CN106632929B - A kind of valoneaic acid dilactone copolymerization phenolic foam process for preparing resins - Google Patents
A kind of valoneaic acid dilactone copolymerization phenolic foam process for preparing resins Download PDFInfo
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- CN106632929B CN106632929B CN201610835315.7A CN201610835315A CN106632929B CN 106632929 B CN106632929 B CN 106632929B CN 201610835315 A CN201610835315 A CN 201610835315A CN 106632929 B CN106632929 B CN 106632929B
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- Prior art keywords
- valoneaic
- phenolic
- resin
- dilactone
- acid dilactone
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- BPAOAXAAABIQKR-UHFFFAOYSA-N valoneic acid dilactone Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1OC1=CC(C(O2)=O)=C3C4=C2C(O)=C(O)C=C4C(=O)OC3=C1O BPAOAXAAABIQKR-UHFFFAOYSA-N 0.000 title claims abstract description 72
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 229920005989 resin Polymers 0.000 title claims abstract description 33
- 239000011347 resin Substances 0.000 title claims abstract description 33
- 239000006260 foam Substances 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
- 238000007334 copolymerization reaction Methods 0.000 title claims abstract description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000007788 liquid Substances 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- 150000003384 small molecules Chemical class 0.000 claims abstract description 9
- -1 aldehyde compound Chemical class 0.000 claims abstract description 7
- 150000002989 phenols Chemical class 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- RUOFGJLCWJUJRS-UHFFFAOYSA-N 4-(6-carboxy-2,3,4-trihydroxyphenoxy)-4',5,5',6,6'-pentahydroxy-[1,1'-biphenyl]-2,2'-dicarboxylic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1OC1=CC(C(O)=O)=C(C=2C(=CC(O)=C(O)C=2O)C(O)=O)C(O)=C1O RUOFGJLCWJUJRS-UHFFFAOYSA-N 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 229920001687 Valoneic acid Polymers 0.000 claims description 5
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 4
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 4
- 229920006324 polyoxymethylene Polymers 0.000 claims description 3
- LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 claims description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 2
- 229940106691 bisphenol a Drugs 0.000 claims description 2
- 150000001896 cresols Chemical class 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002596 lactones Chemical class 0.000 claims 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 claims 1
- 229920001568 phenolic resin Polymers 0.000 abstract description 26
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 abstract description 25
- 239000005011 phenolic resin Substances 0.000 abstract description 23
- 230000000694 effects Effects 0.000 abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 6
- 238000010521 absorption reaction Methods 0.000 abstract description 5
- 238000010382 chemical cross-linking Methods 0.000 abstract description 5
- 229920000728 polyester Polymers 0.000 abstract description 5
- 210000000497 foam cell Anatomy 0.000 abstract description 4
- 230000007935 neutral effect Effects 0.000 abstract description 4
- 238000005187 foaming Methods 0.000 abstract description 3
- 229920003986 novolac Polymers 0.000 abstract description 2
- 235000013824 polyphenols Nutrition 0.000 description 19
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- 229920002866 paraformaldehyde Polymers 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920002725 thermoplastic elastomer Polymers 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 244000044283 Toxicodendron succedaneum Species 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- WQPDQJCBHQPNCZ-UHFFFAOYSA-N cyclohexa-2,4-dien-1-one Chemical compound O=C1CC=CC=C1 WQPDQJCBHQPNCZ-UHFFFAOYSA-N 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/24—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with mixtures of two or more phenols which are not covered by only one of the groups C08G8/10 - C08G8/20
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
A kind of valoneaic acid dilactone copolymerization phenolic foam process for preparing resins, it is related to a kind of process for preparing resins, the following steps are included: quantitative phenolic compound, valoneaic acid dilactone, catalyst are sequentially added in reaction kettle, then quantitative aldehyde compound is added portionwise in reaction kettle within a certain period of time, with in acetic acid and resin liquid is neutral, then the small molecule in system is removed under reduced pressure until no liquid is discharged, and obtaining thick liquid is that valoneaic acid dilactone is copolymerized phenolic foam resin.This method is to replace a part of phenol in the novolak resin stage with resourceful and cheap valoneaic acid dilactone, valoneaic acid dilactone belongs to biology base hyper-branched polyester, reactive active phenolic hydroxyl group is contained in periphery simultaneously, it adds it in phenolic resin system, its effect that can serve as chemical crosslinking point and stress absorption point, to which toughening enhances phenolic resin, mechanical property is promoted.The cystosepiment uniform foam cell prepared after foaming, rate of closed hole are high.
Description
Technical field
The present invention relates to a kind of process for preparing resins, are copolymerized phenolic foam resin more particularly to a kind of valoneaic acid dilactone
Preparation method.
Background technique
Phenolic resin starting material is easy to get, low in cost, and mechanical strength is high, steady performance.But not with industry
Disconnected development, puts forward new requirements High Performance Phenolic Resins, has been unable to meet requirement with pure phenolic resin.Phenolic resin knot
The disadvantages of weak link on structure is that phenolic hydroxyl group and methylene are easy to oxidize, causes phenol formaldehyde foam brittleness big, and dusting degree is high.Mesh
Before until, there is a large amount of material to be exploited for plasticizing phenol formaldehyde, such as rubber particles, thermoplastic elastomer (TPE), inorganic
Particle, core-shell particles etc., but also rarely have research for dissaving polymer phenol-formaldehyde resin modified.
Valoneaic acid dilactone is a kind of natural polyphenol compound, belongs to biology base hyper-branched polyester, is present in a variety of trees
In the bark and fruit of (such as Oak Tree and lacquer tree), while periphery adds it to phenolic aldehyde tree containing reactive active phenolic hydroxyl group
In resin system, the effect of chemical crosslinking point and stress absorption point can be served as, so that toughening enhances phenolic resin, lifting force
Performance is learned, the content of the small molecules such as free phenol in resin (aldehyde) is more reduced, keeps product more environmentally-friendly.And natural plant in recent years
The development and utilization in goods and materials source are more and more valued by people, and environmental protection becomes emphasis topic, so natural polymer is added
Entering to certain Polymer Synthesizings and modified field becomes new research direction.Valoneaic acid dilactone and phenolic resin are copolymerized at present
A kind of novel phenolic Foamex is prepared to have not been reported.
Summary of the invention
The purpose of the present invention is to provide a kind of valoneaic acid dilactones to be copolymerized phenolic foam process for preparing resins, and this method is
A part of phenol, valoneaic acid dilactone are replaced in the novolak resin stage with resourceful and cheap valoneaic acid dilactone
Belong to biology base hyper-branched polyester, while periphery adds it in phenolic resin system containing reactive active phenolic hydroxyl group,
Its effect that can serve as chemical crosslinking point and stress absorption point promotes mechanical property so that toughening enhances phenolic resin.Hair
The cystosepiment uniform foam cell prepared after bubble, rate of closed hole are high.
The purpose of the present invention is what is be achieved through the following technical solutions:
A kind of valoneaic acid dilactone copolymerization phenolic foam process for preparing resins, this method have following reaction:
Formulas I.
A kind of valoneaic acid dilactone is copolymerized phenolic foam process for preparing resins, and the preparation method includes following step
It is rapid:
Quantitative phenolic compound, valoneaic acid dilactone, catalyst are sequentially added in about 60 ~ 80 DEG C of reaction kettles, then
Quantitative aldehyde compound is added portionwise in reaction kettle within a certain period of time, high-speed stirred makes to be uniformly mixed, and reacts 30-
60min is to slowly warm up to 80 ~ 100 DEG C with the heating rate of 1~5 DEG C/min, is cooled to room after constant temperature stirring 1.5-2.5h
Then temperature removes the small molecule in system under reduced pressure until no liquid is discharged, obtaining thick liquid is in acetic acid and resin liquid is neutral
Valoneaic acid dilactone is copolymerized phenolic foam resin.
A kind of valoneaic acid dilactone is copolymerized phenolic foam process for preparing resins, and the phenolic compound is selected from benzene
One of phenol, cresols, xylenol, nonyl phenol, bisphenol-A, resorcinol, propylphenol, ethyl -phenol and anacardol are more
Kind.
A kind of valoneaic acid dilactone is copolymerized phenolic foam process for preparing resins, the aldehyde compound be formaldehyde,
One of acetaldehyde, butyraldehyde, polyformaldehyde and furfural are a variety of.
A kind of valoneaic acid dilactone is copolymerized phenolic foam process for preparing resins, and the catalyst is sodium hydroxide, hydrogen
One of strong base substances such as potassium oxide are a variety of.
The advantages and effects of the present invention are:
(1) valoneaic acid dilactone is added in phenolic resin formulations by the present invention by certain reaction for the first time prepares rubber
Bowl acid dilactone is copolymerized phenolic foam resin, is the system of phenol-formaldehyde resin modified using the feature that valoneaic acid dilactone is resourceful
It is standby that new thinking is provided.
(2) valoneaic acid dilactone provided by the invention is copolymerized phenolic foam resin, modest viscosity, and valoneaic acid dilactone belongs to
Biology base hyper-branched polyester, while periphery adds it in phenolic resin system containing reactive active phenolic hydroxyl group, it can
To serve as the effect of chemical crosslinking point and stress absorption point, so that toughening enhances phenolic resin, mechanical property is promoted.After foaming
The cystosepiment uniform foam cell of preparation, rate of closed hole are high.
(3) simple process of the method for the present invention, environmentally protective, production cost is low, can become the modified phenol of industrialized production
A kind of new technology of urea formaldehyde material.
Specific embodiment
The following describes the present invention in detail with reference to examples.
Embodiment 1
By the phenol solution of 80g, 20g valoneaic acid dilactone, 2g sodium hydroxide solution is sequentially added about 65 DEG C of reaction kettles
In, then 65g paraformaldehyde is added three times in reaction kettle within half an hour, high-speed stirred makes to be uniformly mixed, reaction
30min is to slowly warm up to 90 DEG C with the heating rate of 5 DEG C/min, is cooled to room temperature after constant temperature stirring 1.5h, in acetic acid
With resin liquid neutrality, the small molecule in system is then removed under reduced pressure until no liquid is discharged, obtaining thick liquid is in valoneaic acid two
Ester is copolymerized phenolic resin.
Embodiment 2
By the phenol solution of 85g, 15g valoneaic acid dilactone, 2g sodium hydroxide solution is sequentially added about 65 DEG C of reaction kettles
In, then 65g paraformaldehyde is added three times in reaction kettle within half an hour, high-speed stirred makes to be uniformly mixed, reaction
30min is to slowly warm up to 90 DEG C with the heating rate of 5 DEG C/min, is cooled to room temperature after constant temperature stirring 1.5h, in acetic acid
With resin liquid neutrality, the small molecule in system is then removed under reduced pressure until no liquid is discharged, obtaining thick liquid is in valoneaic acid two
Ester is copolymerized phenolic resin.
Embodiment 3
By the phenol solution of 90g, 10g valoneaic acid dilactone, 2g sodium hydroxide solution is sequentially added about 65 DEG C of reaction kettles
In, then 65g paraformaldehyde is added three times in reaction kettle within half an hour, high-speed stirred makes to be uniformly mixed, reaction
30min is to slowly warm up to 90 DEG C with the heating rate of 5 DEG C/min, is cooled to room temperature after constant temperature stirring 1.5h, in acetic acid
With resin liquid neutrality, the small molecule in system is then removed under reduced pressure until no liquid is discharged, obtaining thick liquid is in valoneaic acid two
Ester is copolymerized phenolic resin.
Embodiment 4
By the phenol solution of 95g, 5g valoneaic acid dilactone, 2g sodium hydroxide solution is sequentially added in about 65 DEG C of reaction kettles,
Then 65g paraformaldehyde being added three times in reaction kettle within half an hour, high-speed stirred makes to be uniformly mixed, 30min is reacted,
90 DEG C are to slowly warm up to the heating rate of 5 DEG C/min, is cooled to room temperature after constant temperature stirring 1.5h, in acetic acid and resin
Liquid is neutral, then removes the small molecule in system under reduced pressure until no liquid discharge, obtains thick liquid as valoneaic acid dilactone copolymerization
Phenolic resin.
Comparative example
The phenol solution of 100g, 2g sodium hydroxide solution are sequentially added in about 65 DEG C of reaction kettles, then by 65g poly
Formaldehyde is added three times in reaction kettle within half an hour, and high-speed stirred makes to be uniformly mixed, and 30min is reacted, with 5 DEG C/min's
Heating rate is to slowly warm up to 90 DEG C, is cooled to room temperature after constant temperature stirring 1.5h, in acetic acid and resin liquid is neutral, then depressurizes
The small molecule in system is evaporated off until no liquid is discharged, obtaining thick liquid is phenolic resin.
The performance comparison of valoneaic acid dilactone prepared by the embodiment of the present invention copolymerization phenolic resin and phenolic resin
It is as follows:
As seen from the above embodiment, valoneaic acid dilactone of the invention is copolymerized phenolic resin modest viscosity, foam rate of closed hole
Raising, bending strength are good.This is because valoneaic acid dilactone belongs to biology base hyper-branched polyester, while periphery is containing reactive
Active phenolic hydroxyl group, adds it in phenolic resin system, can serve as the effect of chemical crosslinking point and stress absorption point,
To which toughening enhances phenolic resin, mechanical property is promoted.The cystosepiment uniform foam cell prepared after foaming, rate of closed hole are high.
Above in conjunction with specific embodiment, an exemplary description of the invention, it is clear that realization of the invention is not by upper
The limitation of mode is stated, as long as using the various improvement that the inventive concept and technical scheme of the present invention carry out, or not improved general
Conception and technical scheme of the invention directly apply to other occasions, are within the scope of the invention.
Claims (3)
1. a kind of valoneaic acid dilactone is copolymerized phenolic foam process for preparing resins, which is characterized in that the preparation method include with
Lower step:
Quantitative phenolic compound, valoneaic acid dilactone, catalyst are sequentially added in 60 ~ 80 DEG C of reaction kettles, then will be quantified
Aldehyde compound be added portionwise in reaction kettle within a certain period of time, high-speed stirred makes to be uniformly mixed, react 30-60min, with
The heating rate of 1~5 DEG C/min is to slowly warm up to 80 ~ 100 DEG C, is cooled to room temperature after constant temperature stirring 1.5-2.5h, uses acetic acid
Resin liquid neutrality is neutralized, then removes the small molecule in system under reduced pressure until no liquid is discharged, obtaining thick liquid is valoneaic acid two
Lactone is copolymerized phenolic foam resin；
The catalyst is sodium hydroxide；
The structural formula of the valoneaic acid dilactone copolymerization phenolic foam resin is as follows:
。
2. a kind of valoneaic acid dilactone according to claim 1 is copolymerized phenolic foam process for preparing resins, which is characterized in that
The phenolic compound is selected from phenol, cresols, xylenol, nonyl phenol, bisphenol-A, resorcinol, propylphenol, ethyl -phenol
With one of anacardol or a variety of.
3. a kind of valoneaic acid dilactone according to claim 1 is copolymerized phenolic foam process for preparing resins, which is characterized in that
The aldehyde compound is one of formaldehyde, acetaldehyde, butyraldehyde, polyformaldehyde and furfural or a variety of.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201610835315.7A CN106632929B (en) | 2016-09-21 | 2016-09-21 | A kind of valoneaic acid dilactone copolymerization phenolic foam process for preparing resins |
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|---|---|---|---|
| CN201610835315.7A CN106632929B (en) | 2016-09-21 | 2016-09-21 | A kind of valoneaic acid dilactone copolymerization phenolic foam process for preparing resins |
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| CN106632929B true CN106632929B (en) | 2018-12-18 |
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| CN105732923B (en) * | 2014-12-11 | 2018-05-25 | 苏州美克思科技发展有限公司 | A kind of preparation method of low in acidity phenolic aldehyde foam thermal insulation material |
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Application publication date: 20170510 Assignee: SHENYANG XINFEIYU RUBBER PRODUCTS CO.,LTD. Assignor: SHENYANG University OF CHEMICAL TECHNOLOGY Contract record no.: X2023210000283 Denomination of invention: A method for preparing valonate diolide copolymer phenolic foam resin Granted publication date: 20181218 License type: Common License Record date: 20231205 |
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