CN101492533A - Novel polyether containing styrene oxide opened loop repetitive units and method for preparing the same - Google Patents
Novel polyether containing styrene oxide opened loop repetitive units and method for preparing the same Download PDFInfo
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- CN101492533A CN101492533A CNA2008100090765A CN200810009076A CN101492533A CN 101492533 A CN101492533 A CN 101492533A CN A2008100090765 A CNA2008100090765 A CN A2008100090765A CN 200810009076 A CN200810009076 A CN 200810009076A CN 101492533 A CN101492533 A CN 101492533A
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Abstract
The invention provides novel polyether of styrene oxide ring-opening repeating unit and a preparation method thereof. The preparation method comprises the following steps: the oxygen in the air is isolated; chemical substances containing reactive hydrogen are used as an initiator for polymerization; according to the required amount of the needed objective product, 0 to 99 percent of solvent, is added, a plurality of types of 0.0001 to 99 percent of catalysts are added by times and polymeric monomers of styrene oxide, propylene oxide, ethylene oxidel, butylene oxide and vinylnaphthalene oxide are added by one time or batch; ring opening polyaddition is carried out to form coarse polyether under the temperature of 0 to 300 DEG C, the coarse polyether is processed by neutralization, adsorptive catalyst, degassing, separation and filtering so as to obtain objective product. The side group of the polymer contains large amount of benzene rings, is suitable for being used as surface active agent with special purpose, polyurethane materials and high molecular materials with special functions and has very wide application prospect.
Description
Technical field:
The present invention relates to a kind of novel polyether that contains styrene oxide opened loop repetitive units and preparation method thereof.
Background technology:
(1) the synthetic of nonionogenic tenside has been to compare proven technique in the industry, the direction of novel surfactant study on the synthesis mainly concentrates in the selection of the selection of oleophilic group and hydrophilic group, because oleophilic group selects face narrower, the tensio-active agent that industrial production needs some special types, special applications to require still fails to develop, particularly the required tensio-active agent of non-aqueous system.The collaborative of kinds of surface promoting agent becomes a kind of unavoidable selection, and the collaborative restriction that is subjected to environmental factors and formulation stability, monomer structure stability of tensio-active agent itself, the effect in many industries is not fully up to expectations.The oleophilic group of tensio-active agent is orientated the alkyl of certain chain length as all the time, and kind is few, and difference is less, and all in the design of hydrophilic-structure, nonionogenic tenside is no exception for the research emphasis of most of novel surfactants.Wherein: middle high molecular nonionic shows natural the having of promoting agent: the various starch that with the W-Gum are representative, semisynthetic have: methylcellulose gum, ethyl cellulose, Natvosol, synthetic has: the ethylene oxide adduct of polyoxyethylene polyoxypropylene ether, polyvinyl alcohol, Soxylat A 25-7, polyacrylamide, alkylphenol formaldehyde polycondensate etc.We find to have a problem to take a broad view of middle high molecular nonionogenic tenside oleophilic group, the part of water insoluble except that polyoxypropylene-polyoxyethylene (oleophilic group) all is difficult tensio-active agents that are suitable for institute's Application Areas by structure design synthetic acquisition molecular weight and structure, but the present invention introduce new monomer Styrene oxide 98min. realize project organization oleophilic group, with the new development that brings tensio-active agent to design and develop.
The present invention is directed to problem and demand in production, the life, make every effort on the structure design of oleophilic group, do the work of some initiatives.Import the notion of " programmable oleophilic group ".Make every effort to oleophilic group, adjustable structure design of hydrophilic group and the synthetic required performance of satisfied macroscopic view that obtains from tensio-active agent microcosmic molecule.
Having a extensive future of new texture tensio-active agent, particularly non-aqueous system.The new texture tensio-active agent will produce far-reaching influence, great commercial value in many industries (tensio-active agent, urethane).
(2) general urethane also is to compare proven technique in the industry with polyether glycol, till the present invention the report of the Styrene oxide 98min. monomer being introduced polyethers production is not arranged as yet.The new monomer structure of polyethers is introduced, and will bring the new performance of polyurethane product, new function.To cause the change of polyurethane industrial.Cinnamic synthesizing of polyoxygenated also just has been in the starting stage, and synthetic method is time-consuming longer, can't realize industrialization.
The present invention is directed to the production requirement of the reality of polyurethane field, introduce solvent, adopt the synthetic extraordinary polyethers that contains styrene oxide opened loop repetitive units of multiple catalyst segments, produce consuming time less, controllability is strong, yield is high, aftertreatment is easy, with existing polyethers production technique can seamless link.
(3) Application Areas: regulate the ratio of initiator and monomer Styrene oxide 98min., propylene oxide, ethylene oxide, oxidation naphthalene ethene, with block or mix the synthetic various polyethers that contains styrene oxide opened loop repetitive units of poly-method, its range of application is as follows:
A) can be used as the nonionogenic tenside of special purposes such as farm chemical emulgent, oil field emulsion splitter, mineral flotation agent, extraordinary urethane foam stabilizer, extraordinary solubilizing agent, extraordinary letex polymerization emulsifying agent, special fibre auxiliary agent.
B) can be used as synthetic extraordinary urethanes, plastics, elastomeric extraordinary polyether glycol.
C) can be used as specialty elastomer, plastic milling component and the mixing aid of macromolecular materials such as polyphenylene oxide, polystyrene.
D) can synthesize novel high polymer material: speciality polymer rubber, speciality polymer chemical fibre material, special adhesive.
E) can synthesize the extraordinary liquid crystal material of novel may command performance.
Summary of the invention:
The objective of the invention is to adopt commercial material to make initiator with reactive hydrogen, under the effect of catalyzer and solvent, than general method the open loop of Styrene oxide 98min. monomer is added on the material with reactive hydrogen, by selecting initiator, catalyzer, adjusting block or mixing poly-monomer: ratio, the order of addition(of ingredients) of propylene oxide, ethylene oxide, oxybutylene, oxidation naphthalene ethene, synthetic polyethers with various structures of broad prospect of application, scale operation easily.
Content of the present invention is material and the varsol that contains reactive hydrogen with commercial, under the katalysis of basic catalyst, bimetallic catalyst, monomer open loop additions such as Styrene oxide 98min., propylene oxide, ethylene oxide, oxybutylene, oxidation naphthalene ethene are being contained on the initiator of reactive hydrogen, according to the needs deisgn product structure of using, synthetic a series of polyethers that contain styrene oxide opened loop repetitive units.
Preparation method of the present invention is as follows: the oxygen in the secluding air, with the chemical substance that contains reactive hydrogen as the polymerization initiator, be metered into 0～99% solvent by required target product requirement, gradation adds 0.0001～99% multiple catalyzer, once or in batches add polymerization single polymerization monomer: Styrene oxide 98min., propylene oxide, ethylene oxide, oxybutylene, oxidation naphthalene ethene, under 0～300 ℃ of temperature, ring opening polyaddition forms, and thick polyethers obtains target product through neutralization, adsorptive catalyst, the degassing, separating and filtering.
The general structure of novel polyether is as follows:
1) R
1H
PBe that the monohydroxy-alcohol, monohydric phenol, monoamine, polyvalent alcohol, polyphenol, polyamine, the hydroxyl value equivalent that contain reactive hydrogen is 67～10000 polyethers or polyester polyol;
2) R
2, R
3Comprising hydrogen, methyl, ethyl, naphthyl etc., is the side group of repeating unit after the open loops such as polymerization single polymerization monomer ethylene oxide, propylene oxide, oxybutylene, oxidation naphthalene ethene;
3) m is 1～10000 integer, and n is 0～10000 integer, and k is 0～10000 integer, and q is 1～10000 integer;
4) p is the integer of 1-100, is the functionality numerical value of initiator.When initiator is monohydroxy-alcohol, monohydric phenol, monoamine p=1, when initiator is dibasic alcohol, dihydric phenol, diamine p=2, p=3 when initiator is trivalent alcohol, trihydric phenol, tertiary amine ...
Require the oxygen in the secluding air during polyreaction of the present invention, the method that can adopt comprises that vacuum tightness is greater than 93kPa or nitrogen atmosphere and other protection of inert gas.
Monohydroxy-alcohol, monohydric phenol, polyvalent alcohol, the polyphenol initiator that contains reactive hydrogen of the present invention is characterized in that monohydroxy-alcohol, phenol, polyvalent alcohol, phenol comprise that general formula meets: C
nH
2n+2-p(OH)
p, C
nH
2n-p(OH)
p, C
nH
2n-2-p(OH)
p, C
nH
2n-4-p(OH)
p, C
nH
2n-6-p(OH)
p, C
nH
2n-8-p(OH)
p, C
nH
2n-10-p(OH)
pPure and mild phenol, the value of n is 1～100 integer herein, the value of p is 1～100 integer; Monohydroxy-alcohol comprises: butanols, amylalcohol, hexanol, enanthol, octanol, nonyl alcohol, decyl alcohol, 12 carbon alcohol, ten four carbon alcohols, 16 carbon alcohol, octadecanol, phenylcarbinol, tetrahydrochysene health alcohol etc.; Monohydric phenol comprises: phenol, naphthols, sylvan etc.; Polyvalent alcohol comprises: ethylene glycol, propylene glycol, butyleneglycol, glycerine, tetramethylolmethane, sorbyl alcohol, N.F,USP MANNITOL, Xylitol etc.; Polyphenol comprises dihydroxyphenyl propane, bisphenol S, bis-phenol X etc.
Monoamine, the polyamine initiator that contains reactive hydrogen of the present invention is characterized in that monoamine, polyamine comprise that general formula meets: (C
mH
2m+1)
qN (H)
p(C
nH
2n+1)
kAlkyl replace amine and general formula meets H
2N (CH
2CH
2NH)
mCH
2CH
2NH
2Polyethylene polyamine, the value of m, n is 0～100 integer herein, the value of q, k is 0～2 integer herein, and the value of p, q, k must satisfy q+p+k=3; The described polyamine that contains reactive hydrogen comprises polyethylene polyamine, trimeric cyanamide, trimethylol melamines etc. such as methylamine, dimethylamine, ethamine, diethylamine, quadrol, diethylenetriamine, triethylene tetramine, tetraethylene pentamine, five ethene hexamines.
Solvent of the present invention is meant varsol, comprises that general formula meets C
nH
2n+2, C
nH
2n, C
nH
2n-2, C
nH
2n-4Alkane, alkene, alkynes: as nonane, decane, dodecane, the tetradecane, n-Hexadecane, eicosane etc., the value of n is 1～100 integer herein; Comprise that general formula meets C
nH
2n-6Aromatic hydrocarbons: benzene, toluene, ethylbenzene, dimethylbenzene, isopropyl benzene, butylbenzene, amylbenzene, trimethylbenzene, durene etc., the value of n is 1～100 integer herein; Comprise biphenyl, naphthalene, tetraline, naphthane, vinylbenzene, indenes etc.When initiator was liquid under temperature of reaction, the per-cent that quantity of solvent accounts for total charging capacity can be 0%, and the per-cent that solvent accounts for total charging capacity when needs prepare the polyethers of ultra-high molecular weight can reach 99%.
Gradation of the present invention adds 0.0001～99% multiple catalyzer and is meant: can be at the two or more catalyzer of use in a kind of target product synthetic, but require gradation to add, catalyzer comprises: higher alcohols potassium such as higher alcohols sodium, potassium methylate, potassium ethylates such as potassium hydroxide, sodium hydroxide, lithium hydroxide, cesium hydroxide, hydrated barta, sodium methylate, sodium ethylate and the polynary sodium alkoxide of deutero-, polynary potassium alcoholate, the title complex of monobasic, polyphenol sodium, monobasic, polyphenol potassium, cobalt zinc prussiate, the title complex of iron zinc prussiate etc.
Once of the present invention or add polymerization single polymerization monomer: Styrene oxide 98min., propylene oxide, ethylene oxide, oxybutylene, oxidation naphthalene ethene are meant that charging process can be criticized to add and even drip multiple monomer and form block or mix poly-polyethers that each monomeric order of addition(of ingredients) and feeding quantity are set by the numerical value of the m in the novel polyether general structure, n, k, q in batches.
The neutralizing agent that the present invention adopts is acetic acid, phosphoric acid, oxalic acid etc.When making neutralizing agent with phosphoric acid, phosphoric acid approached 1: 1 o'clock with the mol ratio of basic catalysts such as KOH, and phosphoric acid is excessive slightly, helps forming bigger potassium primary phosphate crystallization, is convenient to the polyethers press filtration.
The structure of polymkeric substance is confirmed through infrared spectra and nuclear magnetic resonance spectroscopy.Number-average molecular weight is measured with the hydroxyl value method.
The present invention prepares new monomer structure polyethers, raw material sources extensively, be easy to get, simple synthetic method, controllability is good, preparation cost is low.
Embodiment:
The following examples are to further specify of the present invention, rather than limit the scope of the invention.
Embodiment 1:1mol molecular weight is that the polyoxytrimethylene of 400 (the hydroxyl value equivalent is 200) stirs the cobalt zinc DMC catalysts that adds total charging capacity 0.005%; under the nitrogen protection; 140 ℃ of temperature of reaction drip the 10mol Styrene oxide 98min., dropwise the insulation aging reaction 0.5 hour; under 140 ℃; vacuum tightness vacuumized 0.5 hour greater than 93kPa, stopped vacuum adds total charging capacity 0.3% then under nitrogen protection analytical pure potassium hydroxide; under 140 ℃; vacuum tightness vacuumized 0.5 hour greater than 93kPa, stopped vacuum; drip the 72.73mol ethylene oxide; 140 ℃ of temperature of reaction dropwised the insulation aging reaction 0.5 hour, under 140 ℃; vacuum tightness is greater than 93kPa; vacuumized 0.5 hour, and stopped vacuum, be cooled to 80 ℃; add in the acetic acid with the potassium hydroxide equivalent and 0.5 hour, filter finished product.Molecular weight of product is 4800.
Embodiment 2:1mol molecular weight is that 500 glycerine polyoxytrimethylene ether (the hydroxyl value equivalent is 167) stirs the dimethylbenzene that adds total charging capacity 35%; stir the cobalt zinc DMC catalysts that adds total charging capacity 0.005%; under the nitrogen protection; 140 ℃ of temperature of reaction; drip the 30mol Styrene oxide 98min.; dropwised the insulation aging reaction 0.5 hour; under 150 ℃; vacuum tightness is greater than 93kPa, and steam heats up, and vacuumizes and takes off dimethylbenzene; treat that temperature rises to 155 ℃; stop vacuum, be cooled to 80 ℃, filter finished product.Molecular weight of product is 4100.
Embodiment 3:1mol molecular weight is that 500 glycerine polyoxytrimethylene ether (the hydroxyl value equivalent is 167) stirs the dimethylbenzene that adds total charging capacity 35%; stir the cobalt zinc DMC catalysts that adds total charging capacity 0.005%; under the nitrogen protection; 140 ℃ of temperature of reaction; drip the 30mol Styrene oxide 98min.; dropwised the insulation aging reaction 0.5 hour; the analytical pure potassium hydroxide that under nitrogen protection, adds total charging capacity 0.3% then; drip the 20mol ethylene oxide, 140 ℃ of temperature of reaction dropwised the insulation aging reaction 0.5 hour; be cooled to 80 ℃; with 0.5 hour, add the Magnesium Silicate q-agent sorbent material in the phosphate aqueous solution of adding and potassium hydroxide equivalent, be warming up to 150 ℃; vacuum tightness is greater than 93kPa; vacuumize dehydration; take off dimethylbenzene, after moisture content is qualified, stops vacuum filtration and get finished product.Molecular weight of product is 4980.
Claims (9)
1, a kind of novel polyether that contains styrene oxide opened loop repetitive units and preparation method thereof, it is characterized in that the preparation method is: the oxygen in the secluding air, with the chemical substance that contains reactive hydrogen as the polymerization initiator, be metered into 0～99% solvent by required target product requirement, gradation adds 0.0001～99% multiple catalyzer, once or in batches add polymerization single polymerization monomer: Styrene oxide 98min., propylene oxide, ethylene oxide, oxybutylene, oxidation naphthalene ethene, under 0～300 ℃ of temperature, ring opening polyaddition forms, and thick polyethers is through neutralization, adsorptive catalyst, take off vapour, separating and filtering obtains target product.The novel polyether general structure is as follows:
2, the described a kind of novel polyether that contains styrene oxide opened loop repetitive units of method as claimed in claim 1 is characterized in that:
1) R
1H
PBe that the monohydroxy-alcohol, monohydric phenol, monoamine, polyvalent alcohol, polyphenol, polyamine, the hydroxyl value equivalent that contain reactive hydrogen is 67～10000 polyethers or polyester polyol;
2) R
2, R
3Comprising hydrogen, methyl, ethyl, naphthyl etc., is the side group of repeating unit after polymerization single polymerization monomer ethylene oxide, propylene oxide, oxybutylene, the open loop of oxidation naphthalene ethene;
3) m is 1～10000 integer, and n is 0～10000 integer, and k is 0～10000 integer, and q is 1～10000 integer;
4) p is the integer of 1-100, when initiator is unit alcohol, unit phenol p=1, when initiator is dibasic alcohol, dihydric phenol p=2, p=3 when initiator is trivalent alcohol, trihydric phenol, by that analogy ...
3, as in the claim 2 1) described monohydroxy-alcohol, monohydric phenol, polyvalent alcohol, the polyphenol initiator that contains reactive hydrogen is characterized in that monohydroxy-alcohol, phenol, polyvalent alcohol, phenol comprise that general formula meets: C
nH
2n+2-p(OH)
p, C
nH
2n-p(OH)
p, C
nH
2n-2-p(OH)
p, C
nH
2n-4-p(OH)
p, C
nH
2n-6-p(OH)
p, C
nH
2n-8-p(OH)
p, C
nH
2n-10-p(OH)
pPure and mild phenol, the value of n is 1～100 integer herein, the value of p is 1～100 integer; Monohydroxy-alcohol comprises: butanols, amylalcohol, hexanol, enanthol, octanol, nonyl alcohol, decyl alcohol, 12 carbon alcohol, ten four carbon alcohols, 16 carbon alcohol, octadecanol, phenylcarbinol, tetrahydrochysene health alcohol etc.; Monohydric phenol comprises: phenol, naphthols, sylvan etc.; Polyvalent alcohol comprises: ethylene glycol, propylene glycol, butyleneglycol, glycerine, tetramethylolmethane, sorbyl alcohol, N.F,USP MANNITOL, Xylitol, sucrose etc.; Polyphenol comprises dihydroxyphenyl propane, bisphenol S, bis-phenol X etc.
4, as in the claim 2 1) described monoamine, the polyamine initiator that contains reactive hydrogen is characterized in that monoamine, polyamine comprise that general formula meets (C
mH
2m+1)
qN (H)
p(C
nH
2n+1)
kAlkyl replace amine and general formula meets H
2N (CH
2CH
2NH)
mCH
2CH
2NH
2Polyethylene polyamine, the value of m, n is 0～100 integer herein, the value of q, k is 0～2 integer herein, and the value of p, q, k must satisfy q+p+k=3; The described polyamine that contains reactive hydrogen comprises: polyethylene polyamine, trimeric cyanamide, trimethylol melamines etc. such as methylamine, dimethylamine, ethamine, diethylamine, quadrol, diethylenetriamine, triethylene tetramine, tetraethylene pentamine, five ethene hexamines.
5, as in the claim 2 1) describedly contain the polyethers of reactive hydrogen or hydroxyl value equivalent that the polyester polyol initiator is characterized in that polyethers or polyester is 67～10000.
6, the preparation method of novel polyether as claimed in claim 1, described solvent is meant varsol, comprises that general formula meets C
nH
2n+2, C
nH
2n, C
nH
2n-2, C
nH
2n-4Alkane, alkene, alkynes as nonane, decane, dodecane, the tetradecane, n-Hexadecane, eicosane etc., the value of n is 1～100 integer herein; Comprise that general formula meets C
nH
2n-6Aromatic hydrocarbons: benzene, toluene, ethylbenzene, dimethylbenzene, isopropyl benzene, butylbenzene, amylbenzene, trimethylbenzene, durene etc., the value of n is 1～100 integer herein; Comprise biphenyl, naphthalene, tetraline, naphthane, vinylbenzene, indenes etc.
7, the preparation method of novel polyether as claimed in claim 1, described gradation adds that 0.0001～99% multiple catalyzer is characterized in that can be at the two or more catalyzer of use in a kind of target product synthetic, but require gradation to add, catalyzer comprises: potassium hydroxide, sodium hydroxide, lithium hydroxide, cesium hydroxide, hydrated barta, sodium methylate, higher alcohols sodium such as sodium ethylate, potassium methylate, higher alcohols potassium such as potassium ethylate, and the polynary sodium alkoxide of deutero-, polynary potassium alcoholate, monobasic, polyphenol sodium, monobasic, polyphenol potassium, the title complex of cobalt zinc prussiate, the title complex of iron zinc prussiate etc.
8, the preparation method of novel polyether as claimed in claim 1, once described or add polymerization single polymerization monomer: Styrene oxide 98min., propylene oxide, ethylene oxide, oxybutylene, oxidation naphthalene ethene is characterized in that in batches: charging process can be criticized to add and even drip multiple monomer and form block or mix poly-polyethers, and each monomeric order of addition(of ingredients) and feeding quantity are set by the numerical value of the m in the novel polyether general structure, n, k, q.
9, a kind of novel polyether that contains styrene oxide opened loop repetitive units and preparation method thereof is characterized in that the novel polyether that contains styrene oxide opened loop repetitive units that adopts the described preparation method of claim 2～8 to obtain.
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2008
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| CN105237759A (en) * | 2015-11-09 | 2016-01-13 | 淄博德信联邦化学工业有限公司 | Polyether polyol for high-tensile elastomer and preparation method thereof |
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| CN106188521A (en) * | 2016-07-30 | 2016-12-07 | 淄博德信联邦化学工业有限公司 | Synthesis of polymer polyalcohol macromolecule dispersing agent |
| CN106188521B (en) * | 2016-07-30 | 2018-07-10 | 淄博德信联邦化学工业有限公司 | Synthesis of polymer polyalcohol macromolecule dispersing agent |
| CN106380589A (en) * | 2016-08-31 | 2017-02-08 | 江苏擎宇化工科技有限公司 | Environmentally-friendly pesticide wetting dispersant, modified dispersant, and preparation method and application of pesticide wetting dispersant |
| CN111203150A (en) * | 2020-01-03 | 2020-05-29 | 杭州詹姆森新材料科技有限公司 | Novel nonionic surfactant and preparation method thereof |
| CN111518251A (en) * | 2020-04-08 | 2020-08-11 | 上海抚佳精细化工有限公司 | Polyurethane rigid foam and preparation method thereof |
| CN112300380A (en) * | 2020-10-14 | 2021-02-02 | 上海科沣新材料有限公司 | Alkoxylation block copolymer of agricultural auxiliary agent and preparation method and application thereof |
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Application publication date: 20090729 |