CN102775605A - Modified bismaleimide resin and preparation method thereof - Google Patents
Modified bismaleimide resin and preparation method thereof Download PDFInfo
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- CN102775605A CN102775605A CN2012102884309A CN201210288430A CN102775605A CN 102775605 A CN102775605 A CN 102775605A CN 2012102884309 A CN2012102884309 A CN 2012102884309A CN 201210288430 A CN201210288430 A CN 201210288430A CN 102775605 A CN102775605 A CN 102775605A
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Abstract
The invention relates to modified bismaleimide resin and a preparation method of the modified bismaleimide resin. The method comprises the following steps of: uniformly mixing N,N'-4,4'-diphenylmethane bismaleimide, diallyl bisphenol A and N-(beta-aminoethyl)-gamma-aminopropyl trimethoxy silane in proportion under a normal temperature and normal pressure condition, reacting at 40-60 DEG C for 40-100 minutes, rising the temperature to 130-150 DEG C, reacting for 40-100 minutes while keeping stirring, carrying out vacuum debubbling so as to obtain the modified bismaleimide resin, and carrying out the curing process and the curing treatment so as to obtain cured resin. According to the method, the activity of the siloxane upamido and the unique structure are utilized for comixing/copolymerization modification with the resin, so that the process is simple and easy to control. The prepared modified bismaleimide resin is small in melting viscosity and good in solvent dissolubility; and moreover, the prepared cured resin is increased in comprehensive properties such as toughness, heat resistance, dielectric property and the like.
Description
Technical field
The present invention relates to field of compound material, be specifically related to a kind of modified bismaleimide resin and preparation method thereof, be a kind of modified bismaleimide resin with higher toughness, high heat resistance and low-k.
Background technology
Bimaleimide resin (BMI) is a domestic and international resin material newly developed in recent decades, because of advantages such as it have good high temperature resistant, radiation hardness, moisture-proof heat, rate of moisture absorption is low and thermal expansivity is little, and then receives extensive attention in field of materials.But the same big shortcoming of fragility that exists of BMI resin with other thermosetting resins, the manufacturability that is used for preparing matrix material is poor, and mold temperature is high.For improving its shortcoming, improve the important directions that toughness and manufacturability have become the development of BMI polymer matrix composites.Over nearly 20 years, the BMI resin toughening is the important content of performance resins research and development always.On the basis that keeps the original premium properties of BMI resin, it is carried out the important topic that toughening modifying then is present stage macromolecular material research.Existing BMI resin toughening method major part all is to obtain toughening effect on the basis of sacrificing its outstanding resistance toheat.Be the science and technology that satisfies high speed development now and industrial, a kind ofly have excellent manufacturability concurrently, the development of outstanding toughness and stable on heating new type resin system is extremely urgent.
The preparation method of the disclosed relevant hyperbranched silicone-modified thermosetting resin of existing document, it is too fast all to exist the resin viscosity rate of growth, causes reaction to be difficult to problems such as control.University Of Suzhou turns round and look at the beautiful people of grade of beloved daughter and discloses the patented claim about the hyperbranched polyorganosiloxane modified bismaleimide resin; Though these work have confirmed hyperbranched polyorganosiloxane and have produced effect aspect toughness reinforcing at thermosetting resin; But the uncontrollability of its siloxanes hydrolysis degree and cause level of response uncontrollable is to the toughness reinforcing defectives such as unstable that exist of thermosetting resin.
Summary of the invention
The technical problem that solves
Weak point for fear of prior art; The present invention proposes a kind of modified bismaleimide resin system and preparation method thereof; A kind of outstanding toughness that has is provided; Excellent high thermal resistance, excellent dielectric properties and technological modified bismaleimide resin and a kind of preparation method who reacts the strong modified bismaleimide resin of controllability.
Technical scheme
A kind of modified bismaleimide resin is characterized in that material component is by mole: 100 parts of N, and N'-4,4'-diphenyl methane dimaleimide, 40 ~ 80 parts of diallyl bisphenols and 1 ~ 20 part of siloxanes contain the diamine base.
It is a kind of in N-(β-aminoethyl)-γ-An Bingjisanjiayangjiguiwan or N-(β-aminoethyl)-γ-An Bingjisanyiyangjiguiwan or 2 kinds that said siloxanes contains the diamine base.
A kind of method for preparing said modified bismaleimide resin is characterized in that step is following:
Step 1: 100 parts bismaleimidess, 35 ~ 70 parts of diallyl bisphenols and 1 ~ 12 part of N-(β-aminoethyl)-γ-An Bingjisanjiayangjiguiwan are mixed at ambient temperature, and reaction is 40 ~ 100 minutes under 40 ℃ ~ 60 ℃ environment;
Step 2: be warming up to 130 ℃ ~ 150 ℃, under the maintenance stirring condition, reacted 40 ~ 100 minutes, behind the vacuum degassing bubble, obtain modified bismaleimide resin.
The modified bismaleimide resin that step 2 is obtained obtains the bismaleimides cured resin behind the post curing treatment of the curing process of 140 ℃/2h, 160 ℃/h, 180 ℃/2h and 200 ℃/2h and 240 ℃/4h.
Beneficial effect
A kind of modified bismaleimide resin system that the present invention proposes and preparation method thereof, than prior art, the preparation method that the present invention adopts has not only simplified processing condition, and is easy to control.Adopt the Bismaleimides resin pre-polymer of method preparation of the present invention, in acetone and other organic solvent, have good solvability, this is highly beneficial for making high performance composite.In addition; Than other bimaleimide resins; The melting viscosity of the prepared modified bismaleimide resin of the present invention is little, solvent solubility and reactive good, and over-all propertieies such as the toughness of the cured resin that obtains, thermostability and dielectric properties all have obvious lifting.
Embodiment
Combine embodiment that the present invention is further described at present:
Embodiment 1:
The N of 100g, N'-4, the 4'-diphenyl methane dimaleimide, the diallyl bisphenol of 43g and the N-of 6.3g (β-aminoethyl)-γ-An Bingjisanjiayangjiguiwan mix at ambient temperature, are warming up to 50 ℃, and reaction is 90 minutes under this environment; Be warming up to 140 ℃, keep reacting 40 minutes under the stirring condition, after the vacuum stripping bubble is handled, obtain a kind of modified bismaleimide resin.
Above-mentioned modified bismaleimide resin obtains the modified bismaleimide cured resin behind the post curing treatment of the curing process of 140 ℃/2h, 160 ℃/h, 180 ℃/2h and 200 ℃/2h and 240 ℃/4h.
Reference examples: component is N, N'-4,4'-diphenyl methane dimaleimide and diallyl bisphenol;
The N of 100g, N'-4, the diallyl bisphenol of 4'-diphenyl methane dimaleimide and 25 ~ 70g mixes at ambient temperature, is warming up to 50 ℃, and reaction is 90 minutes under this environment; Be warming up to 140 ℃, keep reacting 40 minutes under the stirring condition, after the vacuum stripping bubble is handled, obtain bimaleimide resin.Behind the post curing treatment of the curing process of 140 ℃/2h, 160 ℃/h, 180 ℃/2h and 200 ℃/2h and 240 ℃/4h, obtain the bismaleimides cured resin.
Testing method according to GB/T2570-1995 and GB/T2571-1995 is tested comparison toughness and intensity to the shock strength and the flexural strength of two kinds of resins of the foregoing description 1 and reference examples; With thermogravimetic analysis (TGA) (TGA) and dynamic mechanically mechanical property (DMA) analysis the resistance toheat of two kinds of resins of the foregoing description 1 and reference examples is estimated; Two kinds of resins to the foregoing description 1 and reference examples carry out gel time and tangent of the dielectric loss angle value test sign reactivity and dielectric properties.
Each item performance of the bismaleimides cured resin in 1 resulting modified bismaleimide cured resin of embodiment among the present invention and the reference examples is tested comparison, and the result is shown in table 1, table 2.
Table 1
Table 2 performance data
According to above-mentioned table 1 and table 2 data presentation, compare bimaleimide resin, the toughness of modified bismaleimide resin provided by the invention and intensity have obtained significant raising; From the gel time data presentation, the present invention provides having of modified bismaleimide resin better reactivity; According to the thermal property data, the thermotolerance of modified bismaleimide resin provided by the invention has obtained tangible lifting; The tangent of the dielectric loss angle Value Data shows that modified bismaleimide resin provided by the invention has dielectric properties preferably.
Embodiment 2:
The N of 100g, N'-4, the 4'-diphenyl methane dimaleimide, the diallyl bisphenol of 43g and the N-of 6.3g (β-aminoethyl)-γ-An Bingjisanjiayangjiguiwan mix at ambient temperature, are warming up to 50 ℃, and reaction is 90 minutes under this environment; Be warming up to 140 ℃, keep reacting 40 minutes under the stirring condition, after the vacuum stripping bubble is handled, obtain a kind of modified bismaleimide resin.This resin obtains the modified bismaleimide cured resin behind the post curing treatment of the curing process of 140 ℃/2h, 160 ℃/2h, 180 ℃/2h and 200 ℃/2h and 240 ℃/4h.
Embodiment 3:
The N of 100g, N'-4, the 4'-diphenyl methane dimaleimide, the diallyl bisphenol of 43g and the N-of 6.3g (β-aminoethyl)-γ-An Bingjisanyiyangjiguiwan mix at ambient temperature, are warming up to 50 ℃, and reaction is 90 minutes under this environment; Be warming up to 140 ℃, keep reacting 40 minutes under the stirring condition, after the vacuum stripping bubble is handled, obtain a kind of modified bismaleimide resin.This resin obtains the modified bismaleimide cured resin behind the post curing treatment of the curing process of 140 ℃/2h, 160 ℃/h, 180 ℃/2h and 200 ℃/2h and 240 ℃/4h.
Embodiment 4:
The N of 100g, N'-4, the 4'-diphenyl methane dimaleimide, the diallyl bisphenol of 43g and the N-of 7.56g (β-aminoethyl)-γ-An Bingjisanjiayangjiguiwan mix at ambient temperature, are warming up to 50 ℃, and reaction is 90 minutes under this environment; Be warming up to 140 ℃, keep reacting 40 minutes under the stirring condition, after the vacuum stripping bubble is handled, obtain a kind of modified bismaleimide resin.This resin obtains the modified bismaleimide cured resin behind the post curing treatment of the curing process of 140 ℃/2h, 160 ℃/h, 180 ℃/2h and 200 ℃/2h and 240 ℃/4h.
Embodiment 5:
The N of 100g, N'-4, the 4'-diphenyl methane dimaleimide, the diallyl bisphenol of 43g and the N-of 5.04g (β-aminoethyl)-γ-An Bingjisanjiayangjiguiwan mix at ambient temperature, are warming up to 50 ℃, and reaction is 90 minutes under this environment; Be warming up to 140 ℃, keep reacting 40 minutes under the stirring condition, after the vacuum stripping bubble is handled, obtain a kind of modified bismaleimide resin.This resin obtains the modified bismaleimide cured resin behind the post curing treatment of the curing process of 140 ℃/2h, 160 ℃/h, 180 ℃/2h and 200 ℃/2h and 240 ℃/4h.
Embodiment 6:
The N of 100g, N'-4, the 4'-diphenyl methane dimaleimide, the diallyl bisphenol of 43g and the N-of 3.15g (β-aminoethyl)-γ-An Bingjisanjiayangjiguiwan mix at ambient temperature, are warming up to 50 ℃, and reaction is 90 minutes under this environment; Be warming up to 140 ℃, keep reacting 40 minutes under the stirring condition, after the vacuum stripping bubble is handled, obtain a kind of modified bismaleimide resin.This resin obtains the modified bismaleimide cured resin behind the post curing treatment of the curing process of 140 ℃/2h, 160 ℃/h, 180 ℃/2h and 200 ℃/2h and 240 ℃/4h.
Embodiment 7:
The N of 100g, N'-4, the 4'-diphenyl methane dimaleimide, the diallyl bisphenol of 43g and the N-of 2.52g (β-aminoethyl)-γ-An Bingjisanjiayangjiguiwan mix at ambient temperature, are warming up to 50 ℃, and reaction is 90 minutes under this environment; Be warming up to 140 ℃, keep reacting 40 minutes under the stirring condition, after the vacuum stripping bubble is handled, obtain a kind of modified bismaleimide resin.This resin obtains the modified bismaleimide cured resin behind the post curing treatment of the curing process of 140 ℃/2h, 160 ℃/h, 180 ℃/2h and 200 ℃/2h and 240 ℃/4h.
Embodiment 8:
The N of 100g, N'-4, the 4'-diphenyl methane dimaleimide, the diallyl bisphenol of 50g and the N-of 6.3g (β-aminoethyl)-γ-An Bingjisanjiayangjiguiwan mix at ambient temperature, are warming up to 50 ℃, and reaction is 90 minutes under this environment; Be warming up to 140 ℃, keep reacting 40 minutes under the stirring condition, after the vacuum stripping bubble is handled, obtain a kind of modified bismaleimide resin.This resin obtains the modified bismaleimide cured resin behind the post curing treatment of the curing process of 140 ℃/2h, 160 ℃/h, 180 ℃/2h and 200 ℃/2h and 240 ℃/4h.
Embodiment 9:
The N of 100g, N'-4, the 4'-diphenyl methane dimaleimide, the diallyl bisphenol of 65g and the N-of 6.3g (β-aminoethyl)-γ-An Bingjisanjiayangjiguiwan mix at ambient temperature, are warming up to 50 ℃, and reaction is 90 minutes under this environment; Be warming up to 140 ℃, keep reacting 40 minutes under the stirring condition, after the vacuum stripping bubble is handled, obtain a kind of modified bismaleimide resin.This resin obtains the modified bismaleimide cured resin behind the post curing treatment of the curing process of 140 ℃/2h, 160 ℃/h, 180 ℃/2h and 200 ℃/2h and 240 ℃/4h.
Claims (4)
1. modified bismaleimide resin is characterized in that material component is by mole: 100 parts of N, and N'-4,4'-diphenyl methane dimaleimide, 40 ~ 80 parts of diallyl bisphenols and 1 ~ 20 part of siloxanes contain the diamine base.
2. modified bismaleimide resin according to claim 1 is characterized in that: it is a kind of in N-(β-aminoethyl)-γ-An Bingjisanjiayangjiguiwan or N-(β-aminoethyl)-γ-An Bingjisanyiyangjiguiwan or 2 kinds that said siloxanes contains the diamine base.
3. one kind prepares right 1 or 2
SaidThe method of modified bismaleimide resin; It is characterized in that step is following: step 1: 100 parts bismaleimidess, 35 ~ 70 parts of diallyl bisphenols and 1 ~ 12 part of N-(β-aminoethyl)-γ-An Bingjisanjiayangjiguiwan are mixed at ambient temperature, and reaction is 40 ~ 100 minutes under 40 ℃ ~ 60 ℃ environment;
Step 2: be warming up to 130 ℃ ~ 150 ℃, under the maintenance stirring condition, reacted 40 ~ 100 minutes, behind the vacuum degassing bubble, obtain modified bismaleimide resin.
4. method according to claim 2; It is characterized in that: the modified bismaleimide resin that step 2 is obtained obtains the bismaleimides cured resin behind the post curing treatment of the curing process of 140 ℃/2h, 160 ℃/h, 180 ℃/2h and 200 ℃/2h and 240 ℃/4h.
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103172862A (en) * | 2013-03-28 | 2013-06-26 | 西北工业大学 | Nano-filler bismaleimide resin and preparation method thereof |
| CN103881379A (en) * | 2014-03-20 | 2014-06-25 | 西北工业大学 | Hydroxyl silicate/phosphorus-containing benzoxazine/bismaleimide resin composite material and preparation method thereof |
| CN104592665A (en) * | 2015-02-13 | 2015-05-06 | 芜湖市伟华泡塑有限公司 | Modified polystyrene resin foam plastic |
| CN104610678A (en) * | 2015-02-13 | 2015-05-13 | 芜湖市伟华泡塑有限公司 | Heat-resistant high-tenacity polystyrene resin foamed plastic |
| CN109180947A (en) * | 2018-07-24 | 2019-01-11 | 西北工业大学 | One kind modified bismaleimide resin containing ethenyl cage model sesquialter siloxane and preparation method |
| CN109988305A (en) * | 2017-12-29 | 2019-07-09 | 深圳光启尖端技术有限责任公司 | Modified bismaleimide resin and preparation method thereof |
| WO2021134993A1 (en) * | 2019-12-31 | 2021-07-08 | 广东生益科技股份有限公司 | Resin composition and prepreg sheet using same, and insulating plate |
| CN113929913A (en) * | 2021-10-19 | 2022-01-14 | 福建师范大学 | Bismaleimide/polyether siloxane resin and preparation method thereof |
| TWI756679B (en) * | 2019-12-31 | 2022-03-01 | 大陸商廣東生益科技股份有限公司 | A kind of modified maleimide compound and its preparation method and application |
| CN114561101A (en) * | 2022-04-01 | 2022-05-31 | 焦作市天益科技有限公司 | Diallyl bisphenol A modified bismaleimide resin capable of prolonging shelf life and preparation method thereof |
| WO2022266951A1 (en) * | 2021-06-24 | 2022-12-29 | 穗晔实业股份有限公司 | Thermosetting resin composition and prepreg |
| US11639439B2 (en) | 2021-06-24 | 2023-05-02 | Prior Company Limited | Thermosetting resin composition and prepreg |
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2012
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| CN101775139A (en) * | 2009-12-31 | 2010-07-14 | 苏州大学 | Method for preparing modified bismaleimide resin |
Non-Patent Citations (1)
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Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103172862A (en) * | 2013-03-28 | 2013-06-26 | 西北工业大学 | Nano-filler bismaleimide resin and preparation method thereof |
| CN103881379A (en) * | 2014-03-20 | 2014-06-25 | 西北工业大学 | Hydroxyl silicate/phosphorus-containing benzoxazine/bismaleimide resin composite material and preparation method thereof |
| CN103881379B (en) * | 2014-03-20 | 2016-05-18 | 西北工业大学 | Hydroxy silicate/phosphorous benzoxazine/bismaleimide resin composite material and preparation method thereof |
| CN104592665A (en) * | 2015-02-13 | 2015-05-06 | 芜湖市伟华泡塑有限公司 | Modified polystyrene resin foam plastic |
| CN104610678A (en) * | 2015-02-13 | 2015-05-13 | 芜湖市伟华泡塑有限公司 | Heat-resistant high-tenacity polystyrene resin foamed plastic |
| CN109988305A (en) * | 2017-12-29 | 2019-07-09 | 深圳光启尖端技术有限责任公司 | Modified bismaleimide resin and preparation method thereof |
| CN109180947A (en) * | 2018-07-24 | 2019-01-11 | 西北工业大学 | One kind modified bismaleimide resin containing ethenyl cage model sesquialter siloxane and preparation method |
| WO2021134993A1 (en) * | 2019-12-31 | 2021-07-08 | 广东生益科技股份有限公司 | Resin composition and prepreg sheet using same, and insulating plate |
| TWI742643B (en) * | 2019-12-31 | 2021-10-11 | 大陸商廣東生益科技股份有限公司 | Resin composition, prepreg sheet and insulating board using the same |
| TWI756679B (en) * | 2019-12-31 | 2022-03-01 | 大陸商廣東生益科技股份有限公司 | A kind of modified maleimide compound and its preparation method and application |
| WO2022266951A1 (en) * | 2021-06-24 | 2022-12-29 | 穗晔实业股份有限公司 | Thermosetting resin composition and prepreg |
| US11639439B2 (en) | 2021-06-24 | 2023-05-02 | Prior Company Limited | Thermosetting resin composition and prepreg |
| CN113929913A (en) * | 2021-10-19 | 2022-01-14 | 福建师范大学 | Bismaleimide/polyether siloxane resin and preparation method thereof |
| CN114561101A (en) * | 2022-04-01 | 2022-05-31 | 焦作市天益科技有限公司 | Diallyl bisphenol A modified bismaleimide resin capable of prolonging shelf life and preparation method thereof |
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Application publication date: 20121114 |