US3144299A - Wrinkle resistance finish for cellulosic textiles - Google Patents
Wrinkle resistance finish for cellulosic textiles Download PDFInfo
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- US3144299A US3144299A US115268A US11526861A US3144299A US 3144299 A US3144299 A US 3144299A US 115268 A US115268 A US 115268A US 11526861 A US11526861 A US 11526861A US 3144299 A US3144299 A US 3144299A
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- Prior art keywords
- carbamate
- formaldehyde
- fabric
- solution
- weight
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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
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/12—Aldehydes; Ketones
- D06M13/127—Mono-aldehydes, e.g. formaldehyde; Monoketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with urethanes or thiourethanes
-
- 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 textile fabrics whereby the fabric is given improved resistance to wrinkling or mussing, improved shape-holding properties, and the ability to dry smooth after laundering.
- the cellulosic fabric so finished may be laundered by procedures usually used with textiles of the same type, which procedure can include the use of hypochlorite bleaching agents and acid sours, without sulfering additional damage because of the finish or extensive loss of the improved properties imparted by the finish.
- the mechanism by which the agents mentioned produce the wrinkle resistance and smooth-drying properties in cellulosic textiles is believed to be a crosslinle'ng of the linear cellulose molecules in the fibrous material.
- the effect can be accomplished by etherification of cellulose with-the methylol compound'using an acidic or alkaline catalyst.
- the finishing agent must be polyfunctional, that is, contain two or more reactive methylol groups.
- the agents used therefore, are di-, tri-, or tetra-methylol compounds formed by the reaction of an organic nitrogen compound, containing two or more nitrogen containing groups with formaldehyde-in a ratio'to give at least one molar equivalent of formaldehyde for each nitrogenous group.
- the finishing agent dimethylol ethyleneurea is formed from the reaction of ethyleneurea with two molar-equivalents of formaldehyde.
- the agent trimethylol melamine is formed from the reaction of melamine with three molar equivalents of formaldehyde.
- this agent has been described by some investigators as actually belonging toanother class of agents and producing a nitrogen free finish on the fabric. On the other hand, other investigators have reported that this agent gives a finished fabric very susceptible todamage by hypochlorite bleaching agents, a property normally associated with the presence of nitrogen.
- textiles finished with the agents prepared from monocarbamates are less susceptible to damage from hypochlorite bleaching agents and have properties more durable to acidic souring than those tiles so treated may be laundered by procedures normally used with untreated textiles of similar type, which procedure may includethe use of hypochlorite bleaching agents and the use of acid sours in the rinse, without sufiering any deleterious effects because of the treatment or drastic loss of the properties imparted by the treatment.
- the object of this invention may'be accomplished by applying to the textile a product formed from the reaction of a monocarbamate, such as methyl carbamate, ethyl carbamate, propyl carbamate, or butyl carbamate, and two moles of formaldehyde.
- a monocarbamate such as methyl carbamate, ethyl carbamate, propyl carbamate, or butyl carbamate
- formaldehyde two moles of formaldehyde.
- the product is formed by allowing the carbamate and formaldehyde to react in a slightly alkaline aqueous solution. After the reaction is completed, the solution is diluted to the desired concentr'ation for application to the textile and an acidic catalyst is added to the solution.
- the concentration of the product to be used will vary, usually between 5 and 20% of the solution, depending on the type of textile to be finished.
- the acidic catalyst can be an inorganic or amine salt of a strong mineral acidf
- Particularly suitable as catalysts are zinc nitrate and magnesium chloride used as the readily obtainable hydrates in a quantity 0.5 to 6.0% of the weight of the carbamate-formaldehyde solution containing the desired concentration of the carbamate-formaldehyde condensate.
- the solution can be applied to textiles by usual finishing procedures, such as soaking the textile in the solution and padding or centrifuging so that the textile retains a weight of solution equal to 50 to of its dry weight.
- Thewet textile is dried at relatively low temperature, as 60 to C., and then heated briefly at a higher tem-' may contain other auxiliary agents commonly used in-textile finishing For instance, wetting agents may be in cluded in the bath to provide more rapid impregnation of the applied solution. Softening agents may also be 3 included to modify the hand and feet of the finished textile.
- Example 1 (MgCl -6H O) The solution was padded onto a simple of 80x 80 cotton print cloth to give a 7080% wet pickup. The wet fabric was dried at original dimensions for seven minutes at 60 C., and then cured at original dimensions for 3 minutes at 160 C. The curing step was followed by an afterwash in Warm water with a nonionic detergent and then tumble dried. The finished fabric possessed a crease recovery angle of 262 (warp-i-filling) while an untreated, after-washed sample had a crease recovery angle of only 187 (warp-l-filling).
- Example 2 A sample was treated as described in Example 1, except that the solution contained 0.75% hydrated zinc nitrate (Zn(NO -6H O) instead of magnesium chloride as catalyst.
- the finished fabric had a crease recovery angle of 262 (warp-l-filling).
- Example 3 A sample was treated as described in Example 1, except that 1.5% of 2-amino-2-methyl-l-propanol hydr0 chloride was used as catalyst instead of magnesium chloride.
- the finished fabric had a crease recovery angle of 268 (warp-f-filling).
- Example 4 A sample was treated as described in Example 1 except that 1.5% of emulsified polyethylene was added to the treating bath.
- the finished fabric had a crease recovery angle of 294 (warp-l-filling) and a warp tearing strength of 627 g. by the Elmendorf method.
- a similar sample prepared as in Example 1 had a crease recovery angle of 262 (warp-i-filling) and a Warp tearing strength of 480 g.
- Example 2 For comparison purposes to demonstrate the durability of the finish to an acid sour, a sample treated as described in Example 2 and a sample treated with water solution of 8% by weight of dimethylol ethyleneurea and 0.75% by weight of hydrated zinc nitrate were immersed in a solution buffered to pH 2.2 for 30 minutes at 40 C.
- the dimethylol ethyl carbamate treated sample retained 94% of its original nitrogen content and 94% of its original crease recovery angle after its treatment.
- the dimethylol ethyleneurea treated sample retained only 22% of its original nitrogen content and only 62% of its original crease recovery angle.
- Example 7 A 15% water solution of a butyl carbamate-torrnaldehyde product was prepared in the following manner: butyl carbamate was dissolved in 7.7 times its weight of water and suflicient 36% formaldehyde solution, which was previously adjusted to pH 8 with sodium hydroxide, was added to afford a ratio of formaldehyde to butyl carbamate of 2:1. This solution was allowed to stand overnight at room temperature. After this time hydrated magnesium chloride was added to make 4% of the solution and the solution used to treat fabric as in Example 1. The finished fabric had a crease recovery angle of 254 (warp-t-filling) and retained 91% of its original strength in the scorch test.
- a process for treating a cellulosic textile fabric comprising: wetting the fabric with an aqueous solution containing about from 5 to 20% by weight of a water soluble product of formaldehyde and a carbamate compound selected from the group consisting of methyl carbamate, ethyl carbamate, propyl carbamate, and butyl carbarnatc, said product having been produced by the reaction, in aqueous alkaline solution, of the formaldehyde and the carbamate compound in the mole ratio of 2 to 1, and from 0.5 to 6.0% by weight based on the weight of the carbamate compound-formaldehyde solution of an acidic catalyst, and drying and curing the treated fabric at a temperature of from to C.
- a process for treating a cellulosic textile fabric comprising: wetting the fabric with an aqueous solution containing about from 5 to 20% by weight of a water soluble product of formaldehyde and a carbamate compound selected from the group consisting of methyl carbarnate, ethyl carbamate, propyl carbamate, and butyl carbamate, said product having been produced by the reaction, in aqueous alkaline solution, of the formaldehyde and the carbamate compound in the mole ratio of 2 to 1, and from 0.5 to 6.0% by Weight based on the weight of the carbamate compound-formaldehyde solution of an acidic catalyst selected from the group consisting of zinc nitrate hexahydrate, magnesium chloride hexahydrate, and 2-amino-2-methyl-l-propanol hydro chloride, drying the treated fabric at a temperature of about from to C. for about 7 minutes, and curing the dried, treated fabric at a temperature of from to C. for about from 3
Description
United States Patent of America as represented by the Secretary of Agriculture No Drawing. Filed Jarred, 1961, Ser; No.- 115,268 8'Claims. (Cl. 8-1163) (Granted under Title 35, US. Code (1952), sec. 266)- A non-exclusive, irrevocable, royalty-free license in the invention herein described, throughout the World for all purposes of the United States Government, with the power to grant sublicenses for such purposes, is hereby granted to the Government of the United States of America.
This invention relates to the finishing of cellulosic textile fabrics whereby the fabric is given improved resistance to wrinkling or mussing, improved shape-holding properties, and the ability to dry smooth after laundering. Moreover, the cellulosic fabric so finished may be laundered by procedures usually used with textiles of the same type, which procedure can include the use of hypochlorite bleaching agents and acid sours, without sulfering additional damage because of the finish or extensive loss of the improved properties imparted by the finish.
Because of their poor resiliency, cellulosic textiles fabrics, such as cotton and rayon,-tend to become wrinkled in use and acquire a mussed or unpleasant appearance. To overcome this objectionable property, it has been the practice to treat or finish cellulosic textiles with the methylol derivatives of organic nitrogen compounds,-
such as urea, ethyleneurea, guanidine, or melamine. These agents do produce a finished cellulosic textile that has improved resistance to wrinkling or mussing while in use, and in addition, give the textile, to a greater or lesser extend, the ability to dry smooth after laundering. Textiles finished with many of these agents, however, cannot be bleached with the usual hypochlorite bleaching agents during laundering without the danger of suffering severe strength loss or discoloration. In addition, the souring step common in many laundryprocedures will often partially remove the finish produced by these agents, and cause extensive loss of the imparted properties; Thesedisadvantages of presently used finishes are most pronounced with cotton textiles because of the more rigorous laundry procedures to which cotton textiles are submitted as compared with those which are employed with other cellulosic textiles.
The mechanism by which the agents mentioned produce the wrinkle resistance and smooth-drying properties in cellulosic textiles is believed to be a crosslinle'ng of the linear cellulose molecules in the fibrous material. The effect can be accomplished by etherification of cellulose with-the methylol compound'using an acidic or alkaline catalyst. To obtain the necessary crosslinking,.the finishing agent must be polyfunctional, that is, contain two or more reactive methylol groups. The agents used, therefore, are di-, tri-, or tetra-methylol compounds formed by the reaction of an organic nitrogen compound, containing two or more nitrogen containing groups with formaldehyde-in a ratio'to give at least one molar equivalent of formaldehyde for each nitrogenous group. For example, the finishing agent dimethylol ethyleneurea is formed from the reaction of ethyleneurea with two molar-equivalents of formaldehyde. Similarly, the agent trimethylol melamine is formed from the reaction of melamine with three molar equivalents of formaldehyde. Numerous investigators in this field have reported that similar agents derived from nitrogenous compounds containing a single nitrogenous group are ineffective in pro- 3,144,299 Patented Aug. 11, 1964' ducing the desired Wrinkle resistance and smooth-drying properties. The single known exception to'thisis the reaction product of formamide and formaldehyde. ,Accordingly, this agent has been described by some investigators as actually belonging toanother class of agents and producing a nitrogen free finish on the fabric. On the other hand, other investigators have reported that this agent gives a finished fabric very susceptible todamage by hypochlorite bleaching agents, a property normally associated with the presence of nitrogen.
The use ofdimethylol dicarbamates as wrinkle resistance finishing agents has been described. This type of agent, derived from compounds with two carbamate groups, has the disadvantages previously noted for the agents in present use. We have found, however, that agents can' be prepared from organic monocarbamates, containing a single nitrogenous group, and formaldehyde, and that these agents are effective in producing wrinkle resistance and smooth drying properties in cellulosic textiles. Furthermore, textiles finished with the agents prepared from monocarbamates are less susceptible to damage from hypochlorite bleaching agents and have properties more durable to acidic souring than those tiles so treated may be laundered by procedures normally used with untreated textiles of similar type, which procedure may includethe use of hypochlorite bleaching agents and the use of acid sours in the rinse, without sufiering any deleterious effects because of the treatment or drastic loss of the properties imparted by the treatment.
The object of this invention may'be accomplished by applying to the textile a product formed from the reaction of a monocarbamate, such as methyl carbamate, ethyl carbamate, propyl carbamate, or butyl carbamate, and two moles of formaldehyde. The product is formed by allowing the carbamate and formaldehyde to react in a slightly alkaline aqueous solution. After the reaction is completed, the solution is diluted to the desired concentr'ation for application to the textile and an acidic catalyst is added to the solution. The concentration of the product to be used will vary, usually between 5 and 20% of the solution, depending on the type of textile to be finished. The acidic catalyst can be an inorganic or amine salt of a strong mineral acidf Particularly suitable as catalysts are zinc nitrate and magnesium chloride used as the readily obtainable hydrates in a quantity 0.5 to 6.0% of the weight of the carbamate-formaldehyde solution containing the desired concentration of the carbamate-formaldehyde condensate.
The solution can be applied to textiles by usual finishing procedures, such as soaking the textile in the solution and padding or centrifuging so that the textile retains a weight of solution equal to 50 to of its dry weight.
Thewet textile is dried at relatively low temperature, as 60 to C., and then heated briefly at a higher tem-' may contain other auxiliary agents commonly used in-textile finishing For instance, wetting agents may be in cluded in the bath to provide more rapid impregnation of the applied solution. Softening agents may also be 3 included to modify the hand and feet of the finished textile.
The properties of textiles finished by the method of this invention are illustrated in the following examples. All parts and percentages described are by weight. The degree of wrinkle resistance obtained in the finished textile is shown by the crease recovery angle determined by 4 Example 5 Samples treated as described in Examples 1, 2, and 3 were subjected to launderings in an automatic home type washer using detergent and hypochlorite bleach to give 0.02% available chlorine and to 5 launderings as described in AATCC Test 14-53. The properties of the fabrics are tabulated below.
Original After 20 Home Launderings After 5 AATCC Washes Treatment Crease Elmen- Scorch Crease Elmen- Scorch Crease Elmen- Scorch Recovery dorf Tear Test, per- Recovery dorITear Test,pcr- Recovery dortTear 'Iest,pcr-
Angle, Strength, cent Angle, Strength, cent Angle Strength, cent W-i-F g. Warp Strength W+F Warp Strength W-l-F Warp Strength Retained Retained Retained Example 1 262 480 106 256 307 98 272 487 102 Example 2. 262 480 102 247 413 87 254 580 98 Example 3- 268 533 91 256 433 89 252 567 92 the American Society for Testing Materials Test D1424- Example 6 5 6T. The resistance of the textiles to hypochlorite bleach is shown by the strength retained in the American Association of Textile Chemists and Colorists Test 69-1952. The tearing strength of the textiles is shown by the tearing strengths obtained by the Elmendorf method, American Society for Testing Materials Test D142456T.
Example 1 (MgCl -6H O) The solution was padded onto a simple of 80x 80 cotton print cloth to give a 7080% wet pickup. The wet fabric was dried at original dimensions for seven minutes at 60 C., and then cured at original dimensions for 3 minutes at 160 C. The curing step was followed by an afterwash in Warm water with a nonionic detergent and then tumble dried. The finished fabric possessed a crease recovery angle of 262 (warp-i-filling) while an untreated, after-washed sample had a crease recovery angle of only 187 (warp-l-filling).
Example 2 A sample was treated as described in Example 1, except that the solution contained 0.75% hydrated zinc nitrate (Zn(NO -6H O) instead of magnesium chloride as catalyst. The finished fabric had a crease recovery angle of 262 (warp-l-filling).
Example 3 A sample was treated as described in Example 1, except that 1.5% of 2-amino-2-methyl-l-propanol hydr0 chloride was used as catalyst instead of magnesium chloride. The finished fabric had a crease recovery angle of 268 (warp-f-filling).
Example 4 A sample was treated as described in Example 1 except that 1.5% of emulsified polyethylene was added to the treating bath. The finished fabric had a crease recovery angle of 294 (warp-l-filling) and a warp tearing strength of 627 g. by the Elmendorf method. A similar sample prepared as in Example 1 had a crease recovery angle of 262 (warp-i-filling) and a Warp tearing strength of 480 g.
For comparison purposes to demonstrate the durability of the finish to an acid sour, a sample treated as described in Example 2 and a sample treated with water solution of 8% by weight of dimethylol ethyleneurea and 0.75% by weight of hydrated zinc nitrate were immersed in a solution buffered to pH 2.2 for 30 minutes at 40 C. The dimethylol ethyl carbamate treated sample retained 94% of its original nitrogen content and 94% of its original crease recovery angle after its treatment. The dimethylol ethyleneurea treated sample retained only 22% of its original nitrogen content and only 62% of its original crease recovery angle.
Example 7 A 15% water solution of a butyl carbamate-torrnaldehyde product was prepared in the following manner: butyl carbamate was dissolved in 7.7 times its weight of water and suflicient 36% formaldehyde solution, which was previously adjusted to pH 8 with sodium hydroxide, was added to afford a ratio of formaldehyde to butyl carbamate of 2:1. This solution was allowed to stand overnight at room temperature. After this time hydrated magnesium chloride was added to make 4% of the solution and the solution used to treat fabric as in Example 1. The finished fabric had a crease recovery angle of 254 (warp-t-filling) and retained 91% of its original strength in the scorch test.
We claim:
1. A process for treating a cellulosic textile fabric comprising: wetting the fabric with an aqueous solution containing about from 5 to 20% by weight of a water soluble product of formaldehyde and a carbamate compound selected from the group consisting of methyl carbamate, ethyl carbamate, propyl carbamate, and butyl carbarnatc, said product having been produced by the reaction, in aqueous alkaline solution, of the formaldehyde and the carbamate compound in the mole ratio of 2 to 1, and from 0.5 to 6.0% by weight based on the weight of the carbamate compound-formaldehyde solution of an acidic catalyst, and drying and curing the treated fabric at a temperature of from to C.
2. The process of claim 1 wherein the carbamate compound is ethyl carbamate.
3. The process of claim 1 wherein the carbamate compound is butyl carbamate.
4. The process of claim 1 wherein the acidic catalyst is an inorganic salt of a strong mineral acid.
5. The process of claim 1 wherein the acidic catalyst is the amine salt of a strong mineral acid.
6. A process for treating a cellulosic textile fabric comprising: wetting the fabric with an aqueous solution containing about from 5 to 20% by weight of a water soluble product of formaldehyde and a carbamate compound selected from the group consisting of methyl carbarnate, ethyl carbamate, propyl carbamate, and butyl carbamate, said product having been produced by the reaction, in aqueous alkaline solution, of the formaldehyde and the carbamate compound in the mole ratio of 2 to 1, and from 0.5 to 6.0% by Weight based on the weight of the carbamate compound-formaldehyde solution of an acidic catalyst selected from the group consisting of zinc nitrate hexahydrate, magnesium chloride hexahydrate, and 2-amino-2-methyl-l-propanol hydro chloride, drying the treated fabric at a temperature of about from to C. for about 7 minutes, and curing the dried, treated fabric at a temperature of from to C. for about from 3 to 5 minutes.
7. The process of claim 6 wherein the acidic catalyst is zinc nitrate hexahydrate.
8. The process of claim 6 wherein the acidic catalyst is magnesium chloride hexahydrate.
References Cited in the file of this patent UNITED STATES PATENTS OTHER REFERENCES Hackhs Chemical Dictionary, Third Edition,
Merck Index, Seventh Edition, page 1083 (1960).
Claims (1)
1. A PROCESS FOR TREATING A CELLULOSIC TEXTILE FABRIC COMPRISING: WETTING THE FABRIC WITH AN AQUEOUS SOLUTION CONTAINING ABOUT FROM 5 TO 20% BY WEIGHT OF A WATER SOLUBLE PRODUCT OF FORMALDEHYDE AND A CARBAMATE COMPOUND SELECTED FROM THE GROUP CONSISTING OF METHYL CARBAMATE, ETHYL CARBAMATE, PROPYL CARBOMATE, AND BUTYL CARBAMATE, SAID PRODUCT HAVING BEEN PRODUCED BY THE REACTION, IN AQUEOUS ALKALINE SOLUTION, OF THE FORMALDEHYDE AND THE CARBAMATE COMPOUND IN THE MOLE RATIO OF 2 TO 1, AND FROM 0.5 TO 6.0% BY WEIGHT BASED ON THE WEIGHT OF THE CARBAMATE COMPOUND-FOROMALDEHYDE SOLUTION OF AN ACIDIC CATALYST, AND DRYING AND CURING THE TREATED FABRIC AT A TEMPERATURE OF FROM 130 TO 160*C.
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL125120D NL125120C (en) | 1961-06-06 | ||
| NL279381D NL279381A (en) | 1961-06-06 | ||
| US115268A US3144299A (en) | 1961-06-06 | 1961-06-06 | Wrinkle resistance finish for cellulosic textiles |
| CH655662A CH401897A (en) | 1961-06-06 | 1962-05-29 | Process for achieving a crease-proof finish on cellulose textiles |
| BE618419A BE618419A (en) | 1961-06-06 | 1962-06-01 | Crease resistant primer for cellulosic textiles |
| FR899610A FR1327420A (en) | 1961-06-06 | 1962-06-04 | Method and product for treating cellulosic textile materials to increase their resistance to creasing |
| DEF36990A DE1222037B (en) | 1961-06-06 | 1962-06-05 | Process for the preparation of aqueous solutions of mixtures of N, N-dimethylol-alkyl carbamates, N-monomethylol-alkyl carbamates and free formaldehyde |
| DEF41559A DE1258379B (en) | 1961-06-06 | 1962-06-05 | Process for the anti-crease finishing of cellulose textiles |
| GB21749/62A GB971727A (en) | 1961-06-06 | 1962-06-05 | Improvements in or relating to the production of formaldehyde/carbamate condensationproducts and their use in the finishing of cellulosic textile fabrics |
| CH682962A CH372653A (en) | 1961-06-06 | 1962-06-06 | Process for the preparation of durable aqueous solutions containing N, N-dimethylol urethanes, N-monomethylol urethanes and free formaldehyde |
| US274364A US3219632A (en) | 1961-06-06 | 1962-10-17 | Water soluble carbamate-formaldehyde condensate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US115268A US3144299A (en) | 1961-06-06 | 1961-06-06 | Wrinkle resistance finish for cellulosic textiles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3144299A true US3144299A (en) | 1964-08-11 |
Family
ID=22360276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US115268A Expired - Lifetime US3144299A (en) | 1961-06-06 | 1961-06-06 | Wrinkle resistance finish for cellulosic textiles |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3144299A (en) |
| BE (1) | BE618419A (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3369858A (en) * | 1966-09-30 | 1968-02-20 | Union Carbide Corp | Magnesium fluoborate as cellulosecarbamate reaction catalyst |
| US3376101A (en) * | 1963-10-22 | 1968-04-02 | Agriculture Usa | Process of modifying cellulosic textiles with glyoxal-biscarbamate reaction products |
| US3391181A (en) * | 1965-03-18 | 1968-07-02 | Stevens & Co Inc J P | Preparation of methylolated carbamates |
| US3416880A (en) * | 1964-10-13 | 1968-12-17 | Agriculture Usa | Modification of cellulosic textiles with methylolated hydroxyalkyl carbamates |
| US3420696A (en) * | 1964-06-02 | 1969-01-07 | West Point Pepperell Inc | Aldehyde fixation on polymeric material |
| US3454423A (en) * | 1966-11-21 | 1969-07-08 | Millmaster Onyx Corp | N-propyl carbamate resin composition and method of treating a fabric therewith |
| US3491067A (en) * | 1967-07-12 | 1970-01-20 | Diamond Shamrock Corp | Alkylolated polyurethane resins derived from hydroxy ethyl carbamate and their use |
| US3503701A (en) * | 1965-11-15 | 1970-03-31 | Stevens & Co Inc J P | Textile treating agents and methods of preparing same |
| US3524876A (en) * | 1965-07-27 | 1970-08-18 | Dan River Mills Inc | N,n-dimethylolcarbamates of ether alcohols |
| US3658580A (en) * | 1969-09-15 | 1972-04-25 | American Cyanamid Co | Carbamate-melamine textile finish |
| US3768969A (en) * | 1971-12-21 | 1973-10-30 | Us Agriculture | Sensitized textiles with decreased formaldehyde odor |
| US3949108A (en) * | 1973-06-01 | 1976-04-06 | The United States Of America As Represented By The Secretary Of Agriculture | Process for producing fire resistant organic textile materials |
| US6051034A (en) * | 1998-09-30 | 2000-04-18 | Springs Industries, Inc. | Methods for reducing pilling of towels |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1244098B (en) * | 1964-10-13 | 1967-07-13 | John David Reid | Process for crease-proof and wash-wear finishing of cellulose-containing textiles |
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| BE508202A (en) * | ||||
| US2306185A (en) * | 1940-10-25 | 1942-12-22 | Du Pont | Organic compounds and process of preparing the same |
| US2385911A (en) * | 1941-06-16 | 1945-10-02 | Pittsburgh Plate Glass Co | Condensation products of aldehydes and unsaturated ester amides |
| GB783123A (en) * | 1954-04-27 | 1957-09-18 | Boehme Fettchemie Gmbh | Process for the finishing of textiles |
| US2899263A (en) * | 1949-08-15 | 1959-08-11 | Eneurea | |
| US2904387A (en) * | 1958-04-28 | 1959-09-15 | Olin Mathieson | Composition and process for crease- and wrinkleproofing cellulosic textile material |
| US2926190A (en) * | 1958-06-26 | 1960-02-23 | Wasson Burton Kendall | 2-methyl-2-allyl-1, 3-propanediol dicarbamate |
| US2954396A (en) * | 1958-05-16 | 1960-09-27 | Pure Oil Co | Stabilization of carbamate esters |
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- 1962-06-01 BE BE618419A patent/BE618419A/en unknown
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE508202A (en) * | ||||
| US2306185A (en) * | 1940-10-25 | 1942-12-22 | Du Pont | Organic compounds and process of preparing the same |
| US2385911A (en) * | 1941-06-16 | 1945-10-02 | Pittsburgh Plate Glass Co | Condensation products of aldehydes and unsaturated ester amides |
| US2899263A (en) * | 1949-08-15 | 1959-08-11 | Eneurea | |
| GB783123A (en) * | 1954-04-27 | 1957-09-18 | Boehme Fettchemie Gmbh | Process for the finishing of textiles |
| US2904387A (en) * | 1958-04-28 | 1959-09-15 | Olin Mathieson | Composition and process for crease- and wrinkleproofing cellulosic textile material |
| US2954396A (en) * | 1958-05-16 | 1960-09-27 | Pure Oil Co | Stabilization of carbamate esters |
| US2926190A (en) * | 1958-06-26 | 1960-02-23 | Wasson Burton Kendall | 2-methyl-2-allyl-1, 3-propanediol dicarbamate |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3376101A (en) * | 1963-10-22 | 1968-04-02 | Agriculture Usa | Process of modifying cellulosic textiles with glyoxal-biscarbamate reaction products |
| US3420696A (en) * | 1964-06-02 | 1969-01-07 | West Point Pepperell Inc | Aldehyde fixation on polymeric material |
| US3416880A (en) * | 1964-10-13 | 1968-12-17 | Agriculture Usa | Modification of cellulosic textiles with methylolated hydroxyalkyl carbamates |
| US3391181A (en) * | 1965-03-18 | 1968-07-02 | Stevens & Co Inc J P | Preparation of methylolated carbamates |
| US3524876A (en) * | 1965-07-27 | 1970-08-18 | Dan River Mills Inc | N,n-dimethylolcarbamates of ether alcohols |
| US3503701A (en) * | 1965-11-15 | 1970-03-31 | Stevens & Co Inc J P | Textile treating agents and methods of preparing same |
| US3369858A (en) * | 1966-09-30 | 1968-02-20 | Union Carbide Corp | Magnesium fluoborate as cellulosecarbamate reaction catalyst |
| US3548427A (en) * | 1966-11-21 | 1970-12-22 | Millmaster Onyx Corp | Alkyl carbamate/isopropyl carbamate formaldehyde resin compositions and the modification of fabrics therewith |
| US3454423A (en) * | 1966-11-21 | 1969-07-08 | Millmaster Onyx Corp | N-propyl carbamate resin composition and method of treating a fabric therewith |
| US3491067A (en) * | 1967-07-12 | 1970-01-20 | Diamond Shamrock Corp | Alkylolated polyurethane resins derived from hydroxy ethyl carbamate and their use |
| US3658580A (en) * | 1969-09-15 | 1972-04-25 | American Cyanamid Co | Carbamate-melamine textile finish |
| US3768969A (en) * | 1971-12-21 | 1973-10-30 | Us Agriculture | Sensitized textiles with decreased formaldehyde odor |
| US3949108A (en) * | 1973-06-01 | 1976-04-06 | The United States Of America As Represented By The Secretary Of Agriculture | Process for producing fire resistant organic textile materials |
| US6051034A (en) * | 1998-09-30 | 2000-04-18 | Springs Industries, Inc. | Methods for reducing pilling of towels |
Also Published As
| Publication number | Publication date |
|---|---|
| BE618419A (en) | 1962-12-03 |
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