Bleaching and dyeing; fluid treatment and chemical modification – Dye or potential dye composition – additive – treatment,... – Fluorescent dye – e.g. – stilbene – benzimidazole – benzoxazole,...
Patent
1997-05-07
1999-02-23
Shah, Mukund J.
Bleaching and dyeing; fluid treatment and chemical modification
Dye or potential dye composition, additive, treatment,...
Fluorescent dye, e.g., stilbene, benzimidazole, benzoxazole,...
162162, 442130, 510394, 5441932, C07D25170, C07D40314, D06L 300
Patent
active
058739130
DESCRIPTION:
BRIEF SUMMARY
This invention relates to novel organic compounds based on 4,4'-diaminostilbene-2,2'-disulphonic acid.
4,4'-diaminostilbene-2,2'-disulphonic acid., known generally as "DAS", is the starting material for a number of important products used in industry, most importantly various dyestuffs and optical brighteners. DAS-based optical brighteners (OBAs) find a wide range of uses in detergents, paper, textiles and so on.
One of the standard ways of making an optical brightener is to substitute the amino groups of DAS with substituted triazines. This may be done, for example, by reacting DAS with cyanuric chloride and then further reacting the remaining chlorines on the cyanuric chloride moiety. A popular substitutent for one of these chlorines is provided by sulphanilic acid.
It has now been found that it is possible to make a new class of DAS-based compounds whose performance is substantially better than that of known sulphanilic acid-based materials. The invention therefore provides a compound in free acid or salt form of the formula I ##STR2## wherein R, R.sub.1 are moieties which are the same or different and have the formula -NR.sub.2 R.sub.3, C.sub.1-6 thioalkyl, OH and SO.sub.3 M; and valencies not bonded with groups CO.sub.2 M being bonded with at least one of H, mercapto, C.sub.1-6 thioalkyl, OH and SO.sub.3 M, x is an integer of from 1-4 and M is selected from hydrogen, a colourless cation or an amine-derived cation; group (ii) is substituted with at least both of OH and SO.sub.3 M; with the provisos that R.sub.2 and R.sub.3 cannot both be hydrogen, and when one of R.sub.2, R.sub.3 is hydrogen, the other cannot be --(NHCH.sub.2 CO.sub.2 H); from 5-6 members only one of which is heterocyclic, which ring is singly substituted with --COOM or --SO.sub.3 M; and R.sub.5 are selected independently from the group consisting of hydrogen, methyl, C.sub.1-6 alkoxy and halogen.
In a preferred embodiment of the invention, R.sub.5 is hydrogen and the sulphonic acid groups on the phenylene rings attached to the triazine rings are meta or para to the connecting amino groups, that is, the particular moieties attached to the triazine rings are derived from sulphanilic acid or metanilic acid.
The moieties R and R.sub.1 may be derived from any-suitable compounds known to the art. It is preferred that they be amino-acid residues. Examples of suitable acids include glycine, aspartic acid, serine, hydroxy glutamic acid and alanine, but the preferred acids are glutamic acid and iminodiacetic acid.
The most preferred compounds are those derived from metanilic acid or sulphanilic acid and where R is derived from glutamic or iminodiacetic acid.
In the case where R.sub.2 and R.sub.3 together with the nitrogen atom of groups R, R.sub.1 form a ring, it is preferred that this ring be a pyrollidine ring substituted with --COOM.
The compounds according to the invention may be prepared in free acid form or in salt form such as with an alkali metal cation, an organic amine salt, a mixed or partial salt.
The materials M are preferably either metal cations, particularly sodium and potassium, or simple alkanolamines such as mono-, di-and triethanolamine.
Two of the most preferred compounds have the formulae II and III ##STR3##
Other compounds which also perform well are those which have the formulae IV-XI ##STR4##
The compounds according to this invention may be prepared by standard synthetic methods using readily-obtainable reagents.
The compounds may be used individually or in admixture. It has been found that some of them, particularly the aminodiacetic acid/glutamic acid -sulphanilic acid-derived material referred to hereinabove, exhibit outstanding optical brightening characteristics. The compounds according to the invention are therefore very useful as optical brightening agents (OBAs) in paper, textiles and so on.
The compounds of the invention are particularly effective when used as optical brightening agents for paper. They may be applied to paper either by addition to a paper stock prior to sheet formation or -they may be incorpora
REFERENCES:
patent: 3871898 (1975-03-01), Reinhert et al.
patent: 3979285 (1976-09-01), Wegmuller et al.
patent: 4025507 (1977-05-01), Fleck et al.
patent: 4115124 (1978-09-01), Hamilton et al.
patent: 4200489 (1980-04-01), Tlach et al.
patent: 4271395 (1981-06-01), Brinkmann et al.
patent: 4339238 (1982-07-01), Fringeli et al.
patent: 4364845 (1982-12-01), Fringeli
patent: 4374643 (1983-02-01), Suzuki et al.
patent: 4444871 (1984-04-01), Miyaoka et al.
patent: 4587195 (1986-05-01), Ishikawa et al.
patent: 4605511 (1986-08-01), Fringeli
patent: 4861344 (1989-08-01), Schlafer et al.
patent: 4880726 (1989-11-01), Shiba et al.
patent: 4898933 (1990-02-01), Schlafer et al.
patent: 5051111 (1991-09-01), Anceschi et al.
patent: 5238793 (1993-08-01), Hoyen, Jr.
patent: 5591257 (1997-01-01), Weide et al.
patent: 5656760 (1997-08-01), Bacher et al.
Official Gazette, 1134 OG 198, 98 and 99, Jan. 7, 1992.
Derwent Publication abstract of J5 029-885 Mar. 25, 1975.
Derwent Publication abstract J6 1058-266-A Aug. 19, 1985.
Derwent Publication abstract of J6 2106-965-A May 18, 1987.
Derwent Publication abstract of J6 3282-382-A Nov. 18, 1988.
Derwent Publication abstract of J7 6036-832 Oct. 12, 1976.
Cowman John Stuart
Farrar John Martin
Graham Mark David
Mackinnon Neil
Clariant Finance (BVI) Limited
Hanf Scott E.
Kifle Bruck
Shah Mukund J.
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