CN105440236A - Preparation method of sulfonate type water-borne cellulose acetate emulsion - Google Patents

Preparation method of sulfonate type water-borne cellulose acetate emulsion Download PDF

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Publication number
CN105440236A
CN105440236A CN201510870875.1A CN201510870875A CN105440236A CN 105440236 A CN105440236 A CN 105440236A CN 201510870875 A CN201510870875 A CN 201510870875A CN 105440236 A CN105440236 A CN 105440236A
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preparation
acetic acid
sulfonate type
cellulose acetate
aqueous acetic
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苏秀霞
张祎
张婧
杨晶晶
郭雯
崔明
钱进
陈卓
张海宁
张亚男
杨冬
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Shaanxi University of Science and Technology
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30Low-molecular-weight compounds
    • C08G18/38Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3855Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40High-molecular-weight compounds
    • C08G18/64Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
    • C08G18/6484Polysaccharides and derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/6505Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6523Compounds of group C08G18/3225 or C08G18/3271 or polyamines of C08G18/38
    • C08G18/6529Compounds of group C08G18/3225 or polyamines of C08G18/38
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72Polyisocyanates or polyisothiocyanates
    • C08G18/74Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04Polyurethanes

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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)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

The invention discloses a preparation method of a sulfonate type water-borne cellulose acetate emulsion. The method comprises steps as follows: 1,5-pentanediamine-3-sodium sulfonate, butanone and recrystallized azodiisobutyronitrile are weighed, then 1,5-pentanediamine-3-sodium sulfonate and butanone are added to a flask, recrystallized azodiisobutyronitrile is added, dibutyltin dilaurate and isophorone diisocyanate are added to the flask under the protection of nitrogen, the mixture is stirred for a reaction at the constant temperature of 45-75 DEG C, after the reaction is finished, a product is cooled to the temperature of 40-65 DEG C, then cellulose acetate dissolved in methyl acetate is added, the mixture is cooled to the temperature of 20-45 DEG C after a temperature-keeping reaction, then deionized water is added with stirring, and the sulfonate type water-borne cellulose acetate emulsion is obtained after temperature-keeping dispersion. The sulfonate type water-borne cellulose acetate emulsion prepared with the method has the higher stability and lower VOCs (volatile organic compounds).

Description

A kind of preparation method of sulfonate type aqueous acetic acid fibre emulsion
Technical field
The present invention relates to a kind of preparation method of fibre emulsion, be specifically related to a kind of preparation method of sulfonate type aqueous acetic acid fibre emulsion.
Background technology
Aqueous fiber element ester derivative, using water as basic medium, environmental pollution is little, smell is few, do not fire and process simply, is a kind of environmental protection type resin, progressively instead of solvent-borne type cellulosic products in recent years, be subject to the extensive concern of numerous researchers.Cellulose ethanoate, is called for short CA, is commonly called as cellulose acetate, is a kind of derivatived cellulose obtained through esterification for raw material with Mierocrystalline cellulose and acetic acid; Because it has stronger crushing resistance, good feel, the high selectivity processing feature such as simple, become in derivatived cellulose and carry out merchandized handling the earliest, and the cellulose organic ester of development, cellulose acetate less stable, the volatile organic compounds of cellulose acetate is higher, the actual bodily harm that easily can cause workmen and to problems such as environments.
Summary of the invention
The object of the invention is to the shortcoming overcoming above-mentioned prior art, provide a kind of preparation method of sulfonate type aqueous acetic acid fibre emulsion, the sulfonate type aqueous acetic acid fibre emulsion stability that the method prepares is higher, and volatile organic compounds is lower.
For achieving the above object, the preparation method of sulfonate type aqueous acetic acid fibre emulsion of the present invention comprises the following steps:
Take 1, 5-pentamethylene diamine-3-sodium sulfonate, the Diisopropyl azodicarboxylate of butanone and recrystallization, again by 1, 5-pentamethylene diamine-3-sodium sulfonate and butanone join in flask, and then add the Diisopropyl azodicarboxylate of recrystallization, under the protection of nitrogen, dibutyl tin laurate and isophorone diisocyanate is added in flask, and at the temperature of 45-75 DEG C constant temperature stirring reaction, after it has reacted, be cooled to 40-65 DEG C, add the cellulose acetate that methyl acetate dissolves again, 20-45 DEG C is cooled to after insulation reaction, then deionized water is added while stirring, after insulation dispersion, obtain sulfonate type aqueous acetic acid fibre emulsion, wherein, 1, 5-pentamethylene diamine-3-sodium sulfonate, butanone, the Diisopropyl azodicarboxylate of recrystallization, dibutyl tin laurate, isophorone diisocyanate, the ratio of cellulose acetate and deionized water is: 1.0-8.0g:10-30g:0.1-2g:0.1-0.8g:0.5-7.0g:1.0-6.0g:40ml.
The dibutyl tin laurate after the process of 4A molecular sieve dehydration and isophorone diisocyanate is added in flask.
The speed stirred in constant temperature stirring reaction process is 200rpm, and the constant temperature stirring reaction time is 10min.
The reaction times of insulation reaction is 2h.
It is 2000rpm that limit stirring adds the speed stirred in the process of deionized water.
The time of insulation dispersion is 30min.
The present invention has following beneficial effect:
The preparation method of sulfonate type aqueous acetic acid fibre emulsion of the present invention is in preparation process, using the Diisopropyl azodicarboxylate of recrystallization as initiator, and with 1, 5-pentamethylene diamine-3-sodium sulfonate is hydrophilic component, utilize 1, amino in 5-pentamethylene diamine-3-sodium sulfonate and the isocyanate group in isoflurane chalcone diisocyanate and the hydroxyl in cellulose acetate interact with isocyanate group and are polymerized, by hydrophilic group because being incorporated in cellulosic polymer chain, thus it is higher to obtain stability, the sulfonate type aqueous acetic acid fibre emulsion that volatile organic compounds is lower, possess excellent water tolerance and dispersiveness simultaneously, and the film prepared by this sulfonate type aqueous acetic acid fibre emulsion has good mechanical property.The present invention is successfully that the development of coating and sizing agent industry provides a new approach, has great importance to the Sustainable development of environment protection and coatings industry.
Embodiment
Being described in further detail the present invention below in conjunction with specific embodiment, is below explanation of the invention instead of restriction.
Embodiment one
The preparation method of sulfonate type aqueous acetic acid fibre emulsion of the present invention comprises the following steps:
Take 1, 5-pentamethylene diamine-3-sodium sulfonate, the Diisopropyl azodicarboxylate of butanone and recrystallization, again by 1, 5-pentamethylene diamine-3-sodium sulfonate and butanone join in flask, and then add the Diisopropyl azodicarboxylate of recrystallization, under the protection of nitrogen, the dibutyl tin laurate after the process of 4A molecular sieve dehydration and isophorone diisocyanate is added in flask, and at the temperature of 75 DEG C constant temperature stirring reaction 10min, stirring velocity wherein in constant temperature stirring reaction process is 200rpm, after it has reacted, be cooled to 65 DEG C, add the cellulose acetate that methyl acetate dissolves again, 45 DEG C are cooled to after insulation reaction 2h, then limit adds deionized water with the speed of 2000rpm stirring limit, after insulation dispersion 30min, obtain sulfonate type aqueous acetic acid fibre emulsion, wherein, 1, 5-pentamethylene diamine-3-sodium sulfonate, butanone, the Diisopropyl azodicarboxylate of recrystallization, dibutyl tin laurate, isophorone diisocyanate, the ratio of cellulose acetate and deionized water is: 1.0g:30g:0.1g:0.8g:0.5g:6.0g:40ml.
Embodiment two
The preparation method of sulfonate type aqueous acetic acid fibre emulsion of the present invention comprises the following steps:
Take 1, 5-pentamethylene diamine-3-sodium sulfonate, the Diisopropyl azodicarboxylate of butanone and recrystallization, again by 1, 5-pentamethylene diamine-3-sodium sulfonate and butanone join in flask, and then add the Diisopropyl azodicarboxylate of recrystallization, under the protection of nitrogen, the dibutyl tin laurate after the process of 4A molecular sieve dehydration and isophorone diisocyanate is added in flask, and at the temperature of 45 DEG C constant temperature stirring reaction 10min, stirring velocity wherein in constant temperature stirring reaction process is 200rpm, after it has reacted, be cooled to 40 DEG C, add the cellulose acetate that methyl acetate dissolves again, 20 DEG C are cooled to after insulation reaction 2h, then limit adds deionized water with the speed of 2000rpm stirring limit, after insulation dispersion 30min, obtain sulfonate type aqueous acetic acid fibre emulsion, wherein, 1, 5-pentamethylene diamine-3-sodium sulfonate, butanone, the Diisopropyl azodicarboxylate of recrystallization, dibutyl tin laurate, isophorone diisocyanate, the ratio of cellulose acetate and deionized water is: 8.0g:10g:2g:0.1g:7.0g:1.0g:40ml.
Embodiment three
The preparation method of sulfonate type aqueous acetic acid fibre emulsion of the present invention comprises the following steps:
Take 1, 5-pentamethylene diamine-3-sodium sulfonate, the Diisopropyl azodicarboxylate of butanone and recrystallization, again by 1, 5-pentamethylene diamine-3-sodium sulfonate and butanone join in flask, and then add the Diisopropyl azodicarboxylate of recrystallization, under the protection of nitrogen, the dibutyl tin laurate after the process of 4A molecular sieve dehydration and isophorone diisocyanate is added in flask, and at the temperature of 60 DEG C constant temperature stirring reaction 10min, stirring velocity wherein in constant temperature stirring reaction process is 200rpm, after it has reacted, be cooled to 50 DEG C, add the cellulose acetate that methyl acetate dissolves again, 40 DEG C are cooled to after insulation reaction 2h, then limit adds deionized water with the speed of 2000rpm stirring limit, after insulation dispersion 30min, obtain sulfonate type aqueous acetic acid fibre emulsion, wherein, 1, 5-pentamethylene diamine-3-sodium sulfonate, butanone, the Diisopropyl azodicarboxylate of recrystallization, dibutyl tin laurate, isophorone diisocyanate, the ratio of cellulose acetate and deionized water is: 4g:25g:2g:0.8g:0.5g:2g:40ml.
Embodiment four
The preparation method of sulfonate type aqueous acetic acid fibre emulsion of the present invention comprises the following steps:
Take 1, 5-pentamethylene diamine-3-sodium sulfonate, the Diisopropyl azodicarboxylate of butanone and recrystallization, again by 1, 5-pentamethylene diamine-3-sodium sulfonate and butanone join in flask, and then add the Diisopropyl azodicarboxylate of recrystallization, under the protection of nitrogen, the dibutyl tin laurate after the process of 4A molecular sieve dehydration and isophorone diisocyanate is added in flask, and at the temperature of 50 DEG C constant temperature stirring reaction 10min, stirring velocity wherein in constant temperature stirring reaction process is 200rpm, after it has reacted, be cooled to 45 DEG C, add the cellulose acetate that methyl acetate dissolves again, 30 DEG C are cooled to after insulation reaction 2h, then limit adds deionized water with the speed of 2000rpm stirring limit, after insulation dispersion 30min, obtain sulfonate type aqueous acetic acid fibre emulsion, wherein, 1, 5-pentamethylene diamine-3-sodium sulfonate, butanone, the Diisopropyl azodicarboxylate of recrystallization, dibutyl tin laurate, isophorone diisocyanate, the ratio of cellulose acetate and deionized water is: 6g:20g:1.5g:7g:6.5g:5g:40ml.
Embodiment five
The preparation method of sulfonate type aqueous acetic acid fibre emulsion of the present invention comprises the following steps:
Take 1, 5-pentamethylene diamine-3-sodium sulfonate, the Diisopropyl azodicarboxylate of butanone and recrystallization, again by 1, 5-pentamethylene diamine-3-sodium sulfonate and butanone join in flask, and then add the Diisopropyl azodicarboxylate of recrystallization, under the protection of nitrogen, the dibutyl tin laurate after the process of 4A molecular sieve dehydration and isophorone diisocyanate is added in flask, and at the temperature of 55 DEG C constant temperature stirring reaction 10min, stirring velocity wherein in constant temperature stirring reaction process is 200rpm, after it has reacted, be cooled to 45 DEG C, add the cellulose acetate that methyl acetate dissolves again, 25 DEG C are cooled to after insulation reaction 2h, then limit adds deionized water with the speed of 2000rpm stirring limit, after insulation dispersion 30min, obtain sulfonate type aqueous acetic acid fibre emulsion, wherein, 1, 5-pentamethylene diamine-3-sodium sulfonate, butanone, the Diisopropyl azodicarboxylate of recrystallization, dibutyl tin laurate, isophorone diisocyanate, the ratio of cellulose acetate and deionized water is: 4g:16g:1.2g:0.5g:4g:3g:40ml.
Embodiment six
The preparation method of sulfonate type aqueous acetic acid fibre emulsion of the present invention comprises the following steps:
Take 1, 5-pentamethylene diamine-3-sodium sulfonate, the Diisopropyl azodicarboxylate of butanone and recrystallization, again by 1, 5-pentamethylene diamine-3-sodium sulfonate and butanone join in flask, and then add the Diisopropyl azodicarboxylate of recrystallization, under the protection of nitrogen, the dibutyl tin laurate after the process of 4A molecular sieve dehydration and isophorone diisocyanate is added in flask, and at the temperature of 60 DEG C constant temperature stirring reaction 10min, stirring velocity wherein in constant temperature stirring reaction process is 200rpm, after it has reacted, be cooled to 55 DEG C, add the cellulose acetate that methyl acetate dissolves again, 35 DEG C are cooled to after insulation reaction 2h, then limit adds deionized water with the speed of 2000rpm stirring limit, after insulation dispersion 30min, obtain sulfonate type aqueous acetic acid fibre emulsion, wherein, 1, 5-pentamethylene diamine-3-sodium sulfonate, butanone, the Diisopropyl azodicarboxylate of recrystallization, dibutyl tin laurate, isophorone diisocyanate, the ratio of cellulose acetate and deionized water is: 2g:15g:0.5g:0.3g:2g:2g:40ml.
Emulsion median size d prepared by the present invention n=70nm ~ 500nm size distribution PDI=0.085 ~ 0.166; Emulsion appearance is light yellow (transparent), blueing light, without precipitation; The mechanical property of film prepared by emulsion of the present invention: tensile strength=19.7MPa elongation at break=305.6%.

Claims (6)

1. a preparation method for sulfonate type aqueous acetic acid fibre emulsion, is characterized in that, comprises the following steps:
Take 1, 5-pentamethylene diamine-3-sodium sulfonate, the Diisopropyl azodicarboxylate of butanone and recrystallization, again by 1, 5-pentamethylene diamine-3-sodium sulfonate and butanone join in flask, and then add the Diisopropyl azodicarboxylate of recrystallization, under the protection of nitrogen, dibutyl tin laurate and isophorone diisocyanate is added in flask, and at the temperature of 45-75 DEG C constant temperature stirring reaction, after it has reacted, be cooled to 40-65 DEG C, add the cellulose acetate that methyl acetate dissolves again, 20-45 DEG C is cooled to after insulation reaction, then deionized water is added while stirring, after insulation dispersion, obtain sulfonate type aqueous acetic acid fibre emulsion, wherein, 1, 5-pentamethylene diamine-3-sodium sulfonate, butanone, the Diisopropyl azodicarboxylate of recrystallization, dibutyl tin laurate, isophorone diisocyanate, the ratio of cellulose acetate and deionized water is: 1.0-8.0g:10-30g:0.1-2g:0.1-0.8g:0.5-7.0g:1.0-6.0g:40ml.
2. the preparation method of sulfonate type aqueous acetic acid fibre emulsion according to claim 1, is characterized in that, under the protection of nitrogen, adds the dibutyl tin laurate after the process of 4A molecular sieve dehydration and isophorone diisocyanate in flask.
3. the preparation method of sulfonate type aqueous acetic acid fibre emulsion according to claim 1, is characterized in that, the speed stirred in constant temperature stirring reaction process is 200rpm, and the constant temperature stirring reaction time is 10min.
4. the preparation method of sulfonate type aqueous acetic acid fibre emulsion according to claim 1, is characterized in that, the reaction times of insulation reaction is 2h.
5. the preparation method of sulfonate type aqueous acetic acid fibre emulsion according to claim 1, is characterized in that, it is 2000rpm that limit stirring adds the speed stirred in the process of deionized water.
6. the preparation method of sulfonate type aqueous acetic acid fibre emulsion according to claim 1, is characterized in that, the time of insulation dispersion is 30min.
CN201510870875.1A 2015-12-01 2015-12-01 Preparation method of sulfonate type water-borne cellulose acetate emulsion Pending CN105440236A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108034036A (en) * 2017-12-08 2018-05-15 四川北方硝化棉股份有限公司 A kind of preparation method of aqueous acetic acid cellulose butyrate
CN109180896A (en) * 2018-08-21 2019-01-11 陕西科技大学 A kind of epoxy resin modified aqueous acetate fiber lotion and preparation method thereof
CN110423328A (en) * 2019-08-16 2019-11-08 陕西科技大学 A kind of carboxylic acid sulfonate type aqueous acetic acid fibre emulsion and preparation method thereof

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CN101486798A (en) * 2009-02-13 2009-07-22 西安交通大学 Self-emulsifying aqueous nitrocellulose emulsion and preparation thereof
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CN101486798A (en) * 2009-02-13 2009-07-22 西安交通大学 Self-emulsifying aqueous nitrocellulose emulsion and preparation thereof
CN104479137A (en) * 2014-12-03 2015-04-01 陕西科技大学 Preparation method of water-based nitrocellulose emulsion and nitrocellulose film

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108034036A (en) * 2017-12-08 2018-05-15 四川北方硝化棉股份有限公司 A kind of preparation method of aqueous acetic acid cellulose butyrate
CN109180896A (en) * 2018-08-21 2019-01-11 陕西科技大学 A kind of epoxy resin modified aqueous acetate fiber lotion and preparation method thereof
CN110423328A (en) * 2019-08-16 2019-11-08 陕西科技大学 A kind of carboxylic acid sulfonate type aqueous acetic acid fibre emulsion and preparation method thereof

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