Bleaching and dyeing; fluid treatment and chemical modification – Chemical modification of textiles or fibers or products thereof – Treating textiles or fibers from synthetic resin or natural...
Patent
1984-08-07
1987-05-26
Clingman, A. Lionel
Bleaching and dyeing; fluid treatment and chemical modification
Chemical modification of textiles or fibers or products thereof
Treating textiles or fibers from synthetic resin or natural...
8128R, 8490, 8917, C09K 1530, G03C 192, G03C 1110, D06M 1330
Patent
active
046682350
DESCRIPTION:
BRIEF SUMMARY
This invention relates to a method for protecting synthetic and natural fibres against phototendering by the use of substituted 2-(2'-hydroxyaryl)-2H-benzotriazolesulfonates.
Phototendering is a light-induced phenomenon which manifests itself as a loss in strength and abrasion resistance of the fibre. The resultant damage is particularly noticeable in woollen car upholstery and in woollen curtains of the scrim variety, which sometimes fall apart within a few years upon exposure to sunlight--even through glass. It is of course well known that synthetic fibres and plastics are also damaged by light and it has become commonplace for additives to be added to the polymeric material before fabrication in the hope of retarding such light-induced damage. Particularly effective additives are certain organic compounds, known as ultraviolet absorbers, which absorb ultraviolet radiation preferentially thereby protecting the fibre or plastic from the damaging effects of sunlight.
The present invention had its origin in the notion that suitably modified ultraviolet absorbers might protect natural protein and synthetic fibres against photodegradation, particularly phototendering. Particularly relevant to the present invention was the observation that certain sulfonic acid derivatives of substituted 2-(2'-hydroxyphenyl)-2H-benzotriazoles, a well-known class of ultraviolet absorber, reduced the rate of photoyellowing of bleached wool [Waters and Evans, Text. Res. J., 48, 251-255, (1978)]. Accordingly, a wide variety of benzotriazolesulfonic acids was synthesized and applied to certain natural and synthetic fibres particularly wool, silk and nylon; their effectiveness in reducing photodegradation is the subject of this invention.
The essential structural feature of 2-(2'-hydroxyphenyl)-2H-benzotriazole photostabilizers is the phenolic hydroxyl group, which is capable of forming both intra- and inter-molecular hydrogen bonds. It is the intramolecularly hydrogen-bonded form (Ia) which is responsible for the photoprotective (or photo-stabilizing) effect; if the proportion of the ##STR2## intermolecularly hydrogen-bonded form (Ib) is increased, as can happen in solvents [Heller, Eur. Poly. J., Supplement (1969), 105-132] or polymeric substrates [cf. Leaver, J. Polym. Sci. (Polym. Chem. Ed.) (1982), 20, 2429] capable of disrupting the intramolecular hydrogen bond, then the photostabilizing efficiency is reduced. On the other hand, if the phenolic hydroxyl group is flanked by a bulky substituent (e.g., t-alkyl) located in the ortho position (i.e., at R), then the intramolecular hydrogen bond may be protected to some extent from the disrupting effect of hydrogen bond breaking solvents [see also Heller (reference cited above)]. Particular attention has been paid to this (possibly beneficial) bulky group effect in the research which is the subject of the present application.
There are prior reports of the use of unsulfonated 2-(2'-hydroxyphenyl)-2H-benzotriazoles for the protection, with varying degrees of success, of some natural fibres against light e.g., mohair [van Rensburg, SAWTRI Bull., 12(4), 48-53 (1978)], cotton [van Rensburg, SAWTRI Technical Report No. 309 (1979)] and silk [e.g., Kuwahra, Nakamichi and Shoji, Nippon Sanshigaku Zasshi, 46(6), 486-492 (1977)]. Of particular relevance to the present invention, is the use of sulfonated 2-(2'-hydroxyphenyl)-2H-benzotriazoles for the protection of wool against yellowing [Waters and Evans, Text. Res. J., 48(5), 251-255 (1978); Leaver, Waters and Evans, J. Poly. Sci. (Poly. Chem. Ed.), 17, 1531-1541 (1979)].
The synthesis of substituted sodium 2-(2'-hydroxyphenyl)-2H-benzotriazolesulfonates has been claimed in several recent patents (collected below). However data concerning the specific use of these sulfonates is lacking; in particular, no protection of wool, wool-blends or synthetic fibres against sunlight is disclosed. The following relevant patents are recorded:
It is therefore an object of the present invention to provide means to protect synthetic and natural fibres such as
REFERENCES:
patent: 3383241 (1968-05-01), Davisson et al.
patent: 3849373 (1974-11-01), Siegle et al.
patent: 4001266 (1977-01-01), Rody et al.
patent: 4141903 (1979-02-01), Adler
patent: 4219480 (1980-08-01), White et al.
patent: 4230867 (1980-10-01), Kintopf et al.
P. J. Waters and Evans, N. A., Textile Research J., 1978, vol. 48, (No. 5), pp. 251-255.
Evans Neil A.
Leaver Ian H.
Rosevear Judi
Waters Peter J.
Wilshire John F. K.
Clingman A. Lionel
The Commonwealth of Australia Commonwealth Scientific & Industri
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