US2872351A - Compositions for and methods of finishing textile materials - Google Patents
Compositions for and methods of finishing textile materials Download PDFInfo
- Publication number
- US2872351A US2872351A US46905354A US2872351A US 2872351 A US2872351 A US 2872351A US 46905354 A US46905354 A US 46905354A US 2872351 A US2872351 A US 2872351A
- Authority
- US
- United States
- Prior art keywords
- phosphoric acid
- group
- materials
- water
- textile materials
- 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 claims description 44
- 239000004753 textile Substances 0.000 title claims description 27
- 238000000034 method Methods 0.000 title claims description 19
- 239000000203 mixture Substances 0.000 title description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 38
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 16
- 239000007864 aqueous solution Substances 0.000 claims description 14
- 238000009877 rendering Methods 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000004744 fabric Substances 0.000 description 33
- 239000000243 solution Substances 0.000 description 21
- 235000011007 phosphoric acid Nutrition 0.000 description 19
- 239000005871 repellent Substances 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 229930195733 hydrocarbon Natural products 0.000 description 13
- 239000004215 Carbon black (E152) Substances 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 10
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- 150000005690 diesters Chemical class 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- -1 Phosphoric acid dihexyl ester Phosphoric acid dioctyl ester Phosphoric acid didodecyl ester Phosphoric acid dioleyl ester Phosphoric acid dimontanyl ester Phosphoric acid dimethylcyclohexyl ester Chemical compound 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 6
- 150000003014 phosphoric acid esters Chemical class 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000004900 laundering Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000008233 hard water Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- YZEZMSPGIPTEBA-UHFFFAOYSA-N 2-n-(4,6-diamino-1,3,5-triazin-2-yl)-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(NC=2N=C(N)N=C(N)N=2)=N1 YZEZMSPGIPTEBA-UHFFFAOYSA-N 0.000 description 1
- MJZMMZPWBOZUOB-UHFFFAOYSA-N 5-methyltriazine-4,6-diamine Chemical compound CC=1C(=NN=NC1N)N MJZMMZPWBOZUOB-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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- HZFDBHSQORZXQT-UHFFFAOYSA-N P(=O)(O)(O)O.P(=O)(OCC1=CC=CC=C1)(OCC1=CC=CC=C1)O Chemical compound P(=O)(O)(O)O.P(=O)(OCC1=CC=CC=C1)(OCC1=CC=CC=C1)O HZFDBHSQORZXQT-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- MASBWURJQFFLOO-UHFFFAOYSA-N ammeline Chemical compound NC1=NC(N)=NC(O)=N1 MASBWURJQFFLOO-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- YSRVJVDFHZYRPA-UHFFFAOYSA-N melem Chemical compound NC1=NC(N23)=NC(N)=NC2=NC(N)=NC3=N1 YSRVJVDFHZYRPA-UHFFFAOYSA-N 0.000 description 1
- KQVLODRFGIKJHZ-UHFFFAOYSA-N methylenediurea Chemical compound NC(=O)NCNC(N)=O KQVLODRFGIKJHZ-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
-
- 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
- Y10T442/2164—Coating or impregnation specified as water repellent
-
- 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
- Y10T442/2164—Coating or impregnation specified as water repellent
- Y10T442/2197—Nitrogen containing
Definitions
- This invention relates to compositions for and methods of finishing textile materials, and more particularly to methods of making textile materials water-repellent by impregnating them with a composition containing organic esters of phosphoric acid and organic amido-compounds.
- textile malerials can be rendered water-repellent by impregnating them with aqueous solutions containing acid esters formed by esterifying phosphoric acid with high-molecular alcohols and phenols.
- Acid esters of the above type which may advantageously be employed to make textiles water-repellent in accordance with my invention include mono-esters having the general structural formula Rt-O wherein R is a hydrocarbon radical containing at least 6 carbon atoms selected from the group consisting of high-molecular alkyl, cycloalkyl, alkylcycloalkyl, and
- alkylaryl radicals and di-esters having the general structural formula P-OH wherein R is a hydrocarbon radical as defined above and R is also a hydrocarbon radical containing at least 6 carbon atoms, selected from the group consisting of alkyl, cycloalkyl, alkylcycloalkyl, and alkylaryl radicals.
- R and R may be identical radicals or radicals of ditferent structure; in other Words, the di-esters can'be simple or mixed di-esters.
- R and R may also carry substituents or may be interrupted by oxygen, sulfur or nitrogen atoms or by heteroatom groups derived therefrom.
- phosphoric acid esters which can be used to impart Water-repellent properties to textile materials in accordance with my invention are the following:
- I first immerse the textile material in an aqueous solution containing from 1 to 20 gm./liter of any one of the above monoor di-esters of phosphoric acid. Thereafter, I pass the treated material through a wringer to remove excess amounts of solution, and then dry and heat the wet impregnated material at a temperature in excess of 90 C. to remove the water while leaving the phosphoric acid ester compound afiixed to the textile fibers.
- the water-repellent effect created on textiles by the above procedure can be further improved by treating the dried fabric with dilute solutions of salts of bivalent, trivalent or tetravalent metals, particularly of aluminum salts, or by simply rinsing the dried cloth in hard water.
- Amido-compounds of this type are, for example, the following: Urea, thiourea, alkylated urea, methylenediurea, methane, guanidine, alkylated guanidine, cyanamide, dicyandiamide, dicyandiamidine, as Well as cyclic compounds such as methyldiaminotriazine, triaminotriazine (melamine), melam, melem, mellone, ammeline and the like.
- I first prepare an aqueous solution containing from 1 to 20 gm./liter of the acid phosphoric acid ester, and if desired also, from 1 to 20 gin/liter of the amino-compound.- I then pass the textile material into this solution, subsequently run the material through a wringer to remove ex-. cess solution, and finally dry the wet fabric at a temperature above 90 C.
- Both the treatment with the solutions of acid phosphoric acid esters alone and with the mixed solution of the phosphoric acid ester and the amide-compound can be applied to textile materials in the form of threads, strips, and fabrics.
- it may be applied to cotton, regenerated cellulose, rayon, jute, linen, wool, silk, as well as 100%-syntheti-c fibers.
- Example I Cotton poplin fabric was wetted with a solution containing 3 gm./liter of the monocetyl ester of phosphoric acid. The wetted fabric was then removed from the so lution and passed through a wringer where all of the solution was removed which was in excess of the amount required to bring the weight of the wet cloth up to 3 above the weight of the dry cloth. Thereafter, the wet cloth was dried at 90 C. The finished dry cloth was found to be adequately water-repellent.
- Example Il Unbleached cotton cloth was immersed in a solution containing 3 gm./liter of the monocetyl ester of phosphoric acid and 0.5 gm./liter of ammonia. The "treated fabric was then removed from the solution, passed through a wringer to remove excess solution as in Example I, and dried at 100 C. Subsequently, the dry fabric was rinsed for one hour in hard water, and again dried. Unbleached cotton cloth treated in this manner was found to be satisfactorily water-repellent.
- Example III Cotton poplin cloth was passed into a solution contain ing 15 gm./liter of the monododecylester of phosphoric acid and 7.5 gm./liter of cyanamide. The treated fabric was then removed from the solution and passed through a wringer where all of the solution was removed in excess of the amount required to bring the weight of the wet cloth up to 100% above the weight of the dry cloth. Thereafter, the wet cloth was dried at 60 C. and then exposed to a temperature of 120 C. for minutes. The treated cloth exhibits good water-repellent properties which can be improved by washing the treated cloth under mild conditions at 45 C. The water-repellent effect also survived repeated laundering of the treated fabric.
- Example I'V Unbleached cotton cloth was inserted into a solution containing 2 gm./liter of a dialkyl ester of phosphoric acid, wherein the alkyl radicals contained from 16 to 18 carbon atoms, and 1 gm./ liter of cyanamide.
- the wetted fabric was then removed from the solution and wrung out and dried as described in Example III.
- the result was a hydrophobic textile fabric which retained its waterrepellent properties even after repeated laundering.
- Example V Cotton fabric was passed into a solution which contained 10 gm./liter of a monoalkylester of phosphoric acid, wherein the alkyl radical contained from 16 to 18 carbon atoms, 3 gm./liter of melanine and 50 gm./liter isopropanol. The wetted fabric was then removed from the solution and wrung out and dried as in Example III. The result was a hydrophobic fabric which retained its water-repellent properties even after repeated laundering.
- Example VI Wool cloth was passed at 60 C. into a dispersion con taining 10 gm./liter of a mixture of monoand di-octadecylester of phosphoric acid, gin/liter of cyanamide, and 100 gm./ liter of isopropanol. The treated cloth was then removed from the dispersion, passed through a .wringer to remove excess solution and dried at 105 C.
- the finished dry cloth was found to be satisfactorily water-repellent.
- the water-repellent effect survived repeated laundering.
- the acid esters of phosphoric acid, used according to the invention are not sufficiently water-soluble. Then it is possible to use them in aqueous dispersion. For improving the solubility it 4 V is useful to add small amounts of volatile inorganic or organic bases as described, which are removed during the drying process of the impregnated cloth. Under certain conditions it may be advantageous to use the acid esters in organic solvents such as halogen hydrocarbons or benzene.
- R and R ' are hydrocarbon radicals containing at least 6 carbon atoms selected from the group consisting of high-molecular 'alkyl, cycloalkyl, alkylcycloalkyl, and alkylaryl radicals, and drying said materials at a temperature above C.
- R and R are hydrocarbon radicals containing at least 6 carbon atoms selected from the group consisting of high-molecular alkyl, cycloalkyl, alkylcycloalkyl, and alkylaryl radicals, said solution also comprising at least one amido-compound containing at least one aminogroup bonded to an atom group selected from the group consisting of CO--, CS, C'(NH), and CN-groups, said amino group also containing at least one replaceable hydrogen atom, and drying said materials at a temperature above 90 C.
- the method of rendering textile materials waterrepellent which comprises impregnating said materials with an aqueous solution of at least one compound selected from the group consisting of acid mono-esters of phosphoric acid having a structural formula wherein R is a hydrocarbon radical containing at least 6 carbon atoms selected from the group consisting of alkyl, cycloalkyl, alkylcycloalkyl, and alkylaryl radicals, said solution also comprising at least one amido-compound containing at least one amino-group bonded to an atom group selected from the group consisting of CO-, CS, C(NH)-, and CN-groups, said amino-group also containing at least one replaceable hydrogen atom, and drying said materials at a temperature above 90 .C.
- the method of rendering textile materials water-repellent which comprises impregnating said materials with an aqueous solution of at least one compound selected from the group consisting of acid di-esters of phosphoric acids having the general structural formula Rr-O 0 Rr-O wherein R and R are hydrocarbon radicals containing at least 6 carbon atoms selected from the group consisting of high-molecular alkyl, cycloalkyl, alkylcycloalkyl, and alkylaryl radicals, and drying said materials at a temperature above 90 C.
- R and R are hydrocarbon radicals selected from the group consisting of alkyl, cycloalkyl, alkylcycloalkyl, and alkylaryl radicals, said radicals con taining at least 6 carbon atoms, and drying said materials at a temperature above 90 C.
- the method of rendering textile materials waterrepellent which comprises impregnating said materials with an aqueous solution of at least one compound selected from the group consisting of acid monoand di-esters of phosphoric acid having the general strucrespectively, wherein R and R are hydrocarbon radicals selected from the group consisting of alkyl, cycloalkyl, alkylcycloalkyl, alkylaryl radicals, said hydrocarbon radicals containings at least 6 carbon atoms, drying said impregnated materials at a temperature above C., and contacting said dried impregnated materials with an aqueous solution of salts of metals selected from the group consisting of bivalent, trivalent and tetravalent metals.
- the method of rendering textile materials waterrepellent which comprises impregnating said materials with an aqueous solution of at least one compound selected from the group consisting of acid monoand di-esters of phosphoric acid having the general structural formula P-OH R1O and Bro O i OH Rr-O respectively, wherein R and R are hydrocarbon radicals selected from the group consisting of alkyl, cycloalkyl, alkylcycloalkyl, alkylaryl radicals, said hydrocarbon radicals containing at least 6 carbon atoms, drying said impregnated materials at a temperature above 90 C., and rinsing said dried impregnated materials in hard water.
- R and R are hydrocarbon radicals selected from the group consisting of alkyl, cycloalkyl, alkylcycloalkyl, alkylaryl radicals, said hydrocarbon radicals containing at least 6 carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE765208X | 1953-11-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
US2872351A true US2872351A (en) | 1959-02-03 |
Family
ID=6673043
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US46905354 Expired - Lifetime US2872351A (en) | 1953-11-14 | 1954-11-15 | Compositions for and methods of finishing textile materials |
Country Status (3)
Country | Link |
---|---|
US (1) | US2872351A (fr) |
GB (1) | GB765208A (fr) |
NL (1) | NL102619C (fr) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3019133A (en) * | 1956-05-14 | 1962-01-30 | Bohme Fettchemie Gmbh | Process for waterproofing leather |
US3146105A (en) * | 1962-11-15 | 1964-08-25 | Eastman Kodak Co | Lithographic process using a stop bath |
US4006204A (en) * | 1975-04-30 | 1977-02-01 | Nelson Research & Development Company | Phosphoric acid diesters |
US4600552A (en) * | 1984-04-04 | 1986-07-15 | Agfa-Gevaert, N.V. | Stripping aids for cellulose ester film |
US4908209A (en) * | 1983-08-16 | 1990-03-13 | Interface, Inc. | Biocidal delivery system of phosphate ester and method of preparation thereof |
US4935232A (en) * | 1983-08-16 | 1990-06-19 | Interface Research Corporation | Microbiocidal composition and method of preparation thereof |
US4957948A (en) * | 1988-05-05 | 1990-09-18 | Interface, Inc. | Biocidal protective coating for heat exchanger coils |
US5024840A (en) * | 1984-03-08 | 1991-06-18 | Interface, Inc. | Antimicrobial carpet and carpet tile |
US5032310A (en) * | 1983-08-16 | 1991-07-16 | Interface, Inc. | Microbiocidal cleansing and disinfecting formulations and preparation thereof |
US5133933A (en) * | 1983-08-16 | 1992-07-28 | Interface Research Corporation | Microbiocidal preservative |
US5474739A (en) * | 1978-02-04 | 1995-12-12 | Interface, Inc. | Microbiocidal composition |
US5635192A (en) * | 1988-05-05 | 1997-06-03 | Interface, Inc. | Biocidal polymeric coating for heat exchanger coils |
US6066753A (en) * | 1997-09-12 | 2000-05-23 | Clariant Gmbh | Mixtures of long-chain alkyl phosphates |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2173638A (en) * | 1935-02-27 | 1939-09-19 | Rozenbroek Meindert Danius | Process for manufacturing textile agents |
US2406423A (en) * | 1944-04-20 | 1946-08-27 | Victor Chemical Works | Organic phosphorus and nitrogen containing compounds |
US2482755A (en) * | 1945-05-29 | 1949-09-27 | Bancroft & Sons Co J | Flameproofing of fibrous material |
US2519388A (en) * | 1948-12-09 | 1950-08-22 | American Cyanamid Co | Treatment of fibrous cellulosic materials to impart flame resistance thereto, compositions therefor, and products thereof |
US2634270A (en) * | 1950-12-29 | 1953-04-07 | Monsanto Chemicals | Triazine phosphorus compounds |
US2656372A (en) * | 1948-06-22 | 1953-10-20 | Textilana Inc | Mixtures of orthophosphates |
US2678329A (en) * | 1950-11-06 | 1954-05-11 | Monsanto Chemicals | Dialkyl monoaryl esters of orthophosphoric acid |
US2730498A (en) * | 1952-01-09 | 1956-01-10 | Celanese Corp | Textile lubricants |
US2743193A (en) * | 1953-08-10 | 1956-04-24 | Eastman Kodak Co | Treated cellulose organic acid ester fibers |
-
0
- NL NL102619D patent/NL102619C/xx active
-
1954
- 1954-11-12 GB GB3275554A patent/GB765208A/en not_active Expired
- 1954-11-15 US US46905354 patent/US2872351A/en not_active Expired - Lifetime
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2173638A (en) * | 1935-02-27 | 1939-09-19 | Rozenbroek Meindert Danius | Process for manufacturing textile agents |
US2406423A (en) * | 1944-04-20 | 1946-08-27 | Victor Chemical Works | Organic phosphorus and nitrogen containing compounds |
US2482755A (en) * | 1945-05-29 | 1949-09-27 | Bancroft & Sons Co J | Flameproofing of fibrous material |
US2656372A (en) * | 1948-06-22 | 1953-10-20 | Textilana Inc | Mixtures of orthophosphates |
US2519388A (en) * | 1948-12-09 | 1950-08-22 | American Cyanamid Co | Treatment of fibrous cellulosic materials to impart flame resistance thereto, compositions therefor, and products thereof |
US2678329A (en) * | 1950-11-06 | 1954-05-11 | Monsanto Chemicals | Dialkyl monoaryl esters of orthophosphoric acid |
US2634270A (en) * | 1950-12-29 | 1953-04-07 | Monsanto Chemicals | Triazine phosphorus compounds |
US2730498A (en) * | 1952-01-09 | 1956-01-10 | Celanese Corp | Textile lubricants |
US2743193A (en) * | 1953-08-10 | 1956-04-24 | Eastman Kodak Co | Treated cellulose organic acid ester fibers |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3019133A (en) * | 1956-05-14 | 1962-01-30 | Bohme Fettchemie Gmbh | Process for waterproofing leather |
US3146105A (en) * | 1962-11-15 | 1964-08-25 | Eastman Kodak Co | Lithographic process using a stop bath |
US4006204A (en) * | 1975-04-30 | 1977-02-01 | Nelson Research & Development Company | Phosphoric acid diesters |
US5474739A (en) * | 1978-02-04 | 1995-12-12 | Interface, Inc. | Microbiocidal composition |
US5133933A (en) * | 1983-08-16 | 1992-07-28 | Interface Research Corporation | Microbiocidal preservative |
US4908209A (en) * | 1983-08-16 | 1990-03-13 | Interface, Inc. | Biocidal delivery system of phosphate ester and method of preparation thereof |
US4935232A (en) * | 1983-08-16 | 1990-06-19 | Interface Research Corporation | Microbiocidal composition and method of preparation thereof |
US5032310A (en) * | 1983-08-16 | 1991-07-16 | Interface, Inc. | Microbiocidal cleansing and disinfecting formulations and preparation thereof |
US5024840A (en) * | 1984-03-08 | 1991-06-18 | Interface, Inc. | Antimicrobial carpet and carpet tile |
US4600552A (en) * | 1984-04-04 | 1986-07-15 | Agfa-Gevaert, N.V. | Stripping aids for cellulose ester film |
US4957948A (en) * | 1988-05-05 | 1990-09-18 | Interface, Inc. | Biocidal protective coating for heat exchanger coils |
US5635192A (en) * | 1988-05-05 | 1997-06-03 | Interface, Inc. | Biocidal polymeric coating for heat exchanger coils |
US5639464A (en) * | 1988-05-05 | 1997-06-17 | Interface, Inc. | Biocidal polymeric coating for heat exchanger coils |
US6066753A (en) * | 1997-09-12 | 2000-05-23 | Clariant Gmbh | Mixtures of long-chain alkyl phosphates |
Also Published As
Publication number | Publication date |
---|---|
NL102619C (fr) | 1900-01-01 |
GB765208A (en) | 1957-01-02 |
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