US2123152A - Treatment of cellulosic materials - Google Patents

Treatment of cellulosic materials Download PDF

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US2123152A
US2123152A US48283A US4828335A US2123152A US 2123152 A US2123152 A US 2123152A US 48283 A US48283 A US 48283A US 4828335 A US4828335 A US 4828335A US 2123152 A US2123152 A US 2123152A
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materials
cellulose
reagents
fabric
formaldehyde
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Rivat Georges
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Henry Dreyfuss Associates LLC
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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
    • 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

  • the present invention relates to improvements in the coloration of textile materials, especially cellulosic materials.
  • materials consisting of natural or regenerated cellulose have an afiinity for the cotton colors and little or no aflinity for the acid colors.
  • Basic colors are usually dyed or printed on such materials with the aid of a tannin mordant.
  • cellulose acetate artificial silk has an affinity for the basic colors and little or no afiinity for the acid and direct cotton colors.
  • the present invention is concerned with treating materials made of or containing natural or regenerated cellulose or cellulose derivatives for the purpose of modifying the existing dyeing affinities of these materials and with fixing dyestuffs on the materials.
  • animal fibers e. g. natural silk, may be colored by the new process.
  • the invention comprises incorporating in the materials a complex nitrogen-containing organic compound, preferably of resin character, by interaction, on the materials, of two or more appropriate reagents, one or more of which contain the requisite nitrogen.
  • a dyestufi is applied to the materials either in admixture with one or more of the reagents or separately at a later stage, e. g. after the formation of the complex nitrogenous organic compound on the material.
  • Incorporation of the complex nitrogen-containing organic compounds in natural or regenerated cellulose by the above method generally confers upon the latter an affinity, or increases any existing affinity, for the basic and acid colors, and decreases or suppresses entirely their affinity for the direct cotton colors, Viewed from the point of view of the basic and acid colors, the invention may therefore be considered as a mordanting of the materials, while from the point of view of the direct cotton colors, it may be considered as a reserving process. Similar observations apply, mutatis mutandis, to the cellulose derivative materials.
  • the reagents capable of yielding the complex nitrogenous compound may be applied uniformly over the entire material as, for example, by applying them by a bath treatment or by mechanicalimpregnation methods, for example by means of a padding mangle, but the most important application of the new process consists in modifying the dyeing affinities of the materials under treatment locally so as to produce pattern effects.
  • fabrics or other materials may be produced having the property of producing cross-dyed effects directly. For example immersion of such materials in a single bath containing, for example, either an acid or a direct cotton dye produces a fabric having a coloration only locally on the material, either the treated portion or the untreated portion of the material remaining uncolored according to the character of the dyestuff applied.
  • the coloring matter may also be applied locally, so as to fall at least in part on parts of the material to which the reagents have been applied.
  • a wide range of pattern effects may thus be produced.
  • a fabric printed with the reagents in an fall-over pattern e. g. of small spots or the like, may be over-printed in a large floral or geometric pattern with a dyestuff having affinity for either the unprinted material or for the complex nitrogenous compound.
  • the invention particularly contemplates the incorporation in the materials of synthetic resins containing nitrogen.
  • synthetic resins may, for example, be produced by the condensation of aldehydic, or ketonic bodies, for example formaldehyde, acetaldehyde, benzaldehyde, acetone or the like, with aliphatic or aromatic amines or amides, for example urea, thiourea, guanidine and their derivatives, dicyandiamide, aniline, methyl aniline, diphenylamine, benzyl aniline, ,B-naphthylamine, para-toluenesulphonamide or other aromatic sulphonamides or N-alkyl or other derivatives thereof.
  • aldehydic, or ketonic bodies for example formaldehyde, acetaldehyde, benzaldehyde, acetone or the like
  • aliphatic or aromatic amines or amides for example urea, thiourea, guanidine and their derivatives
  • dicyandiamide aniline,
  • ther group of materials available is the condensation products of gelatine, casein or other albumenoid compounds with formaldehyde for example.
  • the invention is not, however, confined to condensation products of aldehydic or ketonic bodies with nitrogen-containing organic compounds, since any other nitrogen-containing resinous or highly complex organic compound is suitable.
  • condensation to produce the above mentioned resinous materials is most advantageously carried out in the presence of catalysts, which may be alkaline, acid or neutral.
  • the nitrogenous product produced by interaction of the reagents on the material shall be substantially insoluble in water or in aqueous reagents which are customarily applied to the textile materials as, for example, in dyeing or scouring operations.
  • the reagents necessary may be applied together to the materials or may be applied separately or in any suitable combination.
  • the fabric may be first impregnated with a catalyst and the mixture of two bodies for condensation subsequently applied, or alternatively the mixture of the two bodies to undergo condensation may be first applied and the catalyst subsequently applied.
  • One of the bodies to be condensed may be applied with the catalyst and the other body applied separately. This last alternative is specially useful where one of the reagents is to be applied in the form of vapor as may bethe case, for example, with formaldehyde.
  • Reaction between the resin-forming reagents is conveniently effected by heating the materials impregnated with the reagents. Steaming may be utilized if desired.
  • a cellulose or cellulose derivative fiber or fabric is impregnated locally or printed or treated in an analogous manner with a mixture having the following composition, the parts being by weight:
  • the material thus treated can then be dyed by any suitable process with a direct dyestufi which reserves animal fibers.
  • the dyebath may contain any of the usual assistants, for example a sulphonated higher fatty alcohol or other wetting agent or sodium sulphate.
  • the untreated parts of the material take the color normally while the treated parts act as a reserve against the color so that a white pattern on a colored background is obtained.
  • the material may be dyed with an acid color by choosing an acid dyestuif which has good reserve properties for cotton fibers.
  • the treated parts only are dyed so that a colored pattern on a white background is obtained.
  • basic dyestuffs may be employed to color the material.
  • natural or regenerated cellulose materials and also cellulose derivative materials having a certain affinity for these colors the untreated parts also take some of the color while the treated parts have their afiinity for the color enhanced so that deep designs on a paler background are obtained.
  • a plurality of acid, basic and cotton colors may be applied to the materials in succession or, where they are compatible, in a single bath, so as to obtain differential colorations on the design and background.
  • Example 2 A cellulose or cellulose derivative fiber or fabric is impregnated locally or printed or treated in an analogous manner with the following mixture:
  • any other suitable nitrogen-containing bodies may be substituted for the agents therein mentioned.
  • penetrating agents, plasticizers or softeners such as glycerine, oils, sulphonated fatty oils or the like may be added to the mixture.
  • Latex or other suitable agents having the effect of increasing the fixation of the material may likewise be pres- 1' ent.
  • the mixture for producing the condensation product on the material may contain the dyestuif.
  • Example 3 The cellulose or cellulose derivative fiber or fabric is impregnated locally or printed or treated in an analogous manner with the following mixture:
  • Example 4 A fabric of natural silk or regenerated artificial silk is printed with the following mixture:-
  • the fabric After drying the fabric is stoved at 110 C. for 1-2 hours and then washed with water.
  • effects due to the weaving or other arrangement of these animal fibers in the goods may be superimposed upon the effects described above.
  • Paramine Orange 415 Benzo Fast Orange W8 326 Direct Blue 23 406 Direct Sky Blue 520 Direct Blue RWS 512 Direct Pink 126 Direct Black BH 401
  • nitrogenous resin as employed hereinafter in the claims is to be construed as including within its scope condensation products of gelatine, casein or other albumenoid compounds with formaldehyde or other aldehydes.
  • Process of coloring textile materials which comprises impregnating at least part of the material with reagents capable of reacting to yield a nitrogenous resin and then effecting formation of compound from said reagents on the material, and dyeing the materials by applying a dyestufl to at least a portion of the impregnated part at the earliest at the time of applying one of said reagents.
  • Process of coloring cellulosic textile materials which comprises impregnating at least part of the material with reagents capable of reacting to yield a nitrogenous resin and effecting formation of said resin from said reagents on the material, and dyeing the materials by applying a dyestuff to at least a portion of the impregnated part at the earliest at the time of applying one of said reagents.
  • Process of coloring textile fabric containing cellulose filaments which comprises locally impregnating the fabric with reagents capable of reacting to yield a nitrogenous resin, effecting formation of said nitrogenous resin on the materials, and thereafter dyeing the material with a dyestufl having afilnity for animal fibers.
  • Process of coloring textile fabric containing cellulose filaments which comprises locally impregnating the material with a mixture containing formaldehyde and urea. heating the fabric to effect resin formation on the material by interaction of the formaldehyde and urea, and dyeing the material with a dyestuif having affinity for animal fibers.
  • Process of coloring textile fabric containing cellulose filaments which comprises locally impregnating the fabric with a mixture of reagents capable of reacting to yield a nitrogenous resin. effecting formation of said nitrogenous resin on the material, and thereafter dyeing the material with a dyestufl which has ailinity for cellulose materials but which resists animal fibers.
  • Process of coloring textile fabric containing cellulose filaments which comprises locally impregnating the fabric with a mixture of formaldehyde and an aromatic amine, effecting formation of a nitrogenous resin on the material by interaction of the formaldehyde and aromatic amine, and thereafter dyeing the material with a dyestuff having amnity for animal fibers.
  • Process of coloring textile fabric which comprises locally impregnating the fabric with a mixture containing reagents capable of reacting to form a nitrogenous resin and also containing! a dyestuff having afllnity for animal fibers, and thereafter effecting reaction between the said reagents to form a nitrogenous resin on the material.
  • Process of coloring textile fabric containing cellulose filaments which comprises locally impregnating the fabric with a mixture containing reagents capable of reacting to form a nitrogenous resin and also containing a dyestuif having aflinity for animal fibers, and thereafter effecting reaction between the said reagents to form a nitrogeneous resin on the material.
  • Process of coloring textile fabric comprising cellulose filaments,which comprises locally impregnating the fabric with a mixture containing a dyestuff selected from the group consisting of acid and basic dyestuffs, formaldehyde, and urea, and thereafter heating the fabric to produce a resin on the material by interaction of the urea and formaldehyde.
  • a dyestuff selected from the group consisting of acid and basic dyestuffs, formaldehyde, and urea
  • Process of coloring textile fabric containing cellulose filaments which comprises locally impregnating the fabric with analbuminoid and formaldehyde and causing said albuminoid and formaldehyde to interact thereon, and thereafter dyeing the material with a dyestufl having affinity for animal fibers.

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

Description

Patented July 1938 TREATMENT OF CELLULOSIC MATERIALS Georges Rlvat, Lyons, France, asslgnor to Henry Dreyfus, London, England No Drawing, Application November 5, 1935, Serial No. 48,283. In France November 13, 1934 11 Claims.
The present invention relates to improvements in the coloration of textile materials, especially cellulosic materials.
As is well known, materials consisting of natural or regenerated cellulose have an afiinity for the cotton colors and little or no aflinity for the acid colors. Basic colors are usually dyed or printed on such materials with the aid of a tannin mordant. In a similar way, cellulose acetate artificial silk has an affinity for the basic colors and little or no afiinity for the acid and direct cotton colors. The present invention is concerned with treating materials made of or containing natural or regenerated cellulose or cellulose derivatives for the purpose of modifying the existing dyeing affinities of these materials and with fixing dyestuffs on the materials. Cellulosic materials may be, for example, natural cellulose fibers such as cotton, linen, jute or ramie, or regenerated cellulose as, for example, viscose, cu-= prammonium and nitrocellulose artificial silks, or cellulose derivatives, for example cellulose acetate, cellulose formate, cellulose propionate or other esters of cellulose, or cellulose eth-ers, for example methyl, ethyl or benzyl cellulose, or mixed cellulose derivatives, for example mixed ethers. mixed esters or mixed ether-esters. Again animal fibers, e. g. natural silk, may be colored by the new process.
Broadly the invention comprises incorporating in the materials a complex nitrogen-containing organic compound, preferably of resin character, by interaction, on the materials, of two or more appropriate reagents, one or more of which contain the requisite nitrogen. A dyestufi is applied to the materials either in admixture with one or more of the reagents or separately at a later stage, e. g. after the formation of the complex nitrogenous organic compound on the material.
Incorporation of the complex nitrogen-containing organic compounds in natural or regenerated cellulose by the above method generally confers upon the latter an affinity, or increases any existing affinity, for the basic and acid colors, and decreases or suppresses entirely their affinity for the direct cotton colors, Viewed from the point of view of the basic and acid colors, the invention may therefore be considered as a mordanting of the materials, while from the point of view of the direct cotton colors, it may be considered as a reserving process. Similar observations apply, mutatis mutandis, to the cellulose derivative materials.
The reagents capable of yielding the complex nitrogenous compound may be applied uniformly over the entire material as, for example, by applying them by a bath treatment or by mechanicalimpregnation methods, for example by means of a padding mangle, but the most important application of the new process consists in modifying the dyeing affinities of the materials under treatment locally so as to produce pattern effects. By suchlocal application, fabrics or other materials may be produced having the property of producing cross-dyed effects directly. For example immersion of such materials in a single bath containing, for example, either an acid or a direct cotton dye produces a fabric having a coloration only locally on the material, either the treated portion or the untreated portion of the material remaining uncolored according to the character of the dyestuff applied.
Again by applying a dyestuff in admixture with the resin-forming reagents valuable fast colorations, uniform or local, may be produced, for example with dyestuffs having normally no afiinity for the material.
If desired the coloring matter may also be applied locally, so as to fall at least in part on parts of the material to which the reagents have been applied. A wide range of pattern effects may thus be produced. For example a fabric printed with the reagents in an fall-over pattern, e. g. of small spots or the like, may be over-printed in a large floral or geometric pattern with a dyestuff having affinity for either the unprinted material or for the complex nitrogenous compound.
As previously indicated, the invention particularly contemplates the incorporation in the materials of synthetic resins containing nitrogen. The
synthetic resins may, for example, be produced by the condensation of aldehydic, or ketonic bodies, for example formaldehyde, acetaldehyde, benzaldehyde, acetone or the like, with aliphatic or aromatic amines or amides, for example urea, thiourea, guanidine and their derivatives, dicyandiamide, aniline, methyl aniline, diphenylamine, benzyl aniline, ,B-naphthylamine, para-toluenesulphonamide or other aromatic sulphonamides or N-alkyl or other derivatives thereof. ther group of materials available is the condensation products of gelatine, casein or other albumenoid compounds with formaldehyde for example. The invention is not, however, confined to condensation products of aldehydic or ketonic bodies with nitrogen-containing organic compounds, since any other nitrogen-containing resinous or highly complex organic compound is suitable. For example, the condensation prodnet of phenol with methylene diphenyldiamine I A furmay be employed. In most cases. condensation to produce the above mentioned resinous materials is most advantageously carried out in the presence of catalysts, which may be alkaline, acid or neutral.
It is desirable that the nitrogenous product produced by interaction of the reagents on the material shall be substantially insoluble in water or in aqueous reagents which are customarily applied to the textile materials as, for example, in dyeing or scouring operations.
The reagents necessary may be applied together to the materials or may be applied separately or in any suitable combination. For example the fabric may be first impregnated with a catalyst and the mixture of two bodies for condensation subsequently applied, or alternatively the mixture of the two bodies to undergo condensation may be first applied and the catalyst subsequently applied. One of the bodies to be condensed may be applied with the catalyst and the other body applied separately. This last alternative is specially useful where one of the reagents is to be applied in the form of vapor as may bethe case, for example, with formaldehyde.
Reaction between the resin-forming reagents is conveniently effected by heating the materials impregnated with the reagents. Steaming may be utilized if desired.
The following examples illustrate the invention.
- Example 1 A cellulose or cellulose derivative fiber or fabric is impregnated locally or printed or treated in an analogous manner with a mixture having the following composition, the parts being by weight:
Grams Thiourea 100-150 Water 250-300 40% formaldehyde 550 Formic acid 50 The material is then dried at 80 during an hour or two until the condensation has given rise to a product insoluble in boiling water.
The material thus treated can then be dyed by any suitable process with a direct dyestufi which reserves animal fibers. The dyebath may contain any of the usual assistants, for example a sulphonated higher fatty alcohol or other wetting agent or sodium sulphate. The untreated parts of the material take the color normally while the treated parts act as a reserve against the color so that a white pattern on a colored background is obtained.
In a similar way the material may be dyed with an acid color by choosing an acid dyestuif which has good reserve properties for cotton fibers. The treated parts only are dyed so that a colored pattern on a white background is obtained.
Again, basic dyestuffs may be employed to color the material. In this case, natural or regenerated cellulose materials and also cellulose derivative materials having a certain affinity for these colors, the untreated parts also take some of the color while the treated parts have their afiinity for the color enhanced so that deep designs on a paler background are obtained.
A plurality of acid, basic and cotton colors may be applied to the materials in succession or, where they are compatible, in a single bath, so as to obtain differential colorations on the design and background.
Example 2 A cellulose or cellulose derivative fiber or fabric is impregnated locally or printed or treated in an analogous manner with the following mixture:
Grams Dicyandiamide 100-200 Ammonium sulphocyanide 40% formaldehyde 780 The sequence of operations is carried out as indicated in Example 1.
In the above examples, any other suitable nitrogen-containing bodies may be substituted for the agents therein mentioned. In addition, penetrating agents, plasticizers or softeners such as glycerine, oils, sulphonated fatty oils or the like may be added to the mixture. Latex or other suitable agents having the effect of increasing the fixation of the material may likewise be pres- 1' ent. If desired, the mixture for producing the condensation product on the material may contain the dyestuif.
Example 3 The cellulose or cellulose derivative fiber or fabric is impregnated locally or printed or treated in an analogous manner with the following mixture:
Grams Urea M 100-200 Dicyandiamide 60 Glycerine 60 Alkaline or alkaline earth sulphocyanide 20 40% formaldehyde 660 The sequence of operations is effected as indicated in Example 1.
Example 4 A fabric of natural silk or regenerated artificial silk is printed with the following mixture:-
Urea or thiourea "grams" 100 40% formaldehyde ccs 300-500 Formic acid do 50 Dyestuff "grams" 10- 50 Water and thickener sufficient to make 1000 grams in all.
After drying the fabric is stoved at 110 C. for 1-2 hours and then washed with water. By mixing in the fabric or other material natural silk, wool or other animal fibers, effects due to the weaving or other arrangement of these animal fibers in the goods may be superimposed upon the effects described above.
The following are examples of coloring mat ters which may be used according to the inven- Basic coloring matters Color index No. Rhoduline Yellow 815 Acridine Orange 788 Chrysoidine 20 Methylene Blue 922 Toluidine Blue. 925 Rhoduline Blue 658 Victoria Blue- 729 Malachite Green 657 Rhodamine 6G 752 Rhodamine B 749 Methylene Violet 842 Direct colors reserved by the complex nitrogenous compounds Diphenyl Fast Yellow 632 IBenzo Fast Scarlet 838---; 326
Paramine Orange 415 Benzo Fast Orange W8 326 Direct Blue 23 406 Direct Sky Blue 520 Direct Blue RWS 512 Direct Pink 126 Direct Black BH 401 The term nitrogenous resin" as employed hereinafter in the claims is to be construed as including within its scope condensation products of gelatine, casein or other albumenoid compounds with formaldehyde or other aldehydes.
What I claim and desire to secure by Letters Patent is:--
1. Process of coloring textile materials, which comprises impregnating at least part of the material with reagents capable of reacting to yield a nitrogenous resin and then effecting formation of compound from said reagents on the material, and dyeing the materials by applying a dyestufl to at least a portion of the impregnated part at the earliest at the time of applying one of said reagents.
2. Process of coloring cellulosic textile materials, which comprises impregnating at least part of the material with reagents capable of reacting to yield a nitrogenous resin and effecting formation of said resin from said reagents on the material, and dyeing the materials by applying a dyestuff to at least a portion of the impregnated part at the earliest at the time of applying one of said reagents.
3. Process of coloring textile fabric containing cellulose filaments, which comprises locally impregnating the fabric with reagents capable of reacting to yield a nitrogenous resin, effecting formation of said nitrogenous resin on the materials, and thereafter dyeing the material with a dyestufl having afilnity for animal fibers.
reacting with formaldehyde to yield a nitrogenous resin, effecting formation of said nitrogenous resin on the material, and thereafter dyeing the material with a dyestuif having affinity for animal fibers.
5. Process of coloring textile fabric containing cellulose filaments, which comprises locally impregnating the material with a mixture containing formaldehyde and urea. heating the fabric to effect resin formation on the material by interaction of the formaldehyde and urea, and dyeing the material with a dyestuif having affinity for animal fibers. v
6. Process of coloring textile fabric containing cellulose filaments, which comprises locally impregnating the fabric with a mixture of reagents capable of reacting to yield a nitrogenous resin. effecting formation of said nitrogenous resin on the material, and thereafter dyeing the material with a dyestufl which has ailinity for cellulose materials but which resists animal fibers.
7. Process of coloring textile fabric containing cellulose filaments, which comprises locally impregnating the fabric with a mixture of formaldehyde and an aromatic amine, effecting formation of a nitrogenous resin on the material by interaction of the formaldehyde and aromatic amine, and thereafter dyeing the material with a dyestuff having amnity for animal fibers.
8. Process of coloring textile fabric, which comprises locally impregnating the fabric with a mixture containing reagents capable of reacting to form a nitrogenous resin and also containing! a dyestuff having afllnity for animal fibers, and thereafter effecting reaction between the said reagents to form a nitrogenous resin on the material.
9. Process of coloring textile fabric containing cellulose filaments, which comprises locally impregnating the fabric with a mixture containing reagents capable of reacting to form a nitrogenous resin and also containing a dyestuif having aflinity for animal fibers, and thereafter effecting reaction between the said reagents to form a nitrogeneous resin on the material.
10. Process of coloring textile fabric comprising cellulose filaments,which comprises locally impregnating the fabric with a mixture containing a dyestuff selected from the group consisting of acid and basic dyestuffs, formaldehyde, and urea, and thereafter heating the fabric to produce a resin on the material by interaction of the urea and formaldehyde.
11. Process of coloring textile fabric containing cellulose filaments, which comprises locally impregnating the fabric with analbuminoid and formaldehyde and causing said albuminoid and formaldehyde to interact thereon, and thereafter dyeing the material with a dyestufl having affinity for animal fibers.
GEORGES RIVAT.
GERTIFI GATE OF CORRECTION Patent No. 2,12%152; July 5, 1938.
' GEORGES RIVATO It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 5, first column, line 57, claim 1, before compound insert the word said; and that the said Letters Patent should be read with this correction therein that the same may conform to the record of the case in the Patent Office.
Signed and sealed. thie 9th day of August, A. D, 1958.0
Leslie Frazer (Seal) Acting Commissioner of Patents.
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US2417312A (en) * 1943-07-22 1947-03-11 Courtaulds Ltd Improving the dyeing properties of cellulosic textiles by treatment with formaldehyde and a guanidine salt of an alpha-beta unsaturated carboxylic acid
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US2424284A (en) * 1943-02-22 1947-07-22 British Celanese Fixation of finely divided substances
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US3076987A (en) * 1959-01-19 1963-02-12 Leather Ind Res I Process for the stiffening of parts of footwear
US3089784A (en) * 1960-03-24 1963-05-14 Diamond Alkali Co Polyester coating system
US3127363A (en) * 1955-08-05 1964-03-31 Process for the manufacture of elasto-
US3159500A (en) * 1957-06-05 1964-12-01 Glidden Co Method of converting a polyester coating
US3218119A (en) * 1962-02-02 1965-11-16 American Cyanamid Co Method of applying cyclic urea resins to cellulosic textile materials
US3227510A (en) * 1958-03-04 1966-01-04 Tee Pak Inc Dyeing substrates ionically binding in localized areas catalysts for the predyeing olefin polymerization thereon
US3284262A (en) * 1960-03-24 1966-11-08 Diamond Alkali Co Process of applying a polyester coating to a reinforced, coated substrate
US3445177A (en) * 1963-06-20 1969-05-20 Deering Milliken Res Corp Discharge printing a direct-dye dyed haloalkanol crosslinked cellulose fabric and creaseproofing with an aminoplast
US3537808A (en) * 1961-02-17 1970-11-03 Rohm & Haas Method of depositing polymers on fibrous products
US3617190A (en) * 1965-11-16 1971-11-02 Stevens & Co Inc J P Methylolated sulfonamides and crosslinking of polymers therewith
US3935341A (en) * 1969-12-23 1976-01-27 Kanamark International Limited Method for rendering wood resistant to fire

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US2416988A (en) * 1935-09-12 1947-03-04 Tootal Broadhurst Lee Co Ltd Delustring and weighting textile materials
US2453752A (en) * 1940-11-02 1948-11-16 Stein Hall & Co Inc Emulsion adapted for coating textiles
US2431315A (en) * 1941-03-11 1947-11-25 Chemical Developments Corp Process of forming plastic coating compositions on surfaces
US2418696A (en) * 1942-03-09 1947-04-08 Courtaulds Ltd Modifying the dyeing properties of cellulose or cellulose derivative textile materials
US2435591A (en) * 1943-01-06 1948-02-10 Chem Ind Basel Tendering properties of textiles dyed with yellow to orange vat dyestuffs by treatment with certain nitrogenous resins
US2424284A (en) * 1943-02-22 1947-07-22 British Celanese Fixation of finely divided substances
US2415320A (en) * 1943-03-10 1947-02-04 Courtaulds Ltd Differential drying of resin-impregnated fabric to obtain differential dyeing effects
US2417312A (en) * 1943-07-22 1947-03-11 Courtaulds Ltd Improving the dyeing properties of cellulosic textiles by treatment with formaldehyde and a guanidine salt of an alpha-beta unsaturated carboxylic acid
US2440330A (en) * 1943-08-26 1948-04-27 Celanese Corp Improving the fastness of dyed organic derivative of cellulose textiles by impregnation with cyanamide
US2540048A (en) * 1943-11-16 1951-01-30 Interchem Corp Dyed textiles and methods and composition for producing same
US2429073A (en) * 1944-08-05 1947-10-14 Hat Corp America Dyed composite felt and method of making same
US2474909A (en) * 1945-05-08 1949-07-05 Celanese Corp Fixation of pigments on textile materials
US2485250A (en) * 1946-04-29 1949-10-18 Wolsey Ltd Treatment of wool and the like
US2576027A (en) * 1946-07-16 1951-11-20 John E Means Surgical cast
US2515340A (en) * 1947-04-01 1950-07-18 Gardner Board & Carton Co Coated paperboard and method of makign same
US2591904A (en) * 1947-10-29 1952-04-08 John C Zola Coating compositions and preparation thereof
US2599943A (en) * 1948-12-06 1952-06-10 Fed Cartridge Corp Process of making disintegratable top shot wads
US2967117A (en) * 1949-01-25 1961-01-03 Bayer Ag Process for coating a substrate with a mixture of a polyhydroxy polyester and a polyisocyanate
US2681867A (en) * 1949-12-09 1954-06-22 Calico Printers Ass Ltd Process for the ornamentation of textile fabrics
US2632714A (en) * 1950-04-04 1953-03-24 Robert Gair Co Inc Process for coating paper web
US2766142A (en) * 1952-05-03 1956-10-09 American Cyanamid Co Coated glass strands and process of preparing the same
US2736749A (en) * 1952-06-10 1956-02-28 Arnold Hoffman & Co Inc Dye-fixing agents
US2849333A (en) * 1954-01-08 1958-08-26 Owens Corning Fiberglass Corp Method of dyeing tightly wound glass fibers sized with a water swellable material
US3127363A (en) * 1955-08-05 1964-03-31 Process for the manufacture of elasto-
US2955050A (en) * 1956-07-17 1960-10-04 Geigy Ag J R Water fastness of metal lakes of azo dyestuffs containing sulphonic acid groups
US2932583A (en) * 1956-10-12 1960-04-12 Ciro L Grana Method of impregnating a microporous article
US2958880A (en) * 1956-12-10 1960-11-08 Beckwith Arden Inc Process of forming box toes from an aminoplast compound
US3159500A (en) * 1957-06-05 1964-12-01 Glidden Co Method of converting a polyester coating
US2967789A (en) * 1957-11-26 1961-01-10 Borden Co Process of coating granules with phenol-aldehyde resin
US3053690A (en) * 1958-01-21 1962-09-11 Spies Hecker & Company Process for hardening furan resins
US2935753A (en) * 1958-02-06 1960-05-10 Walter H Heaton Process of forming and stiffening shoe quarters
US3227510A (en) * 1958-03-04 1966-01-04 Tee Pak Inc Dyeing substrates ionically binding in localized areas catalysts for the predyeing olefin polymerization thereon
US2978354A (en) * 1958-03-18 1961-04-04 David K Lesser Method of applying a coating
US3076987A (en) * 1959-01-19 1963-02-12 Leather Ind Res I Process for the stiffening of parts of footwear
US3089784A (en) * 1960-03-24 1963-05-14 Diamond Alkali Co Polyester coating system
US3284262A (en) * 1960-03-24 1966-11-08 Diamond Alkali Co Process of applying a polyester coating to a reinforced, coated substrate
US3537808A (en) * 1961-02-17 1970-11-03 Rohm & Haas Method of depositing polymers on fibrous products
US3218119A (en) * 1962-02-02 1965-11-16 American Cyanamid Co Method of applying cyclic urea resins to cellulosic textile materials
US3445177A (en) * 1963-06-20 1969-05-20 Deering Milliken Res Corp Discharge printing a direct-dye dyed haloalkanol crosslinked cellulose fabric and creaseproofing with an aminoplast
US3617190A (en) * 1965-11-16 1971-11-02 Stevens & Co Inc J P Methylolated sulfonamides and crosslinking of polymers therewith
US3935341A (en) * 1969-12-23 1976-01-27 Kanamark International Limited Method for rendering wood resistant to fire

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