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    • 1. 发明授权
    • Asymmetric stilbene compounds
    • 不对称二苯乙烯化合物
    • US06482241B1
    • 2002-11-19
    • US09657737
    • 2000-09-08
    • Georges MetzgerDieter ReinehrClaude EckhardtFabienne Cuesta
    • Georges MetzgerDieter ReinehrClaude EckhardtFabienne Cuesta
    • C07D25108
    • C07D251/68C11D3/42D06M13/07D06M13/358D06M2101/04D06M2101/06D06M2101/10D06M2101/12D06M2101/16D06M2101/28D06M2101/32D06M2101/34D06M2200/25
    • The present invention provides, as a first aspect, an asymmetric compound having the formula: in which M is hydrogen, an alkali metal atom, ammonium or a cation formed from an amine; Xa and Xb are the same or different and each is NH2; NH(C1-C4alkyl); NH(C2-C4alkoxyalkyl); N(C1-C4alkyl)2; N(CH2CH2OH)2; a group NH—Z—NR1R2 in which Z is C2-C14alkylene or optionally substituted arylene, and R1 and R2 are the same or different and each is C1-C12alkyl or R1 and R2, together with the nitrogen atom to which they are each attached, form a morpholino, piperidino or piperazino ring; an aminoacid residue; C1-C4alkoxy; hydroxy-substituted-C2-C4alkoxy; and Ya and Yb are the same or different and each is a substituted amino group having both UVA and UVB-absorbing properties having the formula: in which R3 is CN; SO2R5 in which R5 is, C1-C12alkyl, C1-C12alkoxy, NH2, NH(C1-C4alkyl), N(C1-C4alkyl)2, N(CH2CH2OH)2, C1-C4alkoxy or hydroxy-substituted-C2-C4alkoxy; COR5 in which R5 has its previous significance; COOM in which M has its previous significance or NHCOR5 in which R5 has its previous significance and in which R4 has the same significance as R3 or is H, OH, C1-C4alkyl or C1-C4alkoxy and one of Xa and Xb can be identical to one of Ya and Yb, provided that one of Xa and Xb is different from the other and/or one of Ya and Yb is different from the other. The present invention also relates to a method of improving the sun protection factor (SPF) of textile fibre material, especially cotton, polyamide and wool, comprising treating them with the new compounds.
    • 作为第一方面,本发明提供具有下式的不对称化合物:其中M是氢,碱金属原子,铵或由胺形成的阳离子; Xa和Xb相同或不同,各自为NH 2; NH(C 1 -C 4烷基); NH(C 2 -C 4烷氧基烷基); N(C 1 -C 4烷基)2; N(CH 2 CH 2 OH)2; 其中Z为C 2 -C 14亚烷基或任选取代的亚芳基的基团NH-Z-NR 1 R 2,并且R 1和R 2相同或不同,并且各自为C 1 -C 12烷基或R 1和R 2以及它们各自连接的氮原子 形成吗啉代,哌啶子基或哌嗪基环; 氨基酸残基; C1-C4烷氧基; 羟基取代的C 2 -C 4烷氧基; Ya和Yb相同或不同,并且各自为具有下式的UVA和UVB吸收性质的取代氨基:其中R3为CN; 其中R 5为C 1 -C 12烷基,C 1 -C 12烷氧基,NH 2,NH(C 1 -C 4烷基),N(C 1 -C 4烷基)2,N(CH 2 CH 2 OH)2,C 1 -C 4烷氧基或羟基取代的C 2 -C 4烷氧基的SO 2 R 5; COR5其中R5具有以前的意义; 其中M具有其先前意义的COOM或其中R5具有其先前意义的NHCOR5,并且其中R 4与R 3具有相同的含义或为H,OH,C 1 -C 4烷基或C 1 -C 4烷氧基,X a和X b中的一个可以相同 Ya和Yb中的一个,其中Xa和Xb中的一个与另一个不同,和/或Ya和Yb中的一个与另一个不同。本发明还涉及一种改善防晒因子(SPF)的方法 纺织纤维材料,特别是棉花,聚酰胺和羊毛,包括用新化合物处理它们。
    • 2. 发明授权
    • Asymmetric stilbene compounds
    • 不对称二苯乙烯化合物
    • US6143889A
    • 2000-11-07
    • US209940
    • 1998-12-11
    • Georges MetzgerDieter ReinehrClaude EckhardtFabienne Cuesta
    • Georges MetzgerDieter ReinehrClaude EckhardtFabienne Cuesta
    • C07D251/68C09K3/00C11D3/34C11D3/42D06M13/02D06M13/07D06M13/248D06M13/256D06M13/322D06M13/342D06M13/345D06M13/35D06M13/355D06M13/358D06M101/00D06M101/02D06M101/06D06M101/10D06M101/16D06M101/18D06M101/30D06M101/32D06M101/34C07D251/08
    • C07D251/68C11D3/42D06M13/07D06M13/358D06M2101/04D06M2101/06D06M2101/10D06M2101/12D06M2101/16D06M2101/28D06M2101/32D06M2101/34D06M2200/25
    • Asymmetric compounds having the formula: in which M is hydrogen, an alkali metal atom, ammonium or a cation formed from an amine: Xa and Xb are the same or different and each is NH.sub.2 ; NH(C.sub.1 -C.sub.4 alkyl); NH(C.sub.2 -.sub.4 alkoxyalkyl); N(C.sub.1 -C.sub.4 alkyl).sub.2 ; N(CH.sub.2 CH.sub.2 OH).sub.2 ; a group NH--Z--NR.sub.1 R.sub.2 in which Z is C.sub.2 -C.sub.14 alkylene or optionally substituted arylene, and R.sub.1 and R.sub.2 are the same or different and each is C.sub.1 -C.sub.12 alkyl or R.sub.1 and R.sub.2, together with the nitrogen atom to which they are each attached, form a morpholino, piperidino or piperazino ring; an aminoacid residue; C.sub.1 -C.sub.4 alkoxy; hydroxy-substituted-C.sub.2 -C.sub.4 alkoxy; ##STR1## and Ya and Yb are the same or different and each is a substituted amino group having both UVA and UVB-absorbing properties having the formula: ##STR2## in which R.sub.3 is CN; SO.sub.2 R.sub.5 in which R.sub.5 is C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, NH.sub.2, NH(C.sub.1 -C.sub.4 alkyl), N(C.sub.1 -C.sub.4 alkyl).sub.2, N(CH.sub.2 CH.sub.2 OH).sub.2, C.sub.1 -C.sub.4 alkoxy or hydroxy-substituted-C.sub.2 -C.sub.4 alkoxy; COR.sub.5. In which R.sub.5 has its previous significance; COOM or NHCOR.sub.5 and in which R.sub.4 has the same meaning as R.sub.3 or H, OH, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and one of Xa and Xb can be identical to one of Ya and Yb, provided that one of Xa and Xb is different from the other and/or one of Ya and Yb is different from the other, and their use improve the sun protection factor (SPF) of textile fiber material.
    • 具有下式的不对称化合物:其中M为氢,由胺形成的碱金属原子,铵或阳离子:Xa和Xb相同或不同,分别为NH 2; NH(C 1 -C 4烷基); NH(C 2-4烷氧基烷基); N(C 1 -C 4烷基)2; N(CH 2 CH 2 OH)2; 其中Z为C 2 -C 14亚烷基或任选取代的亚芳基的基团NH-Z-NR 1 R 2,并且R 1和R 2相同或不同,并且各自为C 1 -C 12烷基或R 1和R 2以及它们各自连接的氮原子 形成吗啉代,哌啶子基或哌嗪基环; 氨基酸残基; C1-C4烷氧基; 羟基取代的C 2 -C 4烷氧基; Ya和Yb相同或不同,并且各自为具有下式的UVA和UVB吸收性质的取代氨基:其中R3为CN; SO 2 R 5,其中R 5是C 1 -C 12烷基,C 1 -C 12烷氧基,NH 2,NH(C 1 -C 4烷基),N(C 1 -C 4烷基)2,N(CH 2 CH 2 OH)2,C 1 -C 4烷氧基或羟基取代的C 2 -C 4烷氧基; COR5。 其中R5具有以前的意义; COOM或NHCOR5,其中R4具有与R 3或H,OH,C 1 -C 4烷基或C 1 -C 4烷氧基相同的含义,Xa和Xb之一可以与Ya和Yb之一相同,条件是Xa和Xb之一不同 从另一个和/或Ya和Yb之一是不同的,它们的使用改善纺织纤维材料的防晒因子(SPF)。
    • 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。