GB790663A - Improvements relating to compositions for flame-proofing cellulose containing material, their use, and material treated therewith - Google Patents
Improvements relating to compositions for flame-proofing cellulose containing material, their use, and material treated therewithInfo
- Publication number
- GB790663A GB790663A GB31443/55A GB3144355A GB790663A GB 790663 A GB790663 A GB 790663A GB 31443/55 A GB31443/55 A GB 31443/55A GB 3144355 A GB3144355 A GB 3144355A GB 790663 A GB790663 A GB 790663A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphoric acid
- bis
- ester
- alkyl
- amide
- 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
Links
- -1 their use Substances 0.000 title abstract 8
- 239000000203 mixture Substances 0.000 title abstract 6
- 239000000463 material Substances 0.000 title abstract 4
- 229920002678 cellulose Polymers 0.000 title 1
- 239000001913 cellulose Substances 0.000 title 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 19
- 125000004432 carbon atom Chemical group C* 0.000 abstract 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 6
- USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 4
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 abstract 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 239000007864 aqueous solution Substances 0.000 abstract 3
- 239000006185 dispersion Substances 0.000 abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 3
- 239000000243 solution Substances 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 229920000742 Cotton Polymers 0.000 abstract 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 2
- 229920000877 Melamine resin Polymers 0.000 abstract 2
- MQANGUAOOUEVPA-UHFFFAOYSA-N N-[butyl(methylamino)phosphoryl]methanamine Chemical compound CNP(=O)(NC)CCCC MQANGUAOOUEVPA-UHFFFAOYSA-N 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- CKTNHGVJKUQEBM-UHFFFAOYSA-N ethylazanide Chemical compound CC[NH-] CKTNHGVJKUQEBM-UHFFFAOYSA-N 0.000 abstract 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 abstract 2
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 abstract 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 abstract 1
- SUPOBRXPULIDDX-UHFFFAOYSA-N [[4-amino-6-(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound NC1=NC(NCO)=NC(NCO)=N1 SUPOBRXPULIDDX-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 abstract 1
- 235000013980 iron oxide Nutrition 0.000 abstract 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 abstract 1
- 229910044991 metal oxide Inorganic materials 0.000 abstract 1
- 150000004706 metal oxides Chemical class 0.000 abstract 1
- RPHFGEHBXPSYLK-UHFFFAOYSA-N methanamine;dihydrochloride Chemical compound Cl.Cl.NC RPHFGEHBXPSYLK-UHFFFAOYSA-N 0.000 abstract 1
- MWDCCRWZGLSKGS-UHFFFAOYSA-N n-methylmethanamine;dihydrochloride Chemical compound Cl.Cl.CNC MWDCCRWZGLSKGS-UHFFFAOYSA-N 0.000 abstract 1
- 150000003018 phosphorus compounds Chemical class 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- 150000003139 primary aliphatic amines Chemical class 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000004408 titanium dioxide Substances 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/423—Amino-aldehyde resins
- D06M15/43—Amino-aldehyde resins modified by phosphorus compounds
- D06M15/433—Amino-aldehyde resins modified by phosphorus compounds by phosphoric acids
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/423—Amino-aldehyde resins
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Fireproofing Substances (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Ortho-phosphoric acid derivatives of the general formula <FORM:0790663/IV (b)/1> wherein R = H or alkyl of 1-4 carbon atoms; and X1 and X2 are alkyl of 1-4 carbon atoms or alkoxy or alkylamino with alkyl groups containing 1-4 carbon atoms (used in flameproofing compositions containing a polymethylol melamine (see Groups IV (a) and VIII) are made from alkyl phosphonic acid dichlorides, o-phosphoric acid mono alkyl ester dichlorides, o-phosphoric acid dialkyl ester monochlorides or o-phosphoric acid mono-dialkylamide dichlorides and ammonia or a primary aliphatic amine in an inert solvent, e.g. chlorobenzene, chloroform, carbon tetrachloride or tetrachlorethane. In Example 1, monomethylamine hydrochloride is reacted with phosphorus oxychloride to yield o-phosphoric acid monomethylamide dichloride (B.P. 122-128 DEG C.) which is dissolved in chloroform and added dropwise to a chloroform solution of methylamine at a temperature held between -5 DEG and 5 DEG C. The reaction mixture is stirred, heated, cooled and filtered to remove methylamine hydrochloride. The product has the formula <FORM:0790663/IV (b)/2> In Example 2, o-phosphoric acid di(methyl)-amide-bis-(ethylamide) is similarly prepared from o-phosphoric acid mono-dimethyl-amide dichloride and ethylamine in benzene. In Example 3 o-phosphoric acid monoethyl ester dichloride is dissolved in chlorbenzene and added to a chlorbenzene solution of methylamine. o-phosphoric acid monoethyl ester-bis-(methylamide) (B.P. 110-111 DEG C. at 0.005 mms.) is isolated from the reaction mixture.ALSO:Cellulosic material is rendered flameproof by treatment with an aqueous solution containing 1 mol. of polymethylol melamine which may be etherified and 2/3 -3 mols. of a substance with the general formula <FORM:0790663/IV (a)/1> in which R is H or an alkyl group of 1-4 carbon atoms and X1 and X2 each represent an alkyl radical of 1-4 carbon atoms, an alkoxy radical of 1-4 carbon atoms, or an alkylamino group in which the alkyl groups have 1-4 carbon atoms. Suitable phosphorus compounds are (a) alkyl phosphonic acid amides, e.g. methyl or ethyl phosphonic acid-bis-(mono-methyl or -ethyl amide), or propyl or butyl phosphonic acid-bis-(monomethylamide); (b) o-phosphoric acid dialkyl ester monoamides, e.g. o-phosphoric acid dimethyl or diethyl ester-mono-, monomethyl-or monoethyl-amide; (c) o-phosphoric acid monoalkyl ester diamides, e.g. o-phosphoric acid mono-methyl-, ethyl-, propyl- or butyl-ester-bis-(monomethylamide) or o-phosphoric acid mono-methyl- or ethyl-ester-bis-(monoethylamide); and (d) o-phosphoric acid triamides, e.g. o-phosphoric acid dimethyl- or diethylamide-bis-(monomethyl or monoethyl amide), or o - phosphoric acid - butylamino - bis - (methylamide). Cellulosic materials are impregnated with the aqueous solutions and heated to over 80 DEG C., if desired, after drying. The compositions of the present invention may be used in the aqueous phase of dispersion of polyvinyl compounds which contain metal oxides, e.g. titanium dioxide, antimony trioxide, chromic oxide or iron oxides in suspension. In examples: (1) the tris-(monomethylamide) of o-phosphoric acid and trimethylol melamine are dissolved in water. Mercerized cotton muslin is impregnated with the solution, dried and heated for 20 minutes at 120 DEG C.; (2) o-phosphoric acid (dimethylamido-)-bis-(monoethylamide) is used with trimethylol melamine; (3) o-phosphoric acid monoethyl ester-bis-(monomethylamide) is used with trimethylol melamine trimethyl ether. Various other flame-proofing compositions according to the invention are also listed in this example; (4) methyl, ethyl or butyl phosphonic acid-bis-(methylamide) is used with trimethylol melamine; (5) flame-proofing mixtures contain o-phosphoric acid diethyl ester amide and dimethylol melamine or o-phosphoric dimethyl ester amide and trimethylol melamine; (6) a polyvinyl chloride dispersion is stirred with a dispersion of antimony trioxide, a naphthalene sulphonic acid-formaldehyde condensate and water. An aqueous solution of o-phosphoric acid monoethylester - bis - (methylamide) and trimethylol melamine is added and the mixture used to flameproof cotton.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH790663X | 1954-11-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB790663A true GB790663A (en) | 1958-02-12 |
Family
ID=4536958
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31443/55A Expired GB790663A (en) | 1954-11-05 | 1955-11-03 | Improvements relating to compositions for flame-proofing cellulose containing material, their use, and material treated therewith |
| GB8610/57A Expired GB804745A (en) | 1954-11-05 | 1957-03-15 | Improvements relating to compositions for flame-proofing cellulosic material, their use, and material treated therewith |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8610/57A Expired GB804745A (en) | 1954-11-05 | 1957-03-15 | Improvements relating to compositions for flame-proofing cellulosic material, their use, and material treated therewith |
Country Status (6)
| Country | Link |
|---|---|
| BE (2) | BE555825A (en) |
| CH (1) | CH332777A (en) |
| DE (2) | DE1040498B (en) |
| FR (2) | FR1140874A (en) |
| GB (2) | GB790663A (en) |
| NL (2) | NL201490A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3632297A (en) * | 1970-03-12 | 1972-01-04 | Stevens & Co Inc J P | Process for rendering cellulose-containing fabrics durably flame-retardant by wet-curing a melamine resin and a phosphoric acid amide on the fabric |
| JPS5529196B1 (en) * | 1970-08-05 | 1980-08-01 | ||
| CN105538451A (en) * | 2016-01-28 | 2016-05-04 | 河南森远科技有限公司 | Method for preparing phosphorous-nitrogen synergistic wood fire retardant |
| CN115074853A (en) * | 2022-06-24 | 2022-09-20 | 武汉纺织大学 | Flame-retardant polypropylene fabric and preparation method thereof |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1225073A (en) * | 1959-02-13 | 1960-06-29 | Cfmc | New phosphorus compounds, their preparation processes and their applications in fireproofing |
| DE1287312B (en) * | 1960-02-11 | 1969-01-16 | Schering Ag | Hardening agent for compounds hardenable to polymers |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB691358A (en) * | 1948-11-26 | 1953-05-13 | Glenn L Martin Co | Improvements in or relating to the production of unsaturated aliphatic phosphonamides |
-
0
- NL NL108804D patent/NL108804C/xx active
- BE BE542559D patent/BE542559A/xx unknown
- BE BE555825D patent/BE555825A/xx unknown
- NL NL201490D patent/NL201490A/xx unknown
- DE DENDAT1006386D patent/DE1006386B/en active Pending
-
1954
- 1954-11-05 CH CH332777D patent/CH332777A/en unknown
-
1955
- 1955-11-03 GB GB31443/55A patent/GB790663A/en not_active Expired
- 1955-11-04 FR FR1140874D patent/FR1140874A/en not_active Expired
-
1957
- 1957-03-15 FR FR71440D patent/FR71440E/en not_active Expired
- 1957-03-15 GB GB8610/57A patent/GB804745A/en not_active Expired
- 1957-03-15 DE DEG21708A patent/DE1040498B/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3632297A (en) * | 1970-03-12 | 1972-01-04 | Stevens & Co Inc J P | Process for rendering cellulose-containing fabrics durably flame-retardant by wet-curing a melamine resin and a phosphoric acid amide on the fabric |
| JPS5529196B1 (en) * | 1970-08-05 | 1980-08-01 | ||
| CN105538451A (en) * | 2016-01-28 | 2016-05-04 | 河南森远科技有限公司 | Method for preparing phosphorous-nitrogen synergistic wood fire retardant |
| CN105538451B (en) * | 2016-01-28 | 2017-03-22 | 河南森远科技有限公司 | Method for preparing phosphorous-nitrogen synergistic wood fire retardant |
| CN115074853A (en) * | 2022-06-24 | 2022-09-20 | 武汉纺织大学 | Flame-retardant polypropylene fabric and preparation method thereof |
| CN115074853B (en) * | 2022-06-24 | 2024-05-28 | 武汉纺织大学 | Flame-retardant polypropylene fabric and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| NL108804C (en) | |
| DE1040498B (en) | 1958-10-09 |
| FR71440E (en) | 1960-01-04 |
| NL201490A (en) | |
| BE555825A (en) | |
| FR1140874A (en) | 1957-08-20 |
| BE542559A (en) | |
| GB804745A (en) | 1958-11-19 |
| CH332777A (en) | 1958-09-30 |
| DE1006386B (en) | 1957-04-18 |
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