GB868080A - Process for the manufacture of hardenable condensates from modified ureas and aldehydes - Google Patents
Process for the manufacture of hardenable condensates from modified ureas and aldehydesInfo
- Publication number
- GB868080A GB868080A GB3421457A GB3421457A GB868080A GB 868080 A GB868080 A GB 868080A GB 3421457 A GB3421457 A GB 3421457A GB 3421457 A GB3421457 A GB 3421457A GB 868080 A GB868080 A GB 868080A
- Authority
- GB
- United Kingdom
- Prior art keywords
- urea
- methylol
- groups
- product
- formalin
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
- C08G12/28—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with substituted diazines, diazoles or triazoles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/043—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with at least two compounds covered by more than one of the groups C08G12/06 - C08G12/24
- C08G12/046—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with at least two compounds covered by more than one of the groups C08G12/06 - C08G12/24 one being urea or thiourea
-
- 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)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Paper (AREA)
Abstract
Hardenable condensation products are produced by treating an amine having at least three amino groups to introduce at least two urea groups into it, reacting the product with a long chain compound containing a functional group which reacts with amino or carbonamide groups, and converting the product so obtained into a methylol or substituted methylol derivative by reaction with an aldehyde. Suitable polyamines are diethylene triamine, triethylene tetramine, tetraethylene pentamine, dipropylene triamine, tripropylene tetramine, tetrapropylene pentamine, polyamino benzenes, polyamino naphthalenes, and products obtained by reacting alcohols or amines with acrylonitrile and reducing the product. Introduction of urea groups into the amine may be effected with urea, nitro-urea or potassium cyanate. Suitable long chain compounds are carboxylic acids, esters, anhydrides, halides or azides, carbamide chlorides, isocyanates, chlorcarbonic acids or methylol compounds. The chains contain 10-18 carbon atoms and may be interrupted or substituted by aromatic, cycloaliphatic or heterocyclic radicals or hetero atoms. Mentioned are stearic acid-N-methylol amide, octadecyl-N-methylol urethane, octadecylchloromethyl ether. If desired the poly-amine may be reacted with the long chain compound before the conversion of amino to urea groups. The products are preferably reacted with formaldehyde. Acetaldehyde and glyoxal are also mentioned. The methylol groups may be etherified by reaction with alcohols, e.g. methyl, ethyl, propyl or butyl alcohol in acid medium. The products of the invention may be applied in aqueous media with acid catalysts to paper, textiles or leather, dried and cured at 80 DEG -170 DEG C. Suitable catalysts are lactic acid, glycollic acid, ammonium nitrate or aluminium sulphate. They may be used together with other aminoplasts, polyvinyl acetate, polyvinyl propionate, polyacrylic esters, polyvinyl alcohol, polyacrylic amide, starch, glue, water-soluble cellulose derivatives, paraffins, or waxes. In Examples (1) diethylene triamine is heated with urea, and the product with stearoyl chloride and then with formalin; (2) is similar using octadecyl isocyanate in place of stearyl chloride. The aqueous emulsion of product is used with hexamethylol melamine and ammonium nitrate; (3) Triethylene tetramine was heated with stearic acid and then with urea and the product with paraformaldehyde; (4) Triethylene tetramine was condensed with urea, octadecyl isocyanate and then formalin; (5) is similar to (4) with stearic acid-N-methylol-amide in place of octadecyl isocyanate; (6) Dipropylene triamine was condensed with urea followed by octadecyl isocyanate and formalin. The product was etherified with methanol and the white paste mixed with paraffin and xylol, and diluted, if desired, with water; (7) Tripropylene tetramine was heated with tetradecyl chloride, then with potassium cyanate and then with formalin or glyoxal; (8) Dipropylene monoethylene tetramine was condensed with urea and then with a mixture of stearyl and palmitoyl chlorides, followed by formalin; (9) Tetraethylene pentamine was heated with urea, with octadecyl isocyanate and then with formaldehyde. The aqueous emulsion was mixed with paraffin xylene and an emulsifier. Uses: The products are used for making paper, leather or textiles water-repellent, giving a soft handle to textiles and giving wet strength to paper.ALSO:Methylol or substituted methylol derivatives of substances prepared by treating polyamines in either order with substances to introduce urea groups and with long-chain substances containing groups which react with amino or with carbonamido groups (see Group IV(a)) are used as aqueous pastes or emulsions to treat textiles to make them, after drying and curing, water-repellent, soft and resistant to scraping or shrinking. In an example cotton poplin is impregnated with an aqueous emulsion of ammonium nitrate and a paste obtained by treating diethylene triamine with urea and then with stearyl chloride and formalin. After drying and heating the fabric has a soft and full handle not affected by repeated washing.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3421457A GB868080A (en) | 1957-11-01 | 1957-11-01 | Process for the manufacture of hardenable condensates from modified ureas and aldehydes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3421457A GB868080A (en) | 1957-11-01 | 1957-11-01 | Process for the manufacture of hardenable condensates from modified ureas and aldehydes |
Publications (1)
Publication Number | Publication Date |
---|---|
GB868080A true GB868080A (en) | 1961-05-17 |
Family
ID=10362819
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3421457A Expired GB868080A (en) | 1957-11-01 | 1957-11-01 | Process for the manufacture of hardenable condensates from modified ureas and aldehydes |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB868080A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3528735A1 (en) * | 1985-08-10 | 1987-02-12 | Sueddeutsche Kalkstickstoff | QUICK-HARDING CONDENSATION PRODUCT AND METHOD FOR PRODUCING IT |
-
1957
- 1957-11-01 GB GB3421457A patent/GB868080A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3528735A1 (en) * | 1985-08-10 | 1987-02-12 | Sueddeutsche Kalkstickstoff | QUICK-HARDING CONDENSATION PRODUCT AND METHOD FOR PRODUCING IT |
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