CN1081655C - 三嗪基紫外线吸收剂在造纸工艺中作为猝灭剂的应用 - Google Patents
三嗪基紫外线吸收剂在造纸工艺中作为猝灭剂的应用 Download PDFInfo
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- CN1081655C CN1081655C CN97195231A CN97195231A CN1081655C CN 1081655 C CN1081655 C CN 1081655C CN 97195231 A CN97195231 A CN 97195231A CN 97195231 A CN97195231 A CN 97195231A CN 1081655 C CN1081655 C CN 1081655C
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- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
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- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
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- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
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Abstract
本发明提供了抑制(猝灭)阴离子荧光增白剂对基质作用的方法,该方法包括用三嗪UVA化合物处理基质,其中一些三嗪UVA化合物为新化合物。
Description
本发明涉及通过用某些三嗪基紫外线吸收剂(UVAs)处理基质来抑制(猝灭)阴离子荧光增白剂对基质(尤其是纤维物)作用的方法,其中一些三嗪基紫外线吸收剂为新化合物。
荧光增白作用是荧光增白剂处理纤维物后对所述纤维物显示的作用,这种作用对如此处理过的纤维外表提供了有价值的美白改善作用。
然而,特别是在造纸工业上,某些情形下荧光增白剂所产生的荧光增白作用可能会带来一些问题。例如,许多造纸机要求不仅用于生产增白纸,而且还用于生产非增白纸。因此,当一台造纸机先用于生产增白纸后,如果随后需要用于生产非增白纸,这时就会产生问题。在这些情况下,生产荧光增白纸时残留的荧光增白剂仍遗留在机器部件上,并污染后续非增白纸生产过程中得到的纸。
当然,可以通过彻底清洗已用于生产增白纸的造纸机及其有关循环系统,随后再立刻用于生产非增白纸。但是,这种彻底清洗是昂贵的,并且会降低生产能力。
DE-A-2 448 293中早已提出,可以在纸张形成前后,将未增白的纸质与猝灭剂化合物接触。并且还建议,将这种猝灭剂化合物加到增白用纸中用于生产非增白纸。
然而,最现代化的造纸方法是在中性pH条件下进行,因此DE-A-2 448 293中的化合物不适宜于这种用途,其原因在于这些化合物在中性使用条件下它们仅能部分吸附在纤维上。因此,非吸收性猝灭剂化合物不能良好地排放到废水内。而且,DE-A-2 448 293的化合物往往会发生凝絮,这不利于在造纸工艺的“铜网部”(纸形成)部分使用。
令人惊奇的是,现已发现,当在纸张工艺中用作猝灭剂时,三嗪基紫外线吸收剂(UVAs)比DE-A-2 448 293中的化合物能够更好地吸附在纤维上,并能降低废水污染,以及降低对分散稳定性的影响(低凝絮倾向)。
因此,本发明提供了抑制(猝灭)阴离子荧光增白剂对基质作用的方法,该方法包括用三嗪UVA化合物处理基质。
一类优选的三嗪UV吸收剂具有下式结构:其中R1,R2和R3中至少一个代表下式基团:其中R4,R5和R6独立地代表氢;C1-C12烷氧基;羟基;-O-CH2-CO-NH-CH2OH;SO3M,其中M代表氢,钠,钾,铵,单-、二-、三-或四-C1-C4烷基铵,单-、二-或三-C1-C4羟烷基铵或被C1-C4烷基和C1-C4羟烷基的混合物二-或三-取代的铵;或其中n为2-6的整数,且优选2或3;Y1和Y2独立地代表任选被卤素、氰基、羟基或C1-C4烷氧基取代的C1-C4烷基,或者Y1和Y2与它们各自所连接的氮原子一起形成5-7元杂环,优选为吗啉、吡咯烷、哌啶或六亚甲基亚胺环;Y3代表氢,C3-C4链烯基或任选被氰基、羟基或C1-C4烷氧基取代的C1-C4烷基,或者Y1,Y2和Y3与它们各自所连接的氮原子一起形成吡啶或甲基吡啶环;以及X1 -代表无色阴离子,优选CH3OSO3 -或C2H5OSO3 -;和剩余的取代基R1,R2和R3独立地代表卤素,优选氯,C1-C12烷氧基或苯基,其中苯基取代基任选地被一个或多个羟基、C1-C12-烷氧基、-O-CH2-CO-NH-CH2OH、SO3M取代,其中M的定义同上。
在式(1)化合物中,Y1、Y2和Y3所代表的C1-C4烷基可以为甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基,其中优选甲基和乙基。
R1、R2、R3、R4、R5和R6所代表的C1-C12烷氧基可以为例如甲氧基,乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、叔丁氧基、正戊氧基、正己氧基、正庚氧基、正辛氧基、异辛氧基、正壬氧基、正癸氧基、正十一烷氧基或正十二烷氧基,其中优选甲氧基和乙氧基。
M所代表的单-、二-、三-或四-C1-C4烷基铵基中的烷基优选甲基,M所代表的单-、二-或三-C1-C4羟烷基铵基优选衍生自乙醇胺、二-乙醇胺或三-乙醇胺的基团。当M代表被C1-C4烷基和C1-C4羟烷基的混合基团二-或三-取代的铵时,优选N-甲基-N-乙醇胺或N,N-二甲基-N-乙醇胺。但M优选为氢或钠。
式(1)化合物为已知的或者例如可通过如USP3118887和5197991中所述的方法制备。
R7和R8所代表的C1-C12-烷氧基可以为例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、叔丁氧基、正戊氧基、正己氧基、正庚氧基,正辛氧基、异辛氧基、正壬氧基、正癸氧基、正-十一烷氧基或正-十二烷氧基,其中优选甲氧基和乙氧基。
式(2)化合物为已知的或可按照如USP3118887和5197991中所述的方法制备。
第三类优选的三嗪UVAs为具有下式结构的化合物:其中M的定义同上;n1和n2独立地为0或1,其条件是如果n1为0,则n2也为0;R9代表任选取代的芳基或代表下式基团:其中R11代表任选取代的烷基或任选取代的芳基;或者,当n2为0时,R9还可以为具有下列各式结构之一的基团:其中R11的定义同上;其中R12为M,任选取代的烷基或任选取代的芳基;其中R12的定义同上; 或或其中R13代表氢,任选取代的烷基或任选取代的芳基;且R10代表氢,卤素,优选氯,任选取代的烷基,任选取代的芳基,-NH2、-N(CH2CH2OH)2、-N[CH2CH(OH)CH3]2、-NH-R12、-N(R12)2或-OR12,其中R12的定义同上,或者R10代表氨基上去除氢原子后的氨基酸残基。
当R10、R11、R12和R13中的一个或多个代表任选取代的烷基时,优选的未取代烷基基团R10、R11、R12和R13为C1-C12-,尤其是C1-C4-烷基基团。这些烷基基团可以为支链或非支链的,并可任选地被例如卤素(如氟、氯或溴),C1-C4-烷氧基(如甲氧基或乙氧基),苯基或羧基,C1-C4-烷氧基羰基如乙酰基,单-或二-C1-C4-烷基化氨基或被-SO3M(其中M的定义同上)取代。
当R10、R11、R12和R13中的一个或多个代表任选取代的芳基时,它们优选为苯基或萘基,并且可以被C1-C4-烷基如甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基或叔丁基,C1-C4-烷氧基如甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、仲丁氧基或叔丁氧基,卤素如氟、氯或溴,C2-C5-烷酰基氨基,如乙酰氨基、丙酰氨基或丁酰氨基,硝基,磺基或二-C1-C4烷基化氨基取代。
优选的是,各氨基酸残基R10为相同的。优选的氨基酸残基R10的实例包括具有式-NH-CH(CO2H)-R14的基团,其中R14代表氢或式-CHR15R16基团,其中R15和R16独立地代表氢或被一个或两个选自下列的取代基任选取代的C1-C4烷基:羟基、硫代(thio)、甲硫基、氨基、羧基、磺基、苯基、4-羟苯基、3,5-二碘-4-羟苯基、β-吲哚基,β-咪唑基和NH=C(NH2)NH-。
衍生得到这些优选的氨基酸残基R10的氨基酸具体实例包括甘氨酸、丙氨酸、肌氨酸、丝氨酸、半胱氨酸、苯丙氨酸、酪氨酸(4-羟基苯丙氨酸)、二碘酪氨酸、色氨酸(β-吲哚基丙氨酸)、组氨酸(β-咪唑基丙氨酸)、α-氨基丁酸、甲硫氨酸、缬氨酸(α-氨基异戊酸)、正缬氨酸、亮氨酸(α-氨基异己酸)、异亮氨酸(α-氨基β-甲基戊酸)、正亮氨酸(α-氨基-n-己酸)、精氨酸、鸟氨酸(α,δ-二氨基戊酸)、赖氨酸(α,ε-二氨基己酸)、天冬氨酸(氨基琥珀酸)、谷氨酸(α-氨基戊二酸)、苏氨酸、羟基谷氨酸和牛磺酸、以及它们的混合物和光学异构体。衍生得到这些优选氨基酸残基R10的上述氨基酸中,特别优选谷氨酸和天冬氨酸。
衍生得到氨基酸残基R10的氨基酸的进一步优选实例包括亚氨基二乙酸。
可衍生得到氨基酸残基R10的氨基酸的其它次优选的实例包括胱氨酸,羊毛硫氨酸,脯氨酸和羟基脯氨酸。
在式(3)的各化合物中,优选它们以中性形式使用,即其中的M不为氢,优选由碱金属(特别是钠)或胺形成的阳离子。
在式(3)化合物中,优选R9为苯基、甲基苯基、二甲基苯基或下式基团:其中R11的定义同上,并优选为C1-C4-烷基,尤其是甲基或乙基;且优选R10为苯基、甲基苯基、二甲基苯基、-N(CH2CH2OH)2或-N[CH2CH(OH)CH3]2。
式(3)化合物可按下所述制备:在公知的反应条件下,使氰尿酰氯以任何需要的顺序依次与氨基芪-磺酸,能引入基团R9的氨基化合物和能引入基团R10的化合物反应,其中R9和R10的定义各自同上。式(3)不对称化合物,即其中n2为0的化合物,可以按照GB-A-2,298,422中所述的方法制备。
起始物质为易购得的已知化合物。
大多数式(3)化合物为已知的。但其中R9代表任选取代芳基且R10,M,n1和n2的定义同上的式(3)化合物据信为新化合物,并且这些化合物构成了本发明的另一方面。
式(3)新化合物可如上所述由氰尿酰氯制备,不过优选采用选自下列的合适中间体来制备:2-氯-4,6-二苯基-1,3,5-三嗪[按照A.Ostrogovich的方法(Chemiker Ztg.36(1912)739)制备],2-氨基-4-氯-6-苯基-1,3,5-三嗪[按照H.K.Reimschuessel,N.T.McDevitt;J.Am.Chem.Soc.82(1960)3756-3762中所述方法制备]或新中间体2-氯-4-N-吗啉代-6-苯基-1,3,5-三嗪。后一新中间体可通过在已知的反应条件下反应2,4-二氯-6-苯基-1,3,5-三嗪与吗啉而制得。
根据本发明方法,用作猝灭剂化合物的三嗪基紫外线吸收剂用量优选为受处理基质中荧光增白剂的存在量的0.5-50倍。
本发明用下列实施例进一步说明。
实施例1-5
将5g由漂白山毛榉纤维和漂白云杉纤维的1∶1混合物(Schopper-Riegler)组成的干亚硫酸盐纸浆悬浮在150ml水中。然后向此纤维悬浮液中加入5%碳酸钙填料,接着加入0.2%具有下式结构的荧光增白剂活性物质:(为二乙醇胺盐形式),其中各物质的用量均按纤维重量计。然后在室温下搅拌混合物15分钟。随后加入25ml任一种下述猝灭剂试验化合物的二甲亚砜/水(20∶80)溶液,以得到含有0.2wt%(基于纸浆重量)下列受试猝灭剂化合物的相应纸浆悬浮液:和
然后在室温下再搅拌相应的受试猝灭剂化合物15分钟,以使它们发挥其作用。
尔后采用Rapid-Kothen装置由相应的悬浮液(用10°德国硬度的水稀释到0.2%稠度)制成纸张。干燥所制纸张15分钟后,干纸张的单位面积重量为160g/m2。
为了对比起见,按照相同方式由含有荧光增白剂但不含受试猝灭剂化合物的碱性纸浆悬浮液制备纸张。
制得相应纸张后24小时,采用Spektaflash仪测量Ganz白度和荧光(ISO)。Ganz方法详细记载在Ciba-Geigy Review,1973/1中,同样还记载在Journal of Color and Appearance,l,No.5(1972)中发表的“Whiteness Measurement”一文中(ISCC,Conference onFluorescence and the Colorimetry of Fluorescent Materials,Williamsburg,1972年2月)。
所得结果示于下表内。
表
表内所示结果表明,用本发明猝灭剂化合物处理过的纸的白度和荧光显著降低。
实施例 | 受试猝灭剂 | Ganz白度 | ISO荧光 |
对照例12345 | 无101102103104105 | 187.4142.0126.887.578.5107.5 | 17.813.811.97.48.79.5 |
将4.32g 4,4′-二氨基芪-2,2′-二磺酸在200ml二甲基甲酰胺中搅拌并加热至55℃。然后向此混合物中加入4.32g 2-氯-4,6-二苯基-1,3,5-三嗪[按照A.Ostrogovich;Chemiker Ztg.36(1912)739中的方法制得]和2.27g碳酸钠,并将所得混合物加热至105-110℃反应28小时。冷却后,将此得到的黄色悬浮液与150ml甲醇/甲乙酮/水混合物一起旋转和沸腾,然后冷却并过滤。真空干燥后,得到5.45g表征如下的式(106)黄色粉末:λmax370nm/ε 54000(DMF);1H-NMR(DMSO-d6):δ(ppm)=10.42(s,2H,NH-),8.75(d,2H,芳香质子),8.65(d,8H,芳香质子),8.14(s,2H,-CH=CH-),7.89(dd,2H,芳香质子),7.71(d,2H,芳香质子),7.68-7.56(m,12H,芳香质子)。
实施例7
采用实施例6所述的类似方法,制得式(107)化合物,其表征如下:λmax370nm/ε52900(DMF);1H-NMR(DMSO-d6):δ(ppm)=10.42(s,2H,NH-),8.76(d,2H,芳香质子),8.55(d,8H,芳香质子),8.14(s,2H,-CH=CH-),7.85(dd,2H,芳香质子),7.70(d,2H,芳香质子),7.43(d,8H,芳香质子),2.45(s,12H,-CH3)。
实施例8
采用实施例6所述的类似方法,制得式(108)化合物,表征如下:λmax 364nm/ε 52900(DMF);1H-NMR(DMSO-d6):δ(ppm)=10.31(s,2H,NH-),8.33(d,2H,芳香质子),8.08(s,2H,-CH=CH-),8.02(d,4H,芳香质子),7.90(dd,2H,芳香质子),7.63(d,2H,芳香质子),7.21(d,4H,芳香质子),7.18(s,4H,芳香质子),2.66(s,12H,-CH3),2.36(s,12H,-CH3)。
实施例9A)20℃下,将15.82g 2,4-二氯-6-苯基-1,3,5-三嗪在200ml丙酮中搅拌,并用6.2ml吗啉和9.4ml可力丁(collidine)处理。搅拌混合物6小时,然后加冷水至1000ml,用浓盐酸酸化。搅拌20分钟后,抽滤悬浮液,用去离子水洗涤,然后在五氧化二磷上干燥。由此得到18.21g具有式(109A)结构的米色粉末,表征如下:1H-NMR(丙酮-d6):δ(ppm)=8.41(d,2H,芳香质子),7.62(t,1H,芳香质子),7.52(t,2H,芳香质子),4.05(t,2H,-CH2-),3.87(t,2H,-CH2-),3.80-3.72(m,4H,-CH2-)。B)采用实施例6所述的类似方法,使式(109A)化合物与4,4′-二氨基芪-2,2′-二磺酸反应,得到式(103)化合物,表征如下:λmax 363nm/ε55557(DMF/水);1H-NMR(D2O):δ(ppm)=8.56(s,2H,芳香质子),8.27(d,4H,芳香质子),7.84(s,2H,-CH=CH-),7.73(d,2H,芳香质子),7.63(t,2H,芳香质子),7.59-7.48(m 6H,芳香质子),3.89(s,8H,-CH2-),3.80(s,8H,-CH2-)。
实施例10
采用实施例6中所述的类似方法,使2-氨基-4-氯-6-苯基-1,3,5-三嗪[按照H.K.Reimschuessel,N.T.McDevitt在J.Am.Chem.Soc.82(1960)3756-3762中所述方法制备]与4,4′-二氨基芪-2,2′-二磺酸反应,得到式(110)化合物,其表征如下:λmax 360nm/ε45366(DMF/水);1H-NMR(MeOH-d4):δ(ppm)=8.65(s,2H,芳香质子),8.47(d,4H,芳香质子),8.17(s,2H,-CH=CH-),7.96(d,2H,芳香质子),7.85(dd,2H,芳香质子),7.63-7.52(m 6H,芳香质子)。
实施例11
将1.2g 4-氨基乙酰苯溶于30ml甲基溶纤剂。然后在此溶液内加入3.3g具有下式结构的化合物(91%纯度):在油浴中加热反应混合物到130℃,并在此温度下保持4小时。短暂时间后,结晶出盐化合物(111)的游离酸形式。抽滤后,将滤饼溶于甲醇,然后利用甲醇钠将其转化为式(111)二钠盐。抽滤后,水洗并进行干燥,从而得到4.0g(91%理论值)式(111)二钠盐。元素分析具有式(111)和具有实验式C48H38N12Na2O8S2.11.0H2O的化合物,得到:需要值%C47.29;H4.96;N13.78;S5.26;H2O16.24.计算值%C47.05;H4.96;N13.87;S5.28;H2O15.99.实施例12
将18.81g氰尿酰氯(98%纯度)溶于95ml丙酮内,并倾入到100g冰水混合物内。然后在30分钟内。于-5℃-0℃温度下滴加入18.5g二氨基芪-二磺酸(100%纯度)在320g冰水混合物中的溶液。最后,在15分钟内,于同样温度下滴加入50ml 1摩尔苏打溶液,并进一步搅拌全部反应物1小时。然后加入13.5g 4-氨基乙酰苯,并在90分钟内加热混合物至50℃。在此过程中,通过加入碳酸钠维持反应混合物的pH为7-8。为完成反应,蒸除丙酮至反应混合物的温度达到66℃。趁热抽滤沉淀物,用氯化钠稀溶液(2%)和300ml冷水依次洗涤。干燥后,还剩下44.8g(88%理论值)式(101)化合物。元素分析具有式(101)和具有实验式C36H26N10O8Cl2S2Na2.6.0H2O的化合物,得到:需要值%C42.57;H3.77;N13.79.计算值%C42.59;H3.85;N13.74.实施例13
将5g实施例12得到的式(101)化合物悬浮在100ml水中。加入1.3g牛磺酸,然后加热反应混合物到90℃,并利用碳酸钠维持反应混合物的pH为9-10。在此pH和温度下使反应物进一步反应15小时。最后,浓缩反应混合物并用丙酮沉淀化合物(113)。抽滤后,用丙酮洗涤并干燥,还剩下5.9g(81%理论值)化合物(113)。元素分析具有式(113)和具有实验式C40H36N12Na4O14S4.0.66NaCl.16.5H2O的化合物,得到:需要值%C32.8;H4.74;N11.47;S8.75;Cl1.60;Na7.32计算值%C32.7;H4.7;N11.5;S9.1;Cl1.6;Na7.4
采用实施例13中所述的类似方法,通过反应化合物(101)与0.9g代替牛磺酸的肌氨酸制备化合物(114)。6小时后反应结束,化合物(114)的收率为理论值的93%。元素分析具有式(114)和具有实验式C42H36N12Na4O12S215H2O的化合物,得到:需要值%C38.02;H5.01;N12.66.计算值%C38.10;H4.87;N12.65.
采用实施例13中所述的类似方法,通过反应化合物(101)和代替牛磺酸的N-甲基-乙醇胺制备化合物(115)。6.5小时后反应结束,化合物(115)的收率为理论值的81%。
分析上述物质表明其中有部分以N-甲基-乙醇胺盐形式存在。元素分析具有式(115)和具有实验式C42H42N12Na2O10S2.0.6N-甲基-乙醇胺.5H2O的化合物,得到:需要值%C47.0;H5.02;N15.78;S5.73.计算值%C46.75;H.4.92;N15.46;S5.71.
在油浴中,使10g式(101)化合物与5.8g L-谷氨酸在6∶9(重量比)的水和甲基溶纤剂混合物中于120℃下反应,通过加入碳酸钠保持pH在8-9.6小时后,反应结束。将反应混合物倾入到HCl酸化过的丙酮内,随后式(116)化合物以游离酸形式沉淀析出。抽滤并用丙酮-水洗涤,然后加入计算量氢氧化钠水溶液使滤饼转化为相应的六-钠盐,尔后蒸发至干。收率为理论值的90%。元素分析具有式(116)和具有实验式C46H38N12Na6O10S2.0.3NaCl.17H2O的化合物,得到:需要值%C35.9;H4.71;N10.92;S4.16.计算值%C36.0;H4.7;N10.9;S4.1.
采用实施例16中所述的方法,但用亚氨基乙酸代替L-谷氨酸,制得式(117)化合物,收率为理论值的87%。元素分析具有式(117)和具有实验式C44H34N12Na6O16S2.0.8NaCl.15H2O的化合物,得到:需要值%C35.1;H4.28;N11.16;S4.26.计算值%C35.0;H4.3;N11.2;S4.4.
实施例18-26
按下所述研究本发明所用的各种三嗪基UVAs作为猝灭剂的活性。所用纤维悬浮液为取自造纸机中纸浆循环过程中的工业生产悬浮液,主要由桉树纸浆组成。由于受试纤维悬浮液仅含少量荧光增白剂,因此向纤维悬浮液中加入0.1wt%基于取代四磺基芪的市售造纸用荧光增白剂活性物。进一步经过24小时以使所加入的荧光增白剂发挥其作用,然后向1wt%稠度的纤维悬浮液中加入受试猝灭剂化合物,活性物浓度为0.8wt.%.15分钟吸尽后,采用Rapid Kothen系统制成纸张并干燥。然后用氙灯(Spektraflash SF 500)照射干燥纸张,并通过先使用UV遮光滤片(420nm),随后不使用UV遮光滤片方式测定纸张的荧光强度。这两次测量(440nm处)的差值称作荧光强度(F440)
使用具有不同取代基R的化合物所得到的测试结果示于下表内。
表
实施例 | R | F440 |
- | 对照(无猝灭剂) | 31 |
181920212223242526 | NH2(化合物104)苯胺基(NH-苯基)(化合物111)NH-(CH2)2-OCH3O-(CH2)2-CH3NH-(CH2)5-COOHN(CH3)(CH2COOH)(化合物114)NH-(CH2)2-SO3H(化合物113)N(CH3)-(CH2)2-OH(化合物115)N(C2H5)-(CH2)2-OH | 9109181211121011 |
由于F440的值越高,荧光强度就越强,因此不难发现,与对照试验相比,受试化合物能够显著降低(猝灭)荧光。
Claims (31)
其中R1,R2和R3中至少一个代表下式基团:其中R4,R5和R6独立地代表氢;C1-C12烷氧基;羟基;-O-CH2-CO-NH-CH2OH;SO3M,其中M代表氢,钠,钾,铵,单-、二-、三-或四-C1-C4烷基铵,单-、二-或三-C1-C4羟烷基铵或被C1-C4烷基和C1-C4羟烷基的混合物二-或三-取代的铵;或其中n为2-6的整数;Y1和Y2独立地代表被卤素、氰基、羟基或C1-C4烷氧基任选取代的C1-C4烷基,或者Y1和Y2与它们各自所连接的氮原子一起形成5-7元杂环;Y3代表氢、C3-C4链烯基或被氰基、羟基或C1-C4烷氧基任选取代的C1-C4烷基,或者Y1,Y2和Y3与它们各自所连接的氮原子一起形成吡啶或甲基吡啶环;以及X1 -代表无色阴离子;和剩余取代基R1、R2和R3独立地代表卤素,C1-C12烷氧基或苯基,该苯基取代基任选地被一个或多个羟基、C1-C12-烷氧基,-O-CH2-CO-NH-CH2OH,SO3M取代,其中M的定义同上。
2.根据权利要求1的方法,其中n为2或3。
3.根据权利要求2的方法,其中Y1和Y2与它们各自所连接的氮原子一起形成吗啉、吡咯烷、哌啶或六亚甲基亚胺环。
4.根据权利要求1-3中任一项的方法,其中X1 -代表CH3OSO3 -或C2H5OSO3 -。
5.根据权利要求1-3中任一项的方法,其中剩余取代基R1、R2和R3独立地代表氯。
8.根据权利要求7的方法,其中的卤素是指氯。
10.根据权利要求1的方法,其中三嗪紫外线吸收剂为下式化合物:
其中M的定义同权利要求1;n1和n2独立地为0或1,其条件是如果n1为0,则n2也为0;
R9代表任选取代的芳基或代表下式基团:其中R11代表任选取代的烷基或任选取代的芳基;或者,当n2为0时,R9还可以为具有下列各式结构之一的基团:其中R11代表任选取代的烷基或任选取代的芳基;其中R12为M,任选取代的烷基或任选取代的芳基;其中R12的定义同上; 或
-NH2,-N(CH2CH2OH)2,-N[CH2CH(OH)CH3]2,-NH-R12,-N(R12)2或-OR12,其中R12的定义同上,或者R10代表其中氨基失去氢原子而得到的氨基酸残基。
11.根据权利要求10的方法,其中R10为具有式-NH-CH(CO2H)-R14的氨基酸残基,其中R14代表氢或式-CHR15R16基团,其中R15和R16独立地代表氢或被一个或两个选自下列的取代基任选取代的C1-C4烷基:羟基、硫代、甲硫基、氨基,羧基、磺基、苯基、4-羟苯基、3,5-二碘代-4-羟苯基、β-吲哚基,β-咪唑基和NH=(NH2)NH-。
12.根据权利要求10的方法,其中R10代表衍生自下列氨基酸的氨基酸残基:甘氨酸、丙氨酸、肌氨酸、丝氨酸、半胱氨酸、苯丙氨酸、酪氨酸、二碘酪氨酸、色氨酸、组氨酸、α-氨基丁酸、甲硫氨酸、缬氨酸、正缬氨酸、亮氨酸、异亮氨酸、正亮氨酸、精氨酸、鸟氨酸、赖氨酸、天冬氨酸、谷氨酸、苏氨酸、羟基谷氨酸或氨基磺酸,或其混合物或光学异构体。
13.根据权利要求12的方法,其中衍生得到这些氨基酸残基R10的氨基酸是谷氨酸和天冬氨酸。
14.根据权利要求10的方法,其中R10代表衍生自亚氨基二乙酸的氨基酸残基。
15.根据权利要求10的方法,其中R10代表衍生自牛磺酸、肌氨酸、谷氨酸或亚氨基二乙酸的氨基酸残基。
16.根据权利要求10的方法,其中R10代表氯、氨基、苯基、甲基苯基、二甲基苯基、吗啉代或其中氨基失去氢原子而得到的氨基酸残基。
17.根据权利要求10的方法,其中R9代表苯基、甲基苯基,二甲基苯基或下式基团:
其中R11的定义同权利要求10;和
R10代表苯基、甲基苯基、二甲基苯基,
-NH2,Cl,-N(CH2CH2OH)2,-N[CH2CH(OH)CH3]2,或代表其中氨基失去氢原子而得到的氨基酸残基。
18.根据权利要求17的方法,其中R11代表C1-C4-烷基。
19.根据权利要求17的方法,其中R11代表甲基或乙基。
21.根据权利要求1的方法,其中用作猝灭剂化合物的三嗪基紫外线吸收剂的用量为受处理基质中荧光增白剂存在量的0.5-50倍。
22.按照前述权利要求中任一项所述的方法处理过的基质。
24.根据权利要求23的化合物,其中n1和n2各自为1;R9代表苯基,甲基苯基或二甲基苯基;且R10代表氯、氨基、苯基、甲基苯基或二甲基苯基,-OH,-NH2,-N(CH2CH2OH)2,-N[CH2CH(OH)CH3]2,-NH-R13,-N(R13)2或-OR13,其中R13的定义同权利要求10。
28.下式化合物:
31.下式化合物:
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GB9611614.0 | 1996-06-04 | ||
GBGB9611614.0A GB9611614D0 (en) | 1996-06-04 | 1996-06-04 | Process for inhibiting the effect of flourescent whitening agents |
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EP (1) | EP0912530A2 (zh) |
JP (1) | JP2000512667A (zh) |
KR (1) | KR20000016276A (zh) |
CN (1) | CN1081655C (zh) |
AU (1) | AU728995B2 (zh) |
BR (1) | BR9709637A (zh) |
CA (1) | CA2252575A1 (zh) |
GB (1) | GB9611614D0 (zh) |
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NZ (1) | NZ332430A (zh) |
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CN107109227A (zh) * | 2014-09-30 | 2017-08-29 | 光学转变公司 | 紫外光吸收剂 |
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GB9726365D0 (en) * | 1997-12-13 | 1998-02-11 | Ciba Sc Holding Ag | Compounds |
SG75939A1 (en) * | 1998-04-09 | 2000-10-24 | Ciba Sc Holding Ag | Diresorcinyl-alkoxy-and-aryloxy-s-triazines |
KR20020019068A (ko) * | 1999-06-11 | 2002-03-09 | 에프. 아. 프라저, 에른스트 알테르 (에. 알테르), 한스 페터 비틀린 (하. 페. 비틀린), 피. 랍 보프, 브이. 스펜글러, 페. 아에글러 | 형광 증백제로 처리된 섬유재료의 형광을 억제하기 위한uv 흡수제의 용도 |
US7425222B2 (en) * | 2002-02-18 | 2008-09-16 | Ciba Specialty Chemicals Corp. | Process for improving the sun protection factor of cellulosic fibre material |
US7026570B2 (en) | 2002-03-28 | 2006-04-11 | Aerospace Consulting Corporation Spain, S.L. | Transportable, self-controlled plasma neutralization of highly toxic bio-chemical waste and method therefore |
KR20060073588A (ko) * | 2003-08-06 | 2006-06-28 | 시바 스페셜티 케미칼스 홀딩 인크. | 종이의 형광 표백용 조성물 |
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BR112012029133A2 (pt) | 2010-05-18 | 2016-09-13 | Milliken & Co | abrilhantadores óticos e composições compreendendo os mesmos |
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KR20000016276A (ko) | 2000-03-25 |
EP0912530A2 (en) | 1999-05-06 |
CN1221439A (zh) | 1999-06-30 |
US6143888A (en) | 2000-11-07 |
ID17024A (id) | 1997-12-04 |
NZ332430A (en) | 2000-05-26 |
WO1997046541A3 (en) | 1998-02-19 |
BR9709637A (pt) | 1999-08-10 |
JP2000512667A (ja) | 2000-09-26 |
GB9611614D0 (en) | 1996-08-07 |
AU728995B2 (en) | 2001-01-25 |
WO1997046541A2 (en) | 1997-12-11 |
ZA974870B (en) | 1998-05-12 |
AU3028497A (en) | 1998-01-05 |
CA2252575A1 (en) | 1997-12-11 |
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