DE1770176A1 - Verfahren zur Herstellung von 1,3-Dimethylol-4,5-dihydroxy-2-imidazolidinon - Google Patents
Verfahren zur Herstellung von 1,3-Dimethylol-4,5-dihydroxy-2-imidazolidinonInfo
- Publication number
- DE1770176A1 DE1770176A1 DE19681770176 DE1770176A DE1770176A1 DE 1770176 A1 DE1770176 A1 DE 1770176A1 DE 19681770176 DE19681770176 DE 19681770176 DE 1770176 A DE1770176 A DE 1770176A DE 1770176 A1 DE1770176 A1 DE 1770176A1
- Authority
- DE
- Germany
- Prior art keywords
- formaldehyde
- parts
- dihydroxy
- dimethylol
- glyoxal
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title description 3
- 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 title 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 37
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 19
- 229940015043 glyoxal Drugs 0.000 claims description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000047 product Substances 0.000 description 14
- 239000004744 fabric Substances 0.000 description 8
- 239000004753 textile Substances 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 230000037303 wrinkles Effects 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000004669 nonionic softener Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-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
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 239000004266 EU approved firming agent Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- -1 dihydroxy-2-imidazolidinoL Chemical compound 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
- 229950005308 oxymethurea Drugs 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/40—Two or more oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63084767A | 1967-04-14 | 1967-04-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1770176A1 true DE1770176A1 (de) | 1971-09-23 |
Family
ID=24528804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681770176 Pending DE1770176A1 (de) | 1967-04-14 | 1968-04-10 | Verfahren zur Herstellung von 1,3-Dimethylol-4,5-dihydroxy-2-imidazolidinon |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3487088A (enrdf_load_stackoverflow) |
| BE (1) | BE713651A (enrdf_load_stackoverflow) |
| CH (1) | CH497430A (enrdf_load_stackoverflow) |
| DE (1) | DE1770176A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1558244A (enrdf_load_stackoverflow) |
| GB (1) | GB1199687A (enrdf_load_stackoverflow) |
| NL (1) | NL6805193A (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4016335A (en) * | 1973-05-02 | 1977-04-05 | American Cyanamid Company | Urea-glyoxal-formaldehyde cellulose reactant |
| US3903033A (en) * | 1973-05-02 | 1975-09-02 | American Cyanamid Co | Urea-glyoxal-formaldehyde cellulose reactant |
| US4173645A (en) * | 1976-12-22 | 1979-11-06 | Bayer Aktiengesellschaft | Substituted 4,5-dihydroxy-imidazolidine-2-thiones and their use as ectoparasiticides |
| FR2613361B1 (fr) * | 1987-04-02 | 1989-07-21 | Hoechst France | Urees substituees, leur procede de preparation et leur application notamment dans l'ennoblissement des fibres cellulosiques |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2731472A (en) * | 1956-01-17 | Production of heterocyclic compounds | ||
| DE910475C (de) * | 1951-08-17 | 1954-05-03 | Basf Ag | Verfahren zur Herstellung stickstoffhaltiger Kondensationsprodukte |
| US2755198A (en) * | 1953-02-27 | 1956-07-17 | Monsanto Chemicals | Novel compositions and treatment of textile materials |
| US2876062A (en) * | 1953-09-03 | 1959-03-03 | Phrix Werke Ag | Process of crease-proofing cellulose fibers and fabrics by applying ureaformaldehyde-glyoxal reaction products |
| BE534387A (enrdf_load_stackoverflow) * | 1953-12-31 | |||
| US3112156A (en) * | 1960-10-07 | 1963-11-26 | Sidney L Vail | Treatment of cellulosic textile material with 1, 3-dimethyl-4, 5-dihydroxy-2-imidazolidinone |
| US3209010A (en) * | 1961-11-13 | 1965-09-28 | Gagliardi Res Corp | Polyalkylated monoureins |
-
1967
- 1967-04-14 US US630847A patent/US3487088A/en not_active Expired - Lifetime
-
1968
- 1968-04-02 FR FR1558244D patent/FR1558244A/fr not_active Expired
- 1968-04-03 GB GB16082/68A patent/GB1199687A/en not_active Expired
- 1968-04-10 DE DE19681770176 patent/DE1770176A1/de active Pending
- 1968-04-11 NL NL6805193A patent/NL6805193A/xx not_active Application Discontinuation
- 1968-04-11 CH CH546768A patent/CH497430A/de not_active IP Right Cessation
- 1968-04-12 BE BE713651D patent/BE713651A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR1558244A (enrdf_load_stackoverflow) | 1969-02-21 |
| NL6805193A (enrdf_load_stackoverflow) | 1968-10-15 |
| GB1199687A (en) | 1970-07-22 |
| CH497430A (de) | 1970-10-15 |
| US3487088A (en) | 1969-12-30 |
| BE713651A (enrdf_load_stackoverflow) | 1968-10-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHW | Rejection |