CN101104694A - Organically functionally modified polysiloxane and use thereof - Google Patents

Organically functionally modified polysiloxane and use thereof Download PDF

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Publication number
CN101104694A
CN101104694A CNA2006101032147A CN200610103214A CN101104694A CN 101104694 A CN101104694 A CN 101104694A CN A2006101032147 A CNA2006101032147 A CN A2006101032147A CN 200610103214 A CN200610103214 A CN 200610103214A CN 101104694 A CN101104694 A CN 101104694A
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group
general formula
preferred
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modified polysiloxane
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R·亨塞尔
A·洛斯
A·维特尔
M·费伦兹
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GOLDSCHMIAT GmbH
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Abstract

The invention relates to an organic functional and modified polysiloxane and the use of the polysiloxane for defoaming in the liquid fuel, specifically in diesel. The invention also has demulsification property to the fuel polluted by water.

Description

Organic functionalization modified polysiloxane and uses thereof
Technical field
The present invention relates to organic functionalization modified polysiloxane and to liquid fuel, the concrete diesel oil that is meant, the froth breaking purposes.Polysiloxane of the present invention also has the emulsion breaking performance to the fuel that is polluted by water.
Background technology
As the mixture of the hydrocarbon polymer of diesel oil, they also may comprise aromatic substance, gas oil and kerosene, have to form the foamy undesirable feature with air mixed when being poured into the fuel container of storage container such as storage tanker and motor vehicle.This can cause hindering filling process, and the container perfusion is insufficient.Therefore in diesel oil, to add defoamer usually.These defoamers should be under alap concentration effectively, and these defoamers should not form any deleterious residue during in the engine internal combustion or to the fuel combustion disadvantageous effect at diesel oil.
In addition, also add in the fuel can emulsion breaking to the fuel that is polluted by water composition.
Defoamer based on polysiloxane is described in patent documentation.
Wherein the silicone-polyether copolymer of Miao Shuing is effectively, because they only are partially soluble in diesel oil and have reduced the surface tension of diesel oil.Dimethyl siloxane units has reduced the surface energy of diesel oil, and polyether lateral chain has then reduced the solvability of multipolymer in the fuel.Known multipolymer, they are also referred to as polyether silicone or organic functionalization modified polysiloxane and represent with following general formula
Me 3Si(OSiMe 2) x(OSiMeR) yOSiMe 3
This multipolymer comprises a polyethers as radicals R, and this polyethers is by as propylene oxide, but more generally is oxyethane, and such monomer and initiator alcohol as vinyl carbinol, addition reaction take place generate.
Therefore, GB-B-2 173 510 relates to a kind of method to diesel oil or jet fuel froth breaking, and based on a kind of defoamer of silicone-polyether copolymer, wherein polyethers is with general formula Q (A) nOZ represents that this defoamer is added fuel.Q is a double functional group, itself and a silicon atom bonding, and A is an oxyalkylene group, and wherein at least 80% is ethylene oxide unit, and Z is a hydrogen atom or another monofunctional group.
A shortcoming of this defoamer is that the froth breaking of wet diesel oil is bad.The implication of wet diesel oil is meant the fuel of the water that contains about 250ppm.These water or in fuel, enter the water of condensation of basin, or in the oil tank transportation, be brought in the fuel-since jar in water be not emptied completely.
The common adding fuel that combines with suit additive (additive package) of defoamer.These suit additives are added into and improve its performance in the gas oil.The implication of suit additive is interpreted as being meant the mixture of different additive, for example improves the composition of combustionproperty, the composition that reduces the smog generation, the composition that reduces harmful exhaust formation, the inhibitor that reduces engine and component corrosion thereof, surfactant, lubricant or the like.This suit additive exists, and for example GB-A-2248068 and periodical " mineral oil technology " (Mineral  ltechnik[Mineral oiltechnology]) 37 (4) is described in the 20th page.Each additive in the suit additive is dissolved in and obtains a kind of concentrated mother liquor (stock concentrate) in a kind of organic solvent, and this mother liquor is added in the gas oil.
DE-C-43 43 235 has illustrated a kind of method of diesel oil froth breaking, has used the organic functionalization modified polysiloxane with following general formula
Radicals R 1Be the alkyl or aryl group,
Radicals R 2Be to be selected from following multiple compounds category: butene derivative, alkanol derivatives, polyethers and alkyl group.
These butene derivatives and polyethers comprise the oxyalkylene and the propylene oxide unit of different compositions.
US-A-5 542 960 has also illustrated the purposes of organopolysiloxane to the diesel oil froth breaking.Used organopolysiloxane is the terpolymer with following general formula
MD xD* yD** zM
M is OSi (CH 3) 3,
D is OSi (CH 3) 2,
D* is OSi (CH 3) R,
D** is OSi (CH 3) R ',
R is a polyethers, and
R ' is a phenol derivatives, preferred oxymethoxyallylbenzene,
X+y+z's and be 35 to 350, preferred 90 to 150, quotient x/ (y+z) is 3 to 6, quotient y/z is 0.25 to 9.Polyether group R should have at least 75% oxyethane composition, and molecular weight is 200 to 800g/mol.
DE-C-195 16 360 has illustrated a kind of method of diesel oil froth breaking, has used the organic functionalization modified polysiloxane with following general formula
Figure A20061010321400071
Radicals R 1Be the alkyl or aryl group, radicals R 2Be chosen as and R 1But group identical at least 10% is a phenol derivatives, has 10% to be to be selected from following multiple compounds category again: butene derivative, alkanol derivatives and alkyl group.Optionally be, can use a kind of like this polyethers, this polyethers is made up of oxyethane and propylene oxide monomer and a kind of initiator alcohol.
EP-A-0 849 352 has illustrated a kind of method of diesel oil froth breaking, has used the silicone-polyether copolymer that has following general formula and contain aromatic yl group
Figure A20061010321400081
Radicals R fBe the alkyl or aryl group, but at least 80% R fGroup is a methyl group.R fGroup or and R 1Identical or and the R of group 2Group or R 3Group is identical, and prerequisite is at least one R fGroup is R 2Group, R 2It is polyether group with following general formula
-(Y) c[O(C 2H 4-dR′dO) m(C xH 2xO) pZ] w
Prerequisite is that at least one the R ' group in each copolymer molecule is an optional aryl that replaces.At this, c is 0 or 1, and d is 1 to 3, and m is more than or equal to 1, and x is an integer of 2 to 4, and p is more than or equal to 1, and w is 1 to 4, and m+p and be 3 to 100.
R 3It is a polyether group that does not contain aryl with following general formula
-(F) q[O(C xH 2xO) rZ] g
G might be 1 to 4, and q is 0 or 1, and x is 2 to 4, and r is more than or equal to 3, and F is the hydrocarbyl group of the had side chain of a g valency.
Should comprise a polyethers that contains aryl at this silicone-polyether copolymer more than 65%.
DE-A-197 26 653 has illustrated with having the polysiloxane of following general formula to the diesel oil froth breaking
R 1Be alkyl group or aromatic yl group with 1 to 4 carbon atom, but at least 80% R 1Group is a methyl group,
R 2Be R 2A, R 2BAnd R 2CGroup,
R 2AGroup is selected from following group:
(a) phenyl derivatives with following general formula
-R 3-(C 6H 4-ZR 4 Z)-OR 5
R 3Be a divalent group, it is to be made of one or more hydrocarbyl groups with 1 to 18 carbon atom, and described alkyl can be chosen wantonly and be substituted,
R 4Be an oh group, a alkyl group, or a alkoxy base with 1 to 6 carbon atom with 1 to 6 carbon atom, and
Z is a number of 0 to 4,
R 5Be an identical or different monoradical, constitute by a hydrocarbyl group or an alkyl group with 1 to 6 carbon atom,
(b) polyether group with following general formula
-(Y)[O(C 2H 4-dR 6 dO) m(C xH 2xO) pZ] w
Implication is
D1 to 3,
m≥1，
X2 to 4,
p≥1，
W1 to 4,
M+p and be 3 to 100,
R 6A hydrogen, univalence hydrocarbyl with 1 to 18 carbon atom, described alkyl can also be an aryl, randomly also can be the aryl that replaces, its substituting group is selected from down the group of group: hydrogen, have alkyl group, alkoxy base and the oh group of 1 to 6 carbon atom, R 6Group also may be different, but at least one R in each copolymer molecule 6Group is an optional aryl that replaces,
Hydrogen of Z or a unit price organic group,
The hydrocarbyl group of a w+1 valency of Y, it can also be branched,
R 2BGroup is selected from following group:
(c) alkene derivatives with following general formula
Figure A20061010321400101
R 7Be that general formula is-CR 9Group, the wherein R of H- 9Be a hydrogen atom or one
The unit price organic group,
R 8Be to have general formula C 2H 4-dR 10 dA group, wherein
R 10Be a hydrogen atom or a univalence hydrocarbyl group with 1 to 18 carbon atom, described alkyl can also be an aryl, randomly also can be the aryl that replaces, its substituting group be selected from down group: hydrogen, have alkyl group, alkoxy base and the oh group of 1 to 6 carbon atom, R 10Group might be different,
E and g are respectively 0 or 1, e+g and be 1 or 2,
F and h are respectively 0 or integers, f+h's and on average be 0 to 14,
(d)-(CH 2-) iOR 11Group,
R 11Be a hydrogen or a unit price organic group,
I is a number of 2 to 20,
(e)-(CH 2-) jCH 3Group,
J is a number of 5 to 30,
R 2CGroup is following group
-(CH 2-) k(OC 2H 4-) 1(OC 3H 3-) nOR 12
R 12Be a hydrogen or a unit price organic group,
K is a number of 2 to 6,
1 is a number of 1 to 50,
N is a number of 0 to 20,
Prerequisite is at least 10% R 2Group is R 2AGroup, at least 10% R 2AGroup is group (a), and at least 10% be group (b), a+b's and be a number of 2 to 400, the ratio of b/a is 0.2 to 20.
Summary of the invention
The performance characteristic of complexity below organopolysiloxane of the present invention has:
-they are a kind of like this fuel defoamers, described defoamer all can guarantee good froth breaking stability for a long time in dried firewood oil and wet diesel oil.The implication of wet diesel oil is interpreted as being meant the fuel that comprises about 250ppm water.
-they can make the mixture emulsion breaking of fuel/water, and promote to add the effect of the demulsifying compound in the fuel, so the consumption of demulsifying compound can reduce and is up to 60%.
-they have good consistency with the suit additive that adds in the diesel oil usually.
Therefore the application relates to the organic functionalization modified polysiloxane with general formula I,
General formula I
N is a+b+c+d+2=140 to 200, and is preferred 150 to 180,
A is 100 to 170, and is preferred 110 to 140,
B is 6 to 25, and is preferred 8 to 15,
C is 0.5 to 25, and is preferred 2 to 12,
D is 6 to 25, and is preferred 8 to 15,
Radicals R is methyl or R independently of one another 1, R 2, R 3, prerequisite is that at least 50% radicals R is not a methyl,
Radicals R 1Be identical or different hydrophobic polyether groups independently of one another with general formula I I, prerequisite be the molecular weight of described polyethers greater than 1000g/mol, and the part of propylene oxide is greater than 50%,
Figure A20061010321400121
General formula I I
N is 3 to 6,
M is 0 to 30,
K is 10 to 40,
Radicals R 2Be the identical or different polyether groups that contains butylene oxide ring independently of one another with general formula III,
Figure A20061010321400122
General formula III
1 is 3 to 6,
O is 0 to 30,
P is 0 to 25,
Q is 1 to 30,
R is 0 to 30,
And
Radicals R 4Be identical or different methyl or hydrogen independently of one another,
Radicals R 3Be identical or different phenol derivativess independently of one another with general formula I V,
Figure A20061010321400131
General formula I V
Radicals R 5Be the group of group under identical or different being selected from independently of one another: alkyl, hydrogen, hydroxyl or alkoxyl group, prerequisite are at least one R 5Group is an oh group.Index s is an integer of 3 to 6.
The invention still further relates to these organopolysiloxanes in froth breaking and the purposes of improving liquid fuel emulsion breaking characteristic.
The essence of polysiloxane oxygen alkane of the present invention is to utilize hydrophobic polyethers R 1And contain the polyethers R of butylene oxide ring 2Combination with the siloxanes of relative high molecular (N＞140).The result is, unexpectedly, is not only at dried firewood oil still in wet diesel oil, above-mentionedly all can reach the desirable complex characteristics of fuel defoamer, and improve the emulsion breaking characteristic of fuel.
Described polyethers (structure I I and III) is to generate by the addition reaction of monomer (as oxyethane, propylene oxide or butylene oxide ring) with a kind of initiator alcohol (as vinyl carbinol).These oxyalkyl chains can random alignment, or has block structure.
R 1Be a hydrophobic end capped polyether group, the molecular weight of this polyether group is greater than 1000g/mol, and the part of propylene oxide is higher than 50%.
R 2It is a polyethers that contains butylene oxide ring.R 2The existence of group is necessary for obtaining above-mentioned performance.
R 3Be phenyl derivatives, preferred phenolic groups.An example of corresponding phenol derivatives is chavicol (neighbour-chavicol).
In the presence of hydrosilylation catalysts, by the addition of allyl group or ethenyl derivatives on the SiH of polysiloxane group, organic group can be introduced in the molecule of polysiloxane, for example according to the method for US-A-5 334 227.
Essence of the present invention particularly is, uses hydrophobic polyethers to prepare organic functionalization modified polysiloxane in conjunction with the polyethers that contains butylene oxide ring.Because the consistency of hydrophobic polyethers in diesel oil, this hydrophobic polyethers has been stablized inconsistent high molecular polydimethylsiloxane chain.
By selecting R 1, R 2And R 3Group and these groups ratio each other might be optimized the consistency of defoamer, thereby obtain best defoaming effect.Be necessary between hydrophilic and hydrophobic structure element, to set up a kind of balance.Be rich in the polyethers of more PO or have the polyethers of high BO content by use, hydrophobicity is strengthened.In addition, the hydrophobicity of siloxanes can be subjected to the influence through the polyethers number of addition.Also can control hydrophobic performance by the phenolic group ratio.Real situation is among the present invention, and the phenolic group number is big more, and the wetting ability of defoamer is strong more.
The present invention's organic functionalization modified siloxanes to be used can directly add in the diesel oil.But, preferably defoamer is added so-called suit additive in the practice.The suit additive consists essentially of the improving agent of a kind of stain remover, a kind of demulsifying compound/anti-clouding agent (dehazer) and a kind of cetane value.In order to improve the consistency of the present invention's organic functionalization modified siloxanes to be used and suit additive, advantageously with defoamer and 2-Ethylhexyl Alcohol or ethylene glycol or contain the solvent of aromatic hydrocarbons.According to the diesel oil foam performance, preferred anti-foam agent concentration is 2 to 8ppm in diesel oil.It is the influence that directly adds diesel oil or add the form of diesel oil by the suit additive that the selection of anti-foam agent concentration is not subjected to defoamer.
Embodiment
The preparation of defoamer A1:
At first with 22.3% SiH functionalized poly dimethyl siloxane (MD 150D ' 35M contains 0.26% hydrogen) mixture and 16.7% the solvent that contains aromatic hydrocarbons introduce.Add a kind of multipolymer of 43.0% again, this multipolymer is initial with vinyl carbinol, with methyl chloride stop and by 80% propylene oxide units and 20% ethylene oxide unit form, molar mass is 1400g/mol.Add 2.1% chavicol and a kind of multipolymer of 15.9% in addition, this multipolymer is initial with vinyl carbinol, form (EO/BO polyethers) by 12 ethylene oxide units and 4 epoxybutane units.Be heated to 120 ℃ under stirring.The platinum catalyst that adds 10ppm.Method with the SiH value detects transformation efficiency, and recording the SiH transformation efficiency after 5 hours is 98%.The propylene glycol of adding 5% in product.
The preparation of defoamer A2:
At first with 19.9% the polydimethylsiloxane (MD of SiH functional group 150D ' 35M contains 0.26% hydrogen) mixture and 16.7% the solvent that contains aromatic hydrocarbons introduce.Add a kind of multipolymer of 49.2% again, this multipolymer is initial with vinyl carbinol, with methyl chloride stop and by 60% propylene oxide units and 40% ethylene oxide unit form, molar mass is 1600g/mol.Add 1.8% chavicol and a kind of multipolymer of 12.4% in addition, this multipolymer is initial with vinyl carbinol, form (EO/BO polyethers) by 12 ethylene oxide units and 4 epoxybutane units.Be heated to 120 ℃ under stirring.The platinum catalyst that adds 10ppm.Method with the SiH value detects transformation efficiency, and recording the SiH transformation efficiency after 6 hours is 98%.The propylene glycol of adding 5% in product.
The froth breaking ability:
In order to test the froth breaking ability of siloxanes of the present invention, defoamer is dissolved in the suit additive of prior art.According to explanation, the consumption of this suit additive in diesel oil is 340ppm.Diesel oil defoamer with 8ppm joins in the suit additive in advance.Diesel oil used herein contains the sulphur of 50ppm.
In contrast, also following product is tested: commercially available defoamer TEGOPREN (TP) 5851 (silicone-polyether copolymer is from Th. Goldschmidt AG (Goldschmidt)) and the defoamer TP325 (OSI) that forms by polyethers that contains EO and oxymethoxyallylbenzene according to prior art.
Foam decomposition situation to the diesel oil that adds additive and defoamer in a pressure assembly has carried out testing (BNP é test).
The froth breaking test-results:
(implication of blank value is interpreted as being meant diesel oil and the suit additive that does not have defoamer)
Defoamer Used concentration (ppm) Foam height 0 day (ml) The foam resolving time (s) Foam height 28 days (ml) The foam resolving time (s)
Blank value 105 40 100 45
A1 8 32 1 37 1
A2 8 36 1 38 1
TP 325 8 39 2 50 4
TP 5851 8 38 2 58 6
Result in wet diesel oil:
(water that in diesel oil, adds 250ppm)
Defoamer Used concentration (ppm) Foam height 0 day (ml) The foam resolving time (s) Foam height 28 days (ml) The foam resolving time (s)
Blank value 107 42 101 44
A1 8 31 1 35 1
A2 8 35 1 39 1
TP 325 8 40 2 65 6
TP 5851 8 40 4 68 10
The emulsion breaking ability:
In order to test the emulsion breaking ability of siloxanes of the present invention, used the test of ASTM D1094 method.In this method, the water with 20ml in an axial graduated cylinder adds in the diesel oil of 80ml 2 minutes postevaluation water sepn of jolting situation.
It is 7 that described water transfers to the pH value with phosphate buffer soln.
The results are shown in following table.In contrast, used the commercially available suit additive that contains and do not contain demulsifying compound.The working concentration of suit additive is 340ppm.
Sample The amount ml of the water that separates
The complete product that does not contain demulsifying compound 0
The complete product that contains the 8ppm demulsifying compound 18
The complete product that contains the 4ppm demulsifying compound 17
The complete product that contains 8ppm demulsifying compound and 8ppmA1 19
The complete product that contains 4ppm demulsifying compound and 8ppmA1 19

Claims (5)

1. organically-modified polysiloxane with general formula I
Figure A2006101032140002C1
General formula I
N is a+b+c+d+2=140 to 200, and is preferred 150 to 180,
A is 100 to 170, and is preferred 110 to 140,
B is 6 to 25, and is preferred 8 to 15,
C is 0.5 to 25, and is preferred 2 to 12,
D is 6 to 25, and is preferred 8 to 15,
Radicals R is methyl or R independently of one another 1, R 2, R 3, prerequisite is that at least 50% R group is not a methyl,
Radicals R 1Be identical or different hydrophobic polyether groups independently of one another with general formula I I, prerequisite be the molecular weight of described polyethers greater than 1000g/mol, and the propylene oxide part is greater than 50%,
Figure A2006101032140002C2
General formula I I
N is 3 to 6,
M is 0 to 30,
K is 10 to 40,
Radicals R 2Be the identical or different polyether groups that contains butylene oxide ring independently of one another with general formula III,
General formula III
L is 3 to 6,
O is 0 to 30,
P is 0 to 25,
Q is 1 to 30,
R is 0 to 30,
And
R 4Be the identical or different groups that is selected from methyl or hydrogen independently of one another, radicals R 3Be identical or different phenol derivativess independently of one another with general formula I V,
Figure A2006101032140003C2
General formula I V
R 5Be the group of group under identical or different being selected from independently of one another: alkyl, hydrogen, hydroxyl or alkoxyl group, prerequisite are at least one R 5Group is oh group (preferred phenol derivatives is neighbour-chavicol).
2. the described organically-modified polysiloxane of claim 1, described polysiloxane is dissolved in a kind of organic solvent.
3. the described organically-modified polysiloxane of claim 2, described solvent is 2-Ethylhexyl Alcohol, ethylene glycol or a kind of solvent that contains aromatic hydrocarbons.
4. the purposes of the described organically-modified polysiloxane froth breaking in diesel oil and oil fuel of one of claim 1 to 3.
5. the purposes of the described organically-modified polysiloxane of claim 4, the concentration of wherein said polysiloxane are 2 to 8ppm, in described fuel.
CNA2006101032147A 2006-07-14 2006-07-14 Organically functionally modified polysiloxane and use thereof Pending CN101104694A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102675647A (en) * 2012-05-08 2012-09-19 浙江大学 Organic silicon modifier and preparation method and application thereof
CN103154164A (en) * 2010-03-22 2013-06-12 蓝星有机硅法国公司 Cross-linkable silicone composition for the production of non-stick coatings for flexible substrates and an attachment-promoting additive contained in said composition
CN111566191A (en) * 2017-11-10 2020-08-21 莫门蒂夫性能材料股份有限公司 Organically modified silicone fuel additives, compositions, and methods of use thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103154164A (en) * 2010-03-22 2013-06-12 蓝星有机硅法国公司 Cross-linkable silicone composition for the production of non-stick coatings for flexible substrates and an attachment-promoting additive contained in said composition
CN103154164B (en) * 2010-03-22 2015-11-25 蓝星有机硅法国公司 The crosslinkable silicon composition producing the anti-stick coating being used for flexible carrier and the attachment comprised in such a composition promote additive
CN102675647A (en) * 2012-05-08 2012-09-19 浙江大学 Organic silicon modifier and preparation method and application thereof
CN111566191A (en) * 2017-11-10 2020-08-21 莫门蒂夫性能材料股份有限公司 Organically modified silicone fuel additives, compositions, and methods of use thereof

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