CN105061714A - Synthetic method and application of silicon alkane terminated polyurethane prepolymer - Google Patents
Synthetic method and application of silicon alkane terminated polyurethane prepolymer Download PDFInfo
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- CN105061714A CN105061714A CN201510481187.6A CN201510481187A CN105061714A CN 105061714 A CN105061714 A CN 105061714A CN 201510481187 A CN201510481187 A CN 201510481187A CN 105061714 A CN105061714 A CN 105061714A
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- 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
- C08G18/4825—Polyethers containing two hydroxy groups
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- 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
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- 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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3893—Low-molecular-weight compounds having heteroatoms other than oxygen containing silicon
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- 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
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/6696—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/36 or hydroxylated esters of higher fatty acids of C08G18/38
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- 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
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention relates to a snthetic method and application of a silicon alkane terminated polyurethane prepolymer. The synthetic method comprises the steps of: firstly enabling diphenyl methane diisocyanate to react with polyether diol so as to generate a NCO-terminated reactant, then, enabling the NCO-terminated reactant to perform a polyreaction with bis-(- ( 3- methoxyl group silicon propyl ) amine or bis-[- 3-(triethoxysily propyl)]amine, after polyreaction, dropwise adding an appropriate amount of N- n-butyl -3- aminopropyl-trimethoxysilane to enable the un-completely-terminaed NCO functional groups to be totally terminated, and adjusting the consistency so as to obtain the silicon alkane terminated polyurethane prepolymer. The prepolymer can be widely applied in an adhesive formula, can obviously improve the ageing resistance of an adhesive and improve the interface adhesivity.
Description
Technical field
The present invention relates to a kind of synthetic method and application of silane end capped polyurethane prepolymer.
Background technology
In recent years, silane end capped polyurethane utilisation technology is more and more extensive.Common technological line is first with polyethers or polyester diol and di-isocyanate reaction, obtains isocyanate terminated base polyurethane prepolymer, then reacts with the Siloxysilane with active hydrogen, obtain Silante terminated polyurethane prepolymer.The prepolymer obtained based on this kind of synthetic method is linear oligomer, opposite end NCO base enclosed is incomplete, the functionalityization of silane is relatively low, be applied to the raw material title complex of tackiness agent, one is the bonding force that cannot be designed effectively in advance, and two is that package stability and weathering resistance also cannot effectively improve.
Summary of the invention
Incomplete in order to solve opposite end NCO base enclosed in prior art, the situation that alkoxy functionality is lower, the problem of bonding force difference, the invention provides a kind of Silante terminated urethane oligomer, alkoxy functionality can reach 8-10, this prepolymer can be widely used in adhesive formulation, obviously can increase the package stability of tackiness agent and improve interface cohesive force.
The technical scheme that the present invention solves the problems of the technologies described above is as follows:
First make molecular weight be 2000 polyether Glycols and diphenylmethanediisocyanate (MDI-100) carry out polyreaction, reaction generates end NCO base polyurethane prepolymer, and NCO content controls as 10-15%;
Then reactant is carried out polyreaction with two-(3-methoxyl group silicon propyl group) amine or two-(3-oxyethyl group silicon propyl group) amine again, by calculating design, NCO enclosed is made to control about 90%, obtain the mixture of cross-linking type end NCO oligopolymer and part end NCO prepolymer, NCO content controls at 3-4%;
After having reacted, drip N-normal-butyl-3-aminopropyl trimethoxysilane, by the whole end-blocking of NCO functional group of not complete totally enclosed 3-4% surplus, and adjust viscosity simultaneously, obtain a Silante terminated polyurethane prepolymer.
Synthetic technology condition concrete is further as follows:
The first step, by load weighted molecular weight be 2000 polyether Glycols (the commercially available trade mark is D2120, hydroxyl value 56) put into there-necked flask, vacuum hydro-extraction 2 ~ 3h at 120 ± 5 DEG C, then less than 60 DEG C are cooled to, gradation adds the diphenylmethanediisocyanate (MDI-100) measured, and controls temperature of reaction 80 ± 5 DEG C, reaction 2h;
Second step, less than 60 DEG C are cooled to after the first step completes, start to drip two [3-(trimethoxy silicon) propyl group] amine (the commercially available trade mark is Dynasylan1124) or two [3-(triethoxysilicane) propyl group] amine (the commercially available trade mark is Dynasylan1122) with dropping funnel, it is per second that rate of addition is that 1-2 drips, and controlling temperature of reaction is 80 ± 5 DEG C, until after being added dropwise to complete, continue reaction 2h, after having reacted, cooling, inflated with nitrogen is protected;
3rd step, after second step has reacted, start to drip N-normal-butyl-3-aminopropyl trimethoxysilane (the commercially available trade mark is Dynasylan1189) with dropping funnel, it is per second that rate of addition is that 1-2 drips, controlling temperature of reaction is 80 ± 5 DEG C, until after being added dropwise to complete, continues reaction 2h, after having reacted, obtain tackiness agent prepolymer.
The invention still further relates to this silane end capped polyurethane prepolymer in tackiness agent and the application in polyurethane hot melt.
Compared with prior art, in prepolymer prepared by the present invention, viscoelastic state is in use temperature district as the polysiloxane segment of soft section and polyether segment, and hard section such as carbamate groups, urea groups are in vitreous state or crystal form, the existence of soft section makes material have good elasticity, hard section part makes the strength of materials increase as physical crosslinking point, prepolymer of the present invention is used to make reactive polyurethane hot melt, except not producing except bubble, also can reduce the surface energy of polarity adhesive for polyurethane, realize the infiltration of low polar material bonding.
Embodiment
Embodiment 1:
(the commercially available trade mark is D2120 to weigh polyether Glycols, hydroxyl value 56) 132 grams put in there-necked flask, vacuum hydro-extraction 2.5h at 120 ± 5 DEG C, then less than 60 DEG C are cooled to, gradation adds the diphenylmethanediisocyanate (MDI-100) 100 grams measured, control temperature of reaction 80 ± 5 DEG C, reaction 2h;
50 DEG C are cooled to after the time, start to drip two [3-(triethoxysilicane) propyl group] amine (the commercially available trade mark is Dynasylan1122) 188 grams with dropping funnel, it is per second that rate of addition is that 1-2 drips, after being added dropwise to complete, controlling temperature of reaction is 80 ± 5 DEG C, continues reaction 2h, after having reacted, cooling, inflated with nitrogen is protected; After having reacted, cooling, inflated with nitrogen is protected;
Start to drip N-normal-butyl-3-aminopropyl trimethoxysilane (the commercially available trade mark is Dynasylan1189) 100 grams with dropping funnel, rate of addition be 2 per second, control temperature of reaction be 80 ± 5 DEG C, until after being added dropwise to complete, continue reaction 2h, after having reacted, obtain tackiness agent prepolymer.
Embodiment 2:
(the commercially available trade mark is D2120 to weigh polyether Glycols, hydroxyl value 56) 132 grams put in there-necked flask, vacuum hydro-extraction 2.5h at 120 ± 5 DEG C, then less than 60 DEG C are cooled to, gradation adds the diphenylmethanediisocyanate (MDI-100) 100 grams measured, control temperature of reaction 80 ± 5 DEG C, reaction 2h;
50 DEG C are cooled to after the time, start to drip two [3-(trimethoxy silicon) propyl group] amine (the commercially available trade mark is Dynasylan1124) 150 grams with dropping funnel, it is per second that rate of addition is that 1-2 drips, after being added dropwise to complete, controlling temperature of reaction is 80 ± 5 DEG C, continues reaction 2h, after having reacted, cooling, inflated with nitrogen is protected; After having reacted, cooling, inflated with nitrogen is protected;
Start to drip N-normal-butyl-3-aminopropyl trimethoxysilane (the commercially available trade mark is Dynasylan1189) 90 grams with dropping funnel, rate of addition be 2 per second, control temperature of reaction be 80 ± 5 DEG C, until after being added dropwise to complete, continue reaction 2h, after having reacted, obtain tackiness agent prepolymer.
Embodiment 3: performed polymer is applied to tackiness agent.
By the prepolymer 350 parts of the embodiment of the present invention 1, hydrophobicity gas-phase silicon 39 parts, dibutyl tin laurate 0.4 part, under anhydrous condition, pinch be mixed even, obtained a adhesion type tackiness agent.This tackiness agent self-vulcanizing is after 24 hours, and aluminium aluminium bonding strength can reach 5-6MPa, and self-vulcanizing is after 7 days, and aluminium aluminium bonding strength can reach more than 10MPa, shows excellent bonding force.This tackiness agent initial viscosity is 450Pa.s, and after in sealed vessel, room temperature deposits 21 days, viscosity is 460Pa.s, shows good storage stability.
Embodiment 4: performed polymer is applied to hot melt adhesive.
By PUR isocyanate prepolymer 100 parts, the prepolymer of the embodiment of the present invention 2 10 parts, tackifying resin 10 parts, two (2,2-morpholine ethyl) 0.05 part, ether, 2 parts, oxidation inhibitor, under nitrogen atmosphere, be heated to 80 degree and mix, obtained a PUR hot melt adhesive.Namely the bonding strength of this hot melt adhesive to PC can reach more than 8MPa in 24 hours, shows very excellent infiltration cementability.
Claims (4)
1. a synthetic method for silane end capped polyurethane prepolymer, comprises following steps:
1) first make molecular weight be 2000 polyether Glycols and diphenylmethanediisocyanate carry out polyreaction, reaction generates end NCO base polyurethane prepolymer, and NCO content controls as 10-15%;
2) then reactant is carried out polyreaction with two-(3-methoxyl group silicon propyl group) amine or two-(3-oxyethyl group silicon propyl group) amine again, by calculating design, NCO enclosed is made to control about 80%, obtain the mixture of cross-linking type end NCO oligopolymer and part end NCO prepolymer, NCO content controls at 3-4%;
3), after having reacted, drip N-normal-butyl-3-aminopropyl trimethoxysilane, by the whole end-blocking of NCO functional group of not complete totally enclosed 3-4% surplus, and adjust viscosity simultaneously, obtain a Silante terminated polyurethane prepolymer.
2. the synthetic method of a kind of silane end capped polyurethane prepolymer according to claim 1, is characterized in that:
The technical qualification of step 1) are: by load weighted molecular weight be 2000 polyether Glycols put into there-necked flask, vacuum hydro-extraction 2-3h at 120 ± 5 DEG C, is then cooled to less than 60 DEG C, and gradation adds the diphenylmethanediisocyanate measured, control temperature of reaction 80 ± 5 DEG C, reaction 2h;
Step 2) technical qualification be: be cooled to less than 60 DEG C after step 1) completes, start to drip two-(3-methoxyl group silicon propyl group) amine or two-(3-oxyethyl group silicon propyl group) amine with dropping funnel, it is per second that rate of addition is that 1-2 drips, controlling temperature of reaction is 80 ± 5 DEG C, until after being added dropwise to complete, continue reaction 2h, after having reacted, cooling, inflated with nitrogen is protected;
The technical qualification of step 3) are: step 2) reacted after, start to drip N-normal-butyl-3-aminopropyl trimethoxysilane with dropping funnel, it is per second that rate of addition is that 1-2 drips, controlling temperature of reaction is 80 ± 5 DEG C, until after being added dropwise to complete, continue reaction 2h, after having reacted, obtain tackiness agent prepolymer.
3. the synthetic method of a kind of silane end capped polyurethane prepolymer described in claim 1 or 2 prepares the application in tackiness agent.
4. the synthetic method of a kind of silane end capped polyurethane prepolymer described in claim 1 or 2 prepares the application in polyurethane hot melt.
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| CN201510481187.6A CN105061714B (en) | 2015-08-10 | 2015-08-10 | A kind of synthetic method of silane end capped polyurethane prepolymer and its application |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105542110A (en) * | 2016-01-06 | 2016-05-04 | 江门市长河化工实业集团有限公司 | Ms resin and preparation method thereof |
| CN107760245A (en) * | 2016-08-18 | 2018-03-06 | 摩田化学（昆山）有限公司 | The compound PUR Reactive hot melt adhesives and preparation method thereof of fabric |
| CN109666115A (en) * | 2017-10-16 | 2019-04-23 | 万华化学集团股份有限公司 | A kind of amino-silane terminated modified polyurethane resin and preparation method thereof |
| CN112029467A (en) * | 2020-09-16 | 2020-12-04 | 深圳市安伯斯科技有限公司 | High-transparency MS glue with pencil hardness reaching 3H and preparation method thereof |
| CN113025260A (en) * | 2021-02-25 | 2021-06-25 | 悦声纸业(中国)有限公司 | Preparation method of single-component thermosetting polyurethane adhesive |
| CN115850642A (en) * | 2022-12-05 | 2023-03-28 | 宁波聚泰新材料科技有限公司 | Preparation method of high-performance polyurethane elastomer |
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| CN101402845A (en) * | 2008-11-11 | 2009-04-08 | 北京市化学工业研究院 | Process for producing flame-proof fluid sealant for construction |
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| 姚晓宁: "SPU密封胶的制备及结构与力学性能关系的研究", 《中国优秀硕士学位论文全文数据库工程科技I辑》 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105542110A (en) * | 2016-01-06 | 2016-05-04 | 江门市长河化工实业集团有限公司 | Ms resin and preparation method thereof |
| CN107760245A (en) * | 2016-08-18 | 2018-03-06 | 摩田化学（昆山）有限公司 | The compound PUR Reactive hot melt adhesives and preparation method thereof of fabric |
| CN109666115A (en) * | 2017-10-16 | 2019-04-23 | 万华化学集团股份有限公司 | A kind of amino-silane terminated modified polyurethane resin and preparation method thereof |
| CN112029467A (en) * | 2020-09-16 | 2020-12-04 | 深圳市安伯斯科技有限公司 | High-transparency MS glue with pencil hardness reaching 3H and preparation method thereof |
| CN112029467B (en) * | 2020-09-16 | 2021-11-30 | 深圳市安伯斯科技有限公司 | High-transparency MS glue with pencil hardness reaching 3H and preparation method thereof |
| CN113025260A (en) * | 2021-02-25 | 2021-06-25 | 悦声纸业(中国)有限公司 | Preparation method of single-component thermosetting polyurethane adhesive |
| CN115850642A (en) * | 2022-12-05 | 2023-03-28 | 宁波聚泰新材料科技有限公司 | Preparation method of high-performance polyurethane elastomer |
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| CN105061714B (en) | 2017-09-26 |
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Address after: No.3-3, Kaifeng Road, Yantai Economic and Technological Development Zone, Shandong Province 264006 Patentee after: Yantai Debang Technology Co.,Ltd. Address before: No.98 Jinshajiang Road, Yantai Development Zone, Shandong Province 264006 Patentee before: DARBOND TECHNOLOGY Co.,Ltd. |
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