CN109762122A - A kind of Effect of Organosilicon-modified Phenol-formaldehyde Resin, preparation method and applications - Google Patents
A kind of Effect of Organosilicon-modified Phenol-formaldehyde Resin, preparation method and applications Download PDFInfo
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- CN109762122A CN109762122A CN201811625802.6A CN201811625802A CN109762122A CN 109762122 A CN109762122 A CN 109762122A CN 201811625802 A CN201811625802 A CN 201811625802A CN 109762122 A CN109762122 A CN 109762122A
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Abstract
The present invention provides a kind of Effect of Organosilicon-modified Phenol-formaldehyde Resin, preparation method and applications, it is related to phenolic resin field, Effect of Organosilicon-modified Phenol-formaldehyde Resin is made by raw materials such as resorcinol, formaldehyde, organosilicon modifiers in the present invention, substitutes resorcinol or resorcinol formaldehyde resin.While resorcinol is reduced using bring smoke and toxicity problem, alkoxy in product can be chemically reacted with the hydroxyl on white carbon black surface, the molecular structure of long-chain can open the reunion of filler simultaneously, improve the dispersion performance of filler, reduce the heat of belt in use；Benzothiazole sulfydryl in structure, can react in sulfidation with rubber molecular chain, and the network of vulcanized rubber and resin network are combined, and reduce the increase of heat caused by rubber rubs when deformation occurs with resin network between each other.
Description
Technical field
The present invention relates to be related to phenolic resin field, and in particular to a kind of Effect of Organosilicon-modified Phenol-formaldehyde Resin, preparation method and
It is applied.
Background technique
In rubber industry, resorcinol or resorcinol formaldehyde resin have for a long time as the complex and adhesive of rubber
Usage history, especially in radial industry.In radial industry, coppered steel wire is main as framework material
It is to play humidification, the superiority and inferiority of tire belt rubber and steel wire bond properties determines the good of tire used performance
It is bad.Therefore, in order to ensure the excellent bonds between steel wire and rubber, make usually using resorcinol or resorcinol formaldehyde resin
For binder resin.But resorcinol is easy to smolder at the process conditions, and its be more toxic to staff's actual bodily harm compared with
Greatly, resorcinol formaldehyde resin solves its smoke and toxicity problem, but there is also resorcinol formaldehyde resins in use,
Rubber network and resin network cannot form chemical bonding, and rubber is when deformation occurs, the friction of resin network and rubber network,
Lead to the increase of heat, in addition, the use of resorcinol formaldehyde resin causes rubber the problem of delay vulcanization occur.
In the use process of tire, belt position distortions are larger and bear the most stress of tire, and rubber is viscous
Elastic material, sizing material generate hysteresis loss, and the mechanical energy during deformations of tyre is changed into thermal energy, and belt position generates a large amount of
Heat is declined using properties of rubber for a long time, while sizing material also declines with all-steel cord bonding force, is generated banding and is detached from, to wheel
The durability that tire uses is very unfavorable.Belt heat is solved the problems, such as, mainly by silane coupled containing adding in silica compound
Agent changes carbon black types realization, and addition silane coupling agent usually requires to change processing technology and formula, changes carbon black types
It will cause the decline for the physical property such as stretching surely, two methods less effective.As invented a kind of novel silicon in patent CN101492593B
Alkane coupling agent reduces the hysteresis loss of belt sizing material.
Therefore, tire belt rubber and steel wire bond and the heat problem of belt position rubber has become rubber
The important research direction of tire industry.The present invention provides a kind of Effect of Organosilicon-modified Phenol-formaldehyde Resin, can be improved rubber and steel wire
Bond properties and aging between cord bond conservation rate, extend the vulcanization time for shortening rubber while burnt rubber burns the time, drop
The heat of low rubber.
Summary of the invention
(1) the technical issues of solving
In view of the deficiencies of the prior art, it the present invention provides a kind of Effect of Organosilicon-modified Phenol-formaldehyde Resin, preparation method and its answers
With can be improved the adhesive strength and aging adhesive strength between rubber and all-steel cord, while extending burnt rubber and burning the time
The vulcanization time for shortening rubber simultaneously, reduces the heat of rubber size, guarantees the durability of tire, and that improves tire uses the longevity
Life.
(2) technical solution
In order to achieve the above object, the present invention is achieved by the following technical programs:
A kind of Effect of Organosilicon-modified Phenol-formaldehyde Resin, the Effect of Organosilicon-modified Phenol-formaldehyde Resin have formula (1) structure:
In formula (1), m, n are positive integer, n > m；R1For methylene, ethylidene, propylidene or C4-C30Straight chained alkyl；R2For
Identical or different alkyl, polyether base-O- (R4-O)x-R5；R4Be it is identical or different and represent linear chain or branched chain, saturation or
Unsaturated aliphatic divalent C1-C30Alkyl, x 1-30；R5It is 1-30 carbon atom and represents unsubstituted or substituted straight
Chain or linear monovalent alkyl, alkenyl, aryl or aralkyl.
The preparation method of above-mentioned Effect of Organosilicon-modified Phenol-formaldehyde Resin, comprising the following steps:
(1) resorcinol heating is added in reaction kettle, catalyst 1 is added in temperature-rise period, after reaching 90-100 DEG C of temperature,
Formaldehyde is added dropwise under reflux conditions, 60-90min is added completely into back flow reaction 0.5-1.5h after formaldehyde；
(2) it is warming up to 100-110 DEG C, a small amount of resorcinol is added in reactant and is flowed back, reaction temperature, decompression are increased
Distilled water is distilled off；Distillation is completed, and adjusts reaction temperature to 100-140 DEG C, catalyst 2 is added, organosilicon is added dropwise and changes
Property agent, is stirred, obtains Effect of Organosilicon-modified Phenol-formaldehyde Resin；
Wherein, the organosilicon modifier has formula (2) structure:
In formula (2), R3It is identical or different and represents R2、C1-C12Alkyl or R6O group；R6For H, methyl, ethyl, third
Base, C4-C30Linear chain or branched chain monovalent alkyl, alkenyl, aryl or aralkyl or (R7)3Si group；R7For C1-C30Straight chain or straight chain
Alkyl or alkene.
Preferably, catalyst 1 described in step (1) is toluenesulfonic acid, sulfuric acid, one or more combinations in phosphoric acid or oxalic acid
Object.
Preferably, the molar ratio of resorcinol described in step (1) and formaldehyde is 1:0.4-0.6.
Preferably, a small amount of resorcinol of supplement described in step (2) is the 1%-2% that resorcinol amount has been added.
Preferably, catalyst 2 described in step (2) is sodium hydroxide.
Preferably, the additional amount of the organosilicon modifier is the 2-6% of resorcinol quality.
Application of the above-mentioned Effect of Organosilicon-modified Phenol-formaldehyde Resin in tire belt.
(3) beneficial effect
The present invention provides a kind of Effect of Organosilicon-modified Phenol-formaldehyde Resin, preparation method and applications, have the advantages that
1. resorcinol use can be reduced after structure of the invention resin substitution resorcinol or resorcinol formaldehyde resin
Smoke and toxicity problem in the process；
2. the benzothiazole sulfydryl in resin network structure of the present invention can occur in sulfidation with rubber molecular chain
Reaction, the network of vulcanized rubber and resin network are combined, reduce rubber when deformation occurs with resin network phase
The increase of heat caused by rubbing between mutually；
3. sizing material aging can be significantly improved after resin substitution resorcinol of the present invention or resorcinol formaldehyde resin
Bond conservation rate.
4. the introducing of organosilicon radical promotes the crosslinking of rubber and filler (white carbon black) in resin of the present invention, sizing material adds
Work performance improvement, while the bonding heat resistance of its rubber is improved, heat aging performance is greatly improved.
Detailed description of the invention
In order to make the object, technical scheme and advantages of the embodiment of the invention clearer, below in conjunction with the embodiment of the present invention,
Technical scheme in the embodiment of the invention is clearly and completely described, it is clear that described embodiment is the present invention one
Divide embodiment, instead of all the embodiments.Based on the embodiments of the present invention, those of ordinary skill in the art are not making
Every other embodiment obtained, shall fall within the protection scope of the present invention under the premise of creative work.
Fig. 1 is the reaction principle figure of step (1) in preparation method of the present invention；
Fig. 2 is the reaction principle figure of step (2) in preparation method of the present invention.
Specific embodiment
In order to make the object, technical scheme and advantages of the embodiment of the invention clearer, below in conjunction with the embodiment of the present invention,
Technical scheme in the embodiment of the invention is clearly and completely described, it is clear that described embodiment is the present invention one
Divide embodiment, instead of all the embodiments.Based on the embodiments of the present invention, those of ordinary skill in the art are not making
Every other embodiment obtained, shall fall within the protection scope of the present invention under the premise of creative work.
Embodiment 1:
Into the 1L four round flask equipped with stirring, temperature control, reflux condensing tube and constant pressure funnel, isophthalic two is added
Phenol 110g (1mol) is added the 1:1 mixed acid 1.88g (0.02mol) of catalyst oxalic acid and sulfuric acid, is warming up to 95 DEG C, 95 DEG C by
48.65g, 37% formaldehyde (0.6mol) is added dropwise in drop, drips heat preservation reflux 1h, is warming up to 105 DEG C, heating air-distillation to 160
DEG C, -0.08mpa be evaporated under reduced pressure 60min, distillation complete, adjust reaction temperature to 100 DEG C, be added 4g, 50% sodium hydroxide it is molten
3.53g organosilicon modifier is added dropwise in liquid, is stirred reaction 60min, obtains the Effect of Organosilicon-modified Phenol-formaldehyde Resin of 115g.
The wherein structural formula of organosilicon modifier are as follows:
Embodiment 2:
Into the 1L four round flask equipped with stirring, temperature control, reflux condensing tube and constant pressure funnel, isophthalic two is added
Phenol 110g (1mol) is added the 1:1 mixed acid 1.88g (0.02mol) of catalyst oxalic acid and sulfuric acid, is warming up to 95 DEG C, 90min by
48.65g, 37% formaldehyde (0.6mol) is added dropwise in drop, drips heat preservation reflux 1h, is warming up to 100 DEG C, 1.1g is added in reactant
(0.01mol) resorcinol insulation reaction 0.5h, and flow back and heat up air-distillation to 160 DEG C, -0.08mpa is evaporated under reduced pressure
60min, distillation are completed, and are adjusted reaction temperature to 120 DEG C, the sodium hydroxide solution of 4g, 50% are added, 3.67g, which is added dropwise, to be had
Machine silica modifier is stirred reaction 60min, obtains the Effect of Organosilicon-modified Phenol-formaldehyde Resin of 120g.
Wherein, the structural formula of organosilicon modifier are as follows:
Embodiment 3:
Into the 1L four round flask equipped with stirring, temperature control, reflux condensing tube and constant pressure funnel, isophthalic two is added
Phenol 110g (1mol) is added the 1:1 mixed acid 1.88g (0.02mol) of catalyst oxalic acid and sulfuric acid, is warming up to 95 DEG C, 60min by
48.65g, 37% formaldehyde (0.6mol) is added dropwise in drop, drips heat preservation reflux 1h, is warming up to 100 DEG C, 1.1g is added in reactant
(0.01mol) resorcinol insulation reaction 0.5h, and flow back and heat up air-distillation to 160 DEG C, -0.08mpa is evaporated under reduced pressure
60min, distillation are completed, and are adjusted reaction temperature to 120 DEG C, the sodium hydroxide solution of 4g, 50% are added, 3.67g, which is added dropwise, to be had
Machine silica modifier is stirred reaction 60min, obtains the Effect of Organosilicon-modified Phenol-formaldehyde Resin of 118.0g.
Wherein, the structural formula of organosilicon modifier are as follows:
Embodiment 4:
Into the 1L four round flask equipped with stirring, temperature control, reflux condensing tube and constant pressure funnel, isophthalic two is added
Phenol 110g (1mol) is added the 1:1 mixed acid 1.88g (0.02mol) of catalyst oxalic acid and sulfuric acid, is warming up to 100 DEG C, 100 DEG C
40.54g, 37% formaldehyde (0.5mol) are added dropwise dropwise, drips heat preservation reflux 1h, 1.1g (0.01mol) is added in reactant
Resorcinol insulation reaction 0.5h, and flow back and heat up air-distillation to 160 DEG C, -0.08mpa is evaporated under reduced pressure 60min, has distilled
At adjusting reaction temperature is added the sodium hydroxide solution of 4g, 50%, 3.40g organosilicon modifier is added dropwise, stirs to 120 DEG C
Hybrid reaction 60min is mixed, the Effect of Organosilicon-modified Phenol-formaldehyde Resin of 111.0g is obtained.
Wherein, the structural formula of organosilicon modifier are as follows:
Embodiment 5:
Into the 1L four round flask equipped with stirring, temperature control, reflux condensing tube and constant pressure funnel, isophthalic two is added
Phenol 110g (1mol) is added the 1:1 mixed acid 1.88g (0.02mol) of catalyst oxalic acid and sulfuric acid, is warming up to 95 DEG C, 95 DEG C by
56.75g, 37% formaldehyde (0.7mol) is added dropwise in drop, drips heat preservation reflux 1h, is warming up to 100 DEG C, 1.1g is added in reactant
(0.01mol) resorcinol insulation reaction 0.5h, and flow back and heat up air-distillation to 160 DEG C, -0.08mpa is evaporated under reduced pressure
60min, distillation are completed, and are adjusted reaction temperature to 120 DEG C, the sodium hydroxide solution of 4g, 50% are added, 3.64g, which is added dropwise, to be had
Machine silica modifier is stirred reaction 60min, obtains the Effect of Organosilicon-modified Phenol-formaldehyde Resin of 118.92g.
Wherein, the structural formula of organosilicon modifier are as follows:
Embodiment 6:
Into the 1L four round flask equipped with stirring, temperature control, reflux condensing tube and constant pressure funnel, isophthalic two is added
Phenol 110g (1mol) is added the 1:1 mixed acid 1.88g (0.02mol) of catalyst oxalic acid and sulfuric acid, is warming up to 90 DEG C, 90 DEG C by
48.65g, 37% formaldehyde (0.6mol) is added dropwise in drop, drips heat preservation reflux 1h, is warming up to 100 DEG C, 1.1g is added in reactant
(0.01mol) resorcinol insulation reaction 0.5h, and flow back and heat up air-distillation to 160 DEG C, -0.08mpa is evaporated under reduced pressure
60min, distillation are completed, and are adjusted reaction temperature to 120 DEG C, the sodium hydroxide solution of 4g, 50% are added, 6.11g, which is added dropwise, to be had
Machine silica modifier is stirred reaction 60min, obtains the Effect of Organosilicon-modified Phenol-formaldehyde Resin of 122.5g.
Wherein, the structural formula of organosilicon modifier are as follows:
Embodiment 7:
Into the 1L four round flask equipped with stirring, temperature control, reflux condensing tube and constant pressure funnel, isophthalic two is added
Phenol 110g (1mol) is added the 1:1 mixed acid 1.88g (0.02mol) of catalyst oxalic acid and sulfuric acid, is warming up to 95 DEG C, 95 DEG C by
48.65g, 37% formaldehyde (0.6mol) is added dropwise in drop, drips heat preservation reflux 1h, is warming up to 110 DEG C, 1.1g is added in reactant
(0.01mol) resorcinol insulation reaction 0.5h, and flow back and heat up air-distillation to 160 DEG C, -0.08mpa is evaporated under reduced pressure
60min, distillation are completed, and are adjusted reaction temperature to 140 DEG C, the sodium hydroxide solution of 4g, 50% are added, 2.44g, which is added dropwise, to be had
Machine silica modifier is stirred reaction 60min, obtains the Effect of Organosilicon-modified Phenol-formaldehyde Resin of 119g.
Wherein, the structural formula of organosilicon modifier are as follows:
Beneficial effect in order to further illustrate the present invention, select 1-7 of the embodiment of the present invention preparation final product with it is right
Ratio carries out every correlated performance test and comparison, and result is recorded in table 1-5；
Wherein, the operating procedure of comparative example is as follows:
Into the 1L four round flask equipped with stirring, temperature control, reflux condensing tube and constant pressure funnel, isophthalic two is added
Phenol 110g (1mol) is added catalyst oxalic acid 1.8g (0.02mol), is warming up to 95 DEG C, and 95 DEG C are added dropwise 48.65g, 37% first dropwise
Aldehyde (0.6mol) drips heat preservation 1h, is warming up to 105 DEG C, to 160 DEG C, -0.08mpa is evaporated under reduced pressure for heating air-distillation
60min obtains the resorcinol formaldehyde resin of 108.8g, this is traditional resorcinol formaldehyde resin.
(1) by liquid-phase chromatographic analysis free phenol content, the results are shown in Table 1.
1 synthetic resin free phenol content of table
(2) rubber internal mixing temperature is 130-140 DEG C, simulates rubber internal mixing condition, resin is put into crucible as 140 DEG C
Muffle furnace in after 30min, with electronic balance weighing and calculating volatile contents: volatile contents=[(weight after weight-placement before placing
Amount)/place preceding weight] * 100%.
2 synthetic resin volatile contents of table
(3) synthetic resin storage is tested
After preparing sold resin, obtained resin is tested into its moisture using karl Fischer moisture titration at once, it
After be divided to two groups to place 30 days by resin opening and under confined conditions under conditions of 25 DEG C of temperature, humidity 60-80%, test its water
Point, then impregnated 15 days in 25 DEG C of water, test its sample moisture content.Test result is as shown in table 3.
Moisture content is tested in 3 embodiment of table and comparative example
(4) application of the synthetic resin in rubber product, experimental formula are as shown in table 4:
4 recipe ingredient detail of table
| Raw material | Parts by weight |
| Natural rubber (5# marks glue) | 100 |
| Carbon black (N375) | 50 |
| White carbon black (HCSIL-833MP) | 10 |
| Zinc oxide | 8 |
| Stearic acid | 1 |
| Anti-aging agent (4020) | 1.5 |
| Anti-aging agent (RD) | 1.0 |
| Cobalt salt (Texibond225) | 0.8 |
| Resin (comparative example 1, embodiment 1-7) | 1.5 |
| Insoluble sulfur (HDOT20) | 5 |
| Adhesive (RA-65) | 5 |
| Promotor (DZ) | 1 |
Rubber compound prepared by reference formulations 1 and Example formulations 1-7, according to following standard testings:
Curability measurement: it is measured with reference to curability of the GB/T 16584-1996 to sizing material；
Mechanics Performance Testing: it is tested by GB/T528-2009.
Vulcanized rubber hardness: Determination of Hardness is carried out by GBT531.1-2008.
Compression heat generation: being tested by GB/T 1687-1993, and experimental temperature is 55 DEG C, load 1.5Mpa, compression frequency
Rate 30Hz, temperature rise of the test sample in compression process, compression temperature rise is lower, and the heat for reacting vulcanizate is lower.
DMA test: vulcanizate is tested using dynamic mechanical analysis, test condition are as follows: test pattern is stretching die
Formula, dynamic strain 0.25%, static strain 1%, heating rate 3K/min.60 DEG C of tan δ values are smaller, belt sizing material
Calorific value it is lower.
Rubber and all-steel cord bonding force are tested: reference standard GB/T 16586-2014 is tested, and numerical value is bigger, card
Bright performance is better.
Table 5: comparative example and embodiment performance test
It is found that the advantageous resorcinol content and volatile contents of embodiment resin are far below comparative example resin from table 1-2.
As can be known from Table 3, comparative example and embodiment are not much different in the moisture content of starting, but either place in opening
Or embodiment resin all shows lower water imbibition after closed placement, while in impregnating the experiment placed, Ke Yifa
The resin of current embodiment possesses lower water absorption, and water resistance is more preferable, is easier to store.
As can be known from Table 5, using structure of the invention resin: sizing material time of scorch increases；50% and 300% stress at definite elongation,
The physical property such as tensile strength have increased trend；Sizing material heat is lower；All-steel cord and the enhancing of rubber adhesion power, it is old after bonding aging
It is high to change conservation rate, is very helpful to the durability of tire.
It should be noted that, in this document, relational terms such as first and second and the like are used merely to a reality
Body or operation are distinguished with another entity or operation, are deposited without necessarily requiring or implying between these entities or operation
In any actual relationship or order or sequence.Moreover, the terms "include", "comprise" or its any other variant are intended to
Non-exclusive inclusion, so that the process, method, article or equipment including a series of elements is not only wanted including those
Element, but also including other elements that are not explicitly listed, or further include for this process, method, article or equipment
Intrinsic element.In the absence of more restrictions, including the element that sentence "including a ..." limits, it is not excluded that
There is also other identical elements in the process, method, article or apparatus that includes the element.
The above embodiments are merely illustrative of the technical solutions of the present invention, rather than its limitations, although with reference to the foregoing embodiments
Invention is explained in detail, those skilled in the art should understand that: it still can be to aforementioned each implementation
Technical solution documented by example is modified or equivalent replacement of some of the technical features；And these modification or
Replacement, the spirit and scope for technical solution of various embodiments of the present invention that it does not separate the essence of the corresponding technical solution.
Claims (8)
1. a kind of Effect of Organosilicon-modified Phenol-formaldehyde Resin, which is characterized in that the Effect of Organosilicon-modified Phenol-formaldehyde Resin has formula (1) structure:
In formula (1), m, n are positive integer, n > m；R1For methylene, ethylidene, propylidene or C4-C30Straight chained alkyl；R2It is identical
Or different alkyl, polyether base-O- (R4-O)x-R5；R4Be it is identical or different and represent linear chain or branched chain, saturation or insatiable hunger
The aliphatic divalent C of sum1-C30Alkyl, x 1-30；R5Be 1-30 carbon atom and represent unsubstituted or substituted linear or
Linear monovalent alkyl, alkenyl, aryl or aralkyl.
2. the preparation method of Effect of Organosilicon-modified Phenol-formaldehyde Resin as described in claim 1, which comprises the following steps:
(1) resorcinol heating is added in reaction kettle, catalyst 1 is added in temperature-rise period, after reaching 90-100 DEG C of temperature, is returning
Formaldehyde is added dropwise under the conditions of stream, 60-90min is added completely into back flow reaction 0.5-1.5h after formaldehyde；
(2) it is warming up to 100-110 DEG C, a small amount of resorcinol is added in reactant and is flowed back, reaction temperature, vacuum distillation are increased
Remove distilled water；Distillation is completed, and adjusts reaction temperature to 100-140 DEG C, catalyst 2 is added, organosilicon modifier is added dropwise,
It is stirred, obtains Effect of Organosilicon-modified Phenol-formaldehyde Resin；
Wherein, the organosilicon modifier has formula (2) structure:
In formula (2), R3It is identical or different and represents R2、C1-C12Alkyl or R6O group；R6For H, methyl, ethyl, propyl,
C4-C30Linear chain or branched chain monovalent alkyl, alkenyl, aryl or aralkyl or (R7)3Si group；R7For C1-C30Straight chain or straight chained alkyl
Or alkene.
3. the preparation method of Effect of Organosilicon-modified Phenol-formaldehyde Resin as claimed in claim 2, which is characterized in that described in step (1)
Catalyst 1 is toluenesulfonic acid, sulfuric acid, one or more compositions in phosphoric acid or oxalic acid.
4. the preparation method of Effect of Organosilicon-modified Phenol-formaldehyde Resin as claimed in claim 2, which is characterized in that described in step (1)
The molar ratio of resorcinol and formaldehyde is 1:0.4-0.6.
5. the preparation method of Effect of Organosilicon-modified Phenol-formaldehyde Resin as claimed in claim 2, which is characterized in that described in step (2)
Supplementing a small amount of resorcinol is the 1%-2% that resorcinol amount has been added.
6. the preparation method of Effect of Organosilicon-modified Phenol-formaldehyde Resin as claimed in claim 2, which is characterized in that described in step (2)
Catalyst 2 is sodium hydroxide.
7. the preparation method of Effect of Organosilicon-modified Phenol-formaldehyde Resin as claimed in claim 2, which is characterized in that described organic-silicon-modified
The additional amount of agent is the 2-6% of resorcinol quality.
8. such as application of the described in any item Effect of Organosilicon-modified Phenol-formaldehyde Resin of claim 1-7 in tire belt.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1784462A (en) * | 2003-05-28 | 2006-06-07 | 茵迪斯佩克化学公司 | Silane-modified phenolic resins and applications thereof |
| CN102344462A (en) * | 2011-07-20 | 2012-02-08 | 江苏麒祥高新材料有限公司 | Low-volatility benzothiazolyl mercaptosilanes and preparation method thereof |
| CN106496476A (en) * | 2016-11-14 | 2017-03-15 | 东莞兆舜有机硅科技股份有限公司 | A kind of Effect of Organosilicon-modified Phenol-formaldehyde Resin and its application |
| CN106916267A (en) * | 2015-12-25 | 2017-07-04 | 广东生益科技股份有限公司 | A kind of organic-silicon-modified phenolic resin, Preparation method and use |
| CN109749146A (en) * | 2018-12-28 | 2019-05-14 | 江苏麒祥高新材料有限公司 | A kind of low-heat-generation rubber composition for bead wire belt |
-
2018
- 2018-12-28 CN CN201811625802.6A patent/CN109762122A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1784462A (en) * | 2003-05-28 | 2006-06-07 | 茵迪斯佩克化学公司 | Silane-modified phenolic resins and applications thereof |
| CN102344462A (en) * | 2011-07-20 | 2012-02-08 | 江苏麒祥高新材料有限公司 | Low-volatility benzothiazolyl mercaptosilanes and preparation method thereof |
| CN106916267A (en) * | 2015-12-25 | 2017-07-04 | 广东生益科技股份有限公司 | A kind of organic-silicon-modified phenolic resin, Preparation method and use |
| CN106496476A (en) * | 2016-11-14 | 2017-03-15 | 东莞兆舜有机硅科技股份有限公司 | A kind of Effect of Organosilicon-modified Phenol-formaldehyde Resin and its application |
| CN109749146A (en) * | 2018-12-28 | 2019-05-14 | 江苏麒祥高新材料有限公司 | A kind of low-heat-generation rubber composition for bead wire belt |
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Application publication date: 20190517 |