CN107057035A - Double end-blocking dimethyl silicone polymers of a kind of pair of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl and its preparation method and application - Google Patents
Double end-blocking dimethyl silicone polymers of a kind of pair of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl and its preparation method and application Download PDFInfo
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- CN107057035A CN107057035A CN201610846431.9A CN201610846431A CN107057035A CN 107057035 A CN107057035 A CN 107057035A CN 201610846431 A CN201610846431 A CN 201610846431A CN 107057035 A CN107057035 A CN 107057035A
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- -1 methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl Chemical group 0.000 title claims abstract description 74
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 title claims abstract description 45
- 229920005573 silicon-containing polymer Polymers 0.000 title claims abstract description 45
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 claims abstract description 3
- 230000000694 effects Effects 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 7
- 238000001514 detection method Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 5
- 239000003921 oil Substances 0.000 claims description 5
- 238000007654 immersion Methods 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 238000005070 sampling Methods 0.000 claims description 2
- JZZIHCLFHIXETF-UHFFFAOYSA-N dimethylsilicon Chemical compound C[Si]C JZZIHCLFHIXETF-UHFFFAOYSA-N 0.000 claims 4
- 238000000034 method Methods 0.000 abstract description 11
- 239000000017 hydrogel Substances 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 230000008569 process Effects 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- 229920001296 polysiloxane Polymers 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 230000035699 permeability Effects 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 230000010148 water-pollination Effects 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 102100026735 Coagulation factor VIII Human genes 0.000 description 2
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 229910002808 Si–O–Si Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000004087 cornea Anatomy 0.000 description 2
- 229940113088 dimethylacetamide Drugs 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 230000010220 ion permeability Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- XJKVPKYVPCWHFO-UHFFFAOYSA-N silicon;hydrate Chemical compound O.[Si] XJKVPKYVPCWHFO-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- HEKCXLNLIMLZJU-UHFFFAOYSA-N C(C(=C)C)(=O)[N+]#[C-] Chemical class C(C(=C)C)(=O)[N+]#[C-] HEKCXLNLIMLZJU-UHFFFAOYSA-N 0.000 description 1
- 206010058490 Hyperoxia Diseases 0.000 description 1
- 238000012356 Product development Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 230000000222 hyperoxic effect Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- 238000005272 metallurgy Methods 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
Classifications
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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
- C08G18/81—Unsaturated isocyanates or isothiocyanates
- C08G18/8108—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
- C08G18/8116—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
-
- 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
- C08G18/61—Polysiloxanes
-
- 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
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
- G02C7/04—Contact lenses for the eyes
- G02C7/049—Contact lenses having special fitting or structural features achieved by special materials or material structures
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Ophthalmology & Optometry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Silicon Polymers (AREA)
Abstract
The invention discloses double end-blocking dimethyl silicone polymers of a kind of pair of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl and its preparation method and application, the general structure of the compound is as follows：
Description
Technical field：
The present invention relates to polysiloxane macromers technical field of compound preparation, and in particular to a kind of pair of methacryl
Double end-blocking dimethyl silicone polymers of oxygen ethylamino methanoyl ethoxycarbonyl propyl and its preparation method and application.
Background technology：
Polysiloxanes is the organic polymer synthetic material containing elemental silicon in molecular structure.Because Si-O-Si keys are longer,
Bond angle is larger, hence in so that Si-O-Si easily rotates.Intermolecular force is small and molecule is in high submissive state, causes polysiloxanes
With low glass transition temperature, surface tension and surface can, and solubility parameter and dielectric constant etc. are smaller.Polysiloxanes has
There are many excellent physics, a chemical property, such as high and low temperature resistance, radiation resistance, oxidative resistance, highly-breathable, weatherability, de-
Mould, hydrophobicity and physiological inertia etc., in electronic apparatus, chemical industry, metallurgy, building, space flight, aviation, medical material etc.
It is widely used in various fields.
It is balance eyes adaptability and user's comfort need in the soft contact lens worn daytime are designed, develops methyl
The polymer and copolymer of acrylic acid 2- hydroxyl ethyl esters.These hydrophilic polymers can well be moved on eyes and worn for daytime
Wear and sufficient oxygen permeability is provided.Some soft contact lens are ratified by FDA and widely used in the whole world.However, user
The extension time cycle of these polymethylacrylic acid 2- hydroxyl ethyl esters eyeglass to seven days or more can not be securely and comfortably worn, because
It is not enough for its oxygen permeability (Barrer of Dk ＜ 20).(such as, wear sleep in the evening) these mirrors are temporally worn in real extension
Piece may cause the expansion of vascular surface in cornea swelling and cornea.
To improve oxygen permeability, the polymer containing siloxy group is developed.Having been disclosed a variety of has hyperoxia impervious
The polymer of the silicone-containing of rate.For example, with reference to US3228741, US3341490, US3996187 and US3996189.However,
Polysiloxanes is typically highly lipophilic.Known polysiloxanes performance (for example lipophilicity, ultralow glass transition temperature,
High resiliency mechanical performance) cause contact lenses to adhere to eyes, suppress necessary eyeglass movement.In addition, the lipophilic of polysiloxanes
Property promote lipids and protein in tear fluid to stick at eyeglass, produce mist, interference passes through the sight of eyeglass.
To overcome the disadvantages mentioned above of polysiloxane-based contact lenses, it has thus been sought to which the lipophilicity for weakening polysiloxanes both improves it
Hydrophily, has synthesized containing polysiloxanes and hydrophilic radical and the monomer that can polymerize, has been successfully used to the silicon water of high oxygen transmission rate
Hydrogel contact lenses products.For example, with reference to US5010141, US5760100, US6312706, US6596294 and
US6762264.These silicone hydrogel contact lens products include Purevision, Night＆Day, AirOptix, etc..So
And, these monomers containing polysiloxanes it is complicated, generally comprise synthesis steps more than two steps, cause purification difficult, into
This height is looked forward to.Therefore, it is still necessary to which new synthesis is simple, inexpensively, hydrophily and the monomer of the polarity polysiloxanes of high oxygen transmission rate are had concurrently,
Silicone hydrogel contact lens product development for the Barrer of Dk ＞ 60.
The content of the invention：
1. the technical problem to be solved
To solve the problem of above-mentioned prior art is present, the invention provides double methacryloxypropyl ethylamino methanoyl second
Double end-blocking dimethyl silicone polymers of epoxide propyl group and preparation method thereof, using this pair of methacryloxypropyl ethylamino methanoyl second
The double end-blocking dimethyl silicone polymers of epoxide propyl group make the material of monomer, have the oxygen permeability of balance, ion permeability, in eyes
Upper movement and tears are exchanged, all these performances corneal health and wearer enough within the extension time cycle continuously worn
Feel comfortably cool.
2. technical scheme
Realize technical scheme that above-mentioned purpose of the present invention used for：
The double end-blocking dimethyl silicone polymers of a kind of pair of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl, its structure is led to
Formula is as follows：
Wherein n is 0-30 integer.
A kind of double methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyls double end-blocking poly dimethyls described in claim 1
The preparation method of siloxanes, it is characterised in that comprise the following steps：Under the effect of catalyst dibutyltin dilaurylate, hydroxyl ethoxy
The double end-blocking dimethyl silicone polymers of base propyl group and isocyanatoethyl react at 0-40 DEG C, and double methyl-props are made
The double end-blocking dimethyl silicone polymers of alkene acyl-oxygen ethylamino methanoyl ethoxycarbonyl propyl, the double end-blockings poly- two of described hydroxy ethoxy propyl group
Methylsiloxane structural formula is as follows：
Wherein n is 0-30 integer.
The preparation of the double end-blocking dimethyl silicone polymers of described double methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyls
Method, it is characterised in that：Described high selectivity prepares double double end-blockings of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl
The concrete operation step of dimethyl silicone polymer reaction is as follows：The double end-blockings of dry hydroxy ethoxy propyl group are added in dry reaction bottle
Dimethyl silicone polymer, then adds isocyanatoethyl, dibutyltin dilaurate catalyst is with stirrer one
Rise and add, in reaction bulb immersion oil bath, 0-40 DEG C of stir about 24h.Sampling detection.If the double poly- diformazans of end-blocking of hydroxy ethoxy propyl group
Radical siloxane does not have reaction complete, adds isocyanatoethyl, then reacts 24h, obtains double methacryloxypropyl second ammonia
The double end-blocking dimethyl silicone polymers of base methanoyl ethoxycarbonyl propyl.
The mol ratio of the double end-blocking dimethyl silicone polymers of hydroxy ethoxy propyl group and isocyanatoethyl is 1:
1.5-3.0。
The weight ratio of dibutyl tin laurate and the double end-blocking dimethyl silicone polymers of hydroxy ethoxy propyl group is 0.01%-
1%: 1.
The double end-blocking dimethyl silicone polymers of a kind of pair of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl are used for silicon water
The raw material of gel-like medicine equipment.
3. beneficial effect
Compared with prior art, its advantage and advantage are the present invention：
1) the double end-blocking poly dimethyls of a kind of pair of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl made from this method
Siloxanes is a kind of new polysiloxane macromers compound with certain polarity.
2) this method raw material is easy to get, and technological process is simple, and process conditions are easy to control, easy to operate, workable, and raw
Produce cost low.
3) the double end-blocking poly dimethyls of a kind of pair of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl made from this method
Siloxanes, monomer is made using the double end-blocking dimethyl silicone polymers of this pair of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl
Material.Because end group is big polar group, the more nonpolar dimethyl silicone polymer class monomer of the monomeric compound has one
Fixed hydrophily, it is easily miscible with other hydrophilic monomeric components in contact lenses polymer fluid.These hydrophilic monomers include exploitation
HEMA (HEMA), NVP (NVP), dimethyl acetamide (DMA), etc..Thus
The silicone hydrogel contact lens of preparation have the oxygen permeability balanced, ion permeability, moved on eyes and tears exchange,
Corneal health and wearer's all these performances feel comfortably cool within the extension time cycle continuously worn enough.
Embodiment：
Following examples are used to illustrate the present invention, but are not limited to the scope of application of the present invention.
Embodiment 1
A kind of preparation side of the double end-blocking dimethyl silicone polymers of pair of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl
Method, its step is：
N2The double end-blocking dimethyl silicone polymers of hydroxy ethoxy propyl group that 18.0g is dried are added in protection, dry reaction bottle, so
2.8g isocyanatoethyls are added afterwards, and 0.032g dibutyltin dilaurate catalysts are added together with stirrer,
In reaction bulb immersion oil bath, 25-35 DEG C of stir about 24h.Sample TLC points plate detection (solvent：Petroleum ether: ethyl acetate=4:
1, the colour developing of iodine cylinder).The double end-blocking dimethyl silicone polymers of hydroxy ethoxy propyl group do not have reaction complete, add 1.4g methacrylic acid isocyanides
Base ethyl ester, then 25-35 DEG C of stirring reaction about 24h.Sample TLC points plate detection (solvent：Petroleum ether: ethyl acetate=4: 1, iodine
Cylinder develops the color).The double end-blocking dimethyl silicone polymer reactions of hydroxy ethoxy propyl group are complete, obtain double methacryloxypropyl ethylamino formyls
The double end-blocking dimethyl silicone polymer 21.3g of oxygen ethoxycarbonyl propyl.1H NMR(CDCl3, 400MHz) compose and see accompanying drawing 1：δ 6.10 (s,
2H, C-H), 5.58 (s, 2H, C-H), 5.05 (s, 2H, NH), 4.21 (m, 8H, CH2), 3.59 (dd, 4H, CH2), 3.49 (dd,
4H, CH2), 3.39 (t, 4H, CH2), 1.93 (s, 6H, CH3), 1.60 (ddd, 4H, CH2), 0.51 (dt, 4H, CH2), -0.25-
0.25 (m, 114H, Si-CH3)。
As the above analysis, the organic compound is double double envelopes of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl
Dimethyl silicone polymer is held, its structural formula is as follows：
A kind of preparation side of the double end-blocking dimethyl silicone polymers of pair of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl
Method, its step is：
N2 is protected, and the double end-blocking dimethyl silicone polymers of hydroxy ethoxy propyl group that 18.0g is dried is added in dry reaction bottle, so
2.8g isocyanatoethyls are added afterwards, and 0.018g dibutyltin dilaurate catalysts are added together with stirrer,
In reaction bulb immersion oil bath, 25-35 DEG C of stir about 24h.Sample TLC points plate detection (solvent：Petroleum ether: ethyl acetate=4:
1, the colour developing of iodine cylinder).The double end-blocking dimethyl silicone polymer reactions of hydroxy ethoxy propyl group are complete, obtain double methacryloxypropyl ethylaminos
The double end-blocking dimethyl silicone polymer 21.1g of methanoyl ethoxycarbonyl propyl.1H NMR(CDCl3, 400MHz) compose and see accompanying drawing 2：δ6.10
(s, 2H, C-H), 5.57 (s, 2H, C-H), 5.07 (s, 2H, NH), 4.20 (m, 8H, CH2), 3.60 (dd, 4H, CH2), 3.48
(dd, 4H, CH2), 3.40 (t, 4H, CH2), 1.92 (s, 6H, CH3), 1.60 (ddd, 4H, CH2), 0.50 (dt, 4H, CH2) ,-
0.25-0.25 (m, 139H, Si-CH3)。
As the above analysis, the organic compound is double double envelopes of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl
Dimethyl silicone polymer is held, its structural formula is as follows：
Embodiment 3
A kind of preparation side of the double end-blocking dimethyl silicone polymers of pair of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl
Method, its step is：
The double end-blocking dimethyl silicone polymers of hydroxy ethoxy propyl group that 18.1g is dried are added in dry reaction bottle, are then added
2.8g isocyanatoethyls, 0.018g dibutyltin dilaurate catalysts are added together with stirrer, reaction bulb
Immerse in oil bath, 25-35 DEG C of stir about 24h.Sample TLC points plate detection (solvent：Petroleum ether: ethyl acetate=4: 1, iodine cylinder
Colour developing).The double end-blocking dimethyl silicone polymer reactions of hydroxy ethoxy propyl group are complete, obtain double methacryloxypropyl ethylamino methanoyls
The double end-blocking dimethyl silicone polymer 21.2g of ethoxycarbonyl propyl.1H NMR(CDCl3, 400MHz) compose and see accompanying drawing 3：δ 6.09 (s, 2H,
C-H), 5.57 (s, 2H, C-H), 5.07 (s, 2H, NH), 4.20 (m, 8H, CH2), 3.59 (dd, 4H, CH2), 3.48 (dd, 4H,
CH2), 3.40 (t, 4H, CH2), 1.92 (s, 6H, CH3), 1.59 (ddd, 4H, CH2), 0.50 (dt, 4H, CH2), -0.25-0.25
(m, 134H, Si-CH3)。
As the above analysis, the organic compound is double double envelopes of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl
Dimethyl silicone polymer is held, its structural formula is as follows：
Brief description of the drawings
The embodiment 1 of accompanying drawing 1.1H H NMR spectroscopies.
The embodiment 2 of accompanying drawing 2.1H H NMR spectroscopies.
The embodiment 3 of accompanying drawing 3.1H H NMR spectroscopies.
Claims (5)
1. the double end-blocking dimethyl silicone polymers of a kind of pair of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl, its general structure
It is as follows：
Wherein n is 0-30 integer.
2. the double end-blocking poly dimethyl silicon of double methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyls described in a kind of claim 1
The preparation method of oxygen alkane, it is characterised in that comprise the following steps：Under the effect of catalyst dibutyltin dilaurylate, hydroxy ethoxy
The double end-blocking dimethyl silicone polymers of propyl group and isocyanatoethyl react at 0-40 DEG C, and double metering systems are made
The double end-blocking dimethyl silicone polymers of acyl-oxygen ethylamino methanoyl ethoxycarbonyl propyl, the double poly- diformazans of end-blocking of described hydroxy ethoxy propyl group
Radical siloxane general structure is as follows：
Wherein n is 0-30 integer.
3. the double end-blocking poly dimethyl silicon of according to claim 2 pair of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl
The preparation method of oxygen alkane, it is characterised in that：Described high selectivity prepares double methacryloxypropyl ethylamino methanoyl ethyoxyls
The concrete operation step of the double end-blocking dimethyl silicone polymer reactions of propyl group is as follows：Dry hydroxy ethoxy is added in dry reaction bottle
The double end-blocking dimethyl silicone polymers of propyl group, then add isocyanatoethyl, dibutyltin dilaurate catalyst
Added together with stirrer, in reaction bulb immersion oil bath, 0-40 DEG C of stir about 24h.Sampling detection.If hydroxy ethoxy propyl group is double
End-blocking dimethyl silicone polymer does not have reaction complete, adds isocyanatoethyl, then reacts 24h, obtains double methyl-props
The double end-blocking dimethyl silicone polymers of alkene acyl-oxygen ethylamino methanoyl ethoxycarbonyl propyl.
4. the double end-blocking poly dimethyl silicon of according to claim 2 pair of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl
The preparation method of oxygen alkane, it is characterised in that：The double end-blocking dimethyl silicone polymers of hydroxy ethoxy propyl group and methacrylic acid isocyano group
The mol ratio of ethyl ester is 1: 1.5-3.0.
5. the double end-blocking poly dimethyl silicon of according to claim 2 pair of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl
The preparation method of oxygen alkane, it is characterised in that：Dibutyl tin laurate and the double end-blocking dimethyl silicone polymers of hydroxy ethoxy propyl group
Weight ratio be 0.01%-1%: 1.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610846431.9A CN107057035A (en) | 2016-09-18 | 2016-09-18 | Double end-blocking dimethyl silicone polymers of a kind of pair of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl and its preparation method and application |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610846431.9A CN107057035A (en) | 2016-09-18 | 2016-09-18 | Double end-blocking dimethyl silicone polymers of a kind of pair of methacryloxypropyl ethylamino methanoyl ethoxycarbonyl propyl and its preparation method and application |
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| CN109602941A (en) * | 2018-11-27 | 2019-04-12 | 吉林大学 | A kind of high oxygen permeability hydrogel dressing and preparation method thereof |
| CN116535651A (en) * | 2023-03-20 | 2023-08-04 | 华诺森（武汉）生物医药技术有限公司 | Macromolecular organic silicon monomer for silicon hydrogel contact lens and preparation method and application thereof |
| CN118006051A (en) * | 2024-04-08 | 2024-05-10 | 寿光福麦斯轮胎有限公司 | Rubber composition for tire inner liner and preparation method thereof |
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| CN109602941B (en) * | 2018-11-27 | 2021-07-13 | 吉林大学 | A kind of high oxygen permeability hydrogel dressing and preparation method thereof |
| CN116535651A (en) * | 2023-03-20 | 2023-08-04 | 华诺森（武汉）生物医药技术有限公司 | Macromolecular organic silicon monomer for silicon hydrogel contact lens and preparation method and application thereof |
| CN118006051A (en) * | 2024-04-08 | 2024-05-10 | 寿光福麦斯轮胎有限公司 | Rubber composition for tire inner liner and preparation method thereof |
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