CN101099926A - Masked non-ionic surfactant, preparation method and application thereof - Google Patents
Masked non-ionic surfactant, preparation method and application thereof Download PDFInfo
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Abstract
The present invention discloses one kind of terminated non-ionic surfactant and its preparation process and application. The surfactant is allyl terminated polyether with molecular weight controllable in 700-9500 Da, narrow molecular weight distribution and high reaction activity. It has methylol terminating rate up to 95 % and double bond terminating rate up to 93 %, and possesses structure as shown.
Description
Technical field
The present invention relates to a kind of surfactant, preparation method and application thereof, more specifically to a kind of masked non-ionic surfactant, preparation method and application thereof.
Background technology
Non-ionic surface active agent is to contain hydroxyl or ehter bond is a class amphiphilic structure molecule of hydrophilic group.Ionization does not take place in non-ionic surface active agent in water, so it all has dissolubility preferably in water He in the organic solvent, have excellent emulsifiability, and chemical stability height in solution has purposes very widely.Non-ionic surface active agent can be divided into types such as polyoxyethylene-type, polyalcohol type, alkylolamides, alkyl polyglycoside by its hydrophilic group.Allyl-terminated polyether has good hydrophilicity and superior emulsifying capacity, is a kind of non-ionic surface active agent of excellent performance, because its two ends are respectively two keys and hydroxy functional group, therefore also has very consequence in Polymer Synthesizing.
Masked non-ionic surfactant, refer to allyl-terminated polyether among the present invention with two keys and hydroxyl activity functional group, it is group end cappings such as 1～4 alkyl, acyloxy, silicon methyl that wherein terminal hydroxy group adopts carbon number, and the allyl double bonds of the other end and hydrogen containing siloxane carry out the addition end-blocking, thereby have synthesized the masked non-ionic surfactant that has than low surface tension, well emulsify performance and nucleation performance.
As disclosing the synthetic method of the end capped polyether that contains thiazolinyl in " technical progress of etherified sealed end polyethers " literary composition in 2002 19 phases " fine chemistry industry ", the end-blocking rate can reach 90% in the prior art; In 2004 02 phases " fragrance flavor and cosmetic " in " the synthetic and application of polyether type organic silicone surfactant " literary composition a kind of surfactant of being made up of polyethers section and poly-silica is disclosed also; The applying date is that July 28 nineteen ninety-five, application number are that 95115232.7 Chinese patent discloses a kind of polyether silicone surfactants that polyurethane foam is made that is used for, and its mean molecule quantity is 2250.These copolymer relative molecular weights of the prior art all are no more than 3000 simultaneously, the end-blocking rate also has only 90%, owing to the end-blocking rate of polyethers is omited to some extent and reduced along with the increase of its molecular weight, if raising molecular weight, its end-blocking rate can be lower, and the surface-active of these surfactants, emulsifiability and comprehensive balance quality all have much room for improvement in addition.
Summary of the invention
The objective of the invention is to solve deficiency and the problem that exists in the above-mentioned present technology, the masked non-ionic surfactant of serial excellent performance is provided.
The present invention simultaneously also provides the preparation method of this masked non-ionic surfactant and the application in soft polyurethane foam thereof.
Technical scheme of the present invention is as follows:
Masked non-ionic 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 15～210, and the value of n is 5～25, and m+n=20～235;
R is polyether segment R1, the R2...Ri of the serial different molecular weight that links to each other with silicon atom, 1≤i≤6 wherein, the general structure of R
Be following formula (II)
Wherein in the structural formula (II): different Ri molecular weight differ, its scope is 700～9500, the value of x is 3～160, the value of y is 0～140, and the weight proportion of PEO and PPOX segment in the segment: the PEO segment is 20～70%, and the PPOX segment is 30～80%;
M is that carbon number is 1～4 alkane, hydrogen atom, acyloxy or silicon methyl in the structural formula (II).
The preparation method of masked non-ionic surfactant of the present invention may further comprise the steps:
A) with the allyl alcohol be initiator, in reactor, add oxirane and expoxy propane, in the presence of the catalyst a, pressure≤0.2Mpa, reaction temperature be to react 4～6 hours under 100～130 ℃ of conditions, obtain the end acrylic polyethers R ' 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) terminal hydroxy group with polyethers R ' carries out modification, and the terminal hydroxy group of polyethers R ' employing soon contains sodium or the potassium compounds carries out pure salinization replacement, obtains the Aethoxy Sklerol metal, adopts chloride to carry out chlorination reaction then, obtains blocking modification polyethers Ri;
C) make octamethylcy-clotetrasiloxane, containing hydrogen silicone oil, HMDO under catalyst b effect, in reaction temperature is to react 4～6 hours under 60～90 ℃ of conditions, obtain polysiloxanes (I), wherein the mol ratio between octamethylcy-clotetrasiloxane, containing hydrogen silicone oil, the HMDO is 10-120: 1-5: 1.0-2.0;
D) different modified polyether R1～Ri 80-130 part and polysiloxanes (I) 10-35 part of the weight portion that top reaction is obtained, under the Pt of the 5-15ppm catalyst action and in the presence of the solvent, in reaction temperature is to carry out polymerisation under 60～120 ℃ of conditions to carry out decompression distillation after 8～10 hours, after stirring it is squeezed into falling film evaporator and carry out second distillation, promptly make masked non-ionic surfactant.
The preparation method of masked non-ionic surfactant of the present invention, its steps A) the catalyst a described in is preferably bimetallic catalyst, is preferably the zinc hexacyanocobaltate compounds, and its consumption is the 5-100ppm of oxirane and expoxy propane consumption sum; The weight proportion of oxirane its steps A) and expoxy propane is preferably as follows:
Oxirane is 20～70%
Expoxy propane is 30～80%.
In the preparation method of masked non-ionic surfactant of the present invention, its step B) it is as follows that the terminal hydroxy group that will hold acrylic polyethers R ' described in carries out the further technical scheme of its step of modification:
To hold acrylic polyethers, sodium or potassium compounds to add reactor successively, sodium or potassium compounds consumption are 0.1～2% of polyethers weight, be warming up to 90～130 ℃ of insulations 2～4 hours under the normal pressure, carry out decompression distillation then, material is cooled to 70～90 ℃ again, the slowly logical chloride controlled pressure≤0.45MPa that adds, be incubated 0.5～2 hour, regulating PH then is 5～6 o'clock, adds the filter aid of weight of material 3～5% again, stir after 2 hours, material filtering is obtained modified polyether Ri; Wherein said chloride is for being preferably chloromethanes or chlorobutane.
In the preparation method of masked non-ionic surfactant of the present invention, its step C) the catalyst b described in is preferably lewis acid, and its consumption is 0.1～3% of octamethylcy-clotetrasiloxane, containing hydrogen silicone oil and a HMDO weight sum; The content of hydrogen is 0.03～0.5% in the described containing hydrogen silicone oil; Its step D) catalyst described in is preferably chloroplatinic acid, and described solvent is preferably benzene or dimethylbenzene, and solvent load is 50～120% of polyethers and a polysiloxanes weight sum.
Technical scheme of the present invention also comprises the application of above-mentioned masked non-ionic surfactant in polyurethane foam technology.
Compared with prior art the invention has the beneficial effects as follows:
1) molecular weight of allyl-terminated polyether is between 700～9500, and molecular weight is controlled and its molecular weight distribution is narrower, and reactivity is higher;
2) carried out innovative design on production process, the control process conditions, made reaction more fully, efficiently, the methyl blocking rate of polyethers terminal hydroxy group can reach more than 95%, and polyethers terminal double bond end-blocking rate can reach more than 93%;
3) solved the problem of industrialization enlarge-effect, broken through the bottleneck of preparation high-performance masked non-ionic surfactant, process units has been amplified to 3M at present
3Scale has been produced the industrialization product of steady quality and excellent performance.
4) other preparation method of the present invention is simple, the constant product quality of production, and raw material is easy to get, and is lower from its production cost of original raw material.
5) this masked non-ionic surfactant is when being applied to the flexible polyurethane foams stabilizing agent, performances such as good emulsifying, nucleation and foam stabilization have been shown, and has comparatively broad processing tolerance, can be applied to the foaming formulation system of different densities, and on performances such as organotin tolerance, the even tiny degree of abscess, foaming height, falling height, also be better than prior art.
The specific embodiment
Embodiment 1
A) in reactor, add allyl alcohol 5.8g, oxirane 150g and expoxy propane 100g, in the presence of 0.0025g 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, carry out decompression distillation then, 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.Adjust material proportion, make modified polyether R2;
B) make octamethylcy-clotetrasiloxane, containing hydrogen silicone oil, HMDO under effect of sulfuric acid, in reaction temperature is to react 5 hours under 70 ℃ of conditions, obtain polysiloxanes (II), wherein the consumption mole proportioning between octamethylcy-clotetrasiloxane, containing hydrogen silicone oil, the HMDO is 40: 2: 1.2;
C) modified polyether R1+R2 (I) 600g that top two-step reaction is obtained and polysiloxanes (II) 100g are under the 10ppm Pt catalyst action and in the presence of the toluene 700g, in reaction temperature is to carry out polymerisation under 100 ℃ of conditions to carry out decompression distillation after 9 hours, after stirring it is squeezed into falling film evaporator and carry out second distillation, promptly make masked non-ionic surfactant, result behind phenetic analysis is as follows for its structure:
R is respectively R1 and R2 in the formula, and wherein R1 accounts for 47% of R1 and R2 sum, and R2 accounts for 53% of R1 and R2 sum
The structural formula of R1 is:
The structural formula of R2 is:
Product properties and effect that this masked non-ionic surfactant is applied to polyurethane foam see Table 1 through detecting.
Embodiment 2
A) in reactor, add allyl alcohol 5.8g, oxirane 200g and expoxy propane 100g, in the presence of 0.003g bimetallic catalyst zinc hexacyanocobaltate compounds, pressure≤0.2Mpa, reaction temperature be reaction 6 hours under 100 ℃ of conditions, obtains holding the acrylic polyethers; And then add 3.5g NaOH, and be warming up to 125 ℃ of insulations 3 hours under the normal pressure, carry out decompression distillation then, material is cooled to 70 ℃ again, add chloromethanes and controlled pressure≤0.4Mpa and be incubated 1 hour, regulating PH then is 5～6, and material filtering is obtained modified polyether R1.Adjust material proportion, make modified polyether R2;
B) make octamethylcy-clotetrasiloxane, containing hydrogen silicone oil, HMDO under effect of sulfuric acid, in reaction temperature is to react 4 hours under 75 ℃ of conditions, obtain polysiloxanes (II), wherein the consumption mole proportioning between octamethylcy-clotetrasiloxane, containing hydrogen silicone oil, the HMDO is 40: 1: 1.2;
C) modified polyether R1+R2 (I) 650g that top two-step reaction is obtained and polysiloxanes (II) 100g are under the 5ppm Pt catalyst action and in the presence of the dimethylbenzene 500g, in reaction temperature is to carry out polymerisation under 105 ℃ of conditions to carry out decompression distillation after 8 hours, after stirring it is squeezed into falling film evaporator and carry out second distillation, promptly make masked non-ionic surfactant, result behind phenetic analysis is as follows for its structure:
R is respectively R1 and R2 in the formula, and wherein R1 accounts for 63% of R1 and R2 sum, and R2 accounts for 37% of R1 and R2 sum
The structural formula of R1 is:
The structural formula of R2 is:
Product properties and effect that this masked non-ionic surfactant is applied to polyurethane foam see Table 1 through detecting
Embodiment 3
A) in reactor, add allyl alcohol 5.8g, oxirane 200g and expoxy propane 100g, in the presence of 0.003g bimetallic catalyst zinc hexacyanocobaltate compounds, pressure≤0.2Mpa, reaction temperature be reaction 4 hours under 130 ℃ of conditions, obtains holding the acrylic polyethers; And then add 3.5g NaOH, and be warming up to 125 ℃ of insulations 3 hours under the normal pressure, carry out decompression distillation then, material is cooled to 70 ℃ again, add excess chlorine butane and controlled pressure≤0.4Mpa and be incubated 1 hour, regulating PH is 5～6, and material filtering is obtained modified polyether R1.Adjust material proportion, make modified polyether R2;
B) make octamethylcy-clotetrasiloxane, containing hydrogen silicone oil, HMDO under effect of sulfuric acid, in reaction temperature is to react 4 hours under 75 ℃ of conditions, obtain polysiloxanes (II), wherein the consumption mole proportioning between octamethylcy-clotetrasiloxane, containing hydrogen silicone oil, the HMDO is 40: 1.5: 1.2;
C) modified polyether R1+R2 (I) 650g that top two-step reaction is obtained and polysiloxanes (II) 100g are under the 8ppm Pt catalyst action and in the presence of the toluene 400g, in reaction temperature is to carry out polymerisation under 105 ℃ of conditions to carry out decompression distillation after 8 hours, after stirring it is squeezed into falling film evaporator and carry out second distillation, promptly make masked non-ionic surfactant, result behind phenetic analysis is as follows for its structure:
R is respectively R1 and R2 in the formula, and wherein R1 accounts for 66% of R1 and R2 sum, and R2 accounts for 34% of R1 and R2 sum
The structural formula of R1 is:
The structural formula of R2 is:
Product properties and effect that this masked non-ionic surfactant is applied to polyurethane foam see Table 1 through detecting.
Embodiment 4
A) in reactor, add allyl alcohol 5.8g, oxirane 100g and expoxy propane 90g, in the presence of 0.0020g 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, carry out decompression distillation then, material is cooled to 75 ℃ again, add excess chlorine methane controlled pressure≤0.4Mpa and be incubated 1 hour, regulating PH is 5～6, and material filtering is obtained modified polyether R1.Adjust material proportion, make modified polyether R2, R3;
B) make octamethylcy-clotetrasiloxane, containing hydrogen silicone oil, HMDO under effect of sulfuric acid, in reaction temperature is to react 5 hours under 70 ℃ of conditions, obtain polysiloxanes (II), wherein the consumption mole proportioning between octamethylcy-clotetrasiloxane, containing hydrogen silicone oil, the HMDO is 40: 1.5: 1.2;
C) modified polyether R1+R2+R3 (I) 550g that top two-step reaction is obtained and polysiloxanes (II) 100g are under the 10ppm Pt catalyst action and in the presence of the solvent, in reaction temperature is to carry out polymerisation under 100 ℃ of conditions to carry out decompression distillation after 9 hours, after stirring it is squeezed into falling film evaporator and carry out second distillation, promptly make masked non-ionic surfactant, result behind phenetic analysis is as follows for its structure:
R is respectively R1, R2 and R3 in the formula, and wherein R1 accounts for 15% of R1, R2 and R3 sum, and R2 accounts for 34% of R1, R2 and R3 sum, and R3 accounts for 51% of R1, R2 and R3 sum.
The structural formula of R1 is:
The structural formula of R2 is:
The structural formula of R3 is:
Product properties and effect that this masked non-ionic surfactant is applied to polyurethane foam see Table 1 through detecting.
This foam stabiliser of table 1 is applied to the product properties of polyurethane foam
| The abscess outward appearance | Density range kg/m 3 | The processing tolerance * | The organotin tolerance * | Foam height * cm | Fall after rise * cm | |
| Embodiment 1 | Fine and closely woven even | 8-40 | 0.5-2 | 0.2-0.6 | 86.6 | 2.3 |
| Embodiment 2 | Fine and closely woven even | 8-40 | 0.5-2 | 0.2-0.6 | 86.3 | 2.4 |
| Embodiment 3 | Fine and closely woven even | 8-40 | 0.5-2 | 0.2-0.6 | 87.1 | 2.2 |
| Embodiment 4 | Fine and closely woven even | 8-40 | 0.5-2 | 0.2-0.6 | 86.3 | 2.5 |
| External product 1 | Fine and closely woven even | 10-35 | 0.5-2 | 0.2-0.4 | 86.2 | 3.0 |
| External product 2 | Fine and closely woven even | 15-30 | 0.7-2 | 0.2-0.6 | 86.1 | 2.6 |
| Domestic mill run | Abscess is thicker | 12-40 | 0.7-2 | 0.2-0.4 | 84.2 | 4.3 |
In the last table
*Data based following foaming formulation (foam density 13kg/m
3): 2,802 100 parts of polyalcohols; 5 parts in water; 0.3 part of A-33; 1.8 parts of foam stabilisers; 25 parts of MC; 0.5 part of T-9; 67.3 parts of TDI, weight proportion, and foaming evaluation is all carried out under the same conditions.
Claims (10)
1, a kind of masked non-ionic surfactant is characterized in that having the structure of following structural formula (I):
Wherein in the structural formula (I):
The value of m is 15～210, and the value of n is 5～25, and m+n=20～235;
R is polyether segment R1, the R2...Ri of the serial different molecular weight that links to each other with silicon atom, 1≤i≤6 wherein, the structure of R
General formula is following formula (II)
Wherein in the structural formula (II): different Ri molecular weight differ, its scope is 700～9500, the value of x is 3～160, the value of y is 0～140, and the weight proportion of PEO and PPOX segment in the segment: the PEO segment is 20～70%, and the PPOX segment is 30～80%;
M is that carbon number is 1～4 alkane, hydrogen atom, acyloxy or silicon methyl in the structural formula (II).
2, the preparation method of a kind of masked non-ionic surfactant according to claim 1 is characterized in that may further comprise the steps:
A) with the allyl alcohol be initiator, in reactor, add oxirane and expoxy propane, in the presence of the catalyst a, pressure≤0.2Mpa, reaction temperature be to react 4～6 hours under 100～130 ℃ of conditions, obtain the end acrylic polyethers R ' 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) terminal hydroxy group with polyethers R ' carries out modification, and the terminal hydroxy group of polyethers R ' employing soon contains sodium or the potassium compounds carries out pure salinization replacement, obtains the Aethoxy Sklerol metal, adopts chloride to carry out chlorination reaction then, obtains blocking modification polyethers Ri;
C) make octamethylcy-clotetrasiloxane, containing hydrogen silicone oil, HMDO under catalyst b effect, in reaction temperature is to react 4～6 hours under 60～90 ℃ of conditions, obtain polysiloxanes (I), wherein the mol ratio between octamethylcy-clotetrasiloxane, containing hydrogen silicone oil, the HMDO is 10-120: 1-5: 1.0-2.0;
D) different modified polyether R1～Ri80-130 part and polysiloxanes (I) 10-35 part of the weight portion that top reaction is obtained, under the Pt of the 5-15ppm catalyst action and in the presence of the solvent, in reaction temperature is to carry out polymerisation under 60～120 ℃ of conditions to carry out decompression distillation after 8～10 hours, after stirring it is squeezed into falling film evaporator and carry out second distillation, promptly make masked non-ionic surfactant.
3, the preparation method of masked non-ionic surfactant according to claim 2 is characterized in that steps A) described in catalyst a be bimetallic catalyst, its consumption is the 5-100ppm of oxirane and expoxy propane consumption sum.
4, the preparation method of masked non-ionic surfactant according to claim 3 is characterized in that described bimetallic catalyst is the zinc hexacyanocobaltate compounds.
5, the preparation method of masked non-ionic surfactant according to claim 2 is characterized in that steps A) described in the oxirane and the weight proportion of expoxy propane as follows:
Oxirane is 20～70%
Expoxy propane is 30～80%.
6, the preparation method of masked non-ionic surfactant according to claim 2 is characterized in that step B) described in the terminal hydroxy group that will hold acrylic polyethers R ' to carry out its step of modification as follows:
To hold acrylic polyethers, sodium or potassium compounds to add reactor successively, sodium or potassium compounds consumption are 0.1～2% of polyethers weight, be warming up to 90～130 ℃ of insulations 2～4 hours under the normal pressure, carry out decompression distillation then, material is cooled to 70～90 ℃ again, the slowly logical chloride controlled pressure≤0.45MPa that adds, be incubated 0.5～2 hour, regulating PII then is 5～6 o'clock, adds the filter aid of weight of material 3～5% again, stir after 2 hours, material filtering is obtained modified polyether Ri.
7, the preparation method of masked non-ionic surfactant according to claim 6 is characterized in that described chloride is chloromethanes or chlorobutane.
8, the preparation method of masked non-ionic surfactant according to claim 2, it is characterized in that step C) described in catalyst b be lewis acid, its consumption is 0.1～3% of octamethylcy-clotetrasiloxane, containing hydrogen silicone oil and a HMDO weight sum; The content of hydrogen is 0.03～0.5% in the described containing hydrogen silicone oil.
9, the preparation method of masked non-ionic surfactant according to claim 2, it is characterized in that step D) described in catalyst be chloroplatinic acid, described solvent is benzene or dimethylbenzene, and solvent load is 50～120% of polyethers and a polysiloxanes weight sum.
10, the application of a kind of masked non-ionic surfactant as claimed in claim 1 in polyurethane foam technology.
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