CA2030378A1 - Process for the preparation of aminopolyalkylene oxides - Google Patents
Process for the preparation of aminopolyalkylene oxidesInfo
- Publication number
- CA2030378A1 CA2030378A1 CA002030378A CA2030378A CA2030378A1 CA 2030378 A1 CA2030378 A1 CA 2030378A1 CA 002030378 A CA002030378 A CA 002030378A CA 2030378 A CA2030378 A CA 2030378A CA 2030378 A1 CA2030378 A1 CA 2030378A1
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- raney
- oxides
- aluminum powder
- weight
- 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.)
- Abandoned
Links
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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/325—Polymers modified by chemical after-treatment with inorganic compounds containing nitrogen
- C08G65/3255—Ammonia
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyethers (AREA)
Abstract
Mo3493 LeA 27,380 A PROCESS FOR THE PREPARATION OF
AMINOPOLYALKYLENE OXIDES
ABSTRACT OF THE DISCLOSURE
The invention relates to a process for the preparation of aminopolyalkylene oxides by the reaction of (a) hydroxypolyalkylene oxide, (b) ammonia and/or primary or secondary amines, and (c) hydrogen gas, in the presence of (d) a mixture of (i) Raney catalysts and (ii) 1 to 50 percent by weight, based on the Raney catalyst, of aluminum powder as co-catalyst.
Mo3493
AMINOPOLYALKYLENE OXIDES
ABSTRACT OF THE DISCLOSURE
The invention relates to a process for the preparation of aminopolyalkylene oxides by the reaction of (a) hydroxypolyalkylene oxide, (b) ammonia and/or primary or secondary amines, and (c) hydrogen gas, in the presence of (d) a mixture of (i) Raney catalysts and (ii) 1 to 50 percent by weight, based on the Raney catalyst, of aluminum powder as co-catalyst.
Mo3493
Description
~'03~378 Mo3493 A PROCESS FOR THE PREPARATION OF
AMINOPOLYALKYLFNE OXIDES
BACKGROUND OF THE INVENTION
This invention relates to a process for the preparation of aminopolyalkylene oxides by reductive amination of hydroxypolyalkylene oxides in the presence of Raney nickel or Raney nickel/iron or Raney cobalt (hereinafter referred to as Raney catalysts) in admixture with aluminum powder as catalyst.
lo Raney nickel, Raney nickel/iron, or Raney cobalt are suitable for the reductive amination of compounds containing hydroxyl groups. See, for example Houben-Weyl XI/l (1957), pages 108-134.
U.S. Patent 4,766,245 describes the use as a catalyst for reductive amination of Raney nickel containing residual aluminum from the starting alloy after treatment with sodium hydroxide. In this catalyst, the aluminum is the embedding material, or rather the support, for the catalytically active nickel and does not contact atmospheric oxygen in this form.
It has now surprisingly been found that the activity of Raney nickel, Raney nickel/iron, or Raney cobalt can be considerably increased by the sole addition of aluminum powder.
SUMMARY OF THE INVENTION
Accordingly, the present invention relates to a simplified amination process for the preparation of aminopolyalkylene oxides comprising reacting (a) hydroxypolyalkylene oxides, (b) ammonia and/or primary or secondary amines, and (c) hydrogen gas, 30 - i n the presence of (d) a mixture of (i) Raney catalysts and (ii) 1 to 50 percent by weight, based on the Raney catalyst, of aluminum powder as co-catalyst.
Le A 27 380 DETAILED DESCRIPTION OF THE INVENTION
It was particularly surprising to find that the catalytic activity of the Raney catalyst could be considerably increased by the simple addition of aluminum powder, even after the aluminum has been exposed to air for several weeks and thus no intimate contact (such as would be found in an alloy with the catalytically active metal) can be expected. The aluminum powder may be introduced into the reaction mixture either as a mixture with the Raney catalyst or separately before or after addition of the Raney catalyst. The aluminum powder is used in a particle size of from about 4 to about 100 ~m, preferably from 10 to 50 ~m. The quantity of aluminum powder ranges from about 1 to about 50 percent by weight, based on the quantity of Raney catalyst.
Suitable hydroxypolyalkylene oxides used in the reductive amination process according to the invention are known hydroxypolyethers corresponding to the general formula R[-(A)-~]m wherein R is an m-functional residue of a Zerewitinoff-active compound obtainable by removal of m active hydrogen atoms;
A is a chain of linear and/or branched alkylene groups interrupted by oxygen atoms and having an average molecular weight (Mn) in the range from about 500 to about 10,000; and m is a number from 1 to 4.
Compounds of this type are described, for example, in British Patent 971,173.
Preferred hydroxypolyalkylene oxides are those in which R is a phendioxy group obtainable by removal of two phenolic hydrogen atoms. The phenolic OH groups from which the hydrogen atoms are removed may be located on one benzene ring or on two benzene rings in the same molecule. Examples of Mo3493 3 2 ~ 3 0 3 7 8 suitable compounds of this type include hydroquinone, 4,4'-diydroxybiphenyl, 4,4'-dihydroxydiphenylmethane, 2,2-bis(4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)ethane, 1,1-bis(4-hydroxyphenyl)cyclopentane, 1,1-bis(4-hydroxyphenyl)-cyclohexane, 1,1-bis(4-hydroxyphenyl), 4,4'-dihydroxystilbene, 4,4'-dihydroxytolane, 4,4'-dihydroxydiphenyl ether, 3,3'-di-hydroxydiphenyl ether, 1,4-dihydroxynaphthalene, 1,5-dihydroxy-naphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaph-thalene, 2,6-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1,4-bis(2-hydroxyethoxy)benzene, 1,5-bis(2-hydroxyethoxy)-naphthalene, and 2,2-bis[4-(2-hydroxyethoxy)phenyl]propane.
Although compounds in which R is a phendioxy group are preferred, it is not essential for R to be a phendioxy group.
Suitable hydroxypolyethers can be prepared, for example, from cyclic oxides, such as ethylene oxide, propylene oxide, butylene oxide, or tetrahydrofuran, in the presence of a catalyst and optionally in the presence of a compound containing several active hydrogen atoms (such as the preferred phendioxy compounds discussed above). See Encvclopedia of PolYmer Science and TechnoloqY, Vol. 6, pages 103-209, or Vol.
13, pages 670-689, Interscience Publishers, Inc., 1969. In any given hydroxypolyether, the alkylene groups need not all be identical. The alkylene groups may optionally be linear and/or branched (i.e., linear with alkyl substitution) and can be added randomly or in a particular sequence, depending on the quantity and sequence in which the cyclic oxides are added.
The amination reaction to form amine-terminated polyethers from the corresponding hydroxypolyethers takes place in the presence of ammonia, hydrogen, and the catalyst mixture of Raney nickel or Raney nickel/iron or Raney cobalt and aluminum powder. It is preferred to use ammonia as solvent.
When carrying out the amination reaction, 4 to 150 mole of ammonia and 0.5 to 10 mole of hydrogen are used per hydroxyl group of the polyether. In addition to ammonia, certain Mo3493 203~378 amines, preferably methylamine, dimethylamine, and morpholine, can be used for the process of the invention.
The reaction is conducted at temperatures in the range from about 140 to about 250C at a pressure of about 35 to about 350 atms gauge pressure ~preferably 140 to 180 atms gauge pressure). When using a batch process, the reaction times are in the range from about 0.5 to about 20 hours. When using a continuous process, the throughput rate should be about 0.1 to about 1.5 9 of starting hydroxypolyether per cm3 of catalyst per hour.
The compounds prepared according to the invention are particularly suitable as a chain-extending agent for polyurethane plastics and epoxides, as epoxy hardener, as a component of adhesives, as a modifier in polyamides, as a component in surface-active compounds (e.g., emulsifiers or antistatic finishing of textiles), or as a lubricating oil additive.
The following examples further illustrate details for the process of this invention. The invention, which is set forth in the foregoing disclosure, is not to be limited either in spirit or scope by these examples. Those skilled in the art will readily understand that known variations of the conditions of the following procedures can be used. Unless otherwise noted, all temperatures are degrees Celsius and all percentages are percentages by weight.
EXAMPLES
ExamPle 1 A polytetrahydrofuran having an OH number of 56 (1,500 9) was introduced into a 3 liter stirred autoclave at room temperature with 55 g of Raney Ni/Fe (70:30) (as disclosed e.g. in U.S. Patent Nb. 4,287,365) and 5.5 g of aluminum powder.
After purging with hydrogen, liquid ammonia (380 ml) was introduced and a hydrogen pressure of 30 bar was established. The reaction mixture was heated with stirring to 225C, with the pressure rising to approximately 180 bar.
Mo3493 After 20 hours at 225C, the autoclave was cooled and vented. The Raney Ni/Fe was filtered off and the filtrate was freed from volatile constituents (such as ammonia and water) in vacuo at 150C.
The NH2 content was 1.39% by weight, corresponding to a degree of amination of 87% (as determined by titration with 1 N HCl using bromphenol blue as indicator).
Comparison for Example 1 The corresponding amination of polytetrahydrofuran (OH value 56) without Al powder led to an NH2 content of 1.18%
by weight, corresponding to a degree of amination of 74%:
Example 2 A polyethylene glycol having an OH number of 14 (1,500 9) was aminated as described in Example 1. The 15 resultant product had an NH2 content of 0.40% by weight, corresponding to a degree of amination of 100%.
ComDarison for Exam~le 2 The corresponding amination without Al powder gave an NH2 content of 0.30% by weight, corresponding to a degree of 20 . amination of 75%.
Example 3 A bis(4-hydroxyphenyl)methane-started polypropylene glycol having an OH number of 112 (1,500 9) was aminated as in Example 1. The resultant product had an NH2 content of 2.85%
25 by weight, corresponding to a degree of amination of 89%.
Comparison for Example 3 The corresponding amination without Al powder gave an NH2 content of 1.69% by weight, corresponding to a degree of amination of 53%.
30 ExamDle 4 A bis(4-hydroxyphenyl)methane-started polypropylene glycol having an OH number of 112 (1,500 9) was aminated in the same way as in Example 3, except that 2.75 9 of aluminum powder was used instead of 5.5 9 of aluminum powder. The reaction Mo3493 product had an NH2 content of 2.30% by weight, corresponding to a degree of amination of 72%.
Example 5 A bis(4-hydroxyphenyl)methane-started polypropylene glycol having an OH number of 112 (1,500 g) was aminated in the same way as in Example 1, except that 55 g Raney nickel was used instead of 55 g Raney Ni/Fe. The resultant product had an NH2 content of 2.63% by weight, corresponding to a degree of amination of 82%.
o ComParison for Example 5 The corresponding amination without the Al powder gave an NH2 content of 1.92% by weight, corresponding to a degree of amination of 60%.
Mo3493
AMINOPOLYALKYLFNE OXIDES
BACKGROUND OF THE INVENTION
This invention relates to a process for the preparation of aminopolyalkylene oxides by reductive amination of hydroxypolyalkylene oxides in the presence of Raney nickel or Raney nickel/iron or Raney cobalt (hereinafter referred to as Raney catalysts) in admixture with aluminum powder as catalyst.
lo Raney nickel, Raney nickel/iron, or Raney cobalt are suitable for the reductive amination of compounds containing hydroxyl groups. See, for example Houben-Weyl XI/l (1957), pages 108-134.
U.S. Patent 4,766,245 describes the use as a catalyst for reductive amination of Raney nickel containing residual aluminum from the starting alloy after treatment with sodium hydroxide. In this catalyst, the aluminum is the embedding material, or rather the support, for the catalytically active nickel and does not contact atmospheric oxygen in this form.
It has now surprisingly been found that the activity of Raney nickel, Raney nickel/iron, or Raney cobalt can be considerably increased by the sole addition of aluminum powder.
SUMMARY OF THE INVENTION
Accordingly, the present invention relates to a simplified amination process for the preparation of aminopolyalkylene oxides comprising reacting (a) hydroxypolyalkylene oxides, (b) ammonia and/or primary or secondary amines, and (c) hydrogen gas, 30 - i n the presence of (d) a mixture of (i) Raney catalysts and (ii) 1 to 50 percent by weight, based on the Raney catalyst, of aluminum powder as co-catalyst.
Le A 27 380 DETAILED DESCRIPTION OF THE INVENTION
It was particularly surprising to find that the catalytic activity of the Raney catalyst could be considerably increased by the simple addition of aluminum powder, even after the aluminum has been exposed to air for several weeks and thus no intimate contact (such as would be found in an alloy with the catalytically active metal) can be expected. The aluminum powder may be introduced into the reaction mixture either as a mixture with the Raney catalyst or separately before or after addition of the Raney catalyst. The aluminum powder is used in a particle size of from about 4 to about 100 ~m, preferably from 10 to 50 ~m. The quantity of aluminum powder ranges from about 1 to about 50 percent by weight, based on the quantity of Raney catalyst.
Suitable hydroxypolyalkylene oxides used in the reductive amination process according to the invention are known hydroxypolyethers corresponding to the general formula R[-(A)-~]m wherein R is an m-functional residue of a Zerewitinoff-active compound obtainable by removal of m active hydrogen atoms;
A is a chain of linear and/or branched alkylene groups interrupted by oxygen atoms and having an average molecular weight (Mn) in the range from about 500 to about 10,000; and m is a number from 1 to 4.
Compounds of this type are described, for example, in British Patent 971,173.
Preferred hydroxypolyalkylene oxides are those in which R is a phendioxy group obtainable by removal of two phenolic hydrogen atoms. The phenolic OH groups from which the hydrogen atoms are removed may be located on one benzene ring or on two benzene rings in the same molecule. Examples of Mo3493 3 2 ~ 3 0 3 7 8 suitable compounds of this type include hydroquinone, 4,4'-diydroxybiphenyl, 4,4'-dihydroxydiphenylmethane, 2,2-bis(4-hydroxyphenyl)propane, 1,1-bis(4-hydroxyphenyl)ethane, 1,1-bis(4-hydroxyphenyl)cyclopentane, 1,1-bis(4-hydroxyphenyl)-cyclohexane, 1,1-bis(4-hydroxyphenyl), 4,4'-dihydroxystilbene, 4,4'-dihydroxytolane, 4,4'-dihydroxydiphenyl ether, 3,3'-di-hydroxydiphenyl ether, 1,4-dihydroxynaphthalene, 1,5-dihydroxy-naphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaph-thalene, 2,6-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1,4-bis(2-hydroxyethoxy)benzene, 1,5-bis(2-hydroxyethoxy)-naphthalene, and 2,2-bis[4-(2-hydroxyethoxy)phenyl]propane.
Although compounds in which R is a phendioxy group are preferred, it is not essential for R to be a phendioxy group.
Suitable hydroxypolyethers can be prepared, for example, from cyclic oxides, such as ethylene oxide, propylene oxide, butylene oxide, or tetrahydrofuran, in the presence of a catalyst and optionally in the presence of a compound containing several active hydrogen atoms (such as the preferred phendioxy compounds discussed above). See Encvclopedia of PolYmer Science and TechnoloqY, Vol. 6, pages 103-209, or Vol.
13, pages 670-689, Interscience Publishers, Inc., 1969. In any given hydroxypolyether, the alkylene groups need not all be identical. The alkylene groups may optionally be linear and/or branched (i.e., linear with alkyl substitution) and can be added randomly or in a particular sequence, depending on the quantity and sequence in which the cyclic oxides are added.
The amination reaction to form amine-terminated polyethers from the corresponding hydroxypolyethers takes place in the presence of ammonia, hydrogen, and the catalyst mixture of Raney nickel or Raney nickel/iron or Raney cobalt and aluminum powder. It is preferred to use ammonia as solvent.
When carrying out the amination reaction, 4 to 150 mole of ammonia and 0.5 to 10 mole of hydrogen are used per hydroxyl group of the polyether. In addition to ammonia, certain Mo3493 203~378 amines, preferably methylamine, dimethylamine, and morpholine, can be used for the process of the invention.
The reaction is conducted at temperatures in the range from about 140 to about 250C at a pressure of about 35 to about 350 atms gauge pressure ~preferably 140 to 180 atms gauge pressure). When using a batch process, the reaction times are in the range from about 0.5 to about 20 hours. When using a continuous process, the throughput rate should be about 0.1 to about 1.5 9 of starting hydroxypolyether per cm3 of catalyst per hour.
The compounds prepared according to the invention are particularly suitable as a chain-extending agent for polyurethane plastics and epoxides, as epoxy hardener, as a component of adhesives, as a modifier in polyamides, as a component in surface-active compounds (e.g., emulsifiers or antistatic finishing of textiles), or as a lubricating oil additive.
The following examples further illustrate details for the process of this invention. The invention, which is set forth in the foregoing disclosure, is not to be limited either in spirit or scope by these examples. Those skilled in the art will readily understand that known variations of the conditions of the following procedures can be used. Unless otherwise noted, all temperatures are degrees Celsius and all percentages are percentages by weight.
EXAMPLES
ExamPle 1 A polytetrahydrofuran having an OH number of 56 (1,500 9) was introduced into a 3 liter stirred autoclave at room temperature with 55 g of Raney Ni/Fe (70:30) (as disclosed e.g. in U.S. Patent Nb. 4,287,365) and 5.5 g of aluminum powder.
After purging with hydrogen, liquid ammonia (380 ml) was introduced and a hydrogen pressure of 30 bar was established. The reaction mixture was heated with stirring to 225C, with the pressure rising to approximately 180 bar.
Mo3493 After 20 hours at 225C, the autoclave was cooled and vented. The Raney Ni/Fe was filtered off and the filtrate was freed from volatile constituents (such as ammonia and water) in vacuo at 150C.
The NH2 content was 1.39% by weight, corresponding to a degree of amination of 87% (as determined by titration with 1 N HCl using bromphenol blue as indicator).
Comparison for Example 1 The corresponding amination of polytetrahydrofuran (OH value 56) without Al powder led to an NH2 content of 1.18%
by weight, corresponding to a degree of amination of 74%:
Example 2 A polyethylene glycol having an OH number of 14 (1,500 9) was aminated as described in Example 1. The 15 resultant product had an NH2 content of 0.40% by weight, corresponding to a degree of amination of 100%.
ComDarison for Exam~le 2 The corresponding amination without Al powder gave an NH2 content of 0.30% by weight, corresponding to a degree of 20 . amination of 75%.
Example 3 A bis(4-hydroxyphenyl)methane-started polypropylene glycol having an OH number of 112 (1,500 9) was aminated as in Example 1. The resultant product had an NH2 content of 2.85%
25 by weight, corresponding to a degree of amination of 89%.
Comparison for Example 3 The corresponding amination without Al powder gave an NH2 content of 1.69% by weight, corresponding to a degree of amination of 53%.
30 ExamDle 4 A bis(4-hydroxyphenyl)methane-started polypropylene glycol having an OH number of 112 (1,500 9) was aminated in the same way as in Example 3, except that 2.75 9 of aluminum powder was used instead of 5.5 9 of aluminum powder. The reaction Mo3493 product had an NH2 content of 2.30% by weight, corresponding to a degree of amination of 72%.
Example 5 A bis(4-hydroxyphenyl)methane-started polypropylene glycol having an OH number of 112 (1,500 g) was aminated in the same way as in Example 1, except that 55 g Raney nickel was used instead of 55 g Raney Ni/Fe. The resultant product had an NH2 content of 2.63% by weight, corresponding to a degree of amination of 82%.
o ComParison for Example 5 The corresponding amination without the Al powder gave an NH2 content of 1.92% by weight, corresponding to a degree of amination of 60%.
Mo3493
Claims (4)
1. A process for the preparation of an aminopolyalkylene oxide comprising reacting (a) a hydroxypolyalkylene oxide, (b) ammonia and/or a primary or secondary amine, and (c) hydrogen gas, in the presence of (d) a mixture of (i) a Raney catalyst and (ii) 1 to 50 percent by weight, based on the Raney catalyst, of aluminum powder as co-catalyst.
2. A process according to Claim 1 wherein the aluminum powder has a particle size of from 4 to 100 µm.
3. A process according to Claim 1 wherein the hydroxypolyalkylene oxide corresponds to the formula R[-(A)-OH]m wherein R is an m-functional residue of a Zerewitinoff-active compound obtainable by removal of m active hydrogen atoms;
A is a chain of linear and/or branched alkylene groups interrupted by oxygen atoms and having an average molecular weight in the range from 500 to 10,000; and m is a number from 1 to 4.
A is a chain of linear and/or branched alkylene groups interrupted by oxygen atoms and having an average molecular weight in the range from 500 to 10,000; and m is a number from 1 to 4.
4. A process according to Claim 1 wherein the hydroxypolyalkylene oxide corresponds to the formula R[-(A)-OH]2 wherein R is a phendioxy group; and A is a chain of linear and/or branched alkylene groups interrupted by oxygen atoms and having an average molecular weight in the range from 500 to 10,000.
Mo3493
Mo3493
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3941789.1 | 1989-12-19 | ||
| DE3941789A DE3941789A1 (en) | 1989-12-19 | 1989-12-19 | METHOD FOR PRODUCING AMINOPOLYALKYLENE OXIDES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2030378A1 true CA2030378A1 (en) | 1991-06-20 |
Family
ID=6395722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002030378A Abandoned CA2030378A1 (en) | 1989-12-19 | 1990-11-20 | Process for the preparation of aminopolyalkylene oxides |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0433777B1 (en) |
| JP (1) | JPH04117422A (en) |
| CA (1) | CA2030378A1 (en) |
| DE (2) | DE3941789A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5483008A (en) * | 1992-02-07 | 1996-01-09 | Research Development Corporation Of Japan | Polyether having heterofunctional groups at both ends, process for the preparation thereof and polymerization initiator therefor |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2614103B1 (en) * | 2010-09-10 | 2015-04-15 | Invista Technologies S.a r.l. | Polyetheramines, compositions including polyetheramines, and methods of making |
| CN107075067A (en) | 2014-09-25 | 2017-08-18 | 巴斯夫欧洲公司 | Polyetheramine based on 1,3 glycol |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1590871A (en) * | 1968-11-06 | 1970-04-20 | ||
| US4766245A (en) * | 1985-03-01 | 1988-08-23 | Texaco Inc. | Process for the preparation of polyoxyalkylene polyamines |
| DE3608716A1 (en) * | 1985-05-31 | 1986-12-04 | Texaco Development Corp., White Plains, N.Y. | METHOD FOR PRODUCING POLYOXYALKYLENE POLYAMINES |
-
1989
- 1989-12-19 DE DE3941789A patent/DE3941789A1/en not_active Withdrawn
-
1990
- 1990-11-20 CA CA002030378A patent/CA2030378A1/en not_active Abandoned
- 1990-12-06 EP EP90123368A patent/EP0433777B1/en not_active Expired - Lifetime
- 1990-12-06 DE DE59008589T patent/DE59008589D1/en not_active Expired - Fee Related
- 1990-12-17 JP JP2411081A patent/JPH04117422A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5483008A (en) * | 1992-02-07 | 1996-01-09 | Research Development Corporation Of Japan | Polyether having heterofunctional groups at both ends, process for the preparation thereof and polymerization initiator therefor |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3941789A1 (en) | 1991-06-20 |
| EP0433777A2 (en) | 1991-06-26 |
| EP0433777A3 (en) | 1991-12-18 |
| EP0433777B1 (en) | 1995-03-01 |
| JPH04117422A (en) | 1992-04-17 |
| DE59008589D1 (en) | 1995-04-06 |
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