US3908051A - Method for processing cellulose containing materials to impart thereto flame resistance - Google Patents
Method for processing cellulose containing materials to impart thereto flame resistance Download PDFInfo
- Publication number
- US3908051A US3908051A US44680274A US3908051A US 3908051 A US3908051 A US 3908051A US 44680274 A US44680274 A US 44680274A US 3908051 A US3908051 A US 3908051A
- Authority
- US
- United States
- Prior art keywords
- flame resistance
- groups
- compound
- impart
- cellulose containing
- 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
- 238000000034 method Methods 0.000 title claims abstract description 30
- 239000000463 material Substances 0.000 title claims abstract description 14
- 229920002678 cellulose Polymers 0.000 title description 10
- 239000001913 cellulose Substances 0.000 title description 10
- -1 phosphorus compound Chemical class 0.000 claims abstract description 15
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 6
- 239000011574 phosphorus Substances 0.000 claims abstract description 6
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical group O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 11
- 238000005406 washing Methods 0.000 abstract description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 30
- 239000004744 fabric Substances 0.000 description 14
- 150000003018 phosphorus compounds Chemical class 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002657 fibrous material Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 229920003180 amino resin Polymers 0.000 description 4
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 230000002045 lasting effect Effects 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DZHMRSPXDUUJER-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;dihydrogen phosphate Chemical compound NC(N)=O.OP(O)(O)=O DZHMRSPXDUUJER-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- DHWBZDYABPGLMV-UHFFFAOYSA-N (1-amino-2-methyl-1-oxopropan-2-yl)-ethoxyphosphinic acid Chemical compound CC(C(=O)N)(C)P(=O)(OCC)O DHWBZDYABPGLMV-UHFFFAOYSA-N 0.000 description 1
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 206010042618 Surgical procedure repeated Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ONTAEZSXZGCILH-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)-methoxyamino]methanol Chemical compound CON(CO)C1=NC(N)=NC(N)=N1 ONTAEZSXZGCILH-UHFFFAOYSA-N 0.000 description 1
- RFYJMHCYVBBXAZ-UHFFFAOYSA-N [3-oxo-3-[(3-phosphonopropanoylamino)methoxymethylamino]propyl]phosphonic acid Chemical compound P(=O)(O)(O)CCC(=O)NCOCNC(CCP(=O)(O)O)=O RFYJMHCYVBBXAZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- WVJOGYWFVNTSAU-UHFFFAOYSA-N dimethylol ethylene urea Chemical compound OCN1CCN(CO)C1=O WVJOGYWFVNTSAU-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 235000011147 magnesium chloride Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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
- D06M13/288—Phosphonic or phosphonous 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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2631—Coating or impregnation provides heat or fire protection
- Y10T442/2672—Phosphorus containing
- Y10T442/268—Phosphorus and nitrogen containing compound
Definitions
- nalkyl groups are preferred, of the alkyl groups methyl lA :ielatlvJely new nliaethogI for6glla gggr l irlg 8 (118- group is preferred and of the halogenalkyl groups the c ose in apanese at. o.
- thyleneurea 5-hydroxypropyleneurea and dlalkoxye-
- ethyleneurea propyleneurea and N, odor and tend to generate formaldehyde easily in the N -d1methylurea are preferred.
- the prepara tion of the phosphorus compounds (I) used in accor- An oblect of the preem mventlon ls to provlde a dance with the method of the present invention may nmiel for reducmg the frma1dehde conveniently be made by one of the following methods: sociated with the flameproofing of cellulosic containing materials.
- the residue of the nitrogen containing compound, produced by the splitting of methylene ether bonds, provides a cross-linking reaction with the cellulosic fiber, so that the treated cloth exhibits not only flame resistance coupled with excellent fastness upon washing, but also greatly enhanced crease resistance. Since the phosphorus compounds (I) do not emit a formaldehyde odor and do not generate of formaldehyde in the course of processing, the working environment is significantly improved.
- reaction catalysts used to react the cellulose con taining materials with the phosphorus compounds of formula (I) used in are those catalysts conventional in the curing of amino resins, for example ammonium chloride, orthophosphoric acid, magnesium chloride, zinc nitrate or zinc borofluoride.
- the concentration in the processing solution of the phosphorus compound (I) used, for wetting the cellulosic fibrous materials may be varied in accordance with the desired degree of flame resistance to be imparted, although it will generally be within the range of from 5 to 80 percent by weight, and preferably in the range of from to 50 percent by weight.
- processing solutions may be applied to the cellulose containing material, by any of a variety of known methods, such as pressing between rolls, spraying or centrifugation.
- manner of drying the wetted or impregnated material is conventional and practically any temperature between room temperature and 200C suffices. With regard to curing conditions, satisfactory results are obtainable by curing at temperatures of the order on from 120 to 200C for periods of time of from seconds to 10 minutes.
- amino resins may simultaneously be applied to the material by inclusion in the treatment bath.
- Suitable resins include the reaction products of a variety of low molecular amino compounds with formaldehyde and the alkoxylated derivatives thereof.
- the amino compounds usually used as starting materials for the manufacture of amino resins include, for example, urea, melamine, thiourea, ethyleneurea, guanidine and urone.
- This viscous liquid was found to contain 0.3 percent free formaldehyde, 1.8 percent methylol-type formaldehyde and 19.14 percent methylene ether-type formaldehyde (determined as formaldehyde after decomposition with a dilute aqueous acid solution).
- the analytic results show that the product is of 89.4 percent purity.
- a cotton No. 40 broadcloth was treated in an aqueous solution containing a 30 percent by weight of the product produced above to which solution 0.4 percent ammonium chloride had been added, washed 5 times with a 0.2 percent aqueous detergent aqueous solution and dried.
- the combustion test with the processed cloth showed incombustibility and the crease resistance of the processed cloth was 287 (original cloth 17.8).
- EXAMPLE 2 Flame resistance tests were conducted with a cotton twill processed with the various urea derivatives as shown in Table 1 below.
- the composition of each of the respective processing baths as well as the test results before and after washing are also shown in Table
- the processing procedure was as follows: The cloth was, after impregnation, picked up percent by weight pick up), dried at 90C for 4 minutes and cured at C for 4 minutes.
- the cured cloth was subjected to 10 minutes of soaping at 40C in a 0.2 percent by weight detergent (manufactured by Kao Sekken Co., Ltd.; Trade Name ZABU) aqueous solution and then rinsed for 5 minutes with water, this procedure repeated 5 times. The finally dried cloth was used as the test cloth for after washmg.
- a 0.2 percent by weight detergent manufactured by Kao Sekken Co., Ltd.; Trade Name ZABU
- the flame resistance test was carried out in accordance with Japanese Industrial Standards (J IS )-L-l091 Al.
- This test method is also referred to as the 45 microbumer method.
- the test cloth is spread over a 25 X 15 cm frame and set in a combustion test chamber at an angle of 45.
- the microbumer is ignited, the cloth heated for 1 minute and the flame duration or lasting time (the length of time from the end of heating to a point where flaming of the test cloth ends) is determined.
- the microburner is adjusted beforehand to a flame length of 4.5 cm with the tip of the flame in contact with the test cloth. Subsequently, the
- R R R and R ized length and area are determined. are alkyl or halogenalkyl groups of 4 or less carbon Table 1 Processing Bath by weigt) Before Washing After Washing R X Ac- NH4CI l-LJO.
- a method for flameproofing cellulosic materials comprising applying to the cellulosic material an aqueous solution of a phosphorus compound represented by the following general formula:
- R to R are the same or different alkyl, alkenyl or alkoxyalkyl groups which may be substituted by one
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Fireproofing Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2326673A JPS49109700A (sv) | 1973-02-28 | 1973-02-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3908051A true US3908051A (en) | 1975-09-23 |
Family
ID=12105787
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US44680274 Expired - Lifetime US3908051A (en) | 1973-02-28 | 1974-02-28 | Method for processing cellulose containing materials to impart thereto flame resistance |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3908051A (sv) |
| JP (1) | JPS49109700A (sv) |
| GB (1) | GB1462076A (sv) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4007318A (en) * | 1975-05-21 | 1977-02-08 | General Electric Company | Phosphorylated polystyrene and method for forming same |
| US4013813A (en) * | 1975-02-27 | 1977-03-22 | Leblanc Research Corporation | Aminoalkylphosphonic acid ester-based textile fire retardants |
| US4198328A (en) * | 1977-10-10 | 1980-04-15 | Montedison S.P.A. | Flame-resisting intumescent paints |
| CN105220452A (zh) * | 2014-06-26 | 2016-01-06 | 香港理工大学 | 抗皱整理剂、织物抗皱整理方法和抗皱织物 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004015356A1 (de) * | 2004-03-30 | 2005-10-20 | Clariant Gmbh | Phosphorhaltige Flammschutzmittelzusammensetzung für cellulosehaltige Materialien |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3658952A (en) * | 1968-07-11 | 1972-04-25 | Ciba Ltd | Bis((dialkyl)phosphonoalkylamido) alkyls |
| US3699192A (en) * | 1970-10-20 | 1972-10-17 | U S Oil Co Inc | Phosphonium compounds |
| US3754981A (en) * | 1970-06-11 | 1973-08-28 | Ciba Geigy Ag | Process for flameproofing cellulose-containing fibre material |
| US3763283A (en) * | 1969-10-17 | 1973-10-02 | Patrick & Co Inc C | N hydroxymethylated dialkyl phosphonoalkyl carbamates |
-
1973
- 1973-02-28 JP JP2326673A patent/JPS49109700A/ja active Pending
-
1974
- 1974-02-22 GB GB829574A patent/GB1462076A/en not_active Expired
- 1974-02-28 US US44680274 patent/US3908051A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3658952A (en) * | 1968-07-11 | 1972-04-25 | Ciba Ltd | Bis((dialkyl)phosphonoalkylamido) alkyls |
| US3763283A (en) * | 1969-10-17 | 1973-10-02 | Patrick & Co Inc C | N hydroxymethylated dialkyl phosphonoalkyl carbamates |
| US3754981A (en) * | 1970-06-11 | 1973-08-28 | Ciba Geigy Ag | Process for flameproofing cellulose-containing fibre material |
| US3699192A (en) * | 1970-10-20 | 1972-10-17 | U S Oil Co Inc | Phosphonium compounds |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4013813A (en) * | 1975-02-27 | 1977-03-22 | Leblanc Research Corporation | Aminoalkylphosphonic acid ester-based textile fire retardants |
| US4007318A (en) * | 1975-05-21 | 1977-02-08 | General Electric Company | Phosphorylated polystyrene and method for forming same |
| US4198328A (en) * | 1977-10-10 | 1980-04-15 | Montedison S.P.A. | Flame-resisting intumescent paints |
| CN105220452A (zh) * | 2014-06-26 | 2016-01-06 | 香港理工大学 | 抗皱整理剂、织物抗皱整理方法和抗皱织物 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS49109700A (sv) | 1974-10-18 |
| DE2408502A1 (de) | 1974-08-29 |
| DE2408502B2 (de) | 1976-09-02 |
| GB1462076A (en) | 1977-01-19 |
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