Hypochlorite free method for preparation of stable...

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C536S001110, C536S056000, C536S063000, C536S102000, C536S105000, C536S110000

Reexamination Certificate

active

06919447

ABSTRACT:
A method of making a carboxylated carbohydrate is disclosed, cellulose being a preferred carbohydrate material. Carboxylated cellulose fibers can be produced whose fiber strength and degree of polymerization is not significantly sacrificed. The method involves the use of a catalytic amount of a hindered cyclic oxammonium compounds as a primary oxidant and chlorine dioxide as a secondary oxidant in an aqueous environment. The oxammonium compounds may be formed in situ from their corresponding amine, hydroxylamine, or nitroxyl compounds. The oxidized cellulose may be stabilized against D.P. loss and color reversion by further treatment with an oxidant such as sodium chlorite or a chlorine dioxide/hydrogen peroxide mixture. Alternatively it may be treated with a reducing agent such as sodium borohydride. In the case of cellulose the method results in a high percentage of carboxyl groups located at the fiber surface. The product is especially useful as a papermaking fiber where it contributes strength and has a higher attraction for cationic additives. The product is also useful as an additive to recycled fiber to increase strength. The method can be used to improve properties of either virgin or recycled fiber. It does not require high α-cellulose fiber but is suitable for regular market pulps.

REFERENCES:
patent: 3575177 (1971-04-01), Briskin et al.
patent: 4100341 (1978-07-01), Brasey et al.
patent: 4401810 (1983-08-01), Tang et al.
patent: 4480089 (1984-10-01), Chen et al.
patent: 4505775 (1985-03-01), Harding et al.
patent: 4679278 (1987-07-01), Caumont
patent: 4889654 (1989-12-01), Mason et al.
patent: 5667637 (1997-09-01), Jewell et al.
patent: 5755828 (1998-05-01), Westland
patent: 5824462 (1998-10-01), Ashida et al.
patent: 6031101 (2000-02-01), Devine et al.
patent: 6117833 (2000-09-01), Racherla
patent: 6127573 (2000-10-01), Li et al.
patent: 6228126 (2001-05-01), Cimecioglu et al.
patent: 6242245 (2001-06-01), Amann et al.
patent: 6379494 (2002-04-01), Jewell et al.
patent: 6409881 (2002-06-01), Jaschinski
patent: 6447644 (2002-09-01), Seltzer et al.
patent: 6514384 (2003-02-01), Jewell et al.
patent: 6524348 (2003-02-01), Jewell et al.
patent: 2002/0072600 (2002-06-01), Bragd et al.
patent: 0 574 666 (1993-04-01), None
patent: 1 077 221 (2001-02-01), None
patent: 1 077 285 (2001-02-01), None
patent: 1 077 286 (2001-02-01), None
patent: 2674528 (1992-10-01), None
patent: 2001/49591 (2001-02-01), None
patent: WO 95/07303 (1995-03-01), None
patent: WO 96/36621 (1996-11-01), None
patent: WO 96/38484 (1996-12-01), None
patent: WO 98/27117 (1998-06-01), None
patent: WO 99/23117 (1999-05-01), None
patent: WO 99/57158 (1999-11-01), None
patent: WO 00/50388 (2000-08-01), None
patent: WO 00/50462 (2000-08-01), None
patent: WO 00/50463 (2000-08-01), None
patent: WO 00/50621 (2000-08-01), None
patent: WO 00/56978 (2000-09-01), None
patent: WO 01/29309 (2001-04-01), None
patent: WO 01/23657 (2001-05-01), None
U.S. Appl. No. 09/875,240.
U.S. Appl. No. 10/390,354.
U.S. Appl. No. 10/635,097.
U.S. Appl. No. 10/635,109.
U.S. Appl. No. 10/635,284.
Andersson, R., J. Hoffman, N. Nahar, and E. Scholander. An n.m.r. study of the products of oxidation of cellulose and (1 → 4)-β-D-xylan with sodium nitrite in orthophosphoric acid.Carbohydrate Research206: 340-346 (1990).
Anelli, P.L., S. Banfi, F. Montanari, and S. Quichi. Oxidation of diols with alkali hypochlorites catalyzed by oxammonium salts under two-phase conditions.Journal of Organic Chemistry54: 2970-2972 (1989).
Barzyk, D., D. H. Page, and A. Ragauskas. Acidic group topochemistry and fibre-to-fibre bond strength.Journal of Pulp and Paper Science23(2): J59-J61 (1997).
Barzyk, D., D. H. Page, and A. Ragauskas. Carboxylic acid groups and fibre bonding. InThe Fundamentals of Papermaking Materials: Transactions of 11thFundamental Research Symposium, Cambridge, 2: 893-907 (Sep. 1997).
Besemer, A. C., A. E. J. de Nooy. and H. van Bekkum. Methods for selective oxidation of cellulose: Preparation of 2,3-dicarboxycellulose and 6-carboxy- cellulose. InCellulose Derivatives, T. J. Heinze and W. G. Glasser eds., Ch. 5, pp 73-82 (1996).
Chang, P. S. and J. F. Robyt. Oxidation of primary alcohol groups of naturally occurring polysaccharides with 2,2,6,6-tetramethylpiperidine oxoammonium ion.Journal of Carbohydrate Chemistry15(7): 819-830 (1996).
Datye, K. V. and G. M. Nabar. Studies in the reaction of formaldehyde with unmodified, modified, and dyed celluloses. Part III: The reaction of formaldehyde and oxycelluloses.Textile Research Journal33(7): 500-510 (1963).
Davis, N. J. and S. L. Flitsch. Selective oxidation of monosaccharide derivatives to uronic acids.Tetrahedron Letters34(7): 1181-1184 (1993).
Einhorn, J., C. Einhorn, F. Ratajczak, and J-L. Pierre. Efficient and highly selective oxidation of primary alcohols to aldehydes by N-chlorosuccinimide mediated by oxammonium salts.Journal of Organic Chemistry61: 7452-7454 (1996).
Ganiev, I. M., Q. K. Timerghazin, A. F. Khalizov, V. V. Shereshovets, I. M. Grigor'ev, and G. A. Tolskitov. Complex of Chlorine dioxide with TEMPO and its conversion into oxoammonium salt.Journal of Physical Organic Chemistry14: 38-42 (2001).
Isogai, A. Application of stable nitroxyl radical reagents to cellulose modification.Cellulose Communications5(3): 153-164 (1998).
Isogai, A. and Y. Kato. Preparation of polyuronic acid from cellulose by TEMPO-mediated oxidation.Cellulose5: 153-164 (1998).
Kitaoka, T., A. Isogai, and F. Onabe. Surface modification of pulp fibers by TEMPO-mediated oxidation.Sen'i GakukaiPreprint 1998.
Kitaoka, T., A Isogai, and F. Onabe. Chemical modification of pulp fibers by TEMPO-mediated oxidation.Nordic Pulp and Paper Research Journal14 (4): 279-284 (1999).
Luner, P., K. P. Vemuri, and B. Leopold. The effect of chemical modification on the mechanical properties of paper. II. Wet strength of oxidized springwood and summerwood southern pine kraft fibers.Tappi50(3): 1127-120 (1967).
Luner, P., K. P. Vemuri, and F. Womeldorff. The effect of chemical modification on the mechanical properties of paper. III. Dry strength of oxidized springwood and summerwood southern pine kraft fibers.Tappi50(5): 227-230 (1967).
de Nooy, A. E. J., A. C. Besemer, and H. van Bekkum. Highly selective TEMPO mediated oxidation of primary alcohol groups in polysaccharides.Receuil des Traveau Chimiques des Pays-Bas113(3): 165-166 (1994).
de Nooy, A. E. J., A. C. Besemer, and H. van Bekkum. Highly selective nitroxyl radical-mediated oxidation of primary alcohol groups in water soluble glucans.Carbohydrate Research269:89-98 (1995).
de Nooy, A. E. J., A. C. Besemer, and H. van Beckum. On the use of stable organic nitroxyl radicals for the oxidation of primary and secondary alcohols.Synthesis: Journal of Synthetic Organic ChemistryOct. 1996 pp 1153-1174.
Shenai, V. A. and A. S. Narkhede. Hypochlorite oxidation of cellulose in the presence of cobalt sulfide.Textile Dyer and Printer20: 17-22 (1987).
Shet, R. T. and A. M. Yabani. Crease-recovery and tensile-strength properties of unmodified and modified cotton cellulose treated with crosslinking agents.Textile Research Journal51(11): 740-744 (1981).
Young, R. A. Bonding of oxidized cellulose fibers and interaction with wet strength resins.Wood and Fiber10(2): 112-119 (1978).
Zhao, M., J. Li, E. Mano, Z. Song, D. M. Tschaen, E. J. J. Grabowski, and P. J. Reider. Oxidation of primary alcohols to carboxylic acids with sodium chlorite catalyzed by TEMPO and bleach.Journal of Organic Chemistry64: 2564-2566 (1999).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Hypochlorite free method for preparation of stable... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Hypochlorite free method for preparation of stable..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Hypochlorite free method for preparation of stable... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3370451

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.