CN104558019B - A kind of Halogen abietyl fire retardant and preparation method thereof - Google Patents
A kind of Halogen abietyl fire retardant and preparation method thereof Download PDFInfo
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- CN104558019B CN104558019B CN201410814646.3A CN201410814646A CN104558019B CN 104558019 B CN104558019 B CN 104558019B CN 201410814646 A CN201410814646 A CN 201410814646A CN 104558019 B CN104558019 B CN 104558019B
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Abstract
The open a kind of Halogen abietyl fire retardant of the present invention, described fire retardant does not contains halogen, and its molecule has phenanthrene ring rigid structure, belongs to abietyl phosphorus flame retardant, does not produce toxic gas during its high temperature, has that the compatibility is good, molecular weight big, softening point high.Additionally, invention additionally discloses the preparation method of a kind of described Halogen abietyl fire retardant, described method uses and derives from natural reproducible resource is raw material, expand the new opplication of Colophonium further, the Halogen abietyl fire retardant prepared can be widely used in the industry such as adhesive, coating, does not affect its chemical machinery performance.
Description
Technical field
The present invention relates to a kind of fire retardant and preparation method thereof, a kind of fire retardant containing abietyl and preparation thereof
Method.
Background technology
At present, preferably at most addition type halogen compounds and organic phosphorus compound.Wherein use the resistance of halogen compounds
Fuel efficiency fruit is preferable, but during its burning, poisonous and corrosive gas produces, and pollutes environment；Used organophosphorous fire retardant has ring
Border friendly and efficiently etc. feature and be recognized the important kind that is to replace halogenated flame retardant.
Adhesive, as current most important polymeric adhesion composite, is widely used in industry-by-industry, but due to easily
Combustion property and make it apply and be restricted.The organic phosphorus compound poor heat stability of use, Yi Hui in adhesive industry at present
Send out, intermiscibility is poor, most importantly affect the adhesive property of adhesive.
Summary of the invention
One is provided to derive from natural reproducible in place of it is an object of the invention to overcome above-mentioned the deficiencies in the prior art
Resource, molecule have phenanthrene ring rigid structure, have excellent flame retardancy, have simultaneously the extensive compatibility, the most volatile, weatherability and
The Halogen abietyl fire retardant of the features such as temperature tolerance is good, the chemical machinery performance not affecting composite；Meanwhile, the present invention also carries
Supply the preparation method of described Halogen abietyl fire retardant.
For achieving the above object, the technical scheme that the present invention takes is: a kind of Halogen abietyl fire retardant, described fire retardant
Molecular structural formula as follows:
Halogen abietyl fire retardant of the present invention, has molecular structural formula as above, can by its molecular structural formula
Finding out, its molecule has phenanthrene ring rigid structure, belongs to abietyl phosphorus flame retardant, without halogen, has not produced poison during high temperature
Body；Having abietyl, the compatibility is good, can be widely used in the industry such as adhesive, coating, does not affect its chemical machinery performance,
And molecular weight is big, softening point is high, the most volatile.
Meanwhile, present invention also offers the preparation method of a kind of Halogen abietyl fire retardant described above, described method bag
Include following steps:
(1) abienol, solvent and catalyst being put in reactor, heating for dissolving also stirs, the most again by phosphorous
Compound adds in reactor, catalytic reaction；
(2) after reaction terminates, it is cooled to room temperature, the acid adding in sodium hydroxide and generating；
(3) by step (2) gained reactant after filtering, washing, remove solvent, obtain product.
As the preferred implementation of the preparation method of Halogen abietyl fire retardant of the present invention, in described step (1)
Abienol be at least one in abietinol, dehydroabietinol, dihydroabietyl alcohol, tetrahydroabietyl alcohol.As Halogen Colophonium of the present invention
The more preferably embodiment of the preparation method of based flameproofing, the abienol in described step (1) be in abietinol, dehydroabietinol extremely
Few one.
As the preferred implementation of the preparation method of Halogen abietyl fire retardant of the present invention, in described step (1)
Abienol be in Pinus massoniana Lamb, pinus elliottii, Yunnan Colophonium, Starex, newtrex, hydrogenated rosin, disproportionated rosin at least
A kind of prepared through Lithium Aluminium Hydride reduction.
As the preferred implementation of the preparation method of Halogen abietyl fire retardant of the present invention, in described step (1)
Solvent be saturated solvent；Catalyst in described step (1) is magnesium chloride, calcium chloride or calcium sulfate.As of the present invention
The more preferably embodiment of the preparation method of Halogen abietyl fire retardant, the solvent in described step (1) be toluene, dimethylbenzene or
Send alkane；Catalyst in described step (1) is magnesium chloride.Preparation method as Halogen abietyl fire retardant of the present invention
Most preferred embodiment, the solvent in described step (1) is toluene.
As the preferred implementation of the preparation method of Halogen abietyl fire retardant of the present invention, in described step (1)
Phosphorus-containing compound be phosphorus oxychloride, Phosphorous chloride. or DOPO.Preparation side as Halogen abietyl fire retardant of the present invention
The more preferably embodiment of method, the phosphorus-containing compound in described step (1) is phosphorus oxychloride or Phosphorous chloride..
As the preferred implementation of the preparation method of Halogen abietyl fire retardant of the present invention, in described preparation method
The addition of each material is: abienol 1100～1600 weight portion, solvent 1100～1600 weight portion, catalyst 1～15 weight
Part, phosphorus-containing compound 100～180 weight portion, sodium hydroxide 38～140 weight portion.Hinder as Halogen abietyl of the present invention
The more preferably embodiment of preparation method of combustion agent, in described preparation method, the addition of each material is: abienol 1200～
1500 weight portions, solvent 1200～1500 weight portion, catalyst 1.2～6 weight portion, phosphorus-containing compound 154 weight portion, hydroxide
Sodium 40 weight portion.In described preparation method, the generation of products obtained therefrom is directly affected by the addition of each material, the interpolation of material
Amount difference, it is likely that the Halogen abietyl fire retardant of molecular structural formula of the present invention cannot be prepared, or increase secondary anti-
The generation answered, present inventor, through substantial amounts of research, finds when described each material selects the addition of scope described above
Time, it is possible to preferably prepare the Halogen abietyl fire retardant with molecular structural formula described above, farthest reduce
The generation of side reaction.
As the preferred implementation of the preparation method of Halogen abietyl fire retardant of the present invention, in described step (1)
The temperature of catalytic reaction is 30～150 DEG C, and the time of catalytic reaction is 2～10 hours.As Halogen abietyl of the present invention
The more preferably embodiment of the preparation method of fire retardant, in described step (1), the temperature of catalytic reaction is 50～80 DEG C, and catalysis is anti-
The time answered is 4～6 hours.In step (1), the temperature and time of catalytic reaction has vital shadow to the inventive method
Ringing, present inventor finds through numerous studies, when the temperature and time of catalytic reaction is in above-mentioned scope, it is possible to the most anti-
The Halogen abietyl fire retardant with molecular structural formula described above should be obtained, farthest reduce the generation of side reaction.
As the preferred implementation of the preparation method of Halogen abietyl fire retardant of the present invention, in described step (3)
Washing use the hot water of 50～80 DEG C, wash 3～4 times.Preparation method as Halogen abietyl fire retardant of the present invention
More preferably embodiment, the washing in described step (3) uses the hot water of 60 DEG C, washes 3 times.
As the preferred implementation of the preparation method of Halogen abietyl fire retardant of the present invention, in described step (3)
Removing solvent use following methods: under conditions of vacuum is-0.1～-0.08MPa, vacuum 0.5～2 hours, remove molten
Agent.As the more preferably embodiment of the preparation method of Halogen abietyl fire retardant of the present invention, removing in described step (3)
Solvent is gone to use following methods: under conditions of vacuum is for-0.09MPa, vacuum 1 hour, remove solvent.
Halogen abietyl fire retardant of the present invention, wherein without halogen, high temperature does not produce toxic gas, and its molecule
Having phenanthrene ring rigid structure, its abietyl having makes its compatibility good, can be widely used in the row such as adhesive, coating
Industry, does not affect its chemical machinery performance, and molecular weight is big, and softening point is high, the most volatile, has preferable weatherability, heatproof
The advantages such as property, excellent anti-flammability.The preparation method of Halogen abietyl fire retardant of the present invention, use derive from natural can be again
Production-goods source is raw material, has expanded the new opplication of Colophonium further, it is possible to effectively prepare Halogen abietyl as above resistance
Combustion agent.
Accompanying drawing explanation
Fig. 1 is the molecular structural formula of Halogen abietyl fire retardant of the present invention.
Detailed description of the invention
For better illustrating the object, technical solutions and advantages of the present invention, below in conjunction with the drawings and specific embodiments pair
The present invention is described further.
Embodiment 1
A kind of embodiment of the preparation method of Halogen abietyl fire retardant of the present invention, Halogen abietyl resistance described in the present embodiment
Combustion agent uses following methods to be prepared from:
(1) abietinol 1200 weight portion, toluene 1200 weight portion, magnesium chloride 1.2 weight portion are put in reactor, add thermosol
Solve and stir, the most again phosphorus oxychloride 100 weight portion being added in reactor, catalytic reaction 4h at 50 DEG C；
(2) after reaction terminates, it is cooled to room temperature, the acid adding in sodium hydroxide 40 weight portion and generating；
(3) by step (2) gained reactant through filter, washing (using 50 DEG C of hot water, wash 4 times) after, vacuum be-
Under conditions of 0.09MPa, vacuum 1 hour, remove solvent, obtain Halogen abietyl fire retardant.
The molecular structural formula of the present embodiment gained Halogen abietyl fire retardant is as shown in Figure 1.The present embodiment gained Halogen
The softening point of Colophonium fire retardant is 81 DEG C, and acid number is 0.4mgKOH/g.
Embodiment 2
A kind of embodiment of the preparation method of Halogen abietyl fire retardant of the present invention, Halogen abietyl resistance described in the present embodiment
Combustion agent uses following methods to be prepared from:
(1) dehydroabietinol 1350 weight portion, dimethylbenzene 1500 weight portion, magnesium chloride 4 weight portion are put in reactor, add
Heat of solution also stirs, and adds in reactor by Phosphorous chloride. 120 weight portion the most again, catalytic reaction 8h at 30 DEG C；
(2) after reaction terminates, it is cooled to room temperature, the acid adding in sodium hydroxide 38 weight portion and generating；
(3) by step (2) gained reactant through filter, washing (using 80 DEG C of hot water, wash 3 times) after, vacuum be-
Under conditions of 0.1MPa, vacuum 0.5 hour, remove solvent, obtain Halogen abietyl fire retardant.
The molecular structural formula of the present embodiment gained Halogen abietyl fire retardant is as shown in Figure 1.The present embodiment gained Halogen
The softening point of Colophonium fire retardant is 81.2 DEG C, and acid number is 0.3mgKOH/g.
Embodiment 3
A kind of embodiment of the preparation method of Halogen abietyl fire retardant of the present invention, Halogen abietyl resistance described in the present embodiment
Combustion agent uses following methods to be prepared from:
(1) by dihydroabietyl alcohol 1500 weight portion, alkane 1350 weight portion, calcium sulfate 6 weight portion is sent to put in reactor, heating
Dissolve and stir, the most again phosphorus oxychloride 154 weight portion being added in reactor, catalytic reaction 3h at 150 DEG C；
(2) after reaction terminates, it is cooled to room temperature, the acid adding in sodium hydroxide 50 weight portion and generating；
(3) by step (2) gained reactant through filter, washing (using 60 DEG C of hot water, wash 3 times) after, vacuum be-
Under conditions of 0.08MPa, vacuum 2 hours, remove solvent, obtain Halogen abietyl fire retardant.
The molecular structural formula of the present embodiment gained Halogen abietyl fire retardant is as shown in Figure 1.The present embodiment gained Halogen
The softening point of Colophonium fire retardant is 80.1 DEG C, and acid number is 0.43mgKOH/g.
Embodiment 4
A kind of embodiment of the preparation method of Halogen abietyl fire retardant of the present invention, Halogen abietyl resistance described in the present embodiment
Combustion agent uses following methods to be prepared from:
(1) tetrahydroabietyl alcohol 1350 weight portion, toluene 1100 weight portion, calcium chloride 8 weight portion are put in reactor, heating
Dissolve and stir, the most again DOPO140 weight portion being added in reactor, catalytic reaction 6h at 65 DEG C；
(2) after reaction terminates, it is cooled to room temperature, the acid adding in sodium hydroxide 90 weight portion and generating；
(3) by step (2) gained reactant through filter, washing (using 55 DEG C of hot water, wash 4 times) after, vacuum be-
Under conditions of 0.09MPa, vacuum 1 hour, remove solvent, obtain Halogen abietyl fire retardant.
The molecular structural formula of the present embodiment gained Halogen abietyl fire retardant is as shown in Figure 1.The present embodiment gained Halogen
The softening point of Colophonium fire retardant is 83.8 DEG C, and acid number is 0.3mgKOH/g.
Embodiment 5
A kind of embodiment of the preparation method of Halogen abietyl fire retardant of the present invention, Halogen abietyl resistance described in the present embodiment
Combustion agent uses following methods to be prepared from:
(1) abietinol and dehydroabietinol totally 1100 weight portions, toluene 1600 weight portion, magnesium chloride 10 weight portion are put into reaction
In still, heating for dissolving also stirs, and adds in reactor by phosphorus oxychloride 160 weight portion the most again, and at 80 DEG C, catalysis is anti-
Answer 2h；
(2) after reaction terminates, it is cooled to room temperature, the acid adding in sodium hydroxide 140 weight portion and generating；
(3) by step (2) gained reactant through filter, washing (using 70 DEG C of hot water, wash 3 times) after, vacuum be-
Under conditions of 0.1MPa, vacuum 1 hour, remove solvent, obtain Halogen abietyl fire retardant.
The molecular structural formula of the present embodiment gained Halogen abietyl fire retardant is as shown in Figure 1.The present embodiment gained Halogen
The softening point of Colophonium fire retardant is 83.2 DEG C, and acid number is 0.29mgKOH/g.
Embodiment 6
A kind of embodiment of the preparation method of Halogen abietyl fire retardant of the present invention, Halogen abietyl resistance described in the present embodiment
Combustion agent uses following methods to be prepared from:
(1) by dihydroabietyl alcohol and tetrahydroabietyl alcohol totally 1200 weight portions, dimethylbenzene 1350 weight portion, magnesium chloride 2.7 weight portion
Putting in reactor, heating for dissolving also stirs, and adds in reactor by Phosphorous chloride. 170 weight portion the most again, at 60 DEG C
Lower catalytic reaction 10h；
(2) after reaction terminates, it is cooled to room temperature, the acid adding in sodium hydroxide 40 weight portion and generating；
(3) by step (2) gained reactant through filter, washing (using 80 DEG C of hot water, wash 4 times) after, vacuum be-
Under conditions of 0.09MPa, vacuum 0.5 hour, remove solvent, obtain Halogen abietyl fire retardant.
The molecular structural formula of the present embodiment gained Halogen abietyl fire retardant is as shown in Figure 1.The present embodiment gained Halogen
The softening point of Colophonium fire retardant is 85.8 DEG C, and acid number is 0.35mgKOH/g.
Embodiment 7
A kind of embodiment of the preparation method of Halogen abietyl fire retardant of the present invention, Halogen abietyl resistance described in the present embodiment
Combustion agent uses following methods to be prepared from:
(1) abietinol 1300 weight portion, toluene 1500 weight portion, calcium sulfate 5.4 weight portion are put in reactor, add thermosol
Solve and stir, the most again phosphorus oxychloride 180 weight portion being added in reactor, catalytic reaction 4h at 90 DEG C；
(2) after reaction terminates, it is cooled to room temperature, the acid adding in sodium hydroxide 40 weight portion and generating；
(3) by step (2) gained reactant through filter, washing (using 50 DEG C of hot water, wash 3 times) after, vacuum be-
Under conditions of 0.09MPa, vacuum 2 hours, remove solvent, obtain Halogen abietyl fire retardant.
The molecular structural formula of the present embodiment gained Halogen abietyl fire retardant is as shown in Figure 1.The present embodiment gained Halogen
The softening point of Colophonium fire retardant is 85.2 DEG C, and acid number is 0.51mgKOH/g.
Embodiment 8
A kind of embodiment of the preparation method of Halogen abietyl fire retardant of the present invention, Halogen abietyl resistance described in the present embodiment
Combustion agent uses following methods to be prepared from:
(1) by dehydroabietinol 1600 weight portion, send alkane 1500 weight portion, calcium chloride 2.7 weight portion to put in reactor, add
Heat of solution also stirs, and adds in reactor by phosphorus oxychloride 154 weight portion the most again, catalytic reaction 6h at 65 DEG C；
(2) after reaction terminates, it is cooled to room temperature, the acid adding in sodium hydroxide 40 weight portion and generating；
(3) by step (2) gained reactant through filter, washing (using 60 DEG C of hot water, wash 4 times) after, vacuum be-
Under conditions of 0.08MPa, vacuum 1 hour, remove solvent, obtain Halogen abietyl fire retardant.
The molecular structural formula of the present embodiment gained Halogen abietyl fire retardant is as shown in Figure 1.The present embodiment gained Halogen
The softening point of Colophonium fire retardant is 87 DEG C, and acid number is 0.28mgKOH/g.
Embodiment 9
A kind of embodiment of the preparation method of Halogen abietyl fire retardant of the present invention, Halogen abietyl resistance described in the present embodiment
Combustion agent uses following methods to be prepared from:
(1) dehydroabietinol 1500 weight portion, toluene 1600 weight portion, magnesium chloride 15 weight portion are put in reactor, add
Heat of solution also stirs, and adds in reactor by Phosphorous chloride. 154 weight portion the most again, catalytic reaction 6h at 100 DEG C；
(2) after reaction terminates, it is cooled to room temperature, the acid adding in sodium hydroxide 80 weight portion and generating；
(3) by step (2) gained reactant through filter, washing (using 60 DEG C of hot water, wash 3 times) after, vacuum be-
Under conditions of 0.09MPa, vacuum 0.5 hour, remove solvent, obtain Halogen abietyl fire retardant.
The molecular structural formula of the present embodiment gained Halogen abietyl fire retardant is as shown in Figure 1.The present embodiment gained Halogen
The softening point of Colophonium fire retardant is 83 DEG C, and acid number is 0.21mgKOH/g.
Embodiment 10
A kind of embodiment of the preparation method of Halogen abietyl fire retardant of the present invention, Halogen abietyl resistance described in the present embodiment
Combustion agent uses following methods to be prepared from:
(1) abietinol 1350 weight portion, toluene 1350 weight portion, magnesium chloride 2.7 weight portion are put in reactor, add thermosol
Solve and stir, the most again Phosphorous chloride. 154 weight portion being added in reactor, catalytic reaction 4h at 65 DEG C；
(2) after reaction terminates, it is cooled to room temperature, the acid adding in sodium hydroxide 40 weight portion and generating；
(3) by step (2) gained reactant through filter, washing (using 75 DEG C of hot water, wash 3 times) after, vacuum be-
Under conditions of 0.09MPa, vacuum 1 hour, remove solvent, obtain Halogen abietyl fire retardant.
The molecular structural formula of the present embodiment gained Halogen abietyl fire retardant is as shown in Figure 1.The present embodiment gained Halogen
The softening point of Colophonium fire retardant is 88 DEG C, and acid number is 0.18mgKOH/g.
Last institute is it should be noted that, the present invention is only protected by above example in order to technical scheme to be described
Protecting the restriction of scope, although being explained in detail the present invention with reference to preferred embodiment, those of ordinary skill in the art should
Understand, technical scheme can be modified or equivalent, without deviating from the essence of technical solution of the present invention
And scope.
Claims (7)
1. a Halogen abietyl fire retardant, it is characterised in that the molecular structural formula of described fire retardant is as follows:
2. the preparation method of Halogen abietyl fire retardant as claimed in claim 1, it is characterised in that described method includes following step
Rapid:
(1) abietinol, solvent and catalyst being put in reactor, heating for dissolving also stirs, the most again by phosphorus-containing compound
Add in reactor, catalytic reaction；
(2) after reaction terminates, it is cooled to room temperature, the acid adding in sodium hydroxide and generating；
(3) by step (2) gained reactant after filtering, washing, remove solvent, obtain product；
Catalyst in described step (1) is magnesium chloride, calcium chloride or calcium sulfate；
Phosphorus-containing compound in described step (1) is phosphorus oxychloride, Phosphorous chloride. or DOPO.
3. the preparation method of Halogen abietyl fire retardant as claimed in claim 2, it is characterised in that in described step (1)
Solvent is toluene or dimethylbenzene.
4. the preparation method of Halogen abietyl fire retardant as claimed in claim 2, it is characterised in that each in described preparation method
The addition of material is: abietinol 1100～1600 weight portion, solvent 1100～1600 weight portion, catalyst 1～15 weight portion, contain
Phosphorus compound 100～180 weight portion, sodium hydroxide 38～140 weight portion.
5. the preparation method of Halogen abietyl fire retardant as claimed in claim 4, it is characterised in that each in described preparation method
The addition of material is: abietinol 1200～1500 weight portion, solvent 1200～1500 weight portion, catalyst 1.2～6 weight portion,
Phosphorus-containing compound 154 weight portion, sodium hydroxide 40 weight portion.
6. the preparation method of Halogen abietyl fire retardant as claimed in claim 2, it is characterised in that described step is urged in (1)
The temperature changing reaction is 30～150 DEG C, and the time of catalytic reaction is 2～10 hours.
7. the preparation method of Halogen abietyl fire retardant as claimed in claim 6, it is characterised in that described step is urged in (1)
The temperature changing reaction is 50～80 DEG C, and the time of catalytic reaction is 4～6 hours.
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