CN1944472A - Water soluble cyclic dextrin clathrate complex initiator and its preparing method - Google Patents

Water soluble cyclic dextrin clathrate complex initiator and its preparing method Download PDF

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CN1944472A
CN1944472A CN 200510108025 CN200510108025A CN1944472A CN 1944472 A CN1944472 A CN 1944472A CN 200510108025 CN200510108025 CN 200510108025 CN 200510108025 A CN200510108025 A CN 200510108025A CN 1944472 A CN1944472 A CN 1944472A
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initiator
cyclodextrin
alkyl
carbon number
phenyl
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吴飞鹏
李姝静
李妙贞
王尔鑑
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Technical Institute of Physics and Chemistry of CAS
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Abstract

The present invention relates to organic functional compound, and is especially water soluble cyclodextrin included complex initiator and its preparation process. The present invention has water soluble cyclodextrin including the hydrophobic initiator to form water soluble initiator and the molar ratio between the initiator and the cyclodextrin is 1/5-1/2. Excessive cyclodextrin can form mixture together with the included initiator for raised water solubility. Water solution polymerization proves the high water solubility and high initiating activity of the cyclodextrin included complex initiator.

Description

Water soluble cyclic dextrin clathrate complex initiator and preparation method
Technical field
The invention belongs to organic functions compound field, particularly water soluble cyclic dextrin clathrate complex initiator and preparation method thereof.
Background technology
Current, because environmental protection requirement, development environmental protection novel material product and coming of new technology, the discharging that reduces organic solvent has become current urgent task, and developing water soluble polymer and aqueous solution polymerization manufacturing process (technology that refers to the polyreaction that can take place in the aqueous solution) become an important development direction of present polymeric material field again.Need to develop energetically new water-soluble starting material under such situation, but a kind of birth of quality matetrial need constantly improve and perfect through design and synthetic, performance and structure etc. are many-sided, process is long, expense is big.And manage existing high-quality, material is converted into water-soluble products efficiently, will be not only to spend less but also be the high shortcut of success ratio, this is the advantage of the technology of the present invention route.
Cyclodextrin (CD) is a kind of cyclic oligosaccharide, has hydrophilic periphery and hydrophobic inner chamber, and wherein common have α, β and a γ cyclodextrin, and they contain 6,7 and 8 glucose units respectively.The starting material of producing cyclodextrin are starch, therefore be fit to big production application (" Cyclodextrins and their uses:a review " Martin Del Valle E.M.Progress Biochemistry 2004,39,1033～1046 (cyclodextrin and application thereof, 2004,39 volumes, 1033～1046 pages)).The cyclodextrin product has been widely used in food, household chemicals, cosmetic and sanitary product, medicine, agricultural and environmental protection aspect at present.It is also relatively more rare that yet cyclodextrin is applied to the polymer process industry.In view of initiator of polyreaction is the key reagents of producing macromolecular material, especially for Raolical polymerizable, need a large amount of radical initiators that use, at present, existing diversified radical initiator compound commodity on the market, their major parts are insoluble in water, are not suitable for using in the polymerizable aqueous system.
Summary of the invention
A purpose of the present invention is to use the inclusion complexing action of cyclodextrin, make the hydrophobicity initiator be converted into water soluble starter, thereby provide water soluble cyclic dextrin clathrate complex initiator, by aqueous solution polymerization reaction confirmation, this initiator not only has good water-solubility, simultaneously have very high initiating activity again, kept the original characteristic of initiator.
Another object of the present invention provides the preparation method of water soluble cyclic dextrin clathrate complex initiator.
The feature of water soluble cyclic dextrin clathrate complex initiator of the present invention is: the hydrophobic part of initiator is made water-insoluble initiator be modified as water miscible initiator by cyclic dextrin clathrate; The mol ratio of initiator and cyclodextrin is 1: 2～1: 5.Excessive cyclodextrin can constitute mixture by the initiator after inclusion, increases the inclusion effect, makes the water-soluble better effects if of initiator.
Water soluble cyclic dextrin clathrate complex initiator of the present invention makes hydrophobicity initiator and water soluble Beta-cyclodextrin form master-object inclusion complex under certain conditions, generates water soluble cyclic dextrin clathrate complex initiator.Be suitable for the commercial initiators that this technology obtains the water soluble cyclic dextrin clathrate complex product, comprise following polytype hydrophobicity free radical and ionic initiator:
(1) superoxide
Figure A20051010802500071
R 1, R 2: phenyl, alkyl, 6 〉=alkyl carbon number 〉=2, or cycloalkyl
R 3, R 4: phenyl, alkyl, 6 〉=alkyl carbon number 〉=2, or cycloalkyl
R 5, R 6: phenyl, alkyl, 6 〉=alkyl carbon number 〉=2, or cycloalkyl
R 7-O-O-H R 7: phenyl or alkyl, 6 〉=alkyl carbon number 〉=2
(2) azo-compound
R 8-N=N-R 9R 8, R 9: isopropyl cyanide, different heptonitrile or phenyl
(3) carbonyl compound
Figure A20051010802500081
R 10, R 11: H, CH 3, COOH, N (CH 3) 2, Cl or OH
Figure A20051010802500082
R 12, R 13: H, CH 3, COOH, N (CH 3) 2, Cl or OH
Figure A20051010802500083
R 14: H, OH, CH 3, OCH 3Or OC 2H 5R 15: OH, OCH 3Or OC 2H 5 R 16: H, CH 3, Cl, CH (CH 3) 2, C (CH 3) 3, R 17: OH, OCH 3, OC 2H 5,
Figure A20051010802500086
(4) salt compound
Figure A20051010802500087
R 18, R 19: H, CH 3Or OC 9H 9X -: Cl -, Br -, BF 4 -, PF 6 -, AsF 6 -Or SbF 6 -
R 20, R 21, R 22: H or CH 3X -: Cl -, Br, BF 4 -, PF 6 -, AsF 6 -Or SbF 6 -
The preparation condition of water soluble cyclic dextrin clathrate complex initiator of the present invention is, at first will select for use the cyclodextrin of suitable cavity size and character to be complementary according to geometrical shape, size and the polarity of initiator molecule, forms stable water-soluble inclusion complex compound.Cyclodextrin (CD) is modal three kinds, by cavity size: α-CD＜β-CD＜γ-CD, wherein is applied as manyly especially with β-CD, has also comprised the CDs derivative of they varied structural modifications.The substituted radical that they are introduced has alkyl, amido, carbonyl, alkoxyl group, hydroxyalkyl etc., and is wherein many with alkyl and hydroxyalkyl application especially, good water solubility.In addition according to the size and the quantity of the hydrophobic body of object initiator molecule, the mol ratio of cyclodextrin/initiator, it is enough water-soluble that requirement should make inclusion complex have, and keeps initiator inherent reactive behavior and initiating power again simultaneously, and technical qualification provided by the invention can meet this requirement.For example: adopt the solution light polymerization process to prepare polyacrylamide, light trigger is benzoin dimethylether (I-651), this is a hydrophobic compound, under inclusion situation not, polyreaction is carried out in the mixed solvent that water-organic solvent is formed, and the beta-cyclodextrin if the I-651 employing methylates (Me-β-CD) do the inclusion complexing to handle, then photopolymerization reaction just can carry out in the aqueous solution, and the light trigger after the inclusion has kept original efficiency of initiation, measurement result such as following table.
Me-β-CD/I-651 Water-soluble K p/K t 1/2 φ p
Inclusion not Insoluble 4.75 1.2×10 4
Me-β-CD/I-651 1: 1 (mol ratio) Bad - -
Me-β-CD/I-651 2: 1 (mol ratio) Well 4.43 1.06×10 4
Me is a methyl;
K pVelocity constant for the polyreaction chainpropagation;
K tVelocity constant for chain termination;
Φ pBe the quantum yield of polyreaction, promptly absorb a photon generation polymeric number of monomers;
The preparation method of water soluble cyclic dextrin clathrate complex initiator of the present invention: comprise molten altogether method, suspension method and be total to three kinds of methods of polishing.Wherein:
(1) is total to molten method
Molten method is applicable to that cyclodextrin and initiator all can be dissolved in in a kind of organic solvent or the mixed solvent altogether.At first be in the mixed solvent of 1: 2～1: 5 ratio (volume ratio is 9: 1) that be dissolved in organic solvent or organic solvent and water in molar ratio with initiator and cyclodextrin, the mass percentage concentration that makes initiator and cyclodextrin is 3%～35%, placed under the vibrator normal temperature continuous oscillation then 3～7 hours, normal temperature left standstill 2～5 hours again, detect inclusion reaction whether fully (it is that mass percentage concentration is that 95% chloroform and mass percentage concentration are 5% alcohol mixed solution that thin layer chromatography detects used developping agent) with thin layer chromatography, rotary evaporation removes and desolvates then, product obtains solid, water soluble inclusion complex product 30 ℃～50 ℃ following vacuum-dryings.If will be further purified, solid product can be dissolved in the distilled water again, through handling with lyophilize behind the membrane filtration, can obtain pure Powdered inclusion complex.
(2) suspension method
Suspension method is applicable to that initiator can be dissolved in the organic solvent that can mix with water.At first initiator is dissolved in the organic solvent, be configured to the solution of 5～25wt% concentration, cyclodextrin is made into the aqueous solution of 30～60wt%, keeping initiator and the two mol ratio of cyclodextrin is 1: 2～1: 5, under stirring at room, initiator solution is progressively joined in the aqueous solution of cyclodextrin then, obtain finely divided aaerosol solution, and continuously stirring makes it generate clear solution, placed under the room temperature 2～5 hours, after detection is confirmed to react completely, rotary evaporation removes and desolvates, and product obtains the dry powder inclusion complex 30 ℃～50 ℃ following vacuum-dryings.Sometimes in order to accelerate the formation of inclusion complex, can after generating clear solution, use ultrasonication again 10～20 minutes.If will be further purified, solid product can be dissolved in the distilled water again, through handling with lyophilize behind the membrane filtration, can obtain pure Powdered inclusion complex.
(3) be total to polishing
Polishing is applicable to the preparation of most solid, liquid initiator inclusion complex altogether.At first cyclodextrin is placed shredder, and adding less water (relative humidity 60%～75%) grinds to form lotion, it in initiator and cyclodextrin mol ratio 1: 2～1: 5 ratio, adding concentration in lotion is the organic solvent solution of the initiator of 10～40wt%, continue to grind 3～4 hours, the viscosity increase of mixture has shown the generation of inclusion complex.In mixing process,, can replenish an amount of water and make the inclusion reaction more complete for keeping the plastic yield of lotion.Final product carries out vacuum-drying under 30 ℃～50 ℃, obtain the inclusion complex of powder.If will be further purified, solid product can be dissolved in the distilled water again, through handling with lyophilize behind the membrane filtration, can obtain pure Powdered inclusion complex.
Described cyclodextrin is selected from α-CD, β-CD, alkylating α-CD, wherein 4 〉=alkyl carbon number 〉=1, aminated α-CD, the α-CD of carbonylation, oxyalkylated α-CD, the α-CD of hydroxyalkylation, alkylating β-CD, wherein a kind of among the β-CD of 4 〉=alkyl carbon number 〉=1, aminated β-CD, the β-CD of carbonylation, oxyalkylated β-CD, hydroxyalkylation.
Described organic solvent is selected from one or more the mixed solvent etc. in methyl alcohol, ethanol, acetone, acetonitrile, methane amide, the dioxane.
The preparation method's of water soluble cyclic dextrin clathrate complex initiator of the present invention condition comprises that the temperature of concentration, preparation process and drying temperature and solvent all will decide according to the character of the initiator of concrete use, avoid high temperature as far as possible, also want lucifuge for light trigger, should be under the low light level in preparation process, even in the darkroom, carry out.
Embodiment
Molten legal system is equipped with water soluble cyclic dextrin clathrate complex initiator (carrying out in the preparation process) in the darkroom altogether
Embodiment 1.
(Me-β-CD) and 0.3g (1.17mmol) benzoin dimethylether (I-651) are dissolved in 10ml ethanol/water (9: 1V/V) in the mixing solutions with 3.1g (2.34mmol) methyl flamprop, vibrated at normal temperatures 3 hours with vibrator, normal temperature was placed 3～8 hours down again, detected with thin chromatography then.After reacting completely, rotary evaporation removes and to desolvate, and 40 ℃ of vacuum-dryings obtain Me-β-CD/I-651 mol ratio and be 2: 1 inclusion complex solid, and product can be water-soluble.Solid product is dissolved in the distilled water again, through handling with lyophilize behind the membrane filtration, can obtain pure Powdered inclusion complex.
Embodiment 2.
(Me-β-CD) and 0.2g (1.17mmol) Diisopropyl azodicarboxylate (AIBN) are dissolved in 10ml ethanol/water (9: 1V/V) in the mixing solutions with 3.1g (2.34mmol) methyl flamprop, vibrated at normal temperatures 3 hours with vibrator, normal temperature was placed 3～8 hours down again, detected with thin chromatography then.After reacting completely, rotary evaporation removes and to desolvate, and 40 ℃ of vacuum-dryings obtain Me-β-CD/AIBN mol ratio and be 2: 1 inclusion complex solid, and product can be water-soluble.
Suspension method prepares water soluble cyclic dextrin clathrate complex initiator (carrying out in the preparation process) in the darkroom
Embodiment 3.
0.3g I-651 (1.17mmol) is dissolved in the 2mL acetonitrile, 3.1g Me-β-CD (2.34mmol) is dissolved in the 5ml distilled water, under strong mixing, progressively adds in the cyclodextrin aqueous solution then the I-651 acetonitrile solution, obtain dispersion soln, and continue to be stirred to the generation clear solution, placed under the room temperature 3～8 hours, after reacting completely after testing, rotary evaporation removes and desolvates, 40 ℃ of vacuum-dryings obtain Me-β-CD/I-651 mol ratio and are 2: 1 inclusion complex solid, and product can be water-soluble.Solid product is dissolved in the distilled water again, through handling with lyophilize behind the membrane filtration, can obtain pure Powdered inclusion complex.
Embodiment 4.
0.28g benzoyl peroxide (BPO) (1.17mmol) is dissolved in the 2mL acetonitrile, 3.1gMe-β-CD (2.34mmol) is dissolved in the 5ml distilled water, then under strong mixing, progressively add in the cyclodextrin aqueous solution BPO acetonitrile solution, obtain dispersion soln, and continue to be stirred to the generation clear solution, placed under the room temperature 3～8 hours, after reacting completely after testing, rotary evaporation removes and desolvates, 40 ℃ of vacuum-dryings obtain Me-β-CD/BPO mol ratio and are 2: 1 inclusion complex solid, and product can be water-soluble.
Polishing prepares water soluble cyclic dextrin clathrate complex initiator (carrying out in the preparation process) in the darkroom altogether
Embodiment 5.
65.5g (0.05mol) Me-β-CD placed with 15ml distilled water fine grinding becomes lotion in the shredder.The 30% ethanolic soln 20ml that in lotion, adds 6.34g (0.025mmol) I-651 then.With lotion continuously grinding 3～6 hours, treat that inclusion reacts completely after, product carries out vacuum-drying, obtains pulverulent water-soluble inclusion complex product.Solid product is dissolved in the distilled water again, through handling with lyophilize behind the membrane filtration, can obtain pure Powdered inclusion complex.
Embodiment 6.
65.5g (0.05mol) Me-β-CD placed with 15ml distilled water fine grinding becomes lotion in the shredder.The 30% ethanolic soln 30ml that in lotion, adds 9.2g (0.025mmol) diphenyl iodnium a tetrafluoro borate then.With lotion continuously grinding 3～6 hours, treat that inclusion reacts completely after, product carries out vacuum-drying, obtains pulverulent water-soluble inclusion complex product.

Claims (10)

1. water soluble cyclic dextrin clathrate complex initiator, it is characterized in that: the hydrophobic part of initiator is made water-insoluble initiator be modified as water miscible initiator by cyclic dextrin clathrate; The mol ratio of initiator and cyclodextrin is 1: 2～1: 5.
2. initiator according to claim 1 is characterized in that: described initiator is selected from a kind of in the following initiator:
Figure A2005101080250002C1
R 1, R 2: phenyl, alkyl, 6 〉=alkyl carbon number 〉=2, or cycloalkyl;
R 3, R 4: phenyl, alkyl, 6 〉=alkyl carbon number 〉=2, or cycloalkyl;
Figure A2005101080250002C3
R 5, R 6: phenyl, alkyl, 6 〉=alkyl carbon number 〉=2, or cycloalkyl; R 7-O-O-H R 7: phenyl or alkyl, 6 〉=alkyl carbon number 〉=2; R 8-N=N-R 9R 8, R 9: isopropyl cyanide, different heptonitrile or phenyl;
R 10, R 11: H, CH 3, COOH, N (CH 3) 2, Cl or OH;
R 12, R 13: H, CH 3, COOH, N (CH 3) 2, Cl or OH;
R 14: H, OH, CH 3, OCH 3Or OC 2H 5R 15: OH, OCH 3Or OC 2H 5R 16: H, CH 3, Cl, CH (CH 3) 2, C (CH 3) 3,
Figure A2005101080250002C7
OC 2H 4OH, SCH 3Or
Figure A2005101080250002C8
R 17: OH, OCH 3, OC 2H 5,
Figure A2005101080250002C9
R 18, R 19: H, CH 3Or OC 9H 9, X -: Cl -, Br -, BF 4 -, PF 6 -, AsF 6 -Or SbF 6 -
R 20, R 21, R 22: H or CH 3, X -: Cl -, Br -, BF 4 -, PF 6 -, AsF 6 -Or SbF 6 -
3. water soluble cyclic dextrin clathrate complex initiator according to claim 1, it is characterized in that: described cyclodextrin is selected from α-CD, β-CD, alkylating α-CD, wherein 4 〉=alkyl carbon number 〉=1, aminated α-CD, the α-CD of carbonylation, oxyalkylated α-CD, the α-CD of hydroxyalkylation, alkylating β-CD, wherein a kind of among the β-CD of 4 〉=alkyl carbon number 〉=1, aminated β-CD, the β-CD of carbonylation, oxyalkylated β-CD, hydroxyalkylation.
4. preparation method according to each described water soluble cyclic dextrin clathrate complex initiator of claim 1～3, this preparation method comprises molten altogether method, suspension method and common polishing, it is characterized in that:
(1) adopts molten method altogether
Can be dissolved in cyclodextrin in a kind of organic solvent or the mixed solvent and initiator is that 1: 2～1: 5 ratio is dissolved in the mixed solvent of organic solvent or organic solvent and water in molar ratio, place continuous oscillation under the vibrator normal temperature then, normal temperature leaves standstill again, after inclusion reacts completely, rotary evaporation removes and desolvates, product vacuum-drying obtains solid, water soluble inclusion complex product; Or
(2) adopt suspension method
Initiator is dissolved in the organic solvent that can mix with water, is configured to solution, cyclodextrin is made into the aqueous solution; Keeping initiator and the two mol ratio of cyclodextrin is 1: 2～1: 5, under stirring at room, initiator solution is progressively joined in the aqueous solution of cyclodextrin, obtain finely divided aaerosol solution, and continuously stirring makes it generate clear solution, place under the room temperature, after reacting completely, rotary evaporation removes and desolvates, product vacuum-drying obtains the dry powder inclusion complex; Or
(3) adopt polishing altogether
Cyclodextrin being placed shredder, and add entry and grind to form lotion, is 1: 2～1: 5 ratio in initiator and cyclodextrin mol ratio, adds the organic solvent solution of initiator in lotion, continues to grind, and the viscosity increase of mixture has shown the generation of inclusion complex.
5. method according to claim 4 is characterized in that: described preparation process is to carry out at the low light level or in the darkroom.
6. method according to claim 1 is characterized in that: described organic solvent is selected from one or more the mixed solvent in methyl alcohol, ethanol, acetone, acetonitrile, methane amide, the dioxane.
7. method according to claim 4 is characterized in that: described solid product is dissolved in the distilled water again, through handling with lyophilize behind the membrane filtration, obtains pure Powdered inclusion complex.
8. method according to claim 4 is characterized in that: described employing suspension method, the clear solution that generates is carried out ultrasonication.
9. method according to claim 4 is characterized in that: described step (3) grinds to form cyclodextrin the relative humidity 60%～75% of lotion.
10. method according to claim 4 is characterized in that: described initiator is selected from a kind of in the following initiator:
R 1, R 2: phenyl, alkyl, 6 〉=alkyl carbon number 〉=2, or cycloalkyl;
R 3, R 4: phenyl, alkyl, 6 〉=alkyl carbon number 〉=2, or cycloalkyl;
R 5, R 6: phenyl, alkyl, 6 〉=alkyl carbon number 〉=2, or cycloalkyl;
R 7-O-O-H R 7: phenyl or alkyl, 6 〉=alkyl carbon number 〉=2;
R 8-N=N-R 9R 8, R 9: isopropyl cyanide, different heptonitrile or phenyl;
Figure A2005101080250004C4
R 10, R 11: H, CH 3, COOH, N (CH 3) 2, Cl or OH;
Figure A2005101080250004C5
R 12, R 13: H, CH 3, COOH, N (CH 3) 2, Cl or OH;
R 14: H, OH, CH 3, OCH 3Or OC 2H 5, R 15: OH, OCH 3Or OC 2H 5R 16: H, CH 3, Cl, CH (CH 3) 2, C (CH 3) 3,
OC 2H 4OH, SCH 3Or
Figure A2005101080250004C8
R 17: OH, OCH 3, OC 2H 5,
Figure A2005101080250005C1
R 18, R 19: H, CH 3Or OC 9H 9, X -: Cl, Br -, BF 4 -, PF 6 -, AsF 6 -Or SbF 6 -
R 20, R 21, R 22: H or CH 3, X -: Cl -, Br -, BF 4 -, PF 6 -, AsF 6 -Or SbF 6 -
Described cyclodextrin is selected from α-CD, β-CD, alkylating α-CD, wherein 4 〉=alkyl carbon number 〉=1, aminated α-CD, the α-CD of carbonylation, oxyalkylated α-CD, the α-CD of hydroxyalkylation, alkylating β-CD, wherein a kind of among the β-CD of 4 〉=alkyl carbon number 〉=1, aminated β-CD, the β-CD of carbonylation, oxyalkylated β-CD, hydroxyalkylation.
CN 200510108025 2005-10-09 2005-10-09 Water soluble cyclic dextrin clathrate complex initiator and its preparing method Pending CN1944472A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102445369A (en) * 2011-09-28 2012-05-09 中山大学 Sample pretreatment method for testing thermal parameters of organic peroxide
CN102516420A (en) * 2011-11-29 2012-06-27 上海交通大学 Hydrogen abstraction type host-guest water-soluble light trigger and preparation method thereof
CN102516421A (en) * 2011-12-08 2012-06-27 上海交通大学 Cracking type host-guest water-soluble photoinitiator and its preparation method
CN109331784A (en) * 2018-11-12 2019-02-15 中国石油大学(华东) A kind of Chagerdβcyclodextrins derivative and its preparation and application method for removing organic pollutants

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102445369A (en) * 2011-09-28 2012-05-09 中山大学 Sample pretreatment method for testing thermal parameters of organic peroxide
CN102445369B (en) * 2011-09-28 2013-03-20 中山大学 Sample pretreatment method for testing thermal parameters of organic peroxide
CN102516420A (en) * 2011-11-29 2012-06-27 上海交通大学 Hydrogen abstraction type host-guest water-soluble light trigger and preparation method thereof
CN102516421A (en) * 2011-12-08 2012-06-27 上海交通大学 Cracking type host-guest water-soluble photoinitiator and its preparation method
CN109331784A (en) * 2018-11-12 2019-02-15 中国石油大学(华东) A kind of Chagerdβcyclodextrins derivative and its preparation and application method for removing organic pollutants
CN109331784B (en) * 2018-11-12 2021-06-11 中国石油大学(华东) Monosubstituted beta-cyclodextrin derivative for removing organic pollutants in water and preparation and use method thereof

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