CN101415733A - 制备聚合物水分散体的方法 - Google Patents
制备聚合物水分散体的方法 Download PDFInfo
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- CN101415733A CN101415733A CNA2007800123654A CN200780012365A CN101415733A CN 101415733 A CN101415733 A CN 101415733A CN A2007800123654 A CNA2007800123654 A CN A2007800123654A CN 200780012365 A CN200780012365 A CN 200780012365A CN 101415733 A CN101415733 A CN 101415733A
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- Prior art keywords
- alkene
- methyl
- monomer
- weight
- heavenly stems
- Prior art date
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- 239000004815 dispersion polymer Substances 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 150000001336 alkenes Chemical class 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 239000000178 monomer Substances 0.000 claims description 111
- -1 carbon atom alkene Chemical class 0.000 claims description 54
- 150000003254 radicals Chemical class 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 37
- 238000006116 polymerization reaction Methods 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 230000002776 aggregation Effects 0.000 claims description 24
- 238000004220 aggregation Methods 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 22
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 239000006185 dispersion Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- 239000003999 initiator Substances 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 12
- 230000000379 polymerizing effect Effects 0.000 claims description 10
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- 238000005259 measurement Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 description 36
- 239000003995 emulsifying agent Substances 0.000 description 19
- 150000001721 carbon Chemical group 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000000126 substance Substances 0.000 description 16
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 15
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 12
- 230000007704 transition Effects 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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- 229910052757 nitrogen Inorganic materials 0.000 description 9
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
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- 125000004494 ethyl ester group Chemical group 0.000 description 7
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 6
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- 229910052783 alkali metal Inorganic materials 0.000 description 6
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 6
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- 150000003839 salts Chemical class 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
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- 239000002253 acid Substances 0.000 description 5
- 239000000084 colloidal system Substances 0.000 description 5
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- 230000001681 protective effect Effects 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
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- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 238000013103 analytical ultracentrifugation Methods 0.000 description 4
- 239000012874 anionic emulsifier Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000007046 ethoxylation reaction Methods 0.000 description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical group [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052728 basic metal Inorganic materials 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 2
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 2
- MLMGJTAJUDSUKA-UHFFFAOYSA-N 2-ethenyl-1h-imidazole Chemical compound C=CC1=NC=CN1 MLMGJTAJUDSUKA-UHFFFAOYSA-N 0.000 description 2
- YBOZNTGUYASNRA-UHFFFAOYSA-N 2-methyloct-2-ene Chemical compound CCCCCC=C(C)C YBOZNTGUYASNRA-UHFFFAOYSA-N 0.000 description 2
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- 125000002091 cationic group Chemical group 0.000 description 2
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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
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
-
- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/14—Monomers containing five or more carbon atoms
-
- 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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- 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
- C08F220/40—Esters of unsaturated alcohols, e.g. allyl (meth)acrylate
Abstract
本发明涉及一种使用具有5-12个碳原子的链烯烃制备聚合物水分散体的方法。
Description
本发明提供了一种通过烯属不饱和单体在至少一种分散剂和至少一种自由基引发剂存在下的自由基引发水乳液聚合而制备聚合物水分散体的方法,其中将
1-50重量%具有5-12个碳原子的链烯烃[单体A],和
50-99重量%基于具有3-6个碳原子的α,β-单烯属不饱和单羧酸或二羧酸和具有1-12个碳原子的链烷醇的酯[单体B],以及合适的话
0-10重量%具有3-6个碳原子的α,β-单烯属不饱和单羧酸或二羧酸和/或其酰胺[单体C],和
0-30重量%不同于单体A-C的α,β-烯属不饱和化合物[单体D],
用于乳液聚合,其中单体A-D加起来为100重量%,其中在引发聚合反应之前将单体A的总量中至少50重量%和任选将单体B-D总量中各自至多10重量%包括在聚合容器的初始进料中,并在聚合条件下将任何剩余的单体A和全部量或合适的话剩余的单体B-D供入聚合容器中。
制备基于链烯烃和其他可共聚烯属不饱和化合物的聚合物的方法对熟练技术人员是众所周知的。共聚基本以溶液聚合形式(例如参见A.Sen等,Journal American Chemical Society,2001,123,第12738-39页,B.Klumperman等,Macromolecules,2004,37,第4406-16页;A.Sen等,Journal of Polymer Science,Part A:Polymer Chemistry,2004,42(24),第6175-92页;WO 03/042254、WO 03/091297或EP-A 1384729)或以水乳液聚合形式进行,这尤其基于最低级链烯烃乙烯进行(例如参见US-A 4921898、US-A 5070134、US-A 5110856、US-A 5629370、EP-A295727、EP-A 757065、EP-A 1114833或DE-A 19620817)。
涉及使用高级链烯烃的自由基引发的水乳液聚合的现有技术如下:
DE-A 1720277公开了一种使用乙烯基酯和1-辛烯制备成膜聚合物水分散体的方法。乙烯基酯与1-辛烯的重量比可以为99:1-70:30。任选可以将少量乙烯基酯以与其他可共聚烯属不饱和化合物的混合物用于乳液聚合。
S.M.Samoilov在J.Macromol.Sci.Chem.,1983,A19(1),第107-22页中描述了丙烯与不同烯属不饱和化合物的自由基引发的水乳液聚合。其中所观察到的结果是与使用自由基引发的水乳液聚合的典型烯属不饱和化合物,即乙酸乙烯酯、氯乙烯、丙烯酸甲酯和丙烯酸丁酯时相比,丙烯与具有强吸电子基团的烯属不饱和化合物如一氯三氟乙烯、三氟丙烯腈、马来酸酐或三氟丙烯酸甲酯的共聚得到具有显著更高丙烯含量的聚合物,或具有更高分子量的共聚物。得到这一结果的原因尤其包括高级链烯烃常有的氢自由基转移反应。
在本申请人所提交的申请号为DE 10 2005 035 692.3的德国专利申请中,公开了基于具有5-12个碳原子的链烯烃的聚合物水分散体的制备。此时在聚合条件下将具有5-12个碳原子的链烯烃计量加入聚合混合物中。
本发明的目的是在可以实现的单体转化率方面改进在德国专利申请DE 10 2005 035 692.3中所公开的聚合物水分散体的制备方法。
惊人的是该目的已经由开头所定义的方法实现。
烯属不饱和单体在含水介质中的自由基引发的乳液聚合的实施以前已经有过很多描述,因此对熟练技术人员而言完全是众所周知的[就此而言参见Emulsion Polymerization in Encyclopedia of Polymer Science andEngineering,第8卷,第659页及随后各页(1987);D.C.Blackley,HighPolymer Latices,第1卷,第35页及随后各页(1966);H.Warson,TheApplications of Synthetic Resin Emulsions,第5章,第246页及随后各页(1972);D.Diederich,Chemie in unserer Zeit24,第135-42页(1990);Emulsion Polymerisation,Interscience Publishers,New York(1965);DE-A40 03 422,以及Dispersionen synthetischer Hochpolymerer,F.,Springer-Verlag,Berlin(1969)]。自由基引发的水乳液聚合反应的进行通常应使烯属不饱和单体使用分散剂以单体液滴形式分散性地分布在含水介质中并借助自由基聚合引发剂聚合。本发明方法与该程序的不同仅在于使用特定的单体组成和特定的单体进料方式。
在本发明方法中,使用水,通常为饮用水,但特别优选去离子水,其总量的计算应使得其用量为≥30重量%且≤90重量%,有利的是≥40重量%且≤75重量%,在每种情况下基于可以通过本发明方法得到的聚合物水分散体。
按照本发明,可以将一部分或全部水包括在聚合容器的初始进料中并在引发聚合反应之后计量加入任何剩余的水。就此而言,可以将任何剩余的水以恒定或变化的流速一次或分多次断续或连续计量加入聚合容器中。特别有利的是以恒定流速连续进行水进料,尤其作为单体水乳液和/或自由基引发剂水溶液的一部分进料。
有用的单体A包括所有具有5-12个碳原子,优选5-10个碳原子,更优选6-8个碳原子的线性或环状链烯烃,所述链烯烃可以自由基共聚且除了碳和氢外不含其他元素。这例如包括线性链烯烃2-甲基丁-1-烯、3-甲基丁-1-烯、3,3-二甲基-2-异丙基丁-1-烯、2-甲基丁-2-烯、3-甲基丁-2-烯、戊-1-烯、2-甲基戊-1-烯、3-甲基戊-1-烯、4-甲基戊-1-烯、戊-2-烯、2-甲基戊-2-烯、3-甲基戊-2-烯、4-甲基戊-2-烯、2-乙基戊-1-烯、3-乙基戊-1-烯、4-乙基戊-1-烯、2-乙基戊-2-烯、3-乙基戊-2-烯、4-乙基戊-2-烯、2,4,4-三甲基戊-1-烯、2,4,4-三甲基戊-2-烯、3-乙基-2-甲基戊-1-烯、3,4,4-三甲基戊-2-烯、2-甲基-3-乙基戊-2-烯、己-1-烯、2-甲基己-1-烯、3-甲基己-1-烯、4-甲基己-1-烯、5-甲基己-1-烯、己-2-烯、2-甲基己-2-烯、3-甲基己-2-烯、4-甲基己-2-烯、5-甲基己-2-烯、己-3-烯、2-甲基己-3-烯、3-甲基己-3-烯、4-甲基己-3-烯、5-甲基己-3-烯、2,2-二甲基己-3-烯、2,3-二甲基己-2-烯、2,5-二甲基己-3-烯、2,5-二甲基己-2-烯、3,4-二甲基己-1-烯、3,4-二甲基己-3-烯、5,5-二甲基己-2-烯、2,4-二甲基己-1-烯、庚-1-烯、2-甲基庚-1-烯、3-甲基庚-1-烯、4-甲基庚-1-烯、5-甲基庚-1-烯、6-甲基庚-1-烯、庚-2-烯、2-甲基庚-2-烯、3-甲基庚-2-烯、4-甲基庚-2-烯、5-甲基庚-2-烯、6-甲基庚-2-烯、庚-3-烯、2-甲基庚-3-烯、3-甲基庚-3-烯、4-甲基庚-3-烯、5-甲基庚-3-烯、6-甲基庚-3-烯、6,6-二甲基庚-1-烯、3,3-二甲基庚-1-烯、3,6-二甲基庚-1-烯、2,6-二甲基庚-2-烯、2,3-二甲基庚-2-烯、3,5-二甲基庚-2-烯、4,5-二甲基庚-2-烯、4,6-二甲基庚-2-烯、4-乙基庚-3-烯、2,6-二甲基庚-3-烯、4,6-二甲基庚-3-烯、2,5-二甲基庚-4-烯、辛-1-烯、2-甲基辛-1-烯、3-甲基辛-1-烯、4-甲基辛-1-烯、5-甲基辛-1-烯、6-甲基辛-1-烯、7-甲基辛-1-烯、辛-2-烯、2-甲基辛-2-烯、3-甲基辛-2-烯、4-甲基辛-2-烯、5-甲基辛-2-烯、6-甲基辛-2-烯、7-甲基辛-2-烯、辛-3-烯、2-甲基辛-3-烯、3-甲基辛-3-烯、4-甲基辛-3-烯、5-甲基辛-3-烯、6-甲基辛-3-烯、7-甲基辛-3-烯、辛-4-烯、2-甲基辛-4-烯、3-甲基辛-4-烯、4-甲基辛-4-烯、5-甲基辛-4-烯、6-甲基辛-4-烯、7-甲基辛-4-烯、7,7-二甲基辛-1-烯、3,3-二甲基辛-1-烯、4,7-二甲基辛-1-烯、2,7-二甲基辛-2-烯、2,3-二甲基辛-2-烯、3,6-二甲基辛-2-烯、4,5-二甲基辛-2-烯、4,6-二甲基辛-2-烯、4,7-二甲基辛-2-烯、4-乙基辛-3-烯、2,7-二甲基辛-3-烯、4,7-二甲基辛-3-烯、2,5-二甲基辛-4-烯、壬-1-烯、2-甲基壬-1-烯、3-甲基壬-1-烯、4-甲基壬-1-烯、5-甲基壬-1-烯、6-甲基壬-1-烯、7-甲基壬-1-烯、8-甲基壬-1-烯、壬-2-烯、2-甲基壬-2-烯、3-甲基壬-2-烯、4-甲基壬-2-烯、5-甲基壬-2-烯、6-甲基壬-2-烯、7-甲基壬-2-烯、8-甲基壬-2-烯、壬-3-烯、2-甲基壬-3-烯、3-甲基壬-3-烯、4-甲基壬-3-烯、5-甲基壬-3-烯、6-甲基壬-3-烯、7-甲基壬-3-烯、8-甲基壬-3-烯、壬-4-烯、2-甲基壬-4-烯、3-甲基壬-4-烯、4-甲基壬-4-烯、5-甲基壬-4-烯、6-甲基壬-4-烯、7-甲基壬-4-烯、8-甲基壬-4-烯、4,8-二甲基壬-1-烯、4,8-二甲基壬-4-烯、2,8-二甲基壬-4-烯、癸-1-烯、2-甲基癸-1-烯、3-甲基癸-1-烯、4-甲基癸-1-烯、5-甲基癸-1-烯、6-甲基癸-1-烯、7-甲基癸-1-烯、8-甲基癸-1-烯、9-甲基癸-1-烯、癸-2-烯、2-甲基癸-2-烯、3-甲基癸-2-烯、4-甲基癸-2-烯、5-甲基癸-2-烯、6-甲基癸-2-烯、7-甲基癸-2-烯、8-甲基癸-2-烯、9-甲基癸-2-烯、癸-3-烯、2-甲基癸-3-烯、3-甲基癸-3-烯、4-甲基癸-3-烯、5-甲基癸-3-烯、6-甲基癸-3-烯、7-甲基癸-3-烯、8-甲基癸-3-烯、9-甲基癸-3-烯、癸-4-烯、2-甲基癸-4-烯、3-甲基癸-4-烯、4-甲基癸-4-烯、5-甲基癸-4-烯、6-甲基癸-4-烯、7-甲基癸-4-烯、8-甲基癸-4-烯、9-甲基癸-4-烯、癸-5-烯、2-甲基癸-5-烯、3-甲基癸-5-烯、4-甲基癸-5-烯、5-甲基癸-5-烯、6-甲基癸-5-烯、7-甲基癸-5-烯、8-甲基癸-5-烯、9-甲基癸-5-烯、2,4-二甲基癸-1-烯、2,4-二甲基癸-2-烯、4,8-二甲基癸-1-烯、十一碳-1-烯、2-甲基十一碳-1-烯、3-甲基十一碳-1-烯、4-甲基十一碳-1-烯、5-甲基十一碳-1-烯、6-甲基十一碳-1-烯、7-甲基十一碳-1-烯、8-甲基十一碳-1-烯、9-甲基十一碳-1-烯、10-甲基十一碳-1-烯、十一碳-2-烯、2-甲基十一碳-2-烯、3-甲基十一碳-2-烯、4-甲基十一碳-2-烯、5-甲基十一碳-2-烯、6-甲基十一碳-2-烯、7-甲基十一碳-2-烯、8-甲基十一碳-2-烯、9-甲基十一碳-2-烯、10-甲基十一碳-2-烯、十一碳-3-烯、2-甲基十一碳-3-烯、3-甲基十一碳-3-烯、4-甲基十一碳-3-烯、5-甲基十一碳-3-烯、6-甲基十一碳-3-烯、7-甲基十一碳-3-烯、8-甲基十一碳-3-烯、9-甲基十一碳-3-烯、10-甲基十一碳-3-烯、十一碳-4-烯、2-甲基十一碳-4-烯、3-甲基十一碳-4-烯、4-甲基十一碳-4-烯、5-甲基十一碳-4-烯、6-甲基十一碳-4-烯、7-甲基十一碳-4-烯、8-甲基十一碳-4-烯、9-甲基十一碳-4-烯、10-甲基十一碳-4-烯、十一碳-5-烯、2-甲基十一碳-5-烯、3-甲基十一碳-5-烯、4-甲基十一碳-5-烯、5-甲基十一碳-5-烯、6-甲基十一碳-5-烯、7-甲基十一碳-5-烯、8-甲基十一碳-5-烯、9-甲基十一碳-5-烯、10-甲基十一碳-5-烯、十二碳-1-烯、十二碳-2-烯、十二碳-3-烯、十二碳-4-烯、十二碳-5-烯或十二碳-6-烯,以及环烯烃环戊烯、2-甲基环戊-1-烯、3-甲基环戊-1-烯、4-甲基环戊-1-烯、3-丁基环戊-1-烯、乙烯基环戊烷、环己烯、2-甲基环己-1-烯、3-甲基环己-1-烯、4-甲基环己-1-烯、1,4-二甲基环己-1-烯、3,3,5-三甲基环己-1-烯、4-环戊基环己-1-烯、乙烯基环己烷、环庚烯、1,2-二甲基环庚-1-烯、环辛烯、2-甲基环辛-1-烯、3-甲基环辛-1-烯、4-甲基环辛-1-烯、5-甲基环辛-1-烯、环壬烯、环癸烯、环十一碳烯、环十二碳烯、双环[2.2.1]庚-2-烯、5-乙基双环[2.2.1]庚-2-烯、2-甲基双环[2.2.2]辛-2-烯、双环[3.3.1]壬-2-烯或双环[3.2.2]壬-6-烯。
优选使用1-链烯烃,实例是戊-1-烯、己-1-烯、庚-1-烯、辛-1-烯、壬-1-烯、癸-1-烯、十一碳-1-烯、十二碳-1-烯、2,4,4-三甲基戊-1-烯、2,4-二甲基己-1-烯、6,6-二甲基庚-1-烯或2-甲基辛-1-烯。作为单体A有利的是使用具有6-8个碳原子的链烯烃,优选具有6-8个碳原子的1-链烯烃。特别优选使用己-1-烯、庚-1-烯或辛-1-烯。应理解的是还可以使用上述单体A的混合物。
作为单体B使用的是基于具有3-6个碳原子,尤其是3或4个碳原子的α,β-单烯属不饱和单羧酸或二羧酸和具有1-12个碳原子的链烷醇,优选具有1-8个碳原子的链烷醇,尤其是具有1-4个碳原子的链烷醇的酯,所述单羧酸或二羧酸尤其如丙烯酸、甲基丙烯酸、马来酸、富马酸和衣康酸,而所述链烷醇尤其如甲醇、乙醇、正丙醇、异丙醇、正丁醇、2-甲基丙-1-醇、叔丁醇、正戊醇、3-甲基丁-1-醇、正己醇、4-甲基戊-1-醇、正庚醇、5-甲基己-1-醇、正辛醇、6-甲基庚-1-醇、正壬醇、7-甲基辛-1-醇、正癸醇、8-甲基壬-1-醇、正十二烷醇、9-甲基癸-1-醇或2-乙基己-1-醇。优选使用丙烯酸和甲基丙烯酸的甲基酯、乙基酯、正丁基酯、异丁基酯、戊基酯、己基酯、庚基酯、辛基酯、壬基酯、癸基酯、2-乙基己基酯或十二烷基酯,富马酸和马来酸的二甲基酯或二正丁基酯。应理解的是还可以使用上述酯的混合物。
所用单体C任选为具有3-6个碳原子的α,β-单烯属不饱和单羧酸或二羧酸和/或其酰胺,尤其如丙烯酸、甲基丙烯酸、马来酸、富马酸或衣康酸以及丙烯酰胺或甲基丙烯酰胺。应理解的是还可以使用上单体C的混合物。
用作与单体A-C不同的单体D的单体实例包括α,β-烯属不饱和化合物,例如乙烯基芳族单体,如苯乙烯、α-甲基苯乙烯、邻氯苯乙烯或乙烯基甲苯,乙烯基卤,如氯乙烯或偏二氯乙烯,乙烯醇和具有1-18个碳原子的单羧酸的酯,如乙酸乙烯酯、丙酸乙烯酯、正丁酸乙烯酯、月桂酸乙烯酯和硬脂酸乙烯酯,α,β-单烯属或二烯属不饱和羧酸的腈,如丙烯腈、甲基丙烯腈、富马腈、马来腈,以及具有4-8个碳原子的共轭二烯烃,如1,3-丁二烯和异戊二烯,还有乙烯基磺酸、2-丙烯酰胺基-2-甲基丙烷磺酸、苯乙烯磺酸,及其水溶性盐,还有N-乙烯基吡咯烷酮、2-乙烯基吡啶、4-乙烯基吡啶、2-乙烯基咪唑、丙烯酸2-(N,N-二甲基氨基)乙基酯、甲基丙烯酸2-(N,N-二甲基氨基)乙基酯、丙烯酸2-(N,N-二乙基氨基)乙基酯、甲基丙烯酸2-(N,N-二乙基氨基)乙基酯、甲基丙烯酸2-(N-叔丁基氨基)乙基酯、N-(3-N’,N’-二甲基氨基丙基)甲基丙烯酰胺或甲基丙烯酸2-(1-咪唑啉-2-酮基)乙基酯。其他单体D具有至少一个环氧基、羟基、N-羟甲基或羰基,或至少两个非共轭烯属不饱和双键。其实例是含有两个乙烯基的单体、含有两个亚乙烯基的单体以及含有两个链烯基的单体。就此而言特别优选二元醇与α,β-单烯属不饱和单羧酸的二酯,其中优选丙烯酸和甲基丙烯酸。含有两个非共轭烯属不饱和双键的这类单体的实例是亚烷基二醇二丙烯酸酯和二甲基丙烯酸酯,如乙二醇二丙烯酸酯、1,2-丙二醇二丙烯酸酯、1,3-丙二醇二丙烯酸酯、1,3-丁二醇二丙烯酸酯、1,4-丁二醇二丙烯酸以及乙二醇二甲基丙烯酸酯、1,2-丙二醇二甲基丙烯酸酯、1,3-丙二醇二甲基丙烯酸酯、1,3-丁二醇二甲基丙烯酸酯和1,4-丁二醇二甲基丙烯酸酯,还有二乙烯基苯、甲基丙烯酸乙烯酯、丙烯酸乙烯酯、甲基丙烯酸烯丙基酯、丙烯酸烯丙基酯、马来酸二烯丙基酯、富马酸二烯丙基酯、亚甲基双丙烯酰胺、丙烯酸环戊二烯基酯、氰脲酸三烯丙基酯或异氰脲酸三烯丙基酯。就此而言特别重要的还有丙烯酸和甲基丙烯酸的C1-C8羟烷基酯如丙烯酸和甲基丙烯酸的1-羟基乙基、1-羟基丙基或1-羟基丁基酯,以及化合物如丙烯酸或甲基丙烯酸的缩水甘油酯,双丙酮丙烯酰胺和丙烯酸或甲基丙烯酸的乙酰乙酰氧基乙酯。应理解的是还可以使用上述单体D的混合物。
然而,优选使用如下单体进行自由基引发的水乳液聚合:
1-49.99重量%单体A,
50-98.99重量%单体B,和
0.01-10重量%单体C。
所用单体A尤其为戊-1-烯、己-1-烯、庚-1-烯、辛-1-烯、3-甲基己-1-烯、3-甲基庚-1-烯和/或3-甲基辛-1-烯,所用单体B尤其为丙烯酸正丁基酯、丙烯酸甲酯、丙烯酸2-乙基己基酯、甲基丙烯酸甲酯和/或丙烯酸叔丁基酯,以及所用单体C尤其为丙烯酸、甲基丙烯酸和/或衣康酸。
特别优选自由基引发的水乳液聚合使用如下单体进行:
5-40重量%戊-1-烯、己-1-烯和/或辛-1-烯[单体A],
56-94.9重量%丙烯酸正丁基酯、丙烯酸甲酯、丙烯酸2-乙基己基酯、甲基
丙烯酸甲酯和/或丙烯酸叔丁基酯[单体B],和
0.1-4重量%丙烯酸和/或甲基丙烯酸[单体C]。
对该方法必要的是在引发聚合反应之前,单体A的总量中至少50重量%应包括在聚合容器的初始进料中,并且任何剩余的单体A和全部量或合适的话剩余的单体B-D应在聚合条件下供入聚合容器中。
有利的是在引发聚合反应之前,单体A的总量中≥60重量%或≥70重量%,特别有利的是≥80重量%或≥90重量%或甚至全部量的单体A包括在聚合容器的初始进料中。在已经引发自由基聚合反应之后,任何剩余的单体A,即单体A的总量中≤50重量%,≤40重量%,≤30重量%,≤20重量%或≤10重量%的计量加入此时可以以恒定或变化流速一次断续、两次或更多次断续或连续进行。优选在引发聚合反应之前将全部量的单体A包括在聚合容器的初始进料中。
按照本发明可以在引发聚合反应之前任选将单体B-D总量中各自至多10重量%,通常≤5重量%包括在聚合容器的初始进料中。有利的是不将任何单体B-D包括在聚合容器的初始进料中。可以在已经引发自由基聚合反应之后将任何剩余的或全部量的单体B-D加入聚合容器中,并且这可以以恒定或变化流速一次断续、两次或更多次断续或连续进行。有利的是以恒定流速连续加入单体B-D。有利的是以单体混合物形式加入单体B-D,特别有利的是以单体水乳液形式加入。
按照本发明,对于本方法而言,使用分散剂,其不仅维持单体液滴而且维持所得聚合物颗粒在含水介质中的分散性分布并因此确保所产生的聚合物水分散体的稳定性。合适的分散剂不仅包括常用于实施自由基水乳液聚合的保护性胶体,而且包括乳化剂。
合适的保护性胶体实例包括聚乙烯醇,聚亚烷基二醇,聚丙烯酸和聚甲基丙烯酸的碱金属盐,明胶衍生物或包含丙烯酸、甲基丙烯酸、马来酸酐、2-丙烯酰胺基-2-甲基丙烷磺酸和/或4-苯乙烯磺酸的共聚物,以及该类共聚物的碱金属盐,还有包含N-乙烯基吡咯烷酮、N-乙烯基己内酰胺、N-乙烯基咔唑、1-乙烯基咪唑、2-乙烯基咪唑、2-乙烯基吡啶、4-乙烯基吡啶、丙烯酰胺、甲基丙烯酰胺、带有氨基的丙烯酸酯、甲基丙烯酸酯、丙烯酰胺和/或甲基丙烯酰胺的均聚物和共聚物。其他合适保护性胶体的详细描述在Houben-Weyl,Methoden der organischen Chemie,第XIV/1卷,Makromolekulare Stoffe[大分子化合物],Georg-Thieme-Verlag,Stuttgart,1961,第411-20页中找到。
应理解的是还可以使用保护性胶体和/或乳化剂的混合物。所用分散剂通常仅为乳化剂,其相对分子量与保护性胶体不同的是通常低于1000。事实上它们可以是阴离子、阳离子或非离子型的。应理解的是当使用表面活性物质的混合物时,各组分必须相互相容,对此有怀疑时可以借助几个初步试验确定。通常而言,阴离子乳化剂相互相容且与非离子乳化剂相容。阳离子乳化剂也同样如此,而阴离子乳化剂和阳离子乳化剂通常相互不相容。合适乳化剂的综述在Houben-Weyl,Methoden der organischenChemie,第XIV/1卷,Makromolekulare Stoffe[大分子化合物],Georg-Thieme-Verlag,Stuttgart,1961,第192-208页中找到。
然而,按照本发明尤其将乳化剂用作分散剂。
常规非离子乳化剂例如为乙氧基化单-、二-和三烷基酚(EO程度:3-50,烷基:C4-C12)以及乙氧基化脂肪醇(EO程度:3-80;烷基:C8-C36)。其实例是A品级(C12C14脂肪醇乙氧基化物,EO程度:3-8),AO品级(C13C15羰基合成醇乙氧基化物,EO程度:3-30),AT品级(C16C18脂肪醇乙氧基化物,EO程度:11-80),ON品级(C10羰基合成醇乙氧基化物,EO程度:3-11)和TO品级(C13羰基合成醇乙氧基化物,EO程度:3-20),全部来自BASF AG。
典型的阴离子乳化剂例如为烷基硫酸(烷基:C8-C12)、乙氧基化链烷醇(EO程度:4-30,烷基:C12-C18)和乙氧基化烷基酚(EO程度:3-50,烷基:C4-C12)的硫酸单酯、烷基磺酸(烷基:C12-C18)和烷基芳基磺酸(烷基:C9-C18)的碱金属盐和铵盐。
已经证明适合作为其他阴离子乳化剂的化合物还有通式(I)化合物:
其中R1和R2为氢原子或C4-C24烷基,但不同时为氢原子,并且M1和M2可以为碱金属离子和/或铵离子。在通式(I)中,R1和R2优选为具有6-18个碳原子,尤其是具有6、12和16个碳原子的线性或支化烷基,或氢,但R1和R2不同时为氢原子。M1和M2优选为钠、钾或铵,特别优选钠。特别有利的化合物(I)是其中M1和M2为钠,R1为具有12个碳原子的支化烷基且R2为氢原子或R1的那些。通常使用含有50-90重量%单烷基化产物的工业混合物,实例是2A1(Dow Chemical Company的牌号)。化合物(I)例如通常由US-A 4269749已知且可市购。
合适的阳离子活性乳化剂通常为含C6-C18烷基-、C6-C18烷基芳基-或杂环基的伯、仲、叔或季铵盐,链烷醇铵盐,吡啶鎓盐、咪唑啉鎓盐、噁唑啉鎓盐、吗啉鎓盐、噻唑啉鎓盐和胺氧化物的盐、喹啉鎓盐、异喹啉鎓盐、鎓盐、锍盐和鏻盐。可以提到的实例包括十二烷基乙酸铵或对应的硫酸盐,各种链烷酸2-(N,N,N-三甲基铵基)乙基酯的硫酸盐或乙酸盐,硫酸N-十六烷基吡啶鎓盐、硫酸N-月桂基吡啶鎓盐和N-十六烷基-N,N,N-三甲基硫酸铵、N-十二烷基-N,N,N-三甲基硫酸铵、N-辛基-N,N,N-三甲基硫酸铵、N,N-二硬脂基-N,N-二甲基硫酸铵,以及偕表面活性剂N,N’-(月桂基二甲基)乙二胺二硫酸盐、乙氧基化牛脂基-N-甲基硫酸铵和乙氧基化油胺(例如BASF AG的AC,约12个氧化乙烯单元)。许多其他实例在H.Stache,Tensid-Taschenbuch,Carl-Hanser-Verlag,Munich,Vienna,1981以及McCutcheon’s,Emulsifiers & Detergents,MCPublishing Company,Glen Rock,1989中找到。有利的是阴离子抗衡基团尽可能具有低亲核性,例如高氯酸根、硫酸根、磷酸根、硝酸根和羧酸根如乙酸根、三氟乙酸根、三氯乙酸根、丙酸根、草酸根、柠檬酸根和苯甲酸根,以及有机磺酸的共轭阴离子如甲基磺酸根、三氟甲基磺酸根和对甲苯磺酸根,还有四氟硼酸根、四苯基硼酸根、四(五氟苯基)硼酸根、四[二(3,5-三氟甲基)苯基]硼酸根、六氟磷酸根、六氟砷酸根或六氟锑酸根。
优选用作分散剂的乳化剂有利地以≥0.005重量%且≤10重量%,优选≥0.01重量%且≤5重量%,尤其是≥0.1重量%且≤3重量%的总量使用,在每种情况下基于单体总量。
额外或代替乳化剂作为分散剂使用的保护性胶体的总量通常≥0.1重量%且≤10重量%,常常≥0.2重量%且≤7重量%,在每种情况下基于单体总量。
然而,优选使用阴离子和/或非离子乳化剂,特别优选将阴离子乳化剂用作分散剂。
自由基引发的水乳液聚合借助自由基聚合引发剂开始。引发剂原则上可以是过氧化物和偶氮化合物。应理解的是氧化还原引发剂体系也是合适的。所用过氧化物原则上可以是无机过氧化物,如过氧化氢或过氧二硫酸盐,如过氧二硫酸的单-或二-碱金属或铵盐,如它们的单-和二-钠、钾或铵盐,或有机过氧化物如氢过氧化烷基,实例是氢过氧化叔丁基、对基和枯基,还有过氧化二烷基或二酰基,如过氧化二叔丁基或过氧化二枯基。作为偶氮化合物基本使用2,2′-偶氮二(异丁腈)、2,2′-偶氮二(2,4-二甲基戊腈)和2,2′-偶氮二(脒基丙基)二盐酸盐(AIBA,对应于Wako Chemicals的V-50)。氧化还原引发剂体系的合适氧化剂基本包括上述过氧化物。作为对应的还原剂可以使用具有低氧化态的硫化合物,例如碱金属亚硫酸盐,实例是亚硫酸钾和/或钠,碱金属亚硫酸氢盐,实例是亚硫酸氢钾和/或钠,碱金属偏亚硫酸氢盐,实例是偏亚硫酸氢钾和/或钠,甲醛-次硫酸盐,实例是甲醛-次硫酸钾和/或钠,脂族亚磺酸的碱金属盐,尤其是钾盐和/或钠盐,以及碱金属氢硫化物如氢硫化钾和/或钠,多价金属的盐如硫酸铁(II)、硫酸铵铁(II)、磷酸铁(II),烯二醇如二羟基马来酸、苯偶姻和/或抗坏血酸,以及还原性糖如山梨糖、葡萄糖、果糖和/或二羟基丙酮。自由基引发剂的用量基于总单体量通常为0.01-5重量%,优选0.1-3重量%,更优选0.2-1.5重量%。
按照本发明,可以在引发聚合反应之前将全部自由基引发剂包括在含水反应介质中的初始进料中。另一可能性是在引发聚合反应之前,合适的话仅将一部分自由基引发剂包括在含水反应介质中的初始进料中,然后在聚合条件下以其在本发明的自由基乳液聚合过程中的消耗速率加入全部量或合适的话剩余量,该加料连续或断续进行。
引发聚合反应是指由自由基引发剂形成自由基而开始存在于聚合容器中的单体的聚合反应。就此而言,可以通过在聚合条件下将自由基引发剂加入聚合容器中的含水聚合混合物中而引发聚合反应。另一方案是在不适合引发聚合反应的条件下,例如在低温下将部分或所有自由基引发剂加入包含初始单体进料的聚合容器中的含水聚合混合物中,然后在含水聚合混合物中设定聚合条件。就此而言,聚合条件通常是指自由基引发的水乳液聚合以足够聚合速率在其下进行的那些温度和压力。它们尤其取决于所用自由基引发剂。有利的是对自由基引发剂的性质和量、聚合温度和聚合压力都进行选择,以使自由基引发剂的半衰期≤3小时,特别有利的是≤1小时,非常特别有利的是≤30分钟,同时总是存在足够的引发自由基以引发或维持聚合反应。
本发明的自由基水乳液聚合的合适反应温度包括0-170℃的整个范围。所用温度通常为50-120℃,经常为60-110℃,常常为70-100℃。本发明的自由基水乳液聚合可以在小于、等于或大于1巴(绝对)的压力下进行,聚合温度因此可以超过100℃并达到170℃。高度挥发性单体如2-甲基丁-1-烯、3-甲基丁-1-烯、2-甲基丁-2-烯、丁二烯或氯乙烯优选在超级大气压下聚合。该压力可以取1.2、1.5、2、5、10或15巴或甚至更高的值。当乳液聚合在低于一大气压的压力下进行时,设定950毫巴,通常为900毫巴,常常为850毫巴(绝对)的压力。例如,本发明的自由基水乳液聚合有利地在1大气压(1.013绝对巴)下在惰性气体气氛如氮气或氩气下进行。
含水反应介质原则上还可以包含水溶性有机溶剂如甲醇、乙醇、异丙醇、丁醇、戊醇,以及丙酮等。然而,优选本发明方法在不存在该类溶剂下进行。
除了上述组分外,还可以在本发明方法中任选使用自由基链转移化合物以降低或控制可以通过聚合得到的聚合物的分子量。就此而言,合适的化合物基本包括脂族和/或芳脂族卤素化合物,如正丁基氯、正丁基溴、正丁基碘、二氯甲烷、二氯乙烷、氯仿、溴仿、一溴三氯甲烷、二溴二氯甲烷、四氯化碳、四溴化碳、苄基氯、苄基溴,有机硫代化合物,如伯、仲或叔脂族硫醇,如乙硫醇、正丙硫醇、2-丙硫醇、正丁硫醇、2-丁硫醇、2-甲基-2-丙硫醇、正戊硫醇、2-戊硫醇、3-戊硫醇、2-甲基-2-丁硫醇、3-甲基-2-丁硫醇、正己硫醇、2-己硫醇、3-己硫醇、2-甲基-2-戊硫醇、3-甲基-2-戊硫醇、4-甲基-2-戊硫醇、2-甲基-3-戊硫醇、3-甲基-3-戊硫醇、2-乙基丁硫醇、2-乙基-2-丁硫醇、正庚硫醇及其异构体、正辛硫醇及其异构体、正壬硫醇及其异构体、正癸硫醇及其异构体、正十一烷硫醇及其异构体、正十二烷硫醇及其异构体、正十三烷硫醇及其异构体,取代硫醇如2-羟基乙硫醇,芳族硫醇如苯硫酚,邻-、间-或对-甲基苯硫酚,以及所有在PolymerHandbook,第3版,1989,J.Brandrup和E.H.Immergut,John Wiley &Sons,第II节,第133-41页中描述的其他硫化合物,还有脂族和/或芳族醛如乙醛、丙醛和/或苯甲醛,不饱和脂肪酸如油酸,含有非共轭双键的二烯烃如二乙烯基甲烷或乙烯基环己烷,或具有易于遮断的氢原子的烃类如甲苯。然而,还可以使用互相相容的上述自由基链转移化合物的混合物。
任选在本发明方法中使用的自由基链转移化合物的总量基于总单体量通常≤5重量%,经常≤3重量%,常常≤1重量%。
有利的是在引发自由基聚合之前将一部分或全部的任选使用的自由基链转移化合物供入反应介质中。此外,还可以有利地在聚合过程中将一部分或全部自由基链转移化合物与单体B-D一起供入含水反应介质中。
可由本发明方法得到的聚合物原则上可以具有的玻璃化转变温度为-70℃至150℃,通常为-30℃至+100℃,常常为-20℃至+50℃。当将聚合物水分散体用于制备粘合剂,尤其是压敏粘合剂时,选择单体A-D以使所得聚合物的玻璃化转变温度Tg≤+20℃。通常选择单体A-D以形成Tg≤+10℃,≤0℃,≤-10℃,≤-20℃,≤-30℃,≤-40℃或≤-50℃的聚合物。然而,还可以制备玻璃化转变温度为-70℃至+10℃,-60℃至-10℃或-50℃至-20℃的聚合物。玻璃化转变温度这里是指根据ASTM D3418-82由差示热分析(DSC)测定的中点温度[还参见Ullmann′sEncyclopedia of Industrial Chemistry,第169页,Verlag Chemie,Weinheim,1992以及Zosel,Farbe und Lack,82,第125-34页,1976]。
根据Fox(T.G.Fox,Bull.Am.Phys.Soc.1956[Ser.II]1,第123页并按照Ullmann′s der technischen Chemie,第19卷,第18页,第4版,Verlag Chemie,Weinheim,1980),通过以下方程以良好近似给出仅具有低交联度的共聚物的玻璃化转变温度:
1/Tg=x1/Tg 1+x2/Tg 2+....xn/Tg n,
其中x1、x2、....、xn为单体1、2、....、n的质量分数且Tg 1、Tg 2、....、Tg n为在每种情况下仅由单体1、2、....、n之一合成的聚合物的玻璃化转变温度,以开氏温标表示。这些均聚物的玻璃化转变温度对大多数烯属不饱和单体是已知的(或者可以容易地以常规方式通过试验确定)并且例如列于J.Brandrup,E.H.Immergut,Polymer Handbook,第1版,J.Wiley,NewYork,1966,第2版,J.Wiley,New York,1975和第3版,J.Wiley,New York,1989以及Ullmann′s Encyclopedia of Industrial Chemistry,第169页,Verlag Chemie,Weinheim,1992中。
任选自由基引发的水乳液聚合还可以在聚合物种子存在下进行,例如在0.01-3重量%,通常为0.02-2重量%,常常为0.04-1.5重量%的聚合物种子存在下进行,每种情况下基于单体总量。
尤其在要将借助自由基水乳液聚合制备的聚合物颗粒的粒度设定为特定的目标值时使用聚合物种子(就此例如参见US-A 2520959和US-A3397165)。
尤其使用其聚合物种子颗粒具有窄尺寸分布且重均直径Dw≤100nm,常常为≥5nm至≤50nm,经常为≥15nm至≤35nm的聚合物种子。重均粒径的测定对熟练技术人员是已知的且例如通过分析超离心方法完成。重均粒径在本文中是指由分析超离心方法测定的重均Dw50值(就此而言参见S.E.Harding等,Analytical Ultracentrifugation in Biochemistry andPolymer Science,Royal Society of Chemistry,Cambridge,Great Britain1992,第10章,Analysis of Polymer Dispersions with an Eight-Cell AUCMultiplexer:High Resolution Particle Size Distribution and DensityGradient Techniq ues,W.,第147-75页)。
当由分析超离心方法测定的重均粒径Dw50与数均粒径Dn50之比[Dw50/Dn50]为≤2.0,优选≤1.5,更优选≤1.2或≤1.1时,对本文而言存在窄粒度分布。
该聚合物种子通常以聚合物水分散体形式使用。上述值指聚合物种子水分散体的聚合物固体分数;它们因此以基于单体总量的聚合物种子固体重量份数给出。
若使用聚合物种子,则有利的是使用外来聚合物种子。与在开始乳液聚合之前在反应容器中制备并且与通过随后的自由基引发的水乳液聚合制备的聚合物具有相同单体组成的就地聚合物种子不同的是,外来聚合物种子是在单独的反应步骤中制备且其单体组成与自由基引发的水乳液聚合制备的聚合物不同的聚合物种子,但这意味着只不过使用不同单体或具有不同组成的单体混合物来制备外来聚合物种子和制备聚合物水分散体。外来聚合物种子的制备被熟练技术人员所熟知且通常通过将较少量的单体和较大量的乳化剂作为初始进料引入反应容器中并在反应温度下加入足够量的聚合引发剂而完成。
按照本发明优选使用玻璃化转变温度为≥50℃,通常≥60℃或≥70℃,常常≥80℃或≥90℃的外来聚合物种子。特别优选聚苯乙烯或聚甲基丙烯酸甲酯聚合物种子。
全部量的外来聚合物种子可以与单体A一起包括在聚合容器的初始进料中。另一方案是仅将一部分外来聚合物种子与单体A一起包括在聚合容器的初始进料中,并在聚合过程中将剩余量与单体B-D一起加入。然而,需要的话可以在聚合过程中加入全部量的聚合物种子。优选在聚合反应的引发开始之前将全部量的外来聚合物种子包括在聚合容器的初始进料中。
可按照本发明得到的聚合物水分散体具有的聚合物固体含量通常为≥10重量%且≤70重量%,经常为≥20重量%且≤65重量%,常常为≥25重量%且≤60重量%,每种情况下基于聚合物水分散体。由准弹性光散射(ISO标准13321)测定的数均粒径,即累积z-均通常为10-2000nm,常常为20-1000nm,经常为100-700nm或100-400nm。
在所得聚合物水分散体中,未反应单体和其他低沸点化合物的残留量通常通过同样为熟练技术人员已知的化学和/或物理方法降低[例如参见EP-A 771328,DE-A 19624299,DE-A 19621027,DE-A 19741184,DE-A19741187,DE-A 19805122,DE-A 19828183,DE-A 19839199,DE-A19840586和19847115]。
可由本发明方法得到的聚合物水分散体的特征是在相同聚合时间下显著更高的单体转化率或聚合反应完成后更高的聚合物固体含量。
可由本发明方法得到的聚合物水分散体尤其可以用于生产粘合剂、密封剂、聚合物打底剂、纸张涂料、纤维网、油漆和有机基材如皮革或纺织品用涂料,以及用于改性矿物粘合剂的涂料。
在它们的粘合剂应用中,特别是作为压敏粘合剂,优选将可按照本发明方法得到的聚合物水分散体与增粘剂,即增粘树脂混合。增粘剂例如由Adhesives Age,1987年7月,第19-23页或Polym.Mater.Sci.Eng.61(1989),第588-92页已知。
增粘剂例如为天然树脂,如松香或由岐化或异构化、聚合、二聚或氢化得到的其衍生物。它们可以其盐形式存在(例如带有一价或多价反离子[阳离子])或优选以其酯化形式存在。用于酯化的醇可以是一元醇或多元醇。实例是甲醇、乙二醇、二甘醇、三甘醇、1,2,3-丙三醇(甘油)或季戊四醇。
此外还使用烃树脂,实例是香豆酮-茚树脂,聚萜烯树脂,基于不饱和CH化合物如丁二烯、戊烯、甲基丁烯、异戊二烯、戊间二烯、二乙烯基甲烷、戊二烯、环戊烯、环戊二烯、环己二烯、苯乙烯、α-甲基苯乙烯或乙烯基甲苯的烃树脂。
正逐渐被用作增粘剂的其他化合物是低分子量聚丙烯酸酯。这些聚丙烯酸酯优选的重均分子量低于30000g/mol。所述聚丙烯酸酯优选由至少60重量%,尤其至少80重量%的丙烯酸或甲基丙烯酸的C1-C8烷基酯组成。
优选增粘剂为天然或化学改性的松香。松香主要由枞酸或其衍生物组成。
增粘剂可以简单方式加入可以按照本发明得到的聚合物水分散体中。增粘剂优选本身呈含水悬浮液形式。
增粘剂的量优选为5-100重量%,特别是10-50重量%,每种情况下基于聚合物总量(固体/固体)。
除了增粘剂外,应理解的是在配制压敏粘合剂时还可以使用其他常规添加剂,实例是增稠剂、消泡剂、增塑剂、颜料、润湿剂或填料。
聚合物水分散体可以通过常规方法如辊涂、刀涂、铺展等施用于基材如纸张或例如优选由聚乙烯、可能已经双轴或单轴取向的聚丙烯、聚对苯二甲酸乙二醇酯、聚氯乙烯、聚苯乙烯、聚酰胺组成的聚合物带和聚合物膜或金属表面上。水可以通过在50-150℃下干燥而容易地除去。对于后续应用,可以用防粘纸如硅化纸对涂有压敏粘合剂的基材如标签或带的一侧进行衬里。
可由本发明方法得到的聚合物水分散体有利地适合作为粘合剂,尤其是压敏粘合剂中的组分。本发明的这些粘合剂有利地呈现出对塑料表面,尤其是聚乙烯表面的改进粘合性。
下列非限制性实施例用于说明本发明。
实施例
在20-25℃(室温)和氮气下向装有锚式搅拌器、回流冷凝器和两个计量装置的4升四颈烧瓶中加入970g去离子水、42.4g含水聚苯乙烯种子(固体含量为33重量%,数均粒径为32nm)、212g辛-1-烯、12.3g来自Lanxess,Leverkusen的浓度为40重量%的Emulgator 乳化剂水溶液(平均链长为15个碳原子的伯和仲烷基磺酸钠的混合物)和1.5g过硫酸钠并在搅拌下将该初始进料加热到90℃。在达到该温度之后,同时开始加入由600g去离子水、12.3g浓度为40重量%的Emulgator 水溶液、11.2g浓度为25重量%的氢氧化钠水溶液、1184g丙烯酸正丁酯和5.6g甲基丙烯酸烯丙基酯组成的单体进料以及由110g去离子水和8.3g过硫酸钠组成的引发剂进料,其中单体进料在3小时内连续计量加入,而引发剂进料在3.5小时内连续计量加入。然后使所得聚合物水分散体在冷却至室温之前在90℃下后反应2小时。所得聚合物水分散体的固体含量基于聚合物水分散体的总重量为45重量%。该聚合物的玻璃化转变温度为-47℃。
通过在干燥箱中于140℃下将确定量的聚合物水分散体(约5g)干燥到恒重而测定固体含量。进行两次单独的测量。实施例中所记录的值表示这两个结果的平均值。
按照DIN 53765使用来自Mettler-Toledo的TA 8000系列DSC 820仪器测定玻璃化转变温度。
对比例
以与本发明实施例相同的方式进行该对比例,但不同在于全部量的212g辛-1-烯与单体进料一起计量加入。所得聚合物水分散体的固体含量基于聚合物水分散体的总重量为40重量%。该聚合物的玻璃化转变温度为-44℃。
Claims (10)
1.一种通过烯属不饱和单体在至少一种分散剂和至少一种自由基引发剂存在下的自由基引发的水乳液聚合而制备聚合物水分散体的方法,其中将
1-50重量%具有5-12个碳原子的链烯烃[单体A],和
50-99重量%基于具有3-6个碳原子的α,β-单烯属不饱和单羧酸或二羧酸和具有1-12个碳原子的链烷醇的酯[单体B],以及合适的话,
0-10重量%具有3-6个碳原子的α,β-单烯属不饱和单羧酸或二羧酸和/或其酰胺[单体C],和
0-30重量%不同于单体A-C的α,β-烯属不饱和化合物[单体D],
用于乳液聚合,其中单体A-D加起来为100重量%,其中在引发聚合反应之前将单体A的总量中至少50重量%和任选全部量的单体B-D中各自至多10重量%包括在聚合容器的初始进料中,并且在聚合条件下将任何剩余的单体A以及全部量或合适的话剩余的单体B-D供入聚合容器中。
2.根据权利要求1的方法,其中使用
1-49.99重量%单体A,
50-98.99重量%单体B,和
01-10重量%单体C。
3.根据权利要求1或2的方法,其中将1-链烯烃用作单体A。
4.根据权利要求1-3中任一项的方法,其中将基于具有3或4个碳原子的α,β-单烯属不饱和单羧酸或二羧酸和具有1-8个碳原子的链烷醇的酯用作单体B。
5.根据权利要求1-4中任一项的方法,其中将具有6-8个碳原子的链烯烃用作单体A。
6.根据权利要求1-5中任一项的方法,其中在引发聚合反应之前将单体A的总量中至少80重量%包括在聚合容器的初始进料中。
7.根据权利要求1-6中任一项的方法,其中在引发聚合反应之前将全部量的单体A包括在聚合容器的初始进料中。
8.根据权利要求1-7中任一项的方法,其中在聚合条件下将全部量或合适的话剩余的单体B-D以恒定流速连续计量加入聚合容器中。
9.根据权利要求1-8中任一项的方法,其中在聚合条件下将全部量或合适的话剩余的单体B-D以单体混合物计量加入聚合容器中。
10.根据权利要求9的方法,其中以单体水乳液形式将全部量或合适的话剩余的单体B-D计量加入聚合容器中。
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JP3592408B2 (ja) * | 1995-07-25 | 2004-11-24 | 旭電化工業株式会社 | 界面活性剤、乳化重合用乳化剤、懸濁重合用分散剤及び樹脂改質剤 |
WO2001029091A1 (de) * | 1999-10-19 | 2001-04-26 | Südzucker Aktiengesellschaft Mannheim/Ochsenfurt | Emulsionspolymerisationsverfahren |
JP4281531B2 (ja) * | 2003-11-26 | 2009-06-17 | Jsr株式会社 | 中空重合体粒子およびその水性分散体並びに製造方法 |
DE102005035692A1 (de) * | 2005-07-27 | 2007-02-01 | Basf Ag | Verfahren zur Herstellung einer wässrigen Polymerisatdispersion |
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- 2007-03-28 DE DE502007001137T patent/DE502007001137D1/de active Active
- 2007-03-28 EP EP07727426A patent/EP2004701B1/de not_active Not-in-force
- 2007-03-28 AT AT07727426T patent/ATE437187T1/de active
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101538345A (zh) * | 2009-02-05 | 2009-09-23 | 上海华谊(集团)公司 | 树枝状高支化聚合物、制备方法及用途 |
CN102471418A (zh) * | 2009-06-30 | 2012-05-23 | 路博润高级材料公司 | 复合聚合物乳液 |
CN102781594A (zh) * | 2009-12-11 | 2012-11-14 | 瓦克化学股份公司 | 具有延展性的矿物粘合涂层的生产 |
CN108473625A (zh) * | 2015-12-17 | 2018-08-31 | Sabic环球技术有限责任公司 | 乙烯共聚物及其生产方法 |
CN108473625B (zh) * | 2015-12-17 | 2020-12-22 | Sabic环球技术有限责任公司 | 乙烯共聚物及其生产方法 |
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WO2007113180A1 (de) | 2007-10-11 |
EP2004701B1 (de) | 2009-07-22 |
ES2328184T3 (es) | 2009-11-10 |
DE502007001137D1 (de) | 2009-09-03 |
EP2004701A1 (de) | 2008-12-24 |
US20100152380A1 (en) | 2010-06-17 |
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