Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/08—Processes
  • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/30—Low-molecular-weight compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
  • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
  • C09J175/04—Polyurethanes
  • C09J175/06—Polyurethanes from polyesters
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
  • C09J175/04—Polyurethanes
  • C09J175/08—Polyurethanes from polyethers

Definitions

• the present invention relates to moisture-curable polyurethane hot-melt resin compositions, adhesives, and industrial belts.
• Moisture-curing polyurethane hot-melt adhesives are widely used as adhesives for interior building materials, clothing, and electronic device assembly applications. Industrial belts are one of the uses of urethane-based adhesives, and solvent-based urethane adhesives are currently used. Moisture-curing polyurethane hot-melt adhesives are desired to be used as non-solvent-based adhesives because of restrictions on solvents, but they are rarely used in this application due to their insufficient performance.
• the problem to be solved by the present invention is to provide a moisture-curable polyurethane hot-melt resin composition that is excellent in mechanical strength, durability, and initial adhesive strength.
• the present invention provides a moisture-curable polyurethane hot-melt resin composition containing a hot-melt urethane prepolymer (X) having an isocyanate group, which is a reaction product of a polyol (A) and a polyisocyanate (B),
• the polyol (A) contains a polycarbonate polyol (a1) and/or polytetramethylene glycol (a2), a polyester polyol (a3), and a chain extender (a4)
• the polyisocyanate (B ) contains a diisocyanate (b1) and a polyfunctional isocyanate (b2) other than the diisocyanate (b1).
• the present invention also provides an adhesive characterized by containing the moisture-curable polyurethane hot-melt resin composition.
• the present invention also provides an industrial belt using the adhesive.
• the moisture-curable polyurethane hot-melt resin composition of the present invention is excellent in mechanical strength, durability, and initial adhesive strength. Therefore, the moisture-curable polyurethane hot-melt resin composition of the present invention can be particularly suitably used as an adhesive for manufacturing industrial belts.
• the moisture-curable urethane hot-melt composition of the present invention is a moisture-curable polyurethane containing a hot-melt urethane prepolymer (X) having an isocyanate group, which is a reaction product of a polyol (A) and a polyisocyanate (B).
• a hot-melt resin composition wherein the polyol (A) comprises a polycarbonate polyol (a1) and/or polytetramethylene glycol (a2), a polyester polyol (a3), a chain extender (a4), and the polyisocyanate (B) contains a diisocyanate (b1) and a polyfunctional isocyanate (b2) other than the diisocyanate (b1).
• the moisture-curable urethane hot-melt composition of the present invention is designed to soften the soft segments of the urethane resin and to strengthen the hard segments by increasing the number of cross-linking points by adopting the above-described structure. You can satisfy the various tasks you are trying to do, but
• the polycarbonate polyol (a1) and/or polytetramethylene glycol (a2) are essential components for obtaining excellent mechanical strength, durability and initial adhesive strength.
• polycarbonate polyol (a1) for example, one obtained by reacting a carbonate ester and/or phosgene with a compound having two or more hydroxyl groups can be used.
• carbonate ester for example, dimethyl carbonate, diethyl carbonate, diphenyl carbonate, ethylene carbonate, propylene carbonate, etc. can be used. These compounds may be used alone or in combination of two or more.
• Examples of the compound having two or more hydroxyl groups include ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, 1,3-butanediol, 1,2-butanediol, 2-methyl -1,3-propanediol, 1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, 1,5-hexanediol, 3-methyl-1,5-pentanediol, 1,7-heptanediol , 1,8-octanediol, 1,9-nonanediol, 1,8-nonanediol, 2-ethyl-2-butyl-1,3-propanediol, 1,10-decanediol, 1,12-dodecanediol , 1,4-cyclohexanedimethanol, 1,3-
• These compounds may be used alone or in combination of two or more.
• the group consisting of 1,4-butanediol, 1,5-pentanediol, and 1,6-hexanediol from the viewpoint of obtaining even better mechanical strength, durability, and initial adhesive strength It is preferable to use one or more selected compounds.
• the number average molecular weight of the polycarbonate polyol (a1) is preferably 700 to 8,000, more preferably 1,000 to 5,000, from the viewpoint of obtaining even better mechanical strength, durability, and initial adhesive strength. is more preferred.
• the number average molecular weight of the polycarbonate polyol (a1) is the value measured by gel permeation chromatography (GPC).
• the number average molecular weight of the polytetramethylene glycol (a2) is preferably 700 to 8,000, more preferably 1,000 to 5, from the viewpoint of obtaining even better mechanical strength, durability, and initial adhesive strength. ,000 is more preferred.
• the number average molecular weight of the polycarbonate polyol (a1) is the value measured by gel permeation chromatography (GPC).
• the total amount of the polycarbonate polyol (a1) and the polytetramethylene glycol (a2) is among the polyols (A) from the viewpoint that even better mechanical strength, durability, and initial adhesive strength can be obtained. 30 to 70% by mass is preferred, and 40 to 60% by mass is more preferred.
• the polyester polyol (a3) is an essential component for obtaining excellent mechanical strength, durability, and initial adhesive strength.
• polyester polyol (a3) for example, a compound having two or more hydroxyl groups and a reactant of a polybasic acid can be used.
• Examples of the compound having two or more hydroxyl groups include ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, and 1,7-heptane.
• polybasic acid examples include cyclohexanedicarboxylic acid, cyclopentanedicarboxylic acid, hydrogenated phthalic anhydride, terephthalic acid, isophthalic acid, phthalic acid, phthalic anhydride, succinic acid, adipic acid, pimelic acid, suberic acid, and azelaine.
• Acids such as sebacic acid, decanedioic acid, dodecanedioic acid, eicosadioic acid, citraconic acid, itaconic acid, citraconic anhydride, itaconic anhydride, and the like can be used.
• the number average molecular weight of the polyester polyol (a3) is preferably 700 to 8,000, more preferably 1,000 to 5,000, from the viewpoint of obtaining even better mechanical strength, durability, and initial adhesive strength. is more preferred.
• the number average molecular weight of the polyester polyol (a3) indicates a value measured by a gel permeation chromatography (GPC) method.
• the amount of the polyester polyol (a3) used is preferably 30 to 60% by mass, and 40 to 55% by mass in the polyol (A) from the viewpoint of obtaining even better mechanical strength, durability, and initial adhesive strength. % by mass is more preferred.
• the chain extender (a4) is an essential component for obtaining excellent mechanical strength, durability, and initial adhesive strength.
• the chain extender (a4) is different from the above (a1) to (a3) and has a number average molecular weight of 50 to 500.
• the number average molecular weight of the chain extender (a4) indicates a value calculated from the chemical structural formula.
• chain extender (a4) examples include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, hexamethylene glycol, tri Chain extenders having a hydroxyl group such as methylolpropane, glycerin, cyclohexanedimethanol, alkylene oxide adducts of bisphenol A; ethylenediamine, 1,2-propanediamine, 1,6-hexamethylenediamine, piperazine, 2-methylpiperazine, 2 ,5-dimethylpiperazine, isophoronediamine, 4,4'-dicyclohexylmethanediamine, 3,3'-dimethyl-4,4'-dicyclohexylmethanediamine, 1,2-cyclohexanediamine, 1,4-cyclohexanediamine, aminoethyl A chain extender having an amino group such as ethanol,
• chain extenders may be used alone or in combination of two or more.
• a chain extender having a hydroxyl group is preferable from the viewpoint that even better mechanical strength, durability, and initial adhesive strength can be obtained.
• One or more chain extenders selected from the group consisting of -butanediol and 1,3-butanediol are more preferable.
• the alkylene oxide to be added to the bisphenol A is preferably ethylene oxide and/or propylene oxide, more preferably ethylene oxide.
• the number of moles of the alkylene oxide to be added is preferably 1-5, more preferably 2-3.
• the amount of the chain extender (a4) used is preferably 1 to 7% by mass in the polyol (A) in terms of obtaining even better mechanical strength, durability, and initial adhesive strength, and 2 to 5% by mass is more preferred.
• the polyol (A) has the above (a1) to (a4) as essential components, but may contain other polyols as necessary.
• polyether polyols for example, polyether polyols, polyacrylic polyols, polybutadiene polyols, etc. can be used. These polyols may be used alone or in combination of two or more.
• the other polyol preferably does not contain a polyester polyol made from an alkylene adduct of bisphenol A from the viewpoint of obtaining even better mechanical strength, durability, and initial adhesive strength.
• Preferred compounds for the chain extender (a4) include alkylene oxide of bisphenol A.
• the polyisocyanate (B) contains a diisocyanate (b1) and a polyfunctional isocyanate (b2) other than the diisocyanate (b1) in order to obtain excellent mechanical strength, durability, and initial adhesive strength. is essential.
• diisocyanate (b1) examples include aromatic polyisocyanates such as diphenylmethane diisocyanate, phenylene diisocyanate, tolylene diisocyanate and naphthalene diisocyanate; Diisocyanates such as aliphatic or cycloaliphatic polyisocyanates such as tetramethylxylylene diisocyanate can be used. These diisocyanates may be used alone or in combination of two or more. Among these, aromatic polyisocyanates are preferred, and diphenylmethane diisocyanate is more preferred, from the viewpoint of obtaining even more excellent mechanical strength, durability, and initial adhesive strength.
• aromatic polyisocyanates such as diphenylmethane diisocyanate, phenylene diisocyanate, tolylene diisocyanate and naphthalene diisocyanate
• Diisocyanates such as aliphatic or cycloaliphatic polyisocyanates such as t
• polyfunctional isocyanate (b2) other than the diisocyanate for example, isocyanurate compound of diisocyanate (b1); adduct compound; buret compound; allophanate compound; polyfunctional polyisocyanate such as polymethylene polyphenyl polyisocyanate can be used. .
• polyfunctional polyisocyanate such as polymethylene polyphenyl polyisocyanate
• B-2) the "polyfunctional" of the "polyfunctional isocyanate (B-2)" means having 3 or more isocyanate groups.
• polyfunctional isocyanate (b2) polymethylene polyphenyl polyisocyanate is preferable from the viewpoint of obtaining even more excellent mechanical strength, durability, and initial adhesive strength.
• polymethylene polyphenyl polyisocyanate is represented by the following formula (2), preferably where n is an integer of 1 to 5.
• n is an integer of 1 or more.
• polymethylene polyphenyl polyisocyanate examples include "Millionate MR-100” and “Millionate MR-200” manufactured by Tosoh Corporation, “WANNATE PM-200” and “WANNATE PM-400” manufactured by Wanhua Japan Co., Ltd., “Cosmonate M-1500” manufactured by Mitsui Chemicals, Inc., "Boranate M-595" manufactured by Dow Chemical Co., Ltd., etc. can be obtained as commercial products.
• the mass ratio [(b1)/(b2)] of the diisocyanate (b1) and the polyfunctional isocyanate (b2) even better mechanical strength, durability, and initial adhesive strength can be obtained. , preferably 5/1 to 3/1, more preferably 4.8/1 to 3.2/1.
• the urethane prepolymer (X) having an isocyanate group is obtained by reacting the polyol (A) and the polyisocyanate (B), and can It has an isocyanate group at the polymer terminal or in the molecule that can react with moisture present in the adherend to form a crosslinked structure.
• the polyisocyanate (B) is added dropwise to a reaction vessel containing the polyol (A), and then the isocyanate groups of the polyisocyanate (B) are heated.
• the isocyanate groups of the polyisocyanate (B) are heated.
• the equivalent ratio ([isocyanate group/hydroxyl group]) of the isocyanate group of the polyisocyanate (B) to the hydroxyl group of the polyol (A) when producing the urethane prepolymer (X) is even more excellent. It is preferably from 1.1 to 5, more preferably from 1.3 to 3, from the viewpoint that good mechanical strength, durability, and initial adhesive strength can be obtained.
• the isocyanate group content (hereinafter abbreviated as "NCO %") of the urethane prepolymer (X) is from 0 to 0 in terms of obtaining even better mechanical strength, durability, and initial adhesive strength. .5 to 10% by mass is preferred, and 1.7 to 5% by mass is more preferred.
• the NCO% of the urethane prepolymer (X) is a value measured by potentiometric titration in accordance with JISK1603-1:2007.
• the moisture-curable polyurethane hot-melt composition of the present invention contains the urethane prepolymer (X) as an essential component, but may contain other additives as necessary.
• antioxidants examples include antioxidants, tackifiers, plasticizers, stabilizers, fillers, dyes, pigments, fluorescent brighteners, silane coupling agents, waxes, thermoplastic resins, and the like. can be done.
• the moisture-curable polyurethane hot-melt resin composition of the present invention is excellent in mechanical strength, durability, and initial adhesive strength. Therefore, the moisture-curable polyurethane hot-melt resin composition of the present invention can be particularly suitably used as an adhesive for manufacturing industrial belts.
• Examples of industrial belts include those used for conveying in factory production lines, and can be used in various applications such as automobiles, machine parts, food, and steel.
• Examples of the configuration of the industrial belt include the following aspects.
• TPU General-purpose type Thermoplastic polyurethane
• the thickness of the adhesive layer in the industrial belt is, for example, 100 to 500 ⁇ m.
• Example 1 A four-necked flask equipped with a thermometer, a stirrer, and an inert gas inlet is charged with 41.8 parts by mass of polytetramethylene glycol (number average molecular weight; 2,000, hereinafter abbreviated as “PTMG”), polyester polyol (Reaction product of neopentyl glycol and orthophthalic acid, number average molecular weight: 1,000, hereinafter abbreviated as “PEs (1)”) 37.4 parts by mass, polyester polyol (1,6-hexanediol, And, reaction product of sebacic acid, number average molecular weight; BisA/EO”) was added and heated under reduced pressure at 100°C to dehydrate the flask until the water content in the flask was 0.05% by mass or less.
• MDI 4,4'-diphenylmethane diisocyanate
• cMDI polymethylene polyphenyl polyisocyanate
• Example 2 A four-necked flask equipped with a thermometer, a stirrer, and an inert gas inlet was charged with 56 polycarbonate polyols (number average molecular weight: 2,000, "Duranol T5652" manufactured by Asahi Kasei Corporation, hereinafter abbreviated as "PC"). 9 parts by mass, 20 parts by mass of PEs (1), 20 parts by mass of PEs (2), and 3.1 parts by mass of BisA/EO were charged, and heated under reduced pressure at 100 ° C. to remove water in the flask. It was dehydrated to 0.05% by mass or less.
• PC polycarbonate polyols
• urethane prepolymer (X-2) was obtained by reacting for a period of time, and a moisture-curable polyurethane hot-melt composition (2) was obtained.
• Example 3 A thermometer, a stirrer, a four-necked flask equipped with an inert gas inlet, 55.1 parts by mass of PC, 19.4 parts by mass of PEs (1), 19.4 parts by mass of PEs (2), BisA 6.1 parts of /EO was charged and heated under reduced pressure at 100° C. to dehydrate the flask until the water content in the flask was 0.05% by mass or less. Next, the inside of the flask is cooled to 70°C, 25 parts by mass of MDI melted at 70°C and 7.5 parts by mass of cMDI are added, and reacted at 100°C for about 3 hours under a nitrogen atmosphere until the NCO% becomes constant. A urethane prepolymer (X-3) was obtained by letting it dry, and a moisture-curable polyurethane hot-melt composition (3) was obtained.
• Example 4 A thermometer, a stirrer, a four-neck flask equipped with an inert gas inlet, 57.9 parts by mass of PC, 20.4 parts by mass of PEs (1), 20.4 parts by mass of PEs (2), cyclohexane 1.4 parts by mass of dimethanol (hereinafter abbreviated as “CHDM”) was charged and heated under reduced pressure at 100° C. to dehydrate the flask until the water content in the flask was 0.05% by mass or less.
• CHDM dimethanol
• a urethane prepolymer (X-4) was obtained by reacting for a period of time to obtain a moisture-curable polyurethane hot-melt composition (4).
• Example 5 A thermometer, a stirrer, a four-neck flask equipped with an inert gas inlet, 58.1 parts by mass of PC, 20.5 parts by mass of PEs (1), 20.5 parts by mass of PEs (2), 1 , 4-butanediol (hereinafter abbreviated as “BG”) was charged and heated under reduced pressure at 100° C. to dehydrate until the water content in the flask was 0.05% by mass or less. Next, the inside of the flask is cooled to 70°C, 26.4 parts by mass of MDI and 7.9 parts by mass of cMDI melted at 70°C are added, and the mixture is heated at 100°C for about 3 hours under a nitrogen atmosphere until the NCO% becomes constant. A urethane prepolymer (X-5) was obtained by reacting for a period of time, and a moisture-curable polyurethane hot-melt composition (5) was obtained.
• BG 4-butanediol
• Example 6 A thermometer, a stirrer, a four-neck flask equipped with an inert gas inlet, 47.3 parts by mass of PTMG, 31.9 parts by mass of PEs (1), 15.8 parts by mass of PEs (2), BisA 5 parts by mass of /EO was charged and heated under reduced pressure at 100° C. to dehydrate the flask until the water content in the flask was 0.05% by mass or less. Next, the inside of the flask is cooled to 70°C, 29 parts by mass of MDI and 6.1 parts by mass of cMDI melted at 70°C are added, and the mixture is reacted at 100°C for about 3 hours under a nitrogen atmosphere until the NCO% becomes constant. A urethane prepolymer (X-6) was obtained by letting it dry, and a moisture-curable polyurethane hot-melt composition (6) was obtained.
• thermometer A thermometer, a stirrer, a four-necked flask equipped with an inert gas inlet, 70 parts by mass of PC, 10 parts by mass of PTMG, other polyester polyols (6 mol adduct of propylene oxide of bisphenol A, and sebacic acid reaction product, number average molecular weight; 2,000, hereinafter abbreviated as “other PEs”). dehydrated until Next, the inside of the flask is cooled to 70° C., 25 parts by mass of MDI melted at 70° C. is added, and the reaction is carried out at 100° C. for about 3 hours until the NCO% becomes constant under a nitrogen atmosphere, whereby the urethane prepolymer (XR- 4) was obtained to obtain a moisture-curable polyurethane hot-melt composition (R4).
• other polyester polyols (6 mol adduct of propylene oxide of bisphenol A, and sebacic acid reaction product, number average molecular weight; 2,000, hereinafter
• the number average molecular weights of the polyols used in Examples and Comparative Examples are values measured under the following conditions by a gel permeation chromatography (GPC) method.
• Measuring device High-speed GPC device ("HLC-8220GPC” manufactured by Tosoh Corporation) Column: The following columns manufactured by Tosoh Corporation were connected in series and used. "TSKgel G5000" (7.8mm I.D. x 30cm) x 1 "TSKgel G4000” (7.8mm I.D. x 30cm) x 1 "TSKgel G3000” (7.8mm I.D. x 30cm) x 1 Book “TSKgel G2000" (7.8 mm I.D.
• Examples 1 to 6 which are moisture-curable polyurethane hot-melt compositions of the present invention, are excellent in mechanical strength, durability, and initial adhesive strength.
• Comparative Example 1 is an embodiment containing no polyfunctional isocyanate (b2), but was poor in strength, 100% modulus, elastic modulus, durability, and initial adhesive strength.
• Comparative Example 2 is an embodiment containing no chain extender (a4) and polyfunctional isocyanate (b2), but was poor in strength, 100% modulus, durability, and initial adhesive strength.
• Comparative Example 3 which is an embodiment containing no chain extender (a4), was poor in strength, 100% modulus, elastic modulus, elongation, and initial adhesive strength.
• Comparative Example 4 is an embodiment that does not contain polyols (a1), (a2), and polyfunctional isocyanate (b2), but was poor in 100% modulus, durability, and initial adhesive strength.
• Comparative Example 5 is an embodiment that does not contain polyols (a1) and (a2), but was poor in durability and initial adhesive strength.

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• Polyurethanes Or Polyureas (AREA)
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• 2022
  • 2022-10-20 CN CN202280080795.4A patent/CN118355047A/zh active Pending
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