CN109790428B - 水基压敏粘着剂组合物及其制备方法 - Google Patents
水基压敏粘着剂组合物及其制备方法 Download PDFInfo
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- CN109790428B CN109790428B CN201680089627.6A CN201680089627A CN109790428B CN 109790428 B CN109790428 B CN 109790428B CN 201680089627 A CN201680089627 A CN 201680089627A CN 109790428 B CN109790428 B CN 109790428B
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- Prior art keywords
- water
- unsaturated monomer
- sensitive adhesive
- conjugate acid
- aqueous medium
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- 239000000203 mixture Substances 0.000 title claims abstract description 76
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000178 monomer Substances 0.000 claims abstract description 48
- 239000002253 acid Substances 0.000 claims abstract description 43
- 239000012736 aqueous medium Substances 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 150000002148 esters Chemical class 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000002383 tung oil Substances 0.000 claims description 18
- 239000004094 surface-active agent Substances 0.000 claims description 17
- 239000003999 initiator Substances 0.000 claims description 15
- 239000000853 adhesive Substances 0.000 claims description 11
- 230000001070 adhesive effect Effects 0.000 claims description 11
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 230000002087 whitening effect Effects 0.000 description 12
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- 239000003795 chemical substances by application Substances 0.000 description 8
- CUXYLFPMQMFGPL-SUTYWZMXSA-N all-trans-octadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-SUTYWZMXSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
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- 239000002318 adhesion promoter Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 4
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- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000012790 adhesive layer Substances 0.000 description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- CUXYLFPMQMFGPL-FWSDQLJQSA-N alpha-Eleostearic acid Natural products CCCCC=CC=C\C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-FWSDQLJQSA-N 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- IXLCRBHDOFCYRY-UHFFFAOYSA-N dioxido(dioxo)chromium;mercury(2+) Chemical compound [Hg+2].[O-][Cr]([O-])(=O)=O IXLCRBHDOFCYRY-UHFFFAOYSA-N 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
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- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- NQSLZEHVGKWKAY-UHFFFAOYSA-N 6-methylheptyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C(C)=C NQSLZEHVGKWKAY-UHFFFAOYSA-N 0.000 description 1
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 1
- COCLLEMEIJQBAG-UHFFFAOYSA-N 8-methylnonyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)=C COCLLEMEIJQBAG-UHFFFAOYSA-N 0.000 description 1
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-araboascorbic acid Natural products OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 1
- 239000004593 Epoxy Chemical class 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Chemical class 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 1
- 240000002834 Paulownia tomentosa Species 0.000 description 1
- -1 Polyethylene Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
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- 229920001400 block copolymer Polymers 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
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- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- GTBGXKPAKVYEKJ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(C)=C GTBGXKPAKVYEKJ-UHFFFAOYSA-N 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
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- 235000019197 fats Nutrition 0.000 description 1
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- 150000002314 glycerols Chemical class 0.000 description 1
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- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229940026239 isoascorbic acid Drugs 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
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- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- YOTGRUGZMVCBLS-UHFFFAOYSA-N pentadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCOC(=O)C(C)=C YOTGRUGZMVCBLS-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- UCWBKJOCRGQBNW-UHFFFAOYSA-M sodium;hydroxymethanesulfinate;dihydrate Chemical compound O.O.[Na+].OCS([O-])=O UCWBKJOCRGQBNW-UHFFFAOYSA-M 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
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
- 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
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
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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
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- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
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- 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
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- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
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- 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
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- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (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
- 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
- C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
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Abstract
提供一种水基压敏粘着剂组合物及其制备方法。所述水基压敏粘着剂组合物包括至少一种分散于水性介质中的互聚物,所述互聚物包括至少一种不饱和单体及至少一种选自以下组成的组的化合物:至少一种共轭酸、共轭酸的至少一种酯及其混合物。
Description
技术领域
本公开涉及压敏粘着剂组合物。更特定而言,本公开涉及具有改进的耐水增白性的水基压敏粘着剂组合物及其制备方法。
背景技术
粘着剂组合物适用于多种目的。粘着剂组合物的一个尤其适用的子集为水基压敏粘着剂。水基压敏粘着剂在不同最终用途应用中的用途一般为已知的。举例来说,水基压敏粘着剂可与标签纸、记事本、胶带、贴花、绷带、装饰性及保护性片材及多种其它产品一起使用。
如所属领域中所用,术语“压敏粘着剂”指代包括一或多种聚合物组合物(其在干燥时在室温下强力地且永久性地保持粘性)的材料。此外,术语“水基”指示压敏粘着剂通过水性载剂制造。典型的水基压敏粘着剂将在仅接触时牢固地粘着于各种不同表面而不需要手指或手部施加压力以外的压力。
通过压敏粘着剂工业(尤其暴露于湿气的那些)辨识的一个压敏粘着剂特性为耐水增白性。改进压敏粘着剂的耐水增白性的尝试(例如通过使用可聚合表面活性剂替代传统表面活性剂)在商业上尚不理想。这是因为可聚合表面活性剂与传统表面活性剂相比相对更昂贵,且不可广泛获得。当粘着剂待用于需要良好的光学件(例如,透明膜标签)的应用中时,水基压敏粘着剂的水增白特性尤其重要。
因此,需要具有改进的耐水增白性及良好粘着力及内聚力的水基压敏粘着剂组合物以及其制备方法。
发明内容
公开一种组合物,其包括至少一种分散于水性介质中的互聚物,所述互聚物包括至少一种不饱和单体及至少一种选自由以下组成的组的化合物:至少一种共轭酸(conjugated acid)、共轭酸的至少一种酯及其混合物。组合物可进一步包括至少一种表面活性剂。
共轭酸可包括脂肪族酸。此外,共轭酸可包括脂肪族羧酸,例如包括至少三个共轭碳-碳双键的脂肪族羧酸。再者,共轭酸可衍生自天然存在的无水油,例如桐油。更进一步,组合物可进一步包含任选地存在的一或多种增稠剂、任选地存在的一或多种消泡剂、任选地存在的一或多种湿润剂、任选地存在的一或多种机械稳定剂、任选地存在的一或多种颜料、任选地存在的一或多种填充剂、任选地存在的一或多种冻融剂、任选地存在的一或多种中和剂、任选地存在的一或多种塑化剂、任选地存在的一或多种增粘剂、任选地存在的一或多种助粘剂及其组合。
还公开用于制备组合物的方法。所述方法包括将至少一种不饱和单体及任选地存在的至少一种表面活性剂分散于水性介质中以形成乳化混合物。所述方法进一步包括将至少一种引发剂引入到乳化混合物,借此使至少一种不饱和单体聚合,且在至少一种不饱和单体聚合期间将至少一种选自由以下组成的组的化合物引入到乳化混合物:至少一种共轭酸、共轭酸的至少一种酯及其混合物,借此形成包括至少一种不饱和单体及所述化合物的互聚物。
通过至少一种表面活性剂使互聚物在乳化混合物中稳定。此外,当不饱和单体引入到水性介质时,将至少一种选自由以下组成的组的化合物引入到乳化混合物:至少一种共轭酸、共轭酸的至少一种酯及其混合物。在一些实施例中,在至少50%的不饱和单体引入到水性介质之后、或至少70%的不饱和单体引入到水性介质之后或至少90%的不饱和单体引入到水性介质之后,将所述化合物引入到水性介质。当单体乳液进料到水性介质时,所述化合物可在任何时间引入到水性介质。
还公开包括根据上文的方法制备的组合物的水基压敏粘着剂。
具体实施方式
本公开涉及具有改进的耐水增白性及良好粘着力及内聚力的水基压敏粘着剂组合物,以及其制备方法。根据本公开的一个实施例,水基压敏粘着剂组合物包括乳液,所述乳液包括至少一种分散于水性介质中的互聚物。互聚物包括至少一种不饱和单体及至少一种选自由以下组成的组的化合物:至少一种共轭酸、共轭酸的至少一种酯及其混合物。互聚物可通过乳液聚合形成。
一般来说,至少一种不饱和单体与表面活性剂一起分散于整个水性介质中,借此形成乳化混合物。表面活性剂充当乳化剂且使得至少一种不饱和单体的小液滴(其为疏水性的)能够在整个水性介质中形成。引发剂随后引入到乳化混合物中。引发剂经配置以与至少一种不饱和单体反应,借此形成包括不饱和单体子单元的聚合物。引发剂与分散于整个水性介质中的至少一种不饱和单体反应直到所有或大体上所有至少一种不饱和单体聚合。最终结果为聚合物粒子分散于水性介质中,聚合物粒子包括至少一种不饱和单体子单元。
根据本公开,至少一种选自由以下组成的组的化合物:至少一种共轭酸、至少一种共轭酸的至少一种酯及其混合物,在引发剂引入到乳化混合物之后,但在所有至少一种不饱和单体进料到水性介质之前引入到乳化混合物。当不饱和单体添加到混合物时,所述化合物可在任何时间添加到混合物。在一些实施例中,所述化合物在至少50%的至少一种不饱和单体引入到水性介质之后添加。在一些实施例中,所述化合物在至少70%的不饱和单体引入到水性介质之后添加。在一些实施例中,所述化合物在至少80%的不饱和单体引入到水性介质之后添加。在一些实施例中,所述化合物在至少90%的不饱和单体引入到水性介质之后添加。
在添加到乳化混合物中时,至少一种选自由以下组成的组的化合物:至少一种共轭酸、至少一种共轭酸的至少一种酯及其混合物,充当共单体且与至少一种不饱和单体一起形成互聚物。最终结果为聚合物(仅包括至少一种不饱和单体子单元)及互聚物(包括至少一种不饱和单体子单元及包括至少一种选自由以下组成的组的化合物的子单元:至少一种共轭酸、至少一种共轭酸的至少一种酯及其混合物)两者均分散于整个水性介质中。
如将在下文进一步详细论述且借助于实例说明,包括不饱和单体子单元及至少一种化合物子单元两者的互聚物的形成产生组合物,当应用于压敏粘着剂应用中时,所述组合物提供相对于现有压敏粘着剂调配物而言改进的耐水增白性。
在一些实施例中,至少一种不饱和单体可引入到水性介质中且聚合,形成聚合物及/或互聚物。至少一种不饱和单体的实例包含但不限于丙烯酸酯,例如丙烯酸丁酯、丙烯酸乙基己酯、丙烯酸乙酯、丙烯酸甲酯、丙烯酸辛酯、丙烯酸异辛酯、丙烯酸癸酯、丙烯酸异癸酯、丙烯酸十二酯及丙烯酸环己酯;甲基丙烯酸酯,例如甲基丙烯酸甲酯、甲基丙烯酸异丁酯、甲基丙烯酸辛酯、甲基丙烯酸异辛酯、甲基丙烯酸癸酯、甲基丙烯酸异癸酯、甲基丙烯酸十二酯、甲基丙烯酸十五酯、甲基丙烯酸硬脂酰酯、甲基丙烯酸C12到C18烷基酯及甲基丙烯酸环己酯;苯乙烯、乙烯酯及其组合。以混合物的总重量计,至少一种不饱和单体以30到70重量百分比存在于最终乳化混合物中。30到70的所有子范围均包含且公开于本文中。举例来说,范围可为下限30、35、40或45重量百分比到上限63、65或70。
在一些实施例中,至少一种表面活性剂可任选地引入到水性介质中,用于使至少一种不饱和单体稳定且使至少一种互聚物分散于整个水性介质中。至少一种表面活性剂的实例包含但不限于阳离子表面活性剂、阴离子表面活性剂、两性离子表面活性剂、非离子表面活性剂及其组合。阴离子表面活性剂的实例包含但不限于磺酸盐、羧酸盐及磷酸盐。阳离子表面活性剂的实例包含但不限于季胺。非离子表面活性剂的实例包含但不限于含有环氧乙烷的嵌段共聚物及硅酮表面活性剂,例如乙氧基化醇、乙氧基化脂肪酸、脱水山梨糖醇衍生物、羊毛蜡衍生物、乙氧基化壬基酚或烷氧基化硅酮烷。至少一种表面活性剂以0.05到10重量百分比存在于乳化混合物中。0.05到10的所有子范围均包含于本文中且公开于本文中。举例来说,范围可为下限0.05、0.07、0.1或0.2到上限0.5、0.7、1、2或10。
在一些实施例中,至少一种选自由以下组成的组的化合物:至少一种共轭酸、至少一种共轭酸的至少一种酯及其混合物,可引入到水性介质中且与不饱和单体子单元一起聚合。至少一种共轭酸的实例包含但不限于不饱和脂肪酸。适合的不饱和脂肪酸包含衍生自天然存在的脱水油(例如桐油)的脂肪酸。特定而言,桐油包括α-桐酸、亚麻油酸、棕榈酸及油酸的甘油酯,适用于本公开的目的。至少一种共轭酸的酯的实例包含天然衍生的油,例如桐油。
桐油脂肪酸一般具有根据(I)的结构作为主要组分,且桐油一般具有根据(II)的说明性结构:
至少一种共轭酸的实例进一步包含但不限于脂肪族酸,尤其包括三个或多于三个共轭碳-碳双键的脂肪族羧酸。特定而言,α-桐酸适用于本公开的目的。至少一种共轭酸以0.01到5重量百分比存在于乳化混合物中。0.01到5的所有个别比值及子范围均包含于本文中且公开于本文中。举例来说,比率可为下限0.01、0.05、0.10或0.25到上限1、2、3、4或5。
在一些实施例中,多于一种引发剂可引入到乳化混合物中,用于使至少一种不饱和单体聚合。至少一种引发剂可为热引发剂或氧化还原系统引发剂。至少一种热引发剂的一个实例包含但不限于过硫酸铵。在引发剂为氧化还原系统引发剂的情况下,还原剂可为例如抗坏血酸、次硫酸盐或异抗坏血酸,而氧化剂可为例如过氧化物或过硫酸盐。至少一种引发剂以0.05到2重量百分比存在于乳化混合物中。0.05到2的所有子范围均包含于本文中且公开于本文中。举例来说,范围可为下限0.05、0.07、0.09或0.1到上限0.8、1、1.3、1.8或2。
如上文所论述,互聚物包括至少一种不饱和单体子单元及包括至少一种选自由以下组成的组的化合物的子单元:至少一种共轭酸、至少一种共轭酸的至少一种酯及其混合物。压敏粘着剂组合物可进一步包含任选地存在的一或多种添加剂。一或多种添加剂的实例包含但不限于至少一种增稠剂、至少一种消泡剂、至少一种湿润剂、至少一种机械稳定剂、至少一种颜料、至少一种填充剂、至少一种冻融剂、至少一种中和剂、至少一种塑化剂、至少一种增粘剂、至少一种助粘剂及/或其组合。
水基压敏粘着剂组合物可包括0到5重量百分比的至少一种增稠剂。0到5重量百分比的所有个别值及子范围均包含于本文中且公开于本文中。举例来说,至少一种增稠剂的重量百分比可为下限0、0.1、0.2、0.3或0.5重量百分比到上限1、2、3、4或5重量百分比。实例增稠剂包含但不限于可购自密歇根州米德兰(Midland,Michigan)陶氏化学公司(The DowChemical Company)的ACRYSOLTM、UCARTM及CELOSIZETM。
水基压敏粘着剂组合物可包括0到2重量百分比的至少一种中和剂。0到2重量百分比的所有个别值及子范围均包含于本文中且公开于本文中。举例来说,至少一种中和剂的重量百分比可为下限0、0.2、0.3或0.5重量百分比到上限0.5、1、1.5或2重量百分比。中和剂通常用于控制pH,以向所调配的压敏粘着剂组合物提供稳定性。至少一种中和剂的实例包含但不限于氨水、水性胺及其它水性无机盐。
水基压敏粘着剂组合物可包括小于50重量百分比的至少一种增粘剂。小于50重量百分比的所有个别值及子范围均包含于本文中且公开于本文中。举例来说,至少一种增粘剂的重量百分比可为下限0、0.1、0.2、0.3、0.5、1、2、3、4或5重量百分比到上限10、20、30、40或50重量百分比。至少一种增粘剂的实例包含但不限于松香树脂(包含松香酸及/或通过松香酸与醇酯化获得的松香酯,环氧化合物及/或其混合物)、未氢化的脂肪族C5树脂、氢化的脂肪族C5树脂、芳香族改质的C5树脂、萜类树脂、氢化的C9树脂及其组合。
水基压敏粘着剂组合物可包括小于5重量百分比的至少一种助粘剂。小于5重量百分比的所有个别值及子范围均包含于本文中且公开于本文中。举例来说,至少一种助粘剂的重量百分比可为下限0、0.1、0.2、0.3、0.5、1、2、3或4重量百分比到上限0.1、0.2、0.3、0.5、1、2、3、4、5重量百分比。
本公开的实例
现将通过论述说明性实例及比较实例进一步详细解释本公开。然而,本公开的范围当然不限于这些说明性实例。
乳液聚合程序
一般来说,根据本公开的乳液混合物如下制备。配备有冷凝器、机械搅拌器、温度受控热电耦及引发剂及单体的入口的4升5颈反应器进料有675g的去离子(“DI”)水且在轻微N2流动下加热到88℃。在单独容器中,单体乳液(“ME”)通过混合以下制备:275g的DI水、10g的十二烷基苯磺酸钠表面活性剂(例如来自比利时布鲁塞尔(Brussels,Belgium)Solvay S.A.的RHODACALTM DS-4(“DS-4”))、11.9g的脂肪醇醚硫酸酯表面活性剂(例如来自德国路德维希港(Ludwigshafen,Germany)BASF SE的DISPONILTM FES77表面活性剂(“FES-77”))、2.5g的Na2CO3及1,672g的包括丙烯酸2-乙基己酯(“2-EHA”)、丙烯酸丁酯(“BA”)、丙烯酸乙酯(“EA”)、甲基丙烯酸甲酯(“MMA”)及丙烯酸(“AA”)的单体混合物。
随后,将Na2CO3与过硫酸铵(“APS”)的混合物于40g DI水中的溶液添加到反应器中。紧接在添加Na2CO3及APS的溶液之后,将单体乳液进料到反应器中。进料进行80分钟。为获得所公开的组合物,将包括桐酸、桐酸与甘油的单官能酯、桐酸与甘油的二官能酯的桐酸混合物(“T-160”),或桐油(两者均可购自中国安徽省瑞芬得油脂深加工有限公司(AnhuiRefined Oil and Fatty Co.,Ltd))添加到单体中
在完成单体乳液添加时,将反应混合物冷却到60℃,随后通过两个独立管道历经30分钟逐渐添加叔丁基氢过氧化物(70%)(“t-BHP”)(9.2g于32g DI水中)的溶液及于34.5g DI水中的6.8g还原剂,例如来自美国宾夕法尼亚州查兹佛德伯格曼化学公司(Brüggemann Chemical US Company,Chadds Ford,Pennsylvania)的BRUGGOLITETM FF6 M(“FF6”)。在完成进料时,将反应物冷却到室温。所获得的组合物随后通过325目滤布过滤,以制备用于后续评估工作的组合物。
压敏粘着剂调配物
除非另外规定,否则所有样品均通过湿润剂轻微调配,例如基于总乳液,0.5%(湿润/湿润)获自新泽西州伍德兰帕氰特公司(Cytec,Woodland Park,New Jersey)的AEROSOLTM GPG湿润剂(“GPG”),以改进浸透以供实验室消耗。粘度随后使用增稠剂(例如来自密歇根州米德兰陶氏化学公司的ACRYSOLTM RM-2020(“RM-2020”))调节到约600cp(Brookfield,RVDV,30rpm,63#),且最终pH使用氨调节到7.0到7.5。
实验室消耗
聚乙烯(“PE”)膜在层压之前通过电晕处理预处理。调配的粘着剂以干物质重量计以18g/m2的量涂布到离型衬垫且在80℃下干燥6分钟。PE膜通过压敏粘着剂涂布的离型衬垫以一定方式层压,使得粘着剂层与PE膜的电晕处理侧接触,以得到粘着剂层制品。
耐水增白性测试
性能测试在粘着剂层制品在受控环境(22-24℃,50-60%相对湿度)测试实验室中调节至少隔夜之后进行。
从制备的层制品去除衬垫之后,在室温下将粘着剂涂布的PE膜浸入于水中3小时。随后,在BYK Haze Gard Plus测量设备上评估粘着剂涂布的PE膜的透明度及浑浊度特性。透明度及浑浊度根据ASTM方法D1003测量。较高透明度指示较佳耐水增白性,同时较低浑浊度指示较佳耐水增白性。
方法允许在工艺内添加及不添加桐油或桐酸而制备的样品之间的比较。在各情况下,发现添加桐酸或桐油显著改进耐水增白性性能。
粘着剂组合物调配物
说明性实例(“IE”)及比较实例(“CE”)(统称为“实例”)根据表1中所列举的调配物制备,单位指示重量份。
表1:IE及CE的组成
实例 | 2-EHA | EA | MMA | AA | 桐油 | 桐酸 | 总计 |
CE1 | 71.5 | 18.5 | 9 | 1 | 100.0 | ||
CE2 | 71.5 | 18.5 | 9 | 1 | 0.5<sup>a</sup> | 100.5 | |
IE1 | 71.5 | 18.5 | 9 | 1 | 1<sup>b</sup> | 101.0 | |
IE2 | 71.5 | 18.5 | 9 | 1 | 0.5<sup>c</sup> | 100.5 | |
IE3 | 71.5 | 18.5 | 9 | 1 | 0.5<sup>b</sup> | 0.5<sup>b</sup> | 101.0 |
IE4 | 71.5 | 18.5 | 9 | 1 | 0.5<sup>d</sup> | 1<sup>c</sup> | 101.5 |
IE5 | 71.5 | 18.5 | 9 | 1 | 0.5<sup>d</sup> | 0.5<sup>c</sup> | 101.0 |
IE6 | 71.5 | 18.5 | 9 | 1 | 1<sup>d</sup> | 101.0 | |
IE7 | 71.5 | 18.5 | 9 | 1 | 1<sup>d</sup> | 101.0 |
a掺合后添加
b95%单体乳液进料时添加
c90%单体乳液进料时添加
d贯穿单体乳液进料添加
性能结果
在如上文所论述的BYK Haze Gard Plus测量设备上测试的实例的性能结果概述于表2中。表2中详述的浑浊度及透明度值表示浑浊度%及透明度%。
表2:IE及CE的性能结果
样品 | 浑浊度(%) | 透明度(%) |
CE1 | 55 | 86 |
CE2 | 55 | 85 |
IE1 | 40 | 89 |
IE2 | 46 | 86 |
IE3 | 38 | 89 |
IE4 | 34 | 90 |
IE5 | 47 | 87 |
IE6 | 34 | 88 |
IE7 | 48 | 83 |
如表2中所指示,出人意料地发现在IE中在聚合期间使用共轭酸或共轭酸的酯(例如桐油及/或桐酸)改进粘着剂组合物的耐水增白性。特定而言,不含有桐油或桐酸的CE1呈现实例的最高浑浊度及实例的低透明度。含有在其余组分掺合之后添加的桐油的CE2呈现实例的最高浑浊度及次最低透明度。IE1-IE7分别与CE1或CE2相比呈现显著较低浑浊度。另外,IE1及IE3-IE6分别与CE1或CE2相比呈现较高透明度。而IE2及IE7仅类似于CE1的透明度,其与CE1相比呈现显著较低浑浊度。
根据实例的比较表明根据本公开制备的用于压敏粘着剂应用的组合物与现有组合物相比呈现增加的耐水增白性。基于上文的比较,可看出这个有利特征可归因于在乳液聚合期间包含至少一种选自由以下组成的组的化合物:共轭酸、共轭酸的酯或其混合物,尤其当衍生自桐油时。
Claims (5)
1.一种水基粘着剂组合物,其包括:
至少一种分散于水性介质中的互聚物,所述互聚物包括至少一种不饱和单体及至少一种选自由以下组成的组的化合物:共轭酸的至少一种酯及所述至少一种酯和至少一种共轭酸的混合物,
其中所述至少一种共轭酸衍生自桐油,
其中所述至少一种酯为桐油,及
其中所述至少一种化合物构成所述互聚物的0.01到5重量百分比。
2.一种用于制备水基粘着剂组合物的方法,其包括:
将至少一种不饱和单体及至少一种表面活性剂分散于水性介质中以形成乳化混合物;
将至少一种引发剂引入到所述乳化混合物,借此使所述至少一种不饱和单体聚合;及
在所述至少一种不饱和单体的聚合期间将至少一种选自以下的化合物引入到所述乳化混合物:共轭酸的至少一种酯及所述至少一种酯和至少一种共轭酸的混合物,借此形成包括所述至少一种不饱和单体及所述至少一种化合物的互聚物,
其中所述至少一种共轭酸衍生自桐油,
其中所述至少一种酯为桐油,及
其中所述至少一种化合物构成所述互聚物的0.01到5重量百分比。
3.如权利要求2所述的方法,其中所述至少一种化合物在至少50%的所述至少一种不饱和单体引入到所述水性介质之后引入到所述乳化混合物。
4.如权利要求2所述的方法,其中所述至少一种化合物在至少90%的所述至少一种不饱和单体引入到所述水性介质之后引入到所述乳化混合物。
5.一种水基压敏粘着剂,其包括根据权利要求2制备的粘着剂组合物。
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