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 numberUS2362915 A
Publication typeGrant
Publication dateNov 14, 1944
Filing dateJan 23, 1942
Priority dateDec 24, 1940
Publication numberUS 2362915 A, US 2362915A, US-A-2362915, US2362915 A, US2362915A
InventorsMacgregor James Hutchison
Original AssigneeCourtaulds Ltd
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Process for improving the fastness to washing of dyed cellulosic textile materials
US 2362915 A
Abstract  available in
Images(2)
Previous page
Next page
Claims  available in
Description  (OCR text may contain errors)

either as such, or more Patented Nov. 14, 1944 PROCESS FOR MPROVING THE FASTNESS T WASHING OF CELLULOSIG TEX- TILE MATERIALS James Hutchison MacGr egor, Bocking, Braintree,

England, assignor to Courtaulds Limited, London, England, a British company No Drawing. Application January-23, 1942, Se-

Great Britain December rial No. 428,012. In

4 Claims.

This inventionrelates to the treatment of cellulosic textile material and in particular to improving the'fastness to washing, without greatly impairing the fastness to light or altering the original shade of the said material which has been dyed with'a direct cotton dyestuff, and at. the same time giving it. a softer silkier handle and appearance.

I have found that the fastness to washing of cellulosic textile materials dyed with direct cotton dyestuffs is improved by treating the dyed material with a solution containing formaldehyde and an arylguanidine or a guanidine salt of an aliphatic dicarboxylic'acid or. a guanidine salt of an alkyl ester of an aliphatic dicarboxylic acid,

probably in the form of, their water-soluble condensate, and then converting the mixture or the soluble condensate into an insoluble condensate, for instance by heating to a temperature of 140 centigrade in the presence of an acidcatalyst. In the case of the guanidine salts of aliphatic dicarboxylic acids and of alkyl esters of aliphatic dicarboxylic acids the condensation with formaldehyde can, if 'desired, be carried out in neutral or alkaline media. As an example of an arylguanidine which can be used according to this invention, I mention diphenylguanidine cm..NH-c'NHctHt It. v Examples of guanidine salts of aliphatic dicarboxylic acids are guanidine adipate and guanidine sebacate, while as an example of a guanidine salt of an alkyl ester of an aliphatic dicarboxylic acid I would mention the guanidine salt of ethyl adipate. The treatment can, if desired, be carried out in the presence of other water-soluble condensates such for instance as urea-formaldehyde, thiourea-formaldehyde and melamineformaldehyde.

When carrying out the process of the present invention I have found that it is desirable to avoid the use of a large excess of formaldehyde.

The following examples illustrate the invention Rigan Sky Blue G (Soc. Chem. Ind. Basle) is im-- mersed therein and after saturation the fabric is removed from the bath and squeezed evenly and is placed in a pin stenter frame and dried at just under 100 centigrade; it is then heated at 140 'centigrade for minutes. The resultant fabric has a good fastness to light, an improved fastness to washing and a soft silk-like handle and appearance.

Example 2 in 30 cubic centimetres of 80 per cent acetic acid and this solution is added to 100 grams of the urea-formaldehyde condensate prepared above and mixed with suflicient distilled water to make 1 litre of solution. A sample of an all viscose satin fabric which has been dyed with Rigan Sky Blue G is immersed therein and after soaking is removed from the solution and squeezed evenly. The fabric but they are not to be considered aslimiting it in any way.

Example! 7 30 grams of diphenilguanidine are dissolved by warming with 30 cubic-centimetres of per cent acetic acid. 160 cubic centimetres of 40 per cent formaldehyde are-added with sufllcient distilled";

water to make 1 litre of solution. A sample of an:

all viscose rayon fabric which has been dyed with at rlcis placed just under placed in a pin stenter frame and dried at just under100 centigr'ade. It is then heated at centigrade for 15 minutes to form the insoluble condensation product. During this heating a part of the formaldehyde is split off from the urea-formaldehyde condensate and combines with the diphenylguanidine. The fastness to'light and the fastness to washing of the dyed treated material are found to be improved. r

If desired, a soluble diphenylguanidine-formaldehyde condensate may be substituted for the diphenylguanidine in this example.

Example 3' 30 grams of guanidine' sebacate are dissolved in a little warm water, the resulting solution cooled, 200 cubic centimetres of 40 per cent formaldehyde added and the whole diluted with distilled water to make 1 litre of solution. The pH of the solution is then adjusted to 8.0; A sample of an all viscose satin fabric which has been dyed with Rigan Sky Blue G (Soc. of Chem. Ind. Basle) is immersed therein and after soaking is removed from the solution and squeezed evenly. I The fabin a pin stenter frame and dried at centlgrade. It is finally heated at 140 centigrade for 15 minutes \to form the insoluble condensation product. The resultant fabric possesses a soft silky handle, has very good fastness to light and is extremely fast to washing, for example when a piece of the fabric of dimensions 4" x a" and a piece of white undyed fabric of dimensions 2" .x 2" are treated in 70 cubic centimetres of a 0.2 per cent soap solution for 90 minutes at 60 centigrade, the fabrics removed and rinsed with distilled water the white piece remains unstained while the shade of the dyed piece is unchanged.

" Example 4 30 grams of guanidine adipate are dissolved in a little warm Water, the solution cooled and 200 1 cubic centimetres of 40 per cent formaldehyde added. Just before use 10 grams of ammonium sulphate dissolved in a little water are added and the whole bulked to 1 litre with distilled water.

A length of an all viscose satin fabric which has What I claim is:

1. The process of improving the fastness to washing of cellulosic textile materials dyed with direct cotton dyestuffs and imparting a soft silks, handle thereto, by treating the dyed material with a solution containing a watersoluble condensate of formaldehyde with a substance selected from the group consisting of an arylguanidine, a guanidine salt of an aliphatic dicarboxylic acid and a guanidine salt of an alkyl ester of an aliphatic dicarboxylic acid, and then converting the soluble condensate into an insoluble condensate.

2. The process of improving the fastness to washing of cellulosic textile materials dyed with direct cotton dyestuffs and imparting a soft silky handle thereto, by treating the dyed material with a solution containing formaldehyde and a. substance selected from the group consisting of an arylguanidine, a guanidine salt of an aliphatic dicarboxylic acid and a guanidine salt of an alkyl ester of an aliphatic dicarboxylic acid, and then converting the said mixture into an insoluble condensate.

8. A process as claimed in claim 1 in which the insoluble condensate is formed by heating in the presence of an acid catalyst.

4. A process as claimed in claim 2 in which the insoluble condensate is formed by heating in the presence of an acid catalyst.

. JAS. H. MACGREGOR.

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US2622075 *Dec 1, 1947Dec 16, 1952Sandoz LtdPolyamine-cyanamide resins
US2736749 *Jun 10, 1952Feb 28, 1956Arnold Hoffman & Co IncDye-fixing agents
US5093525 *Mar 2, 1990Mar 3, 1992State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences UniversityNeuroprotective agents
US5262568 *Mar 4, 1991Nov 16, 1993State Of OregonTri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5312840 *Feb 25, 1993May 17, 1994State Of Oregon, Acting By And Through The Oregon State Board Of Higher EducationSubstituted guanidines having high binding to the sigma receptor and the use thereof
US5336689 *Aug 11, 1993Aug 9, 1994State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of OregonTri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5385946 *Feb 23, 1993Jan 31, 1995State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of OregonAdministering hypotensive agents
US5403861 *Feb 10, 1992Apr 4, 1995Cambridge Neuroscience, Inc.Treating or preventing nerve cell death
US5478863 *Feb 23, 1993Dec 26, 1995State Of Oregon, Oregon Health Sciences University Of OregonSubstituted guanidines having high binding to the sigma receptor and the use thereof
US5502255 *Feb 23, 1993Mar 26, 1996State Of Oregon Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of OregonSubstituted guanidines having high binding to the sigma receptor and the use thereof
US5559154 *Aug 11, 1993Sep 24, 1996Oregon State Board Of Higher EducationTri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5574070 *May 22, 1991Nov 12, 1996State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences UniversitySubstituted guanidines having high binding to the sigma receptor and the use thereof
US5604228 *Apr 12, 1994Feb 18, 1997State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences UniversitySubstituted guanidines having high binding to the sigma receptor and the use thereof
US5614630 *Jun 5, 1995Mar 25, 1997Cambridge Neuroscience, Inc.Neurotransmitter release modulator
US5622968 *Jun 5, 1995Apr 22, 1997Cambridge Neuroscience, Inc.Acenaphthyl substituted guanidines and methods of use thereof
US5637622 *May 22, 1995Jun 10, 1997State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of OregonNervous system disorders
US5637623 *Jun 6, 1995Jun 10, 1997Cambridge Neuroscience, Inc.Substituted adamantyl guanidines and methods of use there of
US5652269 *Jun 5, 1995Jul 29, 1997Cambridge Neuroscience, Inc.Substituted hydrazinecarboximidamides and methods of use thereof
US5670519 *Jun 5, 1995Sep 23, 1997Cambridge Neuroscience, Inc.Acenaphthyl-substituted guanidines and methods of use thereof
US5672608 *Nov 22, 1994Sep 30, 1997Cambridge Neuroscience, Inc.Acenaphthyl substituted guanidines and methods of use thereof
US5677348 *Jun 5, 1995Oct 14, 1997Cambridge Neuroscience, Inc.Substituted aminoguanidines and methods of use thereof
US5681861 *Jun 6, 1995Oct 28, 1997Cambridge Neuroscience, Inc.Aminoguanidines and methods of use of same
US5686495 *Jun 6, 1995Nov 11, 1997Cambridge Neuroscience, Inc.Substituted hydrazinedicarboximidamides and methods of use thereof
US5741661 *Jun 5, 1995Apr 21, 1998Cambridge Neuroscience, Inc.Screening assay
US5767162 *Jun 6, 1995Jun 16, 1998State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of OregonTri-and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5798390 *May 22, 1995Aug 25, 1998State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of OregonTri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5837737 *Jun 7, 1995Nov 17, 1998Cambridge Neuroscience, Inc.Hydrazinedicarboximidamide compounds and pharmaceutical composition comprising same
US5847006 *May 31, 1995Dec 8, 1998Cambridge Neuroscience, Inc.Therapeutic guanidines
US5922772 *Jun 2, 1995Jul 13, 1999Cambridge Neuroscience, Inc.Therapeutic substituted guanidines
US5955507 *Jun 2, 1995Sep 21, 1999Cambridge Neuroscience, Inc.Therapeutic substituted guanidines
US6013675 *Jun 2, 1995Jan 11, 2000Cambridge Neuroscience, Inc.Therapeutic substituted guanidines
US6071969 *Jun 5, 1995Jun 6, 2000Cambridge Neuroscience, Inc.Substituted aminoguanidines and methods of use thereof
US6143791 *Jun 7, 1995Nov 7, 2000Cambridge Neuroscience, Inc.Therapeutic guanidines
US6147063 *Jun 2, 1995Nov 14, 2000Cambridge Neuroscience, Inc.Therapeutic substituted guanidines
US6153604 *Jun 2, 1995Nov 28, 2000Cambridge Neuroscience, Inc.Treating disease of nervous system in which pathophysiology of disorder involves excessive excitation of nerve cells by agonists of nmda receptors, comprising administering to guanidine derivative
US6156741 *Jun 2, 1995Dec 5, 2000Cambridge Neuroscience, Inc.Nervous system disorders
US6174924Jun 5, 1995Jan 16, 2001Cambridge Neuroscience, Inc.Treating nerve cell death comprising administering to a subject exhibiting symptoms of nerve cell death or susceptible to nerve cell death a substituted guanidine compound
US6251948Jun 6, 1995Jun 26, 2001State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of OregonTrisubstituted guanidine useful for treating diseases of the nervous system in which the pathophysiology of the disease involves excessive excitation of nerve cells by agonists of glutamate/n-methyl-d-aspartate receptor
US6288123Jun 5, 1995Sep 11, 2001Cambridge Neurosciences, Inc.Therapeutic guanidines
US6787569Aug 11, 2000Sep 7, 2004Cambridge Neuroscience, Inc.Therapeutic guanidines
US7351743Aug 11, 2000Apr 1, 2008WyethTherapeutic guanidines
WO1991013056A1 *Mar 4, 1991Sep 5, 1991Oregon StateN,n'-disubstituted guanidines and their use as excitatory amino acid antagonists
Classifications
U.S. Classification8/552, 528/259, 8/582, 564/238, 8/598, 528/232, 528/243, 564/60, 528/268, 8/918
International ClassificationD06P3/66
Cooperative ClassificationD06P3/66, Y10S8/918
European ClassificationD06P3/66