US2458397A - Dyeing of nylon fibers by treating with nitrogenous condensation products - Google Patents
Dyeing of nylon fibers by treating with nitrogenous condensation products Download PDFInfo
- Publication number
- US2458397A US2458397A US558469A US55846944A US2458397A US 2458397 A US2458397 A US 2458397A US 558469 A US558469 A US 558469A US 55846944 A US55846944 A US 55846944A US 2458397 A US2458397 A US 2458397A
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- United States
- Prior art keywords
- dyeing
- nylon
- fibres
- formaldehyde
- per cent
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Classifications
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/241—Polyamides; Polyurethanes using acid dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
- D06P1/56—Condensation products or precondensation products prepared with aldehydes
Definitions
- This invention relates to the dyeing of nylon fibres with direct cotton dyestuffs in an acid dyebath.
- nylon fibres containing a water-insoluble condensation product of formaldehyde and cyanamide or a derivative thereof can be dyed with a direct cotton dyestuif from an acid dyebath with a considerably enhanced rate of absorption.
- the water-insoluble condensation product may be incorporated in the nylon fibres by treating the said fibres with an aqueous solution containing formaldehyde and cyanarnide or a derivative thereof, either as such or in the form of a water-soluble precondensate, and subsequently heating to convert the watersoluble condensation product into the insoluble form.
- Cyanamide derivatives which may be used in the present invention are dicyandiamide, melamine, guanidine, biguanide and dicyandiamidine or alkyl, hydroxyalkyl or aryl substitution products of guanidine, biguanide and dicyandiamidine. Salts of any of these compounds may be used in preparing the impregnating solution.
- the process of the present invention is of particular value when it is desired to use direct cotton dyestuffs, such as Chlorazol Fast Pink BKS (Colour Index No. 353 and Chlorazol Black BHS (Colour Index No. 401), which are absorbed very slowly by untreated nylon fibres.
- the Wash fastness of the dyeings obtained b the process of the present invention is extremely good and this result is obtained without impairment of all 2 Y the light fastness.
- the nylon fibres, particularly in the form of fabric, treated according to the present invention lose more or less of their characteristic soapy handle.
- Example 1 A length of an all nylon fabric is padded through an aqueous solution containing 10 grams of diphenylguanidine (dissolved in 10 cubic centimetres of per cent acetic acid) and 50 cubic centimetres of 40 per cent formaldehyde in each litre of solution, at ordinary room temperature. squeezed evenly, so that the fabric retains approximately 70 per cent of its own weight of padding solution, dried at under 100 cen-tigrade and finally heated at 140 centigrade for 10 minutes.
- Example 2 A length of an all nylon fabric is padded through an aqueous solution containing 15 grams of dicyandiamide and 150 cubic centimetres of 40 per cent formaldehyde in each litre of solution at ordinary temperature, squeezed evenly so that the fabric retains approximately '70 per cent of its own weight of padding solution, dried at under centigrade and finally heated at l centigrade for 10 minutes.
- Example 4 43 denier/17 filament scoured bright nylon yarn is padded through an aqueous solution containing 20 grams of monoethanol biguanide neutral sulphate and 150 cubic centimenters of 40 per cent formaldehyde in each litre of solution, at ordinary room temperature, squeezed evenly sothat yard retains approximately 70 per cent of its own weight of padding solution, dried at under 100 centigrade and finally heated at 140 centigrade for 10 minutes. 1 kilogram of the so-treated yarn is then entered at a temperature of 90 centigrade into 50 litres of a dyebath containing 1 percent of Chlorazol Fast Pink BKS and 7.5 per cent of 80 per cent acetic acid, calculated on the weight of nylon, and dyeing continued at this temperature for one hour. A full shade of pink is obtained and the dyebath is well exhausted. The fastness to washing of the dyeing is extremely good.
- a process for dyeing nylon fibres at an enhanced rate of absorption with direct cotton dyestuffs having little afilnity for nylon which comprises incorporating in the nylon fibres a water-insoluble condensation product of formaldehyde and a member of the group consisting of cyanamide, dicyandiamidemelamine, guanidine, biguanide, dicyandiamidine, alkyl, hydroxyalkyl, and aryl substituents of guanidine, biguanide and dicyandiamidine and dyeing the fibres with the direct cotton dyestuff from an acid dyebath.
- a process for dyeing nylon fibres at an enhanced rate of absorption with direct cotton dyestufis having little aflinity for nylon which comprises treating the nylon fibres with an aqueous solution containing formaldehyde and a member of the group consisting of cyanamide, dicyan- 1 kilogram of the so-treat-- dlamide, melamine, guanidlne, biguanide, dlcyandiamidine, alkyl, hydroxyalkyl and aryl substituents of guanldine, biguanide, and dicyandiamidine, converting the formaldehyde and member of the group into a water-insoluble condensation product and dyeing the fibres with the direct cotton dyestuff from an acid dyebath.
- a process for dyeing nylon fibres at an enhanced rate of absorption with direct cotton dyestuffs having little aifinity for nylon which comprises treating the nylon fibres with an aqueous solution containing formaldehyde and cyanamide, converting the formaldehyde and cyanamide into a water-insoluble condensation product and dyeing the fibres with the direct cotton dyestuff from an acid dyebath.
- a process for dyeing nylon fibres at an enhanced rate of absorption with direct cotton dyestuns having little ailinity for nylon which comprises treating the nylon fibres with an aqueous solution containing formaldehyde and diphenylguanidine, converting the formaldehyde and diphenylguanidine into a water-insoluble condensation product and dyeing the fibres with the direct cotton dyestuff from an acid dyebath.
- a process for dyeing nylon fibres at an enhanced rate of absorption with direct cotton dyestufis having little afiinity for nylon which comprises treating the nylon fibres with an aqueous solution containing formaldehyde and guanidine adipate, converting the formaldehyde and guanidine adipate into a water-insoluble condensation product and dyeing the fibres with the direct cotton dyestufi from an acid dyebath.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Description
unm:
Patented Jan. 4, 1949. r
DYEING F NYLON FIBERS BY TREATING WITH PRODUCTS NITROGENOUS CONDENSATION James Hutchlson MacGi-egor, Booking, Braintree,
England, assignor to Courtaulds Limited, London, England, a British company N 0 Drawing.
Application October 12, 1944, Se-
rial No. 558,469. In Great Britain November Claims. 1
This invention relates to the dyeing of nylon fibres with direct cotton dyestuffs in an acid dyebath.
In British Specification No. 547,844. Courtaulds Limited, C. M. Whittaker and C. C. Wilcock have described a process for dyeing nylon with direct cotton dyestuffs in an acid dyebath by carrying out the dyeing in the presence of an organic compound which increases the affinity of the nylon for the dyestuffs. The list of organic compounds in the specification includes cyanamide, guanidine, arylguanidines, dicyandiamide, dicyandiamidine and melamine.
I have now found that nylon fibres containing a water-insoluble condensation product of formaldehyde and cyanamide or a derivative thereof can be dyed with a direct cotton dyestuif from an acid dyebath with a considerably enhanced rate of absorption. The water-insoluble condensation product may be incorporated in the nylon fibres by treating the said fibres with an aqueous solution containing formaldehyde and cyanarnide or a derivative thereof, either as such or in the form of a water-soluble precondensate, and subsequently heating to convert the watersoluble condensation product into the insoluble form.
Cyanamide derivatives which may be used in the present invention are dicyandiamide, melamine, guanidine, biguanide and dicyandiamidine or alkyl, hydroxyalkyl or aryl substitution products of guanidine, biguanide and dicyandiamidine. Salts of any of these compounds may be used in preparing the impregnating solution.
When carrying out the present invention, I prefer to employ a padding process and in this case to use a paddin liquor containing in each litre not more than about grams of the cyanamide formaldehyde compound. If a more concentrated solution is used in the padding process, there is a tendency during the subsequent dyeing process for precipitation of a complex compound of the dyestufi and the cyanamide-formaldehyde condensate to take place, with the consequent production of weak and unlevel dyeings.
The process of the present invention is of particular value when it is desired to use direct cotton dyestuffs, such as Chlorazol Fast Pink BKS (Colour Index No. 353 and Chlorazol Black BHS (Colour Index No. 401), which are absorbed very slowly by untreated nylon fibres. The Wash fastness of the dyeings obtained b the process of the present invention is extremely good and this result is obtained without impairment of all 2 Y the light fastness. The nylon fibres, particularly in the form of fabric, treated according to the present invention lose more or less of their characteristic soapy handle.
The following examples illustrate the nature of the present invention without the invention being limited to these examples.
Example 1 A length of an all nylon fabric is padded through an aqueous solution containing 10 grams of diphenylguanidine (dissolved in 10 cubic centimetres of per cent acetic acid) and 50 cubic centimetres of 40 per cent formaldehyde in each litre of solution, at ordinary room temperature. squeezed evenly, so that the fabric retains approximately 70 per cent of its own weight of padding solution, dried at under 100 cen-tigrade and finally heated at 140 centigrade for 10 minutes. 1 kilogram of the so-treated nylon fabric is then entered at a temperature of centigrade into 50 litres of a dyebath containing 2 per cent of Chlorazol Fast Pink BKS and 7.5 per cent of 80 per cent acetic acid calculated on the weight of nylon, and dyeing continued at this temperature for one hour. A full shade of pink, which is very fast to Washing, is obtained, while the dyebath is almost exhausted. A piece of untreated fabric gives a much paler shade of pink when dyed under similar conditions. Furthermore, the treated fabric possesses a less soapy handle than the untreated fabric.
Example 2 A length of an all nylon fabric is padded through an aqueous solution containing 15 grams of dicyandiamide and 150 cubic centimetres of 40 per cent formaldehyde in each litre of solution at ordinary temperature, squeezed evenly so that the fabric retains approximately '70 per cent of its own weight of padding solution, dried at under centigrade and finally heated at l centigrade for 10 minutes. 1 kilogram of the .so-treated fabric is then entered at a temper- A length of an all nylon fabric is padded through an aqueous solution, containing 10 grams of guanidine adipate and 150 cubic centimetres of 40 per cent formaldehyde in eachlitre of solution, at ordinary tcmperatureysqueezed evenly so that it retains approximately 70 per cent of its own weight of padding solution, dried at under 100 Centigrade and finally heated at 140 centigrade for minutes. ed fabric is then entered at a temperature of 90 centigrade into 50 litres of a dyebath containing 1 per cent of Chlorazol Black BHS and 7.5 per cent of 80 per cent acetic acid, calculated on the weight of nylon and dyeing continued at this temperature for one hour. A full shade is obtained and the dyebath is well exhausted. The fastness to washing of the dyeing is extremely good. Untreated nylon dyed under similar conditions to those just described is dyed a very pale shade.
" Example 4 43 denier/17 filament scoured bright nylon yarn is padded through an aqueous solution containing 20 grams of monoethanol biguanide neutral sulphate and 150 cubic centimenters of 40 per cent formaldehyde in each litre of solution, at ordinary room temperature, squeezed evenly sothat yard retains approximately 70 per cent of its own weight of padding solution, dried at under 100 centigrade and finally heated at 140 centigrade for 10 minutes. 1 kilogram of the so-treated yarn is then entered at a temperature of 90 centigrade into 50 litres of a dyebath containing 1 percent of Chlorazol Fast Pink BKS and 7.5 per cent of 80 per cent acetic acid, calculated on the weight of nylon, and dyeing continued at this temperature for one hour. A full shade of pink is obtained and the dyebath is well exhausted. The fastness to washing of the dyeing is extremely good.
What I claim is:
1. A process for dyeing nylon fibres at an enhanced rate of absorption with direct cotton dyestuffs having little afilnity for nylon which comprises incorporating in the nylon fibres a water-insoluble condensation product of formaldehyde and a member of the group consisting of cyanamide, dicyandiamidemelamine, guanidine, biguanide, dicyandiamidine, alkyl, hydroxyalkyl, and aryl substituents of guanidine, biguanide and dicyandiamidine and dyeing the fibres with the direct cotton dyestuff from an acid dyebath.
2. A process for dyeing nylon fibres at an enhanced rate of absorption with direct cotton dyestufis having little aflinity for nylon which comprises treating the nylon fibres with an aqueous solution containing formaldehyde and a member of the group consisting of cyanamide, dicyan- 1 kilogram of the so-treat-- dlamide, melamine, guanidlne, biguanide, dlcyandiamidine, alkyl, hydroxyalkyl and aryl substituents of guanldine, biguanide, and dicyandiamidine, converting the formaldehyde and member of the group into a water-insoluble condensation product and dyeing the fibres with the direct cotton dyestuff from an acid dyebath.
3. A process for dyeing nylon fibres at an enhanced rate of absorption with direct cotton dyestuffs having little aifinity for nylon which comprises treating the nylon fibres with an aqueous solution containing formaldehyde and cyanamide, converting the formaldehyde and cyanamide into a water-insoluble condensation product and dyeing the fibres with the direct cotton dyestuff from an acid dyebath.
4. A process for dyeing nylon fibres at an enhanced rate of absorption with direct cotton dyestuns having little ailinity for nylon which comprises treating the nylon fibres with an aqueous solution containing formaldehyde and diphenylguanidine, converting the formaldehyde and diphenylguanidine into a water-insoluble condensation product and dyeing the fibres with the direct cotton dyestuff from an acid dyebath.
5. A process for dyeing nylon fibres at an enhanced rate of absorption with direct cotton dyestufis having little afiinity for nylon which comprises treating the nylon fibres with an aqueous solution containing formaldehyde and guanidine adipate, converting the formaldehyde and guanidine adipate into a water-insoluble condensation product and dyeing the fibres with the direct cotton dyestufi from an acid dyebath.
JAMES HUTCHISON MACGREGOR.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS OTHER REFERENCES Stott, Dyeing of Nylon Fibres," article in ,American Dyestuff Reporter for Oct. 2, 1939,
pages P582-P584.
Certificate of Correction Patent No. 2,458,397. January 4, 1949.
JAMES HUTOHISON MACGREGOR It is hereby certified that errors appear in the printed specification of the above numbered patent requiring correction as follows:
Column 3, line 3, before the Word temperature insert room; line 26, strike out yard and insert instead the yam; and that the said Letters Patent should be read with these corrections therein that the same may-conform to the record of the case in the Patent Office.
Signed and sealed this 31st day of May, A. D. 1949.
- THOMAS F. MURPHY,
Assistwnt commissioner of Patents.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB19250/43A GB570602A (en) | 1943-11-18 | 1943-11-18 | Improvements in and relating to the dyeing of nylon fibres |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2458397A true US2458397A (en) | 1949-01-04 |
Family
ID=10126228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US558469A Expired - Lifetime US2458397A (en) | 1943-11-18 | 1944-10-12 | Dyeing of nylon fibers by treating with nitrogenous condensation products |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2458397A (en) |
| GB (1) | GB570602A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2736749A (en) * | 1952-06-10 | 1956-02-28 | Arnold Hoffman & Co Inc | Dye-fixing agents |
| US2823093A (en) * | 1955-01-21 | 1958-02-11 | Rohm & Haas | Process of preventing discoloration of nylon textiles with urea, biuret, dicyandiamide or ammonium cyanate and a crease proofing resin and products produced therefrom |
| US2823094A (en) * | 1956-03-27 | 1958-02-11 | Rohm & Haas | Process of simultaneously heat setting and preventing discoloration of nylon textiles with urea, biuret, dicyandiamide or ammonium cyanate optionally followed by treatment with a crease proofing resin |
| US2903381A (en) * | 1954-09-03 | 1959-09-08 | Shell Dev | Treatment of synthetic textiles with a polyepoxide having a plurality of 1,2 epoxy groups |
| US2989798A (en) * | 1955-06-30 | 1961-06-27 | Du Pont | Filaments of improved dye-receptivity |
| US3314743A (en) * | 1963-11-07 | 1967-04-18 | Gagliardi Domenick Donald | Processes for treatment of preformed articles of olefin polymers and resulting products |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2119189A (en) * | 1933-03-27 | 1938-05-31 | Soc Of Chemical Ind | Pigment and process of making the same |
| US2168336A (en) * | 1935-06-18 | 1939-08-08 | Du Pont | Cellulosic structure and method for producing same |
| US2234905A (en) * | 1941-03-11 | Dyeing of cellulosic textile | ||
| US2253457A (en) * | 1938-06-13 | 1941-08-19 | Courtaulds Ltd | Improving the dyeing of textiles |
| GB547844A (en) * | 1941-03-07 | 1942-09-14 | Courtaulds Ltd | Improvements in and relating to the dyeing of nylon |
| US2317965A (en) * | 1939-05-27 | 1943-04-27 | Gen Aniline & Film Corp | Process of coloring fibrous materials and the materials obtained thereby |
| US2347143A (en) * | 1941-07-17 | 1944-04-18 | Courtaulds Ltd | Dyeing of textile fibers |
| US2356677A (en) * | 1941-05-08 | 1944-08-22 | Courtaulds Ltd | Treatment of cellulosic textile materials |
-
1943
- 1943-11-18 GB GB19250/43A patent/GB570602A/en not_active Expired
-
1944
- 1944-10-12 US US558469A patent/US2458397A/en not_active Expired - Lifetime
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2234905A (en) * | 1941-03-11 | Dyeing of cellulosic textile | ||
| US2119189A (en) * | 1933-03-27 | 1938-05-31 | Soc Of Chemical Ind | Pigment and process of making the same |
| US2168336A (en) * | 1935-06-18 | 1939-08-08 | Du Pont | Cellulosic structure and method for producing same |
| US2253457A (en) * | 1938-06-13 | 1941-08-19 | Courtaulds Ltd | Improving the dyeing of textiles |
| US2317965A (en) * | 1939-05-27 | 1943-04-27 | Gen Aniline & Film Corp | Process of coloring fibrous materials and the materials obtained thereby |
| GB547844A (en) * | 1941-03-07 | 1942-09-14 | Courtaulds Ltd | Improvements in and relating to the dyeing of nylon |
| US2356677A (en) * | 1941-05-08 | 1944-08-22 | Courtaulds Ltd | Treatment of cellulosic textile materials |
| US2347143A (en) * | 1941-07-17 | 1944-04-18 | Courtaulds Ltd | Dyeing of textile fibers |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2736749A (en) * | 1952-06-10 | 1956-02-28 | Arnold Hoffman & Co Inc | Dye-fixing agents |
| US2903381A (en) * | 1954-09-03 | 1959-09-08 | Shell Dev | Treatment of synthetic textiles with a polyepoxide having a plurality of 1,2 epoxy groups |
| US2823093A (en) * | 1955-01-21 | 1958-02-11 | Rohm & Haas | Process of preventing discoloration of nylon textiles with urea, biuret, dicyandiamide or ammonium cyanate and a crease proofing resin and products produced therefrom |
| US2989798A (en) * | 1955-06-30 | 1961-06-27 | Du Pont | Filaments of improved dye-receptivity |
| US2823094A (en) * | 1956-03-27 | 1958-02-11 | Rohm & Haas | Process of simultaneously heat setting and preventing discoloration of nylon textiles with urea, biuret, dicyandiamide or ammonium cyanate optionally followed by treatment with a crease proofing resin |
| US3314743A (en) * | 1963-11-07 | 1967-04-18 | Gagliardi Domenick Donald | Processes for treatment of preformed articles of olefin polymers and resulting products |
Also Published As
| Publication number | Publication date |
|---|---|
| GB570602A (en) | 1945-07-13 |
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