CA1155460A - N,n-dialkylaminoalkyl-ethylenediamines and process for their manufacture - Google Patents
N,n-dialkylaminoalkyl-ethylenediamines and process for their manufactureInfo
- Publication number
- CA1155460A CA1155460A CA000360957A CA360957A CA1155460A CA 1155460 A CA1155460 A CA 1155460A CA 000360957 A CA000360957 A CA 000360957A CA 360957 A CA360957 A CA 360957A CA 1155460 A CA1155460 A CA 1155460A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- alkyl
- ethylenediamines
- glyoxal
- manufacture
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
- C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Cephalosporin Compounds (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
N,N-Dialkylaminoalkyl-ethylenediamines of the formula 1 R1-CH2CH2-NH-(CH2)m-NH-(CH2)2-NH-(CH2)n-NH-CH2CH2-R2 (1) wherein Rl and R2 are identical or different and are alkyl, 2-hydroxyalkyl or alkenyl with from 6 to 28 carbon atoms each or C6-C22-alkoxy-propyl and m and n are 2 or 3 and process for their manufacture.
N,N-Dialkylaminoalkyl-ethylenediamines of the formula 1 R1-CH2CH2-NH-(CH2)m-NH-(CH2)2-NH-(CH2)n-NH-CH2CH2-R2 (1) wherein Rl and R2 are identical or different and are alkyl, 2-hydroxyalkyl or alkenyl with from 6 to 28 carbon atoms each or C6-C22-alkoxy-propyl and m and n are 2 or 3 and process for their manufacture.
Description
~15~60 Subject of the invention are N,N-dialkylaminoalkyl-ethylenediamines of the formula 1 Rl-cH2cH2-NH-(cH2)m-NH-(cH2)2-Nll-(cH2)n NH C 2 2 2 (1) wherein Rl and R2 are identical or different and are alkyl, 2-hydroxyalkyl or alkenyl with from 6 to 28 carbon atoms each or C6-C22-alkoxy-propyl and m and n are 2 or 3.
Compounds of the formula 1, wherein Rl and R2 are identical and are alkyl, 2-hydroxyalkyl or alkenyl with from 8 to 18 carbon atoms each and m=n=3 are preferred.
Moreover, subject of the present invention is a process for the manufacture of compounds of the formula 1, which comprises reacting fatty alkyl-alkylenediamines of the formula 2 Rl-NH-(CH2)m NH2 or R2-NH-(CH2)n-NH2 (2) with glyoxal to give bisaldimines of the formula 3 Rl-NH-~cH2)m(n)-N=cH-cH=N-(cH2)n(m) 2 and subsequently catalytically hydrogenating the Schiff bases obtained.
As alkylalkylene diamines of the formula 2 there can be used, for example, coconut alkyl-propylenediamines, stearyl-propylenediamines or tallow propylenediamines. According to the invention there can also be used the corresponding ethylenediamines such as N-dodecyl-ethylenediamines or N-cetyl-ethylenediamine or even ether alkylenediamines such as lauryloxypropyl-propylenediamine.
In a preferred embodiment according to the invention in the formula 1 Rl and R2 are identical and m=n=3. Starting products preferably suitable and accessible in in-
Compounds of the formula 1, wherein Rl and R2 are identical and are alkyl, 2-hydroxyalkyl or alkenyl with from 8 to 18 carbon atoms each and m=n=3 are preferred.
Moreover, subject of the present invention is a process for the manufacture of compounds of the formula 1, which comprises reacting fatty alkyl-alkylenediamines of the formula 2 Rl-NH-(CH2)m NH2 or R2-NH-(CH2)n-NH2 (2) with glyoxal to give bisaldimines of the formula 3 Rl-NH-~cH2)m(n)-N=cH-cH=N-(cH2)n(m) 2 and subsequently catalytically hydrogenating the Schiff bases obtained.
As alkylalkylene diamines of the formula 2 there can be used, for example, coconut alkyl-propylenediamines, stearyl-propylenediamines or tallow propylenediamines. According to the invention there can also be used the corresponding ethylenediamines such as N-dodecyl-ethylenediamines or N-cetyl-ethylenediamine or even ether alkylenediamines such as lauryloxypropyl-propylenediamine.
In a preferred embodiment according to the invention in the formula 1 Rl and R2 are identical and m=n=3. Starting products preferably suitable and accessible in in-
- 2 -~ . . .
; ~. .
. ~ ' '' '~
1~5~60
; ~. .
. ~ ' '' '~
1~5~60
- 3 ~ 7~/F 254 dustrial amo~nts ~re to this end for example fat,y allcyl-propylenediamilles Oll the basis of natural fats and oils such as tallow or coconut oil. Within khe scope of the present invention, diamines with chain distributions whlch are not accessible industrially or compounds with unif`orm chain can of course be used, too. These substances are prepared in knowrl manner for example by addition of 1 mol of acrylonitrile on primary fatty amines and subsequent catalytic hydrogenakion of the propionitriles. The corres-ponding alkoxypropyl-propylenediamirles are obtained by ad dition of acrylonitrils on fatty alcohols, catalytic hydrogenation of the propionitriles, addition of one more molecule of acrylonitrile on the resulting alkoxypropylami-nes and by another catalytic hydrogenation. The all~yl-ethylenediamilles can be prepared for example by reactionof one mol of alkyl halide with ethylenediamine.
The condensatioll of the diamines of the formula 2 with glyoxal is performed at temperatures below 50C preferably at roo~ temperature by adding a commercially available 40 % glyoxal solution to a solution of the cliamine in a solvent which is indifferent in the reaction preferably an alcohol such as methanol, isopropanol or isobutanol. The Molar ratio of amine to glyoxal is between 2:1 and 2:1.2.
The bisaldimine is formed instantaneously. Especially when using methanol as solvent, the products are difficultly so-luble and deposit in liquid paste-like or solid form. They carl easily be separated by phase separation or filtration and isolated as pure substances after drying.
The suspensions or emulsions of the bisaldimines of 3Q formula 3 which are formed during the condensation are pre-ferably subjected directly to the catalytic hydrogenat-.oll.
According to the invention 2 mols of different N-alkyl-pro-pylenediamirles~ N-alkyl-ethylenediamines or N-alkoxypropyl-propylenediami-les or their mixtures can of course also be reacted with glyoxal. With this method statitistical mix tures of dlfferent Schiff bases are obtained.
The catalytic hydrGgenation is expediently carried out ~ 155~60 at temperatures below 100C, preferably at 40 to 80C. Suitable catalysts are noble metals, such as platinum, palladium or rhodium. Because of economical reasons, however, metal catalysts, such as nickel or cobalt, will be preferably used. Raney nickel is especially suitable. The hydrogen pressures are, accord-ing to the invention, from 50 to 150 bar, especially from 80 to 120 bar.
The isolation of the pure products of the formula 1 according to the invention is performed by separating them by filtration from the hydrogenation catalyst and evaporating the solvent. The resulting compounds of the formula 1 are obtained in a purity of 80 to 90% according to the analysis of the amine nitrogen and can be directly used in this form for most applications. Absolutely pure compounds can be obtained by recrystallization.
The N,N'-dialkylalk~ylene-ethylenediamines of the formula 1 are suitable as starting products for the manufacture of a number of new surface active com-pounds.
In particular, applicants copending Canadian application Serial No.
360,952 describes the step of oxethylation of the diamines of the present inven-tion. These oxethylated compounds are useful as dispersing agents.
The following examples illustrate the invention.
Example 1 900 g ~2.5 mols) of industrial tallow fat alkyl propyldiamine-with an alkyl chain distribution of about 1% of C12, 3% of C14, 31% of C16, 35% of saturated C18 and 30% of unsaturated C18 are dissolved in 2~500 ml of methanol.
190 g (1.3 mols) of 40% glyoxal soltuion are added dropwise within 30 minutes at room temperature and stirring is continued for 2 hours at room temperature.
The crude reaction mixture is passed into a stainless steel autoclave, admixed with 16 g of Raney nickel and hydrogenated at 60C and 100 bar of hydrogen pre-ssure while stirring, until the absorption of hydrogen is terminated. Sub-
The condensatioll of the diamines of the formula 2 with glyoxal is performed at temperatures below 50C preferably at roo~ temperature by adding a commercially available 40 % glyoxal solution to a solution of the cliamine in a solvent which is indifferent in the reaction preferably an alcohol such as methanol, isopropanol or isobutanol. The Molar ratio of amine to glyoxal is between 2:1 and 2:1.2.
The bisaldimine is formed instantaneously. Especially when using methanol as solvent, the products are difficultly so-luble and deposit in liquid paste-like or solid form. They carl easily be separated by phase separation or filtration and isolated as pure substances after drying.
The suspensions or emulsions of the bisaldimines of 3Q formula 3 which are formed during the condensation are pre-ferably subjected directly to the catalytic hydrogenat-.oll.
According to the invention 2 mols of different N-alkyl-pro-pylenediamirles~ N-alkyl-ethylenediamines or N-alkoxypropyl-propylenediami-les or their mixtures can of course also be reacted with glyoxal. With this method statitistical mix tures of dlfferent Schiff bases are obtained.
The catalytic hydrGgenation is expediently carried out ~ 155~60 at temperatures below 100C, preferably at 40 to 80C. Suitable catalysts are noble metals, such as platinum, palladium or rhodium. Because of economical reasons, however, metal catalysts, such as nickel or cobalt, will be preferably used. Raney nickel is especially suitable. The hydrogen pressures are, accord-ing to the invention, from 50 to 150 bar, especially from 80 to 120 bar.
The isolation of the pure products of the formula 1 according to the invention is performed by separating them by filtration from the hydrogenation catalyst and evaporating the solvent. The resulting compounds of the formula 1 are obtained in a purity of 80 to 90% according to the analysis of the amine nitrogen and can be directly used in this form for most applications. Absolutely pure compounds can be obtained by recrystallization.
The N,N'-dialkylalk~ylene-ethylenediamines of the formula 1 are suitable as starting products for the manufacture of a number of new surface active com-pounds.
In particular, applicants copending Canadian application Serial No.
360,952 describes the step of oxethylation of the diamines of the present inven-tion. These oxethylated compounds are useful as dispersing agents.
The following examples illustrate the invention.
Example 1 900 g ~2.5 mols) of industrial tallow fat alkyl propyldiamine-with an alkyl chain distribution of about 1% of C12, 3% of C14, 31% of C16, 35% of saturated C18 and 30% of unsaturated C18 are dissolved in 2~500 ml of methanol.
190 g (1.3 mols) of 40% glyoxal soltuion are added dropwise within 30 minutes at room temperature and stirring is continued for 2 hours at room temperature.
The crude reaction mixture is passed into a stainless steel autoclave, admixed with 16 g of Raney nickel and hydrogenated at 60C and 100 bar of hydrogen pre-ssure while stirring, until the absorption of hydrogen is terminated. Sub-
- 4 -1~554~0 sequently, the catalyst is filtered off via a heated pressure suction filter and methanol is evaporated in vacuum. 900 g of a light beige wax-like product of the formula R NH (CH2)3 NH ~C 2)2 ( 2)3 R = tallow alkyl - 4a -. .
. ~ .
1 ~55d~60
. ~ .
1 ~55d~60
- 5 - _OE 79/~ 54 with a con~ent of ~0 ~ of secondary amine nitrogen and o.8 of tertiary amine nitrogen are obtaine~.
E X A M P L E 2:
-133.5 g (0.7 mol) of octyl-propylenecliamine are dis-solved in 650 ml of methano]. Within 15 minutes 54.8 g (0.38 mol) of a 40 % aqueous glyo~al solution are added dropwise at room temperature and stirring is continued for 2 hours at room temperature. The crude reaction mixture is passed into a stainless steel autoclave and hydrogenated after addition of 5 g of Raney nickel at 60~C and 100 bar of hydrogen pressure until the absorption of hydrogen is terminated. After filtration via a pressure suction filter and evaporating the solvent, 135 g of a light brown liquid product of the formula C8Hl7NH-(cH2)3-NH-(cH2)2-NE~-(cH2)3 N 8 17 with a content of 9.9 % of secondary amine nitrogen and 1.3 p of tertiary amine nitrogen are obtained.
E X A M P L E 3:
1,408 g (5.5 mols) of a distilled la~ryl-propylenedi-amine with an alkyl chain distribution of about 75 g of C12 and 25 ~ of C14 are dissolved in 5.5 l of methanol. Within 30 minutes 433 g (2~98 mols) of a 40 ~ aqueous glyoxal solll-tion are added dropwise at room temperature and stirring is continued for 2 hours at room temperature. The crude reac-tion mixture is passed into a stainless steel autoclave, 38 g of Raney nickel are added and the mixture is hydroge-nated at 60C and a hydrogen pressure of 90 bar until the absorption of hydrogen is terminated. After filtration via a pressure suction filter and evaporating the solvent, 1,400 g of a light beige, wax-like product of the formula R-NH-(CH2)3-NH-(CH2)2-NH-(CH2)3 R -~ 75 g of C12-alkyl and 25 % of C14-alkyl ' :
'. ~
;~ ~55~60
E X A M P L E 2:
-133.5 g (0.7 mol) of octyl-propylenecliamine are dis-solved in 650 ml of methano]. Within 15 minutes 54.8 g (0.38 mol) of a 40 % aqueous glyo~al solution are added dropwise at room temperature and stirring is continued for 2 hours at room temperature. The crude reaction mixture is passed into a stainless steel autoclave and hydrogenated after addition of 5 g of Raney nickel at 60~C and 100 bar of hydrogen pressure until the absorption of hydrogen is terminated. After filtration via a pressure suction filter and evaporating the solvent, 135 g of a light brown liquid product of the formula C8Hl7NH-(cH2)3-NH-(cH2)2-NE~-(cH2)3 N 8 17 with a content of 9.9 % of secondary amine nitrogen and 1.3 p of tertiary amine nitrogen are obtained.
E X A M P L E 3:
1,408 g (5.5 mols) of a distilled la~ryl-propylenedi-amine with an alkyl chain distribution of about 75 g of C12 and 25 ~ of C14 are dissolved in 5.5 l of methanol. Within 30 minutes 433 g (2~98 mols) of a 40 ~ aqueous glyoxal solll-tion are added dropwise at room temperature and stirring is continued for 2 hours at room temperature. The crude reac-tion mixture is passed into a stainless steel autoclave, 38 g of Raney nickel are added and the mixture is hydroge-nated at 60C and a hydrogen pressure of 90 bar until the absorption of hydrogen is terminated. After filtration via a pressure suction filter and evaporating the solvent, 1,400 g of a light beige, wax-like product of the formula R-NH-(CH2)3-NH-(CH2)2-NH-(CH2)3 R -~ 75 g of C12-alkyl and 25 % of C14-alkyl ' :
'. ~
;~ ~55~60
- 6 - HOE 79/F 254 with a content of' 8,05 % of secondary amine nitrogen and 0.95 ~ of tertiary amine nitrogen are obtained.
560 g (5 mols) of a distilled coconut alkylpropylenedi-amine with an alkyl chain distribution of about 7 % of C8, 6 % of C10, 51 % of C12, 19 % of C14~ 8 % of C16 and 9 ~ of C18 are dissolved in 1,700 ml of methanol. At room tem-perature 157.2 g (1.08 mols) of 40 % aqueous glyoxal solu-tion are added dropwise within 30 minutes and stirring is continued for 2 hours at room temperature. The crude reac-tion mixture is passed into a stainless steel autoclave, and after addition of 129 g of Raney nickel it is hydroge-nated for 3 hours at 60C and 100 bar of hydrogen pressure.
After working up as described in the examples above, 550 g of liquid, yellow product of the formula R-NH-(CH2)3-NH-(CH2)2-NH-(CH2)3 are obtained.
R = coconut alkyl with a content of 7.75 ~ of secondary and 0.8 d of tertiary amine nitrogen.
E X A M P L E 5:
390 g (1.5 mols) of a distilled isotridecyl-propylenedi-amine are dissolved in 1,300 ml of methanol. Within 40 mi-nutes 116 g (0.8 mol) of a 40 % aqueous glyoxal solution are added dropwise at room temperature and stirring is con-tinued for 2 hours at room temperature. The crude reaction mixture ~s passed into a stainless steel autoclave, and after additioll of 10 g of Raney nickel it is hydrogenated at 70C and 105 bar of hydrogen pressure, during 4 hours.
After workiDg up as described above, 392 g of an orange, viscous, liquid product of the formula -~H-(cH2)3-NH-~cH2)2-NH-(cH2)3 N
~55~60
560 g (5 mols) of a distilled coconut alkylpropylenedi-amine with an alkyl chain distribution of about 7 % of C8, 6 % of C10, 51 % of C12, 19 % of C14~ 8 % of C16 and 9 ~ of C18 are dissolved in 1,700 ml of methanol. At room tem-perature 157.2 g (1.08 mols) of 40 % aqueous glyoxal solu-tion are added dropwise within 30 minutes and stirring is continued for 2 hours at room temperature. The crude reac-tion mixture is passed into a stainless steel autoclave, and after addition of 129 g of Raney nickel it is hydroge-nated for 3 hours at 60C and 100 bar of hydrogen pressure.
After working up as described in the examples above, 550 g of liquid, yellow product of the formula R-NH-(CH2)3-NH-(CH2)2-NH-(CH2)3 are obtained.
R = coconut alkyl with a content of 7.75 ~ of secondary and 0.8 d of tertiary amine nitrogen.
E X A M P L E 5:
390 g (1.5 mols) of a distilled isotridecyl-propylenedi-amine are dissolved in 1,300 ml of methanol. Within 40 mi-nutes 116 g (0.8 mol) of a 40 % aqueous glyoxal solution are added dropwise at room temperature and stirring is con-tinued for 2 hours at room temperature. The crude reaction mixture ~s passed into a stainless steel autoclave, and after additioll of 10 g of Raney nickel it is hydrogenated at 70C and 105 bar of hydrogen pressure, during 4 hours.
After workiDg up as described above, 392 g of an orange, viscous, liquid product of the formula -~H-(cH2)3-NH-~cH2)2-NH-(cH2)3 N
~55~60
- 7 - HOE 79/F 254 are obtained.
R = isotridecyl with a content of 9.1 ~ of secondary and 0.9 ~ of tertiary amine nitrogen.
E X A M P L E 6:
800 g (2.5 mols) of alkoxypropyl-propylenediamine, the alkoxy radical of which has a chain distribution of from C12 to C15, and about 80 % of which are linear and about 20 % are branched, are dissolved in 2,500 ml of methanol.
At room temperature 190 g (1.3 mols) of 40 % glyoxal solu-tion are added dropwise within 35 minutes and stirring is continued ~or 2 hours at room temperature. The crude reac-tion mixture is passed into a stainless steel autoclave, admixed with 15 g of Raney nickel and hydrogenated at 60C
and 95 bar of hydrogen pressure during 3 1~2 hours. After working up (see above), 790 g of yellow oil of the compound of the formula R-NH-(CH2)3-NH-(CH2)2-NH-(CH2)3 NH
are obtained.
R = C12/C15-alkoxypropyl with a content of 7.1 % of secon-dary and 0.8 ~ of tertiary amine nitrogen.
R = isotridecyl with a content of 9.1 ~ of secondary and 0.9 ~ of tertiary amine nitrogen.
E X A M P L E 6:
800 g (2.5 mols) of alkoxypropyl-propylenediamine, the alkoxy radical of which has a chain distribution of from C12 to C15, and about 80 % of which are linear and about 20 % are branched, are dissolved in 2,500 ml of methanol.
At room temperature 190 g (1.3 mols) of 40 % glyoxal solu-tion are added dropwise within 35 minutes and stirring is continued ~or 2 hours at room temperature. The crude reac-tion mixture is passed into a stainless steel autoclave, admixed with 15 g of Raney nickel and hydrogenated at 60C
and 95 bar of hydrogen pressure during 3 1~2 hours. After working up (see above), 790 g of yellow oil of the compound of the formula R-NH-(CH2)3-NH-(CH2)2-NH-(CH2)3 NH
are obtained.
R = C12/C15-alkoxypropyl with a content of 7.1 % of secon-dary and 0.8 ~ of tertiary amine nitrogen.
Claims (3)
- THE EMBODIMENTS OF THE INVENTION IN WIIICII AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
l. N,N-dialkylalkylene-ethylenediamine of the formula 1 R1-CH2CH2-NH-(CH2)2-NH-(CH2)2-NH-(CH2)n-NH-CH2CH2-R2 (1) wherein Rl and R2 are identical or different and are alkyl, 2-hydroxyalkyl or alkenyl with from 6 to 28 carbon atoms each or C6-C22-alkoxy-propyl and m and n are 2 or 3. - 2. Compounds of the formula 1 according to claim 1, wherein Rl and R2 are identical and are alkyl, 2-hydroxyalkyl or alkenyl with from 8 to 18 carbon atoms each and m=n=3.
- 3. Process for the manufacture of compounds of the formula 1 according to claim l, which comprises first condensing alkyl-alkylenediamines of the formula 2 Rl-NH-(CH2)m-NH2 (2) or R2-NH-(CH2)n-NH2 with glyoxal to give bisaldimines of the formula 3 Rl-NH-(cH2)m(n)-N=CH-CH=N-(CH2)n(m)-NH-R2 (3) and subsequently hydrogenating same catalytically to give the compound of the formula 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792938710 DE2938710A1 (en) | 1979-09-25 | 1979-09-25 | N, N'-DIALKYLAMINOALKYLETHYLENE DIAMINE AND METHOD FOR THE PRODUCTION THEREOF |
| DEP2938710.8 | 1979-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1155460A true CA1155460A (en) | 1983-10-18 |
Family
ID=6081771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000360957A Expired CA1155460A (en) | 1979-09-25 | 1980-09-24 | N,n-dialkylaminoalkyl-ethylenediamines and process for their manufacture |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0025997B1 (en) |
| JP (1) | JPS5657742A (en) |
| AT (1) | ATE3030T1 (en) |
| AU (1) | AU6266880A (en) |
| BR (1) | BR8006096A (en) |
| CA (1) | CA1155460A (en) |
| DE (2) | DE2938710A1 (en) |
| ES (1) | ES8105693A1 (en) |
| ZA (1) | ZA805924B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8198395B2 (en) * | 2007-02-07 | 2012-06-12 | Air Products And Chemicals, Inc. | Alkylated aminopropylated ethylenediamines and uses thereof |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU602186B2 (en) * | 1987-02-03 | 1990-10-04 | Merrell Dow Pharmaceuticals Inc. | Novel polyamine derivatives |
| US4967008A (en) * | 1990-01-12 | 1990-10-30 | Sherex Chemical Company, Inc. | Polyamines and their preparation |
| FR2714052B1 (en) * | 1993-12-22 | 1996-02-02 | Synthelabo | Preparation of substituted polyamines on the two terminal nitrogen. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2641836C2 (en) * | 1976-09-17 | 1978-11-16 | Th. Goldschmidt Ag, 4300 Essen | Alkylated polyamines, their production and use as microbicides & tgr |
| US4126640A (en) * | 1977-08-01 | 1978-11-21 | General Mills Chemicals, Inc. | N-alkyl polyamines and curing of epoxy resins therewith |
| DE2738538A1 (en) * | 1977-08-26 | 1979-03-01 | Henkel Kgaa | DISPERSING PIGMENTS |
-
1979
- 1979-09-25 DE DE19792938710 patent/DE2938710A1/en not_active Withdrawn
-
1980
- 1980-09-19 ES ES495180A patent/ES8105693A1/en not_active Expired
- 1980-09-20 DE DE8080105667T patent/DE3062759D1/en not_active Expired
- 1980-09-20 EP EP80105667A patent/EP0025997B1/en not_active Expired
- 1980-09-20 AT AT80105667T patent/ATE3030T1/en not_active IP Right Cessation
- 1980-09-24 AU AU62668/80A patent/AU6266880A/en not_active Abandoned
- 1980-09-24 CA CA000360957A patent/CA1155460A/en not_active Expired
- 1980-09-24 ZA ZA00805924A patent/ZA805924B/en unknown
- 1980-09-24 JP JP13175080A patent/JPS5657742A/en active Pending
- 1980-09-24 BR BR8006096A patent/BR8006096A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8198395B2 (en) * | 2007-02-07 | 2012-06-12 | Air Products And Chemicals, Inc. | Alkylated aminopropylated ethylenediamines and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| ES495180A0 (en) | 1981-06-16 |
| JPS5657742A (en) | 1981-05-20 |
| ES8105693A1 (en) | 1981-06-16 |
| EP0025997A1 (en) | 1981-04-01 |
| ZA805924B (en) | 1981-09-30 |
| DE3062759D1 (en) | 1983-05-19 |
| ATE3030T1 (en) | 1983-04-15 |
| BR8006096A (en) | 1981-04-07 |
| DE2938710A1 (en) | 1981-04-09 |
| EP0025997B1 (en) | 1983-04-13 |
| AU6266880A (en) | 1981-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |