US3755498A - Textile fiber comprising an admixture of a polyester and an addition polymer having a tribromoneopentyl group in the repeating unit of theaddition polymer - Google Patents

Textile fiber comprising an admixture of a polyester and an addition polymer having a tribromoneopentyl group in the repeating unit of theaddition polymer Download PDF

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Publication number
US3755498A
US3755498A US00224992A US3755498DA US3755498A US 3755498 A US3755498 A US 3755498A US 00224992 A US00224992 A US 00224992A US 3755498D A US3755498D A US 3755498DA US 3755498 A US3755498 A US 3755498A
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United States
Prior art keywords
polyester
fiber
polymer
fibers
textile
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Expired - Lifetime
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US00224992A
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English (en)
Inventor
Intire J Mc
W Dickason
Sickle D Van
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Eastman Kodak Co
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Eastman Kodak Co
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • 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
    • Y10S8/04—Polyester fibers

Definitions

  • flame retardant textile fibers comprising an admixture of a polyester and an addition polymer having the CHZBI --O-CHz-CH1BI CH7BZ group as a portion of the polymer unit.
  • the polyester is derived from at least 90 mole percent terephthalic acid and at least 90 mole percent ethylene glycol, tetramethylene glycol, or 1,4-cyclohexanedimethanol.
  • the addition polymer preferably comprises at least 95 mole percent units of the structure fjl Li it
  • the texile fibers of this invention are flame retardant and exhibit a desirable and unobvious combination of other properties necessary in a commercially acceptable textile fiber.
  • This invention relates to a flame retardant textile fiber exhibiting a combination of properties necessary in a commercially acceptable textile fiber.
  • synthetic textile fibers have increased tremendously over the last several decades. This increased use has resulted in large part from the desirable combination of properties that can be achieved in a textile article by using synthetic fibers or blends of natural and synthetic fibers.
  • a synthetic textile fiber may have any number of desirable properties, every textile fiber must have a number of necessary properties to make the fiber commercially acceptable for typical applications such as wearing apparel, carpets and the like.
  • the necessary properties include desirable mechanical properties, lack of discoloration during and immediately after spinning, light-fastness of the undyed fibers, desirable dye takeup, light-fastness of the dyed fibers and retention of dye after dry cleaning and washing.
  • an advantage of the textile fiber of this invention is the high degree of flame retardancy after washing and dry cleaning.
  • Another advantage of the textile fiber of this invention is the desirable mechanical properties.
  • Another advantage of the textile fiber of this invention is the lack of substantial discoloration of the fibers during and immediately after melt spinning.
  • Still another advantage of the textile fiber of this invention is the desirable dye takeup.
  • Yet another advantage of the textile fiber of this invention is the desirable light-fastness of the dyed fiber.
  • Yet another advantage of the textile fiber of this invention is the retention of dye after dry cleaning and washing.
  • the textile fiber of this invention comprises an admixture of (A) a fiber forming polyester derived from (1) a dicarboxylic acid which is at least 90 mole percent terephthalic acid, and (2) a diol which is at least 90 mole percent ethylene glycol, tetramethylene glycol, or 1,4-cyclohexanedimethanol, and (B) a sufficient quantity to comprise 0.1-10 weight percent bromine, based on the combined weight of (A) and (B), of an addition polymer comprised of units having the above noted group in the polymer unit.
  • A a fiber forming polyester derived from (1) a dicarboxylic acid which is at least 90 mole percent terephthalic acid, and (2) a diol which is at least 90 mole percent ethylene glycol, tetramethylene glycol, or 1,4-cyclohexanedimethanol
  • B a sufficient quantity to comprise 0.1-10 weight percent bromine, based on the combined weight of (A) and (B), of
  • the fiber forming polyester can be derived from a dicarboxylic acid which is at least 90 mole percent terephthalic acid, and a diol which is at least 90 mole percent ethylene glycol, tetramethylene glycol, or 1,4-cyclohexanedimethanol.
  • the remaining dicarboxylic acid can be aliphatic, alicyclic, and aromatic dicarboxylic acids having up to 40 carbon atoms. Examples of such acids include malonic, succinic, adipic, azelaic, sebacic, suberic, 1,4- cyclohexenedicarboxylic, and isophthalic.
  • the remaining dicarboxylic acid can contain substituents that impart basic or acid dyeability to the fiber.
  • the remaining diol can be aliphatic, alicyclic, or aromatic and can have up to 40 carbon atoms.
  • diols include diethylene glycol, 1,2propylene glycol, 1,3-cyclohexanedimethanol and hydroquinone.
  • the remaining diol can contain substituents that impart basic or acid dyeability to the fiber.
  • the polyester can be derived from terephthalic acid and ethylene glycol.
  • the polyesters of this invention have an inherent viscosity of at least 0.4 measured at 25 C. using x23 gram of polymer per 100 ml. of a solvent composed of 60 volumes of phenol and 40 volumes of tetrachloroethane.
  • the addition polymer can be comprised of units corresponding to the structure F ii.
  • R is a covalent bond or a CH -group
  • R is a radical corresponding to the structure 0 Ilia PJ-O-CHg-C-Rg
  • R is -H or a monovalent alkyl radical containing 1-8 carbon atoms, or R wherein R R and R are CH Br, CHBr or CBr and R is H or R
  • R above can be a covalent bond.
  • R can be H or CH;,.
  • R can be a covalent bond
  • R can be H or CH and R is H and R R and R can be CH Br.
  • the addition polymer can be comprised of polymer units formed from tribromoneopentyl acrylate and these polymer units have the structure H H i lit l CH Br.
  • the amount of addition polymer can be a sufiicient quantity to comprise 0.1-10 weight percent bromine, based on the combined weight of polyester and addition polymer. More specifically the amount of addition polymer can comprise 2-8 weight percent, based on the weight of polyester and addition polymer.
  • the addition polymer can contain, even in major quantities, repeating units other than repeating units disclosed above. More specifically, the addition polymer can be a copolymer containing the above-disclosed repeating units and other addition polymer units derived from vinyl and isopropenyl esters of monobasic saturated .fatty acids containing from 2-18 carbon atoms, e.g., vinyl acetate, vinyl propionate, vinyl butyrate, vinyl stearate, etc., and corresponding isopropenyl esters, alkyl vinyl ethers wherein the alkyl group contain from 1-4 carbon atoms, e.g., methyl vinyl ether, ethyl vinyl ether, etc., alkyl vinyl ketones wherein the alkyl group contains from 1-4 carbon atoms, e.g., methyl vinyl lretone, etc., vinyl derivatives of benzene, e.g., styrene, u-methylstyrene, etc.
  • vinyl and vinylidene halides e.g., vinyl chloride, vinyl fluoride, vinylidene chloride, vinylidene fluoride, etc., tetrafiuoroethylene, chlorotrifiuoroethylene, a-olefins containing from 2-8 carbon atoms, e.g., ethylene, isobutylene, etc., and monoalkyl and dialkyl esters of cap-unsaturated dicarboxylic acids wherein, the alkyl groups contains from 1-4- carbon atoms, e.g., monomethyl maleate, monobutyl maleate, dimethyl maleate, dibutyl maleate, etc., and corresponding esters of fumaric, itaconic, and the like.
  • the addition polymer comprises at least 35 mole percent, and in another embodiment at least 95 mole percent, units of the structure ffl Li i1.
  • one desirable characteristic of the textile fibers of this invention is their mechanical properties. More specifically, the mechanical properties of the textile fibers of this invention, such as tenacity, elongation and modulus, are quite similar to a control fiber not containing the addition polymer. In one embodiment the tenacity is less than 35% lower, the elongation is less than 15% lower and the modulus is less than 10% lower than a control fiber containing no addition polymer.
  • Another desirable characteristic of the textile fibers of this invention is the lack of substantial discoloration during and immediately after being melt spun as compared to a control fiber having other types of bromine containing molecules thereon. As is well known in the art, many types of bromine containing molecules cause the fiber to yellow during and after melt spinning.
  • Still another desirable characteristic of the textile fibers of this invention is the very desirable light-fastness of the undyed fibers. Specifically, no yellowing or other discoloration is observed after hours exposure to a carbon-arc Fade-Ometer.
  • a control textile fiber containing other bromine containing molecules can in many instances exhibit significant yellowing after exposure to a Fade- Ometer.
  • One additional characteristic of the textile fibers of this invention is desirable dye takeup.
  • Dye takeup is an essential requirement for a commercial fiber.
  • the textile fibers of this invention dye to deep shades and exhibit commercially acceptable dye takeup levels.
  • a control textile fiber containing many other kinds of bromine-containing compounds does not dye to deep shades.
  • Yet another desirable characteristic of the textile fibers of this invention is the light-fastness of the dyed fibers. No fading of the textile fibers of this invention is observed after 20 hours and in some cases after 80 hours in a carbon-arc Fade-Ometer. A control textile fiber which contains other bromine-containing compounds can in many instances exhibit significant fading in a similar test.
  • One further desirable characteristic of the fibers of this invention is the retention of dye after dry cleaning and washing. Textile fibers containing many other kinds of bromine-containing molecules do not retain a satisfactory level of dye after dry cleaning and washing.
  • the textile fibers of this invention exhibit desirable retention of flame retardancy after washing and dry cleaning because the bromine does not wash or dry clean out of the textile fibers of this invention.
  • the textile fibers of this invention retain at least 90 weight percent bromine, and in some cases at least 95 weight percent bromine, based on the weight of the bromine before washing, after washings in accordance with AATCC Test Method 61-1969, Number III-A.
  • the textile fibers of this invention retain, based on the weight of bromine before dry cleaning, at least 90 weight percent bromine, and in some cases at least 95 weight percent bromine, after dry cleanings in accordance with AATCC Test Method 132-1969.
  • the textile fibers of this invention After washing and dry cleaning the textile fibers of this invention exhibit an Oxygen Index of greater than 21 and in many cases greater than 23.
  • the textile fibers of this invention pass the so called Childrens Sleepwear test (FR Doc. 71-10837).
  • the polymers of this invention can be formed according to conventional well known polymerization techniques.
  • the polyesters of this invention can be formed by direct condensation, ester interchange, or acidolysis.
  • the addition polymers of this invention can be formed by solution, bulk, emulsion or bead polymerization.
  • the monomers from which the addition polymer units are derived can be prepared using materials and procedures Well known in the art such as the reaction of tribromoneopentyl alcohol and the corresponding carboxylic acid anhydride such as described in US. 3,165,502.
  • the admixture of the polyester and the addition polymer can be accomplished by procedures well known in the art such as physically mixing small particles of the materials, co-extrusion, or slurrying a solution of the additive with polyester powder and evaporating off the solvent.
  • EXAMPLE 1 This example describes the preparation of textile fibers of poly(ethylene terephthalate) and poly[3-bromo-2,2- bis (bromomethyl) propyl acrylate] often called poly(tribromoneopentyl acrylate)
  • poly(ethylene terephthalate) powder having an inherent viscosity of 0.60.
  • the solvent is evaporated off at 40 C. with stirring while in a hood. Final drying is performed at 50 C. and 0.1 mm.
  • a mixture of 50 mole percent tribromoneopentyl fumarate and 50 mole percent styrene is polymerized in cyclohexanone solution, is isolated as the powder by precipitation in methanol, and is blended in poly(ethylene terephthalate) to give a 92/8 wt. percent polyester/ addition polymer blend.
  • This composition is melt spun to give a fiber having the following properties:
  • a textile fiber comprising an admixture of (A) a fiber forming polyester having an inherent viscosity of at least 0.4 measured at C. using 0.23 gram of polymer per 100 ml. of a solvent composed of 60 volumes of phenol and 40 volumes tetrachloroethane, the polyester being derived from (1) a dicarboxylic acid which is at least 90 mole percent terephthalic acid, and (2) a diol which is at least 90 mole percent ethylene glycol, tetramethylene glycol, or 11,4-cyclohexanedimethanol, and
  • (B) a sufficient quantity to comprise 0.1-10 weight percent bromine, based on the combined weight of (A) and (B), of an addition polymer comprised of units corresponding to the structure iii u. U.
  • R ' is a covalent bond or a -CH group
  • R is a radical corresponding to the structure 8 4.
  • a textile fiber comprising an admixture of (A) a fiber forming polyester having an inherent viscosity of at least 0.4 measured at 25 C. using 0.23 gram of polymer per 100 ml. of a solvent composed of volumes of phenol and 40 volumes tetrachloroethane, the polyester being derived from terephthalic acid and ethylene glycol,

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Artificial Filaments (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US00224992A 1972-02-09 1972-02-09 Textile fiber comprising an admixture of a polyester and an addition polymer having a tribromoneopentyl group in the repeating unit of theaddition polymer Expired - Lifetime US3755498A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US22499272A 1972-02-09 1972-02-09

Publications (1)

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US3755498A true US3755498A (en) 1973-08-28

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Country Link
US (1) US3755498A (OSRAM)
JP (1) JPS4891316A (OSRAM)
CA (1) CA1000892A (OSRAM)
DE (1) DE2305577A1 (OSRAM)
GB (1) GB1399322A (OSRAM)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USB519486I5 (OSRAM) * 1973-02-20 1976-02-17
US4367315A (en) * 1981-01-29 1983-01-04 Occidental Chemical Corporation Flame retardant polymer systems and polymer compositions
US5407728A (en) * 1992-01-30 1995-04-18 Reeves Brothers, Inc. Fabric containing graft polymer thereon
US5486210A (en) * 1992-01-30 1996-01-23 Reeves Brothers, Inc. Air bag fabric containing graft polymer thereon

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USB519486I5 (OSRAM) * 1973-02-20 1976-02-17
US3992481A (en) * 1973-02-20 1976-11-16 Stauffer Chemical Company Fire retardant thermoplastic polymer compositions
US4367315A (en) * 1981-01-29 1983-01-04 Occidental Chemical Corporation Flame retardant polymer systems and polymer compositions
US5407728A (en) * 1992-01-30 1995-04-18 Reeves Brothers, Inc. Fabric containing graft polymer thereon
US5486210A (en) * 1992-01-30 1996-01-23 Reeves Brothers, Inc. Air bag fabric containing graft polymer thereon
US5552472A (en) * 1992-01-30 1996-09-03 Reeves Brothers, Inc. Fabric containing graft polymer thereon

Also Published As

Publication number Publication date
CA1000892A (en) 1976-11-30
JPS4891316A (OSRAM) 1973-11-28
DE2305577A1 (de) 1973-08-16
GB1399322A (en) 1975-07-02

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