargylsulfonium, diphenylbenzylsulfonium, diphenyl(p-cyanobenzyl)sulfonium, diphenyl(p-methylbenzyl)sulfonium, diphenyl(p-phenylthiobenzyl)sulfonium, diphenyl(3,3-dicyano-2-phenyl-2-propenyl)sulfonium, diphenyl(p-methylphenacyl)sulfonium, diphenyl(ethylcarboxy)methylsulfonium, diphenyl(n-octyl)sulfonium, diphenyl(n-octadecyl)sulfonium, diphenyl(ω-carboxytridecyl)sulfonium, diphenyl(3-oxypropyl)sulfonium, diphenyl(ω-carboxydodecyl)sulfonium, dihexyl-phenylsulfonium, ditolylphenylsulfonium, tritolylsulfonium, m- or p-(tert-butyl)phenyl-diphenylsulfonium, m- or p-methoxyphenyl-diphenylsulfonium, m- or p-CN-phenyl-diphenylsulfonium, m- or p-C6H13S-phenyl-diphenylsulfonium, m- or p-C6H5S-phenyl-diphenylsulfonium, Tri(p-methoxyphenyl)sulfonium, tri[4-(4-acetyl-phenylsulfanyl)phenyl]sulfonium, or tri(4-tert.-butylphenyl)sulfonium. 23. A compound according to claim 1, wherein said cation is of formula (3) and R in each case is independently selected from methyl, ethyl, isopropyl, propyl, n-butyl, sec-butyl, pentyl, hexyl, octyl, decyl or tetradecyl. 24. A compound according to claim 1, wherein said cation is of formula (4) and R2 in each case is independently selected from methyl, ethyl, isopropyl, propyl, n-butyl, sec-butyl, pentyl, hexyl, octyl, decyl or tetradecyl. 25. A compound according to claim 1, wherein said cation is of formula (8) and is selected from: where the substituents R1′ to R4′ each, independently of one another, have the meanings indicated in claim 1. 26. A compound according to claim 1, wherein said cation is selected from 1-butyl-1-methylpyrrolidinium, 1-ethyl-3-methylimidazolium, 1-ethyl-2,3-dimethylimidazolium, 1-(2-methoxyethyl)-3-methylimidazolium, 1-butyl-3-methylimidazolium, tributyl-methylammonium, tetra-n-butylammonium, tributyl-methylphosphonium, tetra-phenylphosphonium, diethyl-methylsulfonium, S-ethyl-N,N,N′,N′-tetramethylisothiouronium, 1-allyl-3-methylimidazolium, 1-allyl-2,3-dimethylimidazolium, 1-cyanomethyl-3-methylimidazolium, 1-methyl-3-propinylimidazlium, 1,1-dimethylpyrrolidinium, or trimethylsulfonium.
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Dalzell Rex J. (Somerset WI) Goettert Edward J. (Lake Elmo MN) Tiers George V. D. (St. Paul MN), Imaging systems with tetra(aliphatic) borate salts.
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