US3247018A

US3247018A - Process for treating textile materials

Info

Publication number: US3247018A
Application number: US232275A
Authority: US
Inventors: Hagge Walter; Dusing Josef; Kolbe Joachim
Original assignee: Bayer AG
Current assignee: Bayer AG
Priority date: 1961-10-25
Filing date: 1962-10-22
Publication date: 1966-04-19
Anticipated expiration: 1983-04-19
Also published as: NL284615A; AT238134B; BE623927A; DE1149687B; GB962421A

Description

United States Patent Ofiice 3,247,913 Patented Apr. 19, 1966 3,247,013 PROQIESS FOR TREATlNt'} TEXTILE MATERIALS Walter Hagge and J osei Busing, Leverlrusen, and Joachim Kolbe, Cologne-Flittard, Germany, assiguors to Farheniabriiren Bayer Airtiengesellschaft, Leverkusen, Germany, a German corporation No Drawing. Filed Oct. 22, 1962, filer. No. 232,275 Claims priority, appiication Germany, Oct. 25, 1961,

10 Claims. 61. 117 139.5

The present invention relates to the treatment of textile materials; more particularly it concerns a process in which the textile materials are treated with reaction products prepared by reacting (A) esters of higher fatty acids containing 12 to 20 carbon atoms condensed with alcohols containing 4 to 12 carbon atoms and/or polyhydric alcohols containing 2 to 6 hydroxyl groups with (B) amide amines in the form of salts or quaternization products, such as are obtainable by the action 1-l.7 mole of a carboxylic acid containing 62() carbon atoms or a functional derivative thereof on 1 mol of a diamine of the formula in which R and R stand independently from one another for an alkyl radical containing 1 to 8 carbon atoms and n is a number from 2-4, the amount of diamine employed being not more than 8 percent by weight of the reaction product.

As esters on which the reaction products to be used according to the present invention can be based, there may be mentioned, for example, tallow, coconut fat, olive oil, castor oil, palm kernel oil, lanolin, sperm oil and Wool fat; there may further be mentioned the esters obtainable from polyglycerol and higher fatty acids containing 12 to 20 carbon atoms, and the esters which result on heating polvglycerol or sorbitol with fats, for example beef taliow or coconut fat, in the presence of caustic alkalies.

As amide amines there may be considered the products which are obtained when carboxylic acids with 6 to 20 carbon atoms, such as caprylic acid, lauric acid, coconut fatty acid, palmitic acid or palm kernel fatty acid, stearic acid or oleic acid or their chlorides or methyl esters are treated dropwise with diamines of the given formula, such as diethylamino ethylamine, dimethylamino propylamine, methylethylamino propylamine or diethylamino butylamine, at about 170-180 C., and then held for two hours in vacuum and a further two hours Without vacuum at this temperature. The amide-amines formed are then converted into salts at about 100-130" C., with for example sulfuric acid, phosphoric -acid, formic acid, acetic acid, or lactic acid. For the transformation of the amide amines into quaternization products, there may be employed for example, dimethylor diethyl-sulfate, ethyl bromide, benzyl chloride, epichiorohydrin, chloracetamide or N-rnethylol chioracetamide.

The reaction of the esters with the salts or quaternization products of the amide amines is expediently carried out by heating for one or two hours at l130 C.

Suitable proportions of the required components may readily be determined from case to case by preliminary experiments. The reaction products can contain up to 70 percent by weight of the ester component, without the stability of the aqueous liquor produced suffering.

The process of the present invention may be applied to textile materials of the most various kinds, e.g., on fibers or threads of wool, cotton, regenerated cellulose, cellulose acetate, polyurethanes, polyamides, polyesters, polyoleilnes, polyacrylonitrile, and/ or mixed polymers of acrylonitrile with other vinyl compounds, or on fabrics or knitted goods produced thereform. The treatment of the textile materials can proceed in the customary manner, for example by agitating the materials in aqueous baths which contain the reaction products and are adjustecl as desired to neutral, alkaline or acid reaction, for some time, expediently at 3060 C., and then drying at about 7090 C. The present process may also be applied to yarns in vats and packing machines, on conical cross-wound bobbins and on piece goods of any kind, on the reel and on the foulard.

In place of water or additional to water, solvents of aliphatic or aromatic nature can also be used for making up the baths. In general, the amount of reaction product in the treatment bath is about 2-20 g./ litre.

With the aid of the process of the present invention it is possible to impart to the textile materials, in particular to those of synthetic origin, a high serviceabili ty. Materials which tend to form electrostatic charges are given an outstanding antistatic finish. In the production of yarns the treatment of the fibres with the reaction products according to the invention insures from every aspect a good textile workability, especially on the carding machine. The treated textile materials also possess an increased thermal stability, which has a favourable account in various finishing treatments. White goods, which has been treated according to the process of the present invention, undergoes no alteration on heating and in textile materials dyed or to be dyed, no deleterious effect is to be observed on the dying. For the treatment of stockings or socks of polyamide threads or fibres, those reaction products are especially suitable which were made with the use of Wool fat, lanolin, or mixtures of wool fat and tallow or of lanolin and castor oil. The stockings and socks treated with these products possess a soft and full handle and the stockings can also be very readily shaped, since they are simultaneously rendered antistatic. Moreover, reaction products which are produced with the use of quaternization products of the amide amines, are outstandingly suitable for finishing and impregnating purposes in combination with paramn or wax emulsions containing aluminum or zirconium salts or in combination with water-soluble urea or melamine formaldehyde precondensates. Other polymeric compounds, such as polyacrylates, can also be used concurrently, and also fatty alcohols or their alkoxylation products as well as mineral oils and mineral fats; thus for example an addition of 3-5 percent by weight of stearyl alcohol, calculated on the reaction product, permits the smoothness of the textile materials treated according to the invention to be significantly increased. If desired, the reaction products of the present invention can be employed also with other textile assistants, eg' with wetting agents or optical brighteners.

It is, moreover, to be emphasized also that the textile materials treated according to the invention in general have no unpleasant amine odour. In order to exclude any possibility of amine odour, it is recommended to use reaction products prepared from salts or quaternization products of amide amines in the presence of polyglycerol; such reaction products are odourless and the textile materials treated therewith likewise possess no undesirable amine smell.

The hitherto known agents proposed for treating textiles do not possess the advantageous properties described, to the same extent.

The following examples serve to illustrate the invention without, however, limiting the scope thereof; the parts are by weight.

Example 1 A fabric of polyacrylonitrile fibres was agitated for 30 minutes at a liquor-to-goods ratio of 20:1 at 40 C., in an aqueous bath which contained per litre 2.5 g. of the paste described below. The fabric was then centrifuged and dried at 80 C. The fabric thus treated which possessed no unpleasant smell, had a full and soft handle; it showed at the same time an antistatic finish.

The paste used was prepared in the following manner:

130 parts of tallow fatty acid glycerol ester, obtained by heating 1 mol of tallow and 2 mols of polyglycerol of molecular weight 170 in the presence of 1% by weight of potassium hydroxide to 18Q200 C., were stirred for 2% hours at 100 C. with 20 parts of Vaseline and 300 parts of the acetate of an amide amine which had been produced, according to col. 1, lines 41-59 of the specification, by heating 152 parts of a fatty acid mixture which contained altogether 98% by weight of saturated fatty acids, i.e., 62% of stearic acid, 32% of palmitic acid and 4% of myristic acid, to a temperature of 170180 C. in the presence of 124 parts of polyglycerol of molecular weight 170 with 33 parts of dimethyl-amino propylarnine and 18 parts of acetic acid anhydride. The reaction product obtained was then mixed with 550 parts of warm distilled water with addition of some glacial acetic acid. The amount of the diamine employed amounts to 7% by weight of the reaction product, and the molar ratio of carboxylic acid to diamine amounts to 1.7: 1. The 1% aqueous solution of the 45% paste obtained possesses a pH value of 4.6 to 4.9.

Example 2 Fibers of polymeric e-caprolactam (thickness 1.4/30 mm.) were treated in the manner described in Example 1 in an aqueous bath which contained 1 g. per litre of the paste there described. The fibres thus treated had a soft and pleasant handle; the further working up proceeded without trouble.

Example 3 Stocking of threads, or socks of fibers, produced from polymeric e-caprolactam, were treated in the manner described in Example 1 with an aqueous liquor containing 3 g. per litre of the paste described below. The stockings and socks thus treated then possessed a full, soft and smooth handle; they no longer felt rough. At the same time they acquired an antistatic finish.

The paste employed was produced in the following manner:

265 parts of the acetate of an amide amine prepared by reacting with one another 215 parts of 98% palmitic acid, 42 parts of dimethylamino propylarnine, 10.5 parts of dimethylamino butylamine and 25 parts of acetic acid anhydride with heating to 170-180 C. corresponding to the instructions of the third paragraph of this specification, are stirred at 100 C. for two hour swith 620 parts of wool fat; the reaction product formed was then stirred with 1300 parts of warm distilled water to a 40% paste.

Example 4 Hanks or piece goods produced from 50 parts of polyester fibres and 50 parts of wool, were agitated for 30 minutes at 45 C. at a liquor-to-goods ratio of :1 in an aqueous bath containing per litre 3 g. of the paste described below. After centrifuging and drying, the goods possessed a clearly improved feel; furthermore, they were given an antistatic finish.

The paste employed was produced in the following manner:

First 260 parts of stearic acid were amidated according to the instructions given in the third paragraph of this specification, by heating to 170-180 C., with 62 parts diethylamino ethylamine; the amide amine formed was quaternized for 1 /2 hours on the boiling water bath with 65 parts of epichlorohydrin and 370 parts of the quaternary compound thus obtained were then stirred at 100 C. for two hours with a mixture of 435 parts of beef tallow and 435 parts of wool fat. The reaction product formed was then stirred to a 40% paste with 1800 parts of warm distilled water. The amine content of the paste came to 5% and the molar ratio of fatty acid to diamine in the amide amine amounted to 1.67: 1.

We claim:

1. A process for treating textile materials comprising impregnating said materials with an active amount of the reaction product of (A) an ester obtained by condensing a higher fatty acid containing 12-20 carbon atoms with a member selected from the group consisting of a monohydric alcohol of 412 carbon atoms, and a polyhydric alcohol containing 26 hydroxyl groups; with (B) a member selected from the group consisting of the salt and the quaternization product of an amide amine obtained by reacting a diamine of the formula wherein R and R stand independently defined as alkyl having 18 carbon atoms and n is an integer of 2-4, with a reactive amount of (b) carboxylic acid having 6-20 carbon atoms,

the amount of diamine being not more than 8% by weight of the reaction product of (A) and (B).

2. The process of claim 1 wherein (B) is obtained by initially reacting 1 mol of the diamine with about 11:7 mol of monocarboxylic acid.

3. The process of claim 1 comprising incorporating the reaction product of (A) and (B) into a treating bath at a concentration of about 2-20 gm. per liter of water, agitating the textile materials therein, and thereafter drying the textile materials.

4. The process of claim 1 wherein the textile materials contain a substantial amount of at least one member of the group consisting of regenerated cellulose, cellulose acetate, polyurethane, polyamide, polyester, poly olefine, polyacrylonitrile, and wool.

5. The process of claim 1 wherein the textile materials consist essentially of polyacrylonitrile.

6. The process of claim 1 wherein the (A) ester is obtained by heating a member selected from the group consisting of polyglycerol of molecular weight and sorbitol with fat in the presence of caustic alkali.

7. The process of claim 1 wherein the (B) amide amine is obtained by reacting carboxylic acid selected from the group consisting of caprylic acid, lauric acid, coconut fatty acid, palmitic acid, palm kernel fatty acid, stearic acid, oleic acid, and the corresponding chlorides and methylesters, with an amine selected from the group consisting of diethylamino-ethylamine, dimethylamino propylamine, methylethylamino propylamine, and diethylamino butylamine.

8. The process of claim 1 wherein the reaction product of (A) and (B) is obtained by employing the quaternization product of the amide amine in the presence of an effective amount of polyglycerol.

9. The process of claim 5 wherein polyacrylonitrile material is agitated in an aqueous bath containing 2-20 gm. per liter of active ingredient in a liquor-to-goods ratio of about 20:1, at about 3060 C., and thereafter drying the material at a temperature of about 70-90 C.

10. A process for treating textile materials comprising impregnating said materials with an active amount of the reaction product of (A) an ester obtained by condensing a fatty acid containing 12-20 carbon atoms with a member selected from the group consisting of tallow, coconut fat, olive oil, caster oil; palm kernel oil, lanolin, sperm oil and wool fat; with (B) a member selected from the group consisting of the salt and the quaternization product of an amide amine obtained by reacting a diamine of the formula wherein R and R stand independently defined as alkyl having 1-8 carbon atoms and n is an integer of 2-4, with a reactive amount of (b) carboxylic acid having 6-20 carbon atoms, the amount of diarnine being not more than 8% by weight of the reaction product of (A) and (B).

References Cited by the Examiner UNITED STATES PATENTS 10 WILLIAM D. MARTIN, Primary Examiner.

RECHARD D. NEVIUS, Examiner.

Claims

1. A PROCESS FOR TREATING TEXTILE MATERIALS COMPRISING IMPREGNATING SAID MATERIALS WITH AN ACTIVE AMOUNT OF THE REACTION PRODUCT OF (A) AN ESTER OBTAINED BY CONDENSING A HIGHER FATTY ACID CONTAINING 12-20 CARBON ATOMS WITH A MEMBER SELECTED FROM THE GROUP CONSISTING OF A MONOHYDRIC ALCOHOL OF 4-12 CARBON ATOMS, AND A POLYHYDRIC ALCOHOL CONTAINING 2-6 HYDROXYL GROUPS; WITH (B) A MEMBER SELECTED FROM THE GROUP CONSISTING OF THE SALT AND THE QUATERNIZATION PRODUCT OF AN AMIDE AMINE OBTAINED BY REACTING A DIAMINE OF THE FORMULA