CN105623188B - A kind of Cardanol Modified PF Resin as rubber and its products adhesion agent - Google Patents
A kind of Cardanol Modified PF Resin as rubber and its products adhesion agent Download PDFInfo
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- CN105623188B CN105623188B CN201510685224.5A CN201510685224A CN105623188B CN 105623188 B CN105623188 B CN 105623188B CN 201510685224 A CN201510685224 A CN 201510685224A CN 105623188 B CN105623188 B CN 105623188B
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Abstract
As the application of adhesion promotor the invention proposes a kind of Cardanol Modified PF Resin and its in rubber and its product, the Cardanol Modified PF Resin is as adhesion promotor, so that the rubber and its product of preparation have the characteristics that the not smoke in mixing process, modulus is high, hardness is high, all-steel cord extraction performance is good.In addition, the invention also provides the tire belt by the rubber composition preparation comprising Cardanol Modified PF Resin and the pneumatic tires prepared by the tire belt.
Description
Technical field
The invention belongs to rubber and its arts, and in particular to a kind of Cardanol Modified PF Resin, and its as rubber
The adhesive of glue and its product, and using the adhesive rubber composition prepare tire belt and by the tire belt
The pneumatic tire of layer preparation.
Background technique
Rubber product, as tire, belt and hose generally require reinforcing material such as steel wire, fiber as framework material.Son
The belt of radial tire is often used steel wire, this just needs to keep good bonding force between vulcanized rubber and steel wire, usually adds
Enter adhesion promotion system to keep bonding force between rubber and steel wire.Existing adhesion promotion system generally comprise resorcinol or
Benzenediol resin is as methylene acceptor and hexa (HMT) or hexamethoxymethyl melamine (HMMM) as sub-
Methyl donor.In sulfidation, methylene acceptor and methylene give precursor reactant and generate resorcinol-formaldehyde resin network
Rubber and steel wire floor are protected, so as to improve the physical property, mechanical performance and bond properties of vulcanized rubber.
Pure resorcinol and modulus height, bond properties that methylene donor is provided as adhesion promotion system are good, but
It is that resorcinol is easy distillation, will appear smoke phenomenon in mixing process and generate health and environmental issue.Resorcinol first
The resorcinol to dissociate in urea formaldehyde or the resorcinol resin of modification substantially reduces, and resorcinol is released in mixing process
Greatly reduce.For example, patent US5021522 discloses the method using phenylethene modified resorcinol, between reducing in resin
Benzenediol content, but to sacrifice resorcin reaction active site as cost, the respond of resin and methylene donor
The modulus for weakening and it being caused to provide is relatively low.Patent CN201310007906.1 discloses the modified resorcinol formaldehyde of cashew nut diphenol
Resin, it is existing that the resorcinol to dissociate in resin still also will appear undesirable smoke between 8~12%, in mixing process
As.
Patent EP082791B1 discloses the resin of phenol, alkyl carbamate and formaldehyde preparation without containing isophthalic two
Phenol, however remaining urethane groups is stayed in resin and is partly released, and leads to smoke, and alkyl-alkyl formic acid esters also consumes
The reaction active sites of phenol.Patent CN102459379, which is disclosed, prepares phenol formaldehyde resin and urethane-urea formaldehyde mixture
As adhesion promotor, complex technical process needs first to prepare urethane-urea formaldehyde, then prepares phenol formaldehyde resin, Er Qieqi
In urethane-aldehyde resin component it is very low with the reactivity of methylene donor.
Summary of the invention
The shortcomings that in order to overcome the prior art, the invention proposes a kind of, Cardanol Modified PF Resins in rubber and its
Application in the adhesion promotor of product.In the prior art, Cardanol Modified PF Resin generally as rubber reinforcing agent,
It is used cooperatively with methylene donor, the modulus of Lai Tigao rubber, hardness (" rubber resin supporting material and its effect ", rubber
Glue industry, 2013 volume 60, page 52), and do not there is research to use Cardanol Modified PF Resin as adhesion promotor
Improve the bonding force of rubber.And the present invention uses Cardanol Modified PF Resin as adhesion promotor and is applied to rubber materials,
It can be added to the bonding force for improving vulcanized rubber and reinforcing material in rubber composition, smoke phenomenon will not be generated and influenced
Environment.And higher modulus and hardness can be provided, reinforcing effect is more preferable, and can significantly improve steel wire in steam ageing and salt
Extraction performance after water aging.
Anacardol is the weak yellow liquid that cashew nut shell oil passes through that vacuum distillation obtains, and composition includes cashew nut single phenol and cashew nut
Diphenol, shown in structural formula such as formula (I).Since long alkyl chain is located at the meta position of phenolic hydroxyl group, their structure and metacresol or isophthalic
Diphenol is similar, all has very high reactivity.Moreover, alkyl chain can increase the compatibility of resin and rubber, to promote
Resin network is compatible with rubber network.Moreover, the double bond on alkyl chain can will also be set in Vulcanization Process of Rubber with sulfur reaction
Rouge network and rubber network are connected by chemical bond.These factors are all conducive to improve modulus, hardness and the steel wire of sizing material
Extraction force.
Cardanol Modified PF Resin can be prepared by following two method, and a kind of method is anacardol and phenols chemical combination
Object is reacted with aldehyde compound in the presence of a catalyst, and the double bond of anacardol alkyl chain is protected in the resin of this method preparation
It stays；Another method is phenolic compound and aldehyde compound is first prepared into resin in the presence of a catalyst, then anacardol with
The resin is prepared into Cardanol Modified PF Resin, the resin anacardol alkyl of this method preparation by the alkylation reaction of double bond
The double bond of chain is greatly consumed.
A kind of the invention proposes Cardanol Modified PF Resins in rubber and its product answering as adhesion promotor
With, wherein shown in Cardanol Modified PF Resin the structure such as formula (a) or formula (b),
In formula (a):
R is selected from one or both of the alkyl of H, C1-C6；
R1One or both of alkyl selected from H, OH, C1-C6；
R2Selected from saturation one or both of C15 alkyl or unsaturation C15 alkyl；
R3Selected from one or both of H, OH；
X, y is respectively the integer of 1-15；
In formula (b):
R is selected from one or both of the alkyl of H, C1-C6；
R1One of alkyl selected from H, OH, C1-C6 is a variety of；
R2Selected from saturation C15 alkyl or unsaturation C15 alkyl；
R3Selected from H or OH；
X, y is respectively the integer of 1-15.
Preferably, the Cardanol Modified PF Resin is shown in formula (a).
Wherein, the quality of the Cardanol Modified PF Resin is the 1-10% of rubber and its quality of item.
The invention also provides one kind Cardanol Modified PF Resins as shown in formula (a) or formula (b) in tire belt
In application.
The invention also provides one kind Cardanol Modified PF Resin as shown in formula (a) or formula (b) answering in tire
With.
The invention proposes a kind of Cardanol Modified PF Resins, shown in structure such as formula (a) or formula (b),
In formula (a):
R is selected from one or both of the alkyl of H, C1-C6；
R1 is selected from one or both of the alkyl of H, OH or C1-C6；
R2 is selected from saturation one or both of C15 alkyl or unsaturation C15 alkyl；
R3 is selected from one or both of H or OH；
X, y is respectively the integer of 1-15.
In formula (b):
R is selected from one or both of the alkyl of H, C1-C6；
R1One of alkyl selected from H, OH or C1-C6 is a variety of；
R2Selected from saturation C15 alkyl or unsaturation C15 alkyl；
R3Selected from H or OH；
X, y is respectively the integer of 1-15.
The present invention also provides a kind of rubber compositions, wherein (is indicated including following component with mass parts):
100 parts of natural rubbers (NR), synthetic rubber or combinations thereof object；
30-100 parts of carbon blacks；
The 1-10 parts of Cardanol Modified PF Resins as shown in following formula (a) or formula (b)；
And 10-1 parts of methylene donor；
In formula (a):
R is selected from one or both of the alkyl of H, C1-C6；
R1One or both of alkyl selected from H, OH or C1-C6；
R2Selected from saturation one or both of C15 alkyl or unsaturation C15 alkyl；
R3Selected from one or both of H or OH；
X, y is respectively the integer of 1-15.
In formula (b):
R is selected from one or both of the alkyl of H, C1-C6；
R1One of alkyl selected from H, OH or C1-C6 is a variety of；
R2Selected from saturation C15 alkyl or unsaturation C15 alkyl；
R3Selected from H or OH；
X, y is respectively the integer of 1-15.
Wherein, the synthetic rubber it is including but not limited to cis--Isosorbide-5-Nitrae-polyisoprene (IR), polybutadiene, neoprene
Diene, the copolymer of isoprene and butadiene, acrylonitrile and butadiene copolymer, acrylonitrile and isoprene copolymerization
The copolymer of object, styrene and butadiene and isoprene, butyl rubber, EPDM, styrene and butadiene copolymer in one
Kind is a variety of.
Wherein, the carbon black is not particularly limited, and be can be used and for tire or any other is answered in the prior art
Any carbon black；The nitrogen adsorption specific surface area of the carbon black is more than or equal to 30m2/g。
Preferably, the nitrogen adsorption specific surface area of the carbon black is 30m2/g-150m2/g。
Preferably, the dosage of the carbon black is 40~80 parts by weight.
Wherein, the Cardanol Modified PF Resin is used together with methylene donor, the methylene
Donor refers to the compound that can form resin network with reactive modified phenolic resin under heating condition；The methylene is given
Body includes but is not limited to hexa (HMT), hexamethoxymethyl melamine (HMMM), six ethoxyl methyl melamines
Amine, metaformaldehyde and paraformaldehyde it is one or more.
Wherein, the weight ratio of the methylene donor and Cardanol Modified PF Resin can change.Usually
The weight ratio range of ground, methylene donor and Cardanol Modified PF Resin is 1:10-10:1, and preferred weight ratio is 1:5-
5:1。
It can further include various additives in rubber composition of the invention, such as vulcanizing agent, promotor, tristearin
The components such as acid, zinc oxide, antioxidant, softening agent, cobalt salt.Wherein, sulphur is common vulcanizing agent, and dosage is art technology
Known to personnel, the sulphur of 0.5-10 parts by weight is added in every 100 parts by weight of rubber.
The present invention also provides the preparation methods of the rubber composition, comprising: (1) by rubber and sulphur removal agent, promotion
Additive component other than agent and adhesion promotor is mixed to form mixture；(2) Cardanol Modified PF Resin is added
Enter in the mixture formed to the first step；(3) vulcanizing agent, promotor, methylene donor are mixed into the mixing of second step formation
In object.
Wherein, it in the step (1), is mixed using mixer, such as Banbury mixer；Mixing temperature is 150~155
℃；
Wherein, the mixing temperature of the step (2) and (3) is 90~150 DEG C.
Wherein, the step of preparation method of the rubber composition further can also be formed and vulcanize.
The invention also provides a kind of tire belts, wherein including the modified by cardanol as shown in formula (a) or formula (b)
Phenolic resin or the rubber composition.It is as follows:
In formula (a):
R is selected from one or both of the alkyl of H, C1-C6；
R1One or both of alkyl selected from H, OH or C1-C6；
R2Selected from saturation one or both of C15 alkyl or unsaturation C15 alkyl；
R3Selected from one or both of H or OH；
X, y is respectively the integer of 1-15.
In formula (b):
R is selected from one or both of the alkyl of H, C1-C6；
R1One of alkyl selected from H, OH or C1-C6 is a variety of；
R2Selected from saturation C15 alkyl or unsaturation C15 alkyl；
R3Selected from H or OH；
X, y is respectively the integer of 1-15.
Preferably, the tire belt includes the Cardanol Modified PF Resin as shown in formula (a)
The invention also provides a kind of tires, which is characterized in that including the modified by cardanol as shown in formula (a) or formula (b)
Phenolic resin or above-mentioned rubber composition；Or including the tire belt.
Preferably, the tire includes the Cardanol Modified PF Resin as shown in formula (a)
Wherein, the tire is pneumatic tire.
The present invention uses Cardanol Modified PF Resin as adhesion promotor, in Vulcanization Process of Rubber, with methylene
Base gives precursor reactant spanning tree rouge network protection rubber and steel wire floor.Since Cardanol Modified PF Resin does not contain isophthalic two
Phenol will not generate smoke phenomenon in mixing process, and influence environment.Moreover, the present invention uses Cardanol Modified PF Resin
As adhesion promotor, the bonding force of vulcanized rubber and reinforcing material is improved, smoke phenomenon, and the modulus provided will not be provided
High, hardness height, all-steel cord extraction performance are good.
Specific embodiment
In conjunction with following specific embodiments, the present invention is described in further detail.Implement process of the invention, condition,
Experimental method etc. is among the general principles and common general knowledge in the art in addition to what is specifically mentioned below, and the present invention does not have
Especially limitation content.
Embodiment 1
In tetra- mouthfuls of round-bottom reaction flasks of 5L equipped with blender, thermometer, reflux condenser and dropping funel, it is added
1880g phenol, 235 grams of anacardols, 25g oxalic acid are heated to 95~100 DEG C, and 37% formalin is then added dropwise in 90 minutes
Solution 1260g continues reflux 30 minutes after being added dropwise, changing reflux unit at this time is distilling apparatus, heats up and steams reaction life
At the unreacted phenol of water and part, there is no water to steam when temperature reaches 114~115 DEG C, is continuously heating to 195~200
DEG C, then it is passed through steam distillation 60 minutes, then continue to be evaporated under reduced pressure 60 minutes (vacuum degree -95KPa) at 195~200 DEG C, break
2250 grams of Cardanol Modified PF Resin are obtained after vacuum.The softening point of resin is 95 DEG C, free-phenol 0.32%.
Embodiment 2
In tetra- mouthfuls of round-bottom reaction flasks of 5L equipped with blender, thermometer, reflux condenser and dropping funel, it is added
1880g phenol, 10g mono- are hydrated p-methyl benzenesulfonic acid, are heated to 95~100 DEG C, and 37% formaldehyde is then added dropwise in 90 minutes
Aqueous solution 1170g continues reflux 30 minutes after being added dropwise, changing reflux unit at this time is distilling apparatus, then heats up and steams
The unreacted phenol of water and part generated is reacted, there is no water to steam when temperature reaches 114~115 DEG C, adds 235 grams of waists
Fruit phenol, changing distilling apparatus is reflux unit, is continuously heating to 180~185 DEG C and reacts 60 minutes, adds 8 grams of triethanolamine
And continue stirring 5~10 minutes, changing reflux unit at this time is distilling apparatus, is continuously heating to 195~200 DEG C, then be passed through water steaming
Steam distillation 60 minutes, then continues to be evaporated under reduced pressure 60 minutes (vacuum degree -95KPa) at 195~200 DEG C, obtain waist after vacuum breaker
2210 grams of fruit phenol phenol-formaldehyde resin modified.The softening point of resin is 99 DEG C, free-phenol 0.41%.
Embodiment 3
Cardanol Modified PF Resin prepared by embodiment 1, embodiment 2 is subjected to test verifying in rubber compounding,
And (butyl carbamate is modified with resorcinol, commercially available SL-3022 resin (resorcinol formaldehyde resin) and PN760 resin
Phenol formaldehyde resin) compare.Wherein the formula of rubber is refined according to formula shown in table 1, wherein each component
Use level on the basis of the rubber of every 100 parts by weight (phr).
The formula of 1 rubber composition of table
| Use level/phr | |
| Natural rubber (NR) | 100.00 |
| Carbon black (N236) | 60.00 |
| Zinc oxide | 7.00 |
| Stearic acid | 0.50 |
| Cobalt salt (CN20.5%, Shepherd Products) | 0.75 |
| Sulphur (80%, OT20) | 5.00 |
| N, N- dicyclohexyl -2-[4-morpholinodithio sulfenamide (DZ) | 1.20 |
| N- (1,3- dimethylbutyl)-N '-diphenyl-para-phenylene diamine (4020) | 1.00 |
| HMMM (65% purity, load is on silica) | 3.50 |
| The resin or resorcinol or SL-3022 or PN760 of embodiment 1,2 | 1.50 |
The mixed process of sizing material is as follows: the first step, by the components such as rubber, carbon black, zinc oxide, stearic acid temperature be 150
It is mixed in~155 DEG C of Banbury mixer.Second step, the Cardanol Modified PF Resin that will be prepared according to embodiment 1 or 2
Or resorcinol or SL-3022, cobalt salt and antioxidant 4020 are mixed into rubber in the Banbury mixer that temperature is 140~145 DEG C
Among glue component.Sulphur, promotor, HMMM are mixed into rubber composite by third step at 90~100 DEG C.This rubber is multiple
Object is closed to stand overnight in the environment of 23 DEG C of constant temperature temperature and 50% constant humidity.Then its cure is tested at 150 DEG C
Can, and mechanical performance and the test of steel wire bond properties after being vulcanized.Wherein, tensile property uses GB/T 528-2009
It is tested；Hardness is tested using GB/T 531.1-2008；Curability uses Alpha Technologies MRD sulphur
Become instrument, is tested referring to GB/T 16584-1996 and GB/T 1233-2008.Vulcanization used by all-steel cord bond properties
Condition: 155 DEG C × 40min, all-steel cord specification: 3+9+15*0.22+1 is tested with standard ASTM D1871-2004.
Table 2 lists the different manifestations of various resins in mixing process, embodiment 1, embodiment 2, resorcinol, SL-
3022, PN760 respectively correspond the sizing material of the resin prepared using embodiment 1, the resin prepared using embodiment 2 sizing material, make
With the sizing material of resorcinol, the sizing material using SL-3022, the sizing material using PN760.Test discovery, with resorcinol, SL-
3022, PN760 is compared, and does not have smog in mixing process using Cardanol Modified PF Resin and the compatibility of resin and rubber
More preferably.
Performance in 2 mixing process of table
| Embodiment 1 | Embodiment 2 | Resorcinol | SL-3022 | PN760 | |
| Smog | Nothing | Nothing | Weight | Gently | Gently |
| Smell | Rubber | Rubber | Resorcinol | Rubber | Rubber |
| Compatibility | It is good | It is good | Difference | It is medium | It is medium |
Table 3 is the physical application test performance of different rubber sizes, compared with resorcinol, SL-3022 and PN760, this
The Cardanol Modified PF Resin of invention, especially 1 method of embodiment preparation resin provide MH, stretch surely, hardness it is higher, tool
There is physically better performance, reinforcing effect is more preferable, and can significantly improve steel wire after steam ageing and salt water aging
Extraction performance.
3 rubber size performance of table
The beneficial effects of the present invention are compared with prior art, rubber composition provided by the invention uses anacardol
Phenol-formaldehyde resin modified and methylene donor effectively overcome resorcinol and send out in mixing process as adhesion promotion system
The problem of cigarette；Compared with resorcinol formaldehyde resin, butyl carbamate phenol-formaldehyde resin modified, Cardanol Modified PF Resin with
Rubber has better compatibility, and the modulus, the hardness that provide are higher, and steel wire extraction performance is more preferable.
Claims (12)
1. a kind of Cardanol Modified PF Resin is in rubber and its product as the application of adhesion promotor, which is characterized in that
Shown in Cardanol Modified PF Resin the structure such as formula (a) or formula (b),
In formula (a):
R is selected from one or both of the alkyl of H, C1-C6；
R1One or both of alkyl selected from H, C1-C6；
R2Selected from saturation one or both of C15 alkyl or unsaturation C15 alkyl；
R3Selected from one or both of H, OH；
X, y is respectively the integer of 1-15；
In formula (b):
R is selected from one or both of the alkyl of H, C1-C6；
R1One or both of alkyl selected from H, C1-C6；
R2Selected from saturation C15 alkyl or unsaturation C15 alkyl；
R3Selected from H or OH；
X, y is respectively the integer of 1-15.
2. application as described in claim 1, which is characterized in that shown in the Cardanol Modified PF Resin structure such as formula (a).
3. application as described in claim 1, which is characterized in that the quality of the Cardanol Modified PF Resin be rubber and its
The 1-10% of quality of item.
4. application as described in claim 1, which is characterized in that the rubber and its product include tire belt.
5. application as described in claim 1, which is characterized in that the rubber and its product include tire.
6. a kind of rubber composition, which is characterized in that Cardanol Modified PF Resin according to claim 1 in rubber and
It include following component as the application of adhesion promotor in its product, wherein the component is indicated with mass parts:
100 parts of natural rubbers, synthetic rubber or combinations thereof object；
30-100 parts of carbon blacks；
The 1-10 parts of Cardanol Modified PF Resins described in claim 1 as shown in formula (a) or formula (b)；
10-1 parts of methylene donors.
7. rubber composition as claimed in claim 6, which is characterized in that the Cardanol Modified PF Resin structure such as formula
(a) shown in.
8. rubber composition as claimed in claim 6, which is characterized in that the methylene donor is selected from hexa-methylene four
One of amine, hexamethoxymethyl melamine, six ethoxyl methyl melamines, paraformaldehyde are a variety of.
9. rubber composition as claimed in claim 6, which is characterized in that the methylene donor is selected from hexa-methylene four
One of amine, hexamethoxymethyl melamine, six ethoxyl methyl melamines, metaformaldehyde are a variety of.
10. rubber composition as claimed in claim 6, which is characterized in that the Cardanol Modified PF Resin and methylene
The mass ratio of base donor is 1:5-5:1.
11. a kind of tire belt, which is characterized in that described in any item rubber compositions including such as claim 6-10.
12. a kind of tire, which is characterized in that described in any item rubber compositions including such as claim 6-10；Or including
Tire belt as claimed in claim 11.
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| CN109721697B (en) * | 2017-10-30 | 2021-11-02 | 彤程化学（中国）有限公司 | Modified cardanol-phenol-formaldehyde resin and preparation and application thereof |
| CN108607528B (en) * | 2018-05-08 | 2021-02-05 | 东北大学 | Diatomite/vulcanized polymer mercury ion adsorption material and preparation method thereof |
| CN112457459B (en) * | 2020-10-20 | 2023-11-21 | 江苏麒祥高新材料有限公司 | Modified resorcinol formaldehyde resin, preparation method and application thereof |
| CN112521666B (en) * | 2020-12-15 | 2022-04-12 | 北京彤程创展科技有限公司 | Rubber composition, preparation method thereof and rubber product |
| CN114672074B (en) * | 2020-12-24 | 2024-02-09 | 彤程新材料集团股份有限公司 | Rubber composition containing xylene modified phenolic resin and application thereof |
| CN114605259A (en) * | 2022-02-24 | 2022-06-10 | 江苏麒祥高新材料有限公司 | Modified cashew nut oil, rubber plasticizer, and preparation method and application thereof |
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| GB720703A (en) * | 1952-05-09 | 1954-12-22 | Us Rubber Co | Improvements in printing plate material |
| FR1112105A (en) * | 1953-10-09 | 1956-03-08 | Us Rubber Co | Improvements in adhesives |
| KR20020016196A (en) * | 2000-08-24 | 2002-03-04 | 신형인 | Rubber composition for tire bead filler |
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