US3660009A - Method of manufacturing ready-to-wear crease-resistive garments - Google Patents
Method of manufacturing ready-to-wear crease-resistive garments Download PDFInfo
- Publication number
- US3660009A US3660009A US821512*A US3660009DA US3660009A US 3660009 A US3660009 A US 3660009A US 3660009D A US3660009D A US 3660009DA US 3660009 A US3660009 A US 3660009A
- Authority
- US
- United States
- Prior art keywords
- fabric
- garment
- crease
- acetal
- glycol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000004744 fabric Substances 0.000 claims abstract description 70
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 34
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000001035 drying Methods 0.000 claims abstract description 11
- 229920005862 polyol Polymers 0.000 claims abstract description 11
- 150000003077 polyols Chemical class 0.000 claims abstract description 11
- 239000004753 textile Substances 0.000 claims abstract description 10
- 239000003377 acid catalyst Substances 0.000 claims abstract description 9
- 238000003825 pressing Methods 0.000 claims abstract description 8
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims abstract 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 45
- 238000011084 recovery Methods 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 27
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- 230000036961 partial effect Effects 0.000 claims description 4
- 239000000600 sorbitol Substances 0.000 claims description 4
- 235000010356 sorbitol Nutrition 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- 239000004925 Acrylic resin Substances 0.000 claims description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 3
- 229930195725 Mannitol Natural products 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 3
- 239000000594 mannitol Substances 0.000 claims description 3
- 235000010355 mannitol Nutrition 0.000 claims description 3
- 230000002035 prolonged effect Effects 0.000 abstract description 7
- 150000001241 acetals Chemical class 0.000 description 36
- 239000000460 chlorine Substances 0.000 description 9
- 235000019645 odor Nutrition 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- -1 mannnitol Chemical compound 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920000877 Melamine resin Polymers 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 230000037303 wrinkles Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000010409 ironing Methods 0.000 description 3
- 238000004900 laundering Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002979 fabric softener Substances 0.000 description 2
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 2
- 229940050906 magnesium chloride hexahydrate Drugs 0.000 description 2
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 238000007655 standard test method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- VREIZDQPOMNWLM-UHFFFAOYSA-N 3-aminobutan-2-ol;hydrochloride Chemical compound Cl.CC(N)C(C)O VREIZDQPOMNWLM-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 101100434016 Caenorhabditis elegans gar-2 gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- MQAXXEDQIMGGLF-UHFFFAOYSA-N [2,3-dihydroxy-2-(hydroxymethyl)propyl] carbamate Chemical compound NC(=O)OCC(O)(CO)CO MQAXXEDQIMGGLF-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004049 embossing Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960002337 magnesium chloride Drugs 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- SXVDZIOMWSPFCO-UHFFFAOYSA-N methyl n,n-bis(hydroxymethyl)carbamate Chemical compound COC(=O)N(CO)CO SXVDZIOMWSPFCO-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- 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
- D06M13/137—Acetals, e.g. formals, or ketals
Definitions
- This invention relates to the method of manufacturing ready-to-wear, crease-retentive garments.
- the method comprises treating a cellulosic fabric with a specific type of polymeric acetal, drying the fabric, forming a garment from such treated fabric, and then subjecting the garment to a prolonged cure, thereby imparting to the fabric a crease-recovery angle of at least about 260.
- thermosetting resins employed therein frequently possess the undesirable qualities described above, that is, they tend to retain chlorine when the fabric is bleached. They tend to cure permaturely while they are stored and they tend to give off unpleasant odors.
- the fabric is impregnated with the thermosetting resin, it is necessary to maintain a certain amount of moisture in the fabric when it is dried so as to avoid premature curing. Therefore, when the fabric is dried, it is essential that the drying process be carried out under very carefully controlled conditions so as to avoid overdrying and pre-curing. Usually about 2-8 percent of moisture must be retained.
- wash-wear garments, and the like exhibiting excellent properties of wrinkle-resistance and crease-retention
- wash-wear garments, and the like exhibiting excellent properties of wrinkle-resistance and crease-retention
- This wrinkle-recovery tester method measures the wrinkle recovery of a fabric quite accurately. Briefly described, test specimens of the size of 1.5 X 4 cm. are cut from a fabric to be tested. The long dimension corresponds to the direction of the test. These specimens are prepared by cutting in both the warp and filling directions. Generally, six specimens of each are used to obtain an average value. The specimens are maintained for at least 24 hours in an atmosphere having a relative humidity of 65 percent and a temperature of 70 F. The fabric is creased under a weight of 500 grams for 5 minutes. Five minutes after the weight is removed, the angle of recovery is measured. The maximum angle of recovery is 180. The angle of recovery of a specimen cut in the warp direction is added to the angle of recovery of a specimen cut in the filling direction in order to arrive at the final angle of recovery value for the fabric. A high angle of recovery indicates good wrinkle recovery.
- the process of this invention completely avoids the aforementioned drawbacks encountered in the use of urea-formaldehyde, melamine-formaldehyde, etc., as wrinkle-proofing agents, both in the manufacture and in the use of garments treated with such reagents. Moreover, it has been found to be of considerable benefit that the polymeric acetals employed according to the present invention are not adversely affected if the fabric is over-dried. Accordingly, the complicated controls that are ordinarily required with the usual impregnating compounds, to prevent over-drying and pre-curing, can be avoided.
- polymeric acetal reagents which are used according to this invention are prepared by reacting formaldehyde with a Water-soluble polyol in the presence of an acid catalyst according to well-known methods. These polyacetals are watersoluble and have a boiling point of at least about 300 F.
- for-rnaldehyde includes the common formaldehyde derivatives, namely, paraformaldehyde, trioxymethylene, methylal, and the like.
- the water-soluble polyols which may be used include ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, sorbitol, glycerine, mannnitol, glycol monoethers, partial esters of polyhydric alcohols, and the like.
- Blends of polymeric acetals may be used as well as single polymeric acetals.
- the acetals may be employed in combination with carbamates, as for example, with dimethylolmethyl carbamate or dimethylol-hydroxyethyl carbamate, or with triazone resins, or with melamine-formaldehyde resins, or with polyvinyl alcohol, or with hydroxyethyl cellulose.
- carbamates as for example, with dimethylolmethyl carbamate or dimethylol-hydroxyethyl carbamate, or with triazone resins, or with melamine-formaldehyde resins, or with polyvinyl alcohol, or with hydroxyethyl cellulose.
- carbamates as for example, with dimethylolmethyl carbamate or dimethylol-hydroxyethyl carbamate, or with triazone resins, or with melamine-formaldehyde resins, or with polyvinyl alcohol, or with hydroxye
- the acetals employed in the process of this invention may be prepared by methods well known in the art.
- a glycol and paraforrnaldehyde may be heated together in the v n r A up presence of a trace of an acid catalyst, such as sulfuric acid, methane sulfonic acid, paratoluene sulfonic acid, and the like, the dihydric alcohol and the aldehyde being in molar proportions.
- An azeotropic vehicle such as benzene, toluene, xylene, ethyl benzene, is employed.
- azeotropic distillation one mol of water is removed and the reaction proceeds essentially to completion in good yield.
- the product may be recovered as a viscous liquid, often with a tendency to crystallize.
- Pad baths must contain, in addition to an appropriate acetal composition, a suitable curing catalyst, such as magnesium chloride, zinc sulfate, zinc nitrate, ammonium chloride, 2- amino-methyl propanol hydrochloride, oxalic acid, citric acid, and the like. These catalysts are preferably salts of strong acids and weak bases, or Lewis acids.
- the acid catalyst is advantageously present in an amount of from about 5-400 percent by weight of the acetal content in the bath, and the acetal content is from about 5 to about 40 percent by weight of the bath.
- Certain antioxidants, reducing agents, or oxidizing agents, sequestrants, and other auxiliaries may also be incorporated into the finishing bath in order to minimize thermal discoloration of the cellulose.
- the fabric After the cellulosic fabric has been impregnated with the pad bath containing the polymeric acetal, the fabric is dried. The drying may be complete or a small amount of moisture may be present, up to about 7-10 percent, for example. Generally, this treated fabric is stored or shipped to garment manufactures, and during this period of storage, the treated fabric does not tend to pre-cure to any undesirable extent.
- the garment After the fabric has been cut and sewn so as to form the desired garment, the garment is pressed into a suitable shape, such as by forming creases or pleats. The garment is then subjected to a prolonged cure, that is, to a temperature between about 320 F. and 400 F.
- the prolonged heating is at a higher temperature and for a longer period of time than ordinarily would be expected.
- the prolonged curing produces a further increase in the crease-recovery angle of the treated fabric to a value over about 260, thereby permitting the garment to be commercially suitable for press-free wash-wear use. If a temperature as low as 320 F, is employed, generally at least about minutes of cure time is required to produce a creaserecovery angle of 260 in the fabric.
- the cellulosic textile material which can be used includes natural cellulose or regenerated cellulose, such as hydrolyzed cellulose acetate, viscose rayon, or any suitable fabric blend having a major portion of cellulosic material therein.
- EXAMPLE 2 A polymeric acetal was prepared by reacting ethylene glycol with paraformaldehyde as described above. Finishing baths were prepared containing the acetal, magnesium chloride hexahydrate catalyst, and a 30 percent polyethylene fabric softener.
- Standard weight shirting broadcloth, scoured, bleached and mercerized was padded through the bath to 60-70 percent wet pickup, framed, dried l is minutes at 280 F stored for 1 week, and then cured for 10 minutes at 340 F.
- Sample swatches were tested for chlorine retention damage by the standard test methods according to the method described in the Technical Manual of the American Association of Textile Chemists and Colorists (1964) Damage By Chlorine Retained Standard Test Method No. 92-1962. The following results were obtained.
- EXAMPLE 3 A bath was prepared containing the diethylene glycol acetal of Example 1, 3 percent of magnesium chloride hexahydrate, 2 percent of a 30 percent polyethylene fabric softener, and 2.7 percent of a 45 percent reactive polyacrylate emulsion, The broadcloth of Example 2 was padded to 60-70 percent wet pickup, framed, dried for l i minutes at 280 F., stored for l week and cured for 10 minutes at 340 F., with the following results;
- a method of making wash-wear, press-free garments having crease-retention properties which comprises impregnating a cellulosic textile fabric with an aqueous solution of (a) a water-soluble polymeric acetal of formaldehyde and a polyol, said acetal having a boiling point of at least about 300 F., and being present in an amount of from about 5 to 40 percent by weight of said solution, and said polyol being a member of the group consisting of ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, sorbitol, glycerine, mannitol, glycol monoethers, and partial esters of polyhydric alcohols, and (b) an acid catalyst present in an amount of from about 5 to 400 percent by weight of the acetal, drying the fabric, forming a garment from the fabric and pressing at least one crease into the garment, and
- a method of making wash-wear, press-free garments having crease-retention properties which comprises impregnating a cellulosic textile fabric with an aqueous solution of (a) a water-soluble polymeric acetal of formaldehyde and a polyol, said acetal having a boiling point of at least about 300 F., and being present in an amount of from about 5 to 40 percent by weight of said solution, and said polyol being a member of the group consisting of ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, sorbitol, glycerine, mannitol, glycol monethers, and partial esters of polyhydric alcohols, (b) an acid catalyst present in an amount of from about 5 to 400 percent by weight of the acetal, and (c) from about 1-15 percent, by weight of said solution, of a self-crosslinking polyacrylate resin, drying the fabric, forming a garment
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Treatment Of Fiber Materials (AREA)
Abstract
Description
Claims (7)
- 2. A method of making wash-wear, press-free garments having crease-retention properties which comprises impregnating a cellulosic textile fabric with an aqueous solution of (a) a water-soluble polymeric acetal of formaldehyde and a polyol, said acetal having a boiling point of at least about 300* F., and being present in an amount of from about 5 to 40 percent by weight of said solution, and said polyol being a member of the group consisting of ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, dipropylene glycol, dibutylene glycol, sorbitol, glycerine, mannitol, glycol monethers, and partial esters of polyhydric alcohols, (b) an acid catalyst present in an amount of from about 5 to 400 percent by weight of the acetal, and (c) from about 1-15 percent, by weight of said solution, of a self-crosslinking polyacrylate resin, drying the fabric, forming a garment from the fabric and pressing at least one crease into the garment, and then heating the garment at a temperature between about 320* F. and 400* F. for a sufficient period of time to impart to the fabric a crease-recovery angle of at least about 260*.
- 3. The method of claim 1 wherein said polyol is ethylene glycol.
- 4. The method of claim 1 in which the impregnated fabric is dried to a moisture content of less than about 2 percent prior to the curing of the treated fabric.
- 5. The method of claim 2 in which a water-soluble polymeric acetal of formaldehyde and ethylene glycol is employed as the acetal.
- 6. A garment produced in accordance with the method of claim 1.
- 7. A garment produced in accordance with the method of claim 2.
- 8. A garment produced in accordance with the method of claim 3.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US82151269A | 1969-02-02 | 1969-02-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3660009A true US3660009A (en) | 1972-05-02 |
Family
ID=25233585
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US821512*A Expired - Lifetime US3660009A (en) | 1969-02-02 | 1969-02-02 | Method of manufacturing ready-to-wear crease-resistive garments |
Country Status (1)
Country | Link |
---|---|
US (1) | US3660009A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2727136A1 (en) * | 1994-11-22 | 1996-05-24 | Dhj Ind Europ | PROCESS FOR TREATMENT OF A THERMO-ADHESIVE REINFORCING SUBSTRATE TO BE INCORPORATED IN A TEXTILE SUBSTRATE TO MAKE CRUSH-RESISTANT AND PRODUCT THUS OBTAINED |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2785948A (en) * | 1954-01-08 | 1957-03-19 | Quaker Chemical Products Corp | Process for stabilizing cellulose textile materials against dimensional changes by applying simple acetals and products resulting therefrom |
US2785949A (en) * | 1954-01-08 | 1957-03-19 | Quaker Chemical Products Corp | Process for the dimensional control of cellulose textile materials by applying polymeric acetals and products resulting therefrom |
US2974432A (en) * | 1956-02-20 | 1961-03-14 | Koret Of California | Press-free crease retained garments and method of manufacture thereof |
US3409387A (en) * | 1966-04-15 | 1968-11-05 | United Merchants & Mfg | Press-free garments and methods of manufacture |
-
1969
- 1969-02-02 US US821512*A patent/US3660009A/en not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2785948A (en) * | 1954-01-08 | 1957-03-19 | Quaker Chemical Products Corp | Process for stabilizing cellulose textile materials against dimensional changes by applying simple acetals and products resulting therefrom |
US2785949A (en) * | 1954-01-08 | 1957-03-19 | Quaker Chemical Products Corp | Process for the dimensional control of cellulose textile materials by applying polymeric acetals and products resulting therefrom |
US2974432A (en) * | 1956-02-20 | 1961-03-14 | Koret Of California | Press-free crease retained garments and method of manufacture thereof |
US3409387A (en) * | 1966-04-15 | 1968-11-05 | United Merchants & Mfg | Press-free garments and methods of manufacture |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2727136A1 (en) * | 1994-11-22 | 1996-05-24 | Dhj Ind Europ | PROCESS FOR TREATMENT OF A THERMO-ADHESIVE REINFORCING SUBSTRATE TO BE INCORPORATED IN A TEXTILE SUBSTRATE TO MAKE CRUSH-RESISTANT AND PRODUCT THUS OBTAINED |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2785947A (en) | Process for producing durable mechanical effects on cellulose fabrics by applying acetals and products resulting therefrom | |
US3236676A (en) | Treatment of cellulose with tetrakis (hydroxymethyl) phosphonium resins | |
US2339203A (en) | Treatment of cellulosic textile material | |
US3597147A (en) | Modification of cellulosic textile materials with pyrimidones | |
US3852829A (en) | Composition and method for producing wrinkle-free permanently pressed cellulosic textile materials | |
US2901463A (en) | Compositions, textiles treated therewith and processes for the treatment thereof | |
US3458869A (en) | Method of producing press-free garments and products thereof | |
US2412832A (en) | Textile material and method of preparing it | |
US3434794A (en) | Delayed cure of cellulosic articles | |
US3420696A (en) | Aldehyde fixation on polymeric material | |
US3052570A (en) | Textile finishing resin, wrinkle resistant cellulose textile, processes of making resin and treated textile | |
US3653805A (en) | Delayed cure process using formaldehyde vapor to cause creaseproofing | |
US4295847A (en) | Finishing process for textiles | |
US3801546A (en) | Manufacture of textile finishing agents comprising condensing urea and hcho followed by condensation with glyoxal | |
US2785948A (en) | Process for stabilizing cellulose textile materials against dimensional changes by applying simple acetals and products resulting therefrom | |
US3026216A (en) | Treatment of textile fabrics with methylglycidyl ethers | |
US3660009A (en) | Method of manufacturing ready-to-wear crease-resistive garments | |
US3617197A (en) | Improving the wrinkle resistance of cellulosic textiles | |
US2889192A (en) | Method of treating cellulose-containing textile materials, materials so treated and diester composition therefor | |
US3576591A (en) | Methylolated cyclic urea compositions containing sodium formate or sodium tetraborate | |
US3015584A (en) | Wrinkle resistance treatment for cellulosic textile fabrics | |
US3039167A (en) | Method for improving the properties of fabrics containing cross-linked regenerated cellulose material | |
US3089747A (en) | Method of preparing rayon plisse | |
US3434161A (en) | Textile fabric treatment | |
US3930087A (en) | Crease resistant cellulosic textile material |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: BARCLAYS AMERICAN, 1 BUSINESS CREDIT, INC. 111 FOU Free format text: SECURITY INTEREST;ASSIGNOR:MILLMASTER ONYX GROUP, INC., A DE CORP.;REEL/FRAME:004139/0941 Effective date: 19821222 Owner name: MILLMASTER ONYX GROUP, INC., A DE CORP. Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:KEWANEE INDUSTRIES, INC.;REEL/FRAME:004139/0909 Effective date: 19830407 |
|
AS | Assignment |
Owner name: FIRST FLORIDA BANK (N.A.), 111 EAST MADISON, TAMPA Free format text: SECURITY INTEREST;ASSIGNOR:LESLIE CO., A NJ. CORP.;REEL/FRAME:004661/0485 |
|
AS | Assignment |
Owner name: HI-TEK POLYMERS, INC., ONE RIVERFRONT PLAZA, LOUIS Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:MILLMASTER ONYX GROUP, INC., A DE CORP.;REEL/FRAME:004791/0249 Effective date: 19871105 Owner name: HI-TEK POLYMERS, INC., ONE RIVERFRONT PLAZA, LOUIS Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:MILLMASTER ONYX GROUP, INC., A DE CORP.;REEL/FRAME:004791/0249 Effective date: 19871105 Owner name: HI-TEK POLYMERS, INC., KENTUCKY Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:MILLMASTER ONYX GROUP, INC.;REEL/FRAME:004791/0249 Effective date: 19871105 |
|
AS | Assignment |
Owner name: COLLOIDS, INC., GEORGIA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:HI-TEK POLYMERS, INC.;REEL/FRAME:005046/0503 Effective date: 19890308 Owner name: COLLOIDS, INC., GEORGIA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:HI-TEK POLYMERS, INC.;REEL/FRAME:005046/0503 Effective date: 19890308 |