GB923086A - Perfluoroacidoguanamines - Google Patents
PerfluoroacidoguanaminesInfo
- Publication number
- GB923086A GB923086A GB43299/59A GB4329959A GB923086A GB 923086 A GB923086 A GB 923086A GB 43299/59 A GB43299/59 A GB 43299/59A GB 4329959 A GB4329959 A GB 4329959A GB 923086 A GB923086 A GB 923086A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formaldehyde resins
- alkyl
- hydrogen
- compounds
- resins
- 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
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 15
- 150000001875 compounds Chemical class 0.000 abstract 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- -1 1,2-propylene- Chemical class 0.000 abstract 5
- 239000000463 material Substances 0.000 abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- 229920005989 resin Polymers 0.000 abstract 4
- 239000011347 resin Substances 0.000 abstract 4
- 239000004753 textile Substances 0.000 abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 229920001807 Urea-formaldehyde Polymers 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical compound OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 abstract 2
- 229920000877 Melamine resin Polymers 0.000 abstract 2
- 229920000297 Rayon Polymers 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 239000003822 epoxy resin Substances 0.000 abstract 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 150000007974 melamines Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229920001778 nylon Polymers 0.000 abstract 2
- 229920001568 phenolic resin Polymers 0.000 abstract 2
- 229920000647 polyepoxide Polymers 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 210000002268 wool Anatomy 0.000 abstract 2
- GJMPSRSMBJLKKB-UHFFFAOYSA-N 3-methylphenylacetic acid Chemical compound CC1=CC=CC(CC(O)=O)=C1 GJMPSRSMBJLKKB-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 abstract 1
- 229940123208 Biguanide Drugs 0.000 abstract 1
- 244000025254 Cannabis sativa Species 0.000 abstract 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 abstract 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 abstract 1
- 240000000491 Corchorus aestuans Species 0.000 abstract 1
- 235000011777 Corchorus aestuans Nutrition 0.000 abstract 1
- 235000010862 Corchorus capsularis Nutrition 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
- 241000238631 Hexapoda Species 0.000 abstract 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract 1
- 239000004677 Nylon Substances 0.000 abstract 1
- 229920001756 Polyvinyl chloride acetate Polymers 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 229920006397 acrylic thermoplastic Polymers 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 235000009120 camo Nutrition 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 235000005607 chanvre indien Nutrition 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 abstract 1
- 238000007598 dipping method Methods 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 239000004744 fabric Substances 0.000 abstract 1
- 210000003746 feather Anatomy 0.000 abstract 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 abstract 1
- 230000002070 germicidal effect Effects 0.000 abstract 1
- 239000004519 grease Substances 0.000 abstract 1
- 210000004209 hair Anatomy 0.000 abstract 1
- 239000011487 hemp Substances 0.000 abstract 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 abstract 1
- 238000007654 immersion Methods 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 235000006408 oxalic acid Nutrition 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 229920002689 polyvinyl acetate Polymers 0.000 abstract 1
- 239000011118 polyvinyl acetate Substances 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- ISYORFGKSZLPNW-UHFFFAOYSA-N propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH3+] ISYORFGKSZLPNW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002964 rayon Substances 0.000 abstract 1
- 239000004627 regenerated cellulose Substances 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 235000002906 tartaric acid Nutrition 0.000 abstract 1
- 239000011975 tartaric acid Substances 0.000 abstract 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 abstract 1
- 229940117957 triethanolamine hydrochloride Drugs 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002023 wood Substances 0.000 abstract 1
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Inorganic materials [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 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
- 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
- D06M13/322—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 nitrogen
- D06M13/35—Heterocyclic compounds
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
Textile treating agents comprise a compound of formula <FORM:0923086/IV(a)/1> <FORM:0923086/IV(a)/2> where n is 0-13, m is 1-8, and R1-R8 are hydrogen, alkyl, cycloalkyl, allyl, phenyl, substituted phenyl, or -CH2OR9, where R9 is hydrogen or C1-4 alkyl, together with conventional textile resins, such as urea p formaldehyde resins and cyclic urea formaldehyde resins, e.g. from 1,2-propylene-, 1,3-propylene- and ethylene urea, and their alkylated derivatives; phenol formaldehyde resins; ketone formaldehyde resins; epoxy resins, e.g. polyglycidy ethers of polyhydric alcohols; and polymethylol melamines.ALSO:The invention comprises compounds of the formula <FORM:0923086/IV(a)/1> <FORM:0923086/IV(a)/2> wherein n is 0-13, m is 1-8, and R1-R8 are hydrogen, alkyl, cycloalkyl, allyl, phenyl, substituted phenyl (e.g. p-chlorophenyl), or -CH2OR9, where R9 is hydrogen or C1-4 alkyl; their production (other than -CH2OR9 compounds) by reacting an ester of a perfluoroalkane carboxylic acid with a biguanide at 15-100 DEG C.; the production of N-CH2OH compounds by reacting an N-H compound with formaldehyde or a formaldehyde-producing substance at an alkaline pH at 30-100 DEG C.; and the alkylation of the N-methylol compounds by means of a C1-4 alkanol at an acid pH. The compounds of the invention are used for treating textiles (see Group IV(c)).ALSO:Textile and other materials are treated with a compound <FORM:0923086/IV(a)/1> <FORM:0923086/IV(a)/2> where n is 0-13, m is 1-8, and R1-R: are hydrogen, alkyl, cycloalkyl, allyl, phenyl, substituted phenyl, or -CH2OR9, where R9 is hydrogen or C1-4 alkyl (see Group IV(b)) to impart properties such as insect repellency, grease and oil repellancy, germicidal activity, and, with cellulosic materials, crease resistance and shrinkage control. The compounds may be applied from aqueous, aqueous alcohol, or solvent solutions or from aqueous dispersion by spraying, immersion, dipping or padding. Suitable materials are proteinaceous or cellulosic fibres and fabrics, including felted, wood, paper and cellulosic films, wool, furs, feathers, hair and hides; proteinaceous materials blended with other materials, such as cellulosics, nylons and acrylics; cotton, regenerated cellulose, viscose, rayon, linen, hemp and jute, alone or blended with, for example, nylon, acrylic, polyester or wool fibres or silk. Specified solvents are dimethylformamide, methanol, water and dimethylformamide or an alcohol, e.g. methanol and ethanol, or mixtures thereof. Curing catalysts may be present in the compositions, e.g. ammonium salts such as the floride and sulphate, amine salts such as triethylamine and isopropylamine hydrochloride, alkanolamine salts such as triethanolamine hydrochloride, metal salts such as Mg Cl2, Zn(NO3)2 and Al Cl3, and free acids such as oxalic and tartaric acid. Drying and curing may be carried out together or in separate steps. Other textile-treating agents may also be present, e.g. polymethylolated melamines; urea formaldehyde resins and cyclic urea formaldehyde resins and their alkylated derivatives; phenol formaldehyde resins; ketone formaldehyde resins; epoxy resins; acrylate and methacrylate polymers and copolymers with styrenes, acrylonitrile, polyvinyl chloride and polyvinyl acetate; and dicyandiamide.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US78264058A | 1958-12-24 | 1958-12-24 | |
US192090A US3162633A (en) | 1958-12-24 | 1962-05-03 | Perfluoroguanamines |
Publications (1)
Publication Number | Publication Date |
---|---|
GB923086A true GB923086A (en) | 1963-04-10 |
Family
ID=26887714
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB43299/59A Expired GB923086A (en) | 1958-12-24 | 1959-12-21 | Perfluoroacidoguanamines |
Country Status (2)
Country | Link |
---|---|
US (1) | US3162633A (en) |
GB (1) | GB923086A (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3687900A (en) * | 1968-06-05 | 1972-08-29 | Du Pont | Homopolymers of substituted guanamines |
US3536710A (en) * | 1968-06-05 | 1970-10-27 | Du Pont | Substituted guanamines and their derivatives |
US4055720A (en) * | 1976-05-25 | 1977-10-25 | The United States Of America, As Represented By The Secretary Of Agriculture | Diaminotrihalopropyl triazines: and their methylol derivatives |
US4932998A (en) * | 1986-09-30 | 1990-06-12 | Idemitsu Kosan Company Limited | Triazine derivatives, and herbicides comprising the same as the effective ingredient |
JPWO2023013697A1 (en) * | 2021-08-03 | 2023-02-09 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2451432A (en) * | 1948-10-12 | High molecular guanamines and a | ||
US2394526A (en) * | 1946-02-05 | Aliphatic substituted guanamines | ||
US2427315A (en) * | 1947-09-09 | Carboxy polymethylene guanamines | ||
US2845421A (en) * | 1958-07-29 | Fluorination of chloro triazines with | ||
US2423353A (en) * | 1947-07-01 | Polymethylene diguanamines | ||
US2385766A (en) * | 1941-08-30 | 1945-09-25 | American Cyanamid Co | Guanamines in textile finishing |
US2535968A (en) * | 1945-04-13 | 1950-12-26 | American Cyanamid Co | Heterocyclic guanamines |
US2526948A (en) * | 1945-10-23 | 1950-10-24 | Phillips Petroleum Co | Process of treating textiles with half-acid amide derivatives |
US2480084A (en) * | 1948-03-20 | 1949-08-23 | Dow Chemical Co | Protection of cellulosic textile materials |
US2734004A (en) * | 1952-08-25 | 1956-02-07 | Water soluble n-methylol polypyrroli- | |
US2871145A (en) * | 1954-05-21 | 1959-01-27 | Hajdu Joseph | Process of impregnating textile material to increase its wear resistance |
BE539990A (en) * | 1954-07-22 | |||
US2892810A (en) * | 1954-08-24 | 1959-06-30 | Ciba Ltd | New derivatives of aldehyde condensation products of the aminotriazine or urea group and their manufacture and use |
-
1959
- 1959-12-21 GB GB43299/59A patent/GB923086A/en not_active Expired
-
1962
- 1962-05-03 US US192090A patent/US3162633A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
US3162633A (en) | 1964-12-22 |
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