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(12) United States Patent (10) Patent No.: US 9,109,331 B2 Li Et Al

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(12) United States Patent (10) Patent No.: US 9,109,331 B2 Li Et Al USOO9109331 B2 (12) United States Patent (10) Patent No.: US 9,109,331 B2 Li et al. (45) Date of Patent: Aug. 18, 2015 (54) FLUORESCENT BRIGHTER #71 USED FOR (52) U.S. Cl. THE PAPERMAKING PROCESS CPC ................ D2IH 21/30 (2013.01); C09K II/06 (2013.01): D06L 3/12 (2013.01); D2IH 17/07 (71) Applicants: Meng Jun Li, Surrey (CA); Eric Ji Wei (2013.01) Li, Surrey (CA) (58) Field of Classification Search CPC. C07D 403/10; C07D 413/10; D06L 3/1207; (72) Inventors: Meng Jun Li, Surrey (CA); Eric Ji Wei DO6L 3/1228 Li, Surrey (CA) USPC .................................... 544/193.2: 8/442, 648 s See application file for complete search history. (*) Notice: Subject to any disclaimer, the term of this (56) References Cited patent is extended or adjusted under 35 U.S.C. 154(b) by 0 days. U.S. PATENT DOCUMENTS (21) Appl. No.: 14/073,868 7,812,156 B2 * 10/2010 Jackson et al. ............. 544, 1932 2003/0054969 A1* 3/2003 Fumagalli et al. ............ 510,394 (22) Filed: Nov. 7, 2013 * cited by examiner (65) Prior Publication Data Primary Examiner — Venkataraman Balasubramanian US 2015/O159331 A1 Jun. 11, 2015 (57) ABSTRACT Fluorescent whitening agent 71 (FB #71) 4,4'-bis(4-anilino (51) Int. Cl. 6-morpholino-1,3,5-triazin-2-yl)amino-2,2'-stilbene diso CO7D 43/10 (2006.01) dium salt (CAS #16090-02-1) is used on the wet-end paper C09K II/06 (2006.01) making process and coating papermaking process to increase D06L 3/12 (2006.01) the brightness of paper. D2 IH 17/07 (2006.01) D2 IIHI 2D/30 (2006.01) 2 Claims, No Drawings US 9,109,331 B2 1. 2 FLUORESCENT BRIGHTER #71 USED FOR U.S. Pat. No. 5,064.570 introduces a new preparation THE PAPERMAKING PROCESS method for fluorescent brightener that involves the use of specific water-insoluble aromatic or carbon-substituted fatty CROSS-REFERENCE TO RELATED alcohol auxiliaries. APPLICATIONS EP1253.191 and US 20030054969 present the composition of detergents, which includes stilbene-triazine-based optical In the following references of related patents, optical brightener (FB #71). brighteners, optical brightening agents (OBAs) and fluores CA 2576882 explores the use of stilbene-based OBA's on cent whitening agents (FWA's) refer to the same type of bleaching towers for pulp along with TAED for increasing specialty chemical. The brightening chemicals present in 10 pulp brightness. these patents do not solve the problem of yellowing caused by overdosage of OBA/FWA. In addition, none of the patents STATEMENT REGARDING FEDERALLY below discuss the use of FWA #71 on the application of SPONSORED RESEARCH ORDEVELOPMENT wet-end and coating papermaking process. 15 U.S. Pat. No. 7,812,156 proposes a modified OBA which Not applicable. maintains the high solubility and strong fluorescent whiten ing effects of previous OBA's while decreases the anionic REFERENCE TO ASEQUENCE LISTING, A load that stresses the papermaking system. TABLE, ORACOMPUTER PROGRAM U.S. Pat. No. 7,566,349 explores the use of a new FWA of amphoteric bis-triazinylaminostilbene derivative on the pro Not applicable. cess of whitening synthetic or natural organic materials such as paper. This new type of FWA is not usually suppressed in BACKGROUND OF THE INVENTION performance when put in the cationic papermaking environ ment or when combined with residual anionic FWA's. 25 In recent years, the consumers’ pursuit for ultra-bright U.S. Pat. No. 3,790.443 presents a technique of utilizing a paper has pushed the market demands for more products with water-soluble hydroxymethylaminonitrile salt in the form of a brightness of 90-110 in ISO standards. In order to produce dry powder on papermaking materials to quench the fluores these ultra-high brightness products, optical brightener cence of optical brightening agents present in the papermak agents (OBAs) or fluorescent whitening agents (FWA's) ing materials. By adding an acid along with the quencher, 30 must be utilized. some undesirable whitening effects of the OBA's could be OBA's or FWA's have chemical properties that absorb neutralized. light in the ultra-violet region (340-370 nm) and then re US20120211188 discloses the preparation techniques for a emitting it back into the visible spectrum, usually in the color specific concentrated aqueous disulfo-stilbene based FWA blue or indigo (420-470 nm). The absorption and re-emission for optically whitening paper. 35 happen at a rapid pace unlike the slow phosphorescence U.S. Pat. No. 8,475,630 introduces an aromatic ring based behaviour. The newly added blue light compensates the yel additive that can increase the retention rate of OBA's on paper lowness of paper products and produces a net whitening materials. By using the aromatic ring on the additive to asso effect that is observable to the naked eye. ciate with the OBA molecules chemically, capacity for reten There is an ongoing need for improved brightness with low tion is improved. 40 cost and with greater stability of the optical properties, i.e. U.S. Pat. No. 7,789,917 reveals the composition of an decreased reversion Such as yellowing (caused by overdos amphoteric stilbene OBA, which consists of a substrate and age), photoyellowing, and higher retention rates. the associated stilbene (one of 4,4'-diamino-2,2'-stilbene dis ulfonic acid, biarylsulfonate-4,4'-diamino-2,2'-stilbene dis SUMMARY OF THE INVENTION ulfonic acid, biaryldisulfonate-4,4'-diamino-2,2'-stilbene 45 disulfonic acid, derivatives thereof, salts thereof, and mix One of the biggest hurdles to using conventional FWA is tures thereof). the limit on overdosing, and low retention. This is especially U.S. Pat. No. 7,497,971 describes the use of a mixture of prominent in lower brightness paper that has significant FWA's based on dicyano-1,4-bis-styrylbenzenes and bisben mechanical pulp present. As an increasing amount of excess ZOxazoles. Such mixtures of two or more components may 50 conventional FWA has been input into the system, the paper exhibit a higher degree of whiteness than that of the sum of the materials coming off the machine would have more of a individual components alone. yellow tinge due to the natural appearance of the conventional U.S. Pat. No. 8,262,858 and U.S. Pat. No. 7,914,646 iden FWA. tify the use of oxidative agents for the paper process which The new generation fluorescent brightener 71 (FB #71) enhances the performance of OBA's and chelants. By ana 55 does not encounter this problem as it has a slightly different lyzing various stages of the papermaking process that involve molecular structure which exhibits an almost pure white oxidative compositions and processes that preserve and appearance. There is a plateauing effect for brightness gain enhance the brightness and improve color of pulp or paper, it associated with injection (at which point the cost effective was found that the use of an oxidative agent could also reduce ness decreases), but the paper products will no longer have a the photoyellowing of aged, bleached pulp materials. 60 yellowish tinge. In short, the machine tender can inject as U.S. Pat. No. 7,638,016 proposes a method of brightening much FWA as needed to increase the brightness, without the pulp fibres with at least one stilbene-based OBA after the last risking yellowing caused by overdosing. bleaching/extraction stage with a chlorine based bleaching FB #71 has been historically used in the detergent industry agent. as a brightener. However its application in papermaking pro US20120199302 presents a new composition using at least 65 cess has not been Successful due to the extremely low solu two specific disulfo-stilbene based FWA for optically whit bility in water caused by repulsions of its morpholino func ening paper or board. tional groups. Even though theoretically speaking, it is US 9,109,331 B2 3 4 possible to be used to brighten paper, it was never commer brightness value compared to the conventional FWA's when cially practical. Therefore FB #71 was not sought after by used on production that requires more mechanical pulp than papermakers. Kraft pulp. On the other hand, the low solubility of the FB #71 would yield a significantly higher retention rate on fibers than any 5 TABLE 1 other FWA's ever used in papermaking. By carefully opti Unbleached ISO Disulfo- Tetrasulfo- FB #71 ISO mizing the dosage in water of various temperatures, dissolu Brightness OBA (%) OBA (%) (%) Brightness tion was achieved. FB #71 re-emits light in the range of 440-450 nm (indigo light). 78 O.O1 O O 79 10 78 O.1 O O 87 The present invention relates to a novel, low-cost method 78 1.O O O 83 of producing high final brightness values in paper production 78 O O.O1 O 78.5 78 O O.1 O 84 not previously achieved, and reducing brightness reversion of 78 O 1.O O 83 paper material. 78 O O O.O1 8O According to the present invention there is provided an 15 78 O O O.1 90 FWA for making high brightness paper. The usage of the 78 O O 1.O 93 FWA comprises of approximately 0.01%-1.0% by weight FB #71 based on dry weight at a temperature of 30°C.-80° C. The invention provides several advantages over conven Example 2 tional FWAS: 1. Lower cost benefits due to the decreased addition of FWA Laboratory Studies while still achieving the same, or greater, ISO brightness values. The incoming paper samples (from a paper mill in British 2.
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