KR100302090B1 - Reactive amine catalysts and their use in polyurethane polymers - Google Patents

Abstract

The present invention provides an amine / amide catalyst for use as a catalyst in a polyurethane forming reaction. Amine / amide catalysts having low volatility due to their reactivity with isocyanate and having good catalytic activity have the structure of the following formula (2).

(2)

In this formula,

Q is C _z H _{2z + 1} or _{(CH 2) n N (R} 3) and _k T, T is both terminals divalent cyclic to form a cyclic attached to the nitrogen group, or or a monovalent alkyl, aminoalkyl K is 0 or 1 if T is 1, k is 1 if T is 2, k is 0, R ² is H or C _z H _{2z + 1} , and R ³ is C _z H _{2z + 1} , R ⁴ is H, R ⁵ is H or CH ₃ , n is 2 to 6, and z is 1 to 4. n is preferably 2 or 3, and z is preferably 1. Each of R < ³ > and T is the same or different depending on the value of each n and z. One especially preferred range of the above formulas is that Q is C _z H _{2z + 1} .

Description

Reactive amine catalysts and their use in polyurethane polymers

Certain amine catalysts are known in the polyurethane industry, one example of which is the simplest N, N-dimethyl-3- [dimethyl < RTI ID = 0.0 > Amino] propanamide (DDPA, shown below).

[Chemical Formula 1]

A similar non-reactive analogue found to be useful as a polyurethane catalyst is 3- [bis- (3- [dimethylamino] propyl)] amino-N, N-dimethylpropanamide as described in U.S. Patent No. 4,049,591.

Also, many hydroxyl and primary / secondary amine containing tertiary amine polyurethane catalysts are described in " Factors Affecting the Discoloration of Vinyl That Has Been Molded Against Urethane Foam, " Zimmerman and T.L. Austin, Polyurethane World Congress 1987, Sept. 20-Oct. 2, pp. 693-697, 1987. However, all of these catalysts have defects in activity in the case of hydroxy substitution, or in volatility in the case of being unsubstituted.

U.S. Pat. No. 4,384,950 describes the use of the substituted form of DDPA as an anti-emulsifier for destroying oil-in-water emulsions from the tar-sand bitumen recovery process. However, the above patent does not disclose the use of the above compound as a catalyst for the urethane system. The reaction used in the preparation of the substituted compound includes addition / condensation of methacrylic acid or acrylic acid with dimethylaminopropylamine. Methods of making such compounds are described in U.S. Patent Nos. 4,256,665 and 4,259,259.

It is an object of the present invention to provide an amine / amide catalyst which catalyzes polyurethane formation with high reactivity and low volatility.

The present invention provides amine / amide catalysts for use in catalyzing polyurethane formation. The amine / amide catalyst has low volatility (i.e., low fogging) in the resulting polyurethane and good reactivity at least as much as the most reactive component in the system (see Priester, RD Jr., et al. , RD Pefley and RB Turner, " High Resiliency Polyurea Foam - An Improved Flexible Foam Matrix, Journal of Cellular Plastics, 30 (2) 1994, pp.147), these compounds have a basic structure similar to DDPA, Unexpectedly, these highly reactive compounds have very similar catalytic activities to fully unsubstituted catalysts DDPA.

The tertiary amine / amide of the present invention has the structure of the following formula (2)

(2)

In this formula,

Q is C _Z H _{2Z + 1} or ((CH ₂ ) _n N (R ³ ) _k T,

T is a divalent cyclic group having both terminals attached to nitrogen to form a cyclic group, or T is a monovalent alkyl, aminoalkyl or alkylaminoalkyl group,

k is 0 or 1, k is 1 when T is 1, k is 0 if T is 2,

R ² is H or C _Z H _{2Z + 1} ,

R ³ is C _Z H _{2Z + 1} ,

R < ⁴ > is H,

R ⁵ is H or CH _3,

n is 2 to 6,

and z is 1 to 4.

n is preferably 2 or 3, and z is preferably 1. 1, T is an alkyl group having 1 to 4 carbon atoms (for example, amino-C ₁ -C ₄ -alkyl) having at least one amine on it, or an alkyl group having 1 to 4 carbon atoms (E.g. mono-or di-C ₁ -C ₄ -alkylamino-C ₁ -C ₄ -alkyl). 2, T is selected from the group consisting of a cyclic structure having 6 or fewer carbon atoms in the ring and a nitrogen atom shown in formula (2) and optionally a second nitrogen atom or oxygen atom in the ring, together with the nitrogen atom shown in formula (2) , For example, alkyl, amine substituted alkyl, alkylamino alkyl or alkoxyalkyl to form morpholino or piperazino. The cyclic structure may comprise a C ₁ to C ₄ alkyl substituent on the ring.

Another aspect of the present invention is a process for preparing a polyurethane by combining the reactants in the presence of an effective amount of at least one compound of formula 2 catalyzing the reaction of the polyol and the polyisocyanate as reactants.

Preferred subgroups of amines / amides according to the invention are those of the formula (2a), in particular of the formula (2b).

(2a)

(2b)

Wherein R ¹ is (R ³ ) ₂ N (CH ₂ ) _n or C _z H _{2z + 1} and R ² , R ³ , R ⁴ , R ⁵ , T, k, n and z are as defined above N is preferably 2 or 3, and z is preferably 1. Each R < ³ > may be the same or different, as in the values of n and z. Particularly preferred compounds of formula (2a) and (2b) are those wherein R ¹ is C _z H _{2z + 1} . Specific preferred compounds are those of the formulas (3) and (4).

(3)

[Chemical Formula 4]

An example of a cyclic terminated structure is a compound of formula (2c)

[Chemical Formula 2c]

These compounds can be prepared by methods known in the art for the preparation of amines / amides. Generally, the catalyst is prepared by directly reacting dimethylaminopropylamine (DMAPA) or other similar amines with methyl acrylate (MA), dimethyl acrylamide (DMAA), or similar unsaturated materials. The product of this reaction is the aminopropionamide of the present invention which contains substantially less unreacted feedstock and other adducts of formulas (5), (6) and (7) below.

[Chemical Formula 5]

[Chemical Formula 6]

(7)

Methods for preparing compounds of formula (4) are disclosed in U.S. Patent Nos. 4,256,665 and 4,259,259, which are incorporated herein by reference.

These amine / amide catalysts are used to catalyze the reaction of the polyurethane forming catalysts, i.e., isocyanate / water and / or isocyanate / alcohol reactions. The polyurethanes described above can be rigid flexible slabs, ester slabs, molded non-porous elastomers or any other type of foam known in the art. The amines / amides of the present invention can be used in the preparation of amine premixes, i.e. other amine catalysts, surfactants or other additives known in the art or mixtures with polyurethane components.

(A) a polyether polyol containing on average more than two hydroxy groups per molecule, (b) an organic polyisocyanate, (c) at least a polyether polyol containing at least two hydroxyl groups per molecule to produce a polyurethane foam, One catalyst, (d) water, (e) a surfactant, preferably a silicone / polyether copolymer known in the art, and (f) an inert gas.

The average number of hydroxy groups per molecule of the polyol is slightly above at least 2, typically 2.1 to 3.5. Generally, the polyol has an equivalent weight of about 400 to 1500, or 400 to 3000 g / equivalent, and the ethylene oxide content is less than 20%. Useful polyols include alkylene oxide adducts of polyhydroxyalkanes, alkylene oxide adducts of non-reducing sugars and sugar derivatives, alkylene oxide adducts of polyphenols, alkylene oxide adducts of polyamines and polyhydroxyamines But are not limited to, polyether polyols. The alkylene oxide is preferably based on ethylene oxide or propylene oxide.

The organic polyisocyanate contains at least two isocyanate groups, for example, toluene diisocyanate (TDI), and the foaming index is typically 60 to 130.

Water is generally contained in 1 to 12 php (parts by weight per 100 parts of polyol)

Other additives may be added to the polyurethane foam to impart other properties to the foam, including, for example, colorants, flame retardants, and GEOLITE (R) reformer foam additives (manufactured by Organo Silicones Group of Witco Corporation, Greenwich, ), But is not limited thereto. The inert gas is soluble in the foam formulation at elevated pressures but is released (i.e., blown) from solution under atmospheric pressure. Examples of such gases include CO ₂ , but other conventional gases including nitrogen, air or hydrocarbon gases such as methane, ethane, etc. may also be used. The inert gas may also contain volatile organic compounds, such as pentane isomers, or chlorinated hydrocarbons boiling above room temperature, but having a sufficiently high vapor pressure at room temperature such that its vapor exhibits substantial gas constituents in the cells of the foam.

The silicone copolymer surfactant should be capable of helping to form a stable foam and be present in an amount effective to stabilize the polyurethane foam, generally about 0.05 to 5 wt%, preferably 02 to 1.5 wt% of the total reaction mixture shall.

The foam is prepared by mixing the components, i.e. components (a) to (f), together so that the gas produced as a by-product during the reaction will foam the polyurethane. The foam may also be prepared by injecting an inert gas such that the reactants are placed under high pressure (at least above atmospheric pressure) and the inert gas is dissolved in the reaction mixture. The pressure is then relaxed to flash the reactants so that the gas forms a bubble in the nucleation position in the foam system to act as a foaming agent. This results in a foam with reduced density. A more detailed description of the present process and apparatus used therein is found in European Patent Application Publication No. 0 645 226 A2, which is incorporated herein by reference.

The compounds of the present invention can also be used for non-foaming polyurethane reactions, for example, polyurethane elastomer formation. For such polyurethanes, water in the formulation can often be replaced by chain extenders, which are low molecular weight (less than 400) active hydrogen containing compounds having at least two reactive groups. Examples are 1,4-butanediol, ethylene glycol, diethylene glycol, and ethylenediamine.

The conditions and compositions for these reactions are known in the art [" Polyurethane Handbook " 2nd Ed. Gunter Ortel ed. Hanser Publishers. Cincinnati, 1995, which is incorporated herein by reference). Generally, these catalysts are used in an amount effective to catalyze the reaction, i. E., Catalyze the reaction to form the polyurethane. Generally, such an effective amount is from about 0.02 to 5.0 parts per 100 parts of polyol in the reaction mixture. For the shaped flexible foams described in the following examples, these catalysts form a cream resulting in a slightly faster release time than DDPA, and the load properties (ILD) and curing properties of the foam are at least as good as DDPA.

[Example]

[Glossary]

php: The number of parts per 100 parts polyol in the composition.

Polyol 1: Ethylene oxide / propylene oxide polyether, marketed by ARCO Chemical, ARCOL Polyol E-656.

Polyol 2: Ethylene oxide / propylene oxide polyether, marketed by ARCO, Inc., ARCOL Polyol E-688.

Polyol 3: Propylene oxide polyether sold by Dow Chemical VORANOL 490.

Polyol 4: Propylene oxide polyether sold by Dow Chemical VORANOL 800.

Polyol 5: Polyester polyol marketed by Stepan Chemical as PS-3152.

Polyol 6: A polyester polyol marketed by Witco under the trade name FOMREZ 53.

Silicone 1: A silicone surfactant marketed by Witco as L-3001, NIAX (NIAX) surfactant.

Silicone 2: a silicone surfactant marketed by Witco as Niacax (NIAX) surfactant Y-10829

Silicone 3: A silicone surfactant marketed by Witco as Niacax (NIAX) surfactant L-6900.

Silicone 4: Silicon surfactant marketed by Witco as L-532.

Surfactant 1: Organic surfactant marketed by Union Carbide Corp. as NP-9.

Catalyst 1: Amine catalyst marketed by Witco as Niax (NIAX) catalyst A-1.

Catalyst 2: An amine catalyst marketed by Witco as Nyax (NIAX) catalyst A-33.

Catalyst 3: An amine catalyst marketed by Witcosa as Niax (NIAX) Catalyst A-99.

Isocyanate 1: Diphenylmethylene diisocyanate (MDI) sold by Dow Chemical Company as isonate 143-L.

Isocyanate 2: A standard commercial mixture of 2,4-toluene diisocyanate 80% and 2,6-toluene diisocyanate 20%.

Isocyanate 3: MDI modifier sold by Dow Chemical Company as PAPI 27.

IFD: Foam load value as measured by ASTM D-3574 Test Method B1.

[General Synthesis]

Non-catalytic reaction of a specific tertiary amine containing a primary amine with an acrylate or methacrylate

The following tertiary amines / amides were synthesized in a 500 ml round bottom four necked flask. The flask was equipped with an addition funnel, mechanical stirrer, nitrogen purge, thermometer and heating mantle to keep the pressure uniform. 1 mole of DMAA and 1 mole of the target amine, or 1 mole of MA and 2 moles of amine were used. First, when the amine is a primary, the amine is added to the flask in a weighed amount and DMAA or MA is added to the addition funnel in weigh. If the amine is not primary, the order is the opposite (i. E., The amine is added to the addition funnel and DMAA or MA is added to the flask) and the reaction is described in detail below.

[Example 1]

(Synthesis of amine / amide of the present invention)

Propanamide, 3- [3-dimethylaminopropyl] amino-N, N-dimethyl

One mole of DMAPA (dimethylaminopropylamine, 102.21 g) was added to the flask and weighed. The system was purged with nitrogen for several minutes. DMAA was added to the flask (6 ml min) while stirring the mixture and monitoring the temperature. The initiation temperature was 24 占 폚 and was not changed during addition. When DMAA addition was complete, the flask was heated to 100 < 0 > C with stirring and held for 2 hours. The structure (Formula 3) was obtained with a conversion of 90% or higher.

Propanamide, 3- [3-dimethylaminopropyl] amino-N- [3-dimethylaminopropyl]

The MA / DMAPA variant of the amine was synthesized by the above procedure using 2 moles of DMAPA (204.42 g) and 1 mole of MA (86.10 g). During the addition of MA, the temperature rose from a starting temperature of 24 占 폚 to a final temperature of 75 占 폚. The temperature was maintained at 75 DEG C for 2 hours. The samples were stripped at 70 ° C and 5 mm Hg in a rotary evaporator for 4 hours to remove methanol. The structure (Formula 4) was obtained with a conversion of 92% or more.

Propanamide, 3- [3-dimethylaminopropyl] amino-N- [3-dimethylaminopropyl], 2-methyl

Amine methyl methacrylate (MMA) / DMAPA variants were synthesized by the above procedure using 2 moles of DMAPA (204.42 g) and 1 mole of MMA (86.10 g). During the addition of MMA, the temperature did not change from the starting temperature of 24 占 폚. The temperature was increased to 120 < 0 > C for a total of 24 hours. The samples were stripped at 70 ° C and 5 mm Hg in a rotary evaporator for 4 hours to remove methanol. The following structure (Formula 8) was obtained with a conversion of about 80%.

[Chemical Formula 8]

[Example 2]

Synthesis of Comparative Catalyst

DMAA (1 mole) was added to a stirred reactor under a nitrogen atmosphere to prepare propanamide, 3- [dimethyl] amino-N, N-dimethyl. Dimethylamine (1 mole) was added at such a rate that the temperature in the reactor was maintained below 35 < 0 > C. When all of the dimethylamine had been added, the reactor was maintained at 35-45 [deg.] C for about 2 hours. The temperature was then increased to 60 DEG C for an additional 5 hours. After cooling to 25 ° C, the reaction was complete and the product was analyzed. As a result of the analysis, it was confirmed that more than 99% of DDPA structure was converted. Similarly, propanamide, 3- [3-methyl-3-hydroxyethyl] amino-N, N-dimethyl (Formula 9) was prepared from DMAA and MEOA (N-methylethanolamine).

[Chemical Formula 9]

Further, propanamide and 3-bis (2-hydroxyethyl) amino] -N, N-dimethyl (Formula 10) were prepared from DMAA and DEOA (diethanolamine).

[Chemical formula 10]

Propanoamide, 3- [3-methyl-3-hydroxyethyl] amino-N-methyl-N-hydroxyethyl (Formula 11) was prepared from MA and MEOA.

(11)

MA and DEOA, propanamide, 3- [bis (2-hydroxyethyl) amino] -N, N- [bis (2-hydroxyethyl)] (Formula 12).

[Chemical Formula 12]

[Example 3]

Evaluation of Simple Water Blown Urethane Foam

Blowing and gel properties of each reactive DDPA catalyst were evaluated for DDPA. To obtain the blowing properties, a simple system of polyol 1 (0.049 eq.) At 97.22 php, water (0.195 eq.) At 179 php, and 1 at 1 php surfactant and isocyanate 1 at index 103 was used. A total of 50 grams of the preformed polyol, water, and surfactant mixture was weighed into a 0.47 liter (one pint) line of paper cups. The catalyst was evaluated by adding 0.25 g (0.5 php) or 0.5 g (1.0 php) to the mixture. Isocyanate was added and the mixture was stirred with a drill press for 5 seconds.

Blowing properties were measured by measuring top-of-cup and blowing time as compared to DDPA. The data are shown in Table 1.

[Table 1]

Waterblowing Foam Example

a: Top-off-cup time refers to the time (in seconds) it takes for the rising foam to reach the height of the cup.

b: The Crél DDPA value represents the relative activity of the catalyst and is obtained by dividing the top-of-cup time of the amine-amide by the top-of-cup time of DDPA at a given use level. Run 3 to 157 sec / 168 sec = 0.93 = Crl DDPA at 0.5 php.

c: Blowing time indicates the time (sec) in which gas escaping from the foam is visually observed.

Table 1 shows a comparison for a simple water-blowing urethane foam composition. Each catalyst was evaluated at 0.5 and 1.0 php levels, and the rise (top-of-cup) and blowing time were recorded. The test substances were divided into two groups, those with activities very similar to the activities of control DDPA (Runs 2 to 6), and those with significantly inferior activities (Runs 7 to 14). Runs 3 to 6 contain the preferred catalysts (structures of formulas 3 and 4), while Runs 7 to 14 use catalysts with hydroxyl inferior performance (structures of formulas 9 to 12) . The overall performance was significantly different, suggesting the unique catalytic properties of the preferred structure.

[Example 4]

Evaluation of urethane elastomer

A similar experiment was performed to evaluate the gel properties of the reactive DDPA catalyst for DDPA. The resin mixture consisted of 94 php (0.047 equivalents) of polyol 1 and 6 php (0.193 equivalents) of ethylene glycol. Isocyanate 1 used Index 103. A total of 100 g of the resin mixture was weighed into a pint (0.47 liters) line-drawn paper cup. The isocyanate was added and stirred by hand. The catalyst was evaluated at 3 php. The gel properties were determined by measuring the gel time (when the mixture was too viscous enough to stir by hand) and the time without viscosity compared to DDPA. The results are shown in Table 2.

[Table 2]

Urethane elastomer Example

Runs 2 and 3 confirm that Structures 3 and 4 have very similar activities to that of DDPA and all other groups are much slower than that. This important difference in the elastomeric system identifies the unique catalytic properties and broad range of applications of these compounds.

[Example 5]

Evaluation of Molded Flexible Foam Composition

The catalysts in the molded flexible foam formulation were evaluated. The control composition is a " DDPA mixture " of polyol 1 at 80 php, polyol 2 at 20 php, silicone 2 at 1.2 php, DEOA at 1.5 php, water at 3.56 php, catalyst 2 at 0.23 php, catalyst 1 at 0.14 php, (See Table 3). The index 100 was used for isocyanate 2. The reactive DDPA catalyst was mixed in the same manner as the " DDPA mixture " except that DDPA was replaced with the respective catalyst to be evaluated. The new mixture was used in place of the " DDPA mixture " in the same parts by weight. The mixture was mixed for 55 seconds (drill press), isocyanate was added, and then mixed for 5 seconds. A foam was made from an aluminum mold with a 1/16 inch belt. The mold temperature was 150 ° F (hot water heating) at a release time of 3.5 minutes. The prepared foams were compared by measuring the cream and release time, 50% or 75% ILD value, and curing reaction. The results are shown in Table 3.

[Table 3]

Comparison of catalysts in flexible forming foams

The performance of the preferred catalyst is shown in Runs 2 to 5. These catalysts induce slightly faster cream and release times than the DDPA control mixture, and the loadability (ILD) and cure properties of the foam are superior to those of the control. Additional evidence of this result is that the typical catalytic activity of tertiary amine / amide compounds is very similar to DDPA. The performance of the hydroxyl containing group is shown in runs 6-13. Similar to the case of DDPA, but tends to exhibit somewhat longer release times (i.e. slower reaction) and smaller loading capacity.

[Example 6]

Check the reactivity of amine / amide with isocyanate

Structure 4 (0.315 g, 0.00265 m) was added to a small reactor and phenyl isocyanate (0.684 g, 0.00265 m) was added. Immediate mixing suggested a significant exothermic reaction resulting in a significant increase in the viscosity of the mixture, leading to a rapid reaction. After about 3 minutes, the mixture sample was taken and all of the phenylisocyanate was consumed. The results demonstrate that these compounds readily react with isocyanates, which react to produce foams and support the notion of non-volatile materials.

[Example 7]

Evaluation of Rigid Foam Composition

The catalysts were evaluated in a rigid foam composition containing 60 php polyol 3, 15 php polyol 4, 25 php polyol 5, 2 php silicone 3, 1.0 php water, 36 php HCFC-141b blowing agent. The index 120 was used for isocyanate 3. Structure 4 was used as a catalyst for evaluation. With the exception of isocyanate, all ingredients were premixed in a paper cup with one pint (0.47 liters) line. The mixture was mixed for 10 seconds (drill press), isocyanate was added and mixed for another 3 seconds. The mixture was transferred to a line paper bucket and the cream, string and gel, and final rise time were measured. The results presented in Table 4 indicate that catalyst 4 of the present invention produces a foam of excellent rigidity.

[Table 4]

Evaluation of catalysts in rigid foams

[Example 8]

Evaluation of polyester foam composition

Structure 4 was also evaluated in a polyester foam composition. Foams using the structure of formula (4) instead of DDPA with both foams, i.e., the control and the same amount of amine, were prepared. The composition is shown in Table 5 below. TDI was added to the polyol and the mixture was hand mixed until clear. The polyol / TDI mixture was then mixed for 8 seconds at 1000 rpm. Water, amine, surfactant premix was added using a syringe and mixed continuously for 7 seconds. The mixture was immediately poured into a card box (20 x 20 x 20 cm) and the cream and blowing time were recorded according to an ascending profile. The painting time of the control foam and the experimental foam was 13 seconds, respectively. The blowing times of the two foams were 119 and 121 seconds, respectively. No difference in the two foams was observed.

[Table 5]

Evaluation of catalyst in polyester foam composition

[Example 9]

Stability verification

The stability study was carried out on a series of polyester foams prepared using N-ethylmorpholine, N-methylmorpholine, N, N-dimethylbenzylamine, n-hexadecyldimethylamine and the catalyst of the structure of Formula 4, respectively . A composition of polyol 6, water, silicone 4, surfactant 1, isocyanate 2 of index 103 was used. Each catalyst was evaluated at the level of use required to exhibit a blowing time of 41 seconds. The polyol was weighed into a 32 ounce paper cup. TDI was added to the polyol and mixed by hand until the mixture became clear. The polyol / TDI mixture was then mixed for 8 seconds at 1000 rpm. Water, amine, and surfactant mixture was added by syringe and mixed continuously for 7 seconds. The mixture was immediately poured into a paper bucket and top-of-cup time was recorded.

Then, about 0.2 g of each foam sample was taken from the center of the foam sample cut at 2 inches from the bottom of the bucket. Samples were placed in glass vials, sealed and analyzed on a DB-1 (30 x 0.32 mm) column using a Varian 3760 gas chromatograph equipped with a Perkin Elmer HS-40 Headspace Autosampler. The results are shown below.

[Table 6]

Stability result

This result indicates that the volatility can not be detected in the structure 4. Thus, Structure 4 is expected to be stable in foam applications.

The amine / amide catalyst of the present invention has high reactivity and low volatility, so that polyurethane formation can be effectively catalyzed.

Claims (17)

And reacting the polyol component and the polyisocyanate component in the presence of an effective amount of an amine / amide of the formula: (2)

In this formula, Q is C _Z H _{2 Z + 1} , or (CH ₂ ) _n N (R ³ ) _k T T 1 is a C ₁ -C ₄ - alkyl, amino -C ₁ -C ₄ - alkyl, mono -C ₁ -C ₄ - alkylamino, -C ₁ -C ₄ - alkyl or di -C ₁ -C ₄ - alkyl, amino -C ₁ -C ₄ - alkyl, or is taken together with the nitrogen atom shown in formula (2) which T is attached a nitrogen atom shown in the formula (2) and not more than 6 carbon atoms in the ring and optionally substituted with C ₁ to C ₄ alkyl An amino-substituted alkyl, an alkylaminoalkyl or an alkoxyalkyl group which forms a cyclic structure, k is 0 or 1, k is 1 when T is 1, k is 0 if T is 2, R ² is H or C _Z H _{2Z + 1} , R ³ is C _Z H _{2Z + 1} , R < ⁴ > is H, R ⁵ is H or CH _3, n is 2 to 6, and z is 1 to 4. The method of claim 1 wherein Q is R ¹ and R ¹ is C _Z H _{2Z + 1} . 2. The method of claim 1, wherein n is 2 to 3 and z is 1. 4. The method of claim 3 wherein R < ¹ > is methyl. 2. The method of claim 1 wherein R < ³ > is methyl. 3. The method of claim 1 wherein R < ⁵ > is hydrogen. The process of claim 1, wherein the amine / amide has the structure of Formula 4: [Chemical Formula 4]

The process according to claim 1, wherein the polyurethane to be produced is an elastomer. The process according to claim 1, wherein the polyurethane to be produced is a polyurethane foam. 10. The method of claim 9, wherein the foam is a molded flexible foam. 10. The method of claim 9, wherein the foam is a rigid foam. The process of claim 1, wherein the amine / amide is present in an amount of from 0.02 to 5 parts per 100 parts of polyol. 13. The method of claim 12, wherein the amine / amide is a compound of formula (2c) [Chemical Formula 2c]

The method of claim 1, wherein the chain extender is present during polyurethane production. The process of claim 1 wherein the polyol has an equivalent weight of from 400 to 1500 and an average number of hydroxyl groups of from about 2.1 to 3.5 and a foam index of from 60 to 130. The method of claim 1, wherein T is a C ₁ to C ₄ alkyl group that may have one or more amines. 2. The compound of claim 1, wherein T is a divalent alkyl, amine substituted alkyl, alkylaminoalkyl or alkoxyalkyl which forms a cyclic structure comprising no more than 6 carbon atoms and nitrogen atoms in the ring with the nitrogen atom to which it is attached Way.