US3911181A - Permanent press textile finish - Google Patents
Permanent press textile finish Download PDFInfo
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- US3911181A US3911181A US351395A US35139573A US3911181A US 3911181 A US3911181 A US 3911181A US 351395 A US351395 A US 351395A US 35139573 A US35139573 A US 35139573A US 3911181 A US3911181 A US 3911181A
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- urea
- aminoplast
- dihydroxyethyleneurea
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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
- 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
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- This invention relates to creaseresistant aminoplast textile finishes for cellulosic fibers. More particularly, it relates to aqueous aminoplast textile finishes containing l,3 dimethylol-4,5-dihydroxyethyleneurea and ureaformaldehyde condensation products. to the method of applying the finishes and to the textile materials thus obtained.
- l,3-Dimethylol-4,5-dihydroxyethyleneurea is a known aminoplast agent for finishing textile materials, particularly cellulosic textile materials, in order to obtain wash-and-wear and durable-press properties as disclosed in U.S. Pat. No. 2,731,364, for example.
- the finish not only gives good wrinkle resistant properties, but also does not cause yellowing or degradation of cellulosic fabrics in the presence of chlorine.
- a further object is to provide such a finish for use on textiles to be subjected to laundering and bleaching.
- a crease-resistant finish for cellulosic textile materials has now been discovered which is essentially equal to l,3-dimethylol-4,5-dihydroxyethyleneurea in all respects and at the same time is more economical than the dihydroxyethyleneurea compound.
- the textile finish of this invention is an aqueous solution of a mixture of l,3-diinethylol-4,5-dihydroxyethyleneurea and a urezrformaldehyde condensate as defined below.
- ureaformaldehyde condensates are considerably cheaper to manufacture than l,3-dimethylol-4,5 dihydroxyethyleneurea.
- urea-forrnaldehyde condensates cause considerable loss in strength of the fabric when the fabric is treated with chlorine, as in a laundering operation, followed by pressing with a hot iron.
- the strength loss is usually termed degradation due to chlorine retention.
- the urea-formaldehyde condensates of use in this in vention are the reaction products of urea with formaldehydc, they are polymethylol derivatives of ureav
- the condensates should contain at least 1.8 moles, preferably between 2.0 and 3.6 moles, of combined formaldehyde per mole of urea. (40 Moles of formaldehyde per mole of urea is the theoretical maximum amount of combined formaldehyde).
- the use of products containing more than 3.6 moles of formaldehyde per mole of urea is not desirable since it may decrease the stability of the textile finish.
- the ureaformaldehyde condensates may be partially alkylated if desired, but it is not necessary.
- urea-formaldehyde condensates for use in this invention are: (l) a condensate containing 2.8 moles of combined formaldehyde per mole of urea with a slight degree of methylation and (2) a condensate containing about 3.43.5 moles of combined formaldehyde, as disclosed in US. Pat. No. 3,335,113.
- the urea-formaldehyde condensates used in the tex tile finish of this invention may be employed in amounts up to 60%, preferably up to 50%, of the com bined aminoplast components of the textile finish.
- the lower limit is 5% and preferably 25% on an economical basis, although there is no lower limit as far as effectiveness goes.
- the amount of combined aminoplast components of the finish applied to the cellulosic textile materials should be between 2 and 20%, preferably between 3 and 10%, o,w.f. (on weight of fabric).
- the application is by conventional methods from an aqueous medium as by padding, spraying, dipping, etc.
- the treated fabrics are dried and then cured.” or dired and cured," at an elevated temperature, normally between 250 and 375F., preferably between 300 and 350F. Curing at the higher end of the temperature range often provides superior results.
- a curing catalyst be used to accelerate the cure of the finish on the fabric.
- Conven tional acid-acting catalysts may be used and they are conveniently applied to the fabric simultaneously with the aminoplast finish from the same padding bath.
- Such catalysts are well-known, for example, as disclosed in U.S. Pat. No. 3,079,279.
- the preferred catalyst is zinc nitrate. Conventional amounts are used, i.e., in the range of 5 to 15% based on the combined aminoplast components.
- Cellulosic textile materials include cotton, rayon (re generated cellulose), linen, and other materials con taining cellulosic fiber. It also includes blends of cellu losic fibers and other fibers, such as the synthetic fibers, e.g., nylons, polyesters, polyacrylonitriles, etc. The blend should contain at least 20%, preferably at least 30%, of cellulosic fibers.
- the pad baths were applied to 80 X 80 cotton percale by a standard padding procedure obtaining an 80% wet pick-up.
- the treated fabrics containing 4.6% of total resin solids were dried at 225F. for 2.5 minutes and then heated at 350F. for 1.5 minutes.
- Example 3 The procedure of Example 1 was followed with the exceptions that the pad baths contained 1 1.5% of total resin solids, the treated fabrics contained 9.2% resin solids, the fabrics were cured at 300F. for 1.5 min utes, and the fabric washes were carried out with detergent and chlorine (Clorox).
- the pad baths were applied to X 80 cotton percale by a standard padding procedure obtaining an 87% wet pick-up.
- the treated fabrics containing 4.6% of total resin solids were dried at 225F. for 2.0 minutes and then heated: (a) at 350F. for 1.5 minutes and (b) at 300F. for 1.5 minutes; see Tables ill and IV, respectively.
- Swatches of untreated and treated fabrics were tested for wrinkle recovery by Tentative Test Method AATCC 66-1959T. Strength loss of the fabrics due to retained chlorine was measured by Standard Test Method AATCC 92-1967 after 5 washes in a homestyle washing machine using water at 140F. with a synthetic detergent and Clorox.
- a method for providing a crease resistance to cellulosic-containing textile materials which comprises applying from about 2 to based on the weight of said textile materials of an aminoplast finish comprising an aqueous solution ol a mixture of l.3-dimethylol-4,5-- dihydroxyethyleneurea and a urea-formaldehyde con densate.
- said ureaiormaldchyde condensate being from 5 to 511% by weight of the total aminoplast and said l,3-dimethylol-4.5-dihydroxyethylencurea being from 50 to 95C?
- said ureaformaldehyde condensate further containing from 1.8 to 3.6 mols of combined formaldehyde, thereafter drying said textile material and curing said finish on said textile at an elevated temperature. in the presence of an acid acting catalyst.
- urea formaldehyde condensate is from 5 to 3U /r by weight ot the total aminoplast and the l.3-dimcthylol-4,5-
- dihydroxyethyleneurea is from 95 to by Weight 01' the total aminoplast.
- a method according to claim 3 which comprises applying about 4.6%, based on the weight 01 said textile materials, of an aminoplast comprising an aqueous solution of a mixture of l 3-dimethylol-4.5 dihydroxyethyleneurea and a urea-formaldehyde con densate.
- said urea iormaldehyde condensate being about 70'
- said l.3-dimethylol-4,5-dihydroxyethyleneurea being about 30% by weight of the total aminoplast.
- said ureal'ormaldehyde condensate containing about 2.8 mols of combined formaldehyde.
- a method according to claim 4 comprising drying said textile material at about 225F. for about 2.1] minutes and curing said dried textile material for about l5 minutes at 350F.
- a material according to claim 2 wherein the ureaformaldehyde condensate is from 5 to 30% by weight of the total aminoplast and the l,3dimethylol-4.5- dihydroxyethyleneurea is from to 70% by weight of the total aminoplast.
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Abstract
Crease-resistant finishes for cellulosic fibers, said finishes containing 1,3-dimethylol-4,5-dihydroxyethyleneurea and up to 60% urea-formaldehyde condensation products, said finishes being resistant to the degradation effects of chlorine.
Description
United States Patent Herbes et a1.
PERMANENT PRESS TEXTILE FINISH Inventors: William Frank Herbes, Bridgewater Township Somerset County, N.J.; Robert George Weyker, Memphis,
Tenn.
Assignee: American Cyanamid Company,
Stamford, Conn Filed: Apr. 16, 1973 App14 No: 351,395
Related U.S. Application Data Continuation-impart of Ser. No. 124910, March 16 1971 abandoned. which is a continuation of Scr. No, 763,344, Septv 27, 1968 abandoned.
US. Cl. t. 427/390; 8/186; 427/392 Int. Cl. D06M 15/12 Field of Search 117/143 A, 145, 13914,
1 Oct. 7, 1975 Primary ExaminerTh0mas J. Herbert, Jrv Assistant ExaminerBruce H. Hess Attorney Agent, or FirmH. G. Jackson 57 ABSTRACT Crease-resistant finishes for cellulosic fibers. said finishes containing l,3-dimethy10|-4 5- dihydroxyethyleneurea and up to 60% mean formaldehyde condensation products said finishes being resistant to the degradation effects of chlorine.
7 Claims, N0 Drawings PERMANENT PRESS TEXTILE FINISH This application is a continuation-in-part of Application Ser. No. 124,910 filed Mar. 16, 1971, now abandoned, which is a continuation of application Ser. No. 763,344 filed Sept. 27, 1968, now abandoned.
This invention relates to creaseresistant aminoplast textile finishes for cellulosic fibers. More particularly, it relates to aqueous aminoplast textile finishes containing l,3 dimethylol-4,5-dihydroxyethyleneurea and ureaformaldehyde condensation products. to the method of applying the finishes and to the textile materials thus obtained.
l,3-Dimethylol-4,5-dihydroxyethyleneurea (i.e., l,3- dimethylol-4,5-dihydroxy-2imidazolidinone) is a known aminoplast agent for finishing textile materials, particularly cellulosic textile materials, in order to obtain wash-and-wear and durable-press properties as disclosed in U.S. Pat. No. 2,731,364, for example. The finish not only gives good wrinkle resistant properties, but also does not cause yellowing or degradation of cellulosic fabrics in the presence of chlorine. The preparation of l,3dimethylol4,5-dihydroxyethyleneurea requires the use of glyoxal, which is a relatively expensive intermediate as compared with the majority of intermediates used in preparing other crease'resistant textile finishes. However, none of the conventionally used, less expensive crease-resistant textile finishes have been found to be equal to l,3-dimethylol-4,5- dihydroxyethyleneurea in all respects. A need exists, therefore, for a textile finish which will perform as well as l,3-dimethylol-4,Sxlihydroxyethyleneurea and yet be less costly to manufacture.
It is therefore an object of this invention to provide a relatively inexpensive, effective permanent-press textile finish which is resistant to the degradation effects of chlorine.
A further object is to provide such a finish for use on textiles to be subjected to laundering and bleaching.
These and other objects of the invention will become apparent as the description thereof proceeds.
A crease-resistant finish for cellulosic textile materials has now been discovered which is essentially equal to l,3-dimethylol-4,5-dihydroxyethyleneurea in all respects and at the same time is more economical than the dihydroxyethyleneurea compound. The textile finish of this invention is an aqueous solution of a mixture of l,3-diinethylol-4,5-dihydroxyethyleneurea and a urezrformaldehyde condensate as defined below.
The ureaformaldehyde condensates are considerably cheaper to manufacture than l,3-dimethylol-4,5 dihydroxyethyleneurea. However, it is well-known that urea-forrnaldehyde condensates cause considerable loss in strength of the fabric when the fabric is treated with chlorine, as in a laundering operation, followed by pressing with a hot iron. The strength loss is usually termed degradation due to chlorine retention.
Therefore, it is very surprising that a considerable portion of the l ,3 dimethylol4,5- dihydroxyethyleneurea normally used in a textile finish can be replaced by a urea-formaldehyde condensate without materially increasing the strength loss due to chlorine retention.
Various methods have been disclosed for the manufacture of l,3-dimethylol-4,5-dihydroxyethyleneurea. All the procedures use urea. glyoxal and formaldehyde with variations in the reaction conditions as disclosed in U.S. Pat. Nos. 2,731,472; 2,764,573 [combination of the two patents], 2,876,062; 1049,4 46; and British Pat. No. 1,032,379.
The urea-formaldehyde condensates of use in this in vention are the reaction products of urea with formaldehydc, they are polymethylol derivatives of ureav The condensates should contain at least 1.8 moles, preferably between 2.0 and 3.6 moles, of combined formaldehyde per mole of urea. (40 Moles of formaldehyde per mole of urea is the theoretical maximum amount of combined formaldehyde). The use of products containing more than 3.6 moles of formaldehyde per mole of urea is not desirable since it may decrease the stability of the textile finish. The ureaformaldehyde condensates may be partially alkylated if desired, but it is not necessary. The solubility of the lower methylolation products is increased by partial a1 kylation, preferably methylation, by well-known procedures. Particularly suitable urea-formaldehyde condensates for use in this invention are: (l) a condensate containing 2.8 moles of combined formaldehyde per mole of urea with a slight degree of methylation and (2) a condensate containing about 3.43.5 moles of combined formaldehyde, as disclosed in US. Pat. No. 3,335,113.
The urea-formaldehyde condensates used in the tex tile finish of this invention may be employed in amounts up to 60%, preferably up to 50%, of the com bined aminoplast components of the textile finish. The lower limit is 5% and preferably 25% on an economical basis, although there is no lower limit as far as effectiveness goes.
The amount of combined aminoplast components of the finish applied to the cellulosic textile materials should be between 2 and 20%, preferably between 3 and 10%, o,w.f. (on weight of fabric). The application is by conventional methods from an aqueous medium as by padding, spraying, dipping, etc.
The treated fabrics are dried and then cured." or dired and cured," at an elevated temperature, normally between 250 and 375F., preferably between 300 and 350F. Curing at the higher end of the temperature range often provides superior results.
It is recommended that a curing catalyst be used to accelerate the cure of the finish on the fabric. Conven tional acid-acting catalysts may be used and they are conveniently applied to the fabric simultaneously with the aminoplast finish from the same padding bath. Such catalysts are well-known, for example, as disclosed in U.S. Pat. No. 3,079,279. The preferred catalyst is zinc nitrate. Conventional amounts are used, i.e., in the range of 5 to 15% based on the combined aminoplast components.
Cellulosic textile materials include cotton, rayon (re generated cellulose), linen, and other materials con taining cellulosic fiber. It also includes blends of cellu losic fibers and other fibers, such as the synthetic fibers, e.g., nylons, polyesters, polyacrylonitriles, etc. The blend should contain at least 20%, preferably at least 30%, of cellulosic fibers.
The following specific examples are given to illus trate the invention and are not intended to be limitativev EXAMPLE 1 Five pad baths were prepared containing the relative amounts of l,3-dimcthylol-4,S-dihydroxyethyleneurea (Resin A) and a slightly methylated urca formaldehyde condensate having about 28 moles of combined formaldehyde per mole of urea (Resin B") shown in Table 1, each bath containing 5.75% (by weight) of total resin" solids and 10% of zinc nitrate based on the "resin" solids.
The pad baths were applied to 80 X 80 cotton percale by a standard padding procedure obtaining an 80% wet pick-up. The treated fabrics containing 4.6% of total resin solids were dried at 225F. for 2.5 minutes and then heated at 350F. for 1.5 minutes.
Swatches of untreated and treated fabrics were tested for wrinkle recovery by Tentative Test Method AATCC 66-1959T.
Strength loss of the fabrics due to retained chlorine was measured by Standard Test Method AATCC 92-1967 after 5 washes in a homestyle washing ma chine using water at 140F. and a synthetic detergent.
The results are shown in Table I.
Similar results were obtained when the procedure of Example 1 was repeated using a urea-formaldehyde condensate containing about 3.4 moles of combined formaldehyde per mole or urea.
EXAMPLE 3 The procedure of Example 1 was followed with the exceptions that the pad baths contained 1 1.5% of total resin solids, the treated fabrics contained 9.2% resin solids, the fabrics were cured at 300F. for 1.5 min utes, and the fabric washes were carried out with detergent and chlorine (Clorox).
The results of the test are shown in Table [1.
TABLE 1] Strength Total Wrinkle Loss Due Resin A Resin 8 Recovery to Chlorine 7: 7: Degrees, W F Retention, X
a. 100 301 14 b. 70 30 300 l l c. (1 50 299 15 d. 30 70 292 39 e. 0 I00 293 52 f Untreated I82 0 Seven pad baths were prepared containing the relative amounts of l.3-dirnethy1ol-4.5- dihydroxyethyleneurea (Resin A) and a slightly methylated urea-formaldehyde condensate having about 2.8 moles of combined formaldehyde per mole of urea ("Resin B") shown in Tables Ill and IV, each bath containing 5.29% (by weight) of total resin solids and 10% of zinc nitrate based on the resin solids.
The pad baths were applied to X 80 cotton percale by a standard padding procedure obtaining an 87% wet pick-up. The treated fabrics containing 4.6% of total resin solids were dried at 225F. for 2.0 minutes and then heated: (a) at 350F. for 1.5 minutes and (b) at 300F. for 1.5 minutes; see Tables ill and IV, respectively. Swatches of untreated and treated fabrics were tested for wrinkle recovery by Tentative Test Method AATCC 66-1959T. Strength loss of the fabrics due to retained chlorine was measured by Standard Test Method AATCC 92-1967 after 5 washes in a homestyle washing machine using water at 140F. with a synthetic detergent and Clorox.
The two sets of test data shown for each application in Tables Ill and 1V represent physical tests measured on randomized duplicates submitted from each treatment. These data demonstrate that low losses in strength due to chlorine retention are obtained at levels of 0-70% of Resin B when the cure is carried out at TABLE III (cured 1.5 mins. at 350F) Strength Total Wrinkle Loss Due Resin A Resin B Recovery to Chlorine "/1 9;. Degrees, W/F Retention. 1
a. 100 l) 303 0.0% 288 7.6% h. 95 5 295 3.5% 301 0.0% c. 8 5 l 5 300 0.0% 30] 71% d. 70 3(1 296 3.3% 295 3.4% e. 50 5t) 29t 3.2% 295 3.3% f. 30 70 296 9.0% 290 6.0% g. 0 I00 280 26.4% 274 32.3% h. Untreated 206 1.7%
TABLE IV (cured 15 mins. at 300F) Total Wrinkle Strength Resin A Resin B Recovery Loss Due 7r It Degrees, W/F to Chlorine Retention.
a. 0 287 2.9% 287 3.0% b. 95 5 290 2.8% 285 0.0% c. 85 15 279 0.0% 285 0.0% d. 70 30 292 2.8% 280 8.3% e. 50 50 277 27.7% 287 27.7% f. 30 70 281 55.2% 28l 65.7% g. (l 100 266 64 7% 278 71.7% h. Untreated 206 l .7%
While we have set forth certain specific embodiments and modes of practice of the invention, it will be understood that this is solely for the purpose of illustration and that various changes and modifications may be made without departing from the scope of the disclosure or spirit of the appended claims.
We claim:
1. A method for providing a crease resistance to cellulosic-containing textile materials which comprises applying from about 2 to based on the weight of said textile materials of an aminoplast finish comprising an aqueous solution ol a mixture of l.3-dimethylol-4,5-- dihydroxyethyleneurea and a urea-formaldehyde con densate. said ureaiormaldchyde condensate being from 5 to 511% by weight of the total aminoplast and said l,3-dimethylol-4.5-dihydroxyethylencurea being from 50 to 95C? of the total aminoplast, said ureaformaldehyde condensate further containing from 1.8 to 3.6 mols of combined formaldehyde, thereafter drying said textile material and curing said finish on said textile at an elevated temperature. in the presence of an acid acting catalyst.
2. A cellulose containing material having an amino plast crease resistant finish cured thereon. said finish comprising from about 2 to 20%, based on the weight of said material. of a mixture of l,3-dimcthy1ol-4 5- dihydroxyethyleneurea and a urea-formaldehyde condensate, said condensate having from 1.8 to 3,6 mols of combined urea and being from about 5 to 50% of said finish and said l.3-dimethylol-4,5- dihydroxyethyleneurea being from 50 to 95% of said finish.
3. A method according to claim 1 wherein the urea formaldehyde condensate is from 5 to 3U /r by weight ot the total aminoplast and the l.3-dimcthylol-4,5-
dihydroxyethyleneurea is from 95 to by Weight 01' the total aminoplast.
4. A method according to claim 3 which comprises applying about 4.6%, based on the weight 01 said textile materials, of an aminoplast comprising an aqueous solution of a mixture of l 3-dimethylol-4.5 dihydroxyethyleneurea and a urea-formaldehyde con densate. said urea iormaldehyde condensate being about 70'?! by weight of the total aminoplast and said l.3-dimethylol-4,5-dihydroxyethyleneurea being about 30% by weight of the total aminoplast. said ureal'ormaldehyde condensate containing about 2.8 mols of combined formaldehyde.
5. A method according to claim 4 comprising drying said textile material at about 225F. for about 2.1] minutes and curing said dried textile material for about l5 minutes at 350F.
6. A material according to claim 2 wherein the ureaformaldehyde condensate is from 5 to 30% by weight of the total aminoplast and the l,3dimethylol-4.5- dihydroxyethyleneurea is from to 70% by weight of the total aminoplast.
7. A cellulose containing textile material finished according to the method ofclaim 4.
Claims (7)
1. A METHOD FOR PROVIDING A CREASE RESISTANCE TO CELLULOSICCONTAINING TEXTILE MATERIALS WHICH COMPRISES APPLYING FROM ABOUT 2TO 20%, BASES ON THE WEIGHT OF SAID TEXTILE MATERIALS OF AN AMINOPLAST FINISH COMPRISING AN AQUEOUS SOLUTION OF A MIXTURE OF 1,3-DIMETHYOL-4,5-DIHYDROXYETHYLENEUREA AND A UREA-FORMALDEHYDE CONDENSATE, SAID UREA-FORMALDEHYDE CONDENSATE BEING FROM 5 TO 50% BY WEIGHT OF THE TOTAL AMINOPLAST AND SAID 1,3-DIMETHYLOL-4,5-DIHYDROXYETHYLENEUREA BEING FROM 50 TO 95% OF THE TOTAL AMINOPLAST, SAID UREA-FORMALDEHYDE CONDENSATE FURTHER CONTAINING FROM 1.8 TO 3.6 MOLS OF COMBINED FORMALDEHYDE, THEREAFTER DRYING SAID TEXTILE MATERIAL AND CURING SAID FINISH ON SAID TEXTILE AT AN ELEVATED TEMPERATURE, IN THE PRESENCE OF AN ACID ACTING CATALYST.
2. A cellulose containing material having an aminoplast crease resistant finish cured thereon, said finish comprising from about 2 to 20%, based on the weight of said material, of a mixture of 1,3-dimethylol-4,5-dihydroxyethyleneurea and a urea-formaldehyde condensate, said condensate having from 1.8 to 3.6 mols of combined urea and being from about 5 to 50% of said finish and said 1,3-dimethylol-4,5-dihydroxyethyleneurea being from 50 to 95% of said finish.
3. A method according to claim 1 wherein the urea-formaldehyde condensate is from 5 to 30% by weight of the total aminoplast and the 1,3-di-methylol-4,5-dihydroxyethyleneurea is from 95 to 70% by weight of the total aminoplast.
4. A method according to claim 3 which comprises applying about 4.6%, based on the weight of said textile materials, of an aminoplast comprising an aqueous solution of a mixture of 1,3-dimethylol-4,5-dihydroxyethyleneurea and a urea-formaldehyde condensate, said urea-formaldehyde condensate being about 70% by weight of the total aminoplast and said 1,3-dimethylol-4,5-dihydroxyethyleneurea being about 30% by weight of the total aminoplast, said urea-formaldehyde condensate containing about 2.8 mols of combined formaldehyde.
5. A method according to claim 4 comprising drying said Textile material at about 225*F. for about 2.0 minutes and curing said dried textile material for about 1-5 minutes at 350*F.
6. A material according to claim 2 wherein the urea-formaldehyde condensate is from 5 to 30% by weight of the total aminoplast and the 1,3-dimethylol-4,5-dihydroxyethyleneurea is from 95 to 70% by weight of the total aminoplast.
7. A cellulose containing textile material finished according to the method of claim 4.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US351395A US3911181A (en) | 1968-09-27 | 1973-04-16 | Permanent press textile finish |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76334468A | 1968-09-27 | 1968-09-27 | |
| US12491071A | 1971-03-16 | 1971-03-16 | |
| US351395A US3911181A (en) | 1968-09-27 | 1973-04-16 | Permanent press textile finish |
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| US3911181A true US3911181A (en) | 1975-10-07 |
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| Application Number | Title | Priority Date | Filing Date |
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| US351395A Expired - Lifetime US3911181A (en) | 1968-09-27 | 1973-04-16 | Permanent press textile finish |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4551350A (en) * | 1982-09-30 | 1985-11-05 | Sws Silicones Corporation | Textile finishing with durable press resin composition |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2731364A (en) * | 1951-08-18 | 1956-01-17 | Basf Ag | Process for improving cellulose textile materials and product thereof |
| US3079279A (en) * | 1961-02-03 | 1963-02-26 | American Cyanamid Co | Blends of imidazolidinones and aminoplasts and method for finishing cellulose containing textile material |
| US3335113A (en) * | 1962-12-06 | 1967-08-08 | American Cyanamid Co | Process for preparing polymethylol ureas |
-
1973
- 1973-04-16 US US351395A patent/US3911181A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2731364A (en) * | 1951-08-18 | 1956-01-17 | Basf Ag | Process for improving cellulose textile materials and product thereof |
| US3079279A (en) * | 1961-02-03 | 1963-02-26 | American Cyanamid Co | Blends of imidazolidinones and aminoplasts and method for finishing cellulose containing textile material |
| US3335113A (en) * | 1962-12-06 | 1967-08-08 | American Cyanamid Co | Process for preparing polymethylol ureas |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4551350A (en) * | 1982-09-30 | 1985-11-05 | Sws Silicones Corporation | Textile finishing with durable press resin composition |
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