US2541101A - Hydantoin derivative textile lubricants - Google Patents

Hydantoin derivative textile lubricants Download PDF

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US2541101A
US2541101A US37048A US2541101A US 2541101 A US2541101 A US 2541101A US 37048 A US37048 A US 37048A US 2541101 A US2541101 A US 2541101A
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Prior art keywords
amine
hydantoin
textile
fabric
reaction
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Jr Hillary Robinette
Carl R Pacifico
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Publicker Ind Inc
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Publicker Ind Inc
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72Two oxygen atoms, e.g. hydantoin
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS, OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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 nitrogen
    • D06M13/35Heterocyclic compounds
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2352Coating or impregnation functions to soften the feel of or improve the "hand" of the fabric

Description

Patented Feb. 13, 1951 HYDANTOIN DERIVATIVE TEXTILE LUBRICANTS Hillary Roblnette, Jr.,

and Carl R. Paciilco, Philadelphia, Pa., assignors to Publicker Industries Inc., Philadelphia, sylvanla Pa., a corporation of Penn- No Drawing. Application January 2, 1948, Serial No. 370

Claims. (Cl. l17'139.5)

The present invention relates to textile lubricents and softeners. More particularly, it is concerned with textile softeners and lubricants comprising a reaction product prepared from a long chain primary or secondary amine and a hydantoin. The structure of such products, however, is not accurately known, although chemical reaction does occur when the desired hydanto n is mixed with a suitable long chain amine inasmuch as substantial quantities of heat are given off and the pH of the reaction mixture is observed to change from the acid side to a substantially neutral pH at the completion of the reaction.

In the past, numerous substances have been proposed as textile lubricants and softeners and have been utilized for this purpose with varying degrees of success. Initially, sulfcnated tallow emulsions were employed to enhance the softness and draping properties of cotton, rayon, cellulose acetate, and other similar materia's. Such emulsions were unsatisfactory, however, inasmuch as cloth treated therewith, on standing, acquired a rancid odor and-on washing lost the softness imparted to it by treatment with these emulsions. A second type of textile softener is that derived from the long chain amines and lower aliphatic acids. The resulting amine salts although capable of imparting a high degree of softness and drapyhand to the fabric treated, materially reduce the light resistance of the direct dyes in the fabrics. Moreover, on contact of cloth so treated with alkalies, the softening agent is decomposed, liberating the free amine and lower aliphatic acid salt, thereby resulting in a fabric having substantially no unnatural softness. Quaternary ammonium salts have likewise been rather widely employed as textile softening agents and while such materials are generally quite stable to alkali and washing, they have a very deleterious effect on the light resistance of the direct dyes in these fabrics.

We have now discovered a completely new class of textile lubricants and softeners, i. e., the hydantoln-long chain amine reaction products of the type mentioned above, which are capable of imparting to the fabric a full, soft, drapy hand and exhibit excellent resistance. to alkalies and washing and have no harmful effect whatever on the light resistance or fastness of direct dyes. The textile softeners of our invention are generally preferably prepared by reacting a hydantoin having the following general structural formula:

wherein R represents either hydrogen, phenyl, or an alkyl group having less than six carbon atoms; R is either phenyl, hydrogen; or an alkyl group of less than six carbon atoms, the sum of the carbon atoms represented by the substituents R and R being less than ten; and an aliphatic amine of the formula:

in which R is an aliphatic chain of from ten to twenty carbon atoms and R is either hydrogen or an alkyl group having less than ten carbon atoms. The long chain primary or secondary amine is reacted with the hydantoin preferably in substantially equimolecular quantities at a temperature slightly above the melting point of the amine utilized. After the amine has melted, the hydantoin is added to it and thereafter the mixture is vigorously stirred while warm water is added. Alternatively, an aqueous solution of hydantoin may be added to the molten amine with agitation. As water is added the hydantoin is dissolved and is then capable of reacting with the amine. As the amine is consumed, the yellow color generally present in pears and a white, smooth, heavy-bodied emulsion is obtained. The product thus produced is well dispersed throughout the reaction mixture and requires no auxiliary emulsifying agent, but may be applied directly to the fabric to be treated by any of the well known methods such as padding, exhaustion, and the like, to give in every instance excellent softness, drape, and ban. dle to the textile material treated. Additionally, the softener thus produced exhibits excellent adherence to cotton, rayon, cellulose acetate, etc, and imparts rag-like characteristics to paper fibers treated therewith.

The concentration of the textile softeners of our invention suitable for use in obtaining the desired softening effect may vary rather widely, and in general it may be said that such concentration depends somewhat upon the density and weave of the fabric to be treated. In the majority of instances, however, we have found that the desired degree of softness can be secured by ereploying emulsions containing as little as 0.2% of softener, and it rarely becomes necessary to em-- ploy emulsions having in excess of 2.0% softener.

Suitable hydantoins that may be utilized in the preparation of the softening agents of our invention comprise a relatively large group of compounds. Typical hydantoins for this purpose are 5-methy1 hydantoin, 5-methyl-5phenyl hydantoin, 5,5-dimethyl hydantoin, 5-phenyl hydantoin, S-ethyl hydantoin, 5-methyl-5-ethyl hydantoin, 5-methyl-5-propyl hydantoin, and the like. Long chain amines suitable for use in preparing the textile softening agents of our invention include dodecyl amine, octadecyl amine, ethyl dosuch solutions disaptadecyl amine.

decyl amine, propyl octyl amine, eicosyl amine,

hexadecyl amine, propyl undecyl amine, mixtures of various of these amines such as those commercially available, for example, mixtures containing 20% to 30% hexadecyl amine, 65% to 75% octadecyl amine and from about 1% to octadecenyl amine, and the like.

Our invention may be further illustrated by the following specific examples:

Example 1 'methyl undecyl amine, propyl tridecyl amine,

A mixture consisting of equimolecular proportions of 5,5-dimethyl hydantoin and octadecyl amine is heated to approximately 44 C. whereupon the mixture is substantially fluid. Thereafter, warm water is slowly added with agitat on and the temperature is allowed to rise exothermically during the introduction of water, the latter. being added in an amount sufficient to give an aqueous emulsion containing 1% of the reaction product of 5,5-dimethyl hydantoin and oc- The emulsion thus prepared is then padded onto 6 oz. vat-dyed shirting fabric and thereafter the cloth so treated is dried at 105 C. After twelve washings there is no noticeable loss in softness or drape of the fabric and the light resistance of the dye is unimpaired.

Example 2 To 1 mole of 5,5-dimethyl hydantoin is added a stoichiometric quantity of a commercially available mixture containing chiefly hexadecyl amine and octadecyl amine. The resulting mixture is then heated to a temperature of between 45 and 50 C., after which there is addedwith vigorous agitation sufficient warm water to produce a final emulsion containing of the hydantoin-amine reaction product. After a white, smooth, heavy-bodied emulsion is obtained indicatin that the reaction has reached substantial completion, the softening agent thus produced is then diluted with water to a 0.2% concentration and exhausted onto a jacquard type directdyed cotton bedspread fabric by immersing the latter into the emulsion. The fabric thus obtained after having been dried and washed twelve times showed no noticeable decrease in softness or drape, nor is there any noticeable deleterious effect on the dye in the fabric on exposure to light.

Example 3 An emulsion containing as the active textile softening agent 0.5% of the reaction product of eicosyl amine and 5-phenyl hydantoin, prepared I in accordance with the general procedure out- A 1% solution of a textile softening agent prepared by reacting 5-methyl-5-phenyl hydantoin with propyl hexadecyl amine, in accordance with the-conditions set forth above, is sprayed onto a tissue paper during the manufacture thereof just prior to its entry into the calender stack. The paper so produced is softened materially to give it the desired rag-like characteristics.

Example 5 An aqueous emulsion containing 1% of a textile softening agent is prepared in accordance with the procedure outlined above by reacting hydantoin with dodecyl amine. Cotton sheeting is then passed through a bath containing the aforesaid aqueous emulsion to give on drying a smooth, soft fabric having an even handle. After washing twelve times there is no noticeable loss in the softness of the fabric.

From the foregoing discussion and examples, it will'b'e apparent to those skilled in the art that our invention provides novel and highly eflicient textile lubricants and softeners. The softening agents of our invention impart to the textile material treated a high degree of softness, drape, flexibility, and handle. but do not cause any appreciable yellowing of the material even after prolonged contact therewith. Moreover, as pre viously pointed out, the softening and lubricating agents of our invention have no deleterious effect whatever on the light resistance of direct dyes and in addition are quite stable to alkali. Additionally, the reaction products of our invention cause less discoloration of the textile materials to which they are applied than do other textile lubricating and softening agents previously employed. Also, the products of our invention are much easier to apply than other softening agents previously utilized, since they may be'dispersed or dissolved in water with great ease in contrast to the difliculties encountered in dispersing or dissolving previously known textile softening agents. Moreover, the softening agents of our invention may be prepared from readily available and inexpensive amines, and,

hence, from an economical standpoint are much more desirable than numerous of the other textile softening agents heretofore employed. Likewise the hydantoins utilized in preparing our novel textile softeners are readily available and the raw materials employed in synthesizing such compounds are relatively inexpensive.

It will be apparent to those skilled in the art that our invention is susceptible of numerous modifications without departing from the scope thereof. For example, the textile lubricants of our invention may be prepared by substituting for the water specified in the description and examples, a suitable alcohol such as ethanol or aqueous solutions thereof. Also, if desired, traces of acid or alkali may be utilized to promote enolization of the hydantoin, thereby assisting in the formation of the reaction products of our invention. In general, it may be said that the utilization of any reaction product of a hydantoir with a long chain primary or secondary aliphatiz amine as a softening agent for textiles lies within the scope of our invention.

What we claim is:

1. In a process for the preparationof reactior. products suitable for improving the softness and handle of textiles, the step which comprises reacting in substantially equimolecular preparations an aqueous mixture of a hydantoin of the general formula 1 R1 ee H-N N-H wherein R represents a member selected from the group consisting of hydrogen, phenyl, and an I alkyl group having less than six carbon atoms: R. is a member of the group consistingof phenyl, hydrogen and an alkyl group of less than six carbon atoms, the sum of the carbon atoms represented by the substituents R and B being less than ten; and an aliphatic amine ofthe formula:

R -N(R=) H in which R is an aliphatic chain of from ten to twenty carbon atoms and R is a member of the group consisting of hydrogen and an alkyl group having less than ten carbon atoms; at a temperature not in substantial excess of the melting point of the amine. I

2. The process of claim 1 in which the hydantoin is 5,5-dlmethyl hydantoin and the amine is octadecyl amine.

3. The process of claim 1 in which the hydantoin is 5,5-dimethyl hydantoin and the amine portion of the reaction product is derived from a mixture of hexadecyl and octadecyl amines.

4. The reaction product of a hydantoin of the formula:

n1 R-C==O having less than ten carbon atoms; said reac- Y tion product having been prepared by heating the amine until it is in a molten condition and thereafter adding with agitation an aqueous mixture containing a substantially equimolecular amount of the hydantoin.

5. A reaction product of the type covered by claim 4 in which hydantoin and product is as and octadecy ,amines. e .6. A r on product covered by claim 4 in which the'tiydahtoin is 5-methyl-5-pheny1 hylie amine portion of the reaction d from a mixture of hexadecyl dantoin the amine is propylhexadecyl amine.

'7. The, reaction product covered by claim 4 in which this hydantoin isas-dimeth i hydantoin and the amine is octadecyl amine.

- '-8.An aqueous bath for the treatment of te x- 18111881111 persed therein a small amount of a textile f ning agent which is active to impart to th e fabric an and even handle. said softening\agent being a reaction product of a hydantoin of the formula:

RI n-oc-o n-N -n an aliphafic amine of the for-- .the hydantoin is lifi-dimethyl' wherein It represents .a member selected from the group consisting of hydrogen, phenyl, and an alkyl group having less than six carbon atoms; R is a member of the group consisting of phenyi, hydrogen and an alkyl group of less than six carbon atoms, the sum of the carbon atoms represented by the substituents R and R being les. than ten; and an aliphatic amine of the formula:

in which R is an aliphatic chain of from ten to twenty carbon atoms and R. is a member 0! h group consisting of hydrogenand an aikyi group having less than ten carbon atoms.

9. The aqueous bath of claim 8 in which the textile softening agent is derived from the interaction of 5,5-dimethyl hydantoin with octadecyl amine.

10. The aqueous bath of claim 8 in which the textile softening agent is derived from the inter action of 5-phenyl-5-rnethyl hydantoin and propyl hexadecyl amine.

11. The aqueous bath of claim 8 in which the textile softening agent is derived from the interaction of 5,5-dimethyl hydantoin and a mixture of hexadecyl and octadecyl amines.

12. A textile fabric having a soft and even handle obtained by impregnating said fabric with an aqueous dispersion of the reaction product of a hydantoin of the general formula:

wherein It represents a member selected from the group consisting of hydrogen, phenyl, and an alkyl group having less than six-carbon atoms; R is a member of the group consisting of phenyl, hydrogen and an alkyl group of less than six carbon atoms, the sum or the carbon atoms represented by the substituents R and B being less than ten; and an aliphatic amine-of the formula:

n n-(n n in which in is an aliphatic chain of from ten to twenty carbon atoms and R is benember of the group consisting of hydrogen and an alkyl group having less than ten carbon atoms. and thereafter drying the impre nated fabric.

13. A textile fabric having a soft and even handle obtained by impr gnating said fabric with an aqueous dispersion of the reaction product of SJ-dimethyl hydantoin and octadecyl amine, and thereafter drying the impregnated fabric.

14. A textile fabric having a soft and. even handle obtained by impregnating said fabric with an aqueous dispersion of the reaction product of SJ-dimethyl hydantoin and an amine mixture containing essentially bs-hexadecyl amine and 56 octadecyi amine, and thereafter drying the imp egnated fabric.

15. A textile fabric having a soft and even handle obtained by impregnating said fabric with an aqueoudiapersion of the reaction product of t-phenyi-b-methyl hydantoinand propyl hexadecyl amine. and thereafter drying the impreg-.

nated fabric.

HILLARY ROBINI'I'II, Jn. CARL R. PACII'ICO.

romaine.

Claims (1)

1. IN A PROCESS FOR THE PREPARATION OF REACTION PRODUCTS SUITABLE FOR IMPROVING THE SOFTNESS AND HANDLE OF TEXTILES, THE STEP WHICH COMPRISES REACTING IN SUBSTANTIALLY EQUIMOLECULAR PREPARATIONS AN AQUEOUS MIXTURE OF A HYDANTOIN OF THE GENERAL FORMULA
US2541101A 1948-01-02 1948-01-02 Hydantoin derivative textile lubricants Expired - Lifetime US2541101A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3956144A (en) * 1974-09-16 1976-05-11 Sandoz, Inc. Flame-retardant softening agents
US3959156A (en) * 1973-12-06 1976-05-25 Sandoz, Inc. Fabric softener
US3969231A (en) * 1974-09-16 1976-07-13 Sandoz, Inc. Flame-retardant softening agents
US4230709A (en) * 1978-05-23 1980-10-28 Lilly Industries Limited Method of treating asthma with alkyl, alkylidene and alkylene hydantoins

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3959156A (en) * 1973-12-06 1976-05-25 Sandoz, Inc. Fabric softener
US3956144A (en) * 1974-09-16 1976-05-11 Sandoz, Inc. Flame-retardant softening agents
US3969231A (en) * 1974-09-16 1976-07-13 Sandoz, Inc. Flame-retardant softening agents
US4230709A (en) * 1978-05-23 1980-10-28 Lilly Industries Limited Method of treating asthma with alkyl, alkylidene and alkylene hydantoins

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