Addition-fragmentation oligomers having high refractive index groups
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IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
A61K-006/083
A61F-002/00
C08G-061/02
C08G-061/04
A61K-006/00
C09J-004/06
B32B-037/10
B32B-037/12
C09D-004/00
C09J-004/00
출원번호
US-0112220
(2015-02-10)
등록번호
US-9730864
(2017-08-15)
국제출원번호
PCT/US2015/015102
(2015-02-10)
국제공개번호
WO2015/126657
(2015-08-27)
발명자
/ 주소
Fornof, Ann R.
Moser, William H.
Joly, Guy D.
출원인 / 주소
3M Innovative Properties Company
대리인 / 주소
Kokko, Kent S.
인용정보
피인용 횟수 :
0인용 특허 :
29
초록▼
Addition-fragmentation oligomers of the general formula Z—By-A-(B-A)x-B-A-By—Z, where the A monomers units are derived from a diester or diacid, the B monomer units are derived from a difunctional monomer having functional groups co-reactive with the acid or ester groups of the A monomer, x+y is zer
Addition-fragmentation oligomers of the general formula Z—By-A-(B-A)x-B-A-By—Z, where the A monomers units are derived from a diester or diacid, the B monomer units are derived from a difunctional monomer having functional groups co-reactive with the acid or ester groups of the A monomer, x+y is zero to 60, Z comprises an ethylenically unsaturated, polymerizable group, A monomers comprise a 1-methylene-3,3-dimethylpropyl group, and at least one B monomer unit comprises a high refractive index group.
대표청구항▼
1. An addition-fragmentation oligomer of the formula wherein RA is RB a (hetero)hydrocarbyl group, wherein at least 50% of the RB units are substituted with a high refractive index group,X1 is —O— or NR5—, where R5 is H or C1-C4 alkyl;Z comprises an ethylenically unsaturated polymerizable group;y i
1. An addition-fragmentation oligomer of the formula wherein RA is RB a (hetero)hydrocarbyl group, wherein at least 50% of the RB units are substituted with a high refractive index group,X1 is —O— or NR5—, where R5 is H or C1-C4 alkyl;Z comprises an ethylenically unsaturated polymerizable group;y is 0 or 1;x is 0 or 1. 2. The addition-fragmentation oligomer of claim 1, wherein at least 75% of the RB units are substituted by a high refractive index group. 3. The addition-fragmentation oligomer of claim 1, wherein the high refractive index group is selected from benzyl, 2-, 3-, and 4-biphenyl, 1-, 2, 3-, 4-, and 9-fluorenyl, 4-(1-methyl-1-phenethyl)phenoxyethyl; phenylthio; 1-, 2-, 3- and 4-napthyl, 1- and 2-naphthylthio; 2,4,6-tribromophenoxy; 2,4-dibromophenoxy; 2-bromophenoxy; 1-, and 2-naphthyloxy; 3-phenoxy-; 2-, 3- and 4-phenylphenoxy; 2,4-dibromo-6-sec-butylphenyl; 2,4-dibromo-6-isopropylphenyl; 2,4-dibromophenyl; pentabromobenzyl and pentabromophenyl. 4. The addition-fragmentation oligomer of claim 1 derived from A compounds of the formula: R1—O—CO—RA—CO—O—R1, wherein RA is a 1-methylene-3,3-dimethylpropyl group and R1 is H, alkyl, aryl or RFG, where RFG is an aryl or an alkyl further substituted with a nucleophilic or electrophilic functional group. 5. The addition-fragmentation oligomer of claim 4 derived from B compounds of the formula: X2—RB—X2, wherein RB is a (hetero)hydrocarbyl group and X2 is functional group reactive with the functional groups of the A compound. 6. The addition-fragmentation oligomer of claim 5 wherein the compound of the formula X2—RB—X2 is selected from difunctional epoxides, diols, aziridines, isocyanates and diamines. 7. The addition-fragmentation oligomer of claim 1 where x+y is 0 to 2. 8. The addition-fragmentation oligomer of claim 1 where x+y is 1 to 2. 9. A polymerizable composition comprising the addition-fragmentation oligomer of claim 1, at least one free-radically polymerizable monomer, and an initiator. 10. The polymerizable composition of claim 9 comprising: a) 85 to 100 parts by weight of an (meth)acrylic acid ester;b) 0 to 15 parts by weight of an acid functional ethylenically unsaturated monomer;c) 0 to 10 parts by weight of a non-acid functional, ethylenically unsaturated polar monomer;d) 0 to 5 parts vinyl monomer; ande) 0 to 100 parts of a multifunctional (meth)acrylate; based on 100 parts by weight total monomer a) to d), andf) 0.1 to 12 parts by weight of the addition-fragmentation oligomer, based on 100 parts by weight of a) to e), andg) an initiator. 11. The polymerizable composition of claim 10 further comprising 0.01 to 100 parts of a multifunctional (meth)acrylate based on 100 parts by weight total monomer a) to d). 12. The polymerizable composition of claim 9 further comprising an inorganic filler. 13. An article comprising the cured polymerizable composition of claim 9 on a substrate. 14. A method of bonding two substrates together comprising the steps of coating the polymerizable composition of claim 9 to a surface of one or both substrates, contacting the coated surfaces, optionally with pressure, and curing the polymerizable compositions. 15. A hardcoat composition comprising one or more multifunctional (meth)acrylate monomers or (meth)acrylate oligomers, and the addition-fragmentation oligomer of claim 1. 16. The hardcoat composition of claim 15 comprising: a) 0.1-10 wt. % of the addition fragmentation oligomer;b) 20-80 wt. % of multifunctional (meth)acrylate monomers and/or multifunctional (meth)acrylate oligomers,c) 0 to 25 wt. % range of (meth)acrylate diluent, (0-25 wt. %); andd) 20 to 75 wt. % of silica. 17. A curable dental composition comprising: a) at least one dental resin comprising at least two ethylenically unsaturated group;b) an addition-fragmentation oligomer of claim 1; andc) optionally an inorganic oxide filler. 18. The dental composition of claim 17 wherein the inorganic oxide filler comprises nanoparticles.
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