CN104761723B - A kind of polysiloxane soft agent with fixing property - Google Patents
A kind of polysiloxane soft agent with fixing property Download PDFInfo
- Publication number
- CN104761723B CN104761723B CN201510165677.5A CN201510165677A CN104761723B CN 104761723 B CN104761723 B CN 104761723B CN 201510165677 A CN201510165677 A CN 201510165677A CN 104761723 B CN104761723 B CN 104761723B
- Authority
- CN
- China
- Prior art keywords
- agent
- fixing property
- polysiloxanes
- tertiary amine
- softening agent
- 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.)
- Active
Links
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
A kind of polysiloxane soft agent with fixing property, the softening agent are with formula DnM polysiloxanes；Wherein, D=SiY2O2/2；M=QSiYO2/2；Y, which is represented, same or different is selected from following group：Alkyl, aryl or alkaryl with 1 30 carbon atoms, preferably methyl or phenyl, particularly preferred methyl；Q represents the same or different organic group with quaternary ammonium salt functional group.The present invention has a polysiloxane soft agent of fixing property, its side chain be with quaternary ammonium salt and（Or）The polysiloxanes of tertiary amine hydrochlorate, the quaternary ammonium salt of side chain and（Or）Tertiary amine hydrochlorate has fixation function, and the polysiloxanes of main chain is the very excellent softening agent of performance, the polysiloxanes good hand touch, has preferably dry, fastness to wet rubbing, and soaping fastness is also preferable, and the composition storage being configured to is stable.The invention provides the softening agent with fixing property for yarn fabric, non-woven fabric.
Description
Technical field
The present invention relates to a kind of polysiloxane soft agent with fixing property and preparation method thereof, belongs to textile auxiliary technology
Field.
Background technology
In order that textile and clothing are soft, bright in luster, it is necessary in textile production and clothing Family Day with washing
Color fixing agent and softening agent are added during washing.In textile production, two can be realized in color fixing process and soft technique respectively
Individual function；But, it is necessary to reach two purposes by once washing, so with fixing property in family's ordinary clothing washing
Softening agent arises at the historic moment.Softening agent with fixing property cannot only be applied in ordinary clothing washing formula, can also answer
Use in textile production, fixation softness technology generations is replaced color fixing process and soft technique, so as to reach energy-efficient purpose.
Initial stage, in the market use compound fixing-softening agent.(the compound fixing-softening agent and its to cotton such as Dong Yongchun
Arrangement Dong Yongchun of fabric, Xu Xue loyalty Tianjin University of Technology journal .2002 (21), 4:12~16) cationic polyamine is used
Class color fixing agent and three kinds of different types of softening agents are prepared for compound fixing-softening agent, three kinds of different types of softening agent difference
It is the polysiloxane-based microemulsion of nonionic, nonionic polyethylene emulsion and water-based polyurethane compound, is knitted for cotton
The fixation of thing and soft one bath, it is believed that the soft component in fixing-softening agent is not produced to the tint retention of fixation component
Raw very big influence.
On the basis of compound fixing-softening agent, develop again integrate fixation and softness environment-friendly type printing and dyeing help
Agent, the polymer and polyfunctional group structure of itself macromolecule, by the component grafting of fixation and softness together, avoid multiple
Mould assembly mixture is long placed in layering and the drawbacks such as component is unstable.Duan Xinfeng (fixing-softening agent RF. prints and dyes, and 2007,22:37~40)
Polyaminoester emulsion is developed, bathes fixation and soft finish for pure cotton fabric one, result of study shows that it has and preferably soaped
Fastness and crock fastness, good hand touch, discoloration is small, and energy-saving and water-saving.
Each polysiloxanes and their compositions are known as fabric softener.(organosilicon is soft by Han Fu etc.
Soft dose of Han Fu, Zhang Gaoyong, Wang Jun daily chemical industry, 2001 (2):38~42) organosilicon (polysiloxanes) is outlined to spin
Development and present situation in terms of fabric softening agent arrangement.Figure (MOMENTIVE) company is stepped in patent of invention (WO2009134364)
Application of the global polysiloxane soft agent in all kinds of textiles is also described in technical background.
The softening agent with fixing property based on prior art, its main chain are polyurethane structurals, and its shortcoming is flexibility
Can be bad, and polysiloxane soft agent does not have clear and definite fixing property.
The content of the invention
The object of the present invention is to for there is no the defects of fixation characteristic, this hair as the polysiloxanes of fabric softener
It is bright to propose a kind of polysiloxane soft agent with fixing property.
Realize the technical scheme is that, a kind of polysiloxane soft agent with fixing property, the softening agent is
With formula DnM polysiloxanes；
Wherein, D=SiY2O2/2；M=QSiYO2/2；
Y, which is represented, same or different is selected from following group：Alkyl, aryl or alkane virtue with 1-30 carbon atom
Base, preferably methyl or phenyl, particularly preferred methyl；
Q represents the same or different organic group with quaternary ammonium salt functional group；
N is 1~200, preferably 5~100, particularly preferred 10~50.
The Q groups are the groups with-R1-R2 structures,
The R1 is preferred to be represented selected from following same or different divalent group：
-(CH2)X- ,-(CH2)3-OCH2CH(OH)CH2-；
The R1 is preferably：-(CH2)3- ,-(CH2)3-OCH2CH(OH)CH2-；
The R2 is preferably as follows same or different group：-N+R3R4R5A-；
Described R3, R4, R5 independently represent hydrogen or the monovalence containing 1-30 carbon atom carries functional group or substituted radical
Alkyl；
The A represents the identical or different counter ion counterionsl gegenions to the positive charge in quaternized amine groups, selects what oneself was known
Acceptable sour HA in prior art, such as organic acid or the anion of inorganic acid, particularly preferably selected from acetic acid, L- hydroxylactic acids
With the anion of the organic or inorganic of aromatic carboxylic acid.
The present invention provides passes through octamethylcy-clotetrasiloxane (D in a usual manner4) balance to prepare the product of the present invention
A kind of method, except annular siloxane, in order to set average modified degree, α, ω-two-SiOH- in a manner of a kind of control
The siloxanes of functional group can also be added to the equilibrium mixture.
The preparation method of polysiloxanes of the present invention comprises the following steps：
(1) reacted with epoxy alkoxy silane and secondary amine, obtain tertiary amine coupling agent, if tertiary amine coupling agent, can save
Slightly this step, directly carry out in next step；
(2) under normal conditions, tertiary amine coupling agent is made to reach balance with annular siloxane or hydroxy silicon oil；It is mixed as balance
Compound, add α, the siloxanes of ω-two-SiOH- functional groups；
(3) it is quaternized to obtain the corresponding polysiloxanes for carrying ammonium.
The epoxy alkoxy silane is epoxy alkyl dialkoxy silicane, preferably epoxy alkyl methyl dimethoxy epoxide silicon
Alkane, particularly preferred 3- [oxygen of (2,3)-epoxy third] hydroxypropyl methyl dimethoxysilane；
The tertiary amine coupling agent is tertiary amine alkyl-alkyl dialkoxy silicane, preferred tertiary amine alkyl methyl dimethoxy silicon
Alkane, particularly preferred dimethylamine propyl methyl dimethoxysilane；
Quaternized the reagent preferably sulfuric acid dialkyl ester and alkyl halide, particularly preferred dimethyl sulfate, sulfuric acid two
The chloro- 1,2- propane diols of ethyl ester, chloromethanes, 3-.
Invention further provides the compound of the present invention be used as yarn fabric, non-woven fabric and/or by it is natural and/
Or the softening agent with fixing property of artificial raw material composition.
The compound of the softening agent with fixing property is preferably used as with general formula DnM, wherein n=1-200.This kind of chemical combination
Thing not only has sufficiently high silicone character and produces comfortable feel, but also has certain molecular weight, can be rear
It is continuous to be configured to stablize composition use.
Used according to the invention has general formula DnContent is existed based on whole composition in the composition of M compound
Between 0.5-99 weight %, preferably between 3-70 weight %, particularly preferably between 5-50 weight %.
Formulation of the polysiloxanes for the softening agent with fixing property, the softening agent and containing softening agent can
It is used for textile industry as printing and dyeing assistant, applies also for ordinary clothing washing.The formulation includes 5-50 weight % institute
State polysiloxanes.
The invention has the advantages that the present invention has the polysiloxane soft agent of fixing property, its side chain is to carry season
The polysiloxanes of ammonium salt and (or) tertiary amine hydrochlorate, the quaternary ammonium salt and (or) tertiary amine hydrochlorate of side chain have good fixation function, main
The polysiloxanes of chain is the very excellent softening agent of performance, the polysiloxanes good hand touch, has preferably dry, fastness to wet rubbing,
Soaping fastness is also preferable, and the composition storage being configured to is stable.It is used as the invention provides the compound of the present invention and is used to weave
Thing, non-woven fabric and/or the softening agent with fixing property being made up of natural and/or artificial raw material.
The present invention is applied to yarn fabric, non-woven fabric makees the softening agent with fixing property.
Embodiment
Embodiment 1：
In 2000ml four-hole boiling flask, by 740g octamethylcy-clotetrasiloxanes (D4), 76.4g (0.4mol) dimethylamine third
Ylmethyl dimethoxysilane and base catalyst are mixed and heating stirring, and 7.2g water is added dropwise, and is heated to 110 DEG C of insulations
3h, 78 DEG C are cooled to, add 222g isopropanols, 22g (0.2mol) 3- chlorine-1,2-propylene glycols are added dropwise, it is anti-in 78~80 DEG C of micro-boilings
2h is answered, is cooled to 50 DEG C, adds 12g (0.2mol) acetic acid, the mixture is distilled out into isopropanol at 80 DEG C, the height for obtaining muddiness glues
The fluid sample 1 of degree, it is described by following statistics formula:
Embodiment 2：
In 2000ml four-hole boiling flask, by 44g (0.2mol) 3- [oxygen of (2,3)-epoxy third] hydroxypropyl methyl dimethoxy
Silane, 20g (0.2mol) methyl piperazine normal temperature are well mixed, and lucifuge isolation air reaction 24h, add the silicon of 740g prestoxs ring four
Oxygen alkane (D4) and base catalyst is mixed and heating stirring, and 3.6g water is added dropwise, and is heated to 110 DEG C of insulation 3h, cools to
78 DEG C, 222g isopropanols are added, 25.2g (0.2mol) dimethyl suflfate is added dropwise, 2h is reacted in 78~80 DEG C of micro-boilings, is cooled to 50
DEG C, add 12g (0.2mol) acetic acid, the mixture is distilled out into isopropanol at 80 DEG C, obtain the highly viscous sample 2 of muddiness, it
By following statistics formula description:
Embodiment 3：
In 2000ml four-hole boiling flask, by 220g (1mol) 3- [oxygen of (2,3)-epoxy third] hydroxypropyl methyl dimethoxy silicon
Alkane, 74g (1mol) diethylamine normal temperature are well mixed, and lucifuge isolation air reaction 24h, add 740g linear bodies (WS-62M) and alkali
Property catalyst mixed and heating stirring, 18g water is added dropwise, is heated to 110 DEG C of insulation 3h, cools to 78 DEG C, adds 222g
Isopropanol, 100.8g (0.8mol) dimethyl suflfate is added dropwise, reacts 2h in 78~80 DEG C of micro-boilings, be cooled to 50 DEG C, add 12g
(0.2mol) acetic acid, the mixture is distilled out into isopropanol at 80 DEG C, obtain the highly viscous sample 3 of muddiness, it is by following system
Count formula description:
Composition embodiment：
The sample 1~3 that above example obtains is emulsified into correspondent composition 1~3.
30 weight % samples 1, sample 2, sample 3 are positioned in the disperser with stirring respectively, it is different to add 5 weight %
Structure tridecanol polyoxyethylene ether (degree of polymerization 5), 10 weight % isomerous tridecanol polyoxyethylene ethers (degree of polymerization 7), stir, and delay
Slowly mixture is supplemented to 100 weight % with water, respectively obtains composition 1~3.Application Example：
30tex × 37tex236 roots/10cm × 433 piece/10cm pure cotton fabric, through desizing, concise, bleaching, pass through respectively
Active red card EBS, reactive turquoise blue EBS, active yellow EBS dyeing are crossed, obtains cloth to be assessed；Color fixing agent, HonesilTM FP-
061, Guangzhou Ao Liesixin Chemical Industry Science Co., Ltd；Softening agent, HonesoftTMHS-15, Guangzhou Australia row, which drain dry chemical science and technology, to be had
Limit company.
Y571L dyeing crock fastness instrument (Laizhou Electron Instrument Co., Ltd.), R-3 laboratories forming machine (Suzhou Feng Yi
Detecting instrument Co., Ltd).
Stability is tested, and after centrifuging 3000r/min × 10min, surveys its stability；GB/ is pressed in soaping fastness test
T3921-1977 is tested and graded；Crock fastness is tested and graded by GB/T3920-1977；Feel uses digital palpation for examination of trauma
Test and grading, 10 grades are divided into, 10 be excellent, and 1 is poor；Discoloration determines, using the fabric of non-fixation as reference, after arrangement
The changes of shade grading of painting cloth.
Finishing technique：Respectively with composition 1~3, color fixing agent, softening agent, dosage 50g/L, an immersing and rolling, baking temperature
130 DEG C × 2min, cloth, acquired results such as table 1 below~4 are assessed in processing.
The outward appearance of 1 present composition of table 1~3 and stability
The Comparison study of the present composition of table 2 and special color fixing agent, softening agent on active red dyed cloth
The Comparison study of the present composition of table 3 and special color fixing agent, softening agent on active emerald green blue dyed cloth
The Comparison study of the present composition of table 4 and special color fixing agent, softening agent on active yellow dyed cloth
The composition 1~3 configured from table 1~4, the embodiment of the present invention 1~3, outward appearance is all oolemma blue streak emulsion,
Stability is good, in the soft application of fixation, can realize the polysiloxanes good hand touch, have preferably dry, fastness to wet rubbing, soap
Fastness is also preferable.
Claims (5)
1. a kind of polysiloxane soft agent with fixing property, the softening agent is with formula DnM polysiloxanes；
Wherein, D=SiY2O2/2；M=QSiYO2/2；
Y, which is represented, same or different is selected from following group：Alkyl, aryl or alkaryl with 1-30 carbon atom；
Q represents the same or different organic group with quaternary ammonium salt functional group；
N is 1~200；
The Q groups are the groups with-R1-R2 structures,
The R1 is selected from following same or different divalent group：
-(CH2)X- ,-(CH2)3-OCH2CH(OH)CH2-；
The R1 is selected from：-(CH2)X- ,-(CH2)3-OCH2CH(OH)CH2-；
The R2 is selected from following same or different group：-N+R3R4R5A-；
Described R3, R4, R5 independently represent hydrogen or alkane of the monovalence with functional group or substituted radical containing 1-30 carbon atom
Base；
Q will the structure containing tertiary amine hydrochlorate and quaternary ammonium salt simultaneously；
The A represents the identical or different counter ion counterionsl gegenions to the positive charge in quaternized amine groups, selected from sour HA, includes
The anion of machine acid or inorganic acid.
A kind of 2. polysiloxane soft agent with fixing property according to claim 1, it is characterised in that the poly- silicon
The preparation method of oxygen alkane comprises the following steps：
(1) reacted with epoxy alkoxy silane and secondary amine, tertiary amine coupling agent is obtained, if tertiary amine coupling agent, it is convenient to omit this
Step, directly carry out in next step；
(2) under normal conditions, tertiary amine coupling agent is made to reach balance with annular siloxane or hydroxy silicon oil；Mixed as balance
Thing, add α, the siloxanes of ω-two-SiOH- functional groups；
(3) it is quaternized to obtain the corresponding polysiloxanes for carrying ammonium.
A kind of 3. polysiloxane soft agent with fixing property according to claim 2, it is characterised in that
The epoxy alkoxy silane is epoxy alkyl dialkoxy silicane；
The tertiary amine coupling agent is tertiary amine alkyl-alkyl dialkoxy silicane；
Quaternized the reagent preferably sulfuric acid dialkyl ester and alkyl halide.
A kind of 4. polysiloxane soft agent with fixing property according to claim 1, it is characterised in that the poly- silicon
Oxygen alkane is used to make the softening agent with fixing property, and the softening agent and the formulation containing softening agent can be used as printing and dyeing assistant to use
In textile industry, ordinary clothing washing is applied also for.
A kind of 5. polysiloxane soft agent with fixing property according to claim 4, it is characterised in that the preparation
Thing includes the 5-50 weight % polysiloxanes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510165677.5A CN104761723B (en) | 2015-04-09 | 2015-04-09 | A kind of polysiloxane soft agent with fixing property |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510165677.5A CN104761723B (en) | 2015-04-09 | 2015-04-09 | A kind of polysiloxane soft agent with fixing property |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104761723A CN104761723A (en) | 2015-07-08 |
| CN104761723B true CN104761723B (en) | 2018-04-06 |
Family
ID=53643843
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510165677.5A Active CN104761723B (en) | 2015-04-09 | 2015-04-09 | A kind of polysiloxane soft agent with fixing property |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104761723B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107916584A (en) * | 2017-11-24 | 2018-04-17 | 陈石生 | Soft dry wet friction fastness improving agent |
| CN111320757B (en) * | 2018-12-14 | 2022-03-22 | 绍兴德美新材料有限公司 | Preparation method of high-fastness ultralow-yellowing silicone oil for polyester fabric and polyester fabric |
| CN115852719B (en) * | 2022-09-30 | 2024-03-26 | 浙江越新印染有限公司 | Silicon-containing color fixing auxiliary agent and application thereof in cotton printing and dyeing |
| CN117468239B (en) * | 2023-10-26 | 2024-04-16 | 清远市宏图助剂有限公司 | Amino acid modified polysiloxane fabric color fixing agent, preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101367941A (en) * | 2008-09-24 | 2009-02-18 | 上海大学 | Synthesis of epoxy quaternised modified amino-silicone oil |
| CN101565896A (en) * | 2008-12-22 | 2009-10-28 | 上海氟聚化学产品有限公司 | Quaternary amino cation modified polysiloxane softening agent and preparation method thereof |
| CN101914206A (en) * | 2010-08-13 | 2010-12-15 | 东华大学 | Quaternized modified amino silicone oil softener and preparation and application thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3505396B2 (en) * | 1998-08-18 | 2004-03-08 | 花王株式会社 | Liquid softener composition |
| DE102013219046A1 (en) * | 2013-09-23 | 2015-03-26 | Rudolf Gmbh | Polysiloxanes with quaternized heterocyclic groups |
-
2015
- 2015-04-09 CN CN201510165677.5A patent/CN104761723B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101367941A (en) * | 2008-09-24 | 2009-02-18 | 上海大学 | Synthesis of epoxy quaternised modified amino-silicone oil |
| CN101565896A (en) * | 2008-12-22 | 2009-10-28 | 上海氟聚化学产品有限公司 | Quaternary amino cation modified polysiloxane softening agent and preparation method thereof |
| CN101914206A (en) * | 2010-08-13 | 2010-12-15 | 东华大学 | Quaternized modified amino silicone oil softener and preparation and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| "多功能硅油柔软剂的合成及应用研究";胡亚楠;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;20150115(第01期);第19,21-22页 * |
| "环氧季铵化改性氨基硅油的合成与应用";丁宏博，等;《宁波化工》;20081231(第2期);第25-28页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104761723A (en) | 2015-07-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104761723B (en) | A kind of polysiloxane soft agent with fixing property | |
| CN104086779B (en) | Sliding block silicone oil of a kind of ultra-soft and preparation method thereof | |
| CN104650364B (en) | A kind of preparation method of hyperbranched polyether amino block organosilicon | |
| CN106521986B (en) | A kind of water-based two-sided matte woven fabric PU synthetic leather and preparation method thereof | |
| US8916511B2 (en) | Polysiloxanes having quaternary ammonium groups and use thereof | |
| CN105367800B (en) | A kind of amphoteric ion type organic silicon surfactant and preparation method and application | |
| CN109535428B (en) | Polyammonium modified polyether silicone oil and preparation method and application thereof | |
| CN106381715A (en) | Quaternary ammonium modified block polyether/amino silicone oil and preparation method thereof | |
| CN105568695B (en) | A kind of fabric wetting softener and its preparation method and application | |
| CN105648778B (en) | A kind of preparation method of non-ionic hydrophilic fatty acid amide Organosiliconcopolymere softening agent | |
| CN106589385A (en) | Low-yellowing quaternary ammonium type hydrophilic amino-modified silicone oil emulsion and preparation method thereof | |
| CN105544220A (en) | Fabric softener | |
| CA3095526A1 (en) | Siloxanes for treating textiles and for use in cleaning and care formulations | |
| CN105862476B (en) | A kind of formaldehyde-free active dye fixing agent and preparation method thereof | |
| CN109403048A (en) | A kind of cotton hydrophilic block polyethers amido silicon oil and preparation method thereof | |
| CN106279710A (en) | Sliding block polyether amino silicone oil of a kind of ultra-soft and preparation method thereof | |
| CN102505496A (en) | Aminosilicone durable hydrophilic potentiating agent, and preparation method and application thereof | |
| CN105755837B (en) | A kind of preparation method of quaternised modified amino-silicone oil softener and application | |
| CN106750324A (en) | A kind of poly- quaternary ammonium polyethers dimethyl silicone polymer and preparation method thereof and hand feel finishing agent | |
| CN102634036A (en) | Novel linear amino and polyester modified organosilicon compound for textiles | |
| CN115305724A (en) | Printing and dyeing method of antibacterial cotton fabric | |
| CN112012019A (en) | Super-smooth silky silicone oil for fabric after-finishing and after-finishing process | |
| CN108252104A (en) | A kind of preparation method for smooth agent of weaving | |
| CN108530635A (en) | A kind of manufacturing method of the hydrophilic block silicone oil of quaternary ammonium salt sealing end | |
| CN109295776A (en) | A kind of color fixing agent and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| EXSB | Decision made by sipo to initiate substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |