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Publication numberUS3918903 A
Publication typeGrant
Publication dateNov 11, 1975
Filing dateJul 25, 1972
Priority dateJul 25, 1972
Publication numberUS 3918903 A, US 3918903A, US-A-3918903, US3918903 A, US3918903A
InventorsKullman Russel M, Reinhardt Robert M
Original AssigneeUs Agriculture
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Dehydration process to impart wrinkle resistance to cellulose-containing fibrous materials
US 3918903 A
Abstract
Crosslinking formulations are applied to cotton and other cellulose-containing textiles and made to react by dehydrating the impregnated textile at ambient temperatures and pressures.
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Description  (OCR text may contain errors)

United States Patent 1191 Kullman et a1.

1 1 DEHYDRATION PROCESS TO IMPART WRINKLE RESISTANCE TO CELLULOSE-CONTAINING FIBROUS MATERIALS [75] Inventors: Russel M. Kullman. Metairie;

Robert M. Reinhardt, New Orleans. both of La.

[73] Assignee: The United States of America as represented by the Secretary of Agriculture, Washington, DC.

[22 Filed: July 25. 1972 [211 App1.No.:274,949

[521 US. Cl. 8/186; 8/187; 8/1164 [51] Int. Cl. D06M 13/34 [58] Field of Search 8/1164. 189, 181-187.

1 56] References Cited UNITED STATES PATENTS 3.224.926 12/1965 Bernurdin 8/1164 X NOV. 11, 1975 3.264.054 8/1966 Reinhardt et 31.... 8/1 16.4 3.278.470 10/1966 Henshall et a1. 8/1164 X 3.285.690 11/1966 Cooper et a1 8/187 x 3.312.521 4/1967 Stenner 8/1164 3.350.162 111/1967 Becltnmn...v 8/1 16.4 X 3.371.983 3/1968 Barber et a1. 8/1 16.4 3.527.558 9/1970 Tomasino et all 8/189 3.533.728 10/1970 Shippee et a1, 8/189 3.653.805 4/1972 Gamnrra et a1, 8/1492 X 3.660.013 5/1972 PLI18111 8/1492 X 3.706.526 12/1972 Swidler et a1 8/1492 X Primar E.\tU11'l I11'SIp1'1n .1. Lechert. Jr. Attorney. Agent. or Fim1-M. Howard Silverstein. Max D. Hensely [57] ABSTRACT Crosslinking formulations are applied to cotton and other cellulose containing textiles and made to react by dehydrating the impregnated textile at ambient temperatures and pressures.

30 Claims. N0 Drawings DEHYDRATION PROCESS T [MPART WRINKLE RESISTANCE T0 CELLULOSE-CONTAINING FIBROUS MATERIALS 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 chemical finishing of textiles. More particularly, this invention relates to a process for chemical finishing of cellulose-containing fibrous materials to effect crosslinking and improvement in wrinkle resistance. Specifically, this invention relates to a new method of curing a cellulose-containing textile material which has been impregnated with certain crosslinking formulations, the novelty comprising removing moisture upon exposure of the impregnated material to an unheated, dehydrating atmosphere at ambient temperatures and pressures thereby generating the conditions necessary for reaction of a crosslinking reagent with the cellulose and enhancing wrinkle resistance. Hereinafter this novel method of textile processing is referred to as dehydration curing.

THE PRIOR ART There are several processes for producing improved wrinkle resistance in cellulosic materials. That most commonly employed is the pad-dry-cure process. Curing is accomplished in this type of process by subjecting the impregnated material to a strongly heated atmosphere (usually 140" to 180C). Another method of treatment employed is the mild cure finishing process wherein the curing is accomplished with heating at mild temperatures of 60 to 100C, so that moisture content within the fiber is critically controlled. This method re quires precise adjustment of the moisture content in the material being treated.

In another process of the prior art for improved wrinkle resistance, the fibrous material is cured by maintaining a moist condition at about 25C for from 4 to 30 hours,, then neutralizing, washing, and drying. Wet finishing treatments also are known wherein the reaction of the cellulosic fiber proceeds while the fiber is maintained at a level of swelling which is controlled by composition of the treatment bath.

Various modifications have been reported in the literature to achieve improved wet wrinkle resistance or improved wet and dry wrinkle resistance wherein the fibrous material must be (1) exposed to elevated temperatures during curing (considerably higher than ambient room temperatures), as in the pad-dry-cure and mild cure processes; or (2) maintained at a predetermined moisture level during curing, as in moist or wet processes.

Among the advantages of the present invention over the prior art are the savings of heat energy afforded, the greater comfort of workers by the absence of elevated temperatures usually encountered in finishing plants, and particularly the superior levels of wrinkle resistance and chlorine resistance of fabrics treated by the process. The value of wrinkle resistance in textile materials is widely recognized by those skilled in the art. It has been estimated that current annual production in the United States alone of fabric for use in durable press and wrinkle reistant products is about three billion yards.

The main object of the present invention is to provide a process for imparting improved wrinkle resistance by the chemical finishing of cellulose-containing textiles without subjecting the textile to elevated temperatures, without the need of maintaining moisture content in the fibers at critical levels, and without the need for controlling swelling of the fibers through adjustment of the composition of the treatment bath.

We have unexpectedly discovered that reaction between certain crosslinking formulations and cellulosecontaining textiles can be effected readily by the process of our invention. Said process requires no heating during curing and no controlled levels of moisture nor swelling of the fiber. By the process of this invention the fibrous material can be dried and cured by treatment with unheated dehydrating air at ambient temperatures and pressures after impregnating the cellulosecontaining textile with the crosslinking formulation and removing the excess by conventional squezze-roll techniques.

The instant invention can best be described as a process for imparting wrinkle resistance to cellulose-containing fibrous material, the process comprising:

a. impregnating the cellulose-containing fibrous material with a formulation containing about from 5 to 25 weight percent of a crosslinking agent selected from the group consisting of glyoxal, formaldehyde, dimethylol dihydroxyethyleneurea, and dimethylol methyl carbamate and about from 0.1 to 1.2 weight percent of an inorganic acid catalyst selected from the group consisting of hydrochloric acid, hydrobromic acid, sulfuric acid, sulfurous acid, phosphoric acid, phosphorous acid, nitric acid, and nitrous acid,

. removing the excess quantity of formulation to obtain a wet pickup of about to percent, and exposing the fibrous material of step (b) to a dehydrating atmosphere at ambient temperatures and pressures, for periods of time about from 30 minutes to 24 hours, the longer periods of time being employed with a static dehydrating atmosphere and the shorter periods of time being employed with a dynamic dehydrating atmosphere.

An optional step can be inserted between above steps (b) and (c) wherein the wet fibrous material of step (b) is dried to a moisture content intermediate between that of the wet fabric and complete dryness by passing the impregnated material through a conventional drying oven. The time of dehydration treatment necessary to produce a given level of wrinkle resistance in fabric can be markedly decreased by such a partial drying step.

The productsproduced by the process are part of this invention. These have outstanding qualities both high dry and wet wrinkle resistance and high levels of resistance to damage due to retained chlorine.

By the process of the present invention fibrous material to be employed therein may be in the form of fibers, yarns, and fabrics; either woven or knitted. The material may be composed entirely of cellulosic fibers,

either natural or regenerated, or may be composed of said cellulosics as components with other non-cellulosic natural and synthetic components.

PREFERRED REAGENTS Preferred reagents for use in the process of this invention are difunctional and polyfunctional chemical agents that react with the hydroxyl groups of cellulose under acidic conditions. These agents include formaldehyde adducts (methylol derivatives) of nitrogenous compounds, such as dimethylol alkyl carbamates, dimethylol dihydroxyethyleneurea, dimethylol propyleneureas, and the like; modified methylol agents, such as N-methoxymethyl, N-isopropoxymethyl, and N-acetoxymethyl derivatives, and the like; monoaldehydes, such as formaldehyde; and dialdehydes, such as glyoxal. The concentration of the crosslinking chemical agent employed in the process may be varied in the range of from about 2.5 percent to 35 percent by weight, based on the total weight of the finishing solution. The preferred range is from about to about percent.

The catalyst employed in the formulation may be an organic acid, a strong Lewis acid, or a mineral acid. The preferred catalyst is an inorganic acid such as hydrochloric, sulfuric, nitric acid and the like. Concentration of the catalyst in the treating solution may be varied from about 0.025 to about 2.5 weight percent but we have found that the range of 0.1 to 1.2 weight percent to be preferred in this invention.

Additives known to those skilled in the art may be used in the treating solution for supplementary effects such as softness of hand and the like.

THE DEl-IYDRATION STEP Dehydration curing by the process of this invention is carried out after impregnation of the fibrous material with a solution containing the chemical crosslinking agent and catalyst, or alternately, after partially drying the impregnated material. impregnation may be accomplished by any suitable means. For fabric treatments, impregnation is most commonly accomplished by immersing the fabric in the treatment solution, then squeezing out excess solution by passing through pad rolls which also facilitates uniform penetration and distribution of the treatment solution within the fibrous material. Based upon the dry weight of the material, a wet pickup of about 60 to 100 percent is preferred.

The fibrous material may then, as shown in the following Examples, be partially dried before curing under ambient pressures and temperatures. The material is heated for about from 1.5 to 7 minutes at a temperature sufficient to partial dry the material, e.g., about 60 C.

Curing conditions which may be employed in the process of this invention include exposure of the suitably impregnated fibrous material to a static or a dynamic (moving) dehydrating atmosphere under ambient pressures and temperatures of about from 20 to 30C, for periods of about from 30 minutes to 24 hours. Time required can vary depending upon selection of a static or dynamic dehydrating atmosphere. An afterwash of the treated fabric by any conventional washing procedure is done after curing to remove residual catalyst, unused reactant, and byproducts. After-washing 4 may be omitted with some catalysts as the cured mate rial regains moisture on removal from the dehydrating atmosphere, said moisture may be sufficient to dilute and render any remaining catalyst or acidic material innocuous.

In summary, this invention provides a process (and products by said process) for finishing fibrous materials containing a cellulosic component to produce a product with improved wrinkle resistance. Wrinkle resistance as a useful fabric property is well known and is a necessity for durable press garments that are in such demand by American and other consumers. The curing treatment of the process is carried out in the presence of an unheated, dehydrating atmosphere. The process may be summarized as:

a. impregnating the fibrous material containing a cellulosic component to about -100 percent wet pickup of of a solution containing 5-25 percent of a chemical agent capable of crosslinking the cellulosic component, and an inorganic acid catalyst; and

b. exposing the impregnated material to a static or a dynamic unheated dehydrating atmosphere at ambient temperatures and pressures, for periods of time sufficient to effect the crosslinking reaction to produce a fibrous material having improved wrinkle resistance.

The following examples are set forth to illustrate certain significant aspects of the invention, and should not be construed as limiting the invention in any manner whatever.

EXAMPLE I Swatches of cotton printcloth were padded to about percent wet pickup with an aqueous solution containing 15 percent (wt./wt.) of dimethylol methyl car- -bamate and 0.4 percent (wt./wt.) of hydrogen chloride (from hydrochloric acid). These swatches were divided into Groups A, B, and C. Samples from each group were partially dried in a 60C atmosphere for 1.5, 3, 5, and 7 minutes which reduced the moisture contents to about 40, 18, 4, and 3 percent, respectively. Group A samples, A-l.5, A-3, A-5, and A-7, immediately after partial drying were neutralized in a dilute solution (approximately 1 percent, wt/wt) of sodium carbonate, then washed and dried. Group B samples, B-l,5, 8-3, 3-5, and 13-7, after partial drying were placed in a reaction chamber in contact with a dehydrating atmosphere (static conditions, normal pressures) over 150, desiccant at 25C for 22 hours, removed, neutralized in the sodium carbonate solution, then washed and dried. Group C samples, C-1.5, C-3, G5, and C-7, after partial drying were immediately sealed in plastic bags and maintained at constant moisture levels for 22 hours at 25C, removed, neutralized in the sodium carbonate solution, then washed and dried. Results are shown in Table 1.

TABLE l-continued Partial Moisture I: Strength drying content WRA,W+F retention in Sample (min. at after HCHO N deg Cl-scorch 60C) partial Dry Wet test drying B-5 5 4 4.42 1.27 272 290 95 8-7 7 3 4.32 1.40 261 288 96 01.5 1.5 40 0.73 0.31 189 180 2 C-3 3 18 1.56 0.44 I92 254 7 C-5 5 4 3.30 L03 269 282 36 C-7 7 3 3.87 1.10 270 27S 65 These data show that samples of Group B, the pro- EXAMPLE 4 cess Of the present invention, are SUPCI'IOT I11 reaction 5 Swatches of cotton printcloth were padded to about efficiency as seen by high nitrogen and formaldehyde contents, high wet and dry wrinkle recovery angles, and high levels of strenth retention in the chlorinationscorch test (AATCC Test Method 92-1967, American Association of Textile Chemists and Colorists). The

' data also reveal that partial drying to too low a level of moisture content prior to exposure to an uneated dehydrating atmosphere gives a lower wrinkle recovery than do treatments in which samples with higher moisture levels are exposed to the unheated dehydrating atmosphere. Furthermore, prevention of moisture loss during the curing reaction as in the treatments of Group C does not produce comparably high levels of wet wrinkle recovery nor of strength retention in the chlorination-scorch test.

EXAMPLE 2 Swatches of cotton printcloth were padded to about 90 percent wet pickup with a solution containing percent (wt./wt.) of formaldehyde and 0.4 percent (wt/wt.) of hydrogen chloride. Four samples were partially dried as in Example 1 for 1.5, 3, 5, and 7 minutes, respectively. These samples were coded D-l.5, D-3, D-5, and D-7. In addition, one sample coded D-O, was not partially dried. The samples were treated in a dehydration chamber over P 0 desiccant at 25C for hours, removed, washed, and dried. Results are shown in Table ll.

TABLE ll WRA, W+F, deg. Sample HCHO Dry Wet D- 0.82 247 276 D-1.S 1.18 287 286 D-3 1.21 284 289 D-5 1.17 283 279 D-7 1.39 288 281 From these data it is shown that the new process for producing improved wrinkle resistance is effective with monoaldehyde crosslinking agents.

EXAMPLE 3 percent wet pickup with a solution containing 15 percent (wt./wt.) of dimethylol methyl carbamate and 0.4 percent (wt./wt.) of hydrogen chloride. These swatches were divided into Groups E and F and partially dried in a 60C atmosphere for 3 minutes (about 18 percent moisture content). Group E swatches, 5%, E36, E-l E-2, and 13-3, after partial drying were placed in a dehydration chamber over P 0 desiccant. An inlet and outlet connection on the chamber allowed unheated, anhydrous air to be passed into, through, and out of the chamber during dehydration of the E samples. Ambient air at 25C was made anhydrous by bubbling through concentrated sulfuric acid and used for the treatment. B samples were treated by this procedure for A, 34, l, 2, and 3 hours at 25C. They were coded E-r, E-ik, E-l E-2, and E-3, respectively. After the treatment, they were removed, neutralized in sodium carbonate solution as in Example 1, then washed and dried. Samples F- l F2, and F-3 were placed in the dehydration chamber over P, O, desiccant at 25C for l, 2, and 3 hours, respectively as done for B samples in Example 1. They were then removed, neutralized in the sodium carbonate solution as in Example 1, washed and dried. Results are shown in Table III.

From data in this table, it is seen that development of dry wrinkle recovery by the new process may be accelerated greatly by dynamic conditions in which anhy drous air at 25C is passed through the reaction chamber during the dehydration curing treatment.

EXAMPLE 5 A swatch of cotton printcloth was padded to about percent wet pickup with a solution containing 15 percent (wt.lwt.) of dimethylol methyl carbamate and 0.4 percent (wt/wt.) of hydrogen chloride. The wetimpregnated fabric was placed in a dehydration chamber as in Example 4 but in the absence of P 0 Ambient air at 28C was'made anhydrous by passing through a heat exchange coil immersed in a dry ice (solid C0,)- acetone bath at 67C such that moisture in the air was condensed, frozen, and thus removed. The anhydrous air was then passed through glass coils to achieve a TABLE IV Time after sample Chamber insertion Chamber relative temperature. in chamber humidity C 65 28 minutes 785 28 45 minutes 80.5 28 3 hours 52 28 The dry wrinkle resistance of the finished fabric was 262 and the wet wrinkle resistance was 264.

The initial increase in relative humidity is due to the moisture introduced by the wet-impregnated fabric. During the course of reaction between the finished agent and cellulose more water is produced which also contributes to imcreased humidity. This is seen in the following equation which represent the crosslinking reaction that produces wrinkle resistance.

Cellulose-OH HOCH, CH,OH HO-Cellulose N l c OCH,

H catalyst Cellulose-OCH,NCH,O-Cellulose 2H,0

OCH,

Dehydration of the fabric and the reaction has occurred to a sufficient extent after three hours at a constant temperature to produce a wrinkle resistant fabric. The relative humidity after three hours reflects that the dehydration of the fabric and the reaction have approached completion.

EXAMPLE 6 A swatch ofa fabric comprised of an equiweight mixture of polyester and cotton was padded to about 80 percent wet pickup with a solution containing 25 percent (wt/wt) of dimethylol methyl carbamate and 0.6 percent (wt/wt) of hydrogen chloride. The swatch labelled G, was partially dried for 3 minutes in a 60C atmosphere, placed in the dehydration chamber over P 0 desiccant at 25C for H6 hours as Sample E in Example 4 with anhydrous air flowing into, through, and out of the chamber. After removal and washing the sample was tumble dried in an automatic home dryer, then evaluated for durable press appearance using the AATCC 3-dimensional standards.

An untreated swatch, labelled H, of the same fabric containing equiweight mixtures of polyester and cotton after being washed and tumble dried in the same manner as Sample G was also evaluated with the AATCC 3-dimensional standards.

8 Sample G and H were also tested for wrinkle recovery and results are shown in Table V.

TABLE V Sample WRA, W-t-F,deg. Durable Press Rating Dry Wet after tumble drying This shows that the new process is effective in improving durable press performance, as measured by improvement in dry and wet wrinkle recovery and smoothness appearance as measured by the durable press rating of fabrics containing up to 50 percent by weight of a cellulosic component.

EXAMPLE 7 Four swatches of cotton printcloth were labelled l, J, K, and L respectively. Swatches were padded to about percent wet pickup with solutions as identified in the following data:

HCl in Dimethylol methyl treatment carbamate in treatment Swatch solution solution I 0. l4 5 I 0.28 10 K 0.59 25 TABLE VI WRA. dry Durable Press Rating after Sample Tumble Drying I 225 2.7 J 259 3.7 K 270 4.5 L 206 L0 Improvement in wrinkle recovery and smoothness appearance was achieved in each instance over a wide range of concentration of catalyst and crosslinking agent by use of this new process over the untreated sample (Sample L).

EXAMPLE 8 Swatches of cotton printcloth, labelled M and N were padded to about 90 percent wet pickup and aqueous solutions identified below:

Swatch %H,SO. DMDHEU M 0.6 Is N 1.2 [5

"DMDHEU is dat m, a .cn-n crosslinking agent.

The swatches were partially dried for 3 minutes in a 60C atmosphere, placed in the dehydration chamber over P 0, desiccant at 25C for 1% hours as Sample E in Example 4 with anhydrous air flowing into, through TABLE. VI]

Sample WRA. dry Durable Press Rating after Tumble drying L (untreated) 206 L This demonstrates that the process is useful with other mineral catalysts and tetrafunctional crosslinking agents.

We claim:

1. A process for imparting wrinkle resistance to cellulose-containing fibrous material comprising:

a. impregnating the cellulose-containing fibrous material with a formulation containing about from 2.5 to 35 weight percent of a crosslinking agent and about from 0.025 to 25 weight percent of an inorganic acid catalyst,

b. removing the excess quantity of formulation to obtain a wet pickup of about 60 to 100 weight percent, and

c. exposing the fibrous material of step (b) to a dehydrating atmosphere at ambient temperatures and pressures, for periods of time about from 30 minutes to 24 hours.

2. A process for imparting wrinkle resistance to cellulose-containing fibrous material comprising:

a. impregnating the cellulose-containing fibrous material with a formulation containing about from 2.5 to 35 weight percent of a crosslinking agent selected from the group consisting of: glyoxal formaldehyde dimethylol dihydroxyethyleneurea, and dimethylol methyl carbamate and about from 0.025 to 2.5 weight percent of an inorganic acid catalyst selected from the group consisting of: hydrochloric acid hydrobromic acid sulfuric acid sulfurous acid phosphoric acid phosphorous acid nitric acid, and nitrous acid,

. removing the excess quantity of formulation to obtain a wet pickup of about 60 to 100 weight percent, and

. exposing the fibrous material of step (b) to a dehydrating atmosphere at ambient temperatures and pressures, for periods of time about from 30 minutes to 24 hours, the longer periods of time being employed with a static dehydrating atmosphere and the shorter periods of time being employed with a dynamic dehydrating atmosphere.

3. The process of claim 2 wherein the crosslinking agent is glyoxal.

4. The process of claim 2 wherein the crosslinking agent is formaldehyde.

5. The process of claim 2 wherein the crosslinking agent is dimethylol dihydroxyethyleneurea.

6. The process of claim 2 wherein the crosslinking agent is dimethylol methyl carbamate.

7. The process of claim 2 wherein the inorganic acid catalyst is hydrochloric acid.

8. The process of claim 2 wherein the inorganic acid catalyst is hydrobromic acid.

9. The process of claim 2 wherein the inorganic acid catalyst is sulfuric acid.

10. The process of claim 2 wherein the inorganic acid catalyst is sulfurous acid.

1 l. The process of claim 2 wherein the inorganic acid catalyst is phosphoric acid.

12. The process of claim 2 wherein the inorganic acid catalyst is phosphorous acid.

13. The process of claim 2 wherein the inorganic acid catalyst is nitric acid.

14. The process of claim 2 wherein the inorganic acid catalyst is nitrous acid.

15. A process for imparting wrinkle resistance to cellulose-containing fibrous material comprising:

a. impregnating the cellulose-containing fibrous material with a formulation containing about from 2.5 to 35 weight percent of a crosslinking agent and about from 0.025 to 2.5 weight percent of an inorganic acid catalyst,

b. removing the excess quantity of formulation to obtain a wet pickup of about 60 to weight percent,

c. heating the fibrous material for about from 1.5 to 7 minutes at a temperature sufficient to partially dry said material, and

d. exposing the fibrous material of step (c) to a dehydrating atmosphere at ambient temperatures and pressures.

16. A process for imparting wrinkle resistance to cellulose-containing fibrous material, comprising:

a. impregnating the cellulose-containing fibrous material with a formulation containing about from 2.5 to 35 weight percent of a crosslinking agent selected from the group consisting of: glyoxal formaldehyde dimethylol dihydroxyethyleneurea, and dimethylol methyl carbamate and about from 0.025 to 2.5 weight percent of an inorganic acid catalyst selected from the group consisting of:

' hydrochloric acid hydrobromic acid sulfuric acid sulfurous acid phosphoric acic phosphorous acid nitric acid, and

nitrous acid removing the excess quantity of formulation to obtain a wet pickup of about 60 to 100 weight percent, and

c. heating the fibrous material for about from 1.5 to 7 minutes at a temperature of about 60 C. and

d. exposing the fibrous material of step (c) to a dehydrating atmosphere at ambient temperatures and presures for periods of time about from 30 minutes to 24 hours.

17. The process of claim 16 wherein the crosslinking agent is glyoxal.

18. The process of claim 16 wherein the crosslinking agent is formaldehyde.

1 1 l2 19. The process of claim 16 wherein the crosslinking 25, The process of claim 16 wherein the inorganic agent is dimethylol dihydroxyethyleneurea. id catalyst i h h i acid,

20. The process of claim 16 wherein the crosslinking The process of claim 16 wherein the inorganic agent is dimethylol methyl carbamate.

21. The process of claim 16 wherein the inorganic 5 acid catalyst is hydrochloric acid.

22. The process of claim 16 wherein the inorganic acid catalyst is hydmbmmic acid 28. The process of claim 16 wherein the inorganic 23. The process of claim 16 wherein the inorganic acid catalyst is nitrous acida id at l t i lf i id 29. The product produced by the process of claim 2. 24. The process of claim 16 wherein the inorganic 0- Th Pr duct produced by the process of claim 16. acid catalyst is sulfurous acid.

acid catalyst is phosphorous acid.

27. The process of claim 16 wherein the inorganic acid catalyst is nitric acid.

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Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US5639281 *Jul 1, 1996Jun 17, 1997Hopkins Chemical IncorporatedMethod of obtaining a uniform surface finish effect on fabrics or garments using a gel and composition therefor
US5958187 *Jul 11, 1997Sep 28, 1999Fort James CorporationBiodegradable tissue paper
US6051034 *Sep 30, 1998Apr 18, 2000Springs Industries, Inc.Applying composition consisting of acidic agent and optionally fabric softener then heating
US6059928 *Sep 18, 1995May 9, 2000Fort James CorporationPrewettable high softness paper product having temporary wet strength
Classifications
U.S. Classification8/186, 8/116.4, 8/187
International ClassificationD06M15/37, D06M13/123, D06M15/423, D06M13/00
Cooperative ClassificationD06M13/123, D06M15/423, D06M13/127
European ClassificationD06M13/123, D06M15/423, D06M13/127