CN103055759A - Polyurethane foam organosilicon surfactant with steady bubbles and opening performance - Google Patents
Polyurethane foam organosilicon surfactant with steady bubbles and opening performance Download PDFInfo
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Abstract
The invention discloses a polyurethane foam organosilicon surfactant with steady bubbles and opening performance. The polyurethane foam organosilicon surfactant with the steady bubbles and the opening performance utilizes an organosilicon surfactant, meanwhile meets the requirements of steady bubbles and the opening performance, and adjusts the proportion of steady bubbles and the opening according to different application requirements to meet demands of practical application better. The organosilicon surfactant has a structure with the following structural formula I, wherein in the structural formula I, a m has a value of 15 to 210, a n1 has a value of 1 to 10, and a n2 has a value of 1 to 10, and m + n1 + n2 = 20 to 235, the structurally general formula of R1 is the following structurally general formula II, and the structurally general formula of R2 is the following structurally general formula III.
Description
Technical field
The present invention relates to a kind of organic silicon surfactant, more specifically to a kind of polyurethane foam organic silicon surfactant that has steady bubble and perforate performance concurrently.
Background technology
Organic silicon surfactant take dimethyl silicone polymer as hydrophobic main chain, connects one or more polar organic groups in main chain interposition or end position and the class surfactant that consists of.Organic silicon surfactant, has the capillary performance of good reduction, wetting and spreadability is good, the emulsibility effect is large, compatibility good, and have foaming, surely steep and press down the bubble effect, and have no side effect, to be widely used in the aspects such as cosmetics, polyurethane foam plastics, weaving, coating, agricultural chemicals.
Organic silicon surfactant is to produce the steady indispensable component of polyurethane foam plastics foam, also is called as foam stabiliser.It plays a part emulsification foam material, stable foam and adjusting abscess, although its consumption is little, cell size and structure, physical property, the manufacturing process of foams is had significant impact.
On the traditional sense, polyurethane foam plastics all requires to have good foam stability energy with organic silicon surfactant.US6166098, US6245824, EP1081177A, and " a kind of preparation method of polyurethane foam stabilizer " (CN102226002) etc. patent all reported copolymer with end group hydroxy polyethers graft modification polysiloxanes, as have foam stability can the structure and preparation method thereof of silicon foams stabilizing agent, and answering in the polyurethane foam plastics factory formula.But such organic silicon surfactant is excessively emphasized its foam stability energy, at some to the demanding application of the dimensional stability of polyurethane foam plastics, such as solar water heater, one-component gap filler etc., will show obvious weak tendency, so that have to add the auxiliary agent with perforate performance in the production process of this series products, make it reach the effect of dimensionally stable.
Chinese invention patent " masked non-ionic surfactant, preparation method and application thereof " (CN100509128) reported, with the end-sealed type surfactant of methyl blocking hydroxyl allyl alcohol polyether modified polyorganosiloxane, and the application in soft polyurethane foam.
The above-mentioned surfactant of preparing with terminal hydroxy group allyl alcohol polyether end group hydroxy polyethers graft modification polysiloxanes in hard polyurethane foam, has higher foam stability energy and rate of closed hole; And with the end-sealed type surfactant of methyl blocking hydroxyl allyl alcohol polyether modified polyorganosiloxane, in soft polyurethane foam, has the perforate effect, although it also has certain steady bubble effect, but it has too high molecular weight, its perforate performance is occupied an leading position when using in hard polyurethane foam, almost without steady bubble effect.
Limitation for above-mentioned two kinds of structures, patent of the present invention is from the Molecular Design angle, kind by control polymer molecular weight and allyl polyether, invented a kind of organic silicon surfactant that has simultaneously foam stability energy and perforate performance, and be applied to have in the production of hard polyurethane foam that dimensional stability requires and monocomponent polyurethane gap filler, obtained good effect.
Summary of the invention
The object of the invention is to solve deficiency and the problem that exists in the above-mentioned present technology, from the structural design angle, a kind of polyurethane foam organic silicon surfactant that has steady bubble and perforate performance concurrently is provided, utilize a kind of organic silicon surfactant, satisfy simultaneously the requirement of steady bubble and perforate performance, and different according to the requirement of using, the ratio that can regulate steady bubble and perforate better meets practical application request.
Organic silicon surfactant of the present invention, it has the structure of following structural formula I:
Wherein in the structural formula I:
The value of m is that the value of 15～210, n1 is that the value of 1～10, n2 is 1～10, and m+n1+n2=20～235;
The general structure of R1 is the following formula II
Wherein in the structural formula II: molecular weight ranges is 400～3500, the value of a is 0～60, the value of b is 5～90, and the weight proportion of PEO and PPOX segment in the segment: the PEO segment is 0～50%, and the PPOX segment is 50～100%; M is that carbon number is 1 ~ 4 alkane, acyloxy;
The general structure of R2 is the following formula III
Wherein in the structural formula III: molecular weight ranges is 400～3500, the value of c is 5～90, the value of d is 0～60, and the weight proportion of PEO and PPOX segment in the segment: the PEO segment is 100～50%, and the PPOX segment is 0～50%.
The preparation method of organic silicon surfactant of the present invention is CN100509128 disclosed " masked non-ionic surfactant, preparation method and application thereof " with publication number, and concrete steps are as follows:
A) take allyl alcohol as initiator, in reactor, add oxirane and expoxy propane, in the presence of the base catalyst, pressure≤0.2Mpa, reaction temperature be to react 4 ~ 6 hours under 100～130 ℃ of conditions, obtain end acrylic polyethers R0 and the R2 of different molecular weight, wherein the mole of the consumption of oxirane and expoxy propane consumption sum and initiator allyl alcohol is 3～300:1;
B) preparation method of modified polyether R1 describes in detail and to see that publication number is " a kind of end capped polyether by the end hydroxy polyether preparation and preparation method thereof " patent of CN101343358, specific as follows: that the terminal hydroxy group of polyethers R0 is carried out modification, the soon terminal hydroxy group of polyethers R0 employing contains sodium or the potassium compounds carries out pure salinization replacement, obtain the Aethoxy Sklerol metal, then adopt chloride to carry out chlorination reaction, obtain blocking modification polyethers R1;
C) preparation method of polysiloxanes describes in detail and sees that publication number is the patent of CN101733142A " a kind of load-type solid acid catalyst, preparation method and application thereof ", be specially: make octamethylcy-clotetrasiloxane, containing hydrogen silicone oil, HMDO under the supported catalyst effect, be to react 4～6 hours under 60～90 ℃ of conditions in reaction temperature, obtain polysiloxanes, wherein the mol ratio between octamethylcy-clotetrasiloxane, containing hydrogen silicone oil, the HMDO is 10-120:1-5:1.0-2.0;
D) 50-85 parts of the R1 that the weight portion that top reaction is obtained is different and R2 polyethers and polysiloxanes 15-50 part, under the Pt of 5-15ppm catalyst action, be to carry out polymerisation under 60～120 ℃ of conditions to make organic silicon surfactant after 8～10 hours in reaction temperature.
Compared with prior art the invention has the beneficial effects as follows:
Crucial part of the present invention is introduced the polyether segment with perforate and foam stability energy at same polysiloxanes segment, so that prepare organic silicon surfactant when having steady bubble function, have perforate function to a certain degree concurrently, utilize this organic silicon surfactant prepare polyurethane foam plastics when having fine and closely woven even foam structure, need not to add any pore-creating agent, can keep good dimensional stability.
Description of drawings
Fig. 1 be on perforate and foam stability can impact concern schematic diagram
The specific embodiment
Embodiment 1
A) in reactor, add allyl alcohol 58g, oxirane 220g and expoxy propane 1450g, in the presence of 0.006g bimetallic catalyst zinc hexacyanocobaltate compounds, pressure≤0.2Mpa, reaction temperature be reaction 5 hours under 115 ℃ of conditions, obtains holding the acrylic polyethers; And then add 2.0g NaOH, and be warming up to 120 ℃ of insulations 3 hours under the normal pressure, then carry out decompression distillation, material is cooled to 75 ℃ again, add excess chlorine methane and controlled pressure≤0.4Mpa, regulating PH is 5.2, and material filtering is obtained modified polyether R1.In reactor, add allyl alcohol 58g, oxirane 485g and expoxy propane 116g, in the presence of 0.0008g bimetallic catalyst zinc hexacyanocobaltate compounds, pressure≤0.2Mpa, reaction temperature be reaction 5 hours under 115 ℃ of conditions, obtains holding acrylic polyethers R2;
B) make octamethylcy-clotetrasiloxane, containing hydrogen silicone oil, HMDO under load acid effect, reaction temperature be under 70 ℃ of conditions the reaction 5 hours, obtain polysiloxanes, wherein the consumption mole proportioning between octamethylcy-clotetrasiloxane, containing hydrogen silicone oil, the HMDO is 33.3:2.8:1;
C) the modified polyether R1360g that top two-step reaction is obtained, R2890g and polysiloxanes 485g are under 10ppm Pt catalyst action, be to carry out polymerisation after 9 hours under 100 ℃ of conditions in reaction temperature, namely make organic silicon surfactant, result behind phenetic analysis is as follows for its structure:
In the formula
The structural formula of R1 is:
The structural formula of R2 is:
Product properties and effect that this organic silicon surfactant is applied to polyurethane foam see Table 1 through detecting.
Embodiment 2
The modified polyether R1540g that embodiment 1 is obtained, R2578g and polysiloxanes 485g are under the 10ppm Pt catalyst action and in the presence of the toluene 700g, be to carry out polymerisation after 9 hours under 100 ℃ of conditions in reaction temperature, namely make masked non-ionic surfactant, result behind phenetic analysis is as follows for its structure:
In the formula
The structural formula of R1 is:
The structural formula of R2 is:
Product properties and effect that this organic silicon surfactant is applied to polyurethane foam see Table 1 through detecting.
Embodiment 3
The modified polyether R1470g that embodiment 1 is obtained, R2350g and polysiloxanes 485g are under the 10ppm Pt catalyst action and in the presence of the toluene 700g, be to carry out polymerisation after 9 hours under 100 ℃ of conditions in reaction temperature, namely make masked non-ionic surfactant, result behind phenetic analysis is as follows for its structure:
In the formula
The structural formula of R1 is:
The structural formula of R2 is:
Product properties and effect that this organic silicon surfactant is applied to polyurethane foam see Table 1 through detecting.
Embodiment 4
The modified polyether R1630g that embodiment 1 is obtained, R2274g and polysiloxanes 485g are under the 10ppm Pt catalyst action and in the presence of the toluene 700g, be to carry out polymerisation after 9 hours under 100 ℃ of conditions in reaction temperature, namely make masked non-ionic surfactant, result behind phenetic analysis is as follows for its structure:
In the formula
The structural formula of R1 is:
The structural formula of R2 is:
Product properties and effect that this organic silicon surfactant is applied to polyurethane foam see Table 1 through detecting.
This foam stabiliser of table 1 is applied to the product properties of monocomponent polyurethane foam
| ? | Foam structure | The contraction situation | Percent opening, % |
| Embodiment 1 | Fine and closely woven even | Slight shrinkage | 16．6 |
| Embodiment 2 | Fine and closely woven even | Slight shrinkage | 24．4 |
| Embodiment 3 | Fine and closely woven even | Slight shrinkage | 37．6 |
| Embodiment 4 | Fine and closely woven even | Dimensionally stable is good | 46．1 |
| External product 1 | Fine and closely woven even | Shrink serious | 6．2 |
| External product 2 | Fine and closely woven even | Shrink serious | 5．8 |
| Domestic mill run | Fine and closely woven even | Shrink serious | 7．3 |
The data based following foaming formulation of * in the upper table: 100 parts of polyalcohols; 5 parts in water; 0.3 part of catalyst DMDEE; 2.8 parts of foam stabilisers; 28 parts of the third butane; 127.3 parts of TDI, weight proportion, and foaming evaluation is all carried out under the same conditions.
By lot of examples, we have obtained different mol ratio R1 and R2, on perforate and foam stability can impact concern schematic diagram, see Fig. 1.Therefore, according to the tendency chart that concerns of the perforate of Fig. 1 and steady bubble, in conjunction with the requirement of different application scenarios and steady bubble and perforate, can prepare the polyurethane foam plastics organic silicon surfactant that has steady bubble and perforate performance when satisfying the demand concurrently.
Claims (1)
1. polyurethane foam organic silicon surfactant that has steady bubble and perforate performance concurrently is characterized in that having the structure of following structural formula I:
Wherein in the structural formula I:
The value of m is that the value of 15～210, n1 is that the value of 1～10, n2 is 1～10, and m+n1+n2=20～235;
The general structure of R1 is the following formula II
Wherein in the structural formula II: molecular weight ranges is 400～3500, the value of a is 0～60, the value of b is 5～90, and the weight proportion of PEO and PPOX segment in the segment: the PEO segment is 0～50%, and the PPOX segment is 50～100%; M is that carbon number is 1 ~ 4 alkane, acyloxy.
The general structure of R2 is the following formula III
Wherein in the structural formula III: molecular weight ranges is 400～3500, the value of c is 5～90, the value of d is 0～60, and the weight proportion of PEO and PPOX segment in the segment: the PEO segment is 100～50%, and the PPOX segment is 0～50%.
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| CN103657518A (en) * | 2013-12-16 | 2014-03-26 | 南京美思德新材料有限公司 | Nonionic organosilicon surfactant and preparation method thereof |
| EP3064532A1 (en) | 2015-03-03 | 2016-09-07 | Evonik Degussa GmbH | Production of porous polyurethane layers |
| EP3115389A1 (en) | 2015-07-07 | 2017-01-11 | Evonik Degussa GmbH | Preparation of polyurethane foam |
| CN109485855A (en) * | 2018-11-19 | 2019-03-19 | 江西麦豪化工科技有限公司 | A kind of flame retardant type organic silicon surfactant and its application |
| EP3459984A1 (en) | 2017-09-25 | 2019-03-27 | Evonik Degussa GmbH | Preparation of polyurethane foam |
| CN110982106A (en) * | 2019-12-27 | 2020-04-10 | 江苏美思德化学股份有限公司 | Organic silicon surfactant, soft polyurethane foam and preparation method thereof |
| CN111004396A (en) * | 2019-12-27 | 2020-04-14 | 江苏美思德化学股份有限公司 | Tertiary amino modified organic silicon polyether copolymer and preparation method and application thereof |
| EP3677610A1 (en) | 2019-01-07 | 2020-07-08 | Evonik Operations GmbH | Preparation of polyurethane foam |
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| EP3805285A1 (en) | 2019-10-08 | 2021-04-14 | Evonik Operations GmbH | Preparation of polyurethane rigid foam |
| DE102020202057A1 (en) | 2020-02-19 | 2021-08-19 | Evonik Operations Gmbh | Polyurethane insulation foams and their manufacture |
| EP3919539A1 (en) | 2020-06-04 | 2021-12-08 | Evonik Operations GmbH | Preparation of polyurethane foam |
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| CN114672029A (en) * | 2022-04-27 | 2022-06-28 | 四川大学 | Preparation method of nonionic organic silicon surfactant |
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| WO2023274699A1 (en) | 2021-07-01 | 2023-01-05 | Evonik Operations Gmbh | Production of hard polyurethane or polyisocyanurate foam |
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| CN103657518B (en) * | 2013-12-16 | 2015-11-04 | 南京美思德新材料有限公司 | A kind of Nonionic organosilicon surfactant and preparation method thereof |
| CN103657518A (en) * | 2013-12-16 | 2014-03-26 | 南京美思德新材料有限公司 | Nonionic organosilicon surfactant and preparation method thereof |
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| EP4372024A1 (en) | 2022-11-15 | 2024-05-22 | Evonik Operations GmbH | New method for recycling of polyisocyanurates |
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Application publication date: 20130424 |