CN101870738A - Alkyl acid esterified glutinous rice flour and preparation method as well as application thereof - Google Patents
Alkyl acid esterified glutinous rice flour and preparation method as well as application thereof Download PDFInfo
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Abstract
The invention relates to alkyl acid esterified glutinous rice flour and a preparation method as well as application thereof. The alkyl acid esterified glutinous rice flour is prepared by reaction of a natural glutinous rice flour product and an esterifying agent and comprises maleic acid esterified glutinous rice flour and the alkyl acid esterified glutinous rice flour containing 3-18 carbon atoms, wherein, the degree of esterification is 0.0001-1. The glutinous rice flour comprises the flour of glutinous rice, sticky corn, sticky rice, husked millet, big glutinous millet, small glutinous millet and sticky sorghum rice and modified products thereof, starch of the sticky rice and the mixture of one or more modified starch thereof, and preferably glutinous rice starch. The alkyl acid esterified glutinous rice flour can be used as a slowly controlled release film for medicines and an auxiliary material for preparations, and can be used for medicine tablets, granules, capsules, gels, ointments, films, masks and patches. After being cured, the hydrate of the alkyl acid esterified glutinous rice flour can be used as a bonding agent to be applied to the fields of patches, labels, coating, non-setting adhesive and the like, can be used as a percutaneous administration substrate, and can be matched with various medicines and penetration enhancers such as synthetic medicines, Chinese traditional medicine extract, medicinal powder, alcohol, acid, polyol, polyacid and the like to be prepared into patches.
Description
Technical field:
The present invention relates to a kind of alkyl acid esterified glutinous rice flour and its production and application, belong to the treated starch series products.
Background technology:
Rice flour such as sticky rice flour are as a kind of natural tack material, cheap and easy to get, except the important source material of using as food, be used as tamanori in fields such as fluting board, label, coating, as utilize sticky rice flour expanded, crosslinked preparation core sand binder, prepare beer label etc. with sticky rice flour.Amylopectin has the weak and good advantage of freeze-thaw stability of retrogradation in the rice flour, and the rice flour that adds thermomaturation has stickiness preferably, can be used as tackiness agent uses, but the slaking rice flour exists the hardening of easily bringing back to life to lose the problem of stickiness, also have rice flour to belong to hydroaropic substance, poor with the consistency of lyophobic dust such as medicine, fat-soluble liquid etc., influence is used.The applicant discloses " being the pressure sensitive adhesive composition and the application thereof of raw material with the rice flour " in patent application (application number 200710059996.3) a few days ago, relate to the rice flour is main raw material, with water, softening agent and properties-correcting agent combination, through crosslinked, tackify, modification such as strengthen, preserve moisture, add thermomaturation formed have can take off the pressure sensitive adhesive composition that pastes purposes, prepared paster is long-time have after placing bring back to life, the viscosity variation, with phenomenons such as consistency difference such as fat-soluble medicine, additive.
There is the component of many natural products itself to have viscosity or after slaking, produce viscosity, utilizes the viscosity of this natural product,, can obtain to have the product of better visco-elasticity, mechanical strength through suitable modification.
Summary of the invention:
The object of the invention is to provide a kind of alkyl acid esterified glutinous rice flour and preparation method thereof, and it is long chain alkyl modified rice flour, has improved the stickiness of slaking rice flour, long-term stability of placing and the use properties that has strengthened the gluing product of rice flour.The novel alkyl acid esterified glutinous rice flour of this class has the viscosity that is better than unmodified rice flour, anti-bring back to life performance and parent/hydrophobic amphiphilic character, is good novel aqueous tackifier and adhesive raw materials of a class.
Natural product glutinous rice of the present invention (also claims glutinous rice, being referred to as " glutinous rice " among the present invention) powder is meant the powder and the modified product thereof of glutinous rice, glutinous corn, glutinous rice, milled glutinous broomcorn millet, Radix Et Rhizoma Rhei rice, small Semen setariae, glutinous indian millet rice, and one or more mixture of the starch of these glutinous rices and treated starch thereof.
Alkyl acid esterified glutinous rice flour provided by the invention is a kind of alkyl acid esterified glutinous rice flour, it is characterized in that it is to comprise toxilic acid esterification rice flour and the alkyl acid esterified glutinous rice flour that contains 3～18 carbon atoms, and gamma value is 0.0001～1.
Alkyl acid esterified glutinous rice flour of the present invention is the alkyl acid esterification glutinous rice starch that contains 3～18 carbon atoms, the alkyl acid esterification glutinous rice starch that contains 3～18 carbon atoms of preferred gamma value 0.1～0.3.
Alkyl acid esterified glutinous rice flour of the present invention, be that maleic anhydride or the alkyl acid anhydrides that contains 3～18 carbon atoms are esterifying agent and natural product rice flour prepared in reaction, the proportioning of acid anhydrides and rice flour is 0.1～3 according to the mol ratio of the starch glucosyl group of acid anhydrides and rice flour, and the gamma value of described esterification rice flour is the ester group mole number of every mole of glucose unit on esterified.
The step that alkyl acid esterified glutinous rice flour preparation method provided by the invention comprises: natural product rice flour and water are mixed with the rice flour emulsion, the pH that regulates emulsion system with NaOH is between the 8-11, the ethanolic soln that adds esterifying agent then, the mol ratio of the starch glucosyl group of acid anhydrides and rice flour is 0.1～3, temperature is controlled at 30～60 ℃, reacted about 3～18 hours, the pH value of regulation system is between 8-11; PH value with hydrochloric acid soln conditioned reaction system after reaction finishes is 6.5～7.0, filters, and the washing with alcohol with 70%, the vacuum drying oven oven dry promptly gets the esterification rice flour.
Described esterifying agent is that maleic anhydride, n Propanoic acid acid anhydride, isopropyl acid acid anhydride, n butanoic anhydride, isobutyric anhydride etc. contain the alkyl acid anhydrides of 3～18 carbon atoms and their mixture thereof.
The application of esterification rice flour of the present invention comprises as medicine sustained and controlled release film, pharmaceutical adjunct, is used for medicinal tablet, granule, capsule, gelifying agent, paste, film, facial mask and patch; Can be used as tamanori after its hydrate slaking and be applied to fields such as label, coating, non-setting adhesive, be used for percutaneous dosing matrix, can with multiple medicine, permeate promotor compatibility, as synthetic drug, Chinese medical concrete, medicinal powder, alcohol, acid, polyvalent alcohol, polyprotonic acid etc. are prepared into patch.
Technical characterstic of the present invention has provided a class esterification rice flour, its hydrate slaking product has better stickiness and the anti-performance of bringing back to life, and by on the molecular side chain of rice flour, introducing hydrophobic alkyl, given amphipathic feature, had consistency preferably with additives such as hydrophilic, hydrophobic medicine, permeate promotors.Therefore, alkyl acid esterified glutinous rice flour provided by the invention and its production and application technology has good application prospects.
Embodiment:
Embodiment 1
The preparation of toxilic acid esterification starch:
Glutinous rice starch and water is mixed with 40% starch emulsion, be heated to about 30 ℃, the pH that regulates emulsion system with NaOH is 8, slowly add 50% maleic anhydride ethanolic soln then, the mol ratio of acid anhydrides and starch glucosyl group is 0.5: 1, temperature is controlled at 35～40 ℃, reacts about 10 hours, frequently the pH value 10 of regulation system.It is 7.0 with the pH value of 2% hydrochloric acid soln conditioned reaction system that reaction finishes the back, filtration, and the washing with alcohol with 70% 3 times is dried at 50 ℃ of vacuum drying ovens, the toxilic acid esterification glutinous rice starch that gets product, gamma value is 0.023, is designated as MN0.023.
The gamma value measuring method: the 1.5g sample adds the ethanolic soln 20ml of 2.5mol/L hydrochloric acid with the wetting back of 1.5ml ethanol, stir the ethanol 40ml of adding 90% after 30 minutes, after continuing to stir 10min, sand core funnel filters, ethanol drip washing filter cake with 90% (with the check of AgNO solution) till do not have a chlorion, then the sample in the sand core funnel is moved in the beaker of 500ml, add the standard sodium hydroxide solution of 7.5ml 0.25mol/L, add 150ml distilled water.Add 10 1% phenolphthalein indicator behind the boiling water bath 20min, after stirring while hot sulphuric acid soln titration to the solution changes color with 0.05mol/L be terminal point, record consumes vitriolic volume number.Make blank with the sample that does not add the acid anhydrides preparation simultaneously, the calculation formula of gamma value is as follows:
M
o＝7.5M
1-V
oM
2
M
x＝[(7.5M
1-V
XM
2)-M
o]/(2W)
Gamma value Ds=162M
x/ (1000-M
*M
x)
In the formula:
M
0The mmole number of-sodium hydroxide that every gram blank sample is consumed; M
XThe mmole number of the sodium hydroxide that the every gram sample in the blank back of-deduction consumes; M
1The volumetric molar concentration of-sodium hydroxide solution: M
2The volumetric molar concentration of-sulphuric acid soln; V
oThe volume of the sulphuric acid soln that-blank sample consumed (mL); V
xThe volume of the sulphuric acid soln that-sample consumed (ml); The quality of w-sample (g); 162: the molecular weight of each glucosyl residue: M
*: the molecular weight of esterified group.
Embodiment 2
Press embodiment 1 method, different is to adopt glutinous Semen Maydis powder, and the mol ratio of maleic anhydride and starch glucosyl group is 1: 10, makes the glutinous Semen Maydis powder MNy0.0001 of toxilic acid esterification of gamma value 0.0001.
Embodiment 3
Press embodiment 1 method, the mol ratio of different is maleic anhydride and starch glucosyl group is 10: 1, adds 5% methanesulfonic, pH regulator to 11, and temperature is controlled at 40 ℃, reacts about 10 hours, makes the toxilic acid esterification glutinous rice starch MN1.03 of gamma value 1.03.
Embodiment 4
Press embodiment 1 method, different is to adopt rheum officinale ground rice, and the mol ratio of maleic anhydride and starch glucosyl group is 2: 1, the dodecyl sodium sulfonate of adding 4% is a catalyzer, pH regulator to 10, and temperature is controlled at 45 ℃, reacted about 10 hours, and made the toxilic acid esterification Radix Et Rhizoma Rhei rice powder MN of gamma value 0.52
Dh0.44.
Embodiment 5
Glutinous rice starch and water is mixed with 40% glutinous rice starch emulsion, be heated to about 50 ℃, the pH that regulates emulsion system with NaOH is 9, the ethanolic soln that slowly adds 50% isopropyl acid acid anhydride then, the mol ratio of acid anhydrides and starch glucosyl group is 0.5: 1, temperature is controlled at 45 ℃, reacts about 10 hours, and the pH value of regulation system is between 9-10 frequently.It is 6.5 with the pH value of 2% hydrochloric acid soln conditioned reaction system that reaction finishes the back, filtration, and the washing with alcohol with 70% 3 times is dried at 80 ℃ of vacuum drying ovens, promptly gets isopropyl acid esterification glutinous rice starch, and gamma value is 0.035, is designated as iC
3N-0.035.
Embodiment 6
Press embodiment 5 methods, different is to adopt oxidation glutinous rice starch and n Propanoic acid acid anhydride, and the mol ratio of acid anhydrides and starch glucosyl group is 3: 1, the dodecyl sodium sulfonate of adding 2% is a catalyzer, temperature is controlled at 35 ℃, reacts about 14 hours, makes the n Propanoic acid esterification glutinous rice starch C of gamma value 1.0
3N-1.0.
Embodiment 7
Press embodiment 5 methods, different is to adopt the n-caprylic acid acid anhydride, and the mol ratio of acid anhydrides and starch glucosyl group is 0.5: 1, temperature is controlled at 30 ℃, the pH that NaOH with 5% regulates emulsion system is 10, reacts about 10 hours, makes the n-caprylic acid esterification glutinous rice starch C of gamma value 0.01
8N-0.01.
Embodiment 8
Press embodiment 5 methods, different is to adopt the n-caprylic acid acid anhydride, and the mol ratio of acid anhydrides and starch glucosyl group is 1.5: 1, the dodecyl sodium sulfonate of adding 2% is a catalyzer, temperature is controlled at 40 ℃, reacts about 14 hours, makes the n-caprylic acid esterification glutinous rice starch C of gamma value 0.15
8N-0.15.
Embodiment 9
Press embodiment 7 methods, the mol ratio of different is acid anhydrides and starch glucosyl group is 1: 1, and temperature is controlled at 30 ℃, reacts about 15 hours, makes the n-caprylic acid esterification glutinous rice starch C of gamma value 0.081
8N-0.081.
Embodiment 10
Press embodiment 5 methods, different is to adopt small Semen setariae starch and isocaprylic acid acid anhydride, and the mol ratio of acid anhydrides and starch glucosyl group is 2: 1, the dodecyl sodium sulfonate of adding 2% is a catalyzer, temperature is controlled at 60 ℃, reacts about 10 hours, makes the isocaprylic acid esterification small Semen setariae starch C of gamma value 0.27
8N
Xh-0.27.
Embodiment 11
Press embodiment 5 methods, different is to adopt the n-capric acid acid anhydride, and the mol ratio of acid anhydrides and starch glucosyl group is 1: 1, temperature is controlled at 40 ℃, the pH that NaOH with 5% regulates emulsion system is 10, reacts about 10 hours, makes the n-capric acid esterification milled glutinous broomcorn millet powder C of gamma value 0.007
10N-0.007.
Embodiment 12
Press embodiment 5 methods, different is to adopt milled glutinous broomcorn millet powder and stearic acid acid anhydride, the mol ratio of acid anhydrides and starch glucosyl group is 1: 1, the pH that NaOH with 5% regulates emulsion system is 11, the dodecyl sodium sulfonate of adding 2% is a catalyzer, temperature is controlled at 35 ℃, reacts about 5 hours, makes the stearic acid esterification glutinous rice starch C of gamma value 0.008
18N
s-0.008.
Embodiment 13
Press embodiment 5 methods, different is to adopt the isodecyl acid anhydrides, and the mol ratio of acid anhydrides and starch glucosyl group is 2: 1, the dodecyl sodium sulfonate of adding 2% is a catalyzer, temperature is controlled at 40 ℃, reacts about 10 hours, makes the n-capric acid esterification glutinous rice starch iC of gamma value 0.15
10N-0.25.
Embodiment 14
Press embodiment 5 methods, different is to adopt glutinous sorghum rice starch and lauric anhydride, and the mol ratio of acid anhydrides and starch glucosyl group is 1: 1, the sodium sulfate of adding 2% is catalyzer, temperature is controlled at 35～40 ℃, reacts about 10 hours, makes the glutinous sorghum rice starch C of laurostearic acid esterification of gamma value 0.057
12N
g-0.057.
Embodiment 15
Press embodiment 5 methods, different is to adopt the n-capric acid acid anhydride, and the mol ratio of acid anhydrides and starch glucosyl group is 1.2: 1, the dodecyl sodium sulfonate of adding 2% is a catalyzer, temperature is controlled at 35 ℃, reacts about 15 hours, makes the n-capric acid esterification glutinous rice starch C of gamma value 0.083
10N-0.083.
Embodiment 16
Press embodiment 5 methods, different is to adopt positive valeric anhydride, and the mol ratio of acid anhydrides and starch glucosyl group is 1: 1, the dodecyl sodium sulfonate of adding 2% is a catalyzer, temperature is controlled at 40 ℃, reacts about 15 hours, makes the n-capric acid esterification glutinous rice starch C of gamma value 0.101
5N-0.101.
Embodiment 17
Press embodiment 5 methods, different is to adopt mixed acid anhydride (1: 1 n Propanoic acid acid anhydride and n-caprylic acid acid anhydride), the mol ratio of acid anhydrides and starch glucosyl group is 1.2: 1, the sodium sulfate of adding 2% is catalyzer, temperature is controlled at 40 ℃, reacted about 15 hours, and made third of gamma value 0.301-sad esterification glutinous rice starch C
3-8N-0.301.
Embodiment 18
Press embodiment 5 methods, different is to adopt mixed acid anhydride (1: 4 n Propanoic acid acid anhydride and n-caprylic acid acid anhydride), the mol ratio of acid anhydrides and starch glucosyl group is 1: 1, the dodecyl sodium sulfonate of adding 2% is a catalyzer, temperature is controlled at 40 ℃, reacted about 15 hours, and made third of gamma value 0.041-sad esterification glutinous rice starch C
3-8N-0.041.
Embodiment 19
Press embodiment 5 methods, different is to adopt mixed acid anhydride (10: 1 isocaprylic acid acid anhydride and lauric anhydrides), the mol ratio of acid anhydrides and starch glucosyl group is 1: 1, the sodium sulfate of adding 2% is catalyzer, temperature is controlled at 40 ℃, reacted about 15 hours, and made third of gamma value 0.002-sad esterification glutinous rice starch C
8-12N-0.002.
By changing the mol ratio and the reaction conditions of rice flour kind, alkyl acid anhydrides kind, acid anhydrides and starch glucosyl group, can prepare alkyl acid esterification products various gamma values, different rice flour according to the foregoing description method.The alkyl acid esterified glutinous rice flour that table 1 has been enumerated embodiment 1～18 preparation mixes with glycerine, water, adds the application performance of thermomaturation product.
The esterification rice flour composition film performance of table 1 slaking
Annotate: according to GB4852-84 test tack; Hold viscous force according to the GB4851-84 test, use the 500g weight.
Embodiment 20～28
The composition of the pressure sensitive adhesive composition that embodiment 20～28 is prepared sees Table 2, and concrete grammar is:
Each component is mixed, is heated to more than 90 ℃ slaking or water vapour and cooks, be put in roll film forming between mould or backing film and protective membrane, room temperature was placed 2～7 days, volatilized redundant moisture, can form paster.
Embodiment 29
4g C
8N-0.03,2g glycerine and 4g water, mix back steam heating slaking, cooling back adds 5% salicylic ethanol (75% ethanol for preparing, 25% deionized water) solution 3g, mix, be coated with on non-woven fabrics, press mold, ethanol is removed in volatilization, the room temperature sealing was placed 4 days, made Whitfield's ointment transdermal patch (TDDs1); Sneak into Ibuprofen BP/EP with same method in the 15th group curable composition of table 1, the percutaneous absorption patch of preparation Ibuprofen BP/EP, TDDs2.
Embodiment 30
The 18th group composition 8g of table 1, mix, be heated to slaking more than 80～100 ℃, cool to room temperature or below 50 ℃, add Chinese medicine then and cough and breathe heavily cream medicinal extract 2.0g, mix under the effect of room temperature shear agitation, on non-woven fabrics and separate paper, carry out roll extrusion and film, the room temperature sealing was placed 3 days, made Chinese medical concrete transdermal patch (TDDs3).
Embodiment 31
5g MN0.023, glycerine 5g, water 6g mixes, and is heated to slaking more than 80～100 ℃, cools to room temperature or below 50 ℃, gets 10g, sneaks into 0.2g povidone iodine, Yunnan white powder powder respectively, obtains film TDDs4, TDDs5.
Embodiment 32
Press the slaking product of embodiment 23 methods preparations, get 50g, sneak into the refining dog skin plaster medicinal extract of 25g (press official method extracts), at the non-woven fabrics backing film be coated with between silicon paper protective membrane and roll film forming, the room temperature sealing was placed after 7 days, cut into slices, and must make with extra care dog skin plaster paster TDDs6.
Embodiment 33
C
8N-0.032 7g, ethylene glycol 1g, glycerine 2g, water 5g mixes each component, is heated to slaking more than 80～100 ℃, cools to room temperature, adds SHANGSHI ZHITONG GAO 5g, the 0.1g azone, after the mixing, press mold, place a week after, obtain patch TDDs7.
Embodiment 34
36g C
8N-0.001 joins in the 15g water and mixes, add thermomaturation after, cooling adds the aqueous solution contain the 0.3g Trisodium trimetaphosphate, adds 5g honey, 1g phosphatide and 1g reed fragrant plant glue oil then, films, sealing is placed and was obtained aquagel membrane in 4 days, can be used for facial mask.Also can make gel-film suck milk before use uses again.
Table 2 embodiment 19～27 raw materials are formed and the curable composition performance
The esterification rice flour composition film performance of table 3 slaking
Claims (8)
1. an alkyl acid esterified glutinous rice flour is characterized in that it is to comprise toxilic acid esterification rice flour and the alkyl acid esterified glutinous rice flour that contains 3～18 carbon atoms, and gamma value is 0.0001～1.
2. according to the described alkyl acid esterified glutinous rice flour of claim 1, it is characterized in that described rice flour is meant the powder and the modified product thereof of glutinous rice, glutinous corn, glutinous rice, milled glutinous broomcorn millet, Radix Et Rhizoma Rhei rice, small Semen setariae, glutinous indian millet rice, and the starch of these glutinous rices and treated starch thereof.
3. according to the described alkyl acid esterified glutinous rice flour of claim 1, it is characterized in that described alkyl acid esterified glutinous rice flour is an alkyl acid esterification glutinous rice starch.
4. according to the described alkyl acid esterified glutinous rice flour of claim 3, it is characterized in that described alkyl acid esterified glutinous rice flour is the alkyl acid esterification glutinous rice starch that contains 3～10 carbon atoms, gamma value is 0.01～0.3.
5. the described alkyl acid esterified glutinous rice flour of claim 1, it is characterized in that it being that maleic anhydride or the alkyl acid anhydrides that contains 3～18 carbon atoms are esterifying agent and natural product rice flour prepared in reaction, the proportioning of acid anhydrides and rice flour is 0.1～3 according to the mol ratio of the starch glucosyl group of acid anhydrides and rice flour.
6. the preparation method of the described alkyl acid esterified glutinous rice flour of claim 1, it is characterized in that the step that it comprises: natural product rice flour and water are mixed with the rice flour emulsion, the pH that regulates emulsion system with NaOH is between the 8-11, the ethanolic soln that adds esterifying agent then, the mol ratio of the starch glucosyl group of acid anhydrides and rice flour is 0.1～3, temperature is controlled at 30～60 ℃, reacts about 3～18 hours, and the pH value of regulation system is between 8-11; PH value with hydrochloric acid soln conditioned reaction system after reaction finishes is 6.5～7.0, filters, and the washing with alcohol with 70%, the vacuum drying oven oven dry promptly gets the esterification rice flour.
7. according to the preparation method of the described alkyl acid esterified glutinous rice flour of claim 5, it is characterized in that described esterifying agent is maleic anhydride or alkyl acid anhydrides that contains 3～18 carbon atoms and their mixture thereof.
8. the application of the described alkyl acid esterified glutinous rice flour of claim 1 is characterized in that being used for medicinal tablet, granule, capsule, gelifying agent, paste, film, facial mask and patch as medicine sustained and controlled release film, pharmaceutical adjunct; Can be used as tamanori after its hydrate slaking and be applied to fields such as label, coating, non-setting adhesive, be used for percutaneous dosing matrix, can with multiple medicine, permeate promotor compatibility, as synthetic drug, Chinese medical concrete, medicinal powder, alcohol, acid, polyvalent alcohol, polyprotonic acid etc. are prepared into patch.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106590468A (en) * | 2017-02-22 | 2017-04-26 | 东北林业大学 | High-temperature cured type esterification modified cassava starch adhesive and preparation method thereof |
| CN111554930A (en) * | 2020-05-08 | 2020-08-18 | 珠海冠宇电池股份有限公司 | Binder and lithium ion battery containing same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1237585A (en) * | 1998-05-12 | 1999-12-08 | 北京降解塑料研究中心 | Modified strach and its preparation method |
-
2009
- 2009-04-23 CN CN2009100685845A patent/CN101870738B/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106590468A (en) * | 2017-02-22 | 2017-04-26 | 东北林业大学 | High-temperature cured type esterification modified cassava starch adhesive and preparation method thereof |
| CN106590468B (en) * | 2017-02-22 | 2018-10-30 | 东北林业大学 | Hot setting type esterification modification Cassava starch adhesive and preparation method thereof |
| CN111554930A (en) * | 2020-05-08 | 2020-08-18 | 珠海冠宇电池股份有限公司 | Binder and lithium ion battery containing same |
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