US2362915A - Process for improving the fastness to washing of dyed cellulosic textile materials - Google Patents

Process for improving the fastness to washing of dyed cellulosic textile materials Download PDF

Info

Publication number
US2362915A
US2362915A US428012A US42801242A US2362915A US 2362915 A US2362915 A US 2362915A US 428012 A US428012 A US 428012A US 42801242 A US42801242 A US 42801242A US 2362915 A US2362915 A US 2362915A
Authority
US
United States
Prior art keywords
fastness
washing
dyed
improving
formaldehyde
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US428012A
Inventor
Macgregor James Hutchison
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Akzo Nobel UK PLC
Original Assignee
Courtaulds PLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Courtaulds PLC filed Critical Courtaulds PLC
Application granted granted Critical
Publication of US2362915A publication Critical patent/US2362915A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58Material containing hydroxyl groups
    • D06P3/60Natural or regenerated cellulose
    • D06P3/66Natural or regenerated cellulose using reactive dyes

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

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.
US428012A 1940-12-24 1942-01-23 Process for improving the fastness to washing of dyed cellulosic textile materials Expired - Lifetime US2362915A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2362915X 1940-12-24

Publications (1)

Publication Number Publication Date
US2362915A true US2362915A (en) 1944-11-14

Family

ID=10904743

Family Applications (1)

Application Number Title Priority Date Filing Date
US428012A Expired - Lifetime US2362915A (en) 1940-12-24 1942-01-23 Process for improving the fastness to washing of dyed cellulosic textile materials

Country Status (1)

Country Link
US (1) US2362915A (en)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2622075A (en) * 1946-12-03 1952-12-16 Sandoz Ltd Polyamine-cyanamide resins
US2736749A (en) * 1952-06-10 1956-02-28 Arnold Hoffman & Co Inc Dye-fixing agents
WO1991013056A1 (en) * 1990-03-02 1991-09-05 STATE OF OREGON, acting by and through THE OREGON STATE BOARD OF HIGHER EDUCATION, acting for and on behalf of THE OREGON HEALTH SCIENCES UNIVERSITY PORTLAND, OREGON, and THE UNIVERSITY OF OREGON, EUGENE, OREGON N,n'-disubstituted guanidines and their use as excitatory amino acid antagonists
US5262568A (en) * 1990-03-02 1993-11-16 State Of Oregon Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5312840A (en) * 1986-07-10 1994-05-17 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education Substituted guanidines having high binding to the sigma receptor and the use thereof
US5336689A (en) * 1990-03-02 1994-08-09 State 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 Oregon Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5385946A (en) * 1986-07-10 1995-01-31 State 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 Oregon Method for treating hypertension with disubstituted granidine compounds
US5403861A (en) * 1991-02-08 1995-04-04 Cambridge Neuroscience, Inc. Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers
US5574070A (en) * 1990-05-25 1996-11-12 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University Substituted guanidines having high binding to the sigma receptor and the use thereof
US5741661A (en) * 1991-02-08 1998-04-21 Cambridge Neuroscience, Inc. Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers
US5847006A (en) * 1991-02-08 1998-12-08 Cambridge Neuroscience, Inc. Therapeutic guanidines
US5922772A (en) * 1993-11-23 1999-07-13 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US6143791A (en) * 1994-02-03 2000-11-07 Cambridge Neuroscience, Inc. Therapeutic guanidines
US6147063A (en) * 1993-05-27 2000-11-14 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US6174924B1 (en) 1994-02-03 2001-01-16 Cambridge Neuroscience, Inc. Therapeutic guanidines
US6251948B1 (en) 1990-03-02 2001-06-26 State 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 Oregon Tri-and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US6787569B1 (en) 1994-02-03 2004-09-07 Cambridge Neuroscience, Inc. Therapeutic guanidines
US7351743B1 (en) 1994-02-03 2008-04-01 Wyeth Therapeutic guanidines

Cited By (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2622075A (en) * 1946-12-03 1952-12-16 Sandoz Ltd Polyamine-cyanamide resins
US2736749A (en) * 1952-06-10 1956-02-28 Arnold Hoffman & Co Inc Dye-fixing agents
US5604228A (en) * 1986-07-10 1997-02-18 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University Substituted guanidines having high binding to the sigma receptor and the use thereof
US5093525A (en) * 1986-07-10 1992-03-03 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University N,N'-disubstituted guanidines and their use as excitatory amino acid antagonists
US5502255A (en) * 1986-07-10 1996-03-26 State 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 Oregon Substituted guanidines having high binding to the sigma receptor and the use thereof
US5312840A (en) * 1986-07-10 1994-05-17 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education Substituted guanidines having high binding to the sigma receptor and the use thereof
US5478863A (en) * 1986-07-10 1995-12-26 State Of Oregon, Oregon Health Sciences University Of Oregon Substituted guanidines having high binding to the sigma receptor and the use thereof
US5385946A (en) * 1986-07-10 1995-01-31 State 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 Oregon Method for treating hypertension with disubstituted granidine compounds
US6251948B1 (en) 1990-03-02 2001-06-26 State 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 Oregon Tri-and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5336689A (en) * 1990-03-02 1994-08-09 State 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 Oregon Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5262568A (en) * 1990-03-02 1993-11-16 State Of Oregon Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5559154A (en) * 1990-03-02 1996-09-24 Oregon State Board Of Higher Education Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
WO1991013056A1 (en) * 1990-03-02 1991-09-05 STATE OF OREGON, acting by and through THE OREGON STATE BOARD OF HIGHER EDUCATION, acting for and on behalf of THE OREGON HEALTH SCIENCES UNIVERSITY PORTLAND, OREGON, and THE UNIVERSITY OF OREGON, EUGENE, OREGON N,n'-disubstituted guanidines and their use as excitatory amino acid antagonists
US5798390A (en) * 1990-03-02 1998-08-25 State 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 Oregon Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5767162A (en) * 1990-03-02 1998-06-16 State 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 Oregon Tri-and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5637622A (en) * 1990-03-02 1997-06-10 State 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 Oregon Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5574070A (en) * 1990-05-25 1996-11-12 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University Substituted guanidines having high binding to the sigma receptor and the use thereof
US5672608A (en) * 1991-02-08 1997-09-30 Cambridge Neuroscience, Inc. Acenaphthyl substituted guanidines and methods of use thereof
US5741661A (en) * 1991-02-08 1998-04-21 Cambridge Neuroscience, Inc. Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers
US5670519A (en) * 1991-02-08 1997-09-23 Cambridge Neuroscience, Inc. Acenaphthyl-substituted guanidines and methods of use thereof
US5637623A (en) * 1991-02-08 1997-06-10 Cambridge Neuroscience, Inc. Substituted adamantyl guanidines and methods of use there of
US5677348A (en) * 1991-02-08 1997-10-14 Cambridge Neuroscience, Inc. Substituted aminoguanidines and methods of use thereof
US5681861A (en) * 1991-02-08 1997-10-28 Cambridge Neuroscience, Inc. Aminoguanidines and methods of use of same
US5686495A (en) * 1991-02-08 1997-11-11 Cambridge Neuroscience, Inc. Substituted hydrazinedicarboximidamides and methods of use thereof
US6071969A (en) * 1991-02-08 2000-06-06 Cambridge Neuroscience, Inc. Substituted aminoguanidines and methods of use thereof
US5622968A (en) * 1991-02-08 1997-04-22 Cambridge Neuroscience, Inc. Acenaphthyl substituted guanidines and methods of use thereof
US5614630A (en) * 1991-02-08 1997-03-25 Cambridge Neuroscience, Inc. Acenaphthyl substituted guanidines and methods of use thereof
US5837737A (en) * 1991-02-08 1998-11-17 Cambridge Neuroscience, Inc. Hydrazinedicarboximidamide compounds and pharmaceutical composition comprising same
US5847006A (en) * 1991-02-08 1998-12-08 Cambridge Neuroscience, Inc. Therapeutic guanidines
US5403861A (en) * 1991-02-08 1995-04-04 Cambridge Neuroscience, Inc. Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers
US5652269A (en) * 1991-02-08 1997-07-29 Cambridge Neuroscience, Inc. Substituted hydrazinecarboximidamides and methods of use thereof
US6153604A (en) * 1993-05-27 2000-11-28 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US6147063A (en) * 1993-05-27 2000-11-14 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US5955507A (en) * 1993-11-23 1999-09-21 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US6013675A (en) * 1993-11-23 2000-01-11 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US6156741A (en) * 1993-11-23 2000-12-05 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US5922772A (en) * 1993-11-23 1999-07-13 Cambridge Neuroscience, Inc. Therapeutic substituted guanidines
US6143791A (en) * 1994-02-03 2000-11-07 Cambridge Neuroscience, Inc. Therapeutic guanidines
US6174924B1 (en) 1994-02-03 2001-01-16 Cambridge Neuroscience, Inc. Therapeutic guanidines
US6288123B1 (en) 1994-02-03 2001-09-11 Cambridge Neurosciences, Inc. Therapeutic guanidines
US6787569B1 (en) 1994-02-03 2004-09-07 Cambridge Neuroscience, Inc. Therapeutic guanidines
US20070265348A1 (en) * 1994-02-03 2007-11-15 Scion Pharmaceuticals, Inc, A Delaware Corporation Therapeutic guanidines
US7351743B1 (en) 1994-02-03 2008-04-01 Wyeth Therapeutic guanidines

Similar Documents

Publication Publication Date Title
US2362915A (en) Process for improving the fastness to washing of dyed cellulosic textile materials
US2370031A (en) Process for improving fibrous material and the material treated by such process
US3216779A (en) Textile materials and process for manufacturing them
US2417312A (en) Improving the dyeing properties of cellulosic textiles by treatment with formaldehyde and a guanidine salt of an alpha-beta unsaturated carboxylic acid
US2726133A (en) Effect threads
US3824076A (en) Liquid ammonia-caustic dye solution and dyeing therewith
US2234889A (en) Dyeing of cellulosic textile materials
US5795354A (en) Process for dyeing wool and other keratin fibres
US2316057A (en) Textile material
US2302777A (en) Process of matting textiles
US2375124A (en) Process for modifying the dyeing and other properties of cellulosic textile materials
US3802835A (en) Alcohol-ammonia dye solution and dyeing therewith
US2095221A (en) Dyeing method and bath
GB570602A (en) Improvements in and relating to the dyeing of nylon fibres
US3619234A (en) Process for the optical brightening of fibrous materials of synthetic polyamides or cellulose esters
US3124412A (en) Continuous- dyeing method for fibrous
US2448448A (en) Dyeing of textile fibers containing nitrogen
US3573858A (en) Permanent press process
US2284614A (en) Process for improving cellulose products
US3597144A (en) Process for continuously dyeing wool fibers with mordant black 11 and treating with sodium nitrite
GB737224A (en) Improvements in or relating to filaments, films and other shaped articles of cellulose esters
US3746505A (en) Treatment of cellulosic textiles with 1,3-dimethylol-4,5-dihydroxy-2-imidazolidinone, zinc nitrate and a sequestering agent
US4154692A (en) Flame retardant process, solution and structures
US2356677A (en) Treatment of cellulosic textile materials
GB361200A (en) Improved manufacture of cellulose acetate threads and textile fabrics of acetate silk