Sound deadener composition

Abstract

SOLUTION: A sound deadener composition comprises at least two carboxyl functional polymers having different glass transition temperatures (Tg), at least one organic compound having at least two aziridinyl groups per molecule, and water.EFFECT: Since the reaction between at least two carboxyl functional polymers having different glass transition temperatures (Tg) and at least one organic compound having at least two aziridinyl groups per molecule forms an IPN structure, the cured product of the sound deadener composition exhibits a widened temperature range for effective damping.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention provides a method for producing a mixture of different glass transition temperatures (T g The present invention relates to a sound deadener composition comprising at least two carboxyl-functional polymers having at least one aziridinyl group per molecule; at least one organic compound having at least two aziridinyl groups per molecule; and water. The cured product of the sound deadener composition according to the present invention exhibits a wide temperature range for effective vibration damping. [Background technology]

[0002] Rubber vibration damping materials are known to be used to damp vibrations and reduce noise. They utilize the viscoelastic properties of the rubber contained in the composition to dissipate the mechanical energy generated by external mechanical or acoustic vibrations through internal friction caused by the internal molecular motion of polymer chains. Tan δ, also known as the loss factor, is usually an indicator of the effectiveness of a material's damping ability. The larger the tan δ, the higher the damping coefficient. The temperature range over which the damping coefficient of a damping material increases is the effective damping temperature range.

[0003] Damping materials are widely used in the machinery, construction, and automotive industries, etc. However, because conventional damping materials are made from only one type of rubber, their effective damping temperature range is narrow, meaning they cannot be used in high-tech fields such as aircraft and rockets, which require damping materials that provide excellent damping effects across a wide range of temperatures. Summary of the Invention [Problem to be solved by the invention]

[0004] Therefore, there is a need to develop sound deadening compositions and their cured products that have a wide temperature range for effective vibration damping. [Means for solving the problem]

[0005] The present invention relates to a sound deadening composition comprising: a) Different glass transition temperatures (Tg ) at least two carboxyl-functional polymers having; b) at least one organic compound having at least two aziridinyl groups per molecule; wherein the aziridinyl groups of the organic compound may be the same or different from each other and independently have the structure (I): [ka] represented by; and c) water; where: R 1 and R 2 are each independently hydrogen or C 1- C 20 optionally substituted monovalent hydrocarbon radicals, preferably hydrogen or C 1- C 10 optionally substituted monovalent hydrocarbon radicals, more preferably hydrogen or C 1- is a C4 optionally substituted monovalent hydrocarbon radical.

[0006] The present invention also relates to the cured product of the sound deadening composition.

[0007] The cured product of the sound deadening composition has a wide temperature range for effective vibration damping.

[0008] The present invention also relates to articles coated or filled with the cured product of the sound deadening composition.

[0009] The present invention also relates to methods for making and curing the sound deadening compositions. DETAILED DESCRIPTION OF THE INVENTION

[0010] The present invention will now be described in more detail. Each aspect so described can be combined with any other aspect unless expressly indicated otherwise. In particular, any feature indicated as being preferred or advantageous can be combined with any other feature indicated as being preferred or advantageous.

[0011] In the context of the present invention, the terms used are to be construed in accordance with the following definitions, unless the context dictates otherwise.

[0012] As used herein, the singular forms "a," "an," and "the" include both the singular and the plural unless the context clearly dictates otherwise.

[0013] As used herein, the terms "comprise," "include," and "comprise" are synonymous with "include," "includes," or "contain," and are inclusive or open-ended and do not exclude additional, unrecited members, elements, or process steps.

[0014] The recitation of numerical endpoints includes all numbers and fractions within each range, not just the recited endpoint.

[0015] All references cited herein are incorporated by reference in their entirety.

[0016] Unless otherwise defined, all terms used in disclosing the present invention, including technical and scientific terms, have the meaning commonly understood by one of ordinary skill in the art to which this invention belongs. By way of further guidance, term definitions are included to better understand the teachings of the present invention.

[0017] In the context of this disclosure, a number of terms will be utilized.

[0018] The term "(meth)acrylate" refers to either or both "acrylate" and "methacrylate."

[0019] The term "(meth)acrylic" refers to either or both "acrylic" and "methacrylic."

[0020] The term "ethylenically unsaturated" refers to at least one site of unsaturation that is not aromatic.

[0021] The term "hydrocarbon group" refers to an organic group composed of carbon and hydrogen. Examples of hydrocarbon groups include, but are not limited to, alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, tert-butyl, isobutyl, and similar groups; alkenyl groups such as vinyl, allyl, butenyl, pentenyl, hexenyl, and similar groups; aralkyl groups such as benzyl, phenethyl, 2-(2,4,6-trimethylphenyl)propyl, and similar groups; aryl groups such as phenyl, tolyl, xylyl, and similar groups; or alkylidene groups such as methylidene, ethylidene, propylidene, and similar groups.

[0022] The term "optionally substituted" in "optionally substituted hydrocarbon group" means that one or more hydrogens on the hydrocarbon group may be replaced with a corresponding number of substituents, preferably selected from halogen, nitro, azido, amino, hydroxyl, carbonyl, ester, cyano, sulfide, sulfate, sulfoxide, sulfone, sulfonic acid group, and the like.

[0023] The term "substantially free" means that a material or functional group may be present in incidental amounts, or that a particular occurrence or reaction occurs only to an insignificant degree that does not affect the desired properties. In other words, the material or functional group is not intentionally added to the indicated composition, but may be present at small or insignificant levels, for example, because it was carried over as an impurity as part of the intended compositional ingredients.

[0024] The term "water soluble" means that the relevant component or ingredient of the composition is capable of dissolving in the aqueous phase at the molecular level.

[0025] The term "water-dispersible" means that the relevant component or ingredient of the composition is capable of being dispersed in an aqueous phase and forming a stable emulsion or suspension.

[0026] The term "glass transition temperature" refers to the temperature at which a polymer transitions between a highly elastic state and a glassy state. Glass transition temperature can be measured, for example, by dynamic mechanical analysis (DMA).

[0027] Carboxyl-functional polymers The sound deadening compositions of the present invention have different glass transition temperatures (T g The sound deadening composition of the present invention comprises at least two carboxyl functional polymers having different T g Two carboxyl-functional polymers with different T g Three carboxyl-functional polymers with different T g The polymer may have more carboxyl functional groups with different glass transition temperatures (T g Preferably, the carboxyl functional polymers having the formula (I) are partially compatible or incompatible with each other.

[0028] The carboxyl-functional polymer can be any common carboxyl-functional polymer known in the art that has at least one carboxyl functional group. The carboxyl-functional polymers with different glass transition temperatures are preferably water-soluble or water-dispersible and are derived from water-soluble or water-dispersible monomers and combinations thereof, and optionally water-insoluble monomers. The carboxyl-functional polymers with different glass transition temperatures can be obtained by polymerizing ethylenically unsaturated carboxylic acid monomers in the presence of an initiator. Suitable ethylenically unsaturated carboxylic acid monomers include, but are not limited to, acrylic acid, glacial acrylic acid, methacrylic acid, isooctyl acrylic acid, crotonic acid, cinnamic acid, maleic acid, 2-methylmaleic acid, isocrotonic acid, fumaric acid, itaconic acid, 2-methylitaconic acid, methacrylic anhydride, isooctyl acrylic anhydride, crotonic anhydride, fumaric anhydride, maleic anhydride, and any combination thereof. Suitable initiators may be selected from peroxide initiators such as acetyl peroxide, dicumyl peroxide (DCP), 2,5-dimethyl-2,5-bis(t-butylperoxy)hexyne (DBPH), benzoyl peroxide (BPO), bis(2,4-dichlorobenzoyl)peroxide (DCBP), tert-butyl peroxypivalate (BPP), dicyclohexyl peroxydicarbonate (DCPD), potassium persulfate (KSP), and ammonium persulfate (ASP); azo compound initiators such as 2,2'-azo-bis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azo-bis-isobutyronitrile, and azobisisoheptonitrile; and persulfate initiators such as potassium persulfate, sodium persulfate, and ammonium persulfate. The initiators may be used alone or in any combination.

[0029] In some embodiments of the present invention, different glass transition temperatures (T g ) preferably have at least two carboxyl functional groups per molecule.

[0030] In some embodiments of the present invention, different glass transition temperatures (T g It is preferred that the carboxyl functional polymer having the formula (I) be water dispersible rather than water soluble.

[0031] In some embodiments of the present invention, the carboxyl functional polymers having different glass transition temperatures are preferably in the range of −40° C. to 60° C., e.g., T of −40° C., −30° C., −20° C., −10° C., 0° C., 10° C., 20° C., 30° C., 40° C., 50° C., and 60° C. g It has a value.

[0032] Examples of commercially available carboxyl functional polymers are, for example, Acousticryl AV 1331, Acousticryl AV 1220, and Primal SD68, from Dow.

[0033] In some embodiments of the present invention, the different glass transition temperatures (T g The amount of the carboxyl functional polymer having the formula (I) is 5% to 35% by weight, preferably 10% to 25% by weight, based on the total weight of the sound deadening composition.

[0034] [Organic compounds having at least two aziridinyl groups] The sound-deadening composition of the present invention comprises at least one organic compound having at least two aziridinyl groups per molecule. The organic compound having at least two aziridinyl groups per molecule has different glass transition temperatures (T g The mechanism by which the IPN structure is formed is as follows: [ka]

[0035] The aziridinyl groups of the organic compounds of the present invention may be the same or different and independently have the structure (I): [ka] [In the formula, R 1 and R 2 are each independently hydrogen or C 1- C 20 optionally substituted monovalent hydrocarbon radicals, preferably hydrogen or C 1- C 10 optionally substituted monovalent hydrocarbon radicals, more preferably hydrogen or C 1- is a C4 optionally substituted monovalent hydrocarbon radical. It is expressed as:

[0036] In some embodiments of the present invention, the organic compound having at least two aziridinyl groups per molecule preferably has the structure (II): [ka] [In the formula, R 1 and R 2 are each independently hydrogen or C 1- C 20 optionally substituted monovalent hydrocarbon radicals, preferably hydrogen or C 1- C 10 optionally substituted monovalent hydrocarbon radicals, more preferably hydrogen or C 1- is a C4 optionally substituted monovalent hydrocarbon radical; R 3 and R 4 are each independently, C 1- C 20 optionally substituted divalent hydrocarbon radicals of the formula C, preferably C 1- C 10 an optionally substituted divalent hydrocarbon radical of the formula C, more preferably C 1- is a C4 optionally substituted divalent hydrocarbon radical; R 5 is C 1- C 20optionally substituted divalent or polyvalent hydrocarbon radicals of the formula C, preferably C 1- C 10 optionally substituted divalent or polyvalent hydrocarbon radicals of the formula C, more preferably C 1- a C4 optionally substituted divalent or polyvalent hydrocarbon radical; and x is an integer between 2 and 4. It is expressed as:

[0037] In some embodiments of the present invention, the organic compound preferably contains at least three aziridinyl groups per molecule.

[0038] Specific examples of organic compounds having at least two aziridinyl groups per molecule include, but are not limited to, the following: [ka] or [ka] or [ka] .

[0039] In some embodiments of the present invention, when the loss factor of the cured product of the sound-deadening composition to be improved is between 0 and 60°C, R in structure (I) or (II) 1 and R 2 Preferably, both are hydrogen.

[0040] In some embodiments of the present invention, when the loss factor of the cured product of the sound-deadening composition to be improved is between −40° C. and 0° C., R in structure (I) or (II) 1 and R 2 At least one of the following is preferably C 1- C 20 an optionally substituted monovalent hydrocarbon radical of, more preferably C 1- C 10and even more preferably C 1- is a C4 optionally substituted monovalent hydrocarbon radical.

[0041] Examples of commercially available organic compounds having at least two aziridinyl groups per molecule are, for example, XC-103, XC-105, and XC-113 from Shanghai Zealchem ​​Co., Ltd.

[0042] In some embodiments of the present invention, different glass transition temperatures (T g The weight ratio between the at least two carboxyl functional polymers having the formula (I) and the organic compound having at least two aziridinyl groups per molecule is preferably 100:0.5 to 100:50, more preferably 100:1 to 100:25, and even more preferably 100:8 to 100:12, in order to further improve the loss factor of the cured product of the sound deadening composition.

[0043] In some embodiments of the present invention, the amount of the organic compound having at least two aziridinyl groups per molecule in the sound-deadening composition is 0.1 to 5 wt %, preferably 0.3 to 3 wt %, based on the total weight of the sound-deadening composition.

[0044] 〔water〕 The sound deadening composition of the present invention contains water to adjust the viscosity of the composition. The water used in the present invention is preferably purified water.

[0045] In some embodiments of the present invention, the amount of water in the sound-deadening composition of the present invention is 10 to 60 wt %, for example, 20 wt %, 30 wt %, 40 wt %, and 50 wt %, based on the total weight of the sound-deadening composition.

[0046] [Additional Additives] The sound-deadening composition of the present invention may further comprise optional additives. The selection of suitable additives for the sound-deadening composition of the present invention may depend on the specific intended use of the sound-deadening composition and can be determined in each case by one skilled in the art.

[0047] <Thickener> The sound-deadening composition of the present invention may further comprise at least one thickener. Examples of thickeners include, but are not limited to, carboxymethyl cellulose, methyl cellulose, cellulose ether, hydroxyethyl cellulose, polyvinyl ether, polyvinyl alcohol, and sodium polyphosphate. The thickeners may be used alone or in combination.

[0048] Examples of commercially available thickeners are, for example, Arbocel ZZ 8 / 1 from Rettenmaier; CMC type 75 A powder from Mikro Technik; Natrosol 250 HHR from Ashland Aqualon; and Kelzan xanthan gum from CP Kelco.

[0049] In some embodiments of the present invention, the amount of thickener in the sound deadening composition of the present invention is 0 to 30% by weight, preferably 0.1 to 1% by weight, based on the total weight of the sound deadening composition.

[0050] <Antifoaming agent> The sound deadening composition of the present invention may further comprise at least one defoaming agent. Exemplary defoaming agents include, but are not limited to, silicone-based defoaming agents and acrylic-based defoaming agents. The defoaming agents may be used alone or in combination.

[0051] Examples of commercially available defoamers are, for example, BYK-051, BYK-052, BYK-053, BYK-054, BYK-055 from BYK-Chemie GmbH; DISPARLON 1930N and DISPARLON 1934 from Kusumoto Chemicals, Ltd.; and Foamaster MO NXZ from BASF.

[0052] In some embodiments of the present invention, the amount of the antifoaming agent in the sound deadening composition of the present invention is 0 to 2 wt %, preferably 0.1 to 1 wt %, based on the total weight of the sound deadening composition.

[0053] <Corrosion inhibitor> The sound-deadening composition of the present invention may further comprise at least one corrosion inhibitor. Examples of corrosion inhibitors include, but are not limited to, cyclohexylamine, diammonium phosphate, dilithium oxalate, dipotassium oxalate, dipotassium phosphate, phosphoric acid, nickel phosphate, and magnesium phosphate. The corrosion inhibitors may be used alone or in combination.

[0054] Examples of commercially available corrosion inhibitors are, for example, PCG 1201, PCG1909, and PCG 2390 from Polygon Chemie AG.

[0055] In some embodiments of the present invention, the amount of corrosion inhibitor in the sound-deadening composition of the present invention is 0 to 10 wt %, preferably 0.1 to 5 wt %, based on the total weight of the sound-deadening composition.

[0056] <Flame retardant> The sound deadening composition of the present invention may further comprise at least one flame retardant. Examples of flame retardants include, but are not limited to, phosphorus-based plasticizers, aluminum hydroxide, magnesium hydroxide, and thermally expandable graphite. The flame retardants may be used alone or in combination.

[0057] Examples of commercially available flame retardants are, for example, aluminum hydroxide from Shanghai Jianghu Industry Co., Ltd.; ADT 20, ADT 150, and ADT 802 from Shijiazhuang ADT Carbonic Material Factory; CX150, CX 200, and CX 325 from Qingdao Tianheda Graphite Co., Ltd.

[0058] In some embodiments of the present invention, the amount of the flame retardant in the sound-absorbing composition of the present invention is 0 to 40% by weight, preferably 15 to 30% by weight, based on the total weight of the sound-absorbing composition.

[0059] <pH adjuster> The sound-absorbing composition of the present invention may further contain at least one pH adjuster. Examples of pH adjusters include, but are not limited to, citric anhydride, alkali metal hydroxides, and buffered organic acid solutions (such as acetic acid, glutamic acid, and citric acid). The pH adjusters can be used alone or in combination.

[0060] Examples of commercially available and obtainable pH adjusters are, for example, potassium pyrophosphate from Redox Chemicals Pty. Ltd.; and aqueous ammonia from Showa Denko.

[0061] In some embodiments of the present invention, the amount of the pH adjuster in the sound-absorbing composition of the present invention is 0 to 5% by weight, preferably 0.1 to 2% by weight, based on the total weight of the sound-absorbing composition.

[0062] <Filler> The sound-absorbing composition of the present invention may further contain at least one filler. Examples of fillers include reinforcing fillers such as fumed silica, precipitated silica, crystalline silica, fused silica, dolomite, and carbon black; fibrous fillers such as asbestos, glass fibers, and filaments; and other fillers such as ground calcium carbonate, colloidal calcium carbonate, magnesium carbonate, barium carbonate, barium sulfate, diatomaceous earth, calcined clay, clay, talc, barite, anhydrous gypsum, titanium oxide, bentonite, organic bentonite, ferric oxide, aluminum fine powder, flint powder, zinc oxide, activated zinc white, mica, zinc white, and white lead, but are not limited thereto. The fillers can be used alone or in combination.

[0063] Examples of commercially available fillers are, for example, glass fiber 4.5 mm from Saint-Gobain; Muscovite mica 247 from Ziegler & Co. GmbH; calcium carbonate from Fengxian Bazi Shifen; and AEROSIL R 974 from Evonik Specialty Chemicals (Shanghai) Co, Ltd.

[0064] In some embodiments of the present invention, the amount of filler in the sound deadening composition of the present invention is 0 to 40% by weight, preferably 5 to 25% by weight, based on the total weight of the sound deadening composition.

[0065] Other optional additives that may be used in the sound deadening compositions of the present invention include, but are not limited to, antioxidants; biocides; dyes; pigments; and mixtures thereof.

[0066] In a preferred embodiment, the sound deadening composition of the present invention comprises: 5 to 35 wt% of different glass transition temperatures (T g ) at least two carboxyl-functional polymers having; 0.1 to 5% by weight of at least one organic compound having at least two aziridinyl groups per molecule; 10-60% by weight water; 0-30% by weight of at least one thickening agent; 0-2 wt. % of at least one antifoaming agent; 0-10% by weight of at least one filler; 0-40% by weight of at least one flame retardant; 0-10 wt. % of at least one corrosion inhibitor; and 0-5 wt. % of at least one pH adjuster; where the weight percentages of all components add up to 100% by weight.

[0067] The sound deadening compositions of the present invention have different glass transition temperatures (T g), and at least one organic compound having at least two aziridinyl groups per molecule, together with optional additives such as at least one thickener, at least one pH adjuster, at least one filler, at least one flame retardant, at least one corrosion inhibitor, and at least one antifoaming agent.

[0068] In some embodiments of the present invention, the sound deadening composition of the present invention is preferably prepared by the following steps: a) Different glass transition temperatures (T g ) in water with at least one thickener and / or at least one pH adjuster to obtain a gel; b) adding at least one filler, and / or at least one flame retardant, and / or at least one corrosion inhibitor, and / or at least one antifoaming agent to the gel and thoroughly mixing all ingredients to obtain a pre-mixer; and c) adding at least one organic compound having at least two aziridinyl groups per molecule to the pre-mixer and mixing all ingredients well under vacuum;

[0069] The sound deadening composition of the present invention is applied to the surface of the substrate by means of a scooper, sprayer or extruder and allowed to cure at room temperature.

[0070] In some embodiments, curing the sound deadening composition of the present invention may include the following steps: a) exposing the sound deadening composition to room conditions for 1 to 4 hours; b) heating the sound-deadening composition at a temperature in the range of 40 to 80°C for 2 to 6 hours; and c) Cooling the sound deadening composition and leaving it at room temperature for 5 to 10 days to cure the sound deadening agent.

[0071] The loss factor of the cured product of the sound deadening composition of the present invention can be measured in accordance with GB / T 16406.

[0072] The cured product of the sound deadening composition of the present invention is a carboxyl functional polymer T g The cured product of the sound deadening composition of the present invention preferably has an improvement in loss factor of 10% or more, more preferably an improvement in loss factor of 20% or more, and even more preferably an improvement in loss factor of 40% or more, compared to a benchmark loss factor measured for a cured product of a sound deadening composition containing the same carboxyl-functional polymer but not containing an organic compound having at least two aziridinyl groups per molecule in the composition. [Example]

[0073] The present invention will be further described and illustrated with reference to the following examples. The examples are intended to help those skilled in the art better understand and practice the present invention, but are not intended to limit the scope of the present invention. Unless otherwise specified, all numerical values ​​in the examples are by weight.

[0074] Examples 1-8 The following materials were used in the examples: water; tetrapotassium pyrophosphate (manufactured by Redox Chemicals Pty. Ltd.); Arbocel ZZ 8 / 1 (natural cellulose fiber, manufactured by Rettenmaier); Fiberglass (4.5mm long, manufactured by Saint Gobain Vetrotex); Acousticryl AV 1331 (containing 50% by weight of acrylic polymer and 50% by weight of water, T g acrylic emulsion with a value, manufactured by Dow); Acousticryl AV 1220 (containing 50% by weight of acrylic polymer and 50% by weight of water, T gacrylic emulsion with a value, manufactured by Dow); Primal SD 68 (containing 50% by weight of acrylic polymer and 50% by weight of water at −20° C. T g acrylic emulsion with a value, manufactured by Dow); XC-103 (trimethylolpropane tris(3-aziridinylpropanoate), manufactured by Shanghai Zealchem ​​Co., Ltd.); XC-113 (trimethylolpropane tris(2-methyl-1-aziridinepropionate), manufactured by Shanghai Zealchem ​​Co., Ltd.); Foamaster MO NXZ (defoamer, manufactured by BASF); CMC Type 75A powder (carboxymethylcellulose sodium salt, manufactured by Mikro Technik); Natrosol 250 HHR (hydroxyethyl cellulose, manufactured by Ashland Aqualon); Muscovite Mica 247 (mica, manufactured by Ziegler & Co. GmbH); Muscovite mica N800 (mica, manufactured by Ziegler & Co. GmbH); aluminum hydroxide (manufactured by Shanghai Jianghu Industry); calcium carbonate (manufactured by Fengxian Bazi Shifen); PCG 1201 (corrosion inhibitor, manufactured by Polygon Chemie); and Kelzan xanthan gum (manufactured by CP Kelco).

[0075] The sound deadening composition was prepared as shown in the experimental example (Ex.).

[0076] <Ex.1> Acousticryl AV 1331 (15 g), Acousticryl AV 1220 (8 g), Primal SD68 (15 g), Arbocel ZZ 8 / 1 (0.6 g), CMC Type 75A powder (0.1 g), Natrosol 250 HHR (0.1 g), Kelzan xanthan gum (0.1 g), and tetrapotassium pyrophosphate (0.3 g) were mixed together in water (4.6 g) at a speed of 1750 r / min for 30 minutes in a mixer (EUROATAR 60 digital, manufactured by IKA) to obtain a gel.

[0077] To the gel, glass fiber (0.8 g), Foamaster MO NXZ (0.1 g), muscovite mica 247 (27 g), calcium carbonate (10 g), aluminum hydroxide (15 g), and PCG 1201 (0.3 g) were added, and the mixture was mixed for 30 seconds at a speed of 1000 r / min using a speed mixer (SpeedMixer DAC 600.2 VAC-P, manufactured by Flack Tek Inc.) to obtain a premixer.

[0078] The pre-mixer was further blended by mixing under vacuum at a speed of 2000 r / min for 60 seconds using a speed mixer (SpeedMixer DAC 600.2 VAC-P, manufactured by Flack Tek Inc.) to obtain a sound deadening composition of Ex. 1.

[0079] The loss factor L1 (benchmark loss factor) of the cured sound deadening composition of Ex.1 was measured in accordance with GB / T 16406. The loss factor was tested using a B&K apparatus, applying the cantilever beam method. The test specimen was prepared by applying the sound deadening composition of Ex.1 to the surface of cold rolled steel (length 200 mm, width 10 mm, and thickness 1 mm).

[0080] The sound deadening composition was cured by the following steps: a) leaving the sound deadening composition on the cold rolled steel at room temperature for 2 hours; b) heating the sound deadening composition at 60°C for 4 hours; and c) cooling the sound deadening composition and leaving it at room temperature for 7 days to harden the sound deadening composition.

[0081] The dimensions of the hardened sound deadening composition on cold rolled steel are 2 mm thick and 180 mm free length.

[0082] The improvement rate M1 of the loss factor was calculated as follows: M1=(L1-L1) / L1

[0083] <Ex.2> Acousticryl AV 1331 (15 g), Acousticryl AV 1220 (8 g), Primal SD68 (15 g), Arbocel ZZ 8 / 1 (0.6 g), CMC Type 75A powder (0.1 g), Natrosol 250 HHR (0.1 g), Kelzan xanthan gum (0.1 g), and tetrapotassium pyrophosphate (0.3 g) were mixed together in water (4.1 g) at a speed of 1750 rpm for 30 minutes in a mixer (EUROATAR 60 digital, manufactured by IKA) to obtain a gel.

[0084] To the gel, glass fiber (0.8 g), Foamaster MO NXZ (0.1 g), muscovite mica 247 (27 g), calcium carbonate (10 g), aluminum hydroxide (15 g), and PCG 1201 (0.3 g) were added, and the mixture was mixed for 30 seconds at 1000 rpm using a speed mixer (SpeedMixer DAC 600.2 VAC-P, manufactured by Flack Tek Inc.) to obtain a pre-mixer.

[0085] XC-103 (0.5 g) was further added to the pre-mixer, and the mixture was mixed under vacuum at a speed of 2000 r / min for 60 seconds using a speed mixer (SpeedMixer DAC 600.2 VAC-P, manufactured by Flack Tek Inc.) to obtain a sound-deadening composition of Ex. 2.

[0086] The sound deadening composition of Ex. 2 was left to harden in the same manner as in Ex. 1. The loss factor L2 of the hardened sound deadening composition of Ex. 2 was measured in the same manner as in Ex. 1.

[0087] The improvement rate of the loss factor M2 was calculated as follows: M2=(L2-L1) / L1

[0088] <Ex.3> The sound deadening composition of Ex.3 was prepared in the same manner as Ex.2, except that 3.6 g of water was used to form a gel, and 1 g of XC-103 was added to the gel to form a pre-mixer.

[0089] The sound deadening composition of Ex. 3 was left to harden in the same manner as in Ex. 1. The loss factor L3 of the hardened sound deadening composition of Ex. 3 was measured in the same manner as in Ex. 1.

[0090] The improvement rate of the loss factor M3 was calculated as follows: M3=(L3-L1) / L1

[0091] <Ex.4> The sound deadening composition of Ex.4 was prepared in the same manner as Ex.2, except that 2.6 g of water was used to form a gel, and 2 g of XC-103 was added to the gel to form a pre-mixer.

[0092] The sound deadening composition of Ex. 4 was left to harden in the same manner as in Ex. 1. The loss factor L4 of the hardened sound deadening composition of Ex. 4 was measured in the same manner as in Ex. 1.

[0093] The improvement rate of the loss factor M4 was calculated as follows: M4=(L4-L1) / L1

[0094] <Ex.5> The sound deadening composition of Ex. 5 was prepared in the same manner as Ex. 2, except that 1.6 g of water was used to form a gel, and 3 g of XC-103 was added to the gel to form a pre-mixer.

[0095] The sound deadening composition of Ex. 5 was left to harden in the same manner as in Ex. 1. The loss factor L5 of the hardened sound deadening composition of Ex. 5 was measured in the same manner as in Ex. 1.

[0096] The improvement rate of the loss factor M5 was calculated as follows: M5=(L5-L1) / L1

[0097] <Ex.6> Acousticryl AV 1331 (15 g), Acousticryl AV 1220 (8 g), Primal SD68 (15 g), Arbocel ZZ 8 / 1 (0.6 g), CMC Type 75A powder (0.1 g), Natrosol 250 HHR (0.1 g), Kelzan xanthan gum (0.1 g), and tetrapotassium pyrophosphate (0.3 g) were mixed together in water (4.6 g) at a speed of 1750 r / min for 30 minutes in a mixer (EUROATAR 60 digital, manufactured by IKA) to obtain a gel.

[0098] To the gel, glass fiber (0.8 g), Foamaster MO NXZ (0.1 g), muscovite mica N800 (27 g), calcium carbonate (10 g), aluminum hydroxide (15 g), and PCG 1201 (0.3 g) were added, and the mixture was mixed for 30 seconds at 1000 rpm using a speed mixer (SpeedMixer DAC 600.2 VAC-P, manufactured by Flack Tek Inc.) to obtain a pre-mixer.

[0099] The pre-mixer was further blended under vacuum using a speed mixer (SpeedMixer DAC 600.2 VAC-P, manufactured by Flack Tek Inc.) at a speed of 2000 r / min for 60 seconds to obtain a sound deadening composition of Ex. 6.

[0100] The sound deadening composition of Ex. 6 was cured in the same manner as in Ex. 1. The loss factor L6 (benchmark loss factor) of the cured sound deadening composition of Ex. 6 was measured in the same manner as in Ex. 1.

[0101] The improvement rate of the loss factor M6 was calculated as follows: M6=(L6-L6) / L6

[0102] <Ex.7> Acousticryl AV 1331 (15 g), Acousticryl AV 1220 (8 g), Primal SD68 (15 g), Arbocel ZZ 8 / 1 (0.6 g), CMC Type 75A powder (0.1 g), Natrosol 250 HHR (0.1 g), Kelzan xanthan gum (0.1 g), and tetrapotassium pyrophosphate (0.3 g) were mixed together in water (2.6 g) at a speed of 1750 r / min for 30 minutes in a mixer (EUROATAR 60 digital, manufactured by IKA) to obtain a gel.

[0103] To the gel, glass fiber (0.8 g), Foamaster MO NXZ (0.1 g), muscovite mica N800 (27 g), calcium carbonate (10 g), aluminum hydroxide (15 g), and PCG 1201 (0.3 g) were added, and the mixture was mixed for 30 seconds at 1000 rpm using a speed mixer (SpeedMixer DAC 600.2 VAC-P, manufactured by Flack Tek Inc.) to obtain a pre-mixer.

[0104] XC-113 (2 g) was further added to the pre-mixer, and the mixture was mixed under vacuum at a speed of 2000 rpm for 60 seconds using a speed mixer (SpeedMixer DAC 600.2 VAC-P, manufactured by Flack Tek Inc.) to obtain a sound-deadening composition of Ex. 7.

[0105] The sound deadening composition of Ex. 7 was cured in the same manner as in Ex. 1. The loss factor L7 of the cured sound deadening composition of Ex. 7 was measured in the same manner as in Ex. 1.

[0106] The improvement rate of the loss factor M7 was calculated as follows: M7=(L7-L6) / L6

[0107] <Ex.8> The sound deadening composition of Ex. 8 was prepared in the same manner as Ex. 7, except that 0.6 g of water was used to form a gel, and 4 g of XC-113 was added to the gel to form a pre-mixer.

[0108] The sound deadening composition of Ex. 8 was left to harden in the same manner as in Ex. 1. The loss factor L8 of the hardened sound deadening composition of Ex. 8 was measured in the same manner as in Ex. 1.

[0109] The improvement rate of the loss factor M8 was calculated as follows: M8=(L8-L6) / L6

[0110] The test results for Ex.1 to Ex.8 are shown in Table 1. The sound-deadening compositions containing either XC-103 (Ex.2-5) or XC-113 (Ex.7-8) had better loss factors than the sound-deadening compositions of Ex.1 or Ex.6. When the loss factor of the cured sound-deadening composition to be improved is at 10°C, the sound-deadening composition containing XC-103 was more preferable. When the loss factor of the cured sound-deadening composition to be improved is at -10°C, the sound-deadening composition containing XC-113 was more preferable.

[0111] [Table 1]

Claims

1. below: a) Different glass transition temperatures (T ｇ at least two carboxyl-functional polymers having b) at least one organic compound having at least two aziridinyl groups per molecule, wherein the aziridinyl groups may be the same or different and independently have the structure (I): 【Chemistry 1】 [In the formula, R １ and R ２ are each independently hydrogen or C １－ C ２０ optionally substituted monovalent hydrocarbon radicals, preferably hydrogen or C １－ C １０ an optionally substituted monovalent hydrocarbon radical of, more preferably hydrogen or C １－ C ４ is an optionally substituted monovalent hydrocarbon radical of the formula: and c) water; A sound deadening composition comprising:

2. The carboxyl functional polymers having different glass transition temperatures range from -40 to 60°C. ｇ 2. The sound deadening composition of claim 1, preferably having a value of

3. 3. The sound deadening composition according to claim 1 or 2, wherein the at least two carboxyl functional polymers having different glass transition temperatures are preferably partially compatible or incompatible with each other.

4. The sound deadening composition according to any one of claims 1 to 3, wherein said at least two carboxyl functional polymers having different glass transition temperatures are preferably water dispersible or water soluble, more preferably water dispersible.

5. The sound deadening composition according to any one of claims 1 to 4, wherein the organic compound preferably contains at least three aziridinyl groups per molecule.

6. The organic compound having at least two aziridinyl groups per molecule has the structure (II): 【Chemistry 2】 [In the formula, R １ and R ２ are each independently hydrogen or C １－ C ２０ optionally substituted monovalent hydrocarbon radicals, preferably hydrogen or C １－ C １０ an optionally substituted monovalent hydrocarbon radical of, more preferably hydrogen or C １－ C ４ is an optionally substituted monovalent hydrocarbon radical of R ３ and R ４ are each independently C １－ C ２０ optionally substituted divalent hydrocarbon radicals of the formula C, preferably C １－ C １０ an optionally substituted divalent hydrocarbon radical of １－ C ４ is an optionally substituted divalent hydrocarbon radical of R ５ is C １－ C ２０ optionally substituted divalent or polyvalent hydrocarbon radicals of the formula C, preferably C １－ C １０ optionally substituted divalent or polyvalent hydrocarbon radicals of the formula C, more preferably C １－ C ４ an optionally substituted divalent or polyvalent hydrocarbon radical of x is an integer from 2 to 4. The sound-deadening composition according to any one of claims 1 to 5, wherein

7. When the loss factor of the cured product of the sound deadening composition to be improved is between 0 and 60°C, R in structure (I) or (II) １ and R ２ The sound deadening composition according to any one of claims 1 to 6, wherein preferably both are hydrogen.

8. When the loss factor of the cured product of the sound deadening composition to be improved is between −40 and 0° C., R in structure (I) or (II) １ and R ２ At least one of the following is preferably C １－ C ２０ and more preferably, C １－ C １０ and even more preferably, C １－ C ４ 8. The sound-deadening composition according to claim 1, wherein the optionally substituted monovalent hydrocarbon group is:

9. Different glass transition temperatures (T ｇ 9. The sound-deadening composition according to claim 1, wherein the weight ratio between the at least two carboxyl-functional polymers having a carboxylic acid group (C1) and an organic compound having at least two aziridinyl groups per molecule is preferably from 100:0.5 to 100:50, more preferably from 100:1 to 100:25, and even more preferably from 100:8 to 100:

12.

10. 10. The sound deadening composition according to any one of claims 1 to 9, further comprising at least one thickener, and / or at least one antifoaming agent, and / or at least one filler, and / or at least one corrosion inhibitor, and / or at least one pH adjuster, and / or at least one flame retardant is further present in the sound deadening composition.

11. 5 to 35% by weight of different glass transition temperatures (T ｇ at least two carboxyl-functional polymers having 0.1 to 5% by weight of at least one organic compound having at least two aziridinyl groups per molecule; 10 to 60% by weight of water; 0-30 wt. % of at least one thickening agent; 0 to 2 wt. % of at least one antifoaming agent; 0-10% by weight of at least one filler; 0-40 wt. % of at least one flame retardant; 0 to 10 wt. % of at least one corrosion inhibitor; and 0-5 wt. % of at least one pH adjuster; 11. The sound deadening composition of any of claims 1 to 10, comprising:

12. A cured product of the sound deadening composition according to any one of claims 1 to 11.

13. 13. An article coated or filled with the cured product of the sound deadening composition of claim 12.

14. Different glass transition temperatures (T ｇ 14. A method for producing the sound-deadening composition according to any one of claims 1 to 13, comprising the step of uniformly mixing in water at least two carboxyl-functional polymers having a carboxyl group selected from the group consisting of carboxyl groups of 1 to 2, and at least one organic compound having at least two aziridinyl groups per molecule, together with optional additives such as at least one thickener, at least one pH adjuster, at least one filler, at least one flame retardant, at least one corrosion inhibitor, and at least one antifoaming agent.

15. Steps below: a) exposing the sound deadening composition to room conditions for 1 to 4 hours; b) heating the sound deadening composition at 40-80°C for 2-6 hours; and c) cooling the sound deadening composition and allowing the sound deadening composition to cure for 5 to 10 days A method for curing the sound-deadening composition according to any one of claims 1 to 14, comprising:

Images