Search Images Maps Play YouTube News Gmail Drive More »
Sign in
Screen reader users: click this link for accessible mode. Accessible mode has the same essential features but works better with your reader.

Patents

  1. Advanced Patent Search
Publication numberUS3532454 A
Publication typeGrant
Publication dateOct 6, 1970
Filing dateApr 25, 1967
Priority dateMay 17, 1966
Also published asDE1619473A1
Publication numberUS 3532454 A, US 3532454A, US-A-3532454, US3532454 A, US3532454A
InventorsKarl Fuhr, Joachim Nentwig, Hans Rudolph, Johannes Romatowski
Original AssigneeBayer Ag
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Process for dyeing articles produced from aromatic polycarbonates
US 3532454 A
Abstract  available in
Images(2)
Previous page
Next page
Claims  available in
Description  (OCR text may contain errors)

United States Patent Int. Cl. D06p 3/54 US. Cl. 8-4 6 Claims ABSTRACT OF THE DISCLOSURE Dyed aromatic polycarbonate articles with a dispersion or developing dyestuff and a process for effecting said dyed articles comprising impregnating the articles with a dye composition containing an effective amount of at least one of an alkoxyalkylbenzyl ether, alkylene glycoldi-benzyl ether, benzoic acid alkoxyalkyl ester, or phenoxy acetic acid-alkoxyalkyl ester.

The present invention relates to a process for the dyeing of articles produced from aromatic polycarbonates with dispersion or developing dyestuffs. The process consists in carrying out the dyeing in the presence of a compound of the formula in which R represents an alkyl radical, or a benzyl or phenyl radical which may be substituted in the aromatic nucleus by alkyl and/or halogen, R means hydrogen or an alkyl radical, and R is a benzyl, benzoyl or phenoxyacetal radical which may be substituted in the aromatic nucleus by alkyl and/ or halogen, and n is a number from 2 to 4.

Examples of the compounds of the Formula I inelude the following: ethyl-glycol-benzyl ether, butylglycol-benzyl ether, butyl-gylcol-p-chlorobenzyl ether, butyl glycol trichlorobenzyl ether, ethyleneglycol-dibenzyl ether, propyleneglycol-1,2-dibenzyl-ether, propyleneglycol 1,3-dibenzyl-ether, butyleneglycol-1,4-dibenzylether, 2-phenoxyethyl-benzyl-ether, benzoic acid-Z-ethoxyethyl ester, benzoic acid-Z-butoxyethyl-ester, p-chlorobenzoic acid 2-butoxyethyl-ester, benzoic acid-2-benzyloXyethyl-ester, benzoic acid-2-phenoxyethyl-ester, phenoxyacetic acid-2-ethoxyethyl-ester, phenoxyacetic acid-2- benzyloxyethyl-ester, phenoxyacetic acid-Z-phenoxyethylester.

In accordance with the present invention, it is possible to effect a dyeing of articles, e.g. filaments, fibres, fabrics and foils, produced from aromatic polycarbonates by means of dispersion or developing dyestuffs yielding deep shades, while substantially accelerating the dyestuff absorption.

The necessary amounts of the compounds of the Formula I to be used according to the invention can be readily determined in each case by preliminary experiments; in general, amounts of 0.2 to 4 g. per litre dyeing liquor are found to be sufficient depending upon the desired depth of colour of the final dyeing and the liquorto-goods ratio.

Since the compounds of the Formula I are water-insoluble, care must be taken that they are present in the dyebath in an emulsified form; for this purpose they can be added in the form of solutions in organic solvents, e.g. in isopropyl alcohol, to the dyebaths which contain an emulsifier or an emulsifier mixture; however, it is also ice possible to proceed in such a manner that mixtures which are prepared from the compounds of the Formula I and emulsifiers are added to the dyebaths. Anion-active and/ or non-ionic compounds are preferably used as emulsifier.

In the present case, there are to be understood by the term aromatic polycarbonates, preferably those polycarbonates which are based on dihydric phenols. Dihydric phenols comprise, for example, hydroquinone, resorcinol, dihydroxy-diphenyl, but chiefly bisphenols, such as bis- (hydroxyphenyl)-alkanes, e.g. 2,2-bis-(4-hydroxyphenyl)- propane (bisphenol A), bis-(hydroxyphenyl)-cycloalk anes, -ethers, -sulphides, -sulphoxides or -sulphones, and mixtures of such dihydric phenols.

Suitable dispersion and developing dyestuffs are, for example, those described in Diserens, Die neuesten Fortschritte in der Anwendung der Farbstolfe, 2nd volume, 2nd edition (1949), pages 254 et seq., and 1st volume, 2nd edition (1946) pages 304 et seq.

The parts given in the following examples are parts by weight.

EXAMPLE 1 Fibres of bisphenol A-polycarbonate =1.75 to 2.15 in methylene chloride, c.=0.5 g./ ml. at 25 C.) are introduced into an aqueous bath having a liquor-to-goods ratio of 40:1 and containing, per litre, 0.75 g. of the dispersion dyestufii 1-hydroxy-(p-tolyamino)-anthraquinone and 2 g. sodium salt of N-oleyl-N-methyl-taurine. 2.5 grams 2-butoxyethyl-benZyl-ether, dissolved in isopropyl alcohol, are then added, per litre, to the bath while stirring. The fibres are subsequently dyed at 96-98 C. for 2 hours, then rinsed and dried. A deep blue dyeing of very good fastness to light is obtained.

Deep blue dyeings of very good fastness are also obtained,'i f 2-butoxyethyl-benZyl-ether is replaced by one of the following compounds: 2-ethoxyethyl-benzyl-ether, 2 propoxy ethyl-benzyl-ether, 2-phenoxyethyl-benzylether, propylene glycol 1,2 dibenzyl-ether, butyleneglycol 1,3-dibenzyl-ether, benzoic acid-2-propoxyethylester, benzoic acid-2-benzyloxy-ethyl-ester, benzoic acid-2- phenoxyethyi ester, phenoxyacetic acid 2-ethoxyethylester, phenoxyacetic acid 2-butoxyethyl-ester, phenoxyacetic acid-2-benzyloxyethyl-ester, phenoxyacetic acid-2- phenoxyethyl-ester.

When the procedure is followed as described above, but with the difference that there are added to the hot dyebath, instead of 2.5 g. 2-butoxyethyl-benzyl-ether, 5 g. of a mixture which is prepared from 50 parts ethyleneglycol-dibenzyl-ether, 35 parts water, 9 parts of the monoethanol ammonium salt of tetrapropylene-benzene-sulphonic acid and 6 parts of the reaction product of 16 mols ethylene oxide with 1 mol. o-benzylphenol, or of 25 parts 2-butoxyethylbenZyl-ether, 25 parts benzoic acid-2-butoxyethyl-ester, 35 parts of water, 9 parts of the mono ethanol-ammonium salt of tetrapropylene-benzene-sulphonic acid and 6 parts of the reaction product of 16 mols ethylene oxide with 1 mol o-benzyl-phenyl-phenol, a deep blue dyeing of very good fastness to light is also obtained.

EXAMPLE 2 Polycarbonate fibres of the type described in Example 1 are introduced into an aqueous bath having a liquorto-goods ratio 40:1 and containing, per litre, 0.75 g. of the dispersion dyestutf 1 amino 4-hydroxy-2-bromoanthraquinone and 3 g. sodium dinaphthyl-methane-disulphonate. 2.5 grams benzoic acid-2-ethoxyethyl-ester, dissolved in isopropyl alcohol, are then added, per litre, to the bath, while stirring. The fibres are subsequently dyed at 9698 C. for two hours, then rinsed and dried. A

3 deep red dyeing of very good fastness to light is obtained.

We claim:

1. A process for dyeing aromatic polycarbonate articles with a dispersion or developing dyestuff, comprising impregnating the articles With a dye composition containing an effective amount of an additive of the formula in which R is alkyl, benzyl, phenyl or the corresponding substituted radicals wherein the substituents are members selected from the group consisting of alkyl and halo; R is hydrogen or alkyl; R is benzyl, benzoyl, phenoxyacetyl or the corresponding substituted radicals wherein the substituents are members selected from the group consisting of alkyl and halo; and n is an integer of 2-4.

2. The process of claim 1 comprising effecting the dyeing in the presence of an alkoxyalkylbenzyl ether or the corresponding chloro substituted components having as substituent in the aromatic nucleus at least one halo radical.

3. The process of claim 1 comprising effecting the dyeing in the presence of an alkyleneglycol-dibenzyl ether or corresponding substituted compounds having as substituent in the aromatic nucleus at least one halo radical.

4. The process of claim 1 comprising effecting the dyeing in the presence of 'a benzoic acid alkoxyalkyl ester or corresponding substituted compounds having a substituent in the aromatic nucleus at least one halo radical.

5. The process of claim 1 comprising effecting the dyeing in the presence of a phenoxy acetic acid-alkoxyalkyl ester or corresponding substituted compounds having as substituent in the aromatic nucleus at least one halo atom radical.

6. The dyed polycarbonate obtained according to claim 1.

References Cited UNITED STATES PATENTS 3,003,843 10/1961 Amick 8-93 X 3,189,641 6/1965 Brack et al. 8173 X 3,385,652 5/1968 Walter et al. 84

GEORGE F. LESMES, Primary Examiner T. I. HERBERT, JR., Assistant Examiner US. Cl. X.R.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US3003843 *Dec 19, 1956Oct 10, 1961American Cyanamid CoMethod of dyeing nitrogenous fibers with premetalized azo dyes and compositions therefor
US3189641 *Nov 4, 1960Jun 15, 1965Bayer AgStyryl dyestuffs
US3385652 *Aug 21, 1963May 28, 1968Union Carbide CorpDyeing polyolefin articles with soluble dye and a short chain polyethylene glycol ether
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3917447 *May 14, 1974Nov 4, 1975Velsicol Chemical CorpDye compositions
US4245991 *Dec 12, 1979Jan 20, 1981American Hoechst CorporationDisperse dye in glycerol or ethylene glycol
US6231784Apr 20, 1998May 15, 2001Henkel CorporationWater insoluble composition of an aldoxime extractant and an equilibrium modifier
US6733543Mar 26, 2002May 11, 2004Bayer Polymers LlcProcess for making dyed articles
US6749646Nov 7, 2001Jun 15, 2004Bayer Polymers LlcDip-dyeable polycarbonate process
US6929666Mar 2, 2004Aug 16, 2005Bayer Materialscience LlcComposition comprising a dye
US6949127Mar 9, 2004Sep 27, 2005Bayer Materialscience Llcimmersing molded polycarbonate in dye bath containing leveling agent, plasticizer, and water; for production of tinted lenses
US6994735 *May 8, 2003Feb 7, 2006Bayer Materialscience LlcProcess for tinting plastic articles
US7094263Mar 14, 2005Aug 22, 2006Bayer Materialscience LlcComposition of matter comprising a dye
US7175675Dec 11, 2003Feb 13, 2007Bayer Materialscience LlcImmersing thermoplastic pellets or strands in an aqueous dye bath of dye(s), water, carrier of a hydroxy ether (e.g., ethylene glycol, monobutyl ether), and a diol (e.g., diethylene glycol); uniform dyeing; after removing the dyed thermoplastic, treating dye batch with activated carbon, for further use
EP1820896A2Nov 1, 2002Aug 22, 2007Bayer MaterialScience LLCProcess for dip-dyeing molded articles from polycarbonate
Classifications
U.S. Classification8/583, 8/610, 8/597, 8/914
International ClassificationD06P3/54, D06P1/651, D06P3/56
Cooperative ClassificationY10S8/914, D06P3/56, D06P3/54, D06P1/65106
European ClassificationD06P3/54, D06P3/56, D06P1/651B