US3427286A - Oxidized polyacroleins as textile sizing agent - Google Patents

Oxidized polyacroleins as textile sizing agent Download PDF

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Publication number
US3427286A
US3427286A US565067A US3427286DA US3427286A US 3427286 A US3427286 A US 3427286A US 565067 A US565067 A US 565067A US 3427286D A US3427286D A US 3427286DA US 3427286 A US3427286 A US 3427286A
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United States
Prior art keywords
oxidized
oxidation
sizing agent
size
yarn
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Expired - Lifetime
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US565067A
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English (en)
Inventor
Heinz Hartel
Ilse Ursula Nebel
Gerhard Bier
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Dynamit Nobel AG
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Dynamit Nobel AG
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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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/31—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated nitriles
    • 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
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof

Definitions

  • This invention relates to the sizing of yarns. It more particularly refers to a novel size for textile fibers.
  • the size also imparts a smooth protective layer to the yarn and to the fibers thereof, which makes the yarn and fibers more resistant to mechanical wear, abrasion and shocks as may be encountered for example in a weaving process.
  • antistatic agents it is known to apply antistatic agents to textiles in order to reduce the static charges thereon which build up when fibers or yarns are worked, particularly when such are Woven or passed over guide means in any operation.
  • Many such antistatic agents are known and well documented in the art, for example, salts of polyacrylic acid.
  • this invention includes, as one of its aspect, the provisions of a textile material, e.g., fiber, yarn, filament, fabric, etc. having as a size thereon a salt of the oxidation product of acrolein polymer, methacrolein polymer or copolymer of acrolein and methacrolein.
  • the polymer prior to oxidation thereof has a molecular weight of about 1,000 to 50,000.
  • the oxidation of the aldehyde groups of the poly mer is suitably at least about 70 percent complete. Generally it is not necessary to carry the oxidation of the aldehyde groups of the polymer to a greater degree of completion than about 98 percent.
  • Oxidized polyaldehydes useful in this invention are per se known materials. They have been produced in the past, for example, by oxidation with alkaline permanganate solutions (I. Am. Chem. Soc., 60 (1938), 1911) or in pyridine solution with hydrogen peroxide or po tassium permanganate (Ang. Chemie, 69 (1957), 162).
  • oxidizing agent a mixture of cupric oxide or cupric hydroxide and a noble metal or noble metal oxide or noble metal hydroxide.
  • the oxidation may be carried out upon the aldehyde polymer in aqueous suspension which may or may not have added thereto an organic solvent.
  • Oxygen or oxygen-containing gases are preferably simultaneously introduced into the oxidation reaction; cf. in this connection German application D 45,008. It is possible to avoid the addition of noble metals or the earlier mentioned noble metal compounds by employing the polymerizates directly while they are still present in their mother liquor obtained during formation of the polymerizates.
  • Salts of the polymer oxidation products are exemplified by salts of sodium, potassium, ammonium or aliphatic amines, such as methylamine, diethylamine, etc., which are used in aqueous or aqueous-alcoholic solution.
  • Noble metals which are useful in the oxidation of polyaldehydes include palladium, platinum, iridium, rhodium, ruthenium, etc.
  • Substantially any textile material can be treated with the oxidized polyaldehyde size of this invention.
  • the greatest economic application of this invention is with respect to textiles which must be discharged of static or in which the tendency to build up static electricity charge should be suppressed, and to which it is desirable to apply protective size. It is particularly desirable to utilize this invention in connection with synthetic fibers such as polyamides, polyesters, acrylics, modacrylics, cellulosics, polyolefins, polyacetals, polybenzimidizoles and the like.
  • the oxidation product of polyacrolein is in some way different from the polyacrylic acids used in the past, since, when these two materials are applied as sizing agents on identical fibers, the electrical properties of the sized fibers are substantially, in order of magnitude, different.
  • a nylon 66 yarn which had an electrical field strength of about 30,000 volts per centimeter, when treated with a polyacrylic acid salt, had an electrical field strength of about 2,000 volts per centimeter.
  • the electrical field strength was reduced to about volts per centimeter.
  • the yarn electrical resistance was 1.5 X10 compared to an electrical resistance of 7 10 for the yarn sized with polyacrylic acid salt and 25x10 for the same yarn sized with oxidized polyacrolein salt.
  • oxidized polyacrolein, methacrolein or copolymer salt size described herein in combination with other known sizing agents, for example, polyacrylates, butyrals of polyacroleinformaldehyde and others.
  • the sizes of the instant invention are suitably applied to the textile being treated as an aqueous solution thereof.
  • Other solvents besides water are suitable, but water is preferred.
  • the size solution is suitably prepared in the concentrations known in the art and generally used, and such solutions are applied to the textile by known techniques.
  • the polyacrolein was prepared in accord with the method of Houben-Weyl, Methoden dcr Organischen Chemie (Makromolekulate Stolfe), p. 5 1084 (1961, 4th ed.). The degree of oxidation was about 80 percent. In the following examples rovings were sized at a temperature of about 80 C. at a speed of about meters per minute. The oxidized polyacrolein was converted to the salt by reaction with 2 N-sodium hydroxide which was neutralized with 2 N-acetic acid to a pH of 7. The size was applied as an aqueous solution of the indi cated concentration.
  • EXAMPLE I The textile treated was a roving of polyester, formed by polycondensation of ethylene glycol and terephthalic acid, fibers 40 mm. in length of 1.5 denier per fiber.
  • the oxidized polyacrolein size was applied as a 7-percentsolution as the sodium salt thereof.
  • EXAMPLE II The same polyester fibers as used in Example I were formed into a single spun yarn having a twist of 1100 turns per meter.
  • the oxidized polyacrolein size was applied as a sodium salt solution of 4 weight percent concentration.
  • the following comparative data was obtained upon testing of the sized and unsized yarn.
  • the textile treated was a roving of polyacrylonitrile fibers of 3 denier and varying lengths up to about 160 mm.
  • the oxidized polyacrolein was applied as a sodium salt as a 7% solution.
  • EXAMPLE VI The same acrylic fibers as used in Example V were formed into a single spun yarn having a twist of 780 turns per meter.
  • the oxidized polyacrolein was applied as a sodium salt solution of 3% concentration.
  • a textile sizing agent comprising at least one watersoluble salt of a partially oxidized polymer of at least one member selected from the group consisting of acrolein, methacrolein and mixtures thereof, which polymer prior to oxidation thereof had a molecular weight of about 1,000 to 50,000 and which oxidation was carried out in an alkaline medium in the presence of a metallic oxidizing agent.
  • a sizing agent as claimed in claim 1 wherein the cation of said salt is at least one member selected from the group consisting of sodium, potassium, ammonium, methylamine and dimethylaminc.
  • a textile having a sizing agent as claimed in claim 1 thereon.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
US565067A 1965-07-16 1966-07-14 Oxidized polyacroleins as textile sizing agent Expired - Lifetime US3427286A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DED0047737 1965-07-16

Publications (1)

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US3427286A true US3427286A (en) 1969-02-11

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ID=7050645

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US565067A Expired - Lifetime US3427286A (en) 1965-07-16 1966-07-14 Oxidized polyacroleins as textile sizing agent

Country Status (8)

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US (1) US3427286A (enrdf_load_stackoverflow)
AT (1) AT265198B (enrdf_load_stackoverflow)
BE (1) BE684250A (enrdf_load_stackoverflow)
CH (1) CH985766D (enrdf_load_stackoverflow)
DE (1) DE1469329A1 (enrdf_load_stackoverflow)
ES (1) ES329093A1 (enrdf_load_stackoverflow)
GB (1) GB1153595A (enrdf_load_stackoverflow)
NL (1) NL6610018A (enrdf_load_stackoverflow)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10732714B2 (en) 2017-05-08 2020-08-04 Cirrus Logic, Inc. Integrated haptic system
US10860202B2 (en) 2018-10-26 2020-12-08 Cirrus Logic, Inc. Force sensing system and method

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3127374A (en) * 1958-01-31 1964-03-31 Process for the production of poly-

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3127374A (en) * 1958-01-31 1964-03-31 Process for the production of poly-

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10732714B2 (en) 2017-05-08 2020-08-04 Cirrus Logic, Inc. Integrated haptic system
US10860202B2 (en) 2018-10-26 2020-12-08 Cirrus Logic, Inc. Force sensing system and method

Also Published As

Publication number Publication date
BE684250A (enrdf_load_stackoverflow) 1967-01-16
GB1153595A (en) 1969-05-29
CH985766D (enrdf_load_stackoverflow)
DE1469329A1 (de) 1969-01-02
NL6610018A (enrdf_load_stackoverflow) 1967-01-17
ES329093A1 (es) 1967-09-01
AT265198B (de) 1968-09-25

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