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US 6,005,137 AGranted
Halogenated acrylates and polymers derived therefrom
Assignee3M Innovative Properties Company
InventorsGeorge G. I. Moore, Fred B. McCormick, Mita Chattoraj, Elisa M. Cross, Junkang Jacob Liu, Ralph R. Roberts, Jay F. Schulz
Life of this patent
Estimating the term…
Abstract
Acrylates having a high degree of halogenation, as well as polymers that include one or more mer units derived from such acrylates provide materials having tailorable optical and physical properties. The polymers find utility particularly in optical devices including optical waveguides and interconnecting devices.
Claims18
A halogenated acrylate having the general formula ##STR21## wherein M is H,
- A is oxygen or sulfur, and
- Z is a group having at most 150 carbon atoms selected from the group consisting of ##STR22## in which each R.sup.1 independently is F, Cl, or Br;
- (2) ##STR23## in which each R.sup.2 independently is (a) a perfluorinated, perchlorinated, or per(chlorofluoro) group (i), (ii), (iii), (iv), or (v) wherein
- (i) is a C.sub.1 -C.sub.20 aliphatic group,
- (ii) is a C.sub.3 to C.sub.20 cycloaliphatic alkyl group,
- (iii) is a C.sub.6 -C.sub.20 aryl group,
- (iv) is a C.sub.7 -C.sub.20 aralkyl group, and
- (v) is a C.sub.7 -C.sub.20 alkaryl group,
- (b) F, Cl, Br, I, Q (defined below), R.sup.4 COO--, R.sup.4 O--, --COOR.sup.4, --OSO.sub.2 R.sup.4, or --SO.sub.2 OR.sup.4, wherein R.sup.4 is any group from (a)(i), (a)(ii), (a)(iii), (a)(iv), and (a)(v),
- or any two adjacent R.sup.2 groups together can form a perfluorinated, perchlorinated, or per(chlorofluoro) cycloaliphatic or aromatic ring moiety which optionally can further include n R.sup.2 groups where n is a whole number in the range of 0 to 25 that describes the number of free sites on the ring moiety, wherein Q is ##STR24## in which A is as defined as above, with the proviso that all R.sup.2 groups in the molecule can be the same only when R.sup.2 is not Cl, F, Br or I;
- and each R.sup.3 independently can be
- (a) a perfluorinated, perchlorinated, or per(chlorofluoro)
- (i) C.sub.1 -C.sub.20 aliphatic group,
- (ii) C.sub.3 -C.sub.20 cycloaliphatic group,
- (iii) C.sub.6 -C.sub.20 aryl group,
- (iv) C.sub.7 -C.sub.20 aralkyl group, and
- (v) C.sub.7 -C.sub.20 alkaryl group,
- (b) F, Cl, Br, I, Q (defined above), R.sup.4 COO--, R.sup.4 O--, --COOR.sup.4, --OSO.sub.2 R.sup.4, or
- --SO.sub.2 OR.sup.4, wherein R.sup.4 is any group from (a)(i), (a)(ii), (a)(iii), (a)(iv), and (a)(v),
- or any two adjacent R.sup.3 groups together can form a perfluorinated, perchlorinated, or per(chlorofluoro) cycloaliphatic or aromatic ring moiety which optionally can further include n R.sup.3 groups where n is a whole number in the range of 0 to 25 that describes the number of free sites on the ring moiety;
- (3) --(R.sub.f).sub.2 E in which
- both R.sub.f groups together are part of a perfluorinated, perchlorinated, or per(chlorofluoro) cycloaliphatic ring group or independently are perfluorinated, perchlorinated, or per(chlorofluoro)
- (a) C.sub.1 -C.sub.20 aliphatic groups,
- (b) C.sub.3 -C.sub.20 cycloaliphatic groups,
- (c) C.sub.6 -C.sub.20 aryl groups,
- (d) C.sub.7 -C.sub.20 aralkyl groups, or
- (e) C.sub.7 -C.sub.20 alkaryl groups,
- (f) C.sub.4 -C.sub.2 heteroaryl groups,
- (g) C.sub.4 -C.sub.20 heteroaralkyl groups,
- (h) C.sub.4 -C.sub.20 heteroalkaryl groups,
- wherein heteroatoms can be one or more of O, N, and S atoms, with the proviso that at least one R.sub.f group includes one or more of (i) at least one straight-chain C.sub.4 -C.sub.20 aliphatic or C.sub.4 -C.sub.20 cycloaliphatic group, (ii) at least one ether oxygen atom, and (iii) at least one branched C.sub.3 -C.sub.20 aliphatic group, and
- E is R.sub.f, ##STR25## wherein R.sup.1, R.sup.2, and R.sub.f, and Q are defined as above, and (4) --CR.sub.f (E).sub.2,
- wherein each E independently is as defined above, and R.sub.f is as defined above.
30 more elements
A halogenated acrylate having structure selected from the group consisting of ##STR32##
A halogenated acrylate having a structure selected from the group consisting of
A polymer comprising at least one mer unit derived by polymerization of the olefinic bond from a halogenated acrylate having the general formula wherein A is oxygen or sulfur, and Z is a group having at most 150 carbon atoms selected from the group consisting of ##STR33## in which each R.sup.1 independently is F, Cl, or Br;
- ##STR34## in which each R.sup.2 independently is (a) a perfluorinated, perchlorinated, or per(chlorofluoro) group (i), (ii), (iii), (iv), or (v) wherein
- (i) is a C.sub.1 -C.sub.20 aliphatic group,
- (ii) is a C.sub.3 to C.sub.20 cycloaliphatic alkyl group,
- (iii) is a C.sub.6 -C.sub.20 aryl group,
- (iv) is a C.sub.7 -C.sub.20 aralkyl group, and
- (v) is a C.sub.7 -C.sub.20 alkaryl group,
- (b) F, Cl, Br, I, Q (defined below), R.sup.4 COO--, R.sup.4 O--, --COOR.sup.4, --OSO.sub.2 R.sup.4, or --SO.sub.2 OR.sup.4, wherein R.sup.4 is any group from (a)(i), (a)(ii), (a)(iii), (a)(iv), and (a)(v),
- or any two adjacent R.sup.2 groups together can form a perfluorinated, perchlorinated, or per(chlorofluoro) cycloaliphatic or aromatic ring moiety in which n fluoro or chloro groups optionally can be replaced by n R.sup.2 groups where n is a whole number in the range of 0 to 25, wherein Q is ##STR35## in which A is as defined as above, with the proviso that all R.sup.2 groups in the molecule can be the same only when R.sup.2 is not Cl, F, Br or I;
- and each R.sup.3 independently can be
- (a) a perfluorinated, perchlorinated, or per(chlorofluoro)
- (i) C.sub.1 -C.sub.20 aliphatic group,
- (ii) C.sub.3 -C.sub.20 cycloaliphatic group,
- (iii) C.sub.6 -C.sub.20 aryl group,
- (iv) C.sub.7 -C.sub.20 aralkyl group, and
- (v) C.sub.7 -C.sub.20 alkaryl group,
- (b) F, Cl, Br, 1, Q (defined above), R.sup.4 COO--, R.sup.4 O--, --COOR.sup.4, --OSO.sub.2 R.sup.4, or
- --SO.sub.2 OR.sup.4, wherein R.sup.4 is any group from (a)(i), (a)(ii), (a)(iii), (a)(iv), and (a)(v),
- or any two adjacent R.sup.3 groups together can form a perfluorinated, perchlorinated, or per(chlorofluoro) cycloaliphatic or aromatic ring moiety in which n fluoro or chloro groups which can be replaced by n R.sup.3 groups wherein n is a whole number in the range of 0 to 25, and R.sup.3 is as defined above;
- (3) --(R.sub.f).sub.2 E
- wherein both R.sub.f groups together comprise a perfluorinated, perchlorinated, or per(chlorofluoro) cycloaliphatic ring group or independently comprise perfluorinated, perchlorinated, or per(chlorofluoro)
- (a) C.sub.1 -C.sub.20 aliphatic groups,
- (b) C.sub.3 -C.sub.20 cycloaliphatic groups,
- (c) C.sub.6 -C.sub.20 aryl groups,
- (d) C.sub.7 -C.sub.20 aralkyl groups, or
- (e) C.sub.7 -C.sub.20 alkaryl groups,
- (f) C.sub.4 -C.sub.20 heteroaryl groups,
- (g) C.sub.4 C.sub.20 heteroaralkyl groups,
- (h) C.sub.4 -C.sub.20 heteroalkaryl groups,
- wherein heteroatoms can be one or more of O, N, and S atoms, with the proviso that at least one R.sub.f group includes one or more of (i) at least one straight-chain C.sub.4 -C.sub.20 aliphatic or C.sub.4 -C.sub.20 cycloaliphatic group, (ii) at least one ether oxygen atom, and (iii) at least one branched C.sub.3 -C.sub.20 aliphatic group, and
- E is R.sub.f, ##STR36## wherein R.sup.1, R .sup.2, and R.sub.f, and Q are defined as above, and (4) --CR.sub.f (E).sub.2,
- wherein each E independently is as defined above, and R.sub.f is as defined above.
28 more elements
Dependencies are inferred from the claim text.