NO124446B - - Google Patents
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- Publication number
- NO124446B NO124446B NO692369A NO236969A NO124446B NO 124446 B NO124446 B NO 124446B NO 692369 A NO692369 A NO 692369A NO 236969 A NO236969 A NO 236969A NO 124446 B NO124446 B NO 124446B
- Authority
- NO
- Norway
- Prior art keywords
- triazine
- biguanide
- diamino
- formic acid
- hydrochloride
- Prior art date
Links
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 23
- -1 N-substituted 2,4-diamino-1,3,5-triazines Chemical class 0.000 claims description 12
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 11
- 229940123208 Biguanide Drugs 0.000 claims description 11
- 235000019253 formic acid Nutrition 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- 150000004283 biguanides Chemical class 0.000 claims description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 150000003918 triazines Chemical class 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims 1
- 230000000171 quenching effect Effects 0.000 claims 1
- WEWFIUPOLKEEJP-UHFFFAOYSA-N triazine-4,6-diamine Chemical class NC1=CC(N)=NN=N1 WEWFIUPOLKEEJP-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 4
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- PMONNILNCNLAKE-UHFFFAOYSA-N 1-(4-nitrophenyl)-2H-1,3,5-triazine-2,4-diamine Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)N1C(N=C(N=C1)N)N PMONNILNCNLAKE-UHFFFAOYSA-N 0.000 description 2
- SFMVRDYQFSSSDQ-UHFFFAOYSA-N 1-ethyl-2H-1,3,5-triazine-2,4-diamine Chemical compound C(C)N1C(N=C(N=C1)N)N SFMVRDYQFSSSDQ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WDHLWDPXBSGOAO-UHFFFAOYSA-N 1-(4-chlorophenyl)-2H-1,3,5-triazine-2,4-diamine hydrochloride Chemical compound Cl.NC1N=C(N)N=CN1C1=CC=C(Cl)C=C1 WDHLWDPXBSGOAO-UHFFFAOYSA-N 0.000 description 1
- GINNVXSTAWRQGT-UHFFFAOYSA-N 1-(4-methylphenyl)-2H-1,3,5-triazine-2,4-diamine hydrochloride Chemical compound Cl.C1(=CC=C(C=C1)N1C(N=C(N=C1)N)N)C GINNVXSTAWRQGT-UHFFFAOYSA-N 0.000 description 1
- ZNJNFUSJCJOWNJ-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(4-methylphenyl)guanidine;hydrochloride Chemical compound Cl.CC1=CC=C(N=C(N)N=C(N)N)C=C1 ZNJNFUSJCJOWNJ-UHFFFAOYSA-N 0.000 description 1
- XWFPIJRFFLYWRN-UHFFFAOYSA-N 1-(diaminomethylidene)-2-ethylguanidine Chemical compound CCN=C(N)N=C(N)N XWFPIJRFFLYWRN-UHFFFAOYSA-N 0.000 description 1
- XRIOQERBDIAZQY-UHFFFAOYSA-N 1-phenyl-2H-1,3,5-triazine-2,4-diamine Chemical compound C1(=CC=CC=C1)N1C(N=C(N=C1)N)N XRIOQERBDIAZQY-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ARKDGVJNZCNKQM-UHFFFAOYSA-N C1(=CC=C(C=C1)N1C(N=C(N=C1)N)N)C Chemical compound C1(=CC=C(C=C1)N1C(N=C(N=C1)N)N)C ARKDGVJNZCNKQM-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- FHUDRDSKZQDCBC-UHFFFAOYSA-N [(e)-n'-(n'-phenylcarbamimidoyl)carbamimidoyl]azanium;chloride Chemical compound Cl.NC(N)=NC(N)=NC1=CC=CC=C1 FHUDRDSKZQDCBC-UHFFFAOYSA-N 0.000 description 1
- NAFSLMFLGYXGIF-UHFFFAOYSA-N [n'-[n'-(4-chlorophenyl)carbamimidoyl]carbamimidoyl]azanium;chloride Chemical compound Cl.NC(N)=NC(N)=NC1=CC=C(Cl)C=C1 NAFSLMFLGYXGIF-UHFFFAOYSA-N 0.000 description 1
- NAOSJVUAQGULFR-UHFFFAOYSA-N [n'-[n'-(4-nitrophenyl)carbamimidoyl]carbamimidoyl]azanium;chloride Chemical compound [Cl-].N\C([NH3+])=N/C(N)=NC1=CC=C([N+]([O-])=O)C=C1 NAOSJVUAQGULFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
- F25C—PRODUCING, WORKING OR HANDLING ICE
- F25C1/00—Producing ice
- F25C1/12—Producing ice by freezing water on cooled surfaces, e.g. to form slabs
Landscapes
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Mechanical Engineering (AREA)
- Thermal Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Devices That Are Associated With Refrigeration Equipment (AREA)
- Cooling Or The Like Of Semiconductors Or Solid State Devices (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Freezing, Cooling And Drying Of Foods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76427768A | 1968-10-01 | 1968-10-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO124446B true NO124446B (da) | 1972-04-17 |
Family
ID=25070230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO692369A NO124446B (da) | 1968-10-01 | 1969-06-09 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3546896A (da) |
| DE (1) | DE1933475C3 (da) |
| DK (1) | DK143369C (da) |
| GB (1) | GB1242324A (da) |
| NO (1) | NO124446B (da) |
| SE (1) | SE354112B (da) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3722227A (en) * | 1970-09-14 | 1973-03-27 | Schneider Metal Mfg Co | Water distribution control for automatic ice cube maker |
| US4192151A (en) * | 1977-09-07 | 1980-03-11 | Vivian Manufacturing Company | Ice making apparatus |
| JPS54127646U (da) * | 1978-02-27 | 1979-09-05 | ||
| US4829782A (en) * | 1988-08-29 | 1989-05-16 | Paul Mueller Company | Ice harvesting/water chiller machine |
| DE9102051U1 (de) * | 1991-02-21 | 1992-06-25 | Klüe, Ulrich, Dipl.-Ing., 2054 Geesthacht | Eiserzeugungsvorrichtung |
| DE19619290C2 (de) * | 1996-05-13 | 1999-07-08 | Kluee Ulrich | Verfahren zum Betrieb eines Kühlers für Gas oder Brüden und Kühler zur Durchführung dieses Verfahrens |
| AU1449000A (en) * | 1998-10-20 | 2000-05-08 | John A. Broadbent | Low cost ice making evaporator |
| JP4994198B2 (ja) * | 2007-11-21 | 2012-08-08 | ホシザキ電機株式会社 | 流下式製氷機 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2297348A (en) * | 1941-08-28 | 1942-09-29 | Kusel Dairy Equipment Co | Heat treating of milk products |
| US2616670A (en) * | 1948-01-10 | 1952-11-04 | Directie Staatsmijnen Nl | Liquid distribution device |
| US2746262A (en) * | 1954-01-11 | 1956-05-22 | Albert M Gallo | Ice making machine |
| US2997861A (en) * | 1958-10-17 | 1961-08-29 | Vilter Manufacturing Corp | Art of producing ice briquettes |
| US3171266A (en) * | 1961-07-06 | 1965-03-02 | Weisco Products Corp | Ice making machine with water distribution means |
| US3430452A (en) * | 1966-12-05 | 1969-03-04 | Manitowoc Co | Ice cube making apparatus |
-
1968
- 1968-10-01 US US764277A patent/US3546896A/en not_active Expired - Lifetime
-
1969
- 1969-06-02 GB GB27820/69A patent/GB1242324A/en not_active Expired
- 1969-06-05 SE SE07983/69A patent/SE354112B/xx unknown
- 1969-06-09 NO NO692369A patent/NO124446B/no unknown
- 1969-07-02 DE DE1933475A patent/DE1933475C3/de not_active Expired
- 1969-09-30 DK DK519869A patent/DK143369C/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK143369B (da) | 1981-08-10 |
| DE1933475C3 (de) | 1974-02-28 |
| US3546896A (en) | 1970-12-15 |
| GB1242324A (en) | 1971-08-11 |
| DE1933475B2 (de) | 1973-07-26 |
| DK143369C (da) | 1981-12-14 |
| DE1933475A1 (de) | 1970-04-23 |
| SE354112B (da) | 1973-02-26 |
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