CN103360562B - A kind of Polysiloxane-polyuregelolyurethane gelolyurethane material and preparation method thereof - Google Patents
A kind of Polysiloxane-polyuregelolyurethane gelolyurethane material and preparation method thereof Download PDFInfo
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- CN103360562B CN103360562B CN201310092208.6A CN201310092208A CN103360562B CN 103360562 B CN103360562 B CN 103360562B CN 201310092208 A CN201310092208 A CN 201310092208A CN 103360562 B CN103360562 B CN 103360562B
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- polysiloxane
- polyuregelolyurethane
- gelolyurethane
- isocyanate group
- terminal isocyanate
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Abstract
The present invention is to provide a kind of Polysiloxane-polyuregelolyurethane gelolyurethane material preparation method.By the polysiloxane of 100-200 part, with the vulcabond of 70-160 part at 60 DEG C of-90 DEG C of temperature, stirring reaction 1-3h, prepares the terminal isocyanate group semi prepolymer A that isocyanate group relative mass percentage composition is 15%-25%; Terminal isocyanate group semi prepolymer A and Amino End Group compound are uniformly mixed, pour into a mould preparation Polysiloxane-polyuregelolyurethane gelolyurethane material; Wherein terminal isocyanate group semi prepolymer A30-60 mass parts, Amino End Group compound 100-400 mass parts.Material of the present invention is not containing any softening agent, introduce polysiloxane and polyureas, enhance resiliency, compressed shape changes little, and organic compound all participates in the chemical reaction of gelinite formation, form cross-linked macromolecular gelinite, can not ooze out and move after long-time use, there is environment friendly well.
Description
Technical field
What the present invention relates to is a kind of organic polymer material, the present invention also relates to a kind of preparation method of organic polymer material.Specifically a kind of Polysiloxane-polyuregelolyurethane gelolyurethane material and preparation method thereof.
Background technology
Silicon gel is the gelatinous material that industrial circle is conventional, has the advantages such as excellent electric property and chemical stability, water-fast, resistance to ozone, weather-resistant, linear shrinkage ratio are low.But conventional silicone gel material needs to be heating and curing usually, and the use for the vibration and noise reducing buffer reagent of acoustic apparatus is rather inconvenient.By polyurea-polyuretahne material, modification is carried out to organosilicon material, improve mechanical and physical performance and the curing speed of gelatinous material.The gelatinous material obtained by modification can be satisfied the demand by normal cure under normal temperature condition.
Because polysiloxane molecule segment and polyurethane(s) segment solubility parameters differ greatly, poor compatibility, directly adopts physical blending mode then to there is serious being separated.In order to improve both consistencies, polysiloxane can be made to be incorporated in polyurethane(s) macromole by chemical bonded refractory.Polysiloxane and polyester or polyether glycol can be used as soft section jointly to participate in polyurethane(s) chemical reaction.But the low surface energy of polysiloxane makes its segment easily migrate to the interface of air-polymkeric substance, cause the degree of being separated serious, the silicone segments number on surface is increased, and surface free energy reduces.Polysiloxane molecule chain is longer, and polysiloxane silicon segment is easier in surface transport, and the degree that is separated is larger, and the silicon segment number on surface is increased, and the shock-absorbing capacity raising of polysiloxane segment to material on gelatinous material surface does not have due effect.Otherwise polysiloxane molecule chain is shorter, the degree that is separated is less, and polysiloxane silicon segment is not easily to surface transport.But adopt short chain polysiloxane molecule, when material internal polysiloxane segment content is identical, the hard segment content of material internal inherently increases, and the increase of hard segment content can reduce the snappiness of gel material, and finally affects the vibration and noise reducing resiliency of material.Therefore, in Polysiloxane-polyuregelne gelne material, introduce urea key, due to the stronger polarity effect of urea key, easily form the van der Waals interactions such as hydrogen bond with polysiloxane soft segment, polysiloxane segment is limited by Van der Waals force, and can not move as material surface.Namely improve the polysiloxane segment content of material internal, the surface transport phenomenon of polysiloxane can be weakened again, reach the effect improving resiliency.
Summary of the invention
The object of the present invention is to provide and a kind ofly have good resiliency, life-time service is without plasticizer migration and ooze out, the Polysiloxane-polyuregelolyurethane gelolyurethane material that compressed shape diminishes.The present invention also aims to provide a kind of preparation method with the Polysiloxane-polyuregelolyurethane gelolyurethane material of good environment friendly.
The object of the present invention is achieved like this:
The general structure of Polysiloxane-polyuregelolyurethane gelolyurethane material of the present invention is:
Wherein: R
1for CH
3, CH
2cH
3, CH
2cH
2cH
3, CH (CH
3)
2in one;
R
2for CH
3, CH
2cH
3, CH
2cH
2cH
3, CH (CH
3)
2in one;
R
3for CH
2cH
2, CH
2cH
2cH
2, CH
2cH (CH
3), CH
2cH
2cH
2cH
2, CH
2cH (CH
3) CH
2in one;
R
4for CH
2cH
2, CH
2cH
2cH
2, CH
2cH (CH
3), CH
2cH
2cH
2cH
2, CH
2cH (CH
3) CH
2in one.
Polysiloxane-polyuregelolyurethane gelolyurethane material preparation method of the present invention comprises two steps;
First step: by the polysiloxane of 100-200 mass parts, with the vulcabond of 70-160 mass parts at 60 DEG C of-90 DEG C of temperature, stirring reaction 1-3h, prepares the terminal isocyanate group semi prepolymer A that isocyanate group relative mass percentage composition is 15%-25%;
Second step: terminal isocyanate group semi prepolymer A and Amino End Group compound are uniformly mixed, pour into a mould preparation Polysiloxane-polyuregelolyurethane gelolyurethane material; Wherein terminal isocyanate group semi prepolymer A30-60 mass parts, Amino End Group compound 100-400 mass parts, and the ratio of the functionality of terminal isocyanate group semi prepolymer A, Amino End Group compound is 1.1-1.3;
The general structure of described polysiloxane is:
The general structure of described vulcabond is: OCN-X-NCO;
The general structure of described terminal isocyanate group semi prepolymer A is:
Wherein, R
1for CH
3, CH
2cH
3, CH
2cH
2cH
3, CH (CH
3)
2in one;
R
2for CH
3, CH
2cH
3, CH
2cH
2cH
3, CH (CH
3)
2in one;
R
1and R
2can be the same or different;
R
3for CH
2cH
2, CH
2cH
2cH
2, CH
2cH (CH
3), CH
2cH
2cH
2cH
2, CH
2cH (CH
3) CH
2in one;
R
4for CH
2cH
2, CH
2cH
2cH
2, CH
2cH (CH
3), CH
2cH
2cH
2cH
2, CH
2cH (CH
3) CH
2in one;
R
3and R
4can be the same or different.
Described polysiloxane relative molecular mass is 800-2000.
Vulcabond be tolylene diisocyanate, diphenylmethanediisocyanate, isophorone diisocyanate, dicyclohexyl methane diisocyanate, carbodiimide-uretonimine-modified diphenylmethanediisocyanate, urethane-modified diphenylmethanediisocyanate, Methylcyclohexyl diisocyanate, tetramethyl-m-xylylene diisocyanate, xylylene diisocyanate, hexamethylene diisocyanate, PPDI one or more.
Described Amino End Group compound be relative molecular mass scope 200 ~ 5000, functionality 2 ~ 3, containing two or more aromatic amine chainextender, aliphatics amine chain extender, Amino Terminated polyether(ATPE) mixture.
Described aromatic amine chainextender is 3,3 '-two chloro-4,4 '-diphenylmethanediamiand, 3,5-dimethythiotoluene diamine, 3,5-diethyl toluene diamine, 4,4 '-methylene-bis (3-chloro-2,6-Diethyl Aniline), 4,4 '-methylene-bis (2,6-diethyl) aniline, 4,4 '-methylene-bis (2,6-di-isopropyl) aniline, 4, one or more of 4 '-methylene-bis (2-sec.-propyl-6-methyl) aniline, 2,4-diamino-3,5-dimethyl sulphur-based chlorobenzenes;
Described aliphatics amine chain extender is N, N '-bis-sec.-amyl sec-pentyl secondary amyl cyclohexane diamine, 3,6-dioxy eight methylene diamine, the two aminopropyl methylamine of N, N-, isophorone diamine one or more;
Amino Terminated polyether(ATPE) is for containing following general formula
the mixture of one or both of polymkeric substance, wherein x, y, z, is the integer being greater than 1.
Polysiloxane-polyuregelolyurethane gelolyurethane material of the present invention is not containing any softening agent, introduce polysiloxane and polyureas, enhance resiliency, compressed shape changes little, and organic compound all participates in the chemical reaction of gelinite formation, form cross-linked macromolecular gelinite, can not ooze out and move after long-time use, there is environment friendly well.
Polysiloxane-polyuregelolyurethane gelolyurethane material can be used as the vibration and noise reducing buffer reagent of underwater sound device.
Embodiment
Polysiloxane-polyuregelolyurethane gelolyurethane material preparation method of the present invention comprises two steps, and wherein first step is the polysiloxane containing following general formula (1)
With the di-isocyanate reaction of following general formula (2),
OCN-X-NCO (2)
The obtained semi prepolymer A containing isocyanate groups containing following general formula (3).
Concrete preparation method is, in the reaction vessel that can heat and stir, as general formula (1) polysiloxane 100-200 part, with the vulcabond 70-160 part as general formula (2) under 60 DEG C of-90 DEG C of conditions, stirring reaction 1-3h, prepares the terminal isocyanate group semi prepolymer A that isocyanate group relative mass percentage composition is 15%-25%.
Wherein, R
1for CH
3, CH
2cH
3, CH
2cH
2cH
3, CH (CH
3)
2in one;
R
2for CH
3, CH
2cH
3, CH
2cH
2cH
3, CH (CH
3)
2in one;
R
1and R
2can be the same or different;
R
3for CH
2cH
2, CH
2cH
2cH
2, CH
2cH (CH
3), CH
2cH
2cH
2cH
2, CH
2cH (CH
3) CH
2in one;
R
4for CH
2cH
2, CH
2cH
2cH
2, CH
2cH (CH
3), CH
2cH
2cH
2cH
2, CH
2cH (CH
3) CH
2in one;
R
3and R
4can be the same or different;
Polysiloxane relative molecular mass is 800-2000;
Vulcabond be tolylene diisocyanate, diphenylmethanediisocyanate, isophorone diisocyanate, dicyclohexyl methane diisocyanate, carbodiimide-uretonimine-modified diphenylmethanediisocyanate, urethane-modified diphenylmethanediisocyanate, Methylcyclohexyl diisocyanate, tetramethyl-m-xylylene diisocyanate, xylylene diisocyanate, hexamethylene diisocyanate, PPDI one or more.
Second step be first step synthesize containing the semi prepolymer A of isocyanic ester and Amino End Group compound, high-speed stirring mixes, pour into a mould preparation Polysiloxane-polyuregelolyurethane gelolyurethane material.
Wherein semi prepolymer A30-60 part, Amino End Group compound 100-400 part are mass fraction, and the ratio of the functionality of semi prepolymer A, Amino End Group compound is 1.1-1.3.
Amino End Group compound be relative molecular mass scope 200 ~ 5000, functionality 2 ~ 3, containing two or more aromatic amine chainextender, aliphatics amine chain extender, Amino Terminated polyether(ATPE) mixture.Described aromatic amine chainextender is preferably 3,3 '-two chloro-4,4 '-diphenylmethanediamiand, 3,5-dimethythiotoluene diamine, 3,5-diethyl toluene diamine, 4,4 '-methylene-bis (3-chloro-2,6-Diethyl Aniline), 4,4 '-methylene-bis (2,6-diethyl) aniline, 4,4 '-methylene-bis (2,6-di-isopropyl) aniline, 4, one or more of 4 '-methylene-bis (2-sec.-propyl-6-methyl) aniline, 2,4-diamino-3,5-dimethyl sulphur-based chlorobenzenes; Described aliphatics amine chain extender is preferably N, N '-bis-sec.-amyl sec-pentyl secondary amyl cyclohexane diamine, 3,6-dioxy eight methylene diamine, the two aminopropyl methylamine of N, N-, isophorone diamine one or more; The one that Amino Terminated polyether(ATPE) is the polymkeric substance containing following general formula (4), (5) or mixture.
Wherein x, y, z can identical also can be different, be the integer being greater than 1;
Wherein x be greater than 1 integer.
Be obtained by reacting final polysilicone-polyurethanes-polyurea gel material by prepolymer and Amino End Group compound, its general structure is shown in (6)
Below in conjunction with embodiment, the present invention is further detailed explanation.The number of following component is mass fraction.
Embodiment one
Get the polydimethylsiloxane 130 parts of molecular weight 1900, diphenylmethanediisocyanate 116 parts, 80 DEG C of stirring reaction 2h, preparing isocyanate content is 20% semi prepolymer A.
Get semi prepolymer A50 part, three-functionality-degree Amino Terminated polyether(ATPE) 12 parts that three-functionality-degree Amino Terminated polyether(ATPE) 126 parts that relative molecular mass is 5000, relative molecular mass are 400, relative molecular mass 4,000 two functionality Amino Terminated polyether(ATPE) 64 parts, isophorone diamine 1 part, 3,5-diethyl toluene diamine 1 part.Be uniformly mixed, casting.
Reach optimum performance after 7 days, without oozing out, VLRH hardness is 36, and permanent compression set is 3.9%, and falling-rebounding ball is 24.
Embodiment two
The three-functionality-degree Amino Terminated polyether(ATPE) 4 parts that the three-functionality-degree Amino Terminated polyether(ATPE) 55 parts that semi prepolymer A40 part of preparation in Example one, relative molecular mass are 3000, relative molecular mass are 400, relative molecular mass is the two functionality Amino Terminated polyether(ATPE) 50 parts of 4000, relative molecular mass 2,000 two functionality Amino Terminated polyether(ATPE) 43 parts, isophorone diamine 1.5 parts, 2,4-diamino-3,5-dimethyl sulphur-based chlorobenzene 1 part.Be uniformly mixed, casting.
Reach optimum performance after 7 days, without oozing out, VLRH hardness is 39, and permanent compression set is 4.2%, and falling-rebounding ball is 26.
Embodiment three
Get the polydiethylsiloxane 100 parts of molecular weight 1300, diphenylmethanediisocyanate 40 parts, tolylene diisocyanate 60 parts, 90 DEG C of stirring reaction 2h, preparing isocyanate content is 25% semi prepolymer A.
Get semi prepolymer A50 part, three-functionality-degree Amino Terminated polyether(ATPE) 8 parts that three-functionality-degree Amino Terminated polyether(ATPE) 205 parts that relative molecular mass is 5000, relative molecular mass are 400, relative molecular mass 4,000 two functionality Amino Terminated polyether(ATPE) 135 parts, 2,4-diamino-3,5-dimethyl sulphur-based chlorobenzene 1.5 parts, 3,5-diethyl toluene diamine 1.2 parts.Be uniformly mixed, casting.
Reach optimum performance after 7 days, without oozing out, VLRH hardness is 30, and permanent compression set is 3.9%, and falling-rebounding ball is 30.
Embodiment four
Get the polydimethylsiloxane 170 parts of molecular weight 800, diphenylmethanediisocyanate 15 parts, hexamethylene diisocyanate 38 parts, PPDI 28 parts, 80 DEG C of stirring reaction 2h, preparing isocyanate content is 15% semi prepolymer A.
Get semi prepolymer A50 part, three-functionality-degree Amino Terminated polyether(ATPE) 16 parts that three-functionality-degree Amino Terminated polyether(ATPE) 27 parts that relative molecular mass is 5000, relative molecular mass are 3000, relative molecular mass be 400 three-functionality-degree Amino Terminated polyether(ATPE) 6 parts, relative molecular mass 2,000 two functionality Amino Terminated polyether(ATPE) 80 parts, 2,4-diamino-3,5-dimethyl sulphur-based chlorobenzene 1 part, 3,5-dimethythiotoluene diamine 1 part.Be uniformly mixed, casting.
Reach optimum performance after 7 days, without oozing out, VLRH hardness is 30, and permanent compression set is 4.5%, and falling-rebounding ball is 24.
Although describe in detail very much the described in the text invention protected with claim with reference to some embodiments; but it will be understood by those skilled in the art that the present invention protected with claim described in literary composition is by realizing except for illustration of other embodiments except those embodiments of object.The spirit and scope of claims should not be limited to the description of the embodiment comprised in literary composition.
Claims (6)
1. a Polysiloxane-polyuregelolyurethane gelolyurethane material, is characterized in that having following general structure:
Wherein: R
1for CH
3, CH
2cH
3, CH
2cH
2cH
3, CH (CH
3)
2in one,
R
2for CH
3, CH
2cH
3, CH
2cH
2cH
3, CH (CH
3)
2in one,
R
3for CH
2cH
2, CH
2cH
2cH
2, CH
2cH (CH
3), CH
2cH
2cH
2cH
2, CH
2cH (CH
3) CH
2in one,
R
4for CH
2cH
2, CH
2cH
2cH
2, CH
2cH (CH
3), CH
2cH
2cH
2cH
2, CH
2cH (CH
3) CH
2in one;
Described Polysiloxane-polyuregelolyurethane gelolyurethane material is adopted and is obtained with the following method,
First step: by the polysiloxane of 100-200 mass parts, with the vulcabond of 70-160 mass parts at 60 DEG C of-90 DEG C of temperature, stirring reaction 1-3h, prepare the terminal isocyanate group semi prepolymer A that isocyanate group relative mass percentage composition is 15%-25%, described polysiloxane relative molecular mass is 800-2000;
Second step: terminal isocyanate group semi prepolymer A and Amino End Group compound are uniformly mixed, pour into a mould preparation Polysiloxane-polyuregelolyurethane gelolyurethane material; Wherein terminal isocyanate group semi prepolymer A 30-60 mass parts, Amino End Group compound 100-400 mass parts, and the ratio of the functionality of terminal isocyanate group semi prepolymer A, Amino End Group compound is 1.1-1.3, described Amino End Group compound be relative molecular mass scope 200 ~ 5000, functionality 2 ~ 3, containing two or more aromatic amine chainextender, aliphatics amine chain extender, Amino Terminated polyether(ATPE) mixture.
2. a Polysiloxane-polyuregelolyurethane gelolyurethane material preparation method, is characterized in that:
First step: by the polysiloxane of 100-200 mass parts, with the vulcabond of 70-160 mass parts at 60 DEG C of-90 DEG C of temperature, stirring reaction 1-3h, prepare the terminal isocyanate group semi prepolymer A that isocyanate group relative mass percentage composition is 15%-25%, described polysiloxane relative molecular mass is 800-2000;
Second step: terminal isocyanate group semi prepolymer A and Amino End Group compound are uniformly mixed, pour into a mould preparation Polysiloxane-polyuregelolyurethane gelolyurethane material; Wherein terminal isocyanate group semi prepolymer A 30-60 mass parts, Amino End Group compound 100-400 mass parts, and the ratio of the functionality of terminal isocyanate group semi prepolymer A, Amino End Group compound is 1.1-1.3, described Amino End Group compound be relative molecular mass scope 200 ~ 5000, functionality 2 ~ 3, containing two or more aromatic amine chainextender, aliphatics amine chain extender, Amino Terminated polyether(ATPE) mixture;
The general structure of described polysiloxane is:
The general structure of described vulcabond is: OCN-X-NCO;
The general structure of described terminal isocyanate group semi prepolymer A is:
Wherein, R
1for CH
3, CH
2cH
3, CH
2cH
2cH
3, CH (CH
3)
2in one;
R
2for CH
3, CH
2cH
3, CH
2cH
2cH
3, CH (CH
3)
2in one;
R
1and R
2can be the same or different;
R
3for CH
2cH
2, CH
2cH
2cH
2, CH
2cH (CH
3), CH
2cH
2cH
2cH
2, CH
2cH (CH
3) CH
2in one;
R
4for CH
2cH
2, CH
2cH
2cH
2, CH
2cH (CH
3), CH
2cH
2cH
2cH
2, CH
2cH (CH
3) CH
2in one;
R
3and R
4can be the same or different.
3. Polysiloxane-polyuregelolyurethane gelolyurethane material preparation method according to claim 2, it is characterized in that: vulcabond is tolylene diisocyanate, diphenylmethanediisocyanate, isophorone diisocyanate, dicyclohexyl methane diisocyanate, carbodiimide-uretonimine-modified diphenylmethanediisocyanate, urethane-modified diphenylmethanediisocyanate, Methylcyclohexyl diisocyanate, tetramethyl-m-xylylene diisocyanate, xylylene diisocyanate, hexamethylene diisocyanate, one or more of PPDI.
4. Polysiloxane-polyuregelolyurethane gelolyurethane material preparation method according to claim 3, it is characterized in that: described aromatic amine chainextender is 3, 3 '-two chloro-4, 4 '-diphenylmethanediamiand, 3, 5-dimethythiotoluene diamine, 3, 5-diethyl toluene diamine, 4, 4 '-methylene-bis (3-chloro-2, 6-Diethyl Aniline), 4, 4 '-methylene-bis (2, 6-diethyl) aniline, 4, 4 '-methylene-bis (2, 6-di-isopropyl) aniline, 4, 4 '-methylene-bis (2-sec.-propyl-6-methyl) aniline, 2, 4-diamino-3, one or more of 5-dimethyl sulphur-based chlorobenzene.
5. Polysiloxane-polyuregelolyurethane gelolyurethane material preparation method according to claim 4, it is characterized in that: described aliphatics amine chain extender is N, N '-bis-sec.-amyl sec-pentyl secondary amyl cyclohexane diamine, 3, one or more of 6-dioxy eight methylene diamine, the two aminopropyl methylamine of N, N-, isophorone diamine.
6. Polysiloxane-polyuregelolyurethane gelolyurethane material preparation method according to claim 5, is characterized in that: described Amino Terminated polyether(ATPE) is for containing following general formula
the mixture of one or both of polymkeric substance, wherein x, y, z, is the integer being greater than 1.
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| CN103834034B (en) * | 2014-02-19 | 2017-02-08 | 湖北大学 | Polyureas copolymer with main chain containing siloxane composition unit and preparation method thereof |
| PL3288996T5 (en) * | 2015-04-27 | 2023-03-27 | Huntsman International Llc | Functionalized isocyanate based porous materials |
| CN109369883A (en) * | 2018-09-01 | 2019-02-22 | 哈尔滨工程大学 | A kind of preparation method of organic silicon modified polyurethane adhesive |
| CN113321846A (en) * | 2021-06-08 | 2021-08-31 | 哈尔滨工程大学 | Super-hydrophobic photo-thermal adsorption material capable of treating viscous crude oil and preparation method thereof |
| CN113462163B (en) * | 2021-06-30 | 2022-07-05 | 成都硅宝科技股份有限公司 | Dealcoholized high-strength transparent flowing silicone rubber and preparation method thereof |
| CN115819711B (en) * | 2022-11-24 | 2024-04-05 | 四川大学 | Reactive extrusion 3D printing silicone rubber-polyurea material and application thereof |
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