WO2013012365A1 - Waterborne homo or copolymer dispersion - Google Patents
Waterborne homo or copolymer dispersion Download PDFInfo
- Publication number
- WO2013012365A1 WO2013012365A1 PCT/SE2012/000100 SE2012000100W WO2013012365A1 WO 2013012365 A1 WO2013012365 A1 WO 2013012365A1 SE 2012000100 W SE2012000100 W SE 2012000100W WO 2013012365 A1 WO2013012365 A1 WO 2013012365A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polymer dispersion
- dispersion according
- crotonate
- isocrotonate
- waterborne polymer
- Prior art date
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Classifications
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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
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
-
- 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
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/02—Acids; Metal salts or ammonium salts thereof, e.g. maleic acid or itaconic acid
-
- 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
Definitions
- the present invention refers to a waterborne homo or copolymer dispersion obtained by homo or copolymerisation in an aqueous medium of at least one alkyl crotonate and/or at least one crotonic acid.
- Emulsion polymerisation is well known in the art and frequently disclosed and discussed in the patent literature, in handbooks and encyclopaedias. Emulsion polymerisation is typically performed in an aqueous medium in the presence of a surfactant and a water-soluble initiator and is usually rapidly giving high molecular weight homo or copolymers at high solids content, typically 30-60%, and low dispersion viscosity.
- a surfactant typically a surfactant and a water-soluble initiator
- Traditional applications for these aqueous dispersions are mainly adhesives, binders for fibres, protective and decorative coatings, foam, paper coatings and thread and textile modifiers.
- the present invention accordingly refers to a novel waterborne homo or preferably copolymer dispersion obtained by homo or preferably copolymerisation in an aqueous medium of at least one alkyl crotonate or isocrotonate, preferably a Ci-Cis alkyl crotonate or isocrotonate, such as methyl crotonate, ethyl crotonate, n-butyl crotonate, isobutyl crotonate, t-butyl crotonate, 2-ethylhexyl crotonate, 2-propylheptyl crotonate, neopentyl crotonate, glycidyl crotonate, vinyl
- alkyl crotonates include alkyl dicrotonates and alkyl diisocrotonates of diols, such as ethylene glycol, 1 ,2-propanediol, 1,3-propanediol, butylene glycols, and 2-alkyl-l ,3-propanediols, 2,2-dialkyl-l,3-propanediols, such as neopentyl glycol and 2-ethyl-2-butyl- 1 ,3-propanediol.
- diols such as ethylene glycol, 1 ,2-propanediol, 1,3-propanediol, butylene glycols, and 2-alkyl-l ,3-propanediols, 2,2-dialkyl-l,3-propanediols, such as neopentyl glycol and 2-ethyl-2-butyl- 1 ,
- mono(iso)crotonates of diols mono, di and tri(iso)crotonates of triols and mono di, tri and higher (iso)crotonates of polyols can be included, such as trimethylolpropane mono, di or tricrotonate or isocrotonate.
- alkyl acrylates and/or alkyl methacrylates preferably Ci-C 18 alkyl acrylates or methacrylates, such as methyl acrylate, ethyl acrylate, butyl acrylate, methyl methacrylate, ethyl methacrylate, and/or acrylic acid and/or methacrylic acid, and/or polymerisable allyl, vinyl, maleic and/or diene monomers, such as, but not limited to, itaconic acid, cinnamic acid, maleic anhydride, fumaric acid, glycidyl acrylates, glycidyl methacrylates, acrylamides, methacrylamides, ethyl imidazolidon methacrylates, ethylene, propylene, styrene, divinylstyrene, vinylacetate, vinyl propionates, vinyl versatates, dibutyl
- the homo or copolymer dispersion of the present invention is yielded in either a one stage or a multistage emulsion homo or copolymerisation.
- Said emulsion polymerisation may for instance yield latex particles having a heterogeneous morphology, such as a core-shell morphology.
- core-shell morphologies are possible.
- spherical core-shell particles are made when a polymer made from a first monomer is more hydrophobic than a polymer made from a second monomer.
- dispersion according to the present invention include species comprising at least one polymerisable surfactant, such as a surfactant comprising at least one alkenyl group, and/or a conventional surfactant.
- a polymerisable surfactant such as a surfactant comprising at least one alkenyl group, and/or a conventional surfactant.
- a copolymer according to the present invention is such that the crotonate based content of the total content, with water and/or other solvents excluded, is 0.1-99.9%, such as 5-60%, 5-30% or 10-25%), by weight.
- Storage stability, glass transition temperature and particle size distribution are important parameters whose optima are to be found within the monomer content levels given above.
- crotonic acid and crotonic acid derivatives can be used together with mercaptans in the so called thiol-ene reaction to produce a crosslinked system.
- Thiol-enes can be part of hybrid systems that involve both thiol-enes and other types of systems, such as radical polymerised unsaturations. By this, the property range of the coatings can be expanded.
- Thiol-ene networks due to their almost perfect network structure that is much more uniform than even epoxy networks, can be fabricated to exhibit a wide range of benchmark properties including rubber-like materials with resiliencies of greater than 95%o, glassy materials with properties resembling traditional rubbery materials (i.e.
- cellulose can be modified, preferably covalently bonded, with crotonic acid and crotonic acid derivatives to obtain increased stability and/or a crosslinked structure.
- the present invention refers to the use of said novel waterborne homo or copolymer dispersion, as disclosed above, in binders for coatings, such as decorative and/or protective paints and lacquers, adhesives and glues.
- binders for coatings such as decorative and/or protective paints and lacquers, adhesives and glues.
- Initiator solution 25% by weight of ammonium persulphate in water, room temperature.
- Example 1 Performed as Example 1 with the difference that the monomer mixture consisted of ethyl crotonate, methyl methacrylate and acrylic acid.
- Example 1 Performed as Example 1 with the difference that the monomer mixture consisted of ethyl crotonate, methyl methacrylate, butyl acrylate and acrylic acid.
- Ammonium persulphate 2 Yielded product exibited following properties:
- Example 1 Performed as Example 1 with the difference that the monomer mixture consisted of ethyl crotonate, methyl methacrylate and acrylic acid.
- Example 1 Performed as Example 1 with the difference that the monomer mixture consisted of ethyl crotonate, methyl methacrylate and acrylic acid. Material Parts by weig
Abstract
Disclosed is a waterbome polymer dispersion is obtained by homo or preferably copolymerisation, together with one or more other polymerisable monomer(s), in an aqueous medium of at least one alkyl crotonate, alkyl isocrotonate, crotonic acid and/or isocrotonic acid.
Description
WATERBOR E HOMO OR COPOLYMER DISPERSION
The present invention refers to a waterborne homo or copolymer dispersion obtained by homo or copolymerisation in an aqueous medium of at least one alkyl crotonate and/or at least one crotonic acid.
The most important industrial method for the manufacture of aqueous dispersion polymers is emulsion polymerisation. Emulsion polymerisation is well known in the art and frequently disclosed and discussed in the patent literature, in handbooks and encyclopaedias. Emulsion polymerisation is typically performed in an aqueous medium in the presence of a surfactant and a water-soluble initiator and is usually rapidly giving high molecular weight homo or copolymers at high solids content, typically 30-60%, and low dispersion viscosity. Traditional applications for these aqueous dispersions are mainly adhesives, binders for fibres, protective and decorative coatings, foam, paper coatings and thread and textile modifiers.
It has now quite unexpectedly been found that alkyl crotonates and/or crotonic acids can, despite previous assumptions and disclosures negating the possibility, yield excellent waterborne homo and copolymer dispersions for use as disclosed above. The present invention accordingly refers to a novel waterborne homo or preferably copolymer dispersion obtained by homo or preferably copolymerisation in an aqueous medium of at least one alkyl crotonate or isocrotonate, preferably a Ci-Cis alkyl crotonate or isocrotonate, such as methyl crotonate, ethyl crotonate, n-butyl crotonate, isobutyl crotonate, t-butyl crotonate, 2-ethylhexyl crotonate, 2-propylheptyl crotonate, neopentyl crotonate, glycidyl crotonate, vinyl crotonate, methyl isocrotonate, ethyl isocrotonate, n-butyl isocrotonate, isobutyl isocrotonate, t-butyl isocrotonate, 2-ethylhexyl isocrotonate, 2-propylheptyl isocrotonate, neopentyl isocrotonate, glycidyl isocrotonate, vinyl isocrotonate and/or at least one crotonic acid, such as crotonic acid and/or isocrotonic acid.
Further suitable alkyl crotonates include alkyl dicrotonates and alkyl diisocrotonates of diols, such as ethylene glycol, 1 ,2-propanediol, 1,3-propanediol, butylene glycols, and 2-alkyl-l ,3-propanediols, 2,2-dialkyl-l,3-propanediols, such as neopentyl glycol and 2-ethyl-2-butyl- 1 ,3-propanediol. Of course, also mono(iso)crotonates of diols, mono, di and tri(iso)crotonates of triols and mono di, tri and higher (iso)crotonates of polyols can be included, such as trimethylolpropane mono, di or tricrotonate or isocrotonate.
Further suitable monomers in a copolymerisation include, but are not limited to alkyl acrylates and/or alkyl methacrylates, preferably Ci-C18 alkyl acrylates or methacrylates, such as methyl acrylate, ethyl acrylate, butyl acrylate, methyl methacrylate, ethyl methacrylate, and/or acrylic acid and/or methacrylic acid, and/or polymerisable allyl, vinyl, maleic and/or diene monomers,
such as, but not limited to, itaconic acid, cinnamic acid, maleic anhydride, fumaric acid, glycidyl acrylates, glycidyl methacrylates, acrylamides, methacrylamides, ethyl imidazolidon methacrylates, ethylene, propylene, styrene, divinylstyrene, vinylacetate, vinyl propionates, vinyl versatates, dibutyl maleate and/or butadiene or isoprene.
The homo or copolymer dispersion of the present invention is yielded in either a one stage or a multistage emulsion homo or copolymerisation. Said emulsion polymerisation may for instance yield latex particles having a heterogeneous morphology, such as a core-shell morphology. When monomers of different solubility or hydrophobicity are used or when staged polymerisations are carried out, core-shell morphologies are possible. In staged polymerisations, spherical core-shell particles are made when a polymer made from a first monomer is more hydrophobic than a polymer made from a second monomer.
Further embodiments of the dispersion according to the present invention include species comprising at least one polymerisable surfactant, such as a surfactant comprising at least one alkenyl group, and/or a conventional surfactant.
A copolymer according to the present invention is such that the crotonate based content of the total content, with water and/or other solvents excluded, is 0.1-99.9%, such as 5-60%, 5-30% or 10-25%), by weight. Storage stability, glass transition temperature and particle size distribution are important parameters whose optima are to be found within the monomer content levels given above.
Furthermore, crotonic acid and crotonic acid derivatives can be used together with mercaptans in the so called thiol-ene reaction to produce a crosslinked system. Thiol-enes can be part of hybrid systems that involve both thiol-enes and other types of systems, such as radical polymerised unsaturations. By this, the property range of the coatings can be expanded. Thiol-ene networks, due to their almost perfect network structure that is much more uniform than even epoxy networks, can be fabricated to exhibit a wide range of benchmark properties including rubber-like materials with resiliencies of greater than 95%o, glassy materials with properties resembling traditional rubbery materials (i.e. glasses that bounce better than conventional crosslinked super balls), and high energy absorbing materials for personal protection. These properties can be advantageous also for coating applications. Yet furthermore, cellulose can be modified, preferably covalently bonded, with crotonic acid and crotonic acid derivatives to obtain increased stability and/or a crosslinked structure.
In a further aspect, the present invention refers to the use of said novel waterborne homo or copolymer dispersion, as disclosed above, in binders for coatings, such as decorative and/or protective paints and lacquers, adhesives and glues.
The following specific embodiments, Examples 1 -5, relating to preparations of polymers according to the present invention, are to be construed as merely illustrative and not limitative in any way whatsoever.
Example 1
Mixtures a), b) and c) were prepared according to the following:
a) Water, emulsifier Disponil® AES 72 (alkylaryl polyglycol ether sulphate, sodium salt, Cognis) and sodium acetate as buffer (calculated on 35% by weight on ammonium persulphate), heated to 80°C.
b) Monomer mixture: Ethyl crotonate, styrene and acrylic acid, room temperature.
c) Initiator solution: 25% by weight of ammonium persulphate in water, room temperature.
Procedure: a) was heated to 80°C and 10% of b) and c) were charged. Portions of b) and c) were every 20 minutes (during 4 hrs.) added. After completed addition, stirring at 80°C was carried out for one hour. Equipment: Teflon stirrer 100-150 rpm, oil bath and reaction vessel equipped with cooler and nitrogen inlet.
Following properties on yielded product were determined: Molecular weight (Mn) and molecular weight (Mw) by GPC (General Purpose Chromatography), polydispersity and glass transition temperature (Tg) by DSC (Differential Scanning Calorimetry).
Material Parts by weig
Water 477
Disponir AES 72 54
Sodium acetate 2 x 0.35
Ethyl crotonate 220
Styrene 220
Acrylic acid 25
Ammonium persulphate 2
Yielded product exibited following properties:
Mn, g/mol: 5800
Mw, g/mol: 17000
Polydispersity: 2.9
Tg, °C: 33
Example 2
Performed as Example 1 with the difference that the monomer mixture consisted of ethyl crotonate, methyl methacrylate and acrylic acid.
Material Parts by weig
Water 477
Disponil® AES 72 54
Sodium acetate 2 x 0.35
Ethyl crotonate 220
Methyl methacrylate 220
Acrylic acid 25
Ammonium persulphate 2
Yielded product exibited following properties:
Mn g/mol (GPC): 8500
Mw g/mol (GPC): 22000
Polydispersity: 2.6
Tg °C, (DSC): -2.6
Example 3
Performed as Example 1 with the difference that the monomer mixture consisted of ethyl crotonate, methyl methacrylate, butyl acrylate and acrylic acid.
Material Parts by weight
Water 477
Disponil® AES 72 54
Sodium acetate 2 x 0.35
Ethyl crotonate 86
Methyl methacrylate 225
Butyl acrylate 139
Acrylic acid 14
Ammonium persulphate 2
Yielded product exibited following properties:
Mn g/mol (GPC): 4300
Mw g/mol (GPC): 48000
Polydispersity: 1 1
Tg °C, (DSC): 4
Example 4
Performed as Example 1 with the difference that the monomer mixture consisted of ethyl crotonate, methyl methacrylate and acrylic acid.
Material Parts by weight
Water 477
Disponil® AES 72 54
Sodium acetate 2 x 0.35
Ethyl crotonate 86
methyl methacrylate 225
Butyl acrylate 139
Acrylic acid 14
Ammonium persulphate 2
Yielded product exibited following properties:
Mn g/mol (GPC): 1100
Mw g/mol (GPC): 158000
Polydispersity: 14.5
Tg °C, (DSC): 15
Example 5
Performed as Example 1 with the difference that the monomer mixture consisted of ethyl crotonate, methyl methacrylate and acrylic acid.
Material Parts by weig
Water 477
Disponil® AES 72 54 Sodium acetate 2 x 0.35 Ethyl crotonate 102 Vinyl acetate 348 Acrylic acid 14
Ammonium persulphate 2
Yielded product exibited following properties:
Mn g/mol (GPC): 900
Mw g/mol (GPC): 5400
Polydispersity: 6.3
Tg °C, (DSC): 10
Claims
1. A waterborne polymer dispersion characterised in, that it is obtained by homo or copolymerisation in an aqueous medium of at least one alkyl crotonate, alkyl isocrotonate, crotonic acid and/or isocrotonic acid.
2. A waterborne polymer dispersion according to Claim 1 characterised in, that it is obtained by homo or copolymerisation in an aqueous medium of at least one Ci-Ci8 alkyl crotonate and/or isocrotonate.
3. A waterborne polymer dispersion according to Claim 1 characterised in, that it is obtained by homo or copolymerisation in an aqueous medium of methyl crotonate, ethyl crotonate, n-butyl crotonate, isobutyl crotonate, t-butyl crotonate, 2-ethylhexyl crotonate, 2-propylheptyl crotonate, neopentyl crotonate, glycidyl crotonate, vinyl crotonate, methyl isocrotonate, ethyl isocrotonate, n-butyl isocrotonate, isobutyl isocrotonate, t-butyl isocrotonate, 2-ethylhexyl isocrotonate, 2-propylheptyl isocrotonate, neopentyl isocrotonate, glycidyl isocrotonate, vinyl isocrotonate and/or at least one crotonic acid, such as crotonic acid and/or isocrotonic acid.
4. A waterborne polymer dispersion according to Claim 1 characterised in, that it is obtained by homo or copolymerisation in an aqueous medium of at least one alkyl mono or dicrotonate and/or at least one alkyl mono or diisocrotonate of a diol.
5. A waterborne polymer dispersion according to claim 4 characterised in, that said diol is ethylene glycol, 1,2-propanediol, 1,3-propanediol and/or a butylene glycol.
6. A waterborne polymer dispersion according to claim 4 characterised in, that said diol is a 2-alkyl- 1,3-propanediol and/or a 2,2-dialkyl- 1,3-propanediol.
7. A waterborne polymer dispersion according to claim 4 characterised in, that said diol is neopentyl glycol and/or 2-ethyl-2-butyl-l,3-propanediol.
8. A waterborne polymer dispersion according to any of the Claims 1-7
characterised in, that said copolymerisation further employs at least one alkyl acrylate and/or alkyl methacrylate.
9. A waterborne polymer dispersion according to Claim 8 characterised in, that said alkyl acrylate or methacrylate is a Ci-Ci8 alkyl acrylate or methacrylate.
10. A waterborne polymer dispersion according to any of the Claims 1-7
characterised in, that said copolymerisation further employs methyl acrylate, ethyl acrylate, butyl acrylate, methyl methacrylate, ethyl methacrylate and/or acrylic acid and/or methacrylic acid.
11. A waterborne polymer dispersion according to any of the Claims 1-10
c h arac t eri s e d i n, that said copolymerisation further employs at least one polymerisable allyl, vinyl, maleic and/or diene monomer.
12. A waterborne polymer dispersion according to any of the Claims 1-10
characteri s ed i n, that said copolymerisation further employs itaconic acid, cinnamic acid, maleic anhydride, fumaric acid, glycidyl acrylates, glycidyl methacrylates, acrylamide, methacrylamide, ethyl imidazolidon methacrylate, ethylene, propylene, styrene, divinylstyrene, vinylacetate, vinyl propionate, vinyl versatate, dibutyl maleate, butadiene and/or isoprene.
13. A waterborne polymer dispersion according to any of the Claims 1-12
c h ar ac t e r i s e d i n, that said copolymerisation further employs at least one polymerisable surfactant and/or a conventional surfactant.
14. A waterborne polymer dispersion according to any of the Claims 1-13
characterised in, that said polymer dispersion is yielded in a one stage emulsion homo or copolymerisation.
15. A waterborne polymer dispersion according to any of the Claims 1-13
c h ar a c t e ri s e d i n, that said polymer dispersion is yielded in a multistage emulsion homo or copolymerisation.
16. A waterborne polymer dispersion according to Claim 14 or 15 characterised in, that said emulsion polymerisation yields latex particles having a heterogeneous morphology.
17. A waterborne polymer dispersion according to Claim 14 or 15 characterised in, that said emulsion polymerisation yields latex particles having a core-shell morphology.
18. Use of a waterborne polymer dispersion according to any of the Claims 1-17, in binders for coatings.
19. Use of a waterborne polymer dispersion according to any of the Claims 1-17, in decorative and/or protective paints and lacquers, adhesives and glues.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161509304P | 2011-07-19 | 2011-07-19 | |
| US61/509,304 | 2011-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2013012365A1 true WO2013012365A1 (en) | 2013-01-24 |
Family
ID=47558348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/SE2012/000100 WO2013012365A1 (en) | 2011-07-19 | 2012-06-29 | Waterborne homo or copolymer dispersion |
Country Status (1)
| Country | Link |
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| WO (1) | WO2013012365A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104387515A (en) * | 2014-11-13 | 2015-03-04 | 常熟市万象涂料有限公司 | Interface agent and preparation method thereof |
| CN105085777A (en) * | 2015-07-17 | 2015-11-25 | 中国石油天然气股份有限公司 | Polystyrene 2-ethyl butenoate and preparation method therefor and application thereof |
| CN109868094A (en) * | 2019-01-24 | 2019-06-11 | 东莞泰康聚合物科技有限公司 | A kind of new waterproof lotion and preparation method instead of ethylene-vinyl acetate lotion |
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| WO2005003186A1 (en) * | 2003-07-01 | 2005-01-13 | Celanese Emulsions Norden Ab | Method for production of a waterborne copolymer dispersion |
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|---|---|---|---|---|
| GB903675A (en) * | 1959-09-11 | 1962-08-15 | Leicester Lovell & Co Ltd | Improvements in or relating to the temporary protection of surfaces |
| JPH04332779A (en) * | 1991-05-08 | 1992-11-19 | Toagosei Chem Ind Co Ltd | Aqueous resin dispersion |
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| US20050004272A1 (en) * | 2003-06-23 | 2005-01-06 | Thauming Kuo | Small-particle latex compositions based on waterborne alkyd seeds |
| WO2005003186A1 (en) * | 2003-07-01 | 2005-01-13 | Celanese Emulsions Norden Ab | Method for production of a waterborne copolymer dispersion |
| WO2011056384A1 (en) * | 2009-11-06 | 2011-05-12 | Columbia Insurance Company | Environmentally friendly colorant compositions and latex paints/coatings |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104387515A (en) * | 2014-11-13 | 2015-03-04 | 常熟市万象涂料有限公司 | Interface agent and preparation method thereof |
| CN105085777A (en) * | 2015-07-17 | 2015-11-25 | 中国石油天然气股份有限公司 | Polystyrene 2-ethyl butenoate and preparation method therefor and application thereof |
| CN109868094A (en) * | 2019-01-24 | 2019-06-11 | 东莞泰康聚合物科技有限公司 | A kind of new waterproof lotion and preparation method instead of ethylene-vinyl acetate lotion |
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