CN105061714B - A kind of synthetic method of silane end capped polyurethane prepolymer and its application - Google Patents

A kind of synthetic method of silane end capped polyurethane prepolymer and its application Download PDF

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CN105061714B
CN105061714B CN201510481187.6A CN201510481187A CN105061714B CN 105061714 B CN105061714 B CN 105061714B CN 201510481187 A CN201510481187 A CN 201510481187A CN 105061714 B CN105061714 B CN 105061714B
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reaction
nco
polyurethane prepolymer
synthetic method
completion
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CN105061714A (en
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许愿
王建斌
陈田安
解海华
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Yantai Darbond Technology Co Ltd
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Yantai Darbond Technology Co Ltd
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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
    • 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
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3893—Low-molecular-weight compounds having heteroatoms other than oxygen 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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 present invention relates to a kind of synthetic method of silane end capped polyurethane prepolymer and application.Synthetic method include methyl diphenylene diisocyanate first with polyether Glycols reaction generation end NCO base reactants, then again with it is double（3 methoxyl group silicon propyl group）Amine is double（3 ethyoxyl silicon propyl group）Amine carries out polymerisation, after the completion of reaction, the appropriate aminopropyl trimethoxysilane of N normal-butyls 3 is added dropwise all to block not completely enclosed NCO functional groups and adjust viscosity, obtain a Silante terminated polyurethane prepolymer, this prepolymer can be widely applied to adhesive formulation, can substantially increase the ageing resistace of adhesive and improve interface cohesive force.

Description

A kind of synthetic method of silane end capped polyurethane prepolymer and its application
Technical field
The present invention relates to a kind of synthetic method of silane end capped polyurethane prepolymer and application.
Background technology
In recent years, silane end capped polyurethane application technology is more and more extensive.Common technology path is first with polyethers or poly- Ester dihydric alcohol and di-isocyanate reaction, obtain isocyanate terminated base polyurethane prepolymer, then with the siloxy with reactive hydrogen Silane reaction, obtains Silante terminated polyurethane prepolymer.The prepolymer obtained based on such a synthetic method is linear oligomer, Opposite end NCO base encloseds are not complete, and the degree of functionalityization of silane is relatively low, are nothings applied to the raw material complex of adhesive, one The bonding force that method is effectively pre-designed, two be that bin stability and weatherability can not also effectively improve.
The content of the invention
For solve opposite end NCO bases enclosed in the prior art incomplete, the relatively low situation of alkoxy functionality, bonding force Poor the problem of, the invention provides a kind of Silante terminated urethane oligomer, alkoxy functionality is up to 8-10, this prepolymer Adhesive formulation is can be widely applied to, can substantially increase the bin stability of adhesive and improve interface cohesive force.
The technical scheme that the present invention solves above-mentioned technical problem is as follows：
First make polyether Glycols and methyl diphenylene diisocyanate that molecular weight is 2000（MDI-100）Progress polymerize instead Should, reaction generation end NCO base polyurethane prepolymers, NCO content control is 10-15%；
Then by reactant again with it is double-（3- methoxyl group silicon propyl group）Amine or double-（3- ethyoxyl silicon propyl group）Amine is polymerize Reaction, is designed by calculating so that NCO encloseds are controlled 90% or so, obtain cross-linking type end NCO oligomer and part end NCO The mixture of prepolymer, NCO content is controlled in 3-4%；
After the completion of reaction, N- normal-butyl -3- aminopropyl trimethoxysilanes are added dropwise, by not completely enclosed 3-4% surpluses NCO functional groups all block, and adjust viscosity simultaneously, obtain a Silante terminated polyurethane prepolymer.
Further specific synthetic technology condition is as follows：
The first step, by the polyether Glycols that load weighted molecular weight is 2000（The commercially available trade mark is D2120, hydroxyl value 56）It is put into In three-necked flask, then 2 ~ 3h of vacuum dehydration at 120 ± 5 DEG C is cooled to less than 60 DEG C, and the diphenyl measured is added by several times Methane diisocyanate（MDI-100）, 80 ± 5 DEG C of controlling reaction temperature, reaction 2h；
Less than 60 DEG C are cooled to after the completion of second step, the first step, is started that double [3- (trimethoxy silicon are added dropwise with dropping funel） Propyl group] amine（The commercially available trade mark is Dynasylan 1124）Or double [3- (triethoxysilicanes）Propyl group] amine（The commercially available trade mark is Dynasylan 1122）, rate of addition is that 1-2 drops are per second, and controlling reaction temperature is 80 ± 5 DEG C, until after being added dropwise to complete, continuing 2h is reacted, after the completion of reaction, cooling, nitrogen charging gas shielded；
3rd step, after the completion of second step reaction, is started that N- normal-butyl -3- aminopropyl trimethoxy silicon is added dropwise with dropping funel Alkane（The commercially available trade mark is Dynasylan 1189）, rate of addition is that 1-2 drops are per second, and controlling reaction temperature is 80 ± 5 DEG C, until drop Plus after the completion of, continue to react 2h, after the completion of reaction, obtain adhesive prepolymer.
The invention further relates to this silane end capped polyurethane prepolymer in adhesive and answering in polyurethane hot melt With.
Compared with prior art, in the prepolymer that prepared by the present invention, the polysiloxanes segment and polyether segment of soft segment are used as Viscoelastic state is in temperature in use area, and hard section such as carbamate groups, urea groups are in glassy state or crystalline state, the presence of soft segment Make material that there is good elasticity, hard section part increases the strength of materials as physical crosslinking point, uses the prepolymer of the present invention Reactive polyurethane hot melt is made, in addition to not producing bubble, can also reduce the surface energy of polarity adhesive for polyurethane, realize To the infiltration bonding of low polar material.
Embodiment
Embodiment 1：
Weigh polyether Glycols（The commercially available trade mark is D2120, hydroxyl value 56）132 grams are put into three-necked flask, 120 ± 5 Vacuum dehydration 2.5h at DEG C, is then cooled to less than 60 DEG C, and the methyl diphenylene diisocyanate measured is added by several times（MDI- 100）100 grams, 80 ± 5 DEG C of controlling reaction temperature reacts 2h；
50 DEG C are cooled to after to the time, is started that double [3- (triethoxysilicanes are added dropwise with dropping funel）Propyl group] amine（Commercially available board Number be Dynasylan 1122）188 grams, rate of addition is that 1-2 drops are per second, after being added dropwise to complete, and controlling reaction temperature is 80 ± 5 DEG C, continue to react 2h, after the completion of reaction, cooling, nitrogen charging gas shielded；After the completion of reaction, cooling, nitrogen charging gas shielded；
Started that N- normal-butyl -3- aminopropyl trimethoxysilanes are added dropwise with dropping funel（The commercially available trade mark is Dynasylan 1189）100 grams, rate of addition is that 2 drops are per second, and controlling reaction temperature is 80 ± 5 DEG C, until after being added dropwise to complete, continue to react 2h, After the completion of reaction, adhesive prepolymer is obtained.
Embodiment 2：
Weigh polyether Glycols（The commercially available trade mark is D2120, hydroxyl value 56）132 grams are put into three-necked flask, 120 ± 5 Vacuum dehydration 2.5h at DEG C, is then cooled to less than 60 DEG C, and the methyl diphenylene diisocyanate measured is added by several times（MDI- 100）100 grams, 80 ± 5 DEG C of controlling reaction temperature reacts 2h；
50 DEG C are cooled to after to the time, is started that double [3- (trimethoxy silicon are added dropwise with dropping funel）Propyl group] amine（Commercially available board Number be Dynasylan 1124）150 grams, rate of addition is that 1-2 drops are per second, after being added dropwise to complete, and controlling reaction temperature is 80 ± 5 DEG C, continue to react 2h, after the completion of reaction, cooling, nitrogen charging gas shielded；After the completion of reaction, cooling, nitrogen charging gas shielded；
Started that N- normal-butyl -3- aminopropyl trimethoxysilanes are added dropwise with dropping funel（The commercially available trade mark is Dynasylan 1189）90 grams, rate of addition is that 2 drops are per second, and controlling reaction temperature is 80 ± 5 DEG C, until after being added dropwise to complete, continue to react 2h, After the completion of reaction, adhesive prepolymer is obtained.
Embodiment 3：Performed polymer is applied to adhesive.
By 350 parts of the prepolymer of the embodiment of the present invention 1,39 parts of hydrophobicity gas-phase silicon, 0.4 part of dibutyl tin laurate, Under the conditions of anhydrous, even, the obtained a adhesion type adhesive that is mixed is pinched.After the adhesive cold curing 24 hours, aluminium aluminium glues Intensity is connect up to 5-6MPa, after cold curing 7 days, aluminium aluminium adhesive strength shows excellent bonding force up to more than 10MPa. The adhesive initial viscosity is 450Pa.s, and after room temperature is deposited 21 days in sealing container, viscosity is 460Pa.s, is shown good Bin stability.
Embodiment 4：Performed polymer is applied to PUR.
By 100 parts of isocyanate prepolymers of PUR, 10 parts of the prepolymer of the embodiment of the present invention 2,10 parts of tackifying resin is double (2,2- morpholine ethyl) 0.05 part of ether, 2 parts of antioxidant under nitrogen atmosphere, is heated to 80 degree and is well mixed, a PUR is made PUR.The PUR can reach more than 8MPa in 24 hours to PC adhesive strength, show very excellent infiltration and glue Connect ability.

Claims (4)

1. a kind of synthetic method of silane end capped polyurethane prepolymer, is comprised the following steps：
1）The polyether Glycols that molecular weight is 2000 are first made to carry out polymerisation, reaction life with methyl diphenylene diisocyanate Into end NCO base polyurethane prepolymers, the control of NCO contents is 10-15%；
2）Then by reactant again with it is double-（3- methoxyl group silicon propyl group）Amine or double-（3- ethyoxyl silicon propyl group）Amine is gathered Reaction is closed, is designed by calculating so that NCO encloseds are controlled 80%, obtain cross-linking type end NCO oligomer and part end The mixture of NCO prepolymers, NCO contents are controlled in 3-4%；
3）After the completion of reaction, N- normal-butyl -3- aminopropyl trimethoxysilanes are added dropwise, more than not completely enclosed 3-4% The NCO functional groups of amount all block, and adjust viscosity simultaneously, obtain a Silante terminated polyurethane prepolymer.
2. a kind of synthetic method of silane end capped polyurethane prepolymer according to claim 1, it is characterised in that：
Step 1）Technical conditions be：Load weighted molecular weight is put into three-necked flask for 2000 polyether Glycols, The vacuum dehydration 2-3h at 120 ± 5 DEG C, is then cooled to less than 60 DEG C, the diphenyl methane two measured is added by several times different Cyanate, 80 ± 5 DEG C of controlling reaction temperature reacts 2h；
Step 2）Technical conditions be：Step 1）After the completion of be cooled to less than 60 DEG C, with dropping funel start to be added dropwise it is double- （3- methoxyl group silicon propyl group）Amine or double-（3- ethyoxyl silicon propyl group）Amine, rate of addition is that 1-2 drops are per second, control reaction temperature Spend for 80 ± 5 DEG C, until after being added dropwise to complete, continue to react 2h, after the completion of reaction, cooling, nitrogen charging gas shielded；
Step 3）Technical conditions be：Step 2）After the completion of reaction, started that N- normal-butyls -3- is added dropwise with dropping funel Aminopropyl trimethoxysilane, rate of addition is that 1-2 drops are per second, and controlling reaction temperature is 80 ± 5 DEG C, until being added dropwise to complete Afterwards, continue to react 2h, after the completion of reaction, obtain adhesive prepolymer.
3. a kind of synthetic method of silane end capped polyurethane prepolymer described in claim 1 or 2 is prepared in adhesive Using.
4. a kind of synthetic method of silane end capped polyurethane prepolymer described in claim 1 or 2 prepares polyurethane-hot melt Application in glue.
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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
CN109666115B (en) * 2017-10-16 2021-09-07 万华化学集团股份有限公司 Amino silane end-capped modified polyurethane resin 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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