GB856466A - Improvements in sulfonated urea-thiourea formaldehyde resins - Google Patents
Improvements in sulfonated urea-thiourea formaldehyde resinsInfo
- Publication number
- GB856466A GB856466A GB10537/57A GB1053757A GB856466A GB 856466 A GB856466 A GB 856466A GB 10537/57 A GB10537/57 A GB 10537/57A GB 1053757 A GB1053757 A GB 1053757A GB 856466 A GB856466 A GB 856466A
- Authority
- GB
- United Kingdom
- Prior art keywords
- added
- product
- mols
- bisulphite
- thiourea
- 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
- 239000011347 resin Substances 0.000 title abstract 2
- 229920005989 resin Polymers 0.000 title abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 6
- 239000000047 product Substances 0.000 abstract 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 5
- 239000000203 mixture Substances 0.000 abstract 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract 4
- 150000001299 aldehydes Chemical class 0.000 abstract 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract 3
- 239000004202 carbamide Substances 0.000 abstract 3
- 239000004677 Nylon Substances 0.000 abstract 2
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 abstract 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical group [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 abstract 2
- 239000004744 fabric Substances 0.000 abstract 2
- 229920001778 nylon Polymers 0.000 abstract 2
- 235000006408 oxalic acid Nutrition 0.000 abstract 2
- 229920002866 paraformaldehyde Polymers 0.000 abstract 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 abstract 2
- 238000005507 spraying Methods 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 abstract 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000003063 flame retardant Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- 229920001187 thermosetting polymer Polymers 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- 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
-
- 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
- C08G12/40—Chemically modified polycondensates
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
A hydrophilic thermosetting resin is produced by reacting 1 mol of urea at a temperature above 40 DEG C. and at a pH of 7 to 9 with 2-6,5 mols of a water-soluble aldehyde in the presence of ,01-,04 mols of bisulphite per mol of aldehyde, polymerizing the reaction product at a pH of 2,2-3,8 at above 40 DEG C., adjusting the pH to 7,0 to 9,0, reacting 0,3-2,5 mols of thiourea with the product, adjusting the pH to 3,5 to 5,5 and alkylating the product with 0,3-4 mols of a saturated aliphatic alcohol having 1-3 carbon atoms, and adjusting the pH to the alkaline side. The alcohol may be added at any stage of the sequence of reactions. The products are stable, i.e. do not deposit floc after standing for two weeks at 25 DEG C. and do not precipitate when diluted with 50 volumes of water at 25 DEG C. Suitable aldehydes are formaldehyde, acetaldehyde, propionaldehyde and glyoal. Formaldehyde may be used as paraformaldehyde. The preferred bisulphite is NaHSO3. Sulphites which yield bisulphite may be used. In a typical example, methanol, formalin, urea NaHSO3 and triethanolamine were heated to 50 DEG C. and an initial pH of 8,1. Paraformaldehyde was added with constant stirring and the mixture refluxed. The pH was adjusted to about 3 with oxalic acid the mixture further refluxed and the pH adjusted to 7-3 with triethanolamine. The mixture was cooled, methanol and thiourea added and the mixture stirred at 50-55 DEG C. Oxalic acid was added to bring the pH to about 5, the mixture further heated at 50-55 DEG C. and then cooled and triethanolamine added to bring the pH to 7,5-8. "Hy-Flor" filtering aid (Registered Trade Mark) was added and the product filtered and concentrated to 80% solids. The product was hydrophilic and stable. The products may be applied, e.g. by pad baths or spraying to fabrics, e.g. nylon netting to impart flame-retardant and stiff, resilent finishes. They are also said to be useful in paper-making.ALSO:Textile fabrics, particularly nylon net, are given a stiff, springy, resilient hand by applying to them, e.g. by padding or spraying, an aqueous solution of a condensate prepared from urea, thiourea, an aldehyde and a bisulphite (see Group IV(a)), and drying and curing the condensate by heating with ammonium bromide or chloride as curing catalyst.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US856466XA | 1956-04-30 | 1956-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB856466A true GB856466A (en) | 1960-12-14 |
Family
ID=22193024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10537/57A Expired GB856466A (en) | 1956-04-30 | 1957-04-01 | Improvements in sulfonated urea-thiourea formaldehyde resins |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB856466A (en) |
-
1957
- 1957-04-01 GB GB10537/57A patent/GB856466A/en not_active Expired
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