CN105418669A - Alkoxy silane acetylenic silicon hydrogen addition inhibitor and preparation method thereof - Google Patents
Alkoxy silane acetylenic silicon hydrogen addition inhibitor and preparation method thereof Download PDFInfo
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- CN105418669A CN105418669A CN201510900212.XA CN201510900212A CN105418669A CN 105418669 A CN105418669 A CN 105418669A CN 201510900212 A CN201510900212 A CN 201510900212A CN 105418669 A CN105418669 A CN 105418669A
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- Prior art keywords
- acetylenic
- alkoxy silane
- degree
- inhibitor
- silicon hydrogen
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- Granted
Links
- -1 Alkoxy silane Chemical compound 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 29
- 239000003112 inhibitor Substances 0.000 title abstract description 16
- 229910052710 silicon Inorganic materials 0.000 title abstract description 13
- 239000010703 silicon Substances 0.000 title abstract description 13
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title abstract description 11
- 239000001257 hydrogen Substances 0.000 title abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 title abstract description 11
- 229910000077 silane Inorganic materials 0.000 title abstract 9
- 238000000034 method Methods 0.000 claims abstract description 8
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 37
- JQZGUQIEPRIDMR-UHFFFAOYSA-N 3-methylbut-1-yn-1-ol Chemical compound CC(C)C#CO JQZGUQIEPRIDMR-UHFFFAOYSA-N 0.000 claims description 21
- 238000007259 addition reaction Methods 0.000 claims description 21
- 238000004821 distillation Methods 0.000 claims description 19
- 239000002683 reaction inhibitor Substances 0.000 claims description 19
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 claims description 13
- 229920001296 polysiloxane Polymers 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 235000015320 potassium carbonate Nutrition 0.000 claims description 8
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 6
- 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 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000001632 sodium acetate Substances 0.000 claims description 6
- 235000017281 sodium acetate Nutrition 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052728 basic metal Inorganic materials 0.000 claims description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 150000003606 tin compounds Chemical class 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 20
- 229920002379 silicone rubber Polymers 0.000 abstract description 7
- 230000001988 toxicity Effects 0.000 abstract description 5
- 231100000419 toxicity Toxicity 0.000 abstract description 5
- 239000003292 glue Substances 0.000 abstract description 3
- 238000003860 storage Methods 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 2
- 125000000962 organic group Chemical group 0.000 abstract description 2
- 230000007547 defect Effects 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 46
- 239000007788 liquid Substances 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 32
- 238000005160 1H NMR spectroscopy Methods 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- 238000010992 reflux Methods 0.000 description 23
- 239000000047 product Substances 0.000 description 20
- 239000003921 oil Substances 0.000 description 18
- 238000009835 boiling Methods 0.000 description 15
- 238000004513 sizing Methods 0.000 description 12
- 238000001816 cooling Methods 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000000605 extraction Methods 0.000 description 7
- 238000010792 warming Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000006459 hydrosilylation reaction Methods 0.000 description 5
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000004945 silicone rubber Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 2
- 239000004324 sodium propionate Substances 0.000 description 2
- 229960003212 sodium propionate Drugs 0.000 description 2
- 235000010334 sodium propionate Nutrition 0.000 description 2
- 238000005987 sulfurization reaction Methods 0.000 description 2
- LMVLVUPTDRWATB-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-ol Chemical compound CO[Si](C)(OC)CCCO LMVLVUPTDRWATB-UHFFFAOYSA-N 0.000 description 1
- UVKLRHLCKNMNHI-UHFFFAOYSA-N COC1(CCCCC1)N Chemical compound COC1(CCCCC1)N UVKLRHLCKNMNHI-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- VSYLGGHSEIWGJV-UHFFFAOYSA-N diethyl(dimethoxy)silane Chemical compound CC[Si](CC)(OC)OC VSYLGGHSEIWGJV-UHFFFAOYSA-N 0.000 description 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- HTSRFYSEWIPFNI-UHFFFAOYSA-N ethyl-dimethoxy-methylsilane Chemical compound CC[Si](C)(OC)OC HTSRFYSEWIPFNI-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229920000260 silastic Polymers 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
-
- C07F7/045—
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
The invention relates to an alkoxy silane acetylenic silicon hydrogen addition inhibitor and a preparation method thereof. The alkoxy silane acetylenic silicon hydrogen addition inhibitor uses alkynol and alkoxy silane as main materials, and an inhibitor which is added through alkoxy silane acetylenic silicon hydrogen is generated under the action of a catalyst. The method for preparing the alkoxy silane acetylenic silicon hydrogen addition inhibitor is simple, the alkoxy silane acetylenic silicon hydrogen addition inhibitor which is obtained through the method for preparing the alkoxy silane acetylenic silicon hydrogen addition inhibitor can overcome the defects that alkynol inhibitors and base glue are poor in compatibility, are easy to volatilize and residue has toxicity and the like. The alkoxy silane acetylenic silicon hydrogen addition inhibitor can prolong storage life in room temperature by being used in additional liquid silicone rubbers, enables the surfaces of the additional liquid silicone rubbers to be smooth after being solidified, can improve bonding with base materials through organic groups which are connected with the inhibitor, and gives better bonding force to glue.
Description
Technical field
The present invention relates to organosilicon material field, be specifically related to a kind of multifunction alkoxyl silicone alkanisation acetylene series Si―H addition reaction inhibitor and preparation method thereof.
Background technology
Addition reaction of silicon with hydrogen is from the people such as Sommer (SommerLH, PietruszaEW, WhitmoreFC.Peroxide-catalyzedadditionoftrichlorosilaneto 1-octene [J] .JournaloftheAmericanChemicalSociety, 1947,69 (1): 188-188.) since finding, become one of most important reaction in organosilicon chemistry, had a wide range of applications in synthesis carbon official energy silicoorganic compound/polymkeric substance, Carbonsilane dendrimer and addition-type silicon rubber sulfuration etc.Addition reaction of silicon with hydrogen speed needs to need to carry out appropriate regulation according to use.Such as in addition-type silicon rubber, for adapting to perfusion, coating or injection molding technique needs, after two the component mixing of dual composition addition type liquid silastic, require the serviceable time having more than 4 hours at least; Single-component add-on type liquid silicon rubber, under room temperature can long time stored ability meaningful.And must complete fast once generation hydrosilation reaction.In order to reach such object, modal is also that the most practical method adds Si―H addition reaction inhibitor exactly in hydrosilation system.Si―H addition reaction inhibitor effectively can suppress catalyst hydrosilation reaction in certain temperature range, and after being heated to curing temperature, Si―H addition reaction inhibitor loses inhibit feature and hydrosilation reaction is occurred fast.
At present, alkynol compound is use the most general Si―H addition reaction inhibitor as methylbutynol and ethynylcyclohexanol, at room temperature has good restraining effect.Si―H addition reaction inhibitor is can be used as United States Patent (USP) (US3445420) discloses alkynol compound.But these alkynol compound have easy volatile and the problem such as organosilicon systems poor compatibility and toxicity.Wherein easy volatile can cause in the mixing deaeration technique of inhibitor before two-component silicone rubber uses volatile, makes inhibitor content unstable, and after causing sulfuration, rubber surface wrinkle is uneven, also result in waste of raw materials and environment murder by poisoning.And due to the fusing point (30-33 DEG C) of ethynylcyclohexanol lower, at room temperature can solidify precipitation, affect sizing material stability in storage.Therefore, some obtain application to the mode that alkynol carries out modification.As the volatility in order to reduce alkynol compound, Dow Corning Corporation discloses a kind of silylated acetylenic inhibitor
(US3445420), this compounds can well be dissolved in sizing material, also reduces the yellow of reaction product simultaneously.But owing to losing the hydroxyl of alkynol, its volatility is still larger.The acetylene series inhibitor of the polysiloxane that methylhydrogenpolysi,oxane and alkynol are obtained by dehydrogenation reaction
(US3933882) volatility, toxicity and and the compatibility problem of sizing material, is completely solved.But its remaining silicon hydrogen will cause A glue stability in storage in two-component silicone rubber to be deteriorated.
In order to overcome current technological difficulties, the invention discloses a class multifunction alkoxyl silicone alkanisation acetylene series Si―H addition reaction inhibitor, significantly can reduce the volatility of alkynol class inhibitor, reduce the toxicity of residue, increase and the consistency of sizing material; Simultaneously active silicon alkoxyl group can react or self hydrolytic crosslinking with the white carbon black in sizing material or other compound containing activity hydroxy, participates in solidification; Also can react with base material the bonding force increasing sizing material and base material.
Summary of the invention
The present invention, in conjunction with the technical foundation of existing acetylene series Si―H addition reaction inhibitor, discloses class multifunction alkoxyl silicone alkanisation acetylene series Si―H addition reaction inhibitor and preparation method thereof.
Multifunction alkoxyl silicone alkanisation acetylene series Si―H addition reaction inhibitor provided by the present invention can significantly reduce alkynol class inhibitor volatility, increase and the consistency of sizing material, simultaneously active silicon alkoxyl group can react or self hydrolytic crosslinking with the white carbon black in sizing material or other compound containing activity hydroxy, participates in solidification.Also can react with base material the bonding force increasing sizing material and base material.
Concrete technical scheme of the present invention is as follows:
A kind of multifunction alkoxyl silicone alkanisation acetylene series Si―H addition reaction inhibitor, structural formula is as follows:
Wherein: R
1for methyl or ethyl; R
2for methoxyl group, oxyethyl group or methyl, ethyl, n-propyl, phenyl or vinyl; R
3for methoxyl group, oxyethyl group, methyl, ethyl, n-propyl, chain alkyl (C
nh
2n+1-, its n>3), phenyl, methacryloxypropyl or (2,3-epoxy third oxygen) propyl group.
The present invention also provides the method preparing above-mentioned multifunction alkoxyl silicone alkanisation acetylene series Si―H addition reaction inhibitor, step is as follows: with methylbutynol or ethynylcyclohexanol for raw material, mix with organoalkoxysilane, add catalyzer, react 6-24 hour under 20-100 degree condition after, removing low-boiling-point substance, obtains product after directly obtaining product or distillation;
Wherein the molar feed ratio of alkoxysilane compound containing trialkylsilyl group in molecular structure and methylbutynol or ethynylcyclohexanol compound is 0.25 ~ 4;
Described catalyzer is one or more in tin compound, titanate ester compound, alkaline carbonate or basic metal organic acid salt.
Described tin compound is dibutyl tin dilaurate; Described titanate ester compound is tetrabutyl titanate; Described alkaline carbonate is salt of wormwood, described basic metal organic acid salt is sodium acetate.
Beneficial effect of the present invention is embodied in:
1, multifunction alkoxyl silicone alkanisation acetylene series Si―H addition reaction inhibitor overcomes methylbutynol and ethynylcyclohexanol as Si―H addition reaction inhibitor consistency and volatile problem, makes the sizing material smooth surface after solidification smooth.
2, multifunction alkoxyl silicone alkanisation acetylene series Si―H addition reaction inhibitor can participate in other reaction and combine together with sizing material, the toxicity problem solving volatility and remain and cause while suppression hydrosilation reaction.
3, the organic group that multifunction alkoxyl silicone alkanisation acetylene series Si―H addition reaction inhibitor connects can improve the bonding problem with base material, gives sizing material better bonding force.
4, synthetic route is simple, and generate without side reaction product, raw material is cheaply easy to get, reaction favorable reproducibility.
Embodiment
Following examples further illustrate content of the present invention, but should not be construed as limitation of the present invention.Without departing from the spirit and substance of the case in the present invention, the amendment do the inventive method, step or condition or replacement, all belong to scope of the present invention.
Embodiment one,
preparation
Magneton is being housed, reflux condensing tube, 8.4g (0.1mol) methylbutynol is added successively, 30.4g (0.2mol) tetramethoxy-silicane, 0.1g dibutyl tin dilaurate in three mouthfuls of round-bottomed flasks of the 250ml of bubbler and logical nitrogen device.React 6 hours at 60 degree of temperature, obtain weak yellow liquid.Be cooled to room temperature, oil pump underpressure distillation removing low-boiling-point substance, underpressure distillation obtains colourless transparent liquid 21.7g.
1H-NMR(CDCl
3)δ[ppm]:3.59(s,9H,OCH
3),2.45(s,1H,-C≡C-H),1.58(s,6H,-CH
3)
Embodiment two,
preparation
Magneton is being housed, reflux condensing tube, is adding successively in 250ml tri-mouthfuls of round-bottomed flasks of bubbler and logical nitrogen device, 12.4g (0.1mol) ethynylcyclohexanol, 30.4g (0.2mol) tetramethoxy-silicane, 0.1g butyl (tetra) titanate.React 24 hours at 60 degree of temperature, obtain blood red liquid.Cooling, oil pump underpressure distillation removing low-boiling-point substance, then be warming up to 90 degree, extract product, obtain colourless transparent liquid 24.0g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:3.60(s,9H,OCH
3)，2.53(s,-C≡C-H)，1.95(br,2H),1.69-1.59(m,5H),1.58-1.49(m,2H),1.26(br,1H)
Embodiment three,
preparation
Magneton is being housed, reflux condensing tube, adds 12.6g (0.15mol) methylbutynol, 44.4g (0.3mol) vinyltrimethoxy silane in 250ml tri-mouthfuls of round-bottomed flasks of bubbler and logical nitrogen device successively, 0.15g stannous iso caprylate, 90 degree of reactions 6 hours.After cooling, obtain weak yellow liquid, oil pump underpressure distillation removing low-boiling-point substance, then be warming up to 60 degree of extraction products, obtain colourless transparent liquid 29.5g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:6.16-5.88(m,3H,-CH＝CH
2),3.58(s,6H,OCH
3),2.45(s,1H,-C≡C-H),1.59(s,6H,-CH
3)
Embodiment 4,
preparation
Magneton is being housed, reflux condensing tube, 14.2g ethynylcyclohexanol (0.11mol) successively in 250ml tri-mouthfuls of round-bottomed flasks of bubbler and logical nitrogen device, 33.8g (0.23mol) vinyltrimethoxy silane, 0.12g salt of wormwood, 20 degree of reactions 20 hours.After cooling, centrifuging removing salt of wormwood.Oil pump underpressure distillation removing low-boiling-point substance, then be warming up to 90 degree of extraction products, obtain colourless transparent liquid 25.9g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:6.11-5.89(m,3H，-CH＝CH
2),3.54(s,9H,OCH
3),2.49(s,-C≡C-H),1.89(br,2H),1.68-1.57(m,5H),1.55-1.48(m,2H),1.26(br,1H)
Embodiment 5,
preparation
Magneton is being housed, reflux condensing tube, in 250ml tri-mouthfuls of round-bottomed flasks of bubbler and logical nitrogen device, is adding 25.2g (0.3mol) methylbutynol successively, 40.8g (0.3mol) methyltrimethoxy silane, 0.3g sodium acetate.20 degree of reactions 18 hours.After cooling, centrifuging removing sodium acetate.Water pump underpressure distillation removing low-boiling-point substance, then the 90 degree of extraction products that heat up, obtain water white transparency product 55.41g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:3.55(s,6H,OCH
3),2.45(s,1H,-C≡C-H),1.57(s,6H,-CH
3),0.22(s,3H,Si-CH
3)
Embodiment 6,
preparation
Magneton is being housed, reflux condensing tube, 12.4g (0.1mol) ethynylcyclohexanol is added successively in 250ml tri-mouthfuls of round-bottomed flasks of bubbler and logical nitrogen device, 27.2g (0.2mol) methyltrimethoxy silane, 0.1g dibutyl tin dilaurate, 40 degree of reactions 24 hours.After cooling, obtain yellow liquid, oil pump underpressure distillation removing is low boil after, then be warming up to 90 degree and extract product, obtain colourless transparent liquid 22.60g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:3.55(s,6H,OCH
3),2.52(s,1H,-C≡C-H),1.91(br,2H),1.66-1.57(m,5H),1.56-1.48(m,2H),1.25(br,2H),0.22(s,3H,Si-CH
3)
Embodiment 7,
preparation
Magneton is being housed, reflux condensing tube, adds 25.2g (0.3mol) methylbutynol, 25.0g (0.126mol) phenyltrimethoxysila,e in 250ml tri-mouthfuls of round-bottomed flasks of bubbler and logical nitrogen device successively, 0.2g stannous iso caprylate, 90 degree of reactions 24 hours.Obtain yellow liquid.Oil pump 90 degree of underpressure distillation go out low boiling, then heat up 120 degree, distill out product, obtain colourless transparent liquid 30g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:7.70-7.68(m,2H,Ar-H),7.44-7.37(m,3H,Ar-H),3.63(s,6H,OCH
3),2.42(s,1H,-C≡C-H),1.61(s,6H,-CH
3).
Embodiment 8,
preparation
Magneton is being housed, reflux condensing tube, adds 49.6g (0.4mol) ethynylcyclohexanol, 19.6g (0.1mol) phenyltrimethoxysila,e in 250ml tri-mouthfuls of round-bottomed flasks of bubbler and logical nitrogen device successively, 0.2g Sodium Propionate, 90 degree of reactions 20 hours.Cooled and filtered removing Sodium Propionate, obtain transparent liquid again 150 degree, oil pump extract low-boiling-point substance, obtain colourless transparent liquid 27.2g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:7.68-7.65(m,2H,Ar-H),7.40-7.35(m,3H,Ar-H),3.59(s,6H,OCH
3),2.46(s,1H,-C≡C-H),1.90(br,2H),1.66-1.56(m,5H),1.22(br,1H).
Embodiment 9,
preparation
Magneton is being housed, reflux condensing tube, 24.8g (0.2mol) ethynylcyclohexanol is added successively in 250ml tri-mouthfuls of round-bottomed flasks of bubbler and logical nitrogen device, 30.4g (0.2mol) ethyl trimethoxy silane, 0.2g sodium carbonate, 70 degree of reactions 15 hours, cooled and filtered removing sodium carbonate, obtain transparent liquid and extract low boiling with oil pump 60 degree of underpressure distillation again, then the 90 degree of extraction products that heat up.
1H-NMR(CDCl
3,300MHz)δ[ppm]:3.57(s,6H,Si-OCH
3),2.51(s,1H,-C≡C-H),1.89(br,2H),1.66-1.56(m,5H),1.55-1.48(m,2H),1.26(br,1H),1.01(t,3H,-CH
3),0.602(q,2H,-SiCH
2-).
Embodiment 10,
preparation
Magneton is being housed, reflux condensing tube, 16.8g (0.2mol) methylbutynol is added successively in 250ml tri-mouthfuls of round-bottomed flasks of bubbler and logical nitrogen device, 41.6g (0.2mol) n-propyl triethoxyl silane, 0.2g dibutyl tin laurate, 0.15g stannous iso caprylate.Obtain yellow liquid.80 degree of reactions 12 hours, oil pump 50 degree of underpressure distillation removings are low boils, 80 degree extraction products.Obtain colourless transparent liquid 42.6g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:3.95-3.84(q,4H,OCH
2-),2.44(s,1H,-C≡C-H),1.61(s,6H,-CH
3),1.45(m,2H,-CH
2-),1.22(s,6H,-CH
3),0.96(t,3H,-CH
3),0.69-0.62(m,2H,Si-CH
2-).
Embodiment 11,
preparation
Magneton is being housed, reflux condensing tube, 25.2g (0.3mol) methylbutynol is added successively, 25.0g (0.1mol) γ-methacryloxypropyl trimethoxy silane, 0.1g sodium propylate in 250ml tri-mouthfuls of round-bottomed flasks of bubbler and logical nitrogen device.90 degree of reactions 24 hours.Reaction terminates rear cooling, crosses and filters sodium propylate.Extract low boiling with 150 degree, oil pump again, obtain colourless transparent liquid 27g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:6.09(s,1H),5.54(s,1H),4.11(t,2H,-CH
2-),3.57(s,6H,OCH
3),2.45(s,1H,-C≡C-H),1.93(s,3H,-CH
3),1.83-1.73(m,2H,-CH
2-),1.57(s,6H,-CH
3),0.77-0.66(m,2H,Si-CH
2-).
Embodiment 12,
preparation
Magneton is being housed, reflux condensing tube, adds 25.3g (0.3mol) methylbutynol, 23.6g (0.1mol) (2 in 250ml tri-mouthfuls of round-bottomed flasks of bubbler and logical nitrogen device successively, 3-epoxy third oxygen) propyl trimethoxy silicane, 0.1g salt of wormwood.90 degree of reactions 24 hours.Reaction terminates rear cooling, crosses and filters salt of wormwood.150 degree, oil pump pumps low boiling, and obtains colourless transparent liquid 26.4g.
1H-NMR(CDCl3,300MHz)δ[ppm]:3.62(d,1H,-CH
2-),3.57-3.40(m,9H),3.14(br,1H,-CH-),2.79-2.59(m,2H,-CH
2-),2.46(s,1H,-C≡C-H),1.67-1.69(m,2H,-CH
2),1.57(s,6H,-CH
3),0.64-0.70(m,2H,Si-CH
2-).
Embodiment 13,
preparation
Magneton is being housed, reflux condensing tube, adds 20.8g (0.1mol) tetraethoxysilane, 16.8g (0.2mol) methylbutynol in 250ml tri-mouthfuls of round-bottomed flasks of bubbler and logical nitrogen device successively, 0.1g butyl (tetra) titanate, 90 degree of reactions 12 hours.Obtain yellow liquid, go low boiling with oil pump 50 degree of underpressure distillation, then be warming up to 70 degree of extraction products, obtain colourless transparent liquid 24.8g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:3.90-3.84(q,6H,OCH
2-),2.43(s,1H,-C≡C-H),1.59(s,6H,-CH
3),1.48(m,6H,-CH
2-)1.24(t,9H,-CH
3).
Embodiment 14,
preparation
Magneton is being housed, reflux condensing tube, 12.4g (0.1mol) ethynylcyclohexanol is added successively, 76.8g (0.4mol) ethyl triethoxysilane, 0.1g Dibutyltin oxide in 250ml tri-mouthfuls of round-bottomed flasks of bubbler and logical nitrogen device.60 degree of reactions 24 hours.Cooled and filtered removing Dibutyltin oxide, low boiling is gone in oil pump 60 degree of underpressure distillation, and 110 degree are extracted product, obtain colourless transparent liquid 28.1g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:3.85-3.77(q,4H,OCH
2-),2.51(s,1H,-C≡C-H),1.89(br,2H),1.68-1.59(m,5H),1.58-1.49(m,2H),1.45(m,4H,-CH
2-),1.30(br,1H),1.22(t,6H,-CH
3),1.03(t,3H,-CH
3),0.63(q,2H,Si-CH
2-).
Embodiment 15,
preparation
Magneton is being housed, reflux condensing tube, 12.4g (0.1mol) ethynylcyclohexanol is added successively, 39.6g (0.3mol) dimethoxymethylvinylchlane, 0.1g butyl (tetra) titanate in 250ml tri-mouthfuls of round-bottomed flasks of bubbler and logical nitrogen device.40 degree of reactions 24 hours.Cooling rear pump or output pump 50 degree goes low boiling, and 90 degree are extracted product, obtain water white transparency product 22.3g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:6.08-5.84(m,3H,-CH＝CH
2),3.58(s,3H,OCH
3),2.52(s,1H,-C≡C-H),1.95(br,2H),1.68-1.59(m,5H),1.58-1.47(m,2H),1.27(br,1H),0.22(s,3H,Si-CH
3).
Embodiment 16,
preparation
Magneton is being housed, reflux condensing tube, 25.2g (0.3mol) methylbutynol is added successively in 250ml tri-mouthfuls of round-bottomed flasks of bubbler and logical nitrogen device, 22.0g (0.1mol) 3-[(2,3)-epoxy third oxygen] hydroxypropyl methyl dimethoxysilane, 0.1g sodium acetate, 90 degree of reaction 36h.Reaction terminates cooling, and cross and filter sodium acetate, 120 degree, oil pump goes low boiling, and obtains colourless transparent liquid 25.8g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:3.62(d,1H,-CH
2-),3.57-3.40(m,6H),3.14(br,1H,-CH-),2.79-2.59(m,2H,-CH
2-),2.46(s,1H,-C≡C-H),1.67-1.69(m,2H,-CH
2-),1.57(s,6H,-CH
3),0.64-0.70(m,2H,-CH
2-),0.20(s,3H,Si-CH
3).
Embodiment 17,
preparation
Magneton is being housed, reflux condensing tube, adds 25.2g (0.3mol) methylbutynol in the 250ml there-necked flask of bubbler and logical nitrogen device, 23.2g (0.1mol) γ-methacryloxypropyl trimethoxy silane, 0.1g salt of wormwood, 90 degree of reactions 24 hours.Reaction terminates rear cooling, and cross and filter salt of wormwood, 120 degree, oil pump pumps low boiling, and obtains colourless transparent liquid 27.2g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:6.09(s,1H),5.54(s,1H),4.11(t,2H),3.57(s,3H,OCH
3),2.45(s,1H,-C≡C-H),1.93(s,3H,-CH
3),1.83-1.73(m,2H,-CH
2-),1.567(s,6H,-CH
3),0.77-0.66(m,2H,-CH
2-),0.21(s,3H,-CH
3).
Embodiment 18,
preparation
Magneton is being housed, reflux condensing tube, in the 250ml there-necked flask of bubbler and logical nitrogen device, is adding 16.8g (0.2mol) methylbutynol, 18.2g (0.1mol) aminomethyl phenyl and methoxy silane, 0.1g dibutyl tin laurate.60 degree of reactions 24 hours.Oil pump 100 degree of underpressure distillation pump low boiling, and 120 degree are extracted product, obtain colourless transparent liquid 29.0g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:7.65-7.60(m,2H,Ar-H),7.41-7.35(m,3H,Ar-H),3.60(s,6H,OCH
3),2.43(s,1H,-C≡C-H),1.61(s,3H,-CH
3),0.21(s,3H,-CH
3).
Embodiment 19,
preparation
Magneton is being housed, reflux condensing tube, 8.4g (0.1mol) methylbutynol is added in the 250ml there-necked flask of bubbler and logical nitrogen device, 24.4g (0.1mol) dimethoxydiphenylsilane, 0.1g butyl (tetra) titanate, 60 degree of reactions 24 hours, obtain yellow liquid, low boiling is gone in oil pump 120 degree of underpressure distillation, being warming up to 160 degree of extraction products, obtains colourless transparent liquid 27.9g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:7.65-7.60(m,4H,Ar-H),7.41-7.35(m,6H,Ar-H),3.61(s,3H,OCH
3),2.43(s,1H,-C≡C-H),1.63(s,3H,-CH
3),0.21(s,3H,Si-CH
3).
Embodiment 20,
preparation
Magneton is being housed, reflux condensing tube, 12.4g (0.1mol) ethynylcyclohexanol is added in the 250ml there-necked flask of bubbler and logical nitrogen device, 48g (0.4mol) dimethyldimethoxysil,ne, 0.1g stannous iso caprylate, 20 degree of reactions 24 hours, obtain yellow liquid, 60 degree, oil pump goes low boiling, and the 80 degree of underpressure distillation that heat up obtain colourless transparent liquid 22.1g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:3.55(s,3H,OCH
3),2.50(s,1H,-C≡C-H),1.87(br,2H),1.63-1.55(m,5H),1.54-1.46(m,2H),1.27(br,1H),0.20(s,6H,Si-CH
3).
Embodiment 21,
preparation
Magneton is being housed, reflux condensing tube, the 250ml there-necked flask of bubbler and logical nitrogen device adds 8.4g (0.1mol) methylbutynol successively, 26.8g (0.2mol) methylethyl dimethoxysilane, 0.1g sodium carbonate.60 degree of reactions 12 hours.Cold filtration removing sodium carbonate, low boiling is gone in water pump 60 degree of underpressure distillation, and 90 degree are extracted product, obtain colourless transparent liquid 19.0g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:3.51(s,3H,OCH
3),2.46(s,1H,-C≡C-H),1.59(6H,-CH
3),1.00(t,3H,-CH
3),0.65(q,2H,-CH
2-),0.19(3H,Si-CH
3).
Embodiment 22,
preparation
Magneton is being housed, reflux condensing tube, the 250ml there-necked flask of bubbler and logical nitrogen device adds 8.4g (0.1mol) methylbutynol successively, 14.8g (0.1mol) trimethoxysilyl propyl methacrylate TMOS, 0.1g stannous iso caprylate.80 degree of reactions 24 hours, obtain yellow liquid, 60 degree, water pump goes low boiling, and 90 degree are extracted products, obtain colourless transparent liquid 19.2g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:3.60(s,3H,OCH
3)2.47(s,1H,-C≡C-H),1.61(s,6H,-CH
3)，1.50(m,2H,-CH
2-),0.96(t,3H,-CH
3),0.69-0.62(m,2H,-CH
2-),0.19(s,3H,Si-CH
3).
Embodiment 23,
preparation
Magneton is being housed, reflux condensing tube, the 250ml there-necked flask of bubbler and logical nitrogen device adds 8.4g (0.1mol) methylbutynol successively, 29.6g (0.2mol) diethyldimethoxysilane, 0.1g butyl (tetra) titanate.90 degree of reactions 12 hours, obtain yellow liquid, low boiling is gone in water pump 60 degree of underpressure distillation, and 90 degree are extracted products, obtain colourless transparent liquid 19.7g.
1H-NMR(CDCl
3,300MHz)δ[ppm]:3.57(s,3H,OCH
3),2.45(s,1H,-C≡C-H),1.58(6H,-CH
3),1.00(t,6H,-CH
3),0.67(q,4H,Si-CH
2-)。
Claims (3)
1. a multifunction alkoxyl silicone alkanisation acetylene series Si―H addition reaction inhibitor, is characterized in that: structural formula is as follows:
Wherein: R
1for methyl or ethyl; R
2for methoxyl group, oxyethyl group or methyl, ethyl, n-propyl, phenyl or vinyl; R
3for methoxyl group, oxyethyl group, methyl, ethyl, n-propyl, chain alkyl (C
nh
2n+1-, its n>3), phenyl, methacryloxypropyl or (2,3-epoxy third oxygen) propyl group.
2. prepare the method for multifunction alkoxyl silicone alkanisation acetylene series Si―H addition reaction inhibitor as claimed in claim 1 for one kind, it is characterized in that: step is as follows: with methylbutynol or ethynylcyclohexanol for raw material, mix with organoalkoxysilane, add catalyzer, react 6-24 hour under 20-100 degree condition after, removing low-boiling-point substance, obtains product after directly obtaining product or distillation; Wherein the molar feed ratio of alkoxysilane compound containing trialkylsilyl group in molecular structure and methylbutynol or ethynylcyclohexanol compound is 0.25 ~ 4;
Described catalyzer is one or more in tin compound, titanate ester compound, alkaline carbonate or basic metal organic acid salt.
3. preparation method as claimed in claim 2, is characterized in that: described tin compound is dibutyl tin dilaurate; Described titanate ester compound is tetrabutyl titanate; Described alkaline carbonate is salt of wormwood, described basic metal organic acid salt is sodium acetate.
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Cited By (9)
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| CN108841005A (en) * | 2018-05-21 | 2018-11-20 | 山东省科学院新材料研究所 | Si―H addition reaction type silicone resin high-temperature catalytic inhibition system and its preparation method and application |
| CN109851629A (en) * | 2019-01-09 | 2019-06-07 | 上海交通大学 | A kind of preparation method of single-component silicon rubber silanization alkynyl inhibitor |
| CN110628221A (en) * | 2019-09-16 | 2019-12-31 | 东莞新东方科技有限公司 | Silanization inhibitor and preparation method thereof |
| CN111100297A (en) * | 2020-01-08 | 2020-05-05 | 东莞新东方科技有限公司 | Preparation method of addition type liquid silicone rubber inhibitor silanized acetylene cyclohexanol |
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