CN116804086A - Long-chain alkyl-polar group co-modified polysiloxane and preparation method thereof - Google Patents
Long-chain alkyl-polar group co-modified polysiloxane and preparation method thereof Download PDFInfo
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- CN116804086A CN116804086A CN202311080972.1A CN202311080972A CN116804086A CN 116804086 A CN116804086 A CN 116804086A CN 202311080972 A CN202311080972 A CN 202311080972A CN 116804086 A CN116804086 A CN 116804086A
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- -1 polysiloxane Polymers 0.000 title claims abstract description 81
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 61
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 125000000962 organic group Chemical group 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims description 37
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 claims description 32
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 19
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 18
- 229920000570 polyether Polymers 0.000 claims description 18
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical group C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000006555 catalytic reaction Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000002981 blocking agent Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229920006112 polar polymer Polymers 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- NVFYKZBOLSIHEI-UHFFFAOYSA-N furan-2,5-dione;2-methylprop-2-enoic acid Chemical group CC(=C)C(O)=O.O=C1OC(=O)C=C1 NVFYKZBOLSIHEI-UHFFFAOYSA-N 0.000 claims description 2
- JPZROSNLRWHSQQ-UHFFFAOYSA-N furan-2,5-dione;prop-2-enoic acid Chemical group OC(=O)C=C.O=C1OC(=O)C=C1 JPZROSNLRWHSQQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920000193 polymethacrylate Polymers 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 229910000105 potassium hydride Inorganic materials 0.000 claims description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012312 sodium hydride Substances 0.000 claims description 2
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims 2
- 238000001125 extrusion Methods 0.000 abstract description 15
- 239000000463 material Substances 0.000 abstract description 14
- 239000002861 polymer material Substances 0.000 abstract description 12
- 238000012545 processing Methods 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 9
- 238000012986 modification Methods 0.000 abstract description 6
- 230000004048 modification Effects 0.000 abstract description 6
- 230000009471 action Effects 0.000 abstract description 4
- 230000007547 defect Effects 0.000 abstract description 4
- 239000000945 filler Substances 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000006116 polymerization reaction Methods 0.000 abstract description 2
- 239000012779 reinforcing material Substances 0.000 abstract description 2
- 230000001050 lubricating effect Effects 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 45
- 239000000203 mixture Substances 0.000 description 28
- 238000010438 heat treatment Methods 0.000 description 12
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 10
- 239000004033 plastic Substances 0.000 description 8
- 229920003023 plastic Polymers 0.000 description 8
- 238000001556 precipitation Methods 0.000 description 8
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000003377 acid catalyst Substances 0.000 description 6
- 239000012752 auxiliary agent Substances 0.000 description 6
- 238000009825 accumulation Methods 0.000 description 5
- 238000005461 lubrication Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 3
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical group CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000006459 hydrosilylation reaction Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical class CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 229910002808 Si–O–Si Inorganic materials 0.000 description 1
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical group CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- RZJRJXONCZWCBN-UHFFFAOYSA-N alpha-octadecene Natural products CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000010094 polymer processing Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Abstract
The invention relates to the technical field of material modification, and discloses a long-chain alkyl-polar group co-modified polysiloxane and a preparation method thereof, wherein the structural formula of the co-modified polysiloxane is shown as (I), and R in (I) 1 、R 2 、R 3 、R 4 、R 5 、R 6 Are monovalent organic groups or atoms independent of each other; m, n and r are integers more than or equal to 4. The preparation method of the long-chain alkyl and polar group co-modified polysiloxane provided by the invention has excellent lubricating and demolding processing performances, can effectively improve the compatible effect of a high polymer material and a filler or a reinforcing material, increases extrusion efficiency, improves extrusion defects, optimizes the structure and enhances the action effect of the long-chain alkyl and polar group co-modified polysiloxane in the high polymer material; the preparation method adopts a fractional polymerization method, so that the structure is easier to control, and the synthesis is simple and convenient.
Description
Technical Field
The invention relates to the technical field of material modification, in particular to long-chain alkyl-polar group co-modified polysiloxane and a preparation method thereof.
Background
The polysiloxane material takes Si-O-Si bond as main chain, and the side chain is connected with organic group, so that the polysiloxane material has inorganic structure and organic structure in structure; because of the structural uniqueness, the polysiloxane material has the characteristics of molecular flexibility, excellent thermal stability, lower surface energy, excellent high-low temperature performance, aging resistance and the like. Although polysiloxane materials have these properties, they have poor compatibility when co-processed with polymeric materials and are therefore greatly limited in their application.
At present, a great deal of research on structural modification of polysiloxane materials is carried out, most of the materials are directly subjected to structural modification on polysiloxane through hydrosilylation reaction on the existing polysiloxane chain, so that organic groups are randomly connected on the polysiloxane chain segments, and the performance of the polysiloxane organic groups is endowed.
The modified polysiloxane materials in the daily chemical industry, the coating industry and the ink industry are widely applied, and most of the modified polysiloxane materials are amino modified polysiloxane, polyether modified polysiloxane, polyester modified polysiloxane, epoxy modified polysiloxane and the like, and are mainly used in the form of emulsion; the modified polysiloxane has less application in the field of high polymer material processing, and along with the continuous development of the organic silicon material, the polysiloxane is often added as a processing aid in the high polymer material processing industry so as to improve the processing performance and the surface performance of products; however, the compatibility of polysiloxanes with polymeric materials is problematic. The polysiloxane is modified to solve the problem of compatibility with the high polymer material structurally, and the organic group on the modified polysiloxane structure is utilized to associate with the high polymer material or the inorganic filler, so that the filler is better dispersed in the plastic and is stronger in combination.
Disclosure of Invention
The invention solves the technical problems that:
the invention is used for solving the problems that the existing high-filling system plastic is difficult to process and extrude, and the high-filling system plastic is easy to have the problems of die accumulation and workpiece surface defects during extrusion.
The invention adopts the technical scheme that:
aiming at the technical problems, the invention provides long-chain alkyl-polar group co-modified polysiloxane and a preparation method thereof.
The specific contents are as follows:
the invention provides long-chain alkyl-polar group co-modified polysiloxane, which has a structural formula shown in (I):
（I）
R 1 、R 2 、R 3 、R 4 、R 5 、R 6 are monovalent organic groups or atoms independent of each other; m, n and r are integers more than or equal to 4;
R 1 methyl or ethyl;
R 2 is long-chain alkyl, the structure is shown as a general formula (I-1),
（I-1）
a is an integer greater than 8;
R 3 、R 4 methyl, ethyl, propyl, phenyl, vinyl, hydroxyl or a hydrogen atom;
R 5 is methyl or ethyl, R 6 Is a long-chain organic group containing a polar structure.
Second, the present invention provides a method for preparing the aforementioned long-chain alkyl-polar group co-modified polysiloxane, comprising the following steps:
s1, preparing cyclosiloxane containing long-chain alkyl groups and cyclosiloxane containing polar groups;
s2, mixing cyclosiloxane containing long-chain alkyl, cyclosiloxane containing polar groups, octamethyl cyclotetrasiloxane, a blocking agent and a catalyst, and carrying out ring opening polymerization to obtain a finished product.
The invention adopts the technical mechanism that:
according to the invention, by utilizing the principles of hydrosilylation and reaction copolymerization, through structural design, different modified structures and polar functional groups are adopted for different application systems, the pertinence is strong, and the molecular chain segments with different structures are arranged in one molecule, and the functional groups with the same structure repeatedly appear, so that the compatibilization and association effects on materials can be improved; the preparation method provided by the invention adopts a step polymerization method, so that the structure is easier to control, and the synthesis is simple and convenient.
The invention has the beneficial effects that:
(1) The synthesis process provided by the invention is simple, easy to operate and strong in structural controllability;
(2) The synthetic raw materials adopted by the invention are simple and easy to obtain, and are beneficial to the amplified production of products;
(3) The modified polysiloxane auxiliary agent structure obtained by the invention contains long-chain alkyl and polar groups, the polysiloxane chain segments with the long-chain alkyl and the polysiloxane chain segments with the polar groups are not randomly and alternately connected, the same modified group units repeatedly appear on the same chain segment, meanwhile, the whole molecular structure takes polysiloxane as a main chain, has the performances of smoothness, high and low temperature resistance and the like of the polysiloxane, the compatibilization is achieved by utilizing the action of a long carbon chain and a carbon-based polymer material, and the association effect is achieved by the action of a polar group part and a filler or a polar polymer material;
(4) The modified polysiloxane auxiliary agent obtained by the invention has excellent processability such as lubrication, demolding and the like, can effectively improve the compatible effect of a high polymer material and a filler or a reinforcing material, increases extrusion efficiency, improves extrusion defects, optimizes the structure and enhances the action effect of the modified polysiloxane auxiliary agent in the high polymer material;
(5) According to the invention, through structural design, different modified structures and polar functional groups are adopted for different application systems, so that the pertinence is strong, and the molecular chain segments with different structures are arranged in one molecule, so that the effects of capacity increasing, lubrication and extrusion improvement are achieved in polymer processing;
(6) The modified polysiloxane with different structures can be compounded to achieve the balance of internal and external lubrication in the high polymer material, and the appearance of the product is not affected due to precipitation;
(7) The modified polysiloxane auxiliary agent provided by the invention can effectively improve the processing and extrusion of high polymer plastic materials and the surface performance of plastic products, and solves the problems of die accumulation, extrusion defects and the like;
(8) The modified polysiloxane auxiliary agent has small addition amount and can not be separated out on the surface of a plastic product;
(9) The modified polysiloxane auxiliary agent has lower VOC when being applied to plastic processing.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention more clear, the technical solutions of the embodiments of the present invention will be clearly and completely described below. The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
The invention aims to provide long-chain alkyl-polar group co-modified polysiloxane and a preparation method thereof. In particular, the method comprises the steps of,
the invention provides long-chain alkyl-polar group co-modified polysiloxane, which has a structural formula shown in (I):
（I）
R 1 、R 2 、R 3 、R 4 、R 5 、R 6 are monovalent organic groups or atoms independent of each other; m, n and r are integers more than or equal to 4;
R 1 methyl or ethyl;
R 2 is long-chain alkyl, the structure is shown as a general formula (I-1),
（I-1）
a is an integer greater than 8;
R 3 、R 4 methyl, ethyl, propyl, phenyl, vinyl, hydroxyl or a hydrogen atom;
R 5 is methyl or ethyl, R 6 Is of a polar structureLong chain organic groups.
Further, R 6 Is a long-chain polyether group, a long-chain polyester group, a long-chain polyamide group, a long-chain polyacrylic group, a long-chain polyacrylate group, a long-chain polymethacrylate group, a long-chain polystyrene group, a long-chain polyurethane group, a long-chain polyacrylic acid-styrene group, a long-chain polyacrylate-styrene group, a long-chain polymethacrylate-styrene group, a long-chain polyacrylamide-methyl acrylate group, a long-chain polyacrylamide-methyl methacrylate group, a long-chain polyacrylamide-maleic anhydride group, a long-chain polystyrene-maleic anhydride group, a long-chain polymethyl acrylate-maleic anhydride group or a long-chain polymethyl methacrylate-maleic anhydride group.
Second, the present invention provides a method for preparing the aforementioned long-chain alkyl-polar group co-modified polysiloxane, comprising the following steps:
s1, preparing cyclosiloxane containing long-chain alkyl groups and cyclosiloxane containing polar groups;
s2, mixing cyclosiloxane containing long-chain alkyl, cyclosiloxane containing polar groups, octamethyl cyclotetrasiloxane, a blocking agent and a catalyst, and carrying out ring opening polymerization to obtain a finished product.
Further, S2 includes at least one of features (1) to (5):
(1) The end-capping agent is hexamethyldisiloxane;
(2) The catalyst comprises at least one of sodium hydroxide, potassium hydroxide, sodium hydride, potassium hydride, tetramethylammonium hydroxide and tetrabutylammonium hydroxide;
(3) The total amount of the raw materials is that the molar ratio of cyclosiloxane containing long-chain alkyl, octamethyl cyclotetrasiloxane, cyclosiloxane containing polar groups and end capping agent is 10-99:10-99:1-40; preferably, the ratio of the raw materials is 1-7:4-10:1-7:1; the specific steps can be as follows: 4:4:4:1, 1:10:1:1, 7:4:1:1, 1:4:7:1.
(4) The catalyst accounts for 0.1-2wt% of the total weight of the raw materials;
(5) The reaction temperature is 100-200 ℃.
Further, in S1, the structure of the cyclosiloxane containing long-chain alkyl is shown as a general formula (II):
（II）
R 1 methyl or ethyl; r is R 2 Is long-chain alkyl, the structure of which is shown as the general formula (I-1),
（I-1）
a is an integer greater than 8.
Further, the preparation method of the cyclosiloxane containing long-chain alkyl comprises the steps of preparing the hydrogen-containing cyclosiloxane by catalytic reaction with unsaturated alkane; comprising at least one of the features (1) to (4):
(1) The catalyst is a platinum catalyst;
(2) The catalyst consumption accounts for 0.1-2wt% of the total reaction amount;
(3) The reaction temperature is 60-200 ℃;
(4) The reaction time is 6-10 h.
Further, in S1, the structure of the cyclosiloxane containing the polar group is shown as a general formula (III):
（III）
R 5 is methyl or ethyl, R 6 Is a long-chain organic group containing a polar structure.
Further, the polar group-containing cyclosiloxane is prepared by a catalytic reaction of hydrogen-containing cyclosiloxane and vinyl-containing long-chain polar polymer, and comprises at least one of the characteristics (1) to (4):
(1) The catalyst is a platinum catalyst;
(2) The catalyst consumption accounts for 0.1-2wt% of the total reaction amount;
(3) The reaction temperature is 60-200 ℃;
(4) The reaction time is 6-10 h.
Thirdly, the invention provides application of the long-chain alkyl-polar group co-modified polysiloxane in processing of high polymer materials.
Examples
Example 1
Step one:
adding alpha-dodecene and tetramethyl cyclotetrasiloxane into a flask according to a molar ratio of 4:1, stirring for 1h at 80 ℃, slowly dripping chloroplatinic acid catalyst with the total feeding mass of 0.1% after stirring uniformly, and continuing stirring for reacting for 8h to obtain the dodecyl modified cyclotetrasiloxane A1 with the structural formula as follows:
the molar ratio of the allyl polyoxyethylene polyoxypropylene ether (Jiangsu sea Ann petrochemical plant) with the molecular weight of 1000 to the tetramethyl cyclotetrasiloxane is 4:1 is added into a flask and stirred for 1h at 80 ℃, and after being stirred uniformly, chloroplatinic acid catalyst accounting for 0.1% of the total feeding mass is slowly dripped into the flask, and the reaction is continued for 8h, so as to prepare the long-chain polyether modified cyclotetrasiloxane B1, the structural formula of which is as follows:
step two:
the molar ratio of the dodecyl modified cyclotetrasiloxane A1, the octamethyl cyclotetrasiloxane, the long-chain polyether modified cyclotetrasiloxane B1 and the hexamethyldisiloxane is 4:4:4:1 adding the mixture into a flask, stirring for 1h at the temperature of 100 ℃, slowly adding tetramethylammonium hydroxide with the total mass of 0.5% into the mixture after uniformly stirring, stirring for 0.5h, and then heating to the temperature of 150 ℃ for continuous reaction for 8h; after the reaction is finished, the temperature is increased to 180 ℃ and reduced pressure is carried out for 2 hours, so that the modified polysiloxane auxiliary C1 is prepared, and the structural formula is as follows:
example 2
Procedure as in example 1;
step two:
the molar ratio of the dodecyl modified cyclotetrasiloxane A1, the octamethyl cyclotetrasiloxane, the long-chain polyether modified cyclotetrasiloxane B1 and the hexamethyldisiloxane is 1:10:1:1 adding the mixture into a flask, stirring for 1h at the temperature of 100 ℃, slowly adding tetramethylammonium hydroxide with the total mass of 0.5% into the mixture after uniformly stirring, stirring for 0.5h, and then heating to the temperature of 150 ℃ for continuous reaction for 8h; after the reaction is finished, the temperature is increased to 180 ℃ and reduced pressure is carried out for 2 hours, so as to prepare the modified polysiloxane auxiliary C2, wherein the structural formula is as follows:
example 3
Procedure as in example 1;
step two:
the molar ratio of the dodecyl modified cyclotetrasiloxane A1, the octamethyl cyclotetrasiloxane, the long-chain polyether modified cyclotetrasiloxane B1 and the hexamethyldisiloxane is 7:4:1:1 adding the mixture into a flask, stirring for 1h at the temperature of 100 ℃, slowly adding tetramethylammonium hydroxide with the total mass of 0.5% into the mixture after uniformly stirring, stirring for 0.5h, and then heating to the temperature of 150 ℃ for continuous reaction for 8h; after the reaction is finished, the temperature is increased to 180 ℃ and reduced pressure is carried out for 2 hours, so as to prepare the modified polysiloxane auxiliary C3, wherein the structural formula is as follows:
example 4
Procedure as in example 1;
step two:
the molar ratio of the dodecyl modified cyclotetrasiloxane A1, the octamethyl cyclotetrasiloxane, the long-chain polyether modified cyclotetrasiloxane B1 and the hexamethyldisiloxane is 1:4:7:1 adding the mixture into a flask, stirring for 1h at the temperature of 100 ℃, slowly adding tetramethylammonium hydroxide with the total mass of 0.5% into the mixture after uniformly stirring, stirring for 0.5h, and then heating to the temperature of 150 ℃ for continuous reaction for 8h; after the reaction is finished, the temperature is increased to 180 ℃ and reduced pressure is carried out for 2 hours, so as to prepare the modified polysiloxane auxiliary C4, wherein the structural formula is as follows:
example 5
Step one:
the molar ratio of the alpha-octadecene to the tetramethyl cyclotetrasiloxane is 4:1 is added into a flask and stirred for 1h at 80 ℃, and after being stirred uniformly, chloroplatinic acid catalyst accounting for 0.1% of the total feeding mass is slowly dripped into the flask, and the reaction is continued for 8h, so that the octadecyl modified cyclotetrasiloxane A2 is prepared, wherein the structural formula is as follows:
the allyl polyoxyethylene polyoxypropylene ether with the molecular weight of 1000 and tetramethyl cyclotetrasiloxane are respectively mixed according to the mole ratio of 4:1 adding the mixture into a flask, stirring for 1h at 80 ℃, slowly dripping chloroplatinic acid catalyst accounting for 0.1% of the total feeding mass after stirring uniformly, and continuing stirring for reacting for 8h to obtain the long-chain polyether modified cyclotetrasiloxane B1;
step two:
the molar ratio of the octadecyl modified cyclotetrasiloxane A2, the octamethyl cyclotetrasiloxane, the long-chain polyether modified cyclotetrasiloxane B1 and the hexamethyldisiloxane is 4:4:4:1 adding the mixture into a flask, stirring for 1h at the temperature of 100 ℃, slowly adding tetramethylammonium hydroxide with the total mass of 0.5% into the mixture after uniformly stirring, stirring for 0.5h, and then heating to the temperature of 150 ℃ for continuous reaction for 8h; after the reaction is finished, the temperature is increased to 180 ℃ and reduced pressure is carried out for 2 hours, so as to prepare the modified polysiloxane auxiliary C5, and the structural formula is as follows:
example 6
Procedure as in example 5;
step two:
the molar ratio of the octadecyl modified cyclotetrasiloxane A2, the octamethyl cyclotetrasiloxane, the long-chain polyether modified cyclotetrasiloxane B1 and the hexamethyldisiloxane is 1:10:1:1 adding the mixture into a flask, stirring for 1h at the temperature of 100 ℃, slowly adding tetramethylammonium hydroxide with the total mass of 0.5% into the mixture after uniformly stirring, stirring for 0.5h, and then heating to the temperature of 150 ℃ for continuous reaction for 8h; after the reaction is finished, the temperature is increased to 180 ℃ and reduced pressure is carried out for 2 hours, so as to prepare the modified polysiloxane auxiliary C6, the structural formula of which is as follows:
example 7
Procedure as in example 5;
step two:
the molar ratio of the octadecyl modified cyclotetrasiloxane A2, the octamethyl cyclotetrasiloxane, the long-chain polyether modified cyclotetrasiloxane B1 and the hexamethyldisiloxane is 7:4:1:1 adding the mixture into a flask, stirring for 1h at the temperature of 100 ℃, slowly adding tetramethylammonium hydroxide with the total mass of 0.5% into the mixture after uniformly stirring, stirring for 0.5h, and then heating to the temperature of 150 ℃ for continuous reaction for 8h; after the reaction is finished, the temperature is increased to 180 ℃ and reduced pressure is carried out for 2 hours, so as to prepare the modified polysiloxane auxiliary C7, wherein the structural formula is as follows:
example 8
Procedure as in example 5;
step two:
the molar ratio of the octadecyl modified cyclotetrasiloxane A2, the octamethyl cyclotetrasiloxane, the long-chain polyether modified cyclotetrasiloxane B1 and the hexamethyldisiloxane is 1:4:7:1 adding the mixture into a flask, stirring for 1h at the temperature of 100 ℃, slowly adding tetramethylammonium hydroxide with the total mass of 0.5% into the mixture after uniformly stirring, stirring for 0.5h, and then heating to the temperature of 150 ℃ for continuous reaction for 8h; after the reaction is finished, the temperature is increased to 180 ℃ and reduced pressure is carried out for 2 hours, so that the modified polysiloxane auxiliary C8 is prepared, and the structural formula is as follows:
example 9
Step one:
the molar ratio of the alpha-dodecene to the tetramethyl cyclotetrasiloxane is 4:1 adding the mixture into a flask, stirring for 1h at 80 ℃, slowly dripping chloroplatinic acid catalyst accounting for 0.1% of the total feeding mass after stirring uniformly, and continuing stirring for reacting for 8h to obtain dodecyl modified cyclotetrasiloxane A1;
the allyl polyoxyethylene polyoxypropylene ether with the molecular weight of 2000 and tetramethyl cyclotetrasiloxane are respectively mixed according to the mole ratio of 4:1 is added into a flask and stirred for 1h at 80 ℃, and after being stirred uniformly, chloroplatinic acid catalyst accounting for 0.1% of the total feeding mass is slowly dripped into the flask, and the reaction is continued for 8h, so as to prepare the long-chain polyether modified cyclotetrasiloxane B2, the structural formula of which is as follows:
step two:
the molar ratio of the dodecyl modified cyclotetrasiloxane A1, the octamethyl cyclotetrasiloxane, the long-chain polyether modified cyclotetrasiloxane B2 and the hexamethyldisiloxane is 4:4:4:1 adding the mixture into a flask, stirring for 1h at the temperature of 100 ℃, slowly adding tetramethylammonium hydroxide with the total mass of 0.5% into the mixture after uniformly stirring, stirring for 0.5h, and then heating to the temperature of 150 ℃ for continuous reaction for 8h; after the reaction is finished, the temperature is increased to 180 ℃ and reduced pressure is carried out for 2 hours, so as to prepare the modified polysiloxane auxiliary C9, the structural formula of which is as follows:
example 10
Procedure as in example 9;
step two:
the molar ratio of the dodecyl modified cyclotetrasiloxane A1, the octamethyl cyclotetrasiloxane, the long-chain polyether modified cyclotetrasiloxane B2 and the hexamethyldisiloxane is 1:10:1:1 adding the mixture into a flask, stirring for 1h at the temperature of 100 ℃, slowly adding tetramethylammonium hydroxide with the total mass of 0.5% into the mixture after uniformly stirring, stirring for 0.5h, and then heating to the temperature of 150 ℃ for continuous reaction for 8h; after the reaction is finished, the temperature is increased to 180 ℃ and reduced pressure is carried out for 2 hours, so that the modified polysiloxane auxiliary C10 is prepared, and the structural formula is as follows:
example 11
Procedure as in example 9;
step two:
the molar ratio of the dodecyl modified cyclotetrasiloxane A1, the octamethyl cyclotetrasiloxane, the long-chain polyether modified cyclotetrasiloxane B2 and the hexamethyldisiloxane is 7:4:1:1 adding the mixture into a flask, stirring for 1h at the temperature of 100 ℃, slowly adding tetramethylammonium hydroxide with the total mass of 0.5% into the mixture after uniformly stirring, stirring for 0.5h, and then heating to the temperature of 150 ℃ for continuous reaction for 8h; after the reaction is finished, the temperature is increased to 180 ℃ and reduced pressure is carried out for 2 hours, so as to prepare the modified polysiloxane auxiliary C11, the structural formula of which is as follows:
example 12
Procedure as in example 9;
step two:
the molar ratio of the dodecyl modified cyclotetrasiloxane A1, the octamethyl cyclotetrasiloxane, the long-chain polyether modified cyclotetrasiloxane B2 and the hexamethyldisiloxane is 1:4:7:1 adding the mixture into a flask, stirring for 1h at the temperature of 100 ℃, slowly adding tetramethylammonium hydroxide with the total mass of 0.5% into the mixture after uniformly stirring, stirring for 0.5h, and then heating to the temperature of 150 ℃ for continuous reaction for 8h; after the reaction is finished, the temperature is increased to 180 ℃ and reduced pressure is carried out for 2 hours, so as to prepare the modified polysiloxane auxiliary C12, the structural formula of which is as follows:
< test example >
Test example-Performance test applied to PP
The modified polysiloxane auxiliary C1-C12 (auxiliary for short) prepared in the examples 1-12 is applied to the processing of PP plastics, and extrusion granulation is carried out by a double screw experimental machine, so that the change of the processing performance (namely the extrusion current reaction lubrication effect) is examined under the same extrusion process condition; and using a torque rheometer to perform capillary extrusion to inspect the die orifice accumulation condition, and adopting a No. 4 capillary; and after the sheet is molded by an injection molding machine, the sheet is subjected to constant temperature and humidity and water boiling at 70 ℃ for 24 hours to examine the precipitation condition. The formulation was formulated at 2Kg and the formulation is shown in tables 1 and 2.
Note that: the antioxidant is antioxidant 1010, tetra [ beta- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionic acid]Pentaerythritol esters; the ultraviolet absorbent is UV-P,2- (2-hydroxy-5-methylphenyl) benzotriazole.
The properties of the auxiliaries synthesized in the examples and comparative examples, the processability and extrusion properties of the auxiliaries added to PP, and the presence or absence of precipitation after thermal oxidative aging and water boiling at 70℃for 24 hours are shown in Table 3.
TABLE 3 influence of the adjuvant State and on PP processing and precipitation
Description: the extruder current was tested under the same extruder set-up parameters. The capillary extrusion die port accumulation is measured by adopting a torque rheometer to extrude the capillary at 200 ℃ and 120 rpm; the constant temperature and humidity precipitation test condition is that whether precipitation exists on the surface of the injection molding piece after the injection molding piece is placed in a constant temperature and humidity test box for 28 days at 80 ℃ and 80 percent humidity; the water boiling precipitation test is to observe whether precipitation exists on the water surface and the surface of a workpiece after water boiling for 24 hours at 70 ℃.
From the results in Table 3, it is clear that under the same conditions, the various additives in the examples all have good lubrication effect and can reduce the accumulation of extrusion dies at high speed and high pressure.
The above description is only of the preferred embodiments of the present invention and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (8)
1. A long-chain alkyl-polar group co-modified polysiloxane is characterized by having a structural formula shown in (I):
（I）
R 1 、R 2 、R 3 、R 4 、R 5 、R 6 are monovalent organic groups or atoms independent of each other; m, n and r are integers more than or equal to 4;
the R is 1 Methyl or ethyl;
the R is 2 Is long-chain alkyl, the structure is shown as a general formula (I-1),
（I-1）
a is an integer greater than 8;
the R is 3 、R 4 Methyl, ethyl, propyl, phenyl, vinyl, hydroxyl or a hydrogen atom;
the R is 5 Is methyl or ethyl, said R 6 Is a long-chain organic group containing a polar structure.
2. The long-chain alkyl-polar group co-modified polysiloxane according to claim 1, wherein R 6 Is long-chain polyether group, long-chain polyester group, long-chain polyamide group, long-chain polyacrylic group and long-chainA long chain polyacrylate group, a long chain polymethacrylate group, a long chain polystyrene group, a long chain polyurethane group, a long chain polyacrylic acid-styrene group, a long chain polyacrylate-styrene group, a long chain polymethacrylate-styrene group, a long chain polyacrylamide-amine group, a long chain polyacrylate-styrene group, a long chain polyacrylamide-methyl acrylate group, a long chain polyacrylamide-methyl methacrylate group, a long chain polyacrylamide-maleic anhydride group, a long chain polystyrene-maleic anhydride group, a long chain polymethyl acrylate-maleic anhydride group, or a long chain polymethyl methacrylate-maleic anhydride group.
3. A process for the preparation of a long chain alkyl-polar group co-modified polysiloxane according to any one of claims 1 to 2, comprising the steps of:
s1, preparing cyclosiloxane containing long-chain alkyl groups and cyclosiloxane containing polar groups;
s2, mixing cyclosiloxane containing long-chain alkyl, cyclosiloxane containing polar groups, octamethyl cyclotetrasiloxane, a blocking agent and a catalyst, and carrying out ring opening polymerization to obtain a finished product.
4. A method of preparing a long chain alkyl-polar group co-modified polysiloxane according to claim 3, wherein S2 comprises at least one of features (1) to (5):
(1) The end-capping agent is hexamethyldisiloxane;
(2) The catalyst comprises at least one of sodium hydroxide, potassium hydroxide, sodium hydride, potassium hydride, tetramethylammonium hydroxide and tetrabutylammonium hydroxide;
(3) The total amount of the raw materials is as follows: the molar ratio of the cyclosiloxane containing long-chain alkyl to the octamethyl cyclotetrasiloxane to the cyclosiloxane containing polar groups to the end capping agent is 10-99:10-99:1-40;
(4) The catalyst accounts for 0.1-2wt% of the total weight of the raw materials;
(5) The reaction temperature is 100-200 ℃.
5. The method for preparing a long-chain alkyl-polar group co-modified polysiloxane according to claim 4, wherein in S1, the structure of the long-chain alkyl-containing cyclosiloxane is represented by the general formula (II):
（II）
R 1 methyl or ethyl; r is R 2 Is long-chain alkyl, the structure of which is shown as the general formula (I-1),
（I-1）
a is an integer greater than 8.
6. The method for preparing long-chain alkyl-polar group co-modified polysiloxane according to claim 5, wherein the method for preparing long-chain alkyl-containing cyclosiloxane is that hydrogen-containing cyclosiloxane and unsaturated alkane are prepared through catalytic reaction; comprising at least one of the features (1) to (4):
(1) The catalyst is a platinum catalyst;
(2) The catalyst accounts for 0.1-2wt% of the total weight of the reactants;
(3) The reaction temperature is 60-200 ℃;
(4) The reaction time is 6-10 h.
7. The method for preparing a long-chain alkyl-polar group co-modified polysiloxane according to claim 4, wherein in S1, the structure of the polar group-containing cyclosiloxane is represented by general formula (III):
（III）
R 5 is methyl or ethyl, R 6 Is a junction containing polarityLong chain organic groups of the structure.
8. The method for producing a long-chain alkyl-polar group co-modified polysiloxane according to claim 7, wherein the polar group-containing cyclosiloxane is produced by a catalytic reaction of a hydrogen-containing cyclosiloxane with a vinyl-containing long-chain polar polymer, and comprises at least one of the features (1) to (4):
(1) The catalyst is a platinum catalyst;
(2) The catalyst accounts for 0.1-2wt% of the total weight of the reactants;
(3) The reaction temperature is 60-200 ℃;
(4) The reaction time is 6-10 h.
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