US2483008A - Proofing proteinaceous fibers against biological attack - Google Patents
Proofing proteinaceous fibers against biological attack Download PDFInfo
- Publication number
- US2483008A US2483008A US569279A US56927944A US2483008A US 2483008 A US2483008 A US 2483008A US 569279 A US569279 A US 569279A US 56927944 A US56927944 A US 56927944A US 2483008 A US2483008 A US 2483008A
- Authority
- US
- United States
- Prior art keywords
- lbs
- acid
- pentachlorphenol
- water
- proofing
- 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
- 239000000835 fiber Substances 0.000 title description 10
- 239000002253 acid Substances 0.000 description 24
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000004744 fabric Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 238000000034 method Methods 0.000 description 13
- 108090000623 proteins and genes Proteins 0.000 description 13
- 102000004169 proteins and genes Human genes 0.000 description 13
- 239000004753 textile Substances 0.000 description 13
- 238000001035 drying Methods 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 11
- 239000000975 dye Substances 0.000 description 10
- 235000015110 jellies Nutrition 0.000 description 10
- 239000008274 jelly Substances 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 238000003801 milling Methods 0.000 description 8
- 210000002268 wool Anatomy 0.000 description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000004078 waterproofing Methods 0.000 description 5
- MJWPFSQVORELDX-UHFFFAOYSA-K aluminium formate Chemical compound [Al+3].[O-]C=O.[O-]C=O.[O-]C=O MJWPFSQVORELDX-UHFFFAOYSA-K 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000084 colloidal system Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000005871 repellent Substances 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000001828 Gelatine Substances 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 241000256602 Isoptera Species 0.000 description 2
- 239000000980 acid dye Substances 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 230000001464 adherent effect Effects 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- KIEOKOFEPABQKJ-UHFFFAOYSA-N sodium dichromate Chemical compound [Na+].[Na+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KIEOKOFEPABQKJ-UHFFFAOYSA-N 0.000 description 2
- HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- -1 that is to say Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 231100000167 toxic agent Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical class ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 108010019160 Pancreatin Proteins 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 159000000013 aluminium salts Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000000622 chloryl group Chemical group O=Cl(=O)[*] 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- SVSHEAJPDAGGCC-UHFFFAOYSA-L disodium 7-hydroxy-8-[[4-[4-[[4-(4-methylphenyl)sulfonyloxyphenyl]diazenyl]phenyl]phenyl]diazenyl]naphthalene-1,3-disulfonate Chemical compound CC1=CC=C(C=C1)S(=O)(=O)OC2=CC=C(C=C2)N=NC3=CC=C(C=C3)C4=CC=C(C=C4)N=NC5=C(C=CC6=CC(=CC(=C65)S(=O)(=O)O)S(=O)(=O)[O-])[O-].[Na+].[Na+] SVSHEAJPDAGGCC-UHFFFAOYSA-L 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 231100000171 higher toxicity Toxicity 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- XCAUINMIESBTBL-UHFFFAOYSA-N lead(ii) sulfide Chemical compound [Pb]=S XCAUINMIESBTBL-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229940055695 pancreatin Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 229940070376 protein Drugs 0.000 description 1
- 239000012460 protein solution Substances 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 231100000046 skin rash Toxicity 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating 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 oxygen
- D06M13/152—Treating 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 oxygen having a hydroxy group bound to a carbon atom of a six-membered aromatic ring
- D06M13/156—Treating 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 oxygen having a hydroxy group bound to a carbon atom of a six-membered aromatic ring containing halogen atoms
-
- 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
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/32—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
- D06M11/36—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
- D06M11/48—Oxides or hydroxides of chromium, molybdenum or tungsten; Chromates; Dichromates; Molybdates; Tungstates
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
- D06M15/15—Proteins or derivatives thereof
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
- D06M15/15—Proteins or derivatives thereof
- D06M15/155—Treatment in the presence of salts derived from amphoteric metal hydroxides
-
- 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
Definitions
- any deposition of the phenol upon cloth for example, by impregnating the cloth with the soluble sodium salt and subsequently precipitating the free phenol in situ by means of an acid bath is not permanent; on storage, the phenol, though colliodal and adherent when formed, crystallises and the fine needle crystals have no attachment to the fibre and come away in the form of dust, thus not only depriving the cloth of its protection but attacking the nose and throat of the wearer, and when worn, causing painful skin rashes which, though they heal by first intention and have no enduring dermititic eifect, are an'effectual bar to the use of the expedient.
- the second is the ready sublimation of the phenol which is specially marked at high temperatures, such as during the normal drying of the treated cloth on tins.
- the present invention is based on the important discovery that in solutions having a pH value of between 7 and .4, pentachlorphenol can form loose addition compounds with proteins possibly of-the nature of chloramines or chloryl compounds involving the nitrogen group of the protein.
- the complex is formed in general with any protein most readily and is most stable at the so-called iso-electric point of the protein.
- the present invention consists in the production of these complexes and the application of pentachlorphenol to the textile fibres by means of them.
- the formation of the compounds by reaction with the protein of the fibre itself may be accomplished, for example, by grinding the pentachlorphenol to micron size, but it is most readily accomplished by precipitating the free phenol from its sodium salt by means of a large excess of volatile acid in the presence of a protective colloid.
- a protective colloid is not necessaryily of a protein nature or origin, although a highly demerised pro-- tein such as lysalbic acid is" very suitable for the purpose, and so is the water-soluble product obtained by profound alkaline degration of wool,
- nating 'bath such as aluminium formate
- the anionic charging of the suspended particles ensures a more intimate initial contact between the fibres and the particles.
- This mode of carrying out the invention is particularly of advantage in the wool industry, in which resistance to moth attack is of special importance since it may be conveniently applied at various stages of the usual woollen treatment.
- the suspension may be added to the mill during acid milling or to the dolly during the finishing operation or to the dye bath when an acid dye bathis used, as is almost always the case.
- the complex compound finally formed is exthen stopped-and the mass allowed to set to a soft jelly, which itself is a form in which the product tremely stable and the'objectiona'ble volatility of the toxic product is completely suppressed, and
- Example 1 10 lbs. of skin glue or gelatine are allowed to swell in 64 lbs. of water and then brought into solution by heating to 80 to 90 C. with continuous stirring. Then, 22% lbs. of neutral sodium pentachlorphenolate is added with thorough stirring part at a time, the stirring being effected until a homogeneous mass is formed.
- Theglue employed is merely a convenient protective colloid for the can be handled in commerce. As already indicated, this fine suspension of pentachlorphenol may then be employed in accordance with the invention to produce the new complex in situ upon protein textiles in a number of ways:
- souring in the usual Way preferably with formic or acetic acid, is run in cold water using the Y customary ratio of about gallons of water to 100 lbs. of cloth. Then 3 lbs. of the jelly described above is dissolved in 2 to 3 gallons of hot water at '70 to C. and poured into-the dolly when the cloth is run until the original cloudy liquor has become clear, indicating the attachment of the pentachlorphenol to the wool. The latter is finished in the usual way.
- a suitable dye bath for lbs. of wool may contain:
- an after-chrome dyestuff such as Fastchrorne cyanine 2B 10 lbs. of Glauber salts 3 lbs. of 30 per cent acetic acid, and 3 lbs. of the jelly described above dissolved in 2 to 3 gallons of hot water.
- the dyeing is carried out as usual, as is the subsequent treatment with 2 lbs. of sodium bichromate.
- An alternative dye bath may contain:
- neutral dyeing dyestuff such as Coulbs. of Glauber salts 0.5 lb. of sodium bichromate 3 lbs. of jelly dissolved in 2 to 3 gallons of hot water.
- the dyeing and subsequent treatment is as above.
- Yet another dye bath contains:
- the treatment in accordance with the invention may be carried out simultaneously with waterproofing treatment by any of the methods described above if a, suitable waterproofing a ent be employed.
- suitable waterproofing a ent be employed.
- the agents described in British Patent Specification No. 380,076 and commercially available under the trade-mark Impregnol are suitable for this purpose.
- the combined treatment may then, for example, be carried out in the following ways:
- the piece is now moth-proof and waterproof and may go straight to the stenter for drying, but better results are obtained if it is washed for 5 to 10 minutes in the dolly in a bath containing 50 gallons of water and 2 lbs. of aluminium triformate, a commercial product at 48 Twad. being approximately 10 normal with respect to aluminium and 5 normal to formic acid, after milling and before drying. During drying a pHvalue between 42 and 5 is established.
- the waterproofing agent mentioned above in an amount of 2 to 3 lbs. for each 100 lbs. of wool, for example, is added to the dyeing formula which may be one of those given above, and the dyeing conducted as usual.
- the pieces are approaching full shade, for example, 1 hour after the bath has reached the boiling temperature.
- Example 2 64 lbs. of gelatine or hide glue aresoaked overnight in 256 lbs. of water so that they are well swollen. Next day the swollen mass is brought into solution while warming to 45 C. and when it is dissolved, 1%. lbs. of ammonium sulphate and 400 cc. of ammonium solution of specific gravity 0.9 are added together with'half an ounce of commercial pancreatin. To effect demerisation by this solution, the temperature is maintained at 45 C., and the mass very thoroughly agitated for 15 minutes. The temperature is then raised very rapidly to 80 C. to kill the ferment, for which purpose the apparatus should be provided with ample heating surface and a large steam supply. The mass is then cooled as rapidly as possible with continuous stirring.
- Cloth may be padded through the solution dried on the tins or stenter, and then padded again through a 1% solution of formic acid and again dried.
- the treatment with' acid causes the pentachlorphenol to be set free in finely dispersed form from its sodium salt and during the final drying, excess formic acid is expelled and a pH between 4 and '7 established.
- Process for the treatment of a proteinaceous textilefiber to render same proofed against biological attack by the combination of penta-- chlorphenol with a protein at the surface of the fiben which comprises treating the said textile fiber with an aqueous liquid containing dispersed pentachlorphenol, a protective colloid and an acid substance and whilst maintaining the pH of the mass below 7 evaporating to dryness the resulting reaction product to render the same irreversibly stable.
- the acid substance is a heat decomposable acid reacting polyvalent metal salt of a volatile acid which decomposes during the drying liberating fiber is mixed with a solution of an alkali metal salt of pentachlorphenol and a protective colloid and the mixture is acidified with a volatile acid to produce an acid dispersion of pentachlorphenol in contact with the fiber.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB170544A GB596362A (en) | 1944-01-29 | Improvements relating to the production of toxic compounds and their use in the treatment of textiles for protection against biological attack |
Publications (1)
Publication Number | Publication Date |
---|---|
US2483008A true US2483008A (en) | 1949-09-27 |
Family
ID=9726585
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US569279A Expired - Lifetime US2483008A (en) | 1944-01-29 | 1944-12-21 | Proofing proteinaceous fibers against biological attack |
Country Status (3)
Country | Link |
---|---|
US (1) | US2483008A (en(2012)) |
BE (1) | BE471973A (en(2012)) |
FR (1) | FR944658A (en(2012)) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2615783A (en) * | 1950-08-11 | 1952-10-28 | Procter & Gamble | Modification of keratin |
US2615782A (en) * | 1950-08-11 | 1952-10-28 | Procter & Gamble | Modification of keratin |
US2710269A (en) * | 1951-07-02 | 1955-06-07 | Higgins Eric Berkeley | Method of treating woolen textile materials with di-pentachlorphenyl-mono-hydrogen phosphate for protecting such textiles against biological attack |
US2945736A (en) * | 1957-12-17 | 1960-07-19 | Hightower Morse & Company | Mothproofing of keratinaceous materials |
US2945735A (en) * | 1957-12-17 | 1960-07-19 | Hightower Morse & Company | Mothproofing of keratinaceous materials |
US3172777A (en) * | 1965-03-09 | Process for depositing a water insoluble bactericide on a fabric | ||
US3398285A (en) * | 1961-10-16 | 1968-08-20 | Perkin Elmer Corp | Spectro-radiometer with means for eliminating background noise |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1085783A (en) * | 1911-02-24 | 1914-02-03 | Condensite Company Of America | Flame-extinguishing material. |
US1618416A (en) * | 1925-07-24 | 1927-02-22 | British Dyestuffs Corp Ltd | Mildew proofing of fibrous material |
US2086676A (en) * | 1930-11-04 | 1937-07-13 | Firm Deutsche Kunstseiden Stud | Process for improving wool |
US2157113A (en) * | 1937-05-20 | 1939-05-09 | Monsanto Chemicals | Preservation of fermentable materials |
US2174475A (en) * | 1937-10-13 | 1939-09-26 | Georg Henning Chem Pharm Werk | Enzymatic manufacture of nucleotides |
US2186134A (en) * | 1938-07-07 | 1940-01-09 | A D Chapman & Company Inc | Preservative composition |
US2196988A (en) * | 1939-03-30 | 1940-04-16 | Dow Chemical Co | Phenol compositions |
US2217264A (en) * | 1937-10-15 | 1940-10-08 | Weizmann Charles | Protein preparation |
US2236921A (en) * | 1936-12-23 | 1941-04-01 | Schering Corp | Process for the manufacture of therapeutically valuable compounds of kerating degradation products |
US2292423A (en) * | 1939-06-09 | 1942-08-11 | Goodrich Co B F | Method of making mildew resistant fibrous products |
-
0
- BE BE471973D patent/BE471973A/xx unknown
-
1944
- 1944-12-21 US US569279A patent/US2483008A/en not_active Expired - Lifetime
-
1947
- 1947-04-02 FR FR944658D patent/FR944658A/fr not_active Expired
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1085783A (en) * | 1911-02-24 | 1914-02-03 | Condensite Company Of America | Flame-extinguishing material. |
US1618416A (en) * | 1925-07-24 | 1927-02-22 | British Dyestuffs Corp Ltd | Mildew proofing of fibrous material |
US2086676A (en) * | 1930-11-04 | 1937-07-13 | Firm Deutsche Kunstseiden Stud | Process for improving wool |
US2236921A (en) * | 1936-12-23 | 1941-04-01 | Schering Corp | Process for the manufacture of therapeutically valuable compounds of kerating degradation products |
US2157113A (en) * | 1937-05-20 | 1939-05-09 | Monsanto Chemicals | Preservation of fermentable materials |
US2174475A (en) * | 1937-10-13 | 1939-09-26 | Georg Henning Chem Pharm Werk | Enzymatic manufacture of nucleotides |
US2217264A (en) * | 1937-10-15 | 1940-10-08 | Weizmann Charles | Protein preparation |
US2186134A (en) * | 1938-07-07 | 1940-01-09 | A D Chapman & Company Inc | Preservative composition |
US2196988A (en) * | 1939-03-30 | 1940-04-16 | Dow Chemical Co | Phenol compositions |
US2292423A (en) * | 1939-06-09 | 1942-08-11 | Goodrich Co B F | Method of making mildew resistant fibrous products |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3172777A (en) * | 1965-03-09 | Process for depositing a water insoluble bactericide on a fabric | ||
US2615783A (en) * | 1950-08-11 | 1952-10-28 | Procter & Gamble | Modification of keratin |
US2615782A (en) * | 1950-08-11 | 1952-10-28 | Procter & Gamble | Modification of keratin |
US2710269A (en) * | 1951-07-02 | 1955-06-07 | Higgins Eric Berkeley | Method of treating woolen textile materials with di-pentachlorphenyl-mono-hydrogen phosphate for protecting such textiles against biological attack |
US2945736A (en) * | 1957-12-17 | 1960-07-19 | Hightower Morse & Company | Mothproofing of keratinaceous materials |
US2945735A (en) * | 1957-12-17 | 1960-07-19 | Hightower Morse & Company | Mothproofing of keratinaceous materials |
US3398285A (en) * | 1961-10-16 | 1968-08-20 | Perkin Elmer Corp | Spectro-radiometer with means for eliminating background noise |
Also Published As
Publication number | Publication date |
---|---|
FR944658A (fr) | 1949-04-12 |
BE471973A (en(2012)) |
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