CN102731391A - Dye compound - Google Patents

Dye compound Download PDF

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CN102731391A
CN102731391A CN2012101167898A CN201210116789A CN102731391A CN 102731391 A CN102731391 A CN 102731391A CN 2012101167898 A CN2012101167898 A CN 2012101167898A CN 201210116789 A CN201210116789 A CN 201210116789A CN 102731391 A CN102731391 A CN 102731391A
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compound
singly
bound
ethylhexyl
parts
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CN102731391B (en
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朴昭妍
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
    • C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • C07D307/89—Benzo [c] furans; Hydrogenated benzo [c] furans with two oxygen atoms directly attached in positions 1 and 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B25/00—Quinophthalones

Abstract

The invention relates to a dye compound represented by the formula (1). In the formula (1), L1 represents a single bond, the alkylene with 1 to 8 carbon atoms, the -SO2-, the -O-, the -CO-, or the -CO-O-. The hydrogen atoms in the alkylene can be replaced by the halogen atoms, and the -CH2- in the alkylene can be replaced by the -O- or -CO-. R1 and R2 independently represent the alkylene with 1 to 8 hydrogen atoms or carbon atoms. A1 and A2 independently represent the benzene ring which has or dose not have the substituent group, the naphthalene ring which has or dose not have the substituent group, or the quinoline ring which has or dose not have the substituent group.

Description

Dye composition
Technical field
The present invention relates to as the useful compound of dyestuff.
Background technology
In for example fields such as filamentary material, liquid crystal indicator, ink-jet printer, dyestuff is used to utilize reflected light or transmitted light to develop the color.
As such dyestuff, that is widely known by the people for example has, the quinophthalone shown in the following formula (quinophthalone) dyestuff C.I. quinoline yellow.
Figure BSA00000704187600011
[prior art document]
[non-patent literature]
The positive husband of [non-patent literature 1] horizontal hand, sesame palace good fortune pine work, " synthetic dyestuff ", first version, daily magazine industry newspaper office, in April, 1978,128 pages
Summary of the invention
Known above-claimed cpd can not fully satisfy the solvability in organic solvent.
The present invention provides following [1]～[10].
[1] compound shown in the formula (1).
Figure BSA00000704187600012
[in the formula (1), L 1The alkylidene group of expression singly-bound, carbonatoms 1～8 ,-SO 2-,-O-,-CO-or-CO-O-, the Wasserstoffatoms that contains in this alkylidene group can be replaced by halogen atom, contain in this alkylidene group-CH 2-can by-O-or-CO-replaces.
R 1And R 2The alkyl of representing Wasserstoffatoms or carbonatoms 1～8 independently of each other.
A 1And A 2Expression independently of each other has or does not have substituent phenyl ring, has or do not have substituent naphthalene nucleus or has or do not have substituent quinoline ring.
M and n represent 0～5 integer independently of each other, and wherein, m+n is 1～8 integer, and is when m+n is the integer more than 2, a plurality of-SO 2NR 1R 2Can be the same or different each other.]
[2] compound of putting down in writing like [1], A 1Be to have or do not have substituent phenyl ring.
[3] compound of putting down in writing like [1] or [2], A 1Be no substituted phenyl ring or phenyl ring with halogen.
[4] like the compound of each record of [1]～[3], A 1And A 2Be to have or do not have substituent phenyl ring independently of each other.
[5] like the compound of each record of [1]～[4], A 1And A 2Be no substituted phenyl ring or phenyl ring independently of each other with halogen.
[6] like the compound of each record of [1]～[5], R 1And R 2Be the branched-chain alkyl of Wasserstoffatoms or carbonatoms 1～8 independently of each other.
[7] like the compound of each record of [1]～[6], L 1Be singly-bound or-SO 2-.
[8] like the compound of each record of [1]～[7], m+n is 1～5 integer.
[9] compound with each record of [1]～[8] is the dyestuff of principal constituent.
[10] coloured composition that contains the dyestuff of [9] record.
The effect of invention
The solvability in organic solvent of compound of the present invention is excellent.
Embodiment
Compound of the present invention is the compound shown in the formula (1) (below, be sometimes referred to as compound (1)).
Figure BSA00000704187600021
[in the formula (1), L 1The alkylidene group of expression singly-bound, carbonatoms 1～8 ,-SO 2-,-O-,-CO-or-CO-O-, the Wasserstoffatoms that contains in this alkylidene group can be replaced by halogen atom, contain in this alkylidene group-CH 2-can by-O-or-CO-replaces.
R 1And R 2The alkyl of representing Wasserstoffatoms or carbonatoms 1～8 independently of each other.
A 1And A 2Expression independently of each other has or does not have substituent phenyl ring, has or do not have substituent naphthalene nucleus or has or do not have substituent quinoline ring.
M and n represent 0～5 integer independently of each other, and wherein, m+n is 1～8 integer, and is when m+n is the integer more than 2, a plurality of-SO 2NR 1R 2Can be the same or different each other.]
L 1The alkylidene group of expression singly-bound, carbonatoms 1～8 ,-SO 2-,-O-,-CO-or-CO-O-.From thermotolerance this point, L 1Be preferably singly-bound or-SO 2-.
The alkylidene group of carbonatoms 1～8 for example is methylene radical, ethylidene, trimethylene, 1; 2-propylidene, 2,2-propylidene, tetramethylene, 1,3-butylidene, 2; 2-butylidene, pentamethylene, 2,2-pentylidene, 2-methyl-3,3-butylidene, 1; 6-hexylidene, 1, the inferior heptyl of 7-, octamethylene etc.
Halogen atom can give an example fluorine atom, chlorine atom, bromine atoms, iodine atom etc.
The Wasserstoffatoms that is contained in the alkylidene group as carbonatoms 1～8 can be given an example by the substituted group of halogen atom, and 1,1,1,3,3,3-hexafluoro-2,2-propylidene, 2,2-two fluoro-trimethylene, 2,2-two chloro-trimethylene etc.
Contain in the alkylidene group as carbonatoms 1～8-CH 2-quilt-O-or-the substituted group of the CO-group shown in the following formula etc. of can giving an example.In the following formula, * representes bonding position.
Figure BSA00000704187600031
R 1And R 2The alkyl of representing Wasserstoffatoms or carbonatoms 1～8 independently of each other.
R 1And R 2In the alkyl of carbonatoms 1～8 can exemplified by methyl, the straight chained alkyl of ethyl, n-propyl, normal-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl etc.;
Sec.-propyl, isobutyl-, sec.-butyl, isopentyl, 1-methyl amyl, 2-methyl amyl, 3-methyl amyl, 4-methyl amyl, 1-ethyl-butyl, 2-ethyl-butyl, 1-methyl hexyl, 2-methyl hexyl, 3-methyl hexyl, 4-methyl hexyl, 5-methyl hexyl, 1-ethyl pentyl group, 2-ethyl pentyl group, 3-ethyl pentyl group, 1-propyl group butyl, 1-(1-methylethyl) butyl, 1-(1-methylethyl)-2-methyl-propyl, 1-methylheptyl, 2-methylheptyl, 3-methylheptyl, 4-methylheptyl, 5-methylheptyl, 6-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 1-n-propyl amyl group, 2-propyl group amyl group, 1-(1-methylethyl) amyl group, 1-butyl butyl, 1-butyl-2-methylbutyl, 1-butyl-3-methylbutyl, 1-(1; The 1-dimethyl ethyl) butyl butyl, the tertiary butyl, 1,1-dimethyl propyl, 1,1-dimethylbutyl, 1; 2-dimethylbutyl, 1; 3-dimethylbutyl, 2,3-dimethylbutyl, 1-ethyl-2-methyl-propyl, 1,1-dimethyl-amyl group, 1; 2-dimethyl-amyl group, 1; 3-dimethyl-amyl group, 1,4-dimethyl-amyl group, 2,2-dimethyl-amyl group, 2; 3-dimethyl-amyl group, 2; 4-dimethyl-amyl group, 3,3-dimethyl-amyl group, 3,4-dimethyl-amyl group, 1-ethyl-1-methylbutyl, 1-ethyl-2-methylbutyl, 1-ethyl-3-methylbutyl, 2-ethyl-1-methylbutyl, 2-ethyl-3-methylbutyl, 1; 1-dimethyl-hexyl, 1; 2-dimethyl-hexyl, 1,3-dimethyl-hexyl, 1,4-dimethyl-hexyl, 1; 5-dimethyl-hexyl, 2; 2-dimethyl-hexyl, 2,3-dimethyl-hexyl, 2,4-dimethyl-hexyl, 2; 5-dimethyl-hexyl, 3; 3-dimethyl-hexyl, 3,4-dimethyl-hexyl, 3,5-dimethyl-hexyl, 4; 4-dimethyl-hexyl, 4; 5-dimethyl-hexyl, 1-ethyl-2-methyl amyl, 1-ethyl-3-methyl amyl, 1-ethyl-4-methyl amyl, 2-ethyl-1-methyl amyl, 2-ethyl-2-methyl amyl, 2-ethyl-3-methyl amyl, 2-ethyl-4-methyl amyl, 3-ethyl-1-methyl amyl, 3-ethyl-2-methyl amyl, 3-ethyl-3-methyl amyl, 3-ethyl-4-methyl amyl, 1-propyl group-1-methylbutyl, 1-propyl group-2-methylbutyl, 1-propyl group-3-methylbutyl, 1-(1-methylethyl)-1-methylbutyl, 1-(1-methylethyl)-2-methylbutyl, 1-(1-methylethyl)-3-methylbutyl, 1,1-diethylammonium butyl, 1, the branched-chain alkyl of 2-diethylammonium butyl etc.
Wherein, R 1And R 2Preferred be the branched-chain alkyl of carbonatoms 3～8 independently of each other, the more preferably branched-chain alkyl of carbonatoms 6～8, the further preferably branched-chain alkyl of carbonatoms 8, most preferably 2-ethylhexyl.
-SO 2NR 1R 2Can give an example no substituted sulfamyl, N-1 replaces sulfamyl and N, and N-2 replaces sulfamyl.
N-1 replaces sulfamyl can give an example N-methyl sulfamyl, N-ethyl sulfamyl, N-propyl group sulfamyl, N-sec.-propyl sulfamyl, N-butyl sulfamyl, N-isobutyl-sulfamyl, N-sec.-butyl sulfamyl, N-tertiary butyl sulfamyl, N-amyl group sulfamyl, N-(1-ethyl propyl) sulfamyl, N-(1; The 1-dimethyl propyl) sulfamyl, N-(1; The 2-dimethyl propyl) sulfamyl, N-(2; The 2-dimethyl propyl) sulfamyl, N-(1-methylbutyl) sulfamyl, N-(2-methylbutyl) sulfamyl, N-(3-methylbutyl) sulfamyl, N-cyclopentyl sulfamyl, N-hexyl sulfamyl, N-(1; The 3-dimethylbutyl) sulfamyl, N-(3; The 3-dimethylbutyl) sulfamyl, N-heptyl sulfamyl, N-(1-methyl hexyl) sulfamyl, N-(1; 4-dimethyl-amyl group) sulfamyl, N-octyl group sulfamyl, N-(2-ethylhexyl) sulfamyl, N-(1, the 5-dimethyl-) hexyl sulfamyl, N-(1,1; 2, the 2-tetramethyl butyl) sulfamyl etc.
N, N-2 replace the sulfamyl N that can give an example, N-dimethylamino alkylsulfonyl, N; N-ethyl-methyl sulfamyl, N, N-diethyl amino alkylsulfonyl, N, N-propyl group methyl sulfamyl, N; N-isopropyl methyl sulfamyl, N, N-tertiary butyl methyl sulfamyl, N, N-butyl ethyl sulfamyl, N; N-two (1-methyl-propyl) sulfamyl, N, N-heptyl methyl sulfamyl etc.
M and n represent 0～5 integer independently of each other.Wherein, m+n is 1～8 integer, preferred 1～5 integer.In addition, preferred m and n are 0 or 1 independently of each other, and m+n is 1.
There is a plurality of-SO 2NR 1R 2The time, preferably between them the group of identical kind.
A 1And A 2Expression independently of each other has or does not have substituent phenyl ring, has or do not have substituent naphthalene nucleus or has or do not have substituent quinoline ring.These substituting group can be given an example-R 3,-OR 3,-COR 3,-O-COR 3, carbonatoms 1～8 fluoroalkyl, halogen, hydroxyl, alkylsulfonyl, carboxyl, nitro, formyl radical ,-NHR 3,-NR 3R 4Deng.Here, R 3And R 4The alkyl of expression carbonatoms 1～8, this alkyl can be and the above-mentioned cited identical group of group.
The fluoroalkyl of carbonatoms 1～8 can give an example fluoro methyl, trifluoromethyl, fluoro ethyl, pentafluoroethyl group, perfluoro propyl, perfluoro butyl, perfluor amyl group, perfluoro hexyl, perfluor heptyl, perfluoro capryl etc.
-OR 3Can give an example methoxyl group, oxyethyl group, propoxy-, butoxy, pentyloxy, hexyloxy, heptan oxygen base, octyloxy, 2-ethyl hexyl oxy etc.
-COR 3Can give an example ethanoyl, propionyl group, butyryl radicals, pentanoyl, valeryl etc.
-O-COR 3Can give an example acetoxyl group, propionyloxy, butyryl acyloxy, penta acyloxy, new pentane acyloxy etc.
-NHR 3Can give an example N-methylamino, N-ethylamino, N-propyl group amino, N-butyl amino, N-amyl group amino, N-octyl group amino etc.
-NR 3R 4The N that can give an example, N-dimethylamino, N, N-diethylamino, N, the N-dipropyl is amino, N, N-dibutylamino, N-butyl-N-methylamino, N, N-dioctyl amino etc.
That halogen can be given an example is fluorine-based, chloro, bromo, iodo etc., preferred chloro.
Wherein, A 1Be preferably and have or do not have substituent phenyl ring, A 1More preferably do not have substituted phenyl ring or have the phenyl ring of halogen.Under such situation, preferred halogen is a chloro.
In addition, preferred A 1And A 2Independently of each other for having or not having substituent phenyl ring, more preferably A 1And A 2Be no substituted phenyl ring or phenyl ring independently of each other with halogen.Under such situation, preferred halogen is a chloro.
In addition, more preferably A 1And A 2Be no substituted phenyl ring or phenyl ring independently of each other with halogen, R 1And R 2Be the branched-chain alkyl of Wasserstoffatoms or carbonatoms 8 independently of each other, L 1For singly-bound or-SO 2-, m and n are 0 or 1 independently of each other, and m+n is 1.Under such situation, preferred halogen is a chloro.
And then, further preferred A 1And A 2Identical and for no substituted phenyl ring or have the phenyl ring of halogen, R 1And R 2Identical and be the branched-chain alkyl of Wasserstoffatoms or carbonatoms 8, L 1Be singly-bound or-SO 2-, m and n are 0 or 1 independently of each other, and m+n is 1.Under such situation, preferred halogen is a chloro.
In the compound (1)
The shown group group shown in following formula (q-1)～formula (q-46) etc. of can giving an example.Wherein, Preferred formula (q-1), formula (q-14), formula (q-24), formula (q-26), formula (q-30), formula (q-31), formula (q-35), formula (q-36) and formula (q-38), the more preferably group shown in formula (q-1), formula (q-14), formula (q-26), formula (q-35) and the formula (q-38).X representes m or n in the following formula.
Figure BSA00000704187600062
Figure BSA00000704187600071
Figure BSA00000704187600081
For the ease of making compound (1), preferred
Figure BSA00000704187600082
Be identical structure.
Compound (1) compound (the 1-1)～compound (1-405) etc. of can giving an example.In addition, Q 1Expression
Q 2Expression
In the table 1, Q 1Hurdle and Q 2The numbering of the chemical formula of above-mentioned illustrative group has been put down in writing on the hurdle.
[table 1]
Compound L 1 Q 1 Q 2 R 1 R 2 m+n
1-1 -SO 2- (q-1) (q-1) CH 3 CH 3 1
1-2 -SO 2- (q-1) (q-1) C 2H 5 C 2H 5 1
1-3 -SO 2- (q-1) (q-1) C 3H 7 C 3H 7 1
1-4 -SO 2- (q-1) (q-1) C 4H 9 C 4H 9 1
1-5 -SO 2- (q-1) (q-1) The 2-ethylhexyl H 1
1-6 -SO 2- (q-14) (q-14) CH 3 CH 3 1
1-7 -SO 2- (q-14) (q-14) C 2H 5 C 2H 5 1
1-8 -SO 2- (q-14) (q-14) C 3H 7 C 3H 7 1
1-9 -SO 2- (q-14) (q-14) C 4H 9 C 4H 9 1
1-10 -SO 2- (q-14) (q-14) The 2-ethylhexyl H 1
1-11 -SO 2- (q-24) (q-24) CH 3 CH 3 1
1-12 -SO 2- (q-24) (q-24) C 2H 5 C 2H 5 1
1-13 -SO 2- (q-24) (q-24) C 3H 7 C 3H 7 1
1-14 -SO 2- (q-24) (q-24) C 4H 9 C 4H 9 1
1-15 -SO 2- (q-24) (q-24) The 2-ethylhexyl H 1
1-16 -SO 2- (q-26) (q-26) CH 3 CH 3 1
1-17 -SO 2- (q-26) (q-26) C 2H 5 C 2H 5 1
1-18 -SO 2- (q-26) (q-26) C 3H 7 C 3H 7 1
1-19 -SO 2- (q-26) (q-26) C 4H 9 C 4H 9 1
1-20 -SO 2- (q-26) (q-26) The 2-ethylhexyl H 1
1-21 -SO 2- (q-30) (q-30) CH 3 CH 3 1
1-22 -SO 2- (q-30) (q-30) C 2H 5 C 2H 5 1
1-23 -SO 2- (q-30) (q-30) C 3H 7 C 3H 7 1
1-24 -SO 2- (q-30) (q-30) C 4H 9 C 4H 9 1
1-25 -SO 2- (q-30) (q-30) The 2-ethylhexyl H 1
1-26 -SO 2- (q-31) (q-31) CH 3 CH 3 1
1-27 -SO 2- (q-31) (q-31) C 2H 5 C 2H 5 1
1-28 -SO 2- (q-31) (q-31) C 3H 7 C 3H 7 1
1-29 -SO 2- (q-31) (q-31) C 4H 9 C 4H 9 1
1-30 -SO 2- (q-31) (q-31) The 2-ethylhexyl H 1
1-31 -SO 2- (q-35) (q-35) CH 3 CH 3 1
1-32 -SO 2- (q-35) (q-35) C 2H 5 C 2H 5 1
1-33 -SO 2- (q-35) (q-35) C 3H 7 C 3H 7 1
1-34 -SO 2- (q-35) (q-35) C 4H 9 C 4H 9 1
1-35 -SO 2- (q-35) (q-35) The 2-ethylhexyl H 1
1-36 -SO 2- (q-36) (q-36) CH 3 CH 3 1
1-37 -SO 2- (q-36) (q-36) C 2H 5 C 2H 5 1
1-38 -SO 2- (q-36) (q-36) C 3H 7 C 3H 7 1
1-39 -SO 2- (q-36) (q-36) C 4H 9 C 4H 9 1
1-40 -SO 2- (q-36) (q-36) The 2-ethylhexyl H 1
1-41 -SO 2- (q-38) (q-38) CH 3 CH 3 1
1-42 -SO 2- (q-38) (q-38) C 2H 5 C 2H 5 1
1-43 -SO 2- (q-38) (q-38) C 3H 7 C 3H 7 1
1-44 -SO 2- (q-38) (q-38) C 4H 9 C 4H 9 1
1-45 -SO 2- (q-38) (q-38) The 2-ethylhexyl H 1
1-46 Singly-bound (q-1) (q-1) CH 3 CH 3 1
1-47 Singly-bound (q-1) (q-1) C 2H 5 C 2H 5 1
1-48 Singly-bound (q-1) (q-1) C 3H 7 C 3H 7 1
1-49 Singly-bound (q-1) (q-1) C 4H 9 C 4H 9 1
1-50 Singly-bound (q-1) (q-1) The 2-ethylhexyl H 1
1-51 Singly-bound (q-14) (q-14) CH 3 CH 3 1
1-52 Singly-bound (q-14) (q-14) C 2H 5 C 2H 5 1
1-53 Singly-bound (q-14) (q-14) C 3H 7 C 3H 7 1
1-54 Singly-bound (q-14) (q-14) C 4H 9 C 4H 9 1
1-55 Singly-bound (q-14) (q-14) The 2-ethylhexyl H 1
1-56 Singly-bound (q-24) (q-24) CH 3 CH 3 1
1-57 Singly-bound (q-24) (q-24) C 2H 5 C 2H 5 1
1-58 Singly-bound (q-24) (q-24) C 3H 7 C 3H 7 1
1-59 Singly-bound (q-24) (q-24) C 4H 9 C 4H 9 1
1-60 Singly-bound (q-24) (q-24) The 2-ethylhexyl H 1
1-61 Singly-bound (q-26) (q-26) CH 3 CH 3 1
1-62 Singly-bound (q-26) (q-26) C 2H 5 C 2H 5 1
1-63 Singly-bound (q-26) (q-26) C 3H 7 C 3H 7 1
1-64 Singly-bound (q-26) (q-26) C 4H 9 C 4H 9 1
1-65 Singly-bound (q-26) (q-26) The 2-ethylhexyl H 1
1-66 Singly-bound (q-30) (q-30) CH 3 CH 3 1
1-67 Singly-bound (q-30) (q-30) C 2H 5 C 2H 5 1
1-68 Singly-bound (q-30) (q-30) C 3H 7 C 3H 7 1
1-69 Singly-bound (q-30) (q-30) C 4H 9 C 4H 9 1
1-70 Singly-bound (q-30) (q-30) The 2-ethylhexyl H 1
1-71 Singly-bound (q-31) (q-31) CH 3 CH 3 1
1-72 Singly-bound (q-31) (q-31) C 2H 5 C 2H 5 1
1-73 Singly-bound (q-31) (q-31) C 3H 7 C 3H 7 1
1-74 Singly-bound (q-31) (q-31) C 4H 9 C 4H 9 1
1-75 Singly-bound (q-31) (q-31) The 2-ethylhexyl H 1
1-76 Singly-bound (q-35) (q-35) CH 3 CH 3 1
1-77 Singly-bound (q-35) (q-35) C 2H 5 C 2H 5 1
1-78 Singly-bound (q-35) (q-35) C 3H 7 C 3H 7 1
1-79 Singly-bound (q-35) (q-35) C 4H 9 C 4H 9 1
1-80 Singly-bound (q-35) (q-35) The 2-ethylhexyl H 1
1-81 Singly-bound (q-36) (q-36) CH 3 CH 3 1
1-82 Singly-bound (q-36) (q-36) C 2H 5 C 2H 5 1
1-83 Singly-bound (q-36) (q-36) C 3H 7 C 3H 7 1
1-84 Singly-bound (q-36) (q-36) C 4H 9 C 4H 9 1
1-85 Singly-bound (q-36) (q-36) The 2-ethylhexyl H 1
1-86 Singly-bound (q-38) (q-38) CH 3 CH 3 1
1-87 Singly-bound (q-38) (q-38) C 2H 5 C 2H 5 1
1-88 Singly-bound (q-38) (q-38) C 3H 7 C 3H 7 1
1-89 Singly-bound (q-38) (q-38) C 4H 9 C 4H 9 1
1-90 Singly-bound (q-38) (q-38) The 2-ethylhexyl H 1
1-91 -CO- (q-1) (q-1) CH 3 CH 3 1
1-92 -CO- (q-1) (q-1) C 2H 5 C 2H 5 1
1-93 -CO- (q-1) (q-1) C 3H 7 C 3H 7 1
1-94 -CO- (q-1) (q-1) C 4H 9 C 4H 9 1
1-95 -CO- (q-1) (q-1) The 2-ethylhexyl H 1
1-96 -CO- (q-14) (q-14) CH 3 CH 3 1
1-97 -CO- (q-14) (q-14) C 2H 5 C 2H 5 1
1-98 -CO- (q-14) (q-14) C 3H 7 C 3H 7 1
1-99 -CO- (q-14) (q-14) C 4H 9 C 4H 9 1
1-100 -CO- (q-14) (q-14) The 2-ethylhexyl H 1
1-101 -CO- (q-24) (q-24) CH 3 CH 3 1
1-102 -CO- (q-24) (q-24) C 2H 5 C 2H 5 1
1-103 -CO- (q-24) (q-24) C 3H 7 C 3H 7 1
1-104 -CO- (q-24) (q-24) C 4H 9 C 4H 9 1
1-105 -CO- (q-24) (q-24) The 2-ethylhexyl H 1
1-106 -CO- (q-26) (q-26) CH 3 CH 3 1
1-107 -CO- (q-26) (q-26) C 2H 5 C 2H 5 1
1-108 -CO- (q-26) (q-26) C 3H 7 C 3H 7 1
1-109 -CO- (q-26) (q-26) C 4H 9 C 4H 9 1
1-110 -CO- (q-26) (q-26) The 2-ethylhexyl H 1
1-111 -CO- (q-30) (q-30) CH 3 CH 3 1
1-112 -CO- (q-30) (q-30) C 2H 5 C 2H 5 1
1-113 -CO- (q-30) (q-30) C 3H 7 C 3H 7 1
1-114 -CO- (q-30) (q-30) C 4H 9 C 4H 9 1
1-115 -CO- (q-30) (q-30) The 2-ethylhexyl H 1
1-116 -CO- (q-31) (q-31) CH 3 CH 3 1
1-117 -CO- (q-31) (q-31) C 2H 5 C 2H 5 1
1-118 -CO- (q-31) (q-31) C 3H 7 C 3H 7 1
1-119 -CO- (q-31) (q-31) C 4H 9 C 4H 9 1
1-120 -CO- (q-31) (q-31) The 2-ethylhexyl H 1
1-121 -CO- (q-35) (q-35) CH 3 CH 3 1
1-122 -CO- (q-35) (q-35) C 2H 5 C 2H 5 1
1-123 -CO- (q-35) (q-35) C 3H 7 C 3H 7 1
1-124 -CO- (q-35) (q-35) C 4H 9 C 4H 9 1
1-125 -CO- (q-35) (q-35) The 2-ethylhexyl H 1
1-126 -CO- (q-36) (q-36) CH 3 CH 3 1
1-127 -CO- (q-36) (q-36) C 2H 5 C 2H 5 1
1-128 -CO- (q-36) (q-36) C 3H 7 C 3H 7 1
1-129 -CO- (q-36) (q-36) C 4H 9 C 4H 9 1
1-130 -CO- (q-36) (q-36) The 2-ethylhexyl H 1
1-131 -CO- (q-38) (q-38) CH 3 CH 3 1
1-132 -CO- (q-38) (q-38) C 2H 5 C 2H 5 1
1-133 -CO- (q-38) (q-38) C 3H 7 C 3H 7 1
1-134 -CO- (q-38) (q-38) C 4H 9 C 4H 9 1
1-135 -CO- (q-38) (q-38) The 2-ethylhexyl H 1
1-136 -SO 2- (q-1) (q-1) CH 3 CH 3 2
1-137 -SO 2- (q-1) (q-1) C 2H 5 C 2H 5 2
1-138 -SO 2- (q-1) (q-1) C 3H 7 C 3H 7 2
1-139 -SO 2- (q-1) (q-1) C 4H 9 C 4H 9 2
1-140 -SO 2- (q-1) (q-1) The 2-ethylhexyl H 2
1-141 -SO 2- (q-14) (q-14) CH 3 CH 3 2
1-142 -SO 2- (q-14) (q-14) C 2H 5 C 2H 5 2
1-143 -SO 2- (q-14) (q-14) C 3H 7 C 3H 7 2
1-144 -SO 2- (q-14) (q-14) C 4H 9 C 4H 9 2
1-145 -SO 2- (q-14) (q-14) The 2-ethylhexyl H 2
1-146 -SO 2- (q-24) (q-24) CH 3 CH 3 2
1-147 -SO 2- (q-24) (q-24) C 2H 5 C 2H 5 2
1-148 -SO 2- (q-24) (q-24) C 3H 7 C 3H 7 2
1-149 -SO 2- (q-24) (q-24) C 4H 9 C 4H 9 2
1-150 -SO 2- (q-24) (q-24) The 2-ethylhexyl H 2
1-151 -SO 2- (q-26) (q-26) CH 3 CH 3 2
1-152 -SO 2- (q-26) (q-26) C 2H 5 C 2H 5 2
1-153 -SO 2- (q-26) (q-26) C 3H 7 C 3H 7 2
1-154 -SO 2- (q-26) (q-26) C 4H 9 C 4H 9 2
1-155 -SO 2- (q-26) (q-26) The 2-ethylhexyl H 2
1-156 -SO 2- (q-30) (q-30) CH 3 CH 3 2
1-157 -SO 2- (q-30) (q-30) C 2H 5 C 2H 5 2
1-158 -SO 2- (q-30) (q-30) C 3H 7 C 3H 7 2
1-159 -SO 2- (q-30) (q-30) C 4H 9 C 4H 9 2
1-160 -SO 2- (q-30) (q-30) The 2-ethylhexyl H 2
1-161 -SO 2- (q-31) (q-31) CH 3 CH 3 2
1-162 -SO 2- (q-31) (q-31) C 2H 5 C 2H 5 2
1-163 -SO 2- (q-31) (q-31) C 3H 7 C 3H 7 2
1-164 -SO 2- (q-31) (q-31) C 4H 9 C 4H 9 2
1-165 -SO 2- (q-31) (q-31) The 2-ethylhexyl H 2
1-166 -SO 2- (q-35) (q-35) CH 3 CH 3 2
1-167 -SO 2- (q-35) (q-35) C 2H 5 C 2H 5 2
1-168 -SO 2- (q-35) (q-35) C 3H 7 C 3H 7 2
1-169 -SO 2- (q-35) (q-35) C 4H 9 C 4H 9 2
1-170 -SO 2- (q-35) (q-35) The 2-ethylhexyl H 2
1-171 -SO 2- (q-36) (q-36) CH 3 CH 3 2
1-172 -SO 2- (q-36) (q-36) C 2H 5 C 2H 5 2
1-173 -SO 2- (q-36) (q-36) C 3H 7 C 3H 7 2
1-174 -SO 2- (q-36) (q-36) C 4H 9 C 4H 9 2
1-175 -SO 2- (q-36) (q-36) The 2-ethylhexyl H 2
1-176 -SO 2- (q-38) (q-38) CH 3 CH 3 2
1-177 -SO 2- (q-38) (q-38) C 2H 5 C 2H 5 2
1-178 -SO 2- (q-38) (q-38) C 3H 7 C 3H 7 2
1-179 -SO 2- (q-38) (q-38) C 4H 9 C 4H 9 2
1-180 -SO 2- (q-38) (q-38) The 2-ethylhexyl H 2
1-181 Singly-bound (q-1) (q-1) CH 3 CH 3 2
1-182 Singly-bound (q-1) (q-1) C 2H 5 C 2H 5 2
1-183 Singly-bound (q-1) (q-1) C 3H 7 C 3H 7 2
1-184 Singly-bound (q-1) (q-1) C 4H 9 C 4H 9 2
1-185 Singly-bound (q-1) (q-1) The 2-ethylhexyl H 2
1-186 Singly-bound (q-14) (q-14) CH 3 CH 3 2
1-187 Singly-bound (q-14) (q-14) C 2H 5 C 2H 5 2
1-188 Singly-bound (q-14) (q-14) C 3H 7 C 3H 7 2
1-189 Singly-bound (q-14) (q-14) C 4H 9 C 4H 9 2
1-190 Singly-bound (q-14) (q-14) The 2-ethylhexyl H 2
1-191 Singly-bound (q-24) (q-24) CH 3 CH 3 2
1-192 Singly-bound (q-24) (q-24) C 2H 5 C 2H 5 2
1-193 Singly-bound (q-24) (q-24) C 3H 7 C 3H 7 2
1-194 Singly-bound (q-24) (q-24) C 4H 9 C 4H 9 2
1-195 Singly-bound (q-24) (q-24) The 2-ethylhexyl H 2
1-196 Singly-bound (q-26) (q-26) CH 3 CH 3 2
1-197 Singly-bound (q-26) (q-26) C 2H 5 C 2H 5 2
1-198 Singly-bound (q-26) (q-26) C 3H 7 C 3H 7 2
1-199 Singly-bound (q-26) (q-26) C 4H 9 C 4H 9 2
1-200 Singly-bound (q-26) (q-26) The 2-ethylhexyl H 2
1-201 Singly-bound (q-30) (q-30) CH 3 CH 3 2
1-202 Singly-bound (q-30) (q-30) C 2H 5 C 2H 5 2
1-203 Singly-bound (q-30) (q-30) C 3H 7 C 3H 7 2
1-204 Singly-bound (q-30) (q-30) C 4H 9 C 4H 9 2
1-205 Singly-bound (q-30) (q-30) The 2-ethylhexyl H 2
1-206 Singly-bound (q-31) (q-31) CH 3 CH 3 2
1-207 Singly-bound (q-31) (q-31) C 2H 5 C 2H 5 2
1-208 Singly-bound (q-31) (q-31) C 3H 7 C 3H 7 2
1-209 Singly-bound (q-31) (q-31) C 4H 9 C 4H 9 2
1-210 Singly-bound (q-31) (q-31) The 2-ethylhexyl H 2
1-211 Singly-bound (q-35) (q-35) CH 3 CH 3 2
1-212 Singly-bound (q-35) (q-35) C 2H 5 C 2H 5 2
1-213 Singly-bound (q-35) (q-35) C 3H 7 C 3H 7 2
1-214 Singly-bound (q-35) (q-35) C 4H 9 C 4H 9 2
1-215 Singly-bound (q-35) (q-35) The 2-ethylhexyl H 2
1-216 Singly-bound (q-36) (q-36) CH 3 CH 3 2
1-217 Singly-bound (q-36) (q-36) C 2H 5 C 2H 5 2
1-218 Singly-bound (q-36) (q-36) C 3H 7 C 3H 7 2
1-219 Singly-bound (q-36) (q-36) C 4H 9 C 4H 9 2
1-220 Singly-bound (q-36) (q-36) The 2-ethylhexyl H 2
1-221 Singly-bound (q-38) (q-38) CH 3 CH 3 2
1-222 Singly-bound (q-38) (q-38) C 2H 5 C 2H 5 2
1-223 Singly-bound (q-38) (q-38) C 3H 7 C 3H 7 2
1-224 Singly-bound (q-38) (q-38) C 4H 9 C 4H 9 2
1-225 Singly-bound (q-38) (q-38) The 2-ethylhexyl H 2
1-226 -CO- (q-1) (q-1) CH 3 CH 3 2
1-227 -CO- (q-1) (q-1) C 2H 5 C 2H 5 2
1-228 -CO- (q-1) (q-1) C 3H 7 C 3H 7 2
1-229 -CO- (q-1) (q-1) C 4H 9 C 4H 9 2
1-230 -CO- (q-1) (q-1) The 2-ethylhexyl H 2
1-231 -CO- (q-14) (q-14) CH 3 CH 3 2
1-232 -CO- (q-14) (q-14) C 2H 5 C 2H 5 2
1-233 -CO- (q-14) (q-14) C 3H 7 C 3H 7 2
1-234 -CO- (q-14) (q-14) C 4H 9 C 4H 9 2
1-235 -CO- (q-14) (q-14) The 2-ethylhexyl H 2
1-236 -CO- (q-24) (q-24) CH 3 CH 3 2
1-237 -CO- (q-24) (q-24) C 2H 5 C 2H 5 2
1-238 -CO- (q-24) (q-24) C 3H 7 C 3H 7 2
1-239 -CO- (q-24) (q-24) C 4H 9 C 4H 9 2
1-240 -CO- (q-24) (q-24) The 2-ethylhexyl H 2
1-241 -CO- (q-26) (q-26) CH 3 CH 3 2
1-242 -CO- (q-26) (q-26) C 2H 5 C 2H 5 2
1-243 -CO- (q-26) (q-26) C 3H 7 C 3H 7 2
1-244 -CO- (q-26) (q-26) C 4H 9 C 4H 9 2
1-245 -CO- (q-26) (q-26) The 2-ethylhexyl H 2
1-246 -CO- (q-30) (q-30) CH 3 CH 3 2
1-247 -CO- (q-30) (q-30) C 2H 5 C 2H 5 2
1-248 -CO- (q-30) (q-30) C 3H 7 C 3H 7 2
1-249 -CO- (q-30) (q-30) C 4H 9 C 4H 9 2
1-250 -CO- (q-30) (q-30) The 2-ethylhexyl H 2
1-251 -CO- (q-31) (q-31) CH 3 CH 3 2
1-252 -CO- (q-31) (q-31) C 2H 5 C 2H 5 2
1-253 -CO- (q-31) (q-31) C 3H 7 C 3H 7 2
1-254 -CO- (q-31) (q-31) C 4H 9 C 4H 9 2
1-255 -CO- (q-31) (q-31) The 2-ethylhexyl H 2
1-256 -CO- (q-35) (q-35) CH 3 CH 3 2
1-257 -CO- (q-35) (q-35) C 2H 5 C 2H 5 2
1-258 -CO- (q-35) (q-35) C 3H 7 C 3H 7 2
1-259 -CO- (q-35) (q-35) C 4H 9 C 4H 9 2
1-260 -CO- (q-35) (q-35) The 2-ethylhexyl H 2
1-261 -CO- (q-36) (q-36) CH 3 CH 3 2
1-262 -CO- (q-36) (q-36) C 2H 5 C 2H 5 2
1-263 -CO- (q-36) (q-36) C 3H 7 C 3H 7 2
1-264 -CO- (q-36) (q-36) C 4H 9 C 4H 9 2
1-265 -CO- (q-36) (q-36) The 2-ethylhexyl H 2
1-266 -CO- (q-38) (q-38) CH 3 CH 3 2
1-267 -CO- (q-38) (q-38) C 2H 5 C 2H 5 2
1-268 -CO- (q-38) (q-38) C 3H 7 C 3H 7 2
1-269 -CO- (q-38) (q-38) C 4H 9 C 4H 9 2
1-270 -CO- (q-38) (q-38) The 2-ethylhexyl H 2
1-271 -SO 2- (q-1) (q-1) CH 3 CH 3 3
1-272 -SO 2- (q-1) (q-1) C 2H 5 C 2H 5 3
1-273 -SO 2- (q-1) (q-1) C 3H 7 C 3H 7 3
1-274 -SO 2- (q-1) (q-1) C 4H 9 C 4H 9 3
1-275 -SO 2- (q-1) (q-1) The 2-ethylhexyl H 3
1-276 -SO 2- (q-14) (q-14) CH 3 CH 3 3
1-277 -SO 2- (q-14) (q-14) C 2H 5 C 2H 5 3
1-278 -SO 2- (q-14) (q-14) C 3H 7 C 3H 7 3
1-279 -SO 2- (q-14) (q-14) C 4H 9 C 4H 9 3
1-280 -SO 2- (q-14) (q-14) The 2-ethylhexyl H 3
1-281 -SO 2- (q-24) (q-24) CH 3 CH 3 3
1-282 -SO 2- (q-24) (q-24) C 2H 5 C 2H 5 3
1-283 -SO 2- (q-24) (q-24) C 3H 7 C 3H 7 3
1-284 -SO 2- (q-24) (q-24) C 4H 9 C 4H 9 3
1-285 -SO 2- (q-24) (q-24) The 2-ethylhexyl H 3
1-286 -SO 2- (q-26) (q-26) CH 3 CH 3 3
1-287 -SO 2- (q-26) (q-26) C 2H 5 C 2H 5 3
1-288 -SO 2- (q-26) (q-26) C 3H 7 C 3H 7 3
1-289 -SO 2- (q-26) (q-26) C 4H 9 C 4H 9 3
1-290 -SO 2- (q-26) (q-26) The 2-ethylhexyl H 3
1-291 -SO 2- (q-30) (q-30) CH 3 CH 3 3
1-292 -SO 2- (q-30) (q-30) C 2H 5 C 2H 5 3
1-293 -SO 2- (q-30) (q-30) C 3H 7 C 3H 7 3
1-294 -SO 2- (q-30) (q-30) C 4H 9 C 4H 9 3
1-295 -SO 2- (q-30) (q-30) The 2-ethylhexyl H 3
1-296 -SO 2- (q-31) (q-31) CH 3 CH 3 3
1-297 -SO 2- (q-31) (q-31) C 2H 5 C 2H 5 3
1-298 -SO 2- (q-31) (q-31) C 3H 7 C 3H 7 3
1-299 -SO 2- (q-31) (q-31) C 4H 9 C 4H 9 3
1-300 -SO 2- (q-31) (q-31) The 2-ethylhexyl H 3
1-301 -SO 2- (q-35) (q-35) CH 3 CH 3 3
1-302 -SO 2- (q-35) (q-35) C 2H 5 C 2H 5 3
1-303 -SO 2- (q-35) (q-35) C 3H 7 C 3H 7 3
1-304 -SO 2- (q-35) (q-35) C 4H 9 C 4H 9 3
1-305 -SO 2- (q-35) (q-35) The 2-ethylhexyl H 3
1-306 -SO 2- (q-36) (q-36) CH 3 CH 3 3
1-307 -SO 2- (q-36) (q-36) C 2H 5 C 2H 5 3
1-308 -SO 2- (q-36) (q-36) C 3H 7 C 3H 7 3
1-309 -SO 2- (q-36) (q-36) C 4H 9 C 4H 9 3
1-310 -SO 2- (q-36) (q-36) The 2-ethylhexyl H 3
1-311 -SO 2- (q-38) (q-38) CH 3 CH 3 3
1-312 -SO 2- (q-38) (q-38) C 2H 5 C 2H 5 3
1-313 -SO 2- (q-38) (q-38) C 3H 7 C 3H 7 3
1-314 -SO 2- (q-38) (q-38) C 4H 9 C 4H 9 3
1-315 -SO 2- (q-38) (q-38) The 2-ethylhexyl H 3
1-316 Singly-bound (q-1) (q-1) CH 3 CH 3 3
1-317 Singly-bound (q-1) (q-1) C 2H 5 C 2H 5 3
1-318 Singly-bound (q-1) (q-1) C 3H 7 C 3H 7 3
1-319 Singly-bound (q-1) (q-1) C 4H 9 C 4H 9 3
1-320 Singly-bound (q-1) (q-1) The 2-ethylhexyl H 3
1-321 Singly-bound (q-14) (q-14) CH 3 CH 3 3
1-322 Singly-bound (q-14) (q-14) C 2H 5 C 2H 5 3
1-323 Singly-bound (q-14) (q-14) C 3H 7 C 3H 7 3
1-324 Singly-bound (q-14) (q-14) C 4H 9 C 4H 9 3
1-325 Singly-bound (q-14) (q-14) The 2-ethylhexyl H 3
1-326 Singly-bound (q-24) (q-24) CH 3 CH 3 3
1-327 Singly-bound (q-24) (q-24) C 2H 5 C 2H 5 3
1-328 Singly-bound (q-24) (q-24) C 3H 7 C 3H 7 3
1-329 Singly-bound (q-24) (q-24) C 4H 9 C 4H 9 3
1-330 Singly-bound (q-24) (q-24) The 2-ethylhexyl H 3
1-331 Singly-bound (q-26) (q-26) CH 3 CH 3 3
1-332 Singly-bound (q-26) (q-26) C 2H 5 C 2H 5 3
1-333 Singly-bound (q-26) (q-26) C 3H 7 C 3H 7 3
1-334 Singly-bound (q-26) (q-26) C 4H 9 C 4H 9 3
1-335 Singly-bound (q-26) (q-26) The 2-ethylhexyl H 3
1-336 Singly-bound (q-30) (q-30) CH 3 CH 3 3
1-337 Singly-bound (q-30) (q-30) C 2H 5 C 2H 5 3
1-338 Singly-bound (q-30) (q-30) C 3H 7 C 3H 7 3
1-339 Singly-bound (q-30) (q-30) C 4H 9 C 4H 9 3
1-340 Singly-bound (q-30) (q-30) The 2-ethylhexyl H 3
1-341 Singly-bound (q-31) (q-31) CH 3 CH 3 3
1-342 Singly-bound (q-31) (q-31) C 2H 5 C 2H 5 3
1-343 Singly-bound (q-31) (q-31) C 3H 7 C 3H 7 3
1-344 Singly-bound (q-31) (q-31) C 4H 9 C 4H 9 3
1-345 Singly-bound (q-31) (q-31) The 2-ethylhexyl H 3
1-346 Singly-bound (q-35) (q-35) CH 3 CH 3 3
1-347 Singly-bound (q-35) (q-35) C 2H 5 C 2H 5 3
1-348 Singly-bound (q-35) (q-35) C 3H 7 C 3H 7 3
1-349 Singly-bound (q-35) (q-35) C 4H 9 C 4H 9 3
1-350 Singly-bound (q-35) (q-35) The 2-ethylhexyl H 3
1-351 Singly-bound (q-36) (q-36) CH 3 CH 3 3
1-352 Singly-bound (q-36) (q-36) C 2H 5 C 2H 5 3
1-353 Singly-bound (q-36) (q-36) C 3H 7 C 3H 7 3
1-354 Singly-bound (q-36) (q-36) C 4H 9 C 4H 9 3
1-355 Singly-bound (q-36) (q-36) The 2-ethylhexyl H 3
1-356 Singly-bound (q-38) (q-38) CH 3 CH 3 3
1-357 Singly-bound (q-38) (q-38) C 2H 5 C 2H 5 3
1-358 Singly-bound (q-38) (q-38) C 3H 7 C 3H 7 3
1-359 Singly-bound (q-38) (q-38) C 4H 9 C 4H 9 3
1-360 Singly-bound (q-38) (q-38) The 2-ethylhexyl H 3
1-361 -CO- (q-1) (q-1) CH 3 CH 3 3
1-362 -CO- (q-1) (q-1) C 2H 5 C 2H 5 3
1-363 -CO- (q-1) (q-1) C 3H 7 C 3H 7 3
1-364 -CO- (q-1) (q-1) C 4H 9 C 4H 9 3
1-365 -CO- (q-1) (q-1) The 2-ethylhexyl H 3
1-366 -CO- (q-14) (q-14) CH 3 CH 3 3
1-367 -CO- (q-14) (q-14) C 2H 5 C 2H 5 3
1-368 -CO- (q-14) (q-14) C 3H 7 C 3H 7 3
1-369 -CO- (q-14) (q-14) C 4H 9 C 4H 9 3
1-370 -CO- (q-14) (q-14) The 2-ethylhexyl H 3
1-371 -CO- (q-24) (q-24) CH 3 CH 3 3
1-372 -CO- (q-24) (q-24) C 2H 5 C 2H 5 3
1-373 -CO- (q-24) (q-24) C 3H 7 C 3H 7 3
1-374 -CO- (q-24) (q-24) C 4H 9 C 4H 9 3
1-375 -CO- (q-24) (q-24) The 2-ethylhexyl H 3
1-376 -CO- (q-26) (q-26) CH 3 CH 3 3
1-377 -CO- (q-26) (q-26) C 2H 5 C 2H 5 3
1-378 -CO- (q-26) (q-26) C 3H 7 C 3H 7 3
1-379 -CO- (q-26) (q-26) C 4H 9 C 4H 9 3
1-380 -CO- (q-26) (q-26) The 2-ethylhexyl H 3
1-381 -CO- (q-30) (q-30) CH 3 CH 3 3
1-382 -CO- (q-30) (q-30) C 2H 5 C 2H 5 3
1-383 -CO- (q-30) (q-30) C 3H 7 C 3H 7 3
1-384 -CO- (q-30) (q-30) C 4H 9 C 4H 9 3
1-385 -CO- (q-30) (q-30) The 2-ethylhexyl H 3
1-386 -CO- (q-31) (q-31) CH 3 CH 3 3
1-387 -CO- (q-31) (q-31) C 2H 5 C 2H 5 3
1-388 -CO- (q-31) (q-31) C 3H 7 C 3H 7 3
1-389 -CO- (q-31) (q-31) C 4H 9 C 4H 9 3
1-390 -CO- (q-31) (q-31) The 2-ethylhexyl H 3
1-391 -CO- (q-35) (q-35) CH 3 CH 3 3
1-392 -CO- (q-35) (q-35) C 2H 5 C 2H 5 3
1-393 -CO- (q-35) (q-35) C 3H 7 C 3H 7 3
1-394 -CO- (q-35) (q-35) C 4H 9 C 4H 9 3
1-395 -CO- (q-35) (q-35) The 2-ethylhexyl H 3
1-396 -CO- (q-36) (q-36) CH 3 CH 3 3
1-397 -CO- (q-36) (q-36) C 2H 5 C 2H 5 3
1-398 -CO- (q-36) (q-36) C 3H 7 C 3H 7 3
1-399 -CO- (q-36) (q-36) C 4H 9 C 4H 9 3
1-400 -CO- (q-36) (q-36) The 2-ethylhexyl H 3
1-401 -CO- (q-38) (q-38) CH 3 CH 3 3
1-402 -CO- (q-38) (q-38) C 2H 5 C 2H 5 3
1-403 -CO- (q-38) (q-38) C 3H 7 C 3H 7 3
1-404 -CO- (q-38) (q-38) C 4H 9 C 4H 9 3
1-405 -CO- (q-38) (q-38) The 2-ethylhexyl H 3
Compound (1) can be made this sulfonic group sulfuryl amine through after in the compound shown in the formula (Z), importing sulfonic group.
[in the formula (Z), L 1, A 1And A 2Represent the meaning same as described above.]
Compound shown in the formula (Z) (below be sometimes referred to as " compound (Z) ".) can make through the compound shown in compound shown in the compound shown in the formula (X), the formula (Y1) and the formula (Y2) is reacted in organic solvent.
Figure BSA00000704187600182
[in formula (X), formula (Y1) and the formula (Y2), L 1, A 1And A 2Represent the meaning same as described above.]
React the employed organic solvent N-Methyl pyrrolidone, 1 of can giving an example, 3-dimethyl--2-imidazolone, tetramethylene sulfone, N, dinethylformamide, DMAC N,N and their mixed solvent.The usage quantity of organic solvent with respect to compound 1 mass parts shown in the formula (X), is 3～50 mass parts according to solvent types and different, preferred 5～20 mass parts.
The total usage quantity of the compound shown in compound shown in the formula (Y1) and the formula (Y2) is with respect to 1 mole of the usage quantity of the compound shown in the formula (X), preferred 2～8 moles, more preferably 3～5 moles.
Preferred 150～250 ℃ of temperature of reaction, more preferably 180～220 ℃.Preferred 5～72 hours of reaction times, more preferably 8～24 hours.
Reaction after finishing mixes the poor solvent of reaction solution with compound (Z), and the leaching precipitate can obtain compound (Z) thus.Poor solvent can be given an example, acetonitrile, ETHYLE ACETATE, THF, diethyl ether etc.
The usage quantity of poor solvent, with respect to reaction solution 1 mass parts, preferred 1～50 mass parts, more preferably 5～20 mass parts.
The precipitate that is obtained by filtration is preferably with cleanings such as alcoholic solvents, and is dry then.In addition, as required, can be further purified through known approaches such as recrystallizations.The alcoholic solvent that is used to clean to give an example methyl alcohol, ethanol, Virahol etc.
Then with compound (Z) thus sulfonated importing sulfonic group.Sulfonated can carrying out with known method preferably uses sulfonated reagent to the direct Sulfonated method of compound (Z).Can contact with sulfonated reagent through making compound (Z), both are reacted, be created on imported in the compound (Z) sulfonic compound (below be sometimes referred to as " sulfoacid compound (Z1) ".)。
Said sulfonated reagent can give an example chlorsulfonic acid, sulfuryl chloride, sulfuric acid, oleum, sulphur trioxide etc., preferred chlorsulfonic acid.The usage quantity of sulfonated reagent is with respect to compound (Z) 1 mass parts, preferred 1～20 mass parts, more preferably 5～10 mass parts.
Preferred 50～150 ℃ of temperature of reaction, more preferably 70～100 ℃.Preferred 2～15 hours of reaction times, more preferably 4～8 hours.
The sulfoacid compound (Z1) that generates can take out through known method, also can sulfonated reacted mixed solution directly be supplied with follow-up sulfonamide reaction.
Then, with sulfoacid compound (Z1) sulfuryl amine.The sulfonic group halogenation that can sulfoacid compound (Z1) be had, generate sulfonyl halogen compound (Z2), then, make this sulfonyl halogen compound (Z2) and amine compound reaction, thereby obtain compound (1).
Sulfoacid compound (Z1) for example can use the halogenation of thionyl halide compound.The thionyl halide compound THIONYL CHLORIDE 97 of can giving an example.The usage quantity of thionyl halide compound, with respect to 1 mole of sulfoacid compound (Z1), preferred 1～10 mole.But the situation that the water cut of the sulfoacid compound of use (Z1) is many is inferior, in reaction system, sneak under the situation of water, thus preferred excessive use water of decomposition.
Reaction can be carried out also can in solvent, carrying out under solvent-free.This solvent THF, 1 of can giving an example, the ethers of 4-dioxane etc.; Chloroform, methylene dichloride, 1, halogenated hydrocarbons such as 2-ethylene dichloride, zellon, propylene dichloride, amyl chloride, glycol dibromide; Nitriles such as acetonitrile; Amidess such as N-N-methyl-2-2-pyrrolidone N-etc.Wherein, preferred chloroform, acetonitrile and N-N-methyl-2-2-pyrrolidone N-.
The usage quantity of solvent is with respect to sulfoacid compound (Z1) 1 mass parts, preferred 3～10 quality, more preferably 5～8 quality.
Preferred 0～100 ℃ of temperature of reaction, more preferably 50～80 ℃.Reaction times is 0.5～10 hour, preferred 1～5 hour.
The sulfonyl halogen compound (Z2) that generates can take out through known method, also can be directly be used for the reaction with amine compound with the mode of reaction mixture.
As the method for taking out sulfonyl halogen compound (Z2), can mix with frozen water through the reaction solution that will react after finishing, the leaching precipitate, thus obtain sulfonyl halogen compound (Z2).The usage quantity of frozen water, with respect to reaction mixture 1 mass parts, preferred 3～20 mass parts, more preferably 5～12 mass parts.The precipitate that obtains through filtration preferably reduces the residual of thionyl halide compound through water cleaning etc.
The reaction of sulfonyl halogen compound (Z2) and amine compound can be carried out through in solvent, mixing.The solvent that the reacts used amidess such as N-N-methyl-2-2-pyrrolidone N-of can giving an example.This reaction can be carried out in the presence of basic catalyst.Preferably, drip amine compound with after sulfonyl halogen compound (Z2) and the solvent.
Amine compound can give an example Tri N-Propyl Amine, n-Butyl Amine 99, normal hexyl Amine, 1,5-dimethylhexylamine, 1,1,3,3-tetramethyl-butylamine, 2 ethyl hexylamine, 3-amino-1-phenyl butane, isopropoxy propylamine, n n dimetylaniline, diethylamine, dipropyl amine, dibutylamine etc.These can use separately or make up more than 2 kinds and use.
The usage quantity of amine compound, with respect to 1 mole of sulfonyl halogen compound (Z2), preferred 3～10 moles, more preferably 3～7 moles.
Tertiary amines such as basic catalyst preference such as triethylamine, trolamine, pyridine.The usage quantity of basic catalyst with respect to 1 mole of amine compound, is 1.1～2 moles.Basic catalyst can drip with amine compound simultaneously, also can drip respectively with amine compound.
Preferred 0～50 ℃ of temperature of reaction, more preferably 0～30 ℃, more preferably 5～20 ℃.Preferred 1～25 hour of reaction times.
Through leaching precipitate the reaction solution after finishing, can obtain compound (1) with the amine compound reaction.Also can in this reaction solution, mix alcoholic solvent and/or acidic aqueous solutions such as methyl alcohol, ethanol, Virahol, resultant is separated out after leaching again.The usage quantity of this alcoholic solvent is with respect to preferred 10～100 mass parts of reaction solution 1 mass parts, more preferably 20～50 mass parts.Acidic aqueous solution can use the aqueous solution of acidic substance.The preferred pH=0 of the Sorensen value of acidic aqueous solution～6, more preferably 1～5.Acidic substance are not special to limit can give an example ammonium chloride, oxalic acid, acetic acid, hydrochloric acid, sulfuric acid etc.The usage quantity of acidic aqueous solution, with respect to reaction solution 1 mass parts, preferred 1～10 mass parts, more preferably 2～5 mass parts.
The compound (1) that obtains through filtration is preferably with cleanings such as alcoholic solvents.Clean employed alcoholic solvent can give an example methyl alcohol, ethanol, Virahol etc.Carry out drying after preferred the cleaning.
The compound of the present invention that obtains like this, thermotolerance is high, therefore, is useful as the colour filter of display unit such as liquid crystal indicator with dyestuff.
Coloured composition of the present invention contains compound of the present invention as tinting material (below be sometimes referred to as " tinting material (A) "), preferably also contains resin (B).Coloured composition of the present invention more preferably also contains and is selected from least a in polymerizable compound (C), polymerization starter (D) and the solvent (E).
Tinting material (A) can also contain pigment and/or dyestuff (being different from compound of the present invention) except compound of the present invention.
Said dyestuff can be given an example in Colour Index (Colour Index) (the Britain tame association that dyes; The Society of Dyers and Colourists publication) is classified as the compound of solvent dye (Solvent), matching stain (Acid), basic dyestuff (Basic), chemically-reactive dyes (reactive), substantive dyestuff (Direct), dispersed dye (Disperse) or vat dyes (Vat) etc. in.More specifically, the dyestuff of the following Colour Index (C.I.) of can giving an example numbering, but be not limited thereto.Wherein, preferred organic solvent-soluble dye.
C.I. solvent yellow 25,79,81,82,83,89;
C.I. turmeric yellow 7,23,25,42,65,76;
C.I. reactive yellow 2,76,116;
C.I. direct yellow 4,28,44,86,132;
C.I. DISPERSE YELLOW 54,76;
C.I. the solvent orange 41,54,56,99;
C.I. von Muller's indicator 56,74,95,108,149,162;
C.I. reactive orange 16;
C.I. direct orange s 26;
C.I. solvent red 24,49,90,91,118,119,122,124,125,127,130,132,160,218;
C.I. Xylene Red 73,91,92,97,138,151,211,274,289;
C.I. acid violet 102;
C.I. solvent green 1,5;
C.I. acid green 3,5,9,25,28;
C.I. 4 b,asi,c g,ree,n 41;
C.I. 1, Va,t g,ree,n 11 etc.
Said pigment pigment dyestuff or the mineral dye commonly used in the colo(u)rant dispersion resist (レ ジ ス ト) of can giving an example.Mineral dye can give an example MOX or the such metallic compound of metallic complex salt, particularly, the oxide compound or the complex metal oxides of the metals such as iron, cobalt, aluminium, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony of can giving an example.In addition, pigment dyestuff and mineral dye specifically can be given an example, and are classified as the compound of pigment (Pigment) according to Colour Index (Colour Index) (the Britain tame association that dyes: The Society of Dyers and Colourists publishes).More specifically, the pigment of the following Colour Index (C.I.) number of can giving an example, but be not limited thereto.
C.I. Pigment Yellow 73 20,24,31,53,83,86,93,94,109,110,117,125,137,138,139,147,148,150,153,154,166,173 and 180;
C.I. pigment Orange 13,31,36,38,40,42,43,51,55,59,61,64,65 and 71;
C.I. Pigment Red 9,97,105,122,123,144,149,166,168,176,177,180,192,215,216,224,242,254,255 and, 264;
C.I. pigment violet 14,19,23,29,32,33,36,37 and 38;
C.I. pigment Green 7,10,15,25,36,47 and 58 etc.
The content of tinting material (A), with respect to the solids component in the coloured composition, preferred 5～60 quality %.Here, solids component is meant, in the coloured composition, removes the total of the composition after desolvating.
Preferred 3～100 quality % of the content of the compound of the present invention that is contained in the tinting material (A).
These dyestuffs and pigment can be distinguished alone or in combination and uses with compound of the present invention more than 2 kinds.
Resin (B) is not special to be limited, and uses which type of resin all can.Resin (B) preferred bases soluble resin more preferably contains the resin by the structural unit of (methyl) vinylformic acid derivation.Here, (methyl) vinylformic acid is represented vinylformic acid and/or methylacrylic acid.
Resin (B) specifically can exemplified by methyl vinylformic acid/methylacrylic acid benzyl ester multipolymer, methylacrylic acid/methylacrylic acid benzyl ester/styrol copolymer, methylacrylic acid/methylacrylic acid benzyl ester/isobornyl methacrylate multipolymer, methylacrylic acid/styrene/methacrylic acid benzyl ester/N-phenylmaleimide multipolymer, methylacrylic acid/styrene/methacrylic acid glycidyl ester copolymer etc.
The polystyrene conversion weight-average molecular weight of resin (B) preferred 5,000～35,000, more preferably 6,000～30,000.
The acid number of resin (B) preferred 50～150, more preferably 60～135.
The content of resin (B), with respect to the solids component of coloured composition, preferred 7～65 quality %, more preferably 13～60 quality %.
Polymerizable compound (C) so long as the living radical that produces through polymerization starter (D), acid etc. can polymeric compounds be just not special limits.For example, the compound etc. that has the ethene property unsaturated link(age) of polymerizability.
Said polymerizable compound (C) preferably has the polymerizable compound of 3 above polymerizable groups.Polymerizable compound with 3 above polymerizable groups can be given an example, pentaerythritol tetracrylate, pentaerythritol tetramethacrylate, five vinylformic acid dipentaerythritol ester, pentamethyl-vinylformic acid dipentaerythritol ester, six vinylformic acid dipentaerythritol ester, hexamethyl vinylformic acid dipentaerythritol ester etc.Above-mentioned polymerizable compound can use separately or make up more than 2 kinds and use.
The content of polymerizable compound (C), with respect to the solids component of coloured composition, preferred 5～65 quality %, more preferably 10～60 quality %.
Said polymerization starter (D) living radical of can giving an example produces agent, acid producing agent etc.Living radical produces the effect generation living radical of agent through heat or light.Above-mentioned living radical produces agent can exemplified by alkyl groups phenyl ketone compound, thioxanthone compound, triazine based compound, oxime compound etc.
Said alkyl phenyl ketone compound can be given an example, 2-methyl-2-morpholino-1-(4-methyl sulphonyl phenyl)-1-acetone, 2-hydroxy-2-methyl-1-phenyl-1-acetone, benzyl dimethyl ketal, 2-hydroxy-2-methyl-1-(4-(2-hydroxyl-oxethyl) phenyl)-1-acetone, 1-hydroxy-cyclohexyl phenyl ketone etc.
Said thioxanthone compound can give an example 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-two clopenthixal ketones, 1-chloro-4-propoxy-thioxanthone etc.Said triaizine compounds can be given an example, and 2,4-two (trichloromethyl)-6-(4-p-methoxy-phenyl)-1,3; 5-triazine, 2,4-two (trichloromethyl)-6-(4-methoxyl group naphthyl)-1,3,5-triazines, 2; 4-two (trichloromethyl)-6-(4-methoxyl-styrene)-1,3,5-triazines, 2,4-two (trichloromethyl)-6-(2-(5-methyl furan-2-yl) vinyl)-1; 3,5-triazine, 2,4-two (trichloromethyl)-6-(2-(furans-2-yl) vinyl)-1,3; 5-triazine, 2,4-two (trichloromethyl)-6-(2-(4-diethylamino-2-aminomethyl phenyl) vinyl)-1,3,5-triazines, 2; 4-two (trichloromethyl)-6-(2-(3, the 4-Dimethoxyphenyl) vinyl)-1,3,5-triazines etc.
Said oxime compound can be given an example; O-acyl group oxime compound; Concrete example has; N-benzoyloxy-1-(4-phenyl sulfonyl phenyl)-1-butanone-2-imines, N-benzoyloxy-1-(4-phenyl sulfonyl phenyl)-1-octanone-2-imines, N-acetoxyl group-1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-yl] ethane-1-imines, N-acetoxyl group-1-[9-ethyl-6-{2-methyl-4-(3; 3-dimethyl--2,4-dioxane amyl group methoxyl group) benzoyl-}-9H-carbazole-3-yl] ethane-1-imines etc.
In addition, living radical produces agent and for example can use 2; 4,6-trimethylbenzoyl diphenyl phosphine oxide, 2,2 '-two (Chloro-O-Phenyl)-4; 4 ', 5,5 '-tetraphenyl-1; 2 '-diimidazole, 10-butyl-2-chloro-acridine ketone, 2-ethyl-anthraquinone, benzil, 9,10-phenanthrenequione, camphorquinone, phenyl oxoethanoic acid methyl ester, two cyclopentadiene titanium compounds etc.
Said acid producing agent can be given an example, the salt of 4-hydroxy phenyl dimethyl sulfonium tosilate, 4-hydroxy phenyl dimethyl sulfonium hexafluoro antimonate, 4-acetoxyl group phenyl dimethyl sulfonium tosilate, 4-acetoxyl group phenyl methyl benzyl sulfonium hexafluoro antimonate, triphenylsulfonium tosilate, triphenylsulfonium hexafluoro antimonate, phenylbenzene iodine tosilate, phenylbenzene iodine hexafluoro antimonate etc., tosic acid nitrobenzyl ester (or salt) class, tosic acid benzoin ester (or salt) class etc.
These polymerization starters can use separately also can make up use more than 2 kinds.
The content of polymerization starter (D) is measured 100 mass parts with respect to the total of resin (B) and polymerizable compound (C), preferred 0.1～30 mass parts, more preferably 1～20 mass parts.The content of polymerization starter in above-mentioned scope, highly sensitiveization, the time shutter shortens, productivity improves, and is therefore comparatively desirable.
Compound of the present invention is just not special to be limited solvent (E) as long as can dissolve, and can give an example ethers, aromatic hydrocarbon based, ketone, alcohols, ester class, amides etc.
Said ethers can be given an example; THF, tetrahydropyrans, 1,4-dioxane, glycol monomethyl methyl ether, ethylene glycol monomethyl ether, glycol monomethyl propyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, TC, Diethylene Glycol single-butyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, Diethylene Glycol dipropyl ether, Diethylene Glycol dibutyl ether, propylene glycol monomethyl ether, Ucar 35 list ethyl ether acetic ester, Ucar 35 list propyl ether acetic ester, terepthaloyl moietie monomethyl ether acetate, ethylene glycol monomethyl ether acetate, TC acetic ester, Diethylene Glycol single-butyl ether acetic ester etc.
Above-mentioned aromatic hydrocarbon based can giving an example, benzene,toluene,xylene, sym-trimethylbenzene etc.
Above-mentioned ketone can be given an example, acetone, 2-butanone, 2-heptanone, 3-heptanone, dipropyl ketone, 4-methyl-2 pentanone, 4-hydroxy-4-methyl-2 pentanone, ketopentamethylene, pimelinketone etc.
Above-mentioned alcohols can be given an example, methyl alcohol, ethanol, propyl alcohol, butanols, hexanol, hexalin, terepthaloyl moietie, USP Kosher etc.
Above-mentioned ester class can be given an example, vinyl acetic monomer, n-butyl acetate, isobutyl acetate, pentyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl n-butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, n-Butyl lactate, Methoxy Methyl Acetate, Methoxy acetic acid ethyl ester, Methoxy acetic acid butyl ester, oxyethyl group ritalin, oxyethyl group vinyl acetic monomer, 3-methoxypropionic acid methyl esters, 3-methoxy propyl acetoacetic ester, 3-ethoxy-propionic acid methyl esters, 3-ethoxyl ethyl propionate, 2-methoxypropionic acid methyl esters, 2-methoxy propyl acetoacetic ester, 2-methoxy propyl propyl propionate, 2-ethoxy-propionic acid methyl esters, 2-ethoxyl ethyl propionate, 2-methoxyl group-2 Methylpropionic acid methyl esters, 2-oxyethyl group-2 Methylpropionic acid ethyl ester, Pyruvic Acid Methyl ester, Pyruvic Acid Ethyl ester, Propyl pyruvate, methyl acetoacetate, ethyl 3-oxobutanoate, 3-methoxyl group butylacetic acid ester, 3-methyl-3-methoxyl group butylacetic acid ester, gamma-butyrolactone etc.
Above-mentioned amides can be given an example, N, dinethylformamide, DMAC N,N, N-Methyl pyrrolidone etc.
These solvents can use separately also can make up use more than 2 kinds.
The content of solvent in the coloured composition (E), with respect to coloured composition, preferred 70～95 quality %, more preferably 75～90 quality %.
Coloured composition of the present invention can also contain various additives such as tensio-active agent, weighting agent, other macromolecular compounds, adhesive accelerant, inhibitor, UV light absorber, photostabilizer, chain-transfer agent as required.
Compound of the present invention is owing to show high heat resistance, especially as the dyestuff of the colour filter that is used for display unit such as liquid crystal indicator and useful.
In addition; Coloured composition of the present invention can be applied to have colour filter in known manner as various machines relevant with rendered image such as the display unit (for example, known liquid crystal indicator, organic El device etc.) of the part of its component parts, solid-state imagers.
[embodiment]
Then, provide embodiment the present invention is described in further detail.In the example, the % of expression content and usage quantity is meant quality criteria with a part short of special qualification.
In following examples, the structure of compound is by ultimate analysis (VARIO-EL; (エ レ メ Application タ one Le (strain) production)) and mass analysis (LC; Agilent produces 1200 types, MASS; Agilent produces the LC/MSD type) confirm.
(embodiment 1)
After in 7.00 parts of compounds shown in the formula (X-1) (Tokyo change into industry (strain) produce), adding 53.26 parts of tetramethylene sulfone, be heated to 180 ℃, make its dissolving.After confirming dissolving, add quinaldine red (Tokyo changes into industry (strain)) 11.19 parts,, make its reaction 200 ℃ of refluxed 9 hours.Reaction is injected into reaction soln in 500 parts of acetonitriles the leaching throw out after finishing.With 500 parts of 500 parts of ethanol and methyl-sulphoxides the throw out that obtains is carried out pulp more respectively, respectively carry out twice, obtain yellow solid.Decompression, 60 ℃ of down dry these yellow solids obtain 4.5 parts of the compounds shown in the formula (z-1).
The evaluation of the compound shown in the formula (z-1);
(ultimate analysis) C70.84 H3.28 N4.75 S5.09
Then, 7.0 parts of the compounds shown in the formula (z-1) are joined in 67.0 parts of the chlorsulfonic acids, stirred 4 hours down at 70 ℃.After the stirring, THIONYL CHLORIDE 97 is added drop-wise in the reaction solution for 10.95 parts, 80 ℃ are stirred after 2 hours down, are cooled to 15 ℃, continue to stir 14 hours again.After reaction finishes, slowly join in 556 parts of the frozen water, stir after-filtration.In 200 parts of the residue adding N-N-methyl-2-2-pyrrolidone N-s that obtains,, keep 20～30 ℃ to stir after 18 hours, obtain residue through filtration to wherein dripping 29.73 parts of 2 ethyl hexylamines.With this residue join stir 2 hours in 800 parts in the 20% acetic acid water after, obtain residue through filtration.With this residue join stir 2 hours in 400 parts of the acetonitriles after, obtain yellow solid through filtration.Decompression, 60 ℃ of down dry these yellow solids 15 hours obtain 4.93 parts of the compounds shown in the formula (I-5).
The evaluation of the compound shown in the formula (I-5)
(mass analysis) ionization mode=ESI+:m/z=780.3 [M]+
Accurate mass: 799.2
Can confirm that from The above results m+n is 1.
(embodiment 2)
After in 7.00 parts of compounds shown in the formula (X-1), adding 53.26 parts of tetramethylene sulfone, be heated to 180 ℃, make its dissolving.After confirming dissolving, add 13.88 parts of 8-chlorine quinaldine reds, 200 ℃ of refluxed 9 hours.Reaction is injected into reaction soln in 500 parts of acetonitriles the leaching throw out after finishing.With 500 parts of 500 parts of ethanol and methyl-sulphoxides the throw out that obtains is carried out pulp more respectively, respectively carry out twice, obtain yellow solid.Decompression, 60 ℃ of down dry these yellow solids obtain 8.15 parts of the compounds shown in the formula (z-2).
The evaluation of the compound shown in the formula (z-2);
(ultimate analysis) C63.3 H2.8 N3.8 Cl10.2 S5.0
Figure BSA00000704187600271
Then, 3.0 parts of the compounds shown in the formula (z-2) are joined in 25.8 parts of the chlorsulfonic acids, stirred 4 hours down at 70 ℃.After the stirring, THIONYL CHLORIDE 97 is added drop-wise in the reaction solution for 4.21 parts, 80 ℃ are stirred after 2 hours down, are cooled to below 15 ℃, continue to stir 14 hours again.After reaction finishes, slowly join in 556 parts of the frozen water, stir after-filtration.In 100 parts of the residue adding N-N-methyl-2-2-pyrrolidone N-s that obtains,, keep 20～30 ℃ to stir after 18 hours, obtain residue through filtration to wherein dripping 5.72 parts of 2 ethyl hexylamines.With this residue join stir 2 hours in 400 parts in the 20% acetic acid water after, obtain residue through filtration.With this residue join stir 2 hours in 400 parts of the acetonitriles after, obtain yellow solid through filtration.Decompression, 60 ℃ of down dry these yellow solids 15 hours obtain 2.93 parts of the compounds shown in the formula (I-20).
The evaluation of the compound shown in the formula (I-20)
(mass analysis) ionization mode=ESI+:m/z=868.3 [M]+
Accurate mass: 867.1
Can confirm that from The above results m+n is 1.
(embodiment 3)
After in 10.0 parts of compounds shown in the formula (X-2) (Tokyo change into industry (strain) produce), adding 92.65 parts of tetramethylene sulfone, be heated to 180 ℃, make its dissolving.After confirming dissolving, add 24.15 parts of quinaldine reds, 200 ℃ of refluxed 9 hours.Reaction is injected into reaction soln in 500 parts of acetonitriles the leaching throw out after finishing.With 500 parts of 500 parts of ethanol and methyl-sulphoxides the throw out that obtains is carried out pulp more respectively, respectively carry out twice, obtain yellow solid.Decompression, 60 ℃ of down dry these yellow solids obtain 13.5 parts of the compound The shown in the formula (z-3).
The evaluation of the compound shown in the formula (z-3);
(ultimate analysis) C79.97 H3.68 N5.31
Figure BSA00000704187600281
Then, 5.0 parts of the compounds shown in the formula (z-3) are joined in 53.5 parts of the chlorsulfonic acids, stirred 4 hours down at 70 ℃.After the stirring, THIONYL CHLORIDE 97 is added drop-wise in the reaction solution for 8.74 parts, 80 ℃ are stirred after 2 hours down, are cooled to 15 ℃, continue to stir 14 hours again.After reaction finishes, slowly join in 556 parts of the frozen water, stir after-filtration.In 200 parts of the residue adding N-N-methyl-2-2-pyrrolidone N-s that obtains,, keep 20～30 ℃ to stir after 18 hours, obtain residue through filtration to wherein dripping 11.87 parts of 2 ethyl hexylamines.With this residue join stir 2 hours in 800 parts in the 20% acetic acid water after, obtain residue through filtration.With this residue join stir 2 hours in 400 parts of the acetonitriles after, obtain yellow solid through filtration.Decompression, 60 ℃ of down dry these yellow solids 15 hours obtain 4.93 parts of the compounds shown in the formula (I-50).
The evaluation of the compound shown in the formula (I-50)
(mass analysis) ionization mode=ESI+:m/z=736.3 [M]+
Accurate mass: 735.2
Can confirm that from The above results m+n is 1.
Figure BSA00000704187600282
(embodiment 4)
After in 7.0 parts of compounds shown in the formula (X-2), adding 64.86 parts of tetramethylene sulfone, be heated to 180 ℃, make its dissolving.After confirming dissolving, add 16.90 parts of 8-chlorine quinaldine reds, 200 ℃ of refluxed 9 hours.Reaction is injected into reaction soln in 500 parts of acetonitriles the leaching throw out after finishing.With 500 parts of 500 parts of ethanol and methyl-sulphoxides the throw out that obtains is carried out pulp more respectively, respectively carry out twice, obtain yellow solid.Decompression, 60 ℃ of down dry these yellow solids obtain 9.0 parts of the compounds shown in the formula (z-4).
The evaluation of the compound shown in the formula (z-4);
(ultimate analysis) C68.5 H3.0 N3.6 Cl10.4
Figure BSA00000704187600291
Then, 5.0 parts of the compounds shown in the formula (z-4) are joined in 47.5 parts of the chlorsulfonic acids, 70 ℃ were stirred 4 hours down.After the stirring, THIONYL CHLORIDE 97 is added drop-wise in the reaction solution for 7.76 parts, 80 ℃ are stirred after 2 hours down, are cooled to 15 ℃, continue to stir 14 hours again.After reaction finishes, slowly join in 556 parts of the frozen water, stir after-filtration.In 200 parts of the residue adding N-N-methyl-2-2-pyrrolidone N-s that obtains,, keep 20～30 ℃ to stir after 18 hours, obtain residue through filtration to wherein dripping 5.27 parts of 2 ethyl hexylamines.With this residue join stir 2 hours in 800 parts in the 20% acetic acid water after, obtain residue through filtration.With this residue join stir 2 hours in 400 parts of the acetonitriles after, obtain yellow solid through filtration.Decompression, 60 ℃ of down dry these yellow solids 15 hours obtain 4.93 parts of the compounds shown in the formula (I-65).
The evaluation of the compound shown in the formula (I-65)
(mass analysis) ionization mode=ESI+:m/z=804.3 [M]+
Accurate mass: 803.2
Can confirm that from The above results m+n is 1.
Figure BSA00000704187600292
(solvability evaluation)
Be described below and obtain the compound that obtains among the embodiment 1～4 and the solubleness of compound in propylene glycol monomethyl ether (hereinafter to be referred as PGME), propylene glycol monomethyl ether (hereinafter to be referred as PGMEA), pimelinketone (hereinafter to be referred as CHN), N-Methyl pyrrolidone (hereinafter to be referred as NMP) of comparative example 1.
In the 50mL sample hose, according to following ratio compound 0.1g and above-mentioned solvent 1g are mixed, then, with sample hose jam-pack stopper, under 30 ℃ with ultrasonic oscillator vibration 3 minutes.Then, at room temperature place 30 minutes after, filter its residue of visual observations.Affirmation is judged as favorable solubility during less than insolubles, in table 2, is designated as zero, and when confirming insolubles is arranged, it is bad to be judged as solvability, in table 2, be designated as *.
[table 1]
Compound PGME PGMEA CHN NMP
Embodiment 1 (I-5) ○ ○ ○ ○
Embodiment 2 (I-20) ○ ○ ○ ○
Embodiment 3 (I-50) ○ ○ ○ ○
Embodiment 4 (I-65) ○ ○ ○ ○
Comparative example 1 (R-1) × × × ×
In the table 2, compound (R-1) is C.I. quinoline yellow (Tokyo changes into industry (strain) and produces).
(embodiment 5)
(preparation of coloured composition)
(A) tinting material: compound (I-5): the synthetic compound is 20 parts among the embodiment 1
(B-1) resin: methylacrylic acid/methylacrylic acid benzyl ester multipolymer (mol ratio; 30/70; Weight-average molecular weight 10700, acid number 70mgKOH/g) 70 parts
(C-1) polymerizable compound: 30 parts of six vinylformic acid dipentaerythritol ester (Japanese chemical drug society produce)
(D-1) Photoepolymerizationinitiater initiater: benzyl dimethyl ketal (イ Le ガ キ ユ ア 651; BASF AG produces)
15 parts
(E-1) solvent: 680 parts of propylene glycol monomethyl ether
Mix above-mentioned substance, obtain coloured composition.
(making of colour filter)
With spin-coating method the above-mentioned coloured composition that obtains is coated on glassly, makes volatile component volatilization.After the cooling, use silica glass system photomask and exposure machine to carry out rayed with pattern.After the rayed, develop, be heated to 200 ℃, obtain colour filter with stove with potassium hydroxide aqueous solution.
(embodiment 6)
Synthetic compound (I-5) among the embodiment 1 is replaced to synthetic compound (I-20) among the embodiment 2, in addition, likewise obtain coloured composition and colour filter with embodiment 5.
(embodiment 7)
Synthetic compound (I-5) among the embodiment 1 is replaced to synthetic compound (I-50) among the embodiment 3, in addition, likewise obtain coloured composition and colour filter with embodiment 5.
(embodiment 8)
Synthetic compound (I-5) among the embodiment 1 is replaced to synthetic compound (I-65) among the embodiment 4, in addition, likewise obtain coloured composition and colour filter with embodiment 5.
Can know that from the result of table 2 compound of the present invention demonstrates high-dissolvability to organic solvent.In addition, contain the coloured composition of this compound, the generation of foreign matter is few, can make high-quality colour filter.
Industrial applicability
The solvability in organic solvent of compound of the present invention is excellent.

Claims (10)

1. the compound shown in the formula (1),
Figure FSA00000704187500011
In the formula (1), L 1The alkylidene group of expression singly-bound, carbonatoms 1～8 ,-SO 2-,-O-,-CO-or-CO-O-, the Wasserstoffatoms that contains in this alkylidene group can be replaced by halogen atom, contain in this alkylidene group-CH 2-can by-O-or-CO-replaces,
R 1And R 2The alkyl of representing Wasserstoffatoms or carbonatoms 1～8 independently of each other,
A 1And A 2Expression independently of each other has or does not have substituent phenyl ring, has or do not have substituent naphthalene nucleus or has or do not have substituent quinoline ring,
M and n represent 0～5 integer independently of each other, and wherein, m+n is 1～8 integer, and is when m+n is the integer more than 2, a plurality of-SO 2NR 1R 2Can be the same or different each other.
2. the compound of putting down in writing like claim 1, A 1Be to have or do not have substituent phenyl ring.
3. the compound of putting down in writing like claim 1, A 1Be no substituted phenyl ring or phenyl ring with halogen.
4. the compound of putting down in writing like claim 1, A 1And A 2Be to have or do not have substituent phenyl ring independently of each other.
5. the compound of putting down in writing like claim 1, A 1And A 2Be no substituted phenyl ring or phenyl ring independently of each other with halogen.
6. the compound of putting down in writing like claim 1, R 1And R 2Be the branched-chain alkyl of Wasserstoffatoms or carbonatoms 1～8 independently of each other.
7. the compound of putting down in writing like claim 1, L 1Be singly-bound or-SO 2-.
8. like the compound of claim 1 record, m+n is 1～5 integer.
9. the compound with claim 1 record is the dyestuff of principal constituent.
10. the coloured composition that contains the dyestuff of claim 9 record.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5948597A (en) * 1991-12-12 1999-09-07 Mitsui Chemicals, Inc. Dyes for color filters and photosensitive resist resin composition containing the same
US5955614A (en) * 1996-09-05 1999-09-21 Bayer Aktiengesellschaft Bridged perinones/quinophthalones
CN1421437A (en) * 2001-11-27 2003-06-04 拜尔公司 Bridged peryleneone/quinolindeone

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Publication number Priority date Publication date Assignee Title
GB1091734A (en) * 1965-03-26 1967-11-22 Ici Ltd Heterocyclic dyestuffs
JPS4830452B1 (en) * 1970-05-12 1973-09-20
JPH0680744A (en) * 1992-03-31 1994-03-22 Mitsui Toatsu Chem Inc Photocurable resin composition for color filter and production of color filter therefrom
JPH07133456A (en) * 1993-09-14 1995-05-23 Sumitomo Chem Co Ltd Composition for printing ink
JP2004339501A (en) * 2003-04-25 2004-12-02 Mitsubishi Chemicals Corp Colored resin composition, color filter, and liquid crystal display device

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5948597A (en) * 1991-12-12 1999-09-07 Mitsui Chemicals, Inc. Dyes for color filters and photosensitive resist resin composition containing the same
US5955614A (en) * 1996-09-05 1999-09-21 Bayer Aktiengesellschaft Bridged perinones/quinophthalones
CN1421437A (en) * 2001-11-27 2003-06-04 拜尔公司 Bridged peryleneone/quinolindeone

Non-Patent Citations (1)

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Title
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