CN102108282B - Alkyl phosphate antistatic agent composition - Google Patents
Alkyl phosphate antistatic agent composition Download PDFInfo
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- CN102108282B CN102108282B CN 200910247338 CN200910247338A CN102108282B CN 102108282 B CN102108282 B CN 102108282B CN 200910247338 CN200910247338 CN 200910247338 CN 200910247338 A CN200910247338 A CN 200910247338A CN 102108282 B CN102108282 B CN 102108282B
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Abstract
The invention relates to an antistatic agent composition which comprises a monohydric alcohol phosphate monoester/diester component and a dihydric alcohol phosphate monoester/diester component. The antistatic property and lubricating property of the antistatic agent composition provided by the invention are obviously superior to those of the corresponding single-component phosphate product.
Description
Technical field
The present invention relates to a kind of antistatic agent composition.Particularly, the present invention relates to a kind of alkyl phosphate antistatic agent composition.
Technical background
Alkyl phosphate (salt) is a class function excellent anionic tensio-active agent, have antistatic, wetting, solubilising concurrently, clean, emulsification, dispersion, chelating, multiple function such as lubricated, and be easy to biological degradation, pungency is low, the thermostability height, thereby be widely used in industrial circles such as chemical fibre, weaving, printing and dyeing, plastics, papermaking, leather, household chemicals and electronics, often be used to prepare permeate agent, static inhibitor, fire retardant, defoamer, fatting agent, emulsifying agent, dispersion agent etc.During as static inhibitor, require product to sprawl, and effectively reduce surface resistivity, be beneficial to the dissipation of static charge on the application surface.For the occasion that has triboelectrification, except above-mentioned requirements, static inhibitor preferably also can have good lubricating property, can reduce surface resistivity like this, and when improving the static charge dissipation ability, the electrostatic of reducing friction produces.
The alkyl phosphate Industrial products comprise alkyl phosphate monoester, dibasic acid esters and composition thereof.Alkyl phosphate (salt) has been widely used in the industry such as weaving, papermaking, plastics as static inhibitor.
Alkyl phosphate (salt) is that neutralizing with alkali makes again by Fatty Alcohol(C12-C14 and C12-C18) and phosphoric acid esterification agent reaction.The auxiliary agent worker furthers investigate the esterification of above-mentioned Fatty Alcohol(C12-C14 and C12-C18) and Vanadium Pentoxide in FLAKES for many years.
As static inhibitor, the most frequently used Fatty Alcohol(C12-C14 and C12-C18) is C
12-18Monohydroxy-alcohol, phosphoric acid esterification agent then are Vanadium Pentoxide in FLAKES.For example:
CN1634938 (2005) (Shanghai Petrochemial Co Ltd, China Petrochemical Corp) discloses a kind of preparation method of alkyl phosphate salt;
CN1247192 (2000) (Huangma Chemical Group Co., Zhejiang) discloses isomery alcohol (ether) phosphate ester salt synthetic method;
CN 1080650 (1994) (Chen Jiaji etc.) discloses a kind of production method of static inhibitor.
Research conclusion in recent years shows that alkyl phosphate (salt) static inhibitor that is made by monohydroxy-alcohol has following feature:
1) alkyl phosphate monoester (salt) has antistatic property preferably, and alkylphosphonic acid carboxylic acid dibasic acid esters (salt) then has level and smooth preferably performance.
2) the finished product antistatic property of alkyl chain length is relatively poor, and the short finished product of alkyl chain then has antistatic property preferably.
3) change the parameters of phosphating reaction, for example the selection of monohydroxy-alcohol, ratio of components, feed way, temperature of reaction and time, hydrolysis time etc. can be regulated the ratio of monoesters and dibasic acid esters in the finished product within the specific limits.
Preparation dibasic alcohol phosphoric acid ester (salt) generally adopts phosphorus oxychloride and diol reaction to make, and for example CN1821252 has narrated a kind of phosphoric acid ester synthetic method.This type of dibasic alcohol phosphoric acid ester seldom is used as static inhibitor, and how as dispersion agent, fire retardant and water conditioner.
Behind alkyl phosphate (salt) finished product that inventor checking is made by monohydroxy-alcohol, when finding that low and ambient moisture is low at consumption, its antistatic property is difficult to satisfy service requirements.Particularly have in the application art of particular requirement at some, require static inhibitor to have static resistance and oilness concurrently such as spinning and spinning process, monohydroxy-alcohol phosphoric acid ester (salt) is difficult to take into account these functions.
Therefore, press for a kind of static resistance and oilness of having concurrently in this area, can satisfy the static inhibitor of spinning and spinning process requirement.
Summary of the invention
The inventor finds pleasantly surprisedly that by a large amount of tests it is composite to adopt monohydroxy-alcohol phosphoric acid ester (salt) and dibasic alcohol phosphoric acid ester (salt) to carry out, and can make the static inhibitor finished product that static resistance and lubricity significantly are better than corresponding one-component phosphoric acid ester (salt).
Antistatic agent composition of the present invention comprises the monohydroxy-alcohol phosphate mono-ester/diester component of general formula (1) expression and the single dibasic acid esters component of dibasic alcohol phosphoric acid ester of general formula (2) expression:
General formula (1)
The two fat of monoester
The two fat of monoester
In the formula:
R
1Be C
4～20Straight chain or branched-chain alkyl, preferred R
1Be C
8～18Straight chain or branched-chain alkyl, more preferably R
1Be C
12～18Straight chain or branched-chain alkyl;
R
2Be C
2～8Straight chain or branched alkylidene ,-CH
2CH
2OCH
2CH
2-,-CH
2CH
2CH
2OCH
2CH
2CH
2-, or-CH (CH
3) CH
2OCH (CH
3) CH
2-;
M is alkalimetal ion, ammonium ion or C
1-3The hydroxyalkyl ammonium ion.
Antistatic agent composition of the present invention has good lubrication to spun polyester thread, compare with corresponding single component phosphate ester salt, the kinetic friction coefficient that can more effectively hang down yarn to friction member with falling, reduced the electrostatic generation when improving the oilness of yarn, can be effectively applied to spinning, spin, weave with technology such as fabric post-treatment in.
Embodiment
One preferred embodiment in, the mol ratio of the single dibasic acid esters component of dibasic alcohol phosphoric acid ester of the monohydroxy-alcohol phosphate mono-ester/diester component of general formula (1) expression and general formula (2) expression is 3～1: 1～3, is preferably 2～1: 1～2.
One preferred embodiment in, the monoesters in the monohydroxy-alcohol phosphate mono-ester/diester component of general formula (1) expression: the dibasic acid esters mol ratio is 80-40: 20-70, is preferably 75-45: 20-55.
One preferred embodiment in, the monoesters in the single dibasic acid esters component of the dibasic alcohol phosphoric acid ester of general formula (2) expression: the dibasic acid esters mol ratio is 80-40: 20-70, is preferably 75-45: 25-55.
One preferred embodiment in, R
1Be preferably C
8～18Straight chain or branched-chain alkyl, more preferably C
12～18Straight chain or branched-chain alkyl.
R
1Object lesson comprise following structure:
The numbering structural formula
(R1-1) CH
3CH
2CH
2CH
2-
(R1-2) (CH
3)
2CHCH
2CH
2-
(R1-3) CH
3CH
2CH
2CH
2CH
2-
(R1-4) CH
3(CH
2)
6CH
2-
(R1-5) CH
3CH
2CH
2CH
2CH(CH
2CH
3)CH
2-
(R1-6) CH
3CH
2CH
2CH
2CH
2CH
2CH(CH
3)-
(R1-7) CH
3(CH
2)
10CH
2-
(R1-8) CH
3(CH
2)
14CH
2-
(R1-9) CH
3(CH
2)
16CH
2-
(R1-10) CH
3(CH
2)
7CH＝CH(CH
2)
7CH
2-
One preferred embodiment in, R
2Be preferably C
2～3Straight chain or branched alkylidene, or-CH
2CH
2OCH
2CH
2-.
R
2Specific examples comprise following structure:
The numbering structural formula
(R2-1) -CH
2CH
2-
(R2-2) -CH
2CH
2CH
2-
(R2-3) -CH(CH
3)CH
2-
(R2-4) -CH
2CH
2CH
2CH
2-
(R2-5) -CH
2(CH
2)
4CH
2-
(R2-6) -CH
2CH
2-O-CH
2CH
2-
(R2-7) -CH
2CH
2CH
2-O-CH
2CH
2CH
2-
(R2-8) -CH(CH
3)CH
2-O-CH(CH
3)CH
2-
One preferred embodiment in, M is preferably Na
+, K
+, NH
4 +, (HOCH
2CH
2)
2NH
2 +, (HOCH
2CH
2)
3NH
+
Antistatic agent composition of the present invention can adopt dual mode to make, that is:
(1) the synthetic separately back of monohydroxy-alcohol phosphoric acid ester (salt) and dibasic alcohol phosphoric acid ester (salt) is composite;
(2) monohydroxy-alcohol and dibasic alcohol are mixed by a certain percentage, carry out phosphating reaction again and make.
Synthesizing of alkyl phosphate salt of the present invention, can make by corresponding Fatty Alcohol(C12-C14 and C12-C18) and Vanadium Pentoxide in FLAKES reaction with reference to CN1634938 (2005).
The antistatic agent composition that the present invention makes can be effectively applied to the antistatic treatment of fiber, improves the static resistance and the lubricity of fiber, also can be as the antistatic treatment of other occasion.
Embodiment
1) among each embodiment below, the various application performances of antistatic agent composition of the present invention are measured by following measuring method.
I. the induction static voltage and the transformation period of polyester piece good
Testing method: with reference to the mensuration fabric of FZ/T01042-1996 textile materials antistatic property static voltage half life: pure polyester knitting thing
Measure environment: 19～21 ℃ of temperature, humidity 40～45%RH.
Induction static voltage and transformation period through the fabric of antistatic agent treatment are littler, and the antistatic property that static inhibitor is described better.
Ii. the volume resistivity of wool fiber
Testing method: with reference to the GB/T14342-1993 synthetic staple than resistance test method
Fiber: 64 wools after combing and washing process processing
Measure environment: 19～21 ℃ of temperature, humidity 64～66%RH.
Ratio resistance through the fiber of antistatic agent treatment is littler, and the antistatic property that static inhibitor is described better.
Iii. the kinetic friction coefficient of polyester filament yarn
Adopt the capstan winch method to test: with reference to the standard test methods of frictional coefficient between ASTM D 3108-2001 yarn and the solid material
Yarn: do not have oily polyester filament yarn 150D/48
Measure environment: 19～21 ℃ of temperature, humidity 64～66%RH.
Test parameter: pretension 35～45cn, ceramic friction member, thread friction speed 300m/min
Kinetic friction coefficient through the yarn of antistatic agent treatment is lower, illustrates that static inhibitor to the lubricity of yarn better.
Iv. the friction static voltage of polyester filament yarn
The same kinetic friction coefficient of condition determination when measuring polyester filament thread friction coefficient, adopts the triboelectrification situation of electro static instrument test yarn, and during test, the electro static instrument discharge cycle is 10s, presses as the standard of weighing the triboelectrification performance with maximum electrostatic.
The friction static voltage of the yarn of process antistatic agent treatment is low more, illustrates that static inhibitor is good more to the lubricated and antistatic over-all properties of yarn.
2) phosphoric acid ester (salt) is synthetic:
The synthetic method of phosphoric acid ester (salt) is with reference to patent CN1634938 (2005).The preparation of monohydroxy-alcohol, dibasic alcohol, alcohol mixture phosphate kalium salt is exemplified below:
A) sample 1-1---the preparation of 2-Ethylhexyl Alcohol phosphate kalium salt
In the there-necked flask that electronics constant speed stirrer, thermometer are housed, add 2-Ethylhexyl Alcohol 440.11g, ortho phosphorous acid 0.50g.Open stirrer, stirring velocity is heated to about 40 ℃ more than 600rpm.159.39gP
20
5Be divided into 9 batches, slowly join in the there-necked flask, reinforced process maintains the temperature at below 70 ℃; P
2O
5After adding, temperature of charge is raised to 80 ℃, and under this temperature, is incubated 4 hours, add 1.2g water, stirred 30 minutes, cool to below 50 ℃.The potassium hydroxide aqueous solution that slowly adds 141.0g 50% while stirring, with suitable quantity of water and potassium hydroxide solution, the solid content of adjusting product is 30 ± 0.5%, pH value 7.5～8.0 stirred 30 minutes, cooled to below 50 ℃, discharging obtains the product that outward appearance is a milky white liquid.
B) sample 1-3---the preparation of ethylene glycol phosphate kalium salt
In the there-necked flask that electronics constant speed stirrer, thermometer are housed, add ethylene glycol 340.47g, ortho phosphorous acid 0.30g.Open stirrer, stirring velocity is heated to about 40 ℃ more than 600rpm.259.53gP
20
5Be divided into 12 batches, slowly join in the there-necked flask, reinforced process maintains the temperature at below 70 ℃; P
2O
5After adding, temperature of charge is raised to 80 ℃, and under this temperature, is incubated 4 hours, cool to below 50 ℃.
Get above-mentioned synthetic good ethylene glycol phosphoric acid ester 100.0g in there-necked flask, the potassium hydroxide aqueous solution that slowly adds 144.8g 50% while stirring, with suitable quantity of water and potassium hydroxide solution, the solid content of adjusting product is 30 ± 0.5%, pH value 7.5～8.0, cool to below 50 ℃, discharging obtains the product that outward appearance is a colourless transparent liquid.
C) sample 1 '-1---mix the preparation of 2-Ethylhexyl Alcohol ethylene glycol phosphate kalium salt
In the there-necked flask that electronics constant speed stirrer, thermometer are housed, add 2-Ethylhexyl Alcohol 336.46, ethylene glycol 80.18g, ortho phosphorous acid 0.30g.Open stirrer, stirring velocity is heated to about 40 ℃ more than 600rpm.183.36gP
2O
5Be divided into 9 batches, slowly join in the there-necked flask, reinforced process maintains the temperature at below 70 ℃; P
2O
5After adding, temperature of charge is raised to 80 ℃, and under this temperature, is incubated 4 hours, cool to below 50 ℃.Get synthetic good alcohol mixture phosphoric acid ester 100.0g in there-necked flask, the potassium hydroxide aqueous solution that slowly adds 102.0g 50% while stirring, with suitable quantity of water and potassium hydroxide solution, the solid content of adjusting product is 30 ± 0.5%, pH value 7.5～8.0, cool to below 50 ℃, discharging obtains the product that outward appearance is a colourless transparent liquid.
Different according to raw material and synthesis condition can make other phosphoric acid ester (salt) static inhibitor finished product.Concrete outcome is listed in the table 1,2.
Claims (9)
1. an antistatic agent composition is characterized in that, it comprises the monohydroxy-alcohol phosphate mono-ester/diester component of general formula (1) expression and the single dibasic acid esters component of dibasic alcohol phosphoric acid ester of general formula (2) expression:
In the formula:
R
1Be C
4 ~ 20Straight chain or branched-chain alkyl,
R
2Be C
2 ~ 8Straight chain or branched alkylidene ,-CH
2CH
2OCH
2CH
2-,-CH
2CH
2CH
2OCH
2CH
2CH
2-, or-CH(CH
3) CH
2OCH(CH
3) CH
2-,
M is alkalimetal ion, ammonium ion or C
1-3The hydroxyalkyl ammonium ion, the mol ratio of the single dibasic acid esters component of dibasic alcohol phosphoric acid ester of the monohydroxy-alcohol phosphate mono-ester/diester component of general formula (1) expression and general formula (2) expression is 3 ~ 1:1 ~ 3.
2. antistatic agent composition as claimed in claim 1 is characterized in that, the mol ratio of the single dibasic acid esters component of dibasic alcohol phosphoric acid ester of the monohydroxy-alcohol phosphate mono-ester/diester component of general formula (1) expression and general formula (2) expression is 2 ~ 1:1 ~ 2.
3. antistatic agent composition according to claim 1 is characterized in that the monoesters in the described monohydroxy-alcohol phosphate mono-ester/diester component: the dibasic acid esters mol ratio is 80-40:20-70.
4. antistatic agent composition according to claim 1 is characterized in that, the monoesters in the single dibasic acid esters component of described dibasic alcohol phosphoric acid ester: the dibasic acid esters mol ratio is 80-40:20-70.
5. as each described antistatic agent composition among the claim 1-4, it is characterized in that R
1Be C
8～18Straight chain or branched-chain alkyl.
6. as each described antistatic agent composition among the claim 1-4, it is characterized in that R
2Be C
2 ~ 3Straight chain or branched alkylidene, or-CH
2CH
2OCH
2CH
2-.
7. as each described antistatic agent composition among the claim 1-4, it is characterized in that M is sodium ion, potassium ion, ammonium ion or triethanol ammonium ion.
8. as each described antistatic agent composition among the claim 1-4, it is characterized in that it also contains water.
9. as each described antistatic agent composition among the claim 1-4, it is characterized in that it makes by the mixture and the phosphoric acid esterification agent reaction of monohydroxy-alcohol and dibasic alcohol.
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|---|---|---|---|
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|---|---|---|---|
| CN 200910247338 CN102108282B (en) | 2009-12-29 | 2009-12-29 | Alkyl phosphate antistatic agent composition |
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| CN102108282B true CN102108282B (en) | 2013-07-31 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1110481A (en) * | 1993-06-07 | 1995-10-18 | 维塔利·伊里奇·克里施托波 | Process for obtaining antistatic polymer compounds |
| JP3220190B2 (en) * | 1991-10-22 | 2001-10-22 | 花王株式会社 | Absorbent articles |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54117554A (en) * | 1978-03-03 | 1979-09-12 | Kureha Chem Ind Co Ltd | Resin composition |
-
2009
- 2009-12-29 CN CN 200910247338 patent/CN102108282B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3220190B2 (en) * | 1991-10-22 | 2001-10-22 | 花王株式会社 | Absorbent articles |
| CN1110481A (en) * | 1993-06-07 | 1995-10-18 | 维塔利·伊里奇·克里施托波 | Process for obtaining antistatic polymer compounds |
Non-Patent Citations (5)
| Title |
|---|
| JP昭54-117554A 1979.09.12 |
| 张济邦.膦酸酯的测试和分析.《印染》.1998,第24卷(第7期),39-42. |
| 林秀熊.烷基磷酸酯的开发前景.《印染助剂》.1996,第13卷(第2期),6-10. |
| 烷基磷酸酯的开发前景;林秀熊;《印染助剂》;19960430;第13卷(第2期);6-10 * |
| 膦酸酯的测试和分析;张济邦;《印染》;19980731;第24卷(第7期);39-42 * |
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