DK178910B1 - Ionic complex of an amino alcohol and a metal carboxylate as a catalyst for polymerization reactions - Google Patents
Ionic complex of an amino alcohol and a metal carboxylate as a catalyst for polymerization reactions Download PDFInfo
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- DK178910B1 DK178910B1 DKPA201500651A DKPA201500651A DK178910B1 DK 178910 B1 DK178910 B1 DK 178910B1 DK PA201500651 A DKPA201500651 A DK PA201500651A DK PA201500651 A DKPA201500651 A DK PA201500651A DK 178910 B1 DK178910 B1 DK 178910B1
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Abstract
The present invention relates to the use of an ionic complex of an amino alcohol and a metal carboxylate as a catalyst for polymerization reactions.
Description
Background of the invention
In many products made by polymerization reactions, the reaction is controlled by use of catalysts to regulate and optimize speed and effectivity of the reaction. Many of these catalysts are toxic (e.g. organotin-catalysts and metal-amidine-complexes, where the amidine is toxic (e.g. DBU or 1-methylimidazole)), and the resulting products will risk leaking these toxic materials during use. Furthermore, the workers handling such catalysts may risk toxic exposure. Catalysts with low toxicity do exist, such as organo-bismuth catalysts; however, these types are often slow in reaction and very expensive.
Hence, there is a need for an alternative polymerization process producing nontoxic products. More specifically, there is a need for a low cost non-toxic high-activity catalyst for polymerization reactions. EP1057857 discloses a curing accelerator for a resin having an unsaturated fatty acid group in its molecules, and contains a cobalt soap (A), a manganese soap (B), and an amino alcohol (C).
Summary of the invention
The inventor of the present invention has developed a new catalyst with low toxicity for polymerization reactions. The new catalyst is an ionic complex of an amino alcohol and a metal carboxylate. The new catalyst is capable of catalyzing polymerization reactions with comparable activity to conventional catalysts based on toxic materials.
The new catalysts of this invention are based on a reaction product of a nontoxic amino alcohol, like triethanolamine, and a non-toxic metal carboxylate, such as zinc 2-ethylhexanoate (zinc bis(2-ethylhexanoate)).
By using this kind of catalyst, it is now possible to produce polymer products for use within the sectors of food, medico, water, and pharma. In addition, it will now be possible always to choose GRAS raw materials. (Generally Recognised As Safe). Typical uses are as catalyst in polymerization of polymers and crosslinking/curing of these polymers to be used in polymer products like sealants, coatings, rubbers plastics, TPV’s (Termoplatic vulcanisates), composites, foams, adhesives, and fibers. A first aspect relates to the use of an ionic complex consisting of an amino alcohol and a metal carboxylate as a catalyst for polymerization reactions; wherein the metal of the metal carboxylate is selected from the group consisting of zinc, lithium, sodium, magnesium, barium, potassium, calcium, bismuth, cadmium, aluminum, 5 zirconium, tin, hafnium, titanium, lanthanum, vanadium, niobium, tantalum, tellurium, molybdenum, tungsten, and cesium; and wherein a moisture-curable silylated resin is part of the polymerization reaction. A second aspect relates to a composition comprising an ionic complex consisting of an amino alcohol and a metal carboxylate, wherein the amino alcohol is selected from the group consisting of trimethanolamine, triethanolamine, tripropanolamine, tributanolamine and mixtures thereof, and wherein the metal carboxylate is selected from the group consisting of metal carboxylate salts of 2-ethyl hexanoates, octanoates, nonanoates, heptanoates, neodecanoates, stearate, oleate, palmitate, laurate, dimethacrylate, diacrylate, isobutyrate, propionate, acetate, isovalerate, pivalic acid salt, maleic acid salt, adipic acid salt, phenylacetate, cinnamate, hydrocinnamate, naphthoate, zinc naphthalene acetate, isophthalic acid salt, phthalic acid salt, and mixtures thereof; wherein the metal of the metal carboxylate is selected from the group consisting of zinc, lithium, sodium, magnesium, barium, potassium, calcium, bismuth, cadmium, aluminum, zirconium, tin, hafnium, titanium, lanthanum, vanadium, niobium, tantalum, tellurium, molybdenum, tungsten, and cesium. A third aspect relates to a process for the production of an elastomeric material comprising the steps of: a) mixing an uncured or substantially uncured elastomeric polymer composition with a moisture-curable silylated resin to provide a moisture-curable elastomeric composition; wherein the moisture-curable silylated resin is present in an amount of 1-99% w/w of the moisture-curable elastomeric composition; wherein the elastomeric polymer composition comprises one or more nonmoisture-curable elastomeric polymers; and b1) allowing the moisture-curable elastomeric composition to cure with water from the surrounding atmosphere as an activator to form the elastomeric material; or b2) allowing the moisture-curable elastomeric composition to cure by adding water as an activator to the moisture-curable elastomeric composition to form the elastomeric material; wherein an ionic complex consisting of an amino alcohol and a metal carboxylate is added in step a) and/or in step b2).
Detailed description of the invention
The present invention has utility in a variety of different polymerization reactions. A first aspect relates to the use of an ionic complex consisting of an amino alcohol and a metal carboxylate as a catalyst for polymerization reactions; wherein the metal of the metal carboxylate is selected from the group consisting of zinc, lithium, sodium, magnesium, barium, potassium, calcium, bismuth, cadmium, aluminum, 5 zirconium, tin, hafnium, titanium, lanthanum, vanadium, niobium, tantalum, tellurium, molybdenum, tungsten, and cesium; and wherein a moisture-curable silylated resin is part of the polymerization reaction. A second aspect relates to a composition comprising an ionic complex consisting of an amino alcohol and a metal carboxylate, wherein the amino alcohol is selected from the group consisting of trimethanolamine, triethanolamine, tripropanolamine, tributanolamine, and mixtures thereof, and wherein the metal carboxylate is selected from the group consisting of metal carboxylate salts of 2-ethyl hexanoates, octanoates, nonanoates, heptanoates, neodecanoates, stearate, oleate, palmitate, laurate, dimethacrylate, diacrylate, isobutyrate, propionate, acetate, isovalerate, pivalic acid salt, maleic acid salt, adipic acid salt, phenylacetate, cinnamate, hydrocinnamate, naphthoate, zinc naphthalene acetate, isophthalic acid salt, phthalic acid salt, and mixtures thereof; wherein the metal of the metal carboxylate is selected from the group consisting of zinc, lithium, sodium, magnesium, barium, potassium, calcium, bismuth, cadmium, aluminum, zirconium, tin, hafnium, titanium, lanthanum, vanadium, niobium, tantalum, tellurium, molybdenum, tungsten, and cesium.
In the present context, the term “an amino alcohol” is to be understood as one or more amino alcohols.
In the present context, the term “a metal carboxylate” is to be understood as one or more metal carboxylates.
The term "amino alcohol" as used herein refers to organic compounds that contain both an amine and an alcohol functional group. A specific subgroup of amino alcohols are alkanolamines, which are chemical compounds that contain both hydroxyl (-OH) and amino (-NH2, -NHR, and -NR2) functional groups on an alkane backbone.
Preferred amino alcohols include triethanol amine, dimethylamino ethanol, diethanolamine, di-ethanoltriamine, and (mono)ethanol amine. Triethanolamine is the most preferred amino alcohol. Other types of amino alcohols include triisopropanolamine, N-methyl diethanolamine, N-ethyl diethanolamine, Ν,Ν-dimethyl ethanolamine, and triethanolamine ethoxylates. Triethanolamine ethoxylates are generally represented by the formula N[CH2CH2(OCH2CH2)nOH]3.
In one or more embodiments, the amino alcohol is a tertiary amino alcohol.
In one or more embodiments, the tertiary amino alcohol is selected from the group consisting of trimethanolamine, triethanolamine, tripropanolamine, tributanolamine, and mixtures thereof.
Examples of suitable metal carboxylate salts are the 2-ethyl hexanoates, octanoates, nonanoates, heptanoates, and neodecanoates. The metal may be zinc, lithium, sodium, magnesium, barium, potassium, calcium, bismuth, cadmium, aluminum, zirconium, tin, hafnium, titanium, lanthanum, vanadium, niobium, tantalum, tellurium, molybdenum, tungsten, or cesium. In a particular embodiment, the metal is zinc.
The ionic complex of an amino alcohol and a metal carboxylate may be formed in an accelerator solution, or they may be formed in situ. The accelerator solution may be able to increase the activity of the ionic complex at lower temperatures and, consequently, to speed up the polymerization reaction. The accelerator solution may also be able to increase the activity by increasing the blendability of the polymerization reaction mixture. The ionic complex may consist of equimolar amounts of the amino alcohol and the metal carboxylate, or may consist of different molar amounts of the amino alcohol and the metal carboxylate.
Specific examples of metal carboxylate salts are magnesium stearate (commercially available from the Aldrich company), calcium 2-ethylhexanoate (commercially available from Shepherd Chemical Company) and zinc 2-ethylhexanoate (also commercially available from Shepherd Chemical
Company). Other examples are zinc stearate, zinc oleate, zinc palmitate, zinc laurate, calcium stearate, calcium oleate, calcium palmitate, calcium laurate, magnesium stearate, magnesium oleate, magnesium laurate, magnesium palmitate, nickel laurate, copper stearate, copper oleate, copper laurate, and copper palmitate.
The metal carboxylates often comprise a low amount of the corresponding carboxylic acid. In the present context, these are considered to be included in the term metal carboxylate.
Other examples of metal carboxylate salts are zinc dimethacrylate, zinc diacrylate, zinc isobutyrate, zinc propionate, zinc acetate, zinc isovalerate, pivalic acid zinc salt, zinc stearate, maleic acid zinc salt, adipic acid zinc salt, zinc phenylacetate, zinc cinnamate, zinc hydrocinnamate, zinc naphthoate, zinc naphthalene acetate, isophthalic acid zinc salt, and phthalic acid zinc salt, and their metal equivalents, such as substituting zinc as the central metal element with lithium, sodium, magnesium, barium, potassium, calcium, bismuth, cadmium, aluminum, zirconium, tin, hafnium, titanium, lanthanum, vanadium, niobium, tantalum, tellurium, molybdenum, tungsten, or cesium.
In one or more embodiments, the composition comprises a mixture of ionic complexes of an amino alcohol and a metal carboxylate.
In one or more embodiments, the carboxylate is a branched or unbranched aliphatic monocarboxylate.
Without being bound by a specific type of ionic complex, it is believed that at least some of the ionic complexes corresponds to the formula MiXnYm, where M represents an (n + m)-valent metal, such as zinc, lithium, sodium, magnesium, barium, potassium, calcium, bismuth, cadmium, aluminum, zirconium, tin, hafnium, titanium, lanthanum, vanadium, niobium, tantalum, tellurium, molybdenum, tungsten, or cesium. In a particular embodiment, the metal is zinc.
In a particular embodiment, the metal is in the +2 oxidation state and/or +3 oxidation state. X represents an amino alcohol, and Y represents a carboxylate. If the carboxylate is a di-carboxylate, the formula will be MiXn(Y/2)m, and if the carboxylate is a tri-carboxylate, the formula will be MiXn(Y/3)m. If M is monovalent, I is at least equal to 2. N and m will at least be equal to 1.
In one or more embodiments, the composition further comprises a compound selected from the group consisting of: an amino alcohol, a metal carboxylate, and a carboxylic acid.
In one or more embodiments, a moisture-curable silylated resin is part of the polymerization reaction. A third aspect relates to a process for the production of an elastomeric material comprising the steps of: a) mixing an uncured or substantially uncured elastomeric polymer composition with a moisture-curable silylated resin to provide a moisture-curable elastomeric composition; wherein the moisture-curable silylated resin is present in an amount of 1-99% w/w of the moisture-curable elastomeric composition; wherein the elastomeric polymer composition comprises one or more nonmoisture-curable elastomeric polymers; and b1) allowing the moisture-curable elastomeric composition to cure with water from the surrounding atmosphere as an activator to form the elastomeric material; or b2) allowing the moisture-curable elastomeric composition to cure by adding water as an activator to the moisture-curable elastomeric composition to form the elastomeric material; wherein an ionic complex consisting of an amino alcohol and a metal carboxylate is added in step a) and/or in step b2).
In the present context, the term “moisture-curable silylated resin” refers to a silylated resin that on exposure to moisture undergoes hydrolysis and subsequent condensation to provide a cured resin. Many moisture-curable silylated resins are known within the art, and the production of a broad range of them can be found in W02009064428, US7319128, W02007037833, US2010/0071849, WO 2007/050538, US2015/0007938, US2015/0007938, and EP0931800; all hereby incorporated by reference.
Silane-functional polymer systems are typically cured in a two-step sequence in which water, either as water vapor (e.g. within the air) or liquid water, hydrolyzes an alkoxysilane group to form a silanol group, followed by condensation of the silanol group with the silanol group of another similarly hydrolyzed alkoxysilane molecule; resulting in the formation of numerous cross-links. In the present context, when the moisture-curable silylated resin is cured, it will form a stabilizing network within the non-moisture-curable elastomeric polymer composition.
As used herein, the term "elastomeric composition” means and includes any viscoelastic composition containing a more or less viscoelastic polymer partly or totally capable of recovering its original size and shape after deformation, which is typically for all known “elastomeric polymers” used in the rubber or alike industries. In other words, an elastomeric polymer is a polymer having elastic properties. Elastomeric polymers may also be referred to as "elastomers" in the art. Elastomeric polymers include, without limitation, homopolymers (polymers having a single chemical unit repeated), copolymers (Polymers having 2 chemical units repeated randomly or in blocks as a co-block polymer), terpolymers (Polymers having 3 chemical units repeated randomly or in blocks) etc. It also includes all types of mixtures of these different polymers.
In one or more embodiments, the moisture-curable silylated resin is obtained by the silylation of at least one resin selected from the group consisting of polyether polyol (i), polyester polyol (ii), hydroxyl-terminated polybutadiene (iii), hydroxyl-terminated or isocyanate-terminated polyurethane prepolymer (iv) derived from at least one of polyether polyol, polyester polyol or hydroxy-terminated polybutadiene, amine-terminated or isocyanate-terminated polyurethane-polyurea prepolymer and/or polyurea prepolymer (v) derived from polyamine, and olefinically unsaturated resin (vi).
In one or more embodiments, the moisture-curable silylated resin is obtained from: - at least one of polyether polyol (i), polyester polyol (ii), hydroxyl-terminated polybutadiene (iii), hydroxyl-terminated polyurethane prepolymer (iv) or amine-terminated polyurethane-polyurea prepolymer and/or amine-terminated polyurea prepolymer (v) by silylation with at least one isocyanatosilane; or - isocyanate-terminated polyurethane prepolymer (vi) or isocyanate-terminated polyurethane-polyurea prepolymer (vii) and/or isocyanate-terminated polyurea prepolymer (viii) by silylation with at least one isocyanate-reactive silane selected from the group consisting of mercaptosilane, primary aminosilane, secondary aminosilane and mixtures thereof; or - olefinically unsaturated resin (ix) by hydrosilation with at least one hydridosilane.
In one or more embodiments, the moisture-curable silylated resin is at least one silylated polyurethane prepolymer obtained from silylation of: - hydroxyl-terminated polyurethane prepolymer derived from polyether diol and diisocyanate; or - isocyanate-terminated polyurethane prepolymer derived from polyether diol and diisocyanate.
In one or more embodiments, the silylation of the hydroxyl-terminated polyurethane prepolymer is carried out with at least one isocyanatosilane; and wherein the silylation of the isocyanate-terminated polyurethane prepolymer is carried out with at least one isocyanate-reactive silane selected from the group consisting of mercaptosilane, primary aminosilane, secondary aminosilane and mixtures thereof.
One type of particular interest among the silane-terminated polymers is notable for the separation of the reactive alkoxysilyl groups only by one methylene spacer from an adjacent heteroatom. These so-called a-alkoxysilylmethyl end groups possess particularly high reactivity with respect to atmospheric moisture. Corresponding polymers are described in WO 03/014226, hereby incorporated by reference. For sufficiently rapid curing, these polymers need only very small amounts of toxicologically critical tin accelerators, or none at all, and are able on requirement to achieve substantially higher curing rates. Accordingly, the use of α-alkoxysilyl-terminated prepolymers of this kind is particularly desirable.
In one or more embodiments, the moisture-curable silylated resin is an alpha-alkoxysilyl-terminated polymer.
In one or more embodiments, the moisture-curable silylated resin is a gamma-alkoxysilyl-terminated polymer.
In one or more embodiments, the moisture-curable silylated resin has polymer end groups that result from the termination with an alpha or gamma silane. Most preferably, the end groups that result from termination with an alpha-silane. Preferably, the terminal functionalities are alkoxy groups, such that difunctional end groups give rise to two alkoxy groups pendant from the Si atom in a silane terminating group; and such that trifunctional end groups give rise to three alkoxy groups pendant from the Si atom in a silane terminating group.
In one or more embodiments, the moisture-curable silylated resin is a silane- terminated polysiloxane.
In one or more embodiments, the moisture-curable silylated resin is present in an amount of 1-99% w/w of the moisture-curable elastomeric composition, such as within the range of 2-95% w/w, e.g. within the range of 3-90% w/w, such as within the range of 4-85% w/w, e.g. within the range of 5-80% w/w, such as within the range of 10-75% w/w, e.g. within the range of 15-70% w/w, such as within the range of 20-65% w/w, e.g. within the range of 35-60% w/w, such as within the range of 40-55% w/w, e.g. within the range of 45-50% w/w of the moisture-curable elastomeric composition.
In one or more embodiments, the moisture-curable silylated resin is present in an amount of 1-50% w/w of the moisture-curable elastomeric composition, such as within the range of 2-45% w/w, e.g. within the range of 3-40% w/w, such as within the range of 4-35% w/w, e.g. within the range of 5-30% w/w, such as within the range of 10-25% w/w of the moisture-curable elastomeric composition.
In situations where an accelerated activation of the curing process is wanted, or where the moisture-curable elastomeric composition is poorly permeable to water from the surrounding atmosphere; water is added to the moisture-curable elastomeric composition.
In one or more embodiments, water is present in an amount of 0.01 -5% w/w of the moisture-curable elastomeric composition, such as within the range of 0.02-4.5% w/w, e.g. within the range of 0.03-4% w/w, such as within the range of 0.05-3.5% w/w, e.g. within the range of 0.1-3% w/w, such as within the range of 0.5-2.5% w/w, e.g. within the range of 1 -2% w/w, preferably within the range of 0.01-1% w/w of the moisture-curable elastomeric composition.
In some embodiments, water is not added to the moisture-curable elastomeric composition, but enters the moisture-curable elastomeric composition from the surrounding moist air.
In one or more embodiments, the weight ratio between the moisture-curable silylated resin and the water in the moisture-curable elastomeric composition is within the range of 10:1 -100:1, e.g. within the range of 15:1 -95:1, such as within the range of 20:1 -90:1, e.g. within the range of 25:1 -85:1, such as within the range of 30:1 -80:1, e.g. within the range of 35:1 -75:1, such as within the range of 40:1 -70:1, e.g. within the range of 45:1 -65:1, such as within the range of 50:1 -60:1, preferably within the range of 20:1 -50:1.
In principle, the elastomeric polymer composition may comprise any type of nonmoisture-curable elastomeric polymers, i.e. elastomeric polymers that cannot be cured by water.
Examples of non-moisture-curable elastomeric polymers include, but are not limited to, polyolefin elastomers like NR(Natural Rubber), IR(lsoprene Rubber), BR(Butadiene Rubber), SBR(Styrene Butadienen Rubber), EPM(Ethylene Propylene Rubber), EPDM (Ethylene-Propylene-DieneMonomer Rubber), IIR(lsobuylenelsopreneRubber), PNR(Norbornene Rubber), more polar and oil resistant elastomers like NBR(acryloNitrile-Butadiene Rubber), HNBR(Hydrogenated-acryloNitrile-Butadiene Rubber, CR(Chloroprene Rubber), CO/ECO(Epichlorhydrine Rubber), ACM(Acrylate Rubber), AU/EU(Polyurethane Rubber), Q(Silicone Rubber) and TPE(Termoplastic Elastomers and compositions) based on styrenic block copolymers, such as styrene-butadiene-styrene ("SBS"), styrene-isoprene-styrene ("SIS"), styrene-ethylene/propylene-styrene ("SEPS"), and styrene-ethylene/butylene-styrene ("SEBS"), and/or based on other TPE-polymers and compositions.
When at least a part of the non-moisture-curable elastomeric polymers are nonpolar, it may be an advantage to add water to the moisture-curable elastomeric material composition as a pre-mix comprising water and one or more surfactants.
In one or more embodiments, the water in step b2) is added as a pre-mix comprising water one or more surfactants.
In one or more embodiments, the water in step b2) is added as a pre-mix comprising water, accelerator, and one or more surfactants.
In one or more embodiments, the elastomeric polymer composition further comprises one or more components selected from the group consisting of accelerator, retarder, activator, particulate material, softener, resin, wax, moisture scavenger, adhesion promoter, U.V. stabilizer, and antioxidant.
In one or more embodiments, the water in step b2) is added as a pre-mix comprising water and accelerator.
Known accelerators for the vulcanization of moisture-curable silylated resin include numerous compounds, for example dialkyltin(IV) compounds such as dibutyltin dilaurate; various metal complexes (chelates and carboxylates), for example of titanium, bismuth, zirconium, amines and salts thereof; and other known acidic and basic accelerators as well. Reference may be had, for example to EP-A 673 972, EP-A 538 880, and US 2012/0225982. However, known accelerators which promote the isocyanate reaction with hydroxyl groups are often those, which also promote silane condensation, for example dialkyltin(IV) compounds and metal complexes (chelates and carboxylates) of bismuth and zinc, or tertiary amine compounds.
In one or more embodiments, the accelerator is present in an amount of 0.1-10% w/w of the moisture-curable elastomeric composition, such as within the range of 0.5-9% w/w, e.g. within the range of 1-8% w/w, such as within the range of 2-7% w/w, e.g. within the range of 3-6% w/w, such as within the range of 4-5% w/w.
Additives used as coupling agent/surface modifier/water scavenger/crosslinking agent, like monomers, oligomers, or mixtures of di/multi-functional organic materials, like organo(amine)functional silanes, can contribute to the regulation of the reaction. Examples are: metoxy- or ethoxy- functional types like N-(3-(Trimethoxysilyl)propyl)butylamin (CAS nr: 31024-56-3), or gamma-aminopropyltriethoxysilane (CAS nr: 919-30-2).
Another aspect relates to an elastomeric material obtainable by the process according to the present invention.
Another aspect relates to an article of an elastomeric material obtainable by the process according to the present invention.
It should be noted that embodiments and features described in the context of one of the aspects of the present invention also apply to the other aspects of the invention.
The invention will now be described in further details in the following non-limiting examples.
Examples
Proof of concept
The main object of this study was to provide documentation that an ionic complex of an amino alcohol and a metal carboxylate can function as a catalyst for polymerization reactions. The examples are not limited to the used material, but can be compositions compounded with one or more liquid or solid rubber elastomers, one or more in-organic or organic fillers, one or more softeners, one or more moisture-curable silylated resins, one or more moisture-curable silylated monomers, one or more moisture-curable silylated oligomers, one or more accelerators, one or more retarders, one or more water donors, such as a water containing fillers, or as a water containing solution/emulsion/micro-emulsion, one or more colors, one or more antioxidants, one or more UV-stabilizers, one or more water scavengers, one or more activators, or one or more ingredients normally used in compounding of industrially known polymer formulations.
Production of an ionic complex of an amino alcohol and a metal carboxylate An amino alcohol is mixed with a metal carboxylate (exothermic reaction), resulting in the ionic complex.
Types of ionic complex
Homo types with only one metal type.
Mixed types with two or more types of metal carboxylates.
Ionic complex used as catalyst in Silane Reactive Polymer - Ethoxy type
The ionic complex was blended directly into the moisture-curable silylated resin, and allowed to react at 20 degrees Celsius. The amount used of the ionic complex in the below example was 1 % w/w. TEA is triethanolamine. Hardening of the product was measured by use of Cone Penetration. As comparative experiments, the Zinc(triethanolamine)bis(2- ethylhexanoate) (5 days) was exchanged with the same amount of a) Zn-Aminidine-complex K-Kat 670 (3 days), b) Organotin catalyst TIB-Kat 223 (3 days), Bismuth(triethanolamin)bis(2-carboxylate) (10 days) ( c) Bismuth-carboxylate (8 weeks), TEA (8 weeks), and e) Zink-2-ethylhexanoate (» 8 weeks). The time for reaching a cone penetration of 100 is shown in parenthesis. Hence, the new catalyst is comparable in activity to the two toxic catalysts, and much more active than the known low-toxic bismuth-carboxylate used alone. In 2 times concentration Zinc(triethanolamine)bis(2-ethylhexanoate) do have same activity as the tin-organic catalyst. In 4-5 times concentration Bismuth(triethanolamin)bis(2-carboxylate) do have same activity as the tin-organic catalyst.
Cone Penetration, 200g, 20°C, 5 sec. (ISO 2137)
Ionic complex used as catalyst in Silane Reactive Polymer - Methoxv type
Cone Penetration, 200g, 20°C, 5 sec. (ISO 2137)
Normally, Silane Reactive Polymers - Methoxy type will be easier to crosslink in shorter time compared to SRP - Etoxy type. This is also the case using the ionic complex of the present invention. The Methoxy type is fully cured in 2 days, the Ethoxy type is fully cured in 2 weeks. TEA alone will also cure in shorter time in Metoxy type (4 days) compared to Etoxy type (8 weeks).
Ionic complex used as catalyst in a rubber formulation with Silane Reactive Polymer - Ethoxy type, as the crosslinker
The performed tests are to document that: a) The material hardens (i.e. the cone penetration is lowered) when changing from the non-cured moisture-curable polymer composition (green compound) to the cured elastomeric material (rubber product). b) The material strengthens (i.e. the yield strength is increased) when changing from the non-cured moisture-curable polymer composition (green compound) to the cured elastomeric material (rubber product).
Claims (7)
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0023084A1 (en) * | 1979-06-26 | 1981-01-28 | The British Petroleum Company p.l.c. | Cross-linked polymer compositions and production thereof |
| EP1057857A2 (en) * | 1999-06-03 | 2000-12-06 | Dainippon Ink And Chemicals, Inc. | Curing accelerator and resin composition |
| EP1659155A1 (en) * | 2003-08-25 | 2006-05-24 | Kaneka Corporation | Curing composition with improved heat resistance |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0023084A1 (en) * | 1979-06-26 | 1981-01-28 | The British Petroleum Company p.l.c. | Cross-linked polymer compositions and production thereof |
| EP1057857A2 (en) * | 1999-06-03 | 2000-12-06 | Dainippon Ink And Chemicals, Inc. | Curing accelerator and resin composition |
| EP1659155A1 (en) * | 2003-08-25 | 2006-05-24 | Kaneka Corporation | Curing composition with improved heat resistance |
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| DK201500651A1 (en) | 2017-05-15 |
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Effective date: 20191021 |