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    • 1. 发明授权
    • Fluorescent whitening agents
    • 荧光增白剂
    • US06458169B2
    • 2002-10-01
    • US09767112
    • 2001-01-22
    • Peter RohringerGeorges MetzgerDieter Reinehr
    • Peter RohringerGeorges MetzgerDieter Reinehr
    • C07D25100
    • C09B23/148C07D251/68C11D3/42D06L4/621D06L4/657D06L4/75D06M13/07D06M13/358D06P1/6426D21H21/30Y10S8/919
    • The present invention provides new compounds having the formula: in which X is O or, preferably, NH; M is hydrogen, an alkali metal atom, ammonium or a cation formed from an amine; each R1, independently, is an aminoacid residue from which a hydrogen atom on the amino group has been removed; n is 1 or 2; and each R2, independently, is hydrogen, C1-C3alkyl, halogen, cyano, COOR in which R is hydrogen or C1-C3alkyl, CONH—R in which R has its previous significance, SO2NH—R in which R has its previous significance, NH—COR in which R has its previous significance, SO3M in which M has its previous significance or, when n is 1, R2 can also be CO—R3 in which R3 is C1-C3alkyl or phenyl; provided that those compounds are excluded in which a) X is NH, n is 1 and R2 is SO3M in which M has its previous significance; or b) X is NH, n is 2 and one R2 is SO3M in which M has its previous significance, and the other R2 is hydrogen, methyl or halogen; or c) X is NH, n is 1, R1 is glycine and R2 is H or CO2H; or d) X is NH, n is 2, each R2 is SO3M in which M has its previous significance and the SO3M groups are in 2,5-positions in the phenyl ring and R1 is D,L-alanine, L-valine, L-leucine, L-isoleucine, L-threonine, L-aspartic acid, L-glutamic acid, L-phenylalanine, L-proline, D,L-methionine or glycine. Most of the new class of 4,4′-diaminostilbene-2,2′-disulfonic acid compounds are useful as fluorescent whitening agents, especially for paper.
    • 本发明提供了新的具有下式的化合物:其中X为O或优选为NH; M是氢,碱金属原子,铵或由胺形成的阳离子; 每个R 1独立地是氨基酸被除去的氨基酸残基; n为1或2; 并且每个R 2独立地是氢,C 1 -C 3烷基,卤素,氰基,其中R是氢或C 1 -C 3烷基的COOR,其中R具有其先前含义的CONH-R,其中R具有其先前含义的SO 2 NH- 其中R具有其先前意义的NH-COR,其中M具有其先前含义的SO 3 M,或当n为1时,R 2也可以是其中R 3为C 1 -C 3烷基或苯基的CO-R 3;条件是将这些化合物排除在 哪一个)X是NH,n是1,R2是SO3M,其中M具有其先前的意义; 环)X是NH,n是2,一个R2是SO3M,其中M具有其先前的意义,另一个R 2是氢,甲基或卤素; orc)X是NH,n是1,R1是甘氨酸,R2是H或CO2H; ord)X是NH,n是2,每个R2是SO3M,其中M具有其先前的意义,SO3M基团在苯环中是2,5位,R1是D,L-丙氨酸,L-缬氨酸,L L-亮氨酸,L-异亮氨酸,L-苏氨酸,L-天冬氨酸,L-谷氨酸,L-苯丙氨酸,L-脯氨酸,D,L-甲硫氨酸或甘氨酸。新的4,4'-二氨基芪 - 2,2'-二磺酸化合物可用作荧光增白剂,特别是用于纸。
    • 2. 发明授权
    • Fluorescent whitening agents
    • 荧光增白剂
    • US06464735B2
    • 2002-10-15
    • US09766984
    • 2001-01-22
    • Peter RohringerGeorges MetzgerDieter Reinehr
    • Peter RohringerGeorges MetzgerDieter Reinehr
    • C07D25100
    • C09B23/148C07D251/68C11D3/42D06L4/621D06L4/657D06L4/75D06M13/07D06M13/358D06P1/6426D21H21/30Y10S8/919
    • The present invention provides new compounds having the formula: in which X is O or, preferably, NH; M is hydrogen, an alkali metal atom, ammonium or a cation formed from an amine; each R1, independently, is an aminoacid residue from which a hydrogen atom on the amino group has been removed; n is 1 or 2; and each R2, independently, is hydrogen, C1-C3alkyl, halogen, cyano, COOR in which R is hydrogen or C1-C3alkyl, CONH—R in which R has its previous significance, SO2NH—R in which R has its previous significance, NH—COR in which R has its previous significance, SO3M in which M has its previous significance or, when n is 1, R2 can also be CO—R3 in which R3 is C1-C3alkyl or phenyl; provided that those compounds are excluded in which a) X is NH, n is 1 and R2 is SO3M in which M has its previous significance; or b) X is NH, n is 2 and one R2 is SO3M in which M has its previous significance, and the other R2 is hydrogen, methyl or halogen; or c) X is NH, n is 1, R1 is glycine and R2 is H or CO2H; or d) X is NH, n is 2, each R2 is SO3M in which M has its previous significance and the SO3M groups are in 2,5-positions in the phenyl ring and R1 is D,L-alanine, L-valine, L-leucine, L-isoleucine, L-threonine, L-aspartic acid, L-glutamic acid, L-phenylalanine, L-proline, (),L- or glycine. Most of the new class of 4,4′-diaminostilbene-2,2′-disulfonic acid compounds are useful as fluorescent whitening agents, especially for paper.
    • 本发明提供了新的具有下式的化合物:其中X为O或优选为NH; M是氢,碱金属原子,铵或由胺形成的阳离子; 每个R 1独立地是氨基酸被除去的氨基酸残基; n为1或2; 并且每个R 2独立地是氢,C 1 -C 3烷基,卤素,氰基,其中R是氢或C 1 -C 3烷基的COOR,其中R具有其先前含义的CONH-R,其中R具有其先前含义的SO 2 NH- 其中R具有其先前意义的NH-COR,其中M具有其先前含义的SO 3 M,或当n为1时,R 2也可以是其中R 3为C 1 -C 3烷基或苯基的CO-R 3;条件是将这些化合物排除在 哪一个)X是NH,n是1,R2是SO3M,其中M具有其先前的意义; 环)X是NH,n是2,一个R2是SO3M,其中M具有其先前的意义,另一个R 2是氢,甲基或卤素; orc)X是NH,n是1,R1是甘氨酸,R2是H或CO2H; ord)X是NH,n是2,每个R2是SO3M,其中M具有其先前的意义,SO3M基团在苯环中是2,5位,R1是D,L-丙氨酸,L-缬氨酸,L L-亮氨酸,L-异亮氨酸,L-苏氨酸,L-天冬氨酸,L-谷氨酸,L-苯丙氨酸,L-脯氨酸,(),L-或甘氨酸。 大多数新类的4,4'-二氨基芪-2,2'-二磺酸化合物可用作荧光增白剂,特别是用于纸。
    • 4. 发明授权
    • Process for the preparation of stilbene compounds
    • 二苯乙烯化合物的制备方法
    • US06365737B1
    • 2002-04-02
    • US09622472
    • 2000-08-17
    • Georges MetzgerFabienne CuestaPeter RohringerDieter ReinehrRené Schlatter
    • Georges MetzgerFabienne CuestaPeter RohringerDieter ReinehrRené Schlatter
    • C07D25168
    • C11D3/42C07D251/68D06L4/621D06M2200/25D21H21/30
    • A process for the preparation of a 4,4′-bis-(triazinylamino)-stilbene-2,2′-disulphonic acid compound of formula (1) is disclosed, characterized in that (a) in a first reaction step cyanurchloride is reacted with the disodium salt of 4,4′-diaminostilbene-2,2′-disulfonic acid to give the intermediate of formula (2); (b) in a second reaction step the compound of formula (2) is reacted with a compound of formula R1—H and/or R2—H to give the compound of formula (3); (c) in a third step the compound of formula (3) is reacted with the compound of the formula R3H, and reaction step (a) and/or (c) are carried out in a medium consisting of a mixture of water and a polyglycol to give the compound of formula (1), wherein R1, R2 and R3, independently, are phenylamino; phenylamino substitued by C1-C3alkyl, halogen, cyano, COOR or COR; CONH—R; SO2NH—R; NH—COR; mono- or disulphonated phenylamino; morpholino; piperidino; pyrrolidino; —NH2; —NH(C1-C4alkyl); —N(C1-C4alkyl)2; —NH(C2-C4hydroxyalkyl); —N(C2-C4hydroxyalkyl)2; —N(C1-C4alkyl)(C2-C4hydroxyalkyl); NHC2-C4 alkylsulphonic acid; —OC1-C4alkyl; an aminoacid or aminoacid amide residue from which a hydrogen atom on the amino group has been removed; R1 and R2 may further independently represent hydrogen; C1-C4alkyl; phenyl; naphthyl; phenyl or naphthyl substituted by C1-C4alkyl, C1-C4alkoxy, halogen, C2-C5alkanoyl-amino, nitro, sulpho or C1-C4alkylated amino; R is hydrogen; or C1-C3alkyl; and M is H, Na, Li, K, Ca, Mg, ammonium, or ammonium that is mono-, di-, tri- or tetrasubstituted by C1-C4alkyl, C2-C4hydroxyalkyl or a mixture thereof.
    • 公开了制备式(1)的4​​,4'-双 - (三嗪基氨基) - 茋-2,2'-二磺酸化合物的方法,其特征在于(a)在第一反应步骤中,氰化氢反应 与4,4'-二氨基芪-2,2'-二磺酸的二钠盐得到式(2)的中间体; (b)在第二反应步骤中,将式(2)化合物与式R 1 -H和/或R 2 -H的化合物反应,得到式(3)化合物; (c)在第三步中,式(3)化合物与式R3H的化合物反应,反应步骤(a)和/或(c)在由水和 得到式(1)化合物,其中R 1,R 2和R 3独立地是苯基氨基; 由C 1 -C 3烷基,卤素,氰基,COOR或COR取代的苯基氨基; CONH-R; SO2NH-R; NH-COR; 单或二磺基苯基氨基; 吗啉代 哌啶子 吡咯烷 -NH2; -NH(C 1 -C 4烷基); -N(C 1 -C 4烷基)2; -NH(C 2 -C 4羟烷基); -N(C 2 -C 4羟烷基)2; -N(C 1 -C 4烷基)(C 2 -C 4羟烷基); NHC2-C4烷基磺酸; -OC1-C4烷基; 已除去氨基上的氢原子的氨基酸或氨基酸酰胺残基; R 1和R 2可以进一步独立地表示氢; C 1 -C 4烷基; 苯基; 萘基; 被C 1 -C 4烷基,C 1 -C 4烷氧基,卤素,C 2 -C 5烷酰基 - 氨基,硝基,磺基或C 1 -C 4烷基化氨基取代的苯基或萘基; R是氢; 或C 1 -C 3烷基; 并且M是被C 1 -C 4烷基,C 2 -C 4羟烷基或其混合物单,二,三或四取代的H,Na,Li,K,Ca,Mg,铵或铵。
    • 5. 发明授权
    • Fluorescent whitening agents
    • 荧光增白剂
    • US06210449B1
    • 2001-04-03
    • US09381468
    • 1999-09-20
    • Peter RohringerGeorges MetzgerDieter Reinehr
    • Peter RohringerGeorges MetzgerDieter Reinehr
    • C07D25100
    • C09B23/148C07D251/68C11D3/42D06L4/621D06L4/657D06L4/75D06M13/07D06M13/358D06P1/6426D21H21/30Y10S8/919
    • The present invention provides new compounds having formula (1), in which X is 0 or, preferably, NH; M is hydrogen, an alkali metal atom, ammonium or a cation formed from an amine; each R1, independently, is an aminoacid residue from which a hydrogen atom on the amino group has been removed; n is 1 or 2; and each R2, independently, is hydrogen, C1-C3alkyl, halogen, cyano, COOR in which R is hydrogen or C1-C3alkyl, CONH—R in which R has its previous significance, SO2NH—R in which R has its previous significance, NH—COR in which R has its previous significance, SO3M in which M has its previous significance or, when n is 1, R2 can also be CO—R3 in which R3 is C1-C3alkyl or phenyl; provided that those compounds are excluded in which a) X is NH, n is 1 and R2 is SO3M in which M has its previous significance; or b) X is NH, n is 2 and one R2 is SO3M in which M has its previous significance, and the other R2 is hydrogen, methyl or halogen; or c) X is NH, n is 1, R1 is glycine and R2 is H or CO2H; or d) X is NH, n is 2, each R2 is SO3M in which M has its previous significance and the SO3M groups are in 2,5-positions in the phenyl ring and R1 is D,L-alanine, L-valine, L-leucine; L-isoleucine, L-threonine, L-aspartic acid, L-glutamic acid, L-phenylalanine, L-proline, D,L-methionine or glycine. Most of the new class of 4,4′-diaminostilbene-2,2′-disulfonic acid compounds are useful as fluorescent whitening agents, especially for paper.
    • 本发明提供具有式(1)的新化合物,其中X为0或优选为NH; M是氢,碱金属原子,铵或由胺形成的阳离子; 每个R 1独立地是氨基酸被除去的氨基酸残基; n为1或2; 并且每个R 2独立地是氢,C 1 -C 3烷基,卤素,氰基,其中R是氢或C 1 -C 3烷基的COOR,其中R具有其先前含义的CONH-R,其中R具有其先前含义的SO 2 NH- 其中R具有其先前含义的NH-COR,其中M具有其先前含义的SO 3 M,或当n为1时,R 2也可以是其中R 3为C 1 -C 3烷基或苯基的CO-R 3; 条件是排除这些化合物,其中a)X是NH,n是1,R2是其中M具有其先前意义的SO 3 M; 或b)X是NH,n是2,一个R2是SO3M,其中M具有其先前的含义,另一个R 2是氢,甲基或卤素; 或c)X是NH,n是1,R1是甘氨酸,R2是H或CO2H; 或d)X是NH,n是2,每个R2是SO3M,其中M具有其先前的意义,SO 3 M基团在苯环中是2.5位,R 1是D,L-丙氨酸,L-缬氨酸, L-亮氨酸 L-异亮氨酸,L-苏氨酸,L-天冬氨酸,L-谷氨酸,L-苯丙氨酸,L-脯氨酸,D,L-甲硫氨酸或甘氨酸。 大多数新类的4,4'-二氨基芪-2,2'-二磺酸化合物可用作荧光增白剂,特别是用于纸。
    • 7. 发明授权
    • Triazinylaminostilbene derivative as fluorescent whitening agents
    • 三嗪基氨基芪衍生物作为荧光增白剂
    • US06723846B1
    • 2004-04-20
    • US10070525
    • 2002-03-06
    • Georges MetzgerSerge HaugerFabienne CuestaChristophe BulliardPeter RohringerMarc Roger Grienenberger
    • Georges MetzgerSerge HaugerFabienne CuestaChristophe BulliardPeter RohringerMarc Roger Grienenberger
    • C07D25168
    • C07D251/68Y10S8/919
    • The present invention relates to compounds having formula (1): wherein each R1 represents, independently, a linear C1-C4-alkylene residue which is unsubstituted or substituted by hydroxy, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-hydroxy- or alkoxy-alkoxy, —OCOM, —OCOC1-C4-alkyl, or an amino acid residue from which a hydrogen atom on the amino group has been removed; each R2 represents, independently, a linear C1-C4-alkylene residue which is unsubstituted or substituted by hydroxy, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-hydroxy- or alkoxy-alkoxy, —OCOM, —OCOC1-C4-alkyl, —CO2M, CO2C1-C4-alkyl SO3M or phenoxy which is unsubstituted or substituted by halogen, C1-C4-alkyl or C1-C4-alkoxy, —CO2M or CO2C1-C4-alkyl, NH3 or mono- or disubstituted amino; or phenyl which is unsubstituted or substituted by 1 to 3 SO3M, SO2NHC1-C4-alkyl, —SO2NH2, —CO2M, —CO2M, —CO2C1-C4-alkyl, —CONH2, —CONHC1-C4-alkyl, —NHCOC1-C4-alkyl or mono- or disubstituted amino groups; each R3 represents independently, hydrogen, C1-C4-alkyl, halogen, cyano, SO3M, —SO2NH2, SO2NHC1-C4-alkyl, —CO2M, —CO2C1-C4-alkyl, —CONH2, —CONHC1-C4-alkyl, or —NHCOC1-C4-alkyl; M is hydrogen, an alkali metal atom, ammonium or a cation formed from an amine and m is an integer of 1 to 3, a process for their preparation and use of the compounds as optical brightening agents for synthetic or natural organic materials or for removing stain in photographic materials.
    • 本发明涉及具有式(1)的化合物:其中每个R 1独立地表示未被取代或被羟基,C 1 -C 4烷基,C 1 -C 4烷氧基,C 1 -C 4烷基取代的直链C 1 -C 4亚烷基 - 羟基 - 或烷氧基 - 烷氧基,-OCOM,-OCOC1-C4-烷基或氨基上氨基的氢原子被除去的氨基酸残基; 每个R 2独立地表示未被取代或被羟基,C 1 -C 4 - 烷基,C 1 -C 4 - 烷氧基,C 1 -C 4 - 羟基 - 或烷氧基 - 烷氧基取代的直链C 1 -C 4 - 亚烷基残基,-OCOM,-OCOC 1 -C 1-4烷基,-CO 2 M,CO 2 C 1 -C 4 - 烷基SO 3 M或苯氧基,其未被取代或被卤素,C 1 -C 4 - 烷基或C 1 -C 4 - 烷氧基,-CO 2 M或CO 2 C 1 -C 4烷基,NH 3或单 - 或 二取代氨基; 或未被取代或被1至3个SO 3 M,SO 2 NHC 1 -C 4烷基,-SO 2 NH 2,-CO 2 M,-CO 2 M,-CO 2 C 1 -C 4 - 烷基,-CONH 2,-CONHC 1 -C 4烷基,-NHCOC 1 -C 4 - 烷基或单或二取代的氨基; 每个R 3独立地表示氢,C 1 -C 4 - 烷基,卤素,氰基,SO 3 M,-SO 2 NH 2,SO 2 NHC 1 -C 4烷基,-CO 2 M,