CN1311798A - 制备粉状交联聚合物的方法 - Google Patents
制备粉状交联聚合物的方法 Download PDFInfo
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- CN1311798A CN1311798A CN99809072A CN99809072A CN1311798A CN 1311798 A CN1311798 A CN 1311798A CN 99809072 A CN99809072 A CN 99809072A CN 99809072 A CN99809072 A CN 99809072A CN 1311798 A CN1311798 A CN 1311798A
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- Prior art keywords
- monomer
- acid
- polymkeric substance
- methyl
- polymerization
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- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 239000000178 monomer Substances 0.000 claims abstract description 42
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
- 125000002091 cationic group Chemical group 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 5
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 claims description 4
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims description 4
- 239000003701 inert diluent Substances 0.000 claims description 3
- 239000012752 auxiliary agent Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract description 16
- 239000001569 carbon dioxide Substances 0.000 abstract description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- 239000003085 diluting agent Substances 0.000 abstract 1
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000010526 radical polymerization reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
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- 229920000642 polymer Polymers 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YBXHSDOJCKEVRI-UHFFFAOYSA-N C(=C)C=1NC=CN1.CC1(CC(C(=O)O)=CC=C1)C(=O)O Chemical compound C(=C)C=1NC=CN1.CC1(CC(C(=O)O)=CC=C1)C(=O)O YBXHSDOJCKEVRI-UHFFFAOYSA-N 0.000 description 3
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- 125000001931 aliphatic group Chemical group 0.000 description 3
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000005451 methyl sulfates Chemical class 0.000 description 3
- 230000005588 protonation Effects 0.000 description 3
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 229920001567 vinyl ester resin Polymers 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 2
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical class C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- QGFSQVPRCWJZQK-UHFFFAOYSA-N 9-Decen-1-ol Chemical compound OCCCCCCCCC=C QGFSQVPRCWJZQK-UHFFFAOYSA-N 0.000 description 2
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- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
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- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
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- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
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- 239000000376 reactant Substances 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
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- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- AKRQMTFHUVDMIL-UHFFFAOYSA-N tetrakis(prop-2-enyl)silane Chemical group C=CC[Si](CC=C)(CC=C)CC=C AKRQMTFHUVDMIL-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C08F226/00—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
- C08F226/10—N-Vinyl-pyrrolidone
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Abstract
本发明涉及制备以含有季铵化或可季铵化氮原子的单烯属不饱和单体为基础的粉状阳离子交联聚合物的方法。本发明方法的特征在于聚合是在作为惰性稀释剂的超临界二氧化碳中通过在31℃-150℃和73巴以上的压力下充分混合而进行的。
Description
本发明涉及在超临界二氧化碳中通过自由基聚合制备粉状阳离子交联聚合物的方法,所述聚合物是以含有季铵化或可季铵化氮原子的单烯属不饱和单体为基础的。
一般而言已知超临界二氧化碳可用作自由基聚合制备聚合物中的溶剂。例如,EP-A220603描述了在超临界二氧化碳中通过自由基聚合制备基于N-乙烯基单体和/或单烯属不饱和羧酸酯的非交联粉状聚合物的方法。EP-A239035描述了通过在超临界二氧化碳中聚合制备基于单烯属不饱和羧酸、或其酰胺和/或酯的交联粉状聚合物的方法。在已知的方法中,一般将反应混合物和液态二氧化碳引入到加压容器中,通过升高温度和压力诱导超临界状态。但是,此处不利的是单体和交联剂在溶剂中不同的溶解度意谓着会形成不均匀形态或不均匀化学组成的产物。
本发明的目的是寻找一种改进的制备交联聚合物的方法。
我们已经发现此目的可通过自由基引发聚合制备粉状阳离子交联聚合物的方法实现,所述聚合物是以含有季铵化或可季铵化氮原子的单烯属不饱和单体为基础的,所述方法包括在作为惰性稀释剂的超临界二氧化碳中于31-150℃和73巴以上压力下混合进行聚合。
聚合在作为惰性稀释剂的超临界二氧化碳中加压进行。二氧化碳在液态和超临界状态的性质已由J.A.Hyatt,J.Org.Chem.49,(1984),5097-5101报道。根据该论文,二氧化碳的临界点在约31℃和73巴。聚合优选在超临界二氧化碳中于约31℃,即二氧化碳的临界温度之上加压进行。制备聚合物的温度上限为比所形成的各聚合物软化起始点高10℃。对于多数聚合物,该温度上限值为150℃。聚合优选在30-130℃进行。反应温度不必保持恒定;也可以建立梯度或直线上升的温度曲线。建议在反应开始时将温度设置在31-100℃。压力为73巴以上,优选为80-300巴,特别优选为120-250巴。
新方法优选通过下列步骤进行:首先将固态、液态或气态二氧化碳引入到本身为常规加压装置的反应空间,然后通过将压力升高到73巴以上并将温度升高到31℃以上而将二氧化碳转化为超临界状态,其后固定反应温度,并随后计量加入起始原料。可将起始原料,如单体、自由基引发剂、交联剂和,如果需要的话,聚合调节剂分别加入或以混合物形式加入。因此,建议例如将自由基引发剂溶解在单体中。所选方法主要依赖于各组分彼此及在稀释剂中的溶解性。但是,也可以将全部或一些起始原料引入到反应空间中并随后加入二氧化碳。如果需要,起始原料可以在反应期间计量加入(半分批法)。
通过分解形成自由基的聚合引发剂引发聚合反应。可以使用所有已知用于单体聚合的引发剂,例如在所选温度分解形成半衰期小于3小时的自由基的引发剂。如果聚合在不同温度进行,即单体在低温开始聚合而在明显更高的温度结束聚合,则使用至少两种在各情况的所选温度范围内具有适当分解速率的不同引发剂是有利的。
以100重量份单体混合物为基准,使用100-3000重量份,优选200-1500重量份二氧化碳。二氧化碳优选是无水的。聚合反应可分批或连续进行,反应物的混合在适当设计的加压装置中进行。为了驱散聚合期间形成的热,要求加压装置带有冷却系统。当然它们还必须是可加热的以将反应混合物加热到聚合所需要的各温度。加压装置应该带有混合装置,例如搅拌器(叶片式、叶轮式、多段脉冲逆流式或条带式搅拌器)或叶轮。
新方法特别适于制备粉状阳离子交联聚合物。
这些粉状阳离子交联聚合物是通过自由基引发聚合下列单体而获得的:
(a1)1-99.99wt%含有季铵化或可季铵化氮原子的可自由基聚合单体,或这种单体的混合物,
(a2)5-95wt%N-乙烯基内酰胺,
(b)0.01-20wt%进行交联的单体,和
(c)0-50wt%其它可自由基共聚的单体。
适宜的单体(a1)选自下列基团之一:
在根据本发明的聚合条件下,这种二烯丙基胺发生关环反应:-式(Ⅲ)丙烯酸或甲基丙烯酸的N,N-二烷基氨基烷基衍生物其中R5和R6彼此独立地为氢或甲基,x=0时Z为氮原子,R7为线性或支化C1-C24-亚烷基基团,而R8和R9彼此独立地为C1-C24-烷基基团。
适宜的式(Ⅲ)单体为例如N,N-二甲基氨基甲基(甲基)丙烯酸酯、N,N-二乙基氨基甲基(甲基)丙烯酸酯、N,N-二甲基氨基乙基(甲基)丙烯酸酯、N,N-二乙基氨基乙基(甲基)丙烯酸酯、N,N-二甲基氨基丁基(甲基)丙烯酸酯、N,N-二乙基氨基丁基(甲基)丙烯酸酯、N,N-二甲基氨基己基(甲基)丙烯酸酯、N,N-二甲基氨基辛基(甲基)丙烯酸酯、N,N-二甲基氨基十二烷基(甲基)丙烯酸酯、N-[3-(二甲基氨基)丙基]丙烯酰胺、N-[3-(二甲基氨基)丁基]甲基丙烯酰胺、N-[8-(二甲基氨基)辛基]甲基丙烯酰胺、N-[12-(二甲基氨基)十二烷基]甲基丙烯酰胺、N-[3-(二乙基氨基)丙基]甲基丙烯酰胺和N-[3-(二乙基氨基)丙基]丙烯酰胺、及其混合物。
优选的单体(a1)为3-甲基-1-乙烯基咪唑鎓氯化物和甲硫酸盐、二甲基二烯丙基氯化铵、和N,N-二甲基氨基乙基甲基丙烯酸酯及N-[3-(二甲基氨基)丙基]甲基丙烯酰胺,如果需要,每一个都可被氯代甲烷、硫酸二甲酯或硫酸二乙酯季铵化。
特别优选的单体(a1)为3-甲基-1-乙烯基咪唑鎓氯化物和甲硫酸盐及二甲基二烯丙基氯化铵;非常特别优选的单体(a1)为3-甲基-1-乙烯基咪唑鎓氯化物和甲硫酸盐。
也可以使用单体(a1)的混合物。
优选使用5-70wt%,特别优选10-50wt%的单体(a1)。
单体(a1)可作为季铵化形式的单体使用或者以未季铵化形式聚合;在后一种情况下,所得共聚物是季铵化或质子化的。如果单体以季铵化形式使用,则它们可作为干燥物质或以在适合这些单体的溶剂例如极性溶剂如水、甲醇、乙醇、丙酮或电解质溶液中的浓溶液形式被使用。
可通过使用下列物质进行质子化反应:例如使用无机酸如HCl、H2SO4,或一元羧酸如甲酸或乙酸,二元羧酸或多元羧酸如草酸或柠檬酸,或可将相应氮原子质子化的任何其它释放质子的化合物或物质。水溶性酸特别适于进行质子化。
聚合物的质子化反应可在聚合之后或配制化妆品制剂期间进行,在此期间一般要建立生理上相容的pH。
术语质子化反应用来表示至少聚合物的一些可质子化基团,优选20-100%被质子化,得到带阳离子总电荷的聚合物。
式(Ⅰ)-(Ⅲ)化合物的季铵化反应是使用下列物质进行的:例如使用烷基基团中含有1-24个碳原子的烷基卤化物,例如氯代甲烷、溴甲烷、碘甲烷、氯乙烷、溴乙烷、氯丙烷、氯己烷、氯代十二烷、月桂基氯化物或苄基卤化物,特别是氯化苄或溴化苄。其它适宜的季铵化试剂为硫酸二烷基酯,特别是硫酸二甲酯或硫酸二乙酯。式(Ⅰ)-(Ⅲ)碱性单体的季铵化反应也可使用氧化烯,如环氧乙烷或环氧丙烷在酸存在下进行。
使用所述季铵化试剂中的一种进行的单体或聚合物的季铵化反应可通过通常已知的方法进行。
优选的季铵化试剂为氯代甲烷、硫酸二甲酯和硫酸二乙酯。
适宜的单体(a2)为N-乙烯基内酰胺,例如N-乙烯基哌啶酮、N-乙烯基吡咯烷酮和N-乙烯基己内酰胺,优选N-乙烯基吡咯烷酮。
适宜的交联剂(单体(b))为例如丙烯酸酯类、甲基丙烯酸酯类、烯丙基醚类和至少二羟基醇的乙烯基醚类。母体醇的一些或全部OH基团可被醚化或酯化;但是,交联剂包含至少两个烯属不饱和基团。
母体醇的实例为二羟基醇,如1,2-乙二醇、1,2-丙二醇、1,3-丁二醇、2,3-丁二醇、1,4-丁二醇、2-丁烯-1,4-二醇、1,2-戊二醇、1,5-戊二醇、1,2-己二醇、1,5-己二醇、1,10-癸二醇、1,2-十二碳二醇、1,12-十二碳二醇、新戊二醇、3-甲基-1,5-戊二醇、2,5-十二碳二醇、1,12-十二碳二醇、新戊二醇、3-甲基戊-1,5-二醇、2,5-二甲基-1,3-己二醇、2,2,4-三甲基-1,3-戊二醇、1,2-环己二醇、1,4-环己二醇、1,4-二(羟甲基)环己烷、羟基新戊酸新戊二醇酯、2,2-二(4-羟基苯基)丙烷、2,2-二[4-(2-羟基丙基)苯基]丙烷、二甘醇、三甘醇、四甘醇、双丙甘醇(dipropylene glycol)、三丙甘醇(tripropylene glycol)、四丙甘醇(tetrapropylene glylcol)、3-硫代-1,5-戊二醇、和分子量为200-10,000的聚乙二醇、聚丙二醇及聚四氢呋喃。除了环氧乙烷或环氧丙烷均聚物外,还可使用环氧乙烷或环氧丙烷的嵌段共聚物或含有引入的环氧乙烷或环氧丙烷基团的共聚物。含有两个以上OH基团的母体醇的实例为三羟甲基丙烷、丙三醇、季戊四醇、1,2,5-戊三醇、1,2,6-己三醇、三乙氧基氰尿酸、脱水山梨糖醇、糖如蔗糖、葡萄糖和甘露糖。当然也可以使用与环氧乙烷或环氧丙烷反应完后相应的乙氧基化物或丙氧基化物的多羟基醇。通过与表氯醇反应也可将多羟基醇首先转化成相应的缩水甘油醚。
其它适宜的交联剂为单羟基不饱和醇与烯属不饱和C3-C6-羧酸如丙烯酸、甲基丙烯酸、衣糠酸、马来酸或富马酸的乙烯基酯或酯。这种醇的实例为烯丙基醇、1-丁烯-3-醇、5-己烯-1-醇、1-辛烯-3-醇、9-癸烯-1-醇、二环戊烯醇、10-十一烯-1-醇、肉桂醇、香茅醇、巴豆醇或顺式-9-十八烯-1-醇。但是,也可以使用多元羧酸,例如丙二酸、酒石酸、偏苯三酸、邻苯二甲酸、对苯二甲酸、柠檬酸或琥珀酸来酯化单羟基不饱和醇。
所用交联剂也可为不饱和羧酸与上述多羟基醇的酯,所述羧酸为例如油酸、巴豆酸、肉桂酸或10-十一烯酸。
同样适宜的为含有至少两个双键的直链或支链、线性或环形、脂族或芳族烃,在脂族烃的情况中双键不能是共轭的,例如二乙烯基苯、二乙烯基甲苯、1,7-辛二烯、1,9-癸二烯、4-乙烯基-1-环己烯、三乙烯基环己烷或分子量为200-20,000的聚丁二烯。
其它适宜的交联剂为丙烯酰胺、甲基丙烯酰胺和至少双官能团胺的N-烯丙基胺。这种胺的实例为1,2-二氨基甲烷、1,2-二氨基乙烷、1,3-二氨基丙烷、1,4-二氨基丁烷、1,6-二氨基己烷、1,12-十二烷二胺、哌嗪、二亚乙基三胺或异佛尔酮二胺。同样适宜的为由烯丙基胺和不饱和羧酸如丙烯酸、甲基丙烯酸、衣糠酸、马来酸或上述的至少二元羧酸制备的酰胺。
另外,三烯丙基胺和三烯丙基单烷基铵盐,例如三烯丙基甲基氯化铵或硫酸甲酯适宜作交联剂。
同样适宜的为脲衍生物、至少双官能团酰胺、氰脲酸酯或聚氨酯,例如脲、亚乙基脲、亚丙基脲或酒石酰胺的N-乙烯基化合物,例如N,N’-二乙烯基亚乙基脲或N,N’-二乙烯基亚丙基脲。
同样适宜的为亚烷基双丙烯酰胺,例如亚甲基双丙烯酰胺和1,1’-双(2,2’-和1,1’-双(3,3’-乙烯基苯并咪唑-2-酮)-1,4-丁烷。
其它适宜交联剂的实例为二(甲基)丙烯酸亚烷基二醇酯,如二丙烯酸乙二醇酯、二甲基丙烯酸乙二醇酯、二丙烯酸四甘醇酯、二甲基丙烯酸四甘醇酯、二丙烯酸二甘醇酯、二甲基丙烯酸二甘醇酯、丙烯酸乙烯酯、丙烯酸烯丙酯、甲基丙烯酸烯丙酯、二乙烯基二氧六环、季戊四醇三烯丙基醚及这些交联剂的混合物。
其它适宜的交联剂为四烯丙基硅烷和四乙烯基硅烷。
特别优选的交联剂的实例为亚甲基双丙烯酰胺、三烯丙基胺和三烯丙基烷基铵盐、二乙烯基咪唑、N,N’-二乙烯基亚乙基脲、多羟基醇与丙烯酸或甲基丙烯酸的反应产物、聚亚烷基氧或已与环氧乙烷和/或环氧丙烷和/或表氯醇反应的多羟基醇的甲基丙烯酸酯和丙烯酸酯。非常特别优选的交联剂为亚甲基双丙烯酰胺、N,N’-二乙烯基亚乙基脲和乙二醇、丁二醇、三羟甲基丙烷或丙三醇的丙烯酸酯或与环氧乙烷和/或表氯醇反应的乙二醇、丁二醇、三羟甲基丙烷或丙三醇的丙烯酸酯。
交联剂在反应介质中是特别易溶的。如果交联剂在反应介质中的溶解度低,则可将其溶解在单体或单体混合物中或者溶解在与反应介质可混溶的溶剂中而计量进样。特别优选可溶于单体混合物中的交联剂。
交联剂的含量可在很大程度上影响新聚合物的溶液粘度。
另外的可自由基聚合单体(c)可为下列化合物:
N-乙烯基乙酰胺、N-甲基-N-乙烯基乙酰胺、丙烯酰胺、甲基丙烯酰胺、N,N-二甲基丙烯酰胺、N-羟甲基甲基丙烯酰胺、N-乙烯基甲酰胺、N-乙烯基噁唑烷酮和N-乙烯基三唑。单体(c)组包括例如丙烯腈、甲基丙烯腈、衍生自单羟基C1-C18-醇的丙烯酸和甲基丙烯酸酯、丙烯酸和甲基丙烯酸的羟基-C2-C4-烷基酯、马来酸酐、乙烯基酯、2-丙烯酰氨基-2-甲基丙磺酸和/或乙烯基磷酸。同样适宜的为丙烯酸和甲基丙烯酸与脂肪醇乙氧基化物和脂肪醇丙氧基化物的酯,其中脂肪醇组分含有10-20个碳原子而环氧乙烷或环氧丙烷的含量为1-20mol%。这种醇组分例如可通过使C10-C20-脂肪醇与环氧乙烷和/或环氧丙烷反应并使用丙烯酸或甲基丙烯酸酯化所得烷氧基化的脂肪醇而获得。使用这些共聚单体可得到具有高抗电解性的交联共聚物。(c)组单体以0-30wt%,优选最多15wt%的量使用。如果它们用于改性来自(a)和(b)的共聚物,则以单体混合物为基准,低限为5wt%。在所有情况下单体(a),(b)和(c)的百分含量总和为100%。丙烯酸和甲基丙烯酸的酯的实例为丙烯酸甲酯、丙烯酸乙酯、甲基丙烯酸甲酯、丙烯酸(2-乙基己基)酯、丙烯酸硬脂酯、甲基丙烯酸硬脂酯及丁基醇异构体的丙烯酸酯。适宜的丙烯酸和甲基丙烯酸的羟基-C2-C4-烷基酯为例如丙烯酸羟乙酯、丙烯酸羟丙酯、丙烯酸羟丁酯、甲基丙烯酸羟乙酯、甲基丙烯酸羟丙酯和甲基丙烯酸羟丁酯。在乙烯基酯中优选乙酸乙烯酯和丙酸乙烯酯。其它适宜的单体为烯烃,如乙烯或丙烯、苯乙烯及含有1-50个乙二醇单元的丙烯酸烷基乙二醇酯和甲基丙烯酸烷基乙二醇酯。
自由基聚合的适宜引发剂为水溶性和水不溶性过氧化物和/或偶氮化物,例如碱金属或铵过二硫酸盐、过氧化氢、过氧化苯甲酰、过新戊酸叔丁酯、2,2’-偶氮二(2,4-二甲基戊腈)、过氧新癸酸叔丁酯、过-2-乙基己酸叔丁酯、二叔丁基过氧化物、叔丁基过氧化氢、偶氮二异丁腈、偶氮二(2-脒基丙烷)二盐酸化物和2,2’-偶氮二(2-甲基丁腈)。同样适宜的为引发剂混合物或氧化还原引发剂体系,例如抗坏血酸/硫酸亚铁(Ⅱ)/过二硫酸钠、叔丁基过氧化氢/亚硫酸氢钠、和叔丁基过氧化氢/羟基甲磺酸钠。引发剂可以常规量使用,例如以待聚合单体的量为基准,为0.05-7wt%。
伴随使用氧化还原共引发剂,例如安息香、二甲苯胺及在有机溶剂中可溶解的重金属如铜、钴、锰、镍和铬且特别是铁的配合物和盐允许所述过氧化物,特别是氢过氧化物的半衰期缩短,因此,例如叔丁基氢过氧化物在5ppm乙酰丙酮合铜(Ⅱ)存在下即使是在100℃也是有效的。
优选使用微溶于水或不溶于水的引发剂。
如果需要,聚合也可在聚合调节剂存在下进行以调节聚合物的分子量。如果需要制备特别低分子量的共聚物,则要使用大量聚合调节剂,而高分子量共聚物的制备则只在很少量的聚合调节剂存在下或不存在这些物质时进行。聚合调节剂的实例为2-巯基乙醇、巯基丙醇、巯基丁醇、巯基乙酸、正十二烷基硫醇、叔十二烷基硫醇、苯硫酚、巯基丙酸、烯丙基醇和乙醛。以所用单体为基准,聚合调节剂的用量为0-10wt%,优选0-5wt%。
由新方法获得的聚合物适于用作粘度改性剂(乳化剂和分散助剂)、用作W/O和O/W乳化剂并且一般用作加工助剂、整理助剂或用作超吸收剂,另外用作清洁添加剂,如污垢和染料转移抑制剂、在造纸业中用作助留剂、在水处理中用作凝聚剂或用于食品技术领域,例如作为助滤剂或配合剂。
该聚合物还特别适于作为化妆品配方中的增稠剂和胶凝剂,尤其是用于皮肤和头发化妆品制剂,例如滋发剂、美发乳、护发素、发乳、发梢护液(tip fluids)、长效卷发剂的匀染剂、焗油剂、定型液或发胶,特别是在皮肤和头发调理剂中。
根据应用领域,头发化妆品制剂可以喷洒剂、泡沫、凝胶、凝胶喷剂或摩丝使用。
另外该聚合物适于用作药物配方中的助剂,例如作为片剂崩解剂。
根据本发明制备的聚合物为具有均匀形态并且实际上无粘结倾向的白色可自由流动粉末。
实施例
一般步骤
将二氧化碳引入高压釜成为超临界状态并通过升高压力和温度将其升至反应温度。然后以混合物形式将起始原料一次计量加入。以600rpm搅拌反应混合物。在反应器中的停留时间为10小时。然后将混合物冷却至室温并卸压,得到无凝结倾向且粒度为10-500μm的白色松散粉末。
各组成及反应条件示于下表中。每种情况下过氧自由基引发剂的用量数据是相对于脂族化合物中75wt%浓度的溶液。
表
1)溶解在1.4g水中2)溶解在2.8g水中
实施例 | 组成 | 反应压力[巴] | 反应温度[℃] |
1 | 1.5g N-甲基-N-乙烯基咪唑鎓甲硫酸盐1)13.5g N-乙烯基吡咯烷酮0.06g 三烯丙基胺0.15g 过氧新戊酸叔丁酯0.03g 2,2’-偶氮二(2-脒基丙烷)二盐酸化物155g 二氧化碳 | 160 | 60 |
2 | 3g N-甲基-N-乙烯基咪唑鎓甲硫酸盐2)13.5g N-乙烯基吡咯烷酮0.86g N-乙烯基己内酰胺0.085g二乙烯基亚乙基脲0.145g过氧新戊酸叔丁酯 | 160 | 60 |
Claims (4)
1.制备以含有季铵化或可季铵化氮原子的单烯属不饱和单体为基础的粉状阳离子交联聚合物的方法,所述方法包括在作为惰性稀释剂的超临界二氧化碳中通过在31℃-150℃和73巴以上混合而进行聚合。
2.权利要求1所要求的制备聚合物的方法,所述聚合物包括
(a1)5-99.99wt%含有季铵化或可季铵化氮原子的可自由基聚合单体,或这种单体的混合物,
(a2)5-95wt%N-乙烯基内酰胺,
(b)0.01-20wt%带有至少两个烯属不饱和基团的进行交联的单体,和
(c)0-50wt%其它可自由基聚合的单体。
3.权利要求1或2所要求的方法,其中可季铵化氮原子是通过与氯代甲烷、硫酸二甲酯或硫酸二乙酯反应而季铵化的。
4.由权利要求1-3任意一项所要求的方法获得的聚合物作为化妆品或药物配方中助剂的应用。
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DE19833287A DE19833287A1 (de) | 1998-07-24 | 1998-07-24 | Verfahren zur Herstellung von pulverförmigen vernetzten Polymerisaten |
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CN100445308C (zh) * | 2002-08-12 | 2008-12-24 | 巴斯福股份公司 | 具有调节剂的交联阳离子共聚物及其在发用化妆品制剂中的用途 |
CN105254781A (zh) * | 2015-11-19 | 2016-01-20 | 湖北鄂皖高新科技有限公司 | 一种利用超临界二氧化碳制备离聚体的方法 |
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US7837742B2 (en) * | 2003-05-19 | 2010-11-23 | The Procter & Gamble Company | Cosmetic compositions comprising a polymer and a colorant |
JP2008535954A (ja) * | 2005-03-18 | 2008-09-04 | ビーエーエスエフ ソシエタス・ヨーロピア | 水系およびアルコール系組成物用の増粘剤としてのカチオン性ポリマー |
US8247507B2 (en) | 2006-09-21 | 2012-08-21 | Basf Se | Cationic polymers as thickeners for aqueous and alcoholic compositions |
JP7132316B2 (ja) * | 2020-12-28 | 2022-09-06 | 高圧ガス工業株式会社 | 二液型硬化性組成物 |
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DE3609829A1 (de) | 1986-03-22 | 1987-09-24 | Basf Ag | Verfahren zur herstellung von pulverfoermigen vernetzten copolymerisaten |
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CN105254781A (zh) * | 2015-11-19 | 2016-01-20 | 湖北鄂皖高新科技有限公司 | 一种利用超临界二氧化碳制备离聚体的方法 |
CN105254781B (zh) * | 2015-11-19 | 2018-01-02 | 湖北鄂皖高新科技有限公司 | 一种利用超临界二氧化碳制备离聚体的方法 |
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