CN102504263B - Polyurethane foam stabilizer with good nucleating property and preparation method thereof - Google Patents
Polyurethane foam stabilizer with good nucleating property and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a polyurethane foam stabilizer with good nucleating property, which can effectively reduce the surface expansion of a foaming system. The organic foam stabilizer has the following structure: the value of a is 1-10, the value of b is 5-85, the value of c is 1-4, the value of x is 8-70, the value of y is 0-30, a+b+c is 7-99, and x+y is 8-100; R1 is alkane, aromatic groups, acyloxy or hydrogen atoms with the carbon atom number being 1-4; and R2 has a structure.
Description
Technical field
The present invention relates to a kind of polyurethane foam stabilizer and preparation method thereof, more specifically to a kind of polyurethane foam stabilizer that possesses good nucleation performance and preparation method thereof, this stablizer can be used for the hard polyurethane foams foam process.
Background technology
Urethane foam is a kind of important synthetic materials, has characteristics such as porousness, relative density are little, specific tenacity height, can be made into common soft bubble, high rebound foam and hard bubbles etc. according to the variation of raw materials used difference and prescription.Urethane foam is (as isocyanic ester by plurality of raw materials, polyvalent alcohol, water or whipping agent) (generally be no more than 1 minute) in the short period of time and carry out chemical reaction at the utmost point, and become colloid by liquid and become superpolymer again, experiencing complex processes such as foaming, gel therebetween.Therefore, must rely on suds-stabilizing agent to play regulating effect, just can make uniform in foaming, foam stabilization, make the uniform foams of abscess.Its role mainly contains: each component during 1. nucleation and emulsification are filled a prescription.The intermiscibility of each component in the foam formulation is relatively poor, needs the tensio-active agent of strong emulsifying capacity that it is mixed, thereby foamable reaction and crosslinking reaction are carried out smoothly.2. stable foam.Owing to add stablizer, the surface tension of material is reduced, make the air of sneaking into form nuclei of bubbles during stirring easily, these nuclei of bubbles play the effect of similar " nucleus ", the CO that produces during reaction
2Enter and namely generate bubble, and abscess is constantly grown up, evenly distribute and do not cause foam aperture and macropore to merge and make that foam seethes with excitement, the hole of collapsing.The number of bubble no longer increases in entire reaction course, and because the existence of suds-stabilizing agent makes the bubble size consistent.3. make foam perforate and " punching ".Bubble in the soft bubble must be that open cell type just can make the soft springiness of goods.Because the effect of suds-stabilizing agent, when system is in low viscosity during the stage, cell wall is stable, and when air bubble growth when being suitable for the thickness of perforate, then can break is " perforate ", and " punching " or " venting " phenomenon when foam is raised to maximum height, is then arranged.
The silicon foams stablizer can significantly reduce the surface tension of foaming system as a kind of tensio-active agent, is widely used.In the foam forming process, the extraneous stirring system acting W
Outward, maximum system energy increases thereupon, and energy difference is Δ E, W so before and after foam produces
OutwardR is more low for=Δ E=rA surface tension, and it is just more big then to apply the bubble area A that same merit produces, and illustrate that the bubble that produces is just more many, and then the abscess quantity of unit volume is just more big, and foam aperture is just more little, and foam is just more fine and closely woven.And the lower foam that can make of surface tension is more stable, plays better steady bubble effect.The Plateau border of bubble intersection and Laplace formula are Δ P=2r/R, and the foam external and internal pressure is poor as shown in Figure 1, and the A point is concave meniscus, and Δ P is less than zero; The B place is close to the plane, and Δ P is zero, and liquid can flow to A from B, thereby causes lather collapse, and when surface tension is more little, pressure difference is also more little, and foam is just more stable.
Therefore use the organic silicon surfactant with special performance and develop stablizer for polyurethane foamed material because its effect is remarkable, the innovation that has brought the polyurethane foamed material moulding process makes polyurethane industrial obtain tremendous development.In recent years, all kinds of polyether-modified polysiloxane can obtain to further develop with its excellent foam stability, have progressively replaced traditional polyurethane foam stabilizer.Siloxane main chain in the polyether-modified polysiloxane is as hydrophobic group, give the performance such as anti-stable, anti-aging, electrical isolation, softness of product fine, and hydrophilic polyether segment makes product have good surfactivity.By change introducing kind, quantity and the position of polyethers, can regulate amphipathic property effectively, thereby obtaining different performances such as steady bubble, froth breaking, lubricated, emulsification.Be that the United States Patent (USP) of US5844010 discloses a kind of organic silicon block copolymer as the macromolecular compound of stablizer as the patent No.; The patent No. is that the US5985948 United States Patent (USP) then discloses a kind of organic silicon polyether copolymer foam stablizer for high rebound foam; The patent No. is the preparation method that the ZL200710025597.5 Chinese patent then discloses a kind of low density and low heat conduction coefficient polyurethane foam stabilizer for the pentamethylene foaming system.Prior art generally all is to be grafted on the containing hydrogen silicone oil with allyl polyether, makes the polyether type organic silicone tensio-active agent, and its foam stabilization performance is still waiting further raising.
Summary of the invention
The object of the present invention is to provide a kind of polyurethane foam stabilizer that possesses good nucleation performance, it can significantly reduce the foaming system surface tension.
The present invention simultaneously also provides the preparation method of this polyurethane foam stabilizer.
Technical scheme of the present invention is as follows:
Silicon foams stablizer of the present invention, it has following structure:
Wherein: the value of a is that the value of 1～10, b is that the value of 5～85, c is that the value of 1～4, x is that the value of 8～70, y is 0～30, and a+b+c is that 7～99, x+y is 8～100; R
1Be 1～4 alkane, aromatic group, acyloxy or hydrogen atom for carbonatoms; R
2Then possess
Structure.
The preparation method of polyurethane foam stabilizer of the present invention may further comprise the steps:
A) with the vinyl carbinol be initiator, in reactor, add oxyethane and propylene oxide, in the presence of basic catalyst, pressure-controlling is at≤0.4MPa, under 100～130 ℃ of conditions, reacted 4～6 hours, obtain allyl-terminated polyether, wherein the mol ratio of oxyethane and propylene oxide consumption sum and initiator vinyl carbinol consumption is 10～50: 1;
B) be that raw material is under the Lewis acid effect with octamethylcyclotetrasiloxane, containing hydrogen silicone oil and hexamethyldisiloxane, be to react 5～7 hours under 60～90 ℃ of conditions in temperature of reaction, obtain polysiloxane, wherein the mol ratio between octamethylcyclotetrasiloxane, containing hydrogen silicone oil, the hexamethyldisiloxane is 1～40: 0.1～0.5: 0～3;
C) allyl-terminated polyether that above two-step reaction is obtained and polysiloxane and glycidyl allyl ether, Pt catalyzer and solvent add reactor, heat temperature raising to 60 under normal pressure～120 ℃ reaction 2～10 hours is opened the reflux condensing tube water coolant to guarantee solvent refluxing in the time of reacting by heating; After reaction finishes, carry out air distillation earlier and carry out underpressure distillation again, treat that solvent has been steamed the back cooling, obtain polyether-modified polysiloxane intermediate, wherein the mol ratio between allyl-terminated polyether, polysiloxane, the glycidyl allyl ether is 7～99: 1～10: 1～4;
D) with step C) the polyether-modified polysiloxane intermediate that obtains and diethanolamine or N-methylcyclohexylamine add reactor, reacted 1～2.5 hour under 60～90 ℃ of conditions of normal pressure, namely obtains possessing the polyurethane foam stabilizer of good nucleation performance.
Among the preparation method of the polyurethane foam stabilizer that possesses good nucleation performance of the present invention, its further technical scheme is steps A) described in basic catalyst be KOH or NaOH, its consumption is 0.1～0.5% of oxyethane and propylene oxide total mass.
Among the preparation method of the polyurethane foam stabilizer that possesses good nucleation performance of the present invention, its further technical scheme can also be step B) described in Lewis acid be sulfuric acid, its consumption is 0.1～3% of used material total mass.
Among the preparation method of the polyurethane foam stabilizer that possesses good nucleation performance of the present invention, its further technical scheme can also be step B) described in containing hydrogen silicone oil in the content of hydrogen be 1.55～1.66%.
Among the preparation method of the polyurethane foam stabilizer that possesses good nucleation performance of the present invention, its further technical scheme can also be step C) described in the Pt catalyst levels be 3～50ppm of material total mass.
Among the preparation method of the polyurethane foam stabilizer that possesses good nucleation performance of the present invention, its further technical scheme can also be step C) described in solvent be toluene or dimethylbenzene, consumption is 30～90% of material total mass.
Compared with prior art the present invention has following beneficial effect:
During modification a part of allyl polyether is replaced with glycidyl allyl ether, again with the epoxide group of glyceryl ether respectively by diethanolamine and N-methylcyclohexylamine open loop, syntheticly contain amino comb-type structure silicon foams stablizer.Amino is polar group, can with combined polyether in polyether glycol and the hydroxyl of water work, its surfactivity is better than polyoxyethylene propylene oxide copolyether.Therefore this suds-stabilizing agent can significantly reduce the surface tension of foaming system, wherein when suds-stabilizing agent contains 2% in combined polyether, surface tension＜the 22.0mN/m of combined polyether, the combined polyether surface tension that contains common silicon foams stablizer significantly reduces.The polyurethane foam that adopts suds-stabilizing agent of the present invention to make is compared with the polyurethane foam abscess of common silicon foams stablizer finer and closely woven.
Description of drawings
Fig. 1 foam external and internal pressure difference structural representation
Fig. 2 embodiment 1 makes product
1The H-NMR spectrogram
Fig. 3 embodiment 3 makes product
1The H-NMR spectrogram
Embodiment
A) in reactor, add vinyl carbinol 6.0g, oxyethane 120g and propylene oxide 95g, in the presence of the 0.9gKOH catalyzer, pressure≤0.4MPa, temperature of reaction be to react 5 hours under 110 ℃ of conditions, obtains allyl-terminated polyether (I);
B) octamethylcyclotetrasiloxane, containing hydrogen silicone oil and hexamethyldisiloxane were reacted 5 hours in 80 ℃ under effect of sulfuric acid, obtain polysiloxane (II), wherein the mol ratio between octamethylcyclotetrasiloxane, containing hydrogen silicone oil (hydrogen richness 1.60%) and the hexamethyldisiloxane is 10: 0.11: 1;
C) allyl-terminated polyether (I) 200g, polysiloxane (II) 80g, the glycidyl allyl ether 2.8g that above two-step reaction is obtained adds reactor, in heat temperature raising to the 60～120 ℃ reaction 8 hours under normal pressure of 30ppmPt catalyzer and 100g toluene solvant, open the reflux condensing tube water coolant in the time of reacting by heating to guarantee solvent refluxing.Reaction is carried out air distillation earlier and is carried out underpressure distillation again after finishing, and treats that solvent has been steamed the back cooling, obtains polyether-modified polysiloxane intermediate (III).
D) polyether-modified polysiloxane intermediate (III) 200g, diethanolamine 2.2g reacted 2 hours at 90 ℃ in normal pressure, the polyurethane foam stabilizer that obtains having good nucleation performance, and its structural formula is:
This suds-stabilizing agent performance sees Table 1.
A) in reactor, add vinyl carbinol 5.8g, oxyethane 130g and propylene oxide 105g, in the presence of the 1.07gKOH catalyzer, pressure≤0.4MPa, temperature of reaction be to react 5.5 hours under 120 ℃ of conditions, obtains allyl-terminated polyether (I);
B) octamethylcyclotetrasiloxane, containing hydrogen silicone oil and hexamethyldisiloxane were reacted 5 hours in 80 ℃ under effect of sulfuric acid, obtain polysiloxane (II), wherein the mol ratio between octamethylcyclotetrasiloxane, containing hydrogen silicone oil (hydrogen richness 1.60%) and the hexamethyldisiloxane is 17: 0.2: 1.5;
C) allyl-terminated polyether (I) 210g, polysiloxane (II) 70g, the glycidyl allyl ether 2.6g that above two-step reaction is obtained adds reactor, in heat temperature raising to the 60～120 ℃ reaction 8 hours under normal pressure of 30ppmPt catalyzer and 100g toluene solvant, open the reflux condensing tube water coolant in the time of reacting by heating to guarantee solvent refluxing.Reaction is carried out air distillation earlier and is carried out underpressure distillation again after finishing, and treats that solvent has been steamed the back cooling, obtains polyether-modified polysiloxane intermediate (III).
D) polyether-modified polysiloxane intermediate (III) 200g, diethanolamine 1.63g reacted 2 hours at 90 ℃ in normal pressure, the polyurethane foam stabilizer that obtains having good nucleation performance, and its structural formula is:
This suds-stabilizing agent performance sees Table 1.
A) in reactor, add vinyl carbinol 6.0g, oxyethane 120g and propylene oxide 95g, in the presence of the 0.9gKOH catalyzer, pressure≤0.4MPa, temperature of reaction be to react 5 hours under 110 ℃ of conditions, obtains allyl-terminated polyether (I);
B) octamethylcyclotetrasiloxane, containing hydrogen silicone oil and hexamethyldisiloxane were reacted 5 hours in 80 ℃ under effect of sulfuric acid, obtain polysiloxane (II), wherein the mol ratio between octamethylcyclotetrasiloxane, containing hydrogen silicone oil (hydrogen richness 1.60%) and the hexamethyldisiloxane is 10: 0.11: 1;
C) allyl-terminated polyether (I) 200g, polysiloxane (II) 80g, the glycidyl allyl ether 2.8g that above two-step reaction is obtained adds reactor, in heat temperature raising to the 60～120 ℃ reaction 8 hours under normal pressure of 30ppmPt catalyzer and 100g toluene solvant, open the reflux condensing tube water coolant in the time of reacting by heating to guarantee solvent refluxing.Reaction is carried out air distillation earlier and is carried out underpressure distillation again after finishing, and treats that solvent has been steamed the back cooling, obtains polyether-modified polysiloxane intermediate (III).
D) polyether-modified polysiloxane intermediate (III) 200g, N-methylcyclohexylamine 2.38g reacted 1.5 hours at 80 ℃ in normal pressure, the polyurethane foam stabilizer that obtains having good nucleation performance, and its structural formula is:
This suds-stabilizing agent performance sees Table 1.
Embodiment 4
A) in reactor, add vinyl carbinol 4.7g, oxyethane 121g and propylene oxide 95g, in the presence of the 0.9gKOH catalyzer, pressure≤0.4MPa, temperature of reaction be to react 5 hours under 110 ℃ of conditions, obtains allyl-terminated polyether (I);
B) octamethylcyclotetrasiloxane, containing hydrogen silicone oil and hexamethyldisiloxane were reacted 5 hours in 80 ℃ under effect of sulfuric acid, obtain polysiloxane (II), wherein the mol ratio between octamethylcyclotetrasiloxane, containing hydrogen silicone oil (hydrogen richness 1.60%) and the hexamethyldisiloxane is 20: 0.3: 1;
C) allyl-terminated polyether (I) 250g, polysiloxane (II) 80g, the glycidyl allyl ether 2.8g that above two-step reaction is obtained adds reactor, in heat temperature raising to the 60～120 ℃ reaction 8 hours under normal pressure of 30ppmPt catalyzer and 100g toluene solvant, open the reflux condensing tube water coolant in the time of reacting by heating to guarantee solvent refluxing.Reaction is carried out air distillation earlier and is carried out underpressure distillation again after finishing, and treats that solvent has been steamed the back cooling, obtains polyether-modified polysiloxane intermediate (III).
D) polyether-modified polysiloxane intermediate (III) 200g, N-methylcyclohexylamine 1.67g reacted 1.5 hours at 80 ℃ in normal pressure, the polyurethane foam stabilizer that obtains having good nucleation performance, and its structural formula is:
This suds-stabilizing agent performance sees Table 1.
This suds-stabilizing agent of table 1 is to the capillary influence (surface tension: mN/m) of polyethers system
Annotate: go up in the table, the quality proportioning of polyethers system is: (4110) 65 parts of polyethers, (653) 35 parts of polyethers, 1.5 parts in water, N, 2 parts of N-dimethylcyclohexylamines, DMP-301.2 part.
Among Fig. 2, chemical shift 2.5,2.7 spectrum peaks belong to NCH in addition
2In hydrogen; Among Fig. 3, chemical shift 2.5 spectrum peaks belong to CH
2Hydrogen among the N, chemical shift 2.1～2.3 belong to NCH
3In hydrogen.This can be used as amino modified polyether silicone oil
1The H-NMR spectrum is different from the obvious characteristic that other foam is used polysiloxane surfactant.
Claims (6)
1. polyurethane foam stabilizer that possesses good nucleation performance is characterized in that having following structural formula:
In the structural formula: the value of a is that the value of 1～10, b is that the value of 5～85, c is that the value of 1～4, x is that the value of 8～70, y is 0～30, and a+b+c is that 7～99, x+y is 8～100;
R
1Be hydrogen atom;
R
2Have
Or
Structure.
2. preparation method who possesses the polyurethane foam stabilizer of good nucleation performance as claimed in claim 1 is characterized in that may further comprise the steps:
A) with the vinyl carbinol be initiator, in reactor, add oxyethane and propylene oxide, in the presence of basic catalyst, pressure-controlling is at≤0.4MPa, under 100～130 ℃ of conditions, reacted 4～6 hours, obtain allyl-terminated polyether, wherein the mol ratio of oxyethane and propylene oxide consumption sum and initiator vinyl carbinol consumption is 10～50:1;
B) be that raw material is under the Lewis acid effect with octamethylcyclotetrasiloxane, containing hydrogen silicone oil and hexamethyldisiloxane, be to react 5～7 hours under 60～90 ℃ of conditions in temperature of reaction, obtain polysiloxane, wherein the mol ratio between octamethylcyclotetrasiloxane, containing hydrogen silicone oil, the hexamethyldisiloxane is 1～40:0.1～0.5:0～3, and wherein the content of hydrogen is 1.55～1.66% in the containing hydrogen silicone oil;
C) allyl-terminated polyether that above two-step reaction is obtained and polysiloxane and glycidyl allyl ether, Pt catalyzer and solvent add reactor, heat temperature raising to 60 under normal pressure～120 ℃ reaction 2～10 hours is opened the reflux condensing tube water coolant to guarantee solvent refluxing in the time of reacting by heating; After reaction finishes, carry out air distillation earlier and carry out underpressure distillation again, treat that solvent has been steamed the back cooling, obtain polyether-modified polysiloxane intermediate, wherein the mol ratio between allyl-terminated polyether, polysiloxane, the glycidyl allyl ether is 7～99:1～10:1～4;
D) with step C) the polyether-modified polysiloxane intermediate that obtains and diethanolamine or N-methylcyclohexylamine add reactor, reacted 1～2.5 hour under 60～90 ℃ of conditions of normal pressure, namely obtains possessing the polyurethane foam stabilizer of good nucleation performance.
3. the preparation method who possesses the polyurethane foam stabilizer of good nucleation performance according to claim 2 is characterized in that steps A) described in basic catalyst be KOH or NaOH, its consumption is 0.1～0.5% of oxyethane and propylene oxide total mass.
4. the preparation method who possesses the polyurethane foam stabilizer of good nucleation performance according to claim 2 is characterized in that step B) described in Lewis acid be sulfuric acid, its consumption is 0.1～3% of used material total mass.
5. the preparation method who possesses the polyurethane foam stabilizer of good nucleation performance according to claim 2 is characterized in that step C) described in the Pt catalyst levels be 3～50ppm of material total mass.
6. the preparation method who possesses the polyurethane foam stabilizer of good nucleation performance according to claim 2 is characterized in that step C) described in solvent be toluene or dimethylbenzene, consumption is 30～90% of material total mass.
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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 |
| JP6956751B2 (en) * | 2016-06-23 | 2021-11-02 | エボニック オペレーションズ ゲーエムベーハー | Composition suitable for the production of rigid polyurethane foam or rigid polyisocyanurate foam |
| CN109096494B (en) * | 2017-06-20 | 2021-02-05 | 中山市东峻化工有限公司 | Preparation method of wood-like polyurethane foam stabilizer |
| CN107805306B (en) * | 2017-11-10 | 2020-12-15 | 苏州思德新材料科技有限公司 | Organic silicon foam stabilizer and preparation method and application thereof |
| CN109942822A (en) * | 2017-12-21 | 2019-06-28 | 江苏美思德化学股份有限公司 | A kind of polyether modified siloxane copolymer of stable storing and preparation method thereof |
| CN109942821B (en) * | 2019-03-26 | 2021-05-18 | 吉林乾仁新材料有限公司 | Preparation method of hydroxyl amino modified silicone oil cationic emulsion, product and application thereof |
| CN110041553B (en) * | 2019-05-15 | 2022-03-11 | 珠海东诚新材料股份有限公司 | Foam stabilizer for full-water foaming system |
| CN111040176A (en) * | 2019-12-27 | 2020-04-21 | 江苏美思德化学股份有限公司 | Organic silicon polyether copolymer and preparation method and application thereof |
| CN111004396B (en) * | 2019-12-27 | 2022-07-05 | 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 |
| CN111499811B (en) * | 2020-06-05 | 2022-02-11 | 中国科学院兰州化学物理研究所 | A wear-resistant anti-fog resin, a preparation method thereof, and an anti-fog coating |
| CN113831537A (en) * | 2021-09-01 | 2021-12-24 | 苏州思德新材料科技有限公司 | Preparation method of novel polyurethane foam stabilizer |
| CN117736484B (en) * | 2023-12-20 | 2024-05-17 | 中山市泰源新材料科技有限公司 | Durable heat-insulating foaming material and preparation method thereof |
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| US5844010A (en) * | 1997-03-29 | 1998-12-01 | Th. Goldschmidt Ag | Method of preparing polyurethane foam utilizing block copolymers having linked siloxane blocks |
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