US3783016A - Method for imparting flame resistance to fibrous materials - Google Patents

Method for imparting flame resistance to fibrous materials Download PDF

Info

Publication number
US3783016A
US3783016A US00148881A US3783016DA US3783016A US 3783016 A US3783016 A US 3783016A US 00148881 A US00148881 A US 00148881A US 3783016D A US3783016D A US 3783016DA US 3783016 A US3783016 A US 3783016A
Authority
US
United States
Prior art keywords
phosphate
compound
flame
fibrous materials
mole
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
US00148881A
Other languages
English (en)
Inventor
D Randall
C Vogel
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.)
ISP Investments LLC
Original Assignee
Individual
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 Individual filed Critical Individual
Application granted granted Critical
Publication of US3783016A publication Critical patent/US3783016A/en
Assigned to CHASE MANHATTAN BANK, THE NATIONAL ASSOCIATION reassignment CHASE MANHATTAN BANK, THE NATIONAL ASSOCIATION SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DORSET INC. A CORP OF DELAWARE
Assigned to GAF CHEMICALS CORPORATION reassignment GAF CHEMICALS CORPORATION CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). EFFECTIVE ON 04/11/1989 Assignors: DORSET INC.
Assigned to DORSET INC., A DE CORP. reassignment DORSET INC., A DE CORP. CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). EFFECTIVE APRIL 10, 1989 Assignors: GAF CORPORATION, A DE CORP.
Assigned to CHASE MANHATTAN BANK (NATIONAL ASSOCIATION), THE reassignment CHASE MANHATTAN BANK (NATIONAL ASSOCIATION), THE SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: GAF CHEMICALS CORPORATION, A CORP. OF DE
Anticipated expiration legal-status Critical
Assigned to ISP 3 CORP reassignment ISP 3 CORP ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: GAF CHEMICALS CORPORATION
Assigned to ISP INVESTMENTS INC. reassignment ISP INVESTMENTS INC. CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). EFFECTIVE ON 06/06/1991 Assignors: ISP 3 CORP.
Assigned to GAF BUILDING MATERIALS CORPORATION, GAF CHEMICALS CORPORATION, SUTTON LABORATORIES, INC. reassignment GAF BUILDING MATERIALS CORPORATION RELEASED BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: CHASE MANHATTAN BANK, THE (NATIONAL ASSOCIATION)
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244Treating 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
    • D06M13/282Treating 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
    • D06M13/292Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • C07F9/08Esters of oxyacids of phosphorus
    • C07F9/09Esters of phosphoric acids
    • C07F9/091Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • C07F9/08Esters of oxyacids of phosphorus
    • C07F9/09Esters of phosphoric acids
    • C07F9/113Esters of phosphoric acids with unsaturated acyclic alcohols
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00Stock material or miscellaneous articles
    • Y10S428/92Fire or heat protection feature
    • Y10S428/921Fire or flameproofing

Definitions

  • each X can be independently chloro or bro-mo or when taken together can form a bond, and the sum of chlorine and bromine atoms in the compound is at least two.
  • This invention relates to a method for imparting flame resistance to fibrous materials. More particularly, the invention relates to the use of halogenated tripropargyl phosphates as flame retardants for fibrous materials.
  • each X can be independently chloro or bromo or when taken together form a bond, each X can be a halogen radical or when taken together can form a bond, and the sum of X and X atoms in the compound is at least two.
  • the flame retardants of the present invention are readily prepared by halogenation of tripropargyl phosphate.
  • the tripropargyl phosphate is dissolved in a halogenated hydrocarbon solvent such as carbon tetrachloride, chloroform, methylene chloride, trichloroethylene, perchloroethylene and the like and a gaseous or liquid halogen is added to the solution.
  • a halogenated hydrocarbon solvent such as carbon tetrachloride, chloroform, methylene chloride, trichloroethylene, perchloroethylene and the like.
  • a gaseous or liquid halogen is added to the solution.
  • the addition of at least two halogen atoms and preferably, at least four halogen atoms, to the compound is considered necessary to impart flame retardation activity to the compound.
  • the halogens employed are chlorine and bromine; however, in the highly halogenated species, other halogens such as iodine and fluorine can additionally be employed, if desired.
  • the degree of halogena- 3,783,016 Patented Jan. 1, 1974 tion follows the reaction stoichiometry. For example, when one mole of tripropargyl phosphate is reacted with three moles of chlorine, tri(2,3-dichloroallyl) phosphate is obtained. If, however, six moles of chlorine are employed, tri(2,2,3,S-tetrachloropropyl)phosphate is obtained.
  • Typical flame retardants encompassed by the present invention are, for example,
  • the flame retardant compositions of the present invention can be applied to fibers and fabrics in any suitable inert vehicle.
  • these compounds are soluble in halogenated hydrocarbons such as carbon tetrachloride, chloroform, methylene chloride, trichloroethylene, perchloroethylene and the like as well as other non-aqueous solvents such as tetrahydrofuran.
  • Solutions or dispersions containing the flame retardant compositions of the present invention in concentrations ranging from about 5 to about 10 percent by weight can be suitably employed.
  • the flame retardant compositions can be applied to fibers and fabrics by any convenient means such as spraying, dipping, immersing, padding and the like. If desired, the flame retardant compositions can be admixed with synthetic polymeric materials and can be co-extruded therewith to form fibers exhibiting flame retardation. Generally, it is considered preferable to impart from about 5 to about 20% by Weight on a dry basis of the flame retardant composition to the fibers or fabrics being treated to obtain effective flame retardation.
  • Typical fibers which can be treated are, for example, cotton, wool, silk, nylon, rayon, polyesters and the like.
  • EXAMPLE V Into a cold solution of 21.2 g. (0.1 mole) tripropargyl phosphate in 100 ml. carbon tetrachloride was passed 49.5 g. (0.7 mole) chlorine gas over the course of two hours. The solution was allowed to stand overnight at ambient temperature. The solvent was removed under vacuum leaving 63.7 g. (100%) of OP (OCH CCl CCI H) 3 EXAMPLE VI The procedure in Example V was repeated using 21.2 g. (0.1 mole) tripropargyl phosphate, 21.3 (0.3 mole) chlorine gas in 100 ml. carbon tetrachloride. There was obtained 42.5 g.
  • Example VII The procedure in Example V was repeated using 21.2 g. (0.1 mole) tripropargyl phosphate, 14.2 g. (0.2 mole) chlorine gas in 100 ml. carbon tetrachloride. There was isolated 35.4 g. (100%) of EXAMPLE VIII A solution of 5 g. of OP(0CH CBr CBr H) prepared as described in Example II, 45 g. tetrahydrofuran, 32.5 g.
  • each X can be independently chloro or bromo or when taken together can form a bond, and the sum of chlorine and bromine atoms in the compound is at least tWO.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Fireproofing Substances (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
US00148881A 1971-06-01 1971-06-01 Method for imparting flame resistance to fibrous materials Expired - Lifetime US3783016A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US14888171A 1971-06-01 1971-06-01

Publications (1)

Publication Number Publication Date
US3783016A true US3783016A (en) 1974-01-01

Family

ID=22527833

Family Applications (1)

Application Number Title Priority Date Filing Date
US00148881A Expired - Lifetime US3783016A (en) 1971-06-01 1971-06-01 Method for imparting flame resistance to fibrous materials

Country Status (11)

Country Link
US (1) US3783016A (fr)
AU (1) AU460997B2 (fr)
BE (1) BE784205A (fr)
CA (1) CA959354A (fr)
DE (1) DE2226107A1 (fr)
FR (1) FR2140161A1 (fr)
GB (1) GB1376979A (fr)
IL (1) IL39556A (fr)
IT (1) IT956077B (fr)
NL (1) NL7207413A (fr)
SE (1) SE380844B (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3892667A (en) * 1969-10-24 1975-07-01 M & T Chemicals Inc Novel flame retardant compositions
US3967041A (en) * 1972-09-01 1976-06-29 Ciba-Geigy Corporation Modifying textiles and fibers
US4055689A (en) * 1973-07-03 1977-10-25 Ciba-Geigy Corporation Process for flameproofing organic fiber material
US4063883A (en) * 1974-08-20 1977-12-20 Hoechst Aktiengesellschaft Manufacture of flame-retardant regenerated cellulose fibres
EP0212622A2 (fr) * 1985-08-29 1987-03-04 Teijin Limited Fibres synthétiques incombustibles

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2338678B2 (de) * 1973-07-31 1978-03-30 Goeppinger Kaliko- Und Kunstlederwerke Gmbh, 7320 Goeppingen Verfahren zur Herstellung von schwer entflammbarem, waschbeständigem Kunstleder
FR2341636A1 (fr) * 1976-02-23 1977-09-16 Velsicol Chemical Corp Produits de finissage durables, a retardement d'inflammation, pour des matieres textiles, notamment des melanges polyester/coton
IT1080551B (it) * 1976-02-23 1985-05-16 Velsicol Chemical Corp Appretti ritardatori di fiamma duraturi per materiali tessili
DE2727479A1 (de) * 1977-06-18 1979-01-04 Bayer Ag Insektizide und akarizide mittel

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3892667A (en) * 1969-10-24 1975-07-01 M & T Chemicals Inc Novel flame retardant compositions
US3967041A (en) * 1972-09-01 1976-06-29 Ciba-Geigy Corporation Modifying textiles and fibers
US4055689A (en) * 1973-07-03 1977-10-25 Ciba-Geigy Corporation Process for flameproofing organic fiber material
US4063883A (en) * 1974-08-20 1977-12-20 Hoechst Aktiengesellschaft Manufacture of flame-retardant regenerated cellulose fibres
EP0212622A2 (fr) * 1985-08-29 1987-03-04 Teijin Limited Fibres synthétiques incombustibles
EP0212622A3 (en) * 1985-08-29 1988-02-17 Teijin Limited Flameproofing synthetic fiber

Also Published As

Publication number Publication date
GB1376979A (en) 1974-12-11
AU4295272A (en) 1973-12-06
NL7207413A (fr) 1972-12-05
BE784205A (fr) 1972-09-18
IT956077B (it) 1973-10-10
FR2140161A1 (fr) 1973-01-12
DE2226107A1 (de) 1972-12-28
IL39556A0 (en) 1972-07-26
SE380844B (sv) 1975-11-17
CA959354A (en) 1974-12-17
IL39556A (en) 1974-12-31
AU460997B2 (en) 1975-05-15

Similar Documents

Publication Publication Date Title
US2574515A (en) Organic compounds containing phosphorus and bromine
US3783016A (en) Method for imparting flame resistance to fibrous materials
US4216261A (en) Semi-durable, water repellant, fire resistant intumescent process
US3324205A (en) Halogenated phosphates and phosphonates and method of preparation
US2357725A (en) Flameproofing
US1955207A (en) Mothproofing agent
CN104220666B (zh) 纤维用防火加工剂
US2678330A (en) Bis-(2,3-dihalopropyl) chlorophosphonate
US2480790A (en) Fireproofing composition
CA1091858A (fr) Finis durables pour textiles, retardant la propagation de la flamme
US4097641A (en) Flame retardant finishes for textile materials
Godfrey Differential thermal analysis (DTA) and thermogravimetric analysis (TGA) studies of flame-retardant rayon fibers
Godfrey et al. Alkoxyphosphazenes as flame retardants for rayon
US3321330A (en) Textile materials and method of making the same
US3803271A (en) Organophosphonates
US2463983A (en) Flameproofing composition
US2926097A (en) Fire resistant composition for fabrics
US3681126A (en) Flame retardant article containing tris-(3 - halo - 2-hydroxypropyl)-hydroxymethylphosphonium chloride
US3729340A (en) Flame retardant polyester-acetate fabric
US2574518A (en) Organic compounds containing phosphorus and bromine
US4058466A (en) Brominated carbamoyl derivatives
US2547671A (en) Fire-resistant article, method of making, and impregnant therefor
CA1077203A (fr) Substrats resistants a la propagation de la flamme
US3989702A (en) Flame retardant
GB1533397A (en) Bromine-containing phosphoramidates having flame-retardant properties

Legal Events

Date Code Title Description
AS Assignment

Owner name: CHASE MANHATTAN BANK, THE NATIONAL ASSOCIATION

Free format text: SECURITY INTEREST;ASSIGNOR:DORSET INC. A CORP OF DELAWARE;REEL/FRAME:005122/0370

Effective date: 19890329

AS Assignment

Owner name: GAF CHEMICALS CORPORATION

Free format text: CHANGE OF NAME;ASSIGNOR:DORSET INC.;REEL/FRAME:005251/0071

Effective date: 19890411

AS Assignment

Owner name: DORSET INC., A DE CORP.

Free format text: CHANGE OF NAME;ASSIGNOR:GAF CORPORATION, A DE CORP.;REEL/FRAME:005250/0940

Effective date: 19890410

AS Assignment

Owner name: CHASE MANHATTAN BANK (NATIONAL ASSOCIATION), THE

Free format text: SECURITY INTEREST;ASSIGNOR:GAF CHEMICALS CORPORATION, A CORP. OF DE;REEL/FRAME:005604/0020

Effective date: 19900917

AS Assignment

Owner name: ISP INVESTMENTS INC.

Free format text: CHANGE OF NAME;ASSIGNOR:ISP 3 CORP.;REEL/FRAME:005949/0051

Effective date: 19910508

Owner name: ISP 3 CORP

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:GAF CHEMICALS CORPORATION;REEL/FRAME:005949/0001

Effective date: 19910508

AS Assignment

Owner name: GAF CHEMICALS CORPORATION

Free format text: RELEASED BY SECURED PARTY;ASSIGNOR:CHASE MANHATTAN BANK, THE (NATIONAL ASSOCIATION);REEL/FRAME:006243/0208

Effective date: 19920804

Owner name: SUTTON LABORATORIES, INC.

Free format text: RELEASED BY SECURED PARTY;ASSIGNOR:CHASE MANHATTAN BANK, THE (NATIONAL ASSOCIATION);REEL/FRAME:006243/0208

Effective date: 19920804

Owner name: GAF BUILDING MATERIALS CORPORATION

Free format text: RELEASED BY SECURED PARTY;ASSIGNOR:CHASE MANHATTAN BANK, THE (NATIONAL ASSOCIATION);REEL/FRAME:006243/0208

Effective date: 19920804