US2202169A - Method of protecting goods containing proteins against insects - Google Patents
Method of protecting goods containing proteins against insects Download PDFInfo
- Publication number
- US2202169A US2202169A US60060A US6006036A US2202169A US 2202169 A US2202169 A US 2202169A US 60060 A US60060 A US 60060A US 6006036 A US6006036 A US 6006036A US 2202169 A US2202169 A US 2202169A
- Authority
- US
- United States
- Prior art keywords
- goods
- treatment
- against insects
- containing proteins
- proteins against
- 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
- 102000004169 proteins and genes Human genes 0.000 title description 18
- 108090000623 proteins and genes Proteins 0.000 title description 18
- 238000000034 method Methods 0.000 title description 13
- 241000238631 Hexapoda Species 0.000 title description 7
- 239000000463 material Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 12
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 11
- 210000002268 wool Anatomy 0.000 description 9
- 238000005406 washing Methods 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- -1 epifluorhydrin Chemical compound 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 239000012084 conversion product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000003292 diminished effect Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- KQSBZNJFKWOQQK-UHFFFAOYSA-N hystazarin Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2 KQSBZNJFKWOQQK-UHFFFAOYSA-N 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- LDIDZFWGINXVSD-UHFFFAOYSA-N sodium 5-amino-3-[[4-[4-[(8-amino-1-hydroxy-3,6-disulfonaphthalen-2-yl)diazenyl]phenyl]phenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=CC(=CC=C1C2=CC=C(C=C2)N=NC3=C(C4=C(C=C(C=C4C=C3S(=O)(=O)O)S(=O)(=O)O)N)O)N=NC5=C(C6=C(C=C(C=C6C=C5S(=O)(=O)O)S(=O)(=O)O)N)O.[Na+] LDIDZFWGINXVSD-UHFFFAOYSA-N 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 1
- XRWMHJJHPQTTLQ-UHFFFAOYSA-N 2-(chloromethyl)thiirane Chemical compound ClCC1CS1 XRWMHJJHPQTTLQ-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- CQPFMGBJSMSXLP-UHFFFAOYSA-M acid orange 7 Chemical compound [Na+].OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 CQPFMGBJSMSXLP-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003275 alpha amino acid group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 229940045713 antineoplastic alkylating drug ethylene imines Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000012928 buffer substance Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- LQJVOKWHGUAUHK-UHFFFAOYSA-L disodium 5-amino-4-hydroxy-3-phenyldiazenylnaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].OC1=C2C(N)=CC(S([O-])(=O)=O)=CC2=CC(S([O-])(=O)=O)=C1N=NC1=CC=CC=C1 LQJVOKWHGUAUHK-UHFFFAOYSA-L 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229940117927 ethylene oxide Drugs 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000009896 oxidative bleaching Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000009895 reductive bleaching Methods 0.000 description 1
- 230000001020 rhythmical effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BZWKPZBXAMTXNQ-UHFFFAOYSA-N sulfurocyanidic acid Chemical compound OS(=O)(=O)C#N BZWKPZBXAMTXNQ-UHFFFAOYSA-N 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 230000003313 weakening effect Effects 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
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
- D06M16/006—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic with wool-protecting agents; with anti-moth agents
-
- 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
- D06M13/11—Compounds containing epoxy groups or precursors 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
- 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
- D06M13/322—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 nitrogen
- D06M13/48—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 nitrogen containing the ethylene imine ring
Definitions
- This invention relates to protecting goods consisting of or containing protein material or conversion products thereof from the attack of small organisms.
- One of its objects is a process of protecting goods of the aforesaid kind from the attack of small organisms.
- Another object are the goods treated according to this process. Further .objects will be seen from the detailed specification following hereafter.
- natural or artificial products from proteins or conversion products of protein such as wool, natural silk, skins,-leather or feathers may be protected to a large degree from being eaten by small organisms or may be completely protected from being eaten by such organisms if they are subjected to the action of an alkylene oxide or a derivative or an analogue thereof under such conditions that a permanent chemical change (substitution) is produced.
- the product may be treated in an aqueous bath, if desired in conjunction with a washing or a dyeing process, particularly dyeing with dyestuffs in a neutral bath, or by impregnation and subsequent steaming or heating under predetermined conditions of hygrometric state of the surrounding atmosphere or by action of the reagent in gaseous or gasified condition, this mode being of particular advantage.
- the fundamentally new treatment with the gaseous or gasified reagent is also applicable for protecting effectively objects which cannot, at all events without further precautions, be subjected to a treatment with solutions of the known agents for protecting goods against damagesby moths; such objects are pieces of furniture, carpets, skins, confectioners wares, military equipments, valuable museum specimens, any of these containing in one part or another a protein substance liable to attack or already attacked by the small organism.
- Objects which have already suffered from moth for instance furniture upholstered with wool or hair, down quilts or cushions, may be very simply both ridden of moth and rendered permanently resistant to moth.
- Suitable reagents are propylene-oxide, cyclohexene-oxide, butadiene-dioxide, epichlorhydrin, epifluorhydrin, 1-chlor-2.3-propylensulphide halogenphenoxypropene-oxide, alkylethyleneimine, such as butylethyleneimine, diethylalkyleneiminium halide, 3-hydroxy-l-dialkyltrimethyleneiminium salts; also products which have in their composition capillary active radicals which are specifically protective groups of an effect in itself known and/or groups lending solubility in water other than basic groups are useful for the invention, for example propene-oxide derivatives of halogen-hydroxy-triphenylmethane sulfonic acids.
- the ction is the more rapid and deep seated the higher the degree of swollenness of the material to be treated.
- the temperature of treatment may be reduced.
- the simplest method of controlling the swollen condition in the gaseous treatment is by adjusting the relative moisture in the atmosphere. This may vary between, for instance, and It is also possible to use saturated vapour insofar as the nature of the material to be-treated permits. The choice of a certain hygrometric state, therefore, is not only an expedient for obtaining the desired effect, but also always depends on the kind of goods to be treated and their resistance to treatment. In the case of pieces of furniture, for example, operating in a highly moist atmosphere requires caution.
- a volatile or non-volatile swelling agent such as iormamide, acetamide, phenol, sodium cresolsulfonate, a sulfocyanide or another substance accelerating the reaction, may be added to the treating bath or padding solutions.
- a particularly powerful efiect is exerted by drin or epifluorhydrin.
- the epihalogenhydrins are of the first importance in the gaseous treatment. It the treatment, for instance with epichlorhydrin, is to be combined with a dyeing or washing operation, for example with the washing of raw wool, it is to be recommended that, so far as the reacting substances are comparatively easily hydrolysed, the operation should be conducted at the lowest possible temperature to begin with, for example 40-50 C. and with as little treating liquid as possible, closed apparatus (dyeing apparatus, washing drum) being used in the case of relatively easily volatile substances.
- the reagents used according to the invention may also be added to organic solvents used in the extraction of raw wool; preferably in this case also care is taken that there is a somewhat increased percentage of moisture in the goods, so that a suilicient eflect may be obtained.
- This effect can be increased by heating or steaming after the organic solvent has been separated, particularly when non-volatile agents, namely such as have afllnity to the goods under treatment, are used.
- a The capacity of the solvent to takeup moisture may be increased by the addition of an alcohol or a benzine soap.
- the treatment may be conducted in the presence of an oxidizing or reducing bleaching agent or of an anti-oxidizing agent.
- the process may also be conducted with exclusion of atmospheric oxygen.
- Uncolored raw or finished products may be bleached with the-usual bleaching agents in known manner after the treatment. When properly carried out the treatment is without influence on the final degree of bleaching.
- an agent adapted to protect fiber or a buffer substance for example an alkali phosphate, magnesium sulfate, a hydroxyalkylated water-soluble protein substance, a tertiary amino-acid, a condensation product of phenol-sulfonic acid and formaldehyde may be added.
- the presence of formaldehyde is sometimes also of advantage.
- the goods may also be treated beforehand with agents that prevent yellowing and are protective to the fiber.
- epichlorhydrin With greater density of packing the quantity of epichlorhydrin in proportion to the weight of the goods may be diminished if it is not preferred to shorten correspondingly the duration of the treatment.
- the unconsumed epichlorhydrin may be recovered in known manner, for example, by absorption in active carbon or by evacuation and compression while cooling.
- the unconsumed gas may be recovered by washing with ammonia and in the form of a hydroxy-alkylamine be used for other purposes.
- Example 2 A piece of furniture upholstered the attack of moth than is the untreated wool.
- epichlorhydrin solution in like manner slivers can be treated with epichlorhydrin solution in a dyeing apparatus.
- the epichlorhydrin is more profitably utilized when there is added to the liquor a salt, for instance sodium sulfate.
- Example 4 Wood piece goods are impregnated on the foulard apparatus with a solution of 5 per cent strength of diethyl-ethyleneiminium chloride, then wrung. out, lightly dried, rolled up and heatedior 8 hours in an atmosphere of 75 per cent saturation with water-vapour. The fabric is thus protected against the attack of moth.
- the method of permanently protecting goods containing proteins against insects which comprises treating the goods at a temperature above 40 C. with a compound selected from the group consisting of alkvlene oxides, alkyiene imines, and alkylene sulfides until the amino groups of the protein material are substantially alkylized.
- the method of permanently protecting goods containing proteins against insects which comprises treating the goods at a temperature above 40 C. with the vaporof a compound selected irom the group consisting of alkylene oxides, alkylene. imines, and alkylen'e sulfides until the amino groups of the protein material are substantially alkylized.
- the method or permanently protecting goods containing proteins against insects which comprises treating the goods at a temperature above 40' C. with an epihalogenhydrin until the amino groups of the protein material are substantially substituted with hydroxyhalogen alkyl groups.
- the method of permanently protecting goods containing proteins against insects which comprises treating the goods at a temperature above 40 C. with a compound selected from the group consisting oi alkylated ethylene imines and the quaternary salts thereoi, until the amino groups or the protein material are substantially alkylized.
- the method of permanently protecting goods containing proteins against insects which comprises treating the goods with a swelling agent and at a temperature above 40 'C. with a compound selected from the group consisting of alkylene oxides, alkylene imines and alkylene sulfldes until the amino groups of the protein material are substantially alkylized.
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 |
---|---|---|---|
DE2202169X | 1935-01-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
US2202169A true US2202169A (en) | 1940-05-28 |
Family
ID=7989820
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US60060A Expired - Lifetime US2202169A (en) | 1935-01-25 | 1936-01-21 | Method of protecting goods containing proteins against insects |
Country Status (3)
Country | Link |
---|---|
US (1) | US2202169A (enrdf_load_stackoverflow) |
BE (1) | BE413312A (enrdf_load_stackoverflow) |
FR (1) | FR800582A (enrdf_load_stackoverflow) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2426125A (en) * | 1944-04-03 | 1947-08-19 | Kelco Co | Manufacture of glycol alginates |
US2925317A (en) * | 1956-09-18 | 1960-02-16 | Joseph E Moore | Shrinkproofing of protein fibers with polyalkyleneimines |
US2926064A (en) * | 1955-06-23 | 1960-02-23 | Bohme Fettchemie Gmbh | Process for making wool resistant to felting and shrinking |
US2928714A (en) * | 1957-04-23 | 1960-03-15 | Varsenig Z Pasternak | Epichlorohydrin treatment of feathers |
US3252948A (en) * | 1960-08-19 | 1966-05-24 | Manecke Georg | Interpolymers of the m-fluoroanilide of methacrylic acid |
US3285691A (en) * | 1963-10-28 | 1966-11-15 | Nathan H Koenig | Epichlorohydrin and acid anhydride treatment of wool |
US3326846A (en) * | 1964-02-20 | 1967-06-20 | Du Pont | Use of fluoroalcohols in the dyeing of synthetic polymers |
US3402012A (en) * | 1964-03-05 | 1968-09-17 | Ciba Ltd | Dyeing nickel-containing polyolefin fibers with o-alkylmercaptoazo dyes |
US3506391A (en) * | 1962-02-15 | 1970-04-14 | Deering Milliken Res Corp | Cross-linking cellulosics with epichlorohydrin vapors |
US3963436A (en) * | 1974-03-21 | 1976-06-15 | Hoechst Aktiengesellschaft | Bis nitrophenyl diethylene triamine dyeing of synthetic acid modified fibers |
US3966405A (en) * | 1974-12-17 | 1976-06-29 | Hoechst Aktiengesellschaft | N-Alkyl nitro phenyl diethylene triamine dyeing of acid modified synthetic fibers |
-
0
- BE BE413312D patent/BE413312A/xx unknown
-
1936
- 1936-01-14 FR FR800582D patent/FR800582A/fr not_active Expired
- 1936-01-21 US US60060A patent/US2202169A/en not_active Expired - Lifetime
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2426125A (en) * | 1944-04-03 | 1947-08-19 | Kelco Co | Manufacture of glycol alginates |
US2926064A (en) * | 1955-06-23 | 1960-02-23 | Bohme Fettchemie Gmbh | Process for making wool resistant to felting and shrinking |
US2925317A (en) * | 1956-09-18 | 1960-02-16 | Joseph E Moore | Shrinkproofing of protein fibers with polyalkyleneimines |
US2928714A (en) * | 1957-04-23 | 1960-03-15 | Varsenig Z Pasternak | Epichlorohydrin treatment of feathers |
US3252948A (en) * | 1960-08-19 | 1966-05-24 | Manecke Georg | Interpolymers of the m-fluoroanilide of methacrylic acid |
US3506391A (en) * | 1962-02-15 | 1970-04-14 | Deering Milliken Res Corp | Cross-linking cellulosics with epichlorohydrin vapors |
US3285691A (en) * | 1963-10-28 | 1966-11-15 | Nathan H Koenig | Epichlorohydrin and acid anhydride treatment of wool |
US3326846A (en) * | 1964-02-20 | 1967-06-20 | Du Pont | Use of fluoroalcohols in the dyeing of synthetic polymers |
US3402012A (en) * | 1964-03-05 | 1968-09-17 | Ciba Ltd | Dyeing nickel-containing polyolefin fibers with o-alkylmercaptoazo dyes |
US3963436A (en) * | 1974-03-21 | 1976-06-15 | Hoechst Aktiengesellschaft | Bis nitrophenyl diethylene triamine dyeing of synthetic acid modified fibers |
US3966405A (en) * | 1974-12-17 | 1976-06-29 | Hoechst Aktiengesellschaft | N-Alkyl nitro phenyl diethylene triamine dyeing of acid modified synthetic fibers |
Also Published As
Publication number | Publication date |
---|---|
BE413312A (enrdf_load_stackoverflow) | |
FR800582A (fr) | 1936-07-08 |
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