CN107556471A - A kind of non-isocyanate organic silicon polyurethane block copolymer and its synthetic method - Google Patents
A kind of non-isocyanate organic silicon polyurethane block copolymer and its synthetic method Download PDFInfo
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- CN107556471A CN107556471A CN201710840323.5A CN201710840323A CN107556471A CN 107556471 A CN107556471 A CN 107556471A CN 201710840323 A CN201710840323 A CN 201710840323A CN 107556471 A CN107556471 A CN 107556471A
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- block copolymer
- cyclic carbonate
- carbonate ester
- copolymer
- polyuretyane
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- 229920001400 block copolymer Polymers 0.000 title claims abstract description 26
- 238000010189 synthetic method Methods 0.000 title claims abstract description 15
- 229920002635 polyurethane Polymers 0.000 title abstract description 15
- 239000004814 polyurethane Substances 0.000 title abstract description 15
- 239000012948 isocyanate Substances 0.000 title abstract description 13
- 150000002513 isocyanates Chemical class 0.000 title abstract description 11
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title abstract description 6
- 229910052710 silicon Inorganic materials 0.000 title abstract description 6
- 239000010703 silicon Substances 0.000 title abstract description 6
- -1 cyclic carbonate ester Chemical class 0.000 claims abstract description 36
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 229920001577 copolymer Polymers 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 6
- CQGUCUVIZJHFOA-UHFFFAOYSA-N [Si+4].[N-]=C=O.[N-]=C=O.[N-]=C=O.[N-]=C=O Chemical compound [Si+4].[N-]=C=O.[N-]=C=O.[N-]=C=O.[N-]=C=O CQGUCUVIZJHFOA-UHFFFAOYSA-N 0.000 claims description 14
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 229920001296 polysiloxane Polymers 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 claims description 3
- 125000005375 organosiloxane group Chemical group 0.000 claims description 2
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 claims 1
- 125000005442 diisocyanate group Chemical group 0.000 abstract description 6
- 230000003487 anti-permeability effect Effects 0.000 abstract description 4
- 230000007613 environmental effect Effects 0.000 abstract description 4
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract description 3
- 230000003373 anti-fouling effect Effects 0.000 abstract description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 239000000835 fiber Substances 0.000 abstract description 3
- 239000010985 leather Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000011247 coating layer Substances 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- 231100000331 toxic Toxicity 0.000 abstract description 2
- 230000002588 toxic effect Effects 0.000 abstract description 2
- 238000009941 weaving Methods 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
Abstract
The present invention relates to a kind of non-isocyanate organic silicon polyurethane block copolymer and its synthetic method, the polyaddition reaction specifically carried out in a solvent with cyclic carbonate ester with α, ω aminoalkylpolysiloxanes.Non-isocyanate organic silicon polyurethane block copolymer prepared by the present invention, avoid the use of toxic raw materials diisocyanate, production technology and product safety environmental protection, and the hydroxyl in carbamate segment on the carbon atom of β positions can form intramolecular hydrogen bond with its carbonyl, with stronger molecular force, the hydrolytic resistance of copolymer, chemical resistance and anti-permeability performance are more excellent, can be according to polysiloxanes chain length, cyclic carbonate ester structure is designed to block copolymer structure, to meet it in antifouling flash coating layer, leather, weaving, papermaking, fiber treatment, the application in the fields such as medicine equipment.
Description
Technical field
The invention belongs to organosilicon macromolecule technical field, more particularly to a kind of non-isocyanate polysiloxane-polyurethane is embedding
Section copolymer and its synthetic method.
Background technology
Synthesis of polysiloxane-polyurethane block copolymer is a kind of rising high polymer material.From molecule segment knot
Structure sees that polysiloxanes segment can provide excellent heat endurance, dielectricity, pliability, water resistance, gas permeability and bio-compatible
Property；Polyurethane segment can then provide good mechanical property, wearability etc..Therefore, this material had both overcome polysiloxanes machine
The shortcomings that tool poor performance, the deficiency of polyurethane weatherability difference is also compensate for, there is good water resistance, low-temperature flexibility, surface
Enriching, dielectricity and excellent biocompatibility, in antifouling flash coating layer, leather, weaving, papermaking, fiber treatment, medicine equipment
There is huge application potential Deng field.
At present, the synthetic method of Silicon Oligomer-polyuretyane Block Copolymer typically has two kinds：A kind of method is the poly- silicon of hydroxyl alkyl
The reaction of oxygen alkane and diisocyanate；Another method is the reaction of aminoalkylpolysiloxanes and diisocyanate.Above two
Synthetic method is required for diisocyanate as raw material, and isocyanates is a kind of very big toxicant of harm to the human body, and
And isocyanates, to the moisture-sensitive in environment, this does not meet safe and environment-friendly developing direction.In recent years, with environmental problem
Increasingly highlight and petroleum resources it is increasingly deficient, green, low-carbon high-efficiency has turned into the main development of polyurethane industries among others
Direction, various renewable biomass based polyurethanes, aqueous polyurethane etc. continues to bring out, but these all no solution isocyanates
Use this critical problem.
Huang Yaocheng etc. on《The synthesis and application of non-isocyanate polyurethane》Research using cyclic carbonate compound with
Polyurethane is prepared in primary amine reaction, but its reaction typically uses two membered ring carbonates and binary primary amine reaction system, primary amine
Short-chain structure greatly limit the introducing of target group in polymerization efficiency and heavy polymer.
The content of the invention
In order to overcome above-mentioned deficiency, the present invention provide a kind of non-isocyanate Silicon Oligomer-polyuretyane Block Copolymer and its
Synthetic method.Reacted using cyclic carbonate ester and polysiloxanes, it is not using diisocyanate as raw material, and production technology and product are in itself
Safety and environmental protection, and the hydroxyl in carbamate segment on the carbon atom of β positions can with its carbonyl formed intramolecular hydrogen bond, have compared with
Strong intermolecular force, the hydrolytic resistance of copolymer, chemical resistance and anti-permeability performance are more excellent；This synthetic method is simple
Efficiently, it is practical, it is easy to spread.
To achieve the above object, the present invention uses following scheme：
A kind of non-isocyanate Silicon Oligomer-polyuretyane Block Copolymer, the copolymer is respectively with cyclic carbonate ester or containing ring
The disiloxane of carbonic acid is used as soft segment as hard section using polysiloxanes.
In order to overcome, existing two membered ring carbonates and binary primary amine reaction system polymer architecture are single, combined coefficient is low
Problem, the present invention chance under study for action：Existing binary primary amine is substituted with the polysiloxanes of Amino End Group, it is poly- being successfully introduced into
While siloxanes segment, polymerizeing for cyclic carbonate ester and amino, the non-isocyanate polysiloxane-polyurethane block of preparation are improved
Copolymer compared with isocyanate silicone-block polymers of polyurethane in terms of hydrolytic resistance, chemical resistance and anti-permeability performance more
To be excellent.
Preferably, the structural formula of the copolymer is any one following：
Wherein, n, x are natural number more than zero, R1Or R2For one in methyl, ethyl, vinyl, phenyl, trifluoro propyl
Kind is several.
Preferably, the R2Structural formula be-CH2-CH2-CH2-。
Present invention also offers a kind of synthetic method of non-isocyanate Silicon Oligomer-polyuretyane Block Copolymer, including：
Reacted in a solvent as raw material using the disiloxane and polysiloxanes of cyclic carbonate ester or the acid containing ring carbon, synthesize non-isocyanide
Acid esters Silicon Oligomer-polyuretyane Block Copolymer.
Preferably, the cyclic carbonate ester structural formula is：
Wherein, R1For one or more of combinations in hydrogen-based, methyl, phenyl or benzyl.
Preferably, the solvent be dioxane, tetrahydrofuran, ethyl acetate, DMF, isopropanol,
One or more of combinations in toluene or acetone.
Preferably, the reaction condition is：1~8h is reacted at room temperature；
Preferably, the mol ratio of the organosiloxane and cyclic carbonate ester is 1:1.
Preferably, the synthetic method of the disiloxane of the acid containing ring carbon is：By cyclic carbonate ester and tetramethyl containing vinyl
The hydrogen-based disiloxane of base two carries out hydrosilylation under karstedt catalyst, produces.
Present invention also offers non-isocyanate Silicon Oligomer-polyuretyane Block Copolymer prepared by any above-mentioned method.
Present invention also offers cyclic carbonate ester or the sour disiloxane containing ring carbon is preparing non-isocyanate organosilicon-poly- ammonia
Application in ester block copolymer.
Beneficial effects of the present invention
1) present invention, avoiding the use of toxic raw materials diisocyanate, production technology and product safety and environmental protection itself；Ammonia
Hydroxyl in carbamate segment on the carbon atom of β positions can form intramolecular hydrogen bond with its carbonyl, have stronger intermolecular interaction
Power, the hydrolytic resistance of copolymer, chemical resistance and anti-permeability performance are more excellent；Can be according to polysiloxanes chain length, cyclic carbonate ester
Structure is designed to block copolymer structure, to meet the requirement in different application field；
2) synthetic method of the present invention is simple efficient, practical, easy to spread.
Embodiment
Feature of present invention and other correlated characteristics are described in further detail by the following examples, in order to the same industry
The understanding of technical staff：
A kind of non-isocyanate Silicon Oligomer-polyuretyane Block Copolymer, it is characterised in that block copolymer structure formula is
Wherein, n, x are the natural number more than zero.
Preferably, the R is the one or more in methyl, ethyl, vinyl, phenyl, trifluoro propyl.
Preferably, the R2Structural formula be-CH2-CH2-CH2-。
Preferably, the structural formula of described cyclic carbonate ester is：
Wherein, R1For one or more of combinations in hydrogen-based, methyl, phenyl or benzyl；
Preferably, the solvent of the reaction be dioxane, it is tetrahydrofuran, ethyl acetate, DMF, different
One or more of combinations in propyl alcohol, toluene or acetone；
Preferably, the reaction time is 1~8h.
Preferably, the mol ratio of α in the reaction, ω-aminoalkyl polysiloxane and cyclic carbonate ester is 1:1.
Present invention also offers it is a kind of containing ring carbon acid disiloxane synthetic method, by the cyclic carbonate ester containing vinyl with
The hydrogen-based disiloxane of tetramethyl two carries out hydrosilylation under karstedt catalyst, produces.
Present invention also offers non-isocyanate Silicon Oligomer-polyuretyane Block Copolymer prepared by any of the above-described method.
Non-isocyanate Silicon Oligomer-polyuretyane Block Copolymer described in any of the above-described all can be used for preparing antifouling work painting
The fields such as layer, leather, textile material, papermaking material, fibre finish, medicine equipment, the product of synthesis can all meet industry
Related needs.
Present invention also offers a kind of synthetic method of preferably non-isocyanate Silicon Oligomer-polyuretyane Block Copolymer,
Including：At room temperature, α, ω-aminoalkylpolysiloxanes react 1~12h in a solvent with cyclic carbonate ester, and rear heat temperature raising removing is molten
Agent, obtain non-isocyanate Silicon Oligomer-polyuretyane Block Copolymer.
Embodiment 1
α, ω-aminoalkylpolysiloxanes10.0g with
Cyclic carbonate ester1.2g (ensures amino and cyclic carbonate ester equimolar ratio), in dioxy
It is well mixed in six ring solvents, reacts 6h at room temperature, rear heat temperature raising desolvation, obtain non-isocyanate polysiloxane-polyurethane
Block copolymer.
GPC obtains MnFor 8315, MwFor 14634, molecular weight distributing index 1.76.
Embodiment 2
The step described in embodiment 1 is repeated, simply α, ω-aminoalkylpolysiloxanes are
GPC obtains MnFor 7968, MwFor 15697, molecular weight distributing index 1.97.
Embodiment 3
The step described in embodiment 1 is repeated, simply α, ω-aminoalkylpolysiloxanes are
GPC obtains MnFor 9324, MwFor 17156, molecular weight distributing index 1.84.
Embodiment 4
The step described in embodiment 1 is repeated, simply α, ω-aminoalkylpolysiloxanes are
GPC obtains MnFor 9167, MwFor 15859, molecular weight distributing index 1.73.
Embodiment 5
The step described in embodiment 1 is repeated, simply α, ω-aminoalkylpolysiloxanes are
GPC obtains MnFor 8654, MwFor 15663, molecular weight distributing index 1.81.
Embodiment 6
The step described in embodiment 1 is repeated, simply α, ω-aminoalkylpolysiloxanes are
GPC obtains MnFor 8279, MwFor 15316, molecular weight distributing index 1.85.
Embodiment 7
The step described in embodiment 1 is repeated, simply the reaction time is 3h.
GPC obtains MnFor 8298, MwFor 15102, molecular weight distributing index 1.82.
Embodiment 8
The step described in embodiment 1 is repeated, simply the reaction time is 9h.
GPC obtains MnFor 8362, MwFor 14634, molecular weight distributing index 1.75.
Embodiment 9
The step described in embodiment 1 is repeated, simply cyclic carbonate ester is
GPC obtains MnFor 9563, MwFor 17596, molecular weight distributing index 1.84.
Embodiment 10
The step described in embodiment 1 is repeated, simply cyclic carbonate ester is
GPC obtains MnFor 9154, MwFor 16294, molecular weight distributing index 1.78.
Embodiment 11
The step described in embodiment 1 is repeated, simply cyclic carbonate ester is
GPC obtains MnFor 8498, MwFor 6146, molecular weight distributing index 1.90.
Finally it should be noted that the foregoing is only the preferred embodiments of the present invention, this hair is not limited to
Bright, although the present invention is described in detail with reference to the foregoing embodiments, for those skilled in the art, it is still
Technical scheme described in previous embodiment can be modified, or equivalent substitution is carried out to which part.It is all in this hair
Within bright spirit and principle, any modification, equivalent substitution and improvements made etc., protection scope of the present invention should be included in
Within.Although the above-mentioned embodiment to the present invention is described, not limiting the scope of the invention, institute
Category art personnel should be understood that on the basis of technical scheme those skilled in the art need not pay wound
The various modifications or deformation that the property made work can be made are still within protection scope of the present invention.
Claims (10)
1. a kind of non-isocyanate Silicon Oligomer-polyuretyane Block Copolymer, it is characterised in that the copolymer is respectively with ring carbon acid
The disiloxane of ester or the acid containing ring carbon is used as soft segment as hard section using polysiloxanes.
2. copolymer as claimed in claim 1, it is characterised in that the structural formula of the copolymer is any one following：
Wherein, n, x are natural number more than zero, R1Or R2For one kind in methyl, ethyl, vinyl, phenyl, trifluoro propyl or
It is several.
3. copolymer as claimed in claim 1, it is characterised in that the R2Structural formula be.
A kind of 4. synthetic method of non-isocyanate Silicon Oligomer-polyuretyane Block Copolymer, it is characterised in that including：
Reacted in a solvent as raw material using the disiloxane and polysiloxanes of cyclic carbonate ester or the acid containing ring carbon, synthesize non-isocyanate
Silicon Oligomer-polyuretyane Block Copolymer.
5. method as claimed in claim 3, it is characterised in that the cyclic carbonate ester structural formula is：
Wherein, R1For one or more of combinations in hydrogen-based, methyl, phenyl or benzyl.
6. method as claimed in claim 3, it is characterised in that the solvent be dioxane, tetrahydrofuran, ethyl acetate,
One or more of combinations in DMF, isopropanol, toluene or acetone.
7. method as claimed in claim 3, it is characterised in that the reaction condition is：1~8h is reacted at room temperature；
Or the mol ratio of the organosiloxane and cyclic carbonate ester is 1:1.
8. method as claimed in claim 3, it is characterised in that the synthetic method of the disiloxane of the acid containing ring carbon is to contain
The cyclic carbonate ester of vinyl carries out hydrosilylation with the hydrogen-based disiloxane of tetramethyl two under karstedt catalyst.
9. non-isocyanate Silicon Oligomer-polyuretyane Block Copolymer prepared by the method as described in claim any one of 4-8.
10. the disiloxane of cyclic carbonate ester or the acid containing ring carbon is in non-isocyanate Silicon Oligomer-polyuretyane Block Copolymer is prepared
Application.
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| CN108774322A (en) * | 2018-06-26 | 2018-11-09 | 湖北新海鸿化工有限公司 | A kind of preparation method of fabric softener |
| CN111378126A (en) * | 2020-05-14 | 2020-07-07 | 管善月 | Preparation method of non-isocyanate polyurethane prepolymer |
| CN112646177A (en) * | 2020-12-21 | 2021-04-13 | 常州大学 | High-strength double-repair non-isocyanate polyurethane and preparation method thereof |
| CN113336949A (en) * | 2021-06-21 | 2021-09-03 | 岭南师范学院 | Amino organic silicon-based pentaerythritol cyclic carbonate and preparation method and application thereof |
| CN113383031A (en) * | 2019-02-08 | 2021-09-10 | 巴斯夫欧洲公司 | Preparation of cured polymers containing urethane groups and silicon atoms |
| CN114763438A (en) * | 2021-01-14 | 2022-07-19 | 万华化学集团股份有限公司 | Organosilicon curing formula, curing method and silicone rubber prepared from organosilicon curing formula |
| CN114773828A (en) * | 2022-05-06 | 2022-07-22 | 盛鼎高新材料有限公司 | Corrosion-resistant polyurethane elastomer and preparation method thereof |
| CN115386091A (en) * | 2022-08-29 | 2022-11-25 | 中国林业科学研究院林产化学工业研究所 | Preparation method, application and regeneration method of high-strength self-healing organic silicon elastomer |
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