CN1468887A - Prepn and application of organosilicon quaternary ammonium salt polymer - Google Patents
Prepn and application of organosilicon quaternary ammonium salt polymer Download PDFInfo
- Publication number
- CN1468887A CN1468887A CNA021343721A CN02134372A CN1468887A CN 1468887 A CN1468887 A CN 1468887A CN A021343721 A CNA021343721 A CN A021343721A CN 02134372 A CN02134372 A CN 02134372A CN 1468887 A CN1468887 A CN 1468887A
- Authority
- CN
- China
- Prior art keywords
- quaternary ammonium
- ammonium salt
- salt polymer
- application method
- organosilicon quaternary
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 19
- 229920000642 polymer Polymers 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- -1 Alkoxy silane Chemical compound 0.000 claims abstract description 9
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 8
- 239000000178 monomer Substances 0.000 claims abstract description 4
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003995 emulsifying agent Substances 0.000 claims description 5
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000008367 deionised water Substances 0.000 claims description 2
- 229910021641 deionized water Inorganic materials 0.000 claims description 2
- 239000012153 distilled water Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 239000012875 nonionic emulsifier Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000005846 sugar alcohols Polymers 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 239000004744 fabric Substances 0.000 abstract description 12
- 241000894006 Bacteria Species 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 4
- 230000002147 killing effect Effects 0.000 abstract description 3
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- 241000192125 Firmicutes Species 0.000 abstract 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract 1
- 229920000578 graft copolymer Polymers 0.000 abstract 1
- 229910000077 silane Inorganic materials 0.000 abstract 1
- 239000000047 product Substances 0.000 description 14
- 230000003115 biocidal effect Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004945 emulsification Methods 0.000 description 3
- 230000002070 germicidal effect Effects 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000002414 glycolytic effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
Landscapes
- Silicon Polymers (AREA)
Abstract
The present invention relates to preparation and application of organosilicon quaternary ammonium salt polymer. Alkoxy silane with gamma-halopropyl radical and tertiary amine react at 70-140 deg.c for 0.5-24 hr, and the product is further copolycondensated with polysiloxane and other siloxane monomer to produce organic grafted polymer with quaternary ammonium salt. The polymer has excellent hydrolysis stability, excellent adhering capacity with fabric and hair, powerful killing effect on various Gram-positive bacteria and Gram-negative bacteria and better flexibilizing effect for fabric and hair.
Description
Technical field:
The present invention relates to organosilicon quaternary ammonium salt polymer preparation and application method.
Technical background:
The like product kind is a lot of at present, and roughly having of having patented is following several:
A kind of polysiloxane copolymer of Chinese patent (99111454.X) report with quaternary ammonium lateral group, it be with the polysiloxane copolymer of γ-halopropyl side group and tertiary amine in polar solvent, form in 100-110 ℃ of reaction 40-96h, the main finishing composition as fabric and fiber of this invention also is used for organic resin properties-correcting agent.
A kind of application of polydiorganosiloxane in fabric softener of Chinese patent (98804641.5) report through selecting.
A kind of organic silicon emulsion of United States Patent (USP) (US5,707,435) report is as fibre finish.
Above existing patent of lifting is at used monomer, and all there is the shortcoming and defect part in many aspects such as reaction mechanism and polymer architecture and Application Areas etc.Specifically exist: stability to hydrolysis with the viscosifying power of fabric, hair, to the killing action of multiple Gram-positive, negative bacteria, has aspects such as soft effect to fabric, hair.
Given this, the purpose of this invention is to provide a kind of organosilicon quaternary ammonium salt polymer preparation and application method, solve the shortcoming and defect part of existing like product.
Summary of the invention: one, the present invention is directed to the problem that similar prior art or product will solve
The present invention compares with above prior art and product, has solved the problem of the following aspects:
1. introduced a plurality of functional groups, made that problem such as the single and function singleness of structure is solved;
2. by introducing soft tackify group, make product and fabric, hair etc. have stronger avidity;
3. reaction scheme of the present invention is more simple, convenient, has stronger operability, greatly reduces life
Produce cost, make it adapt to industrialization demands better.Two, advantage, characteristics of the present invention:
1, realized that a product has the characteristics of multiple function;
2, active quaternary ammonium salt group makes it have good germicidal action, to multiple Gram-positive, negative thin
Bacterium has powerful killing action.
3, the introducing of tackify group and dimethyl siloxane chain link makes product of the present invention have good softness
Act on, and stronger avidity has been arranged with fabric, hair.
4, product of the present invention is easy to use, and Application Areas is widened greatly.
5, product of the present invention has the hair accent that sterilizing power is strong, fastness to washing is high, antibacterial efficacy is lasting and good
The reason function.Three, the technical issues that need to address of the present invention and technical scheme:
1. tertiary amine monomers has following general formula:
Or the nitrogen heterocyclic ring tertiary amine compound,
R wherein
1, R
2, R
3=C
nH
2n+1, n=1 ~ 18
For example: C
18H
37N (CH
3)
2, C
16H
33N (C
2H
5)
2,
Deng.
2. alkylating reagent has following general formula: XCH
2CH
2CH
2-Si-(R
4)
a(OR
5)
3-aR wherein
4, R
5=C
nH
2n+1, n=0 ~ 3, a=0,1, X=Cl, Br, I
3. the silicone compounds that contains alkoxyl group and tackify group has following general formula: (R
6O)
3-b(R
7)
bSi-R
xR wherein
6, R
7=C
nH
2n+1, n=1 ~ 3, b=0,1 R
x=NH
2CH
2CH
2CH
2-, NH
2CH
2CH
2NHCH
2CH
2CH
2-etc.
4. the general formula of polysiloxane performed polymer is as follows:
R wherein
8, R
9=C
nH
2n+1, n=1 ~ 3; Ph; Ar etc., m=10 ~ 200
5. reaction formula of the present invention is as follows:
R wherein
1, R
2, R
3=C
nH
2n+1, n=1 ~ 18 for example: C
18H
37N (CH
3)
2, C
16H
33N (C
2H
5)
2,
Deng R
4, R
5=C
nH
2n+1, n=0 ~ 3, a=0,1, X=Cl, Br, I
R wherein
1, R
2, R
3=C
nH
2n+1, n=1 ~ 18 for example: C
18H
37N (CH
3)
2, C
16H
33N (C
2H
5)
2,
Deng; R
4, R
5=C
nH
2n+1, n=0 ~ 3, X=Cl, Br, I;
R
6, R
7=C
nH
2n+1, n=1 ~ 3, R
x=NH
2CH
2CH
2CH
2-, NH
2CH
2CH
2NHCH
2CH
2CH
2-etc.;
R
8, R
9=C
nH
2n+1, n=1 ~ 3, Ph, Ar etc.;
O=5 ~ 100, r=pm=50 ~ 1000, q=1 ~ 20 4, the beneficial effect that the present invention produced
The product of gained of the present invention is an organosilicon inarch quaternary ammonium salt high-molecular copolymer, and it combines the peculiar advantage of organosilicon and quaternary ammonium salt, has broad-spectrum bactericidal action.In addition, the introducing of the soft group of tackify, making it has stronger affinity interaction with fabric, hair etc., and certain soft effect is arranged.Antibiotic group is an organosilicon quaternary ammonium cation group, can be adsorbed in the surface of bacterium forcefully, change the permeability of bacteria cell wall, endobacillary enzyme, coenzyme and metabolic intermediate are overflowed, hinder breathing and the glycolytic cycle of bacterium, and make the tropina sex change, owing to adopt physical adsorbability antibiotic, so bacterium can not produce resistance, thereby the effect of performance strong antibiotic.The tackify group can be attached to material surfaces such as fabric, hair securely with the covalent linkage form, so its outstanding advantage has the fastness to washing height exactly, antibacterial efficacy is lasting.
Range of application of the present invention includes but not limited to the fabric post-treatment agent, bedding and clothing biocide mildewcide, all spendable sanitizers such as hair adjustment agent in the hair care category makeup and family, hospital, hotel.
Fig. 1 is principle flow chart of the present invention (quaternized, copolymerization, emulsification).
Quaternized:
R wherein1，R
2，R
3＝C
nH
2n+1, n=1～18 for example: C18H
37N(CH
3)
2，C
16H
33N(C
2H
5)
2，
Deng R4，R
5＝C
nH
2n+1, n=0～3, a=0,1, X=Cl, Br, I reaction condition are T=70～140 ℃, t=0.5～24h copolymerization: R wherein1，R
2，R
3＝C
nH
2n+1, n=1 ~ 18 for example: C18H
37N(CH
3)
2，C
16H
33N(C
2H
5)
2, () etc.
R
4，R
5＝C
nH
2n+1，n＝0~3，X＝Cl，Br，I；
R
6，R
7＝C
nH
2n+1，n＝1~3，R
x＝NH
2CH
2CH
2CH
2-，NH
2CH
2CH
2NHCH
2CH
2CH
2-etc.;
R
8，R
9＝C
nH
2n+1, n=1 ~ 3, Ph, Ar etc.;
o＝5~100，r＝pm＝50~1000，q＝1~20
Reaction condition is T=50 ~ 150 ℃, t=0.5 ~ 24h
Emulsification:
Usually, this product is applied with the form of emulsion, and active matter content is 5～30%, and it is possible Emulsifying agent is cationic, anionic, nonionic emulsifier, and acetic acid or phosphoric acid are nertralizer, institute The water that uses is deionized water or distilled water.
The embodiment of the invention is described in detail in detail below with reference to the accompanying drawings:
Embodiment 1
2: 1 in molar ratio ~ 1: 2 adding Br-(CH in container
2)
3Si (OR)
3And C
18H
37-N-(C
2H
5)
2, react 0.5 ~ 24h down at 70 ~ 140 ℃, get a quaterisation thing (I).
Get (I) 100g,
150g, (RO)
3Si-(CH
2)
3-NH-(CH
2)
2-NH
250g reacts under KOH catalysis, and reaction conditions is T=60 ~ 120 ℃, t=0.5 ~ 24h.Get a light yellow transparent liquid product.
With nonionic and the above product of negatively charged ion compound emulsifying agent emulsification, an active matter content is 5～30% light yellow transparent liquid.
This product can be applicable to fabric post-treatment, and among hospital, hotel, family's bedding and clothing germicidal treatment or the shampoo formula, working concentration is 0.01～10%, and sterilizing rate can reach more than 95%.
Embodiment 2 is with C among the embodiment 1
18H
37-N-(C
2H
5)
2Change pyridine into,
Consumption reduces by half, and reaction conditions is example as above.
Use nonionic emulsifying agent instead and cationic emulsifier is compound, must get an active matter content and be 5～30% light yellow transparent liquid.
This product can be applicable to fabric post-treatment, hospital, hotel, family's bedding and clothing germicidal treatment, and working concentration is 0.01～10%, sterilizing rate can reach more than 90%.
Claims (10)
1. an organosilicon quaternary ammonium salt polymer prepares and application method, and it is characterized in that: the synthetic route of the macromolecular grafted multipolymer of organopolysiloxane and synthesis technique are:
R
1，R
2，R
3＝C
nH
2n+1，n＝1~18?C
18H
37N(CH
3)
2，C
16H
33N(C
2H
5)
2，
R
4，R
5＝C
nH
2n+1，n＝0~3，X＝Cl，Br，I；
R
6，R
7＝C
nH
2n+1，n＝1~3，R
x＝NH
2CH
2CH
2CH
2-，NH
2CH
2CH
2NHCH
2CH
2CH
2-；
R
8，R
9＝C
nH
2n+1，n＝1~3，Ph，Ar；
o＝5~100，r＝50~1000，q＝1~20
2. organosilicon quaternary ammonium salt polymer preparation according to claim 1 and application method, it is characterized in that: tertiary amine monomers has following general formula:
The nitrogen heterocyclic ring tertiary amine compound,
R
1，R
2，R
3＝C
nH
2n+1，n＝1～18
C
18H
37N(CH
3)
2，C
16H
33N(C
2H
5)
2，
3. organosilicon quaternary ammonium salt polymer preparation according to claim 1 and application method, it is characterized in that: alkylating reagent has following general formula: XCH
2CH
2CH
2-Si-(R
4)
a(OR
5)
3-a
R
4，R
5＝C
nH
2n+1，n＝0~3，a＝0，1，X＝Cl，Br，I
4. organosilicon quaternary ammonium salt polymer preparation according to claim 1 and application method, it is characterized in that: the silicone compounds that contains alkoxyl group and tackify group has following general formula:
(R
6O)
3-b(R
7)
bSi-R
x
R
6，R
7＝C
nH
2n+1，n＝1～3，b＝0，1
R
x＝NH
2CH
2CH
2CH
2-，NH
2CH
2CH
2NHCH
2CH
2CH
2-
5. organosilicon quaternary ammonium salt polymer preparation according to claim 1 and application method, it is characterized in that: the polysiloxane of two ends hydroxyl has following general formula:
R
8，R
9＝C
nH
2n+1，n＝1～3；Ph；Ar，m＝10～200
6. organosilicon quaternary ammonium salt polymer preparation according to claim 1 and application method, it is characterized in that: product is used with the form of emulsion, active matter content is 5～30%, its emulsifier type is cationic, anionic, nonionic emulsifier, the water that uses is deionized water or distilled water, and its final working concentration is 0.01～10%.
7. organosilicon quaternary ammonium salt polymer according to claim 1 preparation and application method, it is characterized in that: the catalyzer of use comprises bases: KOH, NaOH, quaternary ammonium hydroxide, season phosphine alkali.
8. organosilicon quaternary ammonium salt polymer preparation according to claim 1 and application method, it is characterized in that: used solvent comprises the benzene class: benzene, toluene, dimethylbenzene; C
1～C
8Positive structure or isomery alcohols; Polyalcohols; The ester class; Ketone.
9. organosilicon quaternary ammonium salt polymer preparation according to claim 1 and application method, it is characterized in that: temperature of reaction is 50-150 ℃.
10. organosilicon quaternary ammonium salt polymer preparation according to claim 1 and application method, it is characterized in that: the reaction times is 0.5-24 hour.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA021343721A CN1468887A (en) | 2002-07-17 | 2002-07-17 | Prepn and application of organosilicon quaternary ammonium salt polymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA021343721A CN1468887A (en) | 2002-07-17 | 2002-07-17 | Prepn and application of organosilicon quaternary ammonium salt polymer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1468887A true CN1468887A (en) | 2004-01-21 |
Family
ID=34145763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA021343721A Pending CN1468887A (en) | 2002-07-17 | 2002-07-17 | Prepn and application of organosilicon quaternary ammonium salt polymer |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1468887A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1314320C (en) * | 2005-11-30 | 2007-05-09 | 山东大学 | A kind of preparation method of organosilicon quaternary ammonium salt bactericide |
| CN100339419C (en) * | 2004-06-03 | 2007-09-26 | 瓦克化学股份公司 | Hydrophilic siloxane copolymer and method for manufacturing the same |
| US20080226585A1 (en) * | 2005-03-31 | 2008-09-18 | Institue Curie | Method for Treating Surfaces with Copolymers |
| CN100500985C (en) * | 2006-11-27 | 2009-06-17 | 常熟市亚德实业有限公司 | Feather-down clothing care agent |
| CN101942083A (en) * | 2010-09-10 | 2011-01-12 | 广东标美硅氟新材料有限公司 | Organic silicon compounds, and preparation method and application thereof |
| CN102277746A (en) * | 2011-07-28 | 2011-12-14 | 杭州贝斯特化纤有限公司 | Antimicrobial emulsion used for textile fibers and application method thereof |
| CN102875814A (en) * | 2012-09-19 | 2013-01-16 | 光景生物科技(苏州)有限公司 | Polysiloxane, preparation method, application and bacteriacide containing same |
| CN102952273A (en) * | 2012-10-31 | 2013-03-06 | 上海氟聚化学产品有限公司 | Amphion type amino silicone oil and preparation method thereof |
| CN108290906A (en) * | 2015-09-30 | 2018-07-17 | 爱茉莉太平洋股份有限公司 | A kind of alkoxysilane compound containing trialkylsilyl group in molecular structure or its salt, the preparation method and hair hair composition containing the compound |
| CN109897185A (en) * | 2019-03-18 | 2019-06-18 | 山东交通学院 | A kind of side chain is containing vinyl and quaternary ammonium salt polysiloxanes and its synthetic method and the application in preparation antibacterial silicon rubber |
| CN109912801A (en) * | 2019-03-18 | 2019-06-21 | 山东交通学院 | A kind of functional polysiloxane containing quaternary ammonium salt and synthesis method thereof |
| CN117303836A (en) * | 2023-09-23 | 2023-12-29 | 浙江博宏新材料股份有限公司 | Interface mortar for anticorrosive paint and preparation method thereof |
-
2002
- 2002-07-17 CN CNA021343721A patent/CN1468887A/en active Pending
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100339419C (en) * | 2004-06-03 | 2007-09-26 | 瓦克化学股份公司 | Hydrophilic siloxane copolymer and method for manufacturing the same |
| US8475782B2 (en) * | 2005-03-31 | 2013-07-02 | Institut Curie | Method for treating surfaces with copolymers |
| US20080226585A1 (en) * | 2005-03-31 | 2008-09-18 | Institue Curie | Method for Treating Surfaces with Copolymers |
| CN1314320C (en) * | 2005-11-30 | 2007-05-09 | 山东大学 | A kind of preparation method of organosilicon quaternary ammonium salt bactericide |
| CN100500985C (en) * | 2006-11-27 | 2009-06-17 | 常熟市亚德实业有限公司 | Feather-down clothing care agent |
| CN101942083A (en) * | 2010-09-10 | 2011-01-12 | 广东标美硅氟新材料有限公司 | Organic silicon compounds, and preparation method and application thereof |
| CN101942083B (en) * | 2010-09-10 | 2012-08-22 | 广东标美硅氟新材料有限公司 | Organic silicon compounds, and preparation method and application thereof |
| CN102277746A (en) * | 2011-07-28 | 2011-12-14 | 杭州贝斯特化纤有限公司 | Antimicrobial emulsion used for textile fibers and application method thereof |
| CN102875814A (en) * | 2012-09-19 | 2013-01-16 | 光景生物科技(苏州)有限公司 | Polysiloxane, preparation method, application and bacteriacide containing same |
| CN102952273A (en) * | 2012-10-31 | 2013-03-06 | 上海氟聚化学产品有限公司 | Amphion type amino silicone oil and preparation method thereof |
| CN102952273B (en) * | 2012-10-31 | 2016-12-21 | 上海氟聚化学产品有限公司 | Amphoteric ion type amido silicon oil and preparation method thereof |
| CN108290906A (en) * | 2015-09-30 | 2018-07-17 | 爱茉莉太平洋股份有限公司 | A kind of alkoxysilane compound containing trialkylsilyl group in molecular structure or its salt, the preparation method and hair hair composition containing the compound |
| CN108290906B (en) * | 2015-09-30 | 2021-03-16 | 爱茉莉太平洋股份有限公司 | A kind of alkoxysilane compound or its salt, its preparation method and the hair composition containing this compound |
| CN109897185A (en) * | 2019-03-18 | 2019-06-18 | 山东交通学院 | A kind of side chain is containing vinyl and quaternary ammonium salt polysiloxanes and its synthetic method and the application in preparation antibacterial silicon rubber |
| CN109912801A (en) * | 2019-03-18 | 2019-06-21 | 山东交通学院 | A kind of functional polysiloxane containing quaternary ammonium salt and synthesis method thereof |
| CN117303836A (en) * | 2023-09-23 | 2023-12-29 | 浙江博宏新材料股份有限公司 | Interface mortar for anticorrosive paint and preparation method thereof |
| CN117303836B (en) * | 2023-09-23 | 2024-04-05 | 浙江博宏新材料股份有限公司 | Interface mortar for anticorrosive coating and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1468887A (en) | Prepn and application of organosilicon quaternary ammonium salt polymer | |
| AU2007217780B2 (en) | Generation of antimicrobial surfaces using dendrimer biocides | |
| Sauvet et al. | Amphiphilic block and statistical siloxane copolymers with antimicrobial activity | |
| WO2011063625A1 (en) | Antimicrobial compound and preparation method thereof | |
| EP2176319A1 (en) | Method for producing branched sih functional polysiloxanes and the use thereof for producting sic- and sioc-linked, branched organomodified polysiloxanes | |
| US20060009592A1 (en) | Organosilicon compounds comprising cyclodextrin radicals | |
| DE102008041601A1 (en) | Process for the preparation of branched SiH-functional polysiloxanes and their use for the preparation of liquid, SiC or SiOC-linked, branched organomodified polysiloxanes | |
| EP1362904A4 (en) | Water-based water repellant for treatment of substrates | |
| CN1636031A (en) | High refractive index polysiloxanes and their preparation | |
| CN101734669A (en) | Method for preparing amino group or quaternary ammonium salt functional silicon dioxide mesoporous spherical material | |
| CN110371988B (en) | Preparation method of silicon dioxide antibacterial microspheres | |
| Mu et al. | Graphitic carbon nitride/zeolitic imidazolate framework-8 nanoparticles with antibacterial properties for textile coating | |
| CN102007935B (en) | Siloxane supported quaternary salt type bactericide, and preparation, application and regeneration thereof | |
| CN101298498A (en) | Alkoxy terminated linear polysiloxane coupling agent and its synthesis method | |
| US20210017383A1 (en) | Silicone co-polymers and methods of use thereof to modify silicone elastomers | |
| JP2538426B2 (en) | Method for producing organopolysiloxane | |
| CN111328827A (en) | A kind of quaternized polysilsesquioxane nanosphere hybrid antibacterial material and preparation method thereof | |
| Fortuniak et al. | Polysiloxanes with quaternary ammonium salt biocidal functions and their behavior when incorporated into a silicone elastomer network | |
| US20230151224A1 (en) | Microbial reduction coating compositions and methods of use thereof | |
| EP4442693A1 (en) | Composition containing organosilicon compound | |
| CN114317370B (en) | Preparation method of bionic silicon mineralizing bacteria and its application in treating phenol wastewater | |
| CN1133684C (en) | Polysiloxane copolymer with side quarternary ammonium group and its preparation | |
| CN111511868B (en) | Sustained-release composite agent containing interlayer modified layered inorganic compound and its production method | |
| Shi et al. | Introduction of organosilicon materials | |
| CN119684559A (en) | Inorganic composite polyurethane material containing dynamic boric acid ester bond and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |