Catalyst Composition for Polyurethane

Abstract

The present invention relates to a composition comprising a copper(II) salt which can be used as a catalyst, a process for manufacturing said composition, and the use of said composition as a catalyst, in particular for the reaction of at least one isocyanate compound with at least one isocyanate-reactive compound, especially for the manufacture of polyisocyanate addition products such as polyurethanes, in particular polyurethane foams.

Description

Technical Field

[0001] The present invention relates to a composition comprising a copper(II) salt (Cu(II) salt) that can be used as a catalyst, a process for manufacturing the composition, and the use of the composition as a catalyst, particularly for the reaction of at least one isocyanate compound with at least one isocyanate-reactive compound, particularly for the production of polyisocyanate addition products such as polyurethanes (polyurethane), particularly polyurethane foams. Background Art

[0002] Polyurethane foams are produced by reacting di- or polyisocyanates (or prepolymers thereof) with compounds containing two or more active hydrogens (chain extenders, polyether polyols, polyester polyols, polyetheramines, etc.), typically in the presence of a blowing agent (chemical blowing agents such as water, etc. and physical blowing agents such as pentane, cyclopentane, halogenated hydrocarbons, etc.), a catalyst (tertiary amines, and organometallic derivatives of tin, bismuth, zinc, etc.), a silicone-based surfactant, and other auxiliaries. During the preparation of polyurethane foams (PU), two main reactions, gelation and foaming, are promoted between the reactants by the catalyst. The development of highly catalytically active and efficient gelation catalysts has advantageously made it possible to reduce the curing time required for polyurethane foams and thus advantageously reduce the manufacturing cycle of the final foam products. Organotin compounds have often been the preferred catalysts for promoting the gel reaction. From the perspective of some environmental and worker exposure, organotin catalysts are being increasingly challenged. Therefore, there is a high demand in the PU industry for highly efficient and non-toxic gel catalysts.

[0003] US2017 / 0225158A1 describes the use of a copper catalyst composition comprising a copper(II) compound dissolved in a solvent to prepare mechanically foamed foams and elastomers. WO2012 / 006263A1 describes the use of a copper catalyst to manufacture polyurethane elastomers. The catalyst consists of copper atoms and certain polydentate ligands. The polydentate ligand is usually a derivative of a Schiff base and contains at least one nitrogen. WO2002048229A1 describes a carbamate containing an amine as a catalyst in the manufacture of polyurethanes.

[0004] Most polyurethane foams emit volatile organic compounds. These emissions can consist of contaminants present, for example, in the raw materials, catalysts, degradation products, or unreacted volatile starting materials or other additives. Amine emissions from polyurethane foams have become a major issue, especially in automotive interior applications, in furniture or cushions, and thus there is an increasing market demand for low-emission foams. The automotive industry in particular requires a significant reduction in volatile organic compounds (VOCs) and condensable compounds (fogging or FOG) in foams. The evaluation of the VOC and FOG profiles of PU foams can be carried out by the VDA 278 test. One of the main components of VOCs emitted from flexible molded foams is amine catalysts. To reduce such emissions, catalysts with very low vapor pressures should be used. Alternatively, if the catalysts have reactive hydroxyl or amine groups, they can be linked to the polymer network. If so, only negligible amounts of residual amine catalysts will be detected in the fogging test. However, the use of reactive amines is not without difficulties. It is known that reactive amines deteriorate some fatigue properties such as moisture-aged compression set. In addition, the widely used reactive amines are monofunctional and promote chain termination during polymer growth and lose their catalytic agility by becoming covalently bonded to the polymer matrix. Therefore, the development of highly efficient polyurethane catalysts with low-emission profiles is one of the important goals of the modern polyurethane industry.

[0005] Despite attempts in the prior art, there is still a need for polyurethane foams having improved physical properties such as firmness, stiffness, or load-bearing capacity, as particularly reflected by a higher indentation load (force) deflection or ILD (IFD), which in turn depends on the degree of cure of the polyurethane foam, which itself depends on catalyst performance. SUMMARY OF THE INVENTION

[0006] The present inventors have found that a specific composition comprising a copper(II) salt provides improved catalyst performance resulting in a better degree of cure of polyurethane foams and improved physical properties. The inventive catalyst composition can also be used as a highly efficient catalyst with a low-emission profile in polyurethane formation.

[0007] Accordingly, the present invention provides a composition comprising: at least one Cu(II) salt; at least one compound obtainable by reacting at least one isocyanate compound with at least one isocyanate-reactive compound having at least one tertiary amino group; and optionally one or more diluents.

[0008] In one embodiment of the present invention, the composition can be obtained by reacting at least one isocyanate compound and at least one isocyanate-reactive compound having at least one tertiary amino group in the presence of at least one Cu(II) salt and optionally in the presence of one or more diluents. Alternatively, it is also possible to first react at least one isocyanate compound and at least one isocyanate-reactive compound having at least one tertiary amino group optionally in the presence of one or more diluents, and then mix the reaction product with the Cu(II) salt and optionally one or more diluents.

[0009] In a further embodiment of the present invention, the composition can be obtained by: reacting at least one Multiple isocyanate compound, at least one isocyanate-reactive compound having at least one tertiary amino group and at least one isocyanate-reactive compound not having a tertiary amino group in the presence of at least one Cu(II) salt and optionally in the presence of one or more diluents. Also in this embodiment, it is also possible to first react at least one Multiple isocyanate compound, at least one isocyanate-reactive compound having at least one tertiary amino group and at least one isocyanate-reactive compound not having a tertiary amino group optionally in the presence of one or more diluents, and then mix the reaction product with the Cu(II) salt and optionally one or more diluents.

[0010] In one embodiment of the present invention, the composition comprises: at least one Cu(II) salt; at least one component selected from compounds obtainable by reacting at least one isocyanate compound and at least one isocyanate-reactive compound having at least one tertiary amino group; and optionally one or more diluents.

[0011] By the reaction of an isocyanate compound and an isocyanate-reactive compound having at least one tertiary amino group (which is preferably selected from hydroxy- and / or amino-functional compounds), thus preferably, a composition is formed which comprises: a compound comprising at least one urethane (carbamate) (from the reaction with a hydroxy-functional compound) and / or urea group (from the reaction with an amino-functional compound) and at least one tertiary amino group (which does not react with the isocyanate group); at least one Cu(II) salt and optionally one or more diluents.

[0012] According to the present invention, the isocyanate compounds for preparing the compositions according to the present invention may be selected from mono-isocyanates and poly-isocyanates (having two or more isocyanate groups), and mixtures thereof. The mixtures may include mixtures of mono-isocyanates, mixtures of poly-isocyanates, or mixtures of one or more mono-isocyanates and one or more poly-isocyanates. Poly-isocyanates are preferred. For example, the isocyanate compounds may be selected from: octadecyl isocyanate; octyl isocyanate; butyl and tert-butyl isocyanates; cyclohexyl isocyanate; adamantyl isocyanate; ethyl isocyanatoacetate; ethoxycarbonyl isocyanate; phenyl isocyanate; α-methylbenzyl isocyanate; 2-phenylcyclopropyl isocyanate; 2-ethylphenyl isocyanate; benzyl isocyanate; m- and p-tolyl isocyanates; 2-, 3-, or 4-nitrophenyl isocyanate; 2-ethoxyphenyl isocyanate; 3-methoxyphenyl isocyanate; 4-methoxyphenyl isocyanate; ethyl 4-isocyanatobenzoate; 2,6-dimethylphenyl isocyanate; 1-naphthyl isocyanate; (naphthyl)ethyl isocyanate; isophorone diisocyanate (IPDI); toluene diisocyanate (TDI); diphenylmethane-2,4'-diisocyanate (2,4'-MDI); diphenylmethane-4,4'-diisocyanate (4,4'-MDI); hydrogenated diphenylmethane-4,4'-diisocyanate (H.12MDI); tetramethylxylene diisocyanate (TMXDI); hexamethylene-1,6-diisocyanate (HDI); naphthalene-1,5-diisocyanate; 3,3'-dimethoxy-4,4'-biphenyl diisocyanate; 3,3'-dimethyl-4,4'-dimethyl-4,4'-biphenyl diisocyanate; phenylene diisocyanate; 4,4'-biphenyl diisocyanate; trimethylhexamethylene diisocyanate; tetramethylxylene diisocyanate; 4,4'-methylene-bis(2,6-diethylphenyl isocyanate); 1,12-diisocyanatododecane; 1,5-diisocyanato-2-methylpentane; 1,4-diisocyanatobutane; and cyclohexylene diisocyanate and its isomers; the uretdione dimer of HDI; the trimethylolpropane trimer of TDI; the isocyanurate trimers of TDI, HDI, IPDI; the biuret trimers of TDI, HDI, IPDI; and mixtures thereof, and the poly-isocyanates as described above in which the isocyanate groups are partially reacted with at least one isocyanate-reactive compound that does not have a tertiary amino group, the isocyanate-reactive compound that does not have a tertiary amino group being preferably selected from OH-, NH-, and NH2-functional optionally substituted hydrocarbons, which may contain one or more heteroatoms, such as alcohols like methanol, tert-butanol, isopropanol, sec-butanol, OH-functional mono(ethylene)glycol ethers, OH-functional di(ethylene)glycol ethers, etc.Among them, preferred isocyanates include m- and p-tolyl isocyanate; isophorone diisocyanate (IPDI); toluene-2,4-diisocyanate (2,4-TDI); toluene-2,6-diisocyanate (2,6-TDI); diphenylmethane-2,4'-diisocyanate (2,4'-MDI); diphenylmethane-4,4'-diisocyanate (4,4'-MDI); hydrogenated diphenylmethane-4,4'-diisocyanate (H.12MDI); tetramethylxylene diisocyanate (TMXDI); hexamethylene-1,6-diisocyanate (HDI); naphthalene-1,5-diisocyanate; the uretdione dimer of HDI; the trimethylolpropane trimer of TDI; the isocyanurate trimers of TDI, HDI, and IPDI; the biuret trimers of TDI, HDI, and IPDI, and mixtures thereof. More preferred isocyanates include isophorone diisocyanate (IPDI); toluene-2,4-diisocyanate (2,4-TDI); toluene-2,6-diisocyanate (2,6-TDI); diphenylmethane-2,4'-diisocyanate (2,4'-MDI); diphenylmethane-4,4'-diisocyanate (4,4'-MDI); hydrogenated diphenylmethane-4,4'-diisocyanate (H.12MDI); hexamethylene-1,6-diisocyanate (HDI); naphthalene-1,5-diisocyanate, and mixtures thereof.

[0013] Trivalent or higher aliphatic polyisocyanates include, in particular, biurets, urethanes, carbamates, isocyanurates, and higher oligomers of diisocyanates, said diisocyanates being especially hexamethylene diisocyanate (HDI), 1-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane (IPDI or isophorone diisocyanate), and / or bis(isocyanatocyclohexyl)-methane, etc. Specific examples of such polyisocyanates include, for example:

[0014] - the biuret of hexamethylene diisocyanate and its oligomers, for example:

[0015]

[0016] which can be obtained commercially, for example, as 100.

[0017] - the isocyanurate trimer of hexamethylene diisocyanate, for example:

[0018]

[0019] which can be obtained commercially, for example, as N3300; or its higher oligomers such as the pentamer:

[0020] or an asymmetric trimer such as:

[0021] wherein R is an isocyanate-containing aliphatic residue derived from HDI, or 4,4′-methylenebis(cyclohexyl isocyanate) (HMDI or hydrogenated MDI).

[0022] - an isocyanurate trimer of isophorone diisocyanate, such as:

[0023]

[0024] which can be commercially obtained, for example, as Z4470 or Tolonate IDT 70B.

[0025] Other polyisocyanates can be prepared, for example, from polyhydroxy-functional compounds or polymers and preferably at least an equimolar amount of a diisocyanate such as HDI, IPDI or HMDI to form the corresponding polyisocyanate.

[0026] Preferred isocyanate compounds include aliphatic polyisocyanates, preferably aliphatic diisocyanate compounds, especially isophorone diisocyanate (IPDI).

[0027] In one embodiment of the present invention, the isocyanate-reactive compound having at least one tertiary amino group is selected from alcohols having at least one tertiary amino group and amines having at least one tertiary amino group and at least one additional amino group selected from primary and secondary amino groups. The isocyanate-reactive compound can include a single isocyanate-reactive compound or a mixture thereof. The alcohols and amines used as the isocyanate-reactive compound include saturated, unsaturated and aromatic compounds, preferably saturated aliphatic alcohols and amines.

[0028] Since the tertiary amino group does not react with the isocyanate group, the reaction product of the isocyanate compound and the isocyanate-reactive compound still has a tertiary amino group. A preferred tertiary amino group is especially a dialkylamino group such as dimethylamino or diethylamino, etc., or a cyclic amino group such as piperidyl, pyrrolidinyl, morpholinyl, etc., preferably pyrrolidinyl.

[0029] In one embodiment of the present invention, the isocyanate-reactive compound includes at least one ether group, and preferably the isocyanate-reactive compound is selected from aliphatic alcohols having at least one hydroxyl group, at least one tertiary amino group and optionally at least one ether group.

[0030] As described above, the composition of the present invention may further comprise a compound obtainable by reacting at least one polyisocyanate compound, at least one isocyanate-reactive compound having at least one tertiary amino group, and at least one isocyanate-reactive compound not having a tertiary amino group. The isocyanate-reactive compounds not having a tertiary amino group include various types of alcohols and amines, preferably aliphatic alcohols such as methanol, ethanol, propanol, butanol and their isomers, or amines such as methylamine, ethylamine, propylamine and the like.

[0031] Examples of the isocyanate-reactive compound having at least one tertiary amino group are selected from:

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041] Bicyclic tertiary amines, such as those selected from the following formulae:

[0042]

[0043]

[0044] wherein x, y, z, and u are independently selected from a bond, a C1-C35 hydrocarbon, a sulfonate (R-SO2OR), or a phosphate (RO)3P(O), wherein the C1-C35 hydrocarbon may contain aliphatic, cyclic, saturated, unsaturated, and aromatic groups, halogen groups, ether groups, carbonate groups, amide groups, tertiary amine groups, or a combination of two or more thereof. Preferably, the bicyclic tertiary amine has the following formula:

[0045]

[0046]

[0047] wherein R5-R 17Independently selected from hydrogen, halogen, C1-C10 hydrocarbons, carbonates, ether groups, amides, and tertiary amines, and "u------" represents u-OH, where u is as defined above.

[0048] Specific examples of bicyclic tertiary amines include:

[0049]

[0050]

[0051]

[0052]

[0053] Preferably

[0054]

[0055] Or mixtures thereof. Preferred reaction products of these preferred isocyanate-reactive compounds and their mixtures include, in particular, all reaction products with isophorone diisocyanate.

[0056] The compositions of the present invention can include any reaction product of any isocyanate and any isocyanate-reactive compound as defined above, and should include every possible combination thereof.

[0057] Particularly preferred reaction products of any isocyanate and any isocyanate-reactive compound as described above are reaction products of these isocyanate-reactive compounds with isophorone diisocyanate (IPDI) and hexamethylene-1,6-diisocyanate (HDI), most preferably with isophorone diisocyanate (IPDI). Such compounds include, in particular and most preferably, compounds in which both isocyanate groups of the diisocyanate have been reacted off, but can also include compounds in which only one isocyanate group has been reacted off and all molar ratios between these two molar ratios, as schematically shown for IPDI in the following formula:

[0058]

[0059] Where X is O or N, and

[0060] In the case where X is N, b is 2 and R 4 Is hydrogen and a hydrocarbon group having at least one tertiary amino group, or any hydrocarbon group and a hydrocarbon group having at least one tertiary amino group, and

[0061] In the case where X is O, b is 1 and R 4is a hydrocarbyl group having at least one tertiary amino group, wherein the hydrocarbyl group may be substituted and may include one or more heteroatoms.

[0062] Preferred compositions according to the invention comprise:

[0063] C1 1-[Bis[3-(dimethylamino)propyl]amino]-2-propanol

[0064] and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0065] C2 2-[2-(Dimethylamino)ethoxy]ethanol

[0066]

[0067] and the reaction product with: 1,3-bis(1-isocyanato-1-methylethyl)benzene, isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI), and more preferably 1,3-bis(1-isocyanato-1-methylethyl)benzene,

[0068] C3 2-[2-(Dimethylamino)ethyl-methyl-amino]ethanol

[0069]

[0070] and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI),

[0071] C4 3,3'-iminobis(N,N-dimethylpropylamine) (or (N-[3-(dimethylamino)propyl]-N',N'-dimethyl-propane-1,3-diamine):

[0072]

[0073] with the reaction products of: 1,3-bis(1-isocyanato-1-methylethyl)benzene, isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI), and more preferably 1,3-bis(1-isocyanato-1-methylethyl)benzene,

[0074] C5 dimethylaminoethanol (or 2-(dimethylamino)-ethan-1-ol):

[0075]

[0076] with the reaction products of: 1,3-bis(1-isocyanato-1-methylethyl)benzene, isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI), and more preferably 1,3-bis(1-isocyanato-1-methylethyl)benzene,

[0077] C6 diethylaminoethanol (or 2-(diethylamino)ethanol)

[0078]

[0079] with the reaction products of: 1,3-bis(1-isocyanato-1-methylethyl)benzene, isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI), and more preferably 1,3-bis(1-isocyanato-1-methylethyl)benzene,

[0080] C7 3-(dimethylamino)-1-propylamine

[0081]

[0082] with the reaction products of: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0083] C8 3-(diethylamino)-1-propylamine

[0084]

[0085] and reaction products with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0086] C9 3-(diethylamino)-1-propanol

[0087]

[0088] and reaction products with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0089] C10 1-(3-hydroxypropyl)pyrrolidine

[0090]

[0091] and reaction products with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0092] C11 1-(2-hydroxyethyl)pyrrolidine

[0093]

[0094] and reaction products with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0095] C12 1-(2-hydroxyethyl)piperidine

[0096]

[0097] with the reaction products of: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0098] C13 1-(3-hydroxypropyl)piperidine

[0099]

[0100] with the reaction products of: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0101] C14 1-(2-hydroxypropyl)piperidine

[0102]

[0103] with the reaction products of: hexamethylene-1,6-diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0104] C15 1-(3-aminopropyl)pyrrolidine

[0105]

[0106] with the reaction products of: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0107] C16 1-(2-aminoethyl)pyrrolidine

[0108]

[0109] with the reaction products: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0110] C17 1-(3-aminopropyl)piperidine

[0111]

[0112] with the reaction products: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0113] C18 1-(2-aminoethyl)piperidine

[0114]

[0115] with the reaction products: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0116] C19 1-(piperidin-1-yl)propan-2-ol

[0117]

[0118] with the reaction products: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0119] C20 1-(pyrrolidin-1-yl)propan-2-ol

[0120]

[0121] with the reaction products of: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0122] C21 1-(1-Pyrrolidinyl)-2-propanamine

[0123]

[0124] with the reaction products of: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0125] C22 1-(Piperidin-1-yl)propan-2-amine

[0126]

[0127] with the reaction products of: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0128] C23 2-[2-[2-(Dimethylamino)ethoxy]ethyl-methylamino]ethanol

[0129]

[0130] with the reaction products of: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0131] C24 3-{[3-(Dimethylamino)propyl]-methylamino}propanol

[0132]

[0133] with the reaction products: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI), and

[0134] C25 2-{[3-(dimethylamino)propyl]-methyl-amino}ethanol

[0135]

[0136] with the reaction products: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as their biurets, isocyanurates, urethanes, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI).

[0137] Particularly preferred reaction products include:

[0138] D1 2-[2-(dimethylamino)ethoxy]ethanol

[0139]

[0140] the reaction product with isophorone diisocyanate,

[0141] D2 2-[2-(dimethylamino)ethoxy]ethanol

[0142]

[0143] the reaction product with hexamethylene-1,6-diisocyanate,

[0144] D3 1-[bis[3-(dimethylamino)propyl]amino]-2-propanol

[0145]

[0146] the reaction product with isophorone diisocyanate,

[0147] D4 2-[2-(dimethylamino)ethoxy]ethanol

[0148]

[0149] the reaction product with 1,3-bis(1-isocyanato-1-methylethyl)benzene, D5 dimethylaminoethanol

[0150]

[0151] Reaction product with isophorone diisocyanate,

[0152] D6 2-{[2-(Dimethylamino)ethyl]-methylamino}ethanol

[0153]

[0154] Reaction product with isophorone diisocyanate,

[0155] D7 3,3'-Iminobis(N,N-dimethylpropylamine)

[0156]

[0157] Reaction product with 1,3-bis(1-isocyanato-1-methylethyl)benzene,

[0158] D8 3,3'-Iminobis(N,N-dimethylpropylamine)

[0159]

[0160] Reaction product with isophorone diisocyanate,

[0161] D9 Dimethylaminoethanol

[0162]

[0163] Reaction product with 1,3-bis(1-isocyanato-1-methylethyl)benzene, and D10 Dimethylaminoethanol

[0164]

[0165] Reaction product with hexamethylene diisocyanate.

[0166] D11 3-(Dimethylamino)-1-propylamine

[0167]

[0168] Reaction product with isophorone diisocyanate,

[0169] D12 3-(Dimethylamino)-1-propylamine

[0170]

[0171] Reaction product with hexamethylene-1,6-diisocyanate,

[0172] D13 3-(Diethylamino)-1-propylamine

[0173]

[0174] Reaction product with isophorone diisocyanate,

[0175] D14 3-(Diethylamino)-1-propylamine

[0176]

[0177] Reaction product with hexamethylene-1,6-diisocyanate,

[0178] D15 3-(Diethylamino)-1-propanol

[0179]

[0180] Reaction product with isophorone diisocyanate,

[0181] D16 3-(Diethylamino)-1-propanol

[0182]

[0183] Reaction product with hexamethylene-1,6-diisocyanate,

[0184] D17 1-(3-Hydroxypropyl)pyrrolidine

[0185]

[0186] Reaction product with isophorone diisocyanate,

[0187] D18 1-(3-Hydroxypropyl)pyrrolidine

[0188]

[0189] Reaction product with hexamethylene-1,6-diisocyanate,

[0190] D19 1-(2-Hydroxyethyl)pyrrolidine

[0191]

[0192] Reaction product with isophorone diisocyanate,

[0193] D20 1-(2-Hydroxyethyl)pyrrolidine

[0194]

[0195] Reaction product with hexamethylene-1,6-diisocyanate,

[0196] D21 1-(2-Hydroxyethyl)piperidine

[0197]

[0198] Reaction product with isophorone diisocyanate,

[0199] D22 1-(2-Hydroxyethyl)piperidine

[0200]

[0201] Reaction product with hexamethylene-1,6-diisocyanate,

[0202] D23 1-(3-Hydroxypropyl)piperidine

[0203]

[0204] Reaction product with isophorone diisocyanate,

[0205] D24 1-(3-Hydroxypropyl)piperidine

[0206]

[0207] Reaction product with hexamethylene-1,6-diisocyanate,

[0208] D25 1-(3-Aminopropyl)pyrrolidine

[0209]

[0210] Reaction product with isophorone diisocyanate,

[0211] D26 1-(3-Aminopropyl)pyrrolidine

[0212]

[0213] Reaction product with hexamethylene-1,6-diisocyanate,

[0214] D27 1-(2-Aminoethyl)pyrrolidine

[0215]

[0216] Reaction product with isophorone diisocyanate,

[0217] D28 1-(2-Aminoethyl)pyrrolidine

[0218]

[0219] Reaction product with hexamethylene-1,6-diisocyanate,

[0220] D29 1-(3-Aminopropyl)piperidine

[0221]

[0222] Reaction product with isophorone diisocyanate,

[0223] D30 1-(3-aminopropyl)piperidine

[0224]

[0225] Reaction product with hexamethylene-1,6-diisocyanate,

[0226] D31 1-(2-aminoethyl)piperidine

[0227]

[0228] Reaction product with isophorone diisocyanate,

[0229] D32 1-(2-aminoethyl)piperidine

[0230]

[0231] Reaction product with hexamethylene-1,6-diisocyanate,

[0232] D33 1-(piperidin-1-yl)propan-2-ol

[0233]

[0234] Reaction product with isophorone diisocyanate,

[0235] D34 1-(piperidin-1-yl)propan-2-ol

[0236]

[0237] Reaction product with hexamethylene-1,6-diisocyanate,

[0238] D35 1-(pyrrolidin-1-yl)propan-2-ol

[0239]

[0240] Reaction product with isophorone diisocyanate,

[0241] D36 1-(pyrrolidin-1-yl)propan-2-ol

[0242]

[0243] Reaction product with hexamethylene-1,6-diisocyanate,

[0244] D37 1-(1-Pyrrolidinyl)-2-propanamine

[0245]

[0246] Reaction product with isophorone diisocyanate,

[0247] D38 1-(1-Pyrrolidinyl)-2-propanamine

[0248]

[0249] Reaction product with hexamethylene-1,6-diisocyanate,

[0250] D39 1-(Piperidin-1-yl)propan-2-amine

[0251]

[0252] Reaction product with isophorone diisocyanate,

[0253] D40 1-(Piperidin-1-yl)propan-2-amine

[0254]

[0255] Reaction product with hexamethylene-1,6-diisocyanate,

[0256] D41 2-[2-[2-(Dimethylamino)ethoxy]ethyl-methylamino]ethanol

[0257]

[0258] Reaction product with isophorone diisocyanate,

[0259] D42 2-[2-[2-(Dimethylamino)ethoxy]ethyl-methylamino]ethanol

[0260]

[0261] Reaction product with hexamethylene-1,6-diisocyanate,

[0262] D43 3-{[3-(Dimethylamino)propyl]-methylamino}propanol

[0263]

[0264] Reaction product with isophorone diisocyanate,

[0265] D44 3-{[3-(Dimethylamino)propyl]-methyl-amino}propanol

[0266]

[0267] Reaction product with hexamethylene-1,6-diisocyanate,

[0268] D45 2-{[3-(Dimethylamino)propyl]-methyl-amino}ethanol

[0269]

[0270] Reaction product with isophorone diisocyanate,

[0271] D46 2-{[3-(Dimethylamino)propyl]-methyl-amino}ethanol

[0272]

[0273] Reaction product with hexamethylene-1,6-diisocyanate.

[0274] Preferred compounds obtainable by reacting at least one isocyanate compound with at least one isocyanate-reactive compound having at least one tertiary amino group are selected from:

[0275]

[0276] or their HDMI analogs:

[0277]

[0278] or their HDMI analogs:

[0279]

[0280] or their HDMI analogs:

[0281]

[0282] or their HDMI analogs:

[0283]

[0284] or their HDMI analogs:

[0285]

[0286] or their HDMI analogs:

[0287]

[0288] or their HDMI analogs:

[0289]

[0290] or its HDMI analog:

[0291]

[0292]

[0293] or its HDMI analog:

[0294]

[0295] or its HDMI analog:

[0296]

[0297]

[0298] or its HDMI analog:

[0299]

[0300] or its HDMI analog:

[0301]

[0302] or its HDMI analog:

[0303]

[0304] or its HDMI analog:

[0305]

[0306] or its HDMI analog:

[0307]

[0308]

[0309] or its HDMI analog:

[0310]

[0311] or its HDMI analog:

[0312]

[0313] or its HDMI analog:

[0314]

[0315]

[0316] or its HDMI analog:

[0317]

[0318] or its HDMI analog:

[0319]

[0320] or its HDMI analog:

[0321]

[0322]

[0323] or its HDMI analog:

[0324]

[0325] or its HDMI analog:

[0326]

[0327] In a further embodiment of the present invention, it has been found that certain compounds obtainable by reacting at least one isocyanate compound with at least one isocyanate-reactive compound having at least one tertiary amino group are new and are also active as catalysts, especially in polyurethane formation, even in the absence of Cu(II) salts. Accordingly, the present invention also relates to such compounds selected from:

[0328] (1)

[0329] The reaction product of N′,N′-dimethylpropane-1,3-diamine and isophorone diisocyanate,

[0330] (2)

[0331] The reaction product of N′,N′-dimethylpropane-1,3-diamine and hexamethylene-1,6-diisocyanate,

[0332] (3)

[0333] The reaction product of N′,N′-diethylpropane-1,3-diamine and isophorone diisocyanate,

[0334] (4)

[0335] The reaction product of N′,N′-diethylpropane-1,3-diamine and hexamethylene-1,6-diisocyanate,

[0336] (5)

[0337] Reaction product of 3-(diethylamino)propan-1-ol and isophorone diisocyanate,

[0338] (6)

[0339] Reaction product of 3-(diethylamino)propan-1-ol and hexamethylene-1,6-diisocyanate,

[0340] (7)

[0341] Reaction product of 3-(pyrrolidin-1-yl)propan-1-ol and isophorone diisocyanate,

[0342] (8)

[0343] Reaction product of 3-(pyrrolidin-1-yl)propan-1-ol and hexamethylene-1,6-diisocyanate,

[0344] (9)

[0345] Reaction product of 2-(pyrrolidin-1-yl)ethanol and isophorone diisocyanate,

[0346] (10)

[0347] Reaction product of 2-(pyrrolidin-1-yl)ethanol and hexamethylene-1,6-diisocyanate,

[0348] (11)

[0349] Reaction product of 2-(piperidin-1-yl)ethanol and isophorone diisocyanate,

[0350] (12)

[0351] Reaction product of 2-(piperidin-1-yl)ethanol and hexamethylene-1,6-diisocyanate,

[0352] (13)

[0353] Reaction product of 3-(piperidin-1-yl)propan-1-ol and isophorone diisocyanate,

[0354] (14)

[0355] Reaction product of 3-(pyrrolidin-1-yl)propan-1-amine and isophorone diisocyanate,

[0356] (15)

[0357] Reaction product of 3-pyrrolidin-1-ylpropan-1-amine and hexamethylene-1,6-diisocyanate

[0358] (16)

[0359] Reaction product of 2-pyrrolidin-1-yl ethanamine and isophorone diisocyanate

[0360] (17)

[0361] Reaction product of 2-pyrrolidin-1-yl ethanamine and hexamethylene-1,6-diisocyanate

[0362] (18)

[0363] Reaction product of 3-(piperidin-1-yl)propan-1-amine and isophorone diisocyanate

[0364] (19)

[0365] Reaction product of 3-(piperidin-1-yl)propan-1-amine and hexamethylene-1,6-diisocyanate

[0366] (20)

[0367] Reaction product of 2-(piperidin-1-yl)ethanamine and isophorone diisocyanate

[0368] (21)

[0369] Reaction product of 2-(piperidin-1-yl)ethanamine and hexamethylene-1,6-diisocyanate

[0370] (22)

[0371] Reaction product of 1-(piperidin-1-yl)propan-2-ol and isophorone diisocyanate

[0372] (23)

[0373] Reaction product of 1-(piperidin-1-yl)propan-2-ol and hexamethylene-1,6-diisocyanate

[0374] (24)

[0375] Reaction product of 1-pyrrolidin-1-ylpropan-2-ol and isophorone diisocyanate

[0376] (25)

[0377] Reaction product of 1-pyrrolidin-1-ylpropan-2-ol and hexamethylene-1,6-diisocyanate

[0378] (26)

[0379] Reaction product of 1-pyrrolidin-1-ylpropan-2-amine and isophorone diisocyanate

[0380] (27)

[0381] Reaction product of 1-pyrrolidin-1-ylpropan-2-amine and hexamethylene-1,6-diisocyanate

[0382] (28)

[0383] Reaction product of 1-(piperidin-1-yl)propan-2-amine and isophorone diisocyanate

[0384] (29)

[0385] Reaction product of 1-(piperidin-1-yl)propan-2-amine and hexamethylene-1,6-diisocyanate

[0386] (30)

[0387] Reaction product of 2-[2-[2-(dimethylamino)ethoxy]ethyl-methyl-amino]ethanol and isophorone diisocyanate

[0388] (31)

[0389] Reaction product of 2-[2-[2-(dimethylamino)ethoxy]ethyl-methyl-amino]ethanol and hexamethylene-1,6-diisocyanate

[0390] (32)

[0391] Reaction product of 3-[3-(dimethylamino)propyl-methyl-amino]propane-1-ol and isophorone diisocyanate

[0392] (33)

[0393] Reaction product of 3-[3-(dimethylamino)propyl-methyl-amino]propane-1-ol and hexamethylene-1,6-diisocyanate

[0394] (34)

[0395] Reaction product of 2-[3-(dimethylamino)propyl]-N-methylaminoethanol and isophorone diisocyanate,

[0396] (35)

[0397] Reaction product of 2-[3-(dimethylamino)propyl]-N-methylaminoethanol and hexamethylene-1,6-diisocyanate,

[0398] (36)

[0399] Reaction product of 2-(4-methylpiperazin-1-yl)ethanol and isophorone diisocyanate,

[0400] (37)

[0401] Reaction product of 2-(4-methylpiperazin-1-yl)ethanol and hexamethylene-1,6-diisocyanate,

[0402] (38)

[0403] Reaction product of 1,3-bis(dimethylamino)propan-2-ol and isophorone diisocyanate,

[0404] (39)

[0405] Reaction product of 1,3-bis(dimethylamino)propan-2-ol and hexamethylene-1,6-diisocyanate,

[0406] (40)

[0407] Reaction product of 2,4,6-tris[(dimethylamino)methyl]phenol and isophorone diisocyanate,

[0408] (41)

[0409] Reaction product of 2,4,6-tris[(dimethylamino)methyl]phenol and hexamethylene-1,6-diisocyanate,

[0410] (42)

[0411] Reaction product of N′-[2-[2-(dimethylamino)ethoxy]ethyl]-N′-methylpropane-1,3-diamine and isophorone diisocyanate,

[0412] (43)

[0413] Reaction product of N′-[2-[2-(dimethylamino)ethoxy]ethyl]-N′-methylpropane-1,3-diamine and hexamethylene-1,6-diisocyanate,

[0414] (44)

[0415] Reaction product of 3-imidazol-1-ylpropane-1-amine and isophorone diisocyanate,

[0416] (45)

[0417] Reaction product of 3-imidazol-1-ylpropane-1-amine and hexamethylene-1,6-diisocyanate,

[0418] (46)

[0419] Reaction product of 1-morpholinopropan-2-amine and isophorone diisocyanate,

[0420] (47)

[0421] Reaction product of 1-morpholinopropan-2-amine and hexamethylene-1,6-diisocyanate,

[0422] (48)

[0423] Reaction product of 2-(2-pyrrolidin-1-ylethoxy)ethanol and isophorone diisocyanate,

[0424] (49)

[0425] Reaction product of 2-(2-pyrrolidin-1-ylethoxy)ethanol and hexamethylene-1,6-diisocyanate,

[0426] (50)

[0427] Reaction product of 2-[methyl(2-pyrrolidin-1-ylethyl)amino]ethanol and isophorone diisocyanate,

[0428] (51)

[0429] Reaction product of 2-[methyl(2-pyrrolidin-1-ylethyl)amino]ethanol and hexamethylene-1,6-diisocyanate,

[0430] (52)

[0431] Reaction product of 1-[methyl(2-pyrrolidin-1-ylethyl)amino]propan-2-ol and isophorone diisocyanate,

[0432] (53)

[0433] Reaction product of 1-[methyl(2-pyrrolidin-1-ylethyl)amino]propan-2-ol and hexamethylene-1,6-diisocyanate,

[0434] (54)

[0435] Reaction product of 2-[methyl(3-pyrrolidin-1-ylpropyl)amino]ethanol and isophorone diisocyanate,

[0436] (55)

[0437] Reaction product of 2-[methyl(3-pyrrolidin-1-ylpropyl)amino]ethanol and hexamethylene-1,6-diisocyanate,

[0438] (56)

[0439] Reaction product of 1-[methyl(3-pyrrolidin-1-ylpropyl)amino]propan-2-ol and isophorone diisocyanate,

[0440] (57)

[0441] Reaction product of 1-[methyl(3-pyrrolidin-1-ylpropyl)amino]propan-2-ol and hexamethylene-1,6-diisocyanate,

[0442] (58)

[0443] Reaction product of 2-[methyl-[2-(1-piperidin-1-ylethyl)amino]ethanol and isophorone diisocyanate,

[0444] (59)

[0445] Reaction product of 2-[methyl-[2-(1-piperidin-1-ylethyl)amino]ethanol and hexamethylene-1,6-diisocyanate,

[0446] (60)

[0447] Reaction product of 1-[methyl-[2-(1-piperidin-1-ylethyl)amino]propan-2-ol and isophorone diisocyanate,

[0448] (61)

[0449] Reaction product of 1-[methyl-[2-(1-piperidinyl)ethyl]amino]propan-2-ol and hexamethylene-1,6-diisocyanate,

[0450] (62)

[0451] Reaction product of 2-[methyl-[3-(1-piperidinyl)propyl]amino]ethanol and isophorone diisocyanate,

[0452] (63)

[0453] Reaction product of 2-[methyl-[3-(1-piperidinyl)propyl]amino]ethanol and hexamethylene-1,6-diisocyanate,

[0454] (64)

[0455] Reaction product of 1-[methyl-[3-(1-piperidinyl)propyl]amino]propan-2-ol and isophorone diisocyanate, and

[0456] (65)

[0457] Reaction product of 1-[methyl-[3-(1-piperidinyl)propyl]amino]propan-2-ol and hexamethylene-1,6-diisocyanate.

[0458] As mentioned above, such compounds include especially and most preferably those in which both isocyanate groups of the diisocyanate have reacted, but may also include those in which only one isocyanate group has reacted and all molar ratios between these two molar ratios.

[0459] In a further embodiment of the invention, it relates to: a composition, said composition comprising one or more of the aforementioned specific compounds and at least one carboxylic acid, said carboxylic acid being preferably selected from monocarboxylic acid compounds, polycarboxylic acid compounds such as dicarboxylic acid compounds, and hydroxy-functional carboxylic acid compounds, as described in more detail below; and its use as a catalyst composition. The specific composition may not include a Cu(II) salt, but is also active as a catalyst, especially in polyurethane formation.

[0460] In a further embodiment of the present invention, a compound obtained by reacting at least one isocyanate compound and at least one isocyanate-reactive compound having at least one tertiary amino group is further reacted with at least one isocyanate compound and biuret, urethane, and isocyanurate of the compound are formed, as exemplified in the following scheme. The addition of an isocyanate group to a carbamate forms a urethane:

[0461]

[0462] The addition of an isocyanate group to a urea forms a biuret:

[0463]

[0464] The composition according to the invention comprises at least one copper(II) salt (Cu(II) salt), such as a carboxylic acid Cu(II), a diketone Cu(II), a halogenated Cu(II), or a combination of two or more thereof. According to the invention, the terms copper salt, copper(II) salt or Cu(II) salt also include any form of solvate, in particular hydrate, of such copper(II) salts. The copper salt can especially be in the form of a hydrate. The carboxylate is especially derived from an optionally substituted carboxylic acid such as an optionally substituted aliphatic, saturated monocarboxylic acid; an optionally substituted aliphatic, unsaturated monocarboxylic acid; an optionally substituted aliphatic, saturated poly (e.g., di) carboxylic acid, an optionally substituted heterocyclic carboxylic acid, an optionally substituted aromatic carboxylic acid. Preferably these carboxylic acids include optionally substituted aliphatic saturated carboxylic acids having up to 30 carbon atoms. Optionally substituents include especially hydroxyl, amino (including -NH2, -NHR and -NR2 (wherein R is a hydrocarbon group), halogen, alkoxy (resulting in an ether functionality), heterocyclic group. Among the substituted carboxylic acids, hydroxyl-functional carboxylic acids such as salicylic acid, lactic acid, etc. are most preferred. Preferred carboxylic acid Cu(II) include the following copper(II) salts: carbonic acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, nonadecanoic acid, arachidic acid, saturated and unsaturated fatty acids, dicarboxylic acids such as fumaric acid, maleic acid, hydroxyl-substituted carboxylic acids such as lactic acid (2-hydroxypropanoic acid), tartaric acid, aromatic carboxylic acids such as benzoic acid, salicylic acid, heterocyclic carboxylic acids such as nicotinic acid, pyrrolidine-2-carboxylic acid, amino acids such as glycine, alanine, and aminobutyric acid. The most preferred Cu(II) salts are carboxylic acid Cu(II), especially copper(II) acetate, copper(II) ethylhexanoate, copper(II) ricinoleate, copper(II) stearate, copper(II) palmitate, copper(II) laurate, copper(II) palmitoleate, copper(II) oleate, copper(II) linoleate, copper(II) linolenate. In particular, copper(II) acetate and copper(II) ethylhexanoate are preferred.

[0465] The diketone Cu(II) includes, in particular, diketonates of the following formula:

[0466] wherein R 1 、R 2 、and R 3 are preferably optionally substituted alkyl groups.

[0467] The preferred diketone Cu(II) is copper(II) acetylacetonate. The halogenated Cu(II) includes, in particular, copper(II) chloride.

[0468] The term copper(II) salt shall include all copper compounds as follows: where copper has an oxidation state of +2, regardless of the nature of the bond, which may be ionic, coordination covalent or covalent and any intermediate (transition) stage between those.

[0469] The composition according to the invention preferably comprises:

[0470] 10,000 - 99,991% by weight, preferably 15 - 95% by weight, more preferably 20 - 90% by weight of a compound obtainable by reacting at least one isocyanate compound with at least one isocyanate-reactive compound having at least one tertiary amino group,

[0471] 0.009 - 5% by weight, preferably 0.05 - 3% by weight, more preferably 0.5 - 2% by weight of copper, and

[0472] 0 - 89,991% by weight of a diluent,

[0473] wherein the % by weight is based on the total weight of the composition.

[0474] Without wishing to be bound by theory, it is believed that a compound obtainable by reacting at least one isocyanate compound with at least one isocyanate-reactive compound having at least one tertiary amino group, and in particular the tertiary amino group acts as a ligand in the coordination of Cu(II) in the composition according to the invention.

[0475] The composition according to the invention optionally comprises one or more diluents. Such diluents can be used to reduce the viscosity of the composition or to increase the solubility or incorporation ability of the copper(II) salt in the composition.

[0476] Diluents include isocyanate-reactive compounds or non-isocyanate-reactive compounds, i.e., diluents that do not react with isocyanates. In the case of using isocyanate-reactive compounds, especially when using a molar excess of such isocyanate-reactive compounds, which then act as diluents for the composition according to the invention. Regarding such isocyanate-reactive compounds, reference can be made to the preferred embodiments described above. Of course, any diluent comprising an isocyanate-reactive compound can also be added after the reaction of at least one isocyanate compound with at least one isocyanate-reactive compound having at least one tertiary amino group. Such isocyanate-reactive compounds can include various types of amines or alcohols and can also include known amine catalysts for polyurethane formation as explained below.

[0477] The non-reactive diluent / solvent can include in particular dialkyl sulfoxides such as dimethyl sulfoxide, diethyl sulfoxide, diisobutyl sulfoxide, etc.; N,N-dialkylalkanolamides such as N,N-dimethylformamide, N,N-dimethylacetamide, N,N-diethylacetamide, etc.; phosphonates such as O,O-dimethyl, O,O-diethyl, O,O-diisopropyl methyl phosphonate, O,O-bis(2-chloroethyl) vinyl phosphonate, etc.; aromatic solvents such as toluene, xylene, benzene, etc.; ether solvents such as diethyl ether, dioxane, diethylene glycol dimethyl ether, etc.; tetramethylene sulfone, 1-methyl-2-pyrrolidone, trialkyl phosphates such as trimethyl phosphate and triethyl phosphate, acetonitrile, etc., and organic carbonates like dimethyl carbonate, ethylene carbonate, propylene carbonate, or combinations thereof. The diluent / solvent can be used together with co-solvents such as fatty acids, vegetable oils, or combinations thereof.

[0478] In a preferred embodiment of the composition according to the invention, the one or more isocyanate-reactive compounds having at least one tertiary amino group are used as diluents, which means that they are used in a molar excess relative to the isocyanate compound based on the molar ratio of the isocyanate-reactive groups and the isocyanate groups.

[0479] Preferred solvents also include diols such as ethane-1,2-diol, propane-1,2-diol, propane-1,3-diol, butane-1,4-diol, propane-1,2,3-triol, diethylene glycol, dipropylene glycol, triethylene glycol, tetraethylene glycol, tripropylene glycol, 2-methyl-1,3-propanediol, 2-methyl-2,4-pentanediol. Those diluents / solvents can be used as a mixture or co-solvent together with amines.

[0480] In a further preferred embodiment of the composition according to the invention, it may optionally comprise one or more additional amines or amine catalysts for forming the polyisocyanate addition product, for example amines different from the isocyanate-reactive compounds. Such catalysts include alkylamines such as bis(2-dimethylaminoethyl) ether, N,N-dimethylcyclohexylamine, N,N,N',N',N''-pentamethyldiethylenetriamine, N,N,N',N',N''-pentamethyldipropylenetriamine, triethylenediamine, ethanolamines such as 2-aminoethanol, diethanolamine, triethanolamine, N-methyldiethanolamine, N,N-dimethylethanolamine, N,N-diethylethanolamine, N-methylethanolamine, N-ethylethanolamine, diisopropylamine, bis(2-hydroxypropyl)amine, 2-[2-(dimethylamino)ethoxy]ethanol, 1-[bis[3-(dimethylamino)propyl]amino]-2-propanol, 3-dimethylamino-N,N-dimethylpropanamide, N,N'-dimorpholinodiethylether, N,N'-dimethylpiperazine, N-methylmorpholine, N-ethylmorpholine, 2-{[2-(dimethylamino)ethyl]methylamino}ethanol, 3,3'-iminobis(N,N-dimethylpropylamine), 3-(dimethylamino)-1-propylamine, 3-(diethylamino)-1-propanol, 1-(3-hydroxypropyl)pyrrolidine, 1-(2-hydroxypropyl)pyrrolidine, 1-(2-hydroxyethyl)pyrrolidine, 1-(2-hydroxyethyl)piperidine, 1-(3-hydroxypropyl)piperidine, 1-(2-hydroxypropyl)piperidine, 1-(3-aminopropyl)pyrrolidine, 1-(2-aminoethyl)pyrrolidine, 1-(3-aminopropyl)piperidine, 1-(2-aminoethyl)piperidine, 1-(pyrrolidin-1-yl)-2-propanamine, 1-(piperidin-1-yl)propane-2-amine, N-methoxyethylmorpholine, N-methylimidazole, 1-(3-aminopropyl)imidazole, 2-[2-[2-(dimethylamino)ethoxy]ethyl-methylamino]ethanol, N-methyldicyclohexylamine, 3-{[3-(dimethylamino)propyl]methylamino}propanol, tris(dimethylaminopropyl)amine, 2-{[3-(dimethylamino)propyl]methylamino}ethanol, N,N,N',N'-tetramethyl-hexamethylenediamine, N,N,N',N'-tetramethylethylenediamine, 2,4,6-tris(dimethylaminomethyl)phenol, 1,3,5-tris(dimethylaminopropyl)-hexahydrotriazine, N,N-dimethylbenzylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene, N-methyl-N'-(2-dimethylamino)ethyl-piperazine, N,N'-bis[3-(dimethylamino)propyl]urea, N-[3-(dimethylamino)propyl]urea, N,N,N',N'-tetrakis(2-hydroxypropyl)ethylenediamine, and N,N,N',N'-tetrakis(2-hydroxyethyl)ethylenediamine.Preferred amines include alkylamines such as bis(2-dimethylaminoethyl) ether, N,N-dimethylaminopropylamine, N,N-dimethylcyclohexylamine, N,N,N',N',N''-pentamethyldiethylenetriamine, triethylenediamine, ethanolamines such as diethanolamine, 2(2-dimethylaminoethoxy)ethanol, N-[2-(dimethylamino)ethyl]-N-methylethanolamine, dimethylethanolamine, or other amines such as 3-dimethylamino-N,N-dimethylpropanamide and N-ethylmorpholine, triethanolamine, 2-dimethylaminoethanol, N,N-dimethylaminopropylamine, diethanolamine, trimethylamine, triethylenediamine, bis(2-dimethylaminoethyl) ether.

[0481] In a preferred embodiment, the composition according to the invention further comprises at least one carboxylic acid, such as those described in US6,387,972 B1. Preferably the carboxylic acid is selected from monocarboxylic acid compounds such as benzoic acid, polycarboxylic acid compounds such as dicarboxylic acid compounds such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, azelaic acid, sebacic acid, and hydroxy-functional carboxylic acid compounds, in particular salicylic acid, citric acid. In a particularly preferred embodiment, the composition comprises at least one carboxylic acid selected from the group consisting of: salicylic acid, benzoic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, azelaic acid, sebacic acid, and citric acid.

[0482] The present invention also relates to a process for manufacturing the composition according to the present invention. In a preferred embodiment, such a process comprises reacting at least one isocyanate compound and at least one isocyanate-reactive compound having at least one tertiary amino group in the presence of at least one Cu(II) salt and optionally in the presence of one or more diluents as described above. Non-reactive diluents / solvents include, for example, aprotic organic solvents (ethyl acetate, acetone, acetonitrile, ketones, halogenated alkanes, diethylene glycol dimethyl ether, dioxane, ethers - diethyl ether, methyl butyl ether, tetrahydrofuran, alkanes, dimethyl sulfoxide (DMSO), dimethylformamide (DMF), toluene, benzene, xylene and their analogues or mixtures thereof) that can be used to dissolve or melt the components before mixing them. In a preferred embodiment of the process, the Cu(II) salt is preferably mixed with the one or more isocyanate-reactive compounds having at least one tertiary amino group under vigorous stirring, and then the isocyanate compound is added under an inert atmosphere. The addition of the isocyanate compound is carried out slowly either continuously or in portions discontinuously. Given the exothermic reaction, the temperature rises. The preferred temperature range for the reaction is 20 - 140 °C, more preferably 40 - 120 °C, and most preferably 60 - 100 °C. Generally, it is preferred to carry out the reaction under an inert atmosphere (nitrogen, argon, etc.) to exclude moisture. After the reaction is complete, the diluent / solvent can be partially or completely removed to provide the final compounds, their mixtures or their concentrated solutions. It is recommended to prepare a catalyst blend containing diluents such as water, glycols (ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, 2-methyl-1,3-propanediol, etc.), mono- and dialkyl ethers of glycols, polyether polyols, plasticizers, waxes, and natural oils such as castor oil, soybean oil, etc. and their mixtures to facilitate the metering of the catalyst for use in the manufacture of polyurethanes. The resulting mixture according to the present invention is generally homogeneous and stable and can be used, for example, as a catalyst in the manufacture of polyisocyanate addition polymers as described below.

[0483] However, in another less preferred embodiment, the process for manufacturing the composition according to the present invention comprises reacting at least one isocyanate compound and at least one isocyanate-reactive compound having at least one tertiary amino group, optionally in the presence of one or more diluents, and subsequently adding at least one copper(II) salt.

[0484] The composition according to the invention is preferably used as a catalyst composition, in particular for catalyzing the reaction of at least one isocyanate compound with at least one isocyanate-reactive compound, and most preferably as a catalyst for the production of polyisocyanate addition products (i.e., polymers obtained from polyisocyanates and isocyanate-reactive compounds as compounds having active hydrogen atoms, in particular polyols and polyamines). Depending on which isocyanate-reactive compound is used, the polyisocyanate addition product has one or more functional groups consisting of groups selected from urethane groups and urea groups. Most preferably, the composition of the invention is used as a catalyst for the production of polyurethanes, in particular polyurethane foams. A typical composition for forming polyurethane foams is described, for example, in WO2016 / 039856 and comprises: (a) a polyol; (b) an isocyanate; (c) the composition according to the invention, (d) a surfactant; and (e) optional components such as blowing agents and other optional components such as surfactants, flame retardants, chain extenders, crosslinking agents, adhesion promoters, antistatic additives, hydrolysis and UV stabilizers, lubricants, antimicrobial agents, catalysts and / or other special additives can be used to produce dense or porous polyurethane materials [The polyurethanes book, edited by David Randall and Steve Lee, John Willey & Sons, LTD, 2002]. The polyol (a) component can be any polyol that can be used to form polyurethane foams.

[0485] In a further embodiment of the invention, it relates to a catalyst composition comprising the composition according to the invention as defined above. In a further embodiment, the invention relates to a process for the production of isocyanate addition products, which comprises reacting an isocyanate compound with an isocyanate-reactive compound in the presence of a catalyst composition as defined above. Regarding the preferred isocyanates and isocyanate-reactive compounds, reference may be made to the above description. Most preferably, the catalyst composition is used in a process for the production of isocyanate addition products, wherein the isocyanate is a polyisocyanate and the isocyanate-reactive compound is a polyol, and the process is for the production of polyurethanes, in particular polyurethane foams.

[0486] As used herein, the term "polyurethane" refers to the reaction product of an isocyanate containing two or more isocyanate groups with a compound containing two or more active hydrogens such as a polyol (polyether polyol, polyester polyol, copolymer polyol also referred to as graft polyol) and / or a polymer terminated with primary and secondary amines referred to as polyamines. These reaction products are generally referred to by those skilled in the art as polyurethanes and / or polyureas. The reactions for forming porous and non-porous foams optionally include a blowing agent. In the manufacture of polyurethane foams, the reactions include a blowing agent and other optional components such as surfactants, flame retardants, chain extenders, crosslinking agents, adhesion promoters, antistatic additives, hydrolysis and UV stabilizers, lubricants, antimicrobial agents, catalysts, and / or other specialty additives to produce dense or porous polyurethane materials [The polyurethanes book, edited by David Randall and Steve Lee, John Willey & Sons, LTD, 2002]. The present catalyst material of the invention is particularly suitable for use in the manufacture of flexible, semi-flexible, and rigid foams using one-shot pouring foaming, quasi-prepolymer, and prepolymer processes. The polyurethane manufacturing process of the invention typically involves the reaction of, for example, a polyol (generally, a polyol having a hydroxyl value of about 10 - about 700), an organic polyisocyanate, a blowing agent, and optional additives known to those skilled in the art and one or more catalysts (at least one of which is selected from the subject tertiary amine compounds). As blowing agents and optional additives, flexible and semi-flexible foam formulations (hereinafter simply referred to as flexible foams) also generally include, for example, water, an organic low-boiling auxiliary blowing agent or an optional non-reactive gas, a silicone surfactant, an optional catalyst, and an optional crosslinking agent. Rigid foam formulations often contain both a low-boiling organic material and water for foaming.

[0487] The "one-shot pouring foaming process" for manufacturing polyurethane foams is a one-step process in which all the ingredients necessary (or desirable) for making a foamed polyurethane product, including polyisocyanates, organic polyols, water, catalysts, surfactants, optional blowing agents, etc., are effectively mixed, poured onto a moving conveyor belt or into a mold of a suitable configuration and cured [Chemistry and Technology of Polyols for Polyurethanes, Mihail Ionescu, Rapra Technology LTD. (2005)]. The one-shot pouring process is in contrast to the prepolymer and quasi-prepolymer processes [[Flexible polyurethane foams, Ron Herrington and Kathy Hock, Dow Plastics, 1997]. In the prepolymer process, most of the prepolymers currently in use are isocyanate-tipped. When just enough polyisocyanate is added to react with all the available hydroxyl sites, a strict prepolymer is formed. If there is an excess or residual isocyanate monomer, the product is called a quasi-prepolymer. The prepolymer or quasi-prepolymer is first prepared in the absence of any foam-generating components. In a second step, a high molecular weight polyurethane material is formed by reacting the prepolymer with water and / or a chain extender such as ethylene glycol, diethylene glycol, 1,4-butanediol or diamine in the presence of a catalyst.

[0488] The catalyst composition of the present invention can be used as a sole catalyst or in combination with one or more additional catalysts for forming polyisocyanate adducts, such as the tertiary amine catalysts described above.

[0489] In addition, the catalyst composition of the present invention may include two or more different compounds obtainable by reacting at least one isocyanate compound with at least one isocyanate-reactive compound having at least one tertiary amino group as described above with a tertiary amine compound. The catalyst composition of the present invention may be present in a reactive mixture comprising all the required components in an amount of about 0.005% - about 5%; about 0.01% - about 3.0%; or about 0.03% - about 1.00 based on the total weight of the reactive composition. Other catalysts that can be used to manufacture polyurethane foams include, for example, tertiary amines such as the above alkylamines, organometallic catalysts such as organotin catalysts, metal salt catalysts such as alkali metal or alkaline earth metal carboxylate catalysts, other delayed-action catalysts, or other known polyurethane catalysts. Organometallic catalysts or metal salt catalysts can also and often are used in polyurethane foam formulations. For example, for flexible slabstock foams, the generally preferred metal salt and organometallic catalysts are stannous octoate and dibutyltin dilaurate, respectively. For flexible molded foams, exemplary organometallic catalysts are dibutyltin dilaurate and dibutyltin dialkylthiolate. For rigid foams, exemplary metal salt and organometallic catalysts are potassium acetate, potassium octoate, and dibutyltin dilaurate, respectively. Metal salt or organometallic catalysts are generally used in a small amount, typically in an amount of about 0.001 parts per hundred parts (pphp) - about 0.5 phpp based on the total weight of the composition.

[0490] The polyols that can be used in the process of the present invention for manufacturing polyurethanes, especially via a one-shot foaming process, are of any type currently used in the art for preparing flexible slabstock foams, flexible molded foams, semi-flexible foams, and rigid foams. Such polyols are typically liquids at ambient temperature and pressure and include polyether polyols and polyester polyols having a hydroxyl value in the range of about 15 - about 700. The hydroxyl value is preferably between about 20 - about 60 for flexible foams, between about 100 - about 300 for semi-flexible foams, and between about 250 - about 700 for rigid foams.

[0491] For flexible foams, the preferred functionality of the polyol, i.e., the average number of hydroxyl groups per molecule of the polyol, is about 2 - about 4 and most preferably about 2.3 - about 3.5. For rigid foams, the preferred functionality is about 2 - about 8 and most preferably about 3 - about 5.

[0492] Among the polyamines that can be used in the process of the present invention for manufacturing polyurethanes, diamines such as piperazine, 2,5-dimethylpiperazine, bis(4-aminophenyl) ether, 1,3-phenylenediamine, and hexamethylenediamine are preferred.

[0493] Polyfunctional isocyanate-reactive compounds, which can be used alone or in admixture as copolymers in a process for the production of polyurethanes and / or polyureas in the presence of the catalyst composition of the present invention, include, for example, polyols of any of the following non-limiting classes:

[0494] (a) Polyether polyols obtained by the reaction of polyhydroxyalkanes with one or more alkylene oxides such as ethylene oxide, propylene oxide, etc.;

[0495] (b) Polyether polyols obtained by the reaction of highly functional alcohols, sugar alcohols, sugars, and / or highly functional amines (if desired, in admixture with low-functional alcohols and / or amines) with alkylene oxides such as ethylene oxide, propylene oxide, etc.;

[0496] (c) Polyether polyols obtained by the reaction of phosphoric acid and polyphosphoric acid with alkylene oxides such as ethylene oxide, propylene oxide, etc.,

[0497] (d) Polyether polyols obtained by the reaction of polyaromatic alcohols with alkylene oxides such as ethylene oxide, propylene oxide, etc.;

[0498] (e) Polyether polyols obtained by the ring-opening polymerization of tetrahydrofuran;

[0499] (f) Polyether polyols obtained by the reaction of ammonia and / or amines with alkylene oxides such as ethylene oxide, propylene oxide, etc.;

[0500] (g) Polyester polyols obtained by the reaction of polyfunctional initiators such as diols with hydroxycarboxylic acids or their lactones such as hydroxycaproic acid or ε-caprolactone;

[0501] (h) Polyoxalate polyols obtained by the direct reaction of oxalates and diamines such as hydrazine, ethylenediamine, etc. in polyether polyols;

[0502] (i) Polyurea polyols obtained by the direct reaction of diisocyanates and diamines such as hydrazine, ethylenediamine, etc. in polyether polyols.

[0503] For flexible foams, the preferred type of alkylene oxide adducts of polyhydroxyalkanes are ethylene oxide and propylene oxide adducts of aliphatic triols such as glycerol, trimethylolpropane, etc. For rigid foams, the preferred classes of alkylene oxide adducts are ethylene oxide and propylene oxide adducts of ammonia, toluenediamine, sucrose, and phenol-formaldehyde-amine resins (Mannich bases).

[0504] Grafted or polymer polyols are widely used in the manufacture of flexible foams and, together with standard polyols, are one of the preferred classes of polyols that can be used in the processes of the present invention. Polymer polyols are polyols containing a stable dispersion of polymers (e.g., in the above polyols a)-e) and more preferably polyols of type a)). Other polymer polyols that can be used in the processes of the present invention are polyurea polyols and polycarbamate polyols.

[0505] The polyisocyanates that can be used in the polyurethane foam-forming processes of the present invention are organic compounds containing at least two isocyanate groups and will generally be any known aromatic or aliphatic polyisocyanate. Suitable organic polyisocyanates include, for example, hydrocarbon diisocyanates (e.g., alkylene diisocyanates and arylene diisocyanates), such as methylene diphenyl diisocyanate (MDI) and 2,4- and 2,6-toluene diisocyanate (TDI), as well as known triisocyanates and polymethylene poly(phenylene isocyanate), also referred to as polymeric or crude MDI. For flexible and semi-flexible foams, the preferred isocyanates are typically, for example, mixtures of 2,4-toluene diisocyanate and 2,6-toluene diisocyanate (TDI) in weight ratios of about 80% and about 20% and about 65% and about 35% respectively, based on the total weight of the TDI composition; mixtures of TDI and polymeric MDI, preferably in weight ratios of about 80% TDI and about 20% crude polymeric MDI to about 50% TDI and about 50% crude polymeric MDI, based on the total weight of the composition; and all polyisocyanates of the MDI type. For rigid foams, the preferred isocyanates are, for example, polyisocyanates of the MDI type and preferably crude polymeric MDI.

[0506] The amount of polyisocyanate included in the formulation is described in terms of the "isocyanate index" relative to the amounts of the other materials in the foam formulation used. The "isocyanate index" means the actual amount of polyisocyanate used divided by the stoichiometric amount of polyisocyanate theoretically required to react with all the active hydrogens in the reaction mixture, multiplied by one hundred (100) [see Oertel, Polyurethane Handbook, Hanser Publishers, New York, N.Y. (1985)]. The isocyanate index of the reaction mixture used in the processes of the present invention is typically between 60 and 140. More typically, the isocyanate index is: for flexible TDI foams, typically between 85 and 120; for molded TDI foams, generally between 90 and 105; for molded MDI foams, most often between 70 and 90; and for rigid MDI foams, generally between 90 and 130. Some examples of polyisocyanurate rigid foams are manufactured at indices up to 250 - 400.

[0507] Water is often used as a reactive blowing agent in both flexible and rigid foams. In the manufacture of flexible slabstock foam, water is typically used at a concentration, for example, between 2 and 6.5 parts per hundred parts (pphp) of the polyol blend, and more often between 3.5 and 5.5 pphp of the polyol blend. For TDI molded foams, the water level typically ranges, for example, from 3 to 4.5 pphp of the polyol blend. For MDI molded foams, the water level is, for example, more typically between 2.5 and 15 pphp. For rigid foams, the water level ranges, for example, from 0.5 to 5 pphp of the polyol blend, and more often 0.5 to 2 pphp. In the manufacture of polyurethane foams according to the present invention, physical blowing agents such as blowing agents based on volatile hydrocarbons or halogenated hydrocarbons and other non-reactive gases can also be used. A significant proportion of the rigid insulation foams manufactured are blown with volatile hydrocarbons or halogenated hydrocarbons and the preferred blowing agents are hydrochlorofluorocarbons (HCFCs) as well as the volatile hydrocarbons pentane and cyclopentane. In the manufacture of flexible slabstock foam, water is the primary blowing agent; however, other blowing agents can be used as auxiliary blowing agents. For flexible slabstock foam, the preferred auxiliary blowing agents are carbon dioxide and dichloromethane (methylene chloride). Other blowing agents such as chlorofluorocarbons (CFCs) and trichlorofluoromethane (CFC-11) can also be used.

[0508] Flexible molded foams typically do not use inert auxiliary blowing agents and, in any case, introduce fewer auxiliary blowing agents compared to slabstock foams. However, there is significant interest in the use of carbon dioxide in some molding techniques. MDI molded foams in Asia and some developing countries use methylene chloride, CFC-11, and other blowing agents. The amount of blowing agent varies according to the desired foam density and foam hardness, as recognized by those skilled in the art. When used, the amount of hydrocarbon-type blowing agents varies from, for example, trace amounts to about 50 parts per hundred parts (pphp) of the polyol blend, and CO2 varies from, for example, about 1 to about 10 pphp of the polyol blend.

[0509] Crosslinking agents can also be used in the manufacture of polyurethane foams. Crosslinking agents are typically small molecules; usually having a molecular weight less than 350, which contain hydrogen that is reactive towards reaction with isocyanates. The functionality of the crosslinking agent is greater than 3 and preferably between 3 and 5. The amount of crosslinking agent used can vary between about 0.1 pphp and about 20 pphp based on the polyol blend and the amount used is adjusted to achieve the desired foam stabilization or foam hardness. Examples of crosslinking agents include glycerol, diethanolamine, triethanolamine, and tetra-hydroxyethylenediamine.

[0510] Silicone surfactants useful in the processes of the present invention include, for example, "hydrolyzable" polysiloxane - polyoxyalkylene block copolymers, "non - hydrolyzable" polysiloxane - polyoxyalkylene block copolymers, cyanoalkyl polysiloxanes, alkyl polysiloxanes, and polydimethylsiloxane oils. The type of silicone surfactant used and the amount required depend on the type of foam being manufactured, as will be appreciated by those skilled in the art. The silicone surfactant can be used as such or dissolved in a solvent such as a glycol. For flexible slabstock foams, the reaction mixture typically contains from about 0.1 - about 6 pphp, and more often from about 0.7 - about 2.5 pphp of silicone surfactant. For flexible molded foams, the reaction mixture typically contains from about 0.1 - about 5 pphp, and more often from about 0.5 - about 2.5 pphp of silicone surfactant. For rigid foams, the reaction mixture typically contains from about 0.1 - about 5 pphp, and more often from about 0.5 - about 3.5 pphp of silicone surfactant. The amount used is adjusted to achieve the desired cell structure and foam stabilization.

[0511] The temperature useful for manufacturing polyurethanes varies depending on the type of foam and the specific process used for manufacturing, as will be well understood by those skilled in the art. Flexible slabstock foams are typically manufactured by mixing the reactants at ambient temperature, generally between about 20°C and about 40°C. The conveyor belt on which the foam rises and cures is essentially at ambient temperature, which can vary significantly depending on the geographical area where the foam is manufactured and the time of year. Flexible molded foams are typically manufactured by mixing the reactants at a temperature between about 20°C and about 30°C, and more often between about 20°C and about 25°C. The mixed starting materials are fed into a mold, typically by pouring. The mold is preferably heated to a temperature between about 20°C and about 70°C, and more often between about 40°C and about 65°C. The starting materials for spray - applied rigid foams are mixed and sprayed at ambient temperature. The starting materials for cast rigid foams are mixed at a temperature in the range of about 20°C - about 35°C. A preferred process for manufacturing flexible slabstock foams, molded foams, and rigid foams according to the present invention is the "one - shot" process in which the starting materials are mixed and reacted in one step.

[0512] Accordingly, in one embodiment of the present invention, it relates to a process for manufacturing an isocyanate addition product according to any one of the preceding claims, wherein the isocyanate addition product is a polyurethane, preferably a polyurethane foam, which is selected from porous or non-porous polyurethanes, and the process optionally includes a blowing agent. In such a process, there is optionally included the addition of a surfactant, a flame retardant, a chain extender, a crosslinking agent, an adhesion promoter, an antistatic additive, a hydrolysis stabilizer, a UV stabilizer, a lubricant, an antimicrobial agent, or any other common auxiliary additives used in the manufacture of polyurethanes, or a combination of two or more thereof. Accordingly, in one embodiment of the present invention, it also relates to a foam-forming isocyanate addition product formed by the process for manufacturing an isocyanate addition product as described above using the catalyst composition of the present invention. Such foam-forming isocyanate addition products are, for example, selected from blocks, molded foams, flexible foams, rigid foams, semi-rigid foams, spray foams, thermoformable foams, footwear foams, open-cell foams, closed-cell foams, and adhesives.

[0513] The preferred embodiments of the present invention are summarized below:

[0514] 1. A composition comprising at least one Cu(II) salt, at least one compound obtainable by reacting at least one isocyanate compound with at least one isocyanate-reactive compound having at least one tertiary amino group, and optionally one or more diluents.

[0515] 2. The composition according to embodiment 1, comprising a compound obtainable by reacting at least one isocyanate compound with at least one isocyanate-reactive compound having at least one tertiary amino group in the presence of at least one Cu(II) salt and optionally in the presence of one or more diluents.

[0516] 3. The composition according to embodiment 1 or 2, comprising a compound obtainable by reacting at least one polyisocyanate compound, at least one isocyanate-reactive compound having at least one tertiary amino group, and at least one isocyanate-reactive compound not having a tertiary amino group in the presence of at least one Cu(II) salt and optionally in the presence of one or more diluents.

[0517] 4. The composition according to any one of the preceding embodiments, comprising: a compound containing at least one urethane (carbamate) and / or urea group and at least one tertiary amino group, at least one Cu(II) salt, and optionally one or more diluents.

[0518] 5. A composition according to any of the foregoing embodiments, wherein the isocyanate compound is selected from polyisocyanates and monoisocyanates, such as octadecyl isocyanate; octyl isocyanate; butyl and tert-butyl isocyanates; cyclohexyl isocyanate; adamantyl isocyanate; ethyl isocyanatoacetate; ethoxycarbonyl isocyanate; phenyl isocyanate; α-methylbenzyl isocyanate; 2-phenylcyclopropyl isocyanate; 2-ethylphenyl isocyanate; benzyl isocyanate; m- and p-tolyl isocyanates; 2-, 3-, or 4-nitrophenyl isocyanate; 2-ethoxyphenyl isocyanate; 3-methoxyphenyl isocyanate; 4-methoxyphenyl isocyanate; ethyl 4-isocyanatobenzoate; 2,6-dimethylphenyl isocyanate; 1-naphthyl isocyanate; (naphthyl)ethyl isocyanate; isophorone diisocyanate (IPDI); toluene diisocyanate (TDI); diphenylmethane-2,4'-diisocyanate (2,4'-MDI); diphenylmethane-4,4'-diisocyanate (4,4'-MDI); hydrogenated diphenylmethane-4,4'-diisocyanate (H12 MDI); tetramethylxylene diisocyanate (TMXDI); hexamethylene-1,6-diisocyanate (HDI); naphthalene-1,5-diisocyanate; 3,3'-dimethoxy-4,4'-biphenyl diisocyanate; 3,3'-dimethyl-4,4'-dimethyl-4,4'-biphenyl diisocyanate; phenylene diisocyanate; 4,4'-biphenyl diisocyanate; trimethylhexamethylene diisocyanate; 4,4'-methylene-bis(2,6-diethylphenyl isocyanate); 1,12-diisocyanatododecane; 1,5-diisocyanato-2-methylpentane; 1,4-diisocyanatobutane; and cyclohexylene diisocyanate and its isomers; the uretdione dimer of HDI; the trimethylolpropane trimer of TDI; the isocyanurate trimer of TDI, HDI, or IPDI; the biuret trimer of TDI, HDI, or IPDI; and the polyisocyanate as described above in which the isocyanate groups are partially reacted with at least one isocyanate-reactive compound that does not have a tertiary amino group, the isocyanate-reactive compound being preferably selected from OH-, NH-, and NH2-functional optionally substituted hydrocarbons that may contain one or more heteroatoms, such as alcohols like methanol, tert-butanol, isopropanol, sec-butanol, OH-functional mono(ethylene) glycol ethers, OH-functional di(ethylene) glycol ethers, etc.

[0519] 6. A composition according to any of the foregoing embodiments, wherein the isocyanate compound is selected from polyisocyanates.

[0520] 7. A composition according to any of the foregoing embodiments, wherein the isocyanate compound is isophorone diisocyanate (IPDI).

[0521] 8. A composition according to any of the foregoing embodiments, wherein the isocyanate-reactive compound having at least one tertiary amino group is selected from alcohols having at least one tertiary amino group and amines having at least one tertiary amino group and at least one additional amino group selected from primary and secondary amino groups.

[0522] 9. A composition according to the previous embodiment, wherein the isocyanate-reactive compound comprises at least one ether group (-O-), and preferably the isocyanate-reactive compound is selected from aliphatic alcohols having at least one hydroxyl group, at least one tertiary amino group and optionally at least one ether group.

[0523] 10. A composition according to any of the foregoing embodiments, wherein the isocyanate-reactive compound having at least one tertiary amino group is selected from:

[0524]

[0525]

[0526]

[0527]

[0528]

[0529]

[0530]

[0531]

[0532]

[0533]

[0534] and bicyclic tertiary amines, such as

[0535]

[0536]

[0537]

[0538]

[0539] Preferably

[0540]

[0541]

[0542] or a mixture thereof.

[0543] 11. The composition according to the foregoing embodiments, wherein the compound is selected from:

[0544] C1 1-[Bis[3-(dimethylamino)propyl]amino]-2-propanol and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0545] C2 2-[2-(Dimethylamino)ethoxy]ethanol and the reaction product with: 1,3-bis(1-isocyanato-1-methylethyl)benzene, isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI), and more preferably 1,3-bis(1-isocyanato-1-methylethyl)benzene,

[0546] C3 2-{[2-(Dimethylamino)ethyl]methylamino}ethanol and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI),

[0547] C4 3,3'-iminobis(N,N-dimethylpropylamine) and the reaction product with: 1,3-bis(1-isocyanato-1-methylethyl)benzene, isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI), and more preferably 1,3-bis(1-isocyanato-1-methylethyl)benzene,

[0548] C5 dimethylaminoethanol and the reaction product with the following: 1,3-bis(1-isocyanato-1-methylethyl)benzene, isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI), and more preferably 1,3-bis(1-isocyanato-1-methylethyl)benzene,

[0549] C6 diethylaminoethanol and the reaction product with the following: 1,3-bis(1-isocyanato-1-methylethyl)benzene, isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI), and more preferably 1,3-bis(1-isocyanato-1-methylethyl)benzene,

[0550] C7 3-(dimethylamino)-1-propylamine and the reaction product with the following: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0551] C8 3-(diethylamino)-1-propylamine and the reaction product with the following: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0552] C9 3-(diethylamino)-1-propanol and the reaction product with the following: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0553] C10 1-(3-Hydroxypropyl)pyrrolidine and the reaction product with the following: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0554] C11 1-(2-Hydroxyethyl)pyrrolidine and the reaction product with the following: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0555] C12 1-(2-Hydroxyethyl)piperidine and the reaction product with the following: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0556] C13 1-(3-Hydroxypropyl)piperidine and the reaction product with the following: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0557] C14 1-(2-Hydroxypropyl)piperidine and the reaction product with the following: hexamethylene-1,6-diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0558] C15 1-(3-Aminopropyl)pyrrolidine and the reaction product with the following: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0559] C16 The reaction product of 1-(2-aminoethyl)pyrrolidine with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0560] C17 The reaction product of 1-(3-aminopropyl)piperidine with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0561] C18 The reaction product of 1-(2-aminoethyl)piperidine with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0562] C19 The reaction product of 1-(piperidin-1-yl)propan-2-ol with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0563] C20 The reaction product of 1-(pyrrolidin-1-yl)propan-2-ol with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0564] C21 The reaction product of 1-(1-pyrrolidinyl)-2-propanamine with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0565] C22 1-(Piperidin-1-yl)propan-2-amine and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0566] C23 2-[2-[2-(Dimethylamino)ethoxy]ethyl-methylamino]ethanol and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI),

[0567] C24 3-{[3-(Dimethylamino)propyl]methylamino}propanol and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI), and

[0568] C25 2-{[3-(Dimethylamino)propyl]methylamino}ethanol and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI such as its biuret, isocyanurate, urethane, and oligomers, preferably isophorone diisocyanate (IPDI) or hexamethylene-1,6-diisocyanate (HDI).

[0569] 21. The composition according to the previous embodiment, wherein the compound is selected from:

[0570]

[0571] Or its HDMI analog:

[0572]

[0573] Or its HDMI analog:

[0574]

[0575] Or its HDMI analog:

[0576]

[0577] or its HDMI analog:

[0578]

[0579] or its HDMI analog:

[0580]

[0581]

[0582] or its HDMI analog:

[0583]

[0584] or its HDMI analog:

[0585]

[0586] or its HDMI analog:

[0587]

[0588] or its HDMI analog:

[0589]

[0590] or its HDMI analog:

[0591]

[0592] or its HDMI analog:

[0593]

[0594]

[0595] or its HDMI analog:

[0596]

[0597] or its HDMI analog:

[0598]

[0599] or its HDMI analog:

[0600]

[0601] or its HDMI analog:

[0602]

[0603] or its HDMI analog:

[0604]

[0605]

[0606] or its HDMI analog:

[0607]

[0608] or its HDMI analog:

[0609]

[0610] or its HDMI analog:

[0611]

[0612] or its HDMI analog:

[0613]

[0614] or its HDMI analog:

[0615]

[0616] or its HDMI analog:

[0617]

[0618]

[0619] or its HDMI analog:

[0620]

[0621] 13. A compound selected from:

[0622] (1) The reaction product of 3-(dimethylamino)-1-propylamine and isophorone diisocyanate,

[0623] (2) The reaction product of 3-(dimethylamino)-1-propylamine and hexamethylene-1,6-diisocyanate,

[0624] (3) The reaction product of 3-(diethylamino)-1-propylamine and isophorone diisocyanate,

[0625] (4) The reaction product of 3-(diethylamino)-1-propylamine and hexamethylene-1,6-diisocyanate,

[0626] (5) Reaction product of 3-(diethylamino)-1-propanol and isophorone diisocyanate,

[0627] (6) Reaction product of 3-(diethylamino)-1-propanol and hexamethylene-1,6-diisocyanate,

[0628] (7) Reaction product of 1-(3-hydroxypropyl)pyrrolidine and isophorone diisocyanate,

[0629] (8) Reaction product of 1-(3-hydroxypropyl)pyrrolidine and hexamethylene-1,6-diisocyanate,

[0630] (9) Reaction product of 1-(2-hydroxyethyl)pyrrolidine and isophorone diisocyanate,

[0631] (10) Reaction product of 1-(2-hydroxyethyl)pyrrolidine and hexamethylene-1,6-diisocyanate,

[0632] (11) Reaction product of 1-(2-hydroxyethyl)piperidine and isophorone diisocyanate,

[0633] (12) Reaction product of 1-(2-hydroxyethyl)piperidine and hexamethylene-1,6-diisocyanate,

[0634] (13) Reaction product of 1-(3-hydroxypropyl)piperidine and isophorone diisocyanate,

[0635] (14) Reaction product of 1-(3-aminopropyl)pyrrolidine and isophorone diisocyanate,

[0636] (15) Reaction product of 1-(3-aminopropyl)pyrrolidine and hexamethylene-1,6-diisocyanate,

[0637] (16) Reaction product of 1-(2-aminoethyl)pyrrolidine and isophorone diisocyanate,

[0638] (17) Reaction product of 1-(2-aminoethyl)pyrrolidine and hexamethylene-1,6-diisocyanate,

[0639] (18) Reaction product of 1-(3-aminopropyl)piperidine and isophorone diisocyanate,

[0640] (19) Reaction product of 1-(3-aminopropyl)piperidine and hexamethylene-1,6-diisocyanate,

[0641] (20) Reaction product of 1-(2-aminoethyl)piperidine and isophorone diisocyanate,

[0642] (21) Reaction product of 1-(2-aminoethyl)piperidine and hexamethylene-1,6-diisocyanate,

[0643] (22) Reaction product of 1-(piperidin-1-yl)propan-2-ol and isophorone diisocyanate,

[0644] (23) Reaction product of 1-(piperidin-1-yl)propan-2-ol and hexamethylene-1,6-diisocyanate,

[0645] (24) Reaction product of 1-(pyrrolidin-1-yl)propan-2-ol and isophorone diisocyanate,

[0646] (25) Reaction product of 1-(pyrrolidin-1-yl)propan-2-ol and hexamethylene-1,6-diisocyanate,

[0647] (26) Reaction product of 1-(1-pyrrolidinyl)-2-propanamine and isophorone diisocyanate,

[0648] (27) Reaction product of 1-(1-pyrrolidinyl)-2-propanamine and hexamethylene-1,6-diisocyanate,

[0649] (28) Reaction product of 1-(piperidin-1-yl)propan-2-amine and isophorone diisocyanate,

[0650] (29) Reaction product of 1-(piperidin-1-yl)propan-2-amine and hexamethylene-1,6-diisocyanate,

[0651] (30) Reaction product of 2-[2-[2-(dimethylamino)ethoxy]ethyl-methylamino]ethanol and isophorone diisocyanate,

[0652] (31) Reaction product of 2-[2-[2-(dimethylamino)ethoxy]ethyl-methylamino]ethanol and hexamethylene-1,6-diisocyanate,

[0653] (32) Reaction product of 3-{[3-(dimethylamino)propyl]methylamino}propanol and isophorone diisocyanate,

[0654] (33) Reaction product of 3-{[3-(dimethylamino)propyl]methylamino}propanol and hexamethylene-1,6-diisocyanate,

[0655] (34) Reaction product of 2-{[3-(dimethylamino)propyl]methylamino}ethanol and isophorone diisocyanate,

[0656] (35) Reaction product of 2-{[3-(dimethylamino)propyl]methylamino}ethanol and hexamethylene-1,6-diisocyanate,

[0657] (36) Reaction product of N-hydroxyethyl-N'-methylpiperazine and isophorone diisocyanate

[0658] (37) Reaction product of N-hydroxyethyl-N'-methylpiperazine and hexamethylene-1,6-diisocyanate

[0659] (38) Reaction product of 1,3-bis(dimethylamino)-2-propanol and isophorone diisocyanate

[0660] (39) Reaction product of 1,3-bis(dimethylamino)-2-propanol and hexamethylene-1,6-diisocyanate

[0661] (40) Reaction product of 2,4,6-tris(dimethylaminoethyl)phenol and isophorone diisocyanate

[0662] (41) Reaction product of 2,4,6-tris(dimethylaminoethyl)phenol and hexamethylene-1,6-diisocyanate

[0663] (42) Reaction product of 3-(dimethylamino)-1-propylamine and isophorone diisocyanate

[0664] (43) Reaction product of 3-(dimethylamino)-1-propylamine and hexamethylene-1,6-diisocyanate

[0665] (44) Reaction product of (2-{2-[(3-aminopropyl)(methyl)amino]ethoxy}ethyl)dimethylamine and isophorone diisocyanate

[0666] (45) Reaction product of (2-{2-[(3-aminopropyl)(methyl)amino]ethoxy}ethyl)dimethylamine and hexamethylene-1,6-diisocyanate

[0667] (46) Reaction product of 1-(3-aminopropyl)imidazole and isophorone diisocyanate

[0668] (47) Reaction product of 1-(3-aminopropyl)imidazole and hexamethylene-1,6-diisocyanate

[0669] (48) Reaction product of 4-(2-aminopropyl)morpholine and isophorone diisocyanate

[0670] (49) Reaction product of 4-(2-aminopropyl)morpholine and hexamethylene-1,6-diisocyanate

[0671] (50) Reaction product of 2-(2-pyrrolidinoethoxy)ethanol and isophorone diisocyanate

[0672] (51) Reaction product of 2-(2-pyrrolidinoethoxy)ethanol and hexamethylene-1,6-diisocyanate,

[0673] (52) Reaction product of 2-(2-pyrrolidinoethyl N-methylamino)ethanol and isophorone diisocyanate,

[0674] (53) Reaction product of 2-(2-pyrrolidinoethyl N-methylamino)ethanol and hexamethylene-1,6-diisocyanate,

[0675] (54) Reaction product of N-(2-pyrrolidinoethyl)-N-methyl-2-hydroxypropylamine and isophorone diisocyanate,

[0676] (55) Reaction product of N-(2-pyrrolidinoethyl)-N-methyl-2-hydroxypropylamine and hexamethylene-1,6-diisocyanate,

[0677] (56) Reaction product of 2-(3-pyrrolidinopropyl N-methylamino)ethanol and isophorone diisocyanate,

[0678] (57) Reaction product of 2-(3-pyrrolidinopropyl N-methylamino)ethanol and hexamethylene-1,6-diisocyanate,

[0679] (58) Reaction product of N-(3-pyrrolidinopropyl)-N-methyl-2-hydroxypropylamine and isophorone diisocyanate,

[0680] (59) Reaction product of N-(3-pyrrolidinopropyl)-N-methyl-2-hydroxypropylamine and hexamethylene-1,6-diisocyanate,

[0681] (60) Reaction product of 2-(2-piperidinoethyl N-methylamino)ethanol and isophorone diisocyanate,

[0682] (61) Reaction product of 2-(2-piperidinoethyl N-methylamino)ethanol and hexamethylene-1,6-diisocyanate,

[0683] (62) Reaction product of N-(2-piperidinoethyl)-N-methyl-2-hydroxypropylamine and isophorone diisocyanate,

[0684] (63) Reaction product of N-(2-piperidinoethyl)-N-methyl-2-hydroxypropylamine and hexamethylene-1,6-diisocyanate,

[0685] (64) Reaction product of 2-(3-piperidinopropyl N-methylamino)ethanol and isophorone diisocyanate,

[0686] (65)Reaction product of 2-(3-piperidinopropyl-N-methylamino)ethanol and hexamethylene-1,6-diisocyanate,

[0687] (66)Reaction product of N-(3-piperidinopropyl)-N-methyl-2-hydroxypropylamine and isophorone diisocyanate, and

[0688] (67)Reaction product of N-(3-piperidinopropyl)-N-methyl-2-hydroxypropylamine and hexamethylene-1,6-diisocyanate.

[0689] 13. A composition according to any of the foregoing embodiments, wherein the compound obtained by reacting at least one isocyanate compound and at least one isocyanate-reactive compound having at least one tertiary amino group, optionally in the presence of at least one Cu(II) salt and optionally in the presence of one or more diluents, is further reacted with at least one isocyanate compound and the biuret, urethane, and isocyanurate of the compound are formed.

[0690] 14. A composition according to any of the foregoing embodiments, wherein the at least one Cu(II) salt is selected from Cu(II) carboxylates.

[0691] 15. A composition according to any of the foregoing embodiments, comprising

[0692] 10 - 99.991% by weight, preferably 15 - 95% by weight, more preferably 20 - 90% by weight of a compound obtained by reacting at least one isocyanate compound and at least one isocyanate-reactive compound having at least one tertiary amino group,

[0693] 0.009 - 5% by weight, preferably 0.05 - 3% by weight, more preferably 0.5 - 2% by weight of copper, and

[0694] 0 - 89.991% by weight of a diluent,

[0695] wherein the percentages by weight are based on the total weight of the composition.

[0696] 16. A composition according to any of the foregoing embodiments, comprising one or more isocyanate-reactive compounds having at least one tertiary amino group.

[0697] 17. A composition according to any of the foregoing embodiments, further comprising one or more additional catalysts for forming polyisocyanate addition products.

[0698] 18. A composition according to any of the foregoing embodiments, further comprising at least one carboxylic acid, which is preferably selected from monocarboxylic acid compounds, polycarboxylic acid compounds such as dicarboxylic acid compounds, and hydroxy-functional carboxylic acid compounds.

[0699] 19. A composition according to any of the foregoing embodiments, further comprising at least one carboxylic acid selected from salicylic acid, benzoic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, azelaic acid, sebacic acid, and citric acid, or

[0700] The composition comprises at least one compound of embodiment 13 and at least one carboxylic acid selected from salicylic acid, benzoic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, azelaic acid, sebacic acid, and citric acid, and does not include a Cu(II) salt.

[0701] 20. A process for manufacturing a composition according to any of the foregoing embodiments, the process comprising reacting at least one isocyanate compound and at least one isocyanate-reactive compound having at least one tertiary amino group in the presence of at least one Cu(II) salt and optionally in the presence of one or more diluents.

[0702] 21. A process for manufacturing a composition according to any of the foregoing embodiments, the process comprising reacting at least one isocyanate compound and at least one isocyanate-reactive compound having at least one tertiary amino group, optionally in the presence of one or more diluents, and subsequently adding at least one copper(II) salt.

[0703] 22. A process for manufacturing a composition according to the foregoing embodiments, wherein the reaction is carried out at a temperature of about 20 - 140 °C, more preferably about 40 - 120 °C, and most preferably about 60 - 100 °C.

[0704] 23. Use of a composition according to any of the foregoing embodiments, or a compound of embodiment 13, or a composition of embodiment 20 that does not include a Cu(II) salt as a catalyst.

[0705] 24. Use according to the previous embodiment, as a catalyst for the reaction of at least one isocyanate compound with at least one isocyanate-reactive compound.

[0706] 25. Use according to the foregoing embodiments, as a catalyst for manufacturing a polyisocyanate addition polymerization product.

[0707] 26. Use according to the foregoing embodiments, wherein the polyisocyanate addition polymerization product has one or more functional groups composed of groups selected from urethane groups and urea groups.

[0708] 27. Use according to the foregoing embodiments, as a catalyst for the production of polyurethanes, in particular polyurethane foams.

[0709] 28. A catalyst composition comprising a composition according to any one of the foregoing embodiments, or the compound of embodiment 13, or the composition of embodiment 20 excluding a Cu(II) salt, or the compound of claim 13, or the composition of claim 20 excluding a Cu(II) salt.

[0710] 29. A process for the production of an isocyanate addition product, which comprises reacting an isocyanate compound with an isocyanate-reactive compound in the presence of a composition as defined in any one of the foregoing embodiments.

[0711] 30. A process for the production of an isocyanate addition product according to embodiment 29, wherein the isocyanate is a polyisocyanate and the isocyanate-reactive compound is a polyol, and the process is for the production of polyurethanes, in particular polyurethane foams.

[0712] 31. A process for the production of an isocyanate addition product according to any one of the foregoing embodiments, wherein the isocyanate addition product is a polyurethane, preferably a polyurethane foam, selected from porous or non-porous polyurethanes, and the process optionally comprises a blowing agent.

[0713] 32. A process for the production of an isocyanate addition product according to any one of the foregoing embodiments, wherein the process is for the production of polyurethanes, and the process optionally comprises the addition of a surfactant, a flame retardant, a chain extender, a crosslinking agent, an adhesion promoter, an antistatic additive, a hydrolysis stabilizer, a UV stabilizer, a lubricant, an antimicrobial agent, or a combination of two or more thereof.

[0714] 33. A process for the production of an isocyanate addition product according to any one of the foregoing embodiments, wherein the composition as defined in any one of the foregoing claims is present in an amount of from about 0.005% to about 5% by weight, based on the total weight of the entire composition including all components.

[0715] 34. A foam-forming isocyanate addition product obtainable by a process for the production of an isocyanate addition product according to any one of the foregoing embodiments.

[0716] 35. A foam-forming isocyanate addition product according to the previous embodiment, selected from blocks, molded foams, flexible foams, rigid foams, semi-rigid foams, spray foams, thermoformable foams, microcellular foams, footwear foams, open-cell foams, closed-cell foams, adhesives.

[0717] While the scope of the present invention is defined by the appended claims, the following examples illustrate certain aspects of the invention and, more specifically, describe the evaluation method. The examples are presented for illustrative purposes and should not be construed as limiting the invention. Example

[0718] Example 1 Copper-containing catalyst starting from copper(II) acetate monohydrate

[0719] 5.16 g of copper(II) acetate monohydrate (25.8 mmol) was dissolved in 114.84 g (862 mmol) of 2-[2-(dimethylamino)ethoxy]ethanol at room temperature with vigorous stirring. 65.67 g of isophorone diisocyanate (IPDI) (295 mmol) was added in three portions (33%, 33% and 34%) under a nitrogen atmosphere. After the addition of each portion of IPDI, the reaction temperature was allowed to return to 25 - 35 °C. After the complete addition of IPDI, the reaction mixture was kept at 70 °C for an additional 2 hours. The resulting mixture was cooled to ~40 °C and transferred to a laboratory glass bottle. The catalyst composition was a homogeneous and stable mixture at room temperature.

[0720] Comparative Example 1 [Copper-free catalyst]

[0721] To 94.45 g (709 mmol) of 2-[2-(dimethylamino)ethoxy]ethanol under a nitrogen atmosphere and with vigorous stirring, 54.00 g (234 mmol) of isophorone diisocyanate (IPDI) was added in three portions (33%, 33% and 34%), keeping the temperature below 70 °C. After the addition of each portion of IPDI, the reaction temperature was allowed to return to 25 - 35 °C. After the complete addition of IPDI, the reaction mixture was kept at 70 °C for an additional 2 hours. The resulting mixture was cooled to ~40 °C and transferred to a laboratory glass bottle. The catalyst composition was a homogeneous and stable mixture at room temperature.

[0722] Example 2 [Catalyst mixture containing salicylic acid and copper(II)]

[0723] The reaction was carried out as described in Example 1 above. After the complete addition of IPDI, the reaction mixture was kept at 70 °C for an additional 2 hours. Then, salicylic acid was added at 70 °C and the mixture was kept at 70 °C for an additional 2 hours. The resulting mixture was cooled to ~40 °C and transferred to a laboratory glass bottle. The catalyst composition was a homogeneous and stable mixture at room temperature.

[0724] Comparative Example 2 [Catalyst mixture containing salicylic acid]

[0725] The reaction was carried out as described in the aforementioned Comparative Example 1. After the complete addition of IPDI, the reaction mixture was maintained at 70 °C for an additional 2 hours. Subsequently, salicylic acid was added at 70 °C and the mixture was maintained at 70 °C for an additional 2 hours. The resulting mixture was cooled to ~40 °C and transferred to a laboratory glass bottle. The catalyst composition was a homogeneous and stable mixture at room temperature.

[0726] Table 1 summarizes the aforementioned examples.

[0727] Table 1 - Examples 1, 2 and Comparative Examples 1, 2

[0728] Example 1 CEx 1 2 CEx 2 2-[2-(Dimethylamino)ethoxy]ethanol, in grams 114.84 94.45 114.84 94.45 Copper(II) acetate monohydrate, in grams 5.16 - - - IPDI, in grams 65.67 54 65.67 54 Salicylic acid, in grams - 1.74 1.43

[0729] The catalyst compositions of Examples 1 and 2 and Comparative Examples 1 and 2 (0.8 parts by weight or pbw.) were evaluated in the manufacture of the PU foams shown in Table 2 below.

[0730] Examples 3, 4 and Comparative Examples 3, 4 (Polyurethane foam)

[0731] A polyurethane foam was prepared according to the following procedure. A premix of a reactive polyether polyol ( 1629; hydroxyl value 29.5 - 33.5 mg KOH / g), a reactive polyether polyol modified with styrene - acrylonitrile polymer ( 1639; hydroxyl value 16.5 - 20.5 mg KOH / g), an EO - rich blowing agent (Voranol TM CP 1421; hydroxyl value 33 mg KOH / g), a 90 wt% aqueous solution of diethanolamine (90 wt% DEOA in water), a silicone stabilizer ( L - 3640), a strong foaming catalyst Niax Catalyst EF - 100 and water was prepared as follows: in a plastic bucket, using a paddle stirrer with a ring, it was thoroughly mixed at 1500 rpm for 20 minutes. From this premix, 4 batches each weighing 399.86 g were weighed into suitable plastic mixing containers and the corresponding catalyst compositions (Examples 1 and 2, Comparative Examples 1 and 2) were added accordingly to obtain 4 polyol blends (Table 2). The polyol blends were thoroughly mixed in the plastic containers at 3000 rpm for 30 seconds using a paddle stirrer with a ring. 164.4 g of Scuranate T80 isocyanate (TDI, NCO content 48.1%) was added and the reactive mixture was mixed for 4 - 6 seconds. The reactive mixture was immediately poured into a 30×30×10 cm aluminum mold and the mold was immediately closed and clamped. The mold lid had 4 ventilation openings with a diameter of 0.4 mm at the four corners. The mold temperature was controlled at 65 °C via a hot water circulation thermostat. A mold release agent The mold was coated with PU-1705M. The foam was demolded after 4 minutes. The processing and physical properties of the foam were evaluated as follows:

[0732]

[0733]

[0734] Table 2 – Preparation and evaluation of polyurethane foams (Examples 3, 4 and Comparative Examples 3, 4)

[0735]

[0736] The catalytic performance of the copper-based catalyst composition was evaluated by comparing the processing and physical properties, particularly the thermal ILD and ILD values. The thermal ILD value represents the load-bearing capacity of the porous material after demolding and crushing the foam to open the cells. The higher this value, the firmer, denser, and better cured the foam is after demolding and crushing to open the cells. As is clear from Table 2, compared with Comparative Examples 1 and 2 that do not use the inventive catalyst composition, the polyurethane foams prepared with the inventive catalyst compositions of Examples 1 and 2 based on copper(II) showed significantly higher crushing force (FTC), thermal ILD, and ILD. For example, the thermal ILD of the polyurethane foam from Example 3 was 313 N, while that of Comparative Example 3 was only 263 N. Similarly, the thermal ILD of Example 4 was 314 N, while that of Comparative Example 4 was only 282 N. It is noteworthy that the ILD values of the polyurethane foams from Example 3 and Example 4 (672 N and 583 N, respectively) were also significantly higher compared with Comparative Examples 3 and 4 (402 and 404 N, respectively). Thus, by using the copper-based compositions of Examples 1 and 2, beneficially higher thermal ILD and ILD values of the polyurethane foams of Examples 3 and 4 were surprisingly achieved. The improved catalytic performance of the copper-based composition can beneficially reduce the demolding time, resulting in a faster manufacturing cycle and higher productivity.

[0737] Examples 5 and Comparative Examples 5 - 8

[0738] As described in the above Examples 3, 4 and Comparative Examples 3, 4, new polyurethane foams (Ex 5 and CEx 6-8) were manufactured and their processing and physical properties were evaluated as shown in Table 3 below.

[0739] Table 3

[0740]

[0741] As is clear from Table 3, in contrast to Comparative Catalyst Example 1 (Comparative Example 5), the inventive catalyst composition of Example 1 (Example 5) provided polyurethane foams with significantly higher crush strength, thermal ILD, and ILD values. Comparative Examples 6 - 8, which used only different amounts of copper(II) acetate monohydrate introduced via direct premixing with added water, showed that in the absence of a urethane co-catalyst, copper(II) acetate did not function in a water-blown polyurethane system. In particular, even at higher concentrations, copper(II) acetate did not function in the water-blown polyurethane system (Comparative Examples 7 and 8).

[0742] Examples 6 and Comparative Example 9; Examples 7 and Comparative Example 10 (Evaluation of the storage stability of the formulated multiple alcohol blends including the catalyst composition of the present invention)

[0743] The time during which the formulated polyol system can be stored in a storage tank without losing any of its properties is called the shelf life. The effect of the copper-based catalyst on the shelf life of the formulated polyol system is described by the experiments in Table 4. Three measurements were made for each example and the results were averaged. The reactive polyether polyol ( 1629), reactive polyether polyol modified with styrene-acrylonitrile polymer ( 1639), EO-rich cell opener (Voranol TM CP 1421), 90 wt% aqueous diethanolamine solution, silicone stabilizer ( L-3640), Niax Catalyst EF-100, and water were premixed as follows: Using a paddle stirrer with a ring in a plastic bucket, thoroughly mix for 20 minutes at 1500 rpm. From this premix, 12 batches each weighing 352.95 g were weighed out and placed in suitable plastic containers for mixing. The respective catalyst compositions of Example 1 and Comparative Example 1 were added accordingly to 6 batches each, and the mixtures were then thoroughly mixed for 30 seconds at 3000 rpm in the plastic containers using a paddle stirrer with a ring to obtain the formulated polyol systems. For the three measurements, three feedings of the freshly prepared formulated polyol systems for each catalyst composition of Example 1 (Ex 6) and Comparative Example 1 (CEx 9) were immediately used to prepare polyurethane foam pads. The other 6 batches of the formulated polyol systems (3 batches each with the catalyst compositions of Example 1 and Comparative Example 1) were hermetically sealed with caps and stored at ~20 - 23 °C for 7 days. After storing for 7 days, the batches were used to prepare polyurethane foam pads.

[0744] Polyurethane foams are manufactured from freshly prepared or stored formulated polyol blends in the same manner. Remove the cap from the plastic container and thoroughly mix the formulated polyol system in the plastic container for 30 seconds at 3000 rpm using a paddle stirrer with a ring. Add 145.7 g of Scuranate T80 isocyanate (TDI, NCO content 48.1%) and mix the reactive mixture for 4 - 6 seconds. Pour the reactive mixture into a 30×30×10 cm aluminum mold and immediately close and clamp the mold. The mold lid has 4 vent openings with a diameter of 0.4 mm at the four corners. Control the mold temperature at 65 °C via a hot water circulation thermostat. Coat the mold with a release agent PU-1705M. Demold the foam after 4 minutes.

[0745] Table 4 - Storage stability of the catalyst composition (1,4 pbw) in the polyol blend - 7 days (three measurements)

[0746]

[0747] As shown above and in the foregoing examples, compared to the catalyst composition of Comparative Example 1, the inventive catalyst composition according to Example 1 provided significantly higher FTC, thermal ILD, and ILD values, which confirmed the beneficial catalytic effect of the catalyst composition. Additionally, the significantly improved catalytic performance of the inventive catalyst composition according to Example 1 remained unchanged after storing the formulated polyol blend for 7 days (Table 4, see the values presented in parentheses). The registered negligible differences in the values of thermal ILD and ILD are negligible and can be ignored.

[0748] As described in the procedures of Example 6 and Comparative Example 9 above, as shown in Table 5, new polyurethane foams were formed and evaluated at different catalyst loadings and for longer storage times. Three measurements were made for each example and the results averaged. In parentheses, the values are given for the polyurethane foams obtained after storing the formulated polyol blend in a hermetically sealed plastic cup at ~20 - 23 °C for 11 days.

[0749] Table 5 - Storage stability of the catalyst composition in the formulated polyol blend - 11 days (three measurements)

[0750]

[0751] As in the foregoing examples also in Table 5, compared to the catalyst composition of Comparative Example 1, the inventive catalyst composition according to Example 1 provided higher FTC, thermal ILD, and ILD values. This confirmed the beneficial higher catalytic effect of the catalyst composition of Example 1. In addition, the catalytic performance of the inventive catalyst composition according to Example 1 remained unchanged after storing the corresponding formulated polyol blend for 11 days (Table 5, see the values presented in parentheses). The registered negligible differences in the values of thermal ILD and ILD are negligible and can be ignored. Further, it is shown that by using an even lower catalyst loading (0.80 pbw), the inventive catalyst composition of Example 1 provided higher thermal ILD and ILD values than at a higher catalyst loading (1.40 pbw) in Comparative Example 1. Further, the inventive catalyst composition of 0.80 pbw provided a higher ILD, which highlights its post-molding efficiency (for Examples 1 and 2).

[0752] Examples 8, 9

[0753] Copper(II) 2-ethylhexanoate was purchased from Sigma-Aldrich. According to the procedure of Example 1, a catalyst composition using copper(II) 2-ethylhexanoate was prepared as shown in Table 6. In particular, the molar concentration of copper(II) 2-ethylhexanoate in Example 8 was in the same range as the molar concentration of copper(II) acetate in Example 1. It is noted that the concentration of copper(II) in Example 2 was significantly increased. Both catalyst compositions were homogeneous and stable mixtures at room temperature.

[0754] Table 6 - Manufacture of the catalyst composition using copper(II) ethylhexanoate

[0755] Example 8 9 2-[2-(Dimethylamino)ethoxy]ethanol, in grams 120.00 120.00 2-[2-(Dimethylamino)ethoxy]ethanol, in mmol 901 901 IPDI, in grams 68.61 68.61 <![CDATA[Cu(2-ethylhexanoate)2, in g]]> 9.79 21.30

[0756] It was confirmed that the use of copper(II) 2-ethylhexanoate enabled an increase in the copper(II) loading in the catalyst composition of the present invention.

[0757] Examples 10 and 11

[0758] As described in Examples 6 and Comparative Example 9 above, polyurethane foams corresponding to the compositions of Examples 8 and 9 were manufactured and evaluated as shown in Table 9. Two measurements were made for each example and the results were averaged. In parentheses, the values are given for the polyurethane foam obtained after storing the formulated polyol blend at ~20 - 23 °C for 6 days.

[0759] Table 9 - Comparison of the influence of the type of copper(II) salt on the catalytic performance and shelf life of the formulated polyol blend after 6 days of storage. Comparative Examples 13 - 15

[0760]

[0761]

[0762] Considering the fact that the molar concentration of copper(II) 2-ethylhexanoate in the catalyst composition of Example 8 is in the same range as the molar concentration of copper(II) acetate in Example 1, Table 9 (Examples 10 and 11) highlights that the inventive catalyst composition provides comparable thermal ILD and ILD values. Additionally, the catalytic performance of the inventive catalyst compositions of Example 1 and Example 8 remains unchanged after storing the formulated polyol blend at ~20–23 °C for 6 days (Table 9, see the values presented in parentheses).

[0763] Table 10 - Comparative catalyst compositions based on zinc(2-ethylhexanoate)2 or Zn(EH)2, zirconium(2-ethylhexanoate)4 or Zr(EH)4 and bismuth

[0764] Following the procedure of Example 1, catalyst compositions using zinc(II) 2-ethylhexanoate, zirconium(IV) 2-ethylhexanoate, and bismuth(III) neodecanoate were prepared as shown in Table 10.

[0765] (neodecanoate)3 or Bi(ND)3 ​

[0766]

[0767] Following the procedure of Example 3, when manufacturing foams using the Zr-, Zn-, or Bi-based catalyst compositions of Comparative Examples 13, 14, and 15, it was neither possible to obtain a homogeneous and clear catalyst composition nor higher thermal ILD or ILD values.

Claims

1. A composition comprising at least one Cu(II) salt, at least one compound obtainable by reacting isophorone diisocyanate (IPDI) with at least one isocyanate-reactive compound having at least one tertiary amino group, and a diluent comprising at least one isocyanate-reactive compound having at least one tertiary amino group.

2. The composition according to claim 1, comprising a compound obtainable by: reacting isophorone diisocyanate (IPDI) with at least one isocyanate-reactive compound having at least one tertiary amino group in the presence of at least one Cu(II) salt and optionally in the presence of one or more diluents; or reacting at least one isocyanate compound with at least one isocyanate-reactive compound having at least one tertiary amino group optionally in the presence of one or more diluents and subsequently adding at least one Cu(II) salt.

3. The composition according to claim 1 or 2, comprising a compound obtainable by reacting isophorone diisocyanate (IPDI), at least one isocyanate-reactive compound having at least one tertiary amino group, and at least one isocyanate-reactive compound having no tertiary amino group in the presence of at least one Cu(II) salt and optionally in the presence of one or more diluents.

4. The composition according to claim 1 or 2, comprising: A compound comprising at least one urethane (carbamate) and / or urea group and at least one tertiary amino group, at least one Cu(II) salt, and optionally one or more diluents.

5. The composition according to claim 1 or 2, wherein the isocyanate-reactive compound having at least one tertiary amino group is selected from alcohols having at least one tertiary amino group and amines having at least one tertiary amino group and at least one additional amino group selected from primary and secondary amino groups.

6. The composition according to claim 1 or 2, wherein the isocyanate-reactive compound having at least one tertiary amino group is selected from: and bicyclic tertiary amines selected from: or a mixture thereof.

7. A composition comprising at least one Cu(II) salt, at least one compound obtainable by reacting at least one isocyanate compound with at least one isocyanate-reactive compound having at least one tertiary amino group, and a diluent comprising at least one isocyanate-reactive compound having at least one tertiary amino group, wherein the isocyanate-reactive compound comprises at least one ether group (-O-).

8. The composition comprising at least one Cu(II) salt, at least one compound C1-C25, wherein the compound C1-C25 is selected from: C1 1-[Bis[3-(dimethylamino)propyl]amino]-2-propanol and the reaction product of: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C2 2-[2-(Dimethylamino)ethoxy]ethanol and the reaction product with the following: 1,3-bis(1-isocyanato-1-methylethyl)benzene, isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C3 2-{[2-(Dimethylamino)ethyl]methylamino}ethanol and the reaction product with the following: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C4 3,3'-Iminobis(N,N-dimethylpropylamine) and the reaction product with the following: 1,3-bis(1-isocyanato-1-methylethyl)benzene, isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C5 Dimethylaminoethanol and the reaction product with the following: 1,3-bis(1-isocyanato-1-methylethyl)benzene, isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C6 Diethylaminoethanol and the reaction product with the following: 1,3-bis(1-isocyanato-1-methylethyl)benzene, isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C7 3-(Dimethylamino)-1-propylamine and the reaction product with the following: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C8 3-(Diethylamino)-1-propylamine and the reaction product with the following: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C9 3-(Diethylamino)-1-propanol and the reaction product with the following: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C10 1-(3-Hydroxypropyl)pyrrolidine and the reaction product with the following: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C11 1-(2-Hydroxyethyl)pyrrolidine and the reaction product with the following: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C12 1-(2-Hydroxyethyl)piperidine and the reaction product with the following: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C13 1-(3-Hydroxypropyl)piperidine and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C14 1-(2-Hydroxypropyl)piperidine and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C15 1-(3-Aminopropyl)pyrrolidine and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C16 1-(2-Aminoethyl)pyrrolidine and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C17 1-(3-Aminopropyl)piperidine and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C18 1-(2-Aminoethyl)piperidine and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C19 1-(Piperidin-1-yl)propan-2-ol and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C20 1-(Pyrrolidin-1-yl)propan-2-ol and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C21 1-(1-Pyrrolidinyl)-2-propanamine and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C22 1-(Piperidin-1-yl)propan-2-amine and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C23 2-[2-[2-(Dimethylamino)ethoxy]ethyl-methylamino]ethanol and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, C24 3-{[3-(Dimethylamino)propyl]methylamino}propanol and the reaction product with: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, and C25 2-{[3-(dimethylamino)propyl]methylamino}ethanol and the reaction product with the following: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI, and a diluent comprising at least one isocyanate-reactive compound having at least one tertiary amino group.

9. The composition according to claim 8, wherein the compound is selected from: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog: or its HDMI analog:

10. The composition according to claim 8 or 9, wherein the at least one Cu(II) salt is selected from Cu(II) carboxylates.

11. The composition according to claim 8 or 9, which comprises 10 - 99.991% by weight of a compound obtainable by reacting at least one isocyanate compound and at least one isocyanate-reactive compound having at least one tertiary amino group, 0.009 - 5% by weight of copper, and 0 - 89.991% by weight of a diluent, wherein the % by weight is based on the total weight of the composition.

12. The composition according to claim 8 or 9, which further comprises one or more additional catalysts for forming a polyisocyanate addition product.

13. The composition according to claim 8 or 9, which further comprises at least one carboxylic acid selected from monocarboxylic acid compounds, polycarboxylic acid compounds, and hydroxy-functional carboxylic acid compounds.

14. The composition according to claim 8 or 9, which further comprises at least one carboxylic acid selected from salicylic acid, benzoic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, azelaic acid, sebacic acid, and citric acid.

15. The composition according to claim 8, wherein C12 is selected from the reaction product of 1-(2-hydroxyethyl)piperidine with the following: isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), and derivatives derived from IPDI and / or HDI selected from the following: its biuret, isocyanurate, urethane, and oligomers.

16. A process for manufacturing a composition according to any one of claims 1 - 15, the process comprising reacting at least one isocyanate compound and at least one isocyanate - reactive compound having at least one tertiary amino group in the presence of at least one Cu(II) salt and in the presence of a diluent comprising at least one isocyanate - reactive compound having at least one tertiary amino group, wherein the isocyanate - reactive compound having at least one tertiary amino group is used in a molar excess relative to the isocyanate compound, based on the molar ratio of isocyanate - reactive groups to isocyanate groups.

17. A process for manufacturing a composition according to any one of claims 1 - 15, the process comprising reacting at least one isocyanate compound and at least one isocyanate - reactive compound having at least one tertiary amino group in the presence of a diluent comprising at least one isocyanate - reactive compound having at least one tertiary amino group, and subsequently adding at least one copper(II) salt, wherein the isocyanate - reactive compound having at least one tertiary amino group is used in a molar excess relative to the isocyanate compound, based on the molar ratio of isocyanate - reactive groups to isocyanate groups.

18. The process for manufacturing a composition according to claim 16 or 17, wherein the reaction is carried out at a temperature of 20 - 140 °C.

19. Use of a composition according to any one of claims 1 - 15 as a catalyst.

20. Use of a composition according to any one of claims 1 - 15 as a catalyst for the reaction of at least one isocyanate compound with at least one isocyanate - reactive compound.

21. The use according to claim 19 or 20 as a catalyst for manufacturing a polyisocyanate addition product.

22. The use according to claim 21, wherein the polyisocyanate addition product has one or more functional groups consisting of groups selected from urethane groups and urea groups.

23. The use according to claim 20 as a catalyst for manufacturing a polyurethane foam.

24. A catalyst composition comprising a composition according to any one of claims 1 - 15.

25. A process for manufacturing an isocyanate addition product, which comprises reacting an isocyanate compound with an isocyanate - reactive compound in the presence of a composition as defined in any one of claims 1 - 15.

26. The process for manufacturing an isocyanate addition product according to claim 25, wherein the isocyanate is a polyisocyanate and the isocyanate - reactive compound is a polyol, and the process is for manufacturing a polyurethane foam.

27. The process for manufacturing an isocyanate addition product according to claim 25 or 26, wherein the isocyanate addition product is a polyurethane foam selected from porous or non - porous polyurethanes, and the process optionally comprises a blowing agent.

28. A process for manufacturing an isocyanate addition product according to claim 25 or 26, wherein the process is for manufacturing a polyurethane, and the process optionally comprises adding a surfactant, a flame retardant, a chain extender, a crosslinking agent, an adhesion promoter, an antistatic additive, a hydrolysis stabilizer, a UV stabilizer, a lubricant, an antimicrobial agent, or a combination of two or more thereof.

29. A process for manufacturing an isocyanate addition product according to claim 25 or 26, wherein the composition is present in an amount of 0.005 wt% - 5 wt%, based on the total weight of the entire composition including all components.

30. A foam-forming isocyanate addition product obtainable by a process for manufacturing an isocyanate addition product according to any one of claims 25 - 29.

31. A foam-forming isocyanate addition product according to claim 30, selected from the group consisting of blocks, molded foams, flexible foams, rigid foams, semi-rigid foams, spray foams, heat-formable foams, microcellular foams, footwear foams, open-cell foams, closed-cell foams, adhesives.

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