GB1561617A - High tertiary aminecontent compositions useful as polyurethane catalysts - Google Patents
High tertiary aminecontent compositions useful as polyurethane catalysts Download PDFInfo
- Publication number
- GB1561617A GB1561617A GB3361877A GB3361877A GB1561617A GB 1561617 A GB1561617 A GB 1561617A GB 3361877 A GB3361877 A GB 3361877A GB 3361877 A GB3361877 A GB 3361877A GB 1561617 A GB1561617 A GB 1561617A
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- Prior art keywords
- bis
- dimethylaminopropyl
- alkyl
- compound
- hydrogen
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/14—Amines containing amino groups bound to at least two aminoalkyl groups, e.g. diethylenetriamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/14—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by amino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- 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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1808—Catalysts containing secondary or tertiary amines or salts thereof having alkylene polyamine groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(54) HIGH TERTIARY AMINE CONTENT COMPOSITIONS
USEFUL AS POLYURETHANE CATALYSTS
(71) We, TEXACO DEVELOPMENT CORPORATION. a corporation organised and existing under the laws of the State of Delaware, United States of
America, of 135 East 42nd Street, New York, New York 10017. United States of
America, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- This invention relates to polyurethane catalysts. More particularly, this invention relates to certain amines which are useful as catalysts in the preparation of polyurethanes.
Catalysts are used to prepare polyurethanes by the reaction of a polyisocyanate, a polyol and perhaps other ingredients. The catalyst is employed to promote at least two, and sometimes three, major reactions that must proceed simultaneously and competitively at balanced rates during the process, in order to provide polyurethanes with the desired physical characteristics. One reaction is a chain extending isocyanate/hydroxyl reaction, by which a hydroxyl-containing molecule is reacted with an isocyanate-containing molecule to form a urethane.
This increases the viscosity of the mixture and provides a polyurethane that contains secondary nitrogen atoms in the urethane groups. A second reaction is a cross-linking isocyanate/urethane reaction, by which an isocyanate-containing molecule reacts with a urethane group containing a secondary nitrogen atom. The third reaction which may be involved is an isocyanate/water reaction by which an isocyanate-terminated molecule is extended and by which carbon dioxide is generated to blow, or to assist in the blowing of, a foam. This third reaction is not essential if an extraneous blowing agent, such as halogenated, liquid hydrocarbon, or carbon dioxide. is employed, but is essential if all or even a part of the gas for foam generation is to be generated by this in-situ reaction (e.g. in the preparation of "one-shot" flexible polyurethane foams).
The reactions must proceed simultaneously at optimum balanced rates relative to each other in order to provide a good foam structure. If carbon dioxide evolution is too rapid in comparison with chain extension. the foam will collapse. If the chain extension is too rapid in comparison with carbon dioxide evolution, foam rise will be restricted, resulting in a high density foam with a high percentage of poorly defined cells. The foam will not be stable in the absence of adequate crosslinking.
It is long been known that tertiary amines, such as trimethylamine and triethylamine are effective for catalyzing the second crosslinking reaction. Other typical tertiary amines are set forth in U.S. Patents No. 3,925,268: 3,127,436: and 3,243.389; and in German Offenlegungsschrifls 2,354,952 and 2,259,980. Some of the tertiary amines are effective for catalyzing the third. water/isocyanate reaction for carbon dioxide evolution. Tertiary amines are, however, only partially effective as catalysts for the first chain extension reaction. To overcome this problem. the so-called "prepolymer" technique has been developed, wherein a hydroxycontaining polyol component is partially reacted with the isocyanate component in order to provide a liquid prepolymer containing free isocyanate groups. This prepolymer is then reacted with additional polyol in the presence of a tertiary amine to provide a foam. This method is still commonly employed in preparing rigid urethane foams, but has proven less satisfactory for the production of flexible urethane foams.
For flexible foams, a one-step or "one-shot" process has been developed.
wherein a tertiary amine, such as triethylenediamine, is employed in conjunction with an organic tin compound. Triethylenediamine is particularly active for promoting the water/isocyanate reaction, and the tin compound is particularly active in synergenistic combination with the triethylenediamine for promoting the chain extension reaction. Even here, however, the results obtained leave much to be desired. Triethylenediamine is a solid, and must be dissolved before use to avoid processing difficulties. Also, triethylenediamine and other of the prior art amines can impart a strong amine odour to the polyurethane foam.
In addition to these problems of odour and handling, other tertiary amines have still further defects. For example, in some instances the compounds are relatively volatile, leading to obvious safety problems. In addition, some catalysts of this type do not provide sufficient delay in foaming, which delay is particularly desirable in moulding applications to allow sufficient time to place the preform mix in the mold. Other catalysts, while meeting specifications in this area, do not yield foams with a desirable tack-free time.
Lastly, while certain tertiary amines do not have the defects mentioned above, they nevertheless do not have a sufficient high tertiary amine content. It is believed that the higher the tertiary amine content, the more rapid the catalytic activity.
The present invention provides a compound of the formula
wherein R is alkyl; R1 is a group of the formula -CH2CHR2-Y, -CH2OR3 or
R2 is hydrogen, alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, aralkyl or substituted aralkyl,
R3 is hydrogen or alkyl;
R4 is hydrogen, alkyl, aryl or substituted aryl; and
Y is -OH, -CN, -CONR42, -CO2R4, or COR4.
One preferred group of compounds has the formula
wherein Y is -CN, -CONR42, -CO2R4 or COR4 and R, R2 and R4 have the meanings given above. Preferred compounds of this class are those in which R is methyl, in which Y is -CN and R2 is hydrogen, and in which Y is -CONH2.
Specific preferred compounds are N-cyanoethyl-N,N-bis-(dimethylamino propyl) amine and 3-[bis(dimethylaminopropyl)amino]propionamide.
A second preferred group of compounds has the tormula
(in) wherein R is alkyl and R4 is hydrogen, alkyl or aryl, for instance, bis-[bis-(3 dimethylaminopropyl)amino] methane.
A third preferred group of compounds has the formula
wherein R is alkyl and R3 is hydrogen or alkyl, for instance. [bis-(3dimethylaminopropyl)amino methyl] methyl ether.
A fourth preferred group of compounds has the formula
wherein R and R2 have the meanings given above, for instance. bis-(3dimethylaminopropyl) (2-hydroxypropyl)amine and bis-(3-dimethylaminopropyl) (2-hydroxyethyl)amine.
These components are useful as catalysts in accordance with our co-pending
British Patent Application No. 23635/78 (Serial No. 1,561,618) which relates to a method for producing a polyurethane which comprises reacting an organic polyisocyanate with an organic polyester polyol or polyether polyol in the presence of a catalyst of the formula:
wherein R is alkyl;
R1 is alkyl or a group of the formula -CH2CHR2-Y, -CH2OR3 or
R2 is hydrogen, alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, aralkyl or substituted aralkyl,
R3 is hydrogen or alkyl;
R4 is hydrogen, alkyl or aryl; and
Y is -OH, -CN, -CONR42, -CO2R4, or -COR4.
The compounds set out above may be prepared by a wide variety of synthetic techniques. Preferably, however, they are prepared by first making a bis(dialkylaminopropyl)-amine, (hereinafter referred to as "the bis-amine") which may itself be prepared by a variety of known techniques. One excellent mode of preparation involves a reaction of a dialkylamine, such as dimethylamine, with acrylonitrile, followed by hydrogenation of the resultant condensate to produce dimethylaminopropylamine. In producing dimethylaminopropylamine, one also produces the bis-dimethylaminopropylamine compound, which may be removed from the monomolecule by conventional means such as distillation and the like.
The bis-amine then readily forms the compounds of formula (II) by reacting with a variety of monomers of the type CH2=CHR2Y where R2 and Y have the meaning given above. Typical reactants of this type include acrylamine, acrylonitrile, acrylic acid, and alkyl or aryl esters thereof, N,N-disubstituted acrylamine derivatives, and vinylketones such as methyl vinyl ketone.
Most preferred compounds are those where R in the above formulae is methyl.
Thus, greatly preferred compositions have the formula [(CH3)2NCH2CH2CH2]2NX where X=
1. CH2CH2CN
2. CH2CH2CONH2
3. CH2CH2CO2CH, 4. CH2CH2CHO
5. CH2CH2CO2H
6. CH2CH2COCHo 7. CH2CH(CH3)Y where
Y=CN, CO2CH3, CO2H, CONH2, CHO
8. CH2CH2CO2R4
9. CH2CH2CON42 10. CH2CHR2CO2R4 where
R2 is CH3 or ET
11. CH2CHR2CONR4 Compounds of the general formula (III) can be prepared by.reacting the bisamine with a variety of aldehydes such as formaldehyde, and others of the type
R4CHO where R4 may be hydrogen, alkyl or aryl. A greatly preferred reactant is formaldehyde. Other preferred aldehydes are those in which R4 is alkyl such as methyl, ethyl, propyl and butyl. Thus R4, preferably contains I to 4 carbon atoms.
R4 may also be phenyl or substituted phenyl, such as halosubstituted phenvl.
In order to produce the compounds of formula (IV) one merely reacts the bisamine with formaldehyde (if R3 is H) or with formaldehyde and an alcohol (if R3 is alkyl). The alcohol may be chosen from a wide variety of alkanols, including methyl alcohol, ethyl alcohol, propyl alcohol, and butyl alcohol.
In work performed here in preparing the above compounds another class of materials was synthesized, which though not believed novel, nevertheless were shown to have excellent urethane catalyst activity. These compounds have the formula (I) wherein R and R' are both alkyl.
Again R' is preferably alkyl having 1 to 4 carbon atoms. Materials of this type may be prepared by again reacting the bis-amine with an aldehyde and alcohol
combination. Here, however, instead of removing excess alcohol by vacuum to
prepare compounds of the formula (III), the reaction mixture is hydrogenated over conventional hydrogenation catalysts such as nickel to produce its desired
compounds.
Compounds of the general formula (V) can be obtained by reacting the bis
amines with a variety of olefine oxides of the formula:
where R1 has the meaning given above. Mixtures of olefin oxides may also be employed to form the catalysts of the invention.
The olefin oxides which may be employed as reactants, include ethylene oxide, propylene oxide, butylene oxide, hexylene oxide, octylene oxide. dodecene oxide, styrene oxide, and cyclohexane oxide. Alkyl, cyano, nitro, halo, and other addition substituents may also be present in the above olefine oxides.
Greatly preferred olefin oxide reactants are alkylene oxides having from 2 to
18 carbon atoms, most preferably, ethylene oxide and propylene oxide.
The reaction of an olefin oxide, such as an alkylene oxide, with an aminecontaining reactant as described above is well known to those skilled in the art.
Such a reaction is normally carried out under basic conditions established through the use of alkali metals, their hydroxides, oxides and hydrides, and in some cases basic amines. The reaction of the bis-amine with olefin oxides is substantially on a mol per mol basis.
The compounds described above possess a number of useful characteristics making them exceptionally attractive as polyurethane catalysts. For example, they have a high tertiary amine content and resultant rapid catalytic activity for forming polyurethane foams. Tertiary amine content is calculated as the number of tertiary amino groups divided by the molecular weight times 1,000. For example, the acrylonitrile adduct of bis-(dimethylaminopropyl)-amine has a tertiary amine content of 12.48 meqlg. In addition, the compounds are also relatively non-volatile and possess little if any odour. There are no solids-handling problems such as are present with such well known polyurethane catalysts as triethylenediamine. The catalysts used according to the invention are particularly desirable in foaming urethanes in that they provide a sufficient delay in the foaming operation to aid in processing. Yet the catalysts also give good foams with desirable tackfree times. As noted above, this delay time is particularly desirable in moulding applications to allow sufficient time to place the prefoam mix in the mold. Lastly, the compounds are easily prepared as typically described above, and are relatively inexpensive.
For further details of the use of the compounds according to the invention in the preparation of polyurethanes, attention is directed to our co-pendin,e British
Patent Application No. 23635/78. (Serial No. 1561618).
The invention will be illustrated further with respect to the following specific examples, which are given by way of illustration and not as limitations on the scope of this invention.
EXAMPLE I
187 g of bis-(dimethylaminopropyl)-amine (BDMAPA) and 103 g of isopropanol were placed in a 500 ml reactor equipped with a stirrer, thermometer and nitrogen atmosphere. Acrylonitrile, (64 g), was added and the solution was refluxed for 1 hour, then a further 8 g of acrylonitrile was added. Reflux was continued for 2 hours, then excess acrylonitrile and isopropanol were distilled overhead. A vacuum of 0.8 mm was applied for 0.5 hours to remove traces of volatiles, and the product was recovered in quantitative yield. Its identity as Ncyanoethyl-N,N-bis-(dimethylaminopropyl)-amine was confirmed by infra red and nmr spectroscopy. The flash point of this compound was desirably high. 190"F.
EXAMPLE 2
112 g of BDMAPA was placed in an apparatus similar to that used in Example I. Dropwise addition of 86 g of a 50," solution of acrylamide produced a moderate exotherm. After the addition, the mixture was heated at 50 to 600C for 3 hours.
Water formed in the reaction was removed by benzene azeotrope followed by vacuum application at 0.4 mm of mercy for 2 hours. The product was recovered in quantitive yield and had no detectable odour. IR and NMR spectroscopy
confirmed the identity of the compound as 3-[bis (dimethylaminopropyl)aminolpropionamide.
EXAMPLE 3
A 500 ml reactor equipped with a stirrer, thermometer, and addition funnel
was charged with 100 ml of methanol and 30 g of paraformaldehyde. 187 g of
BDMAPA was added dropwise over 45 min with stirring and the reaction mixture
was allowed to remain overnight at room temperature. This entire procedure was
conducted with a nitrogen atmosphere.
Excess methanol was removed by applying a vacuum of 30 mm of mercy and
heating to 70"C. Filtration of the hazy mixture yielded 189 g of product, identified
as [bis-(3-dimethylaminopropyl)aminomethyli methylether by nmr and ir
spectroscopy.
EXAMPLE 4
A I-litre reactor equipped with a water separator. reflux condenser.
thermometer, and stirrer was charged with 374 g of BDMAPA and 100 g of benzene. Then 28 g of paraformaldehyde was added in 5 g portions, stirring until dissolved. After standing overnight, the solution was refluxed for two hours until 16 ml of water had collected. The product was then stripped of volatiles by applying a
vacuum to 0.2 mm of mercury and heating to 140"C. The product was collected as the bottoms materials and identified by nmr and ir spectroscopy as bis[bis(3- dimethylaminopropyl)amino] methane.
EXAMPLE 5
A mixture of 187 g of BDMAPA and 68 g of propylene oxide was sealed (in nitrogen atmosphere) in a stainless steel 1 litre autoclave and heated at 100"C for 2 hours, then at 130"C for 3 hours. NMR and IR spectroscopy revealed the major product was bis-(3-dimethylaminopropyl) (2-hydroxypropyl) amine.
WHAT WE CLAIM IS:
1. A compound of the formula
wherein R is alkyl; R1 is a group of the formula -CH2CHR2-Y, -CH2OR3 or
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (15)
- **WARNING** start of CLMS field may overlap end of DESC **.For further details of the use of the compounds according to the invention in the preparation of polyurethanes, attention is directed to our co-pendin,e British Patent Application No. 23635/78. (Serial No. 1561618).The invention will be illustrated further with respect to the following specific examples, which are given by way of illustration and not as limitations on the scope of this invention.EXAMPLE I187 g of bis-(dimethylaminopropyl)-amine (BDMAPA) and 103 g of isopropanol were placed in a 500 ml reactor equipped with a stirrer, thermometer and nitrogen atmosphere. Acrylonitrile, (64 g), was added and the solution was refluxed for 1 hour, then a further 8 g of acrylonitrile was added. Reflux was continued for 2 hours, then excess acrylonitrile and isopropanol were distilled overhead. A vacuum of 0.8 mm was applied for 0.5 hours to remove traces of volatiles, and the product was recovered in quantitative yield. Its identity as Ncyanoethyl-N,N-bis-(dimethylaminopropyl)-amine was confirmed by infra red and nmr spectroscopy. The flash point of this compound was desirably high. 190"F.EXAMPLE 2112 g of BDMAPA was placed in an apparatus similar to that used in Example I. Dropwise addition of 86 g of a 50," solution of acrylamide produced a moderate exotherm. After the addition, the mixture was heated at 50 to 600C for 3 hours.Water formed in the reaction was removed by benzene azeotrope followed by vacuum application at 0.4 mm of mercy for 2 hours. The product was recovered in quantitive yield and had no detectable odour. IR and NMR spectroscopy confirmed the identity of the compound as 3-[bis (dimethylaminopropyl)aminolpropionamide.EXAMPLE 3 A 500 ml reactor equipped with a stirrer, thermometer, and addition funnel was charged with 100 ml of methanol and 30 g of paraformaldehyde. 187 g of BDMAPA was added dropwise over 45 min with stirring and the reaction mixture was allowed to remain overnight at room temperature. This entire procedure was conducted with a nitrogen atmosphere.Excess methanol was removed by applying a vacuum of 30 mm of mercy and heating to 70"C. Filtration of the hazy mixture yielded 189 g of product, identified as [bis-(3-dimethylaminopropyl)aminomethyli methylether by nmr and ir spectroscopy.EXAMPLE 4 A I-litre reactor equipped with a water separator. reflux condenser.thermometer, and stirrer was charged with 374 g of BDMAPA and 100 g of benzene. Then 28 g of paraformaldehyde was added in 5 g portions, stirring until dissolved. After standing overnight, the solution was refluxed for two hours until 16 ml of water had collected. The product was then stripped of volatiles by applying a vacuum to 0.2 mm of mercury and heating to 140"C. The product was collected as the bottoms materials and identified by nmr and ir spectroscopy as bis[bis(3- dimethylaminopropyl)amino] methane.EXAMPLE 5 A mixture of 187 g of BDMAPA and 68 g of propylene oxide was sealed (in nitrogen atmosphere) in a stainless steel 1 litre autoclave and heated at 100"C for 2 hours, then at 130"C for 3 hours. NMR and IR spectroscopy revealed the major product was bis-(3-dimethylaminopropyl) (2-hydroxypropyl) amine.WHAT WE CLAIM IS: 1. A compound of the formulawherein R is alkyl; R1 is a group of the formula -CH2CHR2-Y, -CH2OR3 orR2 is hydrogen, alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, aralkyl or substituted aralkyl, R3 is hydrogen or alkyl; R4 is hydrogen, alkyl, aryl; or substituted aryl; and Y is -OH, -CN, -CONR42, -CO2R4 or -COR4.
- 2. A compound of the formula:wherein Y is -CN, -CONR42, -CO2R4 or -COR4 and R, R2 and R4 have the meanings given in Claim 1.
- 3. A compound as claimed in Claim 2 wherein R is methyl.
- 4. A compound as claimed in Claim 2 or 3 wherein Y is CN and R2 is hydrogen.
- 5. A compound as claimed in Claim 2 or 3 wherein Y is CONH2.
- 6. N-cyanoethyl-N,N-bis-(dimethylaminopropyl)amine.
- 7. 3-[bis-(dimethylaminopropyl)amino]propionamide.
- 8. A compound of the formula:wherein R- is alkyl and R4 is hydrogen, alkyl or aryl.
- 9. bis-[bis-(3-dimethylaminopropyl)amino] methane.
- 10. A compound of the formula:wheh is alkyl and R3 is hydrogen or alkyl.
- 11. [bis-(3-dimethylaminopropyl)aminomethyl]-methyl ether.
- 12. A compound of the formula:where R is alkyl, and R2 is hydrogen, alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, aralkyl, or substituted aralkyl.
- 13. A compound as claimed in Claim 12 wherein R is methyl.
- 14. bis-(3-dimethylaminopropyl) (2-hydroxypropyl) amine.
- 15. bis-(3-dimethylaminopropyl) (2-hydroxyethyl amine.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/733,548 US4049591A (en) | 1976-10-18 | 1976-10-18 | Foams and elastomers prepared in the presence of high tertiary amine content polyurethane catalysts |
| US05/740,991 US4101470A (en) | 1976-11-11 | 1976-11-11 | Urethane catalysts |
| US05/746,577 US4101466A (en) | 1976-12-01 | 1976-12-01 | Bis (dimethylaminopropyl)-amine derivatives as polyurethane catalysts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1561617A true GB1561617A (en) | 1980-02-27 |
Family
ID=27419177
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3361877A Expired GB1561617A (en) | 1976-10-18 | 1977-08-10 | High tertiary aminecontent compositions useful as polyurethane catalysts |
| GB2363578A Expired GB1561618A (en) | 1976-10-18 | 1977-08-10 | Polyurethane formation using high tertiary amine content catalysts |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2363578A Expired GB1561618A (en) | 1976-10-18 | 1977-08-10 | Polyurethane formation using high tertiary amine content catalysts |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5350110A (en) |
| BR (1) | BR7706913A (en) |
| FR (1) | FR2367734A1 (en) |
| GB (2) | GB1561617A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8222311B2 (en) | 2004-11-02 | 2012-07-17 | Tosoh Corporation | Hydroxyalkylated polyalkylenepolyamine composition, method of producing the same and their use in polyurethanes |
| EP2695608A2 (en) * | 2006-10-03 | 2014-02-12 | Tekmira Pharmaceuticals Corporation | Lipid containing formulations |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4080343A (en) * | 1976-09-22 | 1978-03-21 | Abbott Laboratories | Polyurethane catalyst |
| US5374666A (en) * | 1990-07-30 | 1994-12-20 | Tosoh Corporation | Amine catalyst for producing polyurethane and process for producing polyurethane |
| US5559161A (en) * | 1994-02-18 | 1996-09-24 | Air Products And Chemicals, Inc. | Hydroxy-functional triamine catalyst compositions for the production of polyurethanes |
| CN107922579B (en) * | 2015-06-01 | 2021-06-08 | 赢创运营有限公司 | Reactive amine catalysts for polyurethane applications |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3036020A (en) * | 1958-06-30 | 1962-05-22 | Mobay Chemical Corp | Process of making cellular polyurethane using n, n-dialkyl-3-(dialkyl amino) propylamine catalyst |
| US3324182A (en) * | 1962-12-26 | 1967-06-06 | Monsanto Res Corp | Penta-alkyldialkylenetriamines |
-
1977
- 1977-08-10 GB GB3361877A patent/GB1561617A/en not_active Expired
- 1977-08-10 GB GB2363578A patent/GB1561618A/en not_active Expired
- 1977-10-04 FR FR7729761A patent/FR2367734A1/en active Granted
- 1977-10-17 BR BR7706913A patent/BR7706913A/en unknown
- 1977-10-18 JP JP12413977A patent/JPS5350110A/en active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8222311B2 (en) | 2004-11-02 | 2012-07-17 | Tosoh Corporation | Hydroxyalkylated polyalkylenepolyamine composition, method of producing the same and their use in polyurethanes |
| US8765008B2 (en) | 2004-11-02 | 2014-07-01 | Tosoh Corporation | Hydroxyalkylated polyalkylenepolyamine composition, method for producing same and method for producing polyurethane resin using such hydroxyalkylated polyalkylenepolyamine composition |
| EP2695608A2 (en) * | 2006-10-03 | 2014-02-12 | Tekmira Pharmaceuticals Corporation | Lipid containing formulations |
| EP2695608A3 (en) * | 2006-10-03 | 2014-05-21 | Tekmira Pharmaceuticals Corporation | Lipid containing formulations |
| US11420931B2 (en) | 2006-10-03 | 2022-08-23 | Arbutus Biopharma Corporation | Lipid containing formulations |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2367734B1 (en) | 1981-04-30 |
| GB1561618A (en) | 1980-02-27 |
| JPS5630340B2 (en) | 1981-07-14 |
| FR2367734A1 (en) | 1978-05-12 |
| BR7706913A (en) | 1978-07-18 |
| JPS5350110A (en) | 1978-05-08 |
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