US3556825A - Flame retardant rayon incorporating bis-diphenyl phosphate derivative of polyalkylene glycols - Google Patents
Flame retardant rayon incorporating bis-diphenyl phosphate derivative of polyalkylene glycols Download PDFInfo
- Publication number
- US3556825A US3556825A US867918A US3556825DA US3556825A US 3556825 A US3556825 A US 3556825A US 867918 A US867918 A US 867918A US 3556825D A US3556825D A US 3556825DA US 3556825 A US3556825 A US 3556825A
- Authority
- US
- United States
- Prior art keywords
- flame
- diphenyl phosphate
- flame retardant
- retardant
- bis
- 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
Links
- 229920000297 Rayon Polymers 0.000 title abstract description 26
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title abstract description 22
- 239000003063 flame retardant Substances 0.000 title abstract description 21
- 239000002964 rayon Substances 0.000 title abstract description 11
- 229920001515 polyalkylene glycol Polymers 0.000 title description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 1
- 150000002334 glycols Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000000835 fiber Substances 0.000 description 6
- 238000009987 spinning Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- 239000004744 fabric Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000004627 regenerated cellulose Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- -1 alkylene glycols Chemical class 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000009781 Myrtillocactus geometrizans Nutrition 0.000 description 1
- 240000009125 Myrtillocactus geometrizans Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
- D01F2/06—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose
- D01F2/08—Composition of the spinning solution or the bath
- D01F2/10—Addition to the spinning solution or spinning bath of substances which exert their effect equally well in either
Definitions
- R is an alkylene radical having 2 to 4 carbon atoms, x is an integer of from 1 to 3; when x is 1, R has at least 3 carbon atoms, and when x is 3, R has 2 carbon atoms.
- Compounds meeting the above formulation include, for example, dipropylene glycolbis-(diphenyl phosphate), dibutylene glycol bis-(diphenyl phosphate), triethylene glycol' bis-(diphenyl phosphate), tripropylene glycol bis- (diphenyl phosphate), tetraethylene glycol bis-(diphenyl phosphate) and the like.
- the flame retardant compounds will consist of mixtures wherein the alkylene glycol residue varies in molecular weight whereby the average molecular weight of the compounds will place them within the above description.
- This invention also includes a method of preparing a flame-retardant filament or filaments wherein the above described flame-retardant. compound is incorporated in viscose, the mixture formed into one or more filaments and the filaments are coagulated and regenerated.
- formed filaments are aftertreated using techniques well known in the rayon field to provide continuous filaments, fibers and yarn as well as staple fibers.
- the filamentary products are then used to prepare any known textile article in which flame retardancy is desirable.
- the number of carbon atoms in the alkylene radical of the above described flame-retardant compounds appears to be related to theretention of these compounds in the filaments during the viscose spinning process, If there are less carbon atoms than prescribed, the compound is more water soluble and consequently not retained in an amount sufficient to provide suitable flame retardancy. On the other hand, if more than the prescribed number of carbon atoms are present in the alkylene radical the percent of phosphorus in the compound is reduced and flame retardancy is greatly impaired.
- the flame-retardant compounds are water-insoluble viscous liquids and are dispersed in the regenerated cellulose filaments in amounts ranging from about 10 to 50%, preferably from about 15 to 35%, based on the weight of the cellulose in the filament.
- the compounds are advantageously injected into the viscose solution prior The following examples are set forth to demonstrate this invention.
- EXAMPLE I Dipropylene glycol bis-(diphenyl phosphate) was injected into the viscose line-supplying the spinnerets for manufacturing rayon in a metered amount to provide a filament containing about 25% by weight of the flame-retardant compound based on the weight of the cellulose. This viscose was spun into a conventional aqueous acid spin bath. The resulting yarn was processed by passing it through a series of baths including water wash, desulfurization, bleaching, bleach acid, anti-chlor (Na S O and soft finish baths. The yarn was dried and collected.
- a yarn flammability test was conducted with yarn produced as described above. The test consisted of first preparing a yarn bundle by wrapping the yarn around the closed fingers of an extended hand to produce a bundle of 6000 denier and then removing it from the hand. The yarn bundle is twisted five times and then doubled on itself to produce an integrated yarn bundle,
- a control yarn bundle contains no flame-retardant inflames'in 1.01 2 passes and flame-retardant yarns are classified for inflammability as follows:
- O OCH u/ U ege'nerated' cellulose filaments of claim 1 containing from about 10 to of said compound based on the weight of the cellulose in the filament.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Artificial Filaments (AREA)
Abstract
BIS-DEPHENYL PHOSPHATE DERIVATIVES OF SPECIFIED ALKYLENE GLYCOLS ARE INCORPORATED INTO VISCOSE SOLUTIONS WHICH ARE THEN SPUN INTO FLAME RETARDANT RAYON.
Description
Uniwd- Sta e Pam- 3,556,825 FLAME RETARDANT RAYON INCORPORATING BIS-DIPHENYL PHOSPHATE- DERIVATIVE 0F POLYALKYLENE GLYCOLS Charles A. Lynch, Severnalark, Md., assignor to FMC Corporation, Philadelphia, Pa., a corporation of Delaware No Drawing. Filed Oct. 20, 1969, Ser. No. 867,918 Int. Cl. C0811 21/20 U.S. Cl. 106-168 3 Claims ABSTRACT OF THE DISCLOSURE Bis-diphenyl phosphate derivatives of specified alkylene glycols are incorporated into viscose solutions which are then spun into flame retardant rayon.
It is desirable for many textile purposes to provide cellulose fibers and yarns having greatly decreased flammability. The production of rayon-which demonstrates acceptable flame-retardant properties for all textile requirements, using inexpensive and commercially suitable chemical flame-retardants, has not been satisfactorily accomplished to date.
The application'of variousorganic and inorganic fiame retardants to the surface of cellulose fibers and fabrics has not produced the desired result for a number of reasons. In many instances, the chemical flame-retardant is effectively removed when thefabric is washed with water or dry cleaned with solvents. Other flame-retardant chemicals which may be applied to the fabric surface and retained after washing are generally too costly. In other cases, the chemicals used may provide some lasting reduction in flammability but destroy fiber and fabric characteristics, such as tenacity, softness, whiteness and dyeability, which are desirable and necessary for textile applications.
In the manufacture of rayon by the viscose method, it has been proposed to add various flame-retardant chemicals to the viscose prior to spinning. This approach presents many additional problems because of the particular chemistry of the viscose process. Accordingly, the flameretardant must be stable and inert with respect to the highly alkaline viscose and also with respect to the acid regenerating bath into which the viscose is extruded. It must not be extracted during spinning and processing. Furthermore, the added material must not interfere with the spinning process, i.e., cause clogging of the spinnerets. The rayon produced from the flame-retardant containing viscose must not be degraded in any of its properties and must have a substantially reduced flammability.
It is an object of this invention to provide a flameretardant rayon fiber without appreciable degradation of any fiber properties.
It is a further object of this invention to provide a process for preparing a flame-retardant rayon fiber which retains substantially all of the properties of ordinary rayon.
These and other objects are achieved in accordance with this invention which comprises a regenerated cellulose filament having dispersed therein a flame-retardant amount of a compound having the following formula:
wherein R is an alkylene radical having 2 to 4 carbon atoms, x is an integer of from 1 to 3; when x is 1, R has at least 3 carbon atoms, and when x is 3, R has 2 carbon atoms.
Compounds meeting the above formulation include, for example, dipropylene glycolbis-(diphenyl phosphate), dibutylene glycol bis-(diphenyl phosphate), triethylene glycol' bis-(diphenyl phosphate), tripropylene glycol bis- (diphenyl phosphate), tetraethylene glycol bis-(diphenyl phosphate) and the like.
In some instances the flame retardant compounds will consist of mixtures wherein the alkylene glycol residue varies in molecular weight whereby the average molecular weight of the compounds will place them within the above description.
This invention also includes a method of preparing a flame-retardant filament or filaments wherein the above described flame-retardant. compound is incorporated in viscose, the mixture formed into one or more filaments and the filaments are coagulated and regenerated. The
ICQ
formed filaments are aftertreated using techniques well known in the rayon field to provide continuous filaments, fibers and yarn as well as staple fibers. The filamentary products are then used to prepare any known textile article in which flame retardancy is desirable.
The number of carbon atoms in the alkylene radical of the above described flame-retardant compounds appears to be related to theretention of these compounds in the filaments during the viscose spinning process, If there are less carbon atoms than prescribed, the compound is more water soluble and consequently not retained in an amount sufficient to provide suitable flame retardancy. On the other hand, if more than the prescribed number of carbon atoms are present in the alkylene radical the percent of phosphorus in the compound is reduced and flame retardancy is greatly impaired.
The flame-retardant compounds are water-insoluble viscous liquids and are dispersed in the regenerated cellulose filaments in amounts ranging from about 10 to 50%, preferably from about 15 to 35%, based on the weight of the cellulose in the filament. The compounds are advantageously injected into the viscose solution prior The following examples are set forth to demonstrate this invention.
EXAMPLE I Dipropylene glycol bis-(diphenyl phosphate) was injected into the viscose line-supplying the spinnerets for manufacturing rayon in a metered amount to provide a filament containing about 25% by weight of the flame-retardant compound based on the weight of the cellulose. This viscose was spun into a conventional aqueous acid spin bath. The resulting yarn was processed by passing it through a series of baths including water wash, desulfurization, bleaching, bleach acid, anti-chlor (Na S O and soft finish baths. The yarn was dried and collected.
A yarn flammability test was conducted with yarn produced as described above. The test consisted of first preparing a yarn bundle by wrapping the yarn around the closed fingers of an extended hand to produce a bundle of 6000 denier and then removing it from the hand. The yarn bundle is twisted five times and then doubled on itself to produce an integrated yarn bundle,
n a nea i ches Qns.. r1d- ...Q9Q sui r. aize.
The free ends of the yarn bundle are clamped in forceps, and the bundle, held in horizontal position, is passed through the tip of the flame of a Fisher burner in an oscillating motion at a rate of one pass per second. The burner flame is adjusted to a two inch height and a blue flame. The number of passes to induce flaming of the sample is determined. A control yarn bundle (yarn contains no flame-retardant) inflames'in 1.01 2 passes and flame-retardant yarns are classified for inflammability as follows:
1-2 passes-poor 3-4 passes--fair 5-6 passes-good 79 passesvery good to excellent 10 or more passesexcellent Polyethylene glycol (200 average M.W.) bis-(diphenyl phosphate) was injected into viscose and the viscose spun into yarn as described in Example I. The yarn was processed and tested for flame-retardancy as in Example I. Retention of the flame retardant in the yarn after spinning and processing was found to be 55% of the amount procedure with no evidence of afterglow.
It is expected that improvement in the flammability test would accompany higher amounts of the flame retardant in the filaments ofthe yarn.
:1. Regenerated cellulosefilaments and filamentary articles, said filaments having dispersed therein aflame retardant amounttof'a compound having the following m wherein R is an alky le'ne radical having from 2 to 4 carbon atorn'sj,=j-x is an integer of from 1' to-fiywhen x is 1 or 2, R has at least 3 carbon atoms, and when g; is 3, R has 2 carbon atoms. 2. The
O OCH u/ U ege'nerated' cellulose filaments of claim 1 containing from about 10 to of said compound based on the weight of the cellulose in the filament.
3. The regenerated cellulose filaments of claim 1 Wherein'R has 3 carbon atoms and x is 1.
7 References Cited p V UNITED STATES PATENTS 3,092,651 6/1963v Friedman 106l77 MORRIS LIEBMAN, Primary Examiner T. MORRIS, Assistant Examiner U.S. Cl. X.R.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86791869A | 1969-10-20 | 1969-10-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3556825A true US3556825A (en) | 1971-01-19 |
Family
ID=25350710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US867918A Expired - Lifetime US3556825A (en) | 1969-10-20 | 1969-10-20 | Flame retardant rayon incorporating bis-diphenyl phosphate derivative of polyalkylene glycols |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3556825A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4242138A (en) * | 1975-07-31 | 1980-12-30 | Sandoz Ltd. | Flameproofed regenerated cellulose and method |
| WO1999005200A1 (en) * | 1997-07-25 | 1999-02-04 | Nycomed Imaging As | Process for the preparation of polyether phosphates |
| KR20180041398A (en) * | 2016-10-14 | 2018-04-24 | 에스디코리아(주) | A producing method of non-halogen phosphorus-based flame retardant |
-
1969
- 1969-10-20 US US867918A patent/US3556825A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4242138A (en) * | 1975-07-31 | 1980-12-30 | Sandoz Ltd. | Flameproofed regenerated cellulose and method |
| WO1999005200A1 (en) * | 1997-07-25 | 1999-02-04 | Nycomed Imaging As | Process for the preparation of polyether phosphates |
| US6500917B1 (en) | 1997-07-25 | 2002-12-31 | Amersham Health As | Process for the preparation of polyether phosphates |
| KR20180041398A (en) * | 2016-10-14 | 2018-04-24 | 에스디코리아(주) | A producing method of non-halogen phosphorus-based flame retardant |
| KR101852521B1 (en) * | 2016-10-14 | 2018-06-07 | 에스디코리아(주) | A producing method of non-halogen phosphorus-based flame retardant |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: WESTERN AND SOUTHERN LIFE INSURANCE COMPANY THE C/ Free format text: AS SECURITY FOR INDEBTEDNESS RECITED ASSIGNOR GRANTS , BARGAINS, MORTGAGES, PLEDGES, SELLS AND CREATES A SECURITY INTEREST WITH A LIEN UNDER SAID PATENTS, SUBJECT TO CONDITIONS RECITED.;ASSIGNOR:AVTEX FIBERS INC. A NY CORP.;REEL/FRAME:003959/0219 Effective date: 19810301 Owner name: BALBOA INSURANCE COMPANY C/O THE PAUL REVERE EQUIT Free format text: AS SECURITY FOR INDEBTEDNESS RECITED ASSIGNOR GRANTS , BARGAINS, MORTGAGES, PLEDGES, SELLS AND CREATES A SECURITY INTEREST WITH A LIEN UNDER SAID PATENTS, SUBJECT TO CONDITIONS RECITED.;ASSIGNOR:AVTEX FIBERS INC. A NY CORP.;REEL/FRAME:003959/0219 Effective date: 19810301 Owner name: PAUL REVERE LIFE INSURANCE COMPANY THE C/O THE PAU Free format text: AS SECURITY FOR INDEBTEDNESS RECITED ASSIGNOR GRANTS , BARGAINS, MORTGAGES, PLEDGES, SELLS AND CREATES A SECURITY INTEREST WITH A LIEN UNDER SAID PATENTS, SUBJECT TO CONDITIONS RECITED.;ASSIGNOR:AVTEX FIBERS INC. A NY CORP.;REEL/FRAME:003959/0219 Effective date: 19810301 Owner name: NEW ENGLAND MUTUAL LIFE INSURANCE COMPANY 501 BOYL Free format text: AS SECURITY FOR INDEBTEDNESS RECITED ASSIGNOR GRANTS , BARGAINS, MORTGAGES, PLEDGES, SELLS AND CREATES A SECURITY INTEREST WITH A LIEN UNDER SAID PATENTS, SUBJECT TO CONDITIONS RECITED.;ASSIGNOR:AVTEX FIBERS INC. A NY CORP.;REEL/FRAME:003959/0219 Effective date: 19810301 Owner name: PROVIDENT ALLIANCE LIFE INSURANCE COMPANY C/O THE Free format text: AS SECURITY FOR INDEBTEDNESS RECITED ASSIGNOR GRANTS , BARGAINS, MORTGAGES, PLEDGES, SELLS AND CREATES A SECURITY INTEREST WITH A LIEN UNDER SAID PATENTS, SUBJECT TO CONDITIONS RECITED.;ASSIGNOR:AVTEX FIBERS INC. A NY CORP.;REEL/FRAME:003959/0219 Effective date: 19810301 Owner name: KELLOGG CREDIT CORPORATION A DE CORP. Free format text: AGREEMENT WHEREBY SAID HELLER AND RAYONIER RELEASES ALL MORTGAGES AND SECURITY INTERESTS HELD BY AVTEX ON APRIL 28, 1978, AND JAN. 11, 1979, RESPECTIVELY AND ASSIGNS ITS ENTIRE INTEREST IN SAID MORT-AGAGE AGREEMENT TO ASSIGNEE;ASSIGNORS:WALTER E. HELLER & COMPANY, INC. A NY CORP.;ITT RAYONIER INCORPORATED, A DE CORP.;AVTEX FIBERS INC., A NY CORP.;REEL/FRAME:003959/0350 Effective date: 19800326 Owner name: WALTER E. HELLER & COMPANY, INC., A CORP. OF DEL. Free format text: AGREEMENT WHEREBY AETNA RELEASES AVTEX FROM ALL MORTAGES AND SECURITY INTERESTS IN SAID INVENTIONS AS OF JANUARY 11,1979, AND ASSIGNS TO ASSIGNEE THE ENTIRE INTEREST IN SAID MORTAGE AGREEMENT TO ASSIGNEE;ASSIGNORS:AETNA BUSINESS CREDIT, INC., A CORP. OF N.Y.;AVTEX FIBERS, INC, A CORP. OF NY;KELLOGG CREDIT CORP., A CORP. OF DEL.;REEL/FRAME:003959/0250 Effective date: 19800326 Owner name: JOHN HANCOCK MUTUAL LIFE INSURANCE COMPANY JOHN HA Free format text: AS SECURITY FOR INDEBTEDNESS RECITED ASSIGNOR GRANTS , BARGAINS, MORTGAGES, PLEDGES, SELLS AND CREATES A SECURITY INTEREST WITH A LIEN UNDER SAID PATENTS, SUBJECT TO CONDITIONS RECITED.;ASSIGNOR:AVTEX FIBERS INC. A NY CORP.;REEL/FRAME:003959/0219 Effective date: 19810301 |