US3816068A - Flame retardant for cellulosic fabrics - Google Patents

Flame retardant for cellulosic fabrics Download PDF

Info

Publication number
US3816068A
US3816068A US00161867A US16186771A US3816068A US 3816068 A US3816068 A US 3816068A US 00161867 A US00161867 A US 00161867A US 16186771 A US16186771 A US 16186771A US 3816068 A US3816068 A US 3816068A
Authority
US
United States
Prior art keywords
pyrovatex
mdmp
polyester
cotton
fabrics
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
Application number
US00161867A
Other languages
English (en)
Inventor
J Rivlin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Burlington Industries Inc
Original Assignee
Burlington Industries Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Burlington Industries Inc filed Critical Burlington Industries Inc
Priority to US00161867A priority Critical patent/US3816068A/en
Priority to GB2189172A priority patent/GB1331039A/en
Priority to DE19722223426 priority patent/DE2223426A1/de
Priority to CH1043972D priority patent/CH1043972A4/xx
Priority to CH1043972A priority patent/CH562906A/xx
Application granted granted Critical
Publication of US3816068A publication Critical patent/US3816068A/en
Assigned to BURLINGTON INDUSTRIES, INC. reassignment BURLINGTON INDUSTRIES, INC. MERGER (SEE DOCUMENT FOR DETAILS). Assignors: BI/MS HOLDS I INC.
Assigned to BURLINGTON INDUSTRIES, INC. reassignment BURLINGTON INDUSTRIES, INC. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: BURLINGTON INDUSTRIES, INC.
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—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 sulfur or phosphorus
    • D06M13/282—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 sulfur or phosphorus with compounds containing phosphorus
    • D06M13/285—Phosphines; Phosphine oxides; Phosphine sulfides; Phosphinic or phosphinous acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5304—Acyclic saturated phosphine oxides or thioxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5397—Phosphine oxides
    • 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
    • Y10S260/00—Chemistry of carbon compounds
    • Y10S260/24—Flameproof
    • 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
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/92—Fire or heat protection feature
    • Y10S428/921—Fire or flameproofing
    • 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

  • CHgCHgPJNHCHgOH has achieved considerable commercial success under the proprietary name of Pyrovatex CP. It is particularly effective because it bonds both phosphorus and nitrogen chemically to the cellulose molecule. Being reactively bonded rather than merely physically coated onto the cellulose, it holds more tenaciously than nonreactive coatings and plasticizers. Besides this advantage Pyrovatex CP, unless it is'combined with textile resins, has far less stiffening effect on fabrics than do the various kinds of coating agents.
  • Pyrovatex CP is not, however, without faults. As a phosphonate ester, it has a potential for hydrolysis under conditions of extended use, as during laundering, weathering, steam ironing, and the like. More important, the efficiency of the reaction between Pyrovatex CP and cellulose is low, thus resulting in considerable loss of expensive reagent during application to fabric. This low efficiency of reaction further manifests itself in the fact that only limited amounts of Pyrovatex CP can be added to cellulosic fibers, a fact which seriously diminishes its utility in fabric blends such as the popular 50/50 polyester/cotton. Being inert to polyester and incapable of heavy add-on to cellulose, Pyrovatex CP cannot be taken up by the blends in amounts sufficient to flameproof them adequately.
  • a further object of the invention is to provide a class of flame retardants effective on polyester/cotton blends.
  • a further object isv to provide flame retardants with exceptional resistance to laundering.
  • N-methylol-3- (dimethylphosphinyl)propionamide adds so well that it is effective even on 50/50 polyester/cotton blend fabrics.
  • This invention comprises a new class of phosphine oxide derivatives of N-methylol propionamides of the general formula R1 0 X 0 ⁇ II E g /BCH1 H NHCHzOR R:
  • R represents hydrogen or alkyl of up to six carbon atoms
  • X represents hydrogen or a methyl radical
  • R, and R represent methyl, ethyl, or propyl radicals.
  • Preferred compounds are those having the formulas where R R and X are as defined above.
  • the most preferred compound is N-methylol-3-(dimethylphosphinyl )propionamide:
  • phosphine oxide compounds of this invention Two particularly surprising features distinguish the phosphine oxide compounds of this invention from compounds known in the art: the high efficiency of their reaction with cellulose, and their superior flame retardant properties. Although neither of these advantages could have been anticipated, they are believed to work together to produce the remarkable overall superiority of these products. From a practical standpoint, the outcome of its particularly favorable combination of properties is that the preferred embodiment of this invention, N-methylol-3-(dimethylphosphinyl)propionamide, hereafter referred to for convenience as MDMP, works effectively as a flame retardant even for 50/50 polyester/cotton blends, an application where Pyrovatex CP falls far short of adequacy.
  • MDMP N-methylol-3-(dimethylphosphinyl)propionamide
  • these compounds having no hydrolysis-susceptible phosphonate groups, and being members of the class of phosphine oxides, among the most stable phosphorus compounds known, are free from the potential of many phosphorus-containing flame retardants, including Pyrovatex CP and its homologs, for forming strong and deleterious phosphorus acid groups on exposure to laundering, ironing, weathering, and like hydrolytic influences.
  • These compounds may be applied to substrates such as fabrics, yarns, and other forms of cellulose by any known means, such as spraying, dipping, padding, and the like, with preferably aqueous solutions of said compounds.
  • the most convenient, and preferred, is padding, followed by drying in the case of aqueous application.
  • Application to the substrate is followed by a curing of cross-linking step, to effect chemical reaction of the compounds hereof with free hydroxy groups in the substrate. This is preferably followed with a washing step to remove any of the compounds not chemically bound to the substrate.
  • the reaction or curing step is brought about by application of heat, although other suitable reaction or curing mechanisms may also be utilized. Heat is normally most convenient and therefore is presently preferred.
  • the amount and duration of heat treatment will normally depend on local practice, the type of substrate being treated, etc., and are not presently believed to be critical to the success of this invention. Usually a temperature of from about l50l75C for from about one to several minutes will suffice for the heating step.
  • blend fabrics treated with MDMP are markedly more resistant to flame than those treated with Pyrovatex CP. It is apparent that, despite their close structural resemblance to each other, MDMP and Pyrovatex CP are actually very dissimilar in effectiveness, and presumably in mechanism of flame-proofing action. These facts are particularly evident when one compares their effects on 50/50 polyester/cottom blends.
  • cellulose-containing materials whether these be made from cotton, rayon, wood pulp, or other sources of cellulose, and whether the articles in which they are incorporated are intended for use in apparel, home furnishings, intermediate, or industrial type products.
  • Modiflcationslo the standard GE instrument were as follows: inside diameter of glass cylinder 3 inches instead of 3% inches; distance from top of screen (4) to top of cylinder 11% inches instead of 6 inches; distance from bead surface (6) to screen (4) 6% inches instead of 3 inches; fabric length 6 inches instead of 5 inches; cover plate removed.
  • Flow rate was set at 4 cm./sec.
  • N-methylol-3- (dimethylphosphinyl)propionamide, MDMP was synthesized as follows: Dimethylphosphine oxide was prepared by the method of Hays, J. Org. Chem., 33, 3690 (1968), and distilled before use. To a stirred solution of 271.7 g, 3.48 mol, dimethylphosphine oxide and 247.1 g, 3.48 mol, acrylamide in 319 ml ethanol was added dropwise a freshly prepared solution of sodium ethoxide, made from 8.4 g, 0.365 atom, sodium and 193 ml ethanol. After about one-fourth of the base had been added a vigorously exothermic reaction began.
  • EXAMPLE 2 To illustrate the utility of the invention, in this and following examples the procedure employed was to pad an aqueous solution of reagent, 1 percent curing catalyst (2-amino-2-methylpropanol hydrochloride), and 0.1 percent detergent (nonylphenylpolyethyleneoxyethanol) onto weighed samples of bleached or normally scoured, but otherwise untreated 100 percent cotton sheeting, 50/50 polyester/cotton sheeting, or other eel; lulosic fabric in a laboratory padder at 30 psi; dry 4 minutes at 93C; cure 3 minutes at 175C; process wash fi'minutes with water containing 0.001 percent detergent in a home washing machine set on warm; tumble-dry; and condition overnight at 72F and 65 percent relative humidity in preparation for final weighing and testing.
  • 1 percent curing catalyst (2-amino-2-methylpropanol hydrochloride)
  • detergent nonylphenylpolyethyleneoxyethanol
  • test fabrics were 100 percent cotton sheeting, 3.75 oz/yd, 95 X 84 count, and 50/50 polyester/cotton sheeting, 3.68 oz/yd, 96 X 88 count.
  • Samples for treatment were usually about 10 X inches, weighing before treatment about 18 g for 50/50 polyester/cotton and 16 g for 100 percent cotton.
  • the treatment cycle was repeated more than one time when ever it was desired to increase the extent of modification (add-on) beyond the maximum obtainable in a single treatment. The most superior results were generally obtained when using freshly prepared padding baths.
  • EXAMPLE 3 For comparative purposes, samples of 50/50 polyester/cotton fabrics were padded with 40 percent aqueous solutions of Pyrovatex CP and MDMP by the procedure of Example 2. Though noneof the once-treated samples passed the vertical test, those padded with MDMP had slightly but significantly higher L01 readings, as may be seen by comparison of the one-cycle entries in Tables 1 and 2. Two and even three cycles of Pyrovatex CP had almost no further effect on increasing the add-on and the L01, and all specimens burned their entire lengths in the vertical test. The L01 of the original fabric for all of the samples was 0.168.
  • Example 4 For comparative purposes, the procedure of Example 4 was repeated, but this time by padding twice onto 65/35 rayon/polyester sheeting at 40 percent concentration according to the method of Example 2. Two MDMP treated samples gave LO1 readings of 0.252 and 0.242. and both samples passed the vertical flame test, giving char lengths of 6.3 and 4.6 inches.
  • EXAMPLE 6 1n using relatively expensive flame retardants such as Pyrovatex CP and MDMP, it is important to achieve a high degree of bonding of the solution padded onto the fabric. Anything removed by the process wash after curing is essentially non-recoverable and wasted. The degree of bonding is expressed as the efficiency, this being calculated from the equation:
  • EXAMPLE 7 1t became apparent from L01 measurements of a large number of test samples that at roughly equivalent phosphorus contents, MDMP-treated fabrics were proving statistically more resistant to burning than comparable Pyrovatex-treated fabrics. A series of both groups of fabrics were therefore submitted to burning in beakers in the LOl apparatus in oxygen concentrations at or above their LOl values. The chars were weighed and analyzed, and the percentage of the original phosphorus remaining in each char was calculated. Data are summarized in Tables 6 and 7.
  • EXAMPLE 8 Samples of MDMP-modified cotton and 50/50 polyester/cotton sheeting were subjected to multiple washings in a home washing machine set on hot, in the presence of 0.l percent TIDE. home detergent. The phosphorus analyses and LO! readings, before and after laundering, are shown in Table 8. It is evident that not only the phosphorus content but also the flame resistance remained constant, within the errrors of measurement of the methods.
  • a process for increasing the flame retardency of a cellulosic textile material which comprises impregnating the material with a solution containing an acidic catalyst and a product of the formula:
  • R represents hydrogen or alkyl of up to six carbon atoms
  • X represents hydrogen or a methyl radical
  • R and R represent methyl, ethyl or propyl radicals and thereafter curing the impregnated material under heating conditions.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US00161867A 1971-07-12 1971-07-12 Flame retardant for cellulosic fabrics Expired - Lifetime US3816068A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US00161867A US3816068A (en) 1971-07-12 1971-07-12 Flame retardant for cellulosic fabrics
GB2189172A GB1331039A (en) 1971-07-12 1972-05-10 Flame retardant phosphine oxides for cellulosic material
DE19722223426 DE2223426A1 (de) 1971-07-12 1972-05-13 N-methylol-(dialkylphosphinyl)-alkylamide und deren verwendung als flammschutzmittel
CH1043972D CH1043972A4 (enrdf_load_stackoverflow) 1971-07-12 1972-07-12
CH1043972A CH562906A (enrdf_load_stackoverflow) 1971-07-12 1972-07-12

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US00161867A US3816068A (en) 1971-07-12 1971-07-12 Flame retardant for cellulosic fabrics

Publications (1)

Publication Number Publication Date
US3816068A true US3816068A (en) 1974-06-11

Family

ID=22583108

Family Applications (1)

Application Number Title Priority Date Filing Date
US00161867A Expired - Lifetime US3816068A (en) 1971-07-12 1971-07-12 Flame retardant for cellulosic fabrics

Country Status (4)

Country Link
US (1) US3816068A (enrdf_load_stackoverflow)
CH (2) CH1043972A4 (enrdf_load_stackoverflow)
DE (1) DE2223426A1 (enrdf_load_stackoverflow)
GB (1) GB1331039A (enrdf_load_stackoverflow)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3997699A (en) * 1975-04-25 1976-12-14 Ethyl Corporation Flame resistant substrates
US4007318A (en) * 1975-05-21 1977-02-08 General Electric Company Phosphorylated polystyrene and method for forming same
US4167603A (en) * 1976-12-13 1979-09-11 Ethyl Corporation Flame resistant cotton/polyester blend substrates
US4839099A (en) * 1985-02-27 1989-06-13 Dainippon Ink And Chemicals, Inc. Fire-retardant for woody materials
US4922012A (en) * 1987-08-24 1990-05-01 Occidental Chemical Corporation Compositions of matter comprising dialkyl-(N,N-dialkylcarbamoylmethyl) phosphine oxides
US9624312B2 (en) 2014-03-26 2017-04-18 International Business Machines Corporation Flame retardant modified cellulosic nanomaterials (FR-CNs) prepared using phosphorus-containing monomers
WO2022263615A1 (en) 2021-06-18 2022-12-22 Ten Cate Protect Bv Flame retardant fabric comprising cotton alternative

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2691567A (en) * 1951-10-23 1954-10-12 Du Pont Polymeric organic phosphorus compounds for increasing flame resistance of textiles and method of using same
US3639539A (en) * 1967-04-11 1972-02-01 Ciba Ltd Phosphorus-containing n n-dimethylolcarboxylic acid amides
US3639532A (en) * 1967-04-25 1972-02-01 Bayer Ag Esters and/or amides of acids of phosphorus containing a group having the formula roch2nhco-
US3766252A (en) * 1970-10-27 1973-10-16 Hoechst Ag Unsaturated carboxylic acid derivatives containing phosphorus

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2691567A (en) * 1951-10-23 1954-10-12 Du Pont Polymeric organic phosphorus compounds for increasing flame resistance of textiles and method of using same
US3639539A (en) * 1967-04-11 1972-02-01 Ciba Ltd Phosphorus-containing n n-dimethylolcarboxylic acid amides
US3639532A (en) * 1967-04-25 1972-02-01 Bayer Ag Esters and/or amides of acids of phosphorus containing a group having the formula roch2nhco-
US3766252A (en) * 1970-10-27 1973-10-16 Hoechst Ag Unsaturated carboxylic acid derivatives containing phosphorus

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Anon., Textile World, p. 132, November, 1968. *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3997699A (en) * 1975-04-25 1976-12-14 Ethyl Corporation Flame resistant substrates
US4007318A (en) * 1975-05-21 1977-02-08 General Electric Company Phosphorylated polystyrene and method for forming same
US4167603A (en) * 1976-12-13 1979-09-11 Ethyl Corporation Flame resistant cotton/polyester blend substrates
US4839099A (en) * 1985-02-27 1989-06-13 Dainippon Ink And Chemicals, Inc. Fire-retardant for woody materials
US4922012A (en) * 1987-08-24 1990-05-01 Occidental Chemical Corporation Compositions of matter comprising dialkyl-(N,N-dialkylcarbamoylmethyl) phosphine oxides
US9624312B2 (en) 2014-03-26 2017-04-18 International Business Machines Corporation Flame retardant modified cellulosic nanomaterials (FR-CNs) prepared using phosphorus-containing monomers
US9856329B2 (en) 2014-03-26 2018-01-02 International Business Machines Corporation Flame retardant modified cellulosic nanomaterials (FR-CNs) prepared using phosphorus-containing monomers
WO2022263615A1 (en) 2021-06-18 2022-12-22 Ten Cate Protect Bv Flame retardant fabric comprising cotton alternative
NL2028484B1 (en) 2021-06-18 2022-12-27 Ten Cate Protect B V Flame Retardant Fabric Comprising Cotton Alternative

Also Published As

Publication number Publication date
CH1043972A4 (enrdf_load_stackoverflow) 1974-11-29
DE2223426A1 (de) 1973-01-25
CH562906A (enrdf_load_stackoverflow) 1975-06-13
GB1331039A (en) 1973-09-19

Similar Documents

Publication Publication Date Title
US3822327A (en) Neutralized polycondensed vinylphosphonates
US3906136A (en) Process of flame retarding substrates by applying hexahydratriazine phosphonate derivatives
US3746572A (en) Process for flame retarding fabrics
US3969437A (en) Cyclic phosphorus esters
US3698854A (en) Process for producing flame resistant organic textiles
US2891877A (en) Flame resistant organic textiles and method of production
US3816068A (en) Flame retardant for cellulosic fabrics
US3054698A (en) Flame proofing of cellulosic materials
US3762865A (en) Flame retarding of solid substrates with allyl 2-carbamoylalkylphosphonates
US3901650A (en) Textile flame retardants
US2901444A (en) Polymers made from 1-aziridinyl phosphine oxides and sulfides and flame resistant organic textiles
US2814573A (en) Organic polymeric compositions containing nitrilo methylol-phosphorus polymers and bromine compounds
US3700403A (en) Process for flameproofing cellulose-containing fibrous materials
US3885912A (en) Method of rendering textiles flame retardant with phosphorus containing melamine
US3695925A (en) Process for flameproofing textiles
US4034141A (en) Brominated phosphoramidates
US3619113A (en) Flame-retardant finish for cellulosic textile materials
US3884628A (en) N-Phosphonomethyl acrylamides as flame retarding agents for textiles
US2861901A (en) Bromine containing nitrilo methylol-phosphorus polymers
US3034919A (en) Fire retardant composition and cellulosic fabric treated therewith
US2886539A (en) Aziridine-methylolphosphorus polymers and flame resistant organic textiles
US3849409A (en) Hexahydrotriazine phosphonate derivatives
CA1076596A (en) Brominated phosphoramidates
US3669725A (en) Flameproofing of polyester-cellulose fibre materials
US3825630A (en) Phosphonate carbamates

Legal Events

Date Code Title Description
AS Assignment

Owner name: BURLINGTON INDUSTRIES, INC.

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:BURLINGTON INDUSTRIES, INC.;REEL/FRAME:004821/0756

Effective date: 19870903

Owner name: BURLINGTON INDUSTRIES, INC.

Free format text: MERGER;ASSIGNOR:BI/MS HOLDS I INC.;REEL/FRAME:004827/0512

Effective date: 19870903

Owner name: BURLINGTON INDUSTRIES, INC.,STATELESS

Free format text: MERGER;ASSIGNOR:BI/MS HOLDS I INC.;REEL/FRAME:004827/0512

Effective date: 19870903