US2559986A - Bacteriostatic cellulosic textile reacted with derivatives of dihydroxy hexachloro diphenyl methane - Google Patents

Bacteriostatic cellulosic textile reacted with derivatives of dihydroxy hexachloro diphenyl methane Download PDF

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US2559986A
US2559986A US694422A US69442246A US2559986A US 2559986 A US2559986 A US 2559986A US 694422 A US694422 A US 694422A US 69442246 A US69442246 A US 69442246A US 2559986 A US2559986 A US 2559986A
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bacteriostatic
dihydroxy
textile
cellulosic textile
derivatives
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US694422A
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David M Musser
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Pacific Mills
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Pacific Mills
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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
    • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/20—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing organic materials

Definitions

  • the present invention relates to a new composition of matter, particularly useful as a textile finish, to processes for preparing this composition, and to textile material, finished with the same, characterized by the desirable property of inhibiting the growth of bacteria.
  • a further object of the invention is to provide cellulosic textile materials having improved bacteriostatic properties and capable of retaining these properties more or less indefinitely.
  • cellulosic material by treatment of the material, involving chemical reaction, in which there is attached to the cellulose molecule a hydrocarbon chain containing bactericidal and hydrophilic groups. The combination of such groups however, causing it to reach a degree of solubility undesirable in textile materials.
  • the cellulosic materials of the present invention provide a bacteriostatic environment which restricts the growth of bacteria thereon under all conditions of moisture and temperature.
  • novel bacteriostatic and hydrophylic compounds of the present invention comprise derivatives of 2,2'-dihydroxy 3,5,6,3.,5,6'-hexachlorodiphenylmethane having the general formula 01 GH c1 wherein R represents one of the group of radicals comprising CH -CHOHCHz-0CH2C1 H2CO-CH2C1 -0H,- -0CH2C1 and their higher homologues.
  • bacteriostatic and hydrophilic compounds may be formed by reacting one of the hydroxyl groups of the chlorinated hydroxy diphenylmethane having the formula I OH OH 0] CH2- c1 I 1- 1 with chlorinated glycerin, paraformaldehyde and hydrochloric acid, or with epichlorohydrin or the like, to form thereon a hydroxylated hydrocarbon chain.
  • the compound contained in the resulting solu-' tion may be applied to textile fabrics in any one of the three following ways, to form a cellulose derivative which is bacteriostatic.
  • Example 2 Cotton fabric is impregnated with caustic soda of mercerizing strength and then exposed to gaseous epichlorohydrin at mm. pressure and a temperature of 50 C. for two hours, washed in water, soured in dilute acetic acid, washed again, and dried with a solvent (alcohol or the like). The fabric is then refluxed for several hours in an alcohol solution (or a carbon tetrachloride solution) of mono potassium salt of 2,2'-dihydroxy 3,5,6,3' ,5 ,6 -hexachlorodiphenylmethane.
  • alcohol solution or a carbon tetrachloride solution
  • the present invention is applicable generally to materials of a cellulosic nature, either native or regenerated, on which there are free hydroxyl groups.
  • Cellulosic textile materials such as cotton'and other natural products, may be treated in the form of fibers, threads, yarns, or in the piece, as a woven, braided, netted or knitted fabric.
  • the treatment of this invention involves a chemical reaction upon the cellulose molecule with the production of a new substance. The bacteriostatic qualities of this substance are not impaired by washing, dyeing or other treatments encountered in the finishing or use of the mate-.
  • a cellulosic textile material which has been rendered bacteriostatic by reaction with a compound of the formula.
  • R represents one of the group of radicals consisting of CH2-CHOH-CH2-O-CH2CI.
  • CEr-O-CHzCl O-GHzCl said textile material being of the class containing free hydroxyl groups.
  • the method of rendering cellulosic textile materials containing free hydroxyl groups bacteriostatic which comprises treating the material, sequentially, with a solution of sodium acetate .and a pyridine neutralized benzene solution of the compound of the formula O-GHzCHOH-CHpO-CEC] C CH Cl Cl C] 0] GE Cl under conditions inducing a reaction between the material and the compounds.
  • the method of rendering cellulosic textile materials containing i'ree hydroxyl groups bacteriostatic which comprises pretreating the material with a solution of sodium acetate and then impregnating it with an aqueous dispersion of the compound having the formula on o-cm-cnorpcnro-cmcl' C] CH 01 under conditions inducing a reaction between the material and the compound.
  • the method of rendering cellulosic textile materials containing free hydroxyl groupsba'cteriostatic which comprises treating the material with a dispersion of the compound having the formula 01 CH 01 g in an aqueous solution of sodium acetate, under conditions inducing a reaction between the material and the compound.
  • a cellulosic textile material of the class containing free hydroxyl groups which has been rendered bacteriostatic by reaction with an epichlorohydrin derivative of 2,2'-dihydroxy 3,5,6,3',5,6' hexachlorodiphenylmethane under conditions inducing a reaction between the material and the derivative.

Description

Patented July 10, 1951 BACTERIOSTATIC CELLULOSIC TEXTILE REACTED WITH DERIVATIVES OF DI- HYDROXY HEXACHLORO DIPHENYL lVIETHANE David M. Musser, Clemson, S. 0., assignor to Pacific Mills, Boston, Mass., a corporation of Mas sachusetts No Drawing. Application August 31, 1946, Serial No. 694,422
1 10 Claims.
The present invention relates to a new composition of matter, particularly useful as a textile finish, to processes for preparing this composition, and to textile material, finished with the same, characterized by the desirable property of inhibiting the growth of bacteria.
Pathogenic germs are frequently present in or on the surface of textile fabrics, either as a result of contact of the fabric with the human body, as in the case of sheets, pillow cases, towels and the like, or simply as a result of exposure of the textile to an atmosphere in which such bacteria are present. These germs cling tenaciously to the textile fibres and may, under favorable moisture and temperature conditions, spread and grow 1 colonies, which then present a serious danger of are adequately bacteriostatic in this relationship,
but the art heretofore has not succeeded in rendering textile materials permanently bacteriostatic by treatment with them. Textiles coated with such materials commonly lose substantially all of their bacteriostatic property upon a single laundering and it is therefore necessary that the employed in the present invention increases the coating treatment be repeated each time the textile article is laundered. Such coating processes.
require considerable mechanical equipment and therefore, are not a practicable procedure in most hotels, hospitals and private homes in which bed linens and towels are used.
It is an object of the present invention to provide an improved bacteriostatic compound, and process for making the same, suitable for use in association with cellulosic materials such as textile fabrics, threads, yarns and fibers. A further object of the invention is to provide cellulosic textile materials having improved bacteriostatic properties and capable of retaining these properties more or less indefinitely.
I have found that the desirable property of inhibiting the growth of bacteria may be imparted to cellulosic material by treatment of the material, involving chemical reaction, in which there is attached to the cellulose molecule a hydrocarbon chain containing bactericidal and hydrophilic groups. The combination of such groups however, causing it to reach a degree of solubility undesirable in textile materials. The cellulosic materials of the present invention provide a bacteriostatic environment which restricts the growth of bacteria thereon under all conditions of moisture and temperature.
The novel bacteriostatic and hydrophylic compounds of the present invention comprise derivatives of 2,2'-dihydroxy 3,5,6,3.,5,6'-hexachlorodiphenylmethane having the general formula 01 GH c1 wherein R represents one of the group of radicals comprising CH -CHOHCHz-0CH2C1 H2CO-CH2C1 -0H,- -0CH2C1 and their higher homologues.
These bacteriostatic and hydrophilic compounds may be formed by reacting one of the hydroxyl groups of the chlorinated hydroxy diphenylmethane having the formula I OH OH 0] CH2- c1 I 1- 1 with chlorinated glycerin, paraformaldehyde and hydrochloric acid, or with epichlorohydrin or the like, to form thereon a hydroxylated hydrocarbon chain. In the finished cellulosic product this hydrocarbon chain is attached to the cellulose Example 1 2,2'-dihydroxy 3,5,6,3,5',6'-hexachlorodiphenylmethane is dissolved in ethyl alcohol and metallic sodium is added slowly to this solution in molar covered by filtration, and the alcohol evaporated or distilled off, leaving a residue having a melting point of 97 C. This residue is dissolved in benzene and then paraformaldehyde is added to the solution in molar proportions (1 to 2 mols of paraformaldehyde to 1 mol of the compound). Gaseous hydrochloric acid is passed through the benzene solution until the paraformaldehyde is completely dissolved. The solution is then neuh pyridine, using litmus paper as an indicator. 1
v The compound contained in the resulting solu-' tion may be applied to textile fabrics in any one of the three following ways, to form a cellulose derivative which is bacteriostatic.
(A) Cotton fabric is pretreated with a 5% to solution of sodium acetate, and squeezed to about 100% pick-up. The treated fabric is then impregnated with a 1% to 21% solution of the compound in benzene. The cloth is passed through squeeze rolls (about 80% to 100% pickup) and then heated to about 130-150 C.
(B) The pyridine neutralized benzene solution of the bacteriostatic compound is evaporated on a water bath and the resulting solid residue dispersed in warm water by stirring. The textile fabric to be treated is pretreated with sodium acetate as in (A) above, and then impregnated with the water dispersion. Thereafter the fabric is heated to 130-150 C.
(C) The pyridine neutralized benzene solution of the bacteriostatic compound is evaporated and the resulting solid residue dispersed in a warm water solution of 5% to 10% sodium acetate. The textile fabric is impregnated directly. without pretreatment, with the water dispersion, and the excess removed by squeezing to a pickup of about 100% and the fabric thereafter heated at 130150 C. as before.
Example 2 Cotton fabric is impregnated with caustic soda of mercerizing strength and then exposed to gaseous epichlorohydrin at mm. pressure and a temperature of 50 C. for two hours, washed in water, soured in dilute acetic acid, washed again, and dried with a solvent (alcohol or the like). The fabric is then refluxed for several hours in an alcohol solution (or a carbon tetrachloride solution) of mono potassium salt of 2,2'-dihydroxy 3,5,6,3' ,5 ,6 -hexachlorodiphenylmethane.
The fabrics resulting from the treatment oi the foregoing examples exhibit very pronounced bacteriostatic properties and retain these properties, even after several commercial launderings.
The present invention is applicable generally to materials of a cellulosic nature, either native or regenerated, on which there are free hydroxyl groups. Cellulosic textile materials, such as cotton'and other natural products, may be treated in the form of fibers, threads, yarns, or in the piece, as a woven, braided, netted or knitted fabric. The treatment of this invention involves a chemical reaction upon the cellulose molecule with the production of a new substance. The bacteriostatic qualities of this substance are not impaired by washing, dyeing or other treatments encountered in the finishing or use of the mate-.
rial.
The foregoing disclosure of preferred embodiments of my invention is made by way of illustration and not of limitation. It will be appreciated that changes may be made therein by those skilled in the art without departure from my invention, as expressed in the following claims.
I claim:
1. A cellulosic textile material which has been rendered bacteriostatic by reaction with a compound of the formula.
OH OR C] CH: C1
wherein R represents one of the group of radicals consisting of CH2-CHOH-CH2-O-CH2CI. and
CEr-O-CHzCl O-GHzCl said textile material being of the class containing free hydroxyl groups.
2. The method of rendering cellulosic textile materials containing free hydroxyl groups bacteriostatic which comprises treating the material with a compound of the formula on on wherein R represents one of the group of radicals consisting of CH2-CHOHCH2OCH2C1; and
cnr-o-cmcl -CHC o-cmcl under conditions inducing a reaction between the material and the compound.
3. The method of rendering cellulosic textile materials containing free hydroxyl groups bacteriostatic which comprises treating the material, sequentially, with a solution of sodium acetate .and a pyridine neutralized benzene solution of the compound of the formula O-GHzCHOH-CHpO-CEC] C CH Cl Cl C] 0] GE Cl under conditions inducing a reaction between the material and the compounds.
5. The method of rendering cellulosic textile materials containing free hydroxyl groups bacteriostatic which comprises exposing the material,
after the same has been impregnated with caustic soda of mercerizing strength, to gaseous epichlorohydrin and thereafter treating the material with an alkali metal salt of 2,2'-dihydroxy 3,5,6,3',5',6' hexachlorodiphenylmethane under reflux conditions.
6. A cellulosic textile material containing free hydroxyl groups, which has been rendered bacteriostatic by reaction with the compound of the formula O-GHr-CHOH-CHz-O-CHzCl 7. A cellulosic textile material containing free hydroxyl groups which has been rendered bacteriostatic by reaction with the compound of the 01 on 01 ii o-cmcl 8. The method of rendering cellulosic textile materials containing i'ree hydroxyl groups bacteriostatic which comprises pretreating the material with a solution of sodium acetate and then impregnating it with an aqueous dispersion of the compound having the formula on o-cm-cnorpcnro-cmcl' C] CH 01 under conditions inducing a reaction between the material and the compound.
9. The method of rendering cellulosic textile materials containing free hydroxyl groupsba'cteriostatic which comprises treating the material with a dispersion of the compound having the formula 01 CH 01 g in an aqueous solution of sodium acetate, under conditions inducing a reaction between the material and the compound.
10. A cellulosic textile material of the class containing free hydroxyl groups which has been rendered bacteriostatic by reaction with an epichlorohydrin derivative of 2,2'-dihydroxy 3,5,6,3',5,6' hexachlorodiphenylmethane under conditions inducing a reaction between the material and the derivative.
DAVID M. MUSSER.
REFERENCES CITED The following references are of record in the file of this patent:
OTHER REFERENCES Ser. No. 416,053, Schussler (A. P. C.) published June 22, 1943.
Weston: Rot-Resistant Amer. Dyes Rep. 34, pp. P91-95 (February 26. 1945).
Textile Materials."

Claims (1)

1. A CELLULOSIC TEXTILE MATERIAL WHICH HAS BEEN RENDERED BACTERIOSTATIC BY REACTION WITH A COMPOUND OF THE FORMULA
US694422A 1946-08-31 1946-08-31 Bacteriostatic cellulosic textile reacted with derivatives of dihydroxy hexachloro diphenyl methane Expired - Lifetime US2559986A (en)

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2574189A (en) * 1951-11-06 Etheksi of pokychtoko
US2684386A (en) * 1950-12-13 1954-07-20 Gen Aniline & Film Corp Halogenated o, o' dihydroxy diphenyl methane alkyl ether
US2697094A (en) * 1950-11-14 1954-12-14 Basf Ag Fungicidal products of cellulose ethers
US3079214A (en) * 1959-07-06 1963-02-26 Ralph J Berni Perfluoroalkoxy-substituted propyl ethers of cellulose textile fiber and process of making
DE1149326B (en) * 1953-02-10 1963-05-30 Basf Ag Process for increasing the resistance of fibers and products made from them to the action of microorganisms
US20080138626A1 (en) * 2006-12-11 2008-06-12 Denes Ferencz S Plasma-enhanced functionalization of substrate surfaces with quaternary ammonium and quaternary phosphonium groups
US20100021654A1 (en) * 2004-03-24 2010-01-28 Wisconsin Alumni Research Foundation Plasma-enhanced functionalization of inorganic oxide surfaces

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1906890A (en) * 1929-01-30 1933-05-02 Ig Farbenindustrie Ag Condensation product from halogenated phenols and aldehydes
US1971436A (en) * 1931-03-07 1934-08-28 Ig Farbenindustrie Ag Compound of the polyarylmethyl series and the process for preparing the same
US2053610A (en) * 1932-07-22 1936-09-08 Ig Farbenindustrie Ag Protecting animal fibers from textile pests
US2163607A (en) * 1930-08-25 1939-06-27 Lilienfeld Leon Manufacture of artificial threads or other products from cellulose compounds
US2252039A (en) * 1936-06-30 1941-08-12 Heberlein Patent Corp Process of rendering textiles water repellent
US2285625A (en) * 1942-06-09 A-pkenylethyl substituted alkoxy-
US2331090A (en) * 1941-02-24 1943-10-05 Dow Chemical Co Cellulose ether composition

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2285625A (en) * 1942-06-09 A-pkenylethyl substituted alkoxy-
US1906890A (en) * 1929-01-30 1933-05-02 Ig Farbenindustrie Ag Condensation product from halogenated phenols and aldehydes
US2163607A (en) * 1930-08-25 1939-06-27 Lilienfeld Leon Manufacture of artificial threads or other products from cellulose compounds
US1971436A (en) * 1931-03-07 1934-08-28 Ig Farbenindustrie Ag Compound of the polyarylmethyl series and the process for preparing the same
US2053610A (en) * 1932-07-22 1936-09-08 Ig Farbenindustrie Ag Protecting animal fibers from textile pests
US2252039A (en) * 1936-06-30 1941-08-12 Heberlein Patent Corp Process of rendering textiles water repellent
US2331090A (en) * 1941-02-24 1943-10-05 Dow Chemical Co Cellulose ether composition

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2574189A (en) * 1951-11-06 Etheksi of pokychtoko
US2697094A (en) * 1950-11-14 1954-12-14 Basf Ag Fungicidal products of cellulose ethers
US2684386A (en) * 1950-12-13 1954-07-20 Gen Aniline & Film Corp Halogenated o, o' dihydroxy diphenyl methane alkyl ether
DE1149326B (en) * 1953-02-10 1963-05-30 Basf Ag Process for increasing the resistance of fibers and products made from them to the action of microorganisms
US3079214A (en) * 1959-07-06 1963-02-26 Ralph J Berni Perfluoroalkoxy-substituted propyl ethers of cellulose textile fiber and process of making
US20100021654A1 (en) * 2004-03-24 2010-01-28 Wisconsin Alumni Research Foundation Plasma-enhanced functionalization of inorganic oxide surfaces
US7723126B2 (en) * 2004-03-24 2010-05-25 Wisconsin Alumni Research Foundation Plasma-enhanced functionalization of inorganic oxide surfaces
US20080138626A1 (en) * 2006-12-11 2008-06-12 Denes Ferencz S Plasma-enhanced functionalization of substrate surfaces with quaternary ammonium and quaternary phosphonium groups
US8029902B2 (en) 2006-12-11 2011-10-04 Wisconsin Alumni Research Foundation Plasma-enhanced functionalization of substrate surfaces with quaternary ammonium and quaternary phosphonium groups

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