IPC분류정보
| 국가/구분 |
United States(US) Patent
등록
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| 국제특허분류(IPC7판) |
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| 출원번호 |
US-0512276
(1974-10-04)
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발명자
/ 주소 |
- Buck Carl J. (Berkeley Heights NJ)
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| 출원인 / 주소 |
- Johnson & Johnson (New Brunswick NJ 02)
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| 인용정보 |
피인용 횟수 :
82 인용 특허 :
0 |
초록
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Difunctional monomers of the formula, OO ��2=C－C－O－R－O－C－C=CH2 ││ CNCN where R is an organic linking group derived from a diol or a dihalide of the formula X-R-X, where X is either chlorine, bromine, iodine, or hydroxy, are prepared by reacting a conjugated diene, exemplified by anthracene, with an
Difunctional monomers of the formula, OO ��2=C－C－O－R－O－C－C=CH2 ││ CNCN where R is an organic linking group derived from a diol or a dihalide of the formula X-R-X, where X is either chlorine, bromine, iodine, or hydroxy, are prepared by reacting a conjugated diene, exemplified by anthracene, with an ester of 2-cyanoacrylic acid to form the Diels-Alder adduct of the ester. The ester adduct is hydrolyzed to ultimately obtain either the Diels-Alder adduct of either 2-cyanoacrylic acid--alkali metal salt or 2-cyanoacryloyl halide. These latter intermediates are respectively reacted with either the dihalide or the diol to afford the bis-Diels-Alder adduct of the R substituted bis (2-cyanoacrylate) monomer. The protective diene group may then be removed, for example, by reaction with excess maleic anhydride and the resulting difunctional monomer isolated. The difunctional monomers thus prepared can be utilized as crosslinking agents in blends comprising one or more of these difunctional monomers and at least one monofunctional monomer, exemplified by an ester of 2-cyanoacrylic acid. Alternately, one or more difunctional monomers can be homopolymerized or copolymerized to a highly crosslinked polymer. The copolymerized compositions of the monomer blends are particularly useful as adhesives, especially in dental applications for coating or sealing enamel surfaces of teeth to allay decay, or for the bonding of brackets to teeth in orthodontics the bond being substantially more resistant to moisture than where the monofunctional monomer is used alone.
대표청구항
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In the preparation of bis (2-cyanoacrylate) monomer represented by the General Formula VI OO��2=C－C－O－R－O－C－C=CH2││CNCN from 2-cyanoacrylic acid ester of the General Formula I O �2=C－C－O－R′ │ CN the steps comprising: a. introducing a blocking group by means of a Diels-Alder reaction in which a cycli
In the preparation of bis (2-cyanoacrylate) monomer represented by the General Formula VI OO��2=C－C－O－R－O－C－C=CH2││CNCN from 2-cyanoacrylic acid ester of the General Formula I O �2=C－C－O－R′ │ CN the steps comprising: a. introducing a blocking group by means of a Diels-Alder reaction in which a cyclic 1,3-diene is reacted with said cyanoacrylic ester of Formula I to give a compound of the General Formula II －CH2D│O �2 D│ │O │�2 D│ │O │�2CH2－D│OO│D│��2-cyanoacrylate) of Formula VI; wherein said blocking group of Formula II, III, And V is any one of the group consisting of where R1 and R2 are the same R1 and R2 are selected from the group consisting of H, an alkyl group of 1 to 5 carbons, phenyl, Br or Cl and where R1 and R2 are different, R1 is H and R2 is a member selected from any of the group consisting of an alkyl group of 1 to 5 carbons, phenyl, Br and Cl; where R3 is H or CH3; and wherein the organo linking group R of Formulas VI and V is the same and is any one of the group consisting of: －(CH2)m－ where m is an integer of from 1 to 20 inclusive; －CH－(CH2)n－CH－, ││ R4R5 where n is an integer of from 0 to 18 inclusive, and R4 and R5 are independently hydrogen or a C1 to C5 alkyl group, R4 and R5 not simultaneously being hydrogen; －(CH2)r－Z－(CH2)s－, where Z is －O－, －S－, －CH=CH－; －C≡C－; R6│－C－,│R7 and where r and s are independent integers of from 1 to 10 inclusive and r and s total from 2 to 20, R6 and R7 are independently hydrogen or a straight or branched chain C1 and C5 alkyl group where x and y are integers of from 1 to 6 inclusive; where x and y are as hereinbefore defined; －CH2－(CF2)z－CH2－, where z is an integer of from 1 to 10 inclusive; and CH3CH3││－CH2－Si－O－Si－CH2－;││CH3CH3 and wherein R′ of Formula I and II is an alcohol moiety selected from C1 to C16 alkyl, cyclohexyl or phenyl.
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