US2472335A - Method of flameproofing combustible cellulosic material - Google Patents
Method of flameproofing combustible cellulosic material Download PDFInfo
- Publication number
- US2472335A US2472335A US62899445A US2472335A US 2472335 A US2472335 A US 2472335A US 62899445 A US62899445 A US 62899445A US 2472335 A US2472335 A US 2472335A
- Authority
- US
- United States
- Prior art keywords
- flame
- pentaerythritol
- flameproofing
- combustible
- polyethyleneimine
- 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
- 239000000463 material Substances 0.000 title description 19
- 238000000034 method Methods 0.000 title description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 18
- 229920002873 Polyethylenimine Polymers 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 235000011007 phosphoric acid Nutrition 0.000 description 9
- NXWHTQVVOSZLDP-UHFFFAOYSA-N [3-phosphonooxy-2,2-bis(phosphonooxymethyl)propyl] dihydrogen phosphate Chemical compound OP(O)(=O)OCC(COP(O)(O)=O)(COP(O)(O)=O)COP(O)(O)=O NXWHTQVVOSZLDP-UHFFFAOYSA-N 0.000 description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000004744 fabric Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 3
- OICWCHGZYYVJHJ-UHFFFAOYSA-N 2-n-(triethoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound CCOC(OCC)(OCC)NC1=NC(N)=NC(N)=N1 OICWCHGZYYVJHJ-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004900 laundering Methods 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000008149 soap solution Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- -1 compound pentaerythritol tetraorthophosphate Chemical class 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- WPEXVRDUEAJUGY-UHFFFAOYSA-B hexacalcium;(2,3,4,5,6-pentaphosphonatooxycyclohexyl) phosphate Chemical compound [Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])(=O)OC1C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C(OP([O-])([O-])=O)C1OP([O-])([O-])=O WPEXVRDUEAJUGY-UHFFFAOYSA-B 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000000644 propagated effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 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
- 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
- D06M15/61—Polyamines polyimines
-
- 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
- Y10T442/2689—A phosphorus containing compound and a nitrogen containing compound
Definitions
- the present invention relates to a new or improved method of flame-proofing combustible cellulosic materials that enables them to be washed or laundered in hot aqueous media'without losing their flame-proof qualities, and to the resulting fiame-proofed cellulosic materials.
- the invention also relates to a new reagent for use as a flame-proofing component according to the aforesaid new or improved method of flame-proofing combustible cellulosic materials.
- the cellulosic materials to which the invention is especially applicable are textile fabrics, for instance woven or pleated fabrics, threads, yarns, filaments, and fibres, made of cotton, linen, regenerated cellulose, jute, cellulose acetate, and the like.
- a process has already been disclosed which comprises treating with an acidic-flre-retardant as for example phosphoric acid or calcium phytate a cellulosic material impregnated with polyethyleneimine.
- an acidic-flre-retardant as for example phosphoric acid or calcium phytate a cellulosic material impregnated with polyethyleneimine.
- An object of the present invention is to provide a method of flame-proofing combustible cellulosic materials, and a new flame-proofing component used in carrying out the method, yielding flame-proof products that retain their flame-proof qualities subsequent to hot water washing and laundering with hot soap solutions in a more satisfactory degree than heretofore.
- compositions comprising the novel compound pentaerythritol tetraorthophosphate can be readily anchored to cellulosic materials impregnated with a polyethyleneimine to give flame-proof cellulosic materials which retain their flame-proof characteristics subsequent to their treatment with soap and water washing.
- the method of flame-proofing combustible cellulosic materials comprises treating the said materials impregnated with .a polyethyleneimine with a solution comprising pentaerythritol tetraorthophosphate.
- Crude pentaerythritol tetra-orthophosphate was prepared from pentaerythritol, ortho-phosphoric acid and phosphorus pentoxide as follows, the quantities employed being based upon the molecular ratio of three parts pentaerythritol, four parts of ortho-phosporic acid and four parts phosphorus pentoxide.
- Phosphoric acid 11 gr. of 88%) was added gradually to phosphorus pentoxide (25 gr.) and when the mixture was cool, pentaerythritol (15.3 gr.) was added thereto, the whole being well stirred.
- the mixture was heated in an oil bath at -130 C. for 20 hours with exclusion of moisture and occasional stirring.
- the crude pentaerythritol tetra-orthophosphate product thus formed probably contained phosphoric acid and pentaerythritol tri-, diand monoorthophosphate in addition to the pentaerythritol tetra-orthophosphate.
- the handle or feel is found to be often improved by cutting down the quantity of polyethyleneimine with which the combustible cellulosic materials is impregnated, as for example by working with polyethyleneimine solutions of strengths lower than 8-12 per cent, but to make certain that in such cases the product remains flame-proof after soap and water washing it is often necessary to treat it subsequent to the pentaerythritol tetra-orthophosphate treatment with an acidified aqueous solution of hexamethoxymethyl melamine or triethoxymethyl melamine followed by baking at about 100 C.
- the said acidification can be efiected for ex-' ample with paratolueue sulphonic acid.
- a piece of cotton cloth (12 sq. ins.) was soaked in 10 ml. or a boiling aqueous solution of polyethyleneimine for one hour, wrung out and baked in a steam oven overnight.
- the clot-h was then steeped in 15 ml. of an aqueous solution of the crude pentaerythritol tetra-orthophosphate for one hour at room temperature, thoroughly rinsed, and dried. The time given for each operation and the quantities used were arbitrarily fixed.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB82145A GB596306A (en) | 1945-01-10 | Improvements in or relating to the flame-proofing of combustible materials and to new reagents used in connection therewith |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2472335A true US2472335A (en) | 1949-06-07 |
Family
ID=9711065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US62899445 Expired - Lifetime US2472335A (en) | 1945-01-10 | 1945-11-15 | Method of flameproofing combustible cellulosic material |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2472335A (enrdf_load_stackoverflow) |
| BE (1) | BE461753A (enrdf_load_stackoverflow) |
| FR (1) | FR919288A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2592544A (en) * | 1950-04-25 | 1952-04-15 | Us Agriculture | Pentaerythrityl phosphoric acid esters of cellulose and processes of making the same |
| DE1155901B (de) * | 1959-11-17 | 1963-10-17 | Agfa Ag | Weichmachungsmittel fuer Cellulosederivate |
| US4205022A (en) * | 1978-09-05 | 1980-05-27 | Velsicol Chemical Corporation | 2,2-Bis(haloalkyl)-3-hydroxy-1-propyl phosphoric acids |
| US4265791A (en) * | 1978-09-05 | 1981-05-05 | Velsicol Chemical Corporation | Novel phosphoric acid |
| US4339357A (en) * | 1978-09-05 | 1982-07-13 | Great Lakes Chemical Corporation | Intumescent composition |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3213784A (en) * | 1961-07-25 | 1965-10-26 | Int Harvester Co | Multiple stage hay waferizer |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1660651A (en) * | 1926-12-31 | 1928-02-28 | Du Pont | Nitration process |
| US2071353A (en) * | 1935-07-13 | 1937-02-23 | Sylvania Ind Corp | Compositions for fireproofing |
| GB476043A (en) * | 1935-05-01 | 1937-11-29 | Baverische Stickstoffwerke Akt | An improved method of fireproofing solid combustible substances |
| US2286726A (en) * | 1939-01-06 | 1942-06-16 | Du Pont | Process of flameproofing cellulosic material and products thereof |
-
0
- BE BE461753D patent/BE461753A/xx unknown
-
1945
- 1945-11-15 US US62899445 patent/US2472335A/en not_active Expired - Lifetime
- 1945-12-22 FR FR919288D patent/FR919288A/fr not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1660651A (en) * | 1926-12-31 | 1928-02-28 | Du Pont | Nitration process |
| GB476043A (en) * | 1935-05-01 | 1937-11-29 | Baverische Stickstoffwerke Akt | An improved method of fireproofing solid combustible substances |
| US2071353A (en) * | 1935-07-13 | 1937-02-23 | Sylvania Ind Corp | Compositions for fireproofing |
| US2286726A (en) * | 1939-01-06 | 1942-06-16 | Du Pont | Process of flameproofing cellulosic material and products thereof |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2592544A (en) * | 1950-04-25 | 1952-04-15 | Us Agriculture | Pentaerythrityl phosphoric acid esters of cellulose and processes of making the same |
| DE1155901B (de) * | 1959-11-17 | 1963-10-17 | Agfa Ag | Weichmachungsmittel fuer Cellulosederivate |
| US4205022A (en) * | 1978-09-05 | 1980-05-27 | Velsicol Chemical Corporation | 2,2-Bis(haloalkyl)-3-hydroxy-1-propyl phosphoric acids |
| US4265791A (en) * | 1978-09-05 | 1981-05-05 | Velsicol Chemical Corporation | Novel phosphoric acid |
| US4339357A (en) * | 1978-09-05 | 1982-07-13 | Great Lakes Chemical Corporation | Intumescent composition |
Also Published As
| Publication number | Publication date |
|---|---|
| FR919288A (fr) | 1947-03-04 |
| BE461753A (enrdf_load_stackoverflow) | 1900-01-01 |
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