CN109575293A - A kind of preparation method of high polymerization degree backbone chain type organic silicon modified by polyether foam stabilizer - Google Patents
A kind of preparation method of high polymerization degree backbone chain type organic silicon modified by polyether foam stabilizer Download PDFInfo
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- CN109575293A CN109575293A CN201811429680.3A CN201811429680A CN109575293A CN 109575293 A CN109575293 A CN 109575293A CN 201811429680 A CN201811429680 A CN 201811429680A CN 109575293 A CN109575293 A CN 109575293A
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- aba
- modified silicon
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- silicone oil
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- 229920000570 polyether Polymers 0.000 title claims abstract description 30
- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 238000006116 polymerization reaction Methods 0.000 title abstract description 17
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title description 8
- 229910052710 silicon Inorganic materials 0.000 title description 8
- 239000010703 silicon Substances 0.000 title description 8
- 239000006260 foam Substances 0.000 title description 7
- 239000003381 stabilizer Substances 0.000 title description 4
- 229920002545 silicone oil Polymers 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 239000003921 oil Substances 0.000 claims abstract description 24
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 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 abstract description 5
- 239000012975 dibutyltin dilaurate Substances 0.000 claims abstract description 4
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 claims abstract 3
- 235000005513 chalcones Nutrition 0.000 claims abstract 3
- 229960002725 isoflurane Drugs 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
- 238000009413 insulation Methods 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 4
- 238000010792 warming Methods 0.000 claims description 4
- 229910002621 H2PtCl6 Inorganic materials 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 2
- 238000010907 mechanical stirring Methods 0.000 claims description 2
- 238000005292 vacuum distillation Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 abstract description 5
- 239000004970 Chain extender Substances 0.000 abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
- 238000007259 addition reaction Methods 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 abstract 1
- 238000001179 sorption measurement Methods 0.000 abstract 1
- 150000003376 silicon Chemical class 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000005058 Isophorone diisocyanate Substances 0.000 description 8
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 8
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- -1 oxygen alkane Chemical class 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses a kind of preparation methods of more block (ABA) N-shaped polyether modified silicon oils.Its technical solution are as follows: using chloroplatinic acid as catalyst, be catalyzed both-end containing hydrogen silicone oil and monoallyl polyethers reacts, obtain the hydroxy-end capped polyether modified silicon oil of three block through activated carbon adsorption.Again with the isoflurane chalcone diisocyanate Hybrid Heating that is added portionwise to 40 ~ 70 DEG C, in dibutyltindilaurate catalyzed lower generation addition reaction, high polymerization degree (ABA) N-shaped polyether modified silicon oil of polymerization degree n > 10 is made.The present invention carries out chain extension to triblock polyether modified silicon oil with reacting for hydroxyl using isocyanato, and using the preparation process that chain extender is added portionwise, is compared with the traditional method the difficulty for reducing reaction, the polyether modified silicon oil of readily available high polymerization degree.
Description
Technical field
The present invention relates to a kind of synthetic methods of high polymerization degree organic silicon modified by polyether, belong to polyurethane auxiliary agent technology neck
Domain.
Background technique
Organic silicon modified by polyether oxygen alkane (also referred to as polyether modified silicon oil) is the Hydrophilicrto polyether segment very big by performance difference
It with hydrophobic polysiloxane segment, is formed by connecting by chemical bond, is widely used as polyurethane foam foam stabilizer.Not according to chain structure
Together, polyether modified silicon oil is divided into side chain type and backbone chain type, and wherein side chain type is comb-like graft copolymer, and main chain is polysiloxanes,
Side chain is polyethers, because preparation process is simple, versatile, is used widely, but it is applied to special urethane foam (as slowly
Rebound foam) when, performance is often difficult to meet the requirements.Backbone chain type is linear multi-block copolymer, can regard triblock polyether as and change
Property silicone oil (ABA type silicone oil) segmented copolymer for being obtained after chain extension, also known as (ABA) n-type silicon oil, wherein n is the degree of polymerization, when
When for special urethane foam foam stabilizer, it is desirable that high polymerization degree (n is not less than 10).
With the increase of the degree of polymerization, the reactivity of segment end group will be significantly reduced, therefore the backbone chain type of high polymerization degree is poly-
The synthesis difficulty of ether modified silicon oil is larger.The present invention is chain extender using the diisocyanate for being easy to react and passes through batch charging
Preparation process, greatly reduce obtain high polymerization degree multi-block polyether modified silicon oil difficulty.
Summary of the invention
In view of the above-mentioned problems, the present invention with triblock polyether modified silicon oil (ABA type silicone oil) be prepolymer, isophorone two
Isocyanates (IPDI) is chain extender, prepares high polymerization degree (ABA) n-type silicon oil by Optimizing Technical, and reaction condition is mild,
It is easily controllable.
To realize this target, (1) present invention reacts to obtain three first with allyl polyether by both-end containing hydrogen silicone oil embedding
Section polyether modified silicon oil, i.e. ABA type silicone oil, reaction are as follows:
Formula 1.
(2) by above-mentioned ABA type silicone oil and IPDI Hybrid Heating, in dibutyltindilaurate catalyzed lower 2 institute of generating polynomial
Show reaction, (ABA) n-type silicon oil is made.
Formula 2.
Specific step is as follows for the technical solution adopted by the present invention.
1) preparation of ABA type silicone oil: preparing catalyst first, by 1g H2PtCl6·6H2O is dissolved in 50g and removes water through distillation
The isopropanol of processing, one night of standing are kept in dark place for use.Then in N2Under protection, the allyl of vacuum distillation removing moisture is gathered
Reaction kettle is added in ether and both-end containing hydrogen silicone oil, and stirring is heated to 90 DEG C, after reaction solution clear, insulation reaction 1.5h is obtained
To yellowish transparency liquid, that is, ABA silicone oil.
2) preparation of (ABA) N-shaped polyether modified silicon oil: ABA type silicone oil 35g made from above-mentioned reaction is taken to be added to three mouthfuls of burnings
In bottle, opens mechanical stirring and be warming up to 40-70 DEG C.After temperature reaches set temperature, reactant gross mass 0.5 ~ 1.25% is added
Dibutyl tin dilaurate, 3.89gIPDI is then added portionwise, in 1 hour be added finish.Continue to stir, insulation reaction 2-
5h。
Preferably, the reaction temperature of step (2) the triblock polyether modified silicon oil and IPDI are 60 ~ 70 DEG C.
Preferably, the catalysts dosage of step (2) the triblock polyether modified silicon oil and IPDI are that reactant is total
The 0.75 ~ 1% of quality.
Preferably, the reaction time of step (2) the triblock polyether modified silicon oil and IPDI are 2 ~ 4h
Preferably, the batch number that step (2) IPDI is added is 6 ~ 10 batches.
Compared with prior art, the invention has the benefit that
The present invention utilizes the addition reaction of isocyanate groups and hydroxyl to ABA type silicone oil chain extension, and combines and chain extension is added portionwise
The preparation process of agent prepares high polymerization degree (ABA) n-type silicon oil.Compared with prior synthesizing method, isocyanate groups and hydroxyl it
Between reaction be easy to happen, the mode of batch charging is conducive to form (ABA) n silicone oil of high polymerization degree, while raw material allyl is poly-
Ether is substantially reduced compared to both-end allyl capped polyethers cost, can meet the requirements and reduce cost in performance.
Specific embodiment
It elaborates below with reference to embodiment to the present invention.
Embodiment 1
The preparation of ABA silicone oil: by 1g H2PtCl6·6H2O is dissolved in the isopropanol that 50g removes water process through distilling, and stands in the dark
It one night and is kept in dark place.In the four-hole boiling flask that device has thermometer, blender and reflux condensing tube, 20g hydrogen content is added
The allyl polyether that both-end containing hydrogen silicone oil and 70g molecular weight for 0.5% are 660 is passed through nitrogen, stirs 10min, is warming up to 80
DEG C, platinum catalyst 20ppm is added, is warming up to 90 DEG C, the insulation reaction 1.5h after reaction solution clarification, removed under reduced pressure low-boiling-point substance obtains
To yellowish transparency liquid, that is, ABA silicone oil.Measuring molecular weight by gel permeation chromatography (GPC) is 1770.(ABA) N-shaped polyethers
The preparation of modified silicon oil: 35g ABA silicone oil is added in the four-hole bottle with agitating device, opens heating, temperature reaches 60 DEG C
Afterwards, catalyst dibutyltin dilaurylate 0.35g is added.Temperature is stablized after 60 DEG C, and IPDI 3.89 is added in point six batches altogether
0.648g is added in g, each batch, and interval time is ten minutes between batch.Continuing mixing control reacting liquid temperature is 60 DEG C, is protected
Temperature reaction 2h.After reaction, it takes product 2.5g product to be dissolved in the ethyl acetate of 50mL, is 0.5- with capillary diameter
The Ubbelohde viscometer of 0.6mm measures the delivery time at 25 DEG C as 108s.It is 20281 that GPC, which measures molecular weight,.Polymerization degree n=
10.2。
Embodiment 2
The preparation of ABA silicone oil: preparation method is identical as the preparation method of embodiment 1.(ABA) preparation of N-shaped polyether modified silicon oil:
35g ABA silicone oil is added in the four-hole bottle with agitating device, opens heating, after temperature reaches 60 DEG C, catalyst two is added
Dibutyl tin laurate 0.35g.Temperature is stablized after 60 DEG C, and 3.89 g of IPDI is added in point ten batches altogether, and each batch is added
0.389g, interval time is six minutes between batch.Continuing mixing control reacting liquid temperature is 60 DEG C, insulation reaction 2h.Reaction
After, take product 2.5g product to be dissolved in the ethyl acetate of 50mL, the Ubbelohde for being 0.5-0.6mm with capillary diameter is viscous
Degree meter measures the delivery time at 25 DEG C as 118s.It is 21281 that GPC, which measures molecular weight,.Polymerization degree n=10.7.
Comparative example 1
The preparation of ABA silicone oil: preparation method is identical as the preparation method of embodiment 1.(ABA) preparation of N-shaped polyether modified silicon oil:
35g ABA silicone oil is added, 3.89gIPDI(is once added) in the four-hole bottle with agitating device, heating is opened, to reaction solution
When temperature is increased to 40 DEG C, catalyst dibutyltin dilaurylate 0.35g is added, continuing mixing control reacting liquid temperature is 40
DEG C, insulation reaction 2h.After reaction, it takes product 2.5g product to be dissolved in the ethyl acetate of 50mL, is with capillary diameter
The Ubbelohde viscometer of 0.5-0.6mm measures the delivery time at 25 DEG C as 87s.It is 10520 that gel chromatography, which measures molecular weight,.Polymerization
Spend n=5.3.
Claims (3)
1. a kind of preparation method of high molecular weight (ABA) N-shaped polyether modified silicon oil, it is characterised in that include the following steps:
1) preparation of ABA type silicone oil: preparing catalyst first, by 1g H2PtCl6·6H2O is dissolved in 50g through distillation except water process
Isopropanol, stand a night be kept in dark place for use;
Then in N2Under protection, reaction kettle is added in the allyl polyether of vacuum distillation removing moisture and both-end containing hydrogen silicone oil, is stirred
It mixes, is heated to 90 DEG C, after reaction solution clear, insulation reaction 1.5h obtains yellowish transparency liquid i.e. ABA silicone oil;
2) it the preparation of (ABA) N-shaped modified silicon oil: takes ABA type silicone oil 35g made from above-mentioned reaction to be added in three-necked flask, opens
It opens mechanical stirring and is warming up to 40-70 DEG C;
After temperature reaches set temperature, the dibutyl tin dilaurate of reactant gross mass 0.5 ~ 1.25% is added, then in batches
3.89g isoflurane chalcone diisocyanate is added, is added and finishes in 1 hour,
Continue to stir, insulation reaction 2-5h.
2. according to the method described in claim 1, it is characterized by: in the step 2 three block ABA silicone oil molecule
Amount is 1500-2000.
3. according to the method described in claim 1, it is characterized by: isoflurane chalcone diisocyanate adds in the step 2
The batch number entered is 2 ~ 10 batches.
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111019140A (en) * | 2019-12-30 | 2020-04-17 | 江苏美思德化学股份有限公司 | Hyperbranched organic silicon foam stabilizer, and preparation method and application thereof |
CN112608478A (en) * | 2020-12-02 | 2021-04-06 | 甘肃银光聚银化工有限公司 | Method for preparing hydroxyl-terminated silicone oil |
CN115894938A (en) * | 2021-09-30 | 2023-04-04 | 浙江华峰新材料有限公司 | Carbon hydroxyl organic silicon polyether copolymer, polyurethane resin and preparation method thereof |
-
2018
- 2018-11-28 CN CN201811429680.3A patent/CN109575293A/en active Pending
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111019140A (en) * | 2019-12-30 | 2020-04-17 | 江苏美思德化学股份有限公司 | Hyperbranched organic silicon foam stabilizer, and preparation method and application thereof |
CN112608478A (en) * | 2020-12-02 | 2021-04-06 | 甘肃银光聚银化工有限公司 | Method for preparing hydroxyl-terminated silicone oil |
CN115894938A (en) * | 2021-09-30 | 2023-04-04 | 浙江华峰新材料有限公司 | Carbon hydroxyl organic silicon polyether copolymer, polyurethane resin and preparation method thereof |
CN115894938B (en) * | 2021-09-30 | 2024-02-02 | 浙江华峰新材料有限公司 | Carbon hydroxyl organic silicon polyether copolymer, polyurethane resin and preparation method thereof |
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Application publication date: 20190405 |