CN108484820A - A kind of synthetic method of novel acrylic ester lotion - Google Patents
A kind of synthetic method of novel acrylic ester lotion Download PDFInfo
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- CN108484820A CN108484820A CN201810192661.7A CN201810192661A CN108484820A CN 108484820 A CN108484820 A CN 108484820A CN 201810192661 A CN201810192661 A CN 201810192661A CN 108484820 A CN108484820 A CN 108484820A
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- acrylate monomer
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
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- Chemical Kinetics & Catalysis (AREA)
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Abstract
A kind of synthetic method of novel acrylic ester lotion,The one kind obtained by emulsion copolymerization in the presence of novel molecular amount conditioning agent (hereinafter referred to as " conditioning agent ") by acrylate monomer is environmentally protective,The controllable novel acrylic ester lotion of molecular weight,Specific preparation process is first by acrylate monomer,Conditioning agent,Distilled water,Stabilizer and emulsifier stir under nitrogen atmosphere carries out pre-emulsification,Then initiator is added into above-mentioned pre-emulsion in proportion under nitrogen atmosphere and causes polymerization,Novel acrylic ester lotion is made,Above-mentioned New Regulator dosage is the 0.01%~30% of acrylate monomer quality,Emulsifier is the 0.1%~20% of acrylate monomer quality,Stabilizing agent dosage is the 0.1%~30% of acrylate monomer quality,Distill 100%~1000% that water consumption is acrylate monomer quality,Initiator amount is the 0.01%~30% of acrylate monomer quality,This method is simple for process,Use novel environment friendly conditioning agent,It is safe and efficient,Not only molecular weight is controllable for gained lotion,Viscosity and grain size are also smaller.
Description
Technical field
The present invention relates to a kind of synthetic method of novel acrylic ester lotion, it more particularly relates to it is a kind of with
The novel addition fracture chain-transferring agent of sulfur-bearing is not the synthetic method of the acrylic acid ester emulsion of molecular weight regulator.
Background technology
Acrylic acid ester emulsion is the product obtained by way of emulsion polymerization by acrylate monomer, is had excellent resistance to
The features such as Hou Xing, corrosion resistance, be adhesive development important directions, be widely used in packaging, coating, building, weaving and
The industries such as the industries such as leather.
Conditioning agent is substantially a kind of chain-transferring agent.Currently, the common molecular weight regulator of acrylic acid ester emulsion is mercaptan
Class compound, such as n- dodecyl mereaptan, tert-dodecyl mercaptan, n-butyl mercaptan, mercaptoethanol.Commercialized thio-alcohol conditioning agent is not only
Stink is larger, and component is more complicated, sulfur alcohol compound similar in usually several or even tens kinds of structures and molecular weight
The mixture of composition, this results in thio-alcohol conditioning agent chain transfer activity to change greatly, polymer molecular weight changes in distribution also compared with
Greatly, the lasting control to polymer molecular weight is difficult to realize by free-radical emulsion polymerization method.In this regard, United States Patent (USP) (patent
Number US6369158B1) a kind of new conditioning agent dibenzyl trithiocarbonate (DBTTC) is described, which can continue
Efficiently adjust the molecular weight of free-radical emulsion polymerization object, and component is single, effect stability, but when dosage is larger still have it is apparent smelly
Taste.
The conditioning agent of emulsion polymerization is based on sulfur-containing compound at present, and sulfur-containing compound is in high volume in use, not only
With apparent penetrating odor, it is unfavorable for production safety, and a degree of pollution can be caused to water body and soil, does not meet
The environmental protection concept of green production.In this regard, many researchs are dedicated to the low labile environment-friendly type conditioning agent of peculiar smell of low toxicity." molecular weight
Influence of the conditioning agent to acrylate emulsion performance " is by ethylene glycol, isopropanol and 2,4- diphenyl -4- methyl-1-pentenes
The New Regulators such as alkene have been introduced into the polymerization system of acrylate pressure-sensitive adhesive, but ethylene glycol and 2,4- diphenyl -4- methyl -
The increase of 1- amylene dosages significantly reduces the polymerization stability of the system, and conditioning agent to the molecular weight of emulsion polymer and its
The specific influence of distribution and mechanism of action are simultaneously not known." free radical emulsion in the presence of irreversible addition-fracture chain-transferring agent is poly-
The research of conjunction " then has studied is applied to styrene emulsion polymerization by 2,3- dichloropropylenes, though as a result show that it can be adjusted really
Polymer molecular weight, but this influence can not be continuously present in entire reaction process, be increased with reaction conversion ratio, with system
Viscosity increases, and the influence to polymer is smaller and smaller, molecular weight actual measurement increasingly deviation theory value, as applied to acrylic acid
Ester emulsion system is not pointed out with the presence or absence of same problem in article.And New Regulator according to the present invention is not only
Not sulfur-containing compound, and the problem of not inquired into the studies above is explored, such as 2,4- diphenyl -4-methyl-1-pentene is answered
For acrylic acid ester emulsion system to the impact effect of polymer molecular weight and its distribution, 2,3- dichloropropylenes are to acrylate breast
Liquid system is different from styrene emulsion system, in addition, the present invention, which also designs, has synthesized conditioning agent 2- phenyl-similar in two kinds of structures
4,4- dimethyl -1- amylenes and 2,4- dimethyl -4- phenyl -1- amylenes, and inquired into its shadow to acrylic acid ester emulsion performance
Effect is rung, as a result will specifically be shown below.
Object of this investigation is that synthesis is a kind of being broken chain-transferring agent as molecular weight regulator using the novel addition of not sulfur-bearing
Acrylic acid ester emulsion.
Invention content
The technical issues of solution：The present invention provides a kind of novel environment friendly molecular weight tune that can replace sulfur alcohol compound
Agent is saved, acrylic acid ester emulsion is applied to, to the molecular-weight adjusting effect of polymer comparable to sulfur alcohol compound.
Technical solution：A kind of synthetic method of novel acrylic ester lotion, includes the following steps：
The first step：By acrylate monomer, conditioning agent, distilled water, stabilizer and emulsifier stir under nitrogen atmosphere into
Row pre-emulsification, reaction condition are that 10min~6h is stirred at 10~80 DEG C, obtain pre-emulsion；
Second step：Initiator is added into above-mentioned pre-emulsion in proportion under nitrogen atmosphere and causes polymerization, polymerisation temperature
Degree is 45~95 DEG C, reacts 2~10h, and novel acrylic ester lotion is made.
Above-mentioned New Regulator dosage is the 0.01%~30% of acrylate monomer quality, and emulsifier is acrylic acid
The 0.1%~20% of ester monomer quality, stabilizing agent dosage are the 0.1%~30% of acrylate monomer quality, distill water consumption
It is the 100%~1000% of acrylate monomer quality, initiator amount is the 0.01%~30% of acrylate monomer quality.
Above-mentioned acrylate monomer is methyl methacrylate, n-butyl acrylate, acrylic acid, hydroxy-ethyl acrylate, first
One kind in base hydroxy-ethyl acrylate, hydroxypropyl acrylate or diallyl phthalate or several mixture.
Above-mentioned New Regulator be 2,4- diphenyl -4-methyl-1-pentene, 2- phenyl -4,4- dimethyl -1- amylenes, 2,
4- dimethyl -4- phenyl -1- amylenes, one kind in 2,3- dichloropropylenes appoint several mixtures.
Aforementioned stable agent be disodium hydrogen phosphate, sodium hydroxide, sodium sulfite, sodium carbonate or sodium bicarbonate in one kind or appoint
It is several.
Mentioned emulsifier is nonylphenol polyoxyethylene ether (OP), lauryl sodium sulfate (SDS), neopelex
(SDBS) or one kind in nonylphenol polyoxyethylene ether maleate sodium (OS) or appoint several mixture.
Above-mentioned initiator is one kind or several mixture in ammonium persulfate, potassium peroxydisulfate or sodium peroxydisulfate.
Advantageous effect：
1. the novel molecular amount conditioning agent used adjusts the regulating effect of polymer molecular weight comparable to traditional thio-alcohol
Agent, and polymer polydispersity is relatively low, illustrates that resulting polymers chain regularity is preferable.
2. research molecular weight regulator used is environment-friendly type conditioning agent, the formaldehydeless and hypertoxic class organic solvent of preparation process
Addition, product without pernicious gas discharge, meet environmentally protective production theory.
3. acrylic acid ester emulsion preparation process is less, easy to operate, good emulsion stability, Storage period is long.
Specific implementation mode
A kind of synthetic method of novel acrylic ester lotion：
The first step：By acrylate monomer, conditioning agent, distilled water, stabilizer and emulsifier stir under nitrogen atmosphere into
Row pre-emulsification, reaction condition are that 10min~6h is stirred at 10~80 DEG C, obtain pre-emulsion；
Second step：Initiator is added into above-mentioned pre-emulsion in proportion under nitrogen atmosphere and causes polymerization, polymerisation temperature
Degree is 45~95 DEG C, reacts 2~10h, and novel acrylic ester lotion is made.
Above-mentioned New Regulator dosage is the 0.01%~30% of acrylate monomer quality, and emulsifier is acrylic acid
The 0.1%~20% of ester monomer quality, stabilizing agent dosage are the 0.1%~30% of acrylate monomer quality, distill water consumption
It is the 100%~1000% of acrylate monomer quality, initiator amount is the 0.01%~30% of acrylate monomer quality.
Above-mentioned acrylate monomer is methyl methacrylate, n-butyl acrylate, acrylic acid, hydroxy-ethyl acrylate, first
One kind in base hydroxy-ethyl acrylate, hydroxypropyl acrylate or diallyl phthalate or several mixture.
Above-mentioned New Regulator be 2,4- diphenyl -4-methyl-1-pentene, 2- phenyl -4,4- dimethyl -1- amylenes, 2,
4- dimethyl -4- phenyl -1- amylenes, one kind in 2,3-, bis- chloro- 1- butylene appoint several mixtures.
Aforementioned stable agent be disodium hydrogen phosphate, sodium hydroxide, sodium sulfite, sodium carbonate or sodium bicarbonate in one kind or appoint
Several mixtures.
Mentioned emulsifier is nonylphenol polyoxyethylene ether (OP), lauryl sodium sulfate (SDS), neopelex
(SDBS) or one kind in nonylphenol polyoxyethylene ether maleate sodium (OS) or appoint several mixture.
Above-mentioned initiator is one kind or several mixture in ammonium persulfate, potassium peroxydisulfate or sodium peroxydisulfate.
The effect that present invention will be further explained below with reference to specific examples：
Embodiment is implemented under the premise of technical solution of the present invention, should not be construed as limiting the invention, and is used
The conventional means that are well known to those skilled in the art of technological means.
Embodiment 1：
By 65 parts of methyl methacrylates, 65 parts of n-butyl acrylates, 0.39 part of 2,4- diphenyl -4-methyl-1-pentene,
0.26 part of 2- phenyl -4,4- dimethyl -1- amylenes, 156 parts of distilled water, 0.16 part of disodium hydrogen phosphate, 0.65 part of OP, 0.65 part of OS
It is stirred under nitrogen atmosphere with 2.60 parts of SDS and carries out pre-emulsification, obtain pre-emulsion, reaction condition is to stir 40min at 25 DEG C, is stirred
It is 300rpm to mix device rotating speed.Then it is added into above-mentioned pre-emulsion and is steamed by 0.65 part of ammonium persulfate and 6.50 parts under nitrogen atmosphere
Initiator solution made of distilled water causes polymerization, and novel acrylic ester lotion is made in reaction 4h.Gained emulsion property result is shown in
Subordinate list 1.
Embodiment 2：
By 63 parts of methyl methacrylates, 4 parts of hydroxy-ethyl acrylates, 63 parts of n-butyl acrylates, 0.65 part of 2,4- hexichol
Base -4-methyl-1-pentene, 0.65 part of 2,3- dichloropropylene, 156 parts of distilled water, 0.16 part of disodium hydrogen phosphate, 1.30 parts of OP and
2.60 parts of SDS are stirred under nitrogen atmosphere carries out pre-emulsification, obtains pre-emulsion, and reaction condition is to stir 30min at 30 DEG C, is stirred
Device rotating speed is 300rpm.Then it is added into above-mentioned pre-emulsion and is distilled by 0.65 part of ammonium persulfate and 6.50 parts under nitrogen atmosphere
Initiator solution made of water causes polymerization, and novel acrylic ester lotion is made in reaction 4h.Gained emulsion property result is shown in attached
Table 1.
Embodiment 3：
By 63 parts of methyl methacrylates, 4 parts of acrylic acid, 63 parts of n-butyl acrylates, 0.13 part of 2,4- diphenyl -4- first
Base -1- amylenes, 0.13 part of 2- phenyl -4,4- dimethyl -1- amylenes, 0.13 part of 2,3- dichloropropylene, 156 parts of distilled water, 0.16
Part sodium bicarbonate, 1.30 parts of OP and 2.60 part of SDBS are stirred under nitrogen atmosphere carries out pre-emulsification, obtains pre-emulsion, reaction condition
It is that 40min, agitator speed 300rpm are stirred at 25 DEG C.Then it is added under nitrogen atmosphere into above-mentioned pre-emulsion by 0.65
Initiator solution made of part ammonium persulfate and 6.50 parts of distilled water causes polymerization, and it is newborn that novel acrylic ester is made in reaction 4h
Liquid.Gained emulsion property result sees attached list 1.
Embodiment 4：
By 60 parts of methyl methacrylates, 5 parts of hydroxy propyl methacrylates, 65 parts of n-butyl acrylates, 0.07 part of 2- benzene
Base -4,4- dimethyl -1- amylenes, 0.06 part of 2,3- dichloropropylene, 156 parts of distilled water, 0.16 part of sodium sulfite, 1.30 parts of OP and
2.60 parts of SDS are stirred under nitrogen atmosphere carries out pre-emulsification, obtains pre-emulsion, and reaction condition is to stir 40min at 25 DEG C, is stirred
Device rotating speed is 300rpm.Then it is added into above-mentioned pre-emulsion and is distilled by 0.65 part of ammonium persulfate and 6.50 parts under nitrogen atmosphere
Initiator solution made of water causes polymerization, and novel acrylic ester lotion is made in reaction 6h.Gained emulsion property result is shown in attached
Table 1.
Embodiment 5：
By 63 parts of methyl methacrylates, 4 portions of diallyl phthalates, 63 parts of n-butyl acrylates, 0.65 part of 2-
Phenyl -4,4- dimethyl -1- amylenes, 0.65 part of 2,4- dimethyl -4- phenyl -1- amylenes, 156 parts of distilled water, 0.16 part of hydrogen-oxygen
Change sodium, 1.30 parts of OP and 2.60 part of SDBS are stirred under nitrogen atmosphere carries out pre-emulsification, obtains pre-emulsion, and reaction condition is 25 DEG C
Lower stirring 40min, agitator speed 300rpm.Then it is added under nitrogen atmosphere into above-mentioned pre-emulsion by 0.65 part of over cure
Initiator solution made of sour potassium and 6.50 parts of distilled water causes polymerization, and novel acrylic ester lotion is made in reaction 6h.Gained
Emulsion property result sees attached list 1.
Embodiment 6：
By 65 parts of methyl methacrylates, 5 parts of hydroxypropyl acrylates, 63 parts of n-butyl acrylates, 0.26 part of 2,4- diformazan
Base -4- phenyl -1- amylenes, 0.52 part of 2,3- dichloropropylene, 156 parts of distilled water, 0.16 part of sodium carbonate, 1.30 parts OP and 2.60 part
SDS is stirred under nitrogen atmosphere carries out pre-emulsification, obtains pre-emulsion, and reaction condition is to stir 40min, agitator speed at 25 DEG C
For 300rpm.Then it is added into above-mentioned pre-emulsion and is made of 0.65 part of sodium peroxydisulfate and 6.50 parts of distilled water under nitrogen atmosphere
Initiator solution cause polymerization, novel acrylic ester lotion is made in reaction 6h.Gained emulsion property result sees attached list 1.
Subordinate list 1
Subordinate list 2
Note：All conditioning agents are replaced with to the dodecyl sulphur of equivalent under " * " representative and corresponding embodiment the same terms
Alcohol
Above-mentioned number-average molecular weight and the measurement of polydispersity are using Britain's Malvern Viscotek3580 type gels
Exclusion chromatography instrument, using linear polystyrene as internal standard, mobile phase is chromatography pure tetrahydrofuran, flow velocity 1mL/min, column temperature 40
DEG C, sample concentration 1mg/mL.
The Comparative result of above-mentioned two subordinate list shows that a series of irreversible addition fracture chain-transferring agents being newly added can be basic
Regulating effect identical with card lauryl mercaptan is played, new conditioning agent is basic to the impact effect of polymer number-average molecular weight
It is consistent with lauryl mercaptan, but the performance of mercaptan then slightly shows stabilization in terms of polydispersity；Meanwhile as can be seen from the table, newly
Influence of the conditioning agent to emulsion particle diameter and card lauryl mercaptan it is almost the same, but the former viscosity is slightly above the latter, the phenomenon
Show that acrylic acid ester emulsion obtained by New Regulator has the potentiality applied to high viscosity latex.In addition, being also not difficult from subordinate list
Find out, the increase of New Regulator dosage can be substantially reduced polymerisation degree to a certain extent, this should be with freedom in emulsion particle
The desorption phenomenon of base is related.
Claims (6)
1. a kind of synthetic method of novel acrylic ester lotion, it is characterised in that：
The first step：It is pre- that acrylate monomer, conditioning agent, distilled water, stabilizer and emulsifier are stirred to progress under nitrogen atmosphere
Emulsification, reaction condition are that 10min~6h is stirred at 10~80 DEG C, obtain pre-emulsion；
Second step：Initiator is added into above-mentioned pre-emulsion in proportion under nitrogen atmosphere and causes polymerization, polymeric reaction temperature is
45~95 DEG C, 2~10h is reacted, novel acrylic ester lotion is made.
Above-mentioned New Regulator dosage is the 0.01%~30% of acrylate monomer quality, and emulsifier is acrylate list
The 0.1%~20% of weight, stabilizing agent dosage are the 0.1%~30% of acrylate monomer quality, and distillation water consumption is third
The 100%~1000% of olefin(e) acid ester monomer quality, initiator amount are the 0.01%~30% of acrylate monomer quality.
2. acrylic acid ester emulsion preparation method according to claim 1, it is characterised in that：Acrylate monomer is methyl-prop
E pioic acid methyl ester, n-butyl acrylate, acrylic acid, hydroxy-ethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate or adjacent benzene
One kind in diformazan diallyl phthalate or several mixture.
3. acrylic acid ester emulsion preparation method according to claim 1, it is characterised in that：New Regulator is 2,4- hexichol
Base -4-methyl-1-pentene, 2- phenyl -4,4- dimethyl -1- amylenes, 2,4- dimethyl -4- phenyl -1- amylenes, 2,3- dichloros third
One kind in alkene or several mixture.
4. acrylic acid ester emulsion preparation method according to claim 1, it is characterised in that：Stabilizer be disodium hydrogen phosphate,
One kind in sodium hydroxide, sodium sulfite, sodium carbonate or sodium bicarbonate or several mixture.
5. acrylic acid ester emulsion preparation method according to claim 1, it is characterised in that：Emulsifier is polyoxyethylene nonyl phenyl second
Alkene ether (OP), lauryl sodium sulfate (SDS), neopelex (SDBS) or nonylphenol polyoxyethylene ether maleate
One kind in sodium (OS) or several mixture.
6. acrylic acid ester emulsion preparation method according to claim 1, it is characterised in that：Initiator is ammonium persulfate, mistake
One kind in potassium sulfate or sodium peroxydisulfate.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1198749A (en) * | 1995-10-06 | 1998-11-11 | 联邦科学和工业研究组织 | Control of molecular weight and end-group functionality in polymers |
| CN101735378A (en) * | 2009-11-24 | 2010-06-16 | 东莞市英科水墨有限公司 | Pure acrylic emulsion for waterborne preprinting gloss oil and preparation method thereof |
| CN101851316A (en) * | 2010-06-13 | 2010-10-06 | 东莞市英科水墨有限公司 | Alkali-soluble emulsion, preparation method thereof and application thereof in water-based ink |
| CN102101901A (en) * | 2010-12-28 | 2011-06-22 | 东莞市英科水墨有限公司 | Core-shell type gold varnish emulsion and preparation method and use thereof |
-
2018
- 2018-03-06 CN CN201810192661.7A patent/CN108484820A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1198749A (en) * | 1995-10-06 | 1998-11-11 | 联邦科学和工业研究组织 | Control of molecular weight and end-group functionality in polymers |
| CN101735378A (en) * | 2009-11-24 | 2010-06-16 | 东莞市英科水墨有限公司 | Pure acrylic emulsion for waterborne preprinting gloss oil and preparation method thereof |
| CN101851316A (en) * | 2010-06-13 | 2010-10-06 | 东莞市英科水墨有限公司 | Alkali-soluble emulsion, preparation method thereof and application thereof in water-based ink |
| CN102101901A (en) * | 2010-12-28 | 2011-06-22 | 东莞市英科水墨有限公司 | Core-shell type gold varnish emulsion and preparation method and use thereof |
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Application publication date: 20180904 |