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United States Patent (19) 11 Patent Number: 4,820,307 Welch Et Al

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United States Patent (19) 11 Patent Number: 4,820,307 Welch Et Al United States Patent (19) 11 Patent Number: 4,820,307 Welch et al. (45) Date of Patent: Apr. 11, 1989 (54) CATALYSTS AND PROCESSES FOR 3,575,960 4/1971 Tesoro .................................... 8/120 FORMALDEHYDE-FREE DURABLE PRESS FINISHING OF COTTON TEXTILES WITH Primary Examiner-Paul Lieberman POLYCARBOXYLIC ACDS Assistant Examiner-John F. McNally Attorney, Agent, or Firm-M. Howard Silverstein; John 75 Inventors: Clark M. Welch, Metairie; Bethlehem D. Fado K. Andrews, New Orleans, both of La. 57 ABSTRACT 73) Assignee: The United States of America as Catalysts for the rapid esterification and crosslinking of represented by the Secretary of fibrous cellulose in textile form by polycarboxylic acids Agriculture, Washington, D.C. at elevated temperatures are disclosed. The catalysts are acidic or weakly basic salts selected from the alkali (21) Appl. No.: 207,461 metal dihydrogen phosphates and alkali metal salts of (22 Filed: Jun. 16, 1988 phosphorous, hypophosphorous, and polyphosphoric (51) Int. Cl.' ............................................ D06M 43/00 acids. Suitable polycarboxylic acids include saturated, (52) U.S. Clo ......................................... 8/120; 8/127.1; unsaturated and aromatic acids, as well as alpha 8/116.1 hydroxy acids. The textiles so treated exhibit high levels 58) Field of Search ................................. 8/120, 127.1 of wrinkle resistance and smooth drying properties durable to repeated laundering in alkaline detergents, 56) References Cited and do not contain or release formaldehyde. U.S. PATENT DOCUMENTS 3,526,048 1/1970 Rowland et al. ....................... 8/120 24 Claims, No Drawings 4,820,307 1. 2 kle resistance to cotton fabric was studied by Gagliardi CATALYSTS AND PROCESSES FOR and Shippee, American Dyestuff Reporter 52, P300-P303 FORMALDEHYDE-FREE DURABLE PRESS (1963). They observed small increases in fabric wrinkle FINISHING OF COTTON TEXT LES WITH resistance after relatively long periods of heating, and POLYCARBOXYLIC ACDS noted larger fabric strength losses than are obtained with formaldehyde-based crosslinking agents. These BACKGROUND OF THE INVENTION excessive strength losses and the low yield of crosslink 1. Field of the Invention ages were attributed to the long heat curing times This invention relates to new esterification catalysts needed with the inefficient catalysts then available. and esterification processes for crosslinking cellulose as 10 A more rapid and effective curing process for intro a means of imparting wrinkle resistance and smooth ducing ester crosslinks into cotton cellulose was de drying properties to cellulosic textiles without the use scribed by Rowland et al, Textile Research Journal 37, of formaldehyde or derivatives that release formalde 933-941 (1967). Polycarboxylic acids were partially hyde. neutralized with sodium carbonate or triethylamine 2. Description of the Prior Art 15 prior to application to the fabric in a pad, dry and heat There are numerous commercial processes for im cure type of treatment. Crosslinking of cellulose was parting wrinkle resistance, shrinkage resistance and obtained whenever the polycarboxylic acid contained smooth drying properties to cotton fabrics and gar three or more carboxyl groups suitably located in each ments, so that they retain their dimensions, smooth appearance and normal shape while in use and also 20 molecule. With certain polycarboxylic acids, a useful when machine washed and tumble dried. In most of level of wrinkle resistance was imparted. The condi these processes, formaldehyde or an addition product of tioned wrinkle recovery angle was measured before and formaldehyde is applied to the cotton textile together after five laundering cycles, and was found to decrease with an acid catalyst, and heat is then applied to pro somewhat as a result of laundering, even though no loss duce crosslinking of the cotton cellulose molecules. 25 ofester groups was detected. Neutralization of carboxyl The crosslinks thus formed in the cellulose impart to groups with 2% sodium carbonate even at room tem the fabrica tendency to return to its original shape and perature caused a 30% loss of ester groups. This indi smoothness when deformed by mechanical forces tem cates a lack of durability of the finish to alkaline solu porarily exerted on the fabric during its use or during tions such as solutions of alkaline laundering detergents. laundering and tumble drying. 30 The curing time needed in fabric finishing was more Formaldehyde addition products with urea, cyclic over too long to permit high speed, mill-scale produc ureas, carbamate esters or with other amides are widely tion. used crosslinking agents for durable press finishing, as Subsequently it was shown by Rowland and Brannan, the above wrinkle resistant, smooth drying treatments Textile Research Journal 38, 634-643 (1968), that cotton are called. The formaldehyde addition products, also 35 fabrics given the above cellulose crosslinking treatment known as N-methylol agents or N-methylolamides, are with polycarboxylic acids were recurable. Creases du effective and inexpensive, but have serious disadvan rable to 5 laundering cycles could be put into the fabrics tages. They continuously release vapors of formalde by wetting the latter, folding, and applying a heated hyde during durable press finishing of cotton fabric, iron. Evidence was obtained that the ester crosslinkages subsequent storage of the treated fabric, manufacture of 40 are mobile under the influence of heat, due to a transes the resulting garment, retailing of the garment, and terification reaction taking place between ester groups finally during use of the garment or textile by the con and adjacent unesterified hydroxyl groups on cotton sumer. The irritating effect of formaldehyde vapor on cellulose. the eyes and skin is a marked disadvantage of such These findings were elaborated by Rowland et al, finishes, but more serious is the knowledge that formal 45 dehyde is a carcinogen to animals and apparently also to U.S. Pat. No. 3,526,048. Sodium carbonate or triethyl humans continuously exposed to formaldehyde vapor amine were again the examples of bases used to partially for very long periods. A need is evident for durable neutralize the polycarboxylic acid subsequently applied press finishing agents and processes that do not require as the cellulose crosslinking agent. Rowland et al de formaldehyde or its unstable derivatives. 50 fined their process as requiring neutralization of 1% to Another disadvantage of the use of N-methylol 50% of all carboxylic acid functionality by a "strong agents in durable press treatments is that Lewis acid base' selected from the group consisting of alkali metal catalysts and high temperatures are required to bring hydroxides, carbonates, bicarbonates, acetates, phos about sufficiently rapid crosslinking of the cotton cellu phates and borates, prior to impregnating the fibrous lose by such finishing agents. The Lewis acid catalysts 55 cellulose with the aqueous polycarboxylic acid and cause undesirable losses of breaking and tearing heating to induce crosslinking. A strong base selected strength in cotton fabric during the heat curing step. from the group consisting of ammonia and certain The strength losses are due to degradation of cellulose amines also was indicated as suitable for the partial molecules by the Lewis acid catalysts at elevated tem neutralization of the polycarboxylic acid. perature. Such strength losses occur over and above the Stated limitations of the process of Rowland etal are adverse effects on strength of the crosslinkages pro that the process cannot be conducted with acids of duced in the cellulose. An added disadvantage of cer fewer than three carboxyl groups per molecule, or with tain nitrogenous finishes is their tendency to retain chlo acids containing olefinic unsaturation or hydroxyl rine from chlorine bleaches, with resultant fabric discol groups. The reasons were lack of reaction with cellu oration and strength loss if subsequently given a touch 65 lose and lack of effective crosslinking of cellulose up ironing. chains for development of high levels of wrinkle resis The use of polycarboxylic acids with or without tance. The limited durability of the finishes noted above catalysts in pad, dry and cure treatments to impart wrin was also a disadvantage, and the time required for com 4,820,307 3 4. plete curing was too long to permit practical rates of cellulosic fiber, such as cotton, that retains its durable cloth finishing. press properties after repeated laundering with alkaline detergents at elevated wash temperatures. SUMMARY OF THE INVENTION A fifth object is to provide esterification catalysts This invention provides rapid processes for durably 5 giving sufficiently rapid esterification and crosslinking imparting to fibrous cellulosic material, such as cotton of cellulosic fiber by polycarboxylic acids to permit and other cellulosic textiles, a high level of wrinkle practical rates of durable press finishing of cellulosic resistance and smooth drying properties by means of fiber-containing fabrics at cure temperatures below the non-nitrogenous cellulose crosslinking agents, without scorch temperature of the cellulose. the use of formaldehyde or derivatives that release O A sixth object is to provide odor-free durable press formaldehyde, and with less loss of tearing strength and finishes for cellulosic fiber-containing fabric that also breaking strength than produced by conventional N impart thermal recurability, soil
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