DE2639754C3 - Verfahren zur Herstellung von härtbaren Kondensationsprodukten und deren Verwendung - Google Patents
Verfahren zur Herstellung von härtbaren Kondensationsprodukten und deren VerwendungInfo
- Publication number
- DE2639754C3 DE2639754C3 DE2639754A DE2639754A DE2639754C3 DE 2639754 C3 DE2639754 C3 DE 2639754C3 DE 2639754 A DE2639754 A DE 2639754A DE 2639754 A DE2639754 A DE 2639754A DE 2639754 C3 DE2639754 C3 DE 2639754C3
- Authority
- DE
- Germany
- Prior art keywords
- formaldehyde
- condensation products
- water
- urea
- mol
- 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
- 239000007859 condensation product Substances 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 claims description 22
- 239000004753 textile Substances 0.000 claims description 19
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 18
- 239000004202 carbamide Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 10
- 150000001298 alcohols Chemical class 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 229920003043 Cellulose fiber Polymers 0.000 claims description 6
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229920002866 paraformaldehyde Polymers 0.000 claims description 6
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 19
- 235000013877 carbamide Nutrition 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000004744 fabric Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006266 etherification reaction Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- -1 alkali hydroxides Chemical class 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 235000019645 odor Nutrition 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 241000251468 Actinopterygii Species 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 238000005299 abrasion Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 150000001923 cyclic compounds Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000008098 formaldehyde solution Substances 0.000 description 3
- 239000012263 liquid product Substances 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 150000008318 pyrimidones Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
- XIOUDVJTOYVRTB-UHFFFAOYSA-N 1-(1-adamantyl)-3-aminothiourea Chemical compound C1C(C2)CC3CC2CC1(NC(=S)NN)C3 XIOUDVJTOYVRTB-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 description 1
- NNTWKXKLHMTGBU-UHFFFAOYSA-N 4,5-dihydroxyimidazolidin-2-one Chemical compound OC1NC(=O)NC1O NNTWKXKLHMTGBU-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- JQALNNOQTGZTJZ-UHFFFAOYSA-N [[4,6-bis[bis(methoxymethyl)amino]-1,3,5-triazin-2-yl]-(methoxymethyl)amino]methanol Chemical compound COCN(CO)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 JQALNNOQTGZTJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000007730 finishing process Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/10—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with acyclic compounds having the moiety X=C(—N<)2 in which X is O, S or —N
- C08G12/12—Ureas; Thioureas
-
- 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
- C08G12/42—Chemically modified polycondensates by etherifying
- C08G12/421—Chemically modified polycondensates by etherifying of polycondensates based on acyclic or carbocyclic compounds
- C08G12/422—Chemically modified polycondensates by etherifying of polycondensates based on acyclic or carbocyclic compounds based on urea or thiourea
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2639754A DE2639754C3 (de) | 1976-09-03 | 1976-09-03 | Verfahren zur Herstellung von härtbaren Kondensationsprodukten und deren Verwendung |
| US05/741,912 US4102840A (en) | 1976-09-03 | 1976-11-15 | PROCESS FOR THE MANUFACTURE OF UREA-HCHO-isobutyraldehyde condesnation products and compositions thereof |
| NL7708477A NL7708477A (nl) | 1976-09-03 | 1977-08-01 | Werkwijze ter bereiding van condensatieproduk- ten en hun toepassing. |
| CH995177A CH622922B (de) | 1976-09-03 | 1977-08-15 | Verfahren zur herstellung von haertbaren kondensationsprodukten und deren verwendung als textilbehandlungsmittel. |
| AR268814A AR214205A1 (es) | 1976-09-03 | 1977-08-16 | Procedimiento para la sintesis de productos de condensacion endurecibles a partir de urea,formaldehido y aldehidos de ch-azidas |
| IT50707/77A IT1126766B (it) | 1976-09-03 | 1977-08-18 | Procedimento per la preparazione di prodotti di condensazione di urea,formaldeide ed aldeidi ch-funzionali e loro impiego per trattamento di materiali tessili |
| FR7725733A FR2363592A1 (fr) | 1976-09-03 | 1977-08-23 | Preparation de condensats uree-isobutyraldehyde-formaldehyde etherifies utiles pour le traitement des textiles |
| MX170314A MX146301A (es) | 1976-09-03 | 1977-08-23 | Procedimiento mejorado para la preparacion de un producto de condensacion de urea y formaldehido |
| SE7709522A SE7709522L (sv) | 1976-09-03 | 1977-08-24 | Sett att framstella kondensationsprodukter samt deras anvendning |
| GB36823/77A GB1576250A (en) | 1976-09-03 | 1977-09-02 | Process for the manufacture of condensation products and compositions thereof |
| ES462075A ES462075A1 (es) | 1976-09-03 | 1977-09-02 | Procedimiento para la preparacion de productos de condensa- cion endurecibles de urea, formaldehido y aldehidos de ch- acidas. |
| BR7705874A BR7705874A (pt) | 1976-09-03 | 1977-09-02 | Processo para a preparacao de produtos de condenacao e seu emprego |
| JP10505177A JPS5331791A (en) | 1976-09-03 | 1977-09-02 | Method of making condensation product and use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2639754A DE2639754C3 (de) | 1976-09-03 | 1976-09-03 | Verfahren zur Herstellung von härtbaren Kondensationsprodukten und deren Verwendung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2639754A1 DE2639754A1 (de) | 1978-03-09 |
| DE2639754B2 DE2639754B2 (de) | 1979-11-15 |
| DE2639754C3 true DE2639754C3 (de) | 1980-07-24 |
Family
ID=5987100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2639754A Expired DE2639754C3 (de) | 1976-09-03 | 1976-09-03 | Verfahren zur Herstellung von härtbaren Kondensationsprodukten und deren Verwendung |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4102840A (Direct) |
| JP (1) | JPS5331791A (Direct) |
| AR (1) | AR214205A1 (Direct) |
| BR (1) | BR7705874A (Direct) |
| CH (1) | CH622922B (Direct) |
| DE (1) | DE2639754C3 (Direct) |
| ES (1) | ES462075A1 (Direct) |
| FR (1) | FR2363592A1 (Direct) |
| GB (1) | GB1576250A (Direct) |
| IT (1) | IT1126766B (Direct) |
| MX (1) | MX146301A (Direct) |
| NL (1) | NL7708477A (Direct) |
| SE (1) | SE7709522L (Direct) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2757176A1 (de) * | 1977-12-22 | 1979-07-05 | Basf Ag | Verfahren zur herstellung von weich- und hartharzen und deren verwendung |
| DE2757220C2 (de) * | 1977-12-22 | 1981-09-24 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Weich- und Hartharzen und deren Verwendung |
| US4238545A (en) * | 1979-03-30 | 1980-12-09 | International Minerals & Chemical Corporation | Modified urea-formaldehyde resin |
| US4219631A (en) * | 1979-03-30 | 1980-08-26 | International Minerals & Chemical Corp. | Modified urea-formaldehyde resin |
| US4298512A (en) * | 1980-04-24 | 1981-11-03 | W. A. Cleary Chemical Corporation | Urea formaldehyde dispersions modified with higher aldehydes |
| US4332610A (en) * | 1980-04-24 | 1982-06-01 | W. A. Cleary Chemical Corporation | Urea formaldehyde dispersions modified with higher aldehydes |
| DE3425131A1 (de) * | 1984-07-07 | 1986-01-16 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von haertbaren veretherten aminoplastharzen und deren verwendung |
| DE3641997A1 (de) * | 1986-12-09 | 1988-06-16 | Basf Ag | Harnstoff-aldehyd-polykondensate, ein verfahren zu deren herstellung sowie deren verwendung als lackbindemittel |
| US5173464A (en) * | 1990-06-11 | 1992-12-22 | Pettijohn Ted M | Olefin polymerization |
| CN100383170C (zh) * | 2006-02-21 | 2008-04-23 | 华南理工大学 | 脲-异丁醛-甲醛共聚树脂的制备方法 |
| CN101418066B (zh) * | 2008-11-28 | 2010-06-02 | 华南理工大学 | 一种脲-异丁醛-甲醛树脂连续生产工艺 |
| WO2013027156A1 (de) | 2011-08-19 | 2013-02-28 | Basf Se | Verfahren zur herstellung von kondensationsharzen und deren verwendung |
| US8957178B2 (en) * | 2011-08-19 | 2015-02-17 | Basf Se | Method for preparing condensation resins and use thereof |
| CN105585993A (zh) * | 2016-03-11 | 2016-05-18 | 广西大学 | 一种异丁醛改性脲醛树脂胶粘剂的制备方法 |
| US11465945B2 (en) | 2017-04-24 | 2022-10-11 | Sabic Global Technologies B.V. | Urea condensation compositions and methods of making the same |
| CN112672986A (zh) | 2018-07-23 | 2021-04-16 | 沙特基础工业全球技术公司 | 球形脲醛缩合物肥料 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1810925U (de) | 1960-02-17 | 1960-05-05 | Behn Verpackung Erwin | Kreuzbodenventilsack |
| GB1069526A (en) | 1963-07-19 | 1967-05-17 | Hoechst Ag | Condensation products of urea and aldehydes and process for making them |
| CH1071265D (Direct) * | 1965-08-17 | |||
| DE2259680C3 (de) | 1972-12-06 | 1975-10-16 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung wasserlöslicher, chlorechter Appreturmittel für Zellulose enthaltende oder daraus bestehende Textilien |
| DE2455420A1 (de) | 1974-11-22 | 1976-05-26 | Lentia Gmbh | Verfahren zur herstellung von formaldehyd-harnstoff-melamin-kondensationsprodukten |
-
1976
- 1976-09-03 DE DE2639754A patent/DE2639754C3/de not_active Expired
- 1976-11-15 US US05/741,912 patent/US4102840A/en not_active Expired - Lifetime
-
1977
- 1977-08-01 NL NL7708477A patent/NL7708477A/xx unknown
- 1977-08-15 CH CH995177A patent/CH622922B/xx not_active IP Right Cessation
- 1977-08-16 AR AR268814A patent/AR214205A1/es active
- 1977-08-18 IT IT50707/77A patent/IT1126766B/it active
- 1977-08-23 FR FR7725733A patent/FR2363592A1/fr active Granted
- 1977-08-23 MX MX170314A patent/MX146301A/es unknown
- 1977-08-24 SE SE7709522A patent/SE7709522L/ unknown
- 1977-09-02 GB GB36823/77A patent/GB1576250A/en not_active Expired
- 1977-09-02 ES ES462075A patent/ES462075A1/es not_active Expired
- 1977-09-02 BR BR7705874A patent/BR7705874A/pt unknown
- 1977-09-02 JP JP10505177A patent/JPS5331791A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH622922B (de) | |
| ES462075A1 (es) | 1978-06-01 |
| DE2639754A1 (de) | 1978-03-09 |
| GB1576250A (en) | 1980-10-01 |
| FR2363592A1 (fr) | 1978-03-31 |
| US4102840A (en) | 1978-07-25 |
| AR214205A1 (es) | 1979-05-15 |
| IT1126766B (it) | 1986-05-21 |
| JPS5331791A (en) | 1978-03-25 |
| CH622922GA3 (Direct) | 1981-05-15 |
| BR7705874A (pt) | 1978-06-27 |
| SE7709522L (sv) | 1978-03-04 |
| FR2363592B1 (Direct) | 1981-11-27 |
| NL7708477A (nl) | 1978-03-07 |
| MX146301A (es) | 1982-06-03 |
| DE2639754B2 (de) | 1979-11-15 |
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| OAM | Search report available | ||
| OAP | Request for examination filed | ||
| OC | Search report available | ||
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: CHEMISCHE FABRIK PFERSEE GMBH, 8901 LANGWEID, DE |
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| 8339 | Ceased/non-payment of the annual fee |