US3153565A - Process for the treatment of synthetic linear polycarbonamide textile fibers - Google Patents
Process for the treatment of synthetic linear polycarbonamide textile fibers Download PDFInfo
- Publication number
- US3153565A US3153565A US62325A US6232560A US3153565A US 3153565 A US3153565 A US 3153565A US 62325 A US62325 A US 62325A US 6232560 A US6232560 A US 6232560A US 3153565 A US3153565 A US 3153565A
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- United States
- Prior art keywords
- treatment
- strength
- rkm
- bath
- peroxide
- 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
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- 239000000835 fiber Substances 0.000 title description 15
- 238000011282 treatment Methods 0.000 title description 14
- 239000004753 textile Substances 0.000 title description 6
- 238000000034 method Methods 0.000 title description 3
- 238000005406 washing Methods 0.000 description 17
- 238000004061 bleaching Methods 0.000 description 13
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 13
- 150000002978 peroxides Chemical class 0.000 description 12
- 239000004952 Polyamide Substances 0.000 description 10
- 229920002647 polyamide Polymers 0.000 description 10
- 235000019353 potassium silicate Nutrition 0.000 description 10
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 10
- 239000003223 protective agent Substances 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000344 soap Substances 0.000 description 8
- 229960001922 sodium perborate Drugs 0.000 description 8
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 6
- 229940048086 sodium pyrophosphate Drugs 0.000 description 6
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 6
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 6
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 5
- 229920002292 Nylon 6 Polymers 0.000 description 5
- 239000002657 fibrous material Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- LHYIWYMOHCIQRH-UHFFFAOYSA-N 1-n',4-n'-dihydroxybutanediimidamide Chemical compound ON=C(N)CCC(N)=NO LHYIWYMOHCIQRH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 206010003549 asthenia Diseases 0.000 description 3
- VDEUYMSGMPQMIK-UHFFFAOYSA-N benzhydroxamic acid Chemical compound ONC(=O)C1=CC=CC=C1 VDEUYMSGMPQMIK-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- -1 peroxide compounds Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NZOXKLBUCRZPQB-UHFFFAOYSA-N (2z)-2-amino-2-hydroxyiminoacetamide Chemical compound NC(=O)C(N)=NO NZOXKLBUCRZPQB-UHFFFAOYSA-N 0.000 description 2
- VTWKXBJHBHYJBI-SOFGYWHQSA-N (ne)-n-benzylidenehydroxylamine Chemical compound O\N=C\C1=CC=CC=C1 VTWKXBJHBHYJBI-SOFGYWHQSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- BTLSLHNLDQCWKS-UHFFFAOYSA-N oxocan-2-one Chemical compound O=C1CCCCCCO1 BTLSLHNLDQCWKS-UHFFFAOYSA-N 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 235000019832 sodium triphosphate Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004973 alkali metal peroxides Chemical class 0.000 description 1
- 150000004974 alkaline earth metal peroxides Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical compound NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 description 1
- MMCOUVMKNAHQOY-UHFFFAOYSA-N carbonoperoxoic acid Chemical compound OOC(O)=O MMCOUVMKNAHQOY-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- PEYVWSJAZONVQK-UHFFFAOYSA-N hydroperoxy(oxo)borane Chemical compound OOB=O PEYVWSJAZONVQK-UHFFFAOYSA-N 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000004137 magnesium phosphate Substances 0.000 description 1
- 235000010994 magnesium phosphates Nutrition 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D9/00—Compositions of detergents based essentially on soap
- C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
- C11D9/22—Organic compounds, e.g. vitamins
- C11D9/30—Organic compounds, e.g. vitamins containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3902—Organic or inorganic per-compounds combined with specific additives
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D9/00—Compositions of detergents based essentially on soap
- C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
- C11D9/42—Per-compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/10—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/10—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
- D06L4/12—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen combined with specific additives
-
- 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
- D06M13/325—Amines
- D06M13/332—Di- or polyamines
-
- 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
- D06M13/325—Amines
- D06M13/335—Amines having an amino group bound to a carbon atom of a six-membered aromatic ring
-
- 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
- D06M13/35—Heterocyclic compounds
-
- 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
- D06M13/376—Oximes
-
- 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
- D06M13/402—Amides imides, sulfamic acids
- D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21C—PRODUCTION OF CELLULOSE BY REMOVING NON-CELLULOSE SUBSTANCES FROM CELLULOSE-CONTAINING MATERIALS; REGENERATION OF PULPING LIQUORS; APPARATUS THEREFOR
- D21C9/00—After-treatment of cellulose pulp, e.g. of wood pulp, or cotton linters ; Treatment of dilute or dewatered pulp or process improvement taking place after obtaining the raw cellulosic material and not provided for elsewhere
- D21C9/02—Washing ; Displacing cooking or pulp-treating liquors contained in the pulp by fluids, e.g. wash water or other pulp-treating agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/06—Resin bleach
Definitions
- the present invention relates to improvements in preventing damage to textile fibers containing a fiber forming synthetic linear polycarbonamide which has recurring amide groups as integral parts of the main polymer chain when treated with peroxidic bleaching compounds.
- polyamide fibers are strongly attacked when treated in washing and bleaching baths containing peroxide compounds, so that appreciable losses in strength occur.
- the decrease in strength of the polyamide fibers may amount to up to 40 to 80% of the original strength if the action of the peroxide containing washing and bleaching baths is carried out at relatively high temperatures over a relatively long period, which is often necessary, for example, in the treatment of mixed fibrous materials containing polyamide for the purpose of producing an adequate bleaching effect, or if, as is necessary when using detergents containing peroxide, the treatment of the articles containing polyamide has to be repeated at intervals of time when the articles become soiled. The same damage to the fibers occurs even if the peroxide containing bleaching and Washing baths are stabilized in the conventional manner with magnesium silicate or phosphates or other additives which moderate the spontaneous evolution of oxygen.
- the peroxide compounds referred to herein include hydrogen peroxide, sodium peroxide, other alkali or alkaline earth metal peroxides, persulphuric acid or its salts, perboric acid or its salts, percarbonic acid or its salts, perphosphoric acid or its salts, or similar compounds which form hydrogen peroxide in acid medium. According to the invention,
- the bleaching or washing baths can contain active oxygen up to a maximum amount of 0.3 mol of H 0 or 0.3 gram atom of active oxygen per liter of bleaching liquid.
- the protective agents described herein are added in amounts of 0.01 to 0.05 mol per liter. However, certain individual agents are effective even in of this concentration.
- peroxide detergents yield maximum concentrations, of 0.25 g. or 0.016 gram atom of active oxygen per liter. In this case, 0.001 to 0.005 mol of the said protective agents per liter of peroxide detergent bath is sufiicient, while once again individual products provide complete protection of the fibers when used with A of this concentration.
- the bleaching and washing baths may as customary also contain stabilizers (water glass, magnesium salts or phosphates) and also means for adjusting the pH value and surface active substances.
- the protective agent can also be products applied in aqueous or alcoholic solution to the polycarbonamide fibers and then dried. The strength of textiles made of polycarbonamide fibers and treated in this manner is scarcely reduced, even after subsequent repeated peroxide treat ment in a bleaching or washing bath which does not contain any protective agent.
- the products may also be used by incorporating them in the Perlon or Nylon substance itself from which the fibers are spun.
- Example 1 A stranded yarn material consisting of e caprolactam filaments with a titre of 60 deniers was treated in the bath ratio of 1:50 with occasional manipulation, for two hours at a temperature of 60 C. in a bath which contained:
- Example 2 e Caprolactam Perlon fabric having a warp and weft both consisting of 60 denier c caprolactam silk was washed for two hours at 90 C. in a washing solution which contained peroxide and to which 0.3 g. of benzaldoxime was added as protective agent per liter of the solution.
- the tensile strength of the e caprolactam fabric dropped after this treatment from 45.5 Rkm. to 43.83 Rkm., this corresponding to a strength loss of 3.7%.
- the bath had the following composition per liter:
- Rkm. the number of kilometers of the yarn which will be sustained by the yarn before breaking.
- Example 4 A length of e-caprolactam underwear material was subjected to a bleaching treatment for four hours at a temperature of 60 C. in a bath containing hydrogen peroxide.
- the bath had the following composition:
- Example 5 A hank of e caprolactam knitting yarn with the metric number 17.1/ 3 was treated for two hours at a temperature of C. in a bath containing:
- Example 6 A hank of yarn consisting of e caprolactam and having a titre of 60 deniers was washed for 2 hours at a temperature of about C. in a bath containing per liter:
- Example 7 A length of material consisting of 60 denier e caprolactam warp and weft was subjected to a washing treatment for two hours at 90 C.
- the washing bath had the fol lowing composition:
- Example 8 2O denier endless e caprolactam polyamide (Perlon) silk was treated at a bath ratio of 1:30 at 90 C. with a solution containing 10 g. per liter of a commercial wash ing agent to which oxalic acid diamide oxime had been added as a protective agent.
- the washing agent was of the following composition, parts by weight:
- the original tensile strength of the e caprolactam filaments was 46.5 Rkm. and was only lowered to 44.8 Rkm. by 2 hours treatment in the bath, this corresponding to a 3.7% loss in strength.
- the treated filaments only had a tensile strength of 34.2 Rkm. which corresponded to a 26.5% loss in strength.
- Example 9 15 denier monofilament e caprolactam polyamide stocking silk delustered with titanium dioxide was treated at a bath ratio of 1:30 for two hours at 85 C. with a washing bath containing 10 g. per liter of the following washing agent:
- Example 10 Strands of 60 denier glossy e caprolactam polyamide silk were treated for 2 hours at 85 C. in a bath ratio of 1:50 with 1% aqueous solution of the following washing agent:
- Example 11 A yarn strand of 60 denier e caprolactam polyamide (Perlon L) was treated for 2 hours at 80 C. in a bath 6 containing 10 g. per liter .of a washing agent of the following composition:
- a process for treating a synthetic linear polycarbonamide fiber material with an aqueous solution containing an inorganic peroxide textile bleaching agent which comprises treating said fiber material with said aqueous solution containing an inorganic peroxide textile bleaching agent in the presence of water soluble organic compound containing at least one hydroxamic acid group in a quantity suflicient to reduce the loss of strength in the polycarbonamide fibers substantially below that which would be suffered in the absence of said water soluble organic compound.
Description
United States Patent 3,153,565 PROCESS FOR THE TREATMENT OF SYNTHETIC LINEAR POLYCARBONAMIDE TEXTILE FIBERS Karl Dithmar and Elfriede Naujoks, Frankfurt am Main,
Germany, assignors to Deutsche Goldund Silber- Scheideanstalt vormals Roessler, Frankfurt am Main, Germany No Drawing. Filed Oct. 13, 1960, Ser. No. 62,325 Claims priority, application Germany, Mar. 12, 1953, D 14,553; Mar. 20, 1954, D 17,356; Nov. 13, 1954, D 19,111; Dec. 11, 1954, D 19,309
1 Claim. (Cl. 8-111) The present invention relates to improvements in preventing damage to textile fibers containing a fiber forming synthetic linear polycarbonamide which has recurring amide groups as integral parts of the main polymer chain when treated with peroxidic bleaching compounds.
It is known that polyamide fibers are strongly attacked when treated in washing and bleaching baths containing peroxide compounds, so that appreciable losses in strength occur. The decrease in strength of the polyamide fibers, for example, of the fibrous materials known under the trade names of Perlon and Nylon, may amount to up to 40 to 80% of the original strength if the action of the peroxide containing washing and bleaching baths is carried out at relatively high temperatures over a relatively long period, which is often necessary, for example, in the treatment of mixed fibrous materials containing polyamide for the purpose of producing an adequate bleaching effect, or if, as is necessary when using detergents containing peroxide, the treatment of the articles containing polyamide has to be repeated at intervals of time when the articles become soiled. The same damage to the fibers occurs even if the peroxide containing bleaching and Washing baths are stabilized in the conventional manner with magnesium silicate or phosphates or other additives which moderate the spontaneous evolution of oxygen.
It has now been found that it is possible to produce a substantial protective action on fibers, spun yarns, woven and knitted fabrics containing synthetic linear polycarbonamides, or articles manufactured therefrom, either alone or together with other fibrous materials during bleaching with peroxide compounds. The peroxide compounds referred to herein include hydrogen peroxide, sodium peroxide, other alkali or alkaline earth metal peroxides, persulphuric acid or its salts, perboric acid or its salts, percarbonic acid or its salts, perphosphoric acid or its salts, or similar compounds which form hydrogen peroxide in acid medium. According to the invention,
materials with peroxide compoundsin h ""eariirfis'i'se arned 6131 iii the P 9meant-oximcspnhygl q 76. T
Illustrative examples ofsuchoxi'fies or hydroxamic acids are:
Oxaldihydroxamic acid HO\ /OH CO x EON NOH 0 0 C-C HOHN NHOH Benzaldoxime 'ice Patented Oct. 20, 1964 Propionic hydroxamic acid /OH CgH5-C\ NOH NHOH Benzhydroxamic acid NOH o Ga NHOH Succinic dialdehyde dioxime H H HON=JJ-CH CH =NOH Succinic diamide dioxime INIYHQ NH HoN=ccHr-oHr 3=NoH Cyclohexanone oxime CHg-CHg OH; C=NOH CHFOHQ The compounds referred to develop their protective effect in the bleaching bath in the presence of peroxides by preventing the attack of the active oxygen on the polycarbonamide fibers. The bleaching or washing baths can contain active oxygen up to a maximum amount of 0.3 mol of H 0 or 0.3 gram atom of active oxygen per liter of bleaching liquid. The protective agents described herein are added in amounts of 0.01 to 0.05 mol per liter. However, certain individual agents are effective even in of this concentration. When used according to instructions, peroxide detergents yield maximum concentrations, of 0.25 g. or 0.016 gram atom of active oxygen per liter. In this case, 0.001 to 0.005 mol of the said protective agents per liter of peroxide detergent bath is sufiicient, while once again individual products provide complete protection of the fibers when used with A of this concentration. They may also be directly incorporated with washing powders to provide peroxide detergent mixtures which in practice do not reduce the tensile strength of polyamide fibers, even when the treatment is repeated several times. The bleaching and washing baths may as customary also contain stabilizers (water glass, magnesium salts or phosphates) and also means for adjusting the pH value and surface active substances. The protective agent can also be products applied in aqueous or alcoholic solution to the polycarbonamide fibers and then dried. The strength of textiles made of polycarbonamide fibers and treated in this manner is scarcely reduced, even after subsequent repeated peroxide treat ment in a bleaching or washing bath which does not contain any protective agent.
Finally, the products may also be used by incorporating them in the Perlon or Nylon substance itself from which the fibers are spun.
The following examples will serve to illustrate several embodiments of the invention.
Example 1 A stranded yarn material consisting of e caprolactam filaments with a titre of 60 deniers was treated in the bath ratio of 1:50 with occasional manipulation, for two hours at a temperature of 60 C. in a bath which contained:
Example 2 e Caprolactam Perlon fabric having a warp and weft both consisting of 60 denier c caprolactam silk was washed for two hours at 90 C. in a washing solution which contained peroxide and to which 0.3 g. of benzaldoxime was added as protective agent per liter of the solution.
The tensile strength of the e caprolactam fabric dropped after this treatment from 45.5 Rkm. to 43.83 Rkm., this corresponding to a strength loss of 3.7%.
The bath had the following composition per liter:
1.0 g. 5.0 g. 0.2 g. 1.5 g. 0.7 g. 1.6 g. 0.3 g.
Rkm.:the number of kilometers of the yarn which will be sustained by the yarn before breaking.
of sodium perborate of soap flakes of dry water glass of calcined soda of sodium bicarbonate of sodium pyrophosphate of a-benzaldoxime Example 3 Stranded material consisting of c caprolactam silk was treated in a bath for 2 hours at a temperature just below boiling point, the material being moved occasionally. The bath had the following composition per liter:
2.5 g. 4.5 g. 0.2 g. 1.2 g. 0.5 g. 1.1 g. 0.5 g.
of sodium perborate of soap powder of dry water glass of calc. soda of sodium bicarbonate of neutral sodium pyrophosphate of propionic hydroxamic acid After being washed by boiling, the strength had dropped from 45.0 to 43.02 Rkm., this being a strength loss of 4.3%, while the strength loss was 31.7% in a comparative test in which no propionic hydroxamic acid was added.
Example 4 A length of e-caprolactam underwear material was subjected to a bleaching treatment for four hours at a temperature of 60 C. in a bath containing hydrogen peroxide.
The bath had the following composition:
4.8 g./liter of active oxygen in the form of hydrogen peroxide (0.3 mol) 0.1 g. of crystallized magnesium sulphate 1.0 cc. of commercially available water glass 1.4 g. of benzhydroxamic acid (0.01 mol) The strength of the e-caprolactam material, which was 45.5 Rkm., prior to the treatment, was reduced to 44.10 Rkm. after the bleaching, this corresponding to a reduction of 3.1%
4 Example 5 A hank of e caprolactam knitting yarn with the metric number 17.1/ 3 was treated for two hours at a temperature of C. in a bath containing:
2.0 g. of sodium perborate 0.1 g. of crystallized magnesium sulphate 1.0 cc. of commercially available water glass 5.0 g. of soap flakes 0.5 g. of succinic dialdehyde dioxime After the treatment, it was established that the reduction in strength was from 29.65 to 27.12 Rkm., this corresponding to a loss of 8.6%.
Example 6 A hank of yarn consisting of e caprolactam and having a titre of 60 deniers was washed for 2 hours at a temperature of about C. in a bath containing per liter:
1.0 g. 5.0 g. 0.2 g. 1.5 g. 0.7 g. 1.6 g. 0.5 g.
of sodium perborate of soap flakes of dry water glass of calc. soda of sodium bicarbonate of sodium pyrophosphate of cyclohexanone oxime The strength of the polyamide silk was lowered from an initial value of 43 Rkm. to 39.15 Rkm., this corresponding to a strength loss of 9.0%
Example 7 A length of material consisting of 60 denier e caprolactam warp and weft was subjected to a washing treatment for two hours at 90 C. The washing bath had the fol lowing composition:
1.0 g. 5.0 g. 0.2 g. 1.5 g. 0.7 g. 1.6 g. 0.5 g.
of sodium perborate of soap flakes of dry water glass of calc. soda of sodium bicarbonate of sodium pyrophosphate of succinic diamide dioxirne The tensile strength of the weft material was reduced from 45.0 Rkm. to 41.49 Rkm., this corresponding to a reduction in strength of 7.8%
Example 8 2O denier endless e caprolactam polyamide (Perlon) silk was treated at a bath ratio of 1:30 at 90 C. with a solution containing 10 g. per liter of a commercial wash ing agent to which oxalic acid diamide oxime had been added as a protective agent.
The washing agent was of the following composition, parts by weight:
Soap Powder 57.0 Caleined soda 15.0 Sodium pyrophosphate 7.5 Sodium tripolyphosphate 7.5 Dry water glass 7.0 Sodium perborate 6.0 Oxalic acid diamide oxime 1.0
The original tensile strength of the e caprolactam filaments was 46.5 Rkm. and was only lowered to 44.8 Rkm. by 2 hours treatment in the bath, this corresponding to a 3.7% loss in strength.
When the same washing agent was employed but without the protective agent, the treated filaments only had a tensile strength of 34.2 Rkm. which corresponded to a 26.5% loss in strength.
Example 9 15 denier monofilament e caprolactam polyamide stocking silk delustered with titanium dioxide was treated at a bath ratio of 1:30 for two hours at 85 C. with a washing bath containing 10 g. per liter of the following washing agent:
Parts by weight Marseilles soap 57.0 Soda 15.0 Pulverized water glass 7.0 Sodium pyrophosphate 7.5 Sodium tripolyphosphate 7.5 Sodium perborate 6.0 Benzhydroxamic acid 2.0
Example 10 Strands of 60 denier glossy e caprolactam polyamide silk were treated for 2 hours at 85 C. in a bath ratio of 1:50 with 1% aqueous solution of the following washing agent:
Parts by weight Soap flakes 42.0 Soda 17.4 Dry water glass 2.6 Trilon BR (chelating agent) 0.4 Cellulose glycolate 0.1
Blankophor BH extra high concentrate (brightener) 0.075 Moisture (from chemicals) 28.425 Sodium perborate 7.0 Succinic diamide dioxime 2.0
The treatment caused a drop in tensile strength from 47.0 Rkm. to 43.4 Rkm. which corresponded to a 7.7% loss in strength. In the absence of the protective agent succinic diamide dioxime but otherwise under the same conditions the loss in strength amounted to 23.8%.
Example 11 A yarn strand of 60 denier e caprolactam polyamide (Perlon L) was treated for 2 hours at 80 C. in a bath 6 containing 10 g. per liter .of a washing agent of the following composition:
Parts by weight The treatment caused a drop in tensile strength from 43.0 Rkm. to 39.1 Rkm. which corresponded to a 9% loss.
In the absence of the oxime protective agent but otherwise under the same conditions the loss in strength amounted to 19.3%.
This application is a continuation-in-part of application Serial No. 494,554, filed March 15, 1955, now abandoned, which in turn is a continuation-in-part of application Serial No. 419,911, filed March 11, 1954, now Patent No. 2,909,404.
We claim:
A process for treating a synthetic linear polycarbonamide fiber material with an aqueous solution containing an inorganic peroxide textile bleaching agent which comprises treating said fiber material with said aqueous solution containing an inorganic peroxide textile bleaching agent in the presence of water soluble organic compound containing at least one hydroxamic acid group in a quantity suflicient to reduce the loss of strength in the polycarbonamide fibers substantially below that which would be suffered in the absence of said water soluble organic compound.
References Cited in the file of this patent UNITED STATES PATENTS 2,153,416 Frenkel Apr. 4, 1939 2,377,066 Baird May 22, 1945 2,620,325 Langkammerer Dec. 2, 1952 2,661,305 Appleton Dec. 1, 1953 2,730,428 Lindner Ian. 10, 1956 2,909,404 Dithmar Oct. 20, 1959 FOREIGN PATENTS 199,158 Austria Aug. 25, 1958 555,998 Great Britain Sept. 15, 1943 OTHER REFERENCES Yale: Chemical Review, vol. 33, pp. 209-256 (1943).
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DED14553A DE976170C (en) | 1953-03-12 | 1953-03-12 | Process for the treatment of polyamide fibers with peroxide-containing bleaches or detergents |
DED17356A DE945443C (en) | 1953-03-12 | 1954-03-20 | Fiber protectants |
DED19111A DE1020433B (en) | 1953-03-12 | 1954-11-13 | Process for the treatment of synthetic polyamide fibers with peroxide-containing bleaches or detergents |
DED19309A DE1025376B (en) | 1953-03-12 | 1954-12-11 | Process for the treatment of polyamide fibers with peroxide-containing bleaches or detergents |
Publications (1)
Publication Number | Publication Date |
---|---|
US3153565A true US3153565A (en) | 1964-10-20 |
Family
ID=27436738
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US419911A Expired - Lifetime US2909404A (en) | 1953-03-12 | 1954-03-11 | Protection of polyamide fibers during treatment with peroxide containing bleaching or washing agents |
US62325A Expired - Lifetime US3153565A (en) | 1953-03-12 | 1960-10-13 | Process for the treatment of synthetic linear polycarbonamide textile fibers |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US419911A Expired - Lifetime US2909404A (en) | 1953-03-12 | 1954-03-11 | Protection of polyamide fibers during treatment with peroxide containing bleaching or washing agents |
Country Status (7)
Country | Link |
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US (2) | US2909404A (en) |
BE (1) | BE536668A (en) |
CH (2) | CH333466A (en) |
DE (4) | DE976170C (en) |
FR (2) | FR1121229A (en) |
GB (2) | GB767025A (en) |
NL (4) | NL295923A (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3480391A (en) * | 1967-08-24 | 1969-11-25 | Sinclair Research Inc | Hydroxylamine solutions stabilized with an amide oxime and method for their preparation |
US3480392A (en) * | 1967-08-24 | 1969-11-25 | Sinclair Research Inc | Hydroxylamine solutions stabilized with a hydroxamic acid and method for their preparation |
US3628906A (en) * | 1967-08-26 | 1971-12-21 | Degussa | Agent for protecting polyamide fibers or threads against the attack of bleaching and washing baths |
US3975153A (en) * | 1975-08-25 | 1976-08-17 | Fmc Corporation | Activation of peroxygen bleaches using isophorone enol acetates and isophorone oximinoacetate |
US4021361A (en) * | 1975-08-25 | 1977-05-03 | Fmc Corporation | Storage-stable detergent composition containing sodium perborate and activator |
EP0384912A2 (en) * | 1989-02-21 | 1990-08-29 | Monsanto Company | Hydroxamate bleach stabilizer |
US5045223A (en) * | 1990-03-16 | 1991-09-03 | Lever Brothers Company, Division Of Conopco, Inc. | N-sulfonyloxaziridines as bleaching compounds |
US5047163A (en) * | 1990-03-16 | 1991-09-10 | Lever Brothers Company, Division Of Conopco, Inc. | Activation of bleach precursors with sulfonimines |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL112268C (en) * | 1953-03-12 | |||
DE1116393B (en) * | 1959-11-14 | 1961-11-02 | Rhodiaceta Ag | Process for increasing the lightfastness of molded polyamides |
BE614157A (en) * | 1961-03-09 | |||
US3293110A (en) * | 1962-06-26 | 1966-12-20 | Du Pont | Polymeric staple fiber blend containing weakened polyamide fibers |
US3740187A (en) * | 1971-06-03 | 1973-06-19 | Monsanto Co | Processes for bleaching textiles |
GB8714898D0 (en) * | 1987-06-25 | 1987-07-29 | Du Pont Canada | Protecting articles from bleaching solutions |
US4959267A (en) * | 1988-11-23 | 1990-09-25 | Du Pont Canada Inc. | Fiber reinforced rubber products |
FR2986798B1 (en) * | 2012-02-14 | 2014-01-31 | Rhodia Operations | NOVEL AGENT INHIBITOR FOR SWELLING OF CLAYS, COMPOSITIONS COMPRISING SAID AGENT AND METHODS EMPLOYING SAID AGENT |
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Publication number | Priority date | Publication date | Assignee | Title |
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US2153416A (en) * | 1936-05-22 | 1939-04-04 | Hatters Fur Exchange Inc | Treatment of animal and vegetable fibers |
GB555998A (en) * | 1942-03-13 | 1943-09-15 | William Baird | Pulverulent cleansing preparations |
US2377066A (en) * | 1941-05-10 | 1945-05-29 | Ici Ltd | Cleansing compositions |
US2620325A (en) * | 1951-06-25 | 1952-12-02 | Du Pont | Polymeric oximes and their preparation |
US2661305A (en) * | 1949-11-01 | 1953-12-01 | Holliday Co Ltd L B | Method for improving the brightness of textile materials and product |
US2730428A (en) * | 1950-10-21 | 1956-01-10 | Tepha Ges Fur Pharmazeutische | Method and composition for washing and bleaching fibrous materials |
AT199158B (en) * | 1956-09-28 | 1958-08-25 | Degussa | Process for the treatment of polyamide fibers with peroxide-containing bleaches or detergents |
US2909404A (en) * | 1953-03-12 | 1959-10-20 | Degussa | Protection of polyamide fibers during treatment with peroxide containing bleaching or washing agents |
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DE737552C (en) * | 1935-06-22 | 1943-07-17 | Chem Fab Gruenau Ag | Process for the bleaching of fibers by means of per compounds |
US2287099A (en) * | 1937-02-15 | 1942-06-23 | Du Pont | Artificial wool |
DE739417C (en) * | 1937-10-03 | 1943-09-25 | Henkel & Cie Gmbh | Laundry detergents containing powdered per-compounds |
US2412945A (en) * | 1945-07-27 | 1946-12-24 | Frederick C Bersworth | Detergent composition and method of preparing same |
US2543852A (en) * | 1946-10-29 | 1951-03-06 | Sandoz Ltd | Surface active derivatives of nitrogen-containing sulfonic acids |
BE498991A (en) * | 1949-10-28 | |||
US2688617A (en) * | 1951-07-17 | 1954-09-07 | American Cyanamid Co | Sulfonated dihalogeno diaminostilbenes |
-
0
- NL NL112268D patent/NL112268C/xx active
- NL NL195727D patent/NL195727A/xx unknown
- NL NL112774D patent/NL112774C/xx active
- FR FR1094713D patent/FR1094713A/fr not_active Expired
- BE BE536668D patent/BE536668A/xx unknown
- NL NL295923D patent/NL295923A/xx unknown
-
1953
- 1953-03-12 DE DED14553A patent/DE976170C/en not_active Expired
-
1954
- 1954-02-25 GB GB5593/54A patent/GB767025A/en not_active Expired
- 1954-03-09 CH CH333466D patent/CH333466A/en unknown
- 1954-03-11 US US419911A patent/US2909404A/en not_active Expired - Lifetime
- 1954-03-20 DE DED17356A patent/DE945443C/en not_active Expired
- 1954-11-13 DE DED19111A patent/DE1020433B/en active Pending
- 1954-12-11 DE DED19309A patent/DE1025376B/en active Pending
-
1955
- 1955-03-18 GB GB7993/55A patent/GB784911A/en not_active Expired
- 1955-03-18 CH CH339688D patent/CH339688A/en unknown
- 1955-03-21 FR FR1121229D patent/FR1121229A/en not_active Expired
-
1960
- 1960-10-13 US US62325A patent/US3153565A/en not_active Expired - Lifetime
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2153416A (en) * | 1936-05-22 | 1939-04-04 | Hatters Fur Exchange Inc | Treatment of animal and vegetable fibers |
US2377066A (en) * | 1941-05-10 | 1945-05-29 | Ici Ltd | Cleansing compositions |
GB555998A (en) * | 1942-03-13 | 1943-09-15 | William Baird | Pulverulent cleansing preparations |
US2661305A (en) * | 1949-11-01 | 1953-12-01 | Holliday Co Ltd L B | Method for improving the brightness of textile materials and product |
US2730428A (en) * | 1950-10-21 | 1956-01-10 | Tepha Ges Fur Pharmazeutische | Method and composition for washing and bleaching fibrous materials |
US2620325A (en) * | 1951-06-25 | 1952-12-02 | Du Pont | Polymeric oximes and their preparation |
US2909404A (en) * | 1953-03-12 | 1959-10-20 | Degussa | Protection of polyamide fibers during treatment with peroxide containing bleaching or washing agents |
AT199158B (en) * | 1956-09-28 | 1958-08-25 | Degussa | Process for the treatment of polyamide fibers with peroxide-containing bleaches or detergents |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3480391A (en) * | 1967-08-24 | 1969-11-25 | Sinclair Research Inc | Hydroxylamine solutions stabilized with an amide oxime and method for their preparation |
US3480392A (en) * | 1967-08-24 | 1969-11-25 | Sinclair Research Inc | Hydroxylamine solutions stabilized with a hydroxamic acid and method for their preparation |
US3628906A (en) * | 1967-08-26 | 1971-12-21 | Degussa | Agent for protecting polyamide fibers or threads against the attack of bleaching and washing baths |
US3975153A (en) * | 1975-08-25 | 1976-08-17 | Fmc Corporation | Activation of peroxygen bleaches using isophorone enol acetates and isophorone oximinoacetate |
US4021361A (en) * | 1975-08-25 | 1977-05-03 | Fmc Corporation | Storage-stable detergent composition containing sodium perborate and activator |
EP0384912A2 (en) * | 1989-02-21 | 1990-08-29 | Monsanto Company | Hydroxamate bleach stabilizer |
EP0384912A3 (en) * | 1989-02-21 | 1991-09-11 | Monsanto Company | Hydroxamate bleach stabilizer |
US5045223A (en) * | 1990-03-16 | 1991-09-03 | Lever Brothers Company, Division Of Conopco, Inc. | N-sulfonyloxaziridines as bleaching compounds |
US5047163A (en) * | 1990-03-16 | 1991-09-10 | Lever Brothers Company, Division Of Conopco, Inc. | Activation of bleach precursors with sulfonimines |
Also Published As
Publication number | Publication date |
---|---|
GB767025A (en) | 1957-01-30 |
NL295923A (en) | |
CH333466A (en) | 1958-10-31 |
NL112774C (en) | |
BE536668A (en) | |
NL195727A (en) | |
DE1025376B (en) | 1958-03-06 |
GB784911A (en) | 1957-10-16 |
US2909404A (en) | 1959-10-20 |
CH339688A (en) | 1959-07-15 |
FR1094713A (en) | 1955-05-24 |
DE976170C (en) | 1963-04-11 |
DE945443C (en) | 1956-07-12 |
DE1020433B (en) | 1957-12-05 |
FR1121229A (en) | 1956-07-25 |
NL112268C (en) |
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