CN103627146B - One has excellent snappiness phosphor-containing halogen-free prime ring epoxy resins preparations and applicatio - Google Patents
One has excellent snappiness phosphor-containing halogen-free prime ring epoxy resins preparations and applicatio Download PDFInfo
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- CN103627146B CN103627146B CN201310547795.3A CN201310547795A CN103627146B CN 103627146 B CN103627146 B CN 103627146B CN 201310547795 A CN201310547795 A CN 201310547795A CN 103627146 B CN103627146 B CN 103627146B
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Abstract
The present invention relates to one and there is the preparation of excellent snappiness phosphor-containing halogen-free prime ring epoxy resins, its point three-step reaction and become: 1. general formula (1) and general formula (2) or general formula (3) add phosphorus-containing catalyst and carry out pre-reaction generation Resin A; 2. phosphorous epoxy resin B is generated by general formula (4) or general formula (5) or general formula (6) and the organo phosphorous compounds phosphorus-containing catalyst with a reactive hydrogen atom again; 3. again A and B is mixed and add phosphorus-containing catalyst generation finished product, drip a solubilizing agent and dissolve. It is applied to prepares plate cured sheets and copper-clad plate. This phosphor-containing halogen-free prime ring epoxy resins does not contain the fire retarding epoxide resin of any halogen and does not use bromine fire-retardant, and the copper panel of covering made has excellent snappiness, high resistance stripping and good process. Solve the problem that anti-stripping is low, snappiness is poor.
Description
Technical field
The present invention relates to one and there is excellent snappiness phosphor-containing halogen-free prime ring epoxy resins preparations and applicatio.
Background technology
At present, various industry field, such as the characteristic that electronics, electronic component all not burnt in heat or flame. Therefore, the phosphorous epoxy resin with flame retardant properties is usually used in covering in copper panel. Halogen is introduced in epoxy resin structural in producing by epoxy resin, it may be possible to provide the flame retardant properties of epoxy resin excellence. Use at present as being exactly the epoxy resin containing bromine widely, it is the main epoxy resin manufacturing and producing electronics and electronic component. Employ the electronic component become containing brominated eopxy production of resins and electronics running into burning or during discarded burn processing, these halogen-containing epoxy resin cured products can produce poisonous have etchant gas, if halogen is for hydrogen, halogen and Dioxins, human health is brought great harm, causes environmental pollution.
Fire retarding epoxide resin mainly phosphorus-containing flame-retardant epoxy resin beyond halogen on Vehicles Collected from Market, phosphorous epoxy resin does and fire-retardant covers copper panel, and there is a common problem is that anti-stripping is low, and snappiness is poor, and non-halogen process is caused very big impact by poor processability.
Summary of the invention
It is an object of the invention to overcome above-mentioned deficiency, it is provided that one has excellent snappiness phosphor-containing halogen-free prime ring epoxy resins preparations and applicatio. This phosphor-containing halogen-free prime ring epoxy resins does not contain the fire retarding epoxide resin of any halogen and does not use bromine fire-retardant, and the copper panel of covering made has excellent snappiness, high resistance stripping and good process. Solve the problem that anti-stripping is low, snappiness is poor.
The object of the present invention is achieved like this:
One has the preparation of excellent snappiness phosphor-containing halogen-free prime ring epoxy resins, and its divides three-step reaction and becomes:
1. general formula (1) and general formula (2) or general formula (3) add phosphorus-containing catalyst carry out pre-reaction generate Resin A;
2. phosphorous epoxy resin B is generated by general formula (4) or general formula (5) or general formula (6) and the organo phosphorous compounds phosphorus-containing catalyst with a reactive hydrogen atom again;
3. again A and B is mixed and add phosphorus-containing catalyst generation finished product, drip a solubilizing agent and dissolve;
Structural formula:
;
R is: H or CH3;
��
Resin A formula of (1) in the present invention is (0.1-1) with the mol ratio of general formula (2) or general formula (3): (2-5), is more suitable for being (0.5-1): (2-4); Also more it is suitable for (0.75-1): (3-4), causes chain extension not enough if ratio is too little, if ratio causes too greatly chain extension too big, section reaction after impact.
The phosphorous epoxy resin B of the present invention is by general formula (4) or general formula (5) or general formula (6) and has an organo phosphorous compounds with the active hydrogen atom of phosphorus atom key connection, such as DOPO(9,10-dihydro-9-oxy is mixed-10-phospho hetero phenanthrene-10-oxide compound), its phosphorus content is 1-4%, it is preferable over 1-3%, preferred selection at 1.5-3%, also more preferably in 2.0-3.0%.
In the present invention reactions steps 3. in the ratio of Resin A be 1-30%, it is preferable to 1-20%, it is more preferable to selection between 1-10, also preferred selection is between 1-8%.
The present invention containing phosphorus Cat is: any one in triphenylphosphine, tributylphosphine, trimethoxy phosphine, triethyl phosphine, ethyl (or butyl) triphenyl phosphate, consumption is 50-1000PPM, it is preferably 650-800PPM, it is more preferable to be 50-600PPM, be also more preferably 50-500PPM.
The present invention is any one or the compound use in acetone ACE, butanone MEK, toluene TOL, propylene glycol monomethyl ether PM containing phosphorus Cat solvent.
As the stiffening agent of the phosphorous epoxy resin of the present invention, it is possible to use the conventional solidifying agent of epoxy resin, such as Dyhard RU 100, these solidifying agent of DDM, DDS can separately can also compound use.
An application with excellent snappiness phosphor-containing halogen-free prime ring epoxy resins, adds solidifying agent at above-mentioned phosphor-containing halogen-free epoxy resin, soaks oven dry with glasscloth and make prepreg, and with being pressed into copper foil coveredization plate after tinsel superposition.
As follows by the prepreg method of the preparation of above-mentioned halogen-free phosphorus-containing epoxy resin: the method preparing prepreg do not the following describes restriction. Containing phosphorus ring oxygen, above-mentioned halogen is added solidifying agent and curing catalyst stir and be evenly made into glue liquid, then glasscloth is put into glue liquid soak, then prepreg is made with baking oven baking, and then prepare upper and lower Ge Jia tinsel by folded for prepreg, then solidify with press intensification pressing.
Compared with prior art, the invention has the beneficial effects as follows:
This phosphor-containing halogen-free prime ring epoxy resins does not contain the fire retarding epoxide resin of any halogen and does not use bromine fire-retardant, and the copper panel of covering made has excellent snappiness, high resistance stripping and good process. Solve the problem that anti-stripping is low, snappiness is poor.
Embodiment
Embodiment 1:
Add 192g dihydroxyphenyl propane (BPA) to being equipped with in the round-bottomed flask of electronic stirring, reflux condensing tube, thermometer, logical nitrogen protection, open heating unit and BPA is heated to molten state, start stirring, temperature is remained between 170 DEG C��175 DEG C. Add 0.06g triphenylphosphine dissolved 10 minutes, start vacuum pump and the air in four mouthfuls of round-bottomed flasks is taken away, be extracted into below-0.095Mpa and keep 10 minutes, lead to into nitrogen vacuum breaker. By 108g discharge ring oxygen (bisphenol A-type liquid epoxy, epoxy equivalent (weight) is 185g/Eq) it is heated to 150 DEG C, at the uniform velocity added in four mouthfuls of round-bottomed flasks with peristaltic pump with 60 minutes, reaction 60 minutes is kept after adding, reaction is evacuated down to below-0.095Mpa 10 minutes after terminating, logical nitrogen vacuum breaker obtains resin a, material flows out the hopper being placed in nitrogen and cools, shatter use, and hydroxyl equivalent is 265g/eq.
Embodiment 2:
Repeating embodiment 1, wherein BPA amount changes 213g into, and discharge ring oxygen amount is 87g, and all the other, all with embodiment 1, obtain resin b, and hydroxyl equivalent is 214g/Eq.
Embodiment 3:
Repeating embodiment 1, wherein BPA amount changes 192g into, and discharge ring epoxy resins is 108g, and all the other, all with embodiment 1, obtain resin c, and hydroxyl equivalent is 224g/Eq.
Embodiment 4:
Repeating embodiment 1, wherein BPA changes BPF into, measures as 213g, and discharge ring oxygen is 87g, and all the other steps, all with embodiment 1, obtain resin d, and hydroxyl equivalent is 181g/Eq.
Embodiment 5:
To electronic stirring is housed, reflux condensing tube, the round-bottomed flask of thermometer adds start after 230.6g novolac epoxy (F51) is heated to 100 DEG C and stir, then 54.4gDOPO and 0.07g triphenylphosphine is added, in control round-bottomed flask, temperature is that 100 DEG C of stirrings were evacuated down to below-0.095Mpa after 5 minutes, keep 10 minutes, logical nitrogen vacuum breaker, rise controlling temperature to 165-170 DEG C, keep reaction within 60 minutes, to cool to the 120-130 DEG C of resin a15g adding embodiment 1 preparation and add 0.15g iodate ethyl triphenyl phosphine, it is evacuated down to below-0.095Mpa, keep 10 minutes, logical nitrogen vacuum breaker, intensification temperature control reacts 90 minutes between 175-180 DEG C, it is evacuated down to below-0.095Mpa, use nitrogen vacuum breaker, 100g butanone is added with pyriform separating funnel, obtain finished product containing phosphorus ring oxygen EP1, phosphorus content is 2.6g, epoxy equivalent (weight) is 301g/Eq.
Embodiment 6:
Repeating embodiment 5, the resin a that wherein prepared by embodiment 1 is replaced by resin b prepared by embodiment 2, and all the other steps all do not change, and obtain finished product phosphorous epoxy resin EP2, and phosphorus content is 2.6g, and epoxy equivalent (weight) is 306g/Eq.
Embodiment 7:
Repeating embodiment 5, the resin a that wherein prepared by embodiment 1 is replaced by resin c prepared by embodiment 3, and all the other steps all do not change, and obtain finished product phosphorous epoxy resin EP3, and phosphorus content is 2.6g, and epoxy equivalent (weight) is 305g/Eq.
Embodiment 8:
Repeating embodiment 5, the resin a that wherein prepared by embodiment 1 is replaced by resin d prepared by embodiment 4, and all the other steps all do not change, and obtain finished product phosphorous epoxy resin EP4, and phosphorus content is 2.6g, and epoxy equivalent (weight) is 310g/Eq.
Comparative example 1:
Phenolic aldehyde ring oxygen 245.6g, DOPO54.4g, triphenylphosphine 0.06g is added to being equipped with in the round-bottomed flask of electronic stirring, reflux condensing tube, thermometer, starting intensification temperature control respectively controls at 100 DEG C, stir after 10 minutes, start vacuum pump and vacuum is extracted into below-0.095Mpa, keep 10 minutes, use nitrogen vacuum breaker, add 100g butanone in resin; Obtaining comparative example resin, phosphorus content is 2.6g, and epoxy equivalent (weight) is 264g/Eq.
The hardening of epoxy resin and the manufacture of prepreg:
In order to control the performance of the epoxy resin of preparation in above-described embodiment, Dyhard RU 100 [consumption is 100g ring oxygen (100% solid) �� 21 �� epoxy resin equivalent �� 0.5] is used to use as stiffening agent, glyoxal ethyline (for the 300ppm of resin measures) is cured reaction as curing catalyst, with DMF as solvent, the solid content of glue liquid is controlled between 60-65%.
Deployed glue liquid is evenly coated on glass pricker dimension cloth (7628 type), and 170 DEG C of dryings 3 minutes, obtains prepreg.
Getting 8 prepregs to stack, upper and lower Ge Jia 1OZ Copper Foil, be placed in press with 35kgf/ 2 pressure, 180 DEG C of hot pressing 120 minutes, obtains band copper-clad laminate.
By the data of table 1 it may be seen that employ the loss respectively having the several years above the phosphor-containing halogen-free prime ring epoxy resins Tg of the technology feature of the present invention, but anti-stripping is greatly improved, and thermal shocking have also been obtained very big lifting. The present invention can provide excellent surperficial anti-stripping and interlaminar bonding power as can be seen here, sheet material obtains good snappiness, it is to increase the processibility of PBC plate, it is to increase working (machining) efficiency, reduces quality bad.
Table 1:
| Resin | Unit | EP1 | EP2 | EP3 | EP4 | Comparative resin 1 |
| Phosphorus content | % | 2.6 | 2.6 | 2.6 | 2.6 | 2.6 |
| Epoxy equivalent (weight) | g/Eq | 301 | 306 | 305 | 310 | 264 |
| Dyhard RU 100 amount | g | 3.49 | 3.43 | 3.44 | 3.39 | 3.98 |
| Methylimidazole amount | g | 0.03 | 0.03 | 0.03 | 0.03 | 0.04 |
| Gel time | s | 230 | 233 | 228 | 235 | 220 |
| Tg | �� | 144 | 145 | 140 | 142 | 148 |
| The anti-stripping in surface | N/mm | 1.58 | 1.6 | 1.57 | 1.59 | 1.41 |
| Anti-stripping between layer | N/mm | 0.62 | 0.64 | 0.62 | 0.60 | 0.45 |
| Floating weldering 288 DEG C | s | > 300 | > 300 | > 300 | > 300 | > 300 |
| Immersed solder 288 DEG C | s | 250 | 230 | 235 | 225 | 230 |
| Thermal shocking 288 DEG C (10s/20s) | Secondary | > 15 | > 15 | > 15 | > 15 | 10 |
| Fire-retardant (UL-94) | Grade | V0 | V0 | V0 | V0 | V0 |
Claims (13)
1. one kind has the preparation of excellent snappiness phosphor-containing halogen-free prime ring epoxy resins, it is characterised in that: its divides three-step reaction and becomes:
1. general formula (1) and general formula (2) add phosphorus-containing catalyst and carry out pre-reaction and generate Resin A;
2. phosphorous epoxy resin B is generated by general formula (4) or general formula (5) or general formula (6) and the organo phosphorous compounds phosphorus-containing catalyst with a reactive hydrogen atom again;
3. again A and B is mixed and add phosphorus-containing catalyst generation finished product, drip a solubilizing agent and dissolve;
Structural formula:
;
R is: H or CH3;
��
2. one according to claim 1 has the preparation of excellent snappiness phosphor-containing halogen-free prime ring epoxy resins, it is characterised in that, the mol ratio of described Resin A formula of (1) and general formula (2) is in (0.1��1): (2��5).
3. one according to claim 1 has the preparation of excellent snappiness phosphor-containing halogen-free prime ring epoxy resins, it is characterised in that, described step 2. in there is a reactive hydrogen atom organo phosphorous compounds be that 9,10-bis-hydrogen-10-oxygen-phosphine is assorted luxuriant and rich with fragrance.
4. one according to claim 1 has the preparation of excellent snappiness phosphor-containing halogen-free prime ring epoxy resins, it is characterised in that, described phosphorous epoxy resin B, its phosphorus content is 1-4%, reactions steps 3. in the ratio of Resin A be 1-30%.
5. one according to claim 4 has the preparation of excellent snappiness phosphor-containing halogen-free prime ring epoxy resins, it is characterised in that, reactions steps 3. in the ratio of Resin A be 1-20%.
6. one according to claim 5 has the preparation of excellent snappiness phosphor-containing halogen-free prime ring epoxy resins, it is characterised in that, reactions steps 3. in the ratio of Resin A be between 1-10%.
7. one according to claim 6 has the preparation of excellent snappiness phosphor-containing halogen-free prime ring epoxy resins, it is characterised in that, reactions steps 3. in the ratio of Resin A between 1-8%.
8. one according to claim 1 has the preparation of excellent snappiness phosphor-containing halogen-free prime ring epoxy resins, it is characterized in that, described phosphorus-containing catalyst be in triphenylphosphine, tributylphosphine, trimethoxy phosphine, triethyl phosphine, ethyl triphenyl phosphoric acid salt, butyl triphenyl phosphoric acid salt any one or several.
9. one according to claim 1 has the preparation of excellent snappiness phosphor-containing halogen-free prime ring epoxy resins, it is characterised in that, described solvent is one or more in acetone, toluene, butanone, propylene glycol monomethyl ether.
10. one kind has the application of excellent snappiness phosphor-containing halogen-free prime ring epoxy resins, it is characterised in that, by the finished product of preparation in one of claim 1-9, add in nitrogen-containing hardener Dyhard RU 100, DDM solidifying agent, DDS solidifying agent any one; Preparation plastic liquid, immerses glasscloth baking in glue liquid and makes prepreg.
11. a kind of application with excellent snappiness phosphor-containing halogen-free prime ring epoxy resins according to claim 10, it is characterized in that, when preparing glue liquid, also adding curing catalyst, described curing catalyst is any one in glyoxal ethyline, 2-methyl-4 ethyl imidazol(e), 2-phenylimidazole.
12. a kind of application with excellent snappiness phosphor-containing halogen-free prime ring epoxy resins according to claim 10, it is characterized in that, the prepreg being prepared from carries out superposition and in prepreg upper and lower Ge Jia 1 tinsel, puts into the press that can rise temperature control and carry out hot pressing and make phosphor-containing halogen-free and cover copper panel.
13. a kind of application with excellent snappiness phosphor-containing halogen-free prime ring epoxy resins according to claim 11, it is characterized in that, the prepreg being prepared from carries out superposition and in prepreg upper and lower Ge Jia 1 tinsel, puts into the press that can rise temperature control and carry out hot pressing and make phosphor-containing halogen-free and cover copper panel.
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| CN110964176A (en) * | 2019-12-18 | 2020-04-07 | 四川东材科技集团股份有限公司 | Preparation method of high-heat-resistance phosphorus-containing epoxy resin |
| CN112538155A (en) * | 2020-11-02 | 2021-03-23 | 建滔（江苏）化工有限公司 | Phosphorus-containing halogen-free epoxy resin and preparation method and application thereof |
| CN114801348B (en) * | 2022-05-25 | 2023-02-03 | 江门建滔积层板有限公司 | Preparation process of high-flame-retardance heat-resistant 22F copper-clad plate |
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| US20120129414A1 (en) * | 2010-11-24 | 2012-05-24 | Chung-Hao Chang | Thermosetting resin composition and prepreg or laminate using the same |
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Effective date of registration: 20160823 Address after: 511600 Guangdong city of Qingyuan province Fogang County Shek Kok town Ring Road South Industrial Zone Kingboard Industrial Park Patentee after: Kingboard (Fogang) Laminate Plate Co., Ltd. Address before: Huang Tu Zhen Shi Zhuang Bei Lu, Jiangyin City, Jiangsu province 214445 Carsem Wuxi City No. 2 Patentee before: Kingboard Chemical Co., Ltd. (Jiangsu) |