US3148937A - Method of preventing yellowing by nitrogen containing resins cured on cellulose fibers by adding hydrogen peroxide or urea peroxide - Google Patents
Method of preventing yellowing by nitrogen containing resins cured on cellulose fibers by adding hydrogen peroxide or urea peroxide Download PDFInfo
- Publication number
- US3148937A US3148937A US33079A US3307960A US3148937A US 3148937 A US3148937 A US 3148937A US 33079 A US33079 A US 33079A US 3307960 A US3307960 A US 3307960A US 3148937 A US3148937 A US 3148937A
- Authority
- US
- United States
- Prior art keywords
- resin
- fibers
- peroxide
- hydrogen peroxide
- cellulose fibers
- 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
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Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/32—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
- D06M11/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with hydrogen peroxide or peroxides of metals; with persulfuric, permanganic, pernitric, percarbonic acids or their salts
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/423—Amino-aldehyde resins
Definitions
- This invention relates to the finishing of cellulosic fibers, and particularly to an improved method of finishing cellulosic fibers with nitrogeneous resins, in accordance with which the discoloration normally imparted to the fibers by these resins, is substantially reduced.
- Fiber products treated in this fashion have met with considerable commercial success, by reason of their improved properties which provide them with many of the characteristics of the more expensive synthetic fiber products.
- the treatment has one major drawback which limits its use.
- the cured resin-fiber product is often yellowed, or discolored, to an objectionable degree by the resin treatment. This yellowing is magnified in cases Where the resin is even slightly overcured, with the result that undue care must be exercised to assure that the resin will be cured completely, and therefore will perform its function, and yet will not cause yellowing of the product.
- cellulosic fibers are impregnated with an aqueous solution of a nitrogenous resin from the class of the polymethylol and polyalkoxymethyl ureas and melamines, an acidic catalyst, and on the Weight of the resin about 0.012% to 0.2% of hydrogen peroxide introduced as aqueous hydrogen peroxide of any desired concentration, or as urea peroxide.
- the impregnated fibers are partially dried, and if desired, mechanically treated or manipulated to provide a particular finish on the fibers while they are in a wet condition, and thereafter the treated fibers are heated at a temperature of about 225 to 500 F. for a time sufficient to react the cellulose of the fibers with the nitrogeneous resin.
- the resulting fiber product is found to have the desirable properties of fiber products treated with the resin in the absence of the peroxide, and also to be free of the objectionable yellowness of such products.
- the important improvements in the products would not be expected to result from the simple addition to the resin formulation of the present small amounts of peroxide.
- This invention is applicable to a variety of cellulosic fibers, particularly to woven and non-woven fabrics made of cotton, rayon formed of regenerated celluloses, such as viscose and cuproammonium rayons, ramie, jute, linen, or other cellulosic fibers or cellulose derivatives which contain hydroxyl groups available for reaction with the nitrogeneous resin. Mixtures of two or more of such fibers may also be treated. Cottons should be free of Waxes before treatment, and if desired, they may have been mercerized.
- the nitrogeneous resin is employed on the fibers in the amount of about 1 to 15% of resin solids on fabric dry weight, and may be introduced by conventional means, such as with padding equipment and squeeze rolls. It is employed as an aqueous solution having any desired conconcentration which will provide the desired amount of resin on the fibers. Normally, a solution of about 5 to 20% concentration in water will be employed. More or less of the resin may be employed, however, the particular amount used will be determined on the bias of the degree of modification of the fibers desired. Normally, the indicated amount of 1 to 15% of the resin will provide excellent crease-resistance and washing resistance in the fabric, yet will provide a desirable hand or feel in the fabric.
- the acidic catalyst employed for promoting the curing reaction of the nitrogeneous resin which is believed to involve reaction of the nitrogeneous resin with cellulose hydroxy groups present in the fibers being treated, is not critical. Normally, about 0.1 to 2% of the acid catalyst on the weight of the resin will be employed, although more of the acid catalyst may be employed if desired.
- the acids commonly employed as catalysts for curing these resins may be employed, particularly the amine hydrochlorides such as morpholine hydrochloride, 2-aminopropanol hydrochloride and the like, ammonium salts of strong acids, for example, ammonium chloride, diammonium phosphate, ammonium sulfate and the like, the fluoroborates such as the zinc and other heavy metal salts, as well as the common acids such as phosphoric,
- the solution may also contain wetting agents, which assist in the impregnation of the fabric by the resin solution. Likewise, it may contain such materials as softeners or lubricants, or other materials known for the treatment of cloth.
- the treating solution importantly contains a small amount of hydrogen peroxide or urea peroxide, which serves to reduce markedly any yellowing which may be imparted to'the cloth by the cured resin.
- certain other active-oxygen chemicals for example, the persulfates such as ammonium and potassium persulfate, degrade the cloth under the conditions of curing, and do not eliminate the yellowing problem, even in some cases contributing to the yellowing rather than to avoidance of it.
- about 0.012 to 0.2% of 100% hydrogen peroxide on the weight of the resin is sufficient to avoid yellowing of the cloth. Use of less than the indicated lower amount of peroxide results in fiber products having little improvement in whiteness.
- the hydrogen peroxide may be introduced in the form of aqueous hydrogen peroxide of any desired concentration, or as the urea peroxide. It has been noted that substantially no reduction in crease recovery, tensile strength or tear strength is imparted to the fibers by incorporation of the peroxide in the resin mix.
- the present resin solutions are impregnated into the fibers by conventional means, for example, by passing the fibers through a solution of the resin followed by squeezing excess resin off with rolls, by spraying the resin onto the fibers and the like.
- Curing of the resin-treated fibers is effected by either simultaneously curing and drying the treated fibers in conventional heating equipment, or by first partially or completely drying the fibers and then curing with heat. In either case, a drying tenter-frame, heated metal cans or the like may be employed to provide the heat required for curing.
- the resins will cure at a temperature of about 225 F. to 500 F.
- the time of curing will, of course, vary in accordance with the temperature employed, from about ten seconds to half an hour. It is preferred to cure at a temperature of about 250 F. to 350 F., and for about two to ten minutes.
- EXAMPLE 1 (a) A cotton cloth sample having an '80 x 80 thread count and a weight of 4.0 yds./lb., measuring 10 inches wide by 3 feet long, was weighed and dipped into an aqueous solution containing 10% of dimethylol ethylene urea and 0.31% of morpholine hydrochloride on the weight of the resin. The sample was then passed through squeeze rolls to provide a pick-up of about 87% of resin solution on the weight of the cloth. Following this, the wet cloth was dried at room temperature, and cured at 320 F. for 5 minutes. It was then tested, with the results reported in Table I.
- Example 1(a) The procedure of Example 1(a) was followed with the exception that the resin solution contained in addition to the indicated ingredients, 0.05% of 35% hydrogen peroxide on the weight of the resin.
- the cloth sample was treated in the same fashion as was the sample in 1(a) above, with the results reported in Table I.
- EXAMPLE 3 This example demonstrates the amounts of hydrogen peroxide which may be employed in the present process.
- the procedure of Example 1(b) was followed, with the amounts of hydrogen peroxide reported in Table II as 100% hydrogen peroxide, being employed on the weight of the resin.
- the peroxide was introduced at 35% hydrogen peroxide.
- Example 1 the hydrogen peroxide was introduced as urea peroxide.
- the procedure followed was that of Example 1(b).
- Table III reports the percent reflectance values of resin-treated cloth products prepared with solutions containing varying amounts of urea peroxide, with amounts reported as 100% hydrogen peroxide.
- EYAMPLE 5 In this example the dimethylol ethylene urea resin was replaced with trimethylol melamine. In all respects, the experimental procedures of Example 1(a) and 1(b) above were followed, with Example 5(a) showing the eflect of having no peroxide in the resin solution, and Example 5(b) showing the effect of using hydrogen peroxide in the solution. Results of these examples are shown in Table IV.
- Example 6 the resin employed was dimethoxy methyl urea.
- the procedures of Example 1(a) and 1(b) were followed, with Examplie 6(a) showing the effect of treating the cloth with a resin formulation not containing hydrogen peroxide, and Example 6(b) showing the eifect EXAMPLE 7
- This example demonstrates the results obtained when the hydrogen peroxide is replaced with ammonium persulfate or potassium persulfate.
- the procedure of Example 1(a) was followed, with the exception that 0.15% of ammonium persulfate, and 0.15% of potassium persulfate, on the weight of the resin, were used in place of the hydrogen peroxide.
- Table Vi which follows.
- hydrogen peroxide introduced as such or as urea peroxide into a nitrogenous resin solution is an effective additive in the treatment of cellulosic fibers with the resin.
- the peroxide serves virtually to eliminate the undesirable yellowing of cellulosic fibers which is produced by treatment of the fibers with a resin solution not containing the peroxide.
- Fibers treated with the peroxide-containing resin solutions are essentially as bright as are the original fibers, in each case having a reflectance value of more than whereas the brightness of fibers treated with resin solutions containing no peroxygen compound are much lower, having reflectances even as low as about 65%.
- the other properties of the resin-treated fibers are not deleteriously affected by addition of the active oxygen compound to the resin used to treat the fibers. It is important to note that certain other activeoxygen compounds, for example ammonium and potassium persulfates, do not reduce yellowing of the fibers, and even damage the cloth when used with the resin. This is despite their effectiveness as carriers of active oxygen in many other applications.
- active oxygen compound for example ammonium and potassium persulfates
- Method of providing a soil-resistant and creaseresistant product having a high reflectance value and otherwise good physical properties from cellulose fibers from the group consisting of natural cellulose fibers and regenerated cellulose fibers comprising introducing onto said cellulose fibers, about 1 to 15% on the dry weight of said fibers of a nitrogenous resin which yellows on being heat cured on said fibers, said resin being from the group consisting of the polyfunctional methylol and alkoxymethyl urea resins and the polyfunctional methylol and alkoxymethyl melamine resins, an acidic curing agent for said resin, and a peroxide from the group consisting .of hydrogen peroxide and urea peroxide in an amount to provide, on the weight of said resin, about 0.012 to 0.2% of hydrogen peroxide, and heating the treated cellulose fibers until the nitrogenous resin is cured to a thermoset condition.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE601367D BE601367A (US08063081-20111122-C00044.png) | 1960-06-01 | ||
NL261866D NL261866A (US08063081-20111122-C00044.png) | 1960-06-01 | ||
US33079A US3148937A (en) | 1960-06-01 | 1960-06-01 | Method of preventing yellowing by nitrogen containing resins cured on cellulose fibers by adding hydrogen peroxide or urea peroxide |
ES0264955A ES264955A1 (es) | 1960-06-01 | 1961-02-17 | Un procedimiento para el acabado de fibras de celulosa con resinas nitrogenadas |
FR854772A FR1283495A (fr) | 1960-06-01 | 1961-03-07 | Procédé d'apprêtage de fibres cellulosiques au moyen de résines azotées |
GB14670/61A GB975821A (en) | 1960-06-01 | 1961-04-24 | Improvements in and relating to the treatment of fibrous cellulosic materials |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US33079A US3148937A (en) | 1960-06-01 | 1960-06-01 | Method of preventing yellowing by nitrogen containing resins cured on cellulose fibers by adding hydrogen peroxide or urea peroxide |
Publications (1)
Publication Number | Publication Date |
---|---|
US3148937A true US3148937A (en) | 1964-09-15 |
Family
ID=21868441
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US33079A Expired - Lifetime US3148937A (en) | 1960-06-01 | 1960-06-01 | Method of preventing yellowing by nitrogen containing resins cured on cellulose fibers by adding hydrogen peroxide or urea peroxide |
Country Status (5)
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4064089A (en) * | 1973-05-24 | 1977-12-20 | Westinghouse Electric Corporation | Accelerated melamine-aldehyde resin and method of making a fast-curing laminate therewith |
US4199322A (en) * | 1978-08-17 | 1980-04-22 | The United States Of America As Represented By The Secretary Of Agriculture | Antibacterial textile finishes utilizing zinc acetate and hydrogen peroxide |
US6100368A (en) * | 1992-06-11 | 2000-08-08 | Johnson; William Bruce | Process for production of acidic aqueous solutions of melamine-aldehyde polymer having low levels of free aldehyde |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2329651A (en) * | 1940-06-08 | 1943-09-14 | Rohm & Haas | Stabilization of knit fabrics |
US2339203A (en) * | 1941-08-30 | 1944-01-11 | American Cyanamid Co | Treatment of cellulosic textile material |
US2889192A (en) * | 1956-12-19 | 1959-06-02 | American Cyanamid Co | Method of treating cellulose-containing textile materials, materials so treated and diester composition therefor |
US2899263A (en) * | 1949-08-15 | 1959-08-11 | Eneurea |
-
0
- NL NL261866D patent/NL261866A/xx unknown
- BE BE601367D patent/BE601367A/xx unknown
-
1960
- 1960-06-01 US US33079A patent/US3148937A/en not_active Expired - Lifetime
-
1961
- 1961-02-17 ES ES0264955A patent/ES264955A1/es not_active Expired
- 1961-04-24 GB GB14670/61A patent/GB975821A/en not_active Expired
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2329651A (en) * | 1940-06-08 | 1943-09-14 | Rohm & Haas | Stabilization of knit fabrics |
US2339203A (en) * | 1941-08-30 | 1944-01-11 | American Cyanamid Co | Treatment of cellulosic textile material |
US2899263A (en) * | 1949-08-15 | 1959-08-11 | Eneurea | |
US2889192A (en) * | 1956-12-19 | 1959-06-02 | American Cyanamid Co | Method of treating cellulose-containing textile materials, materials so treated and diester composition therefor |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4064089A (en) * | 1973-05-24 | 1977-12-20 | Westinghouse Electric Corporation | Accelerated melamine-aldehyde resin and method of making a fast-curing laminate therewith |
US4199322A (en) * | 1978-08-17 | 1980-04-22 | The United States Of America As Represented By The Secretary Of Agriculture | Antibacterial textile finishes utilizing zinc acetate and hydrogen peroxide |
US6100368A (en) * | 1992-06-11 | 2000-08-08 | Johnson; William Bruce | Process for production of acidic aqueous solutions of melamine-aldehyde polymer having low levels of free aldehyde |
Also Published As
Publication number | Publication date |
---|---|
BE601367A (US08063081-20111122-C00044.png) | |
NL261866A (US08063081-20111122-C00044.png) | |
ES264955A1 (es) | 1961-08-16 |
GB975821A (en) | 1964-11-18 |
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