CN104334646B - 包含季铵基团的低粘度聚有机基硅氧烷、其生产方法和用途(ii) - Google Patents
包含季铵基团的低粘度聚有机基硅氧烷、其生产方法和用途(ii) Download PDFInfo
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- CN104334646B CN104334646B CN201380026194.6A CN201380026194A CN104334646B CN 104334646 B CN104334646 B CN 104334646B CN 201380026194 A CN201380026194 A CN 201380026194A CN 104334646 B CN104334646 B CN 104334646B
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- polyorganosiloxane
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- quaternary ammonium
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- 125000001188 haloalkyl group Chemical group 0.000 description 1
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
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Abstract
低粘度聚有机基硅氧烷,其包含:a)至少一个聚有机基硅氧烷基团,b)至少一个季铵基团,c)至少一个末端酯基,其制造方法以及它们用于使基材的表面改性的用途。
Description
相关申请的交叉引用
本申请要求2012年3月29日提交的序列号61/617,180的美国临时专利申请的优先权。
技术领域
本发明提供具有低粘度并且包含季铵基团和末端酯基的聚有机基硅氧烷、其生产方法和用途。
背景技术
有机硅季铵化物(quats)(任选含有聚有机基硅氧烷取代基的含有季铵基团的有机硅)已知为十分直接性的(substantive)。DE 3719086描述了在酸存在下α,ω-双环氧化物与叔胺的反应,得到α,ω-二季铵硅氧烷。它们可用于毛发护理目的。DE 3719086描述了四烷基衍生物以及芳族咪唑鎓衍生物。
在酸存在下α,ω-双环氧化物与二叔胺的反应得到多环聚季铵盐聚有机基硅氧烷(EP-A-282720)。这些材料的优点为改进的毛发耐洗掉性。
在酸存在下α,ω-双环氧化物与二甲基胺的反应得到在硅氧烷嵌段之间具有一个季铵(quat)基团的多环聚季铵盐聚有机基硅氧烷公开于US 6,730,766。
聚季铵盐咪唑鎓衍生物描述于US 6,240,929。在化妆品制剂中这些阳离子化合物与阴离子表面活性剂具有改进的相容性。
在有机硅季铵盐中掺入氧化烯部分是为了进一步提高亲水性。
在侧链中含有季铵基团以及聚环氧乙烷部分的有机硅季铵化物描述于US 5,098,979、US 5,153,294和US 5,166,297。材料的直接性(substantivity)相对低。
还包括聚醚部分的含有季铵官能团的基于有机硅的嵌段共聚物描述于WO 02/10257、WO 02/10259和US 2002/0103094A。氧化烯结构掺入到嵌段共聚物中作为α,ω-二官能的部分。
US 6,242,554描述了含有彼此分隔的一个聚醚官能团和一个季铵官能团的α,ω-二官能的硅氧烷衍生物。这些单季铵化物的直接性不够。
US 4,921,895描述了聚醚硅氧烷和含有季铵基团的硅氧烷嵌段共聚物的共混物,用于纺织品精整目的。此处,使用聚醚硅氧烷改进精整的货品和亲水性。
US 2007/0286837、US 2007/0041929、US 2008/0292575和CN 101198311描述了在硅氧烷链长大于200个D-单元的有机硅季铵化物和第二有机硅之间的组合,用于毛发调理目的。第二有机硅的一个可能的选择是选择源自环氧乙烷或环氧丙烷或它们的混合物的有机硅聚醚。未给出具体的结构。
上述现有技术公开均未描述用于制备包含季铵基团的低粘度聚有机基硅氧烷的直接的方法。低粘度材料将使得亲水性改进取代基(例如聚醚)的掺入变得多余或重复,因此降低系统复杂性。
发明内容
本发明提供如下被季铵基团官能化并且包含一个或多个末端酯基的低粘度有机硅(为均聚物、共聚物或三元共聚物的低聚或聚合硅氧烷):聚有机基硅氧烷化合物,所述化合物包含:
a)至少一个聚有机基硅氧烷基团,
b)至少一个季铵基团,
c)至少一个末端酯基。
本发明还提供制备本发明化合物的方法,所述方法包括以下物质的反应:
(i)至少一种二叔二胺和/或一元仲胺,
(ii)至少一种氨基-烷基化化合物,所述化合物包含至少一种双环氧化物,和
(iii)至少一种单官能的有机酸,
其中在化合物(i)和(ii)中,至少一种化合物包含聚有机基硅氧烷结构单元。
具体实施方式
本发明提供包含季铵基团的低粘度聚有机基硅氧烷、它们的制造和该物质的用途。
意外地,通过制备包含季铵基团和末端酯基的聚有机基硅氧烷化合物,实现具有低粘度的包含季铵基团的聚有机基硅氧烷。也就是,根据本发明,提供聚有机基硅氧烷化合物,所述化合物包含:
a)聚有机基硅氧烷基团,
b)季铵基团,
c)末端酯基,
其中在一种优选实施方式中,季铵基团b)与末端酯基c)的摩尔比小于100:20。
本发明的聚有机基硅氧烷化合物优选为包含上述官能团a)、b)的线性共聚物化合物(形式上[(A-B)x-A]-类型产品(其中x>1)),所述化合物中至少一部分末端基团为由使用单官能的有机酸作为链终止剂得到的末端酯基。然而,取决于反应物的化学计量学,本发明的聚有机基硅氧烷化合物还可包含得自二官能的单体与恰好一种化合物在其每一个末端的反应的化合物([(A-B)x-A]-类型产品(其中x=1))。
在一种优选实施方式中,本发明的聚有机基硅氧烷化合物不含聚氧化烯基团,在末端酯基中的聚氧化烯基团例外,特别是像以下通式的那些:
-[CH2CH2O]q-[CH2CH(CH3)O]r-[CH2CH(C2H5)O]s-
其中
q=0-200,
r=0-200,
s=0-200
并且q+r+s=1-600。
在本发明的聚有机基硅氧烷化合物的一种优选实施方式中,所述至少一个聚有机基硅氧烷基团具有以下通式:
-K-S-K-,
其中
其中R1=C1-C22-烷基、C1-C22-氟烷基或芳基,
n=0-1000,并且如果在聚有机基硅氧烷化合物中存在若干S基团,这些基团可相同或不同,优选例如n例如在0-200或>200-1000范围;
K为二价或三价直链、环状和/或支链C2-C40烃残基,其任选被-O-、-NH-、三价N、-NR1-、-C(O)-、-C(S)-中断,并且任选被-OH取代,其中R1如上定义,从而残基K可彼此相同或不同。在这样的基团-K-S-K-中,经由C-Si-键,残基K与残基S的硅原子连接。
在一种优选实施方式中,本发明的聚有机基硅氧烷化合物包含至少一个重复单元,所述重复单元包含至少一个选自以下通式的季铵基团:
-N+R2-,
-N+R2-T-N+R2-,
下式的饱和或不饱和的单季铵杂环或双季铵杂环
下式的芳族铵杂环
其中R选自具有至多22个碳原子和任选一个或多个杂原子的一价有机基团,和,其中在氮原子处的自由价与碳原子结合,并且T选自具有至多20个碳原子和一个或多个杂原子的二价有机基团。更具体地,T选自包含1-20个碳原子的二价烃基,本文使用的对于T的定义,该词语包含包括选自氧、硫、氮和磷的杂原子的基团。在本发明中,术语季铵基团涉及与4个碳原子结合的带正电荷的氮原子(形式上称为NR4+基团)。
在本发明的一种优选实施方式中,末端酯基选自以下:
-OC(O)-Z
-OS(O)2-Z
-OS(O2)O-Z
-OP(O)(O-Z)OH
-OP(O)(O-Z)2
其中Z选自具有至多40个碳原子、任选包含一个或多个杂原子的一价有机残基。如以下详细解释的,这些末端酯基得自使用单官能的有机酸与双环氧化物反应,所述有机酸像羧酸(-OC(O)-Z)、磺酸(-OS(O)2-Z)、硫酸半酯(-OS(O2)O-Z)、磷酸单酯(-OP(O)(O-Z)OH)、磷酸二酯(-OP(O)(O-Z)2)。
在一种优选实施方式中,本发明的聚有机基硅氧烷化合物具有通式(I):
M-Y-[-(N+R2-T-N+R2)-Y-]mM (I),或
M-Y-[-(N+R2)-Y-]m-M (II)
其中:
m为1-100的平均值,优选1-50,更优选1-20,甚至更优选1-10,
k为0或>0-50的平均值,优选1-20,更优选1-10,
M表示末端基团,包含选自以下的末端酯基:
-OC(O)-Z
-OS(O)2-Z
-OS(O2)O-Z
-OP(O)(O-Z)OH
-OP(O)(O-Z)2
其中Z如上定义,
R2选自氢或R,
Y为T或下式的基团:
-K-S-K-,
各自如上定义,条件是至少一个Y为下式的基团:
-K-S-K-,和
T如上定义。
如果在本发明的聚有机基硅氧烷化合物中存在胺基团,它们可例如被有机酸或无机酸质子化。这样的化合物有时称为本发明的聚有机基硅氧烷化合物的酸加成盐。
在一种优选实施方式中,在聚有机基硅氧烷化合物中,季铵基团b)与末端酯基c)的摩尔比小于100:30,最优选小于100:50。该比率可通过13C-NMR测定。
本发明的聚有机基硅氧烷化合物优选通过一种方法制造,所述方法包括以下物质的反应:
(i)至少一种二叔二胺和/或一元仲胺,
(ii)至少一种氨基-烷基化化合物,所述化合物包含至少一种双环氧化物,和
(iii)至少一种单官能的有机酸,
其中在化合物(i)和(ii)中,至少一种化合物包含聚有机基硅氧烷结构单元。
本发明还涉及聚有机基硅氧烷化合物,所述化合物可通过如前所述的本发明的方法得到。
本发明的其它实施方式涉及聚有机基硅氧烷组合物,所述组合物包含:
A)至少一种本发明的聚有机基硅氧烷化合物,
B)不同于化合物A)的至少一种聚有机基硅氧烷化合物,所述化合物包含至少一个末端酯基。
在组分A)的定义中,其可参考本发明的聚有机基硅氧烷化合物的描述。聚有机基硅氧烷化合物B)不同于聚有机基硅氧烷化合物A),优选在于,化合物B)不含季铵基团。优选的聚有机基硅氧烷化合物B)得自单官能的有机酸(特别是羧酸)与含有双环氧化物的聚有机基硅氧烷的反应。
在本发明的聚有机基硅氧烷组合物中,化合物A)与化合物B)的重量比优选小于90:10。或者换言之,组分B)的含量为至少10%重量。在本发明的聚有机基硅氧烷组合物的其它优选实施方式中,在化合物A)中,季铵基团b)与末端酯基c)的摩尔比小于100:20。
本发明的聚硅氧烷聚有机基硅氧烷化合物或聚硅氧烷聚有机基硅氧烷组合物二者优选在20℃和0.1s-1的剪切速率下的粘度(板-板系统,板直径40mm,间隙宽度0.5mm)小于100000mPas(100Pas)。
本发明还涉及水乳液,所述乳液包含如上或以下定义的至少一种聚有机基硅氧烷化合物和/或至少一种聚有机基硅氧烷组合物。这样的水乳液优选包含至少30%重量,优选至少50%重量,还更优选至少80%重量水,基于乳液的总重量。
本发明还涉及表面处理的方法,所述方法包括向基材的表面施用如前述权利要求中任一项所定义的聚有机基硅氧烷化合物、聚有机基硅氧烷组合物或其水乳液的步骤。可想象施用的任何方法,例如,可涉及本领域常规已知的简单的润湿、接触、洗涤、浸渍、喷雾、刷涂、铺展操作。
在这样的方法中,优选分别施用以下组合物或制剂中的一种:用于皮肤和毛发护理的化妆品制剂,选自冲洗型和滞留型调理剂、香波、定型凝胶、喷雾剂和泵喷雾剂;用于抛光的制剂,用于处理和配备硬表面;用于干燥汽车和其它硬表面的制剂;用于初始配备纺织品和纺织品纤维的制剂;额外包含非离子源或阴离子/非离子源或阳离子或甜菜碱表面活性剂的软化剂制剂,用于在洗涤纺织品期间或之后施用;基于非离子或阴离子/非离子或阳离子或甜菜碱表面活性剂用于纺织品洗涤的洗衣制剂,或用于防止或逆转纺织品起皱的制剂。
本发明的其它优选实施方式:
在具有通式S的聚有机基硅氧烷结构单元中:
其中R1=C1-C22-烷基、C1-C22-氟烷基或芳基,
n=0-1000,优选0-500,更优选0-300,甚至更优选0-200,具体地为0-100,或者在一些情况下,>200-1000。
K(在基团-K-S-K-中)优选为二价或三价直链、环状或支链C2-C20烃残基,其任选被-O-、-NH-、三价N、-NR1-、-C(O)-、-C(S)-中断,并且任选被-OH取代。
在本发明的聚有机基硅氧烷中,得自铵基团的正电荷被无机阴离子(例如氯化物、溴化物、硫酸氢根、硫酸根)或有机阴离子(像源自C1-C30羧酸的羧酸根,例如乙酸根、丙酸根、辛酸根,尤其是源自C10-C18羧酸,例如癸酸根、十二烷酸根、十四烷酸根、十六烷酸根、十八烷酸根和油酸根、烷基聚醚羧酸根、烷基磺酸根、芳基磺酸根、烷基芳基磺酸根、烷基硫酸根、烷基聚醚硫酸根、源自磷酸单烷基/芳基酯和磷酸二烷基/芳基酯的磷酸根)中和。基于所用的酸的选择,可尤其改变聚有机基硅氧烷化合物的性质。
包含在本发明的聚有机基硅氧烷中的季铵基团通常通过二叔二胺与特别是选自双环氧化物(有时也称为二环氧化物)的烷基化剂在单羧酸和二官能的二卤素烷基化合物存在下反应而产生。
R1更优选为C1-C18烷基、C1-C18氟烷基和芳基。此外,R1优选为C1-C18烷基、C1-C6氟烷基和芳基。此外,R1优选为C1-C6烷基、C1-C6氟烷基,更优选C1-C4氟烷基和苯基。甚至更优选,R1为甲基、乙基、三氟丙基和苯基。
在本发明的框架中,术语"C1-C22烷基"指具有1-22个碳原子的脂族烃基,其可为直链或支化的。甲基、乙基、丙基、正丁基、戊基、己基、庚基、壬基、癸基、十一烷基、异丙基、新戊基和1,2,3-三甲基己基用作实例。
在本发明的框架中,概念"C1-C22氟烷基"指具有1-22个碳原子的脂族烃化合物,所述化合物可为直链或支化的并且被至少一个氟原子取代。给出单氟甲基、单氟乙基、1,1,1-三氟乙基、全氟乙基、1,1,1-三氟丙基、1,2,2-三氟丁基作为实例。
在本发明的框架中,"芳基"指未取代的或被OH、F、Cl、CF3、C1-C6烷基、C1-C6烷氧基、C3-C7环烷基、C2-C6烯基或苯基取代一次或若干次的苯基。如果需要,该表述还可指萘基。
在一种优选实施方式中,聚有机基硅氧烷化合物具有通式(I):
M-Y-[-(N+R2-T-N+R2)-Y-]m-M (I),或
M-Y-[-(N+R2)-Y-]m-M (II)
其中每一个基团如上定义。
在如下基团M中的Z优选为直链、环状或支链饱和或不饱和的C1-C20烃基,优选C2-C18烃基,甚至更优选-烃基,其可被一个或多个-O-或-C(O)-中断,并且被-OH取代:
-OC(O)-Z
-OS(O)2-Z
-OS(O2)O-Z
-OP(O)(O-Z)OH
-OP(O)(O-Z)2。
优选的基团M为-OC(O)-Z,其得自正链羧酸,特别是具有多于10个碳原子的正链羧酸例如十二烷酸。
在本发明的一种优选实施方式中,聚有机基硅氧烷含有的重复基团-K-S1-K-和重复基团Y的摩尔比为100:0。当情况需要时,其还可为100:1-1:100,优选20:1-1:20,甚至更优选10:1-1:10。
在基团-(N+R2-T-N+R2)-中,基团R优选表示一价直链、环状或支链C1-C20烃基,其可被一个或多个-O-、-C(O)-中断,并且可被-OH取代,T优选表示二价直链、环状或支链C1-C20烃基,其可被-O-、-C(O)-中断,并且可被羟基取代。
根据本发明的该实施方式的净聚合物的粘度优选<100000mPa.s,优选<70000mPa.s,更优选<50000mPa.s,甚至更优选<20000mPa.s,具体地<10000mPa.s,更具体地,<5.000mPa.s,但是优选达到低于500mPa.s,在20℃和0.1s-1的剪切速率下测定。
分子量为10,000-100,000g/mol,作为重均Mw,根据GPC(凝胶渗透色谱法)和聚苯乙烯作为标准物来测量。
在本发明的一种优选实施方式中,K为具有至少4个碳原子的二价烃基,其含有一个羟基并且可被一个氧原子中断。这样的基团包括例如:
本发明的聚有机基硅氧烷化合物优先在第一实施方式中经由以下方法生产,其中在氢化硅烷化催化剂存在下和在50℃-150℃温度下,使用1.0-1.5mol(基于SiH基团)具有末端烯属键的烯基-环氧化物转化以下通用结构的第一α,ωSi-H官能化的硅氧烷
其中所述烯基-环氧化物含有至少4个碳原子,并且可另外含有非环状醚基团。乙烯基环己烯氧化物和烯丙基缩水甘油醚优选用作环氧-官能的前体,用于生产环氧官能化的硅氧烷。如果需要,随后除去过量的烯属环氧化物。
双环氧化物优选与一种二胺(例如下式的优选的二胺),或一元仲胺(反应两次以被季铵化)的混合物反应:
NR2-T-NR2
其中R和T如上定义。
任选,此外,α,ω羧酸卤素烷基酸酯可用作烷基化剂。反应优选在有机酸存在下,优选在40℃-150℃下进行,其中叔氨基:Σ(环氧基团+任选的羧酸卤代酸酯基)的摩尔比例如≤1:1,优选≤0.98:1,更优选≤0.9:1,甚至更优选≤0.7:1,具体地≤0.5:1,有机酸:环氧基团的摩尔比在3:1-1:1范围,优选2:1-1:1,更优选1.5:1-1:1,甚至更优选1.2:1-1:1,具体地为1:1。
这意味着,即,通过降低叔胺的摩尔量和/或提高有机酸的摩尔量,可合成本发明的低粘度聚有机基硅氧烷化合物。
在实施方式的一种优选的变体中,含有各种氨基的物类可任选与羧酸卤代酸酯衍生物一起加入到批料中,如果需要,同时加入等摩尔量的酸。然而,还在本发明的范围内的是引起第一环氧衍生物、羧酸卤代酸酯衍生物和二叔胺在等同于环氧基团的量的酸存在下反应。
同样可使羧酸卤代酸酯衍生物和二叔胺反应,形成亲水嵌段,如果需要,然后在等同于环氧基团的量的酸存在下,向反应混合物中加入环氧衍生物。
在其中加入单个组分期间,可影响在待形成的聚合物中的序贯分布。
进一步在本发明的范围内的是引起具有各种链长的若干硅氧烷组分反应,同时保持期望的总体化学计量学。由此,接着,例如,通过使用单一硅氧烷组分或通过若干硅氧烷组分的有目的的混合物,可能产生期望的硅氧烷链长。
季铵化和烷基化反应优选在极性有机溶剂中进行。
合适的溶剂为例如有机溶剂和水,特别是包括有机溶剂和水的混合物,优选极性有机溶剂和水的混合物。极性有机溶剂通常包括包含至少一个杂原子(特别是像氧)的那些,例如,醇,尤其是甲醇、乙醇、异丙醇和正丁醇;二醇,例如乙二醇、一缩二乙二醇、二缩三乙二醇、它们的甲基-、乙基-和丁基醚,1,2-丙二醇、一缩二丙二醇、二缩三丙二醇、它们的甲基-、乙基-和丁基醚和1,3-丙二醇;酮,例如丙酮和甲乙酮;酯,例如乙酸乙酯、乙酸丁酯、乙酸甲氧基丙酯和乙酸2-乙基-己酯;醚,例如四氢呋喃;和硝基化合物,例如硝基甲烷。
优选在Σ聚合物组分:Σ(有机溶剂+水)的重量比在100:0-20:80重量范围,优选99.999:0.001-20:80,更优选95:5-20:80,还更优选95:5-50:50,甚至更优选95:5-60:40下进行反应。
在一种实施方式中,在反应的组合物中水的量在0.1-0.5重量%范围,在另一实施方式中,优选0.01-0.1重量%;在另一实施方式中,该量在2-10重量%范围,优选0.5-2重量%。在本发明的一种优选实施方式中,单独加入期望量的水。还可加入期望量的水,即,溶剂共沸物形式或在商品级别中存在的量。
包含季铵官能团和酯官能团的上述聚有机基硅氧烷化合物可包含含有季铵官能团并且不含酯官能团的单一分子、含有季铵官能团和酯官能团的分子以及含有酯官能团并且不含季铵官能团的分子。
包含季铵官能团和酯官能团的上述聚有机基硅氧烷化合物应理解为包含某些平均量和比率的两部分的分子的混合物。
本发明的另一不太优选实施方式涉及聚有机基硅氧烷组合物,所述组合物包含:
A)如上定义的至少一种聚有机基硅氧烷化合物,
B)不同于化合物A)的至少一种聚有机基硅氧烷化合物,所述化合物包含至少一个末端酯基。
将包含季铵官能团的这样的聚有机基硅氧烷组合物和包含酯官能团的聚有机基硅氧烷化合物物理混合,以根据本发明调节期望的季铵(N+):酯比率和期望的粘度。
根据本发明,两种化合物以实现以上描述的粘度要求的比率混合。混合物在20℃和0.1s-1的剪切速率下的粘度为500-100000mPas,优选500-70000mPas,更优选500-50000mPa.s,甚至更优选500-20000mPas,具体地为500-10000mPas,更具体地,500-5000mPa.s。分子量为10,000-100,000g/mol,作为重均Mw,根据GPC(凝胶渗透色谱法)和聚苯乙烯作为标准物来测量。
包含季铵官能团的聚有机基硅氧烷化合物A)由WO 02/10257获知。包含酯官能团的聚有机基硅氧烷化合物的合成由WO 2011/064255获知。它们可由相应的环氧硅氧烷通过在叔胺催化剂存在下与酸酯化而合成。包含酯官能团的优选的聚有机基硅氧烷化合物B)为结构M-(K-Sn-K)-M的α,ω-酯改性的衍生物,其中硅氧烷链长在n=0-1000,优选0-500,更优选0-300,甚至更优选0-200,具体地为0-100范围。或者,也优选相同的链长范围n的梳状衍生物,其在二官能的硅氧烷单元中包含酯官能团作为侧基(OSiMeR*,其中R*=碳连接的酯基))和任选的末端酯部分(O1/2SiMe2R*,其中R*=碳连接的酯基)。含有酯基团的甲硅烷氧基单元的数量优选为1-500,优选1-250,更优选1-150,甚至更优选1-100,具体地为1-50,甚至更具体地为1-25。
产生酯的优选的单官能的有机酸为形成以上提及的反离子的物质。优选的实例为C1-C30羧酸,例如C2、C3、C8酸、C10-C18羧酸,例如C12、C14、C16酸、饱和、不饱和及羟基官能化的C18酸、烷基聚醚羧酸、烷基磺酸、芳基磺酸、烷基芳基磺酸、烷基硫酸、烷基聚醚硫酸、磷酸单烷基/芳基酯和磷酸二烷基/芳基酯。
本发明还涉及上述聚有机基硅氧烷化合物的以下用途:用于皮肤和毛发护理的化妆品制剂,用于处理和涂布硬表面的抛光剂,用于干燥汽车和其它硬表面的制剂,例如在自动洗涤后,用于精整纺织品和纺织品纤维,作为单独的软化剂用于在已使用非离子源或阴离子/非离子源洗涤剂制剂洗涤后的纺织品中使用,作为软化剂用于基于非离子或阴离子/非离子表面活性剂的洗涤纺织品的制剂,和作为防止或除去纺织品中的皱纹的手段。
本发明还涉及使用上述聚有机基硅氧烷化合物作为耐洗、亲水性软化剂,用于纺织品的初始精整。
本发明还涉及组合物,所述组合物含有至少一种聚有机基硅氧烷化合物,以及至少一种常用于这样的组合物的另外的组分。
以下,提供多个这些类型的组合物的典型的实例,其中可有利地使用本发明的聚有机基硅氧烷化合物:
在这些类型的组合物中,典型的助剂为例如在以下描述的那些材料:A.Domsch:Die kosmetischen Praeparate[化妆品制备],第I和II卷,第4版,Verl.fuerchem.Industrie[Publishers for the Chemical Industry],U.Ziolkowsky K G,Augsburg,和International Cosmetic Ingredient Dictionary and Handbook(国际化妆品成分字典和手册),第7版,1997,J.A.Wenninger,G.N.McEwen,第1-4卷,The Cosmetic,Toiletry and Fragrance Association Washington D.C.。
阴离子香波
该制剂实施例旨在作为基本制剂。阴离子香波按照惯例含有但不限于以下组分:
●烷基硫酸盐、烷基醚硫酸盐、月桂基硫酸钠、月桂基醚硫酸钠、月桂基硫酸铵、月桂基醚硫酸铵、TEA-月桂基硫酸盐、TEA-月桂基-醚硫酸盐、烷基苯磺酸盐、α-烯属磺酸盐、石蜡磺酸盐、磺基琥珀酸盐、N-酰基氨基乙磺酸盐、硫酸盐-甘油酯、硫酸盐化的链烷醇酰胺、羧酸盐、N-酰基-氨基酸盐、有机硅等。
非离子香波
该制剂实施例旨在作为基本制剂。非离子香波按照惯例含有但不限于以下组分:
●单链烷醇酰胺、单乙醇酰胺、单异丙醇酰胺、多羟基衍生物、蔗糖单月桂酸酯、聚甘油醚、氧化胺、聚乙氧基化的衍生物、山梨糖醇衍生物、有机硅等。
两性香波
该制剂实施例旨在作为基本制剂。这种类型的制剂按照惯例含有但不限于以下组分:
●N-烷基-亚氨基二丙酸盐、N-烷基-亚氨基丙酸盐、氨基酸、氨基酸衍生物、酰氨基甜菜碱、咪唑鎓衍生物、磺基甜菜碱、磺基甜菜碱、甜菜碱、有机硅等。
阳离子香波
该制剂实施例旨在仅作为基本制剂。这种类型的制剂按照惯例含有但不限于以下组分:
●双-季铵化合物、双-(三烷基铵乙酰基)二胺、酰氨基胺、铵烷基酯、有机硅等。
定型剂
该制剂实施例旨在仅作为基本制剂。这种类型的制剂按照惯例含有但不限于以下组分:
●脂肪酸、脂肪酸酯、乙氧基化的脂肪酸、乙氧基化的脂肪酸酯、脂肪醇、乙氧基化的脂肪醇、二醇、二醇酯、甘油、甘油酯、羊毛脂、羊毛脂衍生物、矿物油、矿脂、卵磷脂、卵磷脂衍生物、蜡、蜡衍生物、阳离子聚合物、蛋白质、蛋白质衍生物、氨基酸、氨基酸衍生物、湿润剂、增稠剂、有机硅等。
"澄清的冲洗型"定型剂
该制剂实施例旨在作为基本制剂。这种类型的制剂按照惯例含有但不限于以下组分:
●脂肪酸、脂肪酸酯、乙氧基化的脂肪酸、乙氧基化的脂肪酸酯、脂肪醇、乙氧基化的脂肪醇、二醇、二醇酯、甘油、甘油酯、羊毛脂、羊毛脂衍生物、矿物油、矿脂、卵磷脂、卵磷脂衍生物、蜡、蜡衍生物、阳离子聚合物、蛋白质、蛋白质衍生物、氨基酸、氨基酸衍生物、湿润剂、增稠剂、有机硅等。
用于毛发的泡沫定型剂
该制剂实施例旨在作为基本制剂。这种类型的制剂含有但不限于以下组分:
●脂肪酸、脂肪酸酯、乙氧基化的脂肪酸、乙氧基化的脂肪酸酯、脂肪醇、乙氧基化的脂肪醇、二醇、二醇酯、甘油、甘油酯、羊毛脂、羊毛脂衍生物、矿物油、矿脂、卵磷脂、卵磷脂衍生物、蜡、蜡衍生物、阳离子聚合物、蛋白质、蛋白质衍生物、氨基酸、氨基酸衍生物、湿润剂、增稠剂、有机硅、溶剂、乙醇、异丙醇、异链烷烃溶剂、丁烷、丙烷、异丁烷、CFC的氟化的气溶胶推进剂、二甲基醚、压缩气体等。
用于毛发的泵喷雾(定型剂)
该制剂实施例旨在仅作为基本制剂。这种类型的制剂按照惯例含有但不限于以下组分:
●脂肪酸、脂肪酸酯、乙氧基化的脂肪酸、乙氧基化的脂肪酸酯、脂肪醇、乙氧基化的脂肪醇、二醇、二醇酯、甘油、甘油酯、羊毛脂、羊毛脂衍生物、矿物油、矿脂、卵磷脂、卵磷脂衍生物、蜡、蜡衍生物、阳离子聚合物、蛋白质、蛋白质衍生物、氨基酸、氨基酸衍生物、湿润剂、增稠剂、有机硅、溶剂、乙醇、异丙醇、异链烷烃溶剂等。
用于毛发的定型剂喷雾
该制剂实施例旨在作为基本制剂。这种类型的制剂按照惯例含有但不限于以下组分:
●脂肪酸、脂肪酸酯、乙氧基化的脂肪酸、乙氧基化的脂肪酸酯、脂肪醇、乙氧基化的脂肪醇、二醇、二醇酯、甘油、甘油酯、羊毛脂、羊毛脂衍生物、矿物油、矿脂、卵磷脂、卵磷脂衍生物、蜡、蜡衍生物、阳离子聚合物、蛋白质、蛋白质衍生物、氨基酸、氨基酸衍生物、湿润剂、增稠剂、有机硅、溶剂、乙醇、异丙醇、异链烷烃溶剂、丁烷、丙烷、异丁烷、CFC的氟化的气溶胶推进剂、二甲基醚、压缩气体等。
用于毛发的凝胶定型剂
该制剂实施例旨在作为基本制剂。这种类型的制剂按照惯例含有但不限于以下组分:增稠剂、纤维素衍生物、丙烯酸衍生物、固定剂聚合物、调理化学品、二醇、二醇酯、甘油、甘油酯、羊毛脂、羊毛脂衍生物、矿物油、矿脂、卵磷脂、卵磷脂衍生物、蜡、蜡衍生物、阳离子聚合物、蛋白质、蛋白质衍生物、氨基酸、氨基酸衍生物、湿润剂、有机硅、溶剂、乙醇、异丙醇、异链烷烃溶剂等。
冲洗型调理剂
该制剂实施例旨在作为基本制剂。这种类型的制剂按照惯例含有但不限于以下组分:基于烃的阳离子调理剂、基于有机硅的阳离子调理剂、高熔点脂肪化合物、低熔点油如酯化合物、增稠剂、纤维素衍生物、固定剂聚合物、乙二醇、丙二醇、二醇酯、甘油、甘油酯、一元醇、多元醇、阳离子聚合物、非离子和甜菜碱辅助乳化剂、有机硅、络合剂、溶剂、香料、维生素、溶剂等。
用于毛发的定型凝胶
该制剂实施例旨在作为基本制剂。这种类型的制剂按照惯例含有但不限于以下组分:
●固定剂聚合物、亮油、丙烯酸衍生物、纤维素衍生物、乙烯基衍生物、调理化学品、二醇、二醇酯、甘油、甘油酯、羊毛脂、羊毛脂衍生物、矿物油、矿脂、卵磷脂、卵磷脂衍生物、蜡、蜡衍生物、阳离子聚合物、蛋白质、蛋白质衍生物、氨基酸、氨基酸衍生物、湿润剂、增稠剂、有机硅、溶剂、乙醇、异丙醇、异链烷烃溶剂等。
用于毛发的定型喷雾
该制剂实施例旨在作为基本制剂。这种类型的制剂按照惯例含有但不限于以下组分:
●固定剂聚合物、亮油、乙烯基衍生物、脂肪酸、脂肪酸酯、乙氧基化的脂肪酸、乙氧基化的脂肪酸酯、脂肪醇、乙氧基化的脂肪醇、二醇、二醇酯、甘油、甘油酯、羊毛脂、羊毛脂衍生物、矿物油、矿脂、卵磷脂、卵磷脂衍生物、蜡、蜡衍生物、阳离子聚合物、蛋白质、蛋白质衍生物、氨基酸、氨基酸衍生物、湿润剂、增稠剂、有机硅、溶剂、乙醇、异丙醇、异链烷烃溶剂、丁烷、丙烷、异丁烷、CFC的氟化的气溶胶推进剂、二甲基醚、压缩气体等。
用于毛发的泵喷雾(定型)
该制剂实施例旨在作为基本制剂。这种类型的制剂按照惯例含有但不限于以下组分:
●乙烯基衍生物、固定剂聚合物、亮油、脂肪酸、脂肪酸酯、乙氧基化的脂肪酸、乙氧基化的脂肪酸酯、脂肪醇、乙氧基化的脂肪醇、二醇、二醇酯、甘油、甘油酯、羊毛脂、羊毛脂衍生物、矿物油、矿脂、卵磷脂、卵磷脂衍生物、蜡、蜡衍生物、阳离子聚合物、蛋白质、蛋白质衍生物、氨基酸、氨基酸衍生物、湿润剂、增稠剂、有机硅、溶剂、乙醇、异丙醇、异链烷烃溶剂、丁烷、丙烷、异丁烷、CFC的氟化的气溶胶推进剂、二甲基醚、压缩气体等。
使用在本发明中指定的聚有机基硅氧烷衍生物应用于毛发护理领域在以下方面产生有利的结果:加强、光泽、固定(保持)、身体、体积、水分调节、颜色保持、保护免于环境因素(UV、盐水等)、易处理性、抗静电性质、染色能力等。
实施例
以下实施例旨在更详细地描述本发明,而不是限制本发明的范围。
实施例1(非本发明的)
在配备回流冷凝器、温度计和机械搅拌器的500ml三颈烧瓶中,将150g(58.7mmol环氧基团)具有以下结构的有机硅双环氧化物、11.76g(58.7mmol)月桂酸、5.06g N,N,N’,N’-四甲基己二胺(58.7mmol叔胺)、31.3g 2-丙醇和10.4g蒸馏水在室温下混合。将混合物加热回流达6小时。随后,除去溶剂,材料借助NMR和粘度测量法分析(参见表1)。在水中的分散性以及乳液的稳定性差。
实施例2(本发明的)
在配备回流冷凝器、温度计和机械搅拌器的500ml三颈烧瓶中,将150g(58.7mmol环氧基团)具有以下结构的有机硅双环氧化物、11.76g(58.7mmol)月桂酸、2.53g N,N,N’,N’-四甲基己二胺(29.35mmol叔胺)、30.8g 2-丙醇和10.3g蒸馏水在室温下混合。将混合物加热回流达6小时。随后,除去溶剂,材料借助NMR和粘度测量法分析(参见表1)。在水中的分散性以及乳液的稳定性得到改进并且为可接受的水平。
表1
*将4g聚有机基硅氧烷材料加入到200g水中,使用Ultra Thurrax进行混合,
**13C-NMR。
数据显示,在实施例1的情况下,非本发明的反应方案得到含有一些酯官能团的材料,但是粘度太高。结果是,在水中形成非常差、不均匀、成块和粘性分散体。实施例2显示本发明的反应方案得到低粘度材料,其可容易分散成为具有足够稳定性的小液滴。
实施例3(本发明的)
将实施例1的非本发明的产品与以下结构的月桂酰基酯改性的硅氧烷混合,该硅氧烷根据WO 2011/064255,由相应的环氧硅氧烷、月桂酸和三乙胺(催化剂)在丙二醇单甲基醚中合成。
共混实验汇总于表2。
表2
样品# | 比率,样品1:月桂酰基酯 | 粘度,mPa.s,20℃,0.1s-1 | 在水中的分散性* |
3.1 | 100:0 | 112,000 | 非常差 |
3.2 | 90:10 | 52,700 | 可接受的 |
3.3 | 75:25 | 20,000 | 良好 |
*将4g聚有机基硅氧烷材料加入到200g水中,使用Ultra Thurrax进行混合。
在表2中,实施例3.2和3.3的数据显示,将实施例1的非本发明的材料与酯改性的硅氧烷物理共混得到落入本发明的混合物。
实施例4(本发明的)
在配备回流冷凝器、温度计和机械搅拌器的500ml三颈烧瓶中,将97.4g(9mmol环氧基团)具有以下结构的有机硅双环氧化物、0.36g(6mmol)乙酸、0.52g N,N,N’,N’-四甲基己二胺(6mmol叔胺)、96.5g甲氧基丙醇和1.97g蒸馏水在室温下混合。将混合物加热回流达4小时。随后,加入0.18g(3mmol)乙酸,混合物保持回流达另外的4小时。除去溶剂。得到聚合材料,其固含量为95.68%(120℃/30分钟),粘度为4300mPa.s(20℃,0.1s-1)。
实施例5(本发明的)
使用Diastron梳理力(Combing Force)设备评价调理性能。将得自InternationalHair Importers的单一漂白的发绺(4g)用10%月桂基硫酸钠溶液洗涤,干燥。将该发绺放置在50%(相对湿度RH)的受控湿度的室中过夜,随后进行梳理力Fb的基线测量。
将有机硅聚合物溶解于异丙醇中,以得到0.014重量%和0.07重量%的溶液。用移液管使约2.8g异丙醇溶液在发绺上均匀分布,在毛发上分别得到100ppm和500ppm有机硅聚合物。在50℃烘箱中干燥过夜后,将该发绺放置在50%RH的受控湿度的室中,随后测量经处理的发绺的梳理力Ft。干梳理力下降相应于值(Fb-Ft).100/Ft。
结果汇总于表3。
表3
)3聚氨基丙基甲基硅氧烷
表3显示在用于毛发处理的组合物中,在低浓度下,本发明的聚有机基硅氧烷提供好得多的干梳理力下降。
Claims (23)
1.一种聚有机基硅氧烷化合物,所述化合物包含:
a)至少一个聚有机基硅氧烷基团,
b)至少一个季铵基团,
c)至少一个末端酯基,
其中所述聚有机基硅氧烷化合物为包含上述官能团a)、b)的线性共聚物化合物,所述化合物中至少一部分末端基团为由使用单官能的有机酸作为链终止剂得到的末端酯基c),并且
其中所述聚有机基硅氧烷化合物具有选自通式(I)或(II)的分子式:
M-Y-[-(N+R2-T-N+R2)-Y-]m-M (I),或
M-Y-[-(N+R2)-Y-]m-M (II)
其中:
m为1-100的平均值,
k为0或>0-50的平均值,
M表示末端基团,包含选自以下的末端酯基:
-OC(O)-Z
-OS(O)2-Z
-OS(O2)O-Z
-OP(O)(O-Z)OH
-OP(O)(O-Z)2
其中Z如上定义,
R2选自氢或R,
Y为T,或下式的基团:
-K-S-K-
各自如上定义,条件是至少一个Y为下式的基团:
-K-S-K-,和
T如上定义。
2.权利要求1的聚有机基硅氧烷化合物,其中所述季铵基团b)与所述末端酯基c)的摩尔比小于100:20。
3.权利要求1或2的聚有机基硅氧烷化合物,所述化合物不含聚氧化烯基团,所述末端酯基除外。
4.权利要求1的聚有机基硅氧烷化合物,所述化合物包含至少一个具有以下通式的聚有机基硅氧烷基团a):
-K-S-K-,
其中
其中R1=C1-C22-烷基、C1-C22-氟烷基或芳基,
n=0-1000,并且如果在聚有机基硅氧烷化合物中存在若干S基团,这些基团可相同或不同,
K为二价或三价直链、环状和/或支链C2-C40烃残基,其任选被-O-、-NH-、三价N、-NR1-、-C(O)-、-C(S)-中断,并且任选被-OH取代,其中R1如上定义,从而残基K可彼此相同或不同。
5.权利要求1的聚有机基硅氧烷化合物,所述化合物包含至少一个重复单元,所述重复单元包含至少一个选自以下通式的季铵基团b):
-N+R2-,
-N+R2-T-N+R2-,
下式的饱和或不饱和的单季铵杂环或双季铵杂环
下式的芳族铵杂环
其中R选自具有至多22个碳原子和任选一个或多个杂原子的一价有机基团,和,其中在氮原子处的自由价与碳原子结合,并且T选自具有至多20个碳原子和一个或多个杂原子的二价有机基团。
6.权利要求1的聚有机基硅氧烷化合物,其中所述末端酯基c)选自以下:
-OC(O)-Z
-OS(O)2-Z
-OS(O2)O-Z
-OP(O)(O-Z)OH
-OP(O)(O-Z)2
其中Z选自具有至多40个碳原子、任选包含一个或多个杂原子的一价有机残基。
7.权利要求1的聚有机基硅氧烷化合物,其中m为1-50的平均值。
8.权利要求1的聚有机基硅氧烷化合物,其中m为1-20的平均值。
9.权利要求1的聚有机基硅氧烷化合物,其中m为1-10的平均值。
10.权利要求1的聚有机基硅氧烷化合物,其中k为1-20的平均值。
11.权利要求1的聚有机基硅氧烷化合物,其中k为1-10的平均值。
12.权利要求1的聚有机基硅氧烷化合物,所述化合物具有质子化的铵基团。
13.一种用于制造权利要求1-12中任一项的聚有机基硅氧烷化合物的方法,所述方法包括使以下物质反应:
(i)至少一种二叔二胺和/或一元仲胺,
(ii)至少一种氨基-烷基化化合物,所述化合物包含至少一种双环氧化物,和
(iii)至少一种单官能的有机酸,
其中在化合物(i)和(ii)中,至少一种化合物包含聚有机基硅氧烷结构单元。
14.一种聚有机基硅氧烷化合物,所述化合物通过权利要求13的方法制备。
15.一种聚有机基硅氧烷组合物,所述组合物包含:
A)至少一种权利要求1-14中任一项定义的聚有机基硅氧烷化合物,和
B)至少一种不同于化合物A)的聚有机基硅氧烷化合物,所述化合物包含至少一个末端酯基。
16.权利要求15的聚有机基硅氧烷组合物,其中所述化合物A)与化合物B)的重量比小于90:10。
17.权利要求15或16的聚有机基硅氧烷组合物,其中在化合物A)中,季铵基团b)与末端酯基c)的摩尔比小于100:20。
18.一种水乳液,所述乳液包含至少一种权利要求1-17中任一项定义的聚有机基硅氧烷化合物和/或至少一种聚有机基硅氧烷组合物。
19.一种表面处理的方法,所述方法包括向基材的表面施用如前述权利要求中任一项所定义的聚有机基硅氧烷化合物、聚有机基硅氧烷组合物或其水乳液的步骤。
20.权利要求19的方法,其中分别施用以下组合物或制剂中的一种:用于皮肤和毛发护理的化妆品制剂,选自冲洗型和免洗型调理剂、香波、定型凝胶、喷雾剂和泵喷雾剂;用于抛光的制剂,用于处理和配备硬表面;用于干燥汽车和其它硬表面的制剂;用于初始配备纺织品和纺织品纤维的制剂;额外包含非离子源或阴离子/非离子源或阳离子或甜菜碱表面活性剂的软化剂制剂,用于在洗涤纺织品期间或之后施用;基于非离子或阴离子/非离子或阳离子或甜菜碱表面活性剂的用于纺织品洗涤的洗衣制剂,或用于防止或逆转纺织品起皱的制剂。
21.一种聚有机基硅氧烷化合物,所述化合物基本上由以下组成:
a)至少一个聚有机基硅氧烷基团,
b)至少一个季铵基团,和
c)至少一个末端酯基,
其中所述聚有机基硅氧烷化合物为包含上述官能团a)、b)的线性共聚物化合物,所述化合物中至少一部分末端基团为由使用单官能的有机酸作为链终止剂得到的末端酯基c),并且
其中所述聚有机基硅氧烷化合物具有选自通式(I)或(II)的分子式:
M-Y-[-(N+R2-T-N+R2)-Y-]m-M (I),或
M-Y-[-(N+R2)-Y-]m-M (II)
其中:
m为1-100的平均值,
k为0或>0-50的平均值,
M表示末端基团,包含选自以下的末端酯基:
-OC(O)-Z
-OS(O)2-Z
-OS(O2)O-Z
-OP(O)(O-Z)OH
-OP(O)(O-Z)2
其中Z如上定义,
R2选自氢或R,
Y为T,或下式的基团:
-K-S-K-
各自如上定义,条件是至少一个Y为下式的基团:
-K-S-K-,和
T如上定义。
22.权利要求21的聚有机基硅氧烷化合物,所述化合物进一步基本上由以下组成,其中所述至少一个季铵基团为
-N+R2-T-N+R2-,
式中T选自包含1-20个碳原子的二价烃基和R选自具有至多22个碳原子和任选一个或多个杂原子的一价有机基团。
23.权利要求1-17中任一项的聚有机基硅氧烷化合物或聚有机基硅氧烷组合物,其在20℃和0.1s-1的剪切速率下的粘度低于100000mPa.s。
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EP2831177A1 (en) | 2015-02-04 |
JP2015514879A (ja) | 2015-05-21 |
WO2013148635A1 (en) | 2013-10-03 |
CN104334646A (zh) | 2015-02-04 |
EP3357973B1 (en) | 2019-07-31 |
WO2013148629A1 (en) | 2013-10-03 |
US9512275B2 (en) | 2016-12-06 |
CN104302705B (zh) | 2017-04-12 |
IN2014MN01877A (zh) | 2015-07-03 |
US20150056155A1 (en) | 2015-02-26 |
IN2014MN01906A (zh) | 2015-07-10 |
EP2831178B1 (en) | 2020-07-22 |
US20150299400A1 (en) | 2015-10-22 |
EP2831177B1 (en) | 2018-05-09 |
JP2015519413A (ja) | 2015-07-09 |
CN104302705A (zh) | 2015-01-21 |
US9428616B2 (en) | 2016-08-30 |
EP2831178A1 (en) | 2015-02-04 |
BR112014024182B1 (pt) | 2021-06-29 |
EP3357973A1 (en) | 2018-08-08 |
BR112014024182A2 (pt) | 2017-06-20 |
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