CN106793773A - 季型有机硅表面活性剂、其制备方法和包含其的应用 - Google Patents
季型有机硅表面活性剂、其制备方法和包含其的应用 Download PDFInfo
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- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 1
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- TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 description 1
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- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
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- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
- A61K8/585—Organosilicon compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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Abstract
本文提供包括具有通式(I):AOaR4 b(BOcR11 d)eC的季型有机硅的表面活性剂组合物。也提供所述季型有机硅(I)的制备方法以及包含所述季型有机硅的农业、涂料、个人护理和家庭护理应用。
Description
本申请要求于2014年10月10日提交的美国临时专利申请62/062,281的优先权,其通过引用以其整体并入本文。
技术领域
本发明涉及表面活性剂,更具体地,季型有机硅(quaternary organosilicon)表面活性剂,和其在农业、涂料(coating)、个人护理和家庭护理应用中的用途。
背景技术
表面活性剂一直在很多领域中广泛地被使用。在表面活性剂的使用中,性质例如润湿、铺展、发泡、洗涤性等在使用它们的多种应用中是重要的。另外,一些表面活性剂已经表现出在多种植物物种中抑制多种农业化学品(agrochemicals)的摄入(吸收)。因此,提供这样的表面活性剂将是有利的:其保持期望的表面活性剂性质,同时还提供在多种植物物种中的增加的农业化学品的摄入。
发明内容
按照本发明,本文已经预料不到地发现,基本上不含烷基卤和牛油胺乙氧基化物的多种季型有机硅表面活性剂的使用提供在多种植物物种中改善的农业化学品的摄入。更特别地,本文已经发现,相比于三硅氧烷烷氧基化物和碳硅烷烷氧基化物,本文描述的季型有机硅表面活性剂在不存在牛油胺乙氧基化物的情况下具有改善的草甘膦在草中的摄入。
按照本发明,本文提供了表面活性剂组合物,其包括具有如下通式(I)的季型有机硅:
AOaR4 b(BOcR11 d)eC (I)
其中:
A=R1R2R3Si-;
B=-Si(R5)(R6)-;
C=R7R8R9Si-;
下标a、b、c、d和e为0或1且满足以下关系:
a+b=1,且当e=1时c+d=1;
R1、R2、R3、R5、R7、R8独立地选自包含1-8个碳原子、更特别地,1-6个碳原子的一价烃基团和包含6-12个碳原子的一价的芳基和烷芳基烃基团,或R10,
其中R10选自包含3-6个碳原子的支化的一价烃基团,例如非限制性实例的异丙基、叔丁基和叔戊基;
R4和R11独立地选自包含1-4个碳原子、更特别地,1-3个碳原子的二价烃基团;
R6和R9选自包含1-8个碳原子、更特别地,1-4个碳原子的线性或支化的一价烃基团,或R12,条件是R6和R9不同且R6或R9之一为R12,
其中R12选自R*或
其中R*为
其中R19和R20独立地选自H或甲基,
R21和R22不同且选自OH或R23;
R23为
其中R13为包含3-12个碳原子、更特别地,3-6个碳原子的且任选地被一个或多个羟基所取代的二价烃基团,
R14选自-OCH2CH(OH)CH2-和如下通式(II)的氧化烯基团:
-[OC2H4]h-[OC3H6]i-[OC4H8]k-OCH2CH(OH)CH2- (II)
其中下标h、i和k为零或正数且满足以下关系:1≤h+i+k≤15,更特别地,1≤h+i+k≤10,甚至更特别地,h为0-8,i为0-5且k为0-4,
R15和R16独立地选自包含1-2个碳原子的一价烃基团,
R17选自可各自任选地被一个或多个羟基所取代的包含1-6个碳原子的线性或支化的烃基团或如下通式(III)的氧化烯基团:
-[OC2H4]m-[OC3H6]n-[OC4H8]p-R18 (III)
其中下标m、n和p为零或正数且满足以下关系:1≤m+n+p≤15,更特别地,1≤m+n+p≤10,甚至更特别地,m为0-8,n为0-5且p为0-4,
R18选自-OH和包含1-4个碳原子的一价烃基团;且
XY为R34或较易于生物降解的基团RPE,
R34选自包含2-22个碳原子、更特别地,2-12个碳原子的羧酸阴离子部分且具有如下通式:
YO-C(=O)-C(R35)(R36)(R37)
其中下标q、r和s为0或1,
R35和R36选自H、OH、1-3个碳原子的烃基团或CH2OH,
R37选自H、OH、1-3个碳原子的烃基团、CH2OH或–(CH R38)f-CH2R39,
其中
R38为H、OH、1-3个碳原子的烃基团或CH2OH;
R39选自H或OH,
下标f为0-3。
RPE为源自对应的羟基羧酸或对应的羟基羧酸和羧酸的混合物的酯化的聚酯部分,其中所述所述羟基羧酸包含2-8个碳原子、更特别地,2-5个碳原子,并且RPE为如下通式(Z):
YO-C(=O)-CH(3-[q+r+s])(R24)q(R25)r(R26)s (Z)
下标q、r和s为0或1,
其中R24、R25、R26独立地选自-OH、-CH2OH、-(CH2)mOR27、-CH3、-CH2CH3、-(CH2)mO-C(=O)(CR30R31)tCH2OR32或R28,
其中R27为-C(=O)-CH(3-[q+r+s])(R24)q(R25)r(R26)s
R28为-R29OR27,其中R29为2-6个碳原子的二价烃自由基,
R30和R31独立地选自H、-OH、-CH2OH、-(CH2)mO-R27、-CH3、-CH2CH3或-(CH2)mO-C(=O)-(CR30R31)tCH2OR32,
R32独立地选自H、-CH2OH、-CH3、-CH2CH3、R27或[-C(=O)(CR30R31)tCH2O]w-R33,
R33独立地选自H、-CH2OH、-CH3或-CH2CH3,
其中,
下标m为0-3,
下标t为1-5,
下标w为1-5,且
RPE的数量为1-10。
以下给出生物可降解的聚酯改性的羟基酸的非限制的说明性实例(图1和2),其中酯键提供相对于常规的三硅氧烷烷氧基化物增强的生物降解性。
本文还提供以上所述的具有通式(I)的季型有机硅的制备方法。
本发明的多个其它特征、方面和优点参考以下描述和所附的权利要求将变得更显然。
具体实施方式
在本文的一个实施方式中,所述季型有机硅具有通式(I),其中XY选自单羧酸、二羧酸、α-羟基酸、β-羟基酸、二羟基酸以及饱和的和不饱和的脂肪酸的阴离子。
在本文的一个更具体的实施方式中,所述季型有机硅具有如下通式(IV):
AR4C (IV)
其中
A=R1R2R3Si-;且
C=R7R8R9Si-;
其中R1、R2、R3、R7和R8为甲基;
R4为-CH2CH2-;
R9为R12,
其中R12为
其中R13为-CH2CH2CH2-;
R14为-OCH2CH(OH)CH2-;
R15和R16为甲基;
R17为-CH2CH(OH)CH2-OH;且
XY为CH3C(CH2OH)2COO-。
在本文的另一更具体的实施方式中,所述季型有机硅具有如下通式(V):
AR4BOC (V)
其中
A=R1R2R3Si-;
B=-Si(R5)(R6)-;且
C=R7R8R9Si-;
其中R1、R2、R3、R5、R6、R7和R8为甲基;
R4为-CH2CH2-;
R9为R12;
其中R12为
其中R13为-CH2CH2CH2-;
R14为-OCH2CH(OH)CH2-;
R15和R16为甲基;
R17为-CH2CH2CH2OH;且
XY为CH3C(CH2OH)2COO-。
在本文的又一优选的实施方式中,所述季型有机硅具有如下通式(V-B):
AOBOC (V-B)
其中
A=R1R2R3Si-;
B=-Si(R5)(R6)-;且
C=R7R8R9Si-;
其中R1、R2、R3、R5、R7、R8和R9为甲基;
R6为R12;
其中R12为
其中R13为-CH2CH2CH2-;
R14为-OCH2CH(OH)CH2-;
R15和R16为甲基;
R17为-CH2CH2CH2OH;且
XY为CH3C(CH2OH)2COO-。
本文还提供具有通式(I)的季型有机硅的制备方法,该方法包括:
(a)使氢化物中间物和烯烃改性的中间物在催化剂如氢化硅烷化催化剂(例如,非限制性实例的贵金属催化剂如本文描述的那些)的存在下进行反应以制造环氧改性的有机硅中间物;且其中所述烯烃改性的中间物为包含一个或多个环氧乙烷或环氧丙烷基团(oxirane or oxetane groups)且包含一个或多个末端或悬垂的碳-碳键且包含4-12个碳原子的分子,例如非限制性实例的烯丙基环氧乙烷,烯烃改性的环氧化物例如如下通式的那些:CH2=CH-(CH2)yO(CH2)zCH(O)CH2,其中下标y和z为1-10,
其中R34和R35独立地选自氢或甲基,且其中烯烃改性的中间物的一个非限制性实例为烯丙基缩水甘油基醚,且其中,在一个实施方式中,所述氢化物中间物具有如下通式(VI):
AOaR4 b(BHOcR11 d)eCH (VI)
其中:
A=R1R2R3Si-;
BH=-Si(R5)(R6H)-;
CH=R7R8R9HSi-;
下标a、b、c、d和e为0或1且满足以下关系:
a+b=1,且当e=1时c+d=1;
R1、R2、R3、R5、R7、R8独立地选自包含1-8个碳原子、更特别地,1-4个碳原子的一价烃基团和包含6-12个碳原子的一价的芳基和烷芳基烃基团,或R10,
其中R10选自包含3-6个碳原子的支化的一价烃基团、例如非限制性实例的异丙基、叔丁基和叔戊基;
R4和R11独立地选自包含1-4个碳原子、更特别地,1-3个碳原子的二价烃基团;
R6H和R9H选自包含1-8个碳原子、更特别地,1-4个碳原子的线性或支化的一价烃基团或氢,条件是R6H和R9H不同且R6H或R9H为氢,且
其中所述烯烃改性的中间物拥有一个或多个环氧乙烷或环氧丙烷基团而且包含一个或多个末端或悬垂的碳-碳双键且包含3-12个碳原子、更特别地,3-6个碳原子;和,
(b)将所述环氧改性的有机硅中间物加入到季型烷基二甲基叔胺阳离子;其中原位制备所述季型烷基二甲基叔胺阳离子以制造所述具有通式(I)的季型有机硅。
在本文的一个实施方式中,适用于制备环氧取代的有机硅中间物的贵金属催化剂也是本领域所熟知的并且包括铑、钌、钯、锇、铱或铂的络合物。用于Si-H烯烃加成反应的铂催化剂的很多类型是已知的,并且这样的铂催化剂可用于产生本文所描述的组合物的任一种。铂化合物可选自如美国专利No.3,159,601(其通过引用并入这里)中记载的具有式(PtCl2烯烃)和H(PtCl3烯烃)的那些。另外的含铂材料可为氯铂酸与每克铂至多2摩尔的选自由醇、醚、醛和其混合物组成的类别的成员的复合物,正如在美国专利No.3,220,972中所记载的,其通过引用并入这里。可用作本发明中的又一组含铂材料记载于美国专利No.3,715,334;3,775,452和3,814,730(Karstedt)中。本领域技术人员可容易地确定铂催化剂的有效量。通常,有效量基于每百万份的总环氧改性的有机硅中间物在约0.1-50份的范围。
具有通式(I)的季型有机硅的另一制备方法包括:
(a)使氢化物中间物和烯烃改性的中间物以1:1-1:1.4的氢化物中间物对烯烃改性的中间物的摩尔比范围在催化剂如氢化硅烷化催化剂(例如,非限制性实例的贵金属催化剂如本文描述的那些)的存在下进行反应以制造环氧改性的有机硅中间物;和其中所述烯烃改性的中间物为包含一个或多个环氧乙烷或环氧丙烷基团且包含一个或多个末端或悬垂的碳-碳键且包含4-12个碳原子的分子,例如非限制性实例的烯丙基环氧乙烷、烯烃改性的环氧化物例如如下通式的那些:CH2=CH-(CH2)yO(CH2)zCH(O)CH2,其中下标y和z为1-10,或
其中R34和R35独立地选自包含1-2个碳原子的一价烃基团,且其中烯烃改性的中间物的一个非限制性实例为烯丙基缩水甘油基醚,且其中,在一个实施方式中,所述氢化物中间物具有如下通式(VI):
AOaR4 b(BHOcR11 d)eCH (VI)
其中:
A=R1R2R3Si-;
BH=-Si(R5)(R6H)-;
CH=R7R8R9HSi-;
下标a、b、c、d和e为0或1且满足以下关系:
a+b=1,且当e=1时c+d=1;
R1、R2、R3、R5、R7、R8独立地选自包含1-8个碳原子、更特别地,1-6个碳原子的一价烃基团和包含6-12个碳原子的一价的芳基和烷芳基烃基团,或R10,
其中R10选自包含3-6个碳原子的支化的一价烃基团,例如非限制性实例的异丙基、叔丁基和叔戊基;
R4和R11独立地选自包含1-4个碳原子、更特别地,1-3个碳原子的二价烃基团;
R6H和R9H选自包含1-8个碳原子、更特别地,1-4个碳原子的线性或支化的一价烃基团或氢,条件是R6H和R9H不同且R6H或R9H为氢,且
其中所述烯烃改性的中间物拥有一个或多个环氧乙烷或环氧丙烷基团且包含一个或多个末端或悬垂的碳-碳双键且包含4-12个碳原子、更特别地,3-6个碳原子;和
(b)使烷基二甲基叔胺和酸反应以制造季型烷基二甲基胺中间物
使所述环氧改性的有机硅中间物和烷基二甲基叔胺反应以制造胺改性的有机硅中间物;和,
(c)使所述季型烷基二甲基胺中间物和环氧改性的有机硅中间物反应以制造具有通式(I)的季型有机硅。
其中可以使用所述表面活性剂组合物的一些应用为农业应用、涂料应用、个人护理应用和家庭护理应用,以及纺织品、衣物和油气应用。通常,在各应用中使用的具有通式(I)的各个季型有机硅的量将随其期望的应用和性质而变化并且可由本领域技术人员按需进行调整。
本发明的组合物可以多种如下的形态单独地或以其它的组合使用:作为液态溶液、固体在液体中的分散液、固体在作为乳液的液体中的分散液、固体混合物或固溶体。
可将本发明的表面活性剂组合物用在其中的多种用途/应用如下:
A.农药–农业、园艺、草坪、装饰品(观赏植物,ornamental)和林业:
农业组合物被定义为涉及在农作物、林业、草坪和装饰品和公路用地(rights-of-way)应用中使用肥料、杀虫剂、除草剂、杀真菌剂和植物生长调节剂的组合物。
许多农药应用要求将助剂加到喷雾混合物中以在叶面上提供润湿和铺展。助剂常常是表面活性剂,其可具有各种功能,例如增加喷雾液滴在难以润湿的叶面上的保持力,提高铺展以改善喷雾的覆盖率,或者提供除草剂进入植物表皮的渗透性。这些助剂或者以罐侧添加剂(tank-side additive)提供,或者用作农药制剂中的组分。
农药的典型用途包括农业、园艺、草坪、装饰品、家庭及花园、兽医和林业的应用。本发明的农药组合物还包括至少一种农药,其中本发明的基于季型有机硅的表面活性剂可以足以释放0.005%-2%的最终使用浓度的量存在,其作为浓缩物或在罐混合物中稀释。任选地,所述农药组合物可包括赋形剂、助表面活性剂、溶剂、泡沫控制剂、沉积助剂、阻流剂(drift retardants)、生物制剂、微量养料、肥料等。术语农药意指用于消灭害虫的任意化合物,例如灭鼠剂、杀虫剂、杀螨剂、杀真菌剂和除草剂。可使用的农药的说明性实例包括但不限于生长调节剂、光合作用抑制剂、颜料抑制剂、有丝分裂破坏剂(mitotic disrupter)、脂质生物合成抑制剂(lipid biosynthesis inhibitors)、细胞壁抑制剂和细胞膜破裂剂(cell membrane disrupter)。用作本发明的组合物中的农药的量随所使用的农药类型而变化。
可与本发明的组合物一起使用的农药化合物化合物的更具体的实例为但不限于除草剂和生长调节剂,例如:苯氧基乙酸、苯氧基丙酸、苯氧基丁酸、苯甲酸、三嗪和均三嗪、取代的尿素、尿嘧啶、苯达松、甜菜胺、灭草定、苯敌草、达草止、基胺三唑、异草酮、氟啶酮、达草灭、二硝基苯胺、异乐灵、黄草消、喷达曼萨林、氨基丙氟灵、氟乐灵、草甘膦、磺酰脲、咪唑啉酮、烯草酮(clethodim)、禾草灵、唑禾草灵、吡氟禾草灵、吡氟氯禾灵(haloxyfop-methyl)、喹禾灵、稀禾定、敌草腈、异草胺和联吡啶化合物。另外,麦草畏和环磺酮(tembotrione)。
可在本发明中使用的杀真菌剂组合物包括但不限于,杀螟丹(aldimorph)、克啉菌、吗菌灵、烯酰吗啉;氟硅唑、戊环唑、环唑醇、氧唑菌、呋菌唑、丙环唑、戊唑醇等;烯菌灵、托布津、苯菌灵、多菌灵、百菌清(chlorothialonil)、氯硝胺、肟菌酯(trifloxystrobin)、氟嘧菌酯(fluoxystrobin)、醚菌胺(dimoxystrobin)、腈嘧菌酯(azoxystrobin)、灭菌胺(furcaranil)、丙氯灵、磺菌胺、恶唑菌酮(famoxadone)、克菌丹、代森锰、代森锰锌、多敌菌、多果定,和甲霜灵。
可与本发明的组合物一起使用的包括杀幼虫剂、杀螨剂和杀卵剂(ovacide)化合物的杀虫剂为但不限于苏云金芽孢杆菌、多杀菌素、阿维菌素、多拉菌素、皮菌素(lepimectin)、除虫菊酯、甲萘威、丙硫菌唑、涕灭威、灭多威、阿米曲唑、硼酸、杀螟螨、敌草胺(novaluron)、双三氟虫脲(bistrifluron)、杀铃脲(triflumuron)、除虫脲(diflubenzuron)、吡虫啉、二嗪农,乙酰甲胺磷、硫丹、克来范(kelevan)、乐果、益棉磷、谷硫磷、唑磷(izoxathion)、毒死蜱、四螨嗪、λ-氯氟氰菊酯、苄氯菊脂、联苯菊酯、氯氰菊酯等。
肥料和微量养料:
肥料或微量养料包括但不限于硫酸锌、硫酸亚铁、硫酸铵,尿素,尿素铵氮(ureaammonium nitrogen)、硫代硫酸铵、硫酸钾、磷酸单铵、磷酸脲、硝酸钙、硼酸、硼酸的钾和钠盐、磷酸、氢氧化镁、碳酸镁、多硫化钙、硫酸铜、硫酸锰、硫酸铁、硫酸钙、钼酸钠、氯化钙。
所述农药或肥料可为液体或固体。如果其为固体,则优选的是,其在施加之前可溶解于溶剂或本发明的基于季型有机硅的表面活性剂中,并且所述有机硅可充当溶剂,或者用于这样的溶解的表面活性剂或另外的表面活性剂可发挥该功能。
农业赋形剂:
缓冲剂、防腐剂和本领域已知的其它标准赋形剂也可包括在所述组合物中。
溶剂也可包括在本发明的组合物中。这些溶剂在室温是液态。实例包括水、醇、芳族溶剂、油类(即矿物油、植物油、硅油等)、植物油的低级烷基酯、脂肪酸、酮、甘醇、聚乙二醇、二醇、石蜡等。具体的溶剂可为如美国专利5,674,832中所述的2,2,4-三甲基-1,3-戊烷二醇及其烷氧基化的(尤其是乙氧基化的)变体,或N-甲基-吡咯烷酮(n-methyl-pyrrilidone),所述美国专利并入本文作为参考。
助表面活性剂:
本文可使用的助表面活性剂包括非离子型表面活性剂、阳离子型表面活性剂、阴离子型表面活性剂、两性表面活性剂、两性离子型表面活性剂、聚合物型表面活性剂或其任何混合物。表面活性剂典型地基于烃、基于有机硅或基于碳氟化合物。
另外,也有用的是其它助表面活性剂,其具有不妨碍超铺展(superspreading)的短链疏水基团,如美国专利5,558,806中所述,所述美国专利通过参考并入本申请。
有用的表面活性剂包括含有嵌段共聚物的烷氧基化物,尤其是乙氧基化物,所述嵌段共聚物包括环氧乙烷、环氧丙烷、环氧丁烷及其混合物的共聚物;烷基芳基烷氧基化物,尤其是乙氧基化物或丙氧基化物,以及它们的衍生物,包括烷基苯酚乙氧基化物;芳基芳基烷氧基化物,尤其是乙氧基化物或丙氧基化物,以及它们的衍生物;胺烷氧基化物,尤其是胺乙氧基化物;脂肪酸烷氧基化物;脂肪醇烷氧基化物;烷基磺酸盐;烷基苯和烷基萘磺酸盐;硫酸化脂肪醇,胺或酰胺;羟乙磺酸钠的酸酯(acid esters of sodiumisethionate);磺基丁二酸钠的酯;硫酸化或磺化脂肪酸酯;石油磺酸盐;N-酰基肌氨酸盐;烷基多糖苷(alkyl polyglycoside);烷基乙氧基化的胺;等。
具体的实例包括烷基炔属二醇(SURFONYL-Air Products)、基于吡咯烷酮(pyrrilodone)的表面活性剂(例如,SURFADONE-LP 100-ISP)、2-乙基己基硫酸盐、异癸醇乙氧基化物(例如,RHODASURF DA 530-Rhodia)、乙二胺烷氧基化物(TETRONICS-BASF)、环氧乙烷/环氧丙烷共聚物(PLURONICS-BASF)、Gemini型表面活性剂(Rhodia)和二苯醚Gemini型表面活性剂(例如DOWFAX-Dow Chemical)。
优选的表面活性剂包括环氧乙烷/环氧丙烷共聚物(EO/PO);胺乙氧基化物;烷基多糖苷;氧代-十三烷醇乙氧基化物,等等。
在优选的实施方式中,本发明的农用化学品组合物还包括一种或多种农用化学品成分。合适的农用化学品成分包括,但不限于,除草剂、杀虫剂、生长调节剂、杀真菌剂、杀螨药(miticide)、杀螨剂(acaricide)、肥料、生物制剂、植物营养物、微量营养素、生物杀灭剂、石蜡矿物油、甲基化种子油(即甲基大豆脂肪酸金属盐(methylsoyate)或甲基油菜油金属盐(methylcanolate))、植物油(例如大豆油和油菜油)、水质调节剂例如(Loveland Industries,Greeley,CO)和Quest(Helena Chemical,Collierville,TN)、改性的粘土例如(Englehard Corp.,)、控泡剂、表面活性剂、润湿剂、分散剂、乳化剂、沉积助剂、防滴组分(antidrift component),和水。
合适的农用化学品组合物以本领域已知的方式通过合并制得,例如,通过将一种或多种上述组分与本发明的有机改性的二硅氧烷混合,作为桶混制剂,或者作为"罐装"制剂。术语"桶混制剂"是指在即将使用时将至少一种农用化学品加到喷雾介质,例如水或油中。术语"罐装"是指含有至少一种农用化学品组分的制剂或浓缩物。然后,在即将使用时可将"罐装"制剂稀释至使用浓度,典型地稀释到桶混制剂中,或者可不稀释而直接使用它。
B.涂料:
典型地,为了乳化、组分的增容、匀化(leveling)、流动和减少表面缺陷的目的,涂料制剂需要润湿剂或表面活性剂。此外,这些添加剂可给固化的或干的膜带来改进,例如改善的耐磨性、防粘连性、亲水性和疏水性。涂料制剂可作为含溶剂的涂料、含水的涂料和粉末涂料存在。
涂料组分可用作:建筑涂料;OEM产品涂料例如汽车涂料和卷材涂料;专用涂料例如工业保养涂料(industrial maintenance coating)和船舶涂料;
典型的树脂类型包括:聚酯、醇酸树脂、丙烯酸类(acrylics)树脂、环氧树脂。
C.个人护理
在优选的实施方式中,本发明的基于季型有机硅的表面活性剂包括每100重量份(“pbw”)的个人护理组合物0.1-99pbw、更优选地0.5pbw-30pbw且甚至更优选地1-15pbw的基于季型有机硅的表面活性剂,和1pbw-99.9pbw、更优选地70pbw-99.5pbw且甚至更优选地85pbw-99pbw的个人护理组合物。
本发明的基于季型有机硅的表面活性剂组合物可在个人护理乳液例如洗剂和霜剂中使用。正如通常所知的,乳液包括至少两个不混溶的相,其中一个为连续相,而另一个为不连续相。另外,乳液可为具有不同粘度的液体或固体。另外,乳液的粒度使得它们成为微乳液,并且当其足够小时,微乳液可为透明的。进一步地,还可制备乳液的乳液,并且这些通常称为多重乳液。这些乳液可为:
1)水乳液,其中不连续相包括水且连续相包括本发明的基于季型有机硅的表面活性剂;
2)水乳液,其中不连续相包括本发明的基于季型有机硅的表面活性剂且连续相包括水;
3)非水乳液,其中不连续相包括非水的羟基溶剂且连续相包括本发明的基于季型有机硅的表面活性剂;和
4)非水乳液,其中连续相包括非水的羟基有机溶剂且不连续相包括本发明的基于季型有机硅的表面活性剂。
包括有机硅相的非水乳液记载于美国专利6,060,546和美国专利6,271,295中,其公开内容通过引用以此和由此特别地并入。
正如本文所使用的,术语“非水羟基有机化合物”是指在室温例如约25℃和约1大气压时为液体的含羟基的有机化合物,示例性的有醇、二醇、多羟基醇和聚合二醇和其混合物。非水的有机羟基溶剂选自在室温例如约25℃和约一个大气压下为液体的含羟基的有机化合物,其包括醇、二醇、多羟基醇和聚合二醇和其混合物。优选地,所述非水的羟基有机溶剂选自乙二醇、乙醇、丙醇、异丙醇、丙二醇、一缩二丙二醇、二缩三丙二醇、丁二醇、异丁二醇、甲基丙二醇、甘油、山梨糖醇、聚乙二醇、聚丙二醇单烷基醚、聚氧化烯共聚物及其混合物。
一旦获得期望的形式,无论是作为有机硅的单相、包括有机硅相的无水混合物、包括有机硅相的含水混合物、油包水乳液、水包油乳液,或者两种非水乳液的任一种或其变体,得到的物质都常常是具有改善的沉积性质和良好的触摸特性的霜或露。可将其共混到毛发护理品、皮肤护理品、止汗剂、遮光剂、化妆品、加色化妆品、驱虫剂、维生素和激素载体、香料载体等的制剂中。
可将本发明的基于季型有机硅的表面活性剂和本发明的由其衍生的有机硅组合物用于其中的个人护理应用包括但不限于,除臭剂,止汗剂,止汗剂/除臭剂,剃须产品,护肤露,保湿剂,收敛剂(toners),浴室用品,清洁产品,护发产品比如香波、调理剂、摩丝、定型发胶、美发喷剂、染发剂、染发产品、头发漂白剂、烫发产品、直发剂,修指甲产品比如指甲油、指甲油去除剂、指甲霜和露、角质层软化剂,防护膏比如遮光剂、驱虫剂和抗老化产品,加色化妆品比如口红、粉底、扑面粉、眼线膏、眼影、胭脂、彩妆用品、睫毛油和常规添加了有机硅组分的其它个人护理品制剂,以及用于要施用于皮肤的医学组合物的局部施用的药物递送系统。
在优选的实施方式中,本发明的个人护理品组合物还包括一种或多种个人护理品成分。合适的个人护理品成分包括,例如,软化剂、保湿剂、湿润剂、颜料,包括珠光颜料例如氯氧化铋和二氧化钛涂覆的云母、着色剂、香料、生物杀灭剂、防腐剂、抗氧化剂、抗微生物剂、抗真菌剂、止汗剂、皮肤角质层剥离剂(exfoliant)、激素、酶、药用化合物、维生素、盐、电解质、醇、多元醇、紫外线吸收剂、植物提取物、表面活性剂、硅油、挥发性硅酮、有机油(organic oil)、蜡、成膜剂、增稠剂例如热解法二氧化硅或水合二氧化硅、粒状填料例如滑石、高岭土、淀粉、改性淀粉、云母、尼龙、粘土例如膨润土和有机改性的粘土。
合适的个人护理品组合物采用本领域已知的方式通过混合而制备,例如,通过将一种或多种上述组分与基于季型有机硅的表面活性剂混合而制得。合适的个人护理品组合物可为单相形式或乳液形式,包括水包油型、油包水型和无水乳液,其中有机硅相可为不连续相或连续相,以及多重乳液,例如,油包水包油型乳液和水包油包水型乳液。
在一个可用的实施方式中,止汗剂组合物包括本发明的基于季型有机硅的表面活性剂和一种或多种活性止汗剂。合适的止汗剂包括例如在美国食品和药品管理局的1993年10月10日的关于对于不需处方但可合法出售的人类用途的止汗剂药物产品的专著中列举的第I类活性止汗剂成分,例如卤化铝、碱式卤化铝(aluminum hydroxyhalide)如水合氯化铝(aluminum chlorohydrate),及其与卤化氧锆(zirconyl oxyhalide)和碱式卤化氧锆(zirconyl hydroxyhalide)的复合物或混合物,例如,水合氯化铝-锆(aluminum-zirconium chlorohydrate)、铝锆甘氨酸复合物(aluminum zirconium glycinecomplexe)如甘氨酸铝锆四氯水合物(aluminum zirconium tetrachlorohydrex gly)。
在另一有用的实施方式中,皮肤护理组合物包括基于季型有机硅的表面活性剂和载剂例如硅油或有机油。皮肤护理组合物可任选地还包括软化剂,例如甘油三酯,蜡酯(waxester),脂肪酸的烷基或烯基酯,或多元醇酯,和一种或多种通常用于皮肤护理组合物中的已知组分,例如颜料,维生素如维生素A、维生素C和维生素E,遮光剂或防晒化合物(sunblock compound)例如二氧化钛、氧化锌、2-羟基-4-甲氧基-二苯甲酮、辛基甲氧基肉桂酸酯、丁基甲氧基二苯甲酰甲烷、对氨基苯甲酸和辛基二甲基对氨基苯甲酸(octyldimethyl-p-aminobenzoic acid)。
在另一有用的实施方式中,加色化妆品组合物例如口红、彩妆用品或睫毛油组合物包括基于季型有机硅的表面活性剂和着色剂,例如颜料,水溶性染料或油溶性染料。
在另一有用的实施方式中,本发明的组合物与香料物质结合使用。这些香料物质可为香料化合物、包胶的香料化合物或释放香气的化合物,它们可为纯化合物或为包胶的。与本发明的组合物特别相容的是释放香气的含硅化合物,如美国专利6,046,156、6,054,547、6,075,111、6,077,923、6,083,901和6,153,578中所披露的;这些专利均在此并入作为参考。
本发明组合物的应用不局限于个人护理品组合物,还预期用本发明组合物处理的其他产品,例如蜡、上光剂和织物。
D.家庭护理品
家庭护理品应用包括衣物洗涤剂和织物柔软剂、餐具洗涤液、木材和家具上光剂、地板蜡、浴盆和瓷砖清洗剂、抽水马桶清洁剂、硬表面清洗剂、窗户清洁剂、防雾剂、排水沟清理剂、自动餐具洗涤剂和被单洗涤剂(sheeting agent)、地毯清洁剂、预洗去污剂(prewash spotter)、除锈剂和除垢剂。
在本文的一项另外的实施方式中,本发明的季型有机硅表面活性剂组合物是这样的:其使得对于包括具有通式(I)的季型有机硅的应用的多种农业化学品的叶片摄入(叶吸收,foliar uptake)比对于包括牛油胺乙氧基化物的等同应用的多种农业化学品的叶片摄入要快。在另一具体的实施方式中,14C-草甘膦-IPA在稗草(Echinachloa crus-galii)中的叶片摄入通过在所附的Gaskin等人的文献中描述的方法在处理之后的2小时时测定,并且其显示出为牛油胺乙氧基化物的8.9倍大。
以下非约束性的实施例对于本发明是进一步说明性的。
实施例
制备实施例1-季型碳硅烷(QC-1/QC-1A)的合成:
在氮气下向连接有冷凝器的三口烧瓶中加入15g(0.0546mol)单环氧官能的碳硅烷(结构1)、7.478g(0.0546mol)二羟甲基丙酸、5.636g(0.0546mol)N,N’-二甲基氨基丙醇和26.7g异丙醇。将该混合物在80-82℃迅速加热并且搅拌18h。将所述烧瓶冷却到室温并且在40-45℃在真空下以4h将异丙醇除去。最后,将样品在烘箱中在50℃干燥3日,从而获得浅黄色粘稠凝胶。
NMR确认,形成了如结构2(图3)中所示的季型盐。这得到了90%的通过LC-MS定量的所述季型盐的转化率(产物ID:QC-1)。该起始材料的后续制备得到了75%的转化率(产物ID:QC-1A)。
制备实施例2-季型碳硅烷(QC-2)的合成:
在氮气下向连接有冷凝器的三口烧瓶中加入14.25g(0.0519mol)单环氧官能的碳硅烷(结构1)、7.10g(0.0519mol)二羟甲基丙酸、6.185g(0.0519mol)N,N’-二甲基氨基丙烷1,2-二醇和27.5g异丙醇。将该混合物在80-82℃下迅速加热并搅拌18h。将所述烧瓶冷却到室温并且在40-45℃下在真空下以4h将异丙醇除去。最后,将样品在烘箱中在50℃干燥3日,从而获得非常浅的黄色粘稠凝胶。MS确认,以80%的转化率形成了如结构3(图4)中所示的季型盐(产物ID:QC-2)。
制备实施例3-季型碳硅烷(QC-3)的合成:
在氮气下向连接有冷凝器的三口烧瓶中加入14.25g(0.0519mol)单环氧官能的碳硅烷(结构1)、7.10g(0.0519mol)二羟甲基丙酸、5.259g(0.0519mol)N,N’-二甲基丁基胺。将该混合物在87-90℃下迅速加热并且搅拌18h。将所述烧瓶冷却到室温。最后,将样品在烘箱中在50℃下干燥3日,从而获得深棕色粘稠凝胶。
NMR确认,形成了如结构4(图5)中所示的季型盐(产物ID:QC-3)。
制备实施例4-季型三硅氧烷(TSQ-1)的合成:
在氮气下向连接有冷凝器的三口烧瓶中加入15g(0.0445mol)2-(3-缩水甘油基氧丙基)-七甲基三硅氧烷(结构5)、6.097g(0.0445mol)二羟甲基丙酸、4.596g(0.0445mol)N,N’-二甲基氨基丙醇和12g异丙醇。将该混合物在60-65℃下迅速加热并搅拌18h。将所述烧瓶冷却到室温并且在25℃在真空下以2h将异丙醇除去,从而获得黄色粘稠凝胶。
MS确认,形成了如结构6(图6)中所示的季铵盐(产物ID:TSQ-1)。
对比性有机硅表面活性剂
对比性有机硅表面活性剂描述于下:
对比性-A:(CH3)3-Si-CH2CH2Si(CH3)2CH2CH2CH2O(CH2CH2O)8CH3
对比性-B:三硅氧烷乙氧基化物(Silwet L-77):
(CH3)3-Si-O-Si(CH3)(Z)-OSi(CH3)3
其中Z=-CH2CH2CH2O(CH2CH2O)8CH3
其它表面活性剂:
其它对比性基于非硅的表面活性剂描述于表1中。
表1.基于非硅的表面活性剂
季型有机硅的铺展性
使用0.1%-0.4%(活性物)表面活性剂测定铺展。在Milli-Pore水(去离子的)中制备溶液,其中将10μL小滴置于聚苯乙烯表面(培养皿)上,并且在30秒之后测定铺展直径。
表2.季型碳硅烷的铺展性
表面活性剂ID | 0.1重量% | 0.2重量% | 0.4重量% |
QC-1 | 13 | 33 | 47 |
QC-2 | 10 | 23 | 40 |
QC-3 | 14 | 23 | 36 |
TSQ-1 | 15 | 30 | nd |
TAE-2 | 5 | 6 | 7 |
对比性-A | 43 | 54 | nd |
对比性-A样品得到最高的铺展度。然而,本发明的组合物相对于基于非硅的阳离子表面活性剂TAE-2得到了在铺展方面预料不到的提高。典型地,本领域技术人员会对季型有机硅表面活性剂的铺展进行预估而得到和TAE-2类似的铺展水平(表2)。
季型三硅氧烷的表面性质
该试验表明本发明组合物的表面张力效力。多种表面活性剂的水表面张力(aqueous surface tension)通过使用喷砂处理的铂叶片作为感测器的Wilhelmy Plate方法测定。使用Kruss表面张力计进行测量。在环境温度(~22℃)下制备0.00001%-1重量%的在0.005M NaCl中的表面活性剂溶液。
表3表明TSQ-1在0.01-1重量%的浓度(用于农业喷雾应用的典型的使用水平)下预料不到地提供了和非离子对应物三硅氧烷乙氧基化物(对比例-B)类似的表面张力和比碳硅烷乙氧基化物(对比例-A)低的表面张力。
表3.季型三硅氧烷的表面性质
助表面活性剂对铺展性的影响
助表面活性剂的使用通常用于赋予除草剂制剂另外的益处。充当相容剂或与主表面活性剂相互作用以显现期望的润湿性。用于草甘膦制剂的常见的助表面活性剂选自包含10-20个环氧乙烷单元的牛油胺乙氧基化物(TAE)、源自8-16个碳单元且包含1.2-1.7个葡糖单元的脂肪醇的烷基多糖苷(APG)和两性表面活性剂例如烷基氨基甜菜碱。
使用0.2%(活性物)总的表面活性剂溶液测定铺展,其中将10μL小滴置于聚苯乙烯表面上并且在30秒之后测定铺展直径。改变QC-1A对助表面活性剂的比率以测定由这两种表面活性剂之间的相互作用引起的协同或对抗效应的可能性。基于QC-1A和助表面活性剂之间的线性关系将每组的铺展结果(实际的)和预期值(加权平均的)进行比较。
表4表明助表面活性剂可对于本发明组合物的铺展性产生影响。如所预期的,QC-1A和TAE-1的共混物对于QC-1A的铺展是对抗的。这通过铺展相对于预期值减少而被观察到。然而,令人惊讶地,QC-1A和APG的混合物在铺展方面相对于预期值得到增加,显示在铺展方面的协同性。QC-1A/两性共混物在包含至少50%QC-1A的共混比率下得到线性响应。然而,在<50%QC-1A的共混比率下,铺展貌似是非线性响应(略微对抗)。
表4.助表面活性剂对季型有机硅铺展的影响
助剂对14C-草甘膦异丙基胺盐在稗草中摄入的作用
14C-草甘膦(除草剂)在稗草(Echinochloa crus-galli)中的摄入在根据Gaskin等人(Gaskin,R.E.;Stevens,P.J.G.1992.Pestic.Sci.38:185-192.)记载的方法的处理(HAT)之后的2小时和24小时测定,以确立表面活性剂对摄入速度的影响。摄入在最幼小的完全伸展的叶子上测定;4叶期的约10cm高的植物。
表5表明本发明的组合物QC-1相对于TAE-2在2HAT时显著提高草甘膦的摄入,甚至在4X的更低的使用比率也是如此(将0.2%的TAE-2相对于0.05%的QC-1作比较)。
表5.表面活性剂对14C-草甘膦在稗草中的摄入的作用
具有共同后标(postscript)的平均值并未显著地不同(P0.05,LSD试验)。
草甘膦中的分散性
用在农业制剂中的表面活性剂的一个重要性质为其在高离子强度的溶液例如硫酸铵或除草剂盐(即草甘膦异丙基胺)中的分散性或溶解性。
制备包含5%的对比性-B或本发明组合物的含水的草甘膦-异丙基胺(480g/L)制剂并且对于分散性进行评价。在20-22℃下视觉上观察所述制剂的澄清度,如果从清澈到混浊,则也测量浊点。
浊点通过将15mL制剂放置在容纳数字温度计的20特拉姆的小瓶中和在磁力搅拌器/加热板上缓慢地加热混合物而测定。将所述溶液变成不透明时的温度记录为所述浊点。
表6表明不同于在草甘膦制剂中不能溶解的对比性-B,本发明的组合物为可溶的或可分散的(混浊的),从而容许在高电解质制剂中使用。表面活性剂(对比性-B)在草甘膦制剂中不能溶解。
表6.表面活性剂以5%在480g/L草甘膦制剂中的浊点
制备实施例5
使用和以上的制备实施例1-4所概述的相似的合成步骤制备以下化合物(制备实施例5)。
制备实施例6-季型碳硅烷(QC-4)的合成:
在氮气下向连接有冷凝器的三口烧瓶中加入3g(0.011mol)单环氧官能的碳硅烷(结构1)和1.5g(0.011mol)N,N’-二甲基氨基丙烷1,2-二醇。将该混合物在25℃搅拌2.5h。向该混合物添加1.12g(0.011mol)乳酸和2.5ml异丙醇并且搅拌18h。在此阶段停止所述反应并且将氮气通入反应混合物。最后,然后将其在25℃在真空(3托)下保持4h以除去挥发物。获得了红棕色粘稠液体,并且MS确认形成了如结构7所示的季铵盐。
生物降解性
在本文的一个实施方式中,本发明的生物可降解的表面活性剂组合物的是这样的:其使得具有通式(I)的聚酯改性的季型有机硅的生物降解性比三硅氧烷烷氧基化物例如聚环氧烷烃(聚氧化烯)改性的七甲基三硅氧烷的生物降解性快。在更具体的实施方式中,所述改善通过标准的28日生化需氧量(BOD)/化学需氧量(COD)双氧化试验测量。在一个非限制性实例中,这样的BOD/COD试验为OECD TG 301°F Ready Biodegradability:Manometric Respirometery Test。在一个非限制性实施方式中,相比于聚环氧烷烃改性的七甲基三硅氧烷,本发明的生物可降解的表面活性剂组合物(式Vll)相对于常规的三硅氧烷烷氧基化物例如Silwet L-77表面活性剂的改善为至少约30%的改善。
尽管参考很多示例性实施方式已经对本发明进行了描述,但是本领域技术人员将领悟到可作出多个改变并且可用等同物取代其元素而没有偏离本发明的范围。另外,可进行很多变更以使具体的情形或材料适用于本发明的教导而不偏离其实质范围。因此,期望本发明不限于本文公开的任何具体的示例性实施方式。
Claims (27)
1.表面活性剂组合物,其包括具有通式(I)的季型有机硅盐:
AOaR4 b(BOcR11 d)eC (I)
其中:
A=R1R2R3Si-;
B=-Si(R5)(R6)-;
C=R7R8R9Si-;
下标a、b、c、d和e为0或1且满足以下关系:
a+b=1,且当e=1时c+d=1;
R1、R2、R3、R5、R7、R8各自独立地选自包含1-8个碳原子的一价烃基团、包含6-12个碳原子的一价的芳基和烷芳基烃基团、和R10,
其中R10选自包含3-6个碳原子的支化的一价烃基团;
R4和R11各自独立地为包含1-4个碳原子的二价烃基团;
R6和R9各自独立地选自包含1-8个碳原子的线性或支化的一价烃基团、和R12,条件是R6和R9不同且R6或R9之一为R12,
其中R12选自R*或-R13R14N⊕(R15)(R16)R17XY,
其中R*为
其中R19和R20独立地选自H或甲基,
R21和R22不相同且选自OH或R23;
R23为-N⊕(R15)(R16)R17XY,
其中R13为包含3-12个碳原子且任选地被一个或多个羟基所取代的二价烃基团,
R14选自-OCH2CH(OH)CH2-和通式(II)的氧化烯基团:
-[OC2H4]h-[OC3H6]i-[OC4H8]k-OCH2CH(OH)CH2- (II)
其中下标h、i和k为零或正数并且满足以下关系:1≤h+i+k≤15,更特别地,1≤h+i+k≤10,甚至更特别地,h为0-8、i为0-5且k为0-4,
R15和R16独立地选自包含1-2个碳原子的一价烃基团,
R17选自可各自任选地被一个或多个羟基所取代的包含1-6个碳原子的线性或支化的烃基团和通式(III)的氧化烯基团:
-[OC2H4]m-[OC3H6]n-[OC4H8]p-R18 (III)
其中下标m、n和p为零或正数并且满足以下关系:1≤m+n+p≤15,
R18选自-OH和包含1-4个碳原子的一价烃基团;且
XY为R34或较易于生物降解的基团RPE,
R34选自包含2-22个碳原子的羧酸阴离子部分且具有通式:
YO-C(=O)-C(R35)(R36)(R37)
其中下标q、r和s为0或1,
R35和R36选自H、OH、1-3个碳原子的烃基团或CH2OH,
R37选自H、OH、1-3个碳原子的烃基团、CH2OH或-(CH R38)f-CH2R39,
其中R38为H、OH、1-3个碳原子的烃基团或CH2OH;R39为H或OH,下标f为0-3,
其中RPE为源自对应的羟基羧酸或对应的羟基羧酸和羧酸的混合物的酯化的聚酯部分,其中所述羟基羧酸包含2-8个碳原子,且RPE为通式(Z):
YO-C(=O)-CH(3-[q+r+s])(R24)q(R25)r(R26)s (Z)
下标q、r和s为0或1,
其中R24、R25、R26独立地选自-OH、-CH2OH、-(CH2)mOR27、-CH3、-CH2CH3、-(CH2)mO-C(=O)(CR30R31)tCH2OR32或R28,
其中R27为-C(=O)-CH(3-[q+r+s])(R24)q(R25)r(R26)s
R28为-R29OR27,其中R29为2-6个碳原子的二价烃自由基,
R30和R31独立地选自H、-OH、-CH2OH、-(CH2)mO-R27、-CH3、-CH2CH3或-(CH2)mO-C(=O)-(CR30R31)tCH2OR32,
R32独立地选自H、-CH2OH、-CH3、-CH2CH3、R27或[-C(=O)(CR30R31)tCH2O]w-R33,
R33独立地选自H、-CH2OH、-CH3或-CH2CH3,
其中,
下标m为0-3,
下标t为1-5,
下标w为1-5,且
RPE中酯键的数量为1-10,
条件是当R24、R25和R26的任何一个或多个为式-(CH2)mO-C(=O)(CR30R31)tCH2OR32时,R24、R25和R26基团包含1-10个-(CH2)mO-C(=O)(CR30R31)tCH2OR32基团。
2.权利要求1的组合物,其中XY选自单羧酸、二羧酸、α-羟基酸、β-羟基酸、二羟基酸以及饱和的和不饱和的脂肪酸的阴离子。
3.权利要求1的组合物,其中所述季型有机硅具有如下通式(IV):
AR4C (IV)
其中:
A=R1R2R3Si-;且
C=R7R8R9Si-;
其中R1、R2、R3、R7和R8为甲基;
R4为-CH2CH2-;
R9为R12,
其中R12为-R13R14N⊕(R15)(R16)R17XY,
其中R13is-CH2CH2CH2-;
R14is-OCH2CH(OH)CH2-;
R15和R16为甲基;
R17为-CH2CH(OH)CH2-OH;和
XY为CH3C(CH2OH)2COO-。
4.权利要求1的组合物,其中所述季型有机硅具有如下通式(V):
AR4BOC (V)
其中:
A=R1R2R3Si-;
B=-Si(R5)(R6)-;且
C=R7R8R9Si-;
其中R1、R2、R3、R5、R6、R7和R8为甲基;
R9为R12;
其中R12为-R13R14N⊕(R15)(R16)R17XY,
其中R13为-CH2CH2CH2-;
R14为-OCH2CH(OH)CH2-;
R15和R16为甲基;
R17为-CH2CH2CH2OH;且
XY为CH3C(CH2OH)2COO-。
5.权利要求1的组合物,其中所述季型有机硅具有如下通式(V-B):
AOBOC (V-B)
其中:
A=R1R2R3Si-;
B=-Si(R5)(R6)-;且
C=R7R8R9Si-;
其中R1、R2、R3、R5、R7、R8和R9为甲基;
R6为R12;
其中R12为-R13R14N⊕(R15)(R16)R17XY,
其中R13为-CH2CH2CH2-;
R14为-OCH2CH(OH)CH2-;
R15和R16为甲基;
R17为-CH2CH2CH2OH;且
XY为CH3C(CH2OH)2COO-。
6.制备权利要求1的具有通式(I)的季型有机硅的方法,其包括:
(a)使氢化物中间物和烯烃改性的中间物在催化剂的存在下进行反应以制造环氧改性的有机硅中间物,
其中:
所述氢化物中间物具有如下通式(VI):
AOaR4 b(BHOcR11 d)eCH (VI)
其中:
A=R1R2R3Si-;
BH=-Si(R5)(R6H)-;
CH=R7R8R9HSi-;
下标a、b、c、d和e为0或1且满足以下关系:
a+b=1且c+d=1(当e=1时);
R1、R2、R3、R5、R7、R8独立地选自包含1-8个碳原子的一价烃基团、包含6-12个碳原子的一价的芳基和烷芳基烃基团、和R10,
其中R10选自包含3-6个碳原子的支化的一价烃基团;
R4和R11独立地选自包含1-4个碳原子的二价烃基团;
R6H和R9H选自包含1-8个碳原子的线性或支化的一价烃基团和氢,条件是R6H和R9H不同且R6H或R9H为氢,且
所述烯烃改性的中间物拥有一个或多个环氧乙烷或环氧丙烷基团且包含一个或多个末端或悬垂的碳-碳双键且包含4-12个碳原子;且,
(b)将所述环氧改性的有机硅中间物加入到季型烷基二甲基叔胺阳离子;
从而制造具有通式(I)的季型有机硅。
7.权利要求6的方法,其中所述烯烃改性的中间物为烯丙基环氧乙烷。
8.权利要求6的方法,其中所述烯烃改性的中间物为烯丙基缩水甘油基醚。
9.权利要求6的方法,其中所述季型烷基二甲基叔胺阳离子是原位形成的。
10.制备权利要求1的具有通式(I)的季型有机硅的方法,其包括:
(a)使氢化物中间物和烯烃改性的中间物在催化剂的存在下进行反应以制造环氧改性的有机硅中间物,其中:
所述氢化物中间物具有如下通式(VI):
AOaR4 b(BHOcR11 d)eCH (VI)
其中:
A=R1R2R3Si-;
BH=-Si(R5)(R6H)-;
CH=R7R8R9HSi-;
下标a、b、c、d和e为0或1且满足以下关系:
a+b=1,且当e=1时c+d=1;
R1、R2、R3、R5、R7、R8独立地选自包含1-8个碳原子的一价烃基团、包含6-12个碳原子的一价的芳基和烷芳基烃基团、和R10,
其中R10选自包含3-6个碳原子的支化的一价烃基团;
R4和R11独立地选自包含1-4个碳原子的二价烃基团;
R6H和R9H选自包含1-8个碳原子的线性或支化的一价烃基团和氢,条件是R6H和R9H不同且R6H或R9H为氢,且
所述烯烃改性的中间物拥有一个或多个环氧乙烷或环氧丙烷基团、且包含一个或多个末端或悬垂的碳-碳双键、且包含4-12个碳原子;
(b)使烷基二甲基叔胺和酸进行反应以制造季型中间物,将该季型中间物加入到所述环氧改性的有机硅中间物以制造具有通式(I)的季型有机硅。
11.权利要求10的方法,其中所述烯烃改性的中间物为烯丙基环氧乙烷。
12.权利要求10的方法,其中所述烯烃改性的中间物为烯丙基缩水甘油基醚。
13.农业组合物,其包括:(i)农业化学活性成分;(ii)权利要求1的表面活性剂组合物;(iii)任选的一种或多种农业化学赋形剂,其选自缓冲剂、防腐剂和溶剂;和(iv)任选的一种或多种助表面活性剂,其选自非离子型、阳离子型、阴离子型、两性型、两性离子型和聚合物型表面活性剂。
14.权利要求13的农业组合物,其中所述组合物为除草剂、杀真菌剂和杀虫剂的一种或多种。
15.权利要求14的农业组合物,其中所述农业化学成分为草甘膦。
16.农作物或植物,其具有向其施加的权利要求13的农业组合物。
17.涂料组合物,其包括权利要求1的表面活性剂组合物,其中涂料应用选自建筑涂料、OEM产品涂料、工业维护涂料和船舶涂料。
18.个人护理组合物,其包括权利要求1的表面活性剂组合物。
19.个人护理组合物,其为水乳液,其中不连续相包括水且连续相包括权利要求1的表面活性剂组合物。
20.个人护理组合物,其为水乳液,其中不连续相包括权利要求1的表面活性剂组合物且连续相包括水。
21.个人护理组合物,其为非水乳液,其中不连续相包括非水的羟基溶剂且连续相包括权利要求1的表面活性剂组合物。
22.个人护理组合物,其为非水乳液,其中连续相包括非水的羟基有机溶剂且不连续相包括权利要求1的表面活性剂组合物。
23.个人护理应用,其包括权利要求18的个人护理组合物,其中所述个人护理应用选自除臭剂,止汗剂,止汗剂/除臭剂,剃须产品,护肤露,保湿剂,收敛剂,浴室用品,清洁产品,护发产品比如香波、调理剂、摩丝、定型发胶、美发喷剂、染发剂、染发产品、头发漂白剂、烫发产品、直发剂,修指甲产品比如指甲油、指甲油去除剂、指甲霜和露、角质层软化剂,防护膏比如遮光剂、驱虫剂和抗老化产品,加色化妆品比如口红、粉底、扑面粉、眼线膏、眼影、胭脂、彩妆用品、睫毛油和常规添加了有机硅组分的其它个人护理品制剂,以及用于要施用于皮肤的医学组合物的局部施用的药物递送系统。
24.权利要求23的个人护理应用,其包括至少一种个人护理成分,其选自:软化剂、保湿剂、湿润剂、颜料,包括珠光颜料例如氯氧化铋和二氧化钛涂覆的云母、着色剂、香料、生物杀灭剂、防腐剂、抗氧化剂、抗微生物剂、抗真菌剂、止汗剂、皮肤角质层剥离剂、激素、酶、药用化合物、维生素、盐、电解质、醇、多元醇、紫外线吸收剂、植物提取物、表面活性剂、硅油、挥发性硅酮、有机油、蜡、成膜剂、增稠剂例如热解法二氧化硅或水合二氧化硅、粒状填料例如滑石、高岭土、淀粉、改性淀粉、云母、尼龙、粘土例如膨润土和有机改性的粘土
25.家庭护理组合物,其包括权利要求1的表面活性剂组合物。
26.家庭护理应用,其包括权利要求25的家庭护理组合物,其中所述家庭护理应用选自:衣物洗涤剂和织物柔软剂、餐具洗涤液、木材和家具上光剂、地板蜡、浴盆和瓷砖清洗剂、抽水马桶清洁剂、硬表面清洗剂、窗户清洁剂、防雾剂、排水沟清理剂、自动餐具洗涤剂和被单洗涤剂、地毯清洁剂、预洗去污剂、除锈剂和除垢剂
27.权利要求1的表面活性剂组合物,其中具有通式(I)的酯改性的有机硅的生物降解性比三硅氧烷烷氧基化物的生物降解性快。
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