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WO2010008154A2 - Résine hybride durcissable par l’humidité à température ambiante, procédé de préparation de celle-ci et application de celle-ci - Google Patents

Résine hybride durcissable par l’humidité à température ambiante, procédé de préparation de celle-ci et application de celle-ci Download PDF

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Publication number
WO2010008154A2
WO2010008154A2 PCT/KR2009/003754 KR2009003754W WO2010008154A2 WO 2010008154 A2 WO2010008154 A2 WO 2010008154A2 KR 2009003754 W KR2009003754 W KR 2009003754W WO 2010008154 A2 WO2010008154 A2 WO 2010008154A2
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WO
WIPO (PCT)
Prior art keywords
room temperature
resin
chemical formula
temperature moisture
linear
Prior art date
Application number
PCT/KR2009/003754
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English (en)
Other versions
WO2010008154A3 (fr
Inventor
Tai-Woong Boo
Chun-Mi Kim
Yeun-Su Lim
Nam-Kyung Lee
Original Assignee
Korea Bio-Gen Co., Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020080068452A external-priority patent/KR100879735B1/ko
Priority claimed from KR1020090033852A external-priority patent/KR20100115225A/ko
Application filed by Korea Bio-Gen Co., Ltd filed Critical Korea Bio-Gen Co., Ltd
Publication of WO2010008154A2 publication Critical patent/WO2010008154A2/fr
Publication of WO2010008154A3 publication Critical patent/WO2010008154A3/fr

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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
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4866—Polyethers having a low unsaturation value
    • 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
    • C08G18/71—Monoisocyanates or monoisothiocyanates
    • C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
    • 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
    • C08G2190/00—Compositions for sealing or packing joints

Definitions

  • the present invention relates to a room temperature moisture-curable hybrid resin, a method of preparing the same and application thereof. More particularly, the present invention relates to a room temperature moisture-curable hybrid resin including a silicon compound introduced thereto, which may be applied to sealants, adhesives, binders, coating agents, etc. for use in various industrial fields including construction, electric/electronic and automobile industries, a method of preparing the same and application thereof.
  • Background Art
  • Silicone materials are hybrid materials having organic characteristics combined with inorganic characteristics. Although such silicone materials have excellent heat resistance, electrical insulation properties and weather resistance, they have poor plastering applicability, mechanical properties and adhesive properties and are expensive due to high-cost starting materials.
  • the resin obtained by one of the above methods is room temperature moisture- curable, and may be applied to sealants, adhesives, binders, coating agents, etc. for use in various industrial fields including construction, electric/electronic and automobile industries.
  • the room temperature moisture-curable hybrid resin obtained by one of the above methods applicable to sealants, adhesives, binders, coating agents, etc.
  • the resin is required for the resin to have various properties tailored for particular use.
  • the resin is provide with low viscosity, good workability, elongation controllability depending on particular use, high elasticity, excellent adhesion to various materials, curing rate controllability, rapid tack-free characteristics, excellent mechanical and physical properties, or the like.
  • the highly reactive isocyanate group may react with a hydroxyl, amine, carboxyl group, etc., so that it may be modified with various silane compounds having a reactive group, such as an amine group, with ease at the end.
  • the prepolymer is end- capped with a hydroxyl group
  • the end may be modified with various silane compounds having a reactive isocyanate group to provide a room temperature moisture-curable resin.
  • US Patent No. 3,632,557 discloses introduction of a primary or secondary aliphatic aminosilane into the prepolymer end-capped with an isocyanate group.
  • US Patent No. 4,645,816 discloses a composition of a room temperature moisture-curable resin obtained by introducing an organofunctional silane having one dialkoxy group and one active hydrogen atom to improve the elongation and elasticity.
  • US Patent No. 4,374,237 discloses a polymer resin composition having improved wet adhesion and obtained using a secondary aminosilane monomer having two trialkoxysilane groups.
  • US Patent No. 4,474,933 discloses a method of preparing a room temperature moisture-curable resin using various primary and secondary di- functional aminosilanes as end cappers.
  • US Patent No. 5,364,955 suggests a method of improving a cured elastomer in its flexibility by reducing the crosslinnking density thereof with N-alkoxysilylalkyl aspartic acid ester having a difunctional group and a sterically hindered amine group.
  • the above methods basically use aminosilanes, they entail urea bond formation, resulting in a significant increase in the viscosity of the resin and limited elongation.
  • US Patent No. 6,197,912 discloses a method of preparing a room temperature moisture-curable resin by introducing various secondary aminoalkoxysilanes into various prepolymers end-capped with NCO.
  • the above methods include reacting an equivalently excessive amount of polyisocyanate compounds with polyoxyalkylene diol compounds to obtain isocyanate-containing prepolymers .
  • the room temperature moisture-curable hybrid polymer resins obtained by the above methods are generally high-modulus type polymer resins having good properties as adhesives and sealing agents for materials of electric/electronic and automobile industries.
  • the cured sealing agent is required to have a good elongation.
  • the polymer resins obtained by the above methods have a low elongation due to the urea and urethane bonds and show an increased viscosity, leading to poor workability.
  • US Patent No. 3,971,751 discloses a method for preparing a polyether diol by reacting a hydroxyl group with sodium alkoxide and then with allyl chloride and dichloromethane.
  • the above method requires polymerization of polyoxyalkylene diol to increase the molecular weight of the polyoxyalkylene polyol to 12,000 or higher.
  • preparation of the high-molecular weight polyoxyalkylene polyol is very complicated, requires a high cost, shows difficulty in controlling the molecular weight of the polyol, and tends to broaden the molecular weight distribution of the polyol.
  • US Patent No. 4,345,053 suggests that a room temperature moisture-curable silicone- terminated organic polymer is prepared by reacting a polyoxyalkylene diol, polyoxyalkylene triol or polyhydroxy polysulfide polyol with an organic polyisocyanate (i.e., diisocyanate) to form a polyurethane prepolymer, followed by end capping with an isocyanato organotrialkoxysilane.
  • an organic polyisocyanate i.e., diisocyanate
  • the resultant urethane bonds and urea bonds improve the heat stability and weather resistance of the prepolymer.
  • the prepolymer has excessively high viscosity, poor workability and low elongation.
  • US Patent No. 5,990,257 discloses a method for preparing a rapidly curable, non-brittle and elastic resin by reacting an equivalently excessive amount of polyether polyol having a high molecular weight and low unsaturation degree for decreasing viscosity with a diisocyanate component to form a high-molecular weight hydroxyl- terminated polyurethane prepolymer, which, in turn, is allowed to react with an isocyanato alkoxy functional silane, i.e., a trialkoxyfunctional silane, such as ⁇ - isocyanato propyl-triethoxy silane or ⁇ -isocyanato propyl-trimethoxy silane.
  • an isocyanato alkoxy functional silane i.e., a trialkoxyfunctional silane, such as ⁇ - isocyanato propyl-triethoxy silane or ⁇ -isocyanato propyl-trimethoxy silane.
  • US Patent No. 5,608,304 discloses a method for preparing a high- molecular weight polyoxyalkylene polyol containing ether bonds alone and having a very low unsaturation degree. Also, it discloses a method for preparing a hydrolyzable silyl group-containing polyether compound by reacting the polyoxyalkylene polyol prepared through the above method with isocyanatoalkylalkoxysilane.
  • the resin or compound suggested in the above patent also has a limited resin structure, resulting in a limitation in controlling the elongation. Moreover, when applying the resin to sealants, gluing agents/adhesives or coating agents, it is difficult to impart adequate elongation characteristics.
  • polyalkoxyalkylene polyols having a molecular weight of at most 4,000 is allowed to react with an isocyanate compound to form a high-molecular weight isocyanate- terminated polyurethane prepolymer, which, in turn, is allowed to react with isocyanato alkylalkoxysilane having two or three hydrolyzable groups to obtain a room temperature curable polymer resin.
  • a polyoxyalkylene polyol having a high molecular weight of 8,000 or higher, specifically 12,000 or higher may be prepared and allowed to react directly with a silane compound.
  • preparation of such high-molecular weight polyols is difficult and needs a high cost.
  • the resultant resin has a good elongation but poor mechanical properties.
  • controlling the crosslinking density in a cured molecule may be required to obtain a room temperature moisture-curable hybrid polymer resin having low viscosity, easily controllable elongation and good physical properties adequate for particular use and work.
  • the resultant polymer resin is a polymer resin both ends of which are bound to a silane having three hydrolyzable groups or to a silane having two hydrolyzable groups.
  • a polymer resin both ends of which are the same is allowed according to the related art.
  • a polymer resin both ends of which are of different types, i.e., a heterogeneous (different types of) silane- bound polymer resin, for example, a polymer resin, one end of which is bound to a silane having three hydrolyzable groups and the other end of which is bound to a silane having two hydrolyzable groups.
  • a heterogeneous (different types of) silane- bound polymer resin for example, a polymer resin, one end of which is bound to a silane having three hydrolyzable groups and the other end of which is bound to a silane having two hydrolyzable groups.
  • An object of the present invention is to provide a room temperature moisture-curable hybrid resin obtained by introducing silane compounds having various hydrolyzable groups to various resins and having controllable physical properties, including elongation, elasticity and strength, to be applied to various applications. Further, an object of the present invention is to provide a method for preparing the resin and use thereof. Solution to Problem
  • the present invention provides a room temperature moisture-curable hybrid resin represented by Chemical Formula I:
  • R a and R b are the same or different and each represents a linear or branched
  • R c and R d are the same or different and each represents a linear or branched (Cl-C4)alkyl; [35] R e and R f are the same or different and each represents a linear or branched
  • A represents a substituent having a weight average molecular weight of 5,000-60,000 and is selected from the group consisting of polyacrylate, polyether, polyester, polyurethane, polyoxyalkylene, polyolefin, polyorganosiloxane and a combination thereof;
  • [38] B represents a substituent having a weight average molecular weight of 300-25,000 and is selected from the group consisting of reaction mixtures between an isocyanate compound and any one compound selected from polyether polyol, polyester polyol, polyurethane polyol, polyoxyalkylene polyol, organosiloxane compound and a combination thereof;
  • Z' and Z" are the same or different and each represents a linear (Cl-C4)alkyl or phenyl;
  • each of h and i is an integer selected from 0 to 3, and a+b is an integer of 0 to 6.
  • Chemical Formula I includes a room temperature moisture-curable hybrid resin represented by Chemical Formula 1 or Chemical Formula 10.
  • A represents a substituent having a weight average molecular weight of 5,000-60,000 and is selected from the group consisting of polyacrylate, polyether, polyester, polyurethane, polyoxyalkylene, polyolefin, polyorganosiloxane and a combination thereof;
  • R' and R are the same or different, and each represents a linear or branched
  • Ri' and R 1 are the same or different, and each represents a (Cl-C4)alkyl;
  • X' and X are the same or different, and each represents a linear or branched
  • each of m and n is a number selected from 0-3 with the proviso that m+n is an integer of 0-6.
  • a method for preparing a room temperature moisture-curable hybrid resin represented by Chemical Formula 1 which includes reacting a hydroxyl-terminated prepolymer represented by Chemical Formula 2 with at least one isocyanatoalkyl silane compound represented by Chemical Formula 3 by simultaneous mixing or continuous introduction:
  • A represents a substituent having a weight average molecular weight of 5,000-60,000 and is selected from the group consisting of polyacrylate, polyether, polyester, polyurethane, polyoxyalkylene, polyolefin, polyorganosiloxane and a combination thereof;
  • R represents a linear or branched (Cl-C6)alkylene
  • R' and R represent substituents derived from R, and are identical or different;
  • R 1 represents a linear or branched (Cl-C4)alkyl
  • R 1 ' and R 1 represent substituents derived from R 1 , and are identical or different;
  • X represents a linear or branched (Cl-C6)alkyl
  • X' and X represent substituents derived from X, and are identical or different;
  • n and n independently represent an integer selected from 0 to 3
  • m+n represents an integer from 0 to 6.
  • an adhesive including the above room tern- perature moisture-curable hybrid resin and gluing agent including the above room temperature moisture-curable hybrid resin.
  • the room temperature curable polymer resin disclosed herein is formed by introducing silicon compounds into both ends thereof, wherein various silane compounds having the same or different hydrolyzable groups are allowed to react with each end of the resin simultaneously (or by mixing) or successively. In this manner, the same or different silane compounds bound to both ends of the resin control the crosslinking density or coagulating degree of the resin upon curing.
  • Formula 1 is obtained by reacting a hydroxyl-terminated prepolymer represented by Chemical Formula 2 with at least one isocyanatoalkyl silane compound represented by Chemical Formula 3.
  • Reaction Scheme 1 illustrates one embodiment of the preparation of the room temperature moisture-curable resin.
  • A represents a substituent having a weight average molecular weight of 5,000-60,000 and is selected from the group consisting of polyacrylate, polyether, polyester, polyurethane, polyoxyalkylene, polyolefin, polyorganosiloxane and a combination thereof;
  • R represents a linear or branched (Cl-C ⁇ )alkylene
  • R' and R represent substituents derived from R, and are identical or different;
  • Ri represents a linear or branched (Cl-C4)alkyl
  • R 1 ' and R 1 represent substituents derived from R 1 , and are identical or different;
  • X represents a linear or branched (Cl-C ⁇ )alkyl
  • X' and X represent substituents derived from X, and are identical or different; and [85] 1, m and n independently represent an integer selected from 0 to 3, and m+n represents an integer from 0 to 6.
  • the backbone, prepolymer A represents a polymer selected from the group consisting of polyacrylate, polyether, polyester, polyurethane, poly oxy alky lene, polyolefin, poly- organosiloxane and a combination thereof. Particularly, A represents polyoxyalkylene, polyether or polyurethane. Additionally, A may have a weight average molecular weight of 5,000-60,000, specifically 5,000-50,000 and more specifically 5,000-45,000. If the resin has a molecular weight less than 5,000, it has poor physical properties. On the other hand, if the resin has a molecular weight greater than 60,000, it has poor pro- cessability.
  • the hydroxyl-terminated prepolymer represented by Chemical Formula 2 may include polyoxyalkylene diols or polyetherpolyols having a weight average molecular weight of 8,000 or higher, particularly 12,000 or higher.
  • a silane compound having hydrolyzable groups may be bound directly to the high-molecular weight hydroxyl-terminated prepolymer without forming a separate prepolymer through the reaction with a diisocyanate compound.
  • the above-described hydroxyl-terminated polyurethane prepolymer may be prepared by a reaction between a polyol and a polyisocyanate.
  • the polyol reactant component is used in an equivalently excessive amount as compared to the polyisocyanate component so that the resultant prepolymer is end-capped with hydroxyl groups.
  • -OH group may be 0.3-0.95, more particularly 0.5-0.85.
  • a catalyst may be used depending on the reactivity of each reactant, and the reaction may be carried out at 60-90 0 C for 2-8 hours.
  • the polyisocyanates that may be used to prepare the hydroxyl-terminated polyurethane prepolymer include diisocyanate or polyisocyanate components, which may be aromatic diisocyanates, aliphatic diisocyanates, cycloaliphatic diisocyanate, etc.
  • polyisocyanates include monomers, such as 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 4,4-diphenylmethane diisocyanate, isophorone diisocyanate, dicyclohexylmethane-4,4-diisocyanate, meta-tetramethylxylene diisocyanate, trimethylhexamethylene diisocyanate or hexamethylene diisocyanate and polymers and combinations thereof.
  • monomers such as 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 4,4-diphenylmethane diisocyanate, isophorone diisocyanate, dicyclohexylmethane-4,4-diisocyanate, meta-tetramethylxylene diisocyanate, trimethylhexamethylene diisocyanate or hexamethylene diisocyanate and polymers and combinations thereof
  • the polyisocyanates may include monomers, such as 2,4-toluene diisocyanate (2,4-TDI), 2,6-toluene diisocyanate (2,6-TDI), 4,4-diphenylmethane diisocyanate (MDI), isophorone diisocyanate (IPDI), meta-tetramethylxylene diisocyanate (TMXDI), dicyclo- hexylmethane-4,4-diisocyanate (H12-MDI), trimethylhexamethylene diisocyanate (TMDI), or hexamethylene diisocyanate (HDI).
  • monomers such as 2,4-toluene diisocyanate (2,4-TDI), 2,6-toluene diisocyanate (2,6-TDI), 4,4-diphenylmethane diisocyanate (MDI), isophorone diisocyanate (IPDI), meta-tetramethylxylene
  • the polyols that may be used to prepare the polyurethane prepolymer disclosed herein may include polyols having one, two or more hydroxyl groups, selected from the group consisting of polyether polyols, polyester polyols, polybutadiene diols, poly oxy alky lene diols, poly oxy alky lene triols, polytetraethylene glycol, polycaprolactone diols, polycaprolactone triols and combinations thereof. More particularly, the polyols that may be used herein includes polyether polyols or poly- oxyalkylene diols.
  • the polyoxyalkylene includes polyoxyethylene, poly- oxypropylene or poly oxybuty lene.
  • the polyols that may be used to prepare the polyurethane polyol disclosed herein may have a very low unsaturation degree and a very high functionality.
  • the polyoxyalkylene diols or polyether polyols may be prepared using a metal complex catalyst for the polymerization of alkylene oxide in a manner generally known to those skilled in the art.
  • the polyols may have a low terminal ethylenic unsaturation degree of 0.2 meq/g or less. Polyols with lower unsaturation are more advisable.
  • Such polyols are ideal starting materials for preparing a high- molecular weight polyurethane prepolymer.
  • the polyols having a low unsaturation degree and high molecular weight may reduce the amount of hard segments used for increasing the chain length of the polyurethane prepolymer, it may significantly reduce the viscosity of the polyurethane prepolymer disclosed herein. Moreover, such a low unsaturation level of polyol allows the polyurethane prepolymer to have an increased molecular weight without any loss of functionality during the chain extension.
  • the polyol may have a weight average molecular weight of 500-50,000, particularly 2,000-40,000.
  • the polyol has a weight average molecular weight less than 500, an increased amount of hard segments is used for the preparation of a high-molecular weight polyurethane prepolymer, resulting in production of a polymer having high viscosity and degradation of the processability thereof.
  • the preparation of polymer is not cost-efficient and is commercially unacceptable.
  • R represents a linear or branched (Cl-C ⁇ )alkylene, particularly methylene or propylene;
  • R 1 represents a linear or branched (Cl-C4)alkyl, particularly methyl or ethyl;
  • X represents a linear or branched (Cl-C ⁇ )alkyl, particularly methyl, ethyl, propyl, butyl, and more particularly methyl;
  • a prepolymer having three hydroxyl groups it is possible to control the cros slinking density through the binding of the silanes having different hydrolyzable functional groups as described above.
  • the silane compounds that may be used herein include at least one silane compound selected from silane compounds having three hydrolyzable groups, silane compounds having two hydrolyzable groups, silane compounds having one hydrolyzable groups and silane compounds having no hydrolyzable groups.
  • the silane compounds are introduced simultaneously or successively to the hydroxyl-terminated prepolymer and are allowed to react with the prepolymer, wherein the total silane equivalents are in excess of the hydroxyl equivalents of the prepolymer by 5-10%. That is, the total silane equivalents are 105-110 equivalents based on 100 equivalents of the hydroxyl groups of the hydroxyl-terminated prepolymer. In this manner, it is possible to obtain a uniform room temperature moisture-curable hybrid resin with various grades tailored for particular use.
  • the room temperature moisture-curable hybrid resin may have a controlled viscosity, elongation, elasticity, strength, modulus (low/middle/high modulus) depending on the mixing ratio and types of the silane compounds used therein, so that it may be used as a binder for sealants, sealing agents, adhesives, gluing agents, coating agents, or the like.
  • isocyanatolakyl silane compounds having various hydrolyzable groups are selected from the group consisting of ⁇ -isocyanato propyl trimethoxysilane, ⁇ -isocyanato propyl methyldimethoxysilane, ⁇ -isocyanato propyl dimethylmethoxysilane, ⁇ -isocyanato propyl trimethylsilane, ⁇ -isocyanato propyl tri- ethoxysilane, ⁇ -isocyanato propyl methyldiethoxysilane, ⁇ -isocyanato methyl dimethylethoxysilane, ⁇ -isocyanato methyl trimethoxysilane, ⁇ -isocyanato methyl dimethoxymethylsilane, ⁇ -isocyanato methyl methoxydimethylsilane, ⁇ -isocyanato methyl trimethylsilane, ⁇ -isocyanato methyl trie
  • the room temperature moisture-curable hybrid resin disclosed herein may be obtained by reacting the hydroxyl-terminated prepolymer prepared as described above (having active hydrogen atoms in the form of hydroxyl groups) with at least one of the above-listed isocyanatoalkyl silane compounds simultaneously (by mixing) or continuously in such a manner that the total silane equivalents are in excess of the hydroxyl equivalents by about 5%-10%.
  • the reaction is carried out under atmospheric pressure in a moisture-free condition. Particularly, a moisture-free condition is required for preventing the hydrolysis of the hydrolyzable silane compounds.
  • the reaction may be performed at a temperature of 60-90 0 C for 4-8 hours.
  • the reaction may be performed in the presence of a catalyst but the catalyst may be introduced in a minimized amount depending on the progress of the reaction.
  • reaction may be completed when any residual NCO groups are not monitored.
  • the room temperature moisture-curable polymer resins obtained after the reaction of the hydroxyl-terminated prepolymer prepared as described above with the isocyana- toalkylsilane compounds, may be classified into the following 10 types of resins depending on the number of hydrolyzable groups bound to the ends of the resins, but are not limited thereto.
  • the room temperature moisture-curable hybrid resins disclosed herein may include resins both ends of which are the same hydrolyzable groups, or resins both ends of which are different hydrolyzable groups.
  • the ten types of resins may be mixed in a suitable ratio depending on the particular types of silanes and proportions thereof. In this manner, the cured resin may have a controlled crosslinking density.
  • starting materials of the sealant may include a filler, a plasticizer, a thixotropic agent, an anti-sagging agent, an adhesion promoter, a water scavenger, a stabilizer and a curing catalyst.
  • the filler that may be used herein includes fumed silica, precipitated silica, treated calcium carbonate with a size of 0.07-4 ⁇ m and reinforced carbon black (for improving the physical properties).
  • the filler is used in a completely dried form containing no moisture.
  • the filler may be used in an amount of 50-250 parts by weight based on 100 parts by weight of the resin. When the filler is used in an amount less than 50 parts by weight, it is not possible to sufficiently improve the physical properties. When the filler is used in an amount greater than 250 parts by weight, the resin has poor pro- cessability.
  • the plasticizer that may be used herein includes dioctyl phthalate (DOP), diisodecyl phthalate (DIDP), benzoflex type plasticizer, etc.
  • the plasticizer may be used in an amount of 50-100 parts by weight based on 100 parts by weight of the resin.
  • the thixotropic agent or anti-sagging agent that may be used herein includes castor wax, fumed silica, treated clay, polyamides, etc.
  • the thixotrophic agent or anti-sagging agent may be used in an amount of 1-10 parts by weight based on 100 parts by weight of the resin.
  • silane compounds may be used as the adhesion promoter or water scavenger.
  • the adhesion promoter that may be used herein includes N- aminoethyl-aminoprpyl trimethoxysilane.
  • the water scavenger that may be used herein includes vinyltrimethoxysilane.
  • the adhesion promoter or water scavenger may be used in an amount of 0.5-5 parts by weight based on 100 parts by weight of the resin, depending on the work condition and particular use.
  • the additive for modifying the physical properties 0-10 parts by weight, particularly 0-7 parts by weight, and more particularly 0-5 parts by weight of phenyltrimethoxysilane may be introduced to 100 parts by weight of the room temperature moisture-curable resin.
  • the additive decreases the viscosity of the resin, resulting in improvement in workability, improves the storage stability of the resin, provides excellent elongation and thermal stability through the formation of a flexible network in a cured polymer, improves the storage stability of a sealant by functioning as a water scavenger, and allows control of the curing rate.
  • the additive may be added preliminarily to the moisture-curable resin or may be introduced upon the formulation of a sealant.
  • the curing catalyst 0.01-10 parts by weight of dibutyltin diacetate, stannous octoate, dibutyltin dilaurate, etc. may be used and introduced based on 100 parts by weight of the resin.
  • the curing catalyst is used in an amount less than 0.01 parts by weight, the resin may be cured too slowly.
  • the curing catalyst is used in an amount greater than 10 parts by weight, excessive curing may occur, resulting in degradation of the storage stability.
  • antioxidants and UV stabilizers such as titanium dioxide (TiO 2 ) may be used depending on particular use.
  • additives that may be used herein are not limited thereto.
  • the antioxidants or UV stabilizers may be used in an amount of 0.2-3 parts by weight based on 100 parts by weight of the resin so as to improve the durability and weather resistance of the sealant.
  • the plasticizer is introduced into an agitator and the filler is introduced thereto under agitation, and the materials are mixed uniformly.
  • the stabilizer and the room temperature moisture-curable resin are introduced thereto, the temperature is controlled to 8O 0 C, and the mixture is agitated vigorously under vacuum for 60-90 minutes. Then, the mixture is cooled to 5O 0 C, the adhesion promoter, water scavenger or dehydrating agent, curing catalyst and other additives are added thereto and the resultant mixture is agitated vigorously for about 30 minutes.
  • N 2 is introduced at any time to prevent the reaction mixture from being in contact with moisture.
  • [148] B represents a substituent having a weight average molecular weight of 300-25,000 and is selected from the group consisting of reaction mixtures between an isocyanate compound and any one compound selected from polyether polyol, polyester polyol, polyurethane polyol, polyoxyalkylene polyol, organosiloxane compound and a combination thereof;
  • Rio' and R 10 represent a linear or branched (Cl-C4)alkyl, and are identical or different;
  • Y' and Y represent a linear or branched (Cl-C ⁇ )alkylene, and are identical or different;
  • Z' and Z represent a linear (Cl-C4)alkyl or phenyl, and are identical or different;
  • T' and T represent a linear or branched (Cl-C ⁇ )alkyl, and are identical or different;
  • p and q independently represent an integer selected from 0 to 3
  • p+q represents an integer from 0 to 6.
  • a method for preparing a room temperature moisture-curable hybrid resin represented by Chemical Formula 10 which includes reacting an isocyanate-terminated prepolymer represented by Chemical Formula 20 with at least one sec-aminoalkyl silane compound represented by Chemical Formula 30 by simultaneous mixing or continuous introduction:
  • B represents a substituent having a weight average molecular weight of 300-25,000 and is selected from the group consisting of reactions mixtures between an isocyanate compound and any one compound selected from polyether polyol, polyester polyol, polyurethane polyol, polyoxyalkylene polyol, organosiloxane compound and a combination thereof;
  • R 10 ' and R 10 represent substituents derived from R 10 , and are identical or different;
  • Y represents a linear or branched (Cl-C6)alkylene
  • Y' and Y represent substituents derived from Y, and are identical or different;
  • Z represents a linear (Cl-C4)alkyl or phenyl derivative
  • Z' and Z represent substituents derived from Z, and are identical or different;
  • T represents a linear or branched (C 1 -C6)alkyl
  • T' and T represent substituents derived from T, and are identical or different;
  • o, p and q independently represent an integer selected from 0 to 3, and p+q represents an integer from 0 to 6.
  • a sealing composition including the sealant.
  • an adhesive including the above room temperature moisture-curable hybrid resin, and a gluing agent including the above room temperature moisture-curable hybrid resin.
  • the room temperature moisture-curable polymer resin disclosed herein is formed by introducing silicon compounds into both ends thereof, wherein various silane compounds having the same or different hydrolyzable groups are allowed to react with each end of the resin simultaneously (or by mixing) or successively. In this manner, the same or different silane compounds bound to both ends of the resin control the crosslinking density or coagulating degree of the resin upon curing.
  • Formula 10 is obtained by reacting an isocyanate-terminated prepolymer represented by Chemical Formula 20 with at least one sec-aminoalkyl silane compound rep- resented by Chemical Formula 30.
  • Reaction Scheme 10 illustrates one embodiment of the preparation of the room temperature moisture-curable resin.
  • B represents a substituent having a weight average molecular weight of 300-25,000 and is selected from the group consisting of reactions mixtures between an isocyanate compound and any one compound selected from polyether polyol, polyester polyol, polyurethane polyol, polyoxyalkylene polyol, organosiloxane compound and a combination thereof;
  • R 10 represents a linear or branched (C 1 -C4)alkyl
  • Y represents a linear or branched (C 1 -C6)alkylene
  • Y' and Y represent substituents derived from Y, and are identical or different;
  • Z represents a linear (Cl-C4)alkyl or phenyl derivative
  • Z' and Z represent substituents derived from Z, and are identical or different;
  • T represents a linear or branched (Cl-C ⁇ )alkyl
  • T' and T represent substituents derived from T, and are identical or different;
  • o, p and q independently represent an integer selected from 0 to 3, and p+q represents an integer from 0 to 6.
  • the isocyanate-terminated prepolymer useful for preparing the room temperature moisture-curable resin disclosed herein is represented by Chemical Formula 20:
  • the backbone, prepolymer B represents a substituent selected from the group consisting of reactions mixtures between an isocyanate compound and any one compound selected from polyether polyol, polyester polyol, polyurethane polyol, poly- oxyalkylene polyol, organosiloxane compound and a combination thereof. Additionally, B may have a weight average molecular weight of 300-25,000, specifically 500-20,000. If the resin has a molecular weight less than 300, it has poor physical properties. On the other hand, if the resin has a molecular weight greater than 25,000, it has poor processability.
  • the isocyanate-terminated prepolymer may be prepared by a reaction between a polyol and a polyisocyanate.
  • the isocyanate component when preparing the isocyanate-terminated polyurethane prepolymer, is used in an equivalently excessive amount as compared to the polyol reactant component so that the resultant prepolymer is end-capped with isocyanate groups.
  • the molar ratio (NCO/OH) of isocyanate groups to hydroxyl groups may be 1.1-3.0, more particularly 1.3-2.0.
  • the prepolymer When the NCO/OH equivalent ratio is less than 1.1, the prepolymer may have an excessively high molecular weight or the prepolymer may not be isocyanate-terminated. On the other hand, when the NCO/OH equivalent ratio is greater than 3.0, the viscosity of prepolymer may be too high to provide good workability.
  • a catalyst may be used depending on reactivity of each reactant, and the reaction may be carried out at 60-90 0 C for 2-6 hours.
  • the isocyanate compounds that may be used to prepare the isocyanate-terminated prepolymer include diisocyanates or polyisocyanates component, which may be aromatic diisocyanates, aliphatic diisocyanates, cycloaliphatic diisocyanate, etc.
  • polyisocyanates include monomers, such as 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 4,4-diphenylmethane diisocyanate, isophorone diisocyanate, dicyclohexylmethane-4,4-diisocyanate, meta-tetramethylxylene diisocyanate, trimethylhexamethylene diisocyanate or hexamethylene diisocyanate and polymers and combinations thereof.
  • monomers such as 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 4,4-diphenylmethane diisocyanate, isophorone diisocyanate, dicyclohexylmethane-4,4-diisocyanate, meta-tetramethylxylene diisocyanate, trimethylhexamethylene diisocyanate or hexamethylene diisocyanate and polymers and combinations thereof
  • the polyisocyanates may include monomers, such as 2,4-toluene diisocyanate (2,4-TDI), 2,6-toluene diisocyanate (2,6-TDI), 4,4-diphenylmethane diisocyanate (MDI), isophorone diisocyanate (IPDI), meta-tetramethylxylene diisocyanate (TMXDI), dicyclo- hexylmethane-4,4-diisocyanate (H12-MDI), trimethylhexamethylene diisocyanate (TMDI), or hexamethylene diisocyanate (HDI).
  • monomers such as 2,4-toluene diisocyanate (2,4-TDI), 2,6-toluene diisocyanate (2,6-TDI), 4,4-diphenylmethane diisocyanate (MDI), isophorone diisocyanate (IPDI), meta-tetramethylxylene
  • the polyols that may be used to prepare the polyurethane prepolymer disclosed herein may include polyols having one, two or more hydroxyl groups, selected from the group consisting of polyether polyols, polyester polyols, polybutadiene diols, poly oxy alky lene diols, poly oxy alky lene triols, polytetraethylene glycol, polycaprolactone diols, polycaprolactone triols and combinations thereof. More particularly, the polyols that may be used herein includes polyether polyols, poly- oxy alky lene diols or poly oxy alky lene triols.
  • the poly oxy alky lene includes polyoxyethylene, polyoxypropylene or polyoxybutylene.
  • the polyol may have a weight average molecular weight of 300-25,000, particularly 500-20,000.
  • the polyol has a weight average molecular weight less than 300, an increased amount of hard segments is used for the preparation of a high- molecular weight polyurethane prepolymer, resulting in production of a gel-like polymer having an excessively high viscosity and degradation of the processability thereof.
  • the preparation of polyol polymer is not cost-efficient and is commercially unacceptable.
  • Chemical formula 30 depicts sec-aminoalkylsilane compounds bound to the isocyanate-terminated prepolymer:
  • R 10 represents a linear or branched (Cl-C4)alkyl, particularly methyl or ethyl;
  • Y represents a linear or branched (Cl-C ⁇ )alkylene, particularly propylene, methyl- propylene or dime thy lbuty lene;
  • Z represents a linear (Cl-C4)alkyl or phenyl, particularly methyl, ethyl, propyl, butyl or phenyl;
  • T represents a linear or branched (Cl-C ⁇ )alkyl, particularly methyl, ethyl, propyl, butyl, and more particularly methyl;
  • the silane compounds that may be used herein includes at least one silane compound selected from silane compounds having three hydrolyzable groups, silane compounds having two hydrolyzable groups, silane compounds having one hydrolyzable groups and silane compounds having no hydrolyzable groups.
  • the silane compounds are introduced simultaneously or successively to the isocyanate-terminated prepolymer and are allowed to react with the prepolymer, wherein the total silane equivalent is in excess of the isocyanate equivalents of the prepolymer by 2-10%. That is, the total silane equivalents are 102-110 equivalents based on 100 equivalents of the isocyanate groups of the isocyanate-terminated prepolymer. In this manner, it is possible to obtain a uniform room temperature moisture-curable hybrid resin with various grades tailored for particular use.
  • the room temperature moisture-curable hybrid resin may have a controlled viscosity, elongation, elasticity, strength, modulus (low/middle/high modulus) depending on the mixing ratio and types of the silane compounds used therein, so that it may be used as a binder for sealants, sealing agents, adhesives, gluing agents, coating agents, or the like.
  • sec-aminoalkyl silane compounds having various hydrolyzable groups include: N- methyl-3-amino-2-methylpropyltrimethoxysilane, N- ethyl-3-amino-2-methylpropyltrimethoxysilane, N- ethyl-3-amino-2-methylpropyldiethoxymethylsilane, N- ethyl-3-amino-2-methylpropyltriethoxysilane, N- ethyl-3-amino-2-methylpropylmethyldimethoxysilane, N- butyl-3-amino-2-methylpropyltrimethoxysilane, 3-(N-methyl-2-amino-l-methyl-l-ethoxy)-propyltrimethoxysilane, N- ethyl-4-amino-3,3-dimethylbutyldimethoxymethylsilane, N- ethyl-4-amino-3,3-di
  • the room temperature moisture-curable hybrid resin disclosed herein may be obtained by reacting the isocyanate-terminated prepolymer prepared as described above with at least one of the above-listed sec-aminoalkyl silane compounds simultaneously (by mixing) or continuously in such a manner that the total silane equivalents are in excess of the isocyanate equivalents by about 2% -10%.
  • the reaction is carried out under atmospheric pressure in a moisture-free condition. Particularly, a moisture-free condition is required for preventing the hydrolysis of the hydrolyzable silane compounds.
  • the reaction may be performed at a temperature of 60-90 0 C for 2-6 hours.
  • the reaction may be performed in the presence of a catalyst but the catalyst may be introduced in a minimized amount depending on the progress of the reaction.
  • reaction completion may be analyzed by standard titration (ASTM 2572-87) or infrared analysis (FT-IR). The reaction may be completed when any residual NCO groups are not monitored or the NCO content reaches 0.8% or lower.
  • the room temperature moisture-curable polymer resins obtained after the reaction of the isocyanate-terminated prepolymer prepared as described above with the sec- aminoalkylsilane compounds, may be classified into the following 10 types of resins depending on the number of hydrolyzable groups bound to the ends of the resins, but are not limited thereto.
  • the room temperature moisture-curable hybrid resins disclosed herein may include resins both ends of which are the same silane compound, or resins both ends of which are different silanes.
  • the resins both ends of which are different silanes include a resin, one hydrolyzable group of which is methoxysilane and the other hy- drolyzable group of which is ethoxysilane.
  • the ten types of resins may be mixed in a suitable ratio depending on the particular types of silanes and proportions thereof. In this manner, the cured resin may have a controlled crosslinking density.
  • starting materials of the sealant may include a filler, a plasticizer, a thixotropic agent, an anti-sagging agent, an adhesion promoter, a water scavenger, a stabilizer and a curing catalyst.
  • the filler that may be used herein includes fumed silica, precipitated silica, treated calcium carbonate with a size of 0.07-4 ⁇ m and reinforced carbon black (for improving the physical properties).
  • the filler is used in a completely dried form containing no moisture.
  • the filler may be used in an amount of 50-250 parts by weight based on 100 parts by weight of the resin. When the filler is used in an amount less than 50 parts by weight, it is not possible to sufficiently improve the physical properties. When the filler is used in an amount greater than 250 parts by weight, the resin has poor pro- cessability.
  • the plasticizer that may be used herein includes dioctyl phthalate (DOP), diisodecyl phthalate (DIDP), benzoflex type plasticizer, etc.
  • the plasticizer may be used in an amount of 50-100 parts by weight based on 100 parts by weight of the resin.
  • the thixotropic agent or anti-sagging agent that may be used herein includes castor wax, fumed silica, treated clay, polyamides, etc.
  • the thixotrophic agent or anti-sagging agent may be used in an amount of 1-10 parts by weight based on 100 parts by weight of the resin.
  • silane compounds may be used as the adhesion promoter or water scavenger.
  • the adhesion promoter that may be used herein includes N- aminoethyl-aminopropyltrimethoxysilane or N- aminoethyl-aminopropylmethyldimethoxysilane.
  • the water scavenger that may be used herein includes vinyltrimethoxysilane.
  • the adhesion promoter or water scavenger may be used in an amount of 0.5-5 parts by weight based on 100 parts by weight of the resin, depending on the work condition and particular use.
  • the stabilizer 0-10 parts by weight, particularly 0-7 parts by weight, and more particularly 0-5 parts by weight of phenyltrimethoxysilane may be introduced to 100 parts by weight of the room temperature moisture-curable resin.
  • the stabilizer decreases the viscosity of the resin, resulting in improvement in workability, improves the storage stability of the resin, provides excellent elongation and thermal stability through the formation of a flexible network in a cured polymer, improves the storage stability of a sealant by functioning as a water scavenger, and allows control of the curing rate.
  • the stabilizer may be added preliminarily to the moisture-curable resin or may be introduced upon the preparation of a sealant.
  • the curing catalyst 0.01-10 parts by weight of dibutyltin acetate, stannous octoate, dibutyltin dilaurate, etc. may be used and introduced based on 100 parts by weight of the resin.
  • the curing catalyst is used in an amount less than 0.01 parts by weight, the resin may be cured too slowly.
  • the curing catalyst is used in an amount greater than 10 parts by weight, excessive curing may occur, resulting in degradation of the storage stability.
  • antioxidants and UV stabilizers such as titanium dioxide (TiO 2 ) may be used depending on particular use.
  • additives that may be used herein are not limited thereto.
  • the antioxidants or UV stabilizers may be used in an amount of 0.2-3 parts by weight based on 100 parts by weight of the resin so as to improve the durability and weather resistance of the sealant.
  • the plasticizer is introduced into an agitator and the filler is introduced thereto under agitation, and the materials are mixed uniformly.
  • the stabilizer and the room temperature moisture-curable resin are introduced thereto, the temperature is controlled to 8O 0 C, and the mixture is agitated vigorously under vacuum for 60-90 minutes. Then, the mixture is cooled to 5O 0 C, the adhesion promoter, water scavenger or dehydrating agent, curing catalyst and other additives are added thereto and the resultant mixture is agitated vigorously for about 30 minutes.
  • N 2 is introduced at any time to prevent the reaction mixture from being in contact with moisture.
  • the room temperature moisture-curable hybrid resin disclosed herein has easily controllable viscosity and good workability.
  • the hybrid resin may be provided with a wide spectrum of mechanical and physical properties, including different ranges of elongation and increased elasticity of a cured resin.
  • the room temperature moisture-curable hybrid resin disclosed herein has easily controllable crosslinking density and physical properties by blending various types of resins, including resins both ends of which are the same or different functional groups.
  • the room temperature moisture-curable hybrid resin is obtained by a simple process that allows easy introduction of various silane groups.
  • the room temperature moisture-curable hybrid resin may be tailored for its particular use, when applied to sealants, adhesives, gluing agents, coating agents, etc. Mode for the Invention
  • the room temperature moisture-curable resin was a blend of a resin including the polyurethane prepolymer, both ends of which were end-capped with trimethoxysilane, a resin including the polyurethane prepolymer, both ends of which were end-capped with dimethoxysilane, and a resin including the polyurethane prepolymer, one end of which was end-capped with trimethoxysilane and the other end of which was end-capped with dimethoxysilane.
  • Example 1 Then, H g of isocyanatopropyl trimethoxysilane was gradually added thereto to react with the polyurethane prepolymer in the same manner as described in Example 1.
  • a polyurethane prepolymer was obtained in the same manner as described in Example 1. Then, 5.5 g of isocyanatopropyl trimethoxysilane, 2.8 g of isocyanatopropyl methyldimethoxysilane, 1.48 g of isocyanatopropyl dimethyl- methoxysilane, and 0.9 g of isocyanatopropyl trimethylsilane were mixed and added drop wise to the polyurethane prepolymer to perform a reaction in the same manner as described in Example 1.
  • the blend included: a resin, both ends of which were end-capped with hydrolyzable trifunctional silanes; a resin, one end of which was end-capped with a hydrolyzable trifunctional silane and the other end of which was end-capped with a hydrolyzable difunctional silane; a resin, one end of which was end-capped with a hydrolyzable trifunctional silane and the other end of which was end-capped with a hydrolyzable monofunctional silane; a resin, one end of which was end-capped with a hydrolyzable trifunctional silane and the other end of which was end-capped with a non- hydrolyzable silane; a resin, both ends of which were end-capped with hydrolyzable difunctional silanes; a resin, one end of which was end-capped with a hydrolyzable difunctional silane and the other end of which was end-capped with a hydrolyzable monofunctional silane; a resin, one end of which was end-capped with a hydrolyzable monofunctional silane;
  • the resin blend included: a resin, both ends of which were end-capped with isocyanatopropyl dimethoxymethylsilane; a resin, one end of which was end-capped with isocyanatopropyl dimethoxylmethylsilane and the other end of which was end-capped with isocyanatomethyl dimethoxymethylsilane; and a resin, both ends of which were end-capped with isocyanatomethyl dimethoxymethylsilane.
  • the films of Examples 1-4 have various properties including controlled elongation properties, and thus may be tailored for various uses.
  • Example 13 [288] 3 phr of phenyltrimethoxysilane (PTMS) was mixed with Polymer-2 as described in Example 2, and a sealant was prepared according to the formulation as shown in Table 3. Then, the sealant was characterized and the results were shown in Table 4.
  • PTMS phenyltrimethoxysilane
  • VTMS * vinyltrimethoxysilane
  • DAS ** N-aminoethyl-aminopropyl trimethoxysilane [293] [Table 4] [294]
  • ASTM D 2572 test method was used as a titration method for determining the free NCO%.
  • the room temperature moisture-curable resin was a blend of a resin including the polyurethane prepolymer, both ends of which were end-capped with trimethoxysilane, a resin including the polyurethane prepolymer, both ends of which were end-capped with dimethoxysilane, and a resin including the polyurethane prepolymer, one end of which was end-capped with trimethoxysilane and the other end of which was end-capped with dimethoxysilane.
  • a prepolymer was obtained in the same manner as described in Example 14. Then, 17 g of N-phenyl-gamma-aminopropyltrimethoxysilane, 8 g of N- butylaminopropylmethyldimethoxysilane, 4 g of N- phenyl-amniopropyldimethylmethoxy silane and 4 g of N- butyl-gamma-aminopropyltrimethylsilane were mixed and added dropwise to the prepolymer to perform a reaction in the same manner as described in Example 14.
  • the blend included: a resin, both ends of which were end-capped with hydrolyzable trifunctional silanes; a resin, one end of which was end-capped with a hydrolyzable trifunctional silane and the other end of which was end-capped with a hydrolyzable difunctional silane; a resin, one end of which was end-capped with a hydrolyzable trifunctional silane and the other end of which was end-capped with a hydrolyzable monofunctional silane; a resin, one end of which was end-capped with a hydrolyzable trifunctional silane and the other end of which was end-capped with a non- hydrolyzable silane; a resin, both ends of which were end-capped with hydrolyzable difunctional silanes; a resin, one end of which was end-capped with a hydrolyzable di- functional silane and the other end of which was end-capped with a hydrolyzable monofunctional silane; a resin, one end of which was end-capped with a hydrolyzable monofunctional silane
  • Example 20 [317] 3 phr of phenyltrimethoxysilane (PTMS) was mixed with Polymer-20 as described in Example 15, and a sealant was prepared according to the formulation as shown in Table 5. Then, the sealant was characterized and the results were shown in Table 6.
  • PTMS phenyltrimethoxysilane

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Abstract

La présente invention concerne une résine hybride durcissable par l’humidité à température ambiante, un procédé de préparation de celle-ci et l’application de celle-ci. Plus particulièrement, la présente invention concerne une résine hybride durcissable par l’humidité à température ambiante obtenue par réaction d’un prépolymère à terminaison hydroxy ou un polyéther polyol ayant un poids moléculaire moyen en poids de 8 000 à 60 000 avec un composé isocyanatoalkylsilane, une résine hybride durcissable par l’humidité à température ambiante obtenue par réaction d’un prépolymère à terminaison isocyanate avec un composé sec-aminosilane, et des procédés de préparation de celles-ci. La résine hybride durcissable par l’humidité à température ambiante a une viscosité aisément contrôlable pour produire une bonne aptitude au traitement, produit une résine polymère ayant une large plage de caractéristiques de module et d'allongement dérivées de celle-ci, et peut être produite avec un large spectre de propriétés mécaniques et physiques comprenant une élasticité augmentée d’une résine durcie. Par conséquent, la résine hybride durcissable par l’humidité à température ambiante peut être appliquée à des étanchéifiants, des adhésifs, des liants, des agents d’enduction, etc., pour utilisation dans divers domaines industriels comprenant les industries de construction, électrique/électronique et automobile.
PCT/KR2009/003754 2008-07-15 2009-07-09 Résine hybride durcissable par l’humidité à température ambiante, procédé de préparation de celle-ci et application de celle-ci WO2010008154A2 (fr)

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101880372A (zh) * 2010-06-25 2010-11-10 广东新劲刚超硬材料有限公司 一种活性预聚体、其制备方法、及含有该活性预聚体的聚脲胶粘剂和环氧树脂胶粘剂
WO2011110384A1 (fr) * 2010-03-12 2011-09-15 Henkel Ag & Co. Kgaa Colle pour carreaux à base de polymères modifiés par un silane
WO2012022494A1 (fr) * 2010-08-20 2012-02-23 Stauf Klebstoffwerk Gmbh Colle à parquet à un composant, modifiée au silane et exempte d'eau, de solvant et de phtalate, et utilisation de celle-ci pour coller de manière extrêmement stable du parquet, des revêtements de sol en bois et des panneaux à base de bois dans le cadre d'un aménagement intérieur
WO2012022493A3 (fr) * 2010-08-20 2012-04-19 Stauf Klebstoffwerk Gmbh Colle à parquet à un composant, modifiée au silane et exempte d'eau, de solvant et de plastifiant, et utilisation de celle-ci pour coller du parquet, des revêtements de sol en bois et des panneaux à base de bois, avec toutes sortes de supports courants en aménagement intérieur, même problématiques
CN102911633A (zh) * 2012-10-18 2013-02-06 四川大学 支化结构聚氨酯-含硅聚丙烯酸酯热熔胶及其制备方法
FR2982157A1 (fr) * 2011-11-09 2013-05-10 Oreal Composition cosmetique ou dermatologique comprenant un alpha-alcoxysilane a base uree ou amide
WO2013079344A1 (fr) * 2011-12-01 2013-06-06 Wacker Chemie Ag Substances réticulables sur la base de polyuréthanes à terminaison organyloxysilane
CN104086784A (zh) * 2014-06-27 2014-10-08 华南理工大学 一种自乳化改性有机硅树脂乳液及其制备方法与应用
EP3216813A1 (fr) * 2016-03-10 2017-09-13 Evonik Degussa GmbH Utilisation de n-(n-butyl)-3-aminopropylmethydialkoxysilane en polymère de polyuréthane terminé par silane pour masses collantes élastiques et masses d'étanchélité élastiques
EP3149095B1 (fr) 2014-05-30 2018-02-28 Wacker Chemie AG Matières réticulables à base de polymères à terminaison organyloxysilane
CN112142945A (zh) * 2019-06-27 2020-12-29 万华化学集团股份有限公司 一种高稳定性的端硅烷基聚合物树脂及其制备方法
IT201900022356A1 (it) * 2019-11-28 2021-05-28 Dow Global Technologies Llc Composizione adesiva
CN113603849A (zh) * 2021-08-05 2021-11-05 常州大学 一种可室温湿固化硅烷封端聚氨酯-g-聚丙烯酸酯接枝共聚物及其制备方法
TWI874470B (zh) 2019-11-28 2025-03-01 美商陶氏全球科技有限責任公司 黏著劑組合物

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6602964B2 (en) * 1998-04-17 2003-08-05 Crompton Corporation Reactive diluent in moisture curable system
US6197912B1 (en) * 1999-08-20 2001-03-06 Ck Witco Corporation Silane endcapped moisture curable compositions
US6635341B1 (en) * 2000-07-31 2003-10-21 Ppg Industries Ohio, Inc. Coating compositions comprising silyl blocked components, coating, coated substrates and methods related thereto
DE102005051921A1 (de) * 2005-10-29 2007-05-03 Henkel Kgaa α-Ethoxysilan modifizierte Polymere, deren Herstellung und Verwendung
CN101341216B (zh) * 2005-12-02 2012-06-13 迈图高新材料日本合同公司 室温固化性的含硅基聚合物组合物

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011110384A1 (fr) * 2010-03-12 2011-09-15 Henkel Ag & Co. Kgaa Colle pour carreaux à base de polymères modifiés par un silane
CN101880372A (zh) * 2010-06-25 2010-11-10 广东新劲刚超硬材料有限公司 一种活性预聚体、其制备方法、及含有该活性预聚体的聚脲胶粘剂和环氧树脂胶粘剂
CN101880372B (zh) * 2010-06-25 2013-02-13 广东新劲刚超硬材料有限公司 一种活性预聚体、其制备方法、及含有该活性预聚体的聚脲胶粘剂和环氧树脂胶粘剂
US8614269B2 (en) 2010-08-20 2013-12-24 Stauf Klebstoffwerk Gmbh Water-, solvent- and plasticizer-free, silane-modified, one-component parquet adhesive and use thereof for gluing parquet, wooden floor coverings and wood-based material boards to all sub-floors which are common in interior fitment, even those which are problematic
WO2012022494A1 (fr) * 2010-08-20 2012-02-23 Stauf Klebstoffwerk Gmbh Colle à parquet à un composant, modifiée au silane et exempte d'eau, de solvant et de phtalate, et utilisation de celle-ci pour coller de manière extrêmement stable du parquet, des revêtements de sol en bois et des panneaux à base de bois dans le cadre d'un aménagement intérieur
WO2012022493A3 (fr) * 2010-08-20 2012-04-19 Stauf Klebstoffwerk Gmbh Colle à parquet à un composant, modifiée au silane et exempte d'eau, de solvant et de plastifiant, et utilisation de celle-ci pour coller du parquet, des revêtements de sol en bois et des panneaux à base de bois, avec toutes sortes de supports courants en aménagement intérieur, même problématiques
US9622954B2 (en) 2011-11-09 2017-04-18 L'oreal Cosmetic composition comprising an urea or amide based alpha-alkoxysilane
WO2013068966A3 (fr) * 2011-11-09 2013-11-21 L'oreal Composition comprenant un apha-alcoxysilane à base urée ou amide
FR2982157A1 (fr) * 2011-11-09 2013-05-10 Oreal Composition cosmetique ou dermatologique comprenant un alpha-alcoxysilane a base uree ou amide
WO2013079344A1 (fr) * 2011-12-01 2013-06-06 Wacker Chemie Ag Substances réticulables sur la base de polyuréthanes à terminaison organyloxysilane
CN102911633A (zh) * 2012-10-18 2013-02-06 四川大学 支化结构聚氨酯-含硅聚丙烯酸酯热熔胶及其制备方法
EP3149095B1 (fr) 2014-05-30 2018-02-28 Wacker Chemie AG Matières réticulables à base de polymères à terminaison organyloxysilane
CN104086784A (zh) * 2014-06-27 2014-10-08 华南理工大学 一种自乳化改性有机硅树脂乳液及其制备方法与应用
CN104086784B (zh) * 2014-06-27 2016-05-04 华南理工大学 一种自乳化改性有机硅树脂乳液及其制备方法与应用
EP3216813A1 (fr) * 2016-03-10 2017-09-13 Evonik Degussa GmbH Utilisation de n-(n-butyl)-3-aminopropylmethydialkoxysilane en polymère de polyuréthane terminé par silane pour masses collantes élastiques et masses d'étanchélité élastiques
CN112142945A (zh) * 2019-06-27 2020-12-29 万华化学集团股份有限公司 一种高稳定性的端硅烷基聚合物树脂及其制备方法
CN112142945B (zh) * 2019-06-27 2022-07-12 万华化学集团股份有限公司 一种高稳定性的端硅烷基聚合物树脂及其制备方法
IT201900022356A1 (it) * 2019-11-28 2021-05-28 Dow Global Technologies Llc Composizione adesiva
WO2021108097A1 (fr) * 2019-11-28 2021-06-03 Dow Global Technologies Llc Composition adhésive
CN114641514A (zh) * 2019-11-28 2022-06-17 陶氏环球技术有限责任公司 粘合剂组合物
CN114641514B (zh) * 2019-11-28 2024-06-14 陶氏环球技术有限责任公司 粘合剂组合物
JP7629918B2 (ja) 2019-11-28 2025-02-14 ダウ グローバル テクノロジーズ エルエルシー 接着剤組成物
TWI874470B (zh) 2019-11-28 2025-03-01 美商陶氏全球科技有限責任公司 黏著劑組合物
CN113603849A (zh) * 2021-08-05 2021-11-05 常州大学 一种可室温湿固化硅烷封端聚氨酯-g-聚丙烯酸酯接枝共聚物及其制备方法
CN113603849B (zh) * 2021-08-05 2022-06-14 常州大学 一种可室温湿固化硅烷封端聚氨酯-g-聚丙烯酸酯接枝共聚物及其制备方法

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