US2574189A - Etheksi of pokychtoko - Google Patents
Etheksi of pokychtoko Download PDFInfo
- Publication number
- US2574189A US2574189A US2574189DA US2574189A US 2574189 A US2574189 A US 2574189A US 2574189D A US2574189D A US 2574189DA US 2574189 A US2574189 A US 2574189A
- Authority
- US
- United States
- Prior art keywords
- bacteriostatic
- textile
- solution
- hydrophilic
- compound
- 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
- 230000003385 bacteriostatic Effects 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 10
- 229920002866 paraformaldehyde Polymers 0.000 claims description 10
- CZZYITDELCSZES-UHFFFAOYSA-N Diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- JKFXHLWOUSFUCN-UHFFFAOYSA-N ClC(CO)(O)CO Chemical compound ClC(CO)(O)CO JKFXHLWOUSFUCN-UHFFFAOYSA-N 0.000 claims description 4
- 239000004753 textile Substances 0.000 description 28
- 239000004744 fabric Substances 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 20
- 239000000463 material Substances 0.000 description 20
- 229920002678 cellulose Polymers 0.000 description 12
- 239000001913 cellulose Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 241000894006 Bacteria Species 0.000 description 8
- 150000002433 hydrophilic molecules Chemical class 0.000 description 8
- 238000000576 coating method Methods 0.000 description 6
- 238000011109 contamination Methods 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 239000001632 sodium acetate Substances 0.000 description 6
- 235000017281 sodium acetate Nutrition 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 4
- 244000052616 bacterial pathogens Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000009877 rendering Methods 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QILSFLSDHQAZET-UHFFFAOYSA-N Diphenylmethanol Chemical class C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 2
- 241000132446 Inula Species 0.000 description 2
- 230000001476 alcoholic Effects 0.000 description 2
- 230000003042 antagnostic Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 230000002349 favourable Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 230000002070 germicidal Effects 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000001145 hydrido group Chemical group *[H] 0.000 description 2
- 230000001771 impaired Effects 0.000 description 2
- 238000004900 laundering Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- -1 mercurial Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000005445 natural product Substances 0.000 description 2
- 229930014626 natural products Natural products 0.000 description 2
- 230000001717 pathogenic Effects 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000000717 retained Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/313—Compounds having groups containing halogen
Definitions
- novel bacteriostatic and hydrophilic compounds of the present invention comprise derivatives of 2,2'-dihydroxy 3,5,6,3',5',6'-hexach1orodiphenylmethane having the general formula OH OR C! -CH2 C1 Cl Cl wherein R represents one of the group of radicals comprising CH2--CHOH-CHz-O--CH2CI, and
- I ris-verdant that the desirable property of iii-E hibiting' the growth oi bacteria' may be ed to 'c iiIOSi ma-terial by treatment of the are: rial, involving chemical reaction, in which my novel bacteriostatic and hydrophilic compound is attached to the cellulose'molecul'eat the hydro carbon c ain, represe ted by R in the above rerinula.
- the combination ofbactericidal and by drophilic groupsemployed in the present inven tim increases the afiinity of the cellulose for water but'without, however, causing it to reach a degree of solubility undesirable in textile ma terials.
- the resulting modified cellulosic materials provide a bacteriostatic environment which restricts the growth of bacteria thereon under all conditions of moisture and temperature.
- the bacteriostatic and hydrophilic compounds of the present invention are formed by reacting one of the hydroxyl groups of the chlorinated hydroxy diphenyl methane represented by the for-'- inula with chlorinated 'elycerine, paraforihaldehyde and hydrochloric acid to provide thereon a Hy: droxyl'ate'd hydrocarbon chain. the finished cellulose product this hydrocarbon chain is an tached to the cellulose molecule.
- Example 2 2-dihydroxy 3,5,6,3',5,6'-hexachlorodlphenylmethane is dissolved in ethyl alcohol and metallic sodium is added slowly to this solution in molar equivalents (1 mol of Na to 1 mol of diphenylmethane) to form a sodium phenolate.
- the solution is heated to the boiling point and a-monochloroglycerine is added slowly in molar proportions, i. e., 1 mol of glycerine to 1 mol of diphenylmethane, with the formation of a sodium chloride precipitate.
- the alcoholic solution is recovered by filtration, and the alcohol evaporated or distilled 01?, leaving a residue having a melting point of 97 C.
- the compound contained in the resulting solution may be applied to textile'fabrics in anyone of the three following ways, to form a cellulose derivative which is bacteriostatic (A)
- Cotton fabric is pretreated with a 'to solution of sodium acetate, and squeezed to about 100% pickup.
- the treated fabric is then impregnated with a 1% to 2% solution of the compound in benzene. I
- the cloth is passed through squeeze rolls (about 80% to 100% pickup) and then heated to about 130-150" C.
- 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. Such treatment involves a chemical reaction upon the cellulose molecule with the production of a new cellulosic substance. The bacteriostatic qualities of this substance are not impaired by washing, dyeing or other treatments usually encountered in the finishing or use of textile material.
- hydrophilic and bacteriostatic compound represented by the formula OCH1-CHOH-CHrOOHzCl 4.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Nov. 6, 1951 nrriinfts oF'PonYcHLofio' METHANE' A liavigl M. Musser, Fair LawnyNs 1.", assignor. to.
Pacific Mills, Boston,
Massachusetts Mass.,; a. corporation of l I o. -.-l )rawing. Original application l iug usif 3i; 1946, Serial N0. 694,422. Divided all! this plication December 23, 1950;8eriaiNo: 202,570
processes" ior preparing this;v composition. The
present application is a' division of my prior ap' u aucnser n No. 694,422, filed August 31, 1 946, new Ratent' No. 2,559,986, datedJuly 10,1951.
Pathogenic germs are frequently present or on the surface of textilefabrics, either as a e ul 9 cont t. o the fa i w t e human body, as in the case of sheets, pillowcases, towels and the like, or as a result of exposure of the textile to an atmosphere in which such bacteria are present. These germs cling tenaciously to the textile fibers and may, under favorable moisture and temperature conditions, spread and grow colonies, which then present a serious danger of contamination. Means have long been sought for rendering a textile material permanently antagonistic or resistant tosuch bacteria so as to prevent their growth into colonies and to lessen the danger oi contamination from contact with the textile material. It has been proposed to overcome this contamination hazard by applying to textile fabric a coating oi' fa, germicidal compound such as mercurial, a phenolic, or like compound. Such compounds are adequately bacteriostatic in this relationship, but the art heretofore has not succeeded in rendering textile materials permanently bacteriostatic by treatment with them. Fabrics coated with suchmaterials commonly lose substantially all of their bacteriostatic property upon a single laundering and it is therefore necessary that the coating treatment be repeated each time the article is laundered Such coating processes require considerable mechanical equipment and, therefore, are -notja practicable procedure for use 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 improved bacteriostatic compounds and processes for making the same, suitable for use in finishing cellulosic materials such as textile fabrics, threads, yarns and fibers, toimpart thereto improved bacteriostatic properties which will be retained more or less indefinitely.
The novel bacteriostatic and hydrophilic compounds of the present invention comprise derivatives of 2,2'-dihydroxy 3,5,6,3',5',6'-hexach1orodiphenylmethane having the general formula OH OR C! -CH2 C1 Cl Cl wherein R represents one of the group of radicals comprising CH2--CHOH-CHz-O--CH2CI, and
I ris-verdant that the desirable property of iii-E hibiting' the growth oi bacteria' may be ed to 'c iiIOSi ma-terial by treatment of the are: rial, involving chemical reaction, in which my novel bacteriostatic and hydrophilic compound is attached to the cellulose'molecul'eat the hydro= carbon c ain, represe ted by R in the above rerinula. The combination ofbactericidal and by drophilic groupsemployed in the present inven tim increases the afiinity of the cellulose for water but'without, however, causing it to reach a degree of solubility undesirable in textile ma terials. The resulting modified cellulosic materials provide a bacteriostatic environment which restricts the growth of bacteria thereon under all conditions of moisture and temperature.
The bacteriostatic and hydrophilic compounds of the present invention are formed by reacting one of the hydroxyl groups of the chlorinated hydroxy diphenyl methane represented by the for-'- inula with chlorinated 'elycerine, paraforihaldehyde and hydrochloric acid to provide thereon a Hy: droxyl'ate'd hydrocarbon chain. the finished cellulose product this hydrocarbon chain is an tached to the cellulose molecule. H
' The following e ainm'e, given by way of illustration and not o'f limitation of the invention, shows a practical method for the preparation of bacteriostatic and hydrophilic compounds suitable for use in finishing cellulosic textile material, and practical methods for finishing such material to provide cellulosic materials having improved bacteriostatic properties.
Example 2,2-dihydroxy 3,5,6,3',5,6'-hexachlorodlphenylmethane is dissolved in ethyl alcohol and metallic sodium is added slowly to this solution in molar equivalents (1 mol of Na to 1 mol of diphenylmethane) to form a sodium phenolate. The solution is heated to the boiling point and a-monochloroglycerine is added slowly in molar proportions, i. e., 1 mol of glycerine to 1 mol of diphenylmethane, with the formation of a sodium chloride precipitate. The alcoholic solution is recovered by filtration, and the alcohol evaporated or distilled 01?, 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' tol mol of the compound). Gaseous hydrochloric acid is passed through the benzene solution until the paraformaldehyde is.
completely dissolved. The solution is then neutralized with pyridine, using litmus paper as an indicator.
The compound contained in the resulting solution may be applied to textile'fabrics in anyone of the three following ways, to form a cellulose derivative which is bacteriostatic (A) Cotton fabric is pretreated with a 'to solution of sodium acetate, and squeezed to about 100% pickup. The treated fabric is then impregnated with a 1% to 2% solution of the compound in benzene. I The cloth is passed through squeeze rolls (about 80% to 100% pickup) and then heated to about 130-150" C.
(B) The neutralized benzene solution is evaporated on a water bath and the 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 heatedto 130150 C.
(C) The neutralized benzene solution is evapo- 4 rated and the 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 losic 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. Such treatment involves a chemical reaction upon the cellulose molecule with the production of a new cellulosic substance. The bacteriostatic qualities of this substance are not impaired by washing, dyeing or other treatments usually encountered in the finishing or use of textile material.
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. Hydrophilic and bacteriostatic compounds 7 of the group having the general formula OH on I g 7 01 on 01 wherein R represents one of the group of radicals consisting of -CH2CHOHCH2O-CH2C1,
and" b cm-o-omm cH-o O-CHzCl 2. The method for the preparation of a derivative of chlorinated diphenyl methane which comprises reacting monochlorglycerine with 2,2- dihydroxy 3,5,6,3,5,6 -hexachlorodiphenylmethane in the presence of metallic sodium and thereafter reacting with paraformaldehyde and gaseous hydrochloric acid. I
3. The hydrophilic and bacteriostatic compound represented by the formula OCH1-CHOH-CHrOOHzCl 4. The hydrophilic and bacteriostatic compound represented by the formula DAVID M. MU SSER,
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Musser July 10, 1951
Claims (2)
1. A HYDROPHILIC AND BACTERIOSTATIC COMPOUNDS OF THE GROUP HAVING THE GENERAL FORMULA
2. THE METHOD FOR THE PREPARATION OF A DERIVATIVE OF CHLORINATED DIPHENYL METHANE WHICH COMPRISES REACTING MONOCHLORGLYCERINE WITH 2,2''DIHYDROXY 3,5,6,3'',5'',6''-HEXACHLORODIPHENYLMETHANE IN THE PRESENCE OF METALLIC SODIUM AND THEREAFTER REACTING WITH PARAFORMALDEHYDE AND GASEOUS HYDROCHLORIC ACID.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2574189A true US2574189A (en) | 1951-11-06 |
Family
ID=3438514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2574189D Expired - Lifetime US2574189A (en) | Etheksi of pokychtoko |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2574189A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2285625A (en) * | 1942-06-09 | A-pkenylethyl substituted alkoxy- | ||
| US2297728A (en) * | 1942-10-06 | Ethers of substituted phenyl | ||
| US2559986A (en) * | 1946-08-31 | 1951-07-10 | Pacific Mills | Bacteriostatic cellulosic textile reacted with derivatives of dihydroxy hexachloro diphenyl methane |
-
0
- US US2574189D patent/US2574189A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2285625A (en) * | 1942-06-09 | A-pkenylethyl substituted alkoxy- | ||
| US2297728A (en) * | 1942-10-06 | Ethers of substituted phenyl | ||
| US2559986A (en) * | 1946-08-31 | 1951-07-10 | Pacific Mills | Bacteriostatic cellulosic textile reacted with derivatives of dihydroxy hexachloro diphenyl methane |
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