US2710269A - Method of treating woolen textile materials with di-pentachlorphenyl-mono-hydrogen phosphate for protecting such textiles against biological attack - Google Patents
Method of treating woolen textile materials with di-pentachlorphenyl-mono-hydrogen phosphate for protecting such textiles against biological attack Download PDFInfo
- Publication number
- US2710269A US2710269A US294484A US29448452A US2710269A US 2710269 A US2710269 A US 2710269A US 294484 A US294484 A US 294484A US 29448452 A US29448452 A US 29448452A US 2710269 A US2710269 A US 2710269A
- Authority
- US
- United States
- Prior art keywords
- pentachlorphenyl
- mono
- protecting
- hydrogen phosphate
- textile materials
- 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
- 239000004753 textile Substances 0.000 title description 12
- 238000000034 method Methods 0.000 title description 7
- 239000000463 material Substances 0.000 title description 5
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 9
- 229910019142 PO4 Inorganic materials 0.000 description 6
- 235000021317 phosphate Nutrition 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 241000282414 Homo sapiens Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- MLJDDAYQOBZFKW-UHFFFAOYSA-N bis(2,3,4,5,6-pentachlorophenyl) hydrogen phosphate Chemical compound OP(=O)(OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl)OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl MLJDDAYQOBZFKW-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 150000003388 sodium compounds Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 241000396431 Anthrenus scrophulariae Species 0.000 description 1
- 241000131286 Attagenus Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- GAHUQIUQVMKJII-UHFFFAOYSA-N [Na]c1c(Cl)c(Cl)c(Cl)c(Cl)c1Cl Chemical compound [Na]c1c(Cl)c(Cl)c(Cl)c(Cl)c1Cl GAHUQIUQVMKJII-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- -1 di-pentachlorphenyl chlor phosphate Chemical compound 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000019980 sodium acid phosphate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
Definitions
- This invention relates to the treatment of woolen textile materials with di-pentachlorphenyl-mono-hydrogen phosphate for protecting them against biological attack.
- chlorinated phenols and particularly pentachlorphenol when applied to textile materials, possess the power to a high degree of protecting such materials from attack by moulds, bacteria and biting insects.
- chlorinated phenols also possess undesirable properties from the point of view of the textile technologist to varying degree, particularly solubility in water and volatility which are large for the orders of magnitude involved, although these undesirable properties are least developed in pentachlorphenol.
- the substances which consequently are employed in accordance with the present invention are the phosphates of pentachlorphenol, in particular the di-pentachlorphenyl mono-hydrogen phosphate which as far as can be ascertained has the composition P Ct.Ol5O O and which it is believed has not been previously prepared.
- the customary method of preparing such compounds is to heat the phenol with phosphorous oxychloride but in the case of pentachlorphenol, the customary method of boiling the reagents together yields a very poor resultat most a few per cent of the theory. The reaction does not begin to take place at temperatures below 180 C.
- the sodium compound forms a fine white power which disperses spontaneously in water or dilute alkali.
- Woolen goods can be dyed with the suspension of the compound used, either per se or together with dyestufi's in the presence of the customary additions in the usual manner.
- Di pentachlorphenyl-mono-hydrogen phosphate is substantive to wool and compatible with the usual dyestuffs.
- the goods may be padded through a dispersion in water under either acid, neutral or alkaline conditions, squeezed and dried, although the dyeing method is preferred.
- the phosphates can be applied in non-aqueous media.
- the acid phosphate from methylated spirits solution. Textiles containing as little as 0.5 per cent of the acid phosphate are immune from the attack of even the carpet beetle, Attagenus pieeus and retain this immunity after repeated washings with soap 3 or soap and soda or after frequent commercial dry cleaning Operations.
- a method for the protection of a woolen textile material against biological attack which comprises impregnating said textile with di-pentachlorphenyl-monohydrogen phosphate.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
*METHOD ()F TREATING WOOLEN TEXTILE MA- Eric Berkeley Higgins, Welwyn Garden City, and Alfred Edward Read, St. Albans, England No Drawing. Application June 19, 1952, Serial No. 294,484
Claims priority, application Great Britain July 2, 1951 1 Claim. (Cl. 117-1385) This invention relates to the treatment of woolen textile materials with di-pentachlorphenyl-mono-hydrogen phosphate for protecting them against biological attack.
It is Well known that the chlorinated phenols and particularly pentachlorphenol, when applied to textile materials, possess the power to a high degree of protecting such materials from attack by moulds, bacteria and biting insects.
Unfortunately these chlorinated phenols also possess undesirable properties from the point of view of the textile technologist to varying degree, particularly solubility in water and volatility which are large for the orders of magnitude involved, although these undesirable properties are least developed in pentachlorphenol.
Various attempts have been made to find compounds of pentachlorphenol which possess the valuable properties of that substance without the undesirable properties.
Although it is recognised that prediction is not possible in regard to the properties of a chemical compound, this is much more so when its physiological properties simultaneously come into question.
Consequently, a very large number of derivatives of pentachlorphenol have now been prepared from among which those found to possess the required properties in the highest degree have been determined by trial and experiment. Such desirable properties include the following:
1. High toxicity to the biological enemies of textile fibres with very low toxicity towards human beings per s and harmless when in contact with the human skin.
2. Substantial non-volatility at temperatures up to the temperature at which textiles are destroyed either in steam or in the dry state.
3. Substantivity and compatibility with dyestuffs and the customary dyebath additions in acid and neutral solutions and highly stable to the action of water and detergents and dry cleaners liquids when dyed upon the textile.
The substances which consequently are employed in accordance with the present invention are the phosphates of pentachlorphenol, in particular the di-pentachlorphenyl mono-hydrogen phosphate which as far as can be ascertained has the composition P Ct.Ol5O O and which it is believed has not been previously prepared.
The customary method of preparing such compounds is to heat the phenol with phosphorous oxychloride but in the case of pentachlorphenol, the customary method of boiling the reagents together yields a very poor resultat most a few per cent of the theory. The reaction does not begin to take place at temperatures below 180 C.
It has now been found, however, that if pentachlorphenol is caused to react with phosphorous oxychloride States Patent 0 F being obtained at'the higher temperature.
2,710,269 Patented June 7, 1955 ice at hightemperatures (between 250and 300? C.), good yields of the desired products are obtained, the best yields This temperature, however, is greatly above the boiling point of the phosphorous oxychloride and therefore a departure from the customary method of boiling is required. Actually it is necessary to pass the phosphorous oxychloride in the vapour form through the pentachlorphenol with the latter in the molten state. Alternatively heating under pressure though possible, gives rise to great difficulties on account of the simultaneous evolution of hydrochloric acid.
Example In the preparation of di-pentachlorphenyl monohydrogen phosphate, 533 grams of pentachlorphenol in the molten state has grams of phosphorous oxychloride in the vapour form passed through it at a temperature of 290 C. for 10 hours. The primary product of the reaction is di-pentachlorphenyl chlor phosphate formed according to the equation:
When cold, the mass is boiled with a solution of caustic soda sufiicient to give a faintly alkaline reaction and the mass breaks up into a sandy mass of the sodium compound as follows:
+ 2NaOH= P NaCl The small amount of neutral phosphate can be separated, if desired, by washing the mixture of it and the pentachlorphenyl sodium acid phosphate with toluene, from which solvent, the neutral phosphate can be recovered by evaporation.
The sodium compound forms a fine white power which disperses spontaneously in water or dilute alkali.
Woolen goods can be dyed with the suspension of the compound used, either per se or together with dyestufi's in the presence of the customary additions in the usual manner. Di pentachlorphenyl-mono-hydrogen phosphate is substantive to wool and compatible with the usual dyestuffs.
Alternatively, the goods may be padded through a dispersion in water under either acid, neutral or alkaline conditions, squeezed and dried, although the dyeing method is preferred.
Finally, the phosphates can be applied in non-aqueous media. For example, the acid phosphate from methylated spirits solution. Textiles containing as little as 0.5 per cent of the acid phosphate are immune from the attack of even the carpet beetle, Attagenus pieeus and retain this immunity after repeated washings with soap 3 or soap and soda or after frequent commercial dry cleaning Operations.
We claim:
A method for the protection of a woolen textile material against biological attack which comprises impregnating said textile with di-pentachlorphenyl-monohydrogen phosphate.
References Cited in the file of this patent UNITED STATES PATENTS Lomrnel Feb. 25, Caprio Jan. 10, Higgins Sept. 27, Weisel et a1. Feb. 20, Moyle Oct. 21,
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB15676/51A GB742782A (en) | 1951-07-02 | 1951-07-02 | Improvements relating to the treatment of textile materials for protection against biological attack |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2710269A true US2710269A (en) | 1955-06-07 |
Family
ID=10063418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US294484A Expired - Lifetime US2710269A (en) | 1951-07-02 | 1952-06-19 | Method of treating woolen textile materials with di-pentachlorphenyl-mono-hydrogen phosphate for protecting such textiles against biological attack |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2710269A (en) |
| BE (1) | BE512531A (en) |
| DE (1) | DE936327C (en) |
| FR (1) | FR1059358A (en) |
| GB (1) | GB742782A (en) |
| NL (1) | NL85053C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4020129A (en) * | 1974-05-03 | 1977-04-26 | Hoechst Aktiengesellschaft | Production of dithiophosphoric acid-O,O-diesters |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2857308A (en) * | 1956-11-15 | 1958-10-21 | Monsanto Chemicals | Method of destroying nematodes employing phosphorodithioates |
| GB1031865A (en) * | 1963-12-09 | 1966-06-02 | Catomance Ltd | Compositions and method for protecting materials against biological attack |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1748675A (en) * | 1926-03-15 | 1930-02-25 | Ig Farbenindustrie Ag | Process for protecting materials against attack by moths |
| US2143639A (en) * | 1936-09-24 | 1939-01-10 | Celluloid Corp | Article of cellulose |
| US2483008A (en) * | 1944-01-29 | 1949-09-27 | Tewin Ind Inc | Proofing proteinaceous fibers against biological attack |
| US2542604A (en) * | 1948-12-01 | 1951-02-20 | Standard Oil Dev Co | Extreme pressure lubricant and extreme pressure agents therefor |
| US2615038A (en) * | 1948-10-15 | 1952-10-21 | Dow Chemical Co | O,o-di(polyhalophenyl) n-substituted amidothiophosphates |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2430017A (en) * | 1945-03-08 | 1947-11-04 | Rohm & Haas | Mildewproofing textiles |
-
0
- NL NL85053D patent/NL85053C/xx active
- BE BE512531D patent/BE512531A/xx unknown
-
1951
- 1951-07-02 GB GB15676/51A patent/GB742782A/en not_active Expired
-
1952
- 1952-06-19 US US294484A patent/US2710269A/en not_active Expired - Lifetime
- 1952-06-25 DE DEH13019A patent/DE936327C/en not_active Expired
- 1952-06-30 FR FR1059358D patent/FR1059358A/en not_active Expired
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1748675A (en) * | 1926-03-15 | 1930-02-25 | Ig Farbenindustrie Ag | Process for protecting materials against attack by moths |
| US2143639A (en) * | 1936-09-24 | 1939-01-10 | Celluloid Corp | Article of cellulose |
| US2483008A (en) * | 1944-01-29 | 1949-09-27 | Tewin Ind Inc | Proofing proteinaceous fibers against biological attack |
| US2615038A (en) * | 1948-10-15 | 1952-10-21 | Dow Chemical Co | O,o-di(polyhalophenyl) n-substituted amidothiophosphates |
| US2542604A (en) * | 1948-12-01 | 1951-02-20 | Standard Oil Dev Co | Extreme pressure lubricant and extreme pressure agents therefor |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4020129A (en) * | 1974-05-03 | 1977-04-26 | Hoechst Aktiengesellschaft | Production of dithiophosphoric acid-O,O-diesters |
Also Published As
| Publication number | Publication date |
|---|---|
| GB742782A (en) | 1956-01-04 |
| BE512531A (en) | |
| NL85053C (en) | |
| FR1059358A (en) | 1954-03-24 |
| DE936327C (en) | 1955-12-07 |
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