CN1194025C - Liquefied dicyandiamide and its preparing process - Google Patents
Liquefied dicyandiamide and its preparing process Download PDFInfo
- Publication number
- CN1194025C CN1194025C CNB021310785A CN02131078A CN1194025C CN 1194025 C CN1194025 C CN 1194025C CN B021310785 A CNB021310785 A CN B021310785A CN 02131078 A CN02131078 A CN 02131078A CN 1194025 C CN1194025 C CN 1194025C
- Authority
- CN
- China
- Prior art keywords
- dicyandiamide
- liquefied
- parts
- ethylene glycol
- dyhard
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title description 3
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 4
- 239000004593 Epoxy Substances 0.000 claims description 24
- -1 neodecanoic acid glycidyl ester Chemical class 0.000 claims description 11
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 8
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 6
- 229940015043 glyoxal Drugs 0.000 claims description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 11
- 239000003822 epoxy resin Substances 0.000 abstract description 8
- 229920000647 polyepoxide Polymers 0.000 abstract description 8
- 239000000203 mixture Substances 0.000 abstract description 4
- 239000011248 coating agent Substances 0.000 abstract description 3
- 238000000576 coating method Methods 0.000 abstract description 3
- 230000007774 longterm Effects 0.000 abstract description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 abstract 1
- 239000007767 bonding agent Substances 0.000 abstract 1
- 239000002131 composite material Substances 0.000 abstract 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 abstract 1
- 230000007794 irritation Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000006641 stabilisation Effects 0.000 abstract 1
- 238000011105 stabilization Methods 0.000 abstract 1
- 229920005989 resin Polymers 0.000 description 19
- 239000011347 resin Substances 0.000 description 19
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000237502 Ostreidae Species 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229940072282 cardura Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- OZCWUNHGNVXCCO-UHFFFAOYSA-N oxiran-2-ylmethyl hydrogen carbonate Chemical group OC(=O)OCC1CO1 OZCWUNHGNVXCCO-UHFFFAOYSA-N 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
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- Epoxy Resins (AREA)
Abstract
The present invention belongs to the field of coating materials, composite materials and bonding agents, particularly relates to liquefacient dicyandiamide and a preparation method thereof. 100 portions of dicyandiamide, 300 to 600 portions of glycidyl neocaprate, 50 to 200 portions of solvent and 0.5 to 1 portion of 2-Ethyl-4-methylimidazole or 2-methyl imidazole are added in a reactor, and the mixture is stirred and heated; then the mixture reacts at 140 to 150 DEG C for 12 to 14 hours, and viscid liquid is obtained after the reactor is pumped to vacuum and the solvent is removed. When the liquefacient dicyandiamide is used with epoxy resin with a proportion, the weight ratio of the liquefacient dicyandiamide to the epoxy resin is 30 to 50: 100. The solidifying agent of the liquefacient dicyandiamide has the advantages of good intermiscibility with the epoxy resin, no irritation, and stabilization in long-term storage; in addition, the good mechanical property of dicyandiamide solidified epoxy resin is kept.
Description
Technical field
The invention belongs to coating, matrix material or sizing agent field, particularly liquefied dicyandiamide and preparation method thereof.
Background technology
Dyhard RU 100 has another name called dicyanodiamide.One, because conjugated double bond and cyano group effect in the molecule descends its alkalescence greatly, so it and epoxy resin composition are at room temperature very stable, can be used as the potentiality solidifying agent; Its two, the cured article mechanical property of it and Resins, epoxy is good; Its three, nontoxic, nonirritant.Thereby Dyhard RU 100 is used widely in fields such as coating, matrix material, sizing agents as curing agent for epoxy resin.
Dyhard RU 100 is a white crystalline powder, and fusing point is 207～209 ℃.Water-soluble and ethanol, but very poor with the Resins, epoxy compatibility, so Dyhard RU 100 must be ground into it superfine powder suspension in Resins, epoxy as the effective solidifying agent of Resins, epoxy, again because of it very easily absorbs water in air part, therefore technology more complicated in process for preparation.
Very poor in view of Dyhard RU 100 and Resins, epoxy reactive behavior, compatibility is bad again each other, so need be to the further modification of Dyhard RU 100.
Summary of the invention
One of purpose of the present invention is in order to overcome the high-melting-point of Dyhard RU 100, immiscible and very easily absorb water and bother in the process for preparation that brings with Resins, epoxy, a kind of good fluidity is provided, very easily mix mutually with Resins, epoxy, low toxicity, non-stimulated flavor is not separated out solid after the placement, and the excellent mechanical properties of the potentiality of maintenance Dyhard RU 100 and cured article thereof, as the liquefied dicyandiamide of epoxy curing agent use.
Another object of the present invention provides a kind of preparation method of liquefied dicyandiamide, makes Dyhard RU 100 and Resins, epoxy after the liquefaction that good intermiscibility be arranged.
Dyhard RU 100 is a kind of dystectic solid (m.p.207 ℃～209 ℃) and is insoluble to Resins, epoxy.Therefore, it is very slow to carry out the reaction of Dyhard RU 100 and Resins, epoxy in the following temperature of the fusing point of Dyhard RU 100.The inventor finds that neodecanoic acid glycidyl ester and Dyhard RU 100 also do not dissolve each other, and does not see reaction in 5-6 hour 150 ℃ of heating.Yet the inventor with a kind of can molten Resins, epoxy again can molten Dyhard RU 100 solvent, add a spot of promotor again, under low relatively temperature (150 ℃), solved Resins, epoxy and be difficult for problem with the Dyhard RU 100 reaction.
Liquefied dicyandiamide of the present invention comprises following component and content, in weight part:
100 parts of Dyhard RU 100s
300～600 parts of neodecanoic acid glycidyl esters
50～200 parts of solvents
0.5～1 part of promotor
Described neodecanoic acid glycidyl ester can be the product of Shell Co. Ltd's commodity Cardura E-10 by name.
Described solvent is selected from ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether etc.
Described promotor is 2-ethyl-4-methylimidazole or glyoxal ethyline etc.
Liquefied dicyandiamide solidifying agent preparation method of the present invention is:
With 100 parts Dyhard RU 100,300～600 parts neodecanoic acid glycidyl ester, 50～200 parts solvent, and 0.5～1 part 2-ethyl-4-methylimidazole or glyoxal ethyline join in the reactor that electric mixer, spherical condensation tube and thermometer are housed; Stir and heat up, reacted 12～14 hours down at 140 ℃～150 ℃; Vacuumize and remove solvent, obtain the liquid of sticky shape.
The present invention is that its chemical formula is with neodecanoic acid glycidyl ester (being the tertiary carbonic acid glycidyl ester that has 10 carbon atoms):
Epoxy equivalent (weight) is 224-256, and its epoxy group(ing) is active big, and light than general mono-epoxy compounds smell, toxicity is low, and is almost non-stimulated to human body skin.Its long carbochain also can play self-plasticizing action.Selecting E-10 for use is properties-correcting agent as liquefied dicyandiamide.
Liquefied dicyandiamide of the present invention is when using with the Resins, epoxy proportioning, and liquefied dicyandiamide: the weight ratio of Resins, epoxy is 30-50: 100.
Liquefied dicyandiamide solidifying agent of the present invention is mutually solvent with Resins, epoxy, nonirritant, and long-term storage is stable, and keeps Dyhard RU 100 cured epoxy resin excellent mechanical properties.Its performance sees Table 1 and 2.
Table 1 liquefied dicyandiamide curing agents
The performance of table 2 liquefied dicyandiamide and epoxy resin cured product
Annotate: in weight part
(1) Comparative Examples: the Dyhard RU 100 consumption is 8 parts, 100 parts of Resins, epoxy;
(2) embodiment 1: the liquefied dicyandiamide consumption is 30 parts, 100 parts of Resins, epoxy; Embodiment 2: the liquefied dicyandiamide consumption is 40 parts, 100 parts of Resins, epoxy; Embodiment 3: the liquefied dicyandiamide consumption is 50 parts, 100 parts of Resins, epoxy.
(3) condition of cure: 140 ℃/12 hours
Embodiment
Embodiment 1:
Electric mixer is being housed, in the there-necked flask of the 250ml of spherical condensation tube and thermometer, add 34 gram Dyhard RU 100s, the 2-ethyl-4-methylimidazole of 0.34 gram, the neodecanoic acid glycidyl ester of 60 gram ethylene glycol monomethyl ethers and 91 grams, start agitator, begin to heat up, maintain the temperature at 140 ℃～150 ℃, reacted 12 hours, vacuumize and remove solvent, about about 10 minutes of time.Obtain the sticky shape liquid of oyster white.Performance sees Table 1 and 2.
Embodiment 2:
Electric mixer is being housed, in the there-necked flask of the 50ml of spherical condensation tube and thermometer, add 34 gram Dyhard RU 100s, the 2-ethyl-4-methylimidazole of 0.34 gram, the neodecanoic acid glycidyl ester of 80 gram ethylene glycol monomethyl ethers and 137 grams, start agitator, begin to heat up, maintain the temperature at 140 ℃～150 ℃, reacted 12 hours, vacuumize and remove solvent, about about 10 minutes of time.Obtain sticky shape and be shallow milky product.Performance sees Table 1 and 2.
Embodiment 3:
Electric mixer is being housed, in the there-necked flask of the 250ml of spherical condensation tube and thermometer, add 34 gram Dyhard RU 100s, the 2-ethyl-4-methylimidazole of 0.34 gram, the neodecanoic acid glycidyl ester of the ethylene glycol monomethyl ether of 100 grams and 182 grams, start agitator, begin to heat up, maintain the temperature at 140 ℃～150 ℃, reacted 14 hours, vacuumize and remove solvent, about 10 minutes of time.Obtain the product that sticky shape is lightcoral.Performance sees Table 1 and 2.
Claims (4)
1. liquefied dicyandiamide, it is characterized in that: the component and the content of described liquefied dicyandiamide are counted with weight part:
100 parts of Dyhard RU 100s
300～600 parts of neodecanoic acid glycidyl esters
50～200 parts of solvents
0.5～1 part of promotor
Described promotor is 2-ethyl-4-methylimidazole or glyoxal ethyline;
Described solvent is selected from ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether.
2. liquefied dicyandiamide as claimed in claim 1 is characterized in that: described neodecanoic acid glycidyl ester chemical formula is:
Epoxy equivalent (weight) is 224-256.
3. the preparation method of a liquefied dicyandiamide as claimed in claim 1, it is characterized in that: in weight part, the preparation method of described liquefied dicyandiamide is:
With 100 parts Dyhard RU 100,300～600 parts neodecanoic acid glycidyl ester, 50～200 parts solvent, and 0.5～1 part 2-ethyl-4-methylimidazole or glyoxal ethyline join in the reactor; Stir and heat up, reacted 12～14 hours down at 140 ℃～150 ℃; Vacuumize and remove solvent, obtain the liquid of sticky shape;
Described solvent is selected from ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether.
4. the preparation method of liquefied dicyandiamide as claimed in claim 3, it is characterized in that: the chemical formula of described neodecanoic acid glycidyl ester is:
Epoxy equivalent (weight) is 224-256.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021310785A CN1194025C (en) | 2002-09-28 | 2002-09-28 | Liquefied dicyandiamide and its preparing process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021310785A CN1194025C (en) | 2002-09-28 | 2002-09-28 | Liquefied dicyandiamide and its preparing process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1485356A CN1485356A (en) | 2004-03-31 |
| CN1194025C true CN1194025C (en) | 2005-03-23 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB021310785A Expired - Fee Related CN1194025C (en) | 2002-09-28 | 2002-09-28 | Liquefied dicyandiamide and its preparing process |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1194025C (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101521362B1 (en) | 2010-09-22 | 2015-05-18 | 세키스이가가쿠 고교가부시키가이샤 | Curable composition for inkjet, and method for producing electronic component |
| JP5416725B2 (en) | 2010-09-24 | 2014-02-12 | 積水化学工業株式会社 | Curable composition for inkjet and method for producing printed wiring board |
| CN102633987A (en) * | 2012-04-26 | 2012-08-15 | 厦门大学 | Liquid dicyandiamide latent type epoxy resin curing agent and preparation method thereof |
-
2002
- 2002-09-28 CN CNB021310785A patent/CN1194025C/en not_active Expired - Fee Related
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| Publication number | Publication date |
|---|---|
| CN1485356A (en) | 2004-03-31 |
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