CN1984875A - Composition comprising choline hydroxide and process for preparing the same - Google Patents

Composition comprising choline hydroxide and process for preparing the same Download PDF

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Publication number
CN1984875A
CN1984875A CNA2005800231541A CN200580023154A CN1984875A CN 1984875 A CN1984875 A CN 1984875A CN A2005800231541 A CNA2005800231541 A CN A2005800231541A CN 200580023154 A CN200580023154 A CN 200580023154A CN 1984875 A CN1984875 A CN 1984875A
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China
Prior art keywords
choline
composition
stablizer
weight
solution
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Pending
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CNA2005800231541A
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Chinese (zh)
Inventor
R·布鲁切克
H·A·沃克尔
J·W·F·L·西茨
G·J·奥登代克
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Akzo Nobel NV
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Akzo Nobel NV
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/005—Stabilisers against oxidation, heat, light, ozone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/40—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton with quaternised nitrogen atoms bound to carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/55—Boron-containing compounds
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/07—Nitrogen-containing compounds
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/03—Non-macromolecular organic compounds
    • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
    • D21H17/11—Halides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Paper (AREA)

Abstract

The present invention relates to a composition comprising choline hydroxide, a solvent, and one or more stabilizers selected from the group consisting of a hydride and choline sulfite.

Description

The composition and method of making the same that contains bursine
The present invention relates to comprise the composition of bursine, stablizer and solvent, the method for preparing said composition with and uses thereof.
Bursine is also referred to as choline or (2-hydroxyethyl) trimethylammonium hydroxide, is the well-known multi-purpose organic bases that is suitable for.
Yet, the composition of bursine, especially the composition in water subjects to progressively decomposition course.The major cause of this decomposition is considered to by itself tendency of the choline attack due to the further reaction of this degradation production.The basic chemofacies of this decomposition is when complicated and not understanding fully, but it has caused choline solution to be become black and produced precipitation by brown in longer-term stores.
For fear of this decomposition, in the known aqueous composition that stablizer is added bursine, thereby allow choline solution to store as the longer-term of clear solution.
US 4,294, and the 911 stable enriched materials that disclose sulphite add in the moisture choline hydroxide composition.Usually the sulphite that adds is sodium sulfite salt cheap and that be easy to obtain.Using the shortcoming of S-WAT is the still blackening in the short period of time of dense choline solution, believes that this is because due to the low-solubility of S-WAT in dense choline solution.For example, in the aqueous choline base solution of 45 weight % solubilized less than the S-WAT of 0.5 weight %.Although there is more solubility sulphite, these are expensive more and/or be difficult to obtain.
US 4,686, and the 002 stable enriched material that discloses formaldehyde adds in the moisture choline hydroxide composition.Because environmental problem, formaldehyde has been forbidden in many application.
The purpose of this invention is to provide a kind of stable choline hydroxide composition that does not have above shortcoming.
This purpose realizes by a kind of choline, solvent and one or more compositions that is selected from the stablizer of hydride and choline sulfite of comprising is provided.
Comparing the stablizer that is used for the present composition with S-WAT makes composition keep its white in more over a long time.Stablizer of the present invention also has following advantage: they introduce salt still less usually in composition; Compare the hydride that needs less amount usually with the conventional composition that contains sodium sulfite salt preventing the composition blackening, and choline sulfite can not introduced any salt in composition.
Should be noted that at US 6,065, a kind of aqueous composition that comprises bursine or hydrogen boron salt has been discussed in 424.Yet this publication does not disclose the composition of bursine and hydrogen boron salt.This publication had not both related to be stablized choline hydroxide solutions even not to admit that also hydrogen boron salt can stablize the fact of bursine.
In the preferred embodiment of the present composition, solvent is water or alcohol, and more preferably water or methyl alcohol most preferably are water.Yet, also can use the mixture of these solvents.
In a further preferred embodiment, the present invention relates to comprise the composition of bursine and borohydride compound, wherein the amount of borohydride compound is by weight less than the amount of bursine.
In a further preferred embodiment, to comprise based on composition total weight be the bursine of 10-60 weight % to the present composition.In a more preferred embodiment, it is the bursine of 20-55 weight % that composition comprises based on composition total weight, and in the most preferred embodiment, it comprises the bursine of 30-50 weight %.
In another preferred embodiment, the present composition comprises hydride as stablizer, and its amount is 1-1,000ppm, preferably 10-500ppm and most preferably 50-200ppm.If stablizer is choline sulfite, then to comprise based on composition total weight be 0.1-19 weight % to the present composition, preferred 0.2-5 weight % and the choline sulfite of 0.5-1 weight % most preferably.The composition exhibiting that comprises the stablizer of this tittle goes out than containing S-WAT as the higher colour stability of the conventional choline composition of stablizer.
The invention still further relates to a kind of masterbatch, its gross weight that comprises based on bursine, stablizer and solvent is the bursine of 10-60 weight %, one or more of 5-20 weight % are selected from the stablizer of hydride and choline sulfite, and rest part is a solvent.In order to stablize the solution of bursine, can will plant the masterbatch that comprises a large amount of stablizers usually with aequum and add in the solution of bursine.It is 8-15 weight % and the stablizer that most preferably is 10-12 weight % that this masterbatch preferably comprises based on the masterbatch gross weight.
Stablizer of the present invention is selected from hydride and choline sulfite.Described hydride is generally strong reductant and but any hydride known to those skilled in the art.The suitable example of hydride is lithium hydride, aluminum hydride and borohydride.Preferred hydride is borohydride.In should using, term " borohydride " refers to comprise any compound of molecule of boron atom and hydrogen atom or the mixture of compound, and it is also referred to as hydroborons, has formula B xH y, wherein x and y are＞0 integer, for example B 2H 6(diborane), B 4H 10(tetraborane), B 5H 9And B 10H 14(Decaboron tetradecahydride) and by them deutero-negatively charged ion such as BH 4 -Not too preferred gaseous hydrogen boride is because they are difficult to operation and have danger.Preferred borohydride comprises one or more by borohydride deutero-negatively charged ion.Preferred borohydride is BH 4 -Salt and special preferred as alkali borohydride salt.Because its commercially available property and the fact that can prepare, operate and use comparatively safely, preferred alkali metal borohydride salt is sodium borohydride (NaBH 4).
In another preferred embodiment of the present invention, composition comprises the hydride that is fixed on the polymer support, especially borohydride.Use this hydrogen (boron) to change thing and have when needed hydrogen (boron) and change the thing stablizer and can be easy to isolating advantage, for example when in the application that has harmful effect in hydrogen (boron) change thing or inorganic counterion during the use choline solution with choline solution.
In a further preferred embodiment, composition comprises one or more other stable compounds.The suitable example of this stable compound comprises sulphite, formaldehyde, oxyamine, their derivative and mixture.Preferred second kind of stable compound is sulphite or sulfite derivative.Sulfite derivative for example comprises hyposulfite.In a more preferred embodiment, sulphite is S-WAT.In another preferred embodiment, use two or more other stable compounds.
The advantage of stablizer, especially the advantage of borohydride be its reducing power and with the consistency of choline base production process.Because its reducing power makes choline solution be limpid and be paper white.Even can be with hydride, especially borohydride adds in the choline base mixture of flavescence, and still obtains limpid white solution.
Another advantage of stablizer of the present invention is that they are stable under strong alkaline condition.The concentration that this means stablizer in the choline can increase to the required character of sufficiently high amount with combining hydrogen oxidation choline and stablizer.This is especially favourable when borohydride is used used as stabilizers.
Present method also relates among the preparation claim 1-5 each method for compositions, and it is to combine with choline hydroxide solutions by the stablizer that one or more is selected from hydride and choline sulfite.
The compatible fact of the preparation technology of stablizer of the present invention and choline makes and in preparing the method for bursine stablizer is added raw material and/or reaction mixture becomes possibility.
Therefore, the present invention also relates to prepare the method for the present composition, it may further comprise the steps: one or more be selected from hydride and choline sulfite stablizer in the presence of make the reaction of oxyethane and Trimethylamine, described stablizer is added in oxyethane, Trimethylamine and/or the reaction mixture.This method for preparing choline is undertaken by oxyethane and Trimethylamine are reacted under 0-70 ℃ temperature in inert atmosphere usually.
If with the choline sulfite used as stabilizers, also can design by making choline hydroxide solutions run into sulfurous gas and the in-situ preparing choline sulfite, wherein said choline hydroxide solutions makes by making the reaction of oxyethane and Trimethylamine.The amount of gained choline sulfite will depend on the time that choline hydroxide solutions and sulfurous gas meet in the choline hydroxide solutions.By choline hydroxide solutions and sulfurous gas are met the regular hour, can regulate the amount of gained choline sulfite on demand.
In the preferred embodiment of the method for preparing choline, stablizer, especially should to make the gross weight based on final product solution be 1-1 to the consumption of borohydride, 000ppm, preferred 10-500ppm, more preferably the borohydride of 50-200ppm exists.
Hope in order on method prepare under the situation of masterbatch of the present invention, it is 5-20 weight % that the consumption of stablizer should make the gross weight based on final product solution, preferred 8-15 weight %, the and most preferably stablizer of 10-12 weight % exists.
In another preferred embodiment of present method, choline prepares under 10-50 ℃ temperature, and by creating inert atmosphere with rare gas element purge reactor and solution, and keep the safe pressure of rare gas element in reactions steps, described rare gas element is generally nitrogen.In the preferred embodiment of this method, temperature is 15-45 ℃, most preferably is the temperature of about room temperature.
Composition of the present invention is suitable for multiple application.As implied above, because the amount of stablizer can be quite high in the choline, described composition also is used in wherein stablizer also in the active application.In this, stablizer of the present invention, especially borohydride is specially adapted to papermaking and bleached paper.
Therefore, during the method for bleached pulp is also included within and should uses.In this method, paper pulp is contacted with composition of the present invention.
The aqueous composition of the hydrogeneous boron salt of known packets can be used for bleached paper and is for example disclosing among the WO 88/10334.Yet, the not open aqueous composition that comprises bursine and hydrogen boron salt that is used for bleached paper for this purposes.In addition, known borohydride is that the borohydride solution of using in the active application is generally the solution of borohydride in caustic alkali therein, this make usually they not too be suitable for the inconsistent application of caustic solution in, for example papermaking.
Now, the present invention will further specify by following examples:
Preparation example A
In 1 liter autoclave by making 116g oxyethane and the solution reaction of 150g Trimethylamine in 417g water prepare aqueous choline base solution.In reaction by make temperature remain on 15-45 ℃ with cooling jacket.Before beginning, use the purging with nitrogen gas reactor, and in ethoxylation step, keep the safe pressure of the nitrogen of 2-3 crust.
The aqueous choline base solution of gained 45 weight % is used for following examples 1-3.
Preparation example B
Solution of choline sulfite is by preparing in the 45 weight % aqueous choline base solution that stoichiometric gaseous sulfur dioxide added preparation example A.Gained 53 weight % solution of choline sulfite are used for following examples 1,2, in 5 and 6.
Preparation example C
The solution of sodium borohydride in choline is by preparing until the borohydride concentration that reaches 12 weight % in the 45 weight % aqueous choline base solution that solid sodium borohydride added preparation example A.The gained aqueous composition is used for following preparation example D.
Preparation example D
In 1 liter autoclave,, 116g oxyethane and 150g Trimethylamine prepare aqueous choline base solution in 417g water by being reacted.In reaction by make temperature remain on 15-45 ℃ with cooling jacket.Before beginning, use the purging with nitrogen gas reactor, and in ethoxylation step, keep the safe pressure of the nitrogen of 2-3 crust.Before the reaction beginning, add the borohydride solution described in the 0.85g Embodiment C.The gained aqueous composition is used for following embodiment 4 and 5.
The comparative example 1
Choline solution sample with the preparation example A of two 110g under purging with nitrogen gas sucks in the 100ml sample bottle.The total concn that adds solution of choline sulfite choline sulfite in sample of preparation example B is 0.2 weight %.Sample bottle is airtight and store under envrionment conditions.The slight flavescence of solution but still limpid (promptly not precipitating) after four months.
The comparative example 2
Choline solution sample with the preparation example A of two 110g under purging with nitrogen gas sucks in the 100ml sample bottle.The total concn that adds solution of choline sulfite choline sulfite in sample of preparation example B is 0.4 weight %.Sample bottle is airtight and store under envrionment conditions.The slight flavescence of solution but still limpid after four months.
The comparative example 3
Choline solution sample with the preparation example A of two 110g under purging with nitrogen gas sucks in the 100ml sample bottle.The total concn that adds paraformaldehyde paraformaldehyde in sample is 0.4wt%.Sample bottle is airtight and store under envrionment conditions.Solution blackening after four months, and at the bottom of the sample bottle, formed one deck brown precipitation.
Embodiment 4
Choline solution sample with the preparation example D of two 110g under purging with nitrogen gas sucks in the 100ml sample bottle.Sample bottle is airtight and store under envrionment conditions.Solution is still limpid and be paper white after four months.
Embodiment 5
Choline solution sample with the preparation example D of two 110g under purging with nitrogen gas sucks in the 100ml sample bottle.The total concn that adds solution of choline sulfite choline sulfite in two samples of preparation example B is 0.4 weight %.Sample bottle is airtight and store under envrionment conditions.Solution is still limpid and be paper white after four months.
Embodiment 6
Choline solution sample with the preparation example D of two 110g under purging with nitrogen gas sucks in the 100ml sample bottle.The total concn that adds solution of choline sulfite choline sulfite in two samples of preparation example B is 2.6 weight %.Sample bottle is airtight and store under envrionment conditions.Solution is still limpid and be paper white after four months.
Embodiment 7
Choline solution sample with the preparation example D of two 110g under purging with nitrogen gas sucks in the 100ml sample bottle.The total concn that adds S-WAT S-WAT in two samples is 0.5 weight %.Sample bottle is airtight and store under envrionment conditions.Solution is still limpid and be paper white after four months, but has formed white insoluble S-WAT layer at the bottom of the sample bottle.

Claims (10)

1. composition, it comprises bursine, solvent and one or more are selected from the stablizer of the group of being made up of hydride and choline sulfite.
2. according to the composition of claim 1, wherein said stablizer is an alkali metal borohydride salt, more preferably the hydroboration sodium salt.
3. according to each composition in claim 1 and 2, wherein the amount of bursine is 10-60 weight % based on the gross weight of composition, preferred 40-50 weight %.
4. according to each composition in the aforementioned claim, wherein the amount of stablizer is 1-500ppm, preferred 50-200ppm.
5. according to each composition in the aforementioned claim, it comprises one or more other stable compounds, the preferred S-WAT of described other stable compound.
6. masterbatch, its gross weight that comprises based on bursine, stablizer and solvent is the bursine of 10-60 weight %, one or more of 5-20 weight % are selected from the stablizer of the group of being made up of hydride and choline sulfite, and rest part is a solvent.
7. one kind prepares according to each method for compositions among the claim 1-5, and it combines with choline hydroxide solutions by the stablizer that one or more is selected from the group of being made up of hydride and choline sulfite and prepares.
8. one kind prepares according to each method for compositions among the claim 1-5, its comprise the steps: one or more be selected from the group of forming by hydride and choline sulfite stablizer in the presence of make the reaction of oxyethane and Trimethylamine, described stablizer is added in oxyethane, Trimethylamine and/or the reaction mixture.
9. according to each method in claim 7 and 8, wherein said stablizer is an alkali metal salt of borohydride, preferred hydroboration sodium salt.
10. according to each the purposes of composition in papermaking among the claim 1-5.
CNA2005800231541A 2004-07-09 2005-07-04 Composition comprising choline hydroxide and process for preparing the same Pending CN1984875A (en)

Applications Claiming Priority (3)

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EP04076991 2004-07-09
EP04076991.1 2004-07-09
US60/607,350 2004-09-07

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CN1984875A true CN1984875A (en) 2007-06-20

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US (1) US20070193708A1 (en)
EP (1) EP1781594A1 (en)
JP (1) JP2008505867A (en)
CN (1) CN1984875A (en)
CA (1) CA2573213A1 (en)
MX (1) MX2007000298A (en)
RU (1) RU2007104939A (en)
WO (1) WO2006005692A1 (en)

Cited By (7)

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Publication number Priority date Publication date Assignee Title
CN104024214A (en) * 2011-11-22 2014-09-03 塔明克公司 Stabilized choline solutions and methods for preparing the same
CN104039143A (en) * 2012-01-19 2014-09-10 陶氏益农公司 Process For Preparing Choline Hydroxide From Trimethylamine And Ethylene Oxide
CN104066711A (en) * 2011-12-29 2014-09-24 塔明克公司 Process for the production of choline hydroxide
CN109503395A (en) * 2018-12-26 2019-03-22 济南蓬勃生物技术有限公司 A kind of stable choline solution and preparation method thereof
CN109748808A (en) * 2018-12-26 2019-05-14 济南蓬勃生物技术有限公司 A kind of preparation method of Choline Bicarbonate and carbonate
CN111712590A (en) * 2018-04-26 2020-09-25 栗田工业株式会社 Stabilization of compositions comprising quaternary trialkylalkanolamine hydroxides
CN113548973A (en) * 2021-07-28 2021-10-26 上海德迈世欧化工有限公司 Preparation method of electronic-grade choline hydroxide solution

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US20140329184A1 (en) * 2011-11-22 2014-11-06 Taminco Stabilized choline solutions and methods for preparing the same
CA2851406C (en) * 2012-04-13 2019-12-17 Huntsman Petrochemical Llc Using novel amines to stabilize quaternary trialkylalkanolamines
CN105228979B (en) 2013-04-11 2018-04-27 塔明克公司 The improved method of bursine
SG11201509933QA (en) 2013-06-06 2016-01-28 Advanced Tech Materials Compositions and methods for selectively etching titanium nitride

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104024214A (en) * 2011-11-22 2014-09-03 塔明克公司 Stabilized choline solutions and methods for preparing the same
CN104039754A (en) * 2011-11-22 2014-09-10 塔明克公司 Stabilized choline solutions and methods for preparing the same
CN104066711A (en) * 2011-12-29 2014-09-24 塔明克公司 Process for the production of choline hydroxide
CN104066711B (en) * 2011-12-29 2017-04-19 塔明克公司 Process for the production of choline hydroxide
CN104039143A (en) * 2012-01-19 2014-09-10 陶氏益农公司 Process For Preparing Choline Hydroxide From Trimethylamine And Ethylene Oxide
CN111712590A (en) * 2018-04-26 2020-09-25 栗田工业株式会社 Stabilization of compositions comprising quaternary trialkylalkanolamine hydroxides
CN109503395A (en) * 2018-12-26 2019-03-22 济南蓬勃生物技术有限公司 A kind of stable choline solution and preparation method thereof
CN109748808A (en) * 2018-12-26 2019-05-14 济南蓬勃生物技术有限公司 A kind of preparation method of Choline Bicarbonate and carbonate
CN109503395B (en) * 2018-12-26 2021-11-16 济南蓬勃生物技术有限公司 Stable choline solution and preparation method thereof
CN109748808B (en) * 2018-12-26 2021-12-24 济南蓬勃生物技术有限公司 Preparation method of choline bicarbonate and carbonate
CN113548973A (en) * 2021-07-28 2021-10-26 上海德迈世欧化工有限公司 Preparation method of electronic-grade choline hydroxide solution

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EP1781594A1 (en) 2007-05-09
RU2007104939A (en) 2008-08-20
CA2573213A1 (en) 2006-01-19
WO2006005692A1 (en) 2006-01-19
JP2008505867A (en) 2008-02-28
US20070193708A1 (en) 2007-08-23

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