CH627749A5 - Verfahren zur herstellung eines neuen gemischten hydroxymethyl-hydroxyalkylisocyanurats. - Google Patents
Verfahren zur herstellung eines neuen gemischten hydroxymethyl-hydroxyalkylisocyanurats. Download PDFInfo
- Publication number
- CH627749A5 CH627749A5 CH744476A CH744476A CH627749A5 CH 627749 A5 CH627749 A5 CH 627749A5 CH 744476 A CH744476 A CH 744476A CH 744476 A CH744476 A CH 744476A CH 627749 A5 CH627749 A5 CH 627749A5
- Authority
- CH
- Switzerland
- Prior art keywords
- isocyanurate
- hydroxymethyl
- agent
- mixed
- hydroxymethylating
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 35
- -1 hydroxymethyl-hydroxy Chemical group 0.000 claims description 23
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000004593 Epoxy Substances 0.000 claims description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 5
- 229920002866 paraformaldehyde Polymers 0.000 claims description 4
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 150000002924 oxiranes Chemical class 0.000 claims description 3
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 229920005862 polyol Polymers 0.000 description 8
- 150000003077 polyols Chemical class 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LDIRKUFENGRHQC-UHFFFAOYSA-N 1-isocyanatopropan-2-ol Chemical compound CC(O)CN=C=O LDIRKUFENGRHQC-UHFFFAOYSA-N 0.000 description 1
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 1
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7506982A NL7506982A (nl) | 1975-06-12 | 1975-06-12 | Gemengde hydroxymethyl-hydroxyalkylisocyanuraten. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH627749A5 true CH627749A5 (de) | 1982-01-29 |
Family
ID=19823936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH744476A CH627749A5 (de) | 1975-06-12 | 1976-06-11 | Verfahren zur herstellung eines neuen gemischten hydroxymethyl-hydroxyalkylisocyanurats. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4063020A (enExample) |
| JP (1) | JPS5225787A (enExample) |
| BE (1) | BE842786A (enExample) |
| CH (1) | CH627749A5 (enExample) |
| DE (1) | DE2626104A1 (enExample) |
| ES (1) | ES448781A1 (enExample) |
| FR (1) | FR2314181A1 (enExample) |
| GB (1) | GB1539943A (enExample) |
| IT (1) | IT1061344B (enExample) |
| NL (1) | NL7506982A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7800770A (nl) * | 1978-01-23 | 1979-07-25 | Stamicarbon | Bereiding van tris (n-beta-hydroxypropyl) isocyanuraat. |
| NL7802413A (nl) * | 1978-03-04 | 1979-09-06 | Stamicarbon | Vernette polyurethanen. |
| NL7802414A (nl) * | 1978-03-04 | 1979-09-06 | Stamicarbon | Bindmiddelen voor lakken op polyurethaanbasis. |
| WO2009086253A1 (en) * | 2007-12-27 | 2009-07-09 | E. I. Du Pont De Nemours And Company | Hydroxy alkyl isocyanurates |
| JP7408591B2 (ja) * | 2021-03-22 | 2024-01-05 | 四国化成工業株式会社 | カルボキシル基を有するイソシアヌレート化合物および該化合物を用いたエポキシ樹脂組成物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2901463A (en) * | 1955-06-21 | 1959-08-25 | Rohm & Haas | Compositions, textiles treated therewith and processes for the treatment thereof |
| US2950553A (en) * | 1957-01-16 | 1960-08-30 | Rohm & Haas | Method of producing wrinkle resistant garments and other manufactured articles of cotton-containing fabrics |
| US3660327A (en) * | 1970-06-08 | 1972-05-02 | George Co P D | Lactone or lactam pre-esterified isocyanurate-containing resins |
| US3870716A (en) * | 1971-03-22 | 1975-03-11 | Allied Chem | Process for production of alkylene oxide adducts of iris(2-hydroxyalkyl)isocyanurate |
| US3981998A (en) * | 1974-03-08 | 1976-09-21 | Waldstein David A | Bactericidal and fungicidal 1,3,5 trialkanol triazines |
-
1975
- 1975-06-12 NL NL7506982A patent/NL7506982A/xx not_active Application Discontinuation
-
1976
- 1976-06-07 GB GB23400/76A patent/GB1539943A/en not_active Expired
- 1976-06-10 BE BE167784A patent/BE842786A/xx not_active IP Right Cessation
- 1976-06-10 DE DE19762626104 patent/DE2626104A1/de not_active Ceased
- 1976-06-10 US US05/694,645 patent/US4063020A/en not_active Expired - Lifetime
- 1976-06-10 IT IT49895/76A patent/IT1061344B/it active
- 1976-06-11 ES ES448781A patent/ES448781A1/es not_active Expired
- 1976-06-11 JP JP51068649A patent/JPS5225787A/ja active Pending
- 1976-06-11 FR FR7617761A patent/FR2314181A1/fr active Granted
- 1976-06-11 CH CH744476A patent/CH627749A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2314181B1 (enExample) | 1980-05-16 |
| IT1061344B (it) | 1983-02-28 |
| JPS5225787A (en) | 1977-02-25 |
| DE2626104A1 (de) | 1976-12-30 |
| ES448781A1 (es) | 1977-12-16 |
| NL7506982A (nl) | 1976-12-14 |
| FR2314181A1 (fr) | 1977-01-07 |
| US4063020A (en) | 1977-12-13 |
| BE842786A (nl) | 1976-12-10 |
| GB1539943A (en) | 1979-02-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |