CN115926173A - Low-ring silicone oil and preparation method thereof - Google Patents
Low-ring silicone oil and preparation method thereof Download PDFInfo
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- CN115926173A CN115926173A CN202211691627.7A CN202211691627A CN115926173A CN 115926173 A CN115926173 A CN 115926173A CN 202211691627 A CN202211691627 A CN 202211691627A CN 115926173 A CN115926173 A CN 115926173A
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- 229920002545 silicone oil Polymers 0.000 title claims abstract description 57
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 40
- 229920000570 polyether Polymers 0.000 claims abstract description 40
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 16
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 7
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 17
- 239000004593 Epoxy Substances 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 13
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- NRTJGTSOTDBPDE-UHFFFAOYSA-N [dimethyl(methylsilyloxy)silyl]oxy-dimethyl-trimethylsilyloxysilane Chemical compound C[SiH2]O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C NRTJGTSOTDBPDE-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000005639 Lauric acid Substances 0.000 claims description 2
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 238000007086 side reaction Methods 0.000 abstract description 4
- 229910018557 Si O Inorganic materials 0.000 abstract description 3
- 238000007142 ring opening reaction Methods 0.000 abstract description 3
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 abstract description 3
- 150000003512 tertiary amines Chemical class 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 7
- 239000003921 oil Substances 0.000 description 6
- 229920013822 aminosilicone Polymers 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000007599 discharging Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Abstract
The invention discloses low-ring silicone oil which is shown as a structural formula I:
wherein n is more than or equal to 5,
Description
Technical Field
The invention relates to the technical field of organic silicon, and particularly relates to low-ring silicone oil and a preparation method thereof.
Background
Amino silicone oil is widely used as a softening agent in various processes of weaving, dyeing and finishing, sewing and the like in the textile industry, and is one of essential raw materials for high added value and high functionality of natural fiber products (such as cotton, hemp, silk, wool and the like) and synthetic fiber products (such as polyester, polyamide, polyacrylonitrile and the like). The amino silicone oil and the modified amino silicone oil endow the fabric with special hand feeling, and simultaneously are difficult to avoid the problems of floating oil demulsification, roller sticking, yellowing and the like in the use process. In recent years, block silicone oils have become popular in the market, and their superior low yellowing property and stability make up for the deficiencies of amino silicone oils, and even surpass amino silicone oils in terms of hand, hydrophilicity and durability. In the synthesis process of the block silicone oil, D4 (octamethylcyclotetrasiloxane) and an epoxy end-capping reagent are generally used as raw materials to synthesize epoxy silicone oil, and then the epoxy silicone oil and polyether amine are used to synthesize the terpolymer silicone oil.
With the strict requirements of countries in the world on environmental protection, developed countries have made a series of rigorous laws and regulations from various aspects such as environment, sanitation, safety and the like, and have formed another sanction for products in other countries. The production of products which are friendly to the environment and reliable by consumers, the realization of sustainable development and the like are the problems which are urgently solved by enterprises. Among the numerous ecological textile certifications, the blue-mark (system) ecological textile certification is gradually becoming a bridge for textile production enterprises to move to high-end consumer markets. Because of the reversible reaction in the production process of the silicone oil, almost all the current terpolymer silicone oil contains about 10 percent of ring bodies (such as D3, D4, D5, D6 and the like), and does not meet the requirement of a blue standard (system).
Therefore, it is necessary to develop a low-ring silicone oil and a preparation method thereof to reduce the content of ring body and meet the requirement of blue standard (system).
Disclosure of Invention
One of the purposes of the invention is to provide low-ring silicone oil, the ring body of the silicone oil is low, even no ring body is formed, and green and environment-friendly effects are realized so as to reach European Union standards such as a blue standard system.
In order to achieve the purpose, the invention provides low-ring silicone oil which is shown as a structural formula I:
wherein n is more than or equal to 5,
In some embodiments, 30 ≧ a ≧ 4, 40 ≧ b ≧ 5, 30 ≧ n ≧ 5, 30 ≧ c ≧ 5, 20 ≧ d ≧ 6.
Correspondingly, the invention also provides a preparation method of the low-ring silicone oil, which comprises the following preparation steps:
(1) Reacting octamethyltetrasiloxane and a hydrogen-containing double-end socket at 30-45 ℃ under the condition of concentrated sulfuric acid serving as a catalyst to prepare an intermediate;
(2) Adding sodium carbonate into the intermediate for neutralization, filtering, and then vacuumizing at high temperature;
(3) Reacting the intermediate treated in the step (2) with allyl epoxy polyether under the condition of chloroplatinic acid catalyst to obtain diepoxy terminated polyether silicone oil;
(4) And (3) carrying out a downward reaction on the diepoxy terminated polyether silicone oil and tertiary aminated polyether amine under a weak acidic condition to prepare the low-ring silicone oil.
In some embodiments, in step (1), the mass ratio of octamethyltetrasiloxane to hydrogen-containing double head is from 100.
In some embodiments, in step (2), the filtered intermediate is evacuated at a temperature of 140-180 ℃ for 1-3 hours. It should be noted that, because the intermediate product also contains D4 ring, the D4 ring can be largely removed by adding sodium carbonate for neutralization, filtering, and then performing vacuum pumping at 140-180 ℃ for 1-3 hours, so that the D4 ring can be largely removed, and the content of the ring is very low, which is noteworthy that the high-temperature vacuum pumping time cannot be too long, otherwise the activity of H at both ends of the product is affected, which is not beneficial for the subsequent reaction, and the effect is not ideal if the time is too short. By way of example, the temperature may be, but is not limited to, 140 ℃, 150 ℃, 160 ℃, 170 ℃, 180 ℃. The time may be, but is not limited to, 1 hour, 1.5 hours, 2 hours, 2.5 hours, 3 hours.
In some embodiments, in step (3), the mass ratio of intermediate to allyl epoxy polyether is 5.
In some embodiments, the reaction temperature in step (3) is less than 85 ℃, preferably less than 85 ℃, and more preferably 75 to 80 ℃.
In some embodiments, in step (4), the mild acid conditions are selected from at least one of acetic acid, propionic acid, lauric acid, isopropanol.
In some embodiments, in step (4), the tertiary aminated polyether amine has a weight average molecular weight of 500-2500. Illustratively, the weight average molecular weight of the tertiary aminated polyether amine can be, but is not limited to, 500, 1000, 1500, 2000, 2500, specifically, the tertiary aminated polyether amine is selected from the group consisting of ER-700, AE-1000, but not limited thereto. It will be appreciated that tertiary aminated polyetheramines are less basic and can avoid side reactions that result in the closure of linear Si — O chains into rings, effectively avoiding the formation of rings.
In some embodiments, in step (4), the mass ratio of diepoxy terminated polyether silicone oil to tertiary aminated polyether amine is from 100.
In some embodiments, the reaction temperature in step (4) is 70-85 ℃, and as an example, the temperature may be, but is not limited to, 70 ℃, 72 ℃, 74 ℃, 76 ℃, 78 ℃, 80 ℃, 82 ℃, 85 ℃.
In some embodiments, the allyl epoxy polyether has the following structural formula:
wherein, c is more than or equal to 30 and more than or equal to 5, d is more than or equal to 20 and more than or equal to 6.
In some embodiments, the allyl epoxy polyether has a molecular weight of 500 to 2000. The molecular weight of the allyl epoxy polyether can be, but is not limited to, 500, 1000, 1500, 2000, and specifically, the allyl epoxy polyether is selected from APE1000, APE600, APE1500, APEG-1000, but not limited thereto.
Wherein, the reaction mechanism is as follows:
step (1):
step (2):
and (4):
wherein the content of the first and second substances,
the invention has the following beneficial effects:
according to the preparation method of the low-ring silicone oil, after an intermediate is prepared, the intermediate is neutralized by adding sodium carbonate, filtered, and then vacuumized at high temperature (140-180 ℃), most of rings can be basically removed, the content of the rings is low, and then ring opening is carried out on the low-alkalinity tertiary amine and the double-epoxy-terminated polyether silicone oil, so that side reaction is avoided, linear Si-O chains are closed to form rings, the low-ring or even almost no rings are produced, and the low-ring silicone oil is green and environment-friendly, and can reach European standards such as a blue standard system.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
A preparation method of low-ring silicone oil comprises the following preparation steps:
(1) Sequentially adding 100g of octamethyltetrasiloxane and 1g of hydrogen-containing double-end socket into a reaction bottle, adding a proper amount of concentrated sulfuric acid serving as a catalyst, and reacting at 40 ℃ for 24 hours to prepare an intermediate;
(2) Adding sodium carbonate into the intermediate for neutralization, filtering, and then vacuumizing for 1.5 hours at the temperature of 150 ℃;
(3) Adding 50g of the intermediate and 10g of allyl epoxy polyether APEG-1000 into a reaction bottle, adding isopropanol, heating to 70 ℃, adding chloroplatinic acid, preserving heat for 1 hour, heating to 80 ℃, and preserving heat for reaction for 6 hours to obtain diepoxy terminated polyether silicone oil;
(4) And sequentially adding 100g of diepoxy terminated polyether silicone oil and 30g of tertiary amine polyether amine AE-1000 into a reaction bottle, adding a proper amount of isopropanol, stirring for 20 minutes, slowly heating to 80 ℃, reacting for 8 hours in a reflux state, cooling and discharging, wherein the product is low-ring silicone oil.
Example 2
A preparation method of low-ring silicone oil comprises the following preparation steps:
(1) Sequentially adding 100g of octamethyltetrasiloxane and 1.5g of hydrogen-containing double-end socket into a reaction bottle, adding a proper amount of concentrated sulfuric acid as a catalyst, and reacting at the temperature of 40 ℃ for 24 hours to obtain an intermediate;
(2) Adding sodium carbonate into the intermediate for neutralization, filtering, and then vacuumizing for 3 hours at the temperature of 140 ℃;
(3) Adding 50g of the intermediate and 10g of allyl epoxy polyether APE600 into a reaction bottle, adding isopropanol, heating to 70 ℃, adding chloroplatinic acid, preserving heat for 2 hours, heating to 80 ℃, and preserving heat for reaction for 8 hours to obtain diepoxy terminated polyether silicone oil;
(4) And sequentially adding 100g of diepoxy terminated polyether silicone oil and 40g of tertiary aminated polyether amine ER-700 into a reaction bottle, adding a proper amount of glacial acetic acid and isopropanol, stirring for 30 minutes, slowly heating to 80 ℃, reacting for 6 hours in a reflux state, cooling and discharging, wherein the product is low-ring silicone oil.
Example 3
A preparation method of low-ring silicone oil comprises the following preparation steps:
(1) Sequentially adding 100g of octamethyltetrasiloxane and 2g of hydrogen-containing double-end socket into a reaction bottle, adding a proper amount of concentrated sulfuric acid as a catalyst, and reacting at the temperature of 35 ℃ for 24 hours to obtain an intermediate;
(2) Adding sodium carbonate into the intermediate for neutralization, filtering, and then vacuumizing for 1 hour at the temperature of 160 ℃;
(3) Adding 50g of the intermediate and 10g of allyl epoxy polyether APE1000 into a reaction bottle, adding isopropanol, heating to 70 ℃, adding chloroplatinic acid as a catalyst, preserving heat for 2 hours, heating to 80 ℃, and preserving heat for reaction for 8 hours to obtain diepoxy terminated polyether silicone oil;
(4) And sequentially adding 100g of diepoxy terminated polyether silicone oil and 35g of tertiary aminated polyether amine AE-1000 into a reaction bottle, adding a proper amount of glacial acetic acid and isopropanol, stirring for 30 minutes, slowly heating to 80 ℃, reacting for 10 hours in a reflux state, cooling and discharging, wherein the product is low-ring silicone oil.
Comparative example 1
This comparative example is essentially the same as example 1 except that step (4) of comparative example 1 employs primary aminated polyetheramine ED-600 and step (4) of example 1 employs tertiary aminated polyetheramine AE-1000.
The primary aminated polyetheramine ED-600 has the following structural formula:
NH 2 CH(CH 3 )CH 2 -[OCH(CH 3 )CH 2 ] x -[OCH 2 CH 2 ] y -[OCH 2 CH(CH 3 )] z -NH 2
wherein Y =9, X + Z =3.6;
the rest is the same as example 1 and is not described here.
The products obtained in examples 1 to 3 and comparative example 1 were subjected to a ring body content test, the test results are shown in table 1, and the test methods are as follows:
weighing the product to obtain a mass m1, drying the product at the temperature of 150 ℃ for 30 minutes, cooling the product, weighing the product again to obtain a mass m2, and calculating according to the following formula:
α＝(m1-m2)/m1×100％；
if alpha is less than or equal to 0.5 percent, the silicone oil belongs to low ring bodies;
if alpha is greater than 0.5%, it is an indication that the silicone oil is not a low ring body.
TABLE 1 test results
| Test group | α |
| Example 1 | 0.42％ |
| Example 2 | 0.45％ |
| Example 3 | 0.43％ |
| Comparative example 1 | 0.74％ |
From the test results in table 1, it can be seen that α in the products of examples 1 to 3 prepared by the preparation method of the present invention is less than 0.5%, which indicates that there is no excessive loss of ring body during the drying process, and it belongs to low ring body silicone oil, while in comparative example 1, α is greater than 0.5%, which indicates that more ring bodies can be removed during the drying process, and it does not belong to low ring body silicone oil, because the present invention can avoid side reaction to cause linear Si-O chain to close ring by ring opening through the tertiary aminated polyether amine with lower basicity and the di-epoxy terminated polyether silicone oil, and therefore, lower ring body content in the product can be achieved, while in comparative example 1, lower ring body content in the product cannot be achieved by using primary aminated polyether amine.
Although the present invention has been described with reference to the preferred embodiments, it will be understood by those skilled in the art that various changes may be made and equivalents may be substituted for elements thereof without departing from the scope of the invention.
Claims (10)
1. A low-ring silicone oil is characterized by being shown in a structural formula I:
wherein n is more than or equal to 5,
2. The low-ring silicone oil as claimed in claim 1, wherein 30. Gtoreq.a.gtoreq.4, 40. Gtoreq.b.gtoreq.5, 30. Gtoreq.n.gtoreq.5, 30. Gtoreq.c.gtoreq.5, and 20. Gtoreq.d.gtoreq.6.
3. The method for preparing the low-ring silicone oil according to claim 1, wherein the preparation step comprises:
(1) Reacting octamethyltetrasiloxane and a hydrogen-containing double-end socket at 30-45 ℃ under the condition of concentrated sulfuric acid serving as a catalyst to prepare an intermediate;
(2) Adding sodium carbonate into the intermediate for neutralization, filtering, and then vacuumizing at high temperature;
(3) Reacting the intermediate treated in the step (2) with allyl epoxy polyether under the condition of chloroplatinic acid catalyst to obtain diepoxy terminated polyether silicone oil;
(4) And (3) carrying out a downward reaction on the diepoxy terminated polyether silicone oil and tertiary aminated polyether amine under a weak acidic condition to prepare the low-ring silicone oil.
4. The method for preparing the low-ring silicone oil according to claim 3, wherein in the step (1), the mass ratio of the octamethyltetrasiloxane to the hydrogen-containing double end enclosure is 100.5-2.
5. The method for preparing low-ring silicone oil according to claim 3, wherein in the step (2), vacuum is applied at 140 to 180 ℃ for 1 to 3 hours.
6. The method for preparing the low-ring silicone oil according to claim 3, wherein in the step (3), the mass ratio of the intermediate to the allyl epoxy polyether is 5.
7. The method for preparing low-ring silicone oil according to claim 3, wherein in step (4), the weak acid condition is at least one selected from the group consisting of acetic acid, propionic acid, lauric acid and isopropyl alcohol.
8. The process for preparing low-ring silicone oils according to claim 3, wherein in step (4), the tertiary aminated polyetheramine has a molecular weight of 500 to 2500.
9. The method for preparing low-ring silicone oil according to claim 3, wherein in the step (4), the mass ratio of the diepoxy-terminated polyether silicone oil to the tertiary aminated polyether amine is 100.
10. The method for preparing low-ring silicone oil according to claim 3, wherein allyl epoxy polyether has a molecular weight of 500 to 2000.
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| CN202211691627.7A CN115926173A (en) | 2022-12-26 | 2022-12-26 | Low-ring silicone oil and preparation method thereof |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102617863A (en) * | 2012-03-30 | 2012-08-01 | 广东工业大学 | Preparation method of hydrophilic block polyether aminosilicone |
| US20130030131A1 (en) * | 2010-04-06 | 2013-01-31 | Dow Corning Corporation | Reactive Amine-Functional Silicone-Polyether Block Copolymers |
| US20190119450A1 (en) * | 2016-04-19 | 2019-04-25 | Wacker Chemie Ag | Amino-organopolysiloxanes and preparation method therefor |
| CN111139652A (en) * | 2020-01-08 | 2020-05-12 | 东阳市德圣印染助剂有限公司 | Novel hydrophilic finishing agent for spinning |
| CN114517411A (en) * | 2022-01-27 | 2022-05-20 | 浙江传化功能新材料有限公司 | Preparation method and application of washable cotton fabric softener |
-
2022
- 2022-12-26 CN CN202211691627.7A patent/CN115926173A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130030131A1 (en) * | 2010-04-06 | 2013-01-31 | Dow Corning Corporation | Reactive Amine-Functional Silicone-Polyether Block Copolymers |
| CN102617863A (en) * | 2012-03-30 | 2012-08-01 | 广东工业大学 | Preparation method of hydrophilic block polyether aminosilicone |
| US20190119450A1 (en) * | 2016-04-19 | 2019-04-25 | Wacker Chemie Ag | Amino-organopolysiloxanes and preparation method therefor |
| CN111139652A (en) * | 2020-01-08 | 2020-05-12 | 东阳市德圣印染助剂有限公司 | Novel hydrophilic finishing agent for spinning |
| CN114517411A (en) * | 2022-01-27 | 2022-05-20 | 浙江传化功能新材料有限公司 | Preparation method and application of washable cotton fabric softener |
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